Seventeen steroids from the pith of Tetrapanax papyriferus.

PubMed

Xu, Jing-Lan; Gu, Li-Hua; Wang, Zheng-Tao; Bligh, Annie; Han, Zhu-Zhen; Liu, Shou-Jin

2016-12-01

Two new steroidal ketones (1, 2), together with 10 known steroids (3-12) and five known steroidal saponins (13-17), have been obtained from the pitch of Tetrapanax papyrierus. The structures of 1 and 2 were elucidated as 3β-hydroxystigmast-8, 22-diene-7,11-dione and 3β-hydroxystigmast-8-ene-7,11-dione by IR, HR-ESI-MS, 1D and 2D NMR techniques. Except for 4, 14, 15, 16, 13 compounds reported in this paper were isolated from Tetrapanax papyriferus for the first time.

[Determination by high performance chromatography, steroid saponins in a biologically active food supplements containing the extract of Tribulus terrestris].

PubMed

Kozlova, O I; Perederiaev, O I; Ramenskaia, G V

2011-01-01

Steroidal saponins are bioactive substances of Tribulus terrestris and can be used to assess the quality of raw materials and processed products from them. For this purpose has been developed the method of qualitative and quantitative determination of steroidal saponins by high performance liquid chromatography with spectrophotometric and mass-selective detection and optimal conditions of sample preparation (70% methanol extraction with sonication and heating); also has been studied steroidal saponins composition of Tribulus terrestris (protodioscin, tribulosaponin B, metilprotodiostsin, terrestrozin H, prototribestin, gracillin and others were found).

Ultrahigh-performance liquid chromatography-ion trap mass spectrometry characterization of the steroidal saponins of Dioscorea panthaica Prain et Burkill and its application for accelerating the isolation and structural elucidation of steroidal saponins.

PubMed

Wang, Weihao; Zhao, Ye; Jing, Wenguang; Zhang, Jun; Xiao, Hui; Zha, Qin; Liu, An

2015-03-01

Dioscorea panthaica is a traditional Chinese medicinal herb used in the treatment of various physiological conditions, including cardiovascular disease, gastropathy and hypertension. Steroidal saponins (SS) are the main active ingredients of this herb and have effects on myocardial ischemia and cancer. The phytochemical evaluation of SS is both time-consuming and laborious, and the isolation and structural determination steps can be especially demanding. For this reason, the development of new methods to accelerate the processes involved in the identification, isolation and structural elucidation of SS is highly desirable. In this study, a new ultrahigh performance liquid chromatography-ion trap mass spectrometry (UHPLC-IT/MS(n)) method has been developed for the identification of the SS in D. panthaica Prain et Burkill. Notably, the current method can distinguish between spirostanol and furostanol-type compounds based on the fragmentation patterns observed by electrospray ionization-ion trap mass spectrometry (ESI-IT/MS(n)) analysis. UHPLC-IT/MS(n) was used to conduct a detailed investigation of the number, structural class and order of the sugar moieties in the sugar chains of the SS present in D. panthaica. The established fragmentation features were used to analyze the compounds found in the 65% ethanol fraction of the water extracts of D. panthaica. Twenty-three SS were identified, including 11 potential new compounds and six groups of isomers. Two of these newly identified SS were selected as representative examples, and their chemical structures were confirmed by (1)H and (13)C NMR analyses. This newly developed UHPLC-IT/MS(n) method therefore allowed for the efficient identification, isolation and structural determination of the SS in D. panthaica. Copyright © 2015 Elsevier Inc. All rights reserved.

Characterization of steroidal saponins from Dioscorea villosa and D Cayennensis using ultrahigh performance liquid chromatography/electrospray ionization quadruple time-of-flight mass spectrometry

USDA-ARS?s Scientific Manuscript database

Steroidal saponins were reported to be the major physiologically active constituents in yams. The structural characteristics of steroidal saponins in methanolic extracts from dried rhizomes of two Dioscorea species (D. villosa L. and D. cayenensis Lam.) and dietary supplements have analyzed using U...

Anemarrhena asphodeloides Non-Steroidal Saponin Components Alter the Pharmacokinetic Profile of Its Steroidal Saponins in Rat.

PubMed

Tang, Zhishu; Li, Guolong; Yang, Jie; Duan, Jinao; Qian, Dawei; Guo, Jianming; Zhu, Zhenhua; Song, Zhongxing

2015-06-26

A rapid, selective and sensitive UPLC-MS/MS assay was established to determine the plasma concentrations of four steroidal saponins. Sprague-Dawley rats were allocated to four groups which were orally administered Anemarrhena asphodeloides extracts (ASE), ASE combined with macromolecular fraction (ASE-MF), ASE combined with small molecule fraction (ASE-SF) and ASE combined with small molecule and macromolecular fraction (ASE-SF-MF) containing approximately the same dose of ASE. At different time points, the concentration of timosaponin BII, anemarsaponin BIII, timosaponin AIII and timosaponin E1 in rat plasma were determined and main pharmacokinetic parameters including Cmax, Tmax, T1/2, AUC were calculated using the DAS 3.2 software package. The statistical analysis was performed using the Student's t-test with p < 0.05 as the level of significance. MF had no effect on the pharmacokinetic behaviors and parameters of four steroidal saponins. It was found that Cmax and AUC of four steroidal saponins in group ASE-SF and ASE-SF-MF, were significantly increased compared with those in group ASE. These results indicate that SF in A. asphodeloides extracts could increase the absorption and improve the bioavailability of the steroidal saponins.

Furostanol saponins from the fruits of Tribulus terrestris.

PubMed

Chen, Gang; Su, Lan; Feng, Sheng-Guang; Lu, Xuan; Wang, Haifeng; Pei, Yue-Hu

2013-01-01

Two new steroidal saponins were isolated from the fruits of Tribulus terrestris. Their structures were assigned by spectroscopic analysis and colour reaction as 26-O-β-D-glucopyranosyl-(25R)-5α-furostane-12-one-3β,22α,26-triol-3-O-β-D-glucopyranosyl(1 → 4)-β-D-galactopyranoside (1); 26-O-β- D-glucopyranosyl-25(R)-5α-furostan-12-one-3β,22α,26-triol-3-O-α-L-rhamnopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 4)]-β-D-galactopyranoside (2).

Ligand fishing from Dioscorea nipponica extract using human serum albumin functionalized magnetic nanoparticles.

PubMed

Qinga, Lin-Sen; Xue, Ying; Zheng, Yi; Xiong, Jing; Liao, Xun; Ding, Li-Sheng; Li, Bo-Gang; Liu, Yi-Ming

2010-07-09

Dioscorea nipponica and the preparations made from it have been used for long to prevent and treat coronary heart disease in traditional Chinese medicine. A group of steroidal saponins present in the plant are believed to be the active ingredients. It has been a challenge to study the individual saponins separately due to the similarities in their chemical and physical properties. In this work, human serum albumin (HSA) functionalized magnetic nanoparticles (MNPs) were used to isolate and identify saponin ligands that bind to HSA from D. nipponica extract. Electrospray ionization mass spectrometry (ESI-MS) was used for compound identification and semi-quantification. Three saponins, i.e. dioscin, gracillin, and pseudo-protodioscin showed affinity to HSA-MNPs and thus isolated effectively from the extract. The other two saponins detected in the extract (i.e. protodioscin and 26-O-β-D-glucopyranosyl-3β,20α,26-triol-25(R)-Δ(5,22)-dienofurostan-3-O-α-L-rhamnopyranosyl (1→2)-[α-L-rhamnopyranosyl (1→4)]-β-D-glucopyranoside) exhibited no affinity at all. Among the three saponins fished out, dioscin bound to HSA much stronger than gracillin and pseudo-protodioscin did. The results indicated that affinity interaction between HSA immobilized on MNPs and small molecule compounds were highly dependent on chemical structures and, potentially, medicinal usefulness. The present work demonstrates a facile and effective way to isolate and identify ligands of receptors from medicinal plants.

A modified spectrophotometric assay to estimate deglycosylation of steroidal saponin to sapogenin by mixed ruminal microbes.

PubMed

Wang, Yuxi; McAllister, Tim A

2010-08-30

The lack of a method for measuring deglycosylation of saponins in ruminal fluid has limited the ability to investigate the impact of these compounds on rumen microorganisms. A simple spectrophotometric assay was adapted and a protocol developed to enable measurement of steroidal saponin and sapogenin in ruminal fluid. The procedure was used for in vitro determination of deglycosylation activity of rumen bacteria obtained from cattle fed or not fed Yucca schidigera saponin, and to determine the relative deglycosylase activities of extracellular and cell-associated enzymes from ruminal content. Modifications to the spectrophotometric assay (i.e. heating time shortened to 10 min and 0.5 mL dH(2)O added to the reaction mixture) improved the stability of the optical density (425 nm) of the chromophore for up to 24 h post-reaction. Centrifugation (12 000 x g, 20 min) enabled differential estimations of steroidal saponin and sapogenin in ruminal fluid. Steroidal saponin added to defaunated ruminal fluid (dRF) or clarified ruminal fluid (cRF) was recovered completely from the mixture as saponin + sapogenin (99.1% and 100.6%, respectively), whereas saponin recovery from the supernatant of dRF was greatly reduced (P < 0.001) compared to that from supernatant of cRF (58.5 vs. 98.7%). Saponin recoveries from the supernatants of dRF and cRF did not differ between donor cattle fed or not fed Yucca schidigera saponin (59.2 vs. 57.3% and 98.4 vs. 99.3%, respectively). The majority (89-90%) of saponin added to a ruminal extracellular enzyme preparation was recoverable in supernatant after 24 h, compared with only 26-32% remaining in supernatant from incubation with a cell-associated enzymes fraction. Mixed rumen bacteria deglycosylate steroidal saponin to sapogenin, at activity levels unaffected by prior exposure to saponin, but they were unable to degrade the sapogenin core structure. Deglycosylation activity occurred primarily in the cell-associated enzyme fraction of ruminal content. Copyright (c) 2008 Crown in the right of Canada. Published by John Wiley & Sons, Ltd.

Isolation, Characterization, and Quantification of Steroidal Saponins in Switchgrass (Panicum virgatum L.)

USDA-ARS?s Scientific Manuscript database

Switchgrass (Panicum virgatum L.) has been identified for development into an efficient and environment friendly biomass energy crop. A recent five-year study demonstrated that switchgrass grown for biofuel production produced 540 percent more energy than what is needed to grow, harvest and process...

A dihydrochalcone derivative and further steroidal saponins from Sansevieria trifasciata Prain.

PubMed

Tchegnitegni, Billy T; Teponno, Rémy B; Jenett-Siems, Kristina; Melzig, Matthias F; Miyamoto, Tomofumi; Tapondjou, Léon A

2017-10-26

Phytochemical investigation of the aerial parts of Sansevieria trifasciata, one of the most common Dracaenaceae plants, has resulted in the isolation of a new dihydrochalcone derivative named trifasciatine C (1), four previously unreported steroidal saponins as two pairs of inseparable regioisomers: trifasciatosides K/L (2/3), M/N (4/5), together with the known 1,2-(dipalmitoyl)-3-O-β-D-galactopyranosylglycerol (6), aconitic acid (7), and 1-methyl aconitic acid (8). Their structures were elucidated mainly by extensive spectroscopic analysis (1D and 2D nuclear magnetic resonance) and high-resolution electronspray ionization-mass spectrometry, as well as chemical methods and comparison of their spectral data with those of related compounds. Compounds 2/3 and 4/5 were evaluated for their antiproliferative activity on Hela cells, and no significant effect was observed.

Determination and fingerprint analysis of steroidal saponins in roots of Liriope muscari (Decne.) L. H. Bailey by ultra high performance liquid chromatography coupled with ion trap time-of-flight mass spectrometry.

PubMed

Li, Yong-Wei; Qi, Jin; Wen-Zhang; Zhou, Shui-Ping; Yan-Wu; Yu, Bo-Yang

2014-07-01

Liriope muscari (Decne.) L. H. Bailey is a well-known traditional Chinese medicine used for treating cough and insomnia. There are few reports on the quality evaluation of this herb partly because the major steroid saponins are not readily identified by UV detectors and are not easily isolated due to the existence of many similar isomers. In this study, a qualitative and quantitative method was developed to analyze the major components in L. muscari (Decne.) L. H. Bailey roots. Sixteen components were deduced and identified primarily by the information obtained from ultra high performance liquid chromatography with ion-trap time-of-flight mass spectrometry. The method demonstrated the desired specificity, linearity, stability, precision, and accuracy for simultaneous determination of 15 constituents (13 steroidal glycosides, 25(R)-ruscogenin, and pentylbenzoate) in 26 samples from different origins. The fingerprint was established, and the evaluation was achieved using similarity analysis and principal component analysis of 15 fingerprint peaks from 26 samples by ultra high performance liquid chromatography. The results from similarity analysis were consistent with those of principal component analysis. All results suggest that the established method could be applied effectively to the determination of multi-ingredients and fingerprint analysis of steroid saponins for quality assessment and control of L. muscari (Decne.) L. H. Bailey. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Fast Centrifugal Partition Chromatography Fractionation of Concentrated Agave (Agave salmiana) Sap to Obtain Saponins with Apoptotic Effect on Colon Cancer Cells.

PubMed

Santos-Zea, Liliana; Fajardo-Ramírez, Oscar R; Romo-López, Irasema; Gutiérrez-Uribe, Janet A

2016-03-01

Separation of potentially bioactive components from foods and plant extracts is one of the main challenges for their study. Centrifugal partition chromatography has been a successful technique for the screening and identification of molecules with bioactive potential, such as steroidal saponins. Agave is a source of steroidal saponins with anticancer potential, though the activity of these compounds in concentrated agave sap has not been yet explored. In this study, fast centrifugal partition chromatography (FCPC) was used coupled with in vitro tests on HT-29 cells as a screening procedure to identify apoptotic saponins from an acetonic extract of concentrated agave sap. The three most bioactive fractions obtained by FCPC at partition coefficients between 0.23 and 0.4 contained steroidal saponins, predominantly magueyoside b. Flow cytometry analysis determined that the fraction rich in kammogenin and manogenin glycosides induced apoptosis, but when gentrogenin and hecogenin glycosides were also found in the fraction, a necrotic effect was observed. In conclusion, this study provides the evidence that steroidal saponins in concentrated agave sap were potential inductors of apoptosis and that it was possible to separate them using fast centrifugal partition chromatography.

Sterol-recognition ability and membrane-disrupting activity of Ornithogalum saponin OSW-1 and usual 3-O-glycosyl saponins.

PubMed

Malabed, Raymond; Hanashima, Shinya; Murata, Michio; Sakurai, Kaori

2017-12-01

OSW-1 is a structurally unique steroidal saponin isolated from the bulbs of Ornithogalum saundersiae, and has exhibited highly potent and selective cytotoxicity in tumor cell lines. This study aimed to investigate the molecular mechanism for the membrane-permeabilizing activity of OSW-1 in comparison with those of other saponins by using various spectroscopic approaches. The membrane effects and hemolytic activity of OSW-1 were markedly enhanced in the presence of membrane cholesterol. Binding affinity measurements using fluorescent cholestatrienol and solid-state NMR spectroscopy of a 3-d-cholesterol probe suggested that OSW-1 interacts with membrane cholesterol without forming large aggregates while 3-O-glycosyl saponin, digitonin, forms cholesterol-containing aggregates. The results suggest that OSW-1/cholesterol interaction is likely to cause membrane permeabilization and pore formation without destroying the whole membrane integrity, which could partly be responsible for its highly potent cell toxicity. Copyright © 2017 Elsevier B.V. All rights reserved.

Natural male contraceptive: phytochemical investigation and anti-spermatogenic activity of Pistia stratiotes Linn.

PubMed

Singh, Kiran; Dubey, Bidhyut Kumar; Tripathi, Avinash C; Singh, Ajeet Pal; Saraf, Shailendra K

2014-01-01

This work is an attempt to explore the anti-spermatogenic activity of Pistia stratiotes and to investigate it as a male contraceptive. The prepared extracts were screened for the presence of alkaloids, glycosides, steroids, flavonoids, saponin and phenolic compounds. To assess the anti-spermatogenic activity, mice were orally administered with the various extracts of P. stratiotes (dose: 100 and 200 mg/kg body weight/day, for 45 days) and the most active, ethanolic extract was subjected to the isolation of phytoconstituent responsible for the activity. Diethyl ether fraction of ethanolic extract was taken to isolate a saponin, sitosterol-3-O-[2,4-di-O-acetyl-6-O-stearyl-β-D-glucopyranoside]. Anti-spermatogenic activity of the isolated saponin was evaluated at a dose of 50 mg/kg body weight/day, for 45 days. The treatment caused significant decrease (P < 0.01) in the weight of reproductive organs (testis, epididymis and seminal vesicle). The sperm count, sperm viability and serum testosterone levels were significantly lowered compared with that of the control group.

Weather and plant age affect the levels of steroidal saponin and Pithomyces chartarum spores in Brachiaria grass

USDA-ARS?s Scientific Manuscript database

Brachiaria species are cultivated worldwide in tropical and subtropical climates as the main forage source for ruminants. Numerous tropical and warm-season grasses cause hepatogenous photosensitization, among them several species of Brachiaria. Steroidal saponins present in these plants may be respo...

The effect of ensiling and haymaking on the concentrations of steroidal saponin in two Brachiaria grass species

USDA-ARS?s Scientific Manuscript database

Brachiaria (signalgrass) is now the most widely used tropical grass genus in Central and South America. However, Brachiaria spp. can cause hepatogenous photosensitization in livestock. Steroidal saponins, specifically protodioscin, present in Brachiaria spp. may be responsible for liver injury and s...

Comparative studies on performance of CCC and preparative RP-HPLC in separation and purification of steroid saponins from Dioscorea zingiberensis C.H.Wright

PubMed Central

Zhang, Xinxin; Liang, Jinru; Zhang, Yongmin; Liu, Jianli; Sun, Wenji; Ito, Yoichiro

2015-01-01

Steroid saponins from Dioscorea zingiberensis C.H.Wright were separated for the first time using two chromatographic methods for comparison: counter-current chromatography (CCC) coupled with evaporative light scattering detector (ELSD) and preparative reversed phase high-performance liquid chromatography (RP-HPLC) with an ultraviolet detector. Ethyl acetate-n-butanol-methanol-water (4:1:2:4, v/v) was chosen as the two-phase solvent system for CCC, while the acetonitrile-water (25:75 for the first step and15:85 for the second step, v/v) was used as the mobile phase in the preparative RP-HPLC. The following five steroid saponins were purified by theses two chromatographic methods, in one-step operation by CCC and by two-step operation in preparative RP-HPLC: 1) 26-O-β-D- glucopyranosyl-(25R)-furost-5-en-3β, 22ζ, 26-triol-3-O-[β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (compound A), 2) 26-O-β-D-glucopyranosyl-(25R)-furost-5-en-3β, 22ζ, 4) 26-triol-3-O-[β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (compound B), 3) 26-O-β-D-glucopyranosyl-(25R)-furost-5-en-3β, 22ζ, 26-triol-3-O-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranoside (compound C), 4) 26-O-β-D-glucopyranosyl-(25R)-furost-5, 20(22)-diene-3β, 26-diol-3-O-{α-L-rhamnopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→2)]}-β-D-glucopyranoside (compound D) and 5) 26-O-β-D-glucopyranosyl-(25R)-furost-5, 20(22)-diene-3β, 26-diol-3-O-[β-D-glucopyranosyl-(1→4)-α-L-rhamnopyranosy-(1→2)]-β-D-glucopyranoside (compound E). The purities of these five steroid saponins separated by both methods were over 95%, and structural identification of these compounds was performed by ESI-MS, and 13C NMR. Comparison of these two established approaches revealed that CCC required a longer separation time but with less solvent consumption, whereas preparative RP-HPLC gave a shorter separation time but with higher solvent consumption. These results demonstrated that either of these two methods of different separation mechanism is feasible, economical and efficient for rapid preparative isolation and purification of steroid saponins from Dioscorea zingiberensis C.H.Wright. PMID:26726306

Comparative studies on performance of CCC and preparative RP-HPLC in separation and purification of steroid saponins from Dioscorea zingiberensis C.H.Wright.

PubMed

Zhang, Xinxin; Liang, Jinru; Zhang, Yongmin; Liu, Jianli; Sun, Wenji; Ito, Yoichiro

2015-03-01

Steroid saponins from Dioscorea zingiberensis C.H.Wright were separated for the first time using two chromatographic methods for comparison: counter-current chromatography (CCC) coupled with evaporative light scattering detector (ELSD) and preparative reversed phase high-performance liquid chromatography (RP-HPLC) with an ultraviolet detector. Ethyl acetate-n-butanol-methanol-water (4:1:2:4, v/v) was chosen as the two-phase solvent system for CCC, while the acetonitrile-water (25:75 for the first step and15:85 for the second step, v/v) was used as the mobile phase in the preparative RP-HPLC. The following five steroid saponins were purified by theses two chromatographic methods, in one-step operation by CCC and by two-step operation in preparative RP-HPLC: 1) 26-O-β-D- glucopyranosyl-(25R)-furost-5-en-3β, 22ζ, 26-triol-3-O-[β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside ( compound A ), 2) 26-O-β-D-glucopyranosyl-(25R)-furost-5-en-3β, 22ζ, 4) 26-triol-3-O-[β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside ( compound B ), 3) 26-O-β-D-glucopyranosyl-(25R)-furost-5-en-3β, 22ζ, 26-triol-3-O-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranoside ( compound C ), 4) 26-O-β-D-glucopyranosyl-(25R)-furost-5, 20(22)-diene-3β, 26-diol-3-O-{α-L-rhamnopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→2)]}-β-D-glucopyranoside ( compound D ) and 5) 26-O-β-D-glucopyranosyl-(25R)-furost-5, 20(22)-diene-3β, 26-diol-3-O-[β-D-glucopyranosyl-(1→4)-α-L-rhamnopyranosy-(1→2)]-β-D-glucopyranoside ( compound E ). The purities of these five steroid saponins separated by both methods were over 95%, and structural identification of these compounds was performed by ESI-MS, and 13 C NMR. Comparison of these two established approaches revealed that CCC required a longer separation time but with less solvent consumption, whereas preparative RP-HPLC gave a shorter separation time but with higher solvent consumption. These results demonstrated that either of these two methods of different separation mechanism is feasible, economical and efficient for rapid preparative isolation and purification of steroid saponins from Dioscorea zingiberensis C.H.Wright.

Preparation of progenin III from total steroidal saponins of Dioscorea nipponica Makino using a crude enzyme from Aspergillus oryzae strain.

PubMed

Liu, Tingqiang; Yu, Hongshan; Liu, Chunying; Bao, Yongming; Hu, Xiangchun; Wang, Yuanhao; Liu, Bing; Fu, Yaoyao; Tang, Sihui; Jin, Fengxie

2013-05-01

Progenin III, one of the most active spirostanol saponins, is a potential candidate for anti-cancer therapy due to its strong antitumor activity and low hemolytic activity. However, the concentration of progenin III is extremely low in natural Dioscorea plants. In this paper, the progenin III production from total steroidal saponins of Dioscorea nipponica Makino was studied using the crude enzyme from Aspergillus oryzae DLFCC-38. The crude enzyme converting total steroidal saponins into progenin III was obtained from the A. oryzae DLFCC-38 culture. For enzyme production, the strain was cultured for 72 h at 30 °C with shaking at 150 rpm in 5 % (w/v) malt extract medium containing 2 % (v/v) extract of D. nipponica as the enzyme inducer. The crude enzyme converted total steroidal saponins into major progenin III with a high yield when the reaction was carried out for 9 h at 50 °C and pH 5.0 with the 20 mg/ml of substrate. In the preparation of progenin III, 117 g of crude progenin III was obtained from 160 g of substrate, and the crude product was purified with silica gel column to obtain 60.3 g progenin III of 93.4 % purity.

Isolation and Identification of Active Compounds from Papaya Plants and Activities as Antimicrobial

NASA Astrophysics Data System (ADS)

Prasetya, A. T.; Mursiti, S.; Maryan, S.; Jati, N. K.

2018-04-01

Extraction and isolation of papaya seeds and leaves (Carica papaya L) has been performed using n-hexane and ethanol solvents. Further isolation of the extract obtained using ethyl acetate and diethyl ether solvents. The result of the phytochemical test of papaya extract obtained by mixture of an active compound of flavonoids, alkaloids, tannins, steroids, and saponins. Ethyl acetate isolates containing only flavonoids and diethyl ether isolates contain only alkaloids. Extracts and isolates from papaya plants had gram-positive antibacterial activity greater than the gram-negative bacteria, but both did not have antifungal activity. Papaya extracts have greater antibacterial activity than flavonoid isolates and alkaloid isolates. Strong antibacterial inhibitory sequences are extracts of papaya plants, flavonoid isolates, and alkaloid isolates.

Metabolic and functional diversity of saponins, biosynthetic intermediates and semi-synthetic derivatives

PubMed Central

Moses, Tessa; Papadopoulou, Kalliope K.

2014-01-01

Saponins are widely distributed plant natural products with vast structural and functional diversity. They are typically composed of a hydrophobic aglycone, which is extensively decorated with functional groups prior to the addition of hydrophilic sugar moieties, to result in surface-active amphipathic compounds. The saponins are broadly classified as triterpenoids, steroids or steroidal glycoalkaloids, based on the aglycone structure from which they are derived. The saponins and their biosynthetic intermediates display a variety of biological activities of interest to the pharmaceutical, cosmetic and food sectors. Although their relevance in industrial applications has long been recognized, their role in plants is underexplored. Recent research on modulating native pathway flux in saponin biosynthesis has demonstrated the roles of saponins and their biosynthetic intermediates in plant growth and development. Here, we review the literature on the effects of these molecules on plant physiology, which collectively implicate them in plant primary processes. The industrial uses and potential of saponins are discussed with respect to structure and activity, highlighting the undoubted value of these molecules as therapeutics. PMID:25286183

The anticancer potential of steroidal saponin, dioscin, isolated from wild yam (Dioscorea villosa) root extract in invasive human breast cancer cell line MDA-MB-231 in vitro

USDA-ARS?s Scientific Manuscript database

Previously, we observed that wild yam (Dioscorea villosa) root extract (WYRE) was able to activate GATA3 in human breast cancer cells targeting epigenome. This study aimed to 'nd out if dioscin (DS), a bioactive compound of WYRE, can modulate GATA3 functions and cellular invasion in human breast can...

Characterization of Steroidal Saponins from Dioscorea villosa and D. cayenensis Using Ultrahigh Performance Liquid Chromatography/Electrospray Ionization Quadrupole Time-of-Flight Mass Spectrometry

PubMed Central

Avula, Bharathi; Wang, Yan-Hong; Wang, Mei; Ali, Zulfiqar; Smillie, Troy J.; Zweigenbaum, Jerry; Khan, Ikhlas A.

2017-01-01

Yam (Dioscorea spp.) is an important edible tuber plant used for medicinal purposes to promote health and longevity in Chinese tradition. Steroidal saponins were reported to be the major physiologically active constituents in yams. In this current work, the structural characteristics of steroidal saponins in methanolic extracts from dried rhizomes of two Dioscorea species (D. villosa L. and D. cayenensis Lam.) and dietary supplements have been identified and analyzed using UHPLC/QTOF-MS in both negative and positive ion modes. The fragmentation patterns of reference standards were determined and the steroidal saponins in the extracts were identified or tentatively characterized from their retention times and mass spectra. The fragments produced by collision-induced dissociation (CID) revealed the characteristic cleavage of glycosidic bonds, and the fragmentation pattern provided structural information about the sugars. Twenty-one saponins, including four tentatively identified compounds, were detected in the crude extracts of two Dioscorea species. These saponins can be used to distinguish D. villosa from D. cayenensis. For example, asperin and gracillin are found only in D. cayenensis, and dioscoreavilloside A and B and parvifloside are only found in D. villosa. This can be used to determine the presence or absence of D. villosa in commercial products, which may help determine the spiking of plant material, and/or prevent the use of potentially mislabeled or misidentified “Dioscorea” material. The analytical method also provided an alternative, fast method for quality control of Dioscorea species in dietary supplements. Principal component analysis showed that Dioscorea species and commercial products were easily distinguished. From this a partial least squares model was constructed to determine what species are in different products. PMID:24510365

The truth about false unicorn (Chamaelirium luteum): total synthesis of 23R,24S-chiograsterol B defines the structure and stereochemistry of the major saponins from this medicinal herb.

PubMed

Matovic, Nicholas J; Stuthe, Julia M U; Challinor, Victoria L; Bernhardt, Paul V; Lehmann, Reginald P; Kitching, William; De Voss, James J

2011-06-27

Chamaelirium luteum is used in traditional medicine systems and commercial botanical dietary supplements for the treatment of female reproductive health problems. Despite the wide use of this herb, only very limited phytochemical characterisation is available. Our investigation of C. luteum roots led to the isolation of two new steroidal saponins 1 and 2 that contain an unusual aglycone 3. The absolute configurations of these molecules were unable to be determined spectroscopically and thus the total synthesis of 3 was undertaken and achieved in 16 steps and 1.6 % overall yield from pregnenolone. The key step in the synthesis was the stereoselective installation of the side chain at C-17 and C-20, which employed anion-accelerated oxy-Cope methodology. The relative configuration of aglycone 3 was determined by X-ray crystallography of an advanced synthetic intermediate. The absolute configuration was based upon that of the pregnenolone-derived steroidal skeleton and determined to be 23R,24S. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Separation of furostanol saponins by supercritical fluid chromatography.

PubMed

Yang, Jie; Zhu, Lingling; Zhao, Yang; Xu, Yongwei; Sun, Qinglong; Liu, Shuchen; Liu, Chao; Ma, Baiping

2017-10-25

Supercritical fluid chromatography (SFC) has good separation efficiency and is suitable for separating weakly polar compounds. Furostanol saponins, as an important kind of steroidal saponins, generally have two sugar chains, which are polar and hydrophilic. The hydroxyl group at the C-22 position of furostanol saponins is active and easily reacts with lower alcohols under appropriate conditions. The separation of hydrophilic furostanol saponins was tested by SFC in this study. The effects of chromatographic conditions on the separation of the mixed furostanol saponins and their hydroxyl derivatives at the C-22 position were studied. The conditions for SFC, which included different column polarity, modifier, additive, and column temperature, were tested. After optimization, the mixed 10 similar structures of furostanol saponins were separated in 22min on the Diol column at a temperature of 40°C. The mobile phase was CO 2 (mobile phase A) and methanol (containing 0.2% NH 3 ∙H 2 O and 3% H 2 O) (mobile phase B). The backpressure was maintained isobarically at 11.03MPa. SFC was found to be effective in separating the furostanol saponins that shared the same aglycone but varied in sugar chains. SFC was sensitive to the number and type of sugars. The resolution of furostanol saponin isomers was not ideal. The extract of Dioscorea zingiberensis C. H. Wright was profiled by SFC-quadrupole time-of-flight mass spectrometry. The main saponins of the extract were well separated. Therefore, SFC could be used for separating hydrophilic furostanol saponins and analyzing traditional Chinese medicines that mainly contained steroidal saponins. Copyright © 2017 Elsevier B.V. All rights reserved.

Interaction of saponin 1688 with phase separated lipid bilayers.

PubMed

Chen, Maohui; Balhara, Vinod; Jaimes Castillo, Ana Maria; Balsevich, John; Johnston, Linda J

2017-07-01

Saponins are a diverse family of naturally occurring plant triterpene or steroid glycosides that have a wide range of biological activities. They have been shown to permeabilize membranes and in some cases membrane disruption has been hypothesized to involve saponin/cholesterol complexes. We have examined the interaction of steroidal saponin 1688-1 with lipid membranes that contain cholesterol and have a mixture of liquid-ordered (L o ) and liquid-disordered (L d ) phases as a model for lipid rafts in cellular membranes. A combination of atomic force microscopy (AFM) and fluorescence was used to probe the effect of saponin on the bilayer. The results demonstrate that saponin forms defects in the membrane and also leads to formation of small aggregates on the membrane surface. Although most of the membrane damage occurs in the liquid-disordered phase, fluorescence results demonstrate that saponin localizes in both ordered and disordered membrane phases, with a modest preference for the disordered regions. Similar effects are observed for both direct incorporation of saponin in the lipid mixture used to make vesicles/bilayers and for incubation of saponin with preformed bilayers. The results suggest that the initial sites of interaction are at the interface between the domains and surrounding disordered phase. The preference for saponin localization in the disordered phase may reflect the ease of penetration of saponin into a less ordered membrane, rather than the actual cholesterol concentration in the membrane. Dye leakage assays indicate that a high concentration of saponin is required for membrane permeabilization consistent with the supported lipid bilayer experiments. Crown Copyright © 2017. Published by Elsevier B.V. All rights reserved.

New pregnane and steroidal glycosides from Tribulus terrestris L.

PubMed

Liu, Tao; Chen, Gang; Yi, Guo-Qing; Xu, Jian-Kun; Zhang, Tian-Long; Hua, Hui-Ming; Pei, Yue-Hu

2010-03-01

Three new steroidal saponins were isolated from the fruits of Tribulus terrestris L. Their structures were elucidated by spectroscopic and chemical analysis as 16beta-(4'-methyl-5'-O-beta-D-glucopyranosyl-pentanoxy)-5alpha-pregn-3beta-ol-12,20-dione-3-O-beta-D-glucopyranosyl-(1 --> 2)-beta-D-glucopyranosyl-(1 --> 4)-beta-D-galactopyranoside (1), 2alpha,3beta-dihydroxy-5alpha-pregn-16-en-20-one 3-O-beta-D-glucopyranosyl-(1 --> 4)-beta-D-galactopyranoside (2) and 26-O-beta-D-glucopyranosyl-(25R)-5alpha-furostan-20(22)-en-2alpha,3beta,26-triol-3-O-beta-D-glucopyranosyl-(1 --> 4)-beta-D-galactopyranoside (3).

Spirostanol saponins and esculin from Rusci rhizoma reduce the thrombin-induced hyperpermeability of endothelial cells.

PubMed

Barbič, M; Willer, E A; Rothenhöfer, M; Heilmann, J; Fürst, R; Jürgenliemk, G

2013-06-01

Rusci rhizoma extracts are traditionally used against chronic venous disorders (CVD). To determine the effect of its secondary plant metabolites on the endothelium, phenolic compounds and saponins from Butcher's broom were isolated from a methanolic extract, and their activity on the thrombin-induced hyperpermeability of human microvascular endothelial cells (HMEC-1) was investigated in vitro. In addition to the six known spirostanol saponins deglucoruscin (5), 22-O-methyl-deglucoruscoside (6), deglucoruscoside (7), ruscin (8), ruscogenin-1-O-(α-l-rhamnopyranosyl-(1→2)-β-d-galactopyranoside (9) and 1-O-sulpho-ruscogenin (10), three new spirostanol derivatives were isolated and identified: 3'-O-acetyl-4'-O-sulphodeglucoruscin (1), 4'-O-(2-hydroxy-3-methylpentanoyl)-deglucoruscin (2) and 4'-O-acetyl-deglucoruscin (3). Furthermore, the coumarin esculin (4), which is also prominently present in other medicinal plants used in the treatment of CVD, was isolated for the first time from Rusci rhizoma. Five of the isolated steroid derivatives (2, 5, 8, 9 and 10) and esculin (4) were tested for their ability to reduce the thrombin-induced hyperpermeability of endothelial cells in vitro, and the results were compared to those of the aglycone neoruscogenin (11). The latter compound showed a slight but concentration-dependent reduction in hyperpermeability to 71.8% at 100μM. The highest activities were observed for the spirostanol saponins 5 and 8 and for esculin (4) at 10μM, and these compounds resulted in a reduction of the thrombin-induced hyperpermeability to 41.9%, 42.6% and 53.3%, respectively. For 2, 5 and 8, the highest concentration tested (100μM) resulted in a drastic increase of the thrombin effect. The effect of esculin observed at a concentration of 10μM was diminished at 100μM. These in vitro data provide insight into the pharmacological mechanism by which the genuine spirostanol saponins and esculin can contribute to the efficacy of Butcher's broom against chronic venous disorders. Copyright © 2013 Elsevier Ltd. All rights reserved.

Determination of three steroidal saponins from Ophiopogon japonicus (Liliaceae) via high-performance liquid chromatography with mass spectrometry.

PubMed

Wang, Yongyi; Xu, Jinzhong; Qu, Haibin

2013-01-01

A simple and accurate analytical method was developed for simultaneous quantification of three steroidal saponins in the roots of Ophiopogon japonicus via high-performance liquid chromatography (HPLC) with mass spectrometry (MS) in this study. Separation was performed on a Tigerkin C(18) column and detection was performed by mass spectrometry. A mobile phase consisted of 0.02% formic acid in water (v/v) and 0.02% formic acid in acetonitrile (v/v) was used with a flow rate of 0.5 mL min(-1). The quantitative HPLC-MS method was validated for linearity, precision, repeatability, stability, recovery, limits of detection and quantification. This developed method provides good linearity (r >0.9993), intra- and inter-day precisions (RSD <4.18%), repeatability (RSD <5.05%), stability (RSD <2.08%) and recovery (93.82-102.84%) for three steroidal saponins. It could be considered as a suitable quality control method for O. japonicus.

Antifungal activity and fungal metabolism of steroidal glycosides of Easter lily (Lilium longiflorum Thunb.) by the plant pathogenic fungus, Botrytis cinerea.

PubMed

Munafo, John P; Gianfagna, Thomas J

2011-06-08

Botrytis cinerea Pers. Fr. is a plant pathogenic fungus and the causal organism of blossom blight of Easter lily (Lilium longiflorum Thunb.). Easter lily is a rich source of steroidal glycosides, compounds which may play a role in the plant-pathogen interaction of Easter lily. Five steroidal glycosides, including two steroidal glycoalkaloids and three furostanol saponins, were isolated from L. longiflorum and evaluated for fungal growth inhibition activity against B. cinerea, using an in vitro plate assay. All of the compounds showed fungal growth inhibition activity; however, the natural acetylation of C-6''' of the terminal glucose in the steroidal glycoalkaloid, (22R,25R)-spirosol-5-en-3β-yl O-α-L-rhamnopyranosyl-(1→2)-[6-O-acetyl-β-D-glucopyranosyl-(1→4)]-β-D-glucopyranoside (2), increased antifungal activity by inhibiting the rate of metabolism of the compound by B. cinerea. Acetylation of the glycoalkaloid may be a plant defense response to the evolution of detoxifying mechanisms by the pathogen. The biotransformation of the steroidal glycoalkaloids by B. cinerea led to the isolation and characterization of several fungal metabolites. The fungal metabolites that were generated in the model system were also identified in Easter lily tissues infected with the fungus by LC-MS. In addition, a steroidal glycoalkaloid, (22R,25R)-spirosol-5-en-3β-yl O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (6), was identified as both a fungal metabolite of the steroidal glycoalkaloids and as a natural product in L. longiflorum for the first time.

Quality control and identification of steroid saponins in crude extracts from Dioscorea zingiberensis C. H. Wright by fingerprint with HPLC-ELSD and HPLC-ESI-Quadrupole/Time-of-fight tandem mass spectrometry

PubMed Central

Zhang, Xinxin; Liang, Jinru; Liu, Jianli; Zhao, Ye; Gao, Juan; Sun, Wenji; Ito, Yoichiro

2014-01-01

In this study, a fingerprint of steroid saponins, the major bioactive constituents in the crude extracts from Dioscorea zingiberensis C. H. Wright (DZW), has been established for the first time by high-performance liquid chromatography coupled with evaporative light scattering detector (HPLC-ELSD) and the simultaneous characterization of the steroid saponins by high-performance liquid chromatography coupled with electrospray ionization-mass spectrometry and quadrupole tandem time-of-fight mass analyzers detection (HPLC-ESI-Q/TOF). These HPLC analyses were both carried out on a Welchrom C18 column (250 mm × 4.6 mm I.D., 5 μm) with a mobile phase composed of water and acetonitrile under gradient elution. There were 68 common characteristic peaks in the fingerprints, in which 12 of them were confirmed by comparing their mass spectra and retention times with those of the reference compounds. In order to identify the other unknown peaks, their fragmentation behaviors characteristic for the major groups of steroid saponins from DZW with six types of aglycone skeletons were discussed in detail, and possible MS/MS fragmentation pathways were proposed for aiding the structural identification of these components. According to the summarized fragmentation patterns, these peaks were tentatively assigned by matching their empirical molecular formula with those of the published compounds, or by elucidating their quasi-molecular ions and fragment ions referring to available literature information when the reference standards were unavailable. As a result, 22 steroid saponins were found in DZW for the first time. In addition, the quantitative analysis of the 12 known peaks was accomplished at the same time which indicated that there was a great variability in the amount of these active compounds in different batches in the crude extracts. This approach could demonstrate that the fingerprint could be considered to be a suitable tool to comprehensively improve the quality control of DZW, and the identification and structural elucidation of the peaks in the fingerprint may provide important experimental data for further pharmacological and clinical researches. PMID:24418811

Simultaneous quantification of five steroid saponins from Dioscorea zingiberensis C.H.Wright in rat plasma by HPLC-MS/MS and its application to the pharmacokinetic studies

PubMed Central

Zhang, Xinxin; Li, Jing; Ito, Yoichiro; Sun, Wenji

2014-01-01

A simple, reliable and sensitive high-performance liquid chromatography tandem mass spectrometry method (HPLC-MS/MS) was established for simultaneous analyses of the following 5 steroid saponins in rat plasma after the single dose administration of total steroid saponins extracted from the rhizome of Dioscorea zingiberensis C.H.Wright for the first time. Protodioscin, huangjiangsu A, zingiberensis new saponin, dioscin, and gracillin were quantified using ginsenoside Rb1 as the internal standard (IS). The plasma samples were pretreated by a single step acetonitrile-mediated protein precipitation. The chromatographic separation was performed on an Inersil ODS-3 C18 column (250 mm × 4.6 mm, 5 μm) with the mobile phase composed of acetonitrile and water containing 0.1% formic acid under a gradient elution mode at 0.2 mL min−1 using a microsplit after the eluent from the HPLC apparatus. The quantification was accomplished on a triple quadrupole tandem mass spectrometer using the multiple reaction monitoring (MRM) in the positive ionization mode. The above five analytes were stable under sample storage and preparation conditions applied in the present study. The linearity, precision, accuracy, and recoveries of the analysis confirmed the requirements for quality-control purposes. After validation, this proposed method was successfully adopted to investigate the pharmacokinetic parameters of these five analytes. PMID:25201262

Greenhouse and Field Evaluation of the Natural Saponin CAY-1, for Control of Several Strawberry Diseases

USDA-ARS?s Scientific Manuscript database

The steroidal saponin from cayenne pepper, CAY-1, was tested as a potential fungicide in detached leaf assays and field trials. Efficacy of CAY-1 against strawberry anthracnose was compared to the commercial fungicide azoxystrobin. Both fungicides prevented anthracnose leaf lesions when applied to...

Saponins from sea cucumber and their biological activities.

PubMed

Zhao, Yingcai; Xue, Changhu; Zhang, Tiantian; Wang, YuMing

2018-06-22

Sea cucumbers, belonging to the phylum Echinodermata, have been valued for centuries as a nutritious and functional food with various bioactivities. Sea cucumbers can produce highly active substances, notably saponins, the main secondary metabolites, which are the basis of their chemical defense. The saponins are mostly triterpene glycosides with triterpenes or steroid in aglycone, which possess multiple biological properties including anti-tumor, hypolipidemic activity, improvement of nonalcoholic fatty liver, inhibition of fat accumulation, anti-hyperuricemia, promotion of bone marrow hematopoiesis, anti-hypertension, etc. Sea cucumber saponins have received attention due to their rich sources, low toxicity, high efficiency, and few side effects. This review summarizes current research on the structure and activities of sea cucumber saponins based on the physiological and pharmacological activities from source, experimental models, efficacy and mechanisms, which may provide a valuable reference for the development of sea cucumber saponins.

Effect of Agave americana and Agave salmiana Ripeness on Saponin Content from Aguamiel (Agave Sap).

PubMed

Leal-Díaz, Ana María; Santos-Zea, Liliana; Martínez-Escobedo, Hilda Cecilia; Guajardo-Flores, Daniel; Gutiérrez-Uribe, Janet Alejandra; Serna-Saldivar, Sergio Othón

2015-04-22

Steroidal saponins have shown beneficial health effects. Agave spp. leaves and rhizomes are sources of these compounds, but their presence has not been reported in the aguamiel. Aguamiel is the sweet edible sap from mature agave, and its quality is influenced by the plant ripening stage. The purpose of this research was to identify and quantitate saponins in aguamiel from Agave americana and Agave salmiana at two ripening stages. Saponins and sapogenins were identified with HPLC/ESI-MS/TOF and quantitated with HPLC/ELSD. Results proved the presence of saponins derived from kammogenin, manogenin, gentrogenin, and hecogenin. The saponin content in aguamiel from immature A. salmiana was 2-fold higher (478.3 protodioscin equivalents (PE) μg/g aguamiel (DM)) compared with A. americana (179.0 PE μg/g aguamiel (DM)). In both species, saponin content decreased when plants reached sexual maturity. This should be considered before evaluating the effects of Agave spp. as a source of bioactive saponins.

Cytotoxicity of the Roots of Trillium govanianum Against Breast (MCF7), Liver (HepG2), Lung (A549) and Urinary Bladder (EJ138) Carcinoma Cells.

PubMed

Khan, Kashif M; Nahar, Lutfun; Al-Groshi, Afaf; Zavoianu, Alexandra G; Evans, Andrew; Dempster, Nicola M; Wansi, Jean D; Ismail, Fyaz M D; Mannan, Abdul; Sarker, Satyajit D

2016-10-01

Trillium govanianum Wall. (Melanthiaceae alt. Trilliaceae), commonly known as 'nag chhatri' or 'teen patra', is a native species of the Himalayas. It is used in various traditional medicines containing both steroids and sex hormones. In folk medicine, the rhizomes of T. govanianum are used to treat boils, dysentery, inflammation, menstrual and sexual disorders, as an antiseptic and in wound healing. With the only exception of the recent report on the isolation of a new steroidal saponin, govanoside A, together with three known steroidal compounds with antifungal property from this plant, there has been no systematic pharmacological and phytochemical work performed on T. govanianum. This paper reports, for the first time, on the cytotoxicity of the methanol extract of the roots of T. govanianum and its solid-phase extraction (SPE) fractions against four human carcinoma cell lines: breast (MCF7), liver (HEPG2), lung (A549) and urinary bladder (EJ138), using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazoliumbromide cytotoxicity assay and liquid chromatography and electrospray ionization quadrupole time-of-flight mass spectrometry analysis of the SPE fractions. The methanol extract and all SPE fractions exhibited considerable levels of cytotoxicity against all cell lines, with the IC 50 values ranging between 5 and 16 µg/mL. Like other Trillium species, presence of saponins and sapogenins in the SPE fractions was evident in the liquid chromatography mass spectrometry data. Copyright © 2016 John Wiley & Sons, Ltd. Copyright © 2016 John Wiley & Sons, Ltd.

New steroidal saponin and antiulcer activity from Solanum paniculatum L.

PubMed

Vieira Júnior, Gerardo Magela; da Rocha, Cláudia Quintino; de Souza Rodrigues, Tamires; Hiruma-Lima, Clélia Akiko; Vilegas, Wagner

2015-11-01

Solanum paniculatum L. (Solanaceae) is a plant species widespread throughout tropical America, especially in the Brazilian Savanna region. It is used in Brazil for culinary purposes and in folk medicine to treat liver and gastric dysfunctions, as well as hangovers. Fractionation of the ethanolic extracts (70%) from aerial parts (leaves and twigs) of S. paniculatum led to the isolation of the two new saponins (22R, 23S, 25R)-3β, 6α, 23-trihydroxy-5α-spirostane 6-O-β-D-xylopyranosyl-(1" → 3"')-O-[β-D-quinovopyranosyl(1″' → 2')]-O-[α-L-rhamnopyranosyl(1" → 3')]-O-β-D-quinovopyranoside (1) and diosgenin 3-O-β-D-glucopyranosyl(1" → 6')-O-β-D-glucopyranoside (2) together with four know compounds: caffeic acid (3), diosgenin β-D-glucopyranoside (4), rutin (5), and quercetin 3-O-α-L-rhamnopyranosyl (1"' → 6 ″)-O-β-D-galactopyranoside (6). The structures of these compounds were elucidated by extensive use of 1D and 2D NMR experiments along with HRESIMS analyses. Different doses (31.25-500 mg/kg) of ethanolic extract of leaves from S. paniculatum were evaluated against gastric ulcer induced by ethanol in rats. The lower dose of extract able to promote antiulcer effect was 125 mg/kg. The treatment with S. paniculatum by oral route was able to decrease gastric lesion area and also reduced levels of myeloperoxidase (MPO) in the gastric mucosa. Our results reveal for the first time, steroidal saponins from S. paniculatum and the antiulcer effect of this species at this lower dose. Copyright © 2014 Elsevier Ltd. All rights reserved.

Quality control and identification of steroid saponins from Dioscorea zingiberensis C. H. Wright by fingerprint with HPLC-ELSD and HPLC-ESI-Quadrupole/Time-of-fight tandem mass spectrometry.

PubMed

Zhang, Xinxin; Liang, Jinru; Liu, Jianli; Zhao, Ye; Gao, Juan; Sun, Wenji; Ito, Yoichiro

2014-03-01

In this study, a fingerprint of steroid saponins, the major bioactive constituents in the crude extracts from Dioscorea zingiberensis C. H. Wright (DZW), has been established for the first time by combined use of the following two methods: high-performance liquid chromatography coupled with evaporative light scattering detector (HPLC-ELSD) and the simultaneous characterization of the steroid saponins by high-performance liquid chromatography coupled with electrospray ionization-mass spectrometry and quadrupole tandem time-of-fight mass analyzers detection (HPLC-ESI-Q/TOF). All HPLC analyses were carried out on a Welchrom C18 column (250mm×4.6mm I.D., 5μm) with a mobile phase composed of water and acetonitrile under gradient elution. There were 68 common characteristic peaks in the fingerprints, in which 12 of them were confirmed by comparing their mass spectra and retention times with those of the reference compounds. In order to identify other unknown peaks, their fragmentation behaviors characteristic of the major groups of steroid saponins from DZW with six types of aglycone skeletons were discussed in detail, and possible MS/MS fragmentation pathways were proposed for aiding the structural identification of these components. According to the summarized fragmentation patterns, these peaks were tentatively assigned by matching their empirical molecular formula with those of the published compounds, or by elucidating their quasi-molecular ions and fragment ions referring to available literature information when the reference standards were unavailable. As a result, 22 new steroid saponins were found in DZW for the first time. In addition, the quantitative analysis of the nine (except for the reference compounds A, B, and C) known peaks was accomplished at the same time which indicated that there was a great variability in the amount of these active compounds in different batches in the crude extracts. This approach could demonstrate that the fingerprint could be considered to be a suitable tool to comprehensively improve the quality control of DZW. The identification and structural elucidation of the peaks in the fingerprint may provide important experimental data for further pharmacological and clinical researches. Copyright © 2014. Published by Elsevier B.V.

Chemical constituents of the genus Polygonatum and their role in medicinal treatment.

PubMed

Zhao, Xueying; Li, Ji

2015-04-01

Polygonatum is a famous traditional Chinese medicine that is widely used in China, Korea and Japan. In the last decade, constituents of the genus have been reported including steroidal saponins, flavones, alkaloids, lignins, amino acids and carbohydrates, some of which show biological properties such as antiviral and antitumor activity, variable effects on the immune system and anticoagulant activity. In addition, some findings provide novel evidence that Polygonatum species may contain potential anti-tumor and anti-viral proteins for possible medical application and large-scale pharmaceutical production. In this review, we focus on the updated research of the chemical constituents of Polygonatum including polysaccharides, steroidal saponins, flavonoids and lectins, and their potential therapeutic roles.

Microwave-assisted extraction (MAE) of bioactive saponin from mahogany seed (Swietenia mahogany Jacq)

NASA Astrophysics Data System (ADS)

Waziiroh, E.; Harijono; Kamilia, K.

2018-03-01

Mahogany is frequently used for medicines for cancer, tumor, and diabetes, as it contains saponin and flavonoid. Saponin is a complex glycosydic compound consisted of triterpenoids or steroids. Saponin can be extracted from a plant by using a solvent extraction. Microwave Assisted Extraction (MAE) is a non-conventional extraction method that use micro waves in the process. This research was conducted by a Complete Random Design with two factors which were extraction time (120, 150, and 180 seconds) and solvent ratio (10:1, 15:1, and 20:1 v/w). The best treatment of MAE were the solvent ratio 15:1 (v/w) for 180 seconds. The best treatment resulting crude saponin extract yield of 41.46%, containing 11.53% total saponins, and 49.17% of antioxidant activity. Meanwhile, the treatment of maceration method were the solvent ratio 20:1 (v/w) for 48 hours resulting 39.86% yield of saponin crude extract, 9.26% total saponins and 56.23% of antioxidant activity. The results showed MAE was more efficient (less time of extraction and solvent amount) than maceration method.

Poecillastrosides, Steroidal Saponins from the Mediterranean Deep-Sea Sponge Poecillastra compressa (Bowerbank, 1866)

PubMed Central

Calabro, Kevin; Kalahroodi, Elaheh Lotfi; Rodrigues, Daniel; Díaz, Caridad; de la Cruz, Mercedes; Cautain, Bastien; Laville, Rémi; Reyes, Fernando; Pérez, Thierry; Soussi, Bassam; Thomas, Olivier P.

2017-01-01

The first chemical investigation of the Mediterranean deep-sea sponge Poecillastra compressa (Bowerbank, 1866) led to the identification of seven new steroidal saponins named poecillastrosides A–G (1–7). All saponins feature an oxidized methyl at C-18 into a primary alcohol or a carboxylic acid. While poecillastrosides A–D (1–4) all contain an exo double bond at C-24 of the side-chain and two osidic residues connected at O-2′, poecillastrosides E–G (5–7) are characterized by a cyclopropane on the side-chain and a connection at O-3′ between both sugar units. The chemical structures were elucidated through extensive spectroscopic analysis (High-Resolution Mass Spectrometry (HRESIMS), 1D and 2D NMR) and the absolute configurations of the sugar residues were assigned after acidic hydrolysis and cysteine derivatization followed by LC-HRMS analyses. Poecillastrosides D and E, bearing a carboxylic acid at C-18, were shown to exhibit antifungal activity against Aspergillus fumigatus. PMID:28672858

Poecillastrosides, Steroidal Saponins from the Mediterranean Deep-Sea Sponge Poecillastra compressa (Bowerbank, 1866).

PubMed

Calabro, Kevin; Kalahroodi, Elaheh Lotfi; Rodrigues, Daniel; Díaz, Caridad; Cruz, Mercedes de la; Cautain, Bastien; Laville, Rémi; Reyes, Fernando; Pérez, Thierry; Soussi, Bassam; Thomas, Olivier P

2017-06-26

The first chemical investigation of the Mediterranean deep-sea sponge Poecillastra compressa (Bowerbank, 1866) led to the identification of seven new steroidal saponins named poecillastrosides A-G ( 1 - 7 ). All saponins feature an oxidized methyl at C-18 into a primary alcohol or a carboxylic acid. While poecillastrosides A-D ( 1 - 4 ) all contain an exo double bond at C-24 of the side-chain and two osidic residues connected at O-2', poecillastrosides E-G ( 5 - 7 ) are characterized by a cyclopropane on the side-chain and a connection at O-3' between both sugar units. The chemical structures were elucidated through extensive spectroscopic analysis (High-Resolution Mass Spectrometry (HRESIMS), 1D and 2D NMR) and the absolute configurations of the sugar residues were assigned after acidic hydrolysis and cysteine derivatization followed by LC-HRMS analyses. Poecillastrosides D and E, bearing a carboxylic acid at C-18, were shown to exhibit antifungal activity against Aspergillus fumigatus .

Trichomonicidal and parasite membrane damaging activity of bidesmosic saponins from Manilkara rufula.

PubMed

de Brum Vieira, Patrícia; Silva, Nícolas Luiz Feijó; Menezes, Camila Braz; da Silva, Márcia Vanusa; Silva, Denise Brentan; Lopes, Norberto Peporine; Macedo, Alexandre José; Bastida, Jaume; Tasca, Tiana

2017-01-01

The infection caused by Trichomonas vaginalis is the most common but overlooked non-viral sexually transmitted disease worldwide. Treatment relies on one class of drugs, the 5-nitroimidazoles, but resistance is widespread. New drugs are urgently needed. We reported the effect of crude and purified saponin fractions of Manilkara rufula against Trichomonas vaginalis. The compound responsible for antitrichomonal activity was isolated and identified as an uncommon bidesmosic saponin, Mi-saponin C. This saponin eliminated parasite viability without toxicity against the human vaginal epithelial line (HMVII). In addition, the isolated saponin fraction improved the metronidazole effect against a metronidazole-resistant isolate and dramatically reduced the cytoadherence of T. vaginalis to human cells. Investigation of the mechanism of death showed that the saponin fraction induced the parasite death due to profound membrane damage, inducing a disturbance of intracellular content without nuclear damage. To the best of our knowledge, this is the first report of antitrichomonal activity in the bidesmosic saponins of Manilkara rufula.

Trichomonicidal and parasite membrane damaging activity of bidesmosic saponins from Manilkara rufula

PubMed Central

Silva, Nícolas Luiz Feijó; Menezes, Camila Braz; da Silva, Márcia Vanusa; Silva, Denise Brentan; Lopes, Norberto Peporine; Macedo, Alexandre José; Bastida, Jaume; Tasca, Tiana

2017-01-01

The infection caused by Trichomonas vaginalis is the most common but overlooked non-viral sexually transmitted disease worldwide. Treatment relies on one class of drugs, the 5-nitroimidazoles, but resistance is widespread. New drugs are urgently needed. We reported the effect of crude and purified saponin fractions of Manilkara rufula against Trichomonas vaginalis. The compound responsible for antitrichomonal activity was isolated and identified as an uncommon bidesmosic saponin, Mi-saponin C. This saponin eliminated parasite viability without toxicity against the human vaginal epithelial line (HMVII). In addition, the isolated saponin fraction improved the metronidazole effect against a metronidazole-resistant isolate and dramatically reduced the cytoadherence of T. vaginalis to human cells. Investigation of the mechanism of death showed that the saponin fraction induced the parasite death due to profound membrane damage, inducing a disturbance of intracellular content without nuclear damage. To the best of our knowledge, this is the first report of antitrichomonal activity in the bidesmosic saponins of Manilkara rufula. PMID:29190689

Flavonoids and other constituents from Aletris spicata and their chemotaxonomic significance.

PubMed

Li, Lin-Zhen; Wang, Meng-Hua; Sun, Jian-Bo; Liang, Jing-Yu

2014-01-01

Eleven compounds, including four flavonoids [(2R,3R)-2,3-dihydro-3,5-dihydroxy-7,4'-dimethoxyflavone (1), 5-hydroxy-7,8,4'-trimethoxy-flavone (2), amentoflavone (10) and apigenin (11)], two penylpropanoids [sinapaldehyde (3) and 3-methoxy-4-hydroxy-cinnamic aldehyde (4)], three phenolic acids [4-hydroxyl-3,5-dimethoxy-benzaldehyde (5), 4-hydroxyacetophen-one (6) and p-hydroxybenzaldehyde (7)], one furan derivative [5-hydroxymethyl furfural (8)] and one steroid saponin [β-sitosterol-3-O-β-d-glucoside (9)], were isolated and identified from Aletris spicata. Among them, compounds 1-7, 9 and 10 were reported from the genus Aletris for the first time. Furthermore, seven of them (1-6, 10) were obtained from the family Liliaceae for the first time. Chemotaxonomy of the isolated compounds is discussed briefly.

Triterpenoid saponins from the roots of Clematis argentilucida.

PubMed

Zhao, Mei; Ma, Ning; Qiu, Feng; Tian, Xiangrong; Zhang, Yan; Tang, Haifeng; Liu, Xinyou

2014-09-01

Reinvestigation of the n-BuOH extract of the roots of Clematis argentilucida led to the isolation of a new ursane-type triterpenoid saponin 1 and a new taraxerane-type saponin 2, four known saponins 3-6 first isolated from the species, together with seven saponins 7-13 reported in the previous papers. The structures of saponins 1-6 were elucidated by extensive spectroscopic analysis and chemical evidences. The ursane-type and taraxerane-type triterpenoid saponins were obtained from genus Clematis for the first time, and the aglycone of saponin 1, 3β,28-dihydroxy-18αH-ursan-20-en was first encountered. The cytotoxicity of all the saponins was evaluated against human glioblastoma U251MG cell lines. The monodesmosidic saponins 1, 2 and 4-8 exhibited cytotoxic activity against the cells with IC50 values ranging from 6.95 to 38.51 μM. Copyright © 2014 Elsevier B.V. All rights reserved.

Saponin Interactions with Model Membrane Systems - Langmuir Monolayer Studies, Hemolysis and Formation of ISCOMs.

PubMed

de Groot, Carolin; Müller-Goymann, Christel C

2016-12-01

Saponins are used in medicine due to their pharmacological and immunological effects. To better understand interactions of saponins with model membranes and natural membranes of, for example, erythrocytes, Langmuir film balance experiments are well established. For most saponins, a strong interaction with cholesterol was demonstrated in dependence of both the aglycone part and the sugar moieties and is suggested to be correlated with a strong hemolytic activity, high toxicity, and high surface activity, as was demonstrated for the steroid saponin digitonin. In general, changes in the sugar chain or in substituents of the aglycone result in a modification of the saponin properties. A promising saponin with regard to fairly low hemolytic activity and high adjuvant effect is α -tomatine, which still shows a high affinity for cholesterol. An interaction with cholesterol and lipids has also been proven for the Quillaja saponin from the bark of Quillaja saponaria Molina. This triterpene saponin was approved in marketed vaccines as an adjuvant due to the formation of immunostimulating complexes. Immunostimulating complexes consist of a Quillaja saponin, cholesterol, phospholipids, and a corresponding antigen. Recently, another saponin from Quillaja brasiliensis was successfully tested in immunostimulating complexes, too. Based on the results of interaction studies, the formation of drug delivery systems such as immunostimulating complexes or similar self-assembled colloids is postulated for a variety of saponins. Georg Thieme Verlag KG Stuttgart · New York.

Triterpenoid saponins from the rhizomes of Anemone flaccida and their inhibitory activities on LPS-induced NO production in macrophage RAW264.7 cells.

PubMed

Huang, Xiao-Jun; Tang, Jing-Qun; Li, Man-Mei; Liu, Qing; Li, Yao-Lan; Fan, Chun-Lin; Pei, Hong; Zhao, Hui-Nan; Wang, Ying; Ye, Wen-Cai

2014-01-01

A new ursane-type triterpenoid saponin, flaccidoside IV (1), and three new oleanane-type triterpenoid saponins, flaccidosides V-VII (2-4), along with 17 known saponins (5-21), were isolated from the rhizomes of Anemone flaccida. The structures of the new triterpenoid saponins were determined based on spectroscopic analyses and chemical methods. All the isolated saponins were tested for their inhibitory activities on lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages, and several bisdesmosidic oleanane-type triterpenoid saponins (2, 7, and 10) showed significant inhibitory activities, which indicated they had potential anti-inflammatory activities under their noncytotoxic concentrations in vitro.

Genomic and Coexpression Analyses Predict Multiple Genes Involved in Triterpene Saponin Biosynthesis in Medicago truncatula[C][W

PubMed Central

Naoumkina, Marina A.; Modolo, Luzia V.; Huhman, David V.; Urbanczyk-Wochniak, Ewa; Tang, Yuhong; Sumner, Lloyd W.; Dixon, Richard A.

2010-01-01

Saponins, an important group of bioactive plant natural products, are glycosides of triterpenoid or steroidal aglycones (sapogenins). Saponins possess many biological activities, including conferring potential health benefits for humans. However, most of the steps specific for the biosynthesis of triterpene saponins remain uncharacterized at the molecular level. Here, we use comprehensive gene expression clustering analysis to identify candidate genes involved in the elaboration, hydroxylation, and glycosylation of the triterpene skeleton in the model legume Medicago truncatula. Four candidate uridine diphosphate glycosyltransferases were expressed in Escherichia coli, one of which (UGT73F3) showed specificity for multiple sapogenins and was confirmed to glucosylate hederagenin at the C28 position. Genetic loss-of-function studies in M. truncatula confirmed the in vivo function of UGT73F3 in saponin biosynthesis. This report provides a basis for future studies to define genetically the roles of multiple cytochromes P450 and glycosyltransferases in triterpene saponin biosynthesis in Medicago. PMID:20348429

Hemolytic and cytotoxic properties of saponin purified from Holothuria leucospilota sea cucumber

PubMed Central

Soltani, Mozhgan; Parivar, Kazem; Baharara, Javad; Kerachian, Mohammad Amin; Asili, Javad

2014-01-01

Background: Holothuroids (sea cucumbers) are members of the phylum echinodermata, which produce saponins. Saponins exhibit a wide spectrum of pharmacological and biological activities. In this study, we isolated the crude saponins from the body wall of the dominant Iranian species of sea cucumber, Holothuria leucospilota (H. leucospilota). The purpose of this study was to confirm the presence of saponins in the Persian Gulf H. leucospilota and study the hemolytic and cytotoxic activities of these compounds. Methods: The body wall of sea cucumber was dried and powdered and the crude saponins were isolated using various solvents. The crude saponins were further purified by column chromatography using HP-20 resin. The foam test, Thin Layer Chromatography (TLC), hemolytic assay, and Fourier Transform Infrared Spectroscopy (FTIR) confirmed the presence of saponins. Cytotoxicity was analyzed using a 3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide (MTT) assay on A549 cells, a human lung cancer cell line. Results: The foam test, hemolytic assay, and TLC supported the presence of saponin compounds in the 80% ethanol fraction of H. leucospilota. The infrared (IR) spectrum of the extract showed hydroxyl (-OH), alkyl (C-H), ether (C-O) and ester (–C=O) absorption characteristic of teriterpenoid saponins. The C-O-C absorption indicated glycoside linkages to the sapogenins. The crude saponin extracted from sea cucumber was cytotoxic to A549 cells. Conclusion: The 80% ethanol fraction of saponin isolated from H. leucospilota exhibited hemolytic activity and offers promise as an anti-cancer candidate. PMID:26989736

Hemolytic and cytotoxic properties of saponin purified from Holothuria leucospilota sea cucumber.

PubMed

Soltani, Mozhgan; Parivar, Kazem; Baharara, Javad; Kerachian, Mohammad Amin; Asili, Javad

2014-10-01

Holothuroids (sea cucumbers) are members of the phylum echinodermata, which produce saponins. Saponins exhibit a wide spectrum of pharmacological and biological activities. In this study, we isolated the crude saponins from the body wall of the dominant Iranian species of sea cucumber, Holothuria leucospilota (H. leucospilota). The purpose of this study was to confirm the presence of saponins in the Persian Gulf H. leucospilota and study the hemolytic and cytotoxic activities of these compounds. The body wall of sea cucumber was dried and powdered and the crude saponins were isolated using various solvents. The crude saponins were further purified by column chromatography using HP-20 resin. The foam test, Thin Layer Chromatography (TLC), hemolytic assay, and Fourier Transform Infrared Spectroscopy (FTIR) confirmed the presence of saponins. Cytotoxicity was analyzed using a 3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide (MTT) assay on A549 cells, a human lung cancer cell line. The foam test, hemolytic assay, and TLC supported the presence of saponin compounds in the 80% ethanol fraction of H. leucospilota. The infrared (IR) spectrum of the extract showed hydroxyl (-OH), alkyl (C-H), ether (C-O) and ester (-C=O) absorption characteristic of teriterpenoid saponins. The C-O-C absorption indicated glycoside linkages to the sapogenins. The crude saponin extracted from sea cucumber was cytotoxic to A549 cells. The 80% ethanol fraction of saponin isolated from H. leucospilota exhibited hemolytic activity and offers promise as an anti-cancer candidate.

A Steroidal Saponin from Ophiopogon japonicus Extends the Lifespan of Yeast via the Pathway Involved in SOD and UTH1

PubMed Central

Sun, Kaiyue; Cao, Shining; Pei, Liang; Matsuura, Akira; Xiang, Lan; Qi, Jianhua

2013-01-01

Nolinospiroside F is a steroidal saponin isolated from Ophiopogon japonicus (O. japonicus). In this study, we found that nolinospiroside F significantly extends the replicative lifespan of K6001 yeast at doses of 1, 3 and 10 μM, indicating that it has an anti-aging effect. This may be attributed to its anti-oxidative effect, as nolinospiroside F could increase yeast survival under oxidative stress conditions and decrease the level of malondialdehyde (MDA), an oxidative stress biomarker. It could also increase anti-oxidative stress genes, SOD1 and SOD2, expression, and the activity of superoxide dismutase (SOD). It increase the activity of SIRT1, an upstream inducer of SOD2 expression. In sod1 and sod2 mutant yeast strains, nolinospiroside F failed to extend their replicative lifespan. These results indicate that SOD participates in the anti-aging effect of nolinospiroside F. Furthermore, nolinospiroside F inhibited the expression of UTH1, a yeast-aging gene that is involved in the oxidative stress of yeast, and failed to extend the replicative lifespan of uth1 or skn7 mutant yeast cells. SKN7 is the transcriptional activator of UTH1. We also demonstrate that SOD and UTH1 regulate each other’s expression. Together, these results suggest that SOD and UTH1 genes are required for and play interactive roles in nolinospiroside F-mediated yeast lifespan extension. PMID:23439553

Two new triterpene saponins from the anti-inflammatory saponin fraction of Ilex pubescens root.

PubMed

Wang, Jing-Rong; Zhou, Hua; Jiang, Zhi-Hong; Liu, Liang

2008-07-01

The saponin fraction from the ethanolic extracts of the root of Ilex pubescens Hook. et Arn. (Ilexaceae) was found to exhibit potent anti-inflammatory effects on carrageenan-induced paw edema in rats. Two novel triterpene saponins, pubescenosides C and D (1 and 2, resp.), together with five known saponins were isolated from this saponin fraction. The structures of 1 and 2 were elucidated as (20beta)-3-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-xylopyranosyl]ursa-12,18-dien-28-oic acid 28-O-beta-D-glucopyranosyl ester, and (20beta)-3-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->2)-beta-D-xylopyranosyl]ursa- 12,18-dien-28-oic acid 28-O-beta-D-glucopyranosyl ester, respectively, on the basis of chemical and spectroscopic data. Five known saponins isolated from the saponin fraction were identified as ilexsaponin B(1), B(2), B(3), A(1), and chikusetsusaponin IV(a).

Polyhydroxy steroids and saponins from China Sea starfish Asterina pectinifera and their biological activities.

PubMed

Peng, Yan; Zheng, Jianxian; Huang, Riming; Wang, Yifei; Xu, Tunhai; Zhou, Xuefeng; Liu, Qiuying; Zeng, Fanli; Ju, Huaiqiang; Yang, Xianwen; Liu, Yonghong

2010-06-01

A new polyhydroxy sterol ester, (25S)-5alpha-cholestane-3beta,6alpha,7alpha,8,15alpha,16beta-hexahydroxyl-26-O-14'Z-eicosenoate (1), together with seven known steroid derivatives (2-8), were isolated from the EtOH extract of the whole body of China Sea starfish Asterina pectinifera. The structure of 1 was determined by using extensive spectra analysis (IR, 1D and 2D NMR, and MS), chemical degradation, and comparison with the known compound (25S)-5alpha-cholestane-3beta,6alpha,7alpha,8,15alpha,16beta,26-heptol (2). All the isolates were evaluated for their antiviral activity against herpes simplex virus type 1 (HSV-1) and their cytotoxicity against human liver carcinoma HepG2 cell line in vitro. Compounds 3-6, and 8 exhibited antiviral activity against HSV-1 virus with the minimal inhibitory concentration (MIC) values of 0.2, 0.05, 0.2, 0.22, and 0.07 microM, respectively. While compounds 4 and 5 exhibited cytotoxicity against HepG2 cells with IC(50) values of 0.2 and 1.6 microM, respectively.

Triterpenoid Saponins from Anemone rivularis var. Flore-Minore and Their Anti-Proliferative Activity on HSC-T6 Cells.

PubMed

Wang, Xiao-Yang; Gao, Hui; Xie, Xiao-Jie; Jurhiin, Jirimubatu; Zhang, Mu-Zi-He; Zhou, Yan-Ping; Liu, Rui; Ning, Meng; Han, Jin; Tang, Hai-Feng

2018-02-23

Five previously undescribed triterpenoid saponins ( 1 - 5 ), along with eight known ones ( 6 - 13 ), were isolated from the whole plants of Anemone rivularis var. flore-minore . Their structures were clarified by extensive spectroscopic data and chemical evidence. For the first time, the lupane-type saponins ( 3 and 12 ) were reported from the Anemone genus. The anti-proliferative activity of all isolated saponins was evaluated on hepatic stellate cells (HSC-T6). Saponins 12 and 13 , which possess more monosaccharides than the others, displayed potent anti-proliferative activity, with IC 50 values of 18.21 and 15.56 μM, respectively.

Isolation and Characterization of Saponin-Producing Fungal Endophytes from Aralia elata in Northeast China

PubMed Central

Wu, Hao; Yang, Hongyan; You, Xiangling; Li, Yuhua

2012-01-01

The purpose of this study was to investigate the diversity of endophytic fungi of Aralia elata distributed in Northeast China as well as their capacity to produce saponins. Ninety-six strains of endophytic fungi were isolated, and polymerase chain reaction (PCR) and sequencing were employed to identify the isolates. The saponin concentrations of the culture filtrates of representative strains were measured. The agar diffusion method was used to test antimicrobial activity, while high-performance liquid chromatography (HPLC) was employed to identify the saponins produced by representative strains. Alternaria, Botryosphaeria, Camarosporium, Cryptosporiopsis, Diaporthe, Dictyochaeta, Penicillium, Fusarium, Nectria, Peniophora, Schizophyllum, Cladosporium and Trichoderma species were isolated in this study. Overall, 25% of the isolates belonged to Diaporthe (Diaporthe eres), and 12.5% belonged to Alternaria. The highest concentration of saponins was produced by G22 (2.049 mg/mL). According to the results of the phylogenetic analysis, G22 belonged to the genus Penicillium. The culture filtrate of G22 exhibited antibacterial activity against Staphylococcus aureus, and ginsenosides Re and Rb2 were detected in G22 culture filtrates by HPLC. PMID:23203194

Triterpenoid saponins from Anemone flaccida induce apoptosis activity in HeLa cells.

PubMed

Han, Lin-Tao; Li, Juan; Huang, Fang; Yu, Shang-Gong; Fang, Nian-Bai

2009-01-01

Five triterpenoid saponins were isolated from Anemone flaccida Fr. Schmidt. Their structures were identified as glycoside St-I4a (1), glycoside St-J (2), anhuienoside E (3), hederasaponin B (4), and flaccidoside II (5). Compounds 1-2 were isolated from Anemone family for the first time, and compounds 3-4 were isolated from this plant for the first time. The inhibitory effects of saponins on proliferation of HeLa cells were studied by MTT assay, the apoptosis-induction activity was observed by cell-cycle analysis and caspase-3 expression assay. The antitumor activities of the saponins were ranked in the following order: 5 > 3 > 4 > 1 > 2. The data presented here indicated that naturally occurring triterpenoid saponins can be regarded as excellent structures for the potential development of new anticancer agents.

Chemical characteristics of saponins from Paris fargesii var. brevipetala and cytotoxic activity of its main ingredient, paris saponin H.

PubMed

Wen, Feiyan; Yin, Hongxiang; Chen, Chu; Liu, Xianbo; Xue, Dan; Chen, Tiezhu; He, Jun; Zhang, Hao

2012-06-01

More attention was paid to the anti-tumor activity of Rhizoma Paridis (RP) recently, of which the wild resource was decreased significantly. This study was aimed to elucidate the chemical characteristics of Paris fargesii var. brevipetala (PFB) that may be administrated as alternate resource of legal RP. A HPLC-ELSD method was established to characterize the steroid saponins in rhizomes of PFB and two legal Paris species [Paris polyphylla var. chinensis (PPC) and P. polyphylla var. yunnanensis (PPY)] in Chinese Pharmacopoeia (CP). Ten saponins (paris saponins I, II, V, VI, VII, H, gracillin and other three paris saponins) were involved as standards. The results indicated that PFB contained pennogenyl saponins as the main components with small amounts of diosgenin saponins. The total contents of the detected saponins in PFB ranged from 9.12mg/g to 85.33mg/g. Nine of the twelve PFB samples own a total content of paris saponins I, II, VI, and VII more than 6.0mg/g (meeting the standard of CP 2010 edition). Principal Component Analysis (PCA) and Partial Least Squares-Discriminate Analysis (PLS-DA) both confirmed the fact that saponin profiles of PFB, PPC and PPY were different from each other. In addition, paris saponin H (Ps H), the predominant saponin of PFB (>50%), was tested in vitro to evaluate its cytotoxic activities on HepG2, A549, RPE and L929 cells with a positive control of Cisplatin. Ps H showed a remarkable cytotoxic activity on A549 cells with an IC(50) value of 1.53±0.08μg/mL. Copyright © 2012 Elsevier B.V. All rights reserved.

Triterpenoid saponins from the fruits of Aesculus pavia.

PubMed

Zhang, Zhizhen; Li, Shiyou; Zhang, Shanmin; Gorenstein, David

2006-04-01

The compounds, named aesculiosides Ia-Ie, IIa-IId, and IVa-IVc, were isolated from an ethanol extract of the fruits of North American Aesculus pavia, along with two known compounds. Their structures were characterized as polyhydroxyoleanene pentacyclic triterpenoid saponins by spectroscopic and chemical analyses. These saponins were divided into three elution zones by chromatography according to the polarity because of the acyl substitution at C-21 and C-22 of the aglycone saponins moiety. These are structurally different from those isolated from Eurasian Aesculus hippocastanum and Aesculus chinensis in their oligosaccharide moieties.

Cytotoxic triterpenoid saponins from husks of Aesculus californica (Spach) Nutt.

PubMed

Yuan, Wei; Wang, Ping; Su, Zushang; Wang, Victoria S; Li, Shiyou

2013-06-01

Fifteen polyhydroxyoleanene saponins, aesculiosides C1-C15 (1-15), were isolated from husks of Aesculus californica. Their structures were established by extensive spectroscopic and chemical analyses. The triterpenoid saponins from A. californica have greater structural diversity than those from any other investigated species thus far in the genus Aesculus. The chemotaxonomic characteristic of aesculiosides C1-C15 is that the unit attached to the C-3 of the aglycone is a glucopyranosyl moiety, instead of a glucuronopyranosyl group in the saponins that have been isolated from other Aesculus species. The saponins isolated from A. californica then provide important evolutionary and chemotaxonomic knowledge of the Aesculus genus, a well-known intercontinental disjunct genus in the Northern hemisphere. Aesculiosides C1-C15 (1-15) showed cytotoxicity to human non-small cell lung tumor (A549) with GI50 ranged from 3.76 to >25μM. Copyright © 2013 Elsevier Ltd. All rights reserved.

Molecular diversity and body distribution of saponins in the sea star Asterias rubens by mass spectrometry.

PubMed

Demeyer, Marie; De Winter, Julien; Caulier, Guillaume; Eeckhaut, Igor; Flammang, Patrick; Gerbaux, Pascal

2014-02-01

Saponins are natural molecules that the common sea star Asterias rubens produces in the form of steroid glycosides bearing a sulfate group attached on the aglycone part. In order to highlight the inter-organ and inter-individual variability, the saponin contents of five distinct body components, namely the aboral body wall, the oral body wall, the stomach, the pyloric caeca and the gonads, from different individuals were separately analyzed by mass spectrometry. MALDI-ToF experiments were selected as the primary tool for a rapid screening of the saponin mixtures, whereas LC-MS and LC-MS/MS techniques were used to achieve chromatographic separation of isomers. First of all, our analyses demonstrated that the diversity of saponins is higher than previously reported. Indeed, nine new congeners were observed in addition to the 17 saponins already described in this species. On the basis of all the collected MS/MS data, we also identified collision-induced key-fragmentations that could be used to reconstruct the molecular structure of both known and unknown saponin ions. Secondly, the comparison of the saponin contents from the five different body components revealed that each organ is characterized by a specific mixture of saponins and that between animals there are also qualitative and quantitative variability of the saponin contents which could be linked to the sex or to the collecting season. Therefore, the observed high variability unambiguously confirms that saponins probably fulfill several biological functions in A. rubens. The current results will pave the way for our future studies that will be devoted to the clarification of the biological roles of saponins in A. rubens at a molecular level. © 2013.

Medicago truncatula CYP716A12 Is a Multifunctional Oxidase Involved in the Biosynthesis of Hemolytic Saponins[W

PubMed Central

Carelli, Maria; Biazzi, Elisa; Panara, Francesco; Tava, Aldo; Scaramelli, Laura; Porceddu, Andrea; Graham, Neil; Odoardi, Miriam; Piano, Efisio; Arcioni, Sergio; May, Sean; Scotti, Carla; Calderini, Ornella

2011-01-01

Saponins, a group of glycosidic compounds present in several plant species, have aglycone moieties that are formed using triterpenoid or steroidal skeletons. In spite of their importance as antimicrobial compounds and their possible benefits for human health, knowledge of the genetic control of saponin biosynthesis is still poorly understood. In the Medicago genus, the hemolytic activity of saponins is related to the nature of their aglycone moieties. We have identified a cytochrome P450 gene (CYP716A12) involved in saponin synthesis in Medicago truncatula using a combined genetic and biochemical approach. Genetic loss-of-function analysis and complementation studies showed that CYP716A12 is responsible for an early step in the saponin biosynthetic pathway. Mutants in CYP716A12 were unable to produce hemolytic saponins and only synthetized soyasaponins, and were thus named lacking hemolytic activity (lha). In vitro enzymatic activity assays indicate that CYP716A12 catalyzes the oxidation of β-amyrin and erythrodiol at the C-28 position, yielding oleanolic acid. Transcriptome changes in the lha mutant showed a modulation in the main steps of triterpenic saponin biosynthetic pathway: squalene cyclization, β-amyrin oxidation, and glycosylation. The analysis of CYP716A12 expression in planta is reported together with the sapogenin content in different tissues and stages. This article provides evidence for CYP716A12 being a key gene in hemolytic saponin biosynthesis. PMID:21821776

Soyasaponin Bh, a Triterpene Saponin Containing a Unique Hemiacetal-Functional Five-Membered Ring from Glycine max (Soybeans)

USDA-ARS?s Scientific Manuscript database

Soybeans (Glycine max L. Merill) and soy-based food products are major dietary sources of saponins. An oleanane triterpenoid saponin, soyasaponin Bh (1) containing a unique five-membered ring with a hemiacetal functionality together with seven known saponins were isolated from soybeans. Their struct...

Three further triterpenoid saponins from Gleditsia caspica fruits and protective effect of the total saponin fraction on cyclophosphamide-induced genotoxicity in mice.

PubMed

Melek, Farouk R; Aly, Fawzia A; Kassem, Iman A A; Abo-Zeid, Mona A M; Farghaly, Ayman A; Hassan, Zeinab M

2015-01-01

Three triterpenoidal saponins were isolated from the saponin fraction derived from a Gleditsia caspica Desf. methanolic fruit extract. The isolated saponins were identified as gleditsiosides B, C, and Q based on spectral data. The saponin-containing fraction was evaluated in vivo for genotoxic and antigenotoxic activities. The fraction caused no DNA damage in Swiss albino male mice treated with a dose of 45 mg/kg body weight for 24 h, although it significantly inhibited the number of chromosomal aberrations induced by cyclophosphamide (CP) in bone marrow and germ cells when applied before or after CP administration. The inhibitory indices in chromosomal aberrations were 59% and 41% for bone marrow and 48% and 43% for germ cells, respectively. In addition, the saponin fraction was found to reduce the viability of the human tumor cell line MCF-7 in a dose-dependent manner with an extrapolated IC50 value in the range of 220 μg/mL.

Antimicrobial steroidal saponin and oleanane-type triterpenoid saponins from Paullinia pinnata.

PubMed

Lunga, Paul K; Qin, Xu-Jie; Yang, Xing W; Kuiate, Jules-Roger; Du, Zhi Z; Gatsing, Donatien

2014-10-02

Paullinia pinnata L. (Sapindaceae) is an African woody vine, which is widely used in traditional medicine for the treatment of human malaria, erectile dysfunction and bacterial infections. A phytochemical investigation of its methanol leaf and stem extracts led to the isolation of seven compounds which were evaluated for their antimicrobial properties. The extracts were fractionated and compounds were isolated by chromatographic methods. Their structures were elucidated from their spectroscopic data in conjunction with those reported in literature. The antimicrobial activities of the crude extracts, fractions and compounds were evaluated against bacteria, yeasts and dermatophytes using the broth micro-dilution technique. Seven compounds: 2-O-methyl-L-chiro-inositol (1), β-sitosterol (2), friedelin (3), 3β-(β-D-Glucopyranosyloxy) stigmast-5-ene (4), (3β)-3-O-(2'-Acetamido-2'-deoxy-β-D-glucopyranosyl) oleanolic acid (5), (3β,16α-hydroxy)-3-O-(2'-Acetamido-2'-deoxy-β-D-glucopyranosyl) echinocystic acid (6) and (3β)-3-O-[β-D-glucopyranosyl-(1″-3')-2'-acetamido-2'-deoxy-β-D-galactopyranosyl]oleanolic acid (7) were isolated. Compounds 5 and 7 showed the best antibacterial and anti-yeast activities respectively (MIC value range of 0.78-6.25 and 1.56-6.25 μg/ml), while 6 exhibited the best anti-dermatophytic activity (MIC value range of 6.25-25 μg/ml). The results of the present findings could be considered interesting, taking into account the global disease burden of these susceptible microorganisms, in conjunction with the search for alternative and complementary medicines.

Cytotoxic triterpenoid saponins from Clematis tangutica.

PubMed

Zhao, Min; Da-Wa, Zhuo-Ma; Guo, Da-Le; Fang, Dong-Mei; Chen, Xiao-Zhen; Xu, Hong-Xi; Gu, Yu-Cheng; Xia, Bing; Chen, Lei; Ding, Li-Sheng; Zhou, Yan

2016-10-01

Eight previously undescribed oleanane-type triterpenoid saponins, clematangoticosides A-H, together with eight known saponins, were isolated from the whole plants of Clematis tangutica (Maxim.) Korsh. Their structures were elucidated by extensive spectroscopic analysis, in combination with chemical methods (acid hydrolysis and mild alkaline hydrolysis). Clematangoticosides D-G were found to be unusual 23, 28-bidesmosidic glycosides. The cytotoxic activities of all of the isolated saponins were evaluated against the four human cancer cell lines SGC-7901, HepG2, HL-60 and U251MG. Clematoside S, sapindoside B, kalopanax saponin A, and koelreuteria saponin A exhibited cytotoxicity against all of the test cancer cell lines with IC50 values in the range of 1.88-27.20 μM, while clematangoticoside D and F showed selective cytotoxicity against SGC-7901 with IC50 values of 24.22 and 21.35 μM, respectively. Copyright © 2016 Elsevier Ltd. All rights reserved.

Dianthosaponins A-F, triterpene saponins, flavonoid glycoside, aromatic amide glucoside and γ-pyrone glucoside from Dianthus japonicus.

PubMed

Nakano, Takahiro; Sugimoto, Sachiko; Matsunami, Katsuyoshi; Otsuka, Hideaki

2011-01-01

From aerial parts of Dianthus japonicus, six new and seven known oleanane-type triterpene saponins were isolated. The structures of the new saponins, named dianthosaponins A-F, were elucidated by means of high resolution mass spectrometry, and extensive inspection of one- and two-dimensional NMR spectroscopic data. A new C-glycosyl flavone, a glycosidic derivative of anthranilic acid amide and a maltol glucoside were also isolated.

Quantitative analysis of steroidal glycosides in different organs of Easter lily (Lilium longiflorum Thunb.) by LC-MS/MS.

PubMed

Munafo, John P; Gianfagna, Thomas J

2011-02-09

The bulbs of the Easter lily ( Lilium longiflorum Thunb.) are regularly consumed in Asia as both food and medicine, and the beautiful white flowers are appreciated worldwide as an attractive ornamental. The Easter lily is a rich source of steroidal glycosides, a group of compounds that may be responsible for some of the traditional medicinal uses of lilies. Since the appearance of recent reports on the role steroidal glycosides in animal and human health, there is increasing interest in the concentration of these natural products in plant-derived foods. A LC-MS/MS method performed in multiple reaction monitoring (MRM) mode was used for the quantitative analysis of two steroidal glycoalkaloids and three furostanol saponins, in the different organs of L. longiflorum. The highest concentrations of the total five steroidal glycosides were 12.02 ± 0.36, 10.09 ± 0.23, and 9.36 ± 0.27 mg/g dry weight in flower buds, lower stems, and leaves, respectively. The highest concentrations of the two steroidal glycoalkaloids were 8.49 ± 0.3, 6.91 ± 0.22, and 5.83 ± 0.15 mg/g dry weight in flower buds, leaves, and bulbs, respectively. In contrast, the highest concentrations of the three furostanol saponins were 4.87 ± 0.13, 4.37 ± 0.07, and 3.53 ± 0.06 mg/g dry weight in lower stems, fleshy roots, and flower buds, respectively. The steroidal glycoalkaloids were detected in higher concentrations as compared to the furostanol saponins in all of the plant organs except the roots. The ratio of the steroidal glycoalkaloids to furostanol saponins was higher in the plant organs exposed to light and decreased in proportion from the aboveground organs to the underground organs. Additionally, histological staining of bulb scales revealed differential furostanol accumulation in the basal plate, bulb scale epidermal cells, and vascular bundles, with little or no staining in the mesophyll of the bulb scale. An understanding of the distribution of steroidal glycosides in the different organs of L. longiflorum is the first step in developing insight into the role these compounds play in plant biology and chemical ecology and aids in the development of extraction and purification methodologies for food, health, and industrial applications. In the present study, (22R,25R)-spirosol-5-en-3β-yl O-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl-(1→4)-β-d-glucopyranoside, (22R,25R)-spirosol-5-en-3β-yl O-α-l-rhamnopyranosyl-(1→2)-[6-O-acetyl-β-d-glucopyranosyl-(1→4)]-β-d-glucopyranoside, (25R)-26-O-(β-d-glucopyranosyl)furost-5-ene-3β,22α,26-triol 3-O-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl-(1→4)-β-d-glucopyranoside, (25R)-26-O-(β-d-glucopyranosyl)furost-5-ene-3β,22α,26-triol 3-O-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranosyl-(1→3)-β-d-glucopyranoside, and (25R)-26-O-(β-d-glucopyranosyl)furost-5-ene-3β,22α,26-triol 3-O-α-l-rhamnopyranosyl-(1→2)-α-l-xylopyranosyl-(1→3)-β-d-glucopyranoside were quantified in the different organs of L. longiflorum for the first time.

Antiinflammatory triterpenoid saponins from the seeds of Aesculus chinensis.

PubMed

Wei, Feng; Ma, Lin-Yun; Jin, Wen-Tao; Ma, Shuang-Cheng; Han, Guo-Zhu; Khan, Ikhlas Ahmad; Lin, Rui-Chao

2004-10-01

Phytochemical study of the ethanol extract of the seeds of Aesculus chinensis led to the isolation of a new triterpenoid saponin (6), together with five known triterpenoid saponins (1-5). The structure of the new compound was elucidated on the basis of spectral data to be 21,28-di-O-acetylprotoaescigenin-3-O-[beta-D-glucopyranosyl(1-2)][beta-D-glucopyranosyl(1-4)]-beta-D-glucopyranosiduronic acid (aesculiside A, 6). The antiinflammatory activities of the four main saponins (1-4) were compared with those of total saponin extracts, and single saponins showed more potent activity than total saponin extracts in mice.

[Structure and biological action on cardiovascular systems of saponins from Panax notoginseng].

PubMed

Li, Juan; Wang, Ru-feng; Yang, Li; Wang, Zheng-tao

2015-09-01

Notoginseng Radix et Rhizoma (Sanqi), the underground part of Panax notoginseng (Burk.) F. H. Chen (Araliaceae) is commonly used in Chinese medicine for treatment of haemorrhage, haemostasis, swelling, etc. The aerial part including leaves, flowers and fruits are also applied for similar functions. Triterpenoid saponins are considered to be responsible for the biological activities of Sanqi. Up to date, more than 100 saponins have been isolated from theroots, rhizomes, leaves, flowers and fruits of P. notoginseng. The reported saponins can be classified into protopanaxadiol (PPD), protopanaxatriol (PPT), C17 side-chain varied and other types, according to the skeletons of the aglycons. The present review summarizes the saponins isolated from P. notoginseng and their distribution in different medicinal organs, as well as the pharmacological actions on cardiovascular system.

Ginseng saponins and the treatment of osteoporosis: mini literature review

PubMed Central

Siddiqi, Muhammad Hanif; Siddiqi, Muhammad Zubair; Ahn, Sungeun; Kang, Sera; Kim, Yeon-Ju; Sathishkumar, Natarajan; Yang, Dong-Uk; Yang, Deok-Chun

2013-01-01

The ginseng plant (Panax ginseng Meyer) has a large number of active ingredients including steroidal saponins with a dammarane skeleton as well as protopanaxadiol and protopanaxatriol, commonly known as ginsenosides, which have antioxidant, anticancer, antidiabetic, anti-adipocyte, and sexual enhancing effects. Though several discoveries have demonstrated that ginseng saponins (ginsenosides) as the most important therapeutic agent for the treatment of osteoporosis, yet the molecular mechanism of its active metabolites is unknown. In this review, we summarize the evidence supporting the therapeutic properties of ginsenosides both in vivo and in vitro, with an emphasis on the different molecular agents comprising receptor activator of nuclear factor kappa-B ligand, receptor activator of nuclear factor kappa-B, and matrix metallopeptidase-9, as well as the bone morphogenetic protein-2 and Smad signaling pathways. PMID:24198650

Transcriptomic analysis of Siberian ginseng (Eleutherococcus senticosus) to discover genes involved in saponin biosynthesis.

PubMed

Hwang, Hwan-Su; Lee, Hyoshin; Choi, Yong Eui

2015-03-14

Eleutherococcus senticosus, Siberian ginseng, is a highly valued woody medicinal plant belonging to the family Araliaceae. E. senticosus produces a rich variety of saponins such as oleanane-type, noroleanane-type, 29-hydroxyoleanan-type, and lupane-type saponins. Genomic or transcriptomic approaches have not been used to investigate the saponin biosynthetic pathway in this plant. In this study, de novo sequencing was performed to select candidate genes involved in the saponin biosynthetic pathway. A half-plate 454 pyrosequencing run produced 627,923 high-quality reads with an average sequence length of 422 bases. De novo assembly generated 72,811 unique sequences, including 15,217 contigs and 57,594 singletons. Approximately 48,300 (66.3%) unique sequences were annotated using BLAST similarity searches. All of the mevalonate pathway genes for saponin biosynthesis starting from acetyl-CoA were isolated. Moreover, 206 reads of cytochrome P450 (CYP) and 145 reads of uridine diphosphate glycosyltransferase (UGT) sequences were isolated. Based on methyl jasmonate (MeJA) treatment and real-time PCR (qPCR) analysis, 3 CYPs and 3 UGTs were finally selected as candidate genes involved in the saponin biosynthetic pathway. The identified sequences associated with saponin biosynthesis will facilitate the study of the functional genomics of saponin biosynthesis and genetic engineering of E. senticosus.

Albiziahexoside: a potential source of bioactive saponin from the leaves of Albizzia lebbeck.

PubMed

Ueda, Minoru; Tokunaga, Takashi; Okazaki, Masayuki; Sata, Noriko U; Ueda, Katsuhiro; Yamamura, Shosuke

2003-10-01

Albiziahexoside (1), a new hexaglycosylated saponin, was isolated from leaves of Albizzia lebbeck. Saponin 1, which is an analog of cytotoxic albiziatrioside A (2), did not show cytotoxicity. However, 1 is a potential source of 2 and related bioactive saponins for medicinal use because leaves, which can be regenerated after collection, contain 1 in substantial quantity.

A new saponin from Acanthopanax koreanum with anti-inflammatory activity.

PubMed

Dat, Le Duc; Thao, Nguyen Phuong; Luyen, Bui Thi Thuy; Tai, Bui Huu; Woo, Mi Hee; Manzoor, Zahid; Ali, Irshad; Koh, Young Sang; Kim, Young Ho

2017-03-01

Twelve saponins were isolated from the leaves of Acanthopanax koreanum, including one new lupane-type triterpene glycoside, named acankoreoside R (1), together with 11 known triterpenoid saponins (2-12). Their structures were elucidated by 1D and 2D nuclear magnetic resonance (NMR), mass spectroscopic data (MS). All of the fractions and isolated saponins were evaluated for anti-inflammatory activities in lipopolysaccharide (LPS)-stimulated bone marrow-derived dendritic cells (BMDCs) by ELISA. Among them, compounds 1-5, 7, 10, and 12 showed strong inhibitions towards interleukin-12 (IL-12) production with IC 50 values ranging from 1.59 to 5.46 µM. Other compounds were weak or inactive toward IL-12 p40 production.

Triterpenoidal saponins: bioactive secondary metabolites from Zygophyllum coccineum L

USDA-ARS?s Scientific Manuscript database

Phytochemical investigation of the aerial parts of Zygophyllum coccineum L., led to the isolation of nine ursane-type triterpene saponins (1-9) including one new: zygophylloside S (1), together with known flavonoid glycoside (10), and sterol glycoside (11). The isolated compounds were tested for ant...

Plant latex: a promising antifungal agent for post harvest disease control.

PubMed

Sibi, G; Wadhavan, Rashmi; Singh, Sneha; Shukla, Abhilasha; Dhananjaya, K; Ravikumar, K R; Mallesha, H

2013-12-01

Bioactive compounds from plant latex are potential source of antifungic against post harvest pathogens. Latex from a total of seven plant species was investigated for its phytochemical and antifungal properties. Six fungi namely Aspergillus fumigatus, A. niger, A. terreus, F. solani, P. digitatum and R. arrhizus were isolated from infected fruits and vegetables and tested against various solvent extracts of latex. Analysis of latex extracts with phytochemical tests showed the presence of alkaloids, flavonoids, glycosides, phenols, saponins, steroids, tannins and terpenoids. Antifungal assay revealed the potential inhibitory activity of petroleum ether extracts against the postharvest fungal isolates. Various degree of sensitivity was observed irrespective of plant species studied with A. terreus and P. digitatum as the most susceptible ones. F. solani and A. fumigatus were moderately sensitive to the latex extracts tested. Among the plants, latex of Thevetia peruviana (75.2%) and Artocarpus heterophyllus (64.8%) were having potential antifungal activity against the isolates followed by Manilkara zapota (51.1%). In conclusion, use of plant latex makes interest to control postharvest fungal diseases and is fitting well with the concept of safety for human health and environment.

Isolation of endophytic fungi from Dioscorea zingiberensis C. H. Wright and application for diosgenin production by solid-state fermentation.

PubMed

Xiang, Haibo; Zhang, Tao; Pang, Xu; Wei, Yuzhen; Liu, Hongyu; Zhang, Yuqin; Ma, Baiping; Yu, Liyan

2018-05-03

In this study, endophytic fungi were isolated from Dioscorea zingiberensis C.H. Wright (DZW), and a novel clean process to prepare diosgenin from DZW was developed. A total of 123 strains of endophytic fungi were isolated from different plant tissues of DZW. Among them, the strain Fusarium sp. (CPCC 400709) showed the best activity of hydrolyzing steroidal saponins in DZW into diosgenin. Thus, this strain was used to prepare diosgenin from DZW by solid-state fermentation. The fermentation parameters were optimized using response surface methodology, and a high yield of diosgenin (2.16%) was obtained at 14.5% ammonium sulfate, an inoculum size of 12.3%, and 22 days of fermentation. Furthermore, the highest diosgenin yield (2.79%) was obtained by co-fermentation with Fusarium sp. (CPCC 400709) and Curvularia lunata (CPCC 400737), which was 98.9% of that obtained by β-glucosidase pretreated acid hydrolysis (2.82%). This process is acid-free and wastewater-free, and shows promise as an effective and clean way to prepare diosgenin for use in industrial applications from DZW.

Oleanane-type saponins from Anemone taipaiensis and their cytotoxic activities.

PubMed

Wang, Xiaoyang; Zhang, Wei; Gao, Kai; Lu, Yunyang; Tang, Haifeng; Sun, Xiaoli

2013-09-01

Phytochemical investigation of the n-BuOH extract of the rhizomes of Anemone taipaiensis led to the isolation of three new oleanane-type triterpenoid saponins (1-3), together with four known saponins (4-7). Their structures were elucidated on the basis of spectroscopic analysis and chemical derivatization. All the compounds were isolated for the first time from A. taipaiensis. The cytotoxicity of these compounds was evaluated in five human cancer cell lines including A549 (lung carcinoma), HeLa (cervical carcinoma), HepG2 (hepatocellular carcinoma), HL-60 (promyelocytic leukemia), and U87MG (glioblastoma). The monodesmosidic saponin 4 exhibited cytotoxic activity toward all cancer cell lines, with IC50 values ranging from 6.42 to 18.16 μM. In addition, the bisdesmosidic saponins 1 and 7 showed selective cytotoxicity against the U87MG cells. Copyright © 2013 Elsevier B.V. All rights reserved.

Nutritive value and qualitative assessment of secondary compounds in seeds of eight tropical browse, shrub and pulse legumes.

PubMed

Babayemi, O J; Demeyer, D; Fievez, V

2004-01-01

Seeds of four tropical multipurpose trees (Albizia saman, Albizia lebbeck, Albizia rhizonse, Leucaena leucocephala), two shrubs (Tephrosia candida, Tephrosia bracteolata) and two pulse legume (Lablab purpureus, Canavalia ensiformis) were chemically analysed for dry matter (DM), ash, crude protein (CP), neutral detergent fibre (NDF) and ether extract (EE). Qualitative evaluation of secondary metabolites (saponins, phenols, steroids, and alkaloids) was elucidated. The DM, ash, CP, NDF and EE ranged between 88.9-93.6 %, 3.0-5.4 %, 24.8-38.2 %, 22.1-46.9 % and 2.0-17.0 % respectively. All seed species contained at least one group of secondary plant metabolites and steroids were common to all except C. ensiformis that was not implicated for any. A. lebbeck and A. rhizonse showed low saponin content. Indications for water soluble tannins were reported for L. leucocephala while the two species of Tephrosia contained flavonoids or condensed tannins. The study suggested the potentials of the legumes seed species as a feed source for ruminants.

Inhibition of amyloid β aggregation and protective effect on SH-SY5Y cells by triterpenoid saponins from the cactus Polaskia chichipe.

PubMed

Fujihara, Koji; Koike, Shin; Ogasawara, Yuki; Takahashi, Kunio; Koyama, Kiyotaka; Kinoshita, Kaoru

2017-07-01

Alzheimer's disease (AD) destroys brain function, especially in the hippocampus, and is a social problem worldwide. A major pathogenesis of AD is related to the accumulation of amyloid beta (Aβ) peptides, resulting in neuronal cell death in the brain. Here, we isolated four saponins (1-4) and elucidated their structures from 1D and 2D NMR and HRFABMS spectral data. The structures of 1 and 2 were determined as new saponins which have cochalic acid as the aglycon, and 3 was determined as a new saponin with oleanolic acid as the aglycon. Compound 4 was confirmed as the known saponin chikusetsusaponin V (=ginsenoside R 0 ). Isolated saponins (1-4) and six previously reported saponins (5-10) were tested for their inhibitory effects of Aβ aggregation and their protective effects on SH-SY5Y cells against Aβ-associated toxicity. As the results, compounds 3 and 4 showed inhibitory effect of Aβ aggregation and compounds 5-8 exerted the protective effects on SH-SY5Y cells against Aβ-associated toxicity. Copyright © 2017 Elsevier Ltd. All rights reserved.

Bioactive constituents of oleanane-type triterpene saponins from the roots of Glycyrrhiza glabra.

PubMed

Wei, Juan-Hua; Zheng, Yun-Feng; Li, Cun-Yu; Tang, Yu-Ping; Peng, Guo-Ping

2014-01-01

Three new oleanane-type triterpene saponins, namely licorice-saponin M3 (1), licorice-saponin N4 (2), and licorice-saponin O4 (3), an artificial product (4), as well as five known triterpene glucuronides (5-9), were isolated from the roots of Glycyrrhiza glabra L. Their structures were established using 1D and 2D NMR spectroscopy, mass spectrometry, and by comparison with spectroscopic data reported in the literature. The inhibitory effects of the selected compounds on neuraminidase were evaluated, and the preliminary structure-activity relationship was also predicted.

Two new triterpenoid saponins from the aerial parts of Anemone taipaiensis.

PubMed

Li, Hui; Wang, Xiao-Yang; Wang, Xia-Yin; Hua, Dong; Liu, Yang; Tang, Hai-Feng

2015-05-01

Phytochemical study on the aerial parts of Anemone taipaiensis for the first time led to the isolation of two new oleanane-type triterpenoid saponins 1 and 2, together with four known saponins (3-6). Their structures were elucidated by extensive spectroscopic analysis and chemical evidences. Saponins 2-4 exhibited cytotoxicity against human glioblastoma U251MG cell line with IC50 values ranging from 1.56 to 80.62 μM.

Impact of Quillaja saponaria saponins on grapevine ecosystem organisms.

PubMed

Fischer, Marc J C; Pensec, Flora; Demangeat, Gérard; Farine, Sibylle; Chong, Julie; Ramírez-Suero, Montserrat; Mazet, Flore; Bertsch, Christophe

2011-08-01

The control of grapevine pathogens is a rising concern in Vitis vinifera culture. The current international trend is toward banning chemicals that are highly toxic to the environment and human workers, and adopting tighter regulations. We evaluated the impact of saponins on three kinds of organisms found in grapevine culture. The ectoparasitic nematode Xiphinema index, the parasitic fungus Botrytis cinerea and various yeast strains representative of the must fermentation population were incubated on synthetic media supplemented with variable concentrations of Quillaja saponaria saponins. Saponins induced reduction in the growth of B. cinerea and showed nematicide effects on X. index. The control of X. index and Botrytis cinerea is discussed in the context of the potential use of these chemicals as environmentally-friendly grapevine treatments. With Saccharomyces cerevisiae and other yeasts, saponins showed higher toxicity against S. cerevisiae strains isolated from wine or palm wine whereas laboratory strains or strains isolated from oak exhibited better resistance. This indicates that Q. saponaria saponins effects against yeast microflora should be assessed in the field before they can be considered an environmentally-safe new molecule against B. cinerea and X. index.

Antimicrobial activity of saponins produced by two novel endophytic fungi from Panax notoginseng.

PubMed

Jin, Zhaoxia; Gao, Lin; Zhang, Lin; Liu, Tianyi; Yu, Fang; Zhang, Zongshen; Guo, Qiong; Wang, Biying

2017-11-01

Endophytes in plants may be co-producer of the bioactive compounds of their hosts. We conducted a study to bioprospect for saponin-producing endophytic fungi from Panax notoginseng and evaluate the antimicrobial activity of saponins. Two novel fungal endophytes, Fusarium sp. PN8 and Aspergillus sp. PN17, were isolated from traditional Chinese medicinal herb P. notoginseng. After eight days of fermentation, the total saponins produced in the culture broth of PN8 and PN17 were 1.061 and 0.583 mg mL -1 , respectively. The saponin extracts exhibited moderate to high (inhibition zone diameter 15.7-28.4 mm, MIC 1.6-12.5 mg mL -1 ) antimicrobial activity against pathogens tested. Further analysis showed that triterpenoid saponins produced by Fusarium PN8 were Rb 1 , Rd and 20(S)-Rg 3 , while Aspergillus PN17 had the ability to synthesise ginsenoside Re, Rd and 20(S)-Rg 3 . The isolated endophytes may be used as potential sources for microbial production of plant secondary metabolites and for antimicrobial agents.

An efficient approach to identify different chemical markers between fibrous root and rhizome of Anemarrhena asphodeloides by ultra high-performance liquid chromatography quadrupole time-of-flight tandem mass spectrometry with multivariate statistical analysis.

PubMed

Wang, Fang-Xu; Yuan, Jian-Chao; Kang, Li-Ping; Pang, Xu; Yan, Ren-Yi; Zhao, Yang; Zhang, Jie; Sun, Xin-Guang; Ma, Bai-Ping

2016-09-10

An ultra high-performance liquid chromatography quadrupole time-of-flight tandem mass spectrometry approach coupled with multivariate statistical analysis was established and applied to rapidly distinguish the chemical differences between fibrous root and rhizome of Anemarrhena asphodeloides. The datasets of tR-m/z pairs, ion intensity and sample code were processed by principal component analysis and orthogonal partial least squares discriminant analysis. Chemical markers could be identified based on their exact mass data, fragmentation characteristics, and retention times. And the new compounds among chemical markers could be isolated rapidly guided by the ultra high-performance liquid chromatography quadrupole time-of-flight tandem mass spectrometry and their definitive structures would be further elucidated by NMR spectra. Using this approach, twenty-four markers were identified on line including nine new saponins and five new steroidal saponins of them were obtained in pure form. The study validated this proposed approach as a suitable method for identification of the chemical differences between various medicinal parts in order to expand medicinal parts and increase the utilization rate of resources. Copyright © 2016 Elsevier B.V. All rights reserved.

Cytotoxic triterpenoid saponins from Aesculus glabra Willd.

PubMed

Yuan, Wei; Wang, Ping; Deng, Guangrui; Li, Shiyou

2012-03-01

Twenty-four acylated polyhydroxyoleanene saponins were isolated from the seeds of Aesculus glabra. Sixteen of them, namely aesculiosides G1-G16 (1-16), were determined as compounds by spectroscopic and chemical analysis. The structural features of all 24 saponins are: (1) arabinofuranosyl units affixed to C-3 of the glucuronopyranosyl unit in the trisaccharide chain; (2) no 24-OH substitution; (3) C-2 sugar moiety substitution of the 3-O-glucuronopyranosyl unit is either glucopyranosyl or galactopyranosyl. The features of these isolated saponin structures provide more evidence for chemical taxonomy within the genus Aesculus. The cytotoxicity of the aesculiosides (1-16) were tested against A549 and PC-3 cancer cell lines with GI₅₀ from 5.4 to >25 μM. Copyright © 2011 Elsevier Ltd. All rights reserved.

Triterpenoid saponins from Echinopsis macrogona (Cactaceae).

PubMed

Okazaki, Sachie; Kinoshita, Kaoru; Ito, Satoru; Koyama, Kiyotaka; Yuasa, Hiroshi; Takahashi, Kunio

2011-01-01

Triterpene saponins, pachanosides C1, E1, F1 and G1 (1-4), and bridgesides A1, C1, C2, D1, D2, E1 and E2 (5-11) were isolated from Echinopsis macrogona. Compounds 1-4 were saponins with pachanane type triterpene saponins, while the others (5-11) were oleanane type triterpene saponins. While the aglycones of 2-4 and 8-11 were hitherto unknown, the structure of pachanol C was revised in this paper. Their structures were elucidated on the basis of chemical and physicochemical evidence. Copyright © 2010 Elsevier Ltd. All rights reserved.

Measurement of steroidal saponins in Panicum and Brachiaria grasses in the USA and Brazil

USDA-ARS?s Scientific Manuscript database

Several grasses in the Panicum genus have been reported to cause hepatogenous photosensitization in animals throughout the world. In the United States, switchgrass (Panicum virgatum L.) has been reported to cause hepatogenous photosensitization in lambs and horses. In Brazil, cultivars of Panicum ...

Isolation of Three Triterpene Saponins, Including Two New Oleanane Derivatives, from Soldanella alpina and Hydrophilic Interaction Liquid Chromatography-Evaporative Light Scattering Detection of these Three Saponins in Four Soldenella Species.

PubMed

Haller, Julia; Schwaiger, Stefan; Stuppner, Hermann; Gafner, Frank; Ganzera, Markus

2017-11-01

The genus Soldanella is one of the few endemic to Europe. Some of its species have relevance in local traditional medicine. Earlier work has indicated the possible presence of saponins in S. alpina. To investigate S. alpina and other related species for the occurrence of saponins. Following sequential extraction with n-hexane, dichloromethane and ethyl acetate the subsequent methanolic extract of S. alpina roots was fractionated after solvent precipitation using fast centrifugal partition chromatography and column chromatography. Structures were elucidated by LC-MS n , high-resolution MS, hydrolysis experiments and one-dimensional (1D)- and two-dimensional (2D)-NMR. A hydrophilic interaction liquid chromatography method was developed to quantitate saponins in the leaves and roots of four Soldanella species. Three triterpene saponins, two of them new natural products, were isolated from S. alpina. Based on an epoxyoleanal aglycone substituted with four sugar units, they were analytically quantitated using a Kinetex 2.6 μm hydrophilic interaction liquid chromatography (HILIC) column together with a mobile phase comprising of ammonium acetate, water and acetonitrile. Method validation confirmed that the assay meets all requirements in respect to linearity, accuracy, sensitivity and precision. All four Soldanella species investigated contained the three saponins. The lowest total level of the three saponins (1.09%) was observed in S. montana leaves while the highest saponin content (5.14%) was determined in S. alpina roots. The detection of saponins within the genus Soldanella is an indication that further phytochemical examination of this genus may reveal more secondary metabolites of interest. Copyright © 2017 John Wiley & Sons, Ltd. Copyright © 2017 John Wiley & Sons, Ltd.

Clerodendrum serratum (L.) Moon. - a review on traditional uses, phytochemistry and pharmacological activities.

PubMed

Patel, Jagruti J; Acharya, Sanjeev R; Acharya, Niyati S

2014-06-11

Clerodendrum serratum (L.) Moon. (Verbenaceae) is an important medicinal plant growing in the tropical and warm temperate regions like Africa, Southern Asia; Malaysia and distributed throughout in forests of India and Sri Lanka. It is traditionally valued and reported for treating pain, inflammation, rheumatism, respiratory disorders, fever and malarial fever in India with a long history. To provide a comprehensive overview of the traditional and ethno medicinal uses, phytochemistry and biological activities of C. serratum with clinical and toxicity data and possibly make recommendations for further research. All relevant worldwide accepted databases were searched for the terms "Clerodendrum", "Clerodendrum serratum", "Bharangi" and "Cheruthekku" along with the other literature from Indian classical texts and pharmacopoeias. There was no specific timeline set for the search. The accessible literatures available on C. serratum were collected via electronic search using Pubmed, Scopus, Science Direct and traditional books reports on ethnopharmacology and traditional medicines. C. serratum has played an important role in Indian system of medicine. In addition to the common local use in respiratory diseases, other ethnomedicinal uses include treatment of pain, inflammation, rheumatism and fever especially malarial fever. Scientific studies on extracts and formulations revealed anti-asthmatic, mast cell stabilization and anti-allergic effects of roots of C. serratum. Reported data on pharmacological activities also includes hepatoprotective, anti-oxidant, anti-inflammatory and anticancer potential of the drug. Saponins (terpenoids and steroids), flavonoids and phenolics isolated from roots have been the focus of phytochemical investigations as the biological activity has been ascribed to the saponins, which are known to possess anti-inflammatory and anti-cancer activity. Isolated bioactives from roots like icosahydropicenic acid and ursolic acid have been claimed to offer anti-allergic and hepatoprotective activity. Therapeutic potential of roots and leaves of C. serratum has been demonstrated in the conditions like asthma, allergy, fever, inflammation and liver disorders attributed to the presence of various flavonoids, phenolics and saponins present in the drug. Many ethnobotanical claims have been confirmed through modern in-vitro and in-vivo pharmacological studies of different extracts and isolates from plant; however, additional studies on the biomarkers are needed to establish mechanism of action and to validate the traditional use of this drug in clinical practices after proper safety assessment. Copyright © 2014 Elsevier Ireland Ltd. All rights reserved.

Simultaneous determination of five components in rat plasma by UPLC-MS/MS and its application to a comparative pharmacokinetic study in Baihe Zhimu Tang and Zhimu extract.

PubMed

Li, Guolong; Tang, Zhishu; Yang, Jie; Duan, Jinao; Qian, Dawei; Guo, Jianming; Zhu, Zhenhua; Liu, Hongbo

2015-04-15

Baihe Zhimu Tang (BZT) is a famous traditional Chinese medicine recipe to treat dry coughing due to yin deficiency and for moisturizing the lungs. Zhimu is an essential ingredient in BZT used to treat inflammation, fever and diabetes. The most important active components in Zhimu are flavonoids such as neomangiferin, mangiferin, and steroid saponins (e.g., timosaponin BII, anemarsaponin BIII, timosaponin AIII). The aim of this study was to compare the pharmacokinetics of mangiferin, neomangiferin, timosaponin BII, anemarsaponin BIII and timosaponin AIII in rat plasma after oral administration of BZT and Zhimu extract (ZME). A sensitive, reliable and robust LC-MS/MS method to simultaneously determine steroid saponins and flavonoids in rat plasma was successfully validated. Significant differences (p < 0.05) were found in the pharmacokinetic parameters of timosaponin BII, anemarsaponin BIII and timosaponin AIII between BZT and ZME. It was surmised that formula compatibility could significantly influence the pharmacokinetics of BZT and our study is the first to study the administration of BZT based on pharmacokinetic studies.

Inhibition of Glucose Transport by Tomatoside A, a Tomato Seed Steroidal Saponin, through the Suppression of GLUT2 Expression in Caco-2 Cells.

PubMed

Li, Baorui; Terazono, Yusuke; Hirasaki, Naoto; Tatemichi, Yuki; Kinoshita, Emiko; Obata, Akio; Matsui, Toshiro

2018-02-14

We investigated whether tomatoside A (5α-furostane-3β,22,26-triol-3-[O-β-d-glucopyranosyl (1→2)-β-d-glucopyranosyl (1→4)-β-d-galactopyranoside] 26-O-β-d-glucopyranoside), a tomato seed saponin, may play a role in the regulation of intestinal glucose transport in human intestinal Caco-2 cells. Tomatoside A could not penetrate through Caco-2 cell monolayers, as observed in the transport experiments using liquid chromatography-mass spectrometry. The treatment of cells with 10 μM tomatoside A for 3 h resulted in a 46.0% reduction in glucose transport as compared to untreated cells. Western blotting analyses revealed that tomatoside A significantly (p < 0.05) suppressed the expression of glucose transporter 2 (GLUT2) in Caco-2 cells, while no change in the expression of sodium-dependent glucose transporter 1 was observed. In glucose transport experiments, the reduced glucose transport by tomatoside A was ameliorated by a protein kinase C (PKC) inhibitor and a multidrug resistance-associated protein 2 (MRP2) inhibitor. The tomatoside A-induced reduction in glucose transport was restored in cells treated with apical sodium-dependent bile acid transporter (ASBT) siRNA or an ASBT antagonist. These findings demonstrated for the first time that the nontransportable tomato seed steroidal saponin, tomatoside A, suppressed GLUT2 expression via PKC signaling pathway during the ASBT-influx/MRP2-efflux process in Caco-2 cells.

Triterpenoid saponins from Albizia lebbeck (L.) Benth and their inhibitory effect on the survival of high grade human brain tumor cells.

PubMed

Noté, Olivier Placide; Jihu, Dong; Antheaume, Cyril; Zeniou, Maria; Pegnyemb, Dieudonné Emmanuel; Guillaume, Dominique; Chneiwess, Hervé; Kilhoffer, Marie Claude; Lobstein, Annelise

2015-03-02

As part of our search of new bioactive triterpenoid saponins from Cameroonian Mimosaceae plants, phytochemical investigation of the roots of Albizia lebbeck led to the isolation of two new oleanane-type saponins, named lebbeckosides A-B (1-2). Their structures were established on the basis of extensive 1D and 2D NMR ((1)H, (13)C NMR, DEPT, COSY, TOCSY, ROESY, HSQC, and HMBC) and HRESIMS studies, and by chemical evidence. Compounds 1-2 were evaluated for their inhibitory effect on the metabolism of high grade human brain tumor cells, the human glioblastoma U-87 MG cell lines and the glioblastoma stem-like TG1 cells isolated from a patient tumor, and known to be particularly resistant to standard therapies. The isolated saponins showed significant cytotoxic activity against U-87 MG and TG1 cancer cells with IC50 values of 3.46 μM and 1.36 μM for 1, and 2.10 μM and 2.24 μM for 2, respectively. Copyright © 2014 Elsevier Ltd. All rights reserved.

Steroidal glycosides from the bulbs of Easter lily (Lilium longiflorum Thunb.) promote dermal fibroblast migration in vitro.

PubMed

Esposito, Debora; Munafo, John P; Lucibello, Teresa; Baldeon, Manuel; Komarnytsky, Slavko; Gianfagna, Thomas J

2013-07-09

Preparations derived from bulbs of various Lilium species have been used to promote the healing of skin abrasions, sores and burns and to aid in healing wounds in Traditional Chinese and Greco-Roman Medicine. To evaluate fractionated Easter lily bulb extracts and their steroidal glycosides (1-5) for the promotion of dermal fibroblast migration in vitro, a model for the early events in wound healing. An activity-guided screening approach was used by coupling sequential solvent extraction, gel permeation chromatography (GPC), and semi-preparative reverse-phase high performance liquid chromatography (RP-HPLC) with an in vitro dermal fibroblast migration assay. Cytotoxicity was evaluated with methyl thiazole tetrazolium (MTT). To gain insight into the mode of action of the steroidal glycosides, nitric oxide (NO) production, and expression of genes for transforming growth factor beta-1 (TGF-β) and its receptors were evaluated. Fractionated bulb extracts and the two isolated steroidal glycoalkaloids (1) and (2) induced NO production and TGF-β receptor I mRNA expression in fibroblast cell culture. In a cytotoxicity assay, steroidal glycosides (1) and (3) had IC50 values of 8.2 and 8.7 µM, but the natural acetylation of the C-6″' hydroxy of the terminal glucose unit in (2) resulted in a 3-fold decrease in cell cytotoxicity when compared with (1). Results from the dermal fibroblast migration assay revealed that the steroidal glycoalkaloids (1) and (2), and the furostanol saponin (3) promoted fibroblast migration from the range of 23.7±5.7 to 37.7±5.1%, as compared with the control. Collectively, our data demonstrate that the steroidal glycosides present in Easter lily bulbs induce, at least in part, the observed dermal fibroblast migration activity of the bulb extracts. This is the first evidence that steroidal glycosides from Lilium longiflorum may potentially play a role in the wound healing process and may provide a scientific basis for the historical use of lily bulbs for this purpose. Copyright © 2013 Elsevier Ireland Ltd. All rights reserved.

Determination and Isolation of Four Anti-tumour Saponins from Lonicera macranthoides by HPLC-ESI-QTOF/MS and HSCCC.

PubMed

Liu, Xuehui; Zhou, Rongrong; Shen, Bingbing; Chen, Lin; Zhou, Qingyijun; Wan, Dan; Huang, Luqi; Zhang, Shuihan

2017-01-01

Lonicera macranthoides is a Chinese herb that contains a large number of bioactive spanions possessing important pharmacological activities, such as anti-tumour activity. However, detailed information about their anti-tumor activity and bioactive compounds is limited. In order to evaluate the scientific basis, the method of high-speed counter-current chromatography (HSCCC) combined with high performance liquid chromatography mass spectrometry (HPLC-ESI-QTOF/MS) has been developed to separate, purify and analyze saponins from Lonicera macranthoides. Four main saponins, Macranthoidin B (I), Macranthoidin A (II), Macranthoides B (III) and Akebia saponin D (IV) were separated by HSCCC with the solvent systems of ethyl acetate-nbutanol- water (3:2:5) and n-butanol-water-methanol-ethyl acetate (1:6:0.5:4). The purities of these four bioactive ingredients (I-IV) identified and detected by HPLC-ESI-QTOF/MS were 95.1%, 92.7%, 91.8% and 96.3%, respectively. The separated saponins were evaluated for their cytotoxic activities against six tumor cell lines (MCF-7, Hela, A549, HepG2, HT29 and Eca109). Results show that compounds I-IV exhibited particular significant anti-tumor activities against human mammary adenocarcinoma MCF-7 cell with IC50 values ranging from 12.7 to 30.8 µM. It was demonstrated that the combinative method using HPLC-ESI-QTOF/MS and HSCCC was suitable for rapid screening and isolating saponins of Lonicera macranthoides and the isolated compounds have great potential for the development of new antitumor drugs. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

Variability in Saponin Content, Cancer Antiproliferative Activity and Physicochemical Properties of Concentrated Agave Sap.

PubMed

Santos-Zea, Liliana; Rosas-Pérez, Aratza Mireya; Leal-Díaz, Ana María; Gutiérrez-Uribe, Janet A

2016-08-01

Concentrated agave sap (CAS) has gained popularity as an unrefined sweetener. It is obtained by boiling "aguamiel" that contains phytochemicals with diverse bioactivities. Saponins have been the most widely studied agave phytochemicals due to their cancer antiproliferative effect but their concentration may vary due to maturity of the agave plant and collection site. In this study, 18 CAS samples produced in different states of Mexico were analyzed using multivariate methods to determine which physicochemical or phytochemical parameters were responsible for variation. Additionally, extracts with different saponin profiles were tested to determine possible correlations with antiproliferative activity. Total soluble solids, pH, and water activity were similar to those reported for other agave sweeteners. Antioxidant capacity of samples was correlated to browning index. Eleven steroidal saponins were found in CAS samples and they were the main source of variability. Magueyoside B, a kammogenin tetraglycoside, was the most abundant saponin in all samples. With respect to bioactivity, multivariate analysis indicated that magueyoside B and a gentrogenin tetraglycoside were compounds strongly related with bioactivity. CAS from Hidalgo, Puebla, and Veracruz had higher concentration of magueyoside B than from the other kamogenin tetraglycoside found in the samples from other Mexican states. These results could be used as a first approach to characterize and standardize CAS to validate the potential health benefits derived from its consumption. © 2016 Institute of Food Technologists®

Saponins from the traditional medicinal plant Momordica charantia stimulate insulin secretion in vitro

PubMed Central

Keller, Amy C.; Ma, Jun; Kavalier, Adam; He, Kan; Brillantes, Anne-Marie B.; Kennelly, Edward J.

2012-01-01

The antidiabetic activity of Momordica charantia (L.), Cucurbitaceae, a widely-used treatment for diabetes in a number of traditional medicine systems, was investigated in vitro. Antidiabetic activity has been reported for certain saponins isolated from M. charantia. In this study insulin secretion was measured in MIN6 β-cells incubated with an ethanol extract, saponin-rich fraction, and five purified saponins and cucurbitane triterpenoids from M. charantia, 3β,7β,25-trihydroxycucurbita-5,23(E)-dien-19-al (1), momordicine I (2), momordicine II (3), 3-hydroxycucurbita-5,24-dien-19-al-7,23-di-O-β-glucopyranoside (4), and kuguaglycoside G (5). Treatments were compared to incubation with high glucose (27 mM) and the insulin secretagogue, glipizide (50 μM). At 125 μg/ml, an LC-ToF-MS characterized saponin-rich fraction stimulated insulin secretion significantly more than the DMSO vehicle, p=0.02. At concentrations 10 and 25 μg/ml, compounds 3 and 5 also significantly stimulated insulin secretion as compared to the vehicle, p≤0.007, and p= 0.002, respectively. This is the first report of a saponin-rich fraction, and isolated compounds from M. charantia, stimulating insulin secretion in an in vitro, static incubation assay. PMID:22133295

Antibacterial Activities of Jatropha curcas (LINN) on Coliforms Isolated from Surface Waters in Akure, Nigeria

PubMed Central

Dada, E. O.; Ekundayo, F. O.; Makanjuola, O. O.

2014-01-01

This study investigated the antibacterial activities of hot water, ethanol and acetone extracts of Jatropha curcas (LINN) leaves on coliforms isolated from surface waters using growth inhibition indices based on agar plate technique. The percentage recovery of the extracts was 19.17%, 18.10% and 18.80% for hot water, ethanol and acetone respectively. Phytochemical screening of the extracts was also determined. Qualitative phytochemical screening showed that the plant extracts contained steroids, tannins, flavonoids and cardiac glycosides, while alkaloids, phlobatannin, terpenoids and anthraquinones were absent. Only ethanolic extract did not possess saponins. Aqueous extracts of J. curcas compared most favourably with the standard antibiotics (gentamycin) on all the coliform bacteria except on K. pneumoniae and E. coli likely due to a measurably higher antibacterial activity compared to the organic extracts. The minimum inhibitory concentration of the aqueous extract ranged from 3.00 to 7.00 mg/L while minimum bactericidal concentration ranged from 4.00 to 10.00 mg/L. Aqueous extract of J. curcas could be used as antibacterial agents against diseases caused by coliforms. PMID:24711746

Solicitation of HPLC and HPTLC Techniques for Determination of Rutin from Polyalthia longifolia Thwaites

PubMed Central

Doshi, Gaurav Mahesh; Zine, Sandeep Prabhakar; Chaskar, Pratip Kashinath; Une, Hemant Devidas

2014-01-01

Background: Polyalthia longifolia Thwaites is an important traditional plant in India. Rutin, an active constituent has been reported to possess good amount of pharmacological as well as therapeutic potential. Objective: The aim of the present study was to find out by analytical techniques how much percentage of rutin is present in the plant leaves’ ethanolic extract by analytical techniques. Materials and Methods: Shade dried leaves of Polyalthia longifolia were subjected to cold ethanolic extraction followed by monitoring the isolated rutin high-pressure liquid chromatography (HPLC) and high performance thin layer chromatography (HPTLC) after carrying out preliminary phytochemical screening. Results: Extraction yield was found to be 13.94% w/w. Phytochemical screening of the extract showed the presence of flavonoids, steroids, diterpenoids, alkaloids, saponins, tannins and phenolic compounds and mucilage. From the Rf value, the ethanolic extract was found to be having constituent identical to rutin. By HPTLC and HPLC the amount of rutin was found to be 11.60% w/w and 4.03% w/v, respectively. Conclusion: The active constituent isolated was found to be equal to rutin. PMID:25002804

Noncariogenic intense natural sweeteners.

PubMed

Kinghorn, A D; Kaneda, N; Baek, N I; Kennelly, E J; Soejarto, D D

1998-09-01

There is a definite relationship between the dietary consumption of sucrose and the incidence of dental caries. Noncaloric sucrose substitutes for use in the sweetening of foods, beverages, and medicines may be either synthetic compounds or natural products. In the United States, four potently sweet artificial sweeteners are approved, namely, saccharin, aspartame, acesulfame potassium, and sucralose. Highly sweet plant constituents are used in Japan and some other countries, including the diterpene glycoside stevioside and the protein thaumatin. Recent progress in a research project oriented towards the discovery and evaluation of novel potentially noncariogenic sweeteners from plants has focused on substances in the sesquiterpenoid, diterpenoid, triterpenoid, steroidal saponin, and proanthocyanidin structural classes. The feasibility of using Mongolian gerbil electrophysiological and behavioral assays to monitor the sweetness of plant extracts, chromatographic fractions, and pure isolates has been investigated. An in vivo cariogenicity study on the commercially available natural sweeteners stevioside and rebaudioside A has been carried out.

New Cytotoxic Triterpenoid Saponins from the Roots of Albizia gummifera (J.F.Gmel.) C.A.Sm.

PubMed

Simo, Line Made; Noté, Olivier Placide; Mbing, Joséphine Ngo; Aouazou, Sarah Ali; Guillaume, Dominique; Muller, Christian Dominique; Pegnyemb, Dieudonné Emmanuel; Lobstein, Annelise

2017-10-01

As part of our search for new bioactive saponins from Cameroonian medicinal plants, two new oleanane-type saponins, named gummiferaosides D and E (1 and 2), along with one known saponin, julibroside J 8 (3), were isolated from the roots of Albizia gummifera. Their structures were established on the basis of extensive 1D- and 2D-NMR ( 1 H- and 13 C-NMR, DEPT, COSY, TOCSY, NOESY, HSQC, HSQC-TOCSY, and HMBC) and HR-ESI-MS studies, and by chemical evidence. The apoptotic effect of saponins 1 - 3 was evaluated on the A431 human epidermoid cancer cell. Flow cytometric analyses showed that saponins 1 - 3 induced apoptosis of human epidermoid cancer cell (A431) in a dose-dependent manner. © 2017 Wiley-VHCA AG, Zurich, Switzerland.

Cuspidate A, new anti-fungal triterpenoid saponin from Lepidagathis cuspidata.

PubMed

Rattan, Rajeev; Inder Fozdar, Bharat; Gautam, Veena; Sharma, Ritika; Kumar, Dinesh; Sharma, Upendra

2017-04-01

One new triterpenoid saponin named cuspidate A (1) along with a known oleanane-based triterpenoid saponin clemontanoside-C were isolated from the roots of Lepidagathis cuspidata. The structure of new compound (1) was established after detailed analysis of spectroscopic data including 1D and 2D NMR spectra. This is the first report on clemontanoside-C from this genus. These saponins were found to be effective against the selected fungal strains Aspergillus flavus, Rhizopus stolinifer, Penicillum nodatum, Aspergillus fumigates. Compound 1 showed better activity, comparable to the synthetic drug, while compound 2 showed a moderate effect against all studied fungal strains.

Cytotoxic triterpenoid saponins from the rhizomes of Anemone taipaiensis.

PubMed

Wang, Xiao-Yang; Chen, Xiao-Li; Tang, Hai-Feng; Gao, Hui; Tian, Xiang-Rong; Zhang, Ping-Hu

2011-09-01

Two new oleanane-type triterpenoid saponins, 1 and 2, and a new natural product, 3, together with five known saponins, 4- 8, were isolated from the rhizomes of ANEMONE TAIPAIENSIS. Their structures were elucidated by extensive spectroscopic analysis and chemical evidences. Six saponins, 1, 2, 4- 7, which possessed a free carboxylic group at C-28, exhibited significant cytotoxicity against human leukemia HL-60 cells and human hepatocellular carcinoma Hep-G2 cells with IC (50) values in the range of 1.31-10.12 µM. © Georg Thieme Verlag KG Stuttgart · New York.

Bacoside A3--a triterpenoid saponin from Bacopa monniera.

PubMed

Rastogi, S; Pal, R; KulshreshthaDK

1994-05-01

A new triterpenoid saponin, bacoside A3, a constituent of bacosides the saponin mixture of Bacopa monniera, was isolated and characterized. Its structure was established as 3-beta-[O-beta-D-glucopyranosyl(1-->3)-O- [alpha-L-arabinofuranosyl(1-->2) ]O-beta-D-glucopyranosyl)oxy]jujubogenin by chemical and spectral analyses. The cis-isomer of ebelin lactone was also obtained as one of the artefacts of the aglycone and its structure revised.

Effects of Saponins against Clinical E. coli Strains and Eukaryotic Cell Line

PubMed Central

Arabski, Michał; Węgierek-Ciuk, Aneta; Czerwonka, Grzegorz; Lankoff, Anna; Kaca, Wiesław

2012-01-01

Saponins are detergent-like substances showing antibacterial as well as anticancer potential. In this study, the effects of saponins from Quillaja saponaria were analyzed against prokaryotic and eukaryotic cells. Multidrug-resistant clinical E. coli strains were isolated from human urine. As eukaryotic cells, the CHO-K1 cell lines were applied. Antibacterial effect of ampicillin, streptomycin, and ciprofloxacin in the presence of saponins was measured by cultivation methods. Properties of saponins against CHO-K1 cells were measured by the MTT test, hemolysis assay and flow cytometry. Saponin from Quillaja saponaria has a cytotoxic effect at concentrations higher than 25 μg/mL and in the range of 12–50 μg/mL significantly increases the level of early apoptotic cells. Saponin at dose of 12 μg/mL enhances the six E. coli strains growth. We postulate that saponins increase the influx of nutrients from the medium into E. coli cells. Saponins do not have synergetic effects on antibacterial action of tested antibiotics. In contrary, in the presence of saponins and antibiotics, more CFU/mL E. coli cells were observed. This effect was similar to saponins action alone towards E. coli cells. In conclusion, saponins was cytotoxic against CHO-K1 cells, whereas against E. coli cells this effect was not observed. PMID:22500084

Immunoaffinity Knockout of Saponin Glycosides from Asparagus racemosus to Assess Anti-lipid Peroxidation.

PubMed

Onlom, Churanya; Phrompittayarat, Watoo; Putalun, Waraporn; Waranuch, Neti; Ingkaninan, Kornkanok

2017-07-01

Asparagus racemosus Willd (Asparagaceae family), known as Shatavari, is important in Ayurveda and traditional Thai medicines. The saponin glycosides, shatavarin I and IV are major constituents in its roots and may be responsible for their actions including protection against lipid peroxidation and carcinogenesis. To develop an immunoaffinity column for isolating compounds with structures related to shatavarin IV from crude extracts of A. racemosus root. The monoclonal antibody recognising shatavarin IV (mAbShavIV) was coupled to an Affi-Gel Hz gel to isolate compounds with structures related to shatavarin IV from the other components of crude extracts of A. racemosus root. The saponin glycosides in each fraction were analysed by mAbShavIV ELISA and LC-MS/MS. The pooled wash-through fractions contained 3% of loaded mAbShavIV reactive saponin glycosides, while eluted fractions released ~ 90% of shatavarin saponin glycosides in a single step. Using thiobarbiturate (TBARs) to measure lipid-peroxidation, the extract, and the pooled wash-through fractions showed moderate protection against Cu + -induced oxidation of human low density lipoprotein (LDL) (IC 50 11.3 ± 1.4 and 12.6 ± 0.9 μg/mL, respectively). In contrast, the saponin glycosides eluted from the mAbShavIV-column had weaker protectant (IC 50 29.7 ± 1.8 μg/mL) suggesting that A. racemosus shatavarins do not inhibit carcinogenesis through preventing lipid peroxidation. The strategy described here demonstrates its utility for isolating a group of related compounds from the rest of the extract with selectivity and recovery rate. Pharmacological efficacy and synergistic effects of the components obtained can be further investigated. Copyright © 2017 John Wiley & Sons, Ltd. Copyright © 2017 John Wiley & Sons, Ltd.

Saponin Isolation as Main Ingredients of Insecticide and Collagen Type I From Crown of Thorn-Starfish (Acanthaster planci)

NASA Astrophysics Data System (ADS)

Wijanarko, Anondho; Januardi Ginting, Mikael; Sahlan, Muhamad; Krisanta Endah Savitri, Imelda; Florensia, Yunita; Sudiarta, Maria Regina; Pastika, Satria; Rafiki, Fakhri; Hermansyah, Heri

2017-10-01

The outbreaks of crown of thorns starfish (Acanthaster planci) resulted in the severe destruction of coral reefs in a large number of Indonesia’s marine ecosystem, especially in the western part. At the moment, control efforts are proven to be ineffective because of its high cost and labor intensive. Recent research found that A. planci contain saponins that act as cytotoxic compound and can be used as an environment-friendly insecticide to eradicate Kalotermitidae pest. Saponins extracted by maceration using ethanol 96.0% with a total yield of saponins 9.04% and 4.66% for two test. Purification of saponin was achieved by utilization of activated carbon with a mass of carbon:volume sample 1:2 (w/v) and stirred for 20 minutes. Sapogenin can be isolated by hydrolyzing using hydrochloric acid, and thus 168.4 mg sapogenin is obtained. In addition to saponins, A. planci also contains collagen Type I. Collagen isolation by multistage extraction began with extracting the collagen with alkaline solvent, with water, NaOH 0.1 M, and Ca(OH)2 0.2 M as the solvent variations. The second step is acid-enzymatic extraction by pepsin digestion in 0.5 M acetic acid. Collagen extract will be further purified by salting out and dialysis method to obtain pure collagen yield called Pepsin Solubilized Collagens (PSC). Characterization of PSC consists of quantitative and qualitative analysis such as Lowry method, gel electrophoresis, UV spectroscopy, amino acid composition analysis, and Scanning Electron Microscopy (SEM). The result shows Ca(OH)2 0.2 M as the best extraction solvent with 2.26% yield of PSC.

Cancer chemopreventive and therapeutic effects of diosgenin, a food saponin.

PubMed

Raju, Jayadev; Mehta, Rekha

2009-01-01

Cancer chemoprevention is a strategy taken to retard, regress, or resist the multistep process of carcinogenesis, including the blockage of its vital morphogenetic milestones viz. normal-preneoplasia-neoplasia-metastasis. For several reasons, including safety, minimal (or no) toxicity and side-effects, and better availability, alternatives such as naturally occurring phytochemicals that are found in foods are becoming increasingly popular over synthetic drugs. Food saponins have been used in complimentary and traditional medicine against a variety of diseases including several cancers. Diosgenin, a naturally occurring steroid saponin found abundantly in legumes and yams, is a well-known precursor of various synthetic steroidal drugs that are extensively used in the pharmaceutical industry. Over the past decade, a series of preclinical and mechanistic studies have been conducted to understand the role of diosgenin as a chemopreventive/therapeutic agent against several cancers. This review highlights the biological activity of diosgenin that contributes to cancer chemoprevention and control. The anticancer mode of action of diosgenin has been demonstrated via modulation of multiple cell signaling events involving critical molecular candidates associated with growth, differentiation, apoptosis, and oncogenesis. Altogether, these preclinical and mechanistic findings strongly implicate the use of diosgenin as a novel, multitarget-based chemopreventive or therapeutic agent against several cancer types. Future research in this field will help to establish not only whether diosgenin is safe and efficacious as a chemopreventive agent against several human cancers, but also to develop and evaluate standards of evidence for health claims for diosgenin-containing foods as they become increasingly popular and enter the marketplace labeled as functional foods and nutraceuticals.

Ultrasound-assisted extraction of ginseng saponins from ginseng roots and cultured ginseng cells.

PubMed

Wu, J; Lin, L; Chau, F T

2001-10-01

Ultrasound-assisted extraction was evaluated as a simpler and more effective alternative to conventional extraction methods for the isolation of ginsenosides (saponins) from various types of ginseng. The ginseng samples were extracted with different solvents, under either direct sonication by an ultrasound probe horn or indirect sonication in an ultrasound cleaning bath. The ultrasonic extraction was compared with the conventional method of refluxing boiling solvents in a soxhlet extractor, on the yields of both the total saponin isolated by thin-layer chromatography and the individual ginsenosides by high performance liquid chromatography. It was found that the sonication-assisted extraction of ginseng saponins was about three times faster than the traditional extraction method. The ultrasonic extraction was not only more efficient but also convenient for the recovery and purification of the active ingredients of plant materials. In addition, the sonication-assisted extraction can be carried out at lower temperatures which are favorable for the thermally unstable compounds.

Triterpenoidal Saponins: Bioactive Secondary Metabolites from Zygophyllum coccineum

DTIC Science & Technology

2011-01-22

isolation of nine ursane-type triterpene saponins (1?9), including the new one; zygophylloside S (1), together with a known flavonoid glycoside (10) and a...1–9), including the new one; zygophylloside S (1), to- gether with a known flavonoid glycoside (10) and a sterol glyco- side (11).The isolated...Moghazy AM. Zygophyllum coccineum. V. The chemistry of the leaf and stem. J Pharm Sci 1960; 1: 135 4 Eskander EF, Won JH. Hypoglycaemic and

Rapid Screening of Chemical Constituents in Rhizoma Anemarrhenae by UPLC-Q-TOF/MS Combined with Data Postprocessing Techniques

PubMed Central

Shan, Lanlan; Wu, Yuanyuan; Yuan, Lei; Zhang, Yani

2017-01-01

Rhizoma Anemarrhenae, a famous traditional Chinese medicine (TCM), is the dried rhizome of Anemarrhena asphodeloides Bge. (Anemarrhena Bunge of Liliaceae). The medicine presents anti-inflammatory, antipyretic, sedative, and diuretic effects. The chemical constituents of Rhizoma Anemarrhenae are complex and diverse, mainly including steroidal saponins, flavonoids, phenylpropanoids, benzophenones, and alkaloids. In this study, UPLC-Q-TOF/MS was used in combination with data postprocessing techniques, including characteristic fragments filter and neutral loss filter, to rapidly classify and identify the five types of substances in Rhizoma Anemarrhenae. On the basis of numerous literature reviews and according to the corresponding characteristic fragments produced by different types of compounds in combination with neutral loss filtering, we summarized the fragmentation patterns of the main five types of compounds and successfully screened and identified 32 chemical constituents in Rhizoma Anemarrhenae. The components included 18 steroidal saponins, 6 flavonoids, 4 phenylpropanoids, 2 alkaloids, and 2 benzophenones. The method established in this study provided necessary data for the study on the pharmacological effects of Rhizoma Anemarrhenae and also provided the basis for the chemical analysis and quality control of TCMs to promote the development of a method for chemical research on TCMs. PMID:29234389

Rapid Screening of Chemical Constituents in Rhizoma Anemarrhenae by UPLC-Q-TOF/MS Combined with Data Postprocessing Techniques.

PubMed

Shan, Lanlan; Wu, Yuanyuan; Yuan, Lei; Zhang, Yani; Xu, Yanyan; Li, Yubo

2017-01-01

Rhizoma Anemarrhenae , a famous traditional Chinese medicine (TCM), is the dried rhizome of Anemarrhena asphodeloides Bge. ( Anemarrhena Bunge of Liliaceae). The medicine presents anti-inflammatory, antipyretic, sedative, and diuretic effects. The chemical constituents of Rhizoma Anemarrhenae are complex and diverse, mainly including steroidal saponins, flavonoids, phenylpropanoids, benzophenones, and alkaloids. In this study, UPLC-Q-TOF/MS was used in combination with data postprocessing techniques, including characteristic fragments filter and neutral loss filter, to rapidly classify and identify the five types of substances in Rhizoma Anemarrhenae . On the basis of numerous literature reviews and according to the corresponding characteristic fragments produced by different types of compounds in combination with neutral loss filtering, we summarized the fragmentation patterns of the main five types of compounds and successfully screened and identified 32 chemical constituents in Rhizoma Anemarrhenae . The components included 18 steroidal saponins, 6 flavonoids, 4 phenylpropanoids, 2 alkaloids, and 2 benzophenones. The method established in this study provided necessary data for the study on the pharmacological effects of Rhizoma Anemarrhenae and also provided the basis for the chemical analysis and quality control of TCMs to promote the development of a method for chemical research on TCMs.

Screening for Triterpenoid Saponins in Plants Using Hyphenated Analytical Platforms.

PubMed

Khakimov, Bekzod; Tseng, Li Hong; Godejohann, Markus; Bak, Søren; Engelsen, Søren Balling

2016-11-24

Recently the number of studies investigating triterpenoid saponins has drastically increased due to their diverse and potentially attractive biological activities. Currently the literature contains chemical structures of few hundreds of triterpenoid saponins of plant and animal origin. Triterpenoid saponins consist of a triterpene aglycone with one or more sugar moieties attached to it. However, due to similar physico-chemical properties, isolation and identification of a large diversity of triterpenoid saponins remain challenging. This study demonstrates a methodology to screen saponins using hyphenated analytical platforms, GC-MS, LC-MS/MS, and LC-SPE-NMR/MS, in the example of two different phenotypes of the model plant Barbarea vulgaris (winter cress), glabrous (G) and pubescent (P) type that are known to differ by their insect resistance. The proposed methodology allows for detailed comparison of saponin profiles from intact plant extracts as well as saponin aglycone profiles from hydrolysed samples. Continuously measured 1D proton NMR data during LC separation along with mass spectrometry data revealed significant differences, including contents of saponins, types of aglycones and numbers of sugar moieties attached to the aglycone. A total of 49 peaks were tentatively identified as saponins from both plants; they are derived from eight types of aglycones and with 2-5 sugar moieties. Identification of two previously known insect-deterrent saponins, hederagenin cellobioside and oleanolic acid cellobioside, demonstrated the applicability of the methodology for relatively rapid screening of bioactive compounds.

[Comparative study on specific chromatograms and main active components of wild and cultivated rhizomes of Paris polyphylla var. yunnanensis].

PubMed

Zan, Ke; Gao, Yu-Ming; Cui, Gan; Liu, Jie; Guo, Li-Nong; Zheng, Jian; Ma, Shuang-Cheng

2017-08-01

The present study is to compare specific chromatograms and main acitive components between wild and cultivated rhizomes of Paris polyphylla var. yunnanensis by HPLC. HPLC analysis was performed on a Waters XSelect HSS T3 C₁₈ clumn (4.6 mm×250 mm, 5 μm), with a mobile phase consisting of acetonitrile (A)-water (B) at a flow rate of 1 mL•min⁻¹ (0-50 min,30%-50%A;50-80 min,50% A,80-85 min,50%-30%A;85-100 min,30% A). The detection wavelength was 203 nm and the column temperature was controlled at 30 ℃, and the injection volume was 10 μL. HPLC specific chromatograms of wild and cultivated rhizomes of P. polyphylla var. yunnanensis were established and nine steroidal saponins were simultaneously determined by the above method. The mean contents of paris saponin Ⅶ, paris saponin H and total average contents of four pennogenyl saponins in Rhizomes of wild samples were significantly higher than those of cultivated ones. However, this result is opposite from the average content of paris saponin Ⅰ and total average contents of five dioscins in the wild and cultivated samples. Because the significant differences occurred for the specific chromatograms and main active components between the wild and cultivated P. polyphylla var. yunnanensis, much more pharmacological and clinical researches are therefore necessary. Copyright© by the Chinese Pharmaceutical Association.

Bioactive saponins from the fruits of Aesculus pavia L.

PubMed

Sun, Zhen-Liang; Zhang, Ming; Wu, Ying; Wan, Ai-Hong; Zhang, Rong

2011-10-01

Continued chemical investigation on the fruits of Aesculus pavia L. resulted in theisolation and identification of two new oleanolic acid saponins, namely vaccaroside A (1) andvaccaroside B (2). The isolated furostanol saponins were evaluated for cytotoxic activity againsthuman normal amniotic and human lung carcinoma cell lines using neutral red and MTT assays.In vitro experiments showed significant cytotoxicity in a dose dependent manner with IC₅₀ valuesin the range of 27.80-79.02 μM. Copyright © 2011 Elsevier B.V. All rights reserved.

A new triterpenoid saponin from Gymnema sylvestre.

PubMed

Zhang, Man-Qi; Liu, Yue; Xie, Sheng-Xu; Xu, Tun-Hai; Liu, Tong-Hua; Xu, Ya-Juan; Xu, Dong-Ming

2012-01-01

Besides four known compounds, a new triterpenoid saponin was isolated from the stems of Gymnema sylvestre. The structure of the new triterpenoid saponin was established as 3β,16β,22α-trihydroxy-olean-12-ene 3-O-β-D-xylopyranosyl-(1 → 6)-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranoside (1) on the basis of 1D and 2D NMR techniques, including COSY, HMBC, HMQC, and NOESY correlations. Four known compounds 2, 3, 4, and 5 were identified on the basis of spectroscopic data.

Triterpenoid saponins from Dianthus versicolor.

PubMed

Ma, Li; Gu, Yu-Cheng; Luo, Jian-Guang; Wang, Jun-Song; Huang, Xue-Feng; Kong, Ling-Yi

2009-04-01

Seven new pentacyclic triterpenoid saponins, named dianversicosides A-G (1-7), together with nine known compounds, were isolated from the aerial parts of Dianthus versicolor. The structures of 1-7 were elucidated on the basis of spectroscopic data and chemical evidence. The absolute configuration of the 3-hydroxyl-3-methylglutaryl (HMG) group in 1-4 was ascertained by chemical analysis combined with a chiral HPLC method. Cytotoxic activities of the isolated compounds were evaluated against a small panel of cancer and other cell lines.

Dianthosaponins G-I, triterpene saponins, an anthranilic acid amide glucoside and a flavonoid glycoside from the aerial parts of Dianthus japonicus and their cytotoxicity.

PubMed

Kanehira, Yuka; Kawakami, Susumu; Sugimoto, Sachiko; Matsunami, Katsuyoshi; Otsuka, Hideaki

2016-10-01

Extensive isolation work on the 1-BuOH-soluble fraction of a MeOH extract of the aerial parts of Dianthus japonicus afforded three further triterpene glycosyl estsers, termed dianthosaponins G-I, an anthranilic acid amide glucoside and a C-glycosyl flavonoid along with one known triterpene saponin. Their structures were elucidated from spectroscopic evidence. The cytotoxicity of the isolated compounds toward A549 cells was evaluated.

Verbesinosides A-F, Novel 15,27-Cyclooleanane Saponins from the American Native Plant Verbesina virginica

USDA-ARS?s Scientific Manuscript database

Verbesinosides A-F (1-6), six novel 15,27-cyclooleanane-type triterpenoid saponins carrying different aromatic acyl moieties on the aglycone, were isolated from the leaf and flower of Verbesina virginica. Their structures were established by interpretation of spectroscopic data and chemical methods....

LC-UV assay method and UPLC/Q-TOF-MS characterisation of saponins from Ilex paraguariensis A. St. Hil. (mate) unripe fruits.

PubMed

Peixoto, Maria Paula Garofo; Kaiser, Samuel; Verza, Simone Gasparin; de Resende, Pedro Ernesto; Treter, Janine; Pavei, Cabral; Borré, Gustavo Luís; Ortega, George González

2012-01-01

Ilex paraguariensis A. St. Hil. (mate) is known in several South American countries because of the use of its leaves in stimulant herbal beverages. High saponin contents were reported in mate leaves and unripe fruits that possess a dissimilar composition. Two LC-UV methods previously reported for mate saponins assay focused on mate leaves and the quantification of the less polar saponin fraction in mate fruits. To develop and validate a LC-UV method to assay the total content of saponins in unripe mate fruits and characterise the chemical structure of triterpenic saponins by UPLC/Q-TOF-MS. From unripe fruits of mate a crude ethanolic extract was prepared (EX40) and the mate saponin fraction (MSF) purified by solid phase extraction. The LC-UV method was validated using ilexoside II as external standard. UPLC/Q-TOF-MS was adjusted from the LC-UV method to obtain the fragmentation patterns of the main saponins present in unripe fruits. Both LC-UV and UPLC/Q-TOF-MS methods indicate a wide range of Ilex saponins polarity. The ilexoside II and total saponin content of EX40 were 8.20% (w/w) and 47.60% (w/w), respectively. The total saponin content in unripe fruits was 7.28% (w/w). The saponins present in MSF characterised by UPLC/Q-TOF-MS are derived mainly from ursolic/oleanolic, acetyl ursolic or pomolic acid. The validated LC-UV method was shown to be linear, precise, accurate and to cover several saponins previously isolated from Ilex species and could be applied for the quality control of unripe fruit saponins. Copyright © 2011 John Wiley & Sons, Ltd.

Saponin B, a novel cytostatic compound purified from Anemone taipaiensis, induces apoptosis in a human glioblastoma cell line.

PubMed

Wang, Yuangang; Tang, Haifeng; Zhang, Yun; Li, Juan; Li, Bo; Gao, Zhenhui; Wang, Xiaoyang; Cheng, Guang; Fei, Zhou

2013-11-01

Glioblastoma multiforme (GBM) is one of the most common malignant brain tumors. Saponin B, a novel compound isolated from the medicinal plant, Anemone taipaiensis, has been found to have a strong time- and dose-dependent cytostatic effect on human glioma cells and to suppress the growth of U87MG GBM cells. In this study, we investigated whether saponin B induces the apoptosis of glioblastoma cells and examined the underlying mechanism(s) of action of saponin B. Saponin B significantly suppressed U87MG cell proliferation. Flow cytometric analysis of DNA in the U87MG cells confirmed that saponin B blocked the cell cycle at the S phase. Furthermore, treatment of the U87MG cells with saponin B induced chromatin condensation and led to the formation of apoptotic bodies, as observed under a fluorescence microscope, and Annexin V/PI assay further suggested that phosphatidylserine (PS) externalization was apparent at higher drug concentrations. Treatment with saponin B activated the receptor-mediated pathway of apoptosis, as western blot analysis revealed the activation of Fas-l. Saponin B increased the Bax and caspase-3 ratio and decreased the protein expression of Bcl-2. The results from the present study demonstrate that the novel compound, saponin B, effectively induces the apoptosis of GBM cells and inhibits glioma cell growth and survival. Therefore, saponin B may be a potential candidate for the development of novel cancer therapeutics with antitumor activity against gliomas.

Hypocholesterolemic property of Yucca schidigera and Quillaja saponaria extracts in human body.

PubMed

Kim, Sang-Woo; Park, Sang-Kyu; Kang, Sung-Il; Kang, Han-Chul; Oh, Han-Jin; Bae, Chul-Young; Bae, Dong-Ho

2003-12-01

This study was undertaken to observe the effects of the blend of partially purified Yucca schidigera and Quillaja saponaria extracts on cholesterol levels in the human's blood and gastrointestinal functions, and to determine if a new cholesterol-lowering drug can be developed by the further purification of the extracts. Ultrafiltration and sequential diafiltration increased the amounts of steroidal saponin in aqueous yucca extract and terpenoid saponin in aqueous quillaja extract from 9.3% and 21.4% to 17.2% and 61.8%, respectively. Taking 0.9 mg of the blend (6:4, v:v) of the resulting filtrates a day for 4 weeks resulted in the decreases in total and LDL cholesterol levels in blood plasma of hyper-cholesterolemic patients with enhancement in gastrointestinal symptoms of patients.

Metabolites profiling of Pulsatilla saponin D in rat by ultra performance liquid chromatography-quadrupole time-of-flight mass spectrometry (UPLC/Q-TOF-MS/MS).

PubMed

Ouyang, Hui; Zhou, Maofu; Guo, Yicheng; He, Mingzhen; Huang, Hesong; Ye, Xide; Feng, Yulin; Zhou, Xin; Yang, Shilin

2014-07-01

Pulsatilla saponin D, an antitumor substance isolated from traditional Chinese herbal medicine Pulsatilla chinensis (Bge.) Regel, is a promising candidate for new drug development. The purpose of the present study is to establish a simple and practical strategy for the metabolite profiling of Pulsatilla saponin D in vivo. A total of 18 metabolites were identified in rat plasma, urine and feces samples based on MS and MS/MS data by using ESI-Q-TOF-MS/MS, and eight of them (M11-M18) were reported for the first time. The results indicated that deglycosylation, dehydrogenation, hydroxylation and sulfation were the major metabolic transformations of Pulsatilla saponin D in vivo. This study has improved our understanding of the metabolic fate of Pulsatilla saponin D in vivo, and the information gained from the current study is relevant to the pharmacological activity of Pulsatilla saponin D. Copyright © 2014 Elsevier B.V. All rights reserved.

An LC-MS/MS method for simultaneous determination of nine steroidal saponins from Paris polyphylla var. in rat plasma and its application to pharmacokinetic study.

PubMed

Yang, Guangyi; Lu, Wei; Pan, Meng; Zhang, Chenning; Zhou, Yuan; Hu, Pei; Hu, Ming; Song, Gao

2017-10-25

Paris polyphylla var is an herbal plant herb widely used in Traditional Chinese Medicine. The purpose of this study is to develop an Ultra Performance Liquid Chromatography-tandem mass spectrometer (UPLC-MS) method to quantify the major components (i.e., nine saponins) from P. polyphylla in plasma samples. A UItra BiPh column (100×2.1mm, 5μm) was used with acetonitrile/0.1% formic acid in water as mobile phases. The analytes were quantified using a Waters XEVO TQ mass spectrometer via multiple reaction monitoring (MRM) with positive scan mode. A protein precipitation method was used to extract the analytes from rat plasma. The inter/intra-day precision, accuracy, recovery, matrix effect, and stability were evaluated per the FDA guidance. The method showed linearity in the concentration ranges of 2.4-1250ng/mL. The intra-day and inter-day precisions (RSD) of these analytes at three different levels were less than 15.0%. The extraction recoveries of these analytes were from 83.8% to 109.4% and the matrix effects ranged from 87.4% to 105.4%. The stabilities of these compounds in plasma were evaluated by analyzing three different concentrations following storage at 25°C for 6h, and -80°C for 30days. All the samples displayed less than 15.0% variations. The validated method was successfully used to a pharmacokinetic (PK) study using Sprague Dawley (SD) rats with intravenous (i.v.) and oral (p.o.) administration of P. polyphylla extract. The applications revealed that this method can be used to analyze major steroidal saponins from P. polyphylla in biological samples. Copyright © 2017 Elsevier B.V. All rights reserved.

Chemical Composition, Toxicity and Vasodilatation Effect of the Flowers Extract of Jasminum sambac (L.) Ait. "G. Duke of Tuscany".

PubMed

Kunhachan, Phanukit; Banchonglikitkul, Chuleratana; Kajsongkram, Tanwarat; Khayungarnnawee, Amonrat; Leelamanit, Wichet

2012-01-01

Phytochemical analysis of the ethanolic Jasmine flower extract of Jasminum sambac (L.) Ait. "G. Duke of Tuscany" revealed the mixtures of coumarins, cardiac glycosides, essential oils, flavonoids, phenolics, saponins, and steroids. However, alkaloids, anthraquinones, and tannins were not detected. By intravenous injection at a single dose of 0.5 mL/mouse (15 mg) of the flower extract, no systemic biological toxicity demonstrated in ICR mice was observed. In Wistar rats, the LD(50) of the extract was higher than 5,000 mg/kg BW by oral administration. Vasodilatation effect of the 95% ethanolic extract on isolated aortic rats was also investigated. Compared with the control group, the Jasmine flowers extract in 0.05% DMSO clearly reduced tonus of isolated endothelium thoracic aortic rings preconstricted with phenylephrine (10(-6) M), as a dose-dependent manner. Nevertheless, this pharmacological effect disappeared after the preincubation of the rings with atropine (10(-6) M) or with N(ω)-nitro-L-arginine (10(-4) M). These are possibly due to the actions of the active components on the vessel muscarinic receptors or by causing the release of nitric oxide.

Isolation and evaluation of cytogenetic effect of Brahmi saponins on cultured human lymphocytes exposed in vitro.

PubMed

Kalachaveedu, Mangathayaru; Papacchan, Sunu; Sanyal, Sudip; Koshy, Teena; Telapolu, Srivani

2015-01-01

Major saponins of Brahmi (Bacopa monniera, Fam: Scrophulariaceae) - bacosides A and B - were isolated from the total methanol extract and characterised based on melting point, TLC, IR, (1)H NMR and (13)C NMR. They were evaluated for their in vitro cytogenetic effects on human peripheral blood lymphocytes by chromosomal aberration (CA) assay and sister chromatid exchange (SCE) assay. The frequency of chromatid type aberrations and reciprocal interchanges between sister chromatids in the treated cells was scored in comparison to the untreated control. At 30 μg/mL dose, bacoside A showed a statistically significant increase in the frequency of both CA and SCE and bacoside B showed an increase only in SCE. Our report of the genotoxicity of the saponins is significant in view of the reports of anticancer activity of Brahmi extracts.

Triterpenoid Saponins from the Seeds of Aesculus chinensis and Their Cytotoxicities.

PubMed

Cheng, Jin-Tang; Chen, Shi-Tao; Guo, Cong; Jiao, Meng-Jiao; Cui, Wen-Jin; Wang, Shu-Hui; Deng, Zhe; Chen, Chang; Chen, Sha; Zhang, Jun; Liu, An

2018-02-01

Six new triterpenoid saponins, aesculusosides A-F (1-6), together with 19 known ones, were isolated from the seeds of Aesculus chinensis. The new structures were elucidated through extensive spectroscopic analyses and by comparison with previously reported data. Some of the isolates were evaluated for their cytotoxic activities against MCF-7 cell line by an MTT assay, and compounds 15, 16, 19, and 23-25 exhibited inhibitory activities against MCF-7 with IC 50 values ranging from 7.1 to 31.3 μM.

Aesculus pavia foliar saponins: defensive role against the leafminer Cameraria ohridella.

PubMed

Ferracini, Chiara; Curir, Paolo; Dolci, Marcello; Lanzotti, Virginia; Alma, Alberto

2010-07-01

Recently, the leafminer Cameraria ohridella Deschka & Dimic has caused heavy damage to the white-flowering horse chestnut in Europe. Among the Aesculus genus, A. pavia L. HBT genotype, characterised by red flowers, showed an atypical resistance towards this pest. Its leaves, shaken in water, originated a dense foam, indicating the presence of saponins, unlike the common horse chestnut tree. The aim was to isolate and identify these leaf saponins and test their possible defensive role against C. ohridella. Spectroscopic analyses showed that A. pavia HBT genotype leaves contained a mixture of saponins, four of which were based on the same structure as commercial escin saponins, the typical saponin mixture produced by A. hippocastanum and accumulated only within bark and fruit tissues. The mixture showed a repellent effect on C. ohridella moth. The number of mines detected on the leaves of A. hippocastanum plants treated with A. pavia HBT saponins through watering and stem brushing was significantly lower than the control, and in many cases no mines were ever observed. The results showed that the exogenous saponins were translocated from roots/stem to the leaf tissues, and their accumulation seemed to ensure an appreciable degree of protection against the leafminer. Copyright (c) 2010 Society of Chemical Industry.

Identification of major xanthones and steroidal saponins in rat urine by liquid chromatography-atmospheric pressure chemical ionization mass spectrometry technology following oral administration of Rhizoma Anemarrhenae decoction.

PubMed

Ma, Chunhui; Wang, Longxing; Tang, Yihong; Fan, Mingsong; Xiao, Hongbin; Huang, Chenggang

2008-10-01

Rhizoma Anemarrhenae (Zhimu in Chinese), the dried rhizome of Anemarrhena asphodeloides Bge. (Fam. Liliaceae), is a well-known traditional Chinese medicinal herb and has been used clinically in China for centuries to cure various diseases. However, like other traditional Chinese medicines, the effective constituents of this medicine, especially the assimilation and metabolites in vivo, which are very important to show their effects, have not been systematically studied. In this paper, solid-phase extraction and liquid chromatography-atmospheric pressure chemical ionization mass spectrometry technologies were used to study the constituents absorbed into rat urine and their metabolites after oral administration of Rhizoma Anemarrhenae decoction. A total of 11 compounds, including two xanthones, three of their metabolites and six steroidal saponins, were identified in rat urine sample. They were neomangiferin (1), glucuronide and monomethyl conjugate of mangiferin (2), mangiferin (3), monomethyl conjugate of mangiferin (4), dimethyl conjugate of mangiferin (5), timosaponin N or timosaponin E1 (6), timosaponin BII (7), timosaponin BIII (8), anemarrhenasaponin I or anemarrhenasaponin II (9), timosaponin AII (10) and timosaponin AIII (11). The results would efficaciously narrow the potentially active compounds range in Rhizoma Anemarrhenae decoction, and pave a helpful way for follow-up mechanism of action research.

Anticancer effect of Polyphyllin Ι in colorectal cancer cells through ROS-dependent autophagy and G2/M arrest mechanisms.

PubMed

Yu, Si; Wang, Lijiao; Cao, Zhixing; Gong, Daoyin; Liang, Qianyi; Chen, Hanting; Fu, Huizhu; Wang, Wenwen; Tang, Xue; Xie, Zihao; He, Yang; Peng, Cheng; Li, Yuzhi

2018-06-01

Polyphyllin Ι is a steroidal saponin isolated from the rhizoma of Paris polyphylla. In the present study, we aimed to investigate the anticancer effects of polyphyllin Ι in colorectal cancer and to elucidate the potential underlying molecular mechanisms. Using, CCK8 assay, flow cytometry, laser confocal microscope analysis and western blot, the anticancer effects of the polyphyllin Ι were analysed in colorectal cells. Our results indicate that polyphyllin Ι significantly decreased cell viability of HCT 116 cells and induced autophagy. Furthermore, we found that polyphyllin Ι induced autophagy in an ROS-dependent cell death and not related with PI3 K/AKT/mTOR pathway. We also provide evidence that excessive ROS triggered by polyphyllin Ι could induce G2/M phase arrest via regulating cycle proteins expression of cell cycle regulators, such as p21 and cyclinB1. In conclusion, polyphyllin Ι exhibit anticancer effect through ROS-dependent autophagy and induces G2/M arrest in colorectal cancer.

Separation and structural analysis of saponins in a bark extract from Quillaja saponaria Molina.

PubMed

Nord, L I; Kenne, L

1999-07-20

Six major saponins were isolated from a bark extract from Quillaja saponaria Molina. Solid-phase extraction, followed by a two-step reversed-phase HPLC separation procedure with phosphate and ammonium acetate buffers of different pH values, was used. The compounds were characterised using NMR spectroscopy, mass spectrometry and chemical methods.

The Gastrointestinal Irritation of Polygala Saponins and Its Potential Mechanism In Vitro and In Vivo

PubMed Central

Wen, Li; Xia, Nan; Tang, PeiPei; Hong, Yi; Wang, ZiZhen; Liu, YaJie; Liu, YanJu; Liu, JianJun; Li, XiangQiong

2015-01-01

Processing alters the pharmacological activity and reduces the gastrointestinal toxicity of the polygalae. To investigate the effect of processing, different glycosyl substituent products were tested. Hypnotic and subhypnotic doses of pentobarbital-induced sleep tests on mice were used to evaluate the sedative activity of polygala saponins with different glycosyl substituents; isolated gut motility experiment was employed to study excitatory effects of different polygala saponins; the gastrointestinal irritation effects of different polygala saponins were compared by measuring the levels of gastric PGE2 and intestinal TNF-α on mice. When compared with control, Onjisaponin B (OJB) and tenuifolin (TEN), but not senegenin (SNG), significantly increased the number of sleeping mice and prolonged the sleeping time (P < 0.05); 80, 40, and 20 mg/L of OJB and 80 mg/L of TEN, but not SNG, obviously changed the amplitude and frequency of isolated jejunum (P < 0.05); all the three compounds significantly decreased the level of gastric PGE2 but had no obvious influences on the reduction of intestinal TNF-α level. For sedative and hypnotic effects, OJB > TEN > SNG; for the protection form gastrointestinal irritation and damages, OJB > TEN > SNG. Therefore, in processing Polygala, glycosyl breaking may be related to the decline of pharmacological activity and gastrointestinal toxicity of polygala saponins. PMID:25705699

Characterization of two minor saponins from Cordia piauhiensis by 1H and 13C NMR spectroscopy.

PubMed

Santos, Renata P; Silveira, Edilberto R; Lemos, Telma Leda G; Viana, Francisco Arnaldo; Braz-Filho, Raimundo; Pessoa, Otília Deusdênia L

2005-06-01

A careful NMR analysis with full assignment of the 1H and 13C spectral data for two minor saponins isolated from stems of Cordia piauhiensis is reported. These saponins were isolated by high-performance liquid chromatography and characterized as 3beta-O-[alpha-L-rhamnopyranosyl-(1 --> 2)-beta-D-glucopyranosyl]pomolic acid 28-O-[beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranosyl] ester (1) and 3beta-O-[alpha-L-rhamnopyranosyl-(1 --> 2)-beta-D-glucopyranosyl]oleanolic acid 28-O-[beta-D-xylopyranosyl-(1 --> 2)-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranosyl] ester (2). Their structures were established using a combination of 1D and 2D (1H, 1H-COSY, TOCSY, NOESY, gs-HMQC and gs-HMBC) NMR techniques, electrospray ionization mass spectrometry and chemical evidence. Copyright 2005 John Wiley & Sons, Ltd.

Triterpenoid saponins from the roots of Acanthophyllum gypsophiloides Regel

PubMed Central

Khatuntseva, Elena A; Men’shov, Vladimir M; Shashkov, Alexander S; Tsvetkov, Yury E; Stepanenko, Rodion N; Vlasenko, Raymonda Ya; Shults, Elvira E; Tolstikov, Genrikh A; Tolstikova, Tatjana G; Baev, Dimitri S; Kaledin, Vasiliy A; Popova, Nelli A; Nikolin, Valeriy P; Laktionov, Pavel P; Cherepanova, Anna V; Kulakovskaya, Tatiana V; Kulakovskaya, Ekaterina V

2012-01-01

Summary Two new triterpenoid saponins 1 and 2 were isolated from the methanol extract of the roots of Acanthophyllum gypsophiloides Regel. These saponins have quillaic acid or gypsogenin moieties as an aglycon, and both bear similar sets of two oligosaccharide chains, which are 3-O-linked to the triterpenoid part trisaccharide α-L-Arap-(1→3)-[α-D-Galp-(1→2)]-β-D-GlcpA and pentasaccharide β-D-Xylp-(1→3)-β-D-Xylp-(1→3)-α-L-Rhap-(1→2)-[β-D-Quip-(1→4)]-β-D-Fucp connected through an ester linkage to C-28. The structures of the obtained saponins were elucidated by a combination of mass spectrometry and 2D NMR spectroscopy. A study of acute toxicity, hemolytic, anti-inflammatory, immunoadjuvant and antifungal activity was carried out. Both saponins 1 and 2 were shown to exhibit immunoadjuvant properties within the vaccine composition with keyhole limpet hemocyanin-based immunogen. The availability of saponins 1 and 2 as individual pure compounds from the extract of the roots of A. gypsophiloides makes it a prospective source of immunoactive agents. PMID:23015825

Bioactive oleanane-type saponins from the rhizomes of Anemone taipaiensis.

PubMed

Wang, Xiao-Yang; Gao, Hui; Zhang, Wei; Li, Yuan; Cheng, Guang; Sun, Xiao-Li; Tang, Hai-Feng

2013-10-15

Investigation of the n-BuOH extract of the rhizomes of Anemone taipaiensis led to the isolation of five new oleanane-type triterpenoid saponins (1-5), together with seven known saponins (6-12). Their structures were determined by the extensive use of (1)D and (2)D NMR experiments along with ESIMS analyses and acid hydrolysis. The aglycone of 1, 2 and 4 was determined as siaresinolic acid, which was reported in this genus for the first time. The cytotoxicities of the saponins 1-12, prosapogenins 4a, 5a, 10a-12a and sapogenins siaresinolic acid (SA), oleanolic acid (OA), hederagenin (HE) were evaluated against five human cancer cell lines, including HepG2, HL-60, A549, HeLa and U87MG. The monodesmosidic saponins 6-8, 5a, 10a-12a and sapogenins SA, OA, HE exhibited cytotoxic activity toward all cancer cell lines, with IC50 values ranging from 2.25 to 57.28 μM. Remarkably, the bisdesmosidic saponins 1-4 and 9 showed selective cytotoxicity against the U87MG cells. Copyright © 2013 Elsevier Ltd. All rights reserved.

The day of the yam.

PubMed

Rosser, A

Yam, the staple food in several tropical countries, is a good source of the steroid used in the manufacture of the pill and other sex hormone preparations -- saponin diosgenin. In the early days of production of oral contraceptives (OCs), most yams were gathered from the wild in Mexico. The type richest in steroids takes 3 years to mature and its cultivation has become something of an art. Yams grow best in light, well-drained soil, and for this reason are grown in mounds which have been heavily manured. Propagation is by planting the tops or heads or by small portions of the tuber which is a swollen shoot. Other varieties are planted before the onset of the rains and the crop harvested about 8 months later. In 1970 the Mexican government nationalized the yam industry as a safeguard. This pushed up prices and the drug companies looked elsewhere for a cheap source. Although Mexico still remains the principal grower, India, South Africa, and the Far East supply the industry with plant origin steroids. As more than 90% of the hefty yam tubers consist of water, well over 100,000 tons have to be harvested every year to provide the 600-700 tons of the saponin diosgenin used by the drug companies. In China, where Western corticosteroids are regarded as too expensive for the barefoot doctors, several species of yam are used. Research has been going on to find another source of diosgenin and the most promising seems to be fenugreek, Trigonella foenumgraecum. "Foenum graecum" is Latin for Greek hay and was used by the early Greeks as a culinary and medicinal herb throughout the Mediterranean area. The richness of fenugreek was used to improve the roundness of women's breasts and to stimulate the flow of milk. Bath University has spent 10 years researching the development of a species of fenugreek which will yield large amounts of diosgenin. A certain amount of steroids come from animal sources. Such steroids are given when there is an adverse reaction from the administeration of the synthetic variety. Placentae are a rich source of steroids and have been found to contain hormones, minerals, and enzymes. Placentae now are becoming big business throughout Europe. Although it is possible to make OCs from placental extract, it is not commercially viable. Over 600 varieties of yam exist and at this time there is no danger of the supply running out.

Cytotoxic saponins from Schefflera fagueti.

PubMed

Cioffi, Giuseppina; Braca, Alessandra; Autore, Giuseppina; Morelli, Ivano; Pinto, Aldo; Venturella, Fabio; De Tommasi, Nunziatina

2003-08-01

Six new lupane (1 - 4) and oleanane saponins (5 and 6) were isolated from the aerial parts of Schefflera fagueti Baill. (Araliaceae). Their structures were determined by 2D-NMR spectroscopy (DQF-COSY, 1D-TOCSY, 2D-HOHAHA, 1D-ROESY, HSQC, HMBC). The antiproliferative activity of compounds 1 - 6 and of their prosapogenins (1a - 6a) was evaluated using three continuous murine and human culture cell lines J774, HEK-293, WEHI-164. Oleanane saponins 5 and 6 were the most active, showing significant inhibitory effects on all cell lines, while their prosapogenins 5a and 6a demonstrated minor activity.

Use of (2-/sup 14/C)mevalonate and saponin-bound (/sup 14/C)-3-hydroxy-3-methylglutaric acid for the biosynthesis of terpenoids in leaves of Dioscorea deltoidea

DOE Office of Scientific and Technical Information (OSTI.GOV)

Gurielidze, K.G.; Paseshnichenko, V.A.; Vasil'eva, I.S.

After the introduction of (2-/sup 14/C)acetate into leaves of Dioscorea deltoidea, a radioactive furonanalog of deltafolin - protodeltofolin, containing two-thirds of the label in the 3-hydroxy-3-methylglutaryl portion - was isolated from them. Radioactive ..beta..-careotene and sterols were isolated from cut young leaves of Dioscorea 24 h after the introduction of (/sup 14/C) protodeltofolin into them, using chromatography on a column of silica gel and precipitation of sterols in the form of digitonins for this purpose. The incorporation of radioactivity from (/sup 14/C)-3-hydroxy-3-methyl-glutaric acid, bound in the form of a saponin, and ..beta..-carotene came to 0.18-0.80%, while incorporation into sterols camemore » to 0.07-2.86% of the radioactivity of the alcohol extract. Thereby it was shown that 3-hydroxyl-3-methylglutaric acid, bound in the form of the saponin, can be used to form terpenoids in Dioscorea leaves. It was suggested that the binding of hydroxymethylglutaric acid to saponin represents one of the mechanisms of regulation of the rate of terpenoid biosynthesis in Dioscorea leaves.« less

Phytochemical constituents of some Indian medicinal plants.

PubMed

Dhandapani, R; Sabna, B

2008-04-01

Alkaloids, tannins, saponins, steroid, terpenoid, flavonoids, phlobatannin and cardie glycoside distribution in seven medicinal plants belonging to different families were assessed and compared. The medicinal plants investigated were Aegle marmelos, Cynodon dactylon, Eclipta prostrata, Moringa pterygosperma, Pongamia pinnata, Sida acuta and Tridax procumbens. The significance of the plants in traditional medicine and the importance of the distribution of these chemical constituents were discussed with respect to the role of these plants in ethnomedicine in India.

Effect of organized assemblies. Part 4. Formulation of highly concentrated coal-water slurry using a natural surfactant

DOE Office of Scientific and Technical Information (OSTI.GOV)

Debadutta Das; Sagarika Panigrahi; Pramila K. Misra

2008-05-15

Coal-water slurry has received considerable research nowadays due to its ability in substituting energy sources. The present work reports the formulation of highly concentrated coal-water slurry using a natural occurring surface active compound, saponin, extracted from the fruits of plant Sapindous laurifolia. The isolation of saponin from the plant and its surface activity has been discussed. The rheological characteristics of coal-water slurry have been investigated as a function of coal loading, ash content of coal, pH, temperature, and amount of saponin. The viscosity of the slurry and zeta potential are substantially decreased with concomitant shift of the isoelectric point ofmore » coal on adsorption of saponin to it. In the presence of 0.8% of saponin, coal-water slurry containing 64% weight fraction of coal could be achieved. The slurry is stable for a period of as long as 1 month in contrast to 4-5 h in the case of bare coal-water slurry. The results confirm the use of saponin as a suitable additive for coal-water slurry similar to the commercially available additive such as sodium dodecyl sulfate. Basing on the effect of pH on the zeta potential and viscosity of slurry, a suitable mechanism for saponin-coal interaction and orientation of saponin at the coal-water interface has been proposed. 47 refs., 12 figs., 5 tabs.« less

Countercurrent chromatography separation of saponins by skeleton type from Ampelozizyphus amazonicus for off-line ultra-high-performance liquid chromatography/high resolution accurate mass spectrometry analysis and characterisation.

PubMed

de Souza Figueiredo, Fabiana; Celano, Rita; de Sousa Silva, Danila; das Neves Costa, Fernanda; Hewitson, Peter; Ignatova, Svetlana; Piccinelli, Anna Lisa; Rastrelli, Luca; Guimarães Leitão, Suzana; Guimarães Leitão, Gilda

2017-01-20

Ampelozizyphus amazonicus Ducke (Rhamnaceae), a medicinal plant used to prevent malaria, is a climbing shrub, native to the Amazonian region, with jujubogenin glycoside saponins as main compounds. The crude extract of this plant is too complex for any kind of structural identification, and HPLC separation was not sufficient to resolve this issue. Therefore, the aim of this work was to obtain saponin enriched fractions from the bark ethanol extract by countercurrent chromatography (CCC) for further isolation and identification/characterisation of the major saponins by HPLC and MS. The butanol extract was fractionated by CCC with hexane - ethyl acetate - butanol - ethanol - water (1:6:1:1:6; v/v) solvent system yielding 4 group fractions. The collected fractions were analysed by UHPLC-HRMS (ultra-high-performance liquid chromatography/high resolution accurate mass spectrometry) and MS n . Group 1 presented mainly oleane type saponins, and group 3 showed mainly jujubogenin glycosides, keto-dammarane type triterpene saponins and saponins with C 31 skeleton. Thus, CCC separated saponins from the butanol-rich extract by skeleton type. A further purification of group 3 by CCC (ethyl acetate - ethanol - water (1:0.2:1; v/v)) and HPLC-RI was performed in order to obtain these unusual aglycones in pure form. Copyright © 2016 Elsevier B.V. All rights reserved.

Comprehensive study of the phenolics and saponins from Helleborus niger L. Leaves and stems by liquid chromatography/tandem mass spectrometry.

PubMed

Duckstein, Sarina M; Stintzing, Florian C

2014-02-01

The aerial parts of the medicinal plant Helleborus niger L. comprise a substantial number of constituents with only few of them identified so far. To expand the knowledge of its secondary metabolite profile, extracts from H. niger leaves and stems were investigated by liquid chromatography/tandem mass spectrometry (LC/MS(n) ). Specific identification strategies using LC/MS are established and discussed in detail. The leaves turned out to contain acylated and non-acylated quercetin and kaempferol oligoglycosides, protoanemonin and its precursor ranunculin, β-ecdysone, and a variety of steroidal saponins, mainly in the furostanol form. The sapogenins were elucidated as of sarsasapogenyl, diosgenyl, and macranthogenyl structures, and confirmed by comparison with the respective reference compounds. The secondary metabolite profiles were almost identical in both plant parts except that the stems lacked kaempferol derivatives and some saponins. The ranunculin derivatives and β-ecdysone were found in both plant parts. Correlations between the location of the compound groups and the plant's defense strategies are proposed. Additionally, the role of the detected secondary metabolites as protective substances against exogenic stress and as a defense against herbivores is discussed. Copyright © 2014 Verlag Helvetica Chimica Acta AG, Zürich.

[Advance in chemical constituents of genus Clematis].

PubMed

Sun, Feng; Yang, Depo

2009-10-01

Progresses in the studies on chemical constituents of Clematis L. (belonging to the family Ranunculaceae) were systematiically reviewed in this article. The plants in this genus have a wide spectrum of constituents as follows: triterpenes, flavonoids, lignans, coumarins, alkaloids, volatile oils, steroids, organic acids, macrocyclic compounds and phenols, etc., among which triterpenoid saponins, flavonoids and lignans are the main components. The triterpenoid saponins are mainly oleanolic type and hederagenin type, most of which are bidesmosidic saponins, substituted with oligosaccharide chains at both C-3 and C-28, and some are substituted with acetyl, caffeoyl, isoferuloyl, p-methoxy cinnamyl and 3,4-dimethoxy cinnamyl groups in the oligosaccharide chains. The flavonoids from Clematis species are mainly flavones, flavonols, flavanones, isoflavones, xanthones and their glucosides (sugar moieties are connected to the aglycone through either the oxygen or the carbon atoms), the aglycones of which are mainly apigenin, kaempferol, luteolin and quercetin. The lignans from Clematis are mainly eupomatene lignans, cyclolignans, monoepoxylignans, bisepoxylignans and lignanolides. Clematis spp. are rich in resources, however, studies on their chemical constituents have only been carried out on twenty or so spp. As a result, it is necessary to expand our study on other spp. from this genus for better utilization of medicinal resources.

Extraction, Identification and Biological Activities of Saponins in Sea Cucumber Pearsonothuria graeffei.

PubMed

Khattab, Rafat Afifi; Elbandy, Mohamed; Lawrence, Andrew; Paget, Tim; Rae-Rho, Jung; Binnaser, Yaser S; Ali, Imran

2018-01-01

Secondary metabolism in marine organisms produces a diversity of biologically important natural compounds that are not present in terrestrial species. Sea cucumbers belong to the invertebrate Echinodermata and are famous for their nutraceutical, medical and food values. They are known for possession triterpenoid glycosides (saponins) with various ecological roles. The current work aimed to separate, identify and test various biological activities (antibacterial, antifungal, antileishmanial and anticancer properties) of saponins produced by the holothurian Pearsonothuria graeffei from the Red Sea, Egypt. The structures were identified by 1D and 2D NMR (1H, 13C, TOCSY, COSY, HSQC, HMBC, and ROESY) experiments and acid hydrolysis. The crude and purified fractions was analyzed using matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS)/MS to identify saponins and characterize their molecular structures. Partially purified fraction, mainly containing compounds 1 and 2, was screened for its antifungal activity against three clinical isolates of Candida albicans (Candida 580 (1), Candida 581(2) and Candida MEO47228. Antileishmanial activity against Leishmania major and toxicity on colon cell-line were also evaluated. Two lanostane type sulfated triterpene monoglycosides were isolated from the Holothurian Pearsonothuria graeffei from the Red Sea, Egypt. Holothurin A (1) and echinoside A (2) triterpene saponins were separated by reversed phase semi-preparative HPLC. LC50 values (µg/mL); calculated for the fraction containing saponins 1 and 2 as major constituents; against Candida albicans, Leishmania major and colon cell-line were 10, 20 and 0.50, respectively. Consequently, this study demonstrated the potential use of sea cucumber Pearsonothuria graeffei not only as appreciated functional food or nutraceuticals but also as the source of functional ingredients for pharmaceutical products with antifungal, antileishmanial and anticancer properties. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

Saponins isolated from Asparagus induce apoptosis in human hepatoma cell line HepG2 through a mitochondrial-mediated pathway

PubMed Central

Ji, Y.; Ji, C.; Yue, L.; Xu, H.

2012-01-01

Objective Many scientific studies have shown that Asparagus officinalis has an antitumour effect and enhances human immunity, but the active components and the antitumour mechanisms are unclear. We investigated the effects of saponins isolated from Asparagus on proliferation and apoptosis in the human hepatoma cell line HepG2. Methods HepG2 cells were treated with varying concentrations of Asparagus saponins at various times. Using mtt and flow cytometry assays, we evaluated the effects of Asparagus saponins on the growth and apoptosis of HepG2 cells. Transmission electron microscopy was used to observe the morphology of cell apoptosis. Confocal laser scanning microscopy was used to analyze intracellular calcium ion concentration, mitochondrial permeability transition pore (mptp), and mitochondrial membrane potential (mmp). Spectrophotometry was applied to quantify the activity of caspase-9 and caspase-3. Flow cytometry was used to investigate the levels of reactive oxygen species (ros) and pH, and the expressions of Bcl2, Bax, CytC, and caspase-3, in HepG2 cells. Results Asparagus saponins inhibited the growth of HepG2 cells in a dose-dependent manner. The median inhibitory concentration (IC50) was 101.15 mg/L at 72 hours. The apoptosis morphology at 72 hours of treatment was obvious, showing cell protuberance, concentrated cytoplasm, and apoptotic bodies. The apoptotic rates at 72 hours were 30.9%, 51.7%, and 62.1% (for saponin concentrations of 50 mg/L, 100 mg/L, 200 mg/L). Treatment with Asparagus saponins for 24 hours increased the intracellular level of ros and Ca2+, lowered the pH, activated intracellular mptp, and decreased mmp in a dose-dependent manner. Treatment also increased the activity of caspase-9 and caspase-3, downregulated the expression of Bcl2, upregulated the expression of Bax, and induced release of CytC and activation of caspase-3. Conclusions Asparagus saponins induce apoptosis in HepG2 cells through a mitochondrial-mediated and caspase-dependent pathway, suggesting that they may be a potent agent for the treatment of hepatocellular carcinoma. PMID:22876162

Anti-Trichomonas vaginalis activity of saponins from Quillaja, Passiflora, and Ilex species.

PubMed

Rocha, Tábitha Dahmer; de Brum Vieira, Patrícia; Gnoatto, Simone Cristina Baggio; Tasca, Tiana; Gosmann, Grace

2012-06-01

Trichomonas vaginalis is a flagellated protozoan that causes trichomonosis, the most prevalent non-viral STD worldwide. The pathogen has been associated with serious health consequences including predisposition to cervical cancer and adverse pregnancy outcomes and infertility. It also acts as a co-factor in HIV transmission and acquisition. The 5-nitroimidazole drugs are used in the treatment, however, treatment noncompliance is observed, and a growing number of T. vaginalis isolates resistant to the drugs have been related. Saponins are natural products possessing many biological activities such as antiprotozoan activity. The aim of this study was to evaluate the anti-T. vaginalis activity of saponins from Quillaja, Passiflora, and Ilex species. Saponins from Passiflora alata and Quillaja saponaria presented the best anti-T. vaginalis activity (MIC = 0.025%). In addition, all samples induced erythrocyte lysis and LDH release. As far as we know, this is the first report demonstrating the potential anti-T. vaginalis activity of these saponins.

Minor dehydrogenated and cleavaged dammarane-type saponins from the steamed roots of Panax notoginseng.

PubMed

Gu, Cheng-Zhen; Lv, Jun-Jiang; Zhang, Xiao-Xia; Yan, Hui; Zhu, Hong-Tao; Luo, Huai-Rong; Wang, Dong; Yang, Chong-Ren; Xu, Min; Zhang, Ying-Jun

2015-06-01

Nine new minor dehydrogenated and cleavaged dammarane-type triterpenoid saponins, namely notoginsenosides ST6-ST14 (1-9) were isolated from the steamed roots of Panax notoginseng, together with 14 known ones. Among them, 5-7 and 21-22 were protopanaxadiol type and the left 18 compounds, including 1-4, 8-20, and 23 were protopanaxatriol type saponins. Their structures were identified by extensive analysis of MS, 1D and 2D NMR spectra, and acidic hydrolysis. Resulted from the side chain cleavage, the new saponins 1 and 2 featured in a ketone group at C-25, and 3-5 had an aldehyde unit at C-23. The known saponins 12, 16 and 18 displayed the enhancing potential of neurite outgrowth of NGF-mediated PC12 cells at a concentration of 10 μM, while 20 exhibited acetyl cholinesterase inhibitory activity, with IC50 value of 13.97 μM. Copyright © 2015 Elsevier B.V. All rights reserved.

Structure revision of hupehensis saponin F and G and characterization of new trace triterpenoid saponins from Anemone hupehensis by tandem electrospray ionization mass spectrometry.

PubMed

Li, Fu; Liu, Xin; Tang, Minghai; Chen, Bin; Ding, Lisheng; Chen, Lijuan; Wang, Mingkui

2012-05-15

Electrospray ionization ion-trap tandem mass spectrometry (ESI-MS(n)) was first employed for reinvestigating the structures of hupehensis saponin F and G previously isolated from Anemone hupehensis in our lab. Hupehensis saponin G was determined to contain one more trisaccharide unit (Rha-(1→4)-Glc-(1→6)-Glc-), not a glucose residue, than saponin F based on their molecular weights deduced from their [M+Na](+) ions in ESI-MS spectra. The (2,4)A(4α)-ion at m/z 551.3 formed by retro-Diels-Alder (RDA) rearrangement in positive mode illustrated that the C-28 sugar chains of the two saponins were composed of trisaccharide repeating moieties with (1→4) linkages rather than (1→3) linkages. The interpretation of 2D-NMR spectra of the two compounds also confirmed the results obtained by ESI-MS(n). Moreover, from the water soluble part of A. hupehensis, two novel triterpene saponins were tentatively characterized to contain 4 and 5 (1→4)-linked above trisaccharide repeating moieties at C-28 position according to their ESI-MS(n) behaviors, respectively. Copyright © 2012 Elsevier Ltd. All rights reserved.

Ingasaponin, a complex triterpenoid saponin with immunological adjuvant activity from Inga laurina.

PubMed

Cruz, Maria de Fátima Simão Jucá; Pereira, Gabriela Moysés; Ribeiro, Marcela Gonçalves; da Silva, Ari Miranda; Tinoco, Luzineide Wanderley; da Silva, Bernadete Pereira; Parente, José Paz

2016-02-01

As part of our search of bioactive saponins from Brazilian plants, phytochemical study of the seeds of Inga laurina led to the isolation of a new complex triterpenoid saponin, named ingasaponin. It is the first saponin isolated from a species of Inga genus. It was isolated by using chromatographic methods and its structural elucidation was performed using detailed analyses of (1)H and (13)C NMR spectra including 2D-NMR spectroscopic techniques and chemical conversions. Its structure was established as 21-[[(2E,6S)-6-[[6-deoxy-4-O-[(2E,6S)-6-[(β-D-glucopyranosyl)oxy]-2,6-dimethyl-1-oxo-2,7-octadienyl]-[(β-D-glucopyranosyl)oxy]-2,6-dimethyl-1-oxo-2,7-octadienyl]-[(β-D-glucopyranosyl)oxy]-2,6-dimethyl-1-oxo-2,7-octadienyl]-[(β-D-glucopyranosyl)oxy]-2-(hydroxymethyl)-6-methyl-1-oxo-2,7-octadienyl]oxy]-16-hydroxy-3-[[O-β-D-xylopyranosyl-(1 → 2)-O-α-L-arabinopyranosyl-(1 → 6)-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl]oxy]-(3β,16α,21β)-olean-12-en-28-oic acid O-α-L-arabinofuranosyl-(1 → 4)-O-[β-D-glucopyranosyl-(1 → 3)]-O-6-deoxy-α-L-mannopyranosyl-(1 → 2)-β-D-glucopyranosyl ester (1). The hemolytic potential of 1 was evaluated using in vitro assays, and its adjuvant activity on the cellular immune response against ovalbumin antigen was investigated using in vivo models. Copyright © 2015 Elsevier Ltd. All rights reserved.

Phytochemical analysis of the triterpenoids with cytotoxicity and QR inducing properties from the total tea seed saponin of Camellia sinensis.

PubMed

Li, Ning; Ma, Zhong-Jun; Chu, Yang; Wang, Ying; Li, Xian

2013-01-01

The tea seed triterpene saponin (TS) from Camellia sinensis was found to exhibit better antitumor activity in vivo in S180 implanted ICR mice and QR inducing activity for hepa lclc7 cells respectively compared with the total tea seed saponin (TTS), hydrolysate of the TTS and tea seed flavonoid glycosides (TF). By bioassay-guided isolation, the TS fraction was separated and seven major components were purified and identified as theasaponin E1 (1), theasaponin E2 (2), theasaponin C1 (3), assamsaponin C (4), theasaponin H1 (5), theasaponin A9 (6), and theasaponin A8 (7), among which compounds 4 and 5 were isolated from this genus for the first time. The antitumor bioassay of the isolated compounds showed that compounds 1, 2 and 3 exhibited potential activities against the human tumor cell lines K562 and HL60. Furthermore, compound 1 (the major constituent with a mass content of over 1%) showed significant QR inducing activity with an IR value of 4.2 at 4μg/ml. So it can be concluded that tea seed especially the compound 1 (theasaponin E1) could be used as an antitumor agent and a chemoprevention agent of cancer. The preliminary structure-activity relationship in the anti-tumor activity and QR inducing activity of tea saponins was discussed briefly. Copyright © 2012 Elsevier B.V. All rights reserved.

Participation of cholinergic pathways in α-hederin-induced contraction of rat isolated stomach strips.

PubMed

Mendel, M; Chłopecka, M; Dziekan, N; Karlik, W; Wiechetek, M

2012-05-15

The dry extract of Hedra helix leaves and its main active compounds, predominantly α-hederin and hederacoside C, has been traditionally believed to act spasmolytic. However, it has been recently proved that both, the extract of ivy and triterpenoid saponins, exhibit strong contractile effect on rat isolated stomach smooth muscle strips. It turned out that the most potent contractile agent isolated from the extract of ivy leaves is α-hederin. Thus, it seems reasonable to estimate the mechanism of the contractile effect of this saponin. The presented study was aimed at verifying the participation of cholinergic pathways (muscarinic and nicotine receptors) in α-hederin-induced contraction. The experiments were carried out on rat isolated stomach corpus and fundus strips under isotonic conditions. The preparations were preincubated with either atropine or hexamethonium and then exposed to α-hederin. All results are expressed as the percentage of the response to acetylcholine - a reference contractile agent. The obtained results revealed that the pretreatment of isolated stomach strips (corpus and fundus) with atropine neither prevented nor remarkably reduced the reaction of the preparations to α-hederin. Similarly, if the application of saponin was preceded by the administration of hexamethonium, the strength of the contraction of stomach fundus strips induced by α-hederin was not modified. Concluding, it can be assumed that the cholinergic pathways do not participate in α-hederin-evoked contraction of rat isolated stomach preparations. Copyright © 2012 Elsevier GmbH. All rights reserved.

The influence of saponins on cell membrane cholesterol.

PubMed

Böttger, Stefan; Melzig, Matthias F

2013-11-15

We studied the influence of structurally different saponins on the cholesterol content of cellular membranes. Therefore a cell culture model using ECV-304 urinary bladder carcinoma cells was developed. To measure the cholesterol content we used radiolabeled (3)H-cholesterol which is chemically and physiologically identical to natural cholesterol. The cells were pre-incubated with (3)H-cholesterol and after a medium change, they were treated with saponins to assess a saponin-induced cholesterol liberation from the cell membrane. In another experiment the cells were pre-incubated with saponins and after a medium change, they were treated with (3)H-cholesterol to assess a saponin-induced inhibition of cholesterol uptake into the cell membrane. Furthermore, the membrane toxicity of all applied saponins was analyzed using extracellular LDH quantification and the general cytotoxicity was analyzed using a colorimetric MTT-assay and DNA quantification. Our results revealed a correlation between membrane toxicity and general cytotoxicity. We also compared the results from the experiments on the saponin-induced cholesterol liberation as well as the saponin-induced inhibition of cholesterol uptake with the membrane toxicity. A significant reduction in the cell membrane cholesterol content was noted for those saponins who showed membrane toxicity (IC50 <60 μM). These potent membrane toxic saponins either liberated (3)H-cholesterol from intact cell membranes or blocked the integration of supplemented (3)H-cholesterol into the cell membrane. Saponins with little influence on the cell membrane (IC50 >100 μM) insignificantly altered the cell membrane cholesterol content. The results suggested that the general cytotoxicity of saponins is mainly dependent on their membrane toxicity and that the membrane toxicity might be caused by the loss of cholesterol from the cell membrane. We also analyzed the influence of a significantly membrane toxic saponin on the cholesterol content of intracellular membranes such as those of endosomes and lysosomes. In these experiments ECV-304 cells were either incubated with (3)H-cholesterol or with (3)H-cholesterol and 5 μM saponin. After isolation of the endosomes/lysosomes their (3)H-cholesterol content was measured. A significant influence of the saponins on the cholesterol content of endosomal/lysosomal membranes was not detected. Copyright © 2013 Elsevier Ltd. All rights reserved.

[Studies on extraction process of the main saponin constituents from the stem bark of Kalopanax septemlobus in Guangxi].

PubMed

Yang, Yue; Yang, Xin-ping; Liu, Xiao-fu; Jiang, Xiao-jun

2009-09-01

Using orthogonal experiment design, the total saponin constituents were obtained by refluxing extraction with alcohol and separated by macroporous adsorption resin and n-Butyl alcohol from the stem bark of Kalopanax septemlobus. According to the purity analysis and the yield, the extraction process was optimized. The results showed that the main saponin constituents were gained with a yield of 1.32% by using macroporous adsorption resin but 1.05% by using n-Butyl alcohol. The former was more efficient than the latter on both yield and color. The optimal process with isolation by macroporous adsorption resin is cheap, simple and practical.

A rapid and sensitive LC-MS/MS method for the determination of Pulsatilla saponin D in rat plasma and its application in a rat pharmacokinetic and bioavailability study.

PubMed

Ouyang, Hui; Guo, Yicheng; He, Mingzhen; Zhang, Jinlian; Huang, Xiaofang; Zhou, Xin; Jiang, Hongliang; Feng, Yulin; Yang, Shilin

2015-03-01

A simple, sensitive and specific liquid chromatography-tandem mass spectrometry method was developed and validated for the determination of Pulsatilla saponin D, a potential antitumor constituent isolated from Pulsatilla chinensis in rat plasma. Rat plasma samples were pretreated by protein precipitation with methanol. The method validation was performed in accordance with US Food and Drug Administration guidelines and the results met the acceptance criteria. The method was successfully applied to assess the pharmacokinetics and oral bioavailability of Pulsatilla saponin D in rats. Copyright © 2014 John Wiley & Sons, Ltd.

Phytochemical constituents of some Indian medicinal plants

PubMed Central

Dhandapani, R.; Sabna, B.

2008-01-01

Alkaloids, tannins, saponins, steroid, terpenoid, flavonoids, phlobatannin and cardie glycoside distribution in seven medicinal plants belonging to different families were assessed and compared. The medicinal plants investigated were Aegle marmelos, Cynodon dactylon, Eclipta prostrata, Moringa pterygosperma, Pongamia pinnata, Sida acuta and Tridax procumbens. The significance of the plants in traditional medicine and the importance of the distribution of these chemical constituents were discussed with respect to the role of these plants in ethnomedicine in India. PMID:22557280

Phytochemical content of hot and cold water extracts of Orthosiphon stamineus leaves

NASA Astrophysics Data System (ADS)

Habboo, Maysam Dahham; Nor, Norefrina Shafinaz Md.; Ibrahim, Nazlina

2018-04-01

Orthosiphon stamineus Benth (Lamiaceae) is a plant with ethnobotanical applications including antifungal and antibacterial properties. This study aimed to evaluate the phytochemical contents of Orthosiphon stamineus leaves water extract prepared in cold and hot distilled water. Phytochemical screening revealed the presence of phytochemicals components such as a flavonoid, terpenoid and steroid in both extracts. Cold water extract has two extra components: saponin and alkaloid that may be destroyed by the exposure to heat.

Screening and identification of steroidal saponins from Anemarrhena asphodeloides employing UPLC tandem triple quadrupole linear ion trap mass spectrometry.

PubMed

Xia, Yong-Gang; Guo, Xin-Dong; Liang, Jun; Yang, Bing-You; Kuang, Hai-Xue

2017-09-01

This study presents a practical and valid strategy for the screening and structural characterization of Anemarrhena asphodeloides Bge steroidal saponins (SSs) using ultra-high performance liquid chromatography coupled with triple quadrupole linear ion trap mass spectrometry. The whole analytical protocols integrate four-step procedures in the positive mode: (1) rational deduction of mass fragmentation pathways of A. asphodeloides SSs; (2) untargeted screening of potential A. asphodeloides SSs by multiple-ion monitoring-information-dependent-acquiring-enhanced product ion (MIM-IDA-EPI) scan through reverse phase liquid chromatography; (3) comprehensive construction of an ammoniated precursor ion database by combining untargeted MIM-IDA-EPI scans and data literature; and (4) structural interpretation of targeted A. asphodeloides SSs using MIM-IDA-EPI and multiple reaction monitoring (MRM)-IDA-EPI with an energy-resolved technique. The protocols were used to analyze SSs in A. asphodeloides; of the 87 detected SSs that were unambiguously characterized or tentatively identified, 19 compounds were the first to be reported from A. asphodeloides and 13 ones were characterized as potential new compounds. Accuracy of the analytical procedure was demonstrated by structural identification of three SSs by NMR spectroscopy. The proposed schemes hold an excellent promise in the structural prediction and interpretation of complex SSs from plant medicines by mass spectrometry. Copyright © 2017 Elsevier Inc. All rights reserved.

A novel ultra high-performance liquid chromatography-tandem mass spectrometry method for the simultaneous determination of xanthones and steroidal saponins in crude and salt-processed Anemarrhenae Rhizoma aqueous extracts.

PubMed

Ji, De; Su, Xiaonan; Huang, Ziyan; Wang, Qiaohan; Lu, Tulin

2018-06-01

We established a rapid and sensitive ultra high-performance liquid chromatography tandem mass spectrometry method for the simultaneous quantification of xanthones and steroidal saponins in rat plasma. Chromatographic separation was achieved on a C 18 column with a mobile phase comprising acetonitrile and 0.1% formic acid. The detection was performed by negative electrospray ionization in multiple reaction monitoring mode. The validated method showed good linearity within the tested range (r > 0.9945). The intra- and interday precision at high, medium, and low concentrations was less than 7.96%. The bias of accuracies ranged from -1.92 to 9.62%. The extraction recoveries of the compounds ranged from 84.78 to 88.69%, and the matrix effects ranged from 96.76 to 108.59%. This method was successfully applied to a pharmacokinetic comparison of crude and salt-processed Anemarrhenae Rhizoma aqueous extracts after oral administration in rats. The maximum plasma concentration and area under concentration-time curve of timosaponin BIII and timosaponin AIII increased significantly (P < 0.05 or 0.01) and those of timosaponin BII decreased significantly (P < 0.05) after processing. These results could contribute to the clinical application of crude and salt-processed Anemarrhenae Rhizoma and reveal the processing mechanism. © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Antiproliferative triterpene saponins from Entada africana.

PubMed

Cioffi, Giuseppina; Dal Piaz, Fabrizio; De Caprariis, Paolo; Sanogo, Rokia; Marzocco, Stefania; Autore, Giuseppina; De Tommasi, Nunziatina

2006-09-01

Nine new ester saponins (1-9) were isolated from the roots of Entada africana. Their structures were elucidated by 1D and 2D NMR experiments including 1D and 2D TOCSY, DQF-COSY, HSQC, and HMBC spectroscopy, as well as ESIMS analysis, and chemical methods. The aglycon moieties were found to be echinocystic acid for compounds 1, 2, 4-6, 8, and 9 and acacic acid for 3 and 7. All isolated compounds were tested for their antiproliferative activity against the J774.A1, HEK-293, and WEHI-164 cell lines. Moderate to high cytotoxic potency was found for almost all compounds tested.

Chemical Composition, Toxicity and Vasodilatation Effect of the Flowers Extract of Jasminum sambac (L.) Ait. “G. Duke of Tuscany”

PubMed Central

Kunhachan, Phanukit; Banchonglikitkul, Chuleratana; Kajsongkram, Tanwarat; Khayungarnnawee, Amonrat; Leelamanit, Wichet

2012-01-01

Phytochemical analysis of the ethanolic Jasmine flower extract of Jasminum sambac (L.) Ait. “G. Duke of Tuscany” revealed the mixtures of coumarins, cardiac glycosides, essential oils, flavonoids, phenolics, saponins, and steroids. However, alkaloids, anthraquinones, and tannins were not detected. By intravenous injection at a single dose of 0.5 mL/mouse (15 mg) of the flower extract, no systemic biological toxicity demonstrated in ICR mice was observed. In Wistar rats, the LD50 of the extract was higher than 5,000 mg/kg BW by oral administration. Vasodilatation effect of the 95% ethanolic extract on isolated aortic rats was also investigated. Compared with the control group, the Jasmine flowers extract in 0.05% DMSO clearly reduced tonus of isolated endothelium thoracic aortic rings preconstricted with phenylephrine (10−6 M), as a dose-dependent manner. Nevertheless, this pharmacological effect disappeared after the preincubation of the rings with atropine (10−6 M) or with Nω-nitro-L-arginine (10−4 M). These are possibly due to the actions of the active components on the vessel muscarinic receptors or by causing the release of nitric oxide. PMID:22536286

Antioxidative and Chemopreventive Properties of Vernonia amygdalina and Garcinia biflavonoid

PubMed Central

Farombi, Ebenezer O.; Owoeye, Olatunde

2011-01-01

Recently, considerable attention has been focused on dietary and medicinal phytochemicals that inhibit, reverse or retard diseases caused by oxidative and inflammatory processes. Vernonia amygdalina is a perennial herb belonging to the Asteraceae family. Extracts of the plant have been used in various folk medicines as remedies against helminthic, protozoal and bacterial infections with scientific support for these claims. Phytochemicals such as saponins and alkaloids, terpenes, steroids, coumarins, flavonoids, phenolic acids, lignans, xanthones, anthraquinones, edotides and sesquiterpenes have been extracted and isolated from Vernonia amygdalina. These compounds elicit various biological effects including cancer chemoprevention. Garcinia kola (Guttiferae) seed, known as “bitter kola”, plays an important role in African ethnomedicine and traditional hospitality. It is used locally to treat illnesses like colds, bronchitis, bacterial and viral infections and liver diseases. A number of useful phytochemicals have been isolated from the seed and the most prominent of them is the Garcinia bioflavonoids mixture called kolaviron. It has well-defined structure and an array of biological activities including antioxidant, antidiabetic, antigenotoxic and hepatoprotective properties. The chemopreventive properties of Vernonia amygdalina and Garcinia biflavonoids have been attributed to their abilities to scavenge free radicals, induce detoxification, inhibit stress response proteins and interfere with DNA binding activities of some transcription factors. PMID:21776245

Leishmanicidal activity of saponins isolated from the leaves of Eclipta prostrata and Gymnema sylvestre.

PubMed

Khanna, Venkatesan Gopiesh; Kannabiran, Krishnan; Getti, Giulia

2009-02-01

To evaluate the leishmanicidal activity of saponin, dasyscyphin C of Eclipta prostrata and sapogenin, gymnemagenol from Gymnema sylvestre leaves under in vitro conditions. Dasyscyphin C/Gymnemagenol were dissolved in phosphate buffered saline (PBS) and diluted with liquid medium to obtain concentrations ranging from 1000 to 15 mug /ml. The leishmanicidal activity against leishmanial parasites, Leishmania major, Leishmania aethiopica and Leishmania tropica promastigotes was studied by the MTS assay. The Dasyscyphin C isolated from E. prostrata showed good leishmanicidal activity at 1000mug/ml concentration, with the IC(50) value of 450mug/ml against L. major promastigote and the percentage of parasitic death was 73; whereas, gymnemagenol of G. sylvestre showed only 52% parasitic death at 1000 mug/ml concentration. The other Leishmania species, L. aethiopica and L. tropica promastigotes, were less sensitive to the saponins of E. prostrata and G. sylvestre. From this study, it can be concluded that the dasyscyphin C of E. prostrata has significant leishmanicidal activity against L. major promastigote.

Paris saponin-induced autophagy promotes breast cancer cell apoptosis via the Akt/mTOR signaling pathway.

PubMed

Xie, Zhan-Zhi; Li, Man-Mei; Deng, Peng-Fei; Wang, Sheng; Wang, Lei; Lu, Xue-Ping; Hu, Liu-Bing; Chen, Zui; Jie, Hui-Yang; Wang, Yi-Fei; Liu, Xiao-Xiao; Liu, Zhong

2017-02-25

Paris saponins possess anticancer, anti-inflammatory, and antiviral effects. However, the anticancer effect of Paris saponins has not been well elucidated and the mechanisms underlying the potential function of Paris saponins in cancer therapy are needed to be further identify. In this study, we report that saponin compounds isolated from Paris polyphylla exhibited antitumor activity against breast cancer cell lines, MCF-7 and MDA-MB-231. Paris saponin XA-2 induced apoptosis in both cell lines, as evidenced by the activation of caspases and cleavage of Poly (ADP-ribose) polymerase. The ability of XA-2 to induce autophagy was confirmed by acridine orange staining, accumulation of autophagosome-bound Long chain 3 (LC3)-II, and measurement of autophagic flux. XA-2-induced autophagy was observed to promote apoptosis by the combined treatment of breast cancer cell lines with XA-2 and autophagy inhibitors 3-methyladenine and bafilomycin A1, respectively. Moreover, we report a decrease in the levels of Akt/mTOR signaling pathway proteins, such as the phosphorylated forms of Akt, mTOR, P70S6K, and eukaryotic translation initiation factor 4E-binding protein 1 (4EBP1). Taken together, these results provide important insights explaining the anticancer activity of Paris saponins and the potential development of XA-2 as a new therapeutic agent. Copyright © 2017 Elsevier B.V. All rights reserved.

Saponins from seeds of Genus Camellia: Phytochemistry and bioactivity.

PubMed

Guo, Na; Tong, Tuantuan; Ren, Ning; Tu, Youying; Li, Bo

2018-05-01

Camellia seeds have been traditionally used as oil raw materials in Asia, and are known for a wide spectrum of applications. Oleanane-type triterpene saponins are the major specialised metabolites in Camellia seeds, and more than seventy saponins have been isolated and characterized. These natural compounds have caught much attention due to their various biological and pharmacological activities, including modulation of gastrointestinal system, anti-cancer, anti-inflammation, anti-microorganism, antioxidation, neuroprotection, hypolipidemic effects, foaming and detergence, as well as helping the accumulation of pollutants by plants. These compounds have a promising application in medicine, agriculture, industry and environmental protection. The present paper summarized the information from current publications on Camellia seed saponins, with a focus on the advances made in chemical structures, determination methods, bioactivities and toxicity. We hope this article will stimulate further investigations on these compounds. Copyright © 2018 Elsevier Ltd. All rights reserved.

Cytotoxic oleanane-type triterpenoid saponins from the Rhizomes of Anemone rivularis var. flore-minore.

PubMed

Wang, Xiaoyang; Wang, Minchang; Xu, Min; Wang, Yi; Tang, Haifeng; Sun, Xiaoli

2014-02-18

Phytochemical investigation of the n-BuOH extract of the rhizomes of Anemone rivularis var. flore-minore led to the isolation of five new oleanane-type triterpenoid saponins 1-5, together with five known saponins 6-10. Their structures were determined by the extensive use of 1D and 2D NMR experiments, along with ESIMS analyses and acid hydrolysis. The aglycone of 4 and 5 was determined as 21α-hydroxyoleanolic acid, which was reported in this genus for the first time. The cytotoxicity of these compounds was evaluated against four human cancer cell line, including HL-60 (promyelocytic leukemia), HepG2 (hepatocellular carcinoma), A549 (lung carcinoma) and HeLa (cervical carcinoma). The monodesmosidic saponins 6-8 exhibited cytotoxic activity toward all tested cancer cell lines, with IC50 values in the 7.25-22.38 μM range.

Comparison of ultra-high performance supercritical fluid chromatography and ultra-high performance liquid chromatography for the separation of spirostanol saponins.

PubMed

Zhu, Ling-Ling; Zhao, Yang; Xu, Yong-Wei; Sun, Qing-Long; Sun, Xin-Guang; Kang, Li-Ping; Yan, Ren-Yi; Zhang, Jie; Liu, Chao; Ma, Bai-Ping

2016-02-20

Spirostanol saponins are important active components of some herb medicines, and their isolation and purification are crucial for the research and development of traditional Chinese medicines. We aimed to compare the separation of spirostanol saponins by ultra-high performance supercritical fluid chromatography (UHPSFC) and ultra-high performance liquid chromatography (UHPLC). Four groups of spirostanol saponins were separated respectively by UHPSFC and UHPLC. After optimization, UHPSFC was performed with a HSS C18 SB column or a Diol column and with methanol as the co-solvent. A BEH C18 column and mobile phase containing water (with 0.1% formic acid) and acetonitrile were used in UHPLC. We found that UHPSFC could be performed automatically and quickly. It is effective in separating the spirostanol saponins which share the same aglycone and vary in sugar chains, and is very sensitive to the number and the position of hydroxyl groups in aglycones. However, the resolution of spirostanol saponins with different aglycones and the same sugar moiety by UHPSFC was not ideal and could be resolved by UHPLC instead. UHPLC is good at differentiating the variation in aglycones, and is influenced by double bonds in aglycones. Therefore, UHPLC and UHPSFC are complementary in separating spirostanol saponins. Considering the naturally produced spirostanol saponins in herb medicines are different both in aglycones and in sugar chains, a better separation can be achieved by combination of UHPLC and UHPSFC. UHPSFC is a powerful technique for improving the resolution when UHPLC cannot resolve a mixture of spirostanol saponins and vice versa. Copyright © 2015 Elsevier B.V. All rights reserved.

Two new triterpenoid saponins from Dianthus superbus L.

PubMed

Chen, Xia; Luo, Jian-Guang; Kong, Ling-Yi

2010-06-01

Two new triterpenoid saponins (1 and 2) were isolated from the dried aerial parts of Dianthus superbus L. (Caryophyllaceae). Their structures were elucidated on the basis of spectral data to be 3-O-beta-D-glucopyranosyl olean-9(11),12-diene-23,28-dioic acid 28-O-beta-D-glucopyranoside (1) and 3-O-beta-D-glucopyranosyl olean-11,13(18)-diene-23,28-dioic acid 28-O-beta-D-glucopyranoside (2).

Screening of Potential Free Radicals Scavenger and Antibacterial Activities of Purwoceng (Pimpinella alpina Molk).

PubMed

Wahyuningrum, Retno; Utami, Pri Iswati; Dhiani, Binar Asrining; Kumalasari, Malikhah; Kusumawardani, Rizka Sari

2016-11-01

Purwoceng ( Pimpinella alpina Molk) is a traditional medicinal plant used for its aphrodisiac values. This plant was originated Dieng Plateu, Central Java, Indonesia. Purwoceng has been reported to contain steroid, flavonoids, glycoside, saponins, tannins, and phenolic. Based on secondary metabolite compounds of Purwoceng herbs, a research need to be done to determine the other potential free radicals scavenger and antibacterial activities of Purwoceng. The objectives of this research are to screen the potential free radicals scavenger activity of in vitro using DPPH (1,1 diphenyl-2-picryl-hydrazil) radicals and NO• (nitric oxide) radicals, and antibacterial activity of Purwoceng. The extraction is done by a maceration method with petroleum ether, ethyl acetate, and ethanol solvent, respectively. Free radicals scavenger test was performed using DPPH radicals and NO• radicals, while antibacterial activity screening was performed using agar diffusion test. The results showed that ethyl acetate extract of Purwoceng has free radical scavenger activity with IC50 53.07 ppm lower than butylated hydroxytoluene. Ethyl acetate extract and ethanol extract of Purwoceng have antibacterial activity against Staphyloccus aureus , Escherichia coli , and MG42 bacterial isolate.

Triterpene saponins from Vietnamese ginseng (Panax vietnamensis) and their hepatocytoprotective activity.

PubMed

Tran, Q L; Adnyana, I K; Tezuka, Y; Nagaoka, T; Tran, Q K; Kadota, S

2001-04-01

The methanol extract of Vietnamese ginseng (Panax vietnamensis) was found to possess hepatocytoprotective effects on D-galactosamine (D-GalN)/tumor necrosis factor-alpha (TNF-alpha)-induced cell death in primary cultured mouse hepatocytes. Further chemical investigation of the extract afforded two new dammarane-type triterpene saponins, ginsenoside Rh(5) (1) and vina-ginsenoside R(25) (2), as well as eight known dammarane-type triterpene saponins, majonoside R(2) (3), pseudo-ginsenoside RT(4) (4), vina-ginsenosides R(1) (5), R(2) (6), and R(10) (7), ginsenosides Rg(1) (8), Rh(1) (9), and Rh(4) (10), and a known sapogenin protopanaxatriol oxide II (11). Their structures were elucidated on the basis of spectral analysis. In addition, by the using LC-electrospray ionization (ESI)-MS method, five known saponins, ginsenosides Rb(1), Rb(2), Rc, Rd, and Re (12--16), were also identified in the extract. Among the compounds isolated, majonoside R(2) (3), the main saponin in Vietnamese ginseng, showed strong protective activity against D-GalN/TNF-alpha-induced cell death in primary cultured mouse hepatocytes. This demonstrates that the hepatocytoprotective effect of Vietnamese ginseng is due to dammarane-type triterpene saponins that have an ocotillol-type side chain, a characteristic constituent of Vietnamese ginseng.

Pulsatilla saponin A, an active molecule from Pulsatilla chinensis, induces cancer cell death and inhibits tumor growth in mouse xenograft models.

PubMed

Liu, Qiang; Chen, Weichang; Jiao, Yang; Hou, Jianquan; Wu, Qingyu; Liu, Yanli; Qi, Xiaofei

2014-05-15

Many natural compounds possess antitumor growth activities. Pulsatilla chinensis is an herb used in traditional Chinese medicine to treat infectious diseases. More recently, extracts from P chinensis have been shown to contain antitumor activities. In this study, we isolated Pulsatilla saponin A as an active compound from P chinensis extracts and tested its anticancer activity in vitro and in vivo. In cell culture, Pulsatilla saponin A significantly inhibited the growth of human hepatocellular carcinoma SMCC-7721 cells and pancreatic BXPC3 and SW1990 cancer cells. Similar inhibitory activities were observed when the compound was tested in mouse xenograft tumor models using human hepatocellular carcinoma Bel-7402 and pancreatic cancer SW1990 cells. In Comet assay and flow cytometric analysis of cell cycle distribution and annexin V expression, DNA damage, G2 arrest, and apoptosis were identified in Pulsatilla saponin A-treated cancer cells. Based on the results of Western blotting, p53 and cyclin B protein levels were higher, whereas Bcl-2 protein levels were lower in Pulsatilla saponin A-treated cancer cells than in vehicle-treated cells. Pulsatilla saponin A may exert its antitumor effect by inducing DNA damage and causing G2 arrest and apoptosis in cancer cells. Pulsatilla saponin A and its derivatives may be developed as a new class of anticancer agents. Crown Copyright © 2014. Published by Elsevier Inc. All rights reserved.

Lebbeckoside C, a new triterpenoid saponin from the stem barks of Albizia lebbeck inhibits the growth of human glioblastoma cells.

PubMed

Noté, Olivier Placide; Ngo Mbing, Joséphine; Kilhoffer, Marie-Claude; Pegnyemb, Dieudonné Emmanuel; Lobstein, Annelise

2018-02-19

One new acacic acid-type saponin, named lebbeckoside C (1), was isolated from the stem barks of Albizia lebbeck. Its structure was established on the basis of extensive analysis of 1D and 2D NMR ( 1 H, 13 C NMR, DEPT, COSY, TOCSY, ROESY, HSQC and HMBC) experiments, HRESIMS studies, and by chemical evidence as 3-O-[β-d-xylopyranosyl-(l→2)-β-d-fucopyranosyl-(1→6)-[β-d-glucopyranosyl(1→2)]-β-d-glucopyranosyl]-21-O-{(2E,6S)-6-O-{4-O-[(2E,6S)-2,6-dimethyl-6-O-(β-d-quinovopyranosyl)octa-2,7-dienoyl]-4-O-[(2E,6S)-2,6-dimethyl-6-O-(β-d-quinovopyranosyl)octa-2,7-dienoyl]-β-d-quinovopyranosyl}-2,6-dimethylocta-2,7-dienoyl}acacic acid 28 O-[β-d-quinovopyranosyl-(l→3)-[α-l-arabinofuranosyl-(l→4)]-α-l-rhamnopyranosyl-(l→2)-β-d-glucopyranosyl] ester. The isolated saponin (1) displayed significant cytotoxic activity against the human glioblastoma cell line U-87 MG and TG1 stem-like glioma cells isolated from a patient tumor with IC 50 values of 1.69 and 1.44 μM, respectively.

Isolation and quantification of Quillaja saponaria Molina saponins and lipids in iscom-matrix and iscoms.

PubMed

Behboudi, S; Morein, B; Rönnberg, B

1995-12-01

In the iscom, multiple copies of antigen are attached by hydrophobic interaction to a matrix which is built up by Quillaja triterpenoid saponins and lipids. Thus, the iscom presents antigen in multimeric form in a small particle with a built-in adjuvant resulting in a highly immunogenic antigen formulation. We have designed a chloroform-methanol-water extraction procedure to isolate the triterpenoid saponins and lipids incorporated into iscom-matrix and iscoms. The triterpenoids in the triterpenoid phase were quantitated using orcinol sulfuric acid detecting their carbohydrate chains and by HPLC. The cholesterol and phosphatidylcholine in the lipid phase were quantitated by HPLC and a commercial colorimetric method for the cholesterol. The quantitative methods showed an almost total separation and recovery of triterpenoids and lipids in their respective phases, while protein was detected in all phases after extraction. The protein content was determined by the method of Lowry and by amino acid analysis. Amino acid analysis was shown to be the reliable method of the two to quantitate proteins in iscoms. In conclusion, simple, reproducible and efficient procedures have been designed to isolate and quantitate the triterpenoids and lipids added for preparation of iscom-matrix and iscoms. The procedures described should also be useful to adequately define constituents in prospective vaccines.

Saponins from Albizia lebbeck.

PubMed

Pal, B C; Achari, B; Yoshikawa, K; Arihara, S

1995-03-01

Three main saponins named albiziasaponins A, B, and C were isolated from the barks of Albizia lebbeck. Their structures were established through spectral analyses as acacic acid lactone 3-O-beta-D-xylopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6)- beta-D-glucopyranoside, 3-O-beta-D-glucopyranosyl-(1-->2)-O-[alpha-L-arabinopyranosyl-(1-- >6)]- beta-D-glucopyranoside and 3-O-beta-D-xylopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6)- O- [beta-D-glucopyranosyl-(1-->2)]-beta-D-glucopyranoside.

Two new triterpenoid saponins from rhizome of Anemone raddeana Regel.

PubMed

Fan, Li; Lu, Jincai; Wang, Jing; Cheng, Weiming; Yao, Yan; Liu, Runxiang; Zhang, Hongfen

2010-01-01

Two new 27-hydroxyoleanolic acid-type triterpenoid saponins, raddeanoside Ra (1) and raddeanoside Rb (2), were isolated from the rhizome of Anemone raddeana Regel. The structures of the two compounds were elucidated to be 27-hydroxyoleanolic acid 3-O-beta-D: -glucopyranosyl-(1 --> 4)-alpha-L: -arabinopyranoside (1) and 27-hydroxyoleanolic acid 3-O-alpha-L: -arabinopyranosyl-(1 --> 3)-alpha-L: -rhamnopyranosyl-(1 --> 2)-alpha- L: -arabinopyranoside (2) on the basis of chemical and spectral evidence.

Saponin Biosynthesis in Saponaria vaccaria. cDNAs Encoding β-Amyrin Synthase and a Triterpene Carboxylic Acid Glucosyltransferase1[OA

PubMed Central

Meesapyodsuk, Dauenpen; Balsevich, John; Reed, Darwin W.; Covello, Patrick S.

2007-01-01

Saponaria vaccaria (Caryophyllaceae), a soapwort, known in western Canada as cowcockle, contains bioactive oleanane-type saponins similar to those found in soapbark tree (Quillaja saponaria; Rosaceae). To improve our understanding of the biosynthesis of these saponins, a combined polymerase chain reaction and expressed sequence tag approach was taken to identify the genes involved. A cDNA encoding a β-amyrin synthase (SvBS) was isolated by reverse transcription-polymerase chain reaction and characterized by expression in yeast (Saccharomyces cerevisiae). The SvBS gene is predominantly expressed in leaves. A S. vaccaria developing seed expressed sequence tag collection was developed and used for the isolation of a full-length cDNA bearing sequence similarity to ester-forming glycosyltransferases. The gene product of the cDNA, classified as UGT74M1, was expressed in Escherichia coli, purified, and identified as a triterpene carboxylic acid glucosyltransferase. UGT74M1 is expressed in roots and leaves and appears to be involved in monodesmoside biosynthesis in S. vaccaria. PMID:17172290

Leishmanicidal activity of saponins isolated from the leaves of Eclipta prostrata and Gymnema sylvestre

PubMed Central

Khanna, Venkatesan Gopiesh; Kannabiran, Krishnan; Getti, Giulia

2009-01-01

Objective: To evaluate the leishmanicidal activity of saponin, dasyscyphin C of Eclipta prostrata and sapogenin, gymnemagenol from Gymnema sylvestre leaves under in vitro conditions. Materials and Methods: Dasyscyphin C/Gymnemagenol were dissolved in phosphate buffered saline (PBS) and diluted with liquid medium to obtain concentrations ranging from 1000 to 15 μg /ml. The leishmanicidal activity against leishmanial parasites, Leishmania major, Leishmania aethiopica and Leishmania tropica promastigotes was studied by the MTS assay. Result: The Dasyscyphin C isolated from E. prostrata showed good leishmanicidal activity at 1000μg/ml concentration, with the IC50 value of 450μg/ml against L. major promastigote and the percentage of parasitic death was 73; whereas, gymnemagenol of G. sylvestre showed only 52% parasitic death at 1000 μg/ml concentration. The other Leishmania species, L. aethiopica and L. tropica promastigotes, were less sensitive to the saponins of E. prostrata and G. sylvestre. Conclusion: From this study, it can be concluded that the dasyscyphin C of E. prostrata has significant leishmanicidal activity against L. major promastigote. PMID:20177579

Protective effect and mechanism of action of saponins isolated from the seeds of gac (Momordica cochinchinensis Spreng.) against cisplatin-induced damage in LLC-PK1 kidney cells.

PubMed

Jung, Kiwon; Lee, Dahae; Yu, Jae Sik; Namgung, Hojin; Kang, Ki Sung; Kim, Ki Hyun

2016-03-01

This study was performed to investigate the renoprotective effect and mechanism of Momordicae Semen, gac seeds, against the cisplatin-induced damage in LLC-PK1 kidney cells. In order to identify the active components, three major saponins were isolated from extract of the gac seed, gypsogenin 3-O-β-d-galactopyranosyl(1→2)-[α-L-rhamnopyranosyl(1→3)]-β-d-glucuronopyranoside (1), quillaic acid 3-O-β-D-galactopyranosyl(1→2)-[α-L-rhamnopyranosyl(1→3)]-β-D-glucuronopyranoside (2), and momordica saponin I (3). Compounds 1 and 2 ameliorated cisplatin-induced nephrotoxicity up to 80% of the control value at both 5 and 25μM. Phosphorylation of MAPKs was decreased along cisplatin treatment after treatment with compounds 1 and 2. These results show that blocking the MAPKs signaling cascade plays a critical role in mediating the renoprotective effect of Momordicae Semen extract and compounds 1 and 2. Copyright © 2016 Elsevier Ltd. All rights reserved.

Platelet P2Y12 receptors are involved in the haemostatic effect of notoginsenoside Ft1, a saponin isolated from Panax notoginseng

PubMed Central

Gao, B; Huang, L; Liu, H; Wu, H; Zhang, E; Yang, L; Wu, X; Wang, Z

2014-01-01

BACKGROUND AND PURPOSE Saponins isolated from Panax notoginseng (Burk.) F.H. Chen have been shown to relieve thrombogenesis and facilitate haemostasis. However, it is not known which saponin accounts for this haemostatic effect. Hence, in the present study we aimed to identify which saponins contribute to its haemostatic activity and to elucidate the possible underlying mechanisms. EXPERIMENTAL APPROACH Platelet aggregation was analysed using a platelet aggregometer. Prothrombin time, activated partial thromboplastin time and thrombin time were measured using a blood coagulation analyser, which was further corroborated with bleeding time and thrombotic assays. The interaction of notoginsenoside Ft1 with the platelet P2Y12 receptor was determined by molecular docking analysis, cytosolic Ca2+ and cAMP measurements, and phosphorylation of PI3K and Akt assays. KEY RESULTS Among the saponins examined, Ft1 was the most potent procoagulant and induced dose-dependent platelet aggregation. Ft1 reduced plasma coagulation indexes, decreased tail bleeding time and increased thrombogenesis. Moreover, it potentiated ADP-induced platelet aggregation and increased cytosolic Ca2+ accumulation, effects that were attenuated by clopidogrel. Molecular docking analysis suggested that Ft1 binds to platelet P2Y12 receptors. The increase in intracellular Ca2+ evoked by Ft1 in HEK293 cells overexpressing P2Y12 receptors could be blocked by ticagrelor. Ft1 also affected the production of cAMP and increased phosphorylation of PI3K and Akt downstream of P2Y12 signalling pathways. CONCLUSION AND IMPLICATIONS Ft1 enhanced platelet aggregation by activating a signalling network mediated through P2Y12 receptors. These novel findings may contribute to the effective utilization of this compound in the therapy of haematological disorders. PMID:24117220

Putative mechanism for apoptosis-inducing properties of crude saponin isolated from sea cucumber (Holothuria leucospilota) as an antioxidant compound

PubMed Central

Soltani, Mozhgan; Parivar, Kazem; Baharara, Javad; Kerachian, Mohammad Amin; Asili, Javad

2015-01-01

Objective(s): Marine organisms are known as a potential source of natural products, which contain bioactive substances with therapeutic properties. Sea cucumbers are prominent among marine organisms because of their dietary and therapeutic applications. In addition, they have capacity of synthesizing saponins molecules and other metabolites with therapeutic properties such as antitumor, antimicrobial, anti-inflammatory and antioxidant activities. The aim of this study was to evaluate the antioxidant and pro-apoptotic effects of sea cucumber saponins (SCS) isolated from Holothuria leucospilota species. Materials and Methods: Evaluation of antioxidant activity of SCS was carried out by DPPH (1, 1-diphenyl-2-picrylhydrazyl), ABTS (azino-bis-3-ethylbenzothiazoline-6-sulfonic acid), power reducing and total antioxidant assays. The anti-proliferative effect was studied by MTT (3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide) assay. Mechanisms leading to apoptosis were also evaluated by fluorescence microscopy, flow cytometry and real time PCR. Results: The results showed that the DPPH and ABTS activities increased in a dose dependent manner. The reducing capacity enhanced with increasing concentration of the saponin extract (0 to 2 mg/ml). The SCS exhibited moderate total antioxidant activity. Evaluation of anti-proliferative effect revealed that SCS with IC50 of about 6 μg/ml, can display a good cytotoxic activity in a dose dependent manner. Further apoptosis induction was confirmed by fluorescence microscopy and flow cytometry. Sea cucumber saponin was also found to exert a pro-apoptotic effect by increasing the expression of Bax and decreasing the expression of Bcl2. Conclusion: These results indicate that the SCS may act as a natural antioxidant and antitumor agent. PMID:25810893

Primary constituents of blue cohosh: quantification in dietary supplements and potential for toxicity.

PubMed

Rader, Jeanne I; Pawar, Rahul S

2013-05-01

Dietary supplements containing dried roots or extracts of the roots and/or rhizomes of blue cohosh (Caulophyllum thalictroides) are widely available. This botanical has a long history of use by Native Americans and its use continues to the present day. The primary constituents of blue cohosh are its alkaloids and saponins. The structures of the alkaloids magnoflorine, baptifoline, anagyrine, and N-methylcytisine have been known for many years. The last 10 years have seen a great increase in isolation and identification of the large number of saponins present in blue cohosh. Important developments in nuclear magnetic resonance techniques have contributed substantially to the increase in elucidation of the structures of the complex saponins. Several authors have described quantitative methods for both the alkaloids and saponins in blue cohosh. Such methods have made it possible to quantify these constituents in dietary supplements containing this botanical ingredient. Concentrations of both alkaloids and saponins vary substantially in dietary supplements of blue cohosh. The nicotinic alkaloid, N-methylcytisine, a potent toxicant, has been found in all dietary supplements of blue cohosh analyzed. The teratogenic alkaloid anagyrine has been found in some but not all dietary supplements.

Synthesis and biological evaluation of Raddeanin A, a triterpene saponin isolated from Anemone raddeana.

PubMed

Qian, Shan; Chen, Quan Long; Guan, Jin Long; Wu, Yong; Wang, Zhou Yu

2014-01-01

First, Raddeanin A, a cytotoxic oleanane-type triterpenoid saponin isolated from Anemone raddeana REGEL, was synthesized. Stepwise glycosylation was adopted in the synthesis from oleanolic acid, employing arabinosyl, glucosyl and rhamnosyl trichloroacetimidate as donors. The chemical structure of Raddeanin A was confirmed by means of (1)H-NMR, (13)C-NMR, IR, MS and elemental analysis, which elucidated the structure to be 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranoside oleanolic acid. Biological activity tests showed that in the range of low concentrations, Raddeanin A displayed moderate inhibitory activity against histone deacetylases (HDACs), indicating that the HDACs' inhibitory activity of Raddeanin A may contribute to its cytotoxicity.

New furostanol saponins with anti-inflammatory and cytotoxic activities from the rhizomes of Smilax davidiana.

PubMed

Zhou, Meng; Huang, Liping; Li, Linyu; Wei, Yifei; Shu, Jicheng; Liu, Xing; Huang, Huilian

2017-11-01

Seven new furostanol saponins have been isolated from the rhizomes of Smilax davidiana. Their structures were established by 2D NMR spectroscopic techniques ( 1 H, 1 H-COSY, NOESY, HSQC and HMBC), mass spectrometry and comparison with the literature. The isolated compounds were subjected to evaluate anti-inflammatory and cytotoxic activities in vitro. Compounds 3, 5 and 7 were found to have modest anti-inflammatory effects through suppression of IL-1β production and promote the expression of IL-10 in LPS-stimulated RAW 264.7 cells. Davidianoside F (6) showed activity against MCF-7 and HELA cell lines at the concentration of 10.2µM and 4.3µM, respectively. Copyright © 2017. Published by Elsevier Inc.

27-Hydroxyoleanolic acid type triterpenoid saponins from Anemone raddeana rhizome.

PubMed

Fan, Li; Lu, Jin-Cai; Xue, Jiao; Gao, Song; Xu, Bei-Bei; Cao, Bai-Yi; Zhang, Jing-Jing

2010-02-01

Two new 27-hydroxyoleanolic acid type triterpenoid saponins were isolated from the rhizomes of Anemone raddeana Regel. The structures of the two compounds were elucidated as 27-hydroxyoleanolic acid 3-O-beta-D-glucopyranosyl (1 --> 2)-alpha-L-arabinopyranoside (1) and 3-O-alpha-L-rhamnopyranosyl (1 --> 2)[beta-D-glucopyranosyl (1 --> 4)]-alpha-L-arabinopyranosyl-27-hydroxyoleanolic acid 28-O-alpha-L-rhamnopyranosyl (1 --> 4)-beta-D-glucopyranosyl (1 --> 6)-beta-D-glucopyranoside (2) on the basis of chemical and spectral evidence.

Anti-inflammatory activities of Ophiopogonis Radix on hydrogen peroxide-induced cellular senescence of normal human dermal fibroblasts.

PubMed

Kitahiro, Yumi; Koike, Atsushi; Sonoki, Aska; Muto, Mei; Ozaki, Kazuo; Shibano, Makio

2018-06-30

Ophiopogonis Radix (Ophiopogon root), which nourishes the yin, has been used in clinical practice to promote fluid secretion and to moisturize the lungs and skin in traditional Chinese and Japanese (Kampo) medicine. To evaluate this traditional medicinal effect, we investigated the anti-chronic inflammatory effect of Radix Ophiopogonis on senescent cells. Conversely, although several phenotypes of Ophiopogon japonicus Ker-Gawler (Liliaceae) are prevalent in Japan and China, we used these Ophiopogon roots by considering them as one crude drug, Ophiopogonis Radix. In this study, it was revealed that there are two chemotypes (Types A and B) in the root of the original plant, O. japonicus. Methylophiopogonanone A (compound 1) and methylophiopogonanone B (compound 2) were isolated as index compounds from Type A and compound 1 and ophiopogonanone A (compound 3) from Type B. In addition, ophiopogonin B (compound 4) was isolated as the main steroidal saponin from both Type A and B. The results indicated that two different methanol extracts (from Types A and B) and the main constituents of O. japonicus (compound 1-4), significantly downregulated the expression of interleukin (IL)-6 and IL-8, which were enhanced by senescent normal human dermal fibroblasts. Moreover, the two different methanol extracts and compounds 1-4 decreased IL-6 production in a strong and concentration-dependent manner by the ELISA method.

[Bioactive saponins and glycosides. XIII. Horse chestnut. (3): Quantitative analysis of escins Ia, Ib, IIa, and IIb by means of high performance liquid chromatography].

PubMed

Yoshikawa, M; Murakami, T; Otuki, K; Yamahara, J; Matsuda, H

1999-01-01

As a part of our studies on the characterization of bioactive saponin constituents of horse chestnut trees, a quantitative method using high performance liquid chromatography (HPLC) has been developed for four principle saponin constituents, such as escins Ia, Ib, IIa, and IIb, isolated from the seeds of European horse chestnut trees (Aesculus hippocastanum L., Hippocastanaceae). As an application of this HPLC method, we examined the contents and compositions of these escins in the seeds of Japanese horse chestnut trees (A. turbinata BLUME) and in several commercial materials named as "beta-escin". Additionally, the distribution of escins in the Japanese horse chestnut trees was examined, and escins were found to be contained only in the seeds.

Antagonistic effect of alkaloids and saponins on bioactivity in the quinine tree (Rauvolfia caffra sond.): further evidence to support biotechnology in traditional medicinal plants.

PubMed

Milugo, Trizah K; Omosa, Leonida K; Ochanda, James O; Owuor, Bethwell O; Wamunyokoli, Fred A; Oyugi, Julius O; Ochieng, Joel W

2013-10-26

The Quinine tree (Rauvolfia caffra) is used as a medicinal plant among traditional communities in many countries to manage tumors and other diseases associated with oxidative stress. To validate indigenous knowledge and possibly position this herb for technology uptake and utilization, we established the level of antioxidant activity in R. caffra, and probed for the presence of associated phytochemicals. Antioxidant activity was determined on 1,1-diphenyl-2-picrylhydrazyl (DPPH) while major phytochemicals were identified by multiple tests on methanol fractions. R. caffra showed promise as a cure, with antioxidant activity comparable to the commercially used drug quercetin (R. caffra = 79.7% ±1.9; quercetin = 82.6% ± 2.0). However, we found two phytochemicals with possible antagonistic effect: co-occurrence of alkaloids and saponins significantly reduced antioxidant activity (alkaloids only = 63%; alkaloids plus saponins = 15%; steroids, terpenoids and cardiac glycosides = 82%), thus alkaloids and saponins should be exclusive to each other in drug formulations. Antagonistic relationship among phytochemicals would affect the efficacy of crude extracts as used in traditional medicine. Unlike in herbal medicine, use of modern biotechnology in extraction, purification and design of optimal combinations will ensure efficient drug formulations with optimum bioactivity and minimum toxicity. Metabolic pathway engineering under a controlled environment may optimize availability of desired compounds.

Oleanane-type triterpene saponins from Calendula stellata.

PubMed

Lehbili, Meryem; Alabdul Magid, Abdulmagid; Kabouche, Ahmed; Voutquenne-Nazabadioko, Laurence; Abedini, Amin; Morjani, Hamid; Sarazin, Thomas; Gangloff, Sophie C; Kabouche, Zahia

2017-12-01

Five previously undescribed bisdesmosidic triterpenoid saponins named calendustellatosides A-E, along with fifteen known compounds were isolated from the 70% ethanol whole plant extract of Calendula stellata Cav. (Asteraceae). Their structures were determined by 1D- and 2D-NMR spectroscopy as well as high resolution mass spectrometry and acid hydrolysis. The saponins comprised oleanolic acid, echinocystic acid, morolic acid or mesembryanthemoidigenic acid as the aglycones and saccharide moieties at C-3 and C-28. Like most Calendula saponins, the sugar moiety linked at C-3 was either β-d-glucose or β-d-glucuronic acid which could be substituted at C-3 by a β-d-galactose and/or C-2 by a supplementary β-d-galactose or a β-d-glucose. The sugar moiety linked to C-28 was determined as β-d-glucose. The antibacterial evaluation of compounds 1-20 by bioautography on Staphylococcus aureus followed by the determination of MIC values of active compounds by serial dilution technique against 5 bacteria revealed that; calendustellatoside D was the most active against Enterococcus faecalis with an antibacterial effect comparable to antibiotics. The cytotoxic activities of isolated compounds were evaluated against fibrosarcoma cell line (HT1080) and human lung cancer cell line (A549). Calendustellatosides B and D exhibited a low cytotoxic activity against HT1080 cell line with IC 50 values of 47 ± 0.6 and 39 ± 0.5 μM, respectively. Copyright © 2017 Elsevier Ltd. All rights reserved.

Insecticidal components from field pea extracts: soyasaponins and lysolecithins.

PubMed

Taylor, Wesley G; Fields, Paul G; Sutherland, Daniel H

2004-12-15

Extracts from field peas (Pisum sativum L.) have previously been shown to have a utility to control insect pests. To identify potentially new bioinsecticides in field crops, we describe the fractionation of impure extracts (C8 extracts) derived from protein-rich fractions of commercial pea flour. The activity of separated fractions was determined by a flour disk antifeedant bioassay with the rice weevil [Sitophilus oryzae (L.)], an insect pest of stored products. Bioassay-guided fractionation showed that the triterpenoid saponin fractions were partly responsible for the antifeedant activity of C8 extracts. Soyasaponin I (soyasaponin Bb), isolated from peas and soybeans, and mixtures of soyasaponins, comprised of soyasaponins I-III and isolated from soybeans, were inactive antifeedants, but dehydrosoyasaponin I (the C-22 ketone derivative of soyasaponin I), a minor component found in C8 extracts, was shown to be an active component. Dehydrosoyasaponin I (soyasaponin Be) and soyasaponin VI (soyasaponin betag) coeluted under conditions of silica gel thin-layer chromatography and C18 high-performance liquid chromatography. However, dehydrosoyasaponin I could be isolated from saponin-enriched fractions with a reversed phase column of styrene/divinylbenzene operated at alkaline pH. Phospholipids of the lysolecithin type were also identified in saponin fractions of C8 extracts from peas. Three of the lysolecithins were inactive alone against rice weevils, but mixtures of these phospholipids enhanced the insecticidal activity of dehydrosoyasaponin I.

Analgesic and antipyretic activities of Momordica charantia Linn. fruits

PubMed Central

Patel, Roshan; Mahobia, Naveen; Upwar, Nitin; Waseem, Naheed; Talaviya, Hetal; Patel, Zalak

2010-01-01

Plant Momordica charantia Linn. belongs to family Cucurbitaceae. It is known as bitter gourd in English and karela in Hindi. Earlier claims show that the plant is used in stomachic ailments as a carminative tonic; as an antipyretic and antidiabetic agent; and in rheumatoid arthritis and gout. The fruit has been claimed to contain charantin, steroidal saponin, momordium, carbohydrates, mineral matters, ascorbic acid, alkaloids, glucosides, etc. The ethanolic extract of the fruit showed the presence of alkaloids, tannins, glycosides, steroids, proteins, and carbohydrates. The present study was carried out using acetic acid-induced writhing and tail-immersion tests in mice, while yeast-induced pyrexia in rats. The ethanolic extracts (250 and 500 mg/kg, po.) showed an analgesic and antipyretic effect, which was significantly higher than that in the control rats. The observed pharmacological activities provide the scientific basis to support traditional claims as well as explore some new and promising leads. PMID:22247882

Analgesic and antipyretic activities of Momordica charantia Linn. fruits.

PubMed

Patel, Roshan; Mahobia, Naveen; Upwar, Nitin; Waseem, Naheed; Talaviya, Hetal; Patel, Zalak

2010-10-01

Plant Momordica charantia Linn. belongs to family Cucurbitaceae. It is known as bitter gourd in English and karela in Hindi. Earlier claims show that the plant is used in stomachic ailments as a carminative tonic; as an antipyretic and antidiabetic agent; and in rheumatoid arthritis and gout. The fruit has been claimed to contain charantin, steroidal saponin, momordium, carbohydrates, mineral matters, ascorbic acid, alkaloids, glucosides, etc. The ethanolic extract of the fruit showed the presence of alkaloids, tannins, glycosides, steroids, proteins, and carbohydrates. The present study was carried out using acetic acid-induced writhing and tail-immersion tests in mice, while yeast-induced pyrexia in rats. The ethanolic extracts (250 and 500 mg/kg, po.) showed an analgesic and antipyretic effect, which was significantly higher than that in the control rats. The observed pharmacological activities provide the scientific basis to support traditional claims as well as explore some new and promising leads.

Apoptosis and pro-death autophagy induced by a spirostanol saponin isolated from Rohdea chinensis (Baker) N. Tanaka (synonym Tupistra chinensis Baker) on HL-60 cells.

PubMed

Yi, Xiaomin; Xiang, Limin; Huang, Yuying; Wang, Yihai; He, Xiangjiu

2018-03-15

Our previous study has revealed that the spirostanol saponins isolated from the rhizomes of Rohdea chinensis (Baker) N. Tanaka (synonym Tupistra chinensis Baker) (Convallariaceae) (a reputed folk medicine) exhibited potent antiproliferative activity. However, the underlying mechanism of purified saponins remains unclear. More studies are necessary to assess the apoptosis and autophagy activities of the saponins from R. chinensis and clarify their antiproliferative mechanisms. The present study certificated the potential antiproliferative activity and mechanism of 5β-spirost-25(27)-en-1β,3β-diol-1-O-α-L-rhamnopyranosyl-(1→2)- β-D-xylopyranosyl-3-O-α-L-rhamnopyranoside (SPD), a spirostanol saponin from R. chinensis, against human acute promyelocytic leukemia cells (HL-60). The antiproliferative activity of SPD in vitro was evaluated by MTT assay compared with cis-dichlorodiammineplatinum (II). The autophagic activity was assessed using MDC staining and western blot, cell apoptosis inspection was detected by Annexin V-FITC/PI double staining and the mitochondrial membrane potential was detected by JC-1 fluorescence dye combined with flow cytometry. The potential mechanisms for protein levels of apoptosis and autophagy were evaluated by western blot. Treatment of HL-60 cells with SPD resulted in growth inhibition (IC 50 value of 2.0 ± 0.2 µM, after 48 h treatment) and induction of apoptosis and autophagy. Results from Annexin V-FITC/PI double-staining assay and mitochondrial membrane potential detection showed that apoptosis was happened after SPD treatment. The regulation of caspase-3, Bax, Bcl-2, PARP following SPD treatment contributed to the induction of mitochondria-dependent apoptosis. Meanwhile, SPD induced autophagy related with Akt/mTOR/p70S6K signaling and activated of AMPK signaling pathway. Furthermore, blocking autophagy with bafilomycin A1 reduced the cytotoxicity of SPD in HL-60 cells. The antiproliferative, apoptosis and pro-death autophagy activities of SPD suggested that spirostanol saponins from R. chinensis would be a potential cytotoxic candidate against acute promyelocytic leukemia. Copyright © 2018 Elsevier GmbH. All rights reserved.

Rapid and Sensitive Determination of the Major Steroidal Saponins of Ypsilandra thibetica Franch by Ultra High-Performance Liquid Chromatography Coupled with Triple Quadrupole Mass Spectrometry.

PubMed

Xia, Li; Ouyang, Pu-Yue; Gao, Wen; Yi, Tao; Zhang, Xian-Tao; Zhao, Zhen-Dong; Yang, Hua

2016-07-01

A rapid and validated method using ultra high-performance liquid chromatography coupled with a triple quadrupole mass spectrometry (UHPLC-QQQ MS) was developed for simultaneous determination of four active steroidal saponins, i.e., dichotomin ( 1: ), pennogenin 3-O-α-l-arabinofuranosyl-(1→4)-[α-l-rhamnopyranosyl-(1→2)]-β-d-glucopyranoside ( 2: ), pennogenin 3-O-α-l-rhamnopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→4)]-β-d-glucopyranoside ( 3: ) and diosgenin 3-O-α-l-rhamnopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→4)]-β-d-glucopyranosidein ( 4: ), in Ypsilandra thibetica Franch. The optimized sample preparation and UHPLC-QQQ MS conditions were chosen for quantitative analysis. The separation was performed on an Agilent Zorbax Eclipse Plus C18 column (2.1 mm × 50 mm, 1.8 µm) with gradient elution of acetonitrile-0.1% formic acid in water. All calibration curves showed good linear regression (r> 0.9985) within the test range. The limits of detection and quantification were in the range of 0.02-4.40 and 0.04-22.0 ng/mL, respectively. The proposed method was applied to analyze two batches of Y. thibetica samples for target compounds within 10 min. This work promoted the quality control method for raw material or preparations of Y. thibetica. © The Author 2016. Published by Oxford University Press. All rights reserved. For permissions, please e-mail: journals.permissions@oup.com.

1H and 13C NMR spectral data of new saponins from Cordia piauhiensis.

PubMed

Santos, Renata P; Silveira, Edilberto R; Uchôa, Daniel Esdras de A; Pessoa, Otília Deusdênia L; Viana, Francisco Arnaldo; Braz-Filho, Raimundo

2007-08-01

Two new bidesmoside triterpenoid saponins were isolated from stems of Cordia piauhiensis. Their structures, characterized as 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-beta-D-glucopyranosyl pomolic acid 28-O-beta-D-glucopyranosyl ester (1) and 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-beta-D-glucopyranosyl oleanolic acid 28-O-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranosyl ester (2), were unequivocally established after extensive NMR (1H, 13C, DEPT 135 degrees, COSY, HSQC, HMBC, TOCSY, and NOESY) studies. Copyright 2007 John Wiley & Sons, Ltd.

Cytotoxic saponins from Schefflera rotundifolia.

PubMed

Braca, Alessandra; Autore, Giuseppina; De Simone, Francesco; Marzocco, Stefania; Morelli, Ivano; Venturella, Fabio; De Tommasi, Nunziatina

2004-10-01

Eight new oleanane and lupane saponins (1-8) as well as two new benzyl glycosides (9 and 10) were isolated from the aerial parts of Schefflera rotundifolia (Ten) Frodin (Araliaceae) together with two known benzyl glycosides. Their structures were established using 1D- and 2D-NMR spectroscopy and mass spectrometry. The antiproliferative activity of all compounds was evaluated using three continuous murine and human culture cell lines J774.A1, HEK-293, and WEHI-164. Compounds 7 and 8, having betulinic acid as aglycone, were the most active constituents.

Method development and application of offline two-dimensional liquid chromatography/quadrupole time-of-flight mass spectrometry-fast data directed analysis for comprehensive characterization of the saponins from Xueshuantong Injection.

PubMed

Yang, Wenzhi; Zhang, Jingxian; Yao, Changliang; Qiu, Shi; Chen, Ming; Pan, Huiqin; Shi, Xiaojian; Wu, Wanying; Guo, Dean

2016-09-05

Xueshuantong Injection (XSTI), derived from Notoginseng total saponins, is a popular traditional Chinese medicine injection for the treatment of thrombus-resultant diseases. Current knowledge on its therapeutic basis is limited to five major saponins, whereas those minor ones are rarely investigated. We herein develop an offline two-dimensional liquid chromatography/quadrupole time-of-flight mass spectrometry-fast data directed analysis (offline 2D LC/QTOF-Fast DDA) approach to systematically characterize the saponins contained in XSTI. Key parameters affecting chromatographic separation in 2D LC (including stationary phase, mobile phase, column temperature, and gradient elution program) and the detection by QTOF MS (involving spray voltage, cone voltage, and ramp collision energy) were optimized in sequence. The configured offline 2D LC system showed an orthogonality of 0.84 and a theoretical peak capacity of 8976. Total saponins in XSTI were fractionated into eleven samples by the first-dimensional hydrophilic interaction chromatography, which were further analyzed by reversed-phase UHPLC/QTOF-Fast DDA in negative ion mode. The fragmentation features evidenced from 36 saponin reference standards, high-accuracy MS and Fast-DDA-MS(2) data, elemental composition (C<80, H<120, O<50), double-bond equivalent (DBE 5-15), and searching an in-house library of Panax notoginseng, were simultaneously utilized for structural elucidation. Ultimately, 148 saponins were separated and characterized, and 80 have not been isolated from P. notoginseng. An in-depth depiction of the chemical composition of XSTI was achieved. The results obtained would benefit better understanding of the therapeutic basis and significant promotion on the quality standard of XSTI as well as other homologous products. Copyright © 2016. Published by Elsevier B.V.

Triterpenoid Saponin Biosynthetic Pathway Profiling and Candidate Gene Mining of the Ilex asprella Root Using RNA-Seq

PubMed Central

Zheng, Xiasheng; Xu, Hui; Ma, Xinye; Zhan, Ruoting; Chen, Weiwen

2014-01-01

Ilex asprella, which contains abundant α-amyrin type triterpenoid saponins, is an anti-influenza herbal drug widely used in south China. In this work, we first analysed the transcriptome of the I. asprella root using RNA-Seq, which provided a dataset for functional gene mining. mRNA was isolated from the total RNA of the I. asprella root and reverse-transcribed into cDNA. Then, the cDNA library was sequenced using an Illumina HiSeq™ 2000, which generated 55,028,452 clean reads. De novo assembly of these reads generated 51,865 unigenes, in which 39,269 unigenes were annotated (75.71% yield). According to the structures of the triterpenoid saponins of I. asprella, a putative biosynthetic pathway downstream of 2,3-oxidosqualene was proposed and candidate unigenes in the transcriptome data that were potentially involved in the pathway were screened using homology-based BLAST and phylogenetic analysis. Further amplification and functional analysis of these putative unigenes will provide insight into the biosynthesis of Ilex triterpenoid saponins. PMID:24722569

[Application of high performance liquid-ion trap mass spectrometry in analyzing saponins in sodium aescinate].

PubMed

Song, Xiao-Hong; Wang, Wei-Hao; Chen, Shi-Tao; Chen, Sha; Zhang, Jun; Wang, Yue-Sheng; Liu, An

2016-07-01

Sodium aescinate, which is produced from saponins of Chinese Buckeye Seed, is a prescription drug for treatment of brain edema and all kinds of swellings caused by surgery. In this article, high-performance liquid chromatography/ion trap (HPLC-IT) mass spectrometry was applied to study the characteristic ions of ten reference substances, namely escin Ⅰa, escin Ⅰb, isoescin Ⅰa, isoescin Ⅰb, aesculiside A, aesculiside B, aesculuside A, escin Ⅳc, escinⅡa and escin Ⅴ, which were isolated from aescinate. Furthermore, 19 saponin compounds were predicted in sodium aescinate, besides the above mentioned reference substances. The study showed that sapogenins in sodium aescinate had two structural types, namely protoaescigenin and barringenol C, and the substituent acetyl, tigloyl or angeloyl was usually located at C-21, C-22 or C-28 position. Among these predicted saponins, their sugar chains were all located at C-3 position consisting of glucose and glucuronide. This study provides experimental data for chemical constituents in sodium aescinate and scientific basis for quality and safety evaluation. Copyright© by the Chinese Pharmaceutical Association.

Characterization and quantification of flavonoids and saponins in adzuki bean (Vigna angularis L.) by HPLC-DAD-ESI-MSn analysis.

PubMed

Liu, Rui; Cai, Zongwei; Xu, Baojun

2017-09-22

Bioactive activities of adzuki bean have been widely reported, however, the phytochemical information of adzuki bean is incomplete. The aim of this study was to characterize and quantify flavonoids and saponins in adzuki bean. High performance liquid chromatography with diode array detection and electro spray ionization-tandem multi-stage mass spectrometry (HPLC-DAD-ESI-MS n ) were applied to do qualitative and quantitative analyses. A total of 15 compounds from adzuki bean were identified by HPLC-DAD-ESI-MS n . Among 15 compounds identified, four flavonoids (catechin, vitexin-4″-O-glucoside, quercetin-3-O-glucoside, and quercetin-3-O-rutinoside) and six saponins (azukisaponin I, II, III, IV, V, and VI) in adzuki bean were further quantified by external calibration method using HPLC-MS with the program of time segment and extract ion chromatogram (EIC) analysis. Current qualitative and quantitative method based on HPLC and MS technique provides a scientific basis for in vitro and in vivo pharmacological study in the future. Graphical abstract Isolation and characterization of flavonoids and saponins from adzuki bean.

Isolation of a 5-Kilodalton Actin-Sequestering Peptide from Human Blood Platelets

NASA Astrophysics Data System (ADS)

Safer, Daniel; Golla, Rajasree; Nachmias, Vivianne T.

1990-04-01

Resting human platelets contain ≈0.3 mM unpolymerized actin. When freshly drawn and washed platelets are treated with saponin, 85-90% of the unpolymerized actin diffuses out. Analysis by polyacrylamide gel electrophoresis under nondenaturing conditions shows that the bulk of this unpolymerized actin migrates with a higher mobility than does pure G-actin, profilactin, or actin-gelsolin complex. When muscle G-actin is added to fresh or boiled saponin extract, the added muscle actin is shifted to the high-mobility form. The saponin extract contains an acidic peptide having a molecular mass in the range of 5 kDa, which has been purified to homogeneity by reverse-phase HPLC. This peptide also shifts muscle actin to the high-mobility form. Addition of either boiled saponin extract or the purified peptide to muscle G-actin also strongly and stoichiometrically inhibits salt-induced polymerization, as assayed by falling-ball viscometry and by sedimentation. We conclude that this peptide binds to the bulk of the unpolymerized actin in platelets and prevents it from polymerizing.

Triterpenoid saponins from the root of Anemone tomentosa.

PubMed

Wang, Yi; Kang, Wei; Hong, Liang-jian; Hai, Wen-li; Wang, Xiao-yang; Tang, Hai-feng; Tian, Xiang-rong

2013-01-01

Three new triterpenoid saponins, tomentoside A (1), B (2) and C (3), along with four known saponins (4-7) were isolated from the root of Anemone tomentosa. The structures of the new compounds were elucidated as 3-O-β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranosyl hederagenin 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (1), 3-O-β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl hederagenin 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (2) and 3-O-β-D-galactopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranosyl oleanolic acid 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (3) on the basis of chemical and spectral evidence. In the oligosaccharide chains of compound 3, the characteristic D-galactose residue is a rare structural feature and secondly encountered among triterpenoid saponins from Anemone.

Molecular elucidation of a new allelic variation at the Sg-5 gene associated with the absence of group A saponins in wild soybean.

PubMed

Sundaramoorthy, Jagadeesh; Park, Gyu Tae; Mukaiyama, Kyosuke; Tsukamoto, Chigen; Chang, Jeong Ho; Lee, Jeong-Dong; Kim, Jeong Hoe; Seo, Hak Soo; Song, Jong Tae

2018-01-01

In soybean, triterpenoid saponin is one of the major secondary metabolites and is further classified into group A and DDMP saponins. Although they have known health benefits for humans and animals, acetylation of group A saponins causes bitterness and gives an astringent taste to soy products. Therefore, several studies are being conducted to eliminate acetylated group A saponins. Previous studies have isolated and characterized the Sg-5 (Glyma.15g243300) gene, which encodes the cytochrome P450 72A69 enzyme and is responsible for soyasapogenol A biosynthesis. In this study, we elucidated the molecular identity of a novel mutant of Glycine soja, 'CWS5095'. Phenotypic analysis using TLC and LC-PDA/MS/MS showed that the mutant 'CWS5095' did not produce any group A saponins. Segregation analysis showed that the absence of group A saponins is controlled by a single recessive allele. The locus was mapped on chromosome 15 (4.3 Mb) between Affx-89193969 and Affx-89134397 where the previously identified Glyma.15g243300 gene is positioned. Sequence analysis of the coding region for the Glyma.15g243300 gene revealed the presence of four SNPs in 'CWS5095' compared to the control lines. One of these four SNPs (G1127A) leads to the amino acid change Arg376Lys in the EXXR motif, which is invariably conserved among the CYP450 superfamily proteins. Co-segregation analysis showed that the missense mutation (Arg376Lys) was tightly linked with the absence of group A saponins in 'CWS5095'. Even though Arg and Lys have similar chemical features, the 3D modelled protein structure indicates that the replacement of Arg with Lys may cause a loss-of-function of the Sg-5 protein by inhibiting the stable binding of a heme cofactor to the CYP72A69 apoenzyme.

Molecular elucidation of a new allelic variation at the Sg-5 gene associated with the absence of group A saponins in wild soybean

PubMed Central

Sundaramoorthy, Jagadeesh; Park, Gyu Tae; Mukaiyama, Kyosuke; Tsukamoto, Chigen; Chang, Jeong Ho; Lee, Jeong-Dong; Kim, Jeong Hoe; Seo, Hak Soo

2018-01-01

In soybean, triterpenoid saponin is one of the major secondary metabolites and is further classified into group A and DDMP saponins. Although they have known health benefits for humans and animals, acetylation of group A saponins causes bitterness and gives an astringent taste to soy products. Therefore, several studies are being conducted to eliminate acetylated group A saponins. Previous studies have isolated and characterized the Sg-5 (Glyma.15g243300) gene, which encodes the cytochrome P450 72A69 enzyme and is responsible for soyasapogenol A biosynthesis. In this study, we elucidated the molecular identity of a novel mutant of Glycine soja, ′CWS5095′. Phenotypic analysis using TLC and LC-PDA/MS/MS showed that the mutant ′CWS5095′ did not produce any group A saponins. Segregation analysis showed that the absence of group A saponins is controlled by a single recessive allele. The locus was mapped on chromosome 15 (4.3 Mb) between Affx-89193969 and Affx-89134397 where the previously identified Glyma.15g243300 gene is positioned. Sequence analysis of the coding region for the Glyma.15g243300 gene revealed the presence of four SNPs in ′CWS5095′ compared to the control lines. One of these four SNPs (G1127A) leads to the amino acid change Arg376Lys in the EXXR motif, which is invariably conserved among the CYP450 superfamily proteins. Co-segregation analysis showed that the missense mutation (Arg376Lys) was tightly linked with the absence of group A saponins in ′CWS5095′. Even though Arg and Lys have similar chemical features, the 3D modelled protein structure indicates that the replacement of Arg with Lys may cause a loss-of-function of the Sg-5 protein by inhibiting the stable binding of a heme cofactor to the CYP72A69 apoenzyme. PMID:29381775

Jacaranda cuspidifolia Mart. (Bignoniaceae) as an antibacterial agent.

PubMed

Arruda, Ana Lúcia A; Vieira, Carla J B; Sousa, Daniella G; Oliveira, Regilene F; Castilho, Rachel O

2011-12-01

This study evaluated, in vitro, the antimicrobial activity of the hexane extract (JCHE), methanol extract (JCME), and chloroform fraction (JCCF) of bark from Jacaranda cuspidifolia Mart. (Family Bignoniaceae), a Brazilian medicinal plant, traditionally used as anti-syphilis and anti-gonorrhea treatment. The antimicrobial activity was evaluated using the disc diffusion method followed by the determination of minimum inhibitory concentration (MIC) values. JCHE was not active against the bacteria evaluated. JCME presented antibacterial activity against Streptococcus pyogenes, Staphylococcus aureus, and Neisseria gonorrhoeae with MIC values of 16.3 mg/mL, 9.1 mg/mL, and 25.2 mg/mL, respectively. JCCF was active against Staphylococcus epidermidis, S. aureus, Proteus mirabilis, Serratia marcescens, S. pyogenes, Enterobacter aerogenes, and N. gonorrhoeae with MIC values of 18.3 mg/mL, 9.3 mg/mL, 6.3 mg/mL, 6.1 mg/mL, 9.2 mg/mL, 6.2 mg/mL, and 25.2 mg/mL, respectively. Phytochemical analysis of JCME and JCCF gave positive results for saponins, coumarins, flavonoids, tannins, quinones, alkaloids, triterpenes, and steroids. Verbascoside was isolated and identified as a major peak in JCME and JCCF high-performance liquid chromatography fingerprints and might contribute to the observed antimicrobial activity.

Phytochemistry and Anticancer Potential of Notoginseng.

PubMed

Wang, Chong-Zhi; Anderson, Samantha; Yuan, Chun-Su

2016-01-01

Asian ginseng, American ginseng, and notoginseng are three major species in the ginseng family. Notoginseng is a Chinese herbal medicine with a long history of use in many Oriental countries. This botanical has a distinct ginsenoside profile compared to other ginseng herbs. As a saponin-rich plant, notoginseng could be a good candidate for cancer chemoprevention. However, to date, only relatively limited anticancer studies have been conducted on notoginseng. In this paper, after reviewing its anticancer data, phytochemical isolation and analysis of notoginseng is presented in comparison with Asian ginseng and American ginseng. Over 80 dammarane saponins have been isolated and elucidated from different plant parts of notoginseng, most of them belonging to protopanaxadiol or protopanaxatriol groups. The role of the enteric microbiome in mediating notoginseng metabolism, bioavailability, and pharmacological actions are discussed. Emphasis has been placed on the identification and isolation of enteric microbiome-generated notoginseng metabolites. Future investigations should provide key insights into notoginseng's bioactive metabolites as clinically valuable anticancer compounds.

Baccharis pteronioides toxicity

USDA-ARS?s Scientific Manuscript database

Baccharis pteronioides DC. occasionally poisons livestock in the southwestern United States. Various toxins including diterpenic lactones, sesquiterpenes , flavonoids, saponins, tannins, phenolic compounds and essential oils have been isolated and described from several Baccharis species, but none...

Isolation and characterization of an oxidosqualene cyclase gene encoding a β-amyrin synthase involved in Polygala tenuifolia Willd. saponin biosynthesis.

PubMed

Jin, Mei Lan; Lee, Dae Young; Um, Yurry; Lee, Jeong Hoon; Park, Chun Geun; Jetter, Reinhard; Kim, Ok Tae

2014-03-01

Expression of PtBS (Polygala tenuifolia β-amyrin synthase) led to the production of β-amyrin as sole product. Polygala tenuifolia Willdenow is a rich source of triterpene saponins, onjisaponins and polygalasaponins, used as herbal medicine to treat phlegms and for detumescence in traditional Asian healing. The Polygala saponins share the oleanane backbone structure and are, therefore, likely synthesized via β-amyrin as a common precursor. We hypothesized that, in analogy to diverse other plant species, this central intermediate should be formed by a β-amyrin synthase catalyzing the complex cyclization of oxidosqualene. This member of the oxidosqualene cyclase (OSC) family of enzymes is thus defining an important branch point between primary and secondary metabolisms, and playing a crucial role in the control of oleanane-type triterpene saponin biosynthesis. From P. tenuifolia roots, we isolated an OSC cDNA containing a reading frame of 2,289 bp nucleotides. The predicted protein of 763 amino acids (molecular weight 87.353 kDa) showed particularly high amino acid sequence identities to known β-amyrin synthases (85-87 %) and was, therefore, named PtBS. Expression of PtBS in the triterpenoid synthase-deficient yeast mutant GIL77 led to the production of β-amyrin as sole product. qRT-PCR analysis of various P. tenuifolia organs showed that PtBS transcript levels were highest in the roots, consistent with onjisaponin accumulation patterns. Therefore, we conclude that PtBS is the β-amyrin synthase enzyme catalyzing the first committed step in the biosynthesis of onjisaponins and polygalasaponins in P. tenuifolia.

Antagonistic effect of alkaloids and saponins on bioactivity in the quinine tree (Rauvolfia caffra sond.): further evidence to support biotechnology in traditional medicinal plants

PubMed Central

2013-01-01

Background The Quinine tree (Rauvolfia caffra) is used as a medicinal plant among traditional communities in many countries to manage tumors and other diseases associated with oxidative stress. To validate indigenous knowledge and possibly position this herb for technology uptake and utilization, we established the level of antioxidant activity in R. caffra, and probed for the presence of associated phytochemicals. Methods Antioxidant activity was determined on 1,1-diphenyl-2-picrylhydrazyl (DPPH) while major phytochemicals were identified by multiple tests on methanol fractions. Results R. caffra showed promise as a cure, with antioxidant activity comparable to the commercially used drug quercetin (R. caffra = 79.7% ±1.9; quercetin = 82.6% ± 2.0). However, we found two phytochemicals with possible antagonistic effect: co-occurrence of alkaloids and saponins significantly reduced antioxidant activity (alkaloids only = 63%; alkaloids plus saponins = 15%; steroids, terpenoids and cardiac glycosides = 82%), thus alkaloids and saponins should be exclusive to each other in drug formulations. Conclusions Antagonistic relationship among phytochemicals would affect the efficacy of crude extracts as used in traditional medicine. Unlike in herbal medicine, use of modern biotechnology in extraction, purification and design of optimal combinations will ensure efficient drug formulations with optimum bioactivity and minimum toxicity. Metabolic pathway engineering under a controlled environment may optimize availability of desired compounds. PMID:24160735

Two new triterpenoid saponins from the leaves of Bupleurum lancifolium (Apiaceae).

PubMed

Achouri, Amel; Derbré, Séverine; Medjroubi, Kamel; Laouer, Hocine; Séraphin, Denis; Akkal, Salah

2017-10-01

Chemical investigation of the leaves of Bupleurum lancifolium led to the isolation and identification of two triterpenoid saponins previously undescribed named 3-O-[α-L-rhamnopyranosyl (1 → 4)-β-D-glucopyranosyl] echinocystic acid 28-O-β-D-glucopyranosyl ester (1) and 3-O-[α-L-rhamnopyranosyl (1 → 4)-β-D-glucopyranosyl] oleanolic acid 28-O-β-D-glucopyranosyl ester (2) along with the two known compounds isorhamnetin 3-rutinoside (3) and rutin (4). Their structures were elucidated by different spectroscopic methods, including HRESIMS analysis as well as 1D and 2D NMR experiments.

Two new furostanol saponins from Tribulus terrestris.

PubMed

Xu, Ya-Juan; Xu, Tun-Hai; Zhou, Hai-Ou; Li, Bo; Xie, Sheng-Xu; Si, Yun-Shan; Liu, Yue; Liu, Tong-Hua; Xu, Dong-Ming

2010-05-01

Two new furostanol saponins were isolated from the fruits of Tribulus terrestris L. Their structures were established as 26-O-beta-D-glucopyranosyl-(25S)-5alpha-furost-20(22)-en-3beta,26-diol-3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-[beta-D-glucopyranosyl-(1 --> 4)]-beta-D-galactopyranoside (1) and 26-O-beta-D-glucopyranosyl-(25S)-5alpha-furost-20(22)-en-12-one-3beta,26-diol-3-O-beta-D-galactopyranosyl-(1 --> 2)-beta-D-glucopyranosyl-(1 --> 4)-beta-D-galactopyranoside (2) on the basis of spectroscopic data as well as chemical evidence.

Structure elucidation of two triterpenoid saponins from rhizome of Anemone raddeana Regel.

PubMed

Lu, Jincai; Xu, Beibei; Gao, Song; Fan, Li; Zhang, Hongfen; Liu, Runxiang; Kodama, Hiroyuki

2009-09-01

Two new 27-hydroxy-oleanolic acid type triterpenoid saponins, raddeanoside 20 (1) and raddeanoside 21(2) were isolated from the rhizome of Anemone raddeana Regel. The structures of the two compounds were elucidated as 27-hydroxy-oleanolic acid 3-O-alpha-L-rhamnopyranosyl(1-->2) [beta-D-glucopyranosyl (1-->4)]-alpha-L-arabinopyranoside (1) and 3-O-alpha-L-rhamnopyranosyl (1-->2)-alpha-L-arabinopyranosyl-27-hydroxy-oleanolic acid 28-O-alpha-L-rhamnopyranosyl(1-->4)-beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranoside (2) on the basis of chemical and spectral evidence.

Medicinal Flowers. XXXII. Structures of oleanane-type triterpene saponins, perennisosides VIII, IX, X, XI, and XII, from the flowers of Bellis perennis.

PubMed

Morikawa, Toshio; Li, Xuezheng; Nishida, Eriko; Nakamura, Seikou; Ninomiya, Kiyofumi; Matsuda, Hisashi; Hamao, Makoto; Muraoka, Osamu; Hayakawa, Takao; Yoshikawa, Masayuki

2011-01-01

Five new triterpene saponins perennisosides VIII (1), IX (2), X (3), XI (4), and XII (5) were isolated from the MeOH-eluated fraction of the methanolic extract from the flowers of Bellis perennis. The MeOH-eluted fraction of the methanolic extract from the flowers of B. perennis was found to inhibit gastric emptying in olive oil-loaded mice at a dose of 200 mg/kg, per os (p.o.). The stereostructures of 1-5 were elucidated on the basis of chemical and spectroscopic evidence.

Two new triterpenoid saponins from Gymnema sylvestre.

PubMed

Zhu, Xu-Min; Xie, Ping; Di, Ying-Tong; Peng, Shu-Lin; Ding, Li-Sheng; Wang, Ming-Kui

2008-05-01

Two new oleanane-type triterpenoid saponins, gymnemoside-W1 and W2, together with seven known compounds were isolated from the leaves of Gymnema sylvestre R. Br. By means of spectral and chemical analysis, the structures of the new compounds were elucidated as 16 beta-hydroxyl olean-12-en-3-O-[beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosyl]-28-O-beta-D-glucopyranoside(1) and 16 beta,21 beta,28-trihydroxyl-olean-12-ene-3-O-glucoronopyranoside (2). The EtOH/H(2)O extracts of this plant were shown to be able to inhibit glucose absorption in rats.

Triterpenes and saponins from Rudgea viburnioides.

PubMed

Young, M C; Araújo, A R; da Silva, C A; Lopes, M N; Trevisan, L M; Bolzani, V S

1998-07-01

A novel triterpene, viburgenin (1), has been isolated from an extract of the ripe fruit rinds of Rudgea viburnioides, together with the known saponins, arjunglucoside I and trachelosperosides B-1 and E-1, and the triterpenes trachelosperogenin B (2) and arjungenin. Compound 2 was previously obtained as a product from enzymatic hydrolysis, and it is reported for the first time as a natural product. The structure of compound 1 was determined as 2alpha,3beta, 19alpha,23,24-pentahydroxyurs-12-ene by extensive use of 1D and 2D NMR spectroscopic methods. Compound 1 exhibited moderate antifungal activity against Cladosporium cladosporioides.

Anti-enteric bacterial activity and phytochemical analysis of the seed kernel extract of Mangifera indica Linnaeus against Shigella dysenteriae (Shiga, corrig.) Castellani and Chalmers.

PubMed

Rajan, S; Thirunalasundari, T; Jeeva, S

2011-04-01

To evaluate the phytochemical and anti-bacterial efficacy of the seed kernel extract of Mangifera indica (M. indica) against the enteropathogen, Shigella dysenteriae (S. dysenteriae), isolated from the diarrhoeal stool specimens. The preliminary phytochemical screening was performed by the standard methods as described by Harborne. Cold extraction method was employed to extract the bioactive compounds from mango seed kernel. Disc diffusion method was adopted to screen antibacterial activity. Minimum inhibitory concentration (MIC) was evaluated by agar dilution method. The crude extracts were partially purified by thin layer chromatography (TLC) and the fractions were analyzed by high performance thin layer chromatography (HPTLC) to identify the bioactive compounds. Phytochemical scrutiny of M. indica indicated the presence of phytochemical constituents such as alkaloids, gums, flavanoids, phenols, saponins, steroids, tannins and xanthoproteins. Antibacterial activity was observed in two crude extracts and various fractions viz. hexane, benzene, chloroform, methanol and water. MIC of methanol fraction was found to be (95±11.8) μg/mL. MIC of other fractions ranged from 130-380 μg/mL. The present study confirmed that each crude extracts and fractions of M. indica have significant antimicrobial activity against the isolated pathogen S. dysenteriae. The antibacterial activity may be due to the phytochemical constituents of the mango seed kernel. The phytochemical tannin could be the reason for its antibacterial activity. Copyright © 2011 Hainan Medical College. Published by Elsevier B.V. All rights reserved.

Phytochemical characterization, antimicrobial activity and reducing potential of seed oil, latex, machine oil and presscake of Jatropha curcas

PubMed Central

Sharma, Amit Kumar; Gangwar, Mayank; Kumar, Dharmendra; Nath, Gopal; Kumar Sinha, Akhoury Sudhir; Tripathi, Yamini Bhushan

2016-01-01

Objective: This study aims to evaluate the antimicrobial activity, phytochemical studies and thin layer chromatography analysis of machine oil, hexane extract of seed oil and methanol extract of presscake & latex of Jatropha curcas Linn (family Euphorbiaceae). Materials and Methods: J. curcas extracts were subjected to preliminary qualitative phytochemical screening to detect the major phytochemicals followed by its reducing power and content of phenol and flavonoids in different fractions. Thin layer chromatography was also performed using different solvent systems for the analysis of a number of constituents in the plant extracts. Antimicrobial activity was evaluated by the disc diffusion method, while the minimum inhibitory concentration, minimum bactericidal concentration and minimum fungicidal concentration were calculated by micro dilution method. Results: The methanolic fraction of latex and cake exhibited marked antifungal and antibacterial activities against Gram-positive and Gram-negative bacteria. Phytochemical analysis revealed the presence of alkaloids, saponins, tannins, terpenoids, steroids, glycosides, phenols and flavonoids. Reducing power showed dose dependent increase in concentration compared to standard Quercetin. Furthermore, this study recommended the isolation and separation of bioactive compounds responsible for the antibacterial activity which would be done by using different chromatographic methods such as high-performance liquid chromatography (HPLC), GC-MS etc. Conclusion: The results of the above study suggest that all parts of the plants possess potent antibacterial activity. Hence, it is important to isolate the active principles for further testing of antimicrobial and other biological efficacy. PMID:27516977

Phytochemical characterization, antimicrobial activity and reducing potential of seed oil, latex, machine oil and presscake of Jatropha curcas.

PubMed

Sharma, Amit Kumar; Gangwar, Mayank; Kumar, Dharmendra; Nath, Gopal; Kumar Sinha, Akhoury Sudhir; Tripathi, Yamini Bhushan

2016-01-01

This study aims to evaluate the antimicrobial activity, phytochemical studies and thin layer chromatography analysis of machine oil, hexane extract of seed oil and methanol extract of presscake & latex of Jatropha curcas Linn (family Euphorbiaceae). J. curcas extracts were subjected to preliminary qualitative phytochemical screening to detect the major phytochemicals followed by its reducing power and content of phenol and flavonoids in different fractions. Thin layer chromatography was also performed using different solvent systems for the analysis of a number of constituents in the plant extracts. Antimicrobial activity was evaluated by the disc diffusion method, while the minimum inhibitory concentration, minimum bactericidal concentration and minimum fungicidal concentration were calculated by micro dilution method. The methanolic fraction of latex and cake exhibited marked antifungal and antibacterial activities against Gram-positive and Gram-negative bacteria. Phytochemical analysis revealed the presence of alkaloids, saponins, tannins, terpenoids, steroids, glycosides, phenols and flavonoids. Reducing power showed dose dependent increase in concentration compared to standard Quercetin. Furthermore, this study recommended the isolation and separation of bioactive compounds responsible for the antibacterial activity which would be done by using different chromatographic methods such as high-performance liquid chromatography (HPLC), GC-MS etc. The results of the above study suggest that all parts of the plants possess potent antibacterial activity. Hence, it is important to isolate the active principles for further testing of antimicrobial and other biological efficacy.

Effects of five oleanolic acid triterpenoid saponins from the rhizome of Anemone raddeana on stimulus-induced superoxide generation, phosphorylation of proteins and translocation of cytosolic compounds to cell membrane in human neutrophils.

PubMed

Wei, Shihu; He, Wenfei; Lu, Jincai; Wang, Zhonghuan; Yamashita, Koichi; Yokoyama, Masanori; Kodama, Hiroyuki

2012-03-01

Five oleanolic acid triterpenoid saponins (OTS-1, 2, 3, 4 and 5) were isolated from the rhizome of Anemone raddeana. The effect of these triterpenoid saponins on stimulus-induced superoxide generation in human neutrophils was assayed by measuring the reduction of ferricytochrome c using a dual-beam spectrophotometer. The phosphorylation of neutrophil proteins, and translocation of p67(phox), p47(phox) and Rac to plasma membrane were investigated using specific monoclonal antibodies. The five oleanolic acid triterpenoid saponins used in this experiment suppressed N-formyl-methionyl-leucyl-phenylalanine (fMLP)-induced superoxide generation in a concentration-dependent manner. OTS-1, 2 and 4 suppressed phorbol 12-myristate 13-acetate (PMA)- and arachidonic acid (AA)-induced superoxide generation in a concentration-dependent manner, but OTS-3 and 5 showed no effect. fMLP- and PMA-induced tyrosyl or serine/threonine phosphorylation, and fMLP-, PMA- and AA-induced translocation of p67(phox), p47(phox) and Rac to plasma membrane were in parallel with the suppression of the stimulus-induced superoxide generation. Copyright © 2011 Elsevier B.V. All rights reserved.

Phytopharmacological evaluation of ethanol extract of Sida cordifolia L. roots.

PubMed

Momin, Mohammad Abdul Motalib; Bellah, Sm Faysal; Rahman, Sarder Mohammad Raussel; Rahman, Ahmed Ayedur; Murshid, Gazi Mohammad Monjur; Emran, Talha Bin

2014-01-01

To investigate the phytochemical screening (group determination) and selected pharmacological activities (antioxidant, antimicrobial and analgesic activity) of the plant Sida cordifolia Linn (S. cordifolia). Eighty percent concentrated ethanol extract of the roots was used. To identify the chemical constituents of plant extract standard procedures were followed. In phytochemical screening the crude extract was tested for the presence of different chemical groups like reducing sugar, tannins, saponins, steroids, flavonoids, gums, alkaloids and glycosides. The antioxidant property of ethanolic extract of S. cordifolia was assessed by DPPH free radical scavenging activity. Analgesic activity of the extract was tested using the model of acetic acid induced writhing in mice. Diclofenac sodium is used as reference standard drug for the analgesic activity test. Antibacterial activity of plant extract was carried out using disc diffusion method with five pathogenic bacteria comparison with kanamycin as a standard. Phytochemical analysis of the ethanolic extract of the roots of S. cordifolia indicated the presence of reducing sugar, alkaloids, steroids and saponins. In DPPH scavenging assay the IC50 value was found to be 50 μg/mL which was not comparable to the standard ascorbic acid. The crude extract produced 44.30% inhibition of writhing at the dose of 500 mg/kg body weight which is statistically significant (P>0.001). The in vitro antimicrobial activity of the ethanol extract of the roots of S. cordifolia showed no antimicrobial activity against five types of microorganisms. The experiment was conducted only with five species of bacteria as test species, which do not at all indicate the total inactivity against micro-organisms. The obtained results provide a support for the use of this plant in traditional medicine but further pharmacological studies are required. Copyright © 2014 Asian Pacific Tropical Biomedical Magazine. Published by Elsevier B.V. All rights reserved.

Phytopharmacological evaluation of ethanol extract of Sida cordifolia L. roots

PubMed Central

Momin, Mohammad Abdul Motalib; Bellah, Sm Faysal; Rahman, Sarder Mohammad Raussel; Rahman, Ahmed Ayedur; Murshid, Gazi Mohammad Monjur; Emran, Talha Bin

2014-01-01

Objective To investigate the phytochemical screening (group determination) and selected pharmacological activities (antioxidant, antimicrobial and analgesic activity) of the plant Sida cordifolia Linn (S. cordifolia). Methods Eighty percent concentrated ethanol extract of the roots was used. To identify the chemical constituents of plant extract standard procedures were followed. In phytochemical screening the crude extract was tested for the presence of different chemical groups like reducing sugar, tannins, saponins, steroids, flavonoids, gums, alkaloids and glycosides. The antioxidant property of ethanolic extract of S. cordifolia was assessed by DPPH free radical scavenging activity. Analgesic activity of the extract was tested using the model of acetic acid induced writhing in mice. Diclofenac sodium is used as reference standard drug for the analgesic activity test. Antibacterial activity of plant extract was carried out using disc diffusion method with five pathogenic bacteria comparison with kanamycin as a standard. Results Phytochemical analysis of the ethanolic extract of the roots of S. cordifolia indicated the presence of reducing sugar, alkaloids, steroids and saponins. In DPPH scavenging assay the IC50 value was found to be 50 µg/mL which was not comparable to the standard ascorbic acid. The crude extract produced 44.30% inhibition of writhing at the dose of 500 mg/kg body weight which is statistically significant (P>0.001). The in vitro antimicrobial activity of the ethanol extract of the roots of S. cordifolia showed no antimicrobial activity against five types of microorganisms. The experiment was conducted only with five species of bacteria as test species, which do not at all indicate the total inactivity against micro-organisms. Conclusions The obtained results provide a support for the use of this plant in traditional medicine but further pharmacological studies are required. PMID:24144125

Isolation, characterization, and in rats plasma pharmacokinetic study of a new triterpenoid saponin from Dianthus superbus.

PubMed

Ren, Yina; Xu, Xiaobao; Zhang, Qianlan; Lu, Yongzhuang; Li, Ximin; Zhang, Lin; Tian, Jingkui

2017-02-01

One new oleanolic acid triterpenoid saponin, 3-O-β-D-glucopyranosyl olean-11, 13(18)-diene-23,28-dioic acid, (hereafter referred to as DS-1) was isolated from the traditional Chinese medicinal plant Dianthus superbus (D. superbus). DS-1 plays an important role in the bioactivity of D. superbus. Thus, a sensitive, reliable and accurate reversed-phased liquid chromatography with tandem mass spectrometry (LC-MS/MS) in negative ion mode was developed and validated for the quantification and pharmacokinetic study of DS-1 in rats plasma. The pharmacokinetic profile showed that DS-1 was rapidly absorbed and eliminated in plasma, indicating that significant accumulation of the compound in biological specimen is unlikely. In addition, poor absorption into systemic circulation was observed after oral administration of DS-1, resulting in low absolute bioavailability (0.92 %).

Antiproliferative and anti-inflammatory furostanol saponins from the rhizomes of Tupistra chinensis.

PubMed

Xiang, Limin; Wang, Yihai; Yi, Xiaomin; He, Xiangjiu

2016-12-01

Phytochemical investigations of the rhizome of Tupistra chinensis led to the isolation of ten new furostanol saponins along with fourteen known spirostanols. Their chemical structures were elucidated on the basis of spectroscopic and chemical methods, including IR, NMR, MS, and GC analyses. The antiproliferative effects against FaDu and Detroit 562 cell lines and inhibitory activities on nitric oxide (NO) production induced by lipopolysaccharide (LPS) in a macrophage cell line RAW 264.7 were assayed for all the isolated compounds. Compound 14 exhibited significant antiproliferative effects against FaDu and Detroit 562 cells with IC 50 values of 1.1±0.1 and 1.2±0.1μM, respectively. Compounds 1, 2, 6, 13, 16, 19 and 24 exhibited inhibitory effects on NO production with IC 50 values ranging from 15.7 to 46.2μM. Copyright © 2016 Elsevier Inc. All rights reserved.

Pennogenyl Saponins from Paris quadrifolia L. Induce Extrinsic and Intrinsic Pathway of Apoptosis in Human Cervical Cancer HeLa Cells

PubMed Central

Stefanowicz-Hajduk, Justyna; Bartoszewski, Rafal; Bartoszewska, Sylwia; Kochan, Kinga; Adamska, Anna; Kosiński, Igor; Ochocka, J. Renata

2015-01-01

Pennogenyl saponins are the active compounds of large number of plant species and consequently many polyherbal formulations. Hence, great interest has been shown in their characterization and in the investigation of their pharmacological and biological properties, especially anticancer. This present study reports on the evaluation of cytotoxic effects and explanation of the molecular mechanisms of action of the two pennogenyl saponins (PS 1 and PS 2) isolated from Paris quadrifolia L. rhizomes on human cervical adenocarcinoma cell line HeLa. To determine the viability of the cells treated with the compounds we used real-time cell proliferation analysis and found that the pennogenyl saponins PS 1 and PS 2 strongly inhibited the tumor cells growth with IC50 values of 1.11 ± 0.04 μg/ml and 0.87 ± 0.05 μg/ml, respectively. The flow cytometry analysis indicated that the two compounds induced apoptosis in a dose-dependent manner and decreased mitochondrial membrane potential in HeLa cells in the early stage of apoptosis. Quantitative PCR and Western Blot analysis showed that the two saponins significantly increased mRNA expression of FADD and BID as well as induced caspase-8 via increased of procaspase-8 processing in the treated cells. The results of this study suggest that both the extrinsic death receptor and intrinsic mitochondrial pathways are involved in the programmed cell death. PMID:26295969

Preliminary phytochemical screening and alpha-glucosidase inhibitory activity of Philippine taro (Colocasia esculenta (L.) Schott var. PSB-VG #9)

NASA Astrophysics Data System (ADS)

Lebosada, Richemae Grace R.; Librando, Ivy L.

2017-01-01

The study was conducted to determine the anti-hyperglycemic property in terms of α-glucosidase inhibitory activity of the various parts (corm, leaf and petiole) of Colocasia esculenta (L.) Schott var. PSB-VG #9. Each of the plant parts were extracted with 95% ethanol and concentrated using a rotary evaporator at 40 °C. The crude extracts were screened for the presence of alkaloids, flavonoids, glycosides and saponins using Thin Layer Chromatography. The α-glucosidase inhibitory activity of the crude extracts (50 mg/L) were assayed spectrophotometrically using a microplate reader. The results of the phytochemical screening revealed the presence of alkaloids, flavonoids, and saponins in the leaf part while flavonoids and saponins were detected in the petiole and only saponins were present in the corm. The assay showed that the percentage α-glucosidase inhibition of the 50 mg/L ethanolic crude extract of the corm, leaves and petiole of C. esculenta are 68.03, 71.64 and 71.39%, respectively. Statistical analysis shows significant differences in the α-glucosidase inhibition among the various plant parts. It can be concluded that the ethanolic crude extracts of the different parts of C. esculenta (L.) Schott var. PSB-VG #9 exhibited inhibitory activity against α-glucosidase and the presence of phytochemicals like alkaloids, flavonoids and saponins may have contributed greatly to the inhibitory activity of the plant extract and can be further subjected for isolation of the therapeutically active compounds with antidiabetes potency.

Triterpenoidal saponins from the fruits of Gleditsia caspica with proapoptotic properties.

PubMed

Shaheen, Usama; Ragab, Ehab A; Abdalla, Ashraf N; Bader, Ammar

2018-01-01

Three previously undescribed oleanane-type triterpenoidal saponins named caspicaosides L-N were isolated from the fruits of Gleditsia caspica Desf. The aglycons of these saponins were echinocystic acid, erythrodiol and 12-oleanene-3,28,30-triol. Caspicaoside L is a bisdesmosidic saponin acylated with two monoterpenic acids. It has a disaccharide moiety made up of glucose and arabinose attached to C-3 and pentasaccharide moiety linked to C-28 made up of one glucose, 2 xyloses, one inner rhamnose and one terminal rhamnose which was acylated with two identical monoterpenic acids. Caspicaoside M is a monodesmosidic saponin with a trisaccharide moiety at C-3 made up of glucose, xylose and arabinose, while caspicaoside N has a disaccharide moiety at C-3 made up of glucose and arabinose. Their structures were determined by extensive 1D and 2D (DQF-COSY, HSQC, TOCSY, 1 H- 13 C-HSQC-TOCSY, HMBC, ROESY, NOESY) NMR, HRESIMS analyses and chemical degradation. The cytotoxicity MTT-based assay showed that caspicaosides M, N and L, respectively, exhibited high cytotoxic activity with IC 50  ≤ 10 μM (72 h) at least against one of the three used cancer cell lines, MCF 7, A2780 and HT 29; and were 2-34 folds selective against the normal fibroblasts (MRC 5). All compounds also induced apoptosis and caused G 2 /M arrest in MCF 7 cells (24 h); thus showing pro-apoptotic properties. Copyright © 2017 Elsevier Ltd. All rights reserved.

Microbial transformation of pseudoprotodioscin by Gibberella fujikuroi.

PubMed

Hu, Hong-Xiu; Gao, Ran-Ran; Gao, Zhao-Hui; Qiao, Yue; Dong, Xin-Ran; Ding, Gang; Sun, Di-An

2018-05-07

Three new (6, 9, and 12) and nine known steroidal saponins were obtained from the fermentation broth of pseudoprotodioscin (PPD) incubated with a fungus Gibberella fujikuroi CGMCC 3.4663. Structures of the metabolites were elucidated by 1-D ( 1 H, 13 C), 2-D (HMBC, HSQC, NOESY) NMR, and HR-MS analyses. The biotransformation pathway of pseudoprotodioscin by Gibberella fujikuroi CGMCC 3.4663 was proposed. Compounds 1-11 were tested in vitro for their cytotoxic activities against two human cancer cell lines (HepG2 and Hela). Compounds 1, 6, 9, and 10 exhibited cytotoxic activity against HepG2 cells. Compound 10 exhibited cytotoxicity to Hela cells.

Effect of Vernonia cinerea Less flower extract in adjuvant-induced arthritis.

PubMed

Latha, R M; Geetha, T; Varalakshmi, P

1998-10-01

1. The anti-inflammatory effect of an alcoholic extract from the flower of Vernonia cinerea (Asteraceae; Less) was tested in adjuvant arthritic rats. 2. Changes in paw volume, body and tissue weights and serum and tissue enzyme activities of ALT, AST, ACP and cathepsin-D in adjuvant rats were reversed by oral administration of 100 mg/kg body weight (BW) of the flower extract. 3. The extract also reversed the major histopathological changes in the hindpaws of the arthritic rats. 4. Phytochemical studies revealed the presence of alkaloids, saponins, steroids and flavonoids. 5. It is concluded that the extract contains as yet unidentified anti-inflammatory principle(s).

Phytochemical analysis, antimicrobial, antioxidant and urease inhibitory potential of Cyphostemma digitatum Lam.

PubMed

Khan, Rasool; Saif, Abdullah Qasem; Quradha, Mohammad Mansour; Ali, Jawad; Rauf, Abdur

2015-01-01

In this paper we report the antimicrobial, antiradical and urease inhibitory potential along with photochemical investigation of the crude extracts of Cyphostemma digitatum Lam. Phytochemical screening of both the crude (hot/cold) alcoholic and aqueous extracts of C. digitatum showed the presence of alkaloids, flavonoids, saponins, coumarins, steroids, terpenoids and tannins. The crude methanolic extract (hot/cold) exhibited good antioxidant activity, while the aqueous extract was a weak antioxidant. The crude methanolic extract was found to be more active against Bacillus subtilis, while both the extracts showed moderate antifungal potential, the methanolic crude extract showed good urease inhibitory activity compared with the aqueous crude extract.

Anti-inflammatory activity of different agave plants and the compound cantalasaponin-1.

PubMed

Monterrosas-Brisson, Nayeli; Ocampo, Martha L Arenas; Jiménez-Ferrer, Enrique; Jiménez-Aparicio, Antonio R; Zamilpa, Alejandro; Gonzalez-Cortazar, Manases; Tortoriello, Jaime; Herrera-Ruiz, Maribel

2013-07-10

Species of the agave genus, such as Agave tequilana, Agave angustifolia and Agave americana are used in Mexican traditional medicine to treat inflammation-associated conditions. These plants' leaves contain saponin compounds which show anti-inflammatory properties in different models. The goal of this investigation was to evaluate the anti-inflammatory capacity of these plants, identify which is the most active, and isolate the active compound by a bio-directed fractionation using the ear edema induced in mice with 12-O-tetradecanoylphorbol-13-acetate (TPA) technique. A dose of 6 mg/ear of acetone extract from the three agave species induced anti-inflammatory effects, however, the one from A. americana proved to be the most active. Different fractions of this species showed biological activity. Finally the F5 fraction at 2.0 mg/ear induced an inhibition of 85.6%. We identified one compound in this fraction as (25R)-5α-spirostan-3β,6α,23α-triol-3,6-di-O-β-D-glucopyranoside (cantalasaponin-1) through 1H- and 13C-NMR spectral analysis and two dimensional experiments like DEPT NMR, COSY, HSQC and HMBC. This steroidal glycoside showed a dose dependent effect of up to 90% of ear edema inhibition at the highest dose of 1.5 mg/ear.

Studies on the antimicrobial effects of Spondias mombin and Baphia nittida on dental caries organism.

PubMed

Amadi, E S; Oyeka, A; Onyeagba, R A; Okoli, I; Ugbogu, O C

2007-02-01

The antimicrobial effect of cold water, hot water and ethanolic extracts of Spondias mombin and Baphia nittida on cariogenic streptococci isolated from dental caries patients attending the Ebonyi State University Teaching hospital dental clinic Abakaliki was investigated using the agar well diffusion technique. The cold water and ethanolic extracts of Baphia nittida showed inhibition zone diameter (IZD) of 10 and 12 mm respectively at 400 mg mL(-1), while the hot water showed no inhibitory effect. All extracts of Spondias mombin did not inhibit the test organism. The cold water and ethanolic extracts of Baphia nittida showed Minimum Inhibitory Concentration (MIC) of 100 and 50 mg mL(-1) respectively. The combination of the cold water extracts of the two herbs showed enhanced activity of 13 mm. Phytochemical analysis of Baphia nittida revealed the presence of flavonoids, glycosides, proteins saponins, tannins, carbohydrate and steroidal aglycone. Acute toxicity testing of Baphia nittida at a range of 250-5000 mg kg(-1) bw using mice showed no clinical signs of acute toxicity. No chemical toxicity was observed amongst rats given Baphia nittida extracts 500 and 1000 mg kg(-1) bw after 30 days. Baphia nittida may be a potential source of an antimicrobial agent for the treatment and management of dental caries.

The Genus Luehea (Malvaceae-Tiliaceae): Review about Chemical and Pharmacological Aspects

PubMed Central

de Morais, Selene Maia; Colares, Aracélio Viana

2016-01-01

Popularly known as “açoita-cavalo” (whips-horse), Luehea species (Malvaceae-Tilioideae) are native to America and are used in folk medicine as anti-inflammatory, antidiarrheal, antiseptic, expectorant, and depurative and against skin infections. Although there are studies showing the chemical constituents of some species, the active substances have not been properly identified. A systematic study was carried out through a computer search of data on CAPES journals, SciELO, ISI Bireme, PubMed, ScienceDirect, ScienceDomain Medline, and Google Scholar from published articles using key words: Luehea, açoita-cavalo, and Malvaceae. Luehea divaricata was the species with the highest number of studies observed. Triterpenes (9), flavonoids (6), and steroids (4), including saponins, organic acids (4), and one lignan, are the main types of secondary metabolites registered and the most cited flavonoids were rutin and quercetin and among triterpenes there was maslinic acid, which might be associated with the popular indication of its anti-inflammatory action. The vitexin, a C-glycosylated flavone, isolated from three different species, is cited as a possible taxonomic marker of the genus. Studies confirm in part the medicinal uses of plants named as “açoita-cavalo” species. Some pharmacological activities, not assigned to the species of the genus Luehea by populations, were observed in laboratory experiments. PMID:27818835

Social isolation stress-induced oxidative damage in mouse brain and its modulation by majonoside-R2, a Vietnamese ginseng saponin.

PubMed

Huong, Nguyen Thi Thu; Murakami, Yukihisa; Tohda, Michihisa; Watanabe, Hiroshi; Matsumoto, Kinzo

2005-08-01

Stressors with a physical factor such as immobilization, electric foot shock, cold swim, etc., have been shown to produce oxidative damage to membrane lipids in the brain. In this study, we investigated the effect of protracted social isolation stress on lipid peroxidation activity in the mouse brain and elucidated the protective effect of majonoside-R2, a major saponin component of Vietnamese ginseng, in mice exposed to social isolation stress. Thiobarbituric acid reactive substance levels, one of the end products of lipid peroxidation reaction, were increased in the brains of mice subjected to 6-8 weeks of social isolation stress. Measurements of nitric oxide (NO) metabolites (NO(x)(-)) also revealed a significant increase of NO production in the brains of socially isolated mice. Moreover, the depletion of brain glutathione content, an endogenous antioxidant, in socially isolated animals occurred in association with the rise in lipid peroxidation. The intraperitoneal administration of majonoside-R2 (10-50 mg/kg) had no effect on thiobarbituric acid reactive substances (TBARS), NO, or glutathione levels in the brains of group-housed control mice but it significantly suppressed the increase in TBARS and NO levels and the decrease in glutathione levels caused by social isolation stress. These results suggest that mice subjected to 6-8 weeks of social isolation stress produces oxidative damage in the brain partly via enhancement of NO production, and that majonoside-R2 exerts a protective effect by modulating NO and glutathione systems in the brain.

Polyhydroxylated spirostanol saponins from the tubers of Dioscorea polygonoides.

PubMed

Osorio, Jaime Niño; Mosquera Martinez, Oscar M; Correa Navarro, Yaned M; Watanabe, Kazuki; Sakagami, Hiroshi; Mimaki, Yoshihiro

2005-07-01

Three new polyhydroxylated spirostanol saponins (1-3) were isolated from the tubers of Dioscorea polygonoides. The structures of these new compounds were determined on the basis of extensive spectroscopic analysis and the results of acid or enzymatic hydrolysis as (23S,24R,25S)-23,24-dihydroxyspirost-5-en-3beta-yl O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside (1), (23S,25R)-12alpha,17alpha,23-trihydroxyspirost-5-en-3beta-yl O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside (2), and (23S,25R)-14alpha,17alpha,23-trihydroxyspirost-5-en-3beta-yl O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside (3), respectively.

Three new triterpenoid saponins from Dianthus superbus.

PubMed

Luo, Jian-Guang; Chen, Xia; Kong, Ling-Yi

2011-01-01

Three new triterpenoid saponins (1-3) were isolated from the dried aerial parts of Dianthus superbus L. (Caryophyllaceae). Their structures were established as 3-O-β-D-glucopyranosyl gypsogenic acid 28-O-[β-D-6-O-((3S)-3-hydroxyl-3-methylglutaryl)glucopyranosyl(1→6)]-β-D-glucopyranoside (1), 3-O-β-D-glucopyranosyl gypsogenic acid 28-O-[β-D-glucopyranosyl(1→3)][β-D-6-O-((3S)-hydroxyl-3-methylglutaryl)glucopyranosyl(1→6)]-β-D-glucopyranoside (2), 3-O-α-L-arabinopyranosyl-3β,16α-dihydroxyolean-12-en-23,28-dioic acid 28-O-[β-D-glucopyranosyl-(1→6)]-β-D-glucopyranoside (3), on the basis of various spectroscopic analyses and chemical degradations.

[Study on triterpenoid saponins in the rhizome of Anemone hofengensis].

PubMed

Han, Lin-Tao; Li, Ming-Ming; Huang, Fang; Hou, An-Wei

2013-10-01

To study the triterpenoid saponins in the rhizome of Anemone hofengensis. The constituents were separated with various chromatographic techniques and their structures were elucidated by physicochemical properties and spectral data. Five compounds were isolated and identified as 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-alpha-L-arabino-pyranosyl-oleanolic acid (1), 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-beta-D-glucopyranosyl-(1 --> 2)-alpha-L-rhamnopyranosyl-oleanolic acid 28-O-alpha-L-rhamnopyranosyl-(1 --> 4) -beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranoside (2), 3-O-alpha-L-rhamnopyranosyl-(1 --> 2) [beta-D-glucopyranosyl-(1 --> 4)]-alpha-L-rhamnopyranosyl-oleanolic acid-28-O-beta-D-glucopyranosyl-(1 --> 6)-beta-D-gluco-pyranoside (3), 3-O-beta-D-glucopyranosyl-(1 --> 2)-beta-D-xylopyranosyl-oleanolic acid 28-O-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranoside (4), oleanolic acid-28-O-alpha-L-rhamnopyra-nosyl-(1 --> 4)-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranoside (5). Compound 1 - 5 are isolated from this plant for the first time.

Chemical sensing of Benzo[a]pyrene using Corchorus depressus fluorescent flavonoids.

PubMed

Ahmad, Wajiha; Rana, Nosheen Fatima; Riaz, Sundus; Ahmad, Nasir Mehmood; Hameed, Maryam; Naeem, Ayesha; Tahir, Rabbiya

2018-04-01

Plant phytochemicals, such as flavonoids are in use for the development of optical biosensor. Benzo[a]pyrene (B[a]P), is a pervasive environmental and dietary carcinogen. A fluorescent assay is developed using plant isolated flavonoid for the detection of B[a]P. High content saponins are excluded from the flavonoid-containing methanolic extract of Corchorus depressus by implying reduction of silver ions by saponins resulting in formation of silver nanoparticles. Isolated plant flavonoids are used to develop a spectrofluorometric assay for the detection of B[a]P. Decrease in the flavonoid fluorescence intensity by B[a]P is found to be based on both static and dynamic quenching. Specificity of the assay for B[a]P was tested for other carcinogens belonging to different classes of compounds. Flavonoids-mediated sensing can be implied for the development of new generation of nanoparticle-based biosensors that can be more sensitive and less susceptible to external factors, such as temperature and humidity.

[Studies on triterpenoid saponins in the rhizome of Anemone flaccida].

PubMed

Han, Lin-Tao; Huang, Fang

2009-07-01

To study the triterpenoid saponins in the rhizome of Anemone flaccida. The constituents were separated with various chromatographic techniques and their structures were elucidated by means of physicochemical properties and the analysis of their spectral datas. Five compounds were isolated and identified as 3-O-beta-D-glucuronypyranosyl-oleanolic acid-28-O-alpha-L-rhamnopyranosyl (1 --> 4)-beta-D-glucopyranosyl(1 --> 6)-beta-D-glucopyra noside (1), 3-O-beta-D-glucuronypyranosyl-oleanolic acid-28-O-beta-D-glucopyranosyl (1 --> 6)-beta-D-glucopyranoside (2), 3-O-alpha-L-rhamnopyranosy (1 --> 2)-beta-D-glucopyranosyl-oleanolic acid-28-O-alpha-L-rhamnopyranosyl (1 --> 4)-beta-D-glucopyranosyl (1 --> 6)-beta-D-glucopyranoside (3), 3-O-alpha-L-rhamnopyranosyl (1 --> 2)-alpha-L-arabinopyrano-syl-oleanolic acid-28-O-alpha-L-rhamnopyranosyl (1 -->4)-beta-D-glucopyranosyl (1 --> 6)-beta-D-glucopyranoside (4), 3-O-alpha-L-rhamnopyranosyl (1 --> 2)-beta-D-xylopyranosyl-oleanolic acid-28-O-alpha-L-rhamnopyranosyl (1 --> 4)-beta-D-glucopyranosyl (1 --> 6)-beta-D-glucopyranoside (5). Compound 1 - 4 are isolated from this plant for the first time. Compound 1,2 are isolated from this genus for the first time.

Biotransformation and metabolic profile of Xian-Ling-Gu-Bao capsule, a traditional Chinese medicine prescription, with rat intestinal microflora by ultra-performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry analysis.

PubMed

Gao, Meng-Xue; Tang, Xi-Yang; Zhang, Feng-Xiang; Yao, Zhi-Hong; Yao, Xin-Sheng; Dai, Yi

2018-04-01

Xian-Ling-Gu-Bao capsule (XLGB), a well-known traditional Chinese medicine prescription, has been used for the prevention and treatment of osteoporosis. The safety and efficacy of XLGB have been confirmed based on the principle of evidence-based medicine. XLGB is usually administered orally, after which its multiple components are brought into contact with intestinal microflora in the alimentary tract and biotransformed. However, investigations on the comprehensive metabolic profile of XLGB are absent. In this study, 12 representative compounds bearing different typical structures (including iridoid glycosides, prenylated flavonol glycosides, prenylated flavonoids, triterpenoid saponins, steroidal saponins, coumarins and monoterpene phenols) were selected and then investigated for their biotransformation in rat intestinal microflora. In addition, the metabolic profile of XLGB in rat intestinal microflora was investigated by ultra-performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry. As a result, a total of 87 biotransformation components were identified from incubated solutions of 12 representative compounds and XLGB, which underwent 16 metabolic reactions (including deglycosylation, glycosylation, dehydrogenation, hydrogenation, oxidation, epoxidation, hydroxylation, dehydration, hydration, hydrolysis, methylation, isomerization, cyclization, pyrolysis reaction, amino acid conjugation and nucleophilic addition reaction with NH 3 ). This demonstrated that the deglycosylation reaction by cleavage of the sugar moieties is the main metabolic pathway of a variety of glycosides, including prenylated flavonol glycosides, coumarin glycosides, iridoid glycosides and saponins. In addition, compared with the biotransformation of 12 representative compounds, a different biotransformed fate was observed in the XLGB incubated samples of rat intestinal microflora. It is worth noting that the amino acid conjugation was first discovered in the metabolism of prenylated flavonol glycosides in rat intestinal microflora. Copyright © 2017 John Wiley & Sons, Ltd.

In vitro and in vivo antidiabetic potential of extracts and a furostanol saponin from Balanites aegyptiaca.

PubMed

Ezzat, Shahira Mohammed; Abdel Motaal, Amira; El Awdan, Sally Abdel Wanees

2017-12-01

Balanites aegyptiaca Del. (Zygophyllaceae) fruits are well-known antidiabetic drug in Egyptian folk medicine. Nevertheless, its mechanism of action is still unclear. Searching for the possible mechanisms of action of the plant and identification of its bioactive compounds. A bio-guided protocol based on the evaluation of α-glucosidase (AG) and aldose reductase (AR) inhibitory activities was adopted to isolate the biologically active compounds from the methanol extract (MeEx). An in vivo antidiabetic study was conducted for the active extract, fraction and compound using streptozotocin-induced diabetic male albino Wistar rats at two dose levels (100 and 200 mg/kg.b/wt) for 2 weeks. Three compounds were isolated and identified: a sterol, (1) stigmasterol-3-O-β-d-glucopyranoside; a pregnane glucoside, (2) pregn-5-ene-3β,16β,20(R)-trio1-3-O-β-d-glucopyranoside; a furostanol saponin, (3) 26-(O-β-d-glucopyranosyl)-22-O-methylfurost-5-ene-3β,26-diol-3-O-β-d-glucopyranosyl-(1 → 4)-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranoside. Only compound 3 possessed significant AG and AR inhibitory activities (IC 50  = 3.12 ± 0.17 and 1.04 ± 0.02 μg/mL, respectively), while compounds 1 and 2 were inactive. The in vivo antidiabetic study revealed that MeEx and furostanol saponin 3 possessed significant activities at a dose of 200 mg/kg through reducing the fasting plasma glucose level by 46.14% and 51.39%, respectively, as well as reducing the total cholesterol by 24.44% and 31.90%, respectively. Compound 3 also caused increment in insulin and C-peptide levels by 63.56% and 65%, respectively. We presented a scientific base for using Balanites aegyptiaca, and shed the light on one of its saponins, as an antidiabetic agent in fasting and postprandial hyperglycaemia along with the improvement of diabetic complications.

The influence of surfactants on cell surface properties of Aeromonas hydrophila during diesel oil biodegradation.

PubMed

Kaczorek, E; Urbanowicz, M; Olszanowski, A

2010-11-01

In this study the capacity of the newly isolated environmental strain Aeromonas hydrophila was evaluated. The influence of three surfactants: rhamnolipides, saponins and Triton X-100 on cell surface properties of the A. hydrophila environmental strain and the biodegradation process of diesel oil was studied. The surface activities in water, a mineral salts medium and in the biological system of all considered surfactants were estimated by means of equilibrium surface tension experiments. The obtained results indicated that critical micellar concentration in the biological system is twice higher for saponins and Triton X-100, and three times higher for rhamnolipides. Our results indicated also, that cell surface hydrophobicity (CSH) of bacteria is correlated with carbon sources in broth medium. The mechanism of surfactant action seems to be dependent on the type and concentration of surfactant used in the studies. The best effect of saponins on diesel oil biodegradation was observed using the A. hydrophila strain, diesel oil biodegradation after 21 days was 78%. Copyright (c) 2010 Elsevier B.V. All rights reserved.

Triterpenoids with Promoting Effects on the Differentiation of PC12 Cells from the Steamed Roots of Panax notoginseng.

PubMed

Gu, Cheng-Zhen; Lv, Jun-Jiang; Zhang, Xiao-Xia; Qiao, Yi-Jun; Yan, Hui; Li, Yan; Wang, Dong; Zhu, Hong-Tao; Luo, Huai-Rong; Yang, Chong-Ren; Xu, Min; Zhang, Ying-Jun

2015-08-28

The roots of Panax notoginseng, an important Chinese medicinal plant, have been used traditionally in both the raw and processed forms, due to the different chemical constituents and bioactivities found. Thirty-eight dammarane-type triterpenoid saponins were isolated from the steam-processed roots of P. notoginseng, including 18 new substances, namely, notoginsenosides SP1-SP18 (1-18). The structures of 1-18 were determined on the basis of spectroscopic analysis and acidic hydrolysis. The absolute configuration of the hydroxy group at C-24 in 1-4, 19, and 20 was determined in each case by Mo2(AcO)4-induced circular dichroism. The new compounds were found to feature a diversity of highly oxygenated side chains, formed by hydrolysis of the C-20 sugar moiety followed by dehydration, dehydrogenation, epoxidation, hydroxylation, or methoxylation of the main saponins in the raw roots. The new saponins 1, 2, 6-8, 14, and 17 and the known compounds 20-27 showed promoting effects on the differentiation of PC12 cells, at a concentration of 10 μM.

Three new triterpenoid saponins from the seeds of Aesculus turbinata.

PubMed

Yang, Xiu-Wei; Zhao, Jing; Hattori, Masao

2008-01-01

Three new triterpenoid saponins, named isoescins VIIa (1), VIa (2), and VIIIa (3), were isolated from the seeds of Aesculus turbinata and identified by spectroscopic analysis and chemical hydrolysis. Their structures were established as 21beta-O-tigloyl-28-O-acetylprotoaescigenin 3beta-O-[beta-d-galactopyranosyl(1 --> 2)][beta-d-glucopyranosyl(1 --> 4)]-beta-d-glucopyranosiduronic acid (Isoescin VIIa, 1), 21beta-O-(2-methylbutyryl)-28-O-acetylprotoaescigenin 3beta-O-[beta-d-glucopyranosyl(1 --> 2)] [beta-d-glucopyranosyl(1 --> 4)]-beta-d-glucopyranosiduronic acid (Isoescin VIa, 2), and 21beta-O-angeloyl-28-O-acetylbarringtogenol C 3beta-O-[beta-d-glucopyranosyl(1 --> 2)] [beta-d-glucopyranosyl(1 --> 4)]-beta-d-glucopyranosiduronic acid (Isoescin VIIIa, 3).

Saponins from Soy and Chickpea: Stability during Beadmaking and in Vitro Bioaccessibility

PubMed Central

Serventi, Luca; Chitchumroonchokchai, Chureeporn; Riedl, Ken M.; Kerem, Zohar; Berhow, Mark A.; Vodovotz, Yael; Schwartz, Steven J.; Failla, Mark L.

2013-01-01

This study investigated the stability of saponins during the making and simulated digestion of soy and soy–chickpea breads and the bioaccessibility of saponins in digested breads. Recovery of saponins in soy bread exceeded that in soy–chickpea breads, and recovery of type A and B saponins was greater than for type E and DDMP saponins. Simulated digestion of breads resulted in greater relative losses of type A and DDMP saponins than type B and E saponins due in part to conversion of DDMP. Bioaccessibility of type B, E, and DDMP saponins in aqueous fraction of chyme exceeded 50%, but was ~30% for type A saponins. Caco-2 cells accumulated 0.8–2.8% of saponins from apical compartment containing diluted aqueous fraction of chyme. These findings suggest that saponin structure and food matrix affect the stability of saponins during processing and digestion and that uptake of saponins by enterocyte-like cells is poor despite moderate apparent bioaccessibility. PMID:23768100

The aphrodisiac herb Tribulus terrestris does not influence the androgen production in young men.

PubMed

Neychev, V K; Mitev, V I

2005-10-03

The aim of the current study is to investigate the influence of Tribulus terrestris extract on androgen metabolism in young males. Twenty-one healthy young 20-36 years old men with body weight ranging from 60 to 125 kg were randomly separated into three groups-two experimental (each n=7) and a control (placebo) one (n=7). The experimental groups were named TT1 and TT2 and the subjects were assigned to consume 20 and 10 mg/kg body weight per day of Tribulus terrestris extract, respectively, separated into three daily intakes for 4 weeks. Testosterone, androstenedione and luteinizing hormone levels in the serum were measured 24 h before supplementation (clear probe), and at 24, 72, 240, 408 and 576 h from the beginning of the supplementation. There was no significant difference between Tribulus terrestris supplemented groups and controls in the serum testosterone (TT1 (mean+/-S.D.: 15.75+/-1.75 nmol/l); TT2 (mean+/-S.D.: 16.32+/-1.57 nmol/l); controls (mean+/-S.D.: 17.74+/-1.09 nmol/l) (p>0.05)), androstenedione (TT1 (mean+/-S.D.: 1.927+/-0.126 ng/ml); TT2 (mean+/-S.D.: 2.026+/-0.256 ng/ml); controls (mean+/-S.D.: 1.952+/-0.236 ng/ml) (p>0.05)) or luteinizing hormone (TT1 (mean+/-S.D.: 4.662+/-0.274U/l); TT2 (mean+/-S.D.: 4.103+/-0.869U/l); controls (mean+/-S.D.: 4.170+/-0.406U/l) (p>0.05)) levels. All results were within the normal range. The findings in the current study anticipate that Tribulus terrestris steroid saponins possess neither direct nor indirect androgen-increasing properties. The study will be extended in the clarifying the probable mode of action of Tribulus terrestris steroid saponins.

Highly hydroxylated steroids of the starfish Archaster typicus from the Vietnamese waters.

PubMed

Ivanchina, Natalia V; Kicha, Alla A; Huong, Trinh T T; Kalinovsky, Anatoly I; Dmitrenok, Pavel S; Agafonova, Irina G; Long, Pham Q; Stonik, Valentin A

2010-12-01

Five new steroidal compounds, including an unusual glucoside, along with several known steroids were isolated from the starfish Archaster typicus collected in shallow waters of Quang Ninh province (Vietnam). Three new compounds are 27-nor-cholestane derivatives and the other two are 24,26-dihydroxycholestane derivatives. A biogenesis pathway for the unusual side chain of 27-nor-cholestane derivatives is proposed. Isolated compounds presented moderate toxic effects in the sperm- and 8-blastomere tests on embryonal development of the sea urchin Strongylocentrotusintermedius. Copyright 2010 Elsevier Inc. All rights reserved.

Potential nephrotoxic effects produced by steroidal saponins from hydro alcoholic extract of Tribulus terrestris in STZ-induced diabetic rats.

PubMed

Gandhi, Sonia; Srinivasan, B P; Akarte, Atul S

2013-09-01

Chronic hyperglycemia leads to the development of microvascular complications like diabetic nephropathy. The present study investigated the potential effects of the hydroalcoholic extract of Tribulus terrestris, a plant of Zygophyllaceae family, on the renal complications in streptozotocin (STZ)-induced diabetic rats. Diabetes was induced by administering STZ (90 mg/kg) to the 2-days old neonates. After 6 weeks of induction, diabetic rats were treated with 50 mg/kg hydroalcoholic extract of T. terrestris for 8 weeks. The anti-hyperglycaemic nature was confirmed by reduction in blood glucose and improvement in insulin levels. Diabetic renal injury associated with decrease in total proteins and albumin levels was observed to be improved by T. terrestris extract. Glomerular filtration rate along with inflammatory and growth factors, adiponectin and erythropoietin were also improved by the treatment, though the findings were not significant. However, the beneficial antidiabetic effects of T. terrestris extract in plasma were not observed in kidney histopathology. This was confirmed by the quantitative estimation of unhydrolyzed fraction of saponins (major component: protodioscin) in plasma and kidney samples of normal and diabetic rats. Hence, it can be concluded that 8 weeks treatment with T. terrestris extract produces potential toxic effects in kidney, which are independent of its anti-diabetic action.

Karaya root saponin exerts a hypocholesterolemic response in rats fed a high-cholesterol diet.

PubMed

Afrose, Sadia; Hossain, Md S; Maki, Takaaki; Tsujii, Hirotada

2009-05-01

Different sources of saponins are known to have hypocholesterolemic activity with varying degrees of efficacy. We hypothesize that karaya root saponin would efficiently reduce cholesterol. The aim of this study is to examine the comparative hypocholesterolemic effect of karaya root saponin in rats fed a high-cholesterol diet. Sixty male Wister-Imamichi rats were divided into 5 groups of 12 rats each constituting of the following: control group, soybean saponin-supplemented group, karaya root saponin-supplemented group, quillaja saponin-supplemented group, and tea saponin-supplemented group. Compared with the control diet, both the karaya root- and quillaja saponin-supplemented diets significantly reduced (P < .05) serum cholesterol and atherogenic index. Karaya root saponin significantly increased the serum high-density lipoprotein cholesterol, high-density lipoprotein cholesterol/cholesterol ratio, and fecal cholesterol concentrations (P < .05). The triacylglycerol concentration was significantly reduced only in the quillaja saponin-supplemented rats (P < .05). All the tea, soybean, karaya root, and quillaja saponins significantly reduced low-density lipoprotein cholesterol, and the greatest reduction was observed with karaya root saponin. Highest fecal bile acid concentration was found with quillaja saponin, whereas highest liver bile acid concentration was observed with karaya root saponin-supplemented rats (P < .05). These results collectively suggest that karaya root saponin can efficiently reduce serum cholesterol concentration in rats.

Anti-dermatophytic activity of marine sponge, Sigmadocia carnosa (Dendy) on clinically isolated fungi.

PubMed

Dhayanithi, N B; Kumar, T T Ajith; Kalaiselvam, M; Balasubramanian, T; Sivakumar, N

2012-08-01

To screen the anti-fungal effects and find out the active metabolites from sponge, Sigmadocia carnosa (S. carnosa) against four dermatophytic fungi. The methanol, ethyl acetate and acetone extract of marine sponge, S. carnosa was examined against Trichophyton mentagrophytes (T. mentagrophytes), Trichophyton rubrum (T. rubrum), Epidermophyton floccosum (E. floccosum) and Microsporum gypseum (M. gypseum) and qualitative analysed to find out the active molecules. The methanol extract of sponge was expressed significant activity than ethyl acetate and acetone. The minimum inhibitory concentration (MIC) of methanol extract of sponge that resulted in complete growth inhibition of T. mentagrophytes, T. rubrum, E. floccosum and M. gypseum were found to 125, 250, 250 and 250 µg/mL respectively. But, 100 % inhibition of fungal spore germination was observed in T. mentagrophytes at 500 µg/mL concentration followed by T. rubrum, E. floccosum and M. gypseum at 1 000 µg/mL concentration. Other two extracts showed weak anti spore germination activity against the tested dermatophytic fungi. Methanol extracts showed presence of terpenoids, steroids, alkaloids, saponins and glycosides. Based on the literature, this is the first study which has conducted to inhibit the growth and spore germination of dermatophytic fungi with S. carnosa. Further research also needs to purify and characterize the secondary metabolites from the sponge, S. carnosa for the valuable source of novel substances for future drug discovery.

Anti-dermatophytic activity of marine sponge, Sigmadocia carnosa (Dendy) on clinically isolated fungi

PubMed Central

Dhayanithi, NB; Kumar, TT Ajith; Kalaiselvam, M; Balasubramanian, T; Sivakumar, N

2012-01-01

Objective To screen the anti-fungal effects and find out the active metabolites from sponge, Sigmadocia carnosa (S. carnosa) against four dermatophytic fungi. Methods The methanol, ethyl acetate and acetone extract of marine sponge, S. carnosa was examined against Trichophyton mentagrophytes (T. mentagrophytes), Trichophyton rubrum (T. rubrum), Epidermophyton floccosum (E. floccosum) and Microsporum gypseum (M. gypseum) and qualitative analysed to find out the active molecules. Results The methanol extract of sponge was expressed significant activity than ethyl acetate and acetone. The minimum inhibitory concentration (MIC) of methanol extract of sponge that resulted in complete growth inhibition of T. mentagrophytes, T. rubrum, E. floccosum and M. gypseum were found to 125, 250, 250 and 250 µg/mL respectively. But, 100 % inhibition of fungal spore germination was observed in T. mentagrophytes at 500 µg/mL concentration followed by T. rubrum, E. floccosum and M. gypseum at 1 000 µg/mL concentration. Other two extracts showed weak anti spore germination activity against the tested dermatophytic fungi. Methanol extracts showed presence of terpenoids, steroids, alkaloids, saponins and glycosides. Conclusion Based on the literature, this is the first study which has conducted to inhibit the growth and spore germination of dermatophytic fungi with S. carnosa. Further research also needs to purify and characterize the secondary metabolites from the sponge, S. carnosa for the valuable source of novel substances for future drug discovery. PMID:23569985

Dioscin relieves endotoxemia induced acute neuro-inflammation and protect neurogenesis via improving 5-HT metabolism

PubMed Central

Yang, Rui; Chen, Wei; Lu, Ye; Li, Yingke; Du, Hongli; Gao, Songyan; Dong, Xin; Yuan, Hongbin

2017-01-01

Sepsis, in addition to causing fatality, is an independent risk factor for cognitive impairment among sepsis survivors. The pathologic mechanism of endotoxemia induced acute neuro-inflammation still has not been fully understood. For the first time, we found the disruption of neurotransmitters 5-HT, impaired neurogenesis and activation of astrocytes coupled with concomitant neuro-inflammation were the potential pathogenesis of endotoxemia induced acute neuro-inflammation in sepsis survivors. In addition, dioscin a natural steroidal saponin isolated from Chinese medicinal herbs, enhanced the serotonergic system and produced anti-depressant effect by enhancing 5-HT levels in hippocampus. What is more, this finding was verified by metabolic analyses of hippocampus, indicating 5-HT related metabolic pathway was involved in the pathogenesis of endotoxemia induced acute neuro-inflammation. Moreover, neuro-inflammation and neurogenesis within hippocampus were indexed using quantitative immunofluorescence analysis of GFAP DCX and Ki67, as well as real-time RT-PCR analysis of some gene expression levels in hippocampus. Our in vivo and in vitro studies show dioscin protects hippocampus from endotoxemia induced cascade neuro-inflammation through neurotransmitter 5-HT and HMGB-1/TLR4 signaling pathway, which accounts for the dioscin therapeutic effect in behavioral tests. Therefore, the current findings suggest that dioscin could be a potential approach for the therapy of endotoxemia induced acute neuro-inflammation. PMID:28059131

The antifungal activity and membrane-disruptive action of dioscin extracted from Dioscorea nipponica.

PubMed

Cho, Jaeyong; Choi, Hyemin; Lee, Juneyoung; Kim, Mi-Sun; Sohn, Ho-Yong; Lee, Dong Gun

2013-03-01

Dioscin is a kind of steroidal saponin isolated from the root bark of wild yam Dioscorea nipponica. We investigated the antifungal effect of dioscin against different fungal strains and its antifungal mechanism(s) in Candida albicans cells. Using the propidium iodide assay and calcein-leakage measurement, we confirmed that dioscin caused fungal membrane damage. Furthermore, we evaluated the ability of dioscin to disrupt the plasma membrane potential, using 3,3'-dipropylthiadicarbocyanine iodide [DiSC(3)(5)] and bis-(1,3-dibarbituric acid)-trimethine oxanol [DiBAC(4)(3)]. Cells stained with the dyes had a significant increase in fluorescent intensity after exposure to dioscin, indicating that dioscin has an effect on the membrane potential. To visualize the effect of dioscin on the cell membrane, we synthesized rhodamine-labeled giant unilamellar vesicles (GUVs) mimicking the outer leaflet of the plasma membrane of C. albicans. As seen in the result, the membrane disruptive action of dioscin caused morphological change and rhodamine leakage of the GUVs. In three-dimensional contour-plot analysis using flow cytometry, we observed a decrease in cell size, which is in agreement with our result from the GUV assay. These results suggest that dioscin exerts a considerable antifungal activity by disrupting the structure in membrane after invading into the fungal membrane, resulting in fungal cell death. Copyright © 2012 Elsevier B.V. All rights reserved.

Chemical Composition of Buddleja polystachya Aerial Parts and its Bioactivity against Aedes aegypti

USDA-ARS?s Scientific Manuscript database

A new acylatediridoid glycoside, 6-O-a-L-(2''-acetyl-4''-O-trans-isoferuloyl) rhamnopyranosyl catalpol (9) together with 18 known compounds belonging to the iridoids, flavonoids, triterpene saponin glycosides and phenylethanoids (1-8, 10-18) were isolated from the aerial parts and the flowers of Bud...

Antibacterial activity of cinnamon ethanol extract (cinnamomum burmannii) and its application as a mouthwash to inhibit streptococcus growth

NASA Astrophysics Data System (ADS)

Waty, Syahdiana; Suryanto, Dwi; Yurnaliza

2018-03-01

Cinnamon bark has been commonly used as spicy and traditional medicine. It contains several antibacterial compounds such as flavonoids, saponins, and cinnamaldehyde. Several studies have been done to know the antibacterial effect on bacteria such as Streptococcus in vitro. This study aimed to examine the antibacterial activity of cinnamon ethanol extract against Streptococcus and its application as mouthwash to inhibit the bacteria. The cinnamon bark was macerated followed by extracted in 80% ethanol. Bacterial samples were isolated from dental plaque of patients visiting dental clinic drg. Syahdiana Waty in Medan, North Sumatra. The isolates were identified using Vitek 2 compact. Secondary metabolites were detected using previously described method. Antibacterial assay was done at extract concentration of 6.25%, 12.5%, and 25%. The result showed that alkaloids, flavonoids, saponins, and glycoside were detected in the extract. Nine bacterial species were identified as Streptococcus mitis, S. sanguinis, S. salivarius, S. pluranimalium, S. pneumoniae, S. alactolyticus, Kocuria rosea, Kocuria kristinae, and Spingomonas paucimolis. It showed that the extract of Cinnamon bark significantly inhibited Streptococcus growth, and it was effective as mouthwash.

[Triterpenoid saponins from flower bud of Jasminum officinale var. grandiflorum].

PubMed

Zhao, Gui-Qin; Dong, Jun-Xing

2008-01-01

To study the chemical constituent bud of the flowers of Jasminum officinale var. grandiflorum. The compounds were isolated and purified by recrystallization and chromatography on silica gel and Sephadex LH - 20 column. Their structures were elucidated on the basis of physicochemical properties and spectral analysis. Six triterpenoid saponins were identified as 3-O-alpha-L-rhamnopyranosyl (1 --> 2)-beta-D-xylopyranosyl- hederagenin-28-O-beta-D-galactopyranosyl (1 --> 6)-beta-D-galactopyranosyl ester (1), hederagenin-3-O-beta-D-glucopyranosyl (1 --> 3)-alpha-L-arabinopyranoside (2), 2alpha, 3beta, 23-trihydroxyolean-12-en-28-oic-O-beta-D-glucopyranosyl ester (3), hederagenin-3-O-beta-D-xylopyranosyl (1 --> 3)-alpha-L-rhamnopyranosyl (1 --> 2)-alpha-L-arabinopyranoside (4), 2alpha, 3beta, 23-trihydroxyolean-12-en-28-oic-O-alpha-L-rhamnopyranosyl (1 --> 4)-beta-D-glucopyranosyl (1 --> 6)-beta-D-glucopyranosyl ester (5), hederagenin-3-O-alpha-L-rhamnopyranosyl (1 --> 2)-alpha-L-arabinopyranoside (6). Compound 1 is a new compound. Compounds 2, 3, 4, 5, 6 were isolated from the genus Jasminum for the first time.

Isolation and characterization of Cepa2, a natural alliospiroside A, from shallot (Allium cepa L. Aggregatum group) with anticancer activity.

PubMed

Abdelrahman, Mostafa; Mahmoud, Hassan Y A H; El-Sayed, Magdi; Tanaka, Shuhei; Tran, L S

2017-07-01

Exploration of new and promising anticancer compounds continues to be one of the main tasks of cancer research because of the drug resistance, high cytotoxicity and limitations of tumor selectivity. Natural products represent a better choice for cancer treatment in comparison with synthetic compounds because of their pharmacokinetic properties and lower side effects. In the current study, we isolated a steroidal saponin, named Cepa2, from the dry roots of shallot (Allium cepa L. Aggregatum group), and determined its structure by using two-dimensional nuclear manganic resonance (2D NMR). The 1 H NMR and 13 C NMR data revealed that the newly isolated Cepa2 compound is identical to alliospiroside A (C 38 H 60 O 12 ) [(25S)-3β-hydroxyspirost-5-en-1β-yl-2-O-(6-deoxy-α-L-mannopyranosyl)-α-L-arabinopyranoside], whose anticancer activity remains elusive. Our in vitro examination of the cytotoxic activity of the identified Cepa2 against P3U1 myeloma cancer cell line showed its high efficiency as an anticancer with 91.13% reduction in P3U1 cell viability 12 h post-treatment. The reduction of cell viability was correlated with the increase in reactive oxygen species levels in Cepa2-treated P3U1 cells, as compared with untreated cells. Moreover, scanning electron microscope results demonstrated apoptosis of the Cepa2-treated P3U1 cells in a time course-dependent manner. The results of our study provide evidence for the anticancer properties of the natural Cepa2/alliospiroside A extracted from shallot plants, and a strong foundation for in-depth investigations to build theoretical bases for cell apoptosis and development of novel anticancer drugs. Copyright © 2017 Elsevier Masson SAS. All rights reserved.

Cycloartane triterpenoid saponins from water soluble of Passiflora edulis Sims and their antidepressant-like effects.

PubMed

Wang, Cong; Xu, Feng-Qing; Shang, Jian-Hua; Xiao, Huai; Fan, Wei-Wei; Dong, Fa-Wu; Hu, Jiang-Miao; Zhou, Jun

2013-07-30

Various species of genus Passiflora have been used as traditional folk medicines owing to their sedative and anti-hypertensive properties. Passiflora edulis Sims most widely grown in the warm temperate for their fragrant fruits and their twigs and leaves are used as a folk medicine for treating both anxiety and nervousness in American countries. The present study was to evaluate the antidepressant-like effect and the active components of this plant. The alcohol extracts of the stems (PES, 10 and 2 g/kg of the plant materials) and leaves (PEL, 10 and 2 g/kg of the plant materials) of Passiflora edulis Sims were orally administered to mice for 7 day. The animals were tested in the forced swim test (FST) and tail suspension test (TST). After behavioral assay of ethanol extract, phytochemical research of the stems and leaves (5.7 kg) of Passiflora edulis Sims were developed and further bioactive verification of monomeric compounds were conducted. There are mainly cycloartane triterpenoids and their saponins isolated from this plant, including two new cycloartane triterpenoid saponins named cyclopassifloside ХII (1) and ХIII (2), together with six known cycloartane triterpenoids, cyclopassifloic acids B and E, cyclopassiflosides II, VI, IX and XI. The ethanol extract of Passiflora edulis Sims together with isolated compounds cyclopassiflosides IX and XI may possess antidepressant-like effect. Cycloartane triterpenoid was one of the main compositions of Passiflora edulis Sims and possess antidepressant-like activity. Crown Copyright © 2013. Published by Elsevier Ireland Ltd. All rights reserved.

Topological disposition of the sequences -QRKIVE- and -KETYY in native (Na sup + + K sup + )-ATPase

DOE Office of Scientific and Technical Information (OSTI.GOV)

Bayer, R.

1990-03-06

The dispositions with respect to the plane of the membrane of lysine-905 in the internal sequence -EQRKIVE- and of lysine-1012 in the carboxy-terminal sequence -RRPGGWVEKETYY of the {alpha}-polypeptide of sodium and potassium ion activated adenosinetriphosphatase have been determined. These lysines are found in peptides released from the intact {alpha}-polypeptide by the extracellular protease from Staphylococcus aureus strain V8 and by trypsin, respectively. Synthetic peptides containing terminal sequences of these were used to prepare polyclonal antibodies, which were then used to prepare immunoadsorbents directed against the respective peptides. Sealed, right-side-out membrane vesicles containing native (Na{sup +} + K{sup +})-ATPase were labeledmore » with pyridoxal phosphate and sodium ({sup 3}H)borohydride in the absence or presence of saponin. The labeled {alpha}-polypeptide was isolated from these vesicles and digested with appropriate proteases. The incorporation of radioactivity into the peptides binding to the immunoadsorbent directed against the sequence pyrERXIVE increased 3-fold int the presence of saponin as a result of the increased accessibility of this portion of the protein to the reagent when the vesicles were breached by saponin; hence, this sequence is located on the cytoplasmic face of the membrane. It was inferred that the carboxy-terminal sequence -KETYY is on the extracytoplasmic face since the incorporation of radioactivity into peptides binding to the immunoadsorbent directed against the sequence -ETYY did not change when the vesicles were breached with saponin.« less

[Expression of saponin biosynthesis related genes in different tissues of Panax quinquefolius].

PubMed

Wang, Kang-Yu; Liu, Wei-Can; Zhang, Mei-Ping; Zhao, Ming-Zhu; Wang, Yan-Fang; Li, Li; Sun, Chun-Yu; Hu, Ke-Xin; Cong, Yue-Yi; Wang, Yi

2018-01-01

The relationship between saponin content of Panax quinquefolius in different parts of the organization and expression of ginsenoside biosynthesis related gene was obtained by the correlation analysis between saponin content and gene expression. The 14 tissue parts of P. quinquefolius were studied, six saponins in P. quinquefolius. Samples (ginsenoside Rg₁, Re, Rb₁, Rc, Rb₂ and Rd), group saponins and total saponins were determined by high performance liquid chromatography and vanillin-sulfuric acid colorimetric method. Simultaneously, the expression levels of 7 ginsenoside biosynthesis related genes ( SQS, OSC, DS, β-AS, SQE, P450 and FPS ) in different tissues of P. quinquefolius were determined by Real-time fluorescence quantitative PCR. Although 7 kinds of ginsenoside biosynthesis related enzyme gene in the P. quinquefolius involved in ginsenoside synthesis, the expression of β-AS and P450 genes had no significant effect on the content of monosodium saponins, grouping saponins and total saponins, FPS, SQS, OSC, DS and SQE had significant or extremely significant on the contents of single saponins Re, Rg1, Rb1, Rd, group saponin PPD and PPT, total saponin TMS and total saponin TS ( P <0.05 or P <0.01). The biosynthesis of partial saponins, grouping saponins and total saponins in P. quinquefolius was affected by the interaction of multiple enzyme genes in the saponin synthesis pathway, the content of saponins in different tissues of P. quinquefolius was determined by the differences in the expression of key enzymes in the biosynthetic pathway. Therefore, this study further clarified that FPS, SQS, OSC, DS and SQE was the key enzyme to control the synthesis of saponins in P. quinquefolius by correlation analysis, the biosynthesis of ginsenosides in P. quinquefolius was regulated by these five kind of enzymes in cluster co-expression of interaction mode. Copyright© by the Chinese Pharmaceutical Association.

Four new triterpene saponins from the seeds of Aesculus chinensis.

PubMed

Zhao, Jing; Yang, Xiu-Wei

2003-09-01

Two pairs of new geometrically isomeric triterpenoid saponins were isolated from the seeds of Aesculus chinensis and characterized as 28-acetyl-21-tigloylprotoaescigenin 3-O-[beta-D-xylopyranosyl (1 --> 2)] [beta-D-glucopyranosyl (1 --> 4)] [beta-D-glucopyranosiduronic acid (isoescin IIa, 1) and 28-acetyl-21-angeloylprotoaescigenin 3-O-[-beta-D-xylopyranosyl (1 --> 2)] [beta-D-glucopyranosyl (1 --> 4)] beta-D-glucopyranosiduronic acid (isoescin IIb, 2); 28-acetyl-21-tigloylbarringtogenol C 3-O-[beta-D-galactopyranosyl (1 --> 2)] [beta-D-glucopyranosyl (1 --> 4)] beta-D-glucopyranosiduronic acid (isoescin IIIa, 3) and 28-acetyl-21-angeloylbarringtogenol C 3-O-[beta-D-galactopyranosyl (1 --> 2)] [beta-D-glucopyranosyl (1 --> 4)] beta-D-glucopyranosiduronic acid (isoescin IIIb, 4). Their structures were established on the basis of spectroscopic and chemical evidence.

Cytotoxic steroids from the leaves of Dysoxylum binectariferum.

PubMed

Yan, Hui-Jiao; Wang, Jun-Song; Kong, Ling-Yi

2014-08-01

Four new cholestane-type (1-4) and two new ergostane-type (5, 6) steroids were isolated from the leaves of Dysoxylum binectariferum. Their structures were elucidated on the basis of spectroscopic analysis, including 1D and 2D NMR techniques. The absolute configurations were established by comparison with the literature and Mo2(OAc)4-induced electronic circular dichroism (ECD) data. All the isolates were evaluated for cytotoxicity against A549 (lung carcinoma), MCF-7 (breast adenocarcinoma), and HepG2 (hepatocellular carcinoma) human cancer cell lines. Three of the new cholestane-type steroids displayed potent antiproliferative effects on the tumor cells with IC50 values ranging from 1.5 to 9.6μM, whereas the two new ergostane-type (5, 6) steroids were deemed inactive. Copyright © 2014 Elsevier Inc. All rights reserved.

A study of antimicrobial activity, acute toxicity and cytoprotective effect of a polyherbal extract in a rat ethanol-HCl gastric ulcer model

PubMed Central

2012-01-01

Background The decoction of the aerial parts of Rhynchosia recinosa (A.Rich.) Bak. [Fabaceae] is used in combination with the stem barks of Ozoroa insignis Del. (Anacardiaceae), Maytenus senegalensis (Lam.) Excell. [Celastraceae] Entada abyssinica Steud. ex A.Rich [Fabaceae] and Lannea schimperi (Hochst.)Engl. [Anacardiaceae] as a traditional remedy for managing peptic ulcers. However, the safety and efficacy of this polyherbal preparation has not been evaluated. This study reports on the phytochemical profile and some biological activities of the individual plant extracts and a combination of extracts of the five plants. Methods A mixture of 80% ethanol extracts of R. recinosa, O. insignis, M. senegalensis, E. abyssinica and L. schimperi at doses of 100, 200, 400 and 800 mg/kg body wt were evaluated for ability to protect Sprague Dawley rats from gastric ulceration by an ethanol-HCl mixture. Cytoprotective effect was assessed by comparison with a negative control group given 1% tween 80 in normal saline and a positive control group given 40 mg/kg body wt pantoprazole. The individual extracts and their combinations were also tested for antibacterial activity against four Gram negative bacteria; Escherichia coli (ATCC 25922), Salmonella typhi (NCTC 8385), Vibrio cholerae (clinical isolate), and Klebsiella pneumoniae (clinical isolate) using the microdilution method. In addition the extracts were evaluated for brine shrimp toxicity and acute toxicity in mice. Phytochemical tests were done using standard methods to determine the presence of tannins, saponins, steroids, cardiac glycosides, flavonoids, alkaloids and terpenoids in the individual plant extracts and in the mixed extract of the five plants. Results The combined ethanolic extracts of the 5 plants caused a dose-dependent protection against ethanol/HCl induced ulceration of rat gastric mucosa, reaching 81.7% mean protection as compared to 87.5% protection by 40 mg/kg body wt pantoprazole. Both the individual plant extracts and the mixed extracts of 5 plants exhibited weak to moderate antibacterial activity against four G-ve bacteria. Despite Ozoroa insignis being toxic to mice at doses above 1000 mg/kg body wt, the other plant extracts and the combined extract of the 5 plants were tolerated by mice up to 5000 mg/kg body wt. The brine shrimp test results showed the same pattern of toxicity with Ozoroa insignis being the most toxic (LC50 = 10.63 μg/ml). Phytochemical tests showed that the combined extract of the five plants contained tannins, saponins, steroids, cardiac glycosides, flavonoids and terpenoids. Flavonoids, tannins and terpenoids are known to have antioxidant activity. Conclusion The combined extract of the five plants exhibited a dose-dependent protective activity in the rat ethanol-HCl gastric ulcer model. The extracts also exhibited weak antibacterial activity against four Gram negative bacteria and low acute toxicity in mice and brine shrimps. Although the results support claims by traditional healers who use a decoction of the five plants for treatment of peptic ulcers, more models of gastric ulceration and proper animal toxicity studies are needed to validate possible clinical use of the polyherbal extract. It is also evident that the doses of the crude extracts showing protection of the gastric mucosa are too large for realistic translation to direct clinical application, but further studies using bioassay guided fractionation are important to either identify more practical fractions or active compound/s. PMID:23031266

Development of a method to screen and isolate potential xanthine oxidase inhibitors from Panax japlcus var via ultrafiltration liquid chromatography combined with counter-current chromatography.

PubMed

Li, Sainan; Tang, Ying; Liu, Chunming; Li, Jing; Guo, Liping; Zhang, Yuchi

2015-03-01

Panax japlcus var is a typical Chinese herb with a large number of saponins existing in all parts of it. The common methods of screening and isolating saponins are mostly labor-intensive and time-consuming. In this study, a new assay based on ultrafiltration-liquid chromatography-mass spectrometry (UF-LC-MS) was developed for the rapid screening and identifying of the ligands for xanthine oxidase from the extract of P. japlcus. Six saponins were identified as xanthine oxidase inhibitors from the extract. Subsequently, the specific binding ligands, namely, 24 (R)-majoroside R1, chikusetsusaponin IVa, oleanolic acid-28-O-β-D-glucopyranoside, notoginsenoside Fe, ginsenoside Rb2 and ginsenoside Rd (the purities of them were 95.74%, 96.12%, 93.19%, 94.83%, 95.07% and 94.62%, respectively) were separated by high-speed counter-current chromatography (HSCCC). The component ratio of the solvent system of HSCCC was calculated with the help of a multiexponential function model was optimized. The partition coefficient (K) values of the target compounds and resolutions of peaks were employed as the research indicators, and exponential function and binomial formulas were used to optimize the solvent system and flow rate of the mobile phases in a two-stage separation. An optimized two-phase solvent system composed of ethyl acetate, isopropanol, 0.1% aqueous formic acid (1.9:1.0:1.3, v/v/v, for the first-stage) and that composed of methylene chloride, acetonitrile, isopropanol, 0.1% aqueous formic acid (5.6:1.0:2.4:5.2, v/v/v/v, for the second-stage) were used to isolate the six compounds from P. japlcus. The targeted compounds isolated, collected and purified by HSCCC were analyzed by high performance liquid chromatography (UPLC), and the chemical structures of all the six compounds were identified by UV, MS and NMR. The results demonstrate that UF-LC-MS combined with HSCCC might provide not only a powerful tool for screening and isolating xanthine oxidase inhibitors in complex samples but also a useful platform for discovering bioactive compounds for the prevention and treatment of gout. Copyright © 2014 Elsevier B.V. All rights reserved.

Corneal reepithelialization and anti-inflammatory agents.

PubMed Central

Srinivasan, B D

1982-01-01

These studies have demonstrated that nonsteroidal anti-inflammatory agents (cyclooxygenase and lipoxygenase inhibitors) can inhibit PMN arrival in the tear fluid following corneal injury but do not inhibit the reepithelialization either by corneal epithelial cells or by conjunctival epithelial cells. Therefore, they can be used safely in ocular inflammatory conditions even when corneal epithelial defects are present. Corticosteroids, on the other hand, inhibit reepithelialization by conjunctival epithelial cells and not by corneal epithelial cells in the doses tested. This inhibition does not occur with pretreatment prior to injury, suggesting that corticosteroids can be used clinically in conditions that have intact corneal epithelium without fear of slowing down wound healing should epithelial defects occur when not on steroid therapy. Furthermore, the steroid inhibition is temporary since there is a breakthrough in steroid inhibition with time, and occurs only if the steroids have been used shortly after deepithelialization. The steroid inhibition can be reversed by specific steroid antagonist, indicating that the steroid effect is mediated through specific receptors. An exciting and new hypothesis proposes that corticosteroids induce the formation of an inhibitory protein that inhibits the phospholipase enzyme to cause a block in arachidonic acid release from cell membranes. This mechanism of action may also be prevalent in the steroid effect on corneal reepithelialization, and experiments are under way to isolate this inhibitory protein from steroid-treated conjunctival epithelium. This isolation and pharmacologic characterization of this inhibitory protein is of obvious advantage to the field of ophthalmic therapeutics since this protein may have the anti-inflammatory potential of the steroids without their steroid sideeffects. Images FIGURE 3 a FIGURE 3 b PMID:6763806

Inhibition of tumor necrosis factor-{alpha}-induced expression of adhesion molecules in human endothelial cells by the saponins derived from roots of Platycodon grandiflorum

DOE Office of Scientific and Technical Information (OSTI.GOV)

Kim, Ji Young; Kim, Dong Hee; Kim, Hyung Gyun

2006-01-15

Adhesion molecules play an important role in the development of atherogenesis and are produced by endothelial cells after being stimulated with various inflammatory cytokines. This study examined the effect of saponins that were isolated from the roots of Platycodon grandiflorum A. DC (Campanulaceae), Changkil saponins (CKS), on the cytokine-induced monocyte/human endothelial cell interaction, which is a crucial early event in atherogenesis. CKS significantly inhibited the TNF{alpha}-induced increase in monocyte adhesion to endothelial cells as well as decreased the protein and mRNA expression levels of vascular adhesion molecule-1 and intercellular cell adhesion molecule-1 on endothelial cells. Furthermore, CKS significantly inhibited themore » TNF{alpha}-induced production of intracellular reactive oxygen species (ROS) and activation of NF-{kappa}B by preventing I{kappa}B degradation and inhibiting I{kappa}B kinase activity. Overall, CKS has anti-atherosclerotic and anti-inflammatory activity, which is least in part the result of it reducing the cytokine-induced endothelial adhesion to monocytes by inhibiting intracellular ROS production, NF-{kappa}B activation, and cell adhesion molecule expression in endothelial cells.« less

Comparison of saponin composition and content in wild soybean (Glycine soja Sieb. and Zucc.) before and after germination.

PubMed

Krishnamurthy, Panneerselvam; Tsukamoto, Chigen; Takahashi, Yuya; Hongo, Yuji; Singh, Ram J; Lee, Jeong Dong; Chung, Gyuhwa

2014-01-01

Eight wild soybean accessions with different saponin phenotypes were used to examine saponin composition and relative saponin quantity in various tissues of mature seeds and two-week-old seedlings by LC-PDA/MS/MS. Saponin composition and content were varied according to tissues and accessions. The average total saponin concentration in 1 g mature dry seeds of wild soybean was 16.08 ± 3.13 μmol. In two-week-old seedlings, produced from 1 g mature seeds, it was 27.94 ± 6.52 μmol. Group A saponins were highly concentrated in seed hypocotyl (4.04 ± 0.71 μmol). High concentration of DDMP saponins (7.37 ± 5.22 μmol) and Sg-6 saponins (2.19 ± 0.59 μmol) was found in cotyledonary leaf. In seedlings, the amounts of group A and Sg-6 saponins reduced 2.3- and 1.3-folds, respectively, while DDMP + B + E saponins increased 2.5-fold than those of mature seeds. Our findings show that the group A and Sg-6 saponins in mature seeds were degraded and/or translocated by germination whereas DDMP saponins were newly synthesized.

Antitumor and anti-angiogenic potentials of isolated crude saponins and various fractions of Rumex hastatus D. Don.

PubMed

Ahmad, Sajjad; Ullah, Farhat; Ayaz, Muhammad; Zeb, Anwar; Ullah, Farman; Sadiq, Abdul

2016-03-12

Cancer, being the foremost challenge of the modern era and the focus of world-class investigators, gargantuan research is in progress worldwide to explore novel therapeutic for its management. The exploitation of natural sources has been proven to be an excellent approach to treat or minify the excessive angiogenesis and proliferation of cells. Similarly, based the ethnomedicinal uses and literature survey, the current study is designed to explore the anti-tumor and anti-angiogenic potentials of Rumex hastatus. Anti-tumor and anti-angiogenic activities were carried out using potato-disc model and chorioallantoic membrane (CAM) assay respectively. Moreover, R. hastatus was also assessed for antibacterial activity against Agrobacterium tumefaciens (tumor causing bacterial strain). The positive controls used in anti-tumor, anti-angiogenic and antibacterial activities were vincristine sulphate, dexamethasone and cefotaxime respectively. The crude saponins (Rh.Sp), methanolic extract (Rh.Cr) and other solvent extracts like n-hexane (Rh.Hex), chloroform (Rh.Chf), ethylacetate (Rh.EtAc) and aqueous fraction (Rh.Aq) exhibited notable anti-tumor and anti-angiogenic activities. In potato tumor assay, the chloroform and saponin fractions were observed to be the most effective showing 86.7 and 93.3 % tumor inhibition at 1000 µg/ml with IC50 values 31.6 and 18.1 µg/ml respectively. Similarly, these two samples i.e., chloroform and saponins also excelled among the entire test samples in anti-angiogenic evaluation exhibiting 81.6 % (IC50 = 17.9 µg/ml) and 78.9 % (IC50 = 64.9 µg/ml) at 1000 µg/ml respectively. In contrast, the antibacterial investigations revealed a negligible potential against A. tumefaciens. Based on our results we can claim that R. hastatus possesses both anti-tumor and anti-angiogenic potentials. In all of the solvent fractions, Rh.Chf and Rh.Sp were most effective against tumor and angiogenesis while having negligible activity against A. tumefaciens. It can be concluded that Rh.Chf and Rh.Sp might be potential targets in the isolation of natural product having anti-neoplastic action.

Physiological and structural properties of saponin-skinned single smooth muscle cells

PubMed Central

1987-01-01

The study of the fundamental events underlying the generation and regulation of force in smooth muscle would be greatly facilitated if the permeability of the cell membrane were increased so that the intracellular environment of the contractile apparatus could be manipulated experimentally. To initiate such an analysis, we developed a saponin permeabilization procedure that was used to "skin" isolated smooth muscle cells from the stomach of the toad, Bufo marinus. Suspensions of single cells isolated enzymatically were resuspended in high-K+ rigor solution (0 ATP, 5 mM EGTA) and exposed for 5 min to 25 micrograms/ml saponin. Virtually all the cells in a suspension were made permeable by this procedure and shortened to less than one-third their initial length when ATP and Ca++ were added; they re-extended when free Ca++ was removed. Analysis of the protein content of the skinned cells revealed that, although their total protein was reduced by approximately 30%, they retained most of their myosin and actin. Skinning was accompanied by a rearrangement of actin and myosin filaments within the cells such that a fine fibrillar structure became visible under the light microscope and a tight clustering of acting filaments around myosin filaments was revealed by the electron microscope. Face-on views of saponin-treated cell membranes revealed the presence of 70-80-A-wide pits or holes. The shortening rate of skinned cells was sensitive to [Ca++] between pCa 7 and pCa 5 and was half-maximal at approximately pCa 6.2. Shortening was also dependent on [ATP] but could be increased at low [ATP] by pretreatment with adenosine-5'-O-(3-thiotriphosphate) (ATP gamma S), which suggests that myosin phosphorylation was more sensitive to low substrate concentrations than was cross-bridge cycling. To determine whether a significant limitation to free diffusion existed in the skinned cells, a computer model of the cell and the unstirred layer surrounding it was developed. Simulations revealed that the membrane, even in skinned cells, could, for short time intervals, significantly inhibit the movement of substances into and out of cells. PMID:3114416

Physiological and structural properties of saponin-skinned single smooth muscle cells.

PubMed

Kargacin, G J; Fay, F S

1987-07-01

The study of the fundamental events underlying the generation and regulation of force in smooth muscle would be greatly facilitated if the permeability of the cell membrane were increased so that the intracellular environment of the contractile apparatus could be manipulated experimentally. To initiate such an analysis, we developed a saponin permeabilization procedure that was used to "skin" isolated smooth muscle cells from the stomach of the toad, Bufo marinus. Suspensions of single cells isolated enzymatically were resuspended in high-K+ rigor solution (0 ATP, 5 mM EGTA) and exposed for 5 min to 25 micrograms/ml saponin. Virtually all the cells in a suspension were made permeable by this procedure and shortened to less than one-third their initial length when ATP and Ca++ were added; they re-extended when free Ca++ was removed. Analysis of the protein content of the skinned cells revealed that, although their total protein was reduced by approximately 30%, they retained most of their myosin and actin. Skinning was accompanied by a rearrangement of actin and myosin filaments within the cells such that a fine fibrillar structure became visible under the light microscope and a tight clustering of acting filaments around myosin filaments was revealed by the electron microscope. Face-on views of saponin-treated cell membranes revealed the presence of 70-80-A-wide pits or holes. The shortening rate of skinned cells was sensitive to [Ca++] between pCa 7 and pCa 5 and was half-maximal at approximately pCa 6.2. Shortening was also dependent on [ATP] but could be increased at low [ATP] by pretreatment with adenosine-5'-O-(3-thiotriphosphate) (ATP gamma S), which suggests that myosin phosphorylation was more sensitive to low substrate concentrations than was cross-bridge cycling. To determine whether a significant limitation to free diffusion existed in the skinned cells, a computer model of the cell and the unstirred layer surrounding it was developed. Simulations revealed that the membrane, even in skinned cells, could, for short time intervals, significantly inhibit the movement of substances into and out of cells.

Sample preparation method influences direct identification of anaerobic bacteria from positive blood culture bottles using MALDI-TOF MS.

PubMed

Jeverica, Samo; Nagy, Elisabeth; Mueller-Premru, Manica; Papst, Lea

2018-05-15

Rapid detection and identification of anaerobic bacteria from blood is important to adjust antimicrobial therapy by including antibiotics with activity against anaerobic bacteria. Limited data is available about direct identification of anaerobes from positive blood culture bottles using MALDI-TOF mass spectrometry (MS). In this study, we evaluated the performance of two sample preparation protocols for direct identification of anaerobes from positive blood culture bottles, the MALDI Sepsityper kit (Sepsityper) and the in-house saponin (saponin) method. Additionally, we compared two blood culture bottle types designed to support the growth of anaerobic bacteria, the BacT/ALERT-FN Plus (FN Plus) and the BACTEC-Lytic (Lytic), and their influence on direct identification. A selection of 30 anaerobe strains belonging to 22 different anaerobic species (11 reference strains and 19 clinical isolates) were inoculated to 2 blood culture bottle types in duplicate. In total, 120 bottles were inoculated and 99.2% (n = 119) signalled growth within 5 days of incubation. The Sepsityper method correctly identified 56.3% (n = 67) of anaerobes, while the saponin method correctly identified 84.9% (n = 101) of anaerobes with at least log(score) ≥1.6 (low confidence correct identification), (p < 0.001). Gram negative anaerobes were better identified with the saponin method (100% vs. 46.5%; p < 0.001), while Gram positive anaerobes were better identified with the Sepsityper method (70.8% vs. 62.5%; p = 0.454). Average log(score) values among only those isolates that were correctly identified simultaneously by both sample preparation methods were 2.119 and 2.029 in favour of the Sepsityper method, (p = 0.019). The inoculated bottle type didn't influence the performance of the two sample preparation methods. We confirmed that direct identification from positive blood culture bottles with MALDI-TOF MS is reliable for anaerobic bacteria. However, the results are influenced by the sample preparation method used. Copyright © 2018 Elsevier Ltd. All rights reserved.

The extraction of antimicrobials component of andaliman (Zanthoxylum acanthopodium DC.) and its application on catfish (Pangasius sutchi) fillet

NASA Astrophysics Data System (ADS)

Muzafri, A.; Julianti, E.; Rusmarilin, H.

2018-02-01

Andaliman (Zanthoxylum acanthopodium DC.) is a well known wild species in North Sumatera and used for seasoning in Batak’s traditional cuisine. This study was aimed to examine the phytochemical constituents of andaliman fruit extracts after simple macerated in water, methanol, ethyl acetate and hexana using qualitative phytochemical analysis, and to determine its potential antimicrobial activity against Staphylococus aureus, Escherichia coli and Salmonella sp by using agar well difussion method and minimum inhibitory concentration (MIC). Phytochemicals such as alkaloids, flavonoid, glycosides, saponins, tannins, triterpene/steroid and glycoside anthroquinones were detected in the methanol extracts, but steroids and glycisode antraquinones were absent in the ethyl acetate extract. The ethyl acetate extracts showed maximum zone of inhibition and minimum inhibitory concentration against all the experimental microorganisms. The minimum zone of inhibition was determined in hexane extracts showing less antimicrobial activity against all the experimental microorganisms. The MIC of the ethyl acetate extracts was 0,5% w/v for all tested bacteria. Apllication of ethyl acetate extracts of andaliman fruits showed effective for catfish (Pangasius Sutchi) fillet stored in refrigerator (5 °C) for 3 days.

Saponin Inhibits Hepatitis C Virus Propagation by Up-regulating Suppressor of Cytokine Signaling 2

PubMed Central

Kang, Sang-Min; Min, Saehong; Son, Kidong; Lee, Han Sol; Park, Eun Mee; Ngo, Huong T. T.; Tran, Huong T. L.; Lim, Yun-Sook; Hwang, Soon B.

2012-01-01

Saponins are a group of naturally occurring plant glycosides which possess a wide range of pharmacological properties, including anti-tumorigenic and antiviral activities. To investigate whether saponin has anti-hepatitis C virus (HCV) activity, we examined the effect of saponin on HCV replication. HCV replication was efficiently inhibited at a concentration of 10 µg/ml of saponin in cell culture grown HCV (HCVcc)-infected cells. Inhibitory effect of saponin on HCV replication was verified by quantitative real-time PCR, reporter assay, and immunoblot analysis. In addition, saponin potentiated IFN-α-induced anti-HCV activity. Moreover, saponin exerted antiviral activity even in IFN-α resistant mutant HCVcc-infected cells. To investigate how cellular genes were regulated by saponin, we performed microarray analysis using HCVcc-infected cells. We demonstrated that suppressor of cytokine signaling 2 (SOCS2) protein level was distinctively increased by saponin, which in turn resulted in inhibition of HCV replication. We further showed that silencing of SOCS2 resurrected HCV replication and overexpression of SOCS2 suppressed HCV replication. These data imply that saponin inhibits HCV replication via SOCS2 signaling pathway. These findings suggest that saponin may be a potent therapeutic agent for HCV patients. PMID:22745742

Where does the toxicity come from in saponin extract?

PubMed

Jiang, Xiaogang; Cao, Yi; Jørgensen, Louise von Gersdorff; Strobel, Bjarne W; Hansen, Hans Chr Bruun; Cedergreen, Nina

2018-08-01

Saponin-rich plant extracts contain bioactive natural compounds and have many applications, e.g. as biopesticides and biosurfactants. The composition of saponin-rich plant extracts is very diverse, making environmental monitoring difficult. In this study various ecotoxicity data as well as exposure data have been collected to explore which compounds in the plant extract are relevant as plant protection agents and furthermore to clarify which compounds may cause undesired side-effects due to their toxicity. Hence, we quantified the toxicity of different fractions (saponins/non-saponins) in the plant extracts on the aquatic crustacean Daphnia magna and zebrafish (Danio rerio) embryos. In addition, we tested the toxicity changes during saponin degradation as well. The results confirm that saponins are responsible for the majority of toxicity (85.1-93.6%) of Quillaja saponaria extract. We, therefore, suggest saponins to be the main target of saponin-rich plant extracts, for instance in the saponin-based biopesticide regulation. Furthermore, we suggest that an abundant saponin fraction, QS-18 from Q. saponaria, can be a key monitoring target to represent the environmental concentration of the saponins, as it contributes with 26% and 61% of the joint toxicity to D. magna and D. rerio, respectively out of the total saponins. The degradation products of saponins are 3-7 times less toxic than the parent compound; therefore the focus should be mainly on the parent compounds. Copyright © 2018 Elsevier Ltd. All rights reserved.

Biosynthesis of 1α-hydroxycorticosterone in the winter skate Leucoraja ocellata: evidence to suggest a novel steroidogenic route.

PubMed

Wiens, J; Ho, R; Brassinga, A K; Deck, C A; Walsh, P J; Ben, R N; Mcclymont, K; Charlton, T; Evans, A N; Anderson, W G

2017-07-01

The present study explores the ability of intracellular bacteria within the renal-inter-renal tissue of the winter skate Leucoraja ocellata to metabolize steroids and contribute to the synthesis of the novel elasmobranch corticosteroid, 1α-hydroxycorticosterone (1α-OH-B). Despite the rarity of C1 hydroxylation noted in the original identification of 1α-OH-B, literature provides evidence for steroid C1 hydroxylation by micro-organisms. Eight ureolytic bacterial isolates were identified in the renal-inter-renal tissue of L. ocellata, the latter being the site of 1α-OH-B synthesis. From incubations of bacterial isolates with known amounts of potential 1α-OH-B precursors, one isolate UM008 of the genus Rhodococcus was seen to metabolize corticosteroids and produce novel products via HPLC analysis. Cations Zn 2+ and Fe 3+ altered metabolism of certain steroid precursors, suggesting inhibition of Rhodococcus steroid catabolism. Genome sequencing of UM008 identified strong sequence and structural homology to that of Rhodococcus erythropolis PR4. A complete enzymatic pathway for steroid-ring oxidation as documented within other Actinobacteria was identified within the UM008 genome. This study highlights the potential role of Rhodococcus bacteria in steroid metabolism and proposes a novel alternative pathway for 1α-OH-B synthesis, suggesting a unique form of mutualism between intracellular bacteria and their elasmobranch host. © 2017 The Fisheries Society of the British Isles.

Methanolic Root Extract of Rauwolfia serpentina Benth Improves the Glycemic, Antiatherogenic, and Cardioprotective Indices in Alloxan-Induced Diabetic Mice.

PubMed

Azmi, Muhammad Bilal; Qureshi, Shamim A

2012-01-01

The aim of the study was to evaluate the phytochemistry and the effect of methanolic root extract (MREt) of Rauwolfia serpentina on alloxan-induced diabetic Wister male mice. Mice were divided in control (distilled water at 1 mL/kg) and alloxan-induced diabetic mice which subdivided into diabetic (distilled water at 1 mL/kg), negative (0.05% dimethyl sulfoxide at 1 mL/kg), positive (glibenclamide at 5 mg/kg) controls, and three test groups (MREt at 10, 30, and 60 mg/kg). All treatments were given orally for 14 days. Qualitatively MREt showed the presence of alkaloids, carbohydrates, flavonoids, glycosides, cardiac glycosides, phlobatannins, resins, saponins, steroids, tannins, and triterpenoids, while quantitatively extract was rich in total phenols. The flavonoids, saponins and alkaloids were also determined in root powder. MREt found effective in improving the body weights, glucose and insulin levels, insulin/glucose ratio, glycosylated and total hemoglobin in test groups as compared to diabetic control. Similarly, significantly decreased levels of total cholesterol, triglycerides, low-density lipoprotein (LDL-c), and very low-density lipoprotein (VLDL-c) cholesterols were found in test groups. Significant lipolysis with improved glycogenesis was also found in liver tissues of all test groups. ALT levels were found normal in all groups. Thus, MREt improves the glycemic, antiatherogenic, coronary risk, and cardioprotective indices in alloxan-induced diabetic mice.

Medicinal flowers. III. Marigold. (1): hypoglycemic, gastric emptying inhibitory, and gastroprotective principles and new oleanane-type triterpene oligoglycosides, calendasaponins A, B, C, and D, from Egyptian Calendula officinalis.

PubMed

Yoshikawa, M; Murakami, T; Kishi, A; Kageura, T; Matsuda, H

2001-07-01

The methanolic extract and its 1-butanol-soluble fraction from the flowers of Calendula officinalis were found to show a hypoglycemic effect, inhibitory activity of gastric emptying, and gastroprotective effect. From the 1-butanol-soluble fraction, four new triterpene oligoglycosides, calendasaponins A, B, C, and D, were isolated, together with eight known saponins, seven known flavonol glycosides, and a known sesquiterpene glucoside. Their structures were elucidated on the basis of chemical and physicochemical evidence. The principal saponin constituents, glycosides A, B, C, D, and F, exhibited potent inhibitory effects on an increase in serum glucose levels in glucose-loaded rats, gastric emptying in mice, and ethanol- and indomethacin-induced gastric lesions in rats. Some structure-activity relationships are discussed.

Two new triterpenoid saponins from rhizome of Anemone amurensis.

PubMed

Lv, Chong-Ning; Fan, Li; Wang, Jing; Qin, Ru-Lan; Xu, Tan-Ye; Lei, Tian-Li; Lu, Jin-Cai

2015-01-01

Two new triterpenoid saponins were isolated from the 70% ethanol extract of the rhizome of Anemone amurensis, they are oleanolic acid 28-O-β-d-glucopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl ester (1) and 23,27-dihydroxy oleanolic acid 3-O-α-l-arabinopyranoside (2). The structures of 1 and 2 were elucidated on the basis of chemical and spectral analysis, including 1D and 2D NMR data and HR-ESI-MS. Compounds 1 and 2 were tested for cytotoxicities against three human cancer cell lines (A549, Hep-G2, and MCF-7). Compound 1 showed potent cytotoxicity with IC50 values of 34.76, 41.17, and 28.92 μM, respectively, while compound 2 with IC50>100 μM.

Effect of dietary karaya saponin on serum and egg yolk cholesterol in laying hens.

PubMed

Afrose, S; Hossain, M S; Tsujii, H

2010-12-01

1. The objective of the study was to investigate the effect of dietary karaya saponin on cholesterol deposition in laying hens. 2. A total of 40 Boris Brown hens were randomly assigned at 20 weeks of age to 4 treatment groups and fed on diets supplemented with 0 (control), 25, 50 or 75 mg/kg karaya saponin for an 8-week experimental period. 3. After 8 weeks of dietary supplementation, karaya-saponin-treated groups had significantly lower serum cholesterol (23·0%) and triglycerides but increased high density lipoproteins cholesterol concentration than controls, irrespective of karaya saponin content in the diet. Egg yolk cholesterol and triglycerides were also significantly reduced by dietary karaya saponin. Hepatic cholesterol and triglycerides were significantly reduced by karaya saponin but bile acids concentration in the faeces and liver were significantly increased by karaya saponin. The concentrations of oleic, linoleic and linolenic acids in the yolk were greater in hens receiving karaya saponin than in controls. Karaya saponin significantly increased egg production, feed efficiency and yolk colour compared with controls. Karaya saponin tended to increase egg weight, feed consumption, Haugh units, albumen weight and yolk index. 4. In conclusion, karaya saponin is a potential agent for reducing yolk cholesterol concentration together with an overall increase of production performance and improvement in egg quality.

Cytotoxic triterpenoids isolated from sweet chestnut heartwood (Castanea sativa) and their health benefits implication.

PubMed

Pérez, Andy J; Pecio, Łukasz; Kowalczyk, Mariusz; Kontek, Renata; Gajek, Gabriela; Stopinsek, Lidija; Mirt, Ivan; Stochmal, Anna; Oleszek, Wiesław

2017-11-01

For centuries wood containers have been used in aging of wines and spirits, due to the pleasant flavors they give to the beverages. Together with oak, sweet chestnut wood (Castanea sativa) have been often used for such purpose. The maturation process involves the transfer of secondary metabolites, mainly phenolics, from the wood to the liquid. At the same time, other metabolites, such as triterpenoids and their glycosides, can also be released. Searching for the extractable triterpenoids from sweet chestnut heartwood (C. sativa), two new ursane-type triterpenoid saponins named chestnoside A (1) and chestnoside B (2), together with two known oleanen-type analogs (3 and 4) were isolated and characterized. The cytotoxicity of isolated compounds was tested against two cancer cell lines (PC3 and MCF-7), and normal lymphocytes. Breast cancer cells (MCF-7) were more affected by tested compounds than prostate cancer cells (PC3). Chestnoside B (2) exhibited the strongest cytotoxicity with an IC 50 of 12.3 μM against MCF-7 cells, lower than those of positive controls, while it was moderately active against normal lymphocytes (IC 50  = 67.2 μM). These results highlight the occurrence of triterpenoid saponins in sweet chestnut heartwood and their potential for the chemoprevention of breast cancer. Copyright © 2017 Elsevier Ltd. All rights reserved.

Alfalfa (Medicago sativa L.) shoot saponins: identification and bio-activity by the assessment of aphid feeding.

PubMed

Mazahery-Laghab, H; Yazdi-Samadi, B; Bagheri, M; Bagheri, A R

2011-01-01

Biochemical components in alfalfa (Medicago sativa L.), such as saponins, can act as protecting factors against bio-stresses. Saponins are also antifeedants and show oral toxicity towards higher and lower animals. Changes in saponins, such as variation in the carbon skeleton, or hydrolysis of saponin glycosides and other conjugates, may change their biological effects. The aims of this research were to study saponin variation in different growth stages of alfalfa and to investigate the biological role of saponins in the spotted alfalfa aphid, Therioaphis maculata. Saponins from alfalfa shoots in different growth stages were extracted, chemically purified and analysed by TLC. Specific saponins such as soyasaponin1 from root and shoot and two bisdesmosides of medicagenic acid, one from shoot and another from root tissues, were identified using reference compounds allowing changes in saponin composition during plant development in different shoot tissues of alfalfa to be assessed. The response of the alfalfa aphid to feeding on alfalfa in different growth stages was studied. No significant difference in the survival of aphids, from neonate to adult, was observed, but due to the antibiotic effects of saponins, two differences were found in the onset of nymph production and cumulative nymph production. The results show that the saponin composition in alfalfa changes with plant development and this, in turn, can often negatively affect the development of specific insect pests such as the spotted alfalfa aphid, suggesting a possible biological role of alfalfa saponins.

Oleiferoside W from the roots of Camellia oleifera C. Abel, inducing cell cycle arrest and apoptosis in A549 cells.

PubMed

Wu, Jiang-Ping; Kang, Nai-Xin; Zhang, Mi-Ya; Gao, Hong-Wei; Li, Xiao-Ran; Liu, Yan-Li; Xu, Qiong-Ming; Yang, Shi-Lin

2017-07-06

Camellia oleifera C. Abel has been widely cultivated in China, and a group of bioactive constituents such as triterpeniod saponin have been isolated from C. oleifera C. Abel. In the current study, a new triterpeniod saponin was isolated from the EtOH extract of the roots of C. oleifera C. Abel, named as oleiferoside W, and the cytotoxic properties of oleiferoside W were evaluated in non-small cell lung cancer A549 cells. At the same time the inducing apoptosis, the depolarization of mitochondrial membrane potential (Δψ), the up-regulation of related pro-apoptotic proteins, such as cleaved-PARP, cleaved-caspase-3, and the down-regulation of anti-apoptotic marker Bcl-2/Bax were measured on oleiferoside W. Furthermore, the function, inducing the generation of reactive oxygen species (ROS) and apoptosis, of oleiferoside W could be reversed by N-acetylcysteine (NAC). In conclusion, our findings showed that oleiferoside W induced apoptosis involving mitochondrial pathway and increasing intracellular ROS production in the A549 cells, suggesting that oleiferoside W may have the possibility to be a useful anticancer agent for therapy in lung cancer.

Four new dammarane-type triterpene saponins from the stems and leaves of Panax ginseng and their cytotoxicity on HL-60 cells.

PubMed

Li, Ke-Ke; Yao, Chun-Mei; Yang, Xiu-Wei

2012-01-01

Four new triterpene saponins, ginsenosides Rh(14)-Rh(17)(1- 4), along with two known compounds, 20(S)-ginsenoside Rg₂ and dammar-(E)-20(22),24-diene-3 β,6 α,12 β-triol, were isolated from the stems and leaves of Panax ginseng. The structures of the new compounds were elucidated as 3 β,6 α,12 β,24 ξ-tetrahydroxy-dammar-(E)-20(22),25-diene 6- O- α- L-rhamnopyranosyl-(1 → 2)- β-D-glucopyranoside (1), 3 β,12 β,24 ξ-trihydroxy-dammar-(E)-20(22),25-diene 3- O- β- D-glucopyranosyl-(1 → 2)- β-D-glucopyranoside (2), 3 β,6 α,12 β-trihydroxy-dammar-(E)-20(22),24-diene 3-O-β-D-glucopyranoside (3), and 3-oxo-6 α,12 β,20(S)-trihydroxy-dammar-24-ene 6-O-α-L-rhamnopyranosyl-(1 → 2)-β-D-glucopyranoside (4) by means of extensive spectroscopic and chemical methods, respectively. The isolated compounds were tested for IN VITRO cytotoxicity against HL-60 cells. © Georg Thieme Verlag KG Stuttgart · New York.

Investigation of Mitochondrial Dysfunction by Sequential Microplate-Based Respiration Measurements from Intact and Permeabilized Neurons

PubMed Central

Clerc, Pascaline; Polster, Brian M.

2012-01-01

Mitochondrial dysfunction is a component of many neurodegenerative conditions. Measurement of oxygen consumption from intact neurons enables evaluation of mitochondrial bioenergetics under conditions that are more physiologically realistic compared to isolated mitochondria. However, mechanistic analysis of mitochondrial function in cells is complicated by changing energy demands and lack of substrate control. Here we describe a technique for sequentially measuring respiration from intact and saponin-permeabilized cortical neurons on single microplates. This technique allows control of substrates to individual electron transport chain complexes following permeabilization, as well as side-by-side comparisons to intact cells. To illustrate the utility of the technique, we demonstrate that inhibition of respiration by the drug KB-R7943 in intact neurons is relieved by delivery of the complex II substrate succinate, but not by complex I substrates, via acute saponin permeabilization. In contrast, methyl succinate, a putative cell permeable complex II substrate, failed to rescue respiration in intact neurons and was a poor complex II substrate in permeabilized cells. Sequential measurements of intact and permeabilized cell respiration should be particularly useful for evaluating indirect mitochondrial toxicity due to drugs or cellular signaling events which cannot be readily studied using isolated mitochondria. PMID:22496810

Ultrasound-assisted extraction and bioaccessibility of saponins from edible seeds: quinoa, lentil, fenugreek, soybean and lupin.

PubMed

Navarro Del Hierro, Joaquín; Herrera, Teresa; García-Risco, Mónica R; Fornari, Tiziana; Reglero, Guillermo; Martin, Diana

2018-07-01

The efficient production of saponin-rich extracts is of increasing interest due to the bioactive properties that have being demonstrated for these compounds. However, saponins have a poor bioavailability. In this respect, the knowledge about the bioaccessibility of saponins as a first step before bioavailability has been scarcely explored. In this study, the production of ultrasound-assisted extracts of saponins from edible seeds (quinoa, soybean, red lentil, fenugreek and lupin) was carried out with ethanol, ethanol:water or water. Extraction yield, total saponin (TSC), fat and total phenolics content (TPC) were determined. Then, the bioaccessibility of saponins after the in vitro gastrointestinal digestion of the extracts was determined and the effect of TPC and fat in the extracts on bioaccessibility was evaluated. The highest saponin-rich extracts were obtained by ethanol, being fenugreek and red lentil the richest extracts (12% and 10%, respectively). Saponins from ethanol:water extracts displayed variable bioaccessibility (from 13% for fenugreek to 83% for lentil), but a bioaccessibility closer to 100% was reached for all ethanol extracts. Correlation studies showed that TPC of the extracts negatively affected the bioaccessibility of saponins, whereas fat of the extracts enhanced this parameter. As summary, ultrasound-assisted extraction is shown as an efficient method for obtaining saponin-rich extracts from edible seeds, being ethanol the most advantageous solvent due to the richness of saponins and the successful bioaccessibility from these extracts, likely caused by the co-extracted fat with ethanol. Regardless of the extracts, phenolic compounds or fat may hinder or enhance the bioaccessibility of saponins, respectively. Additionally, an adequate balance between saponins to lipids has shown to be relevant on such an effect. Copyright © 2018 Elsevier Ltd. All rights reserved.

Cell wall integrity, genotoxic injury and PCD dynamics in alfalfa saponin-treated white poplar cells highlight a complex link between molecule structure and activity.

PubMed

Paparella, Stefania; Tava, Aldo; Avato, Pinarosa; Biazzi, Elisa; Macovei, Anca; Biggiogera, Marco; Carbonera, Daniela; Balestrazzi, Alma

2015-03-01

In the present work, eleven saponins and three sapogenins purified from Medicago sativa were tested for their cytotoxicity against highly proliferating white poplar (Populus alba L.) cell suspension cultures. After preliminary screening, four saponins with different structural features in terms of aglycone moieties and sugar chains (saponin 3, a bidesmoside of hederagenin; saponins 4 and 5, monodesmoside and bidesmoside of medicagenic acid respectively, and saponin 10, a bidesmoside of zanhic acid) and different cytotoxicity were selected and used for further investigation on their structure-activity relationship. Transmission Electron Microscopy (TEM) analyses provided for the first time evidence of the effects exerted by saponins on plant cell wall integrity. Exposure to saponin 3 and saponin 10 resulted into disorganization of the outer wall layer and the effect was even more pronounced in white poplar cells treated with the two medicagenic acid derivatives, saponins 4 and 5. Oxidative burst and nitric oxide accumulation were common hallmarks of the response of white poplar cells to saponins. When DNA damage accumulation and DNA repair profiles were evaluated by Single Cell Gel Electrophoresis, induction of single and double strand breaks followed by effective repair was observed within 24h. The reported data are discussed in view of the current issues dealing with saponin structure-activity relationship. Copyright © 2015 Elsevier Ltd. All rights reserved.

Saponins from soy and chickpea: stability during beadmaking and in vitro bioaccessibility

USDA-ARS?s Scientific Manuscript database

This study investigated the stability of saponins during the making and simulated digestion of soy and soy-chickpea breads and the bioaccessibility of saponins in digested breads. Recovery of saponins in soy bread exceeded that in soy-chickpea breads, and recovery of type A and B saponins was great...

Extraction of heavy metals from MSW incinerator fly ash using saponins.

PubMed

Hong, K J; Tokunaga, S; Ishigami, Y; Kajiuchi, T

2000-08-01

An extraction process with saponins was evaluated for removing heavy metals from MSW (municipal solid waste) incinerator fly ashes. Two different fly ashes, A and B, were treated on a laboratory scale with three triterpene-glycoside type of saponins, M, Q, and T, in the pH range 4-9. The results were compared with those of the HCI and EDTA treatment. The treatment with saponins extracted 20-45% of Cr from the fly ashes. Saponins were also effective in extracting Cu from fly ash A attaining 50-60% extraction. Saponin T extracted 100% of Pb from fly ash A at pH around 4. The extraction of Zn with the saponin treatment was similar to that of the HCl treatment. Further, Cr, Cu, Pb, and Zn were fractionated by sequential extraction to investigate the effect of saponins on each fraction. Extraction behavior of other elements during the saponin treatment was also studied. The leaching test on the residues received after the saponin treatment showed that the fly ashes were successfully detoxified to meet the landfilling guideline.

Qualitative and Quantitative Saponin Contents in Five Sea Cucumbers from the Indian Ocean

PubMed Central

Van Dyck, Séverine; Gerbaux, Pascal; Flammang, Patrick

2010-01-01

To avoid predation, holothuroids produce feeding-deterrent molecules in their body wall and viscera, the so-called saponins. Five tropical sea cucumber species of the family Holothuriidae were investigated in order to study their saponin content in two different organs, the body wall and the Cuvierian tubules. Mass spectrometry techniques (MALDI- and ESI-MS) were used to detect and analyze saponins. The smallest number of saponins was observed in Holothuria atra, which contained a total of four congeners, followed by Holothuria leucospilota, Pearsonothuria graeffei and Actinopyga echinites with six, eight and ten congeners, respectively. Bohadschia subrubra revealed the highest saponin diversity (19 congeners). Saponin mixtures also varied between the two body compartments within a given animal. A semi-quantitative approach completed these results and showed that a high diversity of saponins is not particularly correlated to a high saponin concentration. Although the complexity of the saponin mixtures described makes the elucidation of their respective biological roles difficult, the comparisons between species and between body compartments give some clues about how these molecules may act as predator repellents. PMID:20161976

Improving the antiprotozoal effect of saponins in the rumen by combination with glycosidase inhibiting iminosugars or by modification of their chemical structure.

PubMed

Ramos-Morales, Eva; de la Fuente, Gabriel; Nash, Robert J; Braganca, Radek; Duval, Stephane; Bouillon, Marc E; Lahmann, Martina; Newbold, C Jamie

2017-01-01

The antiprotozoal effect of saponins is transitory, as when saponins are deglycosylated to sapogenins by rumen microorganisms they become inactive. We hypothesised that the combination of saponins with glycosidase-inhibiting iminosugars might potentially increase the effectiveness of saponins over time by preventing their deglycosylation in the rumen. Alternatively, modifying the structure of the saponins by substituting the sugar moiety with other small polar residues might maintain their activity as the sugar substitute would not be enzymatically cleaved. The aim of this in vitro study was to evaluate the acute antiprotozoal effect and the stability of this effect over a 24 h incubation period using ivy saponins, a stevia extract rich in iminosugars, ivy saponins with stevia extract, and a chemically modified ivy saponin, hederagenin bis-succinate (HBS). The effects on fermentation parameters and rumen bacterial communities were also studied. Ivy saponins with stevia and HBS had a greater antiprotozoal effect than ivy saponins, and this effect was maintained after 24 h of incubation (P<0.001). The combination of ivy and stevia extracts was more effective in shifting the fermentation pattern towards higher propionate (+39%) and lower butyrate (-32%) and lower ammonia concentration (-64%) than the extracts incubated separately. HBS caused a decrease in butyrate (-45%) and an increase in propionate (+43%) molar proportions. However, the decrease in ammonia concentration (-42%) observed in the presence of HBS was less than that caused by ivy saponins, either alone or with stevia. Whereas HBS and stevia impacted on bacterial population in terms of community structure, only HBS had an effect in terms of biodiversity (P<0.05). It was concluded that ivy saponins with stevia and the modified saponin HBS had a strong antiprotozoal effect, although they differed in their effects on fermentation parameters and bacteria communities. Ivy saponins combined with an iminosugar-rich stevia extract and/or HBS should be evaluated to determine their antiprotozoal effect in vivo.

Improving the antiprotozoal effect of saponins in the rumen by combination with glycosidase inhibiting iminosugars or by modification of their chemical structure

PubMed Central

de la Fuente, Gabriel; Nash, Robert J.; Braganca, Radek; Duval, Stephane; Bouillon, Marc E.; Lahmann, Martina; Newbold, C. Jamie

2017-01-01

The antiprotozoal effect of saponins is transitory, as when saponins are deglycosylated to sapogenins by rumen microorganisms they become inactive. We hypothesised that the combination of saponins with glycosidase-inhibiting iminosugars might potentially increase the effectiveness of saponins over time by preventing their deglycosylation in the rumen. Alternatively, modifying the structure of the saponins by substituting the sugar moiety with other small polar residues might maintain their activity as the sugar substitute would not be enzymatically cleaved. The aim of this in vitro study was to evaluate the acute antiprotozoal effect and the stability of this effect over a 24 h incubation period using ivy saponins, a stevia extract rich in iminosugars, ivy saponins with stevia extract, and a chemically modified ivy saponin, hederagenin bis-succinate (HBS). The effects on fermentation parameters and rumen bacterial communities were also studied. Ivy saponins with stevia and HBS had a greater antiprotozoal effect than ivy saponins, and this effect was maintained after 24 h of incubation (P<0.001). The combination of ivy and stevia extracts was more effective in shifting the fermentation pattern towards higher propionate (+39%) and lower butyrate (-32%) and lower ammonia concentration (-64%) than the extracts incubated separately. HBS caused a decrease in butyrate (-45%) and an increase in propionate (+43%) molar proportions. However, the decrease in ammonia concentration (-42%) observed in the presence of HBS was less than that caused by ivy saponins, either alone or with stevia. Whereas HBS and stevia impacted on bacterial population in terms of community structure, only HBS had an effect in terms of biodiversity (P<0.05). It was concluded that ivy saponins with stevia and the modified saponin HBS had a strong antiprotozoal effect, although they differed in their effects on fermentation parameters and bacteria communities. Ivy saponins combined with an iminosugar-rich stevia extract and/or HBS should be evaluated to determine their antiprotozoal effect in vivo. PMID:28886130

Alum-type adjuvant effect of non-haemolytic saponins purified from Ilex and Passiflora spp.

PubMed

Silveira, F; Rossi, S; Fernández, C; Gosmann, G; Schenkel, E; Ferreira, F

2011-12-01

Five saponins purified from the leaves of three Ilex species (saponins 1 and 2 from I. dumosa; saponin 3 from I. argentina; saponin 4 from I. paraguariensis) and from Passiflora alata (saponin 5) were evaluated for their in vitro haemolytic activity and in vivo immunostimulatory ability in a mouse model using tetanus toxoid (TT) as a model antigen. The assayed saponins showed very weak or no haemolytic activity over the tested concentration range. Mice were immunized twice with TT formulated with pure saponins 1-5, or with a mixture of saponins from Quillaja saponaria, aluminum hydroxide gel or saline, which were used as controls. The elicited humoral response was evaluated by means of the time course of specific serum antibody levels up to day 131 post-priming (total IgG and isotypes); the cellular response was tested through a delayed-type hypersensitivity (DTH) assay. The assayed saponins, in particular saponins 3 and 5, showed an adjuvant effect similar to that of alum for all tested parameters. The immunostimulating potential of these compounds deserves further investigation, especially taking into account that some Ilex spp. and Passiflora alata are native crops of widespread use and economical importance in Latin America. Copyright © 2011 John Wiley & Sons, Ltd.

Kinetic study of Saponins B stability in navy beans under different processing conditions

USDA-ARS?s Scientific Manuscript database

Saponins are rich in the legumes which are known to provide many health benefits for human beings. Saponins B is the main component in the saponins group present in navy beans. The stability of saponins B during food processing is a key issue to evaluating the quality and nutrition of food products....

Structural Elucidation of Novel Saponins in the Sea Cucumber Holothuria lessoni

PubMed Central

Bahrami, Yadollah; Zhang, Wei; Chataway, Tim; Franco, Chris

2014-01-01

Sea cucumbers are prolific producers of a wide range of bioactive compounds. This study aimed to purify and characterize one class of compound, the saponins, from the viscera of the Australian sea cucumber Holothuria lessoni. The saponins were obtained by ethanolic extraction of the viscera and enriched by a liquid-liquid partition process and adsorption column chromatography. A high performance centrifugal partition chromatography (HPCPC) was applied to the saponin-enriched mixture to obtain saponins with high purity. The resultant purified saponins were profiled using MALDI-MS/MS and ESI-MS/MS which revealed the structure of isomeric saponins to contain multiple aglycones and/or sugar residues. We have elucidated the structure of five novel saponins, Holothurins D/E and Holothurinosides X/Y/Z, along with seven reported triterpene glycosides, including sulfated and non-sulfated saponins containing a range of aglycones and sugar moieties, from the viscera of H. lessoni. The abundance of novel compounds from this species holds promise for biotechnological applications. PMID:25110919

Cytotoxic and anti-colorectal tumor effects of sulfated saponins from sea cucumber Holothuria moebii.

PubMed

Yu, Siran; Ye, Xuewei; Chen, Lu; Xie, Xin; Zhou, Qian; Lian, Xiao-Yuan; Zhang, Zhizhen

2015-11-15

Whether sulfated saponins from Holothuria moebii inhibit the proliferation of colorectal cancer cells and have anti-colorectal tumor effects in animal model has not been investigated. To evaluate the cytotoxic and anti-colorectal tumor effects of sulfated saponins from sea cucumber Holothuria moebii. (1) Column chromatography was used to prepare the total and individual saponins and HPLC was applied to define the components of the total saponins; (2) the activity of the total and individual saponins inhibiting the proliferation of human colorectal cancer cells was determined by SRB assay and the apoptosis induced by the saponins was qualified using cytometric analysis with Annexin V-FITC/PI double staining; and (3) the antitumor effects of the sulfated saponins on colorectal CT-26 tumor-bearing Balb/c mice were tested. The total and individual sulfated saponins significantly inhibited the proliferation of four different human colorectal cancer cells with IC50 values ranging from 1.04 to 4.08 μM (or 1.46 to 3.24 μg/ml for total saponins) and induced late apoptosis at an early treatment time in cancer cells. The total saponins (120 mg/kg) had antitumor activity in colorectal CT-26 tumor-bearing Balb/c mice. The sulfated saponins from H. moebii remarkably inhibited the proliferation of different human colorectal cancer cells and had significant anti-colorectal tumor activity in animal model. Copyright © 2015 Elsevier GmbH. All rights reserved.

[Correlation of gene expression related to amount of ginseng saponin in 15 tissues and 6 kinds of ginseng saponin biosynthesis].

PubMed

Wang, Kang-yu; Zhang, Mei-ping; Li, Chuang; Jiang, Shi-cui; Yin, Rui; Sun, Chun-yu; Wang, Yi

2015-08-01

Fifteen tissues of 4-year-old fruit repining stage Jilin ginseng were chosen as materials, six kinds of monomer saponins (ginsenosides Rg1, Re, Rb1, Rc, Rb2 and Rd) content in 15 tissues was measured by HPLC and vanillin-sulfuric acid method. The relative expression of FPS, SQS, SQE, OSC, β-AS and P450 genes in 15 tissues was analyzed by real-time PCR. The correlations between ginseng saponin content in 15 tissues of Jilin ginseng and biosynthetic pathway -related genes were obtained. The results showed that was a synergistic increase and decrease trend of positive linear correlation among six kinds of monomer saponin content, and there was a significantly (P < 0.01) positive correlation between monomer saponin content and total saponins content. Monomer saponin content and 6 kinds of enzyme gene correlation were different. Biosynthesis of ginseng total saponins and monomer saponin were regulated by six kinds of participation ginsenoside biosynthesis enzyme genes, the expression of these six kinds of genes in different tissues of ginseng showed collaborative increase and decrease trend, and regulated biosynthesis of ginseng ginsenoside by group coordinative manner.

Foam Properties and Detergent Abilities of the Saponins from Camellia oleifera

PubMed Central

Chen, Yu-Fen; Yang, Chao-Hsun; Chang, Ming-Shiang; Ciou, Yong-Ping; Huang, Yu-Chun

2010-01-01

The defatted seed meal of Camellia oleifera has been used as a natural detergent and its extract is commercially utilized as a foam-stabilizing and emulsifying agent. The goal of this study was to investigate the foam properties and detergent ability of the saponins from the defatted seed meal of C. oleifera. The crude saponin content in the defatted seed meal of C. oleifera was 8.34 and the total saponins content in the crude saponins extract was 39.5% (w/w). The foaming power of the 0.5 crude saponins extract solution from defatted seed meal of C. oleifera was 37.1 of 0.5 SLS solution and 51.3% to that of 0.5% Tween 80 solution. The R5 value of 86.0% represents good foam stability of the crude saponins extracted from the defatted seed meal of the plant. With the reduction of water surface tension from 72 mN/m to 50.0 mN/m, the 0.5% crude saponins extract solution has wetting ability. The sebum-removal experiment indicated that the crude saponins extract has moderate detergency. The detergent abilities of the saponins from C. oleifera and Sapindus mukorossi were also compared. PMID:21151446

Panax Notoginseng Saponin Controls IL-17 Expression in Helper T Cells

PubMed Central

Wei, Jia-Ru; Wen, Xiaofeng; Bible, Paul W.; Li, Zhiyu; Nussenblatt, Robert B.

2017-01-01

Abstract Purpose: Panax Notoginseng, a traditional Chinese medicine, is known as an anti-inflammatory herb. However, the molecular mechanism by which it controls helper T cell mediated immune responses is largely unknown. Methods: Naive CD4+ T cells isolated from healthy donors, patients with Behcet's disease, and C57BL/6 mice were polarized into Th1, Th17, and Treg cells. Proliferation and cytokine expression were measured in these cells with the presence or absence of Panax Notoginseng saponins (PNS). Genomewide expression profiles of Th1, Th17, and Treg cells were assessed using Affymetrix microarray analysis. Results: We found that PNS control the proliferation and differentiation of Th17 cells by globally downregulating the expression of inflammatory cytokines and cell cycle genes. Conclusions: These findings demonstrated that PNS function as an anti-inflammatory agent through directly targeting Th17 cell mediated immune response. PMID:28051353

Efficacy of the saponin component of Impatiens capensis Meerb.in preventing urushiol-induced contact dermatitis.

PubMed

Motz, Vicki A; Bowers, Christopher P; Kneubehl, Alexander R; Lendrum, Elizabeth C; Young, Linda M; Kinder, David H

2015-03-13

Many different tribes of American Indians used jewelweed, Impatiens capensis Meerb, as a plant mash to reduce development of poison ivy dermatitis. Saponins are a natural soapy constituent found within plants. A 2012 study suggested that saponins may be present in jewelweed which could be responsible for its efficacy in preventing rash development following contact with Toxicodendron radicans (L.) Kuntze (poison ivy). This study validated this hypothesis and demonstrated additional biological activity of the jewelweed saponin containing extract. Fresh I. capensis leaves were extracted with methanol and further partitioned between ethyl acetate and water, with a final separation between water and n-butanol, to obtain a saponin containing extract. The presence of saponins in the extract was demonstrated by the observation of foaming and using a vanillin colorimetric assay for total saponins. Efficacy of the saponin containing extracts in rash reduction was tested by brushing poison ivy (PI) onto the forearms of volunteers (N=23) in six locations and treating these PI exposed areas with distilled water (control), saponin containing extracts, fresh plant mashes, and soaps made with and without plant extracts. Saponin containing extracts were further tested for biological activity against both gram negative and gram positive bacteria and against cancer cell lines A-375, HT-29, and MCF-7. Additionally, because saponins have been shown to have a stimulatory effect in cardiac muscle 2 µl saponin extract was applied superficially to black worms, Lumbriculus variegatus (N=5). Both saponin containing extracts and all soaps tested were effective in reducing poison ivy dermatitis; thus, saponin content correlates with PI rash prevention. No apparent antibiosis was observed against any bacteria tested; however, dose response cytotoxicity was documented against MCF-7 breast cancer cells and cytostatic activity was seen against the HT-29 colon cancer cell lines. Lumbriculus variegatus exhibited a 138% increase in heart rate over baseline rate five minutes post treatment implying a possible positive chronotropic effect. Copyright © 2014 Elsevier Ireland Ltd. All rights reserved.

Saponin 1 Induces Apoptosis and Suppresses NF-κB-Mediated Survival Signaling in Glioblastoma Multiforme (GBM)

PubMed Central

Tang, Chi; Li, Bo; Wang, Yuangang; Gao, Zhenhui; Luo, Peng; Yin, Anan; Wang, Xiaoyang; Cheng, Guang; Fei, Zhou

2013-01-01

Saponin 1 is a triterpeniod saponin extracted from Anemone taipaiensis, a traditional Chinese medicine against rheumatism and phlebitis. It has also been shown to exhibit significant anti-tumor activity against human leukemia (HL-60 cells) and human hepatocellular carcinoma (Hep-G2 cells). Herein we investigated the effect of saponin 1 in human glioblastoma multiforme (GBM) U251MG and U87MG cells. Saponin 1 induced significant growth inhibition in both glioblastoma cell lines, with a 50% inhibitory concentration at 24 h of 7.4 µg/ml in U251MG cells and 8.6 µg/ml in U87MG cells, respectively. Nuclear fluorescent staining and electron microscopy showed that saponin 1 caused characteristic apoptotic morphological changes in the GBM cell lines. Saponin 1-induced apoptosis was also verified by DNA ladder electrophoresis and flow cytometry. Additionally, immunocytochemistry and western blotting analyses revealed a time-dependent decrease in the expression and nuclear location of NF-κB following saponin 1 treatment. Western blotting data indicated a significant decreased expression of inhibitors of apoptosis (IAP) family members,(e.g., survivin and XIAP) by saponin 1. Moreover, saponin 1 caused a decrease in the Bcl-2/Bax ratio and initiated apoptosis by activating caspase-9 and caspase-3 in the GBM cell lines. These findings indicate that saponin 1 inhibits cell growth of GBM cells at least partially by inducing apoptosis and inhibiting survival signaling mediated by NF-κB. In addition, in vivo study also demonstrated an obvious inhibition of saponin 1 treatment on the tumor growth of U251MG and U87MG cells-produced xenograft tumors in nude mice. Given the minimal toxicities of saponin 1 in non-neoplastic astrocytes, our results suggest that saponin 1 exhibits significant in vitro and in vivo anti-tumor efficacy and merits further investigation as a potential therapeutic agent for GBM. PMID:24278406

Steroid plant hormones: effects outside plant kingdom.

PubMed

Zhabinskii, Vladimir N; Khripach, Natalia B; Khripach, Vladimir A

2015-05-01

Brassinosteroids (BS) are the first group of steroid-hormonal compounds isolated from and acting in plants. Among numerous physiological effects of BS growth stimulation and adaptogenic activities are especially remarkable. In this review, we provide evidence that BS possess similar types of activity also beyond plant kingdom at concentrations comparable with those for plants. This finding allows looking at steroids from a new point of view: how common are the mechanisms of steroid bioregulation in different types of organisms from protozoa to higher animals. Copyright © 2014 Elsevier Inc. All rights reserved.

Hemolytic and antimicrobial activities differ among saponin-rich extracts from guar, quillaja, yucca, and soybean.

PubMed

Hassan, Sherif M; Byrd, James A; Cartwright, Aubry L; Bailey, Chris A

2010-10-01

Hemolytic and antibacterial activities of eight serial concentrations ranged from 5-666 microg/mL of saponin-rich extracts from guar meal (GM), quillaja, yucca, and soybean were tested in 96-well plates and read by enzyme-linked immunosorbent assay plate-well as 650 nm. Hemolytic assay used a 1% suspension of chicken red blood cells with water and phosphate buffered saline as positive and negative controls, respectively. Antibacterial activity against Staphylococcus aureus, Salmonella typhimurium, and Escherichia coli were evaluated using ampicillin and bacteria without saponin-rich extract as positive and negative controls, respectively. The 100% MeOH GM and commercial quillaja saponin-rich extracts were significantly the highest in both hemolytic and antibacterial activities against all bacteria at the same concentration tested. Soybean saponin-rich extract had no antibacterial activity against any of the bacteria at the concentrations tested while yucca saponin-rich extract had no antibacterial activity against the gram-negative bacteria at the concentrations tested. GM and quillaja saponin-rich extracts were hemolytic, while yucca and soybean saponin-rich extracts were not hemolytic at the concentrations tested. No saponin-rich extract source had antibacterial activity against S. typhimurium or E. coli at the concentrations tested. Both GM and quillaja saponin-rich extracts exhibited antibacterial activity against S. aureus. Saponin-rich extracts from different plant sources have different hemolytic and antibacterial activities.

Triterpenoid glycosides from Bacopa monnieri.

PubMed

Sivaramakrishna, Chillara; Rao, Chirravuri V; Trimurtulu, Golakoti; Vanisree, Mulabagal; Subbaraju, Gottumukkala V

2005-12-01

Two triterpenoid glycosides have been isolated along with 10 known saponins from Bacopa monnieri. Structures of the compounds have been elucidated as 3-O-[beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl] jujubogenin (1) and 3-O-[beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl] pseudojujubogenin (2) by high resolution NMR spectral data and chemical correlations. Further, the chemical compositions of bacosides A and B have been delineated.

Soya Saponins Induce Enteritis in Atlantic Salmon (Salmo salar L.).

PubMed

Krogdahl, Åshild; Gajardo, Karina; Kortner, Trond M; Penn, Michael; Gu, Min; Berge, Gerd Marit; Bakke, Anne Marie

2015-04-22

Soybean meal-induced enteritis (SBMIE) is a well-described condition in the distal intestine of salmonids, and saponins have been implicated as the causal agent. However, the question remains whether saponins alone cause SBMIE. Moreover, the dose-response relationship has not been described. In a 10 week feeding trial with Atlantic salmon, a highly purified (95%) soya saponin preparation was supplemented (0, 2, 4, 6, or 10 g/kg) to two basal diets, one containing fishmeal as the major protein source (FM) and the other 25% lupin meal (LP). Saponins caused dose-dependent increases in the severity of inflammation independent of the basal diet, with concomitant alterations in digestive functions and immunological marker expression. Thus, saponins induced inflammation whether the diet contained other legume components or not. However, responses were often the same or stronger in fish fed the corresponding saponin-supplemented LP diets despite lower saponin exposure, suggesting potentiation by other legume component(s).

New cytotoxic steroids from the leaves of Clerodendrum trichotomum.

PubMed

Xu, Rui-Lan; Wang, Rui; Ding, Lan; Shi, Yan-Ping

2013-07-01

A phytochemical investigation of the leaves of Clerodendrum trichotomum led to the isolation of five new (2-6) and two known (1 and 7) steroids, whose structures and relative configurations were elucidated by comprehensive spectroscopic analysis and by comparison of their NMR data with those of related compounds. Steroids 2 and 5 exhibited moderate cytotoxicity in vitro against HeLa cell line. Copyright © 2013 Elsevier Inc. All rights reserved.

Impact of two different saponins on the organization of model lipid membranes.

PubMed

Korchowiec, Beata; Gorczyca, Marcelina; Wojszko, Kamila; Janikowska, Maria; Henry, Max; Rogalska, Ewa

2015-10-01

Saponins, naturally occurring plant compounds are known for their biological and pharmacological activity. This activity is strongly related to the amphiphilic character of saponins that allows them to aggregate in aqueous solution and interact with membrane components. In this work, Langmuir monolayer techniques combined with polarization modulation infrared reflection-absorption spectroscopy (PM-IRRAS) and Brewster angle microscopy were used to study the interaction of selected saponins with lipid model membranes. Two structurally different saponins were used: digitonin and a commercial Merck Saponin. Membranes of different composition, namely, cholesterol, 1,2-dipalmitoyl-sn-glycero-3-phosphocholine or 1,2-dipalmitoyl-sn-glycero-3-phospho-rac-(1-glycerol) were formed at the air/water and air/saponin solution interfaces. The saponin-lipid interaction was characterized by changes in surface pressure, surface potential, surface morphology and PM-IRRAS signal. Both saponins interact with model membranes and change the physical state of membranes by perturbing the lipid acyl chain orientation. The changes in membrane fluidity were more significant upon the interaction with Merck Saponin. A higher affinity of saponins for cholesterol than phosphatidylglycerols was observed. Moreover, our results indicate that digitonin interacts strongly with cholesterol and solubilize the cholesterol monolayer at higher surface pressures. It was shown, that digitonin easily penetrate to the cholesterol monolayer and forms a hydrogen bond with the hydroxyl groups. These findings might be useful in further understanding of the saponin action at the membrane interface and of the mechanism of membrane lysis. Copyright © 2015 Elsevier B.V. All rights reserved.

Immunomodulatory effect of tea saponin in immune T-cells and T-lymphoma cells via regulation of Th1, Th2 immune response and MAPK/ERK2 signaling pathway.

PubMed

Bhardwaj, Jyoti; Chaudhary, Narendra; Seo, Hyo-Jin; Kim, Min-Yong; Shin, Tai-Sun; Kim, Jong-Deog

2014-06-01

The anti-cancer activity of saponins and phenolic compounds present in green tea was previously reported. However, the immunomodulatory and adjuvanticity activity of tea saponin has never been studied. In this study, we investigated the immunomodulatory effect of tea saponin in T-lymphocytes and EL4 cells via regulation of cytokine response and mitogen-activated protein kinases (MAPK) signaling pathway. Quantitative analysis of mRNA expression level of cytokines were performed by reverse transcription polymerase chain reaction following stimulation with tea saponin, ovalbumin (OVA) alone or tea saponin in combination with OVA. Tea saponin inhibited the proliferation of EL4 cells measured in a dose-dependent manner. No cytotoxicity effect of tea saponin was detected in T-lymphocytes; rather, tea saponin enhanced the proliferation of T-lymphocytes. Tea saponin with OVA increased the expression of interleukin (IL)-1, IL-2, IL-12, interferon-γ and tumor necrosis factor (TNF)-α and decreased the expression level of IL-10 and IL-8 in T-lymphocytes. Furthermore, tea saponin, in the presence of OVA, downregulated the MAPK signaling pathway via inhibition of IL-4, IL-8 and nuclear factor kappaB (NF-κB) in EL4 cells. Th1 cytokines enhancer and Th2 cytokines and NF-κB inhibitor, tea saponin can markedly inhibit the proliferation and invasiveness of T-lymphoma (EL4) cells, possibly due to TNF-α- and NF-κB-mediated regulation of MAPK signaling pathway.

Dietary soya saponins increase gut permeability and play a key role in the onset of soyabean-induced enteritis in Atlantic salmon ( Salmo salar L.).

PubMed

Knudsen, David; Jutfelt, Fredrik; Sundh, Henrik; Sundell, Kristina; Koppe, Wolfgang; Frøkiaer, Hanne

2008-07-01

Saponins are naturally occurring amphiphilic molecules and have been associated with many biological activities. The aim of the present study was to investigate whether soya saponins trigger the onset of soyabean-induced enteritis in Atlantic salmon (Salmo salar L.), and to examine if dietary soya saponins increase the epithelial permeability of the distal intestine in Atlantic salmon. Seven experimental diets containing different levels of soya saponins were fed to seawater-adapted Atlantic salmon for 53 d. The diets included a fishmeal-based control diet, two fishmeal-based diets with different levels of added soya saponins, one diet containing 25% lupin kernel meal, two diets based on 25% lupin kernel meal with different levels of added soya saponins, and one diet containing 25% defatted soyabean meal. The effect on intestinal morphology, intestinal epithelial permeability and faecal DM content was examined. Fish fed 25% defatted soyabean meal displayed severe enteritis, whereas fish fed 25% lupin kernel meal had normal intestinal morphology. The combination of soya saponins and fishmeal did not induce morphological changes but fish fed soya saponins in combination with lupin kernel meal displayed significant enteritis. Increased epithelial permeability was observed in fish fed 25% defatted soyabean meal and in fish fed soya saponin concentrate independent of the protein source in the feed. The study demonstrates that soya saponins, in combination with one or several unidentified components present in legumes, induce an inflammatory reaction in the distal intestine of Atlantic salmon. Soya saponins increase the intestinal epithelial permeability but do not, per se, induce enteritis.

Heterologous production of a ginsenoside saponin (compound K) and its precursors in transgenic tobacco impairs the vegetative and reproductive growth.

PubMed

Gwak, Yu Shin; Han, Jung Yeon; Adhikari, Prakash Babu; Ahn, Chang Ho; Choi, Yong Eui

2017-06-01

Production of compound K (a ginsenoside saponin) and its precursors in transgenic tobacco resulted in stunted growth and seed set failure, which may be caused by strong autotoxicity of heterologously produced phytochemicals against the tobacco itself. Panax ginseng roots contain various saponins (ginsenosides), which are major bioactive compounds. A monoglucosylated saponin, compound K (20-O-(β-D-glucopyranosyl)-20(S)-protopanaxadiol), has high medicinal and cosmetic values but is present in undetectable amounts in naturally grown ginseng roots. The production of compound K (CK) requires complicated deglycosylation of ginsenosides using physicochemical and/or enzymatic degradation. In this work, we report the production of CK in transgenic tobacco by co-overexpressing three genes (PgDDS, CYP716A47 and UGT71A28) isolated from P. ginseng. Introduction and expression of the transgenes in tobacco lines were confirmed by genomic PCR and RT-PCR. All the lines of transgenic tobacco produced CK including its precursors, protopanaxadiol and dammarenediol-II (DD). The concentrations of CK in the leaves ranged from 1.55 to 2.64 µg/g dry weight, depending on the transgenic line. Interestingly, production of CK in tobacco brought stunted plant growth and gave rise to seed set failure. This seed set failure was caused by both long-styled flowers and abnormal pollen development in transgenic tobacco. Both CK and DD treatments highly suppressed in vitro germination and tube growth in wild-type pollens. Based on these results, metabolic engineering for CK production in transgenic tobacco was successfully achieved, but the production of CK and its precursors in tobacco severely affects vegetative and reproductive growth due to the cytotoxicity of phytochemicals that are heterologously produced in transgenic tobacco.

Adjuvant effects of protopanaxadiol and protopanaxatriol saponins from ginseng roots on the immune responses to ovalbumin in mice.

PubMed

Sun, Jianhua; Hu, Songhua; Song, Xiaoming

2007-01-22

Protopanaxadiol saponins (Rg3, Rd, Rc, Rb1 and Rb2) and protopanaxatriol saponins (Rg1, Re and Rg2) isolated from the root of Panax ginseng C.A. Meyer were evaluated for their adjuvant effects on the immune responses to ovalbumin (OVA) in mice. BALB/c mice were subcutaneously injected twice at a 3-week interval with 10 microg of ovalbumin or 10 microg of OVA plus 50 microg of ginsenosides Rg3, Rd, Rc, Rb1, Rb2, Rg1, Re or Rg2 or Quil A (n=5). Blood samples were collected for measuring specific total-IgG, IgG1 and IgG2a, and splenocytes were harvested for determining lymphocyte proliferation as well as IFN-gamma and IL-5 production 2 weeks after the boosting. The results indicated that OVA-specific antibody responses were significantly higher in mice immunized with OVA co-administered with Rg1, Re, Rg2, Rg3 and Rb1 but not with Rd, Rc and Rb2 when compared with the control (immunized with OVA only). Significantly enhanced splenocyte proliferative responses to Con A, LPS and OVA as well as the production of both IL-5 and IFN-gamma stimulated by OVA were also detected in mice immunized with OVA co-administered with Rg1 but not with Rb1, Re and Rg3. Of the ginsenosides studied, Rg1, Re, Rg2, Rg3 and Rb1 have more potent adjuvant properties than the others, indicating that they are the major constituents contributing to the adjuvant activities of total ginseng saponins. Varieties of ginsenosides in adjuvant activity might be attributed to the varieties of molecular conformations determined by the side sugar chains attaching to their dammarane skeleton.

Relationship between haemolytic and adjuvant activity and structure of protopanaxadiol-type saponins from the roots of Panax notoginseng.

PubMed

Sun, Hong-Xiang; Qin, Feng; Ye, Yi-Ping

2005-12-01

Four protopanaxadiol-type saponins (PDS), ginsenosides-Rb(1), -Rd, notoginsenosides-K, -R(4) isolated from the roots of Panax notoginseng were evaluated for their haemolytic activities and adjuvant potentials on the cellular and humoral immune responses of ICR mice against ovalbumin (OVA). The effect of the substitution pattern of these PDS on their biological activities was investigated and structure-activity relationships were established. Among four PDS, the ranking of the haemolytic activity was K>R(4)>Rb(1)>Rd (P<0.01 or <0.001). Rd, Rb(1), and K could significantly enhance mitogen- and OVA-induced splenocyte proliferation in the OVA-immunized mice (P<0.001), with the order in terms of stimulation index being Rd>Rb(1)>K>R(4). OVA-specific IgG, IgG1, IgG2a and IgG2b antibody levels in the OVA-immunized mice were significantly enhanced by four PDS. Adjuvant potentials of Rd on antibody responses were higher than those of other three PDS. Meanwhile, Rd also significantly enhanced the production of the Th1 and Th2 cytokines in OVA-immunized mice (P<0.05 or <0.01). The structure-activity relationship studies suggested that the length of sugar side chains at position C-20 and the linkage of glucose moiety at position C-3 of protopanaxadiol could affect the haemolytic and adjuvant activities of PDS. The information about this structure/function relationship might be useful for developing semisynthetic tetracyclic triterpenoid saponin derivatives with immunological adjuvant activity, as well as a reference to the distribution of the functional groups composing the saponin molecule.

Evaluation of remediation process with plant-derived biosurfactant for recovery of heavy metals from contaminated soils.

PubMed

Hong, Kyung-Jin; Tokunaga, Shuzo; Kajiuchi, Toshio

2002-10-01

A washing process was studied to evaluate the efficiency of saponin on remediating heavy metal contaminated soils. Three different types of soils (Andosol: soil A, Cambisol: soil B, Regosol: soil C) were washed with saponin in batch experiments. Utilization of saponin was effective for removal of heavy metals from soils, attaining 90-100% of Cd and 85-98% of Zn extractions. The fractionations of heavy metals removed by saponin were identified using the sequential extraction. Saponin was effective in removing the exchangeable and carbonated fractions of heavy metals from soils. In recovery procedures, the pH of soil leachates was increased to about 10.7, leading to separate heavy metals as hydroxide precipitates and saponin solute. In addition recycle of used saponin is considered to be effective for the subsequent utilization. The limits of Japanese leaching test were met for all of the soil residues after saponin treatment. As a whole, this study shows that saponin can be used as a cleaning agent for remediation of heavy metal contaminated soils.

Characterization and Quantitation of Triterpenoid Saponins in Raw and Sprouted Chenopodium berlandieri spp. (Huauzontle) Grains Subjected to Germination with or without Selenium Stress Conditions.

PubMed

Lazo-Vélez, Marco A; Guajardo-Flores, Daniel; Mata-Ramírez, Daniel; Gutiérrez-Uribe, Janet A; Serna-Saldivar, Sergio O

2016-01-01

Pseudocereal Chenopodium berlandieri spp. (huauzontle) was evaluated to determine saponin composition. Saponins were evaluated in raw and germinated grains subjected to chemical stress induced by sodium selenite. Analysis by liquid chromatography coupled with ELSD detector revealed the presence of 12 saponins, identified according to compounds previously assayed in Chenopodium quinoa. Saponins found at the highest concentrations in raw grains were derived from oleanolic and phytolaccagenic acids. Total saponin concentration significantly decreased in germinated compared to raw grains due to the significant loss of 90.1% and 95.7% of the phytolaccagenic acid without and with chemical selenium stress, respectively. The most abundant saponin in germinated sprouts decreased during normal germination. Interestingly, the concentration of this particular saponin significantly increased during the Se-induced stress germination. Chemical stress with selenium salts proved to change the saponin composition in geminated Chenopodium berlandieri spp. grains, therefore affecting their potential use as ingredient in the food industry. © 2015 Institute of Food Technologists®

New steroids from Anemarrhena asphodeloides rhizome and their α-glucosidase inhibitory activity.

PubMed

Khang, Pham Van; Phuong, Dao Mai; Ma, Lei

2017-05-01

Two new steroids were isolated from acid hydrolysis residue of the rhizomes of Anemarrhena asphodeloides. Their structures were identified on the basis of several spectroscopic analysis approaches including 1D, 2D-NMR techniques, and MS data, and by the comparison of spectral data of the known compounds. The biological activities of these two isolated compounds were explored on α-glucosidase. Compound 1 displayed 4.7 folds inhibitory activity against α-glucosidase compared with the positive control acarbose.

Chemical structures of constituents from the whole plant of Bacopa monniera.

PubMed

Ohta, Tomoe; Nakamura, Seikou; Nakashima, Souichi; Oda, Yoshimi; Matsumoto, Takahiro; Fukaya, Masashi; Yano, Mamiko; Yoshikawa, Masayuki; Matsuda, Hisashi

2016-07-01

Two new dammarane-type triterpene oligoglycosides, bacomosaponins A and B, and three new phenylethanoid glycosides, bacomosides A, B1, and B2, were isolated from the whole plant of Bacopa monniera Wettst. The chemical structures of the new constituents were characterized on the basis of chemical and physicochemical evidence. In the present study, bacomosaponins A and B with acyl groups were obtained from the whole plant of B. monniera. This is the first report of acylated dammarane-type triterpene oligoglycosides isolated from B. monniera. In addition, dammarane-type triterpene saponins significantly inhibited the aggregation of 42-mer amyloid β-protein.

Microbial biotransformation of bioactive and clinically useful steroids and some salient features of steroids and biotransformation.

PubMed

Sultana, Nighat

2018-01-31

Steroids are perhaps one of the most widely used group of drugs in present day. Beside the established utilization as immunosuppressive, anti-inflammatory, anti-rheumatic, progestational, diuretic, sedative, anabolic and contraceptive agents, recent applications of steroid compounds include the treatment of some forms of cancer, osteoporosis, HIV infections and treatment of declared AIDS. Steroids isolated are often available in minute amounts. So biotransformation of natural products provides a powerful means in solving supply problems in clinical trials and marketing of the drug for obtaining natural products in bulk amounts. If the structure is complex, it is often an impossible task to isolate enough of the natural products for clinical trials. The microbial biotransformation of steroids yielded several novel metabolites, exhibiting different activities. The metabolites produced from pregnenolone acetate by Cunning hamella elegans and Rhizopus stolonifer were screened against tyrosinase and cholinesterase showed significant inhibitory activities than the parent compound. Diosgenin and its transformed sarsasapogenin were screened for their acetyl cholinesterase and butyryl cholinesterase inhibitory activities. Sarsasapogenin was screened for phytotoxicity, and was found to be more active than the parent compound. Diosgenin, prednisone and their derivatives were screened for their anti-leishmanial activity. All derivatives were found to be more active than the parent compound. The biotransformation of steroids have been reviewed to a little extent. This review focuses on the biotransformation and functions of selected steroids, the classification, advantages and agents of enzymatic biotransformation and examines the potential role of new enzymatically transformed steroids and their derivatives in the chemoprevention and treatment of other diseases. tyrosinase and cholinesterase inhibitory activities, severe asthma, rheumatic disorders, renal disorders and diseases of inflammatory bowel, skin, gastrointestinal tract. Copyright © 2018 Elsevier Inc. All rights reserved.

Inter- and intra-organ spatial distributions of sea star saponins by MALDI imaging.

PubMed

Demeyer, Marie; Wisztorski, Maxence; Decroo, Corentin; De Winter, Julien; Caulier, Guillaume; Hennebert, Elise; Eeckhaut, Igor; Fournier, Isabelle; Flammang, Patrick; Gerbaux, Pascal

2015-11-01

Saponins are secondary metabolites that are abundant and diversified in echinoderms. Mass spectrometry is increasingly used not only to identify saponin congeners within animal extracts but also to decipher the structure/biological activity relationships of these molecules by determining their inter-organ and inter-individual variability. The usual method requires extensive purification procedures to prepare saponin extracts compatible with mass spectrometry analysis. Here, we selected the sea star Asterias rubens as a model animal to prove that direct analysis of saponins can be performed on tissue sections. We also demonstrated that carboxymethyl cellulose can be used as an embedding medium to facilitate the cryosectioning procedure. Matrix-assisted laser desorption/ionization (MALDI) imaging was also revealed to afford interesting data on the distribution of saponin molecules within the tissues. We indeed highlight that saponins are located not only inside the body wall of the animals but also within the mucus layer that probably protects the animal against external aggressions. Graphical Abstract Saponins are the most abundant secondary metabolites in sea stars. They should therefore participate in important biological activities. Here, MALDI imaging is presented as a powerful method to determine the spatial distribution of saponins within the animal tissues. The inhomogeneity of the intra-organ saponin distribution is highlighted, paving the way for future elegant structure/activity relationship investigations.

On the mode of action of ACTH on the isolated perfused adrenal gland

PubMed Central

Jaanus, Siret D.; Rosenstein, M. J.; Rubin, R. P.

1970-01-01

1. Isolated cat adrenal glands were perfused with Locke solution, and the corticosteroid outputs in response to adrenocorticotrophin (ACTH) were studied. 2. Steroid outputs varied with the ACTH concentration, as well as with the duration of exposure to a given ACTH concentration. 3. Omission of calcium from the perfusion medium markedly depressed ACTH-evoked steroid release. The steroid output was directly related to the extracellular calcium concentration up to 0·5 mM. 4. During a constant exposure to ACTH, steroid output was maintained for at least 2-3 hr, provided that calcium was present in the perfusion medium. 5. Strontium, but not barium or magnesium, replaced calcium in maintaining the secretory response to ACTH. 6. Magnesium depressed ACTH-evoked secretion in the presence of calcium, and this depression of secretion was antagonized by increasing the calcium concentration. 7. Prolonged perfusion with sodium-free or potassium-free solutions did not markedly inhibit steroid output in response to ACTH. Excess potassium (56 mM) did not produce a consistent or marked increase in spontaneous steroid output and did not affect the response to ACTH. 8. The steroid content of adrenal glands perfused with Locke solution and exposed to ACTH was about 10% of the amount which was secreted. By contrast, adrenal glands perfused with calcium-free media and exposed to ACTH contained much higher amounts of steroid, despite the negligible amount secreted. 9. These data suggest that calcium plays a critical role in the mechanism of corticosteroid secretion from the adrenal cortex. PMID:4322584

Investigating Therapeutic Potential of Trigonella foenum-graecum L. as Our Defense Mechanism against Several Human Diseases.

PubMed

Goyal, Shivangi; Gupta, Nidhi; Chatterjee, Sreemoyee

2016-01-01

Current lifestyle, stress, and pollution have dramatically enhanced the progression of several diseases in human. Globally, scientists are looking for therapeutic agents that can either cure or delay the onset of diseases. Medicinal plants from time immemorial have been used frequently in therapeutics. Of many such plants, fenugreek is one of the oldest herbs which have been identified as an important medicinal plant by the researchers around the world. It is potentially beneficial in a number of diseases such as diabetes, hypercholesterolemia, and inflammation and probably in several kinds of cancers. It has industrial applications such as synthesis of steroidal hormones. Its medicinal properties and their role in clinical domain can be attributed to its chemical constituents. The 3 major chemical constituents which have been identified as responsible for principle health effects are galactomannan, 4-OH isoleucine, and steroidal saponin. Numerous experiments have been carried out in vivo and in vitro for beneficial effects of both the crude chemical and of its active constituent. Due to its role in health care, the functional food industry has referred to it as a potential nutraceutical. This paper is about various medicinal benefits of fenugreek and its potential application as therapeutic agent against several diseases.

Activity of Saponins from Medicago species Against HeLa and MCF-7 Cell Lines and their Capacity to Potentiate Cisplatin Effect.

PubMed

Avato, Pinarosa; Migoni, Danilo; Argentieri, Mariapia; Fanizzi, Francesco P; Tava, Aldo

2017-11-24

Saponins from Medicago species display several biological activities, among them apoptotic effects against plant cells have been evidenced. In contrast, their cytotoxic and antitumor activity against animal cells have not been studied in great details. To explore the cytotoxic properties of saponin from Medicago species against animal cells and their effect in combination with the antitumoral drug cisplatin. Cytotoxic activity of saponin mixtures from M. arabica (tops and roots), M. arborea (tops) and M. sativa (tops, roots and seeds) and related prosapogenins from M. arborea and M. sativa (tops) against HeLa and MCF-7 cell lines is described. In addition, cytotoxicity of soyasaponin I and purified saponins (1-8) of hederagenin, medicagenic and zanhic acid is also presented. Combination experiments with cisplatin have been also conducted. Saponins from M. arabica tops and roots (mainly monodesmosides of hederagenin and bayogenin) were the most effective to reduce proliferation of HeLa and MCF-7 cell lines. Among the purified saponins, the most cytotoxic was saponin 1, 3-O-ß-D-glucopyranosyl(1→2)-α-L-arabinopyranosyl hederagenin. When saponins, derived prosapogenins and pure saponins were used in combination with cisplatin, they all, to different extent, were able to potentiate cisplatin activity against HeLa cells but not against MCF-7 cell lines. Moreover uptake of cisplatin in these cell lines was significantly reduced. Overall results showed that specific molecular types of saponins (hederagenin glycosides) have potential as anti-cancer agents or as leads for anti-cancer agents. Moreover saponins from Medicago species have evidenced interesting properties to mediate cisplatin effects in tumor cell lines. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

[Preparation of O/W ginseng saponins-based nanoemulsion and its amplified immune response].

PubMed

Cao, Fahao; Ouyang, Wuqing; Wang, Yanping

2010-02-01

To prepare an O/W ginseng saponins-based nanoemulsion and investigate its amplified immune response. The formulation of ginseng saponins-based nanoemulsion was optimized via the range of nanoemulsion zone in phase diagrams and the solubility of ginseng saponins. Its physicochemical properties were investigated, including morphology, particle size distribution, pH, viscosity and stability. Ginseng saponins-based nanoemulsion as adjuvant was co-administrated with a model antigen ovalbumin (OVA) in mice. Two weeks after the boosting, the serum levels of OVA-specific antibody and its isotypes were determined. The optimized ginseng saponins-based nanoemulsion formulation consisted of ginseng saponins, IPM, Cremophor RH 40, glycerol and water (with the weight ratio of 2 : 4 : 17.8 : 17.8 : 58.4), which was a light yellow fluid. The shape of droplets was spherical under transmission electron microscopy with an average diameter of 72.20 nm and a polydispersity index of 0.052. The viscosity and pH value of it were 4.20 s and 6.02, respectively. And it showed good stability. When co-administered with OVA, no obvious side effects were observed in the mice immunized with ginseng saponin-based nanoemulsion. The serum levels of IgG, IgG1 and IgG2a antibody in the group of ginseng saponin-based nanoemulsion immunized mice was significantly increased compared to the groups of OVA and the saline solution of ginseng saponin. Compared with the adjuvant aluminium hydroxide, the serum levels of IgG and IgG1 antibodys in the groups of ginseng saponins-based nanoemulsion had no significant difference, but the level of IgG2a was obviously higher. ginseng saponin-based nanoemulsion could amplify the Th1 and Th2 immune responses, and can be used as the vaccine adjuvant.

A missense mutation in the human cytochrome b5 gene causes 46,XY disorder of sex development due to true isolated 17,20 lyase deficiency.

PubMed

Idkowiak, Jan; Randell, Tabitha; Dhir, Vivek; Patel, Pushpa; Shackleton, Cedric H L; Taylor, Norman F; Krone, Nils; Arlt, Wiebke

2012-03-01

Isolated 17,20 lyase deficiency is commonly defined by apparently normal 17α-hydroxylase activity but severely reduced 17,20 lyase activity of the bifunctional enzyme cytochrome P450 (CYP) enzyme 17A1 (CYP17A1), resulting in sex steroid deficiency but normal glucocorticoid and mineralocorticoid reserve. Cytochrome b5 (CYB5A) is thought to selectively enhance 17,20 lyase activity by facilitating the allosteric interaction of CYP17A1 with its electron donor P450 oxidoreductase (POR). We investigated a large consanguineous family including three siblings with 46,XY disorder of sex development (DSD) presenting with isolated 17,20 lyase deficiency. We investigated the clinical and biochemical phenotype, conducted genetic analyses, and functionally characterized the identified CYB5A mutation in cell-based CYP17A1 coexpression assays. All three siblings presented with 46,XY DSD, sex steroid deficiency, normal mineralocorticoids and glucocorticoids, and a urine steroid metabolome suggestive of isolated 17,20 lyase deficiency. CYP17A1 and POR sequences were normal, but we detected a homozygous CYB5A missense mutation (g.28,400A→T; p.H44L). Functional in vitro analysis revealed normal CYP17A1 17α-hydroxylase activity but severely impaired 17,20 lyase activity. In silico analysis suggested the disruption of CYB5A heme binding by p.H44L. We have identified the first human CYB5A missense mutation as the cause of isolated 17,20 lyase deficiency in three individuals with 46,XY DSD. Detailed review of previously reported cases with apparently isolated 17,20 lyase deficiency due to mutant CYP17A1 and POR reveals impaired 17α-hydroxylase activity as assessed by steroid metabolome analysis and short cosyntropin testing. This suggests that truly isolated 17,20 lyase deficiency is observed only in individuals with inactivating CYB5A mutations.

Anti-diabetic activity of Holothuria thomasi saponin.

PubMed

El Barky, Amira R; Hussein, Samy A; Alm-Eldeen, Abeer A; Hafez, Yehia A; Mohamed, Tarek M

2016-12-01

Diabetes mellitus represents a global health problem. It characterized by hyperglycemia that induces oxidative stress leading to a generation of free radicals. A wide variety of natural products in plants and other marine animals represent antioxidant activity and other health benefits like those of sea cucumber. Therefore, this study aimed to investigate the antidiabetic activity of glycosidic compound - saponin - derived from the Egyptian sea cucumber, Holothuria thomasi. Saponin has been extracted from the Egyptian sea cucumber and confirmed by hemolysis, Salkowski tests, FT/IR, UV and GC-MS analysis. Eighty white female albino rats were divided into four equal groups. The first two groups of rats; control normal and control normal saponin-treated groups. The last two groups which were made diabetic by intraperitoneal injection of streptozotocin had one diabetic control and the other diabetic group that got 300mg/kg B.wt. of saponin extract after Thirty-five days after diabetes induction and lasted for six weeks. The functional group of saponin extract which established with FT/IR spectroscopy demonstrated the presence of saponin in the extracted materials as shown in the peak of the functional group in relevance to the standard one. The UV spectra revealed that λ max of saponin extract was 282nm which in accordance to the standard saponin. Also, GC-MS analysis indicated that the aglycone part of saponin was methyl esters of octadecanoic acid. Saponin extract significantly decreased serum glucose, α-amylase activity, adiponectin, IL-6, TNF-α concentrations and liver L-MDA. However, serum insulin and liver glycogen levels were significantly increased as compared with the diabetic non-treated groups. The histopathological results supported that saponin extract markedly reduced the degenerative change in β-cells. This study, therefore, depicts that the Egyptian Holothuria thomasi, sea cucumber saponin as a hypoglycemic agent with the potential to normalize aberrant biochemical parameters and preserved the normal histological architecture of the islets cells of pancreatic tissues. Copyright © 2016 Elsevier Masson SAS. All rights reserved.

Studies on saponin production in tropical medicinal plants Maesa argentea and Maesa lanceolata

NASA Astrophysics Data System (ADS)

Faizal, Ahmad; Geelen, Danny

2015-09-01

The continuous need for new compounds with important medicinal activities has lead to the identification and characterization of various plant-derived natural products. As a part of this program, we studied the saponin production from two tropical medicinal plants Maesa argentea and M. lanceolata and evaluated several treatments to enhance their saponin production. In this experiment, we present the analyses of saponin production from greenhouse grown plants by means of TLC and HPLC-MS. We observed that the content of saponin from these plants varied depending on organ and physiological age of the plants. In addition, the impact of elicitors on saponin accumulation on in vitro grown plants was analyzed using TLC. The production of saponin was very stable and not affected by treatment with methyl jasmonate, and salicylic acid. In conclusion, Maesa saponins are constitutively produced in plants and the level of these compounds in plants is mainly affected by the developmental or physiological stage.

Methanolic Root Extract of Rauwolfia serpentina Benth Improves the Glycemic, Antiatherogenic, and Cardioprotective Indices in Alloxan-Induced Diabetic Mice

PubMed Central

Azmi, Muhammad Bilal; Qureshi, Shamim A.

2012-01-01

The aim of the study was to evaluate the phytochemistry and the effect of methanolic root extract (MREt) of Rauwolfia serpentina on alloxan-induced diabetic Wister male mice. Mice were divided in control (distilled water at 1 mL/kg) and alloxan-induced diabetic mice which subdivided into diabetic (distilled water at 1 mL/kg), negative (0.05% dimethyl sulfoxide at 1 mL/kg), positive (glibenclamide at 5 mg/kg) controls, and three test groups (MREt at 10, 30, and 60 mg/kg). All treatments were given orally for 14 days. Qualitatively MREt showed the presence of alkaloids, carbohydrates, flavonoids, glycosides, cardiac glycosides, phlobatannins, resins, saponins, steroids, tannins, and triterpenoids, while quantitatively extract was rich in total phenols. The flavonoids, saponins and alkaloids were also determined in root powder. MREt found effective in improving the body weights, glucose and insulin levels, insulin/glucose ratio, glycosylated and total hemoglobin in test groups as compared to diabetic control. Similarly, significantly decreased levels of total cholesterol, triglycerides, low-density lipoprotein (LDL-c), and very low-density lipoprotein (VLDL-c) cholesterols were found in test groups. Significant lipolysis with improved glycogenesis was also found in liver tissues of all test groups. ALT levels were found normal in all groups. Thus, MREt improves the glycemic, antiatherogenic, coronary risk, and cardioprotective indices in alloxan-induced diabetic mice. PMID:23365565

Phytochemical and nutrient/antinutrient interactions in cherry tomato (Lycopersicon esculentum) fruits.

PubMed

Oyetayo, Folake Lucy; Ibitoye, Muyiwa Femi

2012-07-01

The fruit of the cherry tomato (Lycopersicon esculentum (Solanaceae)) was analysed for mineral and antinutrient composition. Phosphorus (33.04 ± 0.21 mg/100g) was the most abundant mineral in the fruit, followed by calcium (32.04 ± 0.06 mg/100 g), and potassium (11.9 ± 0.1 mg/100 g) and manganese (9.55 ± 0.28 mg/100 g) were also present in appreciable quantities. Antinutrients, including phytate, glycoside, saponin and tannin, were screened and quantified. Phytate (112.82 ± 0.1 mg/100 g), glycoside (2.33 ± 0.00 mg/100 g), saponin (1.31 ± 0.00 mg/100g) and tannin (0.21 ± 0.00 mg/100 g) were present in the fruit but phlobatanin and glycosides with steroidal rings were not found. The calculated calcium:phytate ratio of the fruits was below the critical value and the calculated [calcium] [phytate]:[zinc] molar ratio was less than the critical value. The calcium:phosphorus ratio (0.97 mg/100 g) shows the fruit to be a good source of food nutrients, while the sodium:potassium value was less than 1. Ca/P ratio below 0.5 indicates deficiency of these minerals while Na/K ratio above 1 is detrimental because of excessive sodium levels. The results of the study generally revealed the fruit to be rich in minerals but containing insufficient quantities of antinutrients to result in poor mineral bioavailability.

Functionalized PHB granules provide the basis for the efficient side-chain cleavage of cholesterol and analogs in recombinant Bacillus megaterium.

PubMed

Gerber, Adrian; Kleser, Michael; Biedendieck, Rebekka; Bernhardt, Rita; Hannemann, Frank

2015-07-29

Cholesterol, the precursor of all steroid hormones, is the most abundant steroid in vertebrates and exhibits highly hydrophobic properties, rendering it a difficult substrate for aqueous microbial biotransformations. In the present study, we developed a Bacillus megaterium based whole-cell system that allows the side-chain cleavage of this sterol and investigated the underlying physiological basis of the biocatalysis. CYP11A1, the side-chain cleaving cytochrome P450, was recombinantly expressed in the Gram-positive soil bacterium B. megaterium combined with the required electron transfer proteins. By applying a mixture of 2-hydroxypropyl-β-cyclodextrin and Quillaja saponin as solubilizing agents, the zoosterols cholesterol and 7-dehydrocholesterol, as well as the phytosterol β-sitosterol could be efficiently converted to pregnenolone or 7-dehydropregnenolone. Fluorescence-microscopic analysis revealed that cholesterol accumulates in the carbon and energy storage-serving poly(3-hydroxybutyrate) (PHB) bodies and that the membrane proteins CYP11A1 and its redox partner adrenodoxin reductase (AdR) are likewise localized to their surrounding phospholipid/protein monolayer. The capacity to store cholesterol was absent in a mutant strain devoid of the PHB-producing polymerase subunit PhaC, resulting in a drastically decreased cholesterol conversion rate, while no effect on the expression of the recombinant proteins could be observed. We established a whole-cell system based on B. megaterium, which enables the conversion of the steroid hormone precursor cholesterol to pregnenolone in substantial quantities. We demonstrate that the microorganism's PHB granules, aggregates of bioplastic coated with a protein/phospholipid monolayer, are crucial for the high conversion rate by serving as substrate storage. This microbial system opens the way for an industrial conversion of the abundantly available cholesterol to any type of steroid hormones, which represent one of the biggest groups of drugs for the treatment of a wide variety of diseases.

Direct identification of bacteria from BacT/ALERT anaerobic positive blood cultures by MALDI-TOF MS: MALDI Sepsityper kit versus an in-house saponin method for bacterial extraction.

PubMed

Meex, Cécile; Neuville, Florence; Descy, Julie; Huynen, Pascale; Hayette, Marie-Pierre; De Mol, Patrick; Melin, Pierrette

2012-11-01

In cases of bacteraemia, a rapid species identification of the causal agent directly from positive blood culture broths could assist clinicians in the timely targeting of empirical antimicrobial therapy. For this purpose, we evaluated the direct identification of micro-organisms from BacT/ALERT (bioMérieux) anaerobic positive blood cultures without charcoal using the Microflex matrix-assisted laser desorption/ionization (MALDI) time of flight MS (Bruker), after bacterial extraction by using two different methods: the MALDI Sepsityper kit (Bruker) and an in-house saponin lysis method. Bruker's recommended criteria for identification were expanded in this study, with acceptance of the species identification when the first three results with the best matches with the MALDI Biotyper database were identical, whatever the scores were. In total, 107 monobacterial cultures and six polymicrobial cultures from 77 different patients were included in this study. Among monomicrobial cultures, we identified up to the species level 67 and 66 % of bacteria with the MALDI Sepsityper kit and the saponin method, respectively. There was no significant difference between the two extraction methods. The direct species identification was particularly inconclusive for Gram-positive bacteria, as only 58 and 52 % of them were identified to the species level with the MALDI Sepsityper kit and the saponin method, respectively. Results for Gram-negative bacilli were better, with 82.5 and 90 % of correct identification to the species level with the MALDI Sepsityper kit and the saponin method, respectively. No misidentifications were given by the direct procedures when compared with identifications provided by the conventional method. Concerning the six polymicrobial blood cultures, whatever the extraction method used, a correct direct identification was only provided for one of the isolated bacteria on solid medium in all cases. The analysis of the time-to-result demonstrated a reduction in the turnaround time for identification ranging from 1 h 06 min to 24 h 44 min, when performing the blood culture direct identification in comparison with the conventional method, whatever the extraction method.

Application of aqueous saponin on the remediation of polycyclic aromatic hydrocarbons-contaminated soil.

PubMed

Kobayashi, Takayuki; Kaminaga, Hirohisa; Navarro, Ronald R; Iimura, Yosuke

2012-01-01

The aim of this research was to evaluate the feasibility of aqueous saponin for the removal and biodegradation of polycyclic aromatic hydrocarbons (PAHs) from contaminated soil. Dissolution test confirmed the ability of saponin to increase the apparent solubility of the tested 3-5 rings PAH above the critical micelle concentration (approximately 1000 mg/L). Microbial test with pure culture of Sphingomonas sp. showed that saponin significantly enhanced the degradation of pyrene. For example, the percent degradation was 2.1 times higher in the presence of 2500 mg/L saponin than that of control without saponin after 60 hours incubation at around 10(8) CFU/mL initial cell loading. These results suggest that the binding of pyrene with saponin does not pose a serious constraint to bacterial uptake. Contrary to pyrene, saponin was chemically stable against the PAHs degrader. It is also not toxic to the cell at least up to 2500 mg/L. Finally, using a spiked soil sample, extraction tests with 10,000 mg/L of saponin showed that around 52.7% and 0.3% of pyrene was removed from low and high organic spiked soils, respectively. The results from this study indicate that aqueous saponin is appropriate as a washing agent as well as biodegradation enhancer for the detoxification of PAHs-contaminated low organic carbon soil.

Four new steroids from the endophytic fungus Chaetomium sp. M453 derived of Chinese herbal medicine Huperzia serrata.

PubMed

Yu, Fei-Xue; Li, Zhe; Chen, Yao; Yang, Yin-He; Li, Guo-Hong; Zhao, Pei-Ji

2017-03-01

An endophytic fungus, Chaetomium sp. M453, was isolated from Huperzia serrata (Thunb. ex Murray) Trev. and subjected to phytochemical investigation. Three unusual C25 steroids, neocyclocitrinols E-G (1-3), and 3β-hydroxy-5,9-epoxy-(22E,24R)-ergosta-7,22-dien-6-one (4) together with three known steroids were isolated from solid fermentation products of the fungus, which were elucidated by extensive spectroscopic analyses, including 1D-, 2D-NMR, and HR-ESI-MS experiments. The absolute configuration of 1 was determined by X-ray crystallographic analysis and CD analyses. The acetylcholinesterase inhibitory activities of compounds 1-4 were tested in vitro. Compound 4 showed weak acetylcholinesterase inhibitory activity. Copyright © 2016 Elsevier B.V. All rights reserved.

Control of water-borne parasitic diseases with natural products: the potential of Dialium guineense as a molluscicide.

PubMed

Houghton, P J; Odukoya, O A; Adelusi, A; Omogbai, E K; Sanderson, L; Whitfield, P J

1997-01-01

The molluscicidal activity of the fruit and leaves of Dialium guineense was found to be due to glycosides of the triterpenoid oleanolic acid. Three glycosides were isolated from the fruit and a fourth from the leaves and are known compounds. The amount of total saponins present in D. guineense makes it a good candidate for a readily available molluscicide in Nigerian villages.

Components characterization of total tetraploid jiaogulan (Gynostemma pentaphylla) saponin and its cholesterol-lowering properties

USDA-ARS?s Scientific Manuscript database

This study characterized chemical structures of tetraploid jiaogulan saponins, and investigated their cholesterol-lowering effects and mechanisms in hamsters fed a high-fat diet (HFD). Nine saponins, including five reported for the first time, were obtained from total jiaogulan saponins (TJS) and el...

High-performance liquid chromatography analysis of plant saponins: An update 2005-2010

PubMed Central

Negi, Jagmohan S.; Singh, Pramod; Pant, Geeta Joshi Nee; Rawat, M. S. M.

2011-01-01

Saponins are widely distributed in plant kingdom. In view of their wide range of biological activities and occurrence as complex mixtures, saponins have been purified and separated by high-performance liquid chromatography using reverse-phase columns at lower wavelength. Mostly, saponins are not detected by ultraviolet detector due to lack of chromophores. Electrospray ionization mass spectrometry, diode array detector , evaporative light scattering detection, and charged aerosols have been used for overcoming the detection problem of saponins. PMID:22303089

Five new triterpene saponins, polygalasaponins XXVIII-XXXII from the root of Polygala japonica Houtt.

PubMed

Zhang, D; Miyase, T; Kuroyanagi, M; Umehara, K; Ueno, A

1996-04-01

Five new oleanane-type saponins, polygalasaponins XXVIII-XXXII, along with one known saponin, polygalasaponin XXIV, and one known acylated sucrose, tenuifoliside C, were isolated from the root of Polygala japonica. The structures of these new compounds were elucidated as 3-O-beta-D-glucopyranosyl pesenegenin 28-O-beta-D-xylopyranosyl (1-->4)-alpha-L-rhamnopyranosyl (1-->2)-beta-D-fucopyranosyl ester, 3-O-beta-D-glucopyranosyl presenegenin 28-O-beta-D-galactopyranosyl (1-->5)-beta-D-apiofuranosyl (1-->4)-beta-D-xylopyranosyl (1-->4)-alpha-L-rhamno-pyranosyl (1-->2)-beta-D-fucopyranosyl ester, 3-O-beta-D-glucopyranosyl presenegenin 28-O-beta-D-galactopyranosyl (1-->4)-beta-D-xylopyranosyl (1-->4)-alpha-L-rhamnopyranosyl (1-->2)-[4-O-p-methoxycinnamoyl]-[beta-D-glucopyranosyl (1-->3)]-beta-D-fucopyranosyl ester, 3-O-beta-D-glucopyranosyl presenegenin 28-O-alpha-L-arabinopyranosyl (1-->3)-beta-D-xylopyranosyl (1-->4)-[beta-D-apiofuranosyl (1-->3)]-alpha-L-rhamnopyranosyl (1-->2)-[4-O-3,4,5-trimethoxycinnamoyl]-beta-D-fucopyranosyl ester, 3-O-beta-D-glucopyranosyl persenegenin 28-O-alpha-L-arabinopyranosyl (1-->3)-beta-D-xylopyranosyl (1-->4)-[beta-D-apiofuranosyl (1-->3)-alpha-L-rhamnopyranosyl (1-->2)-[4-O-p-methoxycinnamoyl]-[alpha-L-rhamnopyranosyl (1-->3)-beta-D-fucopyranosyl ester, respectively, on the basis of spectroscopic and chemical evidence.

Direct detection of saponins in crude extracts of soapnuts by FTIR.

PubMed

Almutairi, Meshari Saad; Ali, Muhammad

2015-01-01

Direct detection of saponins in soapnuts (Sapindus mukorossi) using Fourier transform infrared (FTIR) spectroscopy is investigated in this project. Potassium bromide powder was mixed with extracted powder of soapnuts and compressed to a thin pellet for examination process. The outcome of the FTIR spectra of saponin demonstrated characteristic triterpenoid saponin absorptions of OH, C = O, C-H, and C = C, while the glycoside linkages to the sapogenins were indicated by the absorptions of C-O. The significance of this study is that saponin absorption peaks are directly detectable in crude aqueous and 95% ethanol extracts of soapnuts powder using FTIR spectroscopy, thereby eliminating the need of further expensive and exhaustive purification steps. The extracts of soapnuts were screened for saponins along with controls by phytochemical tests, and advanced spectroscopic techniques such as ultra fast liquid chromatography and ultra performance liquid chromatography quadrupole-time of flight-mass spectrometry were also implemented to validate the saponins.

[Investigation on the process of sapindus saponin purified with macroporous adsorption resin and screening of its bacteriostasis].

PubMed

Fu, Yong; Lei, Peng; Han, Yu-mei; Yan, Dan

2010-02-01

To study the technological parameters of the purification process of saponins with macroporous adsorption resin. The adsorptive characteristics and elutive parameters of the process were studied by taking the elutive and purified ratio of saponins as markers. Bacteriostasis activity of each parts eluted was evaluated by the mean of cup-plate method. 13.6 mL of the extraction of sapindus saponin (crude drugs 0.01 g/mL) was purified with a column of macroporous adsorption resin (phi15 mm x H90 mm, dry weight 2.5 g) and washed with 3BV of distilled water, then eluted with 3BV of 30% ethanol and 3BV of 70% ethanol, most of saponins were collected in the 70% ethanol. With macroporous adsorption resin adsorbing and purifying, the elutive ratio of saponins was 93.8% and the purity reached 250.1%. So this process of applying macroporous adsorption resin to adsorb and purify saponins is feasible, and supplies reference to the purification of other types of saponin.

Influence of gastrointestinal digestion and edible plant combination on oral bioavailability of triterpene saponins, using a biomimetic digestion and absorption system and determination by HPLC.

PubMed

Li, Shun-Xing; Mu, Yang; Zheng, Feng-Ying

2013-11-06

Saponins have many biological activities, but their overload could cause toxicity to the human body. Bionic gastrointestinal digestion and monolayer liposome extraction were used for oral bioavailability assessment of triterpene saponins (notoginsenoside R1, ginsenosides Rb1 and Rd1) in an edible herb (San-Chi) and its compound herbal medicine (Pien Tze Huang, PZH). The concentrations of affinity-monolayer liposome saponins in the chyme were determined by HPLC and used for oral bioavailability assessment. With the digestion of San-Chi and PZH from the stomach to the intestine, the release of saponins in their chyme was increased. The intestinal absorption ratios of N-R1, G-Rb1, G-Rd1, and total saponins from San-Chi were 86.57, 18.56, 73.30, and 40.20%, respectively, which were more than those from PZH (i.e., 19.56, 10.11, 30.11, and 16.08%). The oral bioavailability of saponins was controlled by saponin species, gastrointestinal digestion, and edible plants combination.

Effect of saponins on n-hexane removal in biotrickling filters.

PubMed

Tu, Yanhong; Yang, Chunping; Cheng, Yan; Zeng, Guangming; Lu, Li; Wang, Lu

2015-01-01

Saponins was applied to enhance the removal of n-hexane in a biotrickling filter (BTF) in this study. Comparison experiments were carried out to examine the effect of saponins on n-hexane removal in two BTFs at various saponins concentrations, n-hexane loading rates (LRs) and gas empty bed contact times (EBCTs). Results show that the optimum concentration of saponins in nutrient feed was 50.0mgL(-1). When organic LR of n-hexane increased from 47.8 to 120.0gm(-3)h(-1), the removal efficiency (RE) for BTF1 (with saponins) and BTF2 (without saponins) decreased from 91.3% to 83.3% and from 62.8% to 56.8%, respectively. As gas EBCT decreased from 30.0 to 7.5s, the RE declined from 88.4% to 64.5% for BTF1 and from 61.4% to 38.3% for BTF2. Saponins could also decrease the biomass accumulation rate within the medium bed. These results could be referred in the design and operation of BTFs for hydrophobic VOC removal. Copyright © 2014 Elsevier Ltd. All rights reserved.

Application of saponin biosurfactant and its recovery in the MEUF process for removal of methyl violet from wastewater.

PubMed

Samal, Kulbhushan; Das, Chandan; Mohanty, Kaustubha

2017-12-01

The potential of saponin, a biosurfactant, in the micellar enhanced ultrafiltration (MEUF) process was tested systematically for removal of methyl violet from wastewater. For this, the aqueous extract of reetha (Sapindus mukorossi) pericarp which contains saponin was used as the biosurfactant. First, the micellar solubilization of methyl violet in saponin micelles was investigated in terms of molar solubilization power (SP) of saponin. It was observed that the adsorption of methyl violet on the agglomerates of saponin micelles was mainly responsible for the enhanced solubilization. The Gibbs free energy of solubilization (calculated as -29.63 kJ mol -1 ) suggested that process was feasible and spontaneous. The MEUF experiments were performed in batch as well as continuous mode using saponin biosurfactant, and the effect of operating parameters on permeate flux and solute retention were evaluated. The removal of methyl violet in MEUF process was >99% achieved with 10 kDa polyethersulfone (PES) membrane for feed dye concentration of 250 mg L -1 at studied conditions. Finally, the saponin in permeate was recovered using n-heptane and n-butanol by solvent extraction process. The solvent n-butanol showed better extraction efficiency as compared to n-heptane for saponin extraction. Copyright © 2017 Elsevier Ltd. All rights reserved.

Tackling saponin diversity in marine animals by mass spectrometry: data acquisition and integration.

PubMed

Decroo, Corentin; Colson, Emmanuel; Demeyer, Marie; Lemaur, Vincent; Caulier, Guillaume; Eeckhaut, Igor; Cornil, Jérôme; Flammang, Patrick; Gerbaux, Pascal

2017-05-01

Saponin analysis by mass spectrometry methods is nowadays progressively supplementing other analytical methods such as nuclear magnetic resonance (NMR). Indeed, saponin extracts from plant or marine animals are often constituted by a complex mixture of (slightly) different saponin molecules that requires extensive purification and separation steps to meet the requirement for NMR spectroscopy measurements. Based on its intrinsic features, mass spectrometry represents an inescapable tool to access the structures of saponins within extracts by using LC-MS, MALDI-MS, and tandem mass spectrometry experiments. The combination of different MS methods nowadays allows for a nice description of saponin structures, without extensive purification. However, the structural characterization process is based on low kinetic energy CID which cannot afford a total structure elucidation as far as stereochemistry is concerned. Moreover, the structural difference between saponins in a same extract is often so small that coelution upon LC-MS analysis is unavoidable, rendering the isomeric distinction and characterization by CID challenging or impossible. In the present paper, we introduce ion mobility in combination with liquid chromatography to better tackle the structural complexity of saponin congeners. When analyzing saponin extracts with MS-based methods, handling the data remains problematic for the comprehensive report of the results, but also for their efficient comparison. We here introduce an original schematic representation using sector diagrams that are constructed from mass spectrometry data. We strongly believe that the proposed data integration could be useful for data interpretation since it allows for a direct and fast comparison, both in terms of composition and relative proportion of the saponin contents in different extracts. Graphical Abstract A combination of state-of-the-art mass spectrometry methods, including ion mobility spectroscopy, is developed to afford a complete description of the saponin molecules in natural extracts.

Effect of saponin treatment on the sarcoplasmic reticulum of rat, cane toad and crustacean (yabby) skeletal muscle.

PubMed Central

Launikonis, B S; Stephenson, D G

1997-01-01

1. Mechanically skinned fibres from skeletal muscles of the rat, toad and yabby were used to investigate the effect of saponin treatment on sarcoplasmic reticulum (SR) Ca2+ loading properties. The SR was loaded submaximally under control conditions before and after treatment with saponin and SR Ca2+ was released with caffeine. 2. Treatment with 10 micrograms ml-1 saponin greatly reduced the SR Ca2+ loading ability of skinned fibres from the extensor digitorum longus muscle of the rat with a rate constant of 0.24 min-1. Saponin concentrations up to 150 micrograms ml-1 and increased exposure time up to 30 min did not further reduce the SR Ca2+ loading ability of the SR, which indicates that the inhibitory action of 10-150 micrograms ml-1 saponin is not dose dependent. The effect of saponin was also not dependent on the state of polarization of the transverse-tubular system. 3. Treatment with saponin at concentrations up to 100 micrograms ml-1 for 30 min did not affect the Ca2+ loading ability of SR in skinned skeletal muscle fibres from the twitch portion of the toad iliofibularis muscle but SR Ca2+ loading ability decreased markedly with a time constant of 0.22 min-1 in the presence of 150 micrograms ml-1 saponin. 4. The saponin dependent increase in permeability could be reversed in both rat and toad fibres by short treatment with 6 microM Ruthenium Red, a potent SR Ca2+ channel blocker, suggesting that saponin does affect the SR Ca2+ channel properties in mammalian and anuran skeletal muscle. 5. Treatment of skinned fibres of long sarcomere length (> 6 microns) from the claw muscle of the yabby (a freshwater decapod crustacean) with 10 micrograms ml-1 saponin for 30 min abolished the ability of the SR to load Ca2+, indicating that saponin affects differently the SR from skeletal muscles of mammals, anurans and crustaceans. 6. It is concluded that at relatively low concentrations, saponin causes inhibition of the skeletal SR Ca2+ loading ability in a species dependent manner, probably by increasing the Ca2+ loss through SR Ca2+ release channels. PMID:9365915

Effect of saponin treatment on the sarcoplasmic reticulum of rat, cane toad and crustacean (yabby) skeletal muscle.

PubMed

Launikonis, B S; Stephenson, D G

1997-10-15

1. Mechanically skinned fibres from skeletal muscles of the rat, toad and yabby were used to investigate the effect of saponin treatment on sarcoplasmic reticulum (SR) Ca2+ loading properties. The SR was loaded submaximally under control conditions before and after treatment with saponin and SR Ca2+ was released with caffeine. 2. Treatment with 10 micrograms ml-1 saponin greatly reduced the SR Ca2+ loading ability of skinned fibres from the extensor digitorum longus muscle of the rat with a rate constant of 0.24 min-1. Saponin concentrations up to 150 micrograms ml-1 and increased exposure time up to 30 min did not further reduce the SR Ca2+ loading ability of the SR, which indicates that the inhibitory action of 10-150 micrograms ml-1 saponin is not dose dependent. The effect of saponin was also not dependent on the state of polarization of the transverse-tubular system. 3. Treatment with saponin at concentrations up to 100 micrograms ml-1 for 30 min did not affect the Ca2+ loading ability of SR in skinned skeletal muscle fibres from the twitch portion of the toad iliofibularis muscle but SR Ca2+ loading ability decreased markedly with a time constant of 0.22 min-1 in the presence of 150 micrograms ml-1 saponin. 4. The saponin dependent increase in permeability could be reversed in both rat and toad fibres by short treatment with 6 microM Ruthenium Red, a potent SR Ca2+ channel blocker, suggesting that saponin does affect the SR Ca2+ channel properties in mammalian and anuran skeletal muscle. 5. Treatment of skinned fibres of long sarcomere length (> 6 microns) from the claw muscle of the yabby (a freshwater decapod crustacean) with 10 micrograms ml-1 saponin for 30 min abolished the ability of the SR to load Ca2+, indicating that saponin affects differently the SR from skeletal muscles of mammals, anurans and crustaceans. 6. It is concluded that at relatively low concentrations, saponin causes inhibition of the skeletal SR Ca2+ loading ability in a species dependent manner, probably by increasing the Ca2+ loss through SR Ca2+ release channels.

Cytotoxic Oxygenated Steroids from the Soft Coral Nephthea erecta.

PubMed

Tsai, Tsung-Chang; Huang, Yu-Ting; Chou, Shih-Kai; Shih, Ming-Cheng; Chiang, Ching-Ying; Su, Jui-Hsin

2016-10-01

A new 10-demethylated steroid, nephtheasteroid A (1), a new 19-oxygenated steroid, nephtheasteroid B (2) as well as five known steroids 3-7 were isolated from the organic extract of a Taiwanese soft coral Nephthea erecta. The structure was determined by means of IR, MS, and NMR techniques. Among these metabolites, 1 is rarely found in steroids possessing a 19-norergostane skeleton. In vitro cytotoxicity study using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay revealed that compounds 3 and 4 exhibited cytotoxicity against human chronic myelogenous leukemia (K562), human acute lymphoblastic leukemia (Molt-4), human T lymphoblastoid (Sup-T1), and human leukemic monocyte lymphoma (U937), with IC 50 of 6.5-14.0 µM.

40 CFR 180.1278 - Quillaja saponaria extract (saponins); exemption from the requirement of a tolerance.

Code of Federal Regulations, 2014 CFR

2014-07-01

... 40 Protection of Environment 24 2014-07-01 2014-07-01 false Quillaja saponaria extract (saponins... RESIDUES IN FOOD Exemptions From Tolerances § 180.1278 Quillaja saponaria extract (saponins); exemption... (saponins) are exempt from the requirement of a tolerance in or on all food commodities. [72 FR 41935, Aug...

40 CFR 180.1278 - Quillaja saponaria extract (saponins); exemption from the requirement of a tolerance.

Code of Federal Regulations, 2011 CFR

2011-07-01

... 40 Protection of Environment 24 2011-07-01 2011-07-01 false Quillaja saponaria extract (saponins... RESIDUES IN FOOD Exemptions From Tolerances § 180.1278 Quillaja saponaria extract (saponins); exemption... (saponins) are exempt from the requirement of a tolerance in or on all food commodities. [72 FR 41935, Aug...

40 CFR 180.1278 - Quillaja saponaria extract (saponins); exemption from the requirement of a tolerance.

Code of Federal Regulations, 2013 CFR

2013-07-01

... 40 Protection of Environment 25 2013-07-01 2013-07-01 false Quillaja saponaria extract (saponins... RESIDUES IN FOOD Exemptions From Tolerances § 180.1278 Quillaja saponaria extract (saponins); exemption... (saponins) are exempt from the requirement of a tolerance in or on all food commodities. [72 FR 41935, Aug...

40 CFR 180.1278 - Quillaja saponaria extract (saponins); exemption from the requirement of a tolerance.

Code of Federal Regulations, 2012 CFR

2012-07-01

... 40 Protection of Environment 25 2012-07-01 2012-07-01 false Quillaja saponaria extract (saponins... RESIDUES IN FOOD Exemptions From Tolerances § 180.1278 Quillaja saponaria extract (saponins); exemption... (saponins) are exempt from the requirement of a tolerance in or on all food commodities. [72 FR 41935, Aug...

40 CFR 180.1278 - Quillaja saponaria extract (saponins); exemption from the requirement of a tolerance.

Code of Federal Regulations, 2010 CFR

2010-07-01

... 40 Protection of Environment 23 2010-07-01 2010-07-01 false Quillaja saponaria extract (saponins... RESIDUES IN FOOD Exemptions From Tolerances § 180.1278 Quillaja saponaria extract (saponins); exemption... (saponins) are exempt from the requirement of a tolerance in or on all food commodities. [72 FR 41935, Aug...

Saponins from soy bean and mung bean inhibit the antigen specific activation of helper T cells by blocking cell cycle progression.

PubMed

Lee, Suk Jun; Bae, Joonbeom; Kim, Sunhee; Jeong, Seonah; Choi, Chang-Yong; Choi, Sang-Pil; Kim, Hyun-Sook; Jung, Woon-Won; Imm, Jee-Young; Kim, Sae Hun; Chun, Taehoon

2013-02-01

Treatment of helper T (Th) cells with saponins from soy bean and mung bean prevented their activation by inhibiting cell proliferation and cytokine secretion. However, the saponins did not affect the expression of major histocompatibility complex class II (A(b)) and co-stimulatory molecule (CD86) on professional antigen-presenting cells. Instead, the saponins directly inhibited Th cell proliferation by blocking the G(1) to S phase cell cycle transition. Moreover, blocking of the cell cycle by the saponins was achieved by decreased expression of cyclin D1 and cyclin E, and constitutive expression of p27(KIP1). Saponins also increased stability of p27(KIP1) in Th cells after antigenic stimulation.

The plant hopper Issus coleoptratus can detoxify phloem sap saponins including the degradation of the terpene core

PubMed Central

Himmelsbach, Markus; Weth, Agnes; Böhme, Christine; Schwarz, Martin; Bräunig, Peter; Baumgartner, Werner

2016-01-01

ABSTRACT Issus coleoptratus is a small plant hopper which mainly feeds on the phloem sap from ivy. Although all parts of ivy are poisonous as the plant contains saponins, especially hederasaponins, I. coleoptratus can cope with the poison. In contrast to other animals like the stick insect Carausius morosus which accumulates saponins in its body, I. coleoptratus can degrade and disintegrate not only the saponins but even the genines, i.e. the triterpene core of the substances. This is perhaps made possible by a specialised midgut and/or the salivary glands. When the glands and the gut are dissected and added to saponins in solution, the saponins, including the genines, are degraded ex vivo. PMID:26863940

Bioactive steroids and sorbicillinoids isolated from the endophytic fungus Trichoderma sp. Xy24.

PubMed

Zhao, Jin-Lian; Zhang, Min; Liu, Ji-Mei; Tan, Zhen; Chen, Ri-Dao; Xie, Ke-Bo; Dai, Jun-Gui

2017-10-01

A new steroid glucoside (1), along with nine known steroids (2-10) and four known sorbicillinoids (11-14), were isolated from the endophytic fungus Trichoderma sp. Xy24. Their structures were elucidated on the basis of spectroscopic data analyses and by comparison with reported data. Compounds 3, 5-7, 9, 10, and 13 exhibited significant inhibitory effects on HIV-1 virus with IC 50 values ranging 1.9-9.3 μM; compounds 10, 13, and 14 showed potent inhibitory activity on LPS-induced NO production in BV2 microglia cells with inhibitory rates of 108.2, 100, and 75.1% at 10 μM, respectively. In addition, compound 10 displayed moderate cytotoxicity against BCG823 and HePG2 cell lines with IC 50 values of 11.1 and 17.7 μM, respectively.

Phytopharmacological overview of Tribulus terrestris

PubMed Central

Chhatre, Saurabh; Nesari, Tanuja; Somani, Gauresh; Kanchan, Divya; Sathaye, Sadhana

2014-01-01

Tribulus terrestris (family Zygophyllaceae), commonly known as Gokshur or Gokharu or puncture vine, has been used for a long time in both the Indian and Chinese systems of medicine for treatment of various kinds of diseases. Its various parts contain a variety of chemical constituents which are medicinally important, such as flavonoids, flavonol glycosides, steroidal saponins, and alkaloids. It has diuretic, aphrodisiac, antiurolithic, immunomodulatory, antidiabetic, absorption enhancing, hypolipidemic, cardiotonic, central nervous system, hepatoprotective, anti-inflammatory, analgesic, antispasmodic, anticancer, antibacterial, anthelmintic, larvicidal, and anticariogenic activities. For the last few decades or so, extensive research work has been done to prove its biological activities and the pharmacology of its extracts. The aim of this review is to create a database for further investigations of the discovered phytochemical and pharmacological properties of this plant to promote research. This will help in confirmation of its traditional use along with its value-added utility, eventually leading to higher revenues from the plant. PMID:24600195

In vitro antiviral activity of aqueous extract of Phaleria macrocarpa fruit against herpes simplex virus type 1

NASA Astrophysics Data System (ADS)

Ismaeel, Mahmud Yusef Yusef; Dyari, Herryawan Ryadi Eziwar; Yaacob, Wan Ahmad; Ibrahim, Nazlina

2018-04-01

Phaleria macrocarpa fruits have been used as herbal medicine for several diseases. This study aims to determine the cytotoxicity and antiviral activity of aqueous extract of P. macrocarpa fruit (AEPMF). Phytochemical analysis showed the presence of steroids, tannins, flavones aglycones, saponins, terpenoids and alkaloids. AEPMF was found to contain protein with the concentration of 740 µg/mL. The cytotoxicity towards Vero cell was evaluated using MTT assay with 50% cytotoxic concentration (CC50) value of AEPMF 5 mg/mL. The finding indicates that AEPMF is safe and not toxic towards Vero cells. Screening by plaque reduction assay showed that AEPMF have antiviral activity against herpes simplex virus type 1 (HSV-1) with effective concentration (EC50) was 0.28 mg/mL. The selective index (SI=CC50/EC50) of AEPMF is 17.9 indicating AEPMF have potential for further evaluation in antiviral activity.

Recent Advances in Momordica charantia: Functional Components and Biological Activities.

PubMed

Jia, Shuo; Shen, Mingyue; Zhang, Fan; Xie, Jianhua

2017-11-28

Momordica charantia L. ( M. charantia ), a member of the Cucurbitaceae family, is widely distributed in tropical and subtropical regions of the world. It has been used in folk medicine for the treatment of diabetes mellitus, and its fruit has been used as a vegetable for thousands of years. Phytochemicals including proteins, polysaccharides, flavonoids, triterpenes, saponins, ascorbic acid and steroids have been found in this plant. Various biological activities of M. charantia have been reported, such as antihyperglycemic, antibacterial, antiviral, antitumor, immunomodulation, antioxidant, antidiabetic, anthelmintic, antimutagenic, antiulcer, antilipolytic, antifertility, hepatoprotective, anticancer and anti-inflammatory activities. However, both in vitro and in vivo studies have also demonstrated that M. charantia may also exert toxic or adverse effects under different conditions. This review addresses the chemical constituents of M. charantia and discusses their pharmacological activities as well as their adverse effects, aimed at providing a comprehensive overview of the phytochemistry and biological activities of M. charantia .

Recent Advances in Momordica charantia: Functional Components and Biological Activities

PubMed Central

Jia, Shuo; Shen, Mingyue; Zhang, Fan; Xie, Jianhua

2017-01-01

Momordica charantia L. (M. charantia), a member of the Cucurbitaceae family, is widely distributed in tropical and subtropical regions of the world. It has been used in folk medicine for the treatment of diabetes mellitus, and its fruit has been used as a vegetable for thousands of years. Phytochemicals including proteins, polysaccharides, flavonoids, triterpenes, saponins, ascorbic acid and steroids have been found in this plant. Various biological activities of M. charantia have been reported, such as antihyperglycemic, antibacterial, antiviral, antitumor, immunomodulation, antioxidant, antidiabetic, anthelmintic, antimutagenic, antiulcer, antilipolytic, antifertility, hepatoprotective, anticancer and anti-inflammatory activities. However, both in vitro and in vivo studies have also demonstrated that M. charantia may also exert toxic or adverse effects under different conditions. This review addresses the chemical constituents of M. charantia and discusses their pharmacological activities as well as their adverse effects, aimed at providing a comprehensive overview of the phytochemistry and biological activities of M. charantia. PMID:29182587

Phytochemical screening and in-vitro evaluation of pharmacological activities of peels of Musa sapientum and Carica papaya fruit.

PubMed

Siddique, Sarmad; Nawaz, Shamsa; Muhammad, Faqir; Akhtar, Bushra; Aslam, Bilal

2018-06-01

Aqueous, absolute and 80% ethanolic extract of fruit peels of Musa sapientum and Carica papaya were investigated for their antibacterial activity, measured by disc diffusion method and antioxidant activity, measured by four different methods. Papaya and banana peels were found to contain terpenoids, tannins, alkaloids, saponins steroid, phenols, fixed oils and fats. 80% ethanolic extract of banana peel was found to contain highest total phenolic content (TPC), total flavonoid content (TFC) and antioxidant activity but in papaya peel, highest TPC and reducing activity was shown by water extract while, TFC and radical scavenging activity was given by 80% ethanolic extract. In banana, water extract showed highest antibacterial activity against tested bacteria while in case of papaya, absolute ethanolic extract showed highest antibacterial activity. The present study revealed that peels of banana and papaya fruits are potentially good source of antioxidant and antibacterial agents.

Cure of tuberculosis using nanotechnology: An overview.

PubMed

Kerry, Rout George; Gouda, Sushanto; Sil, Bikram; Das, Gitishree; Shin, Han-Seung; Ghodake, Gajanan; Patra, Jayanta Kumar

2018-05-01

Mycobacterium tuberculosis is the causative agent of tuberculosis (TB), a major health issue of the present era. The bacterium inhabits the host macrophage and other immune cells where it modulates the lysosome trafficking protein, hinders the formation of phagolysosome, and blocks the TNF receptor-dependent apoptosis of host macrophage/monocytes. Other limitations such as resistance to and low bioavailability and bio-distribution of conventional drugs aid to their high virulence and human mortality. This review highlights the use of nanotechnology-based approaches for drug formulation and delivery which could open new avenues to limit the pathogenicity of tuberculosis. Moreover phytochemicals, such as alkaloids, phenols, saponins, steroids, tannins, and terpenoids, extracted from terrestrial plants and mangroves seem promising against M. tuberculosis through different molecular mechanisms. Further understanding of the genomics and proteomics of this pathogenic microbe could also help overcome various research gaps in the path of developing a suitable therapy against tuberculosis.

A review on Insulin plant (Costus igneus Nak).

PubMed

Hegde, Prakash K; Rao, Harini A; Rao, Prasanna N

2014-01-01

Costus igneus Nak and Costus pictus D. Don, commonly known as Spiral flag, is a member of Costaceae and a newly introduced plant in India from South and Central America. It is a perennial, upright, spreading plant reaching about two feet tall, with spirally arranged leaves and attractive flowers. In southern India, it usually grows as an ornamental plant and its leaves are used as a dietary supplement in the treatment of diabetes mellitus. Recently, a number of researches have been carried out to evaluate the anti-diabetic potential of this plant. Besides, it has been proven to possess various pharmacological activities like hypolipidemic, diuretic, antioxidant, anti-microbial, anti-cancerous. Further, various phytochemical investigations reveal the presence of carbohydrates, triterpenoids, proteins, alkaloids, tannins, saponins, flavonoids, steroid, and appreciable amounts of trace elements. This work is an attempt to compile and explore the different pharmacological and phytochemical studies reported till date.

Active immunization against Plasmodium berghei malaria in mice, using different preparations of plasmodial antigen and different pathways of administration*

PubMed Central

Jerusalem, Christoph; Eling, Wynand

1969-01-01

With regard to the effectiveness of the antigens in inducing clinical immunity against malaria parasites, the minimum amount of living antigen developed in mice during controlled low parasitaemia with Plasmodium berghei has been estimated and compared with the amount of non-living antigen obtained by various methods of freeing parasites from their erythrocyte hosts. Whereas about 100 mg of living antigen per kg of body-weight are sufficient to induce a degree of hyperimmunity, 1240 mg/kg of a freshly prepared crude antigen are necessary to enable the mice to survive a challenge infection while 3500 mg—7000 mg/kg of a vaccine prepared from freshly isolated plasmodia are necessary to produce a degree of immunity comparable with hyperimmunity. It appears, therefore, that every manipulation of the parasitized erythrocyte or the isolated plasmodium outside the host organism, as well as a storage time in excess of 36 hours, causes a reduction in antigenicity, up to a factor of 10-2. However, this decrease in antigenicity is disproportionate compared with the reduced rate of infectivity of stored, parasitized erythrocytes and isolated parasites. After an incubation period of 18 hours, the ID100 increases from 2 × 10 to 5 × 107 parasites. Therefore, the differences between the essential amount of living plasmodia and non-living antigen may be due to other, hitherto unknown, factors and not exclusively to degradation of the most important antigen. The saponin method of freeing parasites from their erythrocyte hosts was found to yield the purest antigen. Preparations of parasites obtained by treating parasitized erythrocytes with anti-erythrocyte serum or with formalin were highly contaminated with remnants of the host cells and showed no better antigenic qualities than the parasites isolated by means of saponin. Since the decrease of antigenicity associated with harvesting and isolation procedures is constant, vaccination with a fractionated antigen pool should be possible. ImagesFIG. 4 PMID:5307595

Saponin determination, expression analysis and functional characterization of saponin biosynthetic genes in Chenopodium quinoa leaves.

PubMed

Fiallos-Jurado, Jennifer; Pollier, Jacob; Moses, Tessa; Arendt, Philipp; Barriga-Medina, Noelia; Morillo, Eduardo; Arahana, Venancio; de Lourdes Torres, Maria; Goossens, Alain; Leon-Reyes, Antonio

2016-09-01

Quinoa (Chenopodium quinoa Willd.) is a highly nutritious pseudocereal with an outstanding protein, vitamin, mineral and nutraceutical content. The leaves, flowers and seed coat of quinoa contain triterpenoid saponins, which impart bitterness to the grain and make them unpalatable without postharvest removal of the saponins. In this study, we quantified saponin content in quinoa leaves from Ecuadorian sweet and bitter genotypes and assessed the expression of saponin biosynthetic genes in leaf samples elicited with methyl jasmonate. We found saponin accumulation in leaves after MeJA treatment in both ecotypes tested. As no reference genes were available to perform qPCR in quinoa, we mined publicly available RNA-Seq data for orthologs of 22 genes known to be stably expressed in Arabidopsis thaliana using geNorm, NormFinder and BestKeeper algorithms. The quinoa ortholog of At2g28390 (Monensin Sensitivity 1, MON1) was stably expressed and chosen as a suitable reference gene for qPCR analysis. Candidate saponin biosynthesis genes were screened in the quinoa RNA-Seq data and subsequent functional characterization in yeast led to the identification of CqbAS1, CqCYP716A78 and CqCYP716A79. These genes were found to be induced by MeJA, suggesting this phytohormone might also modulate saponin biosynthesis in quinoa leaves. Knowledge of the saponin biosynthesis and its regulation in quinoa may aid the further development of sweet cultivars that do not require postharvest processing. Copyright © 2016 Elsevier Ireland Ltd. All rights reserved.

Effects of karaya saponin and Rhodobacter capsulatus on yolk cholesterol in laying hens.

PubMed

Afrose, S; Hossain, M S; Maki, T; Tsujii, H

2010-06-01

1. It has been reported that karaya saponin and Rhodobacter capsulatus individually have hypocholesterolaemic activity in laying hens. This study focuses on the effect of adding karaya saponin with R. capsulatus to hen's diet with regard to serum and egg yolk cholesterol and triglycerides. 2. A total of 56 Boris Brown laying hens were divided into 7 groups at 20 weeks of age. Combinations of 25, 50, 75 mg kg(-1) karaya saponin and R. capsulatus 200 and 400 mg kg(-1) were used as treatment groups. 3. After 8 weeks of supplementation, the effects of all the combinations of karaya saponin and R. capsulatus on serum and egg yolk cholesterol, triglycerides, and high-density lipoprotein (HDL)-cholesterol were greater than either karaya saponin or R. capsulatus alone. The combination of karaya saponin 50 mg kg(-1)+ R. capsulatus 400 mg kg(-1) exhibited the greatest reduction of serum (325%) and yolk (225%) cholesterol and the greatest increase of faecal, liver bile acids and yolk fatty acid (oleic, linoleic and linolenic) concentrations. In addition, egg production and yolk colour were significantly improved by the combined use of karaya saponin and R. capsulatus supplementation. 4. Therefore, the dietary supplementation of karaya saponin and R. capsulatus may lead to the production of a low-cholesterol egg, with production performance maintained at a standard level.

Variation of saponin contents and physiological status in Quillaja saponaria under different environmental conditions.

PubMed

Grandón, Angélica S; Espinosa, B Miguel; Ríos, Darcy L; Sánchez, O Manuel; Sáez, C Katia; Hernández, S Víctor; Becerra, A José

2013-12-01

Quillaja saponaria (Quillay), an evergreen tree found in Chile, is one of the main sources of saponins. Quillaja saponins have hypocholesterolaemic, anticarcinogenic, antioxidant and pesticidal properties, and are used as adjuvants for vaccines. Samples of Quillay growing at three zones in O'Higgins Region, Chile (Coastal, Central and Mountain zones) were analyzed for content of saponins and physiological status. The results revealed differences in the content of saponins depending on the zone of sample collection. The highest contents were found in samples from the Mountain zone, where the highest saponin contents were accompanied by the lowest foliar nitrogen contents, the highest antioxidant activity and the highest carotenoid contents. The results suggest a physiological and adaptive mechanism of saponins in plants to survive under unfavourable environmental conditions. The results have important implications for a theoretical basis for the design of a reasonable harvest, to avoid the cost of poor quality material, and also to provide a sustainable use and conservation of this important species. Further research on the effects of stress will improve our understanding of the saponins production and their physiological functions in plants, whereas they have generally been studied for their biological and chemical applications.

The role of the hydrophobic phase in the unique rheological properties of saponin adsorption layers.

PubMed

Golemanov, Konstantin; Tcholakova, Slavka; Denkov, Nikolai; Pelan, Eddie; Stoyanov, Simeon D

2014-09-28

Saponins are a diverse class of natural, plant derived surfactants, with peculiar molecular structure consisting of a hydrophobic scaffold and one or several hydrophilic oligosaccharide chains. Saponins have strong surface activity and are used as natural emulsifiers and foaming agents in food and beverage, pharmaceutical, ore processing, and other industries. Many saponins form adsorption layers at the air-water interface with extremely high surface elasticity and viscosity. The molecular origin of the observed unique interfacial visco-elasticity of saponin adsorption layers is of great interest from both scientific and application viewpoints. In the current study we demonstrate that the hydrophobic phase in contact with water has a very strong effect on the interfacial properties of saponins and that the interfacial elasticity and viscosity of the saponin adsorption layers decrease in the order: air > hexadecane ≫ tricaprylin. The molecular mechanisms behind these trends are analyzed and discussed in the context of the general structure of the surfactant adsorption layers at various nonpolar phase-water interfaces.

Effect of soy saponin on the growth of human colon cancer cells

PubMed Central

Tsai, Cheng-Yu; Chen, Yue-Hwa; Chien, Yi-Wen; Huang, Wen-Hsuan; Lin, Shyh-Hsiang

2010-01-01

AIM: To investigate the effect of extracted soybean saponins on the growth of human colon cancer cells. METHODS: WiDr human colon cancer cells were treated with 150, 300, 600 or 1200 ppm of soy saponin to determine the effect on cell growth, cell morphology, alkaline phosphatase (AP) and protein kinase C (PKC) activities, and P53 protein, c-Fos and c-Jun gene expression. RESULTS: Soy saponin decreased the number of viable cells in a dose-dependent manner and suppressed 12-O-tetradecanol-phorbol-13-acetate-stimulated PKC activity (P < 0.05). Cells treated with saponins developed cytoplasmic vesicles and the cell membrane became rougher and more irregular in a dose-dependent manner, and eventually disassembled. At 600 and 1200 ppm, the activity of AP was increased (P < 0.05). However, the apoptosis markers such as c-Jun and c-Fos were not significantly affected by saponin. CONCLUSION: Soy saponin may be effective in preventing colon cancer by affecting cell morphology, cell proliferation enzymes, and cell growth. PMID:20632438

Sea cucumber saponin liposomes ameliorate obesity-induced inflammation and insulin resistance in high-fat-diet-fed mice.

PubMed

Chen, Cheng; Han, Xiuqing; Dong, Ping; Li, Zhaojie; Yanagita, Teruyoshi; Xue, Changhu; Zhang, Tiantian; Wang, Yuming

2018-02-21

Obesity has become a worldwide concern in recent years, which may cause many diseases. Much attention has been paid to food components that are considered to be beneficial in preventing chronic metabolic diseases. The present study was conducted to investigate the effects of sea cucumber saponin liposomes on certain metabolic markers associated with obesity. C57/BL6 mice fed with high-fat diet were treated with different forms of sea cucumber saponins for eight weeks. The results showed that liposomes exhibited better effects on anti-obesity and anti-hyperlipidemia activities than the common form of sea cucumber saponins. Sea cucumber saponin liposomes could also effectively alleviate adipose tissue inflammation by reducing pro-inflammatory cytokine releases and macrophage infiltration. Moreover, sea cucumber saponin liposomes improved insulin resistance by altering the uptake and utilization of glucose. Taken together, our results indicated that the intake of sea cucumber saponin liposomes might be able to ameliorate obesity-induced inflammation and insulin resistance.

Paris polyphylla: chemical and biological prospectives.

PubMed

Negi, Jagmohan S; Bisht, Vinod K; Bhandari, Arvind K; Bhatt, Vijay P; Singh, Pramod; Singh, Narayan

2014-01-01

Paris polyphylla J.E. Smith is extensively used in traditional systems of Indian and Chinese medicines mainly for its anticancerous property. The national and international demand for P. polyphylla is constantly increasing and most of the supplies come from wild. Illegal and unscientific exploitation coupled with habitat destruction decreases the natural population of the herb, as a consequence this species comes under vulnerable category. Restoration and conservation of the natural population of this potential herb is prerequisites. This article aims to provide an overview on chemical and biological prospective of P. polyphylla. Secondary metabolites such as daucosterol, polyphyllin D, β -ecdysterone, Paris saponins I, II, V, VI, VII, H, dioscin, oligosaccharides, heptasaccharide, octasaccharide, trigofoenoside A, protogracillin, Paris yunnanosides G-J, padelaoside B, pinnatasterone, formosanin C and 20-hydroxyecdyson saponins have been isolated from P. polyphylla. Several biological activities such as anticancerous, antitumor, cytotoxic, anthelmintic, antimicrobial, antiangiogenic, immunostimulating, contractile and hemostatic have also been reported. Consequently, this review will be helpful to the researcher and scientist for further research.

[Analysis of saponins from panax notoginseng using pressurized solvent extraction coupled with liquid chromatography-electrospray mass spectrum].

PubMed

Wan, Jianbo; Li, Changming; Li, Shaopin; Kong, Lingyi; Wang, Yitao

2005-10-01

To establish a method for qualitative analysis of saponins from Panax notoginseng using pressurized solvent extraction coupled with LC-ESI-MS. The PSE technology was applied to the process of extraction for Panax notoginseng, and the negative ion detection and multiple reaction monitoring model were used. The saponins were investigated based on total ion chromatogram (TIC) and MRM chromatogram. According to the fragment character of saponins, the molecular weight and their structures could be identified. The method can be used for qualitative analysis of saponins from Panax notoginseng.

Adsorption of saponin compound in Carica papaya leaves extract using weakly basic ion exchanger resin

NASA Astrophysics Data System (ADS)

Abidin, Noraziani Zainal; Janam, Anathasia; Zubairi, Saiful Irwan

2016-11-01

Adsorption of saponin compound in papaya leaves juice extract using Amberlite® IRA-67 resin was not reported in previous studies. In this research, Amberlite® IRA-67 was used to determine the amount of saponin that can be adsorbed using different weights of dry resin (0.1 g and 0.5 g). Peleg model was used to determine the maximum yield of saponin (43.67 mg) and the exhaustive time (5.7 days) prior to a preliminary resin-saponin adsorption study. After adsorption process, there was no significant difference (p>0.05) in total saponin content (mg) for sample treated with 0.1 g (3.79 ± 0.55 mg) and sample treated with 0.5 g (3.43 ± 0.51 mg) dry weight resin. Long-term kinetic adsorption of resin-saponin method (>24 hours) should be conducted to obtain optimum freed saponin extract. Besides that, sample treated with 0.1 g dry weight resin had high free radical scavenging value of 50.33 ± 2.74% compared to sample treated with 0.5 g dry weight resin that had low free radical scavenging value of 24.54 ± 1.66% dry weights. Total saponin content (mg), total phenolic content (mg GAE) and free radical scavenging activity (%) was investigated to determine the interaction of those compounds with Amberlite® IRA-67. The RP-HPLC analysis using ursolic acid as standard at 203 nm showed no peak even though ursolic acid was one of the saponin components that was ubiquitous in plant kingdom. The absence of peak was due to weak solubility of ursolic acid in water and since it was only soluble in solvent with moderate polarity. The Pearson's correlation coefficient for total saponin content (mg) versus total phenolic content (mg GAE) and radical scavenging activity (%) were +0.959 and +0.807. Positive values showed that whenever there was an increase in saponin content (mg), the phenolic content (mg GAE) and radical scavenging activity (%) would also increase. However, as the resin-saponin adsorption was carried out, there was a significant decrease of radical scavenging activity (%) as the amount of the resin increased. Moreover, the saponin amount did not show any reduction as the amount of resin resin increased. Therefore, there was other active ingredient which has the antioxidant properties were affected by the adsoprtion process. For that reason, the kinetic equilibrium of resin-saponin adsorption studies against the ratio of resin-to-extract has to be carried out to determine the efficacy of the extract therapeutic properties prior to the cell culture studies.

A rabies vaccine adjuvanted with saponins from leaves of the soap tree (Quillaja brasiliensis) induces specific immune responses and protects against lethal challenge.

PubMed

Yendo, Anna Carolina A; de Costa, Fernanda; Cibulski, Samuel P; Teixeira, Thais F; Colling, Luana C; Mastrogiovanni, Mauricio; Soulé, Silvia; Roehe, Paulo M; Gosmann, Grace; Ferreira, Fernando A; Fett-Neto, Arthur G

2016-04-29

Quillaja brasiliensis (Quillajaceae) is a saponin producing species native from southern Brazil and Uruguay. Its saponins are remarkably similar to those of Q. saponaria, which provides most of the saponins used as immunoadjuvants in vaccines. The immunostimulating capacities of aqueous extract (AE) and purified saponin fraction (QB-90) obtained from leaves of Q. brasiliensis were favorably comparable to those of a commercial saponin-based adjuvant preparation (Quil-A) in experimental vaccines against bovine herpesvirus type 1 and 5, poliovirus and bovine viral diarrhea virus in mice model. Herein, the immunogenicity and protection efficacy of rabies vaccines adjuvanted with Q. brasiliensis AE and its saponin fractions were compared with vaccines adjuvanted with either commercial Quil-A or Alum. Mice were vaccinated with one or two doses (on days 0 and 14) of one of the different vaccines and serum levels of total IgG, IgG1 and IgG2a were quantified over time. A challenge experiment with a lethal dose of rabies virus was carried out with the formulations. Viral RNA detection in the brain of mice was performed by qPCR, and RNA copy-numbers were quantified using a standard curve of in vitro transcribed RNA. All Q. brasiliensis saponin-adjuvanted vaccines significantly enhanced levels of specific IgG isotypes when compared with the no adjuvant group (P ≤ 0.05). Overall, one or two doses of saponin-based vaccine were efficient to protect against the lethal rabies exposure. Both AE and saponin fractions from Q. brasiliensis leaves proved potent immunological adjuvants in vaccines against a lethal challenge with a major livestock pathogen, hence confirming their value as competitive or complementary sustainable alternatives to saponins of Q. saponaria. Copyright © 2016 Elsevier Ltd. All rights reserved.

Anti-inflammatory steroids from the rhizomes of Dioscorea septemloba Thunb.

PubMed

Zhang, Yi; Yu, Hai-Yang; Chao, Li-Ping; Qu, Lu; Ruan, Jing-Ya; Liu, Yan-Xia; Dong, Yong-Zhe; Han, Li-Feng; Wang, Tao

2016-08-01

Seven new steroid glycosides, dioscorosides A1 (1), A2 (2), B1 (3), B2 (4), C1 (5), C2 (6), and D (7), together with 22 known ones (8-29) were isolated from the rhizomes of Dioscorea septemloba, their structures were elucidated by chemical and spectroscopic methods. All isolates were evaluated for in vitro anti-inflammatory potential using LPS-stimulated RAW 264.7 murine macrophages. Among them, spirostane glycosides 18 and 21-24 exhibited significant inhibition of nitrite production. Moreover, the structure-activity relationship was summarized. Copyright © 2016 Elsevier Inc. All rights reserved.

Cytotoxic Steroids from the Vietnamese Soft Coral Sinularia conferta.

PubMed

Ngoc, Ninh Thi; Huong, Pham Thi Mai; Thanh, Nguyen Van; Chi, Nguyen Thi Phuong; Dang, Nguyen Hai; Cuong, Nguyen Xuan; Nam, Nguyen Hoai; Thung, Do Cong; Kiem, Phan Van; Minh, Chau Van

2017-03-01

Twelve steroids, including five new compounds 1-5, were isolated and structurally elucidated from a methanol extract of the Vietnamese soft coral Sinularia conferta. Their cytotoxic effects against three human cancer cell lines, lung carcinoma (A-549), cervical adenocarcinoma (HeLa), and pancreatic epithelioid carcinoma (PANC-1), were evaluated using 3-(4,5-dimethylthiazolyl-2)-2,5-diphenyltetrazolium bromide (MTT) assays. Among isolated compounds, 10 exhibited potent cytotoxic effects on all three tested cell lines with IC 50 values of 3.64±0.18, 19.34±0.42, and 1.78±0.69 µM, respectively.

Complexation of phospholipids and cholesterol by triterpenic saponins in bulk and in monolayers.

PubMed

Wojciechowski, Kamil; Orczyk, Marta; Gutberlet, Thomas; Geue, Thomas

2016-02-01

The interactions between three triterpene saponins: α-hederin, hederacoside C and ammonium glycyrrhizate with model lipids: cholesterol and dipalmitoylphosphatidylcholine (DPPC) are described. The oleanolic acid-type saponins (α-hederin and hederacoside C) were shown to form 1:1 complexes with lipids in bulk, characterized by stability constants in the range (4.0±0.2)·10(3)-(5.0±0.4)·10(4) M(-1). The complexes with cholesterol are generally stronger than those with DPPC. On the contrary, ammonium glycyrrhizate does not form complexes with any of the lipids in solution. The saponin-lipid interactions were also studied in a confined environment of Langmuir monolayers of DPPC and DPPC/cholesterol with the saponins present in the subphase. A combined monolayer relaxation, surface dilational rheology, fluorescence microscopy and neutron reflectivity (NR) study showed that all three saponins are able to penetrate pure DPPC and mixed DPPC/cholesterol monolayers. Overall, the effect of the saponins on the model lipid monolayers does not fully correlate with the lipid-saponin complex formation in the homogeneous solution. The best correlation was found for α-hederin, for which even the preference for cholesterol over DPPC observed in bulk is well reflected in the monolayer studies and the literature data on its membranolytic activity. Similarly, the lack of interaction of ammonium glycyrrhizate with both lipids is evident equally in bulk and monolayer experiments, as well as in its weak membranolytic activity. The combined bulk and monolayer results are discussed in view of the role of confinement in modulating the saponin-lipid interactions and possible mechanism of membranolytic activity of saponins. Copyright © 2015 Elsevier B.V. All rights reserved.

[Optimization of extraction technics of total saponins from Pulsatilla cernua].

PubMed

Li, Hai-Yan; Hao, Ning; Xu, Yong-Nan; Piao, Zhong-Yun

2010-04-01

The extraction condition of total saponins from Pulsatilla cenua by ultrasonic wave was optimized by single factor and orthogonal experiments. The largest absorbency of saponin was intended to be 470 nm by wavelength scan method with the pulchinenoside B4 as control sample, the linear relationship was observed between the absorbency and the content of saponin in the range of 0 - 0.040 mg/mL. The optimal conditions of extraction was as following: 80% of alcohol concentration, 40 min of ultrasonic time, 1: 20 of solid to liquid ratio, 80 W of ultrasonic power and one time for extraction. Among them, alcohol had the most significant effect on the extraction of total saponins. The content of total saponins in Pulsatilla cernua was 4. 32% under the optimal condition. The method developed here is efficient, stable, accurate and repeatable.

Stereoisomers of Saponins in Panax notoginseng (Sanqi): A Review

PubMed Central

Peng, Ming; Yi, Ya X.; Zhang, Tong; Ding, Yue; Le, Jian

2018-01-01

Panax notoginseng (Sanqi), a traditional Chinese medical drug which has been applied to medical use for over four centuries, contains high content of dammarane-type tetracyclic triterpenoid saponins. A number of stereoisomeric dammarane-type saponins exist in this precious herb, and some are particularly regarded as “biomarkers” in processed notoginseng. Contemporary researches have indicated that some saponin stereoisomers may show stereospecific pharmacological activities, such as anti-tumor, antioxidative, anti-photoaging, anti-inflammatory, antidiabetic, and neuro-protective activities, as well as stereoselective effects on ion channel current regulation, cardiovascular system, and immune system. The current review provides a comprehensive overview of chemical compositions of raw and processed P. notoginseng with a particular emphasis on saponin stereoisomers. Besides, the pharmacological and pharmacokinetic researches, as well as determination and biotechnological preparation methods of stereoisomeric saponins in notoginseng are discussed extensively. PMID:29593531

Effects of Ultrasound on Extraction of Saponin from Ginseng

NASA Astrophysics Data System (ADS)

Li, Hui; Ohdaira, Etsuzo; Ide, Masao

1994-05-01

We performed a study of the effects of ultrasound on the extraction of saponin from Panax ginseng C. A. Meyer. In this study, the extraction of saponin was examined as functions of irradiation time (0.5 to 6 h) and acoustic pressure (0 to 90 kPa). It has been observed that the yields of both total extract and saponin are larger with ultrasonic irradiation than those without ultrasonic irradiation; the increase in yield of total extract is approximately 15 wt%, and that of saponin is approximately 30 wt% at an acoustic pressure 67 kPa. In addition, the yield increases with the acoustic pressure. It is also demonstrated that saponin was not resolved in the acoustic intensity range of this experiment. The enhancement in liquid-solid extraction caused by ultrasound can be attributed to the phenomenon of cavitation.

Identification and structural characterisation of triterpene saponins from the root of Ardisia mamillata Hance by HPLC-ESI-QTOF-MS/MS.

PubMed

Zhang, Er-Fei; Ling, Yun; Yin, Zi; Zhang, Qing

2018-04-01

Triterpene saponins in medicinal plants attract scientific attentions for their structural diversity and significant bioactivities. In this work, a high-performance liquid chromatography coupled to electrospray ionisation and quadrupole time-of-flight mass spectrometry (HPLC-ESI-QTOF-MS/MS) method is used to rapidly separate and identify triterpene saponins from the extract of Ardisia mamillata Hance (AMH). In the full scan mass spectrum, the accurate determination of molecular formula is obtained by the predominant ion [M + HCOO] - in negative ion mode. As a result, 30 triterpene saponins are identified or tentatively identified in the plant extract. Of these, 17 triterpene saponins are new compounds. In conclusion, the HPLC-ESI-QTOF-MS/MS is an efficient technique to separate and identify triterpene saponins in complex matrices of medicinal plant.

Optimization of ultrasonic-assisted extraction of total saponins from Eclipta prostrasta L. using response surface methodology.

PubMed

Hu, Ting; Guo, Yan-Yun; Zhou, Qin-Fan; Zhong, Xian-Ke; Zhu, Liang; Piao, Jin-Hua; Chen, Jian; Jiang, Jian-Guo

2012-09-01

Eclipta prostrasta L. is a traditional Chinese medicine herb, which is rich in saponins and has strong antiviral and antitumor activities. An ultrasonic-assisted extraction (UAE) technique was developed for the fast extraction of saponins from E. prostrasta. The content of total saponins in E. prostrasta was determined using UV/vis spectrophotometric methods. Several influential parameters like ethanol concentration, extraction time, temperature, and liquid/solid ratio were investigated for the optimization of the extraction using single factor and Box-Behnken experimental designs. Extraction conditions were optimized for maximum yield of total saponins in E. prostrasta using response surface methodology (RSM) with 4 independent variables at 3 levels of each variable. Results showed that the optimization conditions for saponins extraction were: ethanol concentration 70%, extraction time 3 h, temperature 70 °C, and liquid/solid ratio 14:1. Corresponding saponins content was 2.096%. The mathematical model developed was found to fit well with the experimental data. Practical Application: Although there are wider applications of Eclipta prostrasta L. as a functional food or traditional medicine due to its various bioactivities, these properties are limited by its crude extracts. Total saponins are the main active ingredient of E. prostrasta. This research has optimized the extraction conditions of total saponins from E. prostrasta, which will provide useful reference information for further studies, and offer related industries with helpful guidance in practice. © 2012 Institute of Food Technologists®

Effect of tea saponin on ephyrae and polyps of the moon jellyfish Aurelia sp.1.

PubMed

Dong, Zhijun; Sun, Tingting; Liang, Likun; Wang, Lei

2017-01-01

The moon jellyfish (Aurelia sp.1) is thought to be a nuisance for the sea cucumber aquaculture, which commonly occur in the sea cucumber (Apostichopus japonicus) culture ponds of the Yellow Sea, China. To develop an appropriate method to control Aurelia sp.1 blooms, the toxic effects of tea saponin on Aurelia sp.1 ephyrae and polyps were tested in laboratory experiments. Our results revealed that tea saponin caused significant morphological changes, behavioral abnormality and mortality in Aurelia sp.1 ephyrae and polyps in 24 h and 48 h exposure experiments. The 24 h and 48 h median lethal concentrations (LC50) values of tea saponin for Aurelia sp.1 ephyrae were 1.9 and 1.1 mg L-1 respectively, while the LC50 value for Aurelia sp.1 polyps was 0.4 mg L-1 after 24h and 48 h of exposure to tea saponin. Comparison with literature results of tea saponin on A. japonicus indicates that the resistance of A. japonicus to tea saponin is 12-18 times greater than that of Aurelia sp.1 ephyrae. Therefore, the appropriate tea saponin dosage for the control of Aurelia sp.1 should be paid enough attention in order to minimize possible damage for sea cucumber. We suggest that the recommended level of tea saponin to eradicate Aurelia sp.1 ephyrae and polyps in sea cucumber culture ponds be lower than 1.35 mg L-1.

Effect of tea saponin on ephyrae and polyps of the moon jellyfish Aurelia sp.1

PubMed Central

Sun, Tingting; Liang, Likun; Wang, Lei

2017-01-01

The moon jellyfish (Aurelia sp.1) is thought to be a nuisance for the sea cucumber aquaculture, which commonly occur in the sea cucumber (Apostichopus japonicus) culture ponds of the Yellow Sea, China. To develop an appropriate method to control Aurelia sp.1 blooms, the toxic effects of tea saponin on Aurelia sp.1 ephyrae and polyps were tested in laboratory experiments. Our results revealed that tea saponin caused significant morphological changes, behavioral abnormality and mortality in Aurelia sp.1 ephyrae and polyps in 24 h and 48 h exposure experiments. The 24 h and 48 h median lethal concentrations (LC50) values of tea saponin for Aurelia sp.1 ephyrae were 1.9 and 1.1 mg L-1 respectively, while the LC50 value for Aurelia sp.1 polyps was 0.4 mg L-1 after 24h and 48 h of exposure to tea saponin. Comparison with literature results of tea saponin on A. japonicus indicates that the resistance of A. japonicus to tea saponin is 12–18 times greater than that of Aurelia sp.1 ephyrae. Therefore, the appropriate tea saponin dosage for the control of Aurelia sp.1 should be paid enough attention in order to minimize possible damage for sea cucumber. We suggest that the recommended level of tea saponin to eradicate Aurelia sp.1 ephyrae and polyps in sea cucumber culture ponds be lower than 1.35 mg L-1. PMID:28777817

Antimicrobial activity of fermented Theobroma cacao pod husk extract.

PubMed

Santos, R X; Oliveira, D A; Sodré, G A; Gosmann, G; Brendel, M; Pungartnik, C

2014-09-26

Theobroma cacao L. contains more than 500 different chemical compounds some of which have been traditionally used for their antioxidant, anti-carcinogenic, immunomodulatory, vasodilatory, analgesic, and antimicrobial activities. Spontaneous aerobic fermentation of cacao husks yields a crude husk extract (CHE) with antimicrobial activity. CHE was fractioned by solvent partition with polar solvent extraction or by silica gel chromatography and a total of 12 sub-fractions were analyzed for chemical composition and bioactivity. CHE was effective against the yeast Saccharomyces cerevisiae and the basidiomycete Moniliophthora perniciosa. Antibacterial activity was determined using 6 strains: Staphylococcus aureus, Staphylococcus epidermidis, and Bacillus subtilis (Gram-positive) and Pseudomonas aeruginosa, Klebsiella pneumoniae, and Salmonella choleraesuis (Gram-negative). At doses up to 10 mg/mL, CHE was not effective against the Gram-positive bacteria tested but against medically important P. aeruginosa and S. choleraesuis with a minimum inhibitory concentration (MIC) of 5.0 mg/mL. Sub-fractions varied widely in activity and strongest antibacterial activity was seen with CHE8 against S. choleraesuis (MIC of 1.0 mg/mL) and CHE9 against S. epidermidis (MIC of 2.5 mg/mL). All bioactive CHE fractions contained phenols, steroids, or terpenes, but no saponins. Fraction CHE9 contained flavonoids, phenolics, steroids, and terpenes, amino acids, and alkaloids, while CHE12 had the same compounds but lacked flavonoids.

Anti-staphylococcal properties of Eichhornia crassipes, Pistacia vera, and Ziziphus amole leaf extracts: Isolates from cattle and rabbits.

PubMed

Gutiérrez-Morales, Andrea; Velázquez-Ordoñez, Valente; Khusro, Ameer; Salem, Abdelfattah Z M; Estrada-Zúñiga, María Elena; Salem, Mohamed Z M; Valladares-Carranza, Benjamin; Burrola-Aguilar, Cristina

2017-12-01

The desideratum aim of the present context was to assess the biopotency of methanolic extracts of Eichhornia crassipes (E. crassipes), Pistacia vera (P. vera), and Ziziphus amole (Z. amole) leaves against various staphylococcal strains, and to quantify the phenolics as well as saponin content in them. The antibacterial activity of various concentrations (62.5-1000 μg/mL) of plant extracts was tested against control clinical strains (Staphylococcus aureus ATCC 25923, S. aureus ATCC 29213, and S. aureus ATCC 43300), methicillin-resistant S. aureus (MRSA1 and MRSA2), oxacillin sensitive S. aureus (SOSA1 and SOSA2), and coagulase-negative Staphylococcus epidermidis (CoNS1, CoNS2, and CoNS3) using disc diffusion assay. Leaf extracts of the three plants exhibited pronounced growth inhibitory characteristics against staphylococci in a dose dependent manner. E. crassipes extract depicted the highest relative percentage inhibition values against control clinical strains (68.6 ± 0.5%), while P. vera (68.6 ± 0.3%) and Z. amole (74.79 ± 0.3%) extracts showed pronounced relative inhibition values against staphylococcal strains isolated from cattle. Total phenols and saponin content of leaf extracts were investigated by standard in vitro methods. The methanolic extracts of these plants were found to comprise substantial content of phenolics and saponin at varying levels. The highest value of phenolics was estimated in P. vera extract (60.0 ± 1.3 mg gallic acid/g extract), followed by Z. amole (33.6 ± 1.4 mg gallic acid/g extract), and E. crassipes (23.0 ± 1.3 mg gallic acid/g extract). Saponin content for P. vera, Z. amole, and E. crassipes extracts were estimated as 41.0 ± 1.3, 35.8 ± 1.3, and 25.0 ± 1.2 mg diosgenin/g extract, respectively. The outcome of this study suggested the exploitation of methanolic extract of P. vera, Z. amole, and E. crassipes leaves for their possible application in ethnomedicine, particularly as drugs preparation against staphylococcal infections. In conclusion, the study indicates the biopotency of these plants against pathogenic MRSA present in cattle, and SOSA as well as CoNS bacteria present in rabbits, which could be a serious issue for livestock. Copyright © 2017 Elsevier Ltd. All rights reserved.

Antidiarrhoeal Activity of Musa paradisiaca Sap in Wistar Rats

PubMed Central

Yakubu, Musa T.; Nurudeen, Quadri O.; Salimon, Saoban S.; Yakubu, Monsurat O.; Jimoh, Rukayat O.; Nafiu, Mikhail O.; Akanji, Musbau A.; Oladiji, Adenike T.; Williams, Felicia E.

2015-01-01

The folkloric claim of Musa paradisiaca sap in the management of diarrhoea is yet to be substantiated or refuted with scientific data. Therefore, the aim of the current study was to screen the sap of M. paradisiaca for both its secondary metabolites and antidiarrhoeal activity at 0.25, 0.50, and 1.00 mL in rats. Secondary metabolites were screened using standard methods while the antidiarrhoeal activity was done by adopting the castor oil-induced diarrhoeal, castor oil-induced enteropooling, and gastrointestinal motility models. The sap contained flavonoids, phenolics, saponins, alkaloids, tannins, and steroids while cardiac glycosides, anthraquinones, triterpenes, cardenolides, and dienolides were not detected. In the castor oil-induced diarrhoeal model, the sap significantly (P < 0.05) prolonged the onset time of diarrhoea, decreased the number, fresh weight, and water content of feaces, and increased the inhibition of defecations. Na+-K+-ATPase activity in the small intestine increased significantly whereas nitric oxide content decreased. The decreases in the masses and volumes of intestinal fluid by the sap were accompanied by increase in inhibition of intestinal fluid content in the enteropooling model. The sap decreased the charcoal meal transit in the gastrointestinal motility model. In all the models, the 1.00 mL of the sap produced changes that compared well with the reference drugs. Overall, the antidiarrhoeal activity of Musa paradisiaca sap attributed to the presence of alkaloids, phenolics, flavonoids, and/or saponins which may involve, among others, enhancing fluid and electrolyte absorption through de novo synthesis of the sodium potassium ATPase and/or reduced nitric oxide levels. PMID:25893000

Antidiarrhoeal Activity of Musa paradisiaca Sap in Wistar Rats.

PubMed

Yakubu, Musa T; Nurudeen, Quadri O; Salimon, Saoban S; Yakubu, Monsurat O; Jimoh, Rukayat O; Nafiu, Mikhail O; Akanji, Musbau A; Oladiji, Adenike T; Williams, Felicia E

2015-01-01

The folkloric claim of Musa paradisiaca sap in the management of diarrhoea is yet to be substantiated or refuted with scientific data. Therefore, the aim of the current study was to screen the sap of M. paradisiaca for both its secondary metabolites and antidiarrhoeal activity at 0.25, 0.50, and 1.00 mL in rats. Secondary metabolites were screened using standard methods while the antidiarrhoeal activity was done by adopting the castor oil-induced diarrhoeal, castor oil-induced enteropooling, and gastrointestinal motility models. The sap contained flavonoids, phenolics, saponins, alkaloids, tannins, and steroids while cardiac glycosides, anthraquinones, triterpenes, cardenolides, and dienolides were not detected. In the castor oil-induced diarrhoeal model, the sap significantly (P < 0.05) prolonged the onset time of diarrhoea, decreased the number, fresh weight, and water content of feaces, and increased the inhibition of defecations. Na(+)-K(+)-ATPase activity in the small intestine increased significantly whereas nitric oxide content decreased. The decreases in the masses and volumes of intestinal fluid by the sap were accompanied by increase in inhibition of intestinal fluid content in the enteropooling model. The sap decreased the charcoal meal transit in the gastrointestinal motility model. In all the models, the 1.00 mL of the sap produced changes that compared well with the reference drugs. Overall, the antidiarrhoeal activity of Musa paradisiaca sap attributed to the presence of alkaloids, phenolics, flavonoids, and/or saponins which may involve, among others, enhancing fluid and electrolyte absorption through de novo synthesis of the sodium potassium ATPase and/or reduced nitric oxide levels.

A Rapid and Reliable Method for Total Protein Extraction from Succulent Plants for Proteomic Analysis.

PubMed

Lledías, Fernando; Hernández, Felipe; Rivas, Viridiana; García-Mendoza, Abisaí; Cassab, Gladys I; Nieto-Sotelo, Jorge

2017-08-01

Crassulacean acid metabolism plants have some morphological features, such as succulent and reduced leaves, thick cuticles, and sunken stomata that help them prevent excessive water loss and irradiation. As molecular constituents of these morphological adaptations to xeric environments, succulent plants produce a set of specific compounds such as complex polysaccharides, pigments, waxes, and terpenoids, to name a few, in addition to uncharacterized proteases. Since all these compounds interfere with the analysis of proteins by electrophoretic techniques, preparation of high quality samples from these sources represents a real challenge. The absence of adequate protocols for protein extraction has restrained the study of this class of plants at the molecular level. Here, we present a rapid and reliable protocol that could be accomplished in 1 h and applied to a broad range of plants with reproducible results. We were able to obtain well-resolved SDS/PAGE protein patterns in extracts from different members of the subfamilies Agavoideae (Agave, Yucca, Manfreda, and Furcraea), Nolinoideae (Dasylirion and Beucarnea), and the Cactaceae family. This method is based on the differential solubility of contaminants and proteins in the presence of acetone and pH-altered solutions. We speculate about the role of saponins and high molecular weight carbohydrates to produce electrophoretic-compatible samples. A modification of the basic protocol allowed the analysis of samples by bidimensional electrophoresis (2DE) for proteomic analysis. Furostanol glycoside 26-O-β-glucosidase (an enzyme involved in steroid saponin synthesis) was successfully identified by mass spectrometry analysis and de novo sequencing of a 2DE spot from an Agave attenuata sample.

Superiority of SDS lysis over saponin lysis for direct bacterial identification from positive blood culture bottle by MALDI-TOF MS.

PubMed

Caspar, Yvan; Garnaud, Cécile; Raykova, Mariya; Bailly, Sébastien; Bidart, Marie; Maubon, Danièle

2017-05-01

Fast species diagnosis has an important health care impact, as rapid and specific antibacterial therapy is of clear benefit for patient's outcome. Here, a new protocol for species identification directly from positive blood cultures is proposed. Four in-house protocols for bacterial identification by MS directly from clinical positive blood cultures evaluating two lytic agents, SDS and saponin, and two protein extraction schemes, fast (FP) and long (LP) are compared. One hundred and sixty-eight identification tests are carried out on 42 strains. Overall, there are correct identifications to the species level in 90% samples for the SDS-LP, 60% for the SDS-FP, 48% for the saponin LP, and 43% for the saponin FP. Adapted scores allowed 92, 86, 72, and 53% identification for SDS-LP, SDS-FP, saponin LP, and saponin FP, respectively. Saponin lysis is associated with a significantly lower score compared to SDS (0.87 [0.83-0.92], p-value < 0.001). This study supports the use of SDS lysis instead of saponin lysis and the application of this rapid and cost-effective protocol in daily routine for microbiological agents implicated in septicemia. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Saponin Profile of Wild Asparagus Species.

PubMed

Jaramillo-Carmona, Sara; Rodriguez-Arcos, Rocío; Jiménez-Araujo, Ana; López, Sergio; Gil, Juan; Moreno, Roberto; Guillén-Bejarano, Rafael

2017-03-01

The aim of this work was to study the saponin profiles from spears of different wild asparagus species in the context of its genetic diversity aside from geographical seed origin. They included Asparagus pseudoscaber Grecescu, Asparagus maritimus (L.) Mill., Asparagus brachiphyllus Turcz., Asparagus prostrates Dumort., and Asparagus officinalis L. The saponin analysis by LC-MS has shown that saponin profile from wild asparagus is similar to that previously described for triguero asparagus from Huétor-Tájar landrace (triguero HT), which had not ever been reported in the edible part of asparagus. All the samples, except A. officinalis, were characterized for having saponins distinct to protodioscin and the total saponin contents were 10-fold higher than those described for commercial hybrids of green asparagus. In particular, A. maritimus from different origins were rich in saponins previously found in triguero HT. These findings supported previous suggestion, based on genetic analysis, about A. maritimus being the origin of triguero HT. Multivariate statistics including principal component analysis and hierarchical clustering analysis were used to define both similarities and differences among samples. The results showed that the greatest variance of the tested wild asparagus could be attributed to differences in the concentration of particular saponins and this knowledge could be a tool for identifying similar species. © 2017 Institute of Food Technologists®.

Diagnostic ion filtering to characterize ginseng saponins by rapid liquid chromatography with time-of-flight mass spectrometry.

PubMed

Qi, Lian-Wen; Wang, Huai-You; Zhang, Hui; Wang, Chong-Zhi; Li, Ping; Yuan, Chun-Su

2012-03-23

As one of the most commonly used medicinal plants, ginseng has been an attractive model herb for study. A wide range of analytical methods has been used to characterize its constituents. However, less effort has been devoted to the rare ginseng saponins, especially their isomers and sugar linkages. In this study, we used segmental monitoring and diagnostic ion filtering to characterize ginseng saponins by rapid liquid chromatography with time-of-flight mass spectrometry (LC-TOF-MS). By using selected diagnostic ions, specific groups of ginseng saponins were readily extracted from the complicated matrix. 20(R) and 20(S) stereo-saponins were differentiated using the peak abundance ratio of [M-H(2)O+H](+) to [M-2H(2)O+H](+). The fragmentation behavior of ginsenosides was first reported in negative ion mode by MS/MS with high-energy collision-induced dissociation, producing rules to determine sugar numbers, positions and linkages. Using the rules, we identified and compared the nontarget ginseng saponin profiling of raw and steamed American ginseng roots and berries. We characterized 70 saponins in the samples. Our strategy can be extended to screen and characterize other rare ginseng saponins and their metabolites. Copyright © 2012 Elsevier B.V. All rights reserved.

Dietary Karaya Saponin and Rhodobacter capsulatus Exert Hypocholesterolemic Effects by Suppression of Hepatic Cholesterol Synthesis and Promotion of Bile Acid Synthesis in Laying Hens.

PubMed

Afrose, Sadia; Hossain, Md Sharoare; Salma, Ummay; Miah, Abdul Gaffar; Tsujii, Hirotada

2010-01-01

This study was conducted to elucidate the mechanism underlying the hypolipidemic action of karaya saponin or Rhodobacter (R.) capsulatus. A total of 40 laying hens (20-week-old) were assigned into four dietary treatment groups and fed a basal diet (as a control) or basal diets supplemented with either karaya saponin, R. capsulatus, or both for 60 days. The level of serum low-density-lipoprotein cholesterol and the levels of cholesterol and triglycerides in the serum, liver, and egg yolk were reduced by all the supplementations (P < .05). Liver bile acid concentration and fecal concentrations of cholesterol, triacylglycerol, and bile acid were simultaneously increased by the supplementation of karaya saponin, R. capsulatus, and the combination of karaya saponin and R. capsulatus (P < .05). The supplementation of karaya saponin, R. capsulatus, and the combination of karaya saponin and R. capsulatus suppressed the incorporation of (14)C from 1-(14)C-palmitic acid into the fractions of total lipids, phospholipids, triacylglycerol, and cholesterol in the liver in vitro (P < .05). These findings suggest that the hypocholesterolemic effects of karaya saponin and R. capsulatus are caused by the suppression of the cholesterol synthesis and the promotion of cholesterol catabolism in the liver.

Dietary Karaya Saponin and Rhodobacter capsulatus Exert Hypocholesterolemic Effects by Suppression of Hepatic Cholesterol Synthesis and Promotion of Bile Acid Synthesis in Laying Hens

PubMed Central

Afrose, Sadia; Hossain, Md. Sharoare; Salma, Ummay; Miah, Abdul Gaffar; Tsujii, Hirotada

2010-01-01

This study was conducted to elucidate the mechanism underlying the hypolipidemic action of karaya saponin or Rhodobacter (R.) capsulatus. A total of 40 laying hens (20-week-old) were assigned into four dietary treatment groups and fed a basal diet (as a control) or basal diets supplemented with either karaya saponin, R. capsulatus, or both for 60 days. The level of serum low-density-lipoprotein cholesterol and the levels of cholesterol and triglycerides in the serum, liver, and egg yolk were reduced by all the supplementations (P < .05). Liver bile acid concentration and fecal concentrations of cholesterol, triacylglycerol, and bile acid were simultaneously increased by the supplementation of karaya saponin, R. capsulatus, and the combination of karaya saponin and R. capsulatus (P < .05). The supplementation of karaya saponin, R. capsulatus, and the combination of karaya saponin and R. capsulatus suppressed the incorporation of 14C from 1-14C-palmitic acid into the fractions of total lipids, phospholipids, triacylglycerol, and cholesterol in the liver in vitro (P < .05). These findings suggest that the hypocholesterolemic effects of karaya saponin and R. capsulatus are caused by the suppression of the cholesterol synthesis and the promotion of cholesterol catabolism in the liver. PMID:21490913

Brine shrimp lethality assay of Bacopa monnieri.

PubMed

D'Souza, Prashanth; Deepak, Mundkinajeddu; Rani, Padmaja; Kadamboor, Sandhya; Mathew, Anjana; Chandrashekar, Arun P; Agarwal, Amit

2002-03-01

Successive petroleum ether, chloroform, ethanol and water extracts, a saponin rich fraction (SRF) and bacoside A isolated from Bacopa monnieri were tested for brine shrimp lethality. Successive ethanol extracts and SRF showed potent activity. Bacoside A showed the maximum activity with a LC(50) of 38.3 microg/mL. The results confirmed the previous reports of an anticancer effect of Bacopa monnieri and suggest bacoside A as the active constituent. Copyright 2002 John Wiley & Sons, Ltd.

Structural characterization and identification of iridoid glycosides, saponins, phenolic acids and flavonoids in Flos Lonicerae Japonicae by a fast liquid chromatography method with diode-array detection and time-of-flight mass spectrometry.

PubMed

Qi, Lian-Wen; Chen, Chun-Yun; Li, Ping

2009-10-01

A fast liquid chromatography method with diode-array detection (DAD) and time-of-flight mass spectrometry (TOF-MS) has been developed for analysis of constituents in Flos Lonicerae Japonicae (FLJ), a traditional Chinese medicine derived from the flower bud of Lonicera japonica. The chromatographic analytical time decreased to 25 min without sacrificing resolution using a column packed with 1.8-microm porous particles (4.6 x 50 mm), three times faster than the performance of conventional 5.0-microm columns (4.6 x 150 mm). Four major groups of compounds previously isolated from FLJ were structurally characterized by DAD-TOF-MS: iridoid glycosides showed maximum UV absorption at 240 nm; phenolic acids at 217, 242, and 326 nm; flavonoids at 255 and 355 nm; while saponins had no absorption. In electrospray ionization (ESI)-TOF-MS experiments, elimination of a glucose unit (162 Da), and successive losses of H(2)O, CH(3)OH and CO, were generally observed in iridoid glycosides; saponins were characterized by a series of identical aglycone ions; phenolic acids typically generated a base peak at [M-H-caffeoyl](-) by loss of a caffeic acid unit (162 Da) and several marked quinic acid moiety ions; cleavage of the glycosidic bond (loss of 162 or 308 Da), subsequent losses of H(2)O, CO, RDA and C-ring fragmentation were the most possible fragmentation pathways for flavonoids. By accurate mass measurements within 4 ppm error for each molecular ion and subsequent fragment ions, as well as the 'full mass spectral' information of TOF-MS, a total of 41 compounds including 13 iridoid glycosides, 11 phenolic acids, 7 saponins, and 10 flavonoids were identified in a methanolic extract of FLJ. Copyright (c) 2009 John Wiley & Sons, Ltd.

Ophirapstanol trisulfate, a new biologically active steroid sulfate from the deep water marine sponge Topsentia ophiraphidites.

PubMed

Gunasekera, S P; Sennett, S H; Kelly-Borges, M; Bryant, R W

1994-12-01

Ophirapstanol trisulfate [1], a new steroid trisulfate related to sokotrasterol trisulfate was isolated from a deep water marine sponge Topsentia ophiraphidites. Compound 1 exhibited significant inhibition in the guanosine diphosphate/G-protein RAS exchange assay. The structure elucidation of 1 and ophirapstanol [2] by nmr spectroscopy is described.

ROLE OF STEROID HORMONES AND DECIDUAL INDUCTION IN THE REGULATION OF ADENOSINE DIPHOSPHORIBOSYL TRANSFERASE ACTIVITY IN RAT ENDOMETRIUM

EPA Science Inventory

To assess the effect of ovarian steroid hormones on enzyme activity, adenosine diphosphoribosyl transferase (ADPRT) was measured in endometrial nuclei isolated on estrus and on d 4 from rats ovariectomized on estrus (d 0) and treated d 0-3 with (a) vehicle, (b) 1 ug estrone/d (E)...

LC-MS-based quantification method for Achyranthes root saponins.

PubMed

Kawahara, Yuki; Hoshino, Tatsuro; Morimoto, Hidetaka; Shinizu, Tomofumi; Narukawa, Yuji; Fuchino, Hiroyuki; Kawahara, Nobuo; Kiuchi, Fumiyuki

2016-01-01

A liquid chromatography mass spectrometry (LC-MS) method was developed for simultaneous quantitative analysis of Achyranthes root saponins: chikusetsusaponins IVa (1) and V (2), achyranthosides B (3), C (4), D (5), E (6), and G (7), sulfachyranthosides B (8) and D (9), and betavulgarosides II (10) and IV (11). Satisfactory separation of the saponins was achieved with the use of a volatile ion-pair reagent (dihexyl ammonium acetate) on a phenyl-hexylated silica gel column, and the amounts of saponins extracted under three different conditions were determined. When Achyranthes root was extracted with water at room temperature, achyranthosides B (3) and D (5) were the major saponins, and smaller amounts of other saponins (4, 6-11) were present. However, the amounts of chikusetsusaponins (1 and 2) were negligible. Under the condition to make a standard decoction of a Kampo formula, the major saponins were achyranthosides B (3), C (4), and D (5), and small amounts of chikusetsusaponins IVa (1) and V (2) appeared, whereas prolonged heating largely increased the amounts of chikusetsusaponins. This method can be used for quality control of Achyranthes root.

[Studies on extraction process optimization of patrinia scabra Bunge saponins].

PubMed

Wang, Xue-Xi; Chen, Ru; Li, Shi-Gang; Shen, Wei; Cheng, Wei-Dong; Zhao, Jian-Xiong

2007-05-01

To optimize the conditions for the extraction of Patrinia scabra Bunge saponins. Orthogonal experimental design and ultrasonic method were employed to examine the conditions for the extraction by determination of saponins. The optimun condition for the extraction of Patrinia scabra Bunge saponins was as follows: 65% ethanol for 40 minutes, 55 degrees C and 210 watt of ultrasonic efficinecy. The extraction method of Patrinia scabra Bunge sponins is simple and efficient.

Syntheses and mucosal adjuvant activity of simplified oleanolic acid saponins possessing cinnamoyl ester.

PubMed

Shirahata, Tatsuya; Nagai, Takayuki; Hirata, Nozomu; Yokoyama, Masaki; Katsumi, Tatsuya; Konishi, Naruki; Nishino, Takashi; Makino, Kazuishi; Yamada, Haruki; Kaji, Eisuke; Kiyohara, Hiroaki; Kobayashi, Yoshinori

2017-03-15

A series of new simplified oleanolic acid saponins with a glycosyl ester moiety at C28, were efficiently prepared. Furthermore, the effect of nasal administration of the synthetic oleanolic acid saponins on the nasal anti-influenza virus antibody titer against secondary nasal inoculation of the influenza split vaccine was examined. The result revealed cinnamoyl saponin as a suitable candidate vaccine adjuvant. Copyright © 2016. Published by Elsevier Ltd.

[Studies on the process of Herba Clinopodii saponins purified with macroporous adsorption resin].

PubMed

Zhang, Yi; Yan, Dan; Han, Yumei

2005-10-01

To study the technological parameters of the purification process of saponins with macroporous adsorption resin. The adsorptive characteristics and elutive parameters of the process were studied by taking the elutive and purified ratio of saponins as markers. 11.4 ml of the extraction of Herba Clinopodii (crude drugs 0.2 g/ml) was purified with a column of macroporous adsorption resin (phi15 mm x H90 mm, dry weight 2.5 g) and washed with 3BV of distilled water, then eluted with 3BV of 30% ethanol and 3BV of 70% ethanol. Most of saponins were collected in the 70% ethanol. With macroporous adsorption resin adsorbing and purifying,the elutive ratio of saponins is 86.8% and the purity reaches 153.2%. So this process of applying macroporous adsorption resin to adsorb and purify Saponins is feasible.

Promotion of bone growth by dietary soy protein isolate: Comparision with dietary casein, whey hydrolysate and rice protein isolate in growing female rats

USDA-ARS?s Scientific Manuscript database

The effects of different dietary protein sources(casein (CAS), soy protein isolate (SPI), whey protein hydrolysate (WPH) and rice protein isolate (RPI)) on bone were studied in intact growing female rats and in ovarectomized (OVX) rats showing sex steroid deficiency-induced bone loss. In addition, S...

Simultaneous Determination of Four Triterpenoid Saponins in Aralia elata Leaves by HPLC-ELSD Combined with Hierarchical Clustering Analysis.

PubMed

Sun, Yichun; Li, Baimei; Lin, Xiaoting; Xue, Juan; Wang, Zhibin; Zhang, Hongwei; Jiang, Hai; Wang, Qiuhong; Kuang, Haixue

2017-05-01

Aralia elata leaves are known to have several biological activities, including anti-arrythmia, antitumor, anti-inflammatory, anti-fatigue, antimicrobial and antiviral effects. Our previous study found that triterpenoid saponins from the leaves of A. elata had antitumor effects. Quantification of the triterpenoids is important for the quality control of A. elata leaves. To establish high-performance liquid chromatography coupled with evaporative light scattering detection (HPLC-ELSD) for the simultaneous determination of four major triterpenoid saponins, including Aralia-saponin IV, Aralia-saponin VI, 3-O-β-d- glucopyranosyl-(1 → 3)-β-d-glucopyranosyl-(1 → 3)-β-d-glucopyranosyl oleanolic acid 28-O-β-d-glucopyranoside (Aralia-saponin TTP)and Aralia-saponin V. The separation was carried out on a Dikma Diamonsil C 18 column (4.6 mm × 250 mm, 5 μm) efficiently with gradient elution consisting of acetonitrile and water. All calibration curves showed good linear regression (R 2  > 0.9996) within the ranges of tested concentrations. This validated method was applied to determine the contents of the four major triterpenoid saponins in 53 samples from different regions of northeast China. Hierarchical clustering analysis was first used to classify and differentiate Aralia elata leaves. The method developed was successfully applied to analyse four major triterpenoid saponins in Aralia elata leaves which is helpful for quality control of the herb. Copyright © 2017 John Wiley & Sons, Ltd. Copyright © 2017 John Wiley & Sons, Ltd.

Simultaneous quantification of triterpenoid saponins in rat plasma by UHPLC-MS/MS and its application to a pharmacokinetic study after oral total saponin of Aralia elata leaves.

PubMed

Sun, Yichun; Xue, Juan; Li, Baimei; Lin, Xiaoting; Wang, Zhibin; Jiang, Hai; Zhang, Hongwei; Wang, Qiuhong; Kuang, Haixue

2016-11-01

A rapid, sensitive, and reliable analytical ultra performance liquid chromatography with tandem mass spectrometry method was developed for the simultaneous determination of Aralia-saponin IV, 3-O-β-d-glucopyranosyl-(1→3)-β-d-glucopyranosyl-(1→3)-β-d-glucopyranosyl oleanolic acid 28-O-β-d-glucopyranoside, Aralia-saponin A and Aralia-saponin B after the oral administration of total saponin of Aralia elata leaves in rat plasma. Plasma samples were pretreated by protein precipitation with methanol. The analysis was performed on an ACQUITY UPLC HSS T3 column. The detection was performed on a triple quadrupole tandem mass spectrometer in multiple reaction monitoring mode using an electrospray ionization source with negative ionization mode. Under the experimental conditions, the calibration curves of four analytes had good linearity values (r > 0.991). The intra- and inter-day precision values of the four analytes were ≤ 11.6%, and the accuracy was between -6.2 and 4.2%.The extraction recoveries of four triterpenoid saponins were in the range of 84.06-91.66% (RSD < 10.5%), and all values of the matrix effect were more than 90.30%. The developed analytical method was successfully applied to pharmacokinetic study on simultaneous determination of the four triterpenoid saponins in rat plasma after oral administration of total saponin of Aralia elata leaves, which helps guiding clinical usage of Aralia elata leaves. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Insect Attraction versus Plant Defense: Young Leaves High in Glucosinolates Stimulate Oviposition by a Specialist Herbivore despite Poor Larval Survival due to High Saponin Content

PubMed Central

Badenes-Perez, Francisco R.; Gershenzon, Jonathan; Heckel, David G.

2014-01-01

Glucosinolates are plant secondary metabolites used in plant defense. For insects specialized on Brassicaceae, such as the diamondback moth, Plutella xylostella L. (Lepidoptera: Plutellidae), glucosinolates act as “fingerprints” that are essential in host plant recognition. Some plants in the genus Barbarea (Brassicaceae) contain, besides glucosinolates, saponins that act as feeding deterrents for P. xylostella larvae, preventing their survival on the plant. Two-choice oviposition tests were conducted to study the preference of P. xylostella among Barbarea leaves of different size within the same plant. P. xylostella laid more eggs per leaf area on younger leaves compared to older ones. Higher concentrations of glucosinolates and saponins were found in younger leaves than in older ones. In 4-week-old plants, saponins were present in true leaves, while cotyledons contained little or no saponins. When analyzing the whole foliage of the plant, the content of glucosinolates and saponins also varied significantly in comparisons among plants that were 4, 8, and 12 weeks old. In Barbarea plants and leaves of different ages, there was a positive correlation between glucosinolate and saponin levels. This research shows that, in Barbarea plants, ontogenetical changes in glucosinolate and saponin content affect both attraction and resistance to P. xylostella. Co-occurrence of a high content of glucosinolates and saponins in the Barbarea leaves that are most valuable for the plant, but are also the most attractive to P. xylostella, provides protection against this specialist herbivore, which oviposition behavior on Barbarea seems to be an evolutionary mistake. PMID:24752069

Insect attraction versus plant defense: young leaves high in glucosinolates stimulate oviposition by a specialist herbivore despite poor larval survival due to high saponin content.

PubMed

Badenes-Perez, Francisco R; Gershenzon, Jonathan; Heckel, David G

2014-01-01

Glucosinolates are plant secondary metabolites used in plant defense. For insects specialized on Brassicaceae, such as the diamondback moth, Plutella xylostella L. (Lepidoptera: Plutellidae), glucosinolates act as "fingerprints" that are essential in host plant recognition. Some plants in the genus Barbarea (Brassicaceae) contain, besides glucosinolates, saponins that act as feeding deterrents for P. xylostella larvae, preventing their survival on the plant. Two-choice oviposition tests were conducted to study the preference of P. xylostella among Barbarea leaves of different size within the same plant. P. xylostella laid more eggs per leaf area on younger leaves compared to older ones. Higher concentrations of glucosinolates and saponins were found in younger leaves than in older ones. In 4-week-old plants, saponins were present in true leaves, while cotyledons contained little or no saponins. When analyzing the whole foliage of the plant, the content of glucosinolates and saponins also varied significantly in comparisons among plants that were 4, 8, and 12 weeks old. In Barbarea plants and leaves of different ages, there was a positive correlation between glucosinolate and saponin levels. This research shows that, in Barbarea plants, ontogenetical changes in glucosinolate and saponin content affect both attraction and resistance to P. xylostella. Co-occurrence of a high content of glucosinolates and saponins in the Barbarea leaves that are most valuable for the plant, but are also the most attractive to P. xylostella, provides protection against this specialist herbivore, which oviposition behavior on Barbarea seems to be an evolutionary mistake.

Two new triterpenoid glycosides isolated from Aesculus assamica GRIFF.

PubMed

Liu, Hongwei; Zhang, Xue; Gao, Hao; Wang, Nali; Jin, Sanlin; Cai, Bin; Yao, Xinsheng; Cai, Guoping

2005-10-01

Phytochemical study of the ethanol extract of the seeds of Aesculus assamica led to the isolation of two new triterpenoid saponins. The structure of the new compounds were elucidated on the basis of spectral data to be 28-O-acetyl-21-O-(4-O-angeloyl)-6-deoxy-beta-glucopyranosyl-3-O-[beta-glucopyranosyl(1-2)-O-[beta-glucopyranosyl(1-4)]-beta-glucuronopyranosyl]protoaescigenin (1), and 21-O-(4-O-angeloyl)-6-deoxy-beta-glucopyranosyl-3-O-[beta-glucopyranosyl(1-2)-O-[beta-glucopyranosyl(1-4)]-beta-glucuronopyranosyl]protoaescigenin (2). Their in vitro bioactivity against plant pathogenic fungus Pyricularia oryzae and cytotoxicity against K562 and HCT-15 cell lines were evaluated.

Effects of beta-escin and saponin on the transverse-tubular system and sarcoplasmic reticulum membranes of rat and toad skeletal muscle.

PubMed

Launikonis, B S; Stephenson, D G

1999-05-01

Mechanically skinned skeletal muscle fibres from rat and toad were exposed to the permeabilizing agents beta-escin and saponin. The effects of these agents on the sealed transverse tubular system (t-system) and sarcoplasmic reticulum (SR) were examined by looking at changes in the magnitude of the force responses to t-system depolarization, the time course of the fluorescence of fura-2 trapped in the sealed t-system, and changes in the magnitude of caffeine-induced contractures following SR loading with Ca2+ under defined conditions. In the presence of 2 microg ml-1 beta-escin and saponin, the response to t-system depolarization was not completely abolished, decreasing to a plateau, and a large proportion of fura-2 remained in the sealed t-system. At 10 microg ml-1, both agents abolished the ability of both rat and toad preparations to respond to t-system depolarization after 3 min of exposure, but a significant amount of fura-2 remained in sealed t-tubules even after exposure to 100 microg ml-1 beta-escin and saponin for 10 min. beta-Escin took longer than saponin to reduce the t-system depolarizations and fura-2 content of the sealed t-system to a similar level. The ability of the SR to load Ca2+ was reduced to a lower level after treatment with beta-escin than saponin. This direct effect on the SR occurred at much lower concentrations for rat (2 microg ml-1 beta-escin and 10 microg ml-1 saponin) than toad (10 microg ml-1 beta-escin and 150 microg ml-1 saponin). The reverse order in sensitivities to beta-escin and saponin of t-system and SR membranes indicates that the mechanisms of action of beta-escin and saponin are different in the two types of membrane. In conclusion, this study shows that: (1) beta-escin has a milder action on the surface membrane than saponin; (2) beta-escin is a more potent modifier of SR function; (3) simple permeabilization of membranes is not sufficient to explain the effects of beta-escin and saponin on muscle membranes; and (4) the t-system network within muscle fibres is not a homogeneous compartment.

Inhibitory effect of saponins and polysaccharides from Radix ranunculi ternati on human gastric cancer BGC823 cells.

PubMed

Niu, Lidan; Zhou, Yingfeng; Sun, Bing; Hu, Junling; Kong, Lingyu; Duan, Sufang

2013-01-01

The effects of different Radix ranunculi ternati extracts on human gastric cancer BGC823 cells were investigated, different methods were used to extract the saponins and polysaccharides from Radix ranunculi ternati, and MTT assay and colony formation assay were used to observe the effects of saponins and polysaccharides from Radix ranunculi ternati on in-vitro cultured human gastric cancer BGC823 cells. The results found that the saponins and polysaccharides from Radix Ranunculi Ternati had certain effects on both the growth and colony formation of human gastric cancer BGC823 cells, while improving the immune function of normal mice, of which saponins had more significant effects than polysaccharides.

Purification of an Immunoadjuvant Saponin Fraction from Quillaja brasiliensis Leaves by Reversed-Phase Silica Gel Chromatography.

PubMed

Yendo, Anna C A; de Costa, Fernanda; Kauffmann, Carla; Fleck, Juliane D; Gosmann, Grace; Fett-Neto, Arthur G

2017-01-01

Saponins include a large variety of molecules that find several applications in pharmacology. The use of Quillaja saponaria saponins as immunological adjuvants in vaccines is of interest due to their capacity to stimulate both humoral and cellular responses. The congener species Q. brasiliensis has saponins with chemical similarities and adjuvant activity comparable to that of Q. saponaria fraction Quil-A ® , with additional advantages of showing lower toxicity and reduced hemolytic activity. Here we describe in detail the methods for preparing the aqueous extract from Q. brasiliensis leaves, as well as the purification of the bioactive saponin fraction QB-90 using silica reversed-phase chromatography.

Semisynthesis of Analogues of the Saponin Immunoadjuvant QS-21.

PubMed

Fernández-Tejada, Alberto; Walkowicz, William E; Tan, Derek S; Gin, David Y

2017-01-01

Saponins are triterpene glycoside natural products that exhibit many different biological properties, including activation and modulation of the immune system, and have therefore attracted significant interest as immunological adjuvants for use in vaccines. QS-21 is the most widely used and promising saponin adjuvant but suffers from several liabilities, such as scarcity, dose-limiting toxicity, and hydrolytic instability. Chemical synthesis has emerged as a powerful approach to obtain homogeneous, pure samples of QS-21 and to improve its properties and therapeutic profile by providing access to optimized, synthetic saponin variants. Herein, we describe a general method for the semisynthesis of these molecules from QS-21, with detailed synthetic protocols for two saponin variants developed in our recent work.

Metabolism of methylstenbolone studied with human liver microsomes and the uPA⁺/⁺-SCID chimeric mouse model.

PubMed

Geldof, Lore; Lootens, Leen; Polet, Michael; Eichner, Daniel; Campbell, Thane; Nair, Vinod; Botrè, Francesco; Meuleman, Philip; Leroux-Roels, Geert; Deventer, Koen; Eenoo, Peter Van

2014-07-01

Anti-doping laboratories need to be aware of evolutions on the steroid market and elucidate steroid metabolism to identify markers of misuse. Owing to ethical considerations, in vivo and in vitro models are preferred to human excretion for nonpharmaceutical grade substances. In this study the chimeric mouse model and human liver microsomes (HLM) were used to elucidate the phase I metabolism of a new steroid product containing, according to the label, methylstenbolone. Analysis revealed the presence of both methylstenbolone and methasterone, a structurally closely related steroid. Via HPLC fraction collection, methylstenbolone was isolated and studied with both models. Using HLM, 10 mono-hydroxylated derivatives (U1-U10) and a still unidentified derivative of methylstenbolone (U13) were detected. In chimeric mouse urine only di-hydroxylated metabolites (U11-U12) were identified. Although closely related, neither methasterone nor its metabolites were detected after administration of isolated methylstenbolone. Administration of the steroid product resulted mainly in the detection of methasterone metabolites, which were similar to those already described in the literature. Methylstenbolone metabolites previously described were not detected. A GC-MS/MS multiple reaction monitoring method was developed to detect methylstenbolone misuse. In one out of three samples, previously tested positive for methasterone, methylstenbolone and U13 were additionally detected, indicating the applicability of the method. Copyright © 2014 John Wiley & Sons, Ltd.

Structure Elucidation of New Acetylated Saponins, Lessoniosides A, B, C, D, and E, and Non-Acetylated Saponins, Lessoniosides F and G, from the Viscera of the Sea Cucumber Holothuria lessoni

PubMed Central

Bahrami, Yadollah; Franco, Christopher M. M.

2015-01-01

Sea cucumbers produce numerous compounds with a wide range of chemical structural diversity. Among these, saponins are the most diverse and include sulfated, non-sulfated, acetylated and methylated congeners with different aglycone and sugar moieties. In this study, MALDI and ESI tandem mass spectrometry, in the positive ion mode, were used to elucidate the structure of new saponins extracted from the viscera of H. lessoni. Fragmentation of the aglycone provided structural information on the presence of the acetyl group. The presence of the O-acetyl group was confirmed by observing the mass transition of 60 u corresponding to the loss of a molecule of acetic acid. Ion fingerprints from the glycosidic cleavage provided information on the mass of the aglycone (core), and the sequence and type of monosaccharides that constitute the sugar moiety. The tandem mass spectra of the saponin precursor ions [M + Na]+ provided a wealth of detailed structural information on the glycosidic bond cleavages. As a result, and in conjunction with existing literature, we characterized the structure of five new acetylated saponins, Lessoniosides A–E, along with two non-acetylated saponins Lessoniosides F and G at m/z 1477.7, which are promising candidates for future drug development. The presented strategy allows a rapid, reliable and complete analysis of native saponins. PMID:25603350

Chemical profiles and anticancer effects of saponin fractions of different polarity from the leaves of Panax notoginseng.

PubMed

Qian, Mao; Yi, Li; Song-Lin, Li; Jie, Yang; Ping-Hu, Zhang; Qiang, Wang

2014-01-01

To evaluate the chemical profiles and cytotoxic effects among the total saponin fraction (TSF), 25% ethanol fraction (25EF), 50% ethanol fraction (50EF), and 85% ethanol fraction (85EF) prepared by macroporous resin from the leaves of Panax notoginseng. The simultaneous determination of thirteen main saponins, as well as the chemical profiles of saponin fractions of different polarity, was made by HPLC-DAD and LC-ESI-MS(n) analysis. The cytotoxic effects were determined against KP4 cells (human pancreatic cancer), NCI-H727 cells (human lung cancer), HepG2 cells (human hepatocellular cancer), and SGC-7901 cells (human gastric adenocarcinoma). Chemical analysis indicated that 85EF possessed the most abundant cytotoxic protopanaxadiol saponins, including the marker saponins F2, 20(R)-Rg3, 20(S)-Rg3, and Rh2. The MTT assay showed that 85EF also had the strongest cytotoxic effects among the four fractions. 25EF showed no anti-proliferative effects, while 50EF and TSF exhibited weak anti-proliferative activity. From the aspect of comprehensive utilization of resources, 85EF, enriched with low polarity PPD group saponins, is a new alternative source of anticancer saponins, and a promising botanical preparation for further anticancer studies. Copyright © 2014 China Pharmaceutical University. Published by Elsevier B.V. All rights reserved.

Identification of a new steroid degrading bacterial strain H5 from the Baltic Sea and isolation of two estradiol inducible genes.

PubMed

Sang, Yingying; Xiong, Guangming; Maser, Edmund

2012-03-01

The presence of steroid hormones in the aquatic environment is potentially threatening the population dynamics of all kinds of sea animals and public health. Environmental estrogens in water have been reported to be associated with abnormal sexual development and abnormal feminizing responses in some animals. New approaches for the bioremediation of steroid hormones from the environment are therefore urgently sought. We have previously isolated a steroid degrading bacterial strain (H5) from the Baltic Sea, at Kiel, Germany. In the present investigation, 16S rRNA analysis showed that marine strain H5 belongs to the genus Vibrio, family Vibrionaceae and class Gamma-Proteobacteria. To enable identification of steroid inducible genes from bacterial strain H5, a library was constructed of H5 chromosomal DNA fragments cloned into a fluorescent reporter (pKEGFP-2). A reporter plasmid pK3α-4.6-EGFP3 containing the estrogen-inducible gene 3α-hydroxysteroid dehydrogenase/carbonyl reductase (3α-HSD/CR) from Comamonas testosteroni (C. testosteroni) was created as a positive control. Steroid induction could be detected by a microplate fluorescence reader, when the plasmids were transformed into Escherichia coli (E. coli) HB101 cells. With our meta-genomic pKEGFP-2 approach, we identified two estradiol-inducible genes from marine strain H5, which are obviously involved in steroid degradation. Sequencing of the pKEGFP-2 inserts and data base research at NCBI revealed that one gene corresponds to 3-ketosteroid-delta-1-dehydrogenase from several Mycobacterium strains, while the other showed high similarity to carboxylesterase in Sebadella termitidis and Brachyspira murdochii. Both 3-ketosteroid-delta-1-dehydrogenase and carboxylesterase are one of the first enzymes in steroid degradation. In addition, we identified a strain H5 specific DNA sequence of 480bp which allows sensitive PCR detection and quantification of strain H5 bacteria in "unknown" seawater samples. Currently, the exact characterization and systematic classification of the marine steroid degrading bacterial strain H5 is envisaged, which might be used for the bioremediation of steroid contaminations in seawater. Article from a special issue on steroids and microorganisms. Copyright © 2011 Elsevier Ltd. All rights reserved.

[Contents of total anthocyanins and total saponins as well as composition of saponin monomers of Purple and Green Notoginseng Radix et Rhizoma].

PubMed

Zhao, Chang-ling; Yang, Sheng-chao; Chen, Zhong-jian; Shen, Yong; Wei, Fu-gang; Wang, Wu; Long, Ting-ju

2014-10-01

The contents of total anthocyanins and total saponins as well as the composition of saponin monomers of Purple and Green Notoginseng Radix et Rhizoma were studied to compare the medicinal quality and commercial values. Three-year-old Notoginseng Radix et Rhizoma was selected as the research materials. The contents of total anthocyanins and total saponins were determined by spectrophotometry. The compositions of saponin monomers were monitored by HPLC. The significance of content differences was determined by variance analysis. The contents of total anthocyanins and total saponins of Purple Notoginseng Radix et Rhizomawere about 204.85% and 33.86% higher than those of Green Notoginseng Radix et Rhizoma respectively. The Purple and Green Notoginseng Radix et Rhizoma both contained five saponin monomers whose contents were as follows: ginsenoside Rg1 > ginsenoside Rb1 > notoginsenoside R1 > ginsenoside Rd > ginsenoside Re. The contents of notoginsenoside R1, ginsenoside Rd and ginsenoside Re of Purple Notoginseng Radix et Rhizoma were about 16.03%, 10.83% and 5.39% higher than those of Green Notoginseng Radix et Rhizoma respectively. However, the contents of ginsenoside Rg1 and ginsenoside Rb1 of Green Notoginseng Radix et Rhizoma were about 0.93% and 3.33% higher than those of Purple Notoginseng Radix et Rhizoma respectively. With respect to Green Notoginseng Radix et Rhizoma, the increase of the total anthocyanins in Purple Notoginseng Radix et Rhizoma reached a significant level, but the increases of total saponins, notoginsenoside R1, ginsenoside Rd and ginsenoside Re and the decreases of ginsenoside Rg1 and ginsenoside Rb1 did not. The total anthocyanins accumulation in Notoginseng Radix et Rhizoma implies the content increases of the total saponins, notoginsenoside R1, ginsenoside Rd and ginsenoside Re, and the slight decreases of ginsenoside Rg1 and ginsenoside Rb1 contents; but the type and relative contents of saponin monomers remain unchanged. The medicinal quality and commercial value of Purple Notoginseng Radix et Rhizoma are higher than those of Green Notoginseng Radix et Rhizoma.

Saponin 6 derived from Anemone taipaiensis induces U87 human malignant glioblastoma cell apoptosis via regulation of Fas and Bcl‑2 family proteins.

PubMed

Ji, Chen-Chen; Tang, Hai-Feng; Hu, Yi-Yang; Zhang, Yun; Zheng, Min-Hua; Qin, Hong-Yan; Li, San-Zhong; Wang, Xiao-Yang; Fei, Zhou; Cheng, Guang

2016-07-01

Glioblastoma multiforme (GBM) is the most common and aggressive type of brain tumor, and is associated with a poor prognosis. Saponin 6, derived from Anemone taipaiensis, exerts potent cytotoxic effects against the human hepatocellular carcinoma HepG2 cell line and the human promyelocytic leukemia HL‑60 cell line; however, the effects of saponin 6 on glioblastoma remain unknown. The present study aimed to evaluate the effects of saponin 6 on human U87 malignant glioblastoma (U87 MG) cells. The current study revealed that saponin 6 induced U87 MG cell death in a dose‑ and time‑dependent manner, with a half maximal inhibitory concentration (IC50) value of 2.83 µM after treatment for 48 h. However, saponin 6 was needed to be used at a lesser potency in HT‑22 cells, with an IC50 value of 6.24 µM. Cell apoptosis was assessed by flow cytometry using Annexin V‑fluorescein isothiocyanate/propidium iodide double staining. DNA fragmentation and alterations in nuclear morphology were examined by terminal deoxynucleotidyl transferase‑mediated dUTP nick end labeling and transmission electron microscopy, respectively. The present study demonstrated that treatment with saponin 6 induced cell apoptosis in U87 MG cells, and resulted in DNA fragmentation and nuclear morphological alterations typical of apoptosis. In addition, flow cytometric analysis revealed that saponin 6 was able to induce cell cycle arrest. The present study also demonstrated that saponin 6‑induced apoptosis of U87 MG cells was attributed to increases in the protein expression levels of Fas, Fas ligand, and cleaved caspase‑3, ‑8 and ‑9, and decreases in the levels of B‑cell lymphoma 2. The current study indicated that saponin 6 may exhibit selective cytotoxicity toward U87 MG cells by activating apoptosis via the extrinsic and intrinsic pathways. Therefore, saponin 6 derived from A. taipaiensis may possess therapeutic potential for the treatment of GBM.

Three novel degraded steroids from cultures of the Basidiomycete Antrodiella albocinnamomea.

PubMed

Chen, Zi-Ming; Yang, Xiao-Yan; Fan, Qiong-Ying; Li, Zheng-Hui; Wei, Kun; Chen, He-Ping; Feng, Tao; Liu, Ji-Kai

2014-09-01

Three novel degraded steroids, named albocisterols A-C (1-3), have been isolated from cultures of Antrodiella albocinnamomea. Their structures were defined by comprehensive spectroscopic analysis and single crystal X-ray crystallography. The mixture of compounds 2 and 3 exhibited significant inhibitory activities against protein tyrosine phosphatase 1B (PTP1B). Copyright © 2014 Elsevier Ltd. All rights reserved.

LC-MS determination of steroidal glycosides from Dioscorea deltoidea Wall cell suspension culture: Optimization of pre-LC-MS procedure parameters by Latin Square design.

PubMed

Sarvin, Boris; Fedorova, Elizaveta; Shpigun, Oleg; Titova, Maria; Nikitin, Mikhail; Kochkin, Dmitry; Rodin, Igor; Stavrianidi, Andrey

2018-03-30

In this paper, the ultrasound assisted extraction method for isolation of steroidal glycosides from D. deltoidea plant cell suspension culture with a subsequent HPLC-MS determination was developed. After the organic solvent was selected via a two-factor experiment the optimization via Latin Square 4 × 4 experimental design was carried out for the following parameters: extraction time, organic solvent concentration in extraction solution and the ratio of solvent to sample. It was also shown that the ultrasound assisted extraction method is not suitable for isolation of steroidal glycosides from the D. deltoidea plant material. The results were double-checked using the multiple successive extraction method and refluxing extraction. Optimal conditions for the extraction of steroidal glycosides by the ultrasound assisted extraction method were: extraction time, 60 min; acetonitrile (water) concentration in extraction solution, 50%; the ratio of solvent to sample, 400 mL/g. Also, the developed method was tested on D. deltoidea cell suspension cultures of different terms and conditions of cultivation. The completeness of the extraction was confirmed using the multiple successive extraction method. Copyright © 2018 Elsevier B.V. All rights reserved.

Localization of Secondary Metabolites in Marine Invertebrates: Contribution of MALDI MSI for the Study of Saponins in Cuvierian Tubules of H. forskali

PubMed Central

Meriaux, Céline; Bonnel, David; Salzet, Michel; Fournier, Isabelle; Wisztorski, Maxence

2010-01-01

Background Several species of sea cucumbers of the family Holothuriidae possess a particular mechanical defense system called the Cuvierian tubules (Ct). It is also a chemical defense system as triterpene glycosides (saponins) appear to be particularly concentrated in Ct. In the present study, the precise localization of saponins in the Ct of Holothuria forskali is investigated. Classical histochemical labeling using lectin was firstly performed but did not generate any conclusive results. Thus, MALDI mass spectrometry Imaging (MALDI-MSI) was directly applied and completed by statistical multivariate tests. A comparison between the tubules of relaxed and stressed animals was realized. Results These analyses allowed the detection of three groups of ions, corresponding to the isomeric saponins of the tubules. Saponins detected at m/z 1287 and 1303 were the most abundant and were apparently localized in the connective tissue of the tubules of both relaxed and stressed individuals. Saponins at m/z 1125 and 1141 were detected in lower amount and were present in tissues of relaxed animals. Finally, saponin ions at 1433, 1449, 1463 and 1479 were observed in some Ct of stressed holothuroids in the outer part of the connective tissue. The saponin group m/z 14xx seems therefore to be stress-specific and could originate from modifications of the saponins with m/z of 11xx. Conclusions All the results taken together indicate a complex chemical defense mechanism with, for a single organ, different sets of saponins originating from different cell populations and presenting different responses to stress. The present study also reflects that MALDI-MSI is a valuable tool for chemical ecology studies in which specific chemical signalling molecules like allelochemicals or pheromones have to be tracked. This report represents one of the very first studies using these tools to provide a functional and ecological understanding of the role of natural products from marine invertebrates. PMID:21085713

Effects of Adaptation of In vitro Rumen Culture to Garlic Oil, Nitrate, and Saponin and Their Combinations on Methanogenesis, Fermentation, and Abundances and Diversity of Microbial Populations

PubMed Central

Patra, Amlan K.; Yu, Zhongtang

2015-01-01

This study investigated the effects of garlic oil (0.25 g/L), nitrate (5 mM), and quillaja saponin (0.6 g/L), alone and in binary or ternary combinations, on methanogenesis, rumen fermentation, and abundances of select microbial populations using in vitro rumen cultures. Potential adaptation to these compounds was also examined by repeated transfers of the cultures on alternate days until day 18. All treatments except saponin alone significantly decreased methanogenesis. Ternary combinations of garlic oil, nitrate, and saponin additively/synergistically suppressed methane production by 65% at day 2 and by 40% at day 18. Feed digestion was not adversely affected by any of the treatments at day 2, but was decreased by the combinations (binary and ternary) of garlic oil with the other inhibitors at days 10 and 18. Saponin, alone or in combinations, and garlic oil alone lowered ammonia concentration at day 2, while nitrate increased ammonia concentration at days 10 and 18. Total volatile fatty acid concentration was decreased by garlic oil alone or garlic oil-saponin combination. Molar proportions of acetate and propionate were affected to different extents by the different treatments. The abundances of methanogens were similar among treatments at day 2; however, garlic oil and its combination with saponin and/or nitrate at day 10 and all treatments except saponin at day 18 significantly decreased the abundances of methanogens. All the inhibitors, either alone or in combinations, did not adversely affect the abundances of total bacteria or Ruminococcus flavefaciens. However, at day 18 the abundances of Fibrobacter succinogenes and Ruminococcus albus were lowered in the presence of garlic oil and saponin, respectively. The results suggest that garlic oil-nitrate-saponin combination (at the doses used in this study) can effectively decreases methanogenesis in the rumen, but its efficacy may decrease while inhibition to feed digestion can increase over time. PMID:26733975

In-Vitro Activity of Saponins of Bauhinia Purpurea, Madhuca Longifolia, Celastrus Paniculatus and Semecarpus Anacardium on Selected Oral Pathogens

PubMed Central

Jyothi, K. S.; Seshagiri, M.

2012-01-01

Objective: Dental caries, periodontitis and other mucosal diseases are caused by a complex community of microorganisms. This study aimed to investigate the antimicrobial properties of saponins of four important oil yielding medicinal plant extracts on selected oral pathogens that are involved in such diseases. Materials and Methods: Saponins were extracted from Bauhinia purpurea, Madhuca longifolia, Celastrus paniculatus and Semecarpus anacardium and purified. Antimicrobial properties of these saponins against Streptococcus mutans, Streptococcus mitis, Streptococcus salivarius, Staphylococcus aureus and Lactobacillus acidophilus were determined using well diffusion method. The minimum inhibitory concentration (MIC) was determined as the lowest concentration of saponins inhibiting bacterial growth after 14 h of incubation at 37°C. The bactericidal activity was evaluated using the viable cell count method. Results: The minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) of Madhuca longifolia saponin on Streptococcus mutans MTCC 890, Streptococcus mitis and Staphylococcus aureus was 18.3 ± 0.15/34.4 ± 0.24 μg/ml, 19.0 ± 0.05/32.2 ± 0.0 μg/ml and 21.2 ± 0.35/39.0 ± 0.30 μg/ml, respectively and Bauhinia purpurea saponin on Streptococcus mutans MTCC 890, Staphylococcus aureus and Lactobacillus acidophilus was 26.4 ± 0.20/43.0 ± 0.40 μg/ml, 29.0 ± 0.30/39.6 ± 0.12 μg/ml and 20.2 ± 0.05/36.8 ± 0.23 μg/ml, respectively. Conclusion: The strong antimicrobial activity of Madhuca longifolia and Bauhinia purpurea may be due to the presence of complex triterpenoid saponins, oleanane type triterpenoid glycosides or atypical pentacyclic triterpenoid saponin. Hence, these extracted saponins may be used in food and oral products to prevent and control oral diseases. PMID:23323183

4α-Methylated steroids with cytotoxic activity from the soft coral Litophyton mollis.

PubMed

Zovko Končić, Marijana; Ioannou, Efstathia; Sawadogo, Wamtinga Richard; Abdel-Razik, Ayman F; Vagias, Constantinos; Diederich, Marc; Roussis, Vassilios

2016-11-01

Seven new (1-3, 5 and 8-10) and three previously reported (4, 6 and 7) 4α-methylated steroids were isolated from the organic extract of the gorgonian Litophyton mollis. The structures and the relative configurations of the isolated natural products were determined on the basis of extensive analyses of their NMR and MS data. Metabolites 1 and 5-8 exhibited cytotoxic activity against K562 human chronic myelogenous leukemia cells with IC 50 values below 10μM, while at the same time displaying low toxicity against healthy PBMCs. Copyright © 2016 Elsevier Inc. All rights reserved.

Cross-reactivity of Schistosoma mansoni-Fasciola gigantica influenced by saponins.

PubMed

Maghraby, Amany Sayed; Shaker, Kamel H; Gaber, Hanaa M

2009-01-01

The aim of the present work was to investigate the Schistosoma mansoni and Fasciola gigantica cross-reactivity between adult worms and egg homogenates of the parasites. Immunoprophylactic effects of crude Schistosoma mansoni worms and egg antigens mixed with or without saponins extracted from Atriplex nummularia were studied followed by challenge with 80 cercariae of Schistosoma mansoni. Our results showed that post 1st immunization with schistosome egg antigens (SEA) there was a significant change (P approximately 0.05) in the IgM levels against Fasciola egg homogenate (FgEH) without saponins. Post 2nd immunization with SEA mixed with saponins the levels of IgM increased significantly (P approximately 0.05) against Fasciola worm homogenate (FgWH) as compared with a non-immunized group. Post 2nd immunization the level of IgG was significantly elevated (P approximately 0.05) by SEA mixed with saponins against FgWH. Post 2nd immunizations with SEA mixed with saponins showed a significant change (P approximately 0.05) in IgG levels against FgEH. These results clearly demonstrated that there is a cross-reactivity between Schistosoma mansoni eggs and Fasciola gigantica worms and eggs. Saponins were found to be immunostimulatory adjuvants in our study.

Medicinal flowers. XXXVI.1) Acylated oleanane-type triterpene saponins with inhibitory effects on melanogenesis from the flower buds of Chinese Camellia japonica.

PubMed

Nakamura, Seikou; Fujimoto, Katsuyoshi; Nakashima, Souichi; Matsumoto, Takahiro; Miura, Tomoko; Uno, Kaoru; Matsuda, Hisashi; Yoshikawa, Masayuki

2012-01-01

Four acylated oleanane-type triterpene oligoglycosides, sanchakasaponins E-H, were isolated from the flower buds of Camellia japonica cultivated in Yunnan province, China, together with four known triterpene oligoglycosides. The chemical structures of the new triterpene oligoglycosides were elucidated on the basis of chemical and physicochemical evidence. The inhibitory effects of the triterpene oligoglycoside constituents on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells were investigated.

UPLC/Q-TOF MS-Based Metabolomics and qRT-PCR in Enzyme Gene Screening with Key Role in Triterpenoid Saponin Biosynthesis of Polygala tenuifolia

PubMed Central

Li, Zhenyu; Xu, Xiaoshuang; Peng, Bing; Qin, Xuemei; Du, Guanhua

2014-01-01

Background The dried root of Polygala tenuifolia, named Radix Polygalae, is a well-known traditional Chinese medicine. Triterpenoid saponins are some of the most important components of Radix Polygalae extracts and are widely studied because of their valuable pharmacological properties. However, the relationship between gene expression and triterpenoid saponin biosynthesis in P. tenuifolia is unclear. Methodology/Findings In this study, ultra-performance liquid chromatography (UPLC) coupled with quadrupole time-of-flight mass spectrometry (Q-TOF MS)-based metabolomic analysis was performed to identify and quantify the different chemical constituents of the roots, stems, leaves, and seeds of P. tenuifolia. A total of 22 marker compounds (VIP>1) were explored, and significant differences in all 7 triterpenoid saponins among the different tissues were found. We also observed an efficient reference gene GAPDH for different tissues in this plant and determined the expression level of some genes in the triterpenoid saponin biosynthetic pathway. Results showed that MVA pathway has more important functions in the triterpenoid saponin biosynthesis of P. tenuifolia. The expression levels of squalene synthase (SQS), squalene monooxygenase (SQE), and beta-amyrin synthase (β-AS) were highly correlated with the peak area intensity of triterpenoid saponins compared with data from UPLC/Q-TOF MS-based metabolomic analysis. Conclusions/Significance This finding suggested that a combination of UPLC/Q-TOF MS-based metabolomics and gene expression analysis can effectively elucidate the mechanism of triterpenoid saponin biosynthesis and can provide useful information on gene discovery. These findings can serve as a reference for using the overexpression of genes encoding for SQS, SQE, and/or β-AS to increase the triterpenoid saponin production of P. tenuifolia. PMID:25148032

UPLC/Q-TOF MS-based metabolomics and qRT-PCR in enzyme gene screening with key role in triterpenoid saponin biosynthesis of Polygala tenuifolia.

PubMed

Zhang, Fusheng; Li, Xiaowei; Li, Zhenyu; Xu, Xiaoshuang; Peng, Bing; Qin, Xuemei; Du, Guanhua

2014-01-01

The dried root of Polygala tenuifolia, named Radix Polygalae, is a well-known traditional Chinese medicine. Triterpenoid saponins are some of the most important components of Radix Polygalae extracts and are widely studied because of their valuable pharmacological properties. However, the relationship between gene expression and triterpenoid saponin biosynthesis in P. tenuifolia is unclear. In this study, ultra-performance liquid chromatography (UPLC) coupled with quadrupole time-of-flight mass spectrometry (Q-TOF MS)-based metabolomic analysis was performed to identify and quantify the different chemical constituents of the roots, stems, leaves, and seeds of P. tenuifolia. A total of 22 marker compounds (VIP>1) were explored, and significant differences in all 7 triterpenoid saponins among the different tissues were found. We also observed an efficient reference gene GAPDH for different tissues in this plant and determined the expression level of some genes in the triterpenoid saponin biosynthetic pathway. Results showed that MVA pathway has more important functions in the triterpenoid saponin biosynthesis of P. tenuifolia. The expression levels of squalene synthase (SQS), squalene monooxygenase (SQE), and beta-amyrin synthase (β-AS) were highly correlated with the peak area intensity of triterpenoid saponins compared with data from UPLC/Q-TOF MS-based metabolomic analysis. This finding suggested that a combination of UPLC/Q-TOF MS-based metabolomics and gene expression analysis can effectively elucidate the mechanism of triterpenoid saponin biosynthesis and can provide useful information on gene discovery. These findings can serve as a reference for using the overexpression of genes encoding for SQS, SQE, and/or β-AS to increase the triterpenoid saponin production of P. tenuifolia.

Optimized aqueous extraction of saponins from bitter melon for production of a saponin-enriched bitter melon powder.

PubMed

Tan, Sing P; Vuong, Quan V; Stathopoulos, Costas E; Parks, Sophie E; Roach, Paul D

2014-07-01

Bitter melon, Momordica charantia L. (Cucurbitaceae), aqueous extracts are proposed to have health-promoting properties due to their content of saponins and their antioxidant activity. However, the optimal conditions for the aqueous extraction of saponins from bitter melon and the effects of spray drying have not been established. Therefore, this study aimed to optimize the aqueous extraction of the saponins from bitter melon, using response surface methodology, prepare a powder using spray drying, and compare the powder's physical properties, components, and antioxidant capacity with aqueous and ethanol freeze-dried bitter melon powders and a commercial powder. The optimal aqueous extraction conditions were determined to be 40 °C for 15 min and the water-to-sample ratio was chosen to be 20:1 mL/g. For many of its physical properties, components, and antioxidant capacity, the aqueous spray-dried powder was comparable to the aqueous and ethanol freeze-dried bitter melon powders and the commercial powder. The optimal conditions for the aqueous extraction of saponins from bitter melon followed by spray drying gave a high quality powder in terms of saponins and antioxidant activity. This study highlights that bitter melon is a rich source of saponin compounds and their associated antioxidant activities, which may provide health benefits. The findings of the current study will help with the development of extraction and drying technologies for the preparation of a saponin-enriched powdered extract from bitter melon. The powdered extract may have potential as a nutraceutical supplement or as a value-added ingredient for incorporation into functional foods. © 2014 Institute of Food Technologists®

Antihyperglycemic Potential of Saponin-enriched Fraction from Pithecellobium dulce Benth. Seed Extract

PubMed Central

Kumar, Mahesh; Govindrajan, Jeyabalan; Nyola, Narendra Kumar

2017-01-01

Background: Indian traditional system of medicine uses Pithecellobium dulce for the treatment of diabetes mellitus. Objectives: This study aims to develop an extract rich in saponins derived from seeds of the plant and to evaluate its antihyperglycemic potential in vitro and in vivo. Materials and Methods: Defatted seeds were extracted with methanol and processed to afford saponin-enriched fraction (Pithecellobium dulce saponin-enriched fraction [PDSEF]). This fraction was evaluated for its potential to inhibit enzymes such as α-glucosidase and α-amylase, in vitro. The fraction was subjected to oral toxicity study followed by in vivo sucrose tolerance test. An analytical high-performance liquid chromatography method was developed for fingerprinting of the fraction. Results: The method adopted for enrichment of saponins was robust enough to enrich saponin content to 96.37% ±1.21% w/w. PDSEF displayed superior inhibition of enzymes (α-glucosidase and α-amylase with IC50 of 5.12 ± 0.15 μg/ml and 17.28 ± 0.23 μg/ml, respectively) compared to acarbose. It was found to be safe in mice up to 2000 mg/kg and significantly prevented blood glucose level in sucrose tolerance test by inhibiting enzymes responsible for hydrolysis of sucrose. Conclusion: PDSEF displayed excellent antihyperglycemic activity in vitro and in vivo and should be evaluated further to develop it as a promising drug for the management of diabetes mellitus. SUMMARY Saponin enriched fraction from P. dulce seeds showed significant inhibition of key enzymes responsible for digestion of polysaccharides. The saponin enriched fraction was found to be safe in mice and prevented blood glucose level in mice in sucrose tolerance test. Abbreviations Used: PDSEF: Pithecellobium dulce saponin-enriched fraction, IC50: Inhibitory concentration 50, HPLC: High performance liquid chromatography PMID:29333038

The Cytotoxicity of Dacarbazine Potentiated by Sea Cucumber Saponin in Resistant B16F10 Melanoma Cells through Apoptosis Induction.

PubMed

Baharara, Javad; Amini, Elaheh; Nikdel, Najme; Salek-Abdollahi, Farzaneh

2016-01-01

Malignant melanoma is a highly aggressive malignant melanocytic neoplasm which resists against the most conventional therapies. Sea cucumber as one of marine organisms contains bioactive compounds such as polysaccharide, terpenoid and other metabolites which have anti-cancer, anti-tumor, anti-inflammatory and antioxidant properties. The present study was designed to investigate the anticancer potential of saponin extracted from sea cucumber Holothuria leucospilata alone and in combination with dacarbazine on B16F10 melanoma cell line. The B16F10 cell line was treated with different concentrations of saponin (0, 4, 8, 12, 16, 20 μg/ml), dacarbazine (0, 1200, 1400, 1600, 18000, 1200, 1400, 1600, 2000 μg/ml) and co-administration of saponin-dacarbazine (1200 da+8 sp, 1200 da+4 sp) for 24 and 48 hr and the cytotoxic effect was examined by MTT, DAPI, acridine orange/propodium iodide, flow cytometry and caspase colorimetric assay. The results exhibited that sea cucumber saponin, dacarbazine, and co-administration of saponin-dacarbazine inhibited the proliferation of melanoma cells in a dose and time dependent manner with IC50 values of 10, 1400 and 4+1200 μg/ml, respectively. Morphological observation of DAPI and acridine orange/propodium iodide staining documented typical characteristics of apoptotic cell death. Flow cytometry assay indicated accumulation of IC50 treated cells in sub-G1 peak. Additionally, saponin extracted induced intrinsic apoptosis via up-regulation of caspase-3 and caspase-9. These results revealed that the saponin extracted from sea cucumber as a natural anti-cancer compound may be a new treatment modality for metastatic melanoma and the application of sea cucumber saponin in combination with dacarbazine demonstrated the strongest anti-cancer activity as compared with the drug alone.

Semisynthesis of Analogues of the Saponin Immunoadjuvant QS-21

PubMed Central

Fernández-Tejada, Alberto; Walkowicz, William E.; Tan, Derek S.; Gin, David Y.

2016-01-01

Saponins are triterpene glycoside natural products that exhibit many different biological properties, including activation and modulation of the immune system, and have therefore attracted significant interest as immunological adjuvants for use in vaccines. QS-21 is the most widely used and promising saponin adjuvant but suffers from several liabilities, such as scarcity, dose-limiting toxicity, and hydrolytic instability. Chemical synthesis has emerged as a powerful approach to obtain homogeneous, pure samples of QS-21 and to improve its properties and therapeutic profile by providing access to optimized, synthetic saponin variants. Herein, we describe a general method for the semisynthesis of these molecules from QS-21, with detailed synthetic protocols for two saponin variants developed in our recent work. PMID:27718185

Increased synthesis of a new oleanane-type saponin in hairy roots of marigold (Calendula officinalis) after treatment with jasmonic acid.

PubMed

Markowski, Michał; Długosz, Marek; Szakiel, Anna; Durli, Mathieu; Poinsignon, Sophie; Bouguet-Bonnet, Sabine; Vernex-Loset, Lionel; Krier, Gabriel; Henry, Max

2018-04-18

Native plant of marigold (Calendula officinalis L.) synthesizes oleanolic acid saponins classified as glucosides or glucuronides according to the first residue in sugar chain bound to C-3 hydroxyl group. Hairy root culture, obtained by transformation with Agrobacterium rhizogenes strain 15834, exhibit a potent ability of synthesis of oleanolic acid glycosides. The HPLC profile of saponin fraction obtained from C. officinalis hairy roots treated with plant stress hormone, jasmonic acid, showed the 10-times increase of the content of one particular compound, determined by NMR and MALDI TOF as a new bisdesmoside saponin, 3-O-β-d-glucuronopyranosyl-28-O-β-d-galactopyranosyl-oleanolic acid. Such a diglycoside does not occur in native C. officinalis plant. It is a glucuronide, whereas in the native plant glucuronides are mainly accumulated in flowers, while glucosides are the most abundant saponins in roots. Thus, our results revealed that the pathways of saponin biosynthesis, particularly reactions of glycosylation, are altered in C. officinalis hairy root culture.

Platycosides from the Roots of Platycodon grandiflorum and Their Health Benefits

PubMed Central

Nyakudya, Elijah; Jeong, Jong Hoon; Lee, Nam Keun; Jeong, Yong-Seob

2014-01-01

The extracts and pure saponins from the roots of Platycodon grandiflorum (PG) are reported to have a wide range of health benefits. Platycosides (saponins) from the roots of PG are characterized by a structure containing a triterpenoid aglycone and two sugar chains. Saponins are of commercial significance, and their applications are increasing with increasing evidence of their health benefits. The biological effects of saponins include cytotoxic effects against cancer cells, neuroprotective activity, antiviral activity, and cholesterol lowering effects. Saponins with commercial value range from crude plant extracts, which can be used for their foaming properties, to high purity saponins such as platycodin D, which can be used for its health applications (e.g., as a vaccine adjuvant). This review reveals that platycosides have many health benefits and have the potential to be used as a remedy against many of the major health hazards (e.g., cancer, obesity, alzheimer’s) faced by populations around the world. Methods of platycoside purification and analysis are also covered in this review. PMID:25054103

[Saponin 6 of Anemone Taipaiensis inhibits proliferation and induces apoptosis of U87 MG cells].

PubMed

Ji, Chenchen; Cheng, Guang; Tang, Haifeng; Zhang, Yun; Hu, Yiyang; Zheng, Minhua; Fei, Zhou

2015-04-01

To investigate the effect of saponin 6 of Anemone Taipaiensis on the proliferation of human U87 MG glioma cells and the possible mechanism. U87 MG cells were treated with different concentrations of saponin 6 (0.0, 1.6, 3.2, 6.4, 12.8 μg/mL) for 24 hours or 48 hours. Cell viability was measured by MTT assay; the apoptosis rate was detected by flow cytometry combined with annexin V-FITC /PI staining; Western blotting was applied to determine the protein level of activated caspase-3. Compared with control groups, saponin 6 significantly inhibited U87 MG cell proliferation in a time- and dose-depended manner. Apoptosis rate of U87 MG cells and the expression of activated caspase-3 were raised with the increasing concentration of saponin 6. Saponin 6 of Anemone Taipaiensis could depress cell proliferation in a dose-depended manner, increase the expression of activated caspase-3 and promote apoptosis in U87 MG cells.

Indomethacin-induced alterations in corticosteroid and prostaglandin release by isolated adrenocortical cells of the cat.

PubMed Central

Laychock, S G; Rubin, R P

1976-01-01

1 The effects of purported prostaglandin synthesis inhibitors on steroid and prostaglandin (E and F) release from trypsin-dispersed cat adrenocortical cells were investigated. 2 Low indomethacin concentrations potentiated adrenocorticotrophin (ACTH)-evoked prostaglandin and steroid release, whereas higher concentrations depressed both responses to ACTH. The steroidogenic response to exogenous prostaglandin E2 was not markedly altered over a wide range of indomethacin concentrations. 3 Indomethacin enhanced basal steroid release but did not enhance basal prostaglandin E or F release. 4 5,8,11,14-Eicosatetraynoic acid (ETA) elicited a concentration-dependent inhibition of ACTH-induced steroid release, but had little effect on prostaglandin E2-induced steroid release. A high concentration of ETA inhibited prostaglandin E and F release. 5 These data are discussed in relation to the concept that prostaglandins provide a critical link in ACTH-induced corticosteroidogenesis. PMID:181110

Surface rheology of saponin adsorption layers.

PubMed

Stanimirova, R; Marinova, K; Tcholakova, S; Denkov, N D; Stoyanov, S; Pelan, E

2011-10-18

Extracts of the Quillaja saponaria tree contain natural surfactant molecules called saponins that very efficiently stabilize foams and emulsions. Therefore, such extracts are widely used in several technologies. In addition, saponins have demonstrated nontrivial bioactivity and are currently used as essential ingredients in vaccines, food supplements, and other health products. Previous preliminary studies showed that saponins have some peculiar surface properties, such as a very high surface modulus, that may have an important impact on the mechanisms of foam and emulsion stabilization. Here we present a detailed characterization of the main surface properties of highly purified aqueous extracts of Quillaja saponins. Surface tension isotherms showed that the purified Quillaja saponins behave as nonionic surfactants with a relatively high cmc (0.025 wt %). The saponin adsorption isotherm is described well by the Volmer equation, with an area per molecule of close to 1 nm(2). By comparing this area to the molecular dimensions, we deduce that the hydrophobic triterpenoid rings of the saponin molecules lie parallel to the air-water interface, with the hydrophilic glucoside tails protruding into the aqueous phase. Upon small deformation, the saponin adsorption layers exhibit a very high surface dilatational elasticity (280 ± 30 mN/m), a much lower shear elasticity (26 ± 15 mN/m), and a negligible true dilatational surface viscosity. The measured dilatational elasticity is in very good agreement with the theoretical predictions of the Volmer adsorption model (260 mN/m). The measured characteristic adsorption time of the saponin molecules is 4 to 5 orders of magnitude longer than that predicted theoretically for diffusion-controlled adsorption, which means that the saponin adsorption is barrier-controlled around and above the cmc. The perturbed saponin layers relax toward equilibrium in a complex manner, with several relaxation times, the longest of them being around 3 min. Molecular interpretations of the observed trends are proposed when possible. Surprisingly, in the course of our study we found experimentally that the drop shape analysis method (DSA method) shows a systematically lower surface elasticity, in comparison with the other two methods used: Langmuir trough and capillary pressure tensiometry with spherical drops. The possible reasons for the observed discrepancy are discussed, and the final conclusion is that the DSA method has specific problems and may give incorrect results when applied to study the dynamic properties of systems with high surface elasticity, such as adsorption layers of saponins, lipids, fatty acids, solid particles, and some proteins. The last conclusion is particularly important because the DSA method recently became the preferred method for the characterization of fluid interfaces because of its convenience. © 2011 American Chemical Society

Evaluation of the Nitric Oxide and Nitrite Scavenging Capability, N-Nitrosamine Formation Inhibitory Activity, and Optimization of Ultrasound-Assisted Aqueous Two-Phase System Extraction of Total Saponins from Coreopsis tinctoria Flowering Tops by Response Surface Methodology.

PubMed

Luo, Ruiling; Yao, Xincheng; Liu, Xieying; Zhang, Yushang; Ying, Xue

2018-03-01

Coreopsis tinctoria flowering tops (CTFs) is a popular health product as herbal tea or as a traditional medicinal herb that is rich in saponins and exerts substantial biological activity. In this study, an ultrasound-assisted aqueous two-phase system (ATPS) was utilized to extract total saponins from CTFs and optimize the extraction process by response surface methodology. Moreover, the nitric oxide and nitrite scavenging capability, and N-nitrosamine formation inhibitory activity of total saponins were evaluated. Results showed that the optimal conditions for total saponins were 37.76% (w/w) ammonium sulfate and 35.62% (w/w) ethanol in ATPS coupled with ultrasonic-assisted extraction. Under the optimal conditions, the maximum yield of total saponins of 33.4 g/kg can be obtained from the CTFs raw material. The nitric oxide radical scavenging, nitrite scavenging, and N-nitrosamine inhibitory activities (SC 50 ) were 287.92 ± 7.42, 191.63 ± 7.69, and 1787.4 ± 51.26 μg/mL, respectively. The total saponins has a certain nitric oxide and nitrite scavenging capability, and N-nitrosamine formation inhibitory activity in vitro. Given these activities, research on saponins from CTFs provides profound and lasting implications for the novel applications of C. tinctoria.

Simultaneous determination of triterpenoid saponins in dog plasma by a validated UPLC-MS/MS and its application to a pharmacokinetic study after administration of total saponin of licorice.

PubMed

Tao, Weiwei; Duan, Jinao; Guo, Jianming; Li, Jianping; Tang, Yuping; Liu, Pei; Yang, Nianyun

2013-03-05

A rapid and sensitive ultra performance liquid chromatography-tandem mass spectrometry method was developed for simultaneous determination of eight constituents, uralsaponin C, uralsaponin F, 22β-acetoxyl-glycyrrhizin, 24-hydroxy-licorice-saponin E2, licorice-saponin G2, licorice-saponin E2, glycyrrhizin, and licorice-saponin J2, from total saponin of licorice (TSL) in dog plasma. Ardisiacrispin A was used as the internal standard (IS). The separation was performed on Thermo Syncronic C₁₈ column (100 mm × 2.1 mm, 1.7 μm) at a flow rate of 0.4 mL min⁻¹, and acetonitrile/methanol (3:1, v/v)-0.1% formic acid was used as mobile phase. The detection was performed on a triple quadrupole tandem mass spectrometer by multiple reaction monitoring (MRM) via electrospray ionization (ESI) source with negative ionization mode. All calibration curves had good linearity (r>0.991) over the concentration range from 2.03-405 ng mL⁻¹ to 2.63-2625 ng mL⁻¹ for all components. The intra- and inter-day precision was within 15% and the accuracy ranged from -14.08% to 13.8%. The method was successfully applied to pharmacokinetic study of eight triterpenoid saponins in dog plasma after oral administration of TSL. Crown Copyright © 2012. Published by Elsevier B.V. All rights reserved.

Src/Syk-Targeted Anti-Inflammatory Actions of Triterpenoidal Saponins from Gac (Momordica cochinchinensis) Seeds.

PubMed

Yu, Jae Sik; Kim, Jun Ho; Lee, Seulah; Jung, Kiwon; Kim, Ki Hyun; Cho, Jae Youl

2017-01-01

Momordica cochinchinensis Spreng (family Cucurbitaceae), also known as gac, or red melon, is an edible Southeast Asian fruit valued for its nutritional and medicinal properties. Specifically, Momordicae Semen, the seeds of the gac fruit, is used in traditional Chinese medicine to treat boils, rheumatic pain, muscle spasm, hemorrhoids, and hemangiomas. In this study, a chemical investigation into a gac seed ethanol (EtOH) extract resulted in the identification of three triterpenoidal saponins (1-3), which were investigated for their anti-inflammatory effects. Among the saponins, momordica saponin I (compound 3) reduced the production of nitric oxide (NO) in LPS-activated RAW264.7 cells without inducing cytotoxicity. The mRNA levels of inducible NO synthase (iNOS) and cyclooxygenase (COX)-2 were decreased by momordica saponin I. Additionally, the translocation of p65 and p50 (subunits of the transcription factor NF-[Formula: see text]B) into the nucleus was remarkably inhibited. Furthermore, the phosphorylation levels of inflammatory signaling proteins (I[Formula: see text]B[Formula: see text], Src, and Syk) known to be upstream regulatory molecules of p65 were decreased under momordica saponin I-treated conditions. The molecular targets of momordica saponin I were confirmed in overexpression experiments and through immunoblot analyses with Src and Syk. This study provides evidence that momordica saponin I could be beneficial in treating inflammatory diseases, and should be considered a bioactive immunomodulatory agent with anti-inflammatory properties.

Antioxidant and Inhibitory Effects of Saponin Extracts from Dianthus basuticus Burtt Davy on Key Enzymes Implicated in Type 2 Diabetes In vitro.

PubMed

Nafiu, Mikhail Olugbemiro; Ashafa, Anofi Omotayo Tom

2017-01-01

Dianthus basuticus is a plant of South African origin with various acclaimed pharmaceutical potentials. This study explored the antioxidant and antidiabetic activities of saponin extract from D. basuticus in vitro . Antioxidant activity of saponin was evaluated by 2,2-diphenyl-1-picrylhydrazyl (DPPH) and nitric oxide (*NO)-free radical scavenging activity while antidiabetic potentials were measured by the α-amylase and α-glucosidase inhibitory activities of the saponin extract. The results showed that the saponin extract, compared with quercetin, displayed better DPPH (IC 50 = 6.95 mg/ml) and NO (IC 50 = 3.31 mg/ml) radical scavenging capabilities. Similarly, the saponin extracts elicited stronger α-glucosidase (IC 50 = 3.80 mg/ml) and moderate α-amylase (IC 50 = 4.18 mg/ml) inhibitory activities as compared to acarbose. Saponin exhibited a competitive mode of inhibition on α-amylase with same maximum velocity (Vmax) of 0.0093 mM/min for saponin compared with control 0.0095 mM/min and different the Michaelis constant (Km) values of 2.6 × 10 -6 mM and 2.1 × 10 -5 mM, respectively, while for α-glucosidase, the inhibition was uncompetitive, Vmax of 0.027 mM/min compared with control 0.039 mM/min and Km values of 1.02 × 10 -6 mM and 1.38 × 10 -6 mM, respectively. The gas chromatography-mass spectrometric analysis revealed the presence of bioactive like β- and α-amyrin, 3-O-methyl-D-glucose, methyl commate, and olean-12-en-3-beta-ol. Overall, the data suggested that the saponin extract from D. basuticus has potentials as natural antioxidants and antidiabetics. Saponin extract from Dianthus basuticus displayed promising antidiabetic and antioxidant activitySaponin competitively and uncompetitively inhibited a-amylase and a-glucosidase, respectivelyThe stronger inhibition of α-glucosidase and moderate inhibition of α-amylase by saponin extract from D. basuticus is promising good antidiabetes compared with existing drugs with associated side effects. Abbreviations used: DPPH: 2,2-diphenyl-1-picrylhydrazyl, Km: The Michaelis constant, Vmax: Maximum velocity, ROS: Reactive oxygen species, NIDDM: Non-insulin-dependent diabetes mellitus, UFS: University of the Free State, GC-MS: Gas chromatography-mass spectrometric, MS: Mass spectrometry, NIST: National Institute of Standards and Technology, DNS: 3,5-dinitrosalicylic acid, NO: Nitric oxide, RNS: Reactive nitrogen species, PNPG: p-Nitrophenyl-α-D-glucopyranoside.

Antioxidant and Inhibitory Effects of Saponin Extracts from Dianthus basuticus Burtt Davy on Key Enzymes Implicated in Type 2 Diabetes In vitro

PubMed Central

Nafiu, Mikhail Olugbemiro; Ashafa, Anofi Omotayo Tom

2017-01-01

Context: Dianthus basuticus is a plant of South African origin with various acclaimed pharmaceutical potentials. Aims: This study explored the antioxidant and antidiabetic activities of saponin extract from D. basuticus in vitro. Materials and Methods: Antioxidant activity of saponin was evaluated by 2,2-diphenyl-1-picrylhydrazyl (DPPH) and nitric oxide (*NO)-free radical scavenging activity while antidiabetic potentials were measured by the α-amylase and α-glucosidase inhibitory activities of the saponin extract. Results: The results showed that the saponin extract, compared with quercetin, displayed better DPPH (IC50 = 6.95 mg/ml) and NO (IC50 = 3.31 mg/ml) radical scavenging capabilities. Similarly, the saponin extracts elicited stronger α-glucosidase (IC50 = 3.80 mg/ml) and moderate α-amylase (IC50 = 4.18 mg/ml) inhibitory activities as compared to acarbose. Saponin exhibited a competitive mode of inhibition on α-amylase with same maximum velocity (Vmax) of 0.0093 mM/min for saponin compared with control 0.0095 mM/min and different the Michaelis constant (Km) values of 2.6 × 10-6 mM and 2.1 × 10-5 mM, respectively, while for α-glucosidase, the inhibition was uncompetitive, Vmax of 0.027 mM/min compared with control 0.039 mM/min and Km values of 1.02 × 10-6 mM and 1.38 × 10-6 mM, respectively. The gas chromatography-mass spectrometric analysis revealed the presence of bioactive like β- and α-amyrin, 3-O-methyl-D-glucose, methyl commate, and olean-12-en-3-beta-ol. Conclusion: Overall, the data suggested that the saponin extract from D. basuticus has potentials as natural antioxidants and antidiabetics. SUMMARY Saponin extract from Dianthus basuticus displayed promising antidiabetic and antioxidant activitySaponin competitively and uncompetitively inhibited a-amylase and a-glucosidase, respectivelyThe stronger inhibition of α-glucosidase and moderate inhibition of α-amylase by saponin extract from D. basuticus is promising good antidiabetes compared with existing drugs with associated side effects. Abbreviations used: DPPH: 2,2-diphenyl-1-picrylhydrazyl, Km: The Michaelis constant, Vmax: Maximum velocity, ROS: Reactive oxygen species, NIDDM: Non-insulin-dependent diabetes mellitus, UFS: University of the Free State, GC-MS: Gas chromatography-mass spectrometric, MS: Mass spectrometry, NIST: National Institute of Standards and Technology, DNS: 3,5-dinitrosalicylic acid, NO: Nitric oxide, RNS: Reactive nitrogen species, PNPG: p-Nitrophenyl-α-D-glucopyranoside. PMID:29200716

New cytotoxic constituents from the Red Sea soft coral Nephthea sp.

PubMed

Hegazy, Mohamed-Elamir F; Gamal-Eldeen, Amira M; Mohamed, Tarik A; Alhammady, Montaser A; Hassanien, Abuzeid A; Shreadah, Mohamed A; Abdelgawad, Ibrahim I; Elkady, Eman M; Paré, Paul W

2016-06-01

Nephthea are soft coral species rich in sesquiterpenoids and steroids. An organic extract of Nephthea sp. resulted in the isolation of a new steroid (1), as well as several previously reported metabolites (2-9). Structures were elucidated by employing NMR and HR-EI-MS analyses. The total extract, fractions and purified compounds exhibited differential cytotoxicity against the breast cancer MCF-7 cell line.

Triterpenoid Saponin W3 from Anemone flaccida Suppresses Osteoclast Differentiation through Inhibiting Activation of MAPKs and NF-κB Pathways.

PubMed

Kong, Xiangying; Yang, Yue; Wu, Wenbin; Wan, Hongye; Li, Xiaomin; Zhong, Michun; Su, Xiaohui; Jia, Shiwei; Lin, Na

2015-01-01

Excessive bone resorption by osteoclasts within inflamed joints is the most specific hallmark of rheumatoid arthritis. A. flaccida has long been used for the treatment of arthritis in folk medicine of China; however, the active ingredients responsible for the anti-arthritis effects of A. flaccida are still elusive. In this study, W3, a saponin isolated from the extract of A. flaccida was identified as the major active ingredient by using an osteoclast formation model induced by receptor activator of nuclear factor kappa-B ligand (RANKL). W3 dose-dependently suppressed the actin ring formation and lacunar resorption. Mechanistic investigation revealed that W3 inhibited the RANKL-induced TRAF6 expression, decreased phosphorylation of mitogen-activated protein kinases (MAPKs) and IκB-α, and suppressed NF-κB p65 DNA binding activity. Furthermore, W3 almost abrogated the expression of c-Fos and nuclear factor of activated T cells (NFATc1). Therefore, our results suggest that W3 is a potential agent for treating lytic bone diseases although further evaluation in vivo and in clinical trials is needed.

Influence of intramolecular hydrogen bonds on regioselectivity of glycosylation. Synthesis of lupane-type saponins bearing the OSW-1 saponin disaccharide unit and its isomers.

PubMed

Kuczynska, Kinga; Cmoch, Piotr; Rárová, Lucie; Oklešťková, Jana; Korda, Anna; Pakulski, Zbigniew; Strnad, Miroslav

2016-03-24

A series of lupane-type saponins bearing OSW-1 disaccharide unit as well as its regio- and stereoisomers were prepared and used for the structure-activity relationships (SAR) study. Unexpected preference for 1→4-linked regioisomers and an unusual inversion of the conformation of the sugar rings were noted. Cytotoxic activity of new lupane compounds was evaluated in vitro and revealed that some saponins exhibited an interesting bioactivity profile against human cancer cell lines. Influence of the protecting groups on the cytotoxicity was investigated. These results open the way to the synthesis of various lupane-type triterpene and saponin derivatives as potential anticancer compounds. Copyright © 2016 Elsevier Ltd. All rights reserved.

Determination of flavonoids and saponins in Gynostemma pentaphyllum (Thunb.) Makino by liquid chromatography-mass spectrometry.

PubMed

Kao, T H; Huang, S C; Inbaraj, B Stephen; Chen, B H

2008-09-26

Gynostemma pentaphyllum (Thunb.) Makino, a traditional Chinese herb possessing antitumor and antioxidant activities, has been shown to contain several functional components like saponins and flavonoids. However, their identities remain uncertain. The objectives of this study were to develop an appropriate extraction, purification and HPLC-MS method to determine saponins and flavonoids in G. pentaphyllum. Both flavonoids and saponins were extracted with methanol, followed by purification with a C18 cartridge to elute the former with 50% methanol and the latter with 100% methanol. A total of 34 saponins were separated within 40 min by a Gemini C18 column and a gradient mobile phase of acetonitrile and 0.1% formic acid in water, in which 18 saponins were identified by LC-MS with ESI mode and Q-TOF (LC/MS/MS). Similarly, a total of eight flavonoids were separated within 45 min by the same column and a gradient solvent system of methanol and 0.1% formic acid in water, with identification being carried out by a post-column derivatization method and LC-MS with ESI mode. The amounts of flavonoids in G. pentaphyllum ranged from 170.7 to 2416.5 mug g(-1), whereas saponins were from 491.0 to 89,888.9 mug g(-1).

Antiobese effects of novel saponins from edible seeds of Japanese horse chestnut (Aesculus turbinata BLUME) after treatment with wood ashes.

PubMed

Kimura, Hideto; Ogawa, Satoshi; Katsube, Takuya; Jisaka, Mitsuo; Yokota, Kazushige

2008-06-25

Recently, we have identified novel saponins from edible seeds of Japanese horse chestnut ( Aesculus turbinata BLUME) after processing the natural seeds with wood ashes to remove bitterness. We attempted to determine anti-obesity effects of those saponins from edible seeds as well as natural seeds. The purified individual components of saponins from natural and edible seeds inhibited pancreatic lipase in vitro. The potency was in the order of escins > desacylescins > deacetylescins. Escins Ib and IIb as well as deacetylescins Ib and IIb with the angeloyl moiety were more potent than the corresponding Ia and IIa series with the tigloyl moiety. Moreover, in vivo anti-obesity effects of the saponin fractions were monitored for 8 weeks in mice fed high-fat diets. Saponin fractions from both seeds significantly attenuated the elevation in body weight, the mass of peritoneal adipose tissues, and plasma triacylglycerol, which was accompanied by higher contents of undigested fats in feces without changes in food intake, indicating the effective inhibition of fat digestion in vivo. Taken together, saponin fractions including desacylescins and deacetylescins from edible seeds are potentially useful for the development of nutraceutical foods with anti-obesity effects and more attenuated bitter taste.

Biochemical characterization of cholesterol-reducing Eubacterium.

PubMed

Mott, G E; Brinkley, A W; Mersinger, C L

1980-12-01

We characterized two isolates of cholesterol-reducing Eubacterium by conducting conventional biochemical tests and by testing various sterols and glycerolipids as potential growth factors. In media containing cholesterol and plasmenylethanolamine, the tests for nitrate reduction, indole production, and gelatin and starch hydrolyses were negative, and no acid was produced from any of 22 carbohydrates. Both isolates hydrolyzed esculin to esculetin, indicating beta-glycosidase activity. In addition to plasmenylethanolamine, five other lipids which contain an alkenyl ether residue supported growth of Eubacterium strain 403 in a lecithin-cholesterol base medium. Of six steroids tested, cholesterol, cholest-4-en-3-one, cholest-4-en-3 beta-ol (allocholesterol), and androst-5-en-3 beta-ol-17-one supported growth of Eubacterium strain 403. All four steroids were reduced to the 3 beta-ol, 5 beta-H products. The delta 5 steroids cholest-5-en-3 alpha-ol (epicholesterol) and 22,23-bisnor-5-cholenic acid-3-beta-ol were not reduced and did not support growth of the Eubacterium strain.

The role of supplemental ultraviolet-B radiation in altering the metabolite profile, essential oil content and composition, and free radical scavenging activities of Coleus forskohlii, an indigenous medicinal plant.

PubMed

Takshak, Swabha; Agrawal, S B

2016-04-01

The effects of supplemental ultraviolet-B (s-UV-B; 3.6 kJ m(-2) day(-1) above ambient) radiation were investigated on plant metabolite profile, essential oil content and composition, and free radical scavenging capacities of methanolic extracts of Coleus forskohlii (an indigenous medicinal plant) grown under field conditions. Essential oil was isolated using hydrodistillation technique while alterations in metabolite profile and oil composition were determined via gas chromatography-mass spectroscopy (GC-MS). Leaf and root methanolic extracts were investigated via various in vitro assays for their DPPH radical-, superoxide radical-, hydrogen peroxide-, hydroxyl radical-, and nitric oxide radical scavenging activities, ferrous ion chelating activity, and reducing power. Phytochemical analysis revealed the presence of alkaloids, anthocyanins, coumarins, flavonoids, glycosides, phenols, saponins, steroids, tannins, and terpenoids. Oil content was found to be reduced (by ∼7 %) in supplemental UV-B (s-UV-B) treated plants; the composition of the plant extracts as well as essential oil was also considerably altered. Methanolic extracts from treated plant organs showed more potency as free radical scavengers (their EC50 values being lower than their respective controls). Anomalies were observed in Fe(2+) chelating activity for both leaves and roots. The present study concludes that s-UV-B adversely affects oil content in C. forskohlii and also alters the composition and contents of metabolites in both plant extracts and oil. The results also denote that s-UV-B treated plant organs might be more effective in safeguarding against oxidative stress, though further studies are required to authenticate these findings.

Effects of hecogenin and its possible mechanism of action on experimental models of gastric ulcer in mice.

PubMed

Santos Cerqueira, Gilberto; dos Santos e Silva, Gabriela; Rios Vasconcelos, Emiliano; Fragoso de Freitas, Ana Paula; Arcanjo Moura, Brinell; Silveira Macedo, Danielle; Lopes Souto, Augusto; Barbosa Filho, José Maria; de Almeida Leal, Luzia Kalyne; de Castro Brito, Gerly Anne; Souccar, Caden; de Barros Viana, Glauce Socorro

2012-05-15

This study investigates the gastroprotective effects of hecogenin, a steroid saponin isolated from Agave sisalana, on experimental models of gastric ulcer. Male Swiss mice were used in the models of ethanol- and indometacin-induced gastric ulcer. To clarify the hecogenin mechanism of action, the roles of nitric oxide (NO), sulfhydryls (GSH), K⁺(ATP) channels and prostaglandins were also investigated, and measurements of lipid peroxidation (TBARS assay) and nitrite levels in the stomach of hecogenin-treated and untreated animals were performed. Furthermore, the effects of hecogenin on myeloperoxidase (MPO) release from human neutrophils were assessed in vitro. Our results showed that hecogenin (3.1, 7.5, 15, 30, 60 and 90 mg/kg, p.o.) acutely administered, before ethanol or indomethacin, exhibited a potent gastroprotective effect. Although the pretreatments with L-NAME, an iNOS inhibitor, and capsazepine, a TRPV1 receptor agonist, were not able to reverse the hecogenin effect, this was reversed by glibenclamide, a K⁺(ATP) blocker, and indomethacin in the model of ethanol-induced gastric lesions. The hecogenin pretreatment normalized GSH levels and significantly reduced lipid peroxidation and nitrite levels in the stomach, as evaluated by the ethanol-induced gastric lesion model. The drug alone increased COX-2 expression and this effect was further enhanced in the presence of ethanol. It also decreased MPO release and significantly protected the gastric mucosa. In conclusion, we showed that hecogenin presents a significant gastroprotective effect that seems to be mediated by K⁺(ATP) channels opening and the COX-2/PG pathway. In addition, its antioxidant and anti-inflammatory properties may play a role in the gastroprotective drug effect. Copyright © 2012 Elsevier B.V. All rights reserved.

Phytochemical investigation and anti-microbial activity of Clausena anisata (Willd), Hook.

PubMed

Agyepong, Nicholas; Agyare, Christian; Adarkwa-Yiadom, Martin; Gbedema, Stephen Yao

2014-01-01

Clausena anisata belongs to the family Rutaceae, a shrub widely used in West Africa for the treatment of bacterial and fungal infections of the skin including boils, ringworm and eczema. The study was designed to evaluate the antimicrobial activity and phytochemical screening of ethanol leaf extract of C. anisata (CLE). Antimicrobial activity of CLE was investigated using agar well diffusion and micro-dilution methods against four Gram-positive bacteria (Bacillus substilis NCTC 10073, Staphylococcus aureus ATCC 25923, Enterococcus faecalis ATCC 29212, Bacillus thuringiensis ATCC 13838) and two Gram-negative bacteria (Pseudomonas aeruginosa ATCC 4853, Proteus vulgaris ATCC 4175) and a clinical isolate of Candida albicans. CLE was active against all test organisms with minimum inhibitory concentration (MIC), range of 0.5 to 7.0 mg/mL against Gram-positive bacteria, 2.5 to 1.0 mg/mL against Gram-negative bacteria and 5.5mg/mL against C. albicans. The MICs of the methanol fraction of CLE were 0.6 mg to 5.0/mL and 1.0 to 3.0 mg/mL for Gram-positive and Gram-negative bacteria respectively. Chloroform fraction had MIC of 3.0 to 7.5 mg/mL and 2.0 to 6.5 mg/mL for Gram-positive and Gram-negative bacteria, respectively and petroleum ether fraction had 4.5 to 8.0 mg/mL for Gram-positive and Gram-negative bacteria. The CLE exhibited static action against all test organisms within a range of 0.5 to 22.0 mg/mL. Phytochemical screening of C. anisata revealed the presence of tannins, flavonoids, steroids, saponins, glycosides and alkaloids. HPLC finger-printing of the CLE and its fractions were determined. These results may justify the medicinal uses of C. anisata for the treatment of microbial infections.

Identification of novel saponins from edible seeds of Japanese horse chestnut (Aesculus turbinata Blume) after treatment with wooden ashes and their nutraceutical activity.

PubMed

Kimura, Hideto; Ogawa, Satoshi; Jisaka, Mitsuo; Kimura, Yasuo; Katsube, Takuya; Yokota, Kazushige

2006-08-28

Natural seeds of Japanese horse chestnut (Aesculus turbinata Blume) contain large amounts of mixed triterpenoidal saponins called escins. Recent studies have shown that escins have several biological activities including anti-inflammatory action and inhibitory effects on the absorption of ethanol and glucose. For the edible utilization of the seeds, natural seeds are usually treated with wooden ashes to remove harshness. Here, we found the novel compounds derived from escins in the edible seeds after the food processing with wooden ashes. The instrumental analyses revealed the chemical structures of escins and the derivatives. These compounds are identified as four types of deacetylescins Ia, IIa, Ib, and IIb as well as two types of desacylescins I and II. To determine their biological activity, the purified compounds were tested for their potential nutraceutical activity. The oral glucose tolerance test in mice revealed that a single oral administration of the isolated components of deacetylescins at a dose of 100 mg/kg was clearly effective in attenuating the elevation of blood glucose levels. The inhibitory effects of escins and their derivatives were in the order of escins>deacetylescins>desacylescins. Moreover, we found the inhibitory activity of those compounds on pancreatic lipase. Escins were the most potent in inhibiting the enzyme activity, and followed by desacylescins and then deacetylescins. Taken together, our results suggest the potential usefulness of novel saponins including deacetylescins and desacylescins from edible seeds as novel sources for nutraceutical foods with anti-obese effects.

New Triterpenoid Saponins from Green Vegetable Soya Beans and Their Anti-Inflammatory Activities.

PubMed

Lan, Xiuhua; Deng, Kejun; Zhao, Jianping; Chen, Yiyi; Xin, Xuhui; Liu, Yanli; Khan, Ikhlas A; Yang, Shilin; Wang, Taoyun; Xu, Qiongming

2017-12-20

Ten compounds were isolated and identified from green vegetable soya beans, of which five are new triterpenoid saponins (1-5) and five are known compounds (6-10). The chemical structures of the five triterpenoid saponins (1-5) were elucidated to be 3β,24-dihydroxy-22β,30-epoxy-30-oxoolean-12-en 3-O-α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyl-(1 → 2)-β-d-glucuronopyranoside, 1; 3β,24-dihydroxy-22β,30-epoxy-30-oxoolean-12-en 3-O-α-l-rhamnopyranosyl-(1 → 2)-β-d-(3″-O-formyl)-galactopyranosyl-(1 → 2)-β-d-glucuronopyranoside, 2; 22-keto-3β,24-dihydroxy oleanane-12-ene 3-O-α-l-rhamnopyranosyl-(1 → 2)-β-d-(3″-O-formyl)-galactopyranosyl-(1 → 2)-β-d-glucuronopyranoside, 3; 3β,22β,24-trihydroxy oxyolean-18(19)-ene-29-acid 3-O-α-l-rhamnopyranosyl-(1 → 2)-β-d-galactopyranosyl-(1 → 2)-β-d-glucuronopyranoside, 4; and punicanolic acid 3-O-α-l-rhamnopyranosyl-(1 → 2)-β-d-galactopyranosyl-(1 → 2)-β-d-glucuronopyranoside, 5 from the spectroscopic data (IR, GTC/FID, HR-ESI-MS, and 1D and 2D NMR). The nitric oxide release inhibitions of compounds 1-10 in LPS-stimulated RAW264.7 cells were evaluated, and the data suggested that compounds 1, 2, and 5 might possess moderate anti-inflammatory activities, with IC 50 values of 18.8, 16.1, and 13.2 μM, respectively.

A tandem array of UDP-glycosyltransferases from the UGT73C subfamily glycosylate sapogenins, forming a spectrum of mono- and bisdesmosidic saponins.

PubMed

Erthmann, Pernille Østerbye; Agerbirk, Niels; Bak, Søren

2018-05-01

This study identifies six UGT73Cs all able to glucosylate sapogenins at positions 3 and/or 28 which demonstrates that B. vulgaris has a much richer arsenal of UGTs involved in saponin biosynthesis than initially anticipated. The wild cruciferous plant Barbarea vulgaris is resistant to some insects due to accumulation of two monodesmosidic triterpenoid saponins, oleanolic acid 3-O-β-cellobioside and hederagenin 3-O-β-cellobioside. Insect resistance depends on the structure of the sapogenin aglycone and the glycosylation pattern. The B. vulgaris saponin profile is complex with at least 49 saponin-like metabolites, derived from eight sapogenins and including up to five monosaccharide units. Two B. vulgaris UDP-glycosyltransferases, UGT73C11 and UGT73C13, O-glucosylate sapogenins at positions 3 and 28, forming mainly 3-O-β-D-glucosides. The aim of this study was to identify UGTs responsible for the diverse saponin oligoglycoside moieties observed in B. vulgaris. Twenty UGT genes from the insect resistant genotype were selected and heterologously expressed in Nicotiana benthamiana and/or Escherichia coli. The extracts were screened for their ability to glycosylate sapogenins (oleanolic acid, hederagenin), the hormone 24-epibrassinolide and sapogenin monoglucosides (hederagenin and oleanolic acid 3-O-β-D-glucosides). Six UGTs from the UGT73C subfamily were able to glucosylate both sapogenins and both monoglucosides at positions 3 and/or 28. Some UGTs formed bisdesmosidic saponins efficiently. At least four UGT73C genes were localized in a tandem array with UGT73C11 and possibly UGT73C13. This organization most likely reflects duplication events followed by sub- and neofunctionalization. Indeed, signs of positive selection on several amino acid sites were identified and modelled to be localized on the UGT protein surface. This tandem array is proposed to initiate higher order bisdesmosidic glycosylation of B. vulgaris saponins, leading to the recently discovered saponin structural diversity, however, not directly to known cellobiosidic saponins.

The effects of social isolation on steroid hormone levels are modulated by previous social status and context in a cichlid fish.

PubMed

Galhardo, L; Oliveira, R F

2014-01-01

Social isolation is a major stressor which impacts the physiology, behaviour and health of individuals in gregarious species. However, depending on conditional and contextual factors, such as social status and group composition, social isolation may be perceived differently by different individuals or even by the same individuals at different times. Here we tested the effects of social status (territorial vs. non-territorial) and previous group composition (i.e. type of social group: mixed sex group with two territorial males, TT vs. mixed sex group with one territorial and one non-territorial male, TnT) on the hormonal response (androgens and cortisol) to social isolation in a cichlid fish (Oreochromis mossambicus). The different steroid hormones measured responded differentially to social isolation, and their response was modulated by social factors. Social isolation elicited a decrease of 11-keto formation only in territorial males, whereas non-territorial males present a non-significant trend for increasing KT levels. Testosterone did not respond to social isolation. Cortisol only increased in isolated individuals from TnT groups irrespective of social status (i.e. both in territorials and non-territorials). These results suggest that it is the perception of social isolation and not the objective structure of the situation that triggers the hormonal response to isolation. © 2013.

Metabolites profile of Gualou Xiebai Baijiu decoction (a classical traditional Chinese medicine prescription) in rats by ultra-performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry.

PubMed

Lin, Pei; Qin, Zifei; Yao, Zhihong; Wang, Li; Zhang, Weiyang; Yu, Yang; Dai, Yi; Zhou, Hua; Yao, Xinsheng

2018-05-15

Gualou Xiebai Baijiu decoction (GLXB), a well-known classic traditional Chinese medicine prescription, has been widely used to treat coronary heart diseases for thousands of years in Eastern Asian countries due to its remarkable clinical effect. However, due to lack of in vivo metabolism research, the chemical components responsible for the therapeutic effects still remain unclear. In this work, a reliable "representative structure based homologous xenobiotics identification" (RSBHXI) strategy based on ultra-performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry (UPLC/Q-TOF-MS) were applied to investigate the chemical components in GLXB extracts. As a result, 133 chemical components were characterized based on summarized fragmentation patterns, of which 41 components were confirmed unambiguously with authentic standards. Furthermore, a total of 138 GLXB-related xenobiotics were identified or tentatively characterized after oral administration of GLXB extracts. Moreover, to better understand the metabolic pathways of characteristic components in GLXB, metabolites profiles of five steroidal saponins and two flavonoids were performed, respectively. Since the metabolic pathways of five representative saponins had been finished in our previous study, we focused on the in vivo metabolism of two flavonoids. A total of 36 and 20 metabolites were detected in rat biological samples after oral administration of luteolin-7-O-β-D-glucopyranoside and rutin, respectively. The results indicated that dehydration, hydrolysis, hydroxylation, methylation, glucuronidation and sulfation were the main metabolic reactions, following the metabolic soft spots of GLXB-related flavonoids. Taken altogether, this study would be helpful for the further pharmacokinetics, pharmacological evaluation and quality control of GLXB. Copyright © 2018. Published by Elsevier B.V.

Combined Application of UHPLC-QTOF/MS, HPLC-ELSD and 1 H-NMR Spectroscopy for Quality Assessment of DA-9801, A Standardised Dioscorea Extract.

PubMed

Kang, Kyo Bin; Ryu, Jayoung; Cho, Youngwoong; Choi, Sang-Zin; Son, Miwon; Sung, Sang Hyun

2017-05-01

DA-9801, a standardised 50% aqueous ethanolic extract of a mixture of Dioscorea japonica and D. nipponica, is a botanical drug candidate for the treatment of diabetic neuropathy, which finished its US phase II clinical trials recently. An advanced quality control method is needed for further development of DA-9801, considering its high contents of both primary and secondary metabolites. Development of a quality assessment strategy for DA-9801, based on the combination of UHPLC-QTOF/MS, HPLC-ELSD, and 1 H-NMR spectroscopy. The method was developed and tested with 15 batch products of DA-9801. The steroidal saponins of DA-9801 were tentatively identified by UHPLC-QTOF/MS and were quantified with the validated HPLC-ELSD method. Primary metabolites of DA-9801 were identified and profiled using 1 H-NMR spectrometry. The batch-to-batch equivalence of DA-9801 was tested with the 1 H-NMR spectra using spectral binning, correlation analysis, and principal component analysis. Six major saponins of DA-9801 were tentatively identified by UHPLC-QTOF/MS. Among them, protodioscin and dioscin were quantified by the validated HPLC-ELSD method. Twenty-six metabolites were identified in 1 H-NMR spectra. The similarity between DA-9801 batches could be evaluated with the NMR spectra of DA-9801. The 1 H-NMR method also revealed that two Dioscorea species contributed distinct amino acids to the contents of DA-9801. This study validates the effectiveness of UHPLC-QTOF/MS, HPLC-ELSD, and 1 H NMR-combined method for quality control of DA-9801 and its crude materials. Copyright © 2016 John Wiley & Sons, Ltd. Copyright © 2016 John Wiley & Sons, Ltd.

Mate (Ilex paraguariensis St. Hilaire) saponins induce caspase-3-dependent apoptosis in human colon cancer cells in vitro

USDA-ARS?s Scientific Manuscript database

Saponins are naturally occurring metabolites present in Yerba mate (Ilex paraguariensis), and other plant sources which have been associated with several health benefits. Mate saponins were extracted with methanol from dry leaves, partially purified and quantified. UV-HPLC analysis showed that the m...

Assessment of Antioxidant and Cytotoxicity Activities of Saponin and Crude Extracts of Chlorophytum borivilianum

PubMed Central

Abd Aziz, Maheran; Stanslas, Johnson; Abdul Kadir, Mihdzar

2013-01-01

The present paper focused on antioxidant and cytotoxicity assessment of crude and total saponin fraction of Chlorophytum borivilianum as an important medicinal plant. In this study, three different antioxidant activities (2,2-diphenyl-1-picrylhydrazyl radical scavenging (DPPH), ferrous ion chelating (FIC), and β-carotene bleaching (BCB) activity) of crude extract and total saponin fraction of C. borivilianum tubers were performed. Crude extract was found to possess higher free radical scavenging activity (ascorbic acid equivalents 2578 ± 111 mg AA/100 g) and bleaching activity (IC50 = 0.7 mg mL−1), while total saponin fraction displayed higher ferrous ion chelating (EC50 = 1 mg mL−1). Cytotoxicity evaluation of crude extract and total saponin fraction against MCF-7, PC3, and HCT-116 cancer cell lines using 3-(4,5-dimethylthiazol-2-yl)-2,5 diphenyltetrazolium bromide (MTT) cell viability assay indicated a higher cytotoxicity activity of the crude extract than the total saponin fraction on all cell lines, being most effective and selective on MCF-7 human breast cancer cell line. PMID:24223502

Potential of extracts from Saponaria officinalis and Calendula officinalis to modulate in vitro rumen fermentation with respect to their content in saponins.

PubMed

Budan, Alexandre; Bellenot, Denis; Freuze, Ingrid; Gillmann, Louisa; Chicoteau, Pierre; Richomme, Pascal; Guilet, David

2014-01-01

Saponins have the potential to favorably modulate rumen fermentation, but there is generally a lack of the chemical structures associated with the described effects. The activity of extracts from Calendula officinalis and Saponaria officinalis in the rumen was evaluated in vitro. The S. officinalis root extract, reduced CH₄ production by 8.5% and increased total VFA concentration by 25.2%. C. officinalis and S. officinalis root extracts and the S. officinalis aerial part extract decreased the acetate to propionate ratio from 8.6 to 17.4%, according to the extract. An HPLC-ELSD analysis indicated that the saponin content ranged from 43.6 to 57.6 mg/g of dry matter (DM) in the C. officinalis extracts and from 224.0 to 693.8 mg/g of DM in the S. officinalis extracts, expressed as the hederacoside C equivalent. Identification of the saponin compounds present in the extracts by HPLC-MS(n) suggested that the saponin profile modulated the biological activities, showing the importance of determining the structure of saponins when evaluating extracts.

Saponins from Tribulus terrestris L. protect human keratinocytes from UVB-induced damage.

PubMed

Sisto, Margherita; Lisi, Sabrina; D'Amore, Massimo; De Lucro, Raffaella; Carati, Davide; Castellana, Donatello; La Pesa, Velia; Zuccarello, Vincenzo; Lofrumento, Dario D

2012-12-05

Chronic exposure to solar UVB radiation damages skin, increasing the risk to develop cancer. Hence the identification of compounds with a photoprotective efficacy is essential. This study examined the role of saponins derived from Tribulus terrestris L. (TT) on the modulation of apoptosis in normal human keratinocytes (NHEK) exposed to physiological doses of UVB and to evaluate their antitumoral properties. In NHEK, TT saponins attenuate UVB-induced programmed cell death through inhibition of intrinsic apoptotic pathway. In squamous cell carcinomas (SCC) TT saponins do not make the malignant keratinocytes more resistant to UVB and determine an enhanced apoptotic response. The photoprotective effect of TT saponins is tightly correlated to the enhancement of NER genes expression and the block of UVB-mediated NF-κB activation. Collectively, our study shows experimental evidence that TT has a preventive efficacy against UVB-induced carcinogenesis and the molecular knowledge on the mechanisms through which TT saponins regulate cell death suggests great potential for TT to be developed into a new medicine for cancer patients. Copyright © 2012 Elsevier B.V. All rights reserved.

Enhanced removal of lead from contaminated soil by polyol-based deep eutectic solvents and saponin

NASA Astrophysics Data System (ADS)

Mukhopadhyay, Soumyadeep; Mukherjee, Sumona; Hayyan, Adeeb; Hayyan, Maan; Hashim, Mohd Ali; Sen Gupta, Bhaskar

2016-11-01

Deep eutectic solvents (DESs) are a class of green solvents analogous to ionic liquids, but less costly and easier to prepare. The objective of this study is to remove lead (Pb) from a contaminated soil by using polyol based DESs mixed with a natural surfactant saponin for the first time. The DESs used in this study were prepared by mixing a quaternary ammonium salt choline chloride with polyols e.g. glycerol and ethylene glycol. A natural surfactant saponin obtained from soapnut fruit pericarp, was mixed with DESs to boost their efficiency. The DESs on their own did not perform satisfactory due to higher pH; however, they improved the performance of soapnut by up to 100%. Pb removal from contaminated soil using mixture of 40% DES-Gly and 1% saponin and mixture of 10% DES-Gly and 2% saponin were above 72% XRD and SEM studies did not detect any major corrosion in the soil texture. The environmental friendliness of both DESs and saponin and their affordable costs merit thorough investigation of their potential as soil washing agents.

Isolation of angiotensin converting enzyme (ACE) inhibiting triterpenes from Schinus molle.

PubMed

Olafsson, K; Jaroszewski, J W; Smitt, U W; Nyman, U

1997-08-01

Bioactivity-guided fractionation of extracts of Schinus molle leaves, using an in vitro assay, led to the isolation of ACE-inhibitory steroidal triterpenes of the euphane type, identified by means of NMR spectroscopic methods. One of the triterpenes was isolated as an equilibrium mixture of epimeric aldehydes. The triterpenes showed moderate ACE-inhibitory activity (IC(50) about 250 microM).

A high-throughput UPC2-MS/MS method for the separation and quantification of C19 and C21 steroids and their C11-oxy steroid metabolites in the classical, alternative, backdoor and 11OHA4 steroid pathways.

PubMed

du Toit, Therina; Stander, Maria A; Swart, Amanda C

2018-03-30

In the present study an ultra-performance convergence chromatography tandem mass spectrometry (UPC 2 -MS/MS) analytical method was developed and validated for the determination of 17 C 19 and 14 C 21 steroids, including C11-oxy C 19 and C11-oxy C 21 steroids. The limit of detection and limit of quantification ranged from 0.01 to 10 ng/mL and from 0.01 to 20 ng/mL, respectively, and the method shows the recovery, matrix effect and process efficiency of steroids isolated from a serum matrix to be within acceptable limits. Good accuracy, repeatability and reproducibility were also shown and the method provided excellent sensitivity and selectivity as stereoisomers and regioisomers were also resolved and quantified accurately. Clinical conditions such as congenital adrenal hyperplasia, polycystic ovary syndrome in females and disorders of sex development in neonates and in children, amongst others, are characterized by abnormal steroid levels. Steroid profiling is essential to accurately diagnose steroid levels in the above settings as well as in androgen excess or deficiency in adrenal-linked endocrine diseases. Our method, separating C 19 and C 21 steroids in a single chromatographic step, offers a reduced sample turnover rate in the clinical setting, while providing comprehensive steroid profiles of in vivo steroids in the nmol/L range. This is, to our knowledge, the first method reported to simultaneously separate C 19 and C 21 steroids, together with their C11-hydroxy and C11-keto metabolites -one which may hold promise in the identification of new steroid markers in steroid-linked endocrine diseases, in addition to profiling steroid metabolism and abnormal enzyme activity in patients. Copyright © 2018 Elsevier B.V. All rights reserved.

Chemical interaction between Lilium brownii and Rhizoma Anemarrhenae, the herbal constituents of Baihe Zhimu decoction, by liquid chromatography coupled to hybrid triple quadrupole linear ion trap mass spectrometer.

PubMed

Yang, Bo; Liu, Zhirui; Wang, Qian; Xia, Peiyuan

2018-03-01

During the course of decoction, the components of herbal formula interact with each other, such that chemical extraction characteristics are altered. The crude drugs, Lilium brownii (Baihe) and Rhizoma Anemarrhenae (Zhimu), are the herbal constituents of Baihe Zhimu decoction, a traditional herbal formula. To investigate the chemical interaction between Baihe and Zhimu when decocting together, eight marker components in Baihe Zhimu decoction were simultaneously characterized and quantified in one run by a hybrid triple quadrupole linear ion trap mass spectrometer in the multiple reactions monitoring-information dependent acquisition-enhanced product ion mode. The results showed that Zhimu significantly suppressed the extraction of phenolic glycosides (the components from Baihe) when co-decocting, and Baihe clearly suppressed the extraction of xanthones and steroidal saponins (the components from Zhimu). Overall, the presently developed method would be a preferred candidate for the investigation of the chemical interaction between herbal medicines. Copyright © 2017 John Wiley & Sons, Ltd.

Elicitation of Diosgenin Production in Trigonella foenum-graecum (Fenugreek) Seedlings by Methyl Jasmonate

PubMed Central

Chaudhary, Spandan; Chikara, Surendra K.; Sharma, Mahesh C.; Chaudhary, Abhinav; Alam Syed, Bakhtiyar; Chaudhary, Pooja S.; Mehta, Aditya; Patel, Maulik; Ghosh, Arpita; Iriti, Marcello

2015-01-01

The effects of methyl jasmonate (MeJA), an elicitor of plant defense mechanisms, on the biosynthesis of diosgenin, a steroidal saponin, were investigated in six fenugreek (Trigonella foenum-graecum) varieties (Gujarat Methi-2, Kasuri-1, Kasuri-2, Pusa Early Branching, Rajasthan Methi and Maharashtra Methi-5). Treatment with 0.01% MeJA increased diosgenin levels, in 12 days old seedlings, from 0.5%–0.9% to 1.1%–1.8%. In addition, MeJA upregulated the expression of two pivotal genes of the mevalonate pathway, the metabolic route leading to diosgenin: 3-hydroxy-3-methylglutaryl-CoA reductase (HMG) and sterol-3-β-glucosyl transferase (STRL). In particular, MeJA increased the expression of HMG and STRL genes by 3.2- and 22.2-fold, respectively, in the Gujarat Methi-2 variety, and by 25.4- and 28.4-fold, respectively, in the Kasuri-2 variety. Therefore, MeJA may be considered a promising elicitor for diosgenin production by fenugreek plants. PMID:26694357

Computer Aided Screening of Phytochemicals from Garcinia against the Dengue NS2B/NS3 Protease.

PubMed

Qamar, Tahir Ul; Mumtaz, Arooj; Ashfaq, Usman Ali; Azhar, Samia; Fatima, Tabeer; Hassan, Muhammad; Hussain, Syed Sajid; Akram, Waheed; Idrees, Sobia

2014-01-01

Dengue virus NS2/NS3 protease because of its ability to cleave viral proteins is considered as an attractive target to screen antiviral agents. Medicinal plants contain a variety of phytochemicals that can be used as drug against different diseases and infections. Therefore, this study was designed to uncover possible phytochemical of different classes (Aromatic, Carbohydrates, Lignin, Saponins, Steroids, Tannins, Terpenoids, Xanthones) that could be used as inhibitors against the NS2B/NS3 protease of DENV. With the help of molecular docking, Garcinia phytochemicals found to be bound deeply inside the active site of DENV NS2B/NS3 protease among all tested phytochemicals and had interactions with catalytic triad (His51, Asp75, Ser135). Thus, it can be concluded from the study that these Gracinia phytochemicals could serve as important inhibitors to inhibit the viral replication inside the host cell. Further in-vitro investigations require confirming their efficacy.

Phytochemical screening and chemical variability in volatile oils of aerial parts of Morinda morindoides.

PubMed

Kiazolu, J Boima; Intisar, Azeem; Zhang, Lingyi; Wang, Yun; Zhang, Runsheng; Wu, Zhongping; Zhang, Weibing

2016-10-01

Morinda morindoides is an important Liberian traditional medicine for the treatment of malaria, fever, worms etc. The plant was subjected to integrated approaches including phytochemical screening and gas chromatography mass spectrometry (GC-MS) analyses. Phytochemical investigation of the powdered plant revealed the presence of phenolics, tannins, flavonoids, saponins, terpenes, steroidal compounds and volatile oil. Steam distillation followed by GC-MS resulted in the identification of 47 volatiles in its aerial parts: 28 were in common including various bioactive volatiles. Major constituents of leaves were phytol (43.63%), palmitic acid (8.55%) and geranyl linalool (6.95%) and stem were palmitic acid (14.95%), eicosane (9.67%) and phytol (9.31%), and hence, a significant difference in the percentage composition of aerial parts was observed. To study seasonal changes, similarity analysis was carried out by calculating correlation coefficient (r) and vector angle cosine (z) that were more than 0.91 for stem-to-stem and leaf-to-leaf batches indicating considerable consistency.

Enhancement of the functionality of bread by incorporation of Shatavari (Asparagus racemosus).

PubMed

Singh, Nishu; Jha, Alok; Chaudhary, Anand; Upadhyay, Ashutosh

2014-09-01

In view of the wider consumption of bakery products, they could be good choice for the delivery of functionality. The present study attempts to develop a functional formulation of bread by incorporation of shatavari (Asparagus racemosus Willd.), which is an important medicinal plant of India. Central composite rotatable design (CCRD) was used for experiments in which yeast and shatavari powder were taken as variables. Response surface methodology (RSM) was used to optimize the bread formulations on the basis of hardness, adhesiveness, springiness, chewiness and cohesiveness as responses. Qualitative tests were performed for assessing the presence of phytochemicals in shatavari bread. Sensory attributes of the shatavari bread were evaluated using descriptive analysis technique. The optimum acceptable level for shatavari and yeast in bread was found to be 3.5 % and 4.96 %, respectively. All the phytochemicals such as alkaloid, steroid, terpenoid and saponin present in original herbs were also present in bread. However flavonoids were not found in the bread when analysed qualitatively and using TLC.

Computer Aided Screening of Phytochemicals from Garcinia against the Dengue NS2B/NS3 Protease

PubMed Central

Qamar, Tahir ul; Mumtaz, Arooj; Ashfaq, Usman Ali; Azhar, Samia; Fatima, Tabeer; Hassan, Muhammad; Hussain, Syed Sajid; Akram, Waheed; Idrees, Sobia

2014-01-01

Dengue virus NS2/NS3 protease because of its ability to cleave viral proteins is considered as an attractive target to screen antiviral agents. Medicinal plants contain a variety of phytochemicals that can be used as drug against different diseases and infections. Therefore, this study was designed to uncover possible phytochemical of different classes (Aromatic, Carbohydrates, Lignin, Saponins, Steroids, Tannins, Terpenoids, Xanthones) that could be used as inhibitors against the NS2B/NS3 protease of DENV. With the help of molecular docking, Garcinia phytochemicals found to be bound deeply inside the active site of DENV NS2B/NS3 protease among all tested phytochemicals and had interactions with catalytic triad (His51, Asp75, Ser135). Thus, it can be concluded from the study that these Gracinia phytochemicals could serve as important inhibitors to inhibit the viral replication inside the host cell. Further in-vitro investigations require confirming their efficacy. PMID:24748749

Phytochemical screening and antioxidant capacity of the aerial parts of Thymelaea hirsuta L.

PubMed Central

Amari, Nesrine Ouda; Bouzouina, Mohamed; Berkani, Abdellah; Lotmani, Brahim

2014-01-01

Objective To assess antioxidant activities of different aerial parts of Thymelaea hirsuta (T. hirsuta) from west Algeria, and to search for new sources of safe and inexpensive antioxidants. Methods Samples of leaves, stems and flowers from T. hirsuta were tested for total phenolic content, flavonoids content, and evaluation its total antioxidant activity, were done using the spectrophotometric analyses. Results Results of preliminary phytochemical screening of leaf, flower and stem of T. hirsuta revealed the presence of tannins, alkaloids, steroids, saponins, coumarins, reducteurs compound and anthraquinones. The total phenolics and flavonoids were estimated. The aqueous extracts of the aerial parts of T. hirsuta showed potent in vitro antioxydant activities using various models viz, DPPH scavenging assay, ferric reducing antioxidant power (FRAP) and ABTS radical scavenging activity. Conclusions On the basis of the results obtained, T. hirsuta extracts are rich sources of natural antioxidants appears to be an alternative to synthetic antioxidants and this justifies its therapeutic usage.

[Research progress on enlargement of medicinal resources of Paridis Rhizome].

PubMed

Cheng, Li; Zhen, Yan; Chen, Min; Huang, Lu-qi

2015-08-01

Currently, as an important raw material of Chinese traditional patent medicines, Paridis Rhizome is in great demand, which led to its price increases. In order to protect the wild resources and satisfy market demand of Paridis rhizome, the researches in various directions were conducted, involved its chemical composition, pharmacological action, clinical application, resource investigation, artificial cultivation, etc. Herein, the chemical studies of genus Paridis Rhizome, aerial parts of Paridis Rhizome gummy and starchy Paridis Rhizome, and the studies of endophyte in Paridis Rhizome were reviewed and analyzed in order to explore the substitutes of Paridis Rhizome, and provide the reference for the enlargement of medicinal resources of Paridis Rhizome. It manifests that the steroidal saponins, the important chemical compositions in Paridis Rhizome were tested in genus Paridis Rhizome, aerial parts of Paridis Rhizome, gummy Paridis Rhizome and the endophyte in Paridis Rhizome. However, the further experimental studies and clinical verification works should be carried out to confirm the final substitute.

The Cytotoxicity of Dacarbazine Potentiated by Sea Cucumber Saponin in Resistant B16F10 Melanoma Cells through Apoptosis Induction

PubMed Central

Baharara, Javad; Amini, Elaheh; Nikdel, Najme; Salek-Abdollahi, Farzaneh

2016-01-01

Background: Malignant melanoma is a highly aggressive malignant melanocytic neoplasm which resists against the most conventional therapies. Sea cucumber as one of marine organisms contains bioactive compounds such as polysaccharide, terpenoid and other metabolites which have anti-cancer, anti-tumor, anti-inflammatory and antioxidant properties. The present study was designed to investigate the anticancer potential of saponin extracted from sea cucumber Holothuria leucospilata alone and in combination with dacarbazine on B16F10 melanoma cell line. Methods: The B16F10 cell line was treated with different concentrations of saponin (0, 4, 8, 12, 16, 20 μg/ml), dacarbazine (0, 1200, 1400, 1600, 18000, 1200, 1400, 1600, 2000 μg/ml) and co-administration of saponin-dacarbazine (1200 da+8 sp, 1200 da+4 sp) for 24 and 48 hr and the cytotoxic effect was examined by MTT, DAPI, acridine orange/propodium iodide, flow cytometry and caspase colorimetric assay. Results: The results exhibited that sea cucumber saponin, dacarbazine, and co-administration of saponin-dacarbazine inhibited the proliferation of melanoma cells in a dose and time dependent manner with IC50 values of 10, 1400 and 4+1200 μg/ml, respectively. Morphological observation of DAPI and acridine orange/propodium iodide staining documented typical characteristics of apoptotic cell death. Flow cytometry assay indicated accumulation of IC50 treated cells in sub-G1 peak. Additionally, saponin extracted induced intrinsic apoptosis via up-regulation of caspase-3 and caspase-9. Conclusion: These results revealed that the saponin extracted from sea cucumber as a natural anti-cancer compound may be a new treatment modality for metastatic melanoma and the application of sea cucumber saponin in combination with dacarbazine demonstrated the strongest anti-cancer activity as compared with the drug alone. PMID:27563423

Effect of ginseng saponins on the recombinant serotonin type 3A receptor expressed in xenopus oocytes: implication of possible application as an antiemetic.

PubMed

Min, Kyeong T; Koo, Bon N; Kang, Jeong W; Bai, Sun Joon; Ko, Sung R; Cho, Zang-Hee

2003-08-01

Nausea and vomiting are the most frequently reported side-effects by patients who are given general anesthesia perioperatively and patients with cancer who undergo chemotherapy or radiotherapy. Serotonin (5-hydroxytryptamine, 5HT) type 3A receptor (5HT(3A) receptor) is known to mediate nausea and vomiting and its antagonists have been used effectively to prevent and/or reduce the incidence and severity of nausea and vomiting. However, the adverse effects on cardiac function, such as QT interval prolongation, limit their routine use by these patients. This study was designed to elucidate the effect of ginseng saponins on the recombinant 5HT(3A) receptor expressed in the xenopus oocyte. After in vitro transcription of the recombinant human 5HT(3A) receptor in the Xenopus laevis oocyte, we examined Panax ginseng saponins (total saponin [TS], panaxadiol saponin [PD] fraction, panaxatriol saponin [PT] fraction, and ginsenoside-Rb1 and -Rg1) for their ability to inhibit current flow through the 5HT(3A) receptor using the voltage-clamp technique. All saponin fractions (TS, PD, PT fraction, as well as ginsenoside-Rb1 and -Rg1) inhibited the peak current induced by the agonist 5HT on the 5HT(3A) receptor in a concentration-dependent, reversible, and voltage-independent manner. The PT fraction inhibited 5HT-induced currents in 5HT(3A) receptor more than the PD fraction; meanwhile, there was a similar degree of inhibition between ginsenoside-Rg1 and -Rb1, the main substitutes of PT fraction and PD saponin fractions, respectively. These results indicate that ginseng saponins, especially PT fraction, have substantial inhibitory effects on the recombinant 5HT(3A) receptor, suggesting that some of the specific types of ginsenoside might have an antagonistic action against 5HT(3A) receptor related to nausea and vomiting.

Effects of total saponins from Trillium tschonoskii rhizome on grey and white matter injury evaluated by quantitative multiparametric MRI in a rat model of ischemic stroke.

PubMed

Li, Manzhong; Ouyang, Junyao; Zhang, Yi; Cheng, Brian Chi Yan; Zhan, Yu; Yang, Le; Zou, Haiyan; Zhao, Hui

2018-04-06

Trillium tschonoskii rhizome (TTR), a medicinal herb, has been traditionally used to treat traumatic brain injury and headache in China. Although the potential neuroprotective efficacy of TTR has gained increasing interest, the pharmacological mechanism remains unclear. Steroid saponins are the main bioactive components of the herb. To investigate the protective and repair-promoting effects of the total saponins from TTR (TSTT) on grey and white matter damages in a rat model of middle cerebral artery occlusion (MCAO) using magnetic resonance imaging (MRI) assay. Ischemic stroke was induced by MCAO. TSTT and Ginaton (positive control) were administered orally to rats 6h after stroke and daily thereafter. After 15 days of treatment, the survival rate of each group was calculated. We then conducted neurological deficit scores and beam walking test to access the neurological function after ischemic stroke. Subsequently, T2-weighted imaging (T2WI) and T2 relaxometry mapping were performed to measure infarct volume and grey and white matter integrity, respectively. Moreover, diffusion tensor imaging (DTI) was carried out to evaluate the grey and white matter microstructural damage. Additionally, arterial spin labelling (ASL) - cerebral blood flow (CBF) and magnetic resonance angiography (MRA) images provided dynamic information about vascular hemodynamic dysfunction after ischemic stroke. Finally, haematoxylin and eosin (HE) staining was carried out to evaluate the stroke-induced pathological changes in the brain. The survival rate and neurological behavioural outcomes (Bederson scores and beam walking tests) were markedly ameliorated by TSTT (65mg/kg) treatment within 15 days after ischemic stroke. Moreover, T2WI and T2 relaxometry mapping showed that TSTT (65mg/kg) significantly reduced infarct volume and attenuated grey and white matter injury, respectively, which was confirmed by histopathological evaluation of brain tissue. The results obtained from DTI showed that TSTT (65mg/kg) not only significantly alleviated axonal damage and demyelination, but also promoted axonal remodelling and re-myelination. In addition, TSTT treatment also enhanced vascular signal density and increased CBF in rats after MCAO. Our results suggested the potential protective and repair-promoting effects of TSTT on grey and white matter from damage induced by ischemia. This study provides a modern pharmacological basis for the application of TSTT in managing ischemic stroke. Copyright © 2018 Elsevier B.V. All rights reserved.

Sulfated steroid-amino acid conjugates from the Irish marine sponge Polymastia boletiformis.

PubMed

Smyrniotopoulos, Vangelis; Rae, Margaret; Soldatou, Sylvia; Ding, Yuanqing; Wolff, Carsten W; McCormack, Grace; Coleman, Christina M; Ferreira, Daneel; Tasdemir, Deniz

2015-03-24

Antifungal bioactivity-guided fractionation of the organic extract of the sponge Polymastia boletiformis, collected from the west coast of Ireland, led to the isolation of two new sulfated steroid-amino acid conjugates (1 and 2). Extensive 1D and 2D NMR analyses in combination with quantum mechanical calculations of the electronic circular dichroism (ECD) spectra, optical rotation, and 13C chemical shifts were used to establish the chemical structures of 1 and 2. Both compounds exhibited moderate antifungal activity against Cladosporium cucumerinum, while compound 2 was also active against Candida albicans. Marine natural products containing steroidal and amino acid constituents are extremely rare in nature.

Effects of long term feeding of Quillaja saponins on sex ratio, muscle and serum cholesterol and LH levels in Nile tilapia (Oreochromis niloticus (L)).

PubMed

Francis, George; Levavi-Sivan, Berta; Avitan, Ayelet; Becker, Klaus

2002-12-01

Seventeen-day-old Nile tilapia fry were fed a standard diet (C) or diets containing 50-700 mg kg(-1) Quillaja saponin (QS) extract (groups S50, S150, S300, S500 and S700). After the first 8 weeks, 30 randomly selected tilapia from each of the treatments were placed in separate aquaria and fed the standard diet without saponins from then on (these were designated S50/C, S150/C, S300/C, S500/C and S700/C). The fish grew from an initial average weight of approximately 30 mg to a final average weight of 79 g during the 6-month feeding period. The difference between the average weight of C-fed tilapia and the treatment with the highest average weight after 6 months was 53.5%. The sex ratio of tilapia in the saponin-fed groups deviated from the normal 50:50 male:female ratio, with the S700 group showing a significantly higher number of males. Quillaja saponin stimulated LH release from dispersed tilapia pituitary cells in vitro. This effect was abolished in the presence of dilute calf serum. Serum LH values did not show any diet-dependent trend in either male or female tilapia in vivo. In both continuously saponin-fed and only-initially saponin-fed groups, the average serum (but not muscle) cholesterol levels in males showed an increasing trend (R(2) values of 0.62 and 0.69) with increasing dietary saponin level. It was concluded that dietary QS has the potential to change the sex-ratio in favour of males. More investigations are required to determine the mechanism of action and the optimum dietary level of QS for maximum effects.

[Leaching Remediation of Copper and Lead Contaminated Lou Soil by Saponin Under Different Conditions].

PubMed

Deng, Hong-xia; Yang, Ya-li; Li, Zhen; Xu, Yan; Li, Rong-hua; Meng, Zhao-fu; Yang, Ya-ti

2015-04-01

In order to investigate the leaching remediation effect of the eco-friendly biosurfactant saponin for Cu and Pb in contaminated Lou soil, batch tests method was used to study the leaching effect of saponin solution on single Cu, Pb contaminated Lou soil and mixed Cu and Pb contaminated Lou soil under different conditions such as reaction time, mass concentration of saponin, pH, concentration of background electrolyte and leaching times. The results showed that the maximum leaching removal effect of Cu and Pb in contaminated Lou soil was achieved by complexation of the heavy metals with saponin micelle, when the mass concentration of saponin solution was 50 g x L(-1), pH was 5.0, the reaction time was 240 min, and there was no background electrolyte. In single and mixed contaminated Lou soil, the leaching percentages of Cu were 29.02% and 25.09% after a single leaching with 50 g x L(-1) saponin under optimal condition, while the single leaching percentages of Pb were 31.56% and 28.03%, respectively. The result indicated the removal efficiency of Pb was more significant than that of Cu. After 4 times of leaching, the cumulative leaching percentages of Cu reached 58.92% and 53.11%, while the cumulative leaching percentages of Pb reached 77.69% and 65.32% for single and mixed contaminated Lou soil, respectively. The fractionation results of heavy metals in soil before and after a single leaching showed that the contents of adsorbed and exchangeable Cu and Pb increased in the contaminated soil, while the carbonate-bound, organic bound and sulfide residual Cu and Pb in the contaminated Lou soil could be effectively removed by saponin.

Hypocholesterolemic effect of karaya saponin in Japanese laying quails (Coturnix coturnix japonica).

PubMed

Afrose, S; Hossain, M S; Tsujii, H

2011-12-01

The effect of karaya saponin supplementation on the serum and egg yolk cholesterol and fatty acid composition in egg yolk were investigated in Japanese quails. A total of 80 Japanese quails aged 5 weeks were equally divided into four groups of 20. Four levels (0, 25, 50 and 75 mg/kg feed) of karaya saponin were included in the basal diet and experiment was lasted for 6 weeks. The cholesterol fractions in the egg yolk and serum were measured by enzymatic assay, and the fatty acid composition in egg yolk was determined by gas chromatography. The results revealed that the supplementation of 75 mg/kg karaya saponin significantly reduced (p < 0.05) cholesterol and triglycerides concentration in serum and egg yolk. High-density lipoprotein-cholesterol was increased, low-density lipoprotein-cholesterol and the atherogenic index were decreased (p < 0.05) by the dietary supplementations. Hepatic cholesterol was reduced (p < 0.05) by the 25 mg/kg karaya saponin. A higher degree of yolk colour was improved (p < 0.05) when 75 mg/kg saponin was supplemented in the diet. The concentration of polyunsaturated fatty acids (PUFA) in egg yolk was increased (p < 0.05) in a dose-dependent manner in quails fed the supplemented diet than the control diet. The ratio of PUFA to saturated fatty acids in egg yolk was improved (p < 0.05) by 75 mg/kg feed karaya saponin-supplemented diet. Therefore, the dietary supplementation of 75 mg/kg karaya saponin may be a feasible means of producing quail eggs with lower cholesterol and higher PUFA content for health conscious consumers. © 2010 Blackwell Verlag GmbH.

Extraction of saponins and toxicological profile of Teucrium stocksianum boiss extracts collected from District Swat, Pakistan.

PubMed

Shah, Syed Muhammad Mukarram; Sadiq, Abdul; Shah, Syed Muhammad Hassan; Khan, Shahzeb

2014-12-04

The current era is facing challenges in the management of neoplasia and weeds control. The currently available anti-cancer and herbicidal drugs are associated with some serious side effects. Therefore numerous researchers are trying to discover and develop plant based alternative particularly for the rational management of cancer and weed control. Teucrium stocksianum possess antioxidant and analgesic activities. The current study was designed to evaluate crude saponins (CS), methanolic extract and sub-fractions of T. stocksianum for cytotoxic and phytotoxic potentials. CS, methanolic extract and sub-fractions were extracted from powdered plant material using different solvents. Cytotoxic potential of the extracts at a dose of 10, 100 and 1000 μg/ml were evaluated against Brine shrimp's nauplii. Phytotoxic assay also performed at the same concentration against Lemna minor. Etoposide and Paraquat were used as positive controls in cytotoxic and phytotoxic assays respectively. The percent yield of crude saponins was (5%). CS demonstrated tremendous brine shrimp lethality showing < 10 μg/ml LC50. The n-hexane (HF) and chloroform fractions (CF) demonstrated excellent cytotoxicity with 80 and 55 μg/ml LC50 respectively. Whereas the methanolic extract (TSME), ethyl acetate (EAF) and aqueous fractions (AF) revealed moderate cytotoxicity showing 620, 860 and 1000 μg/ml LC50 values respectively. In phytotoxic assay profound inhibition was displayed by HF (96.67%) and TSME (95.56%, 30 μg/ml LC50) against the growth of Lemna minor at 1000 μg/ml respectively. Both CF and EAF demonstrated profound phytoxicity (93.33%) respectively at highest concentration (1000 μg/ml), while AF and CS demonstrated weak phytotoxicity with 1350 and 710 μg/ml LC50 values respectively. Cytotoxicity and phytotoxicity assays indicated that the crude saponins, n-hexane and chloroform fractions of T. stocksianum could play a vital role in the treatment of neoplasia and as potential natural herbicides. Therefore these sub-fractions are recommended for further investigation with the aim to isolate novel anti-cancer and herbicidal compounds.

Anti-invasive effect of Cyclamen pseudibericum extract on A549 non-small cell lung carcinoma cells via inhibition of ZEB1 mediated by miR-200c.

PubMed

Karagur, Ege Riza; Ozay, Cennet; Mammadov, Ramazan; Akca, Hakan

2018-06-01

Scientists are increasingly focusing attention on natural products of plant origin for use as agents in cancer protection and treatment. Cyclamen L. tuber extracts contain saponin glycosides that have been shown to have anti-cancer and other biological activities. The epithelial-to-mesenchymal transition (EMT) is thought to enhance malignant tumour progress. The transcriptional repressor zinc-finger E-box binding homeobox 1 (ZEB1) is an important inducer of EMT in different human tumours and has recently been shown to boost invasion by tumour cells. In this study, we investigated the effects of endemic Cyclamen pseudibericum (CP) saponin-rich tuber extract on the capacity of non-small cell lung cancer line A549 cells to proliferate, invade and migrate and also examined the expression levels of several invasion-migration-related microRNAs (miRNAs) to identify those which directly targeted ZEB1. The cytotoxicity effect of the CP extract on the A549 cancer cells was determined by the luminometric method. The half-minimal (50%) inhibitory concentration dose in the A549 cells was determined to be 41.64 ± 2.35 µg/mL. Using the Matrigel invasion chamber system and the wound healing assay we observed that the CP extract suppressed the invasion and migration capacity of A549 cells, respectively. The expression of miRNAs in A549 cells was evaluated by real-time PCR. Our data showed that overexpression of miRNA miR-200c hindered the EMT by increasing the expression of E-cadherin and decreasing the expression of both N-cadherin and vimentin through the direct targeting of ZEB1. These findings suggest that the saponin-rich tuber extract of CP may have considerable anti-cancer properties in lung cancer. Further studies are required to examine in detail the molecular-based mechanism involved in the EMT process of the extract along with isolation and identification of active saponin components.

[Study on extraction and purification technology of Hubei ophiopogon saponins].

PubMed

Lin, Yun-Han; Li, Chong-Ming; Li, Xiao-Dong; Xiang, Yang; Zhang, Ya-Qin; Zhang, Xiao-Cun; Liu, Xia

2013-05-01

To explore the extraction and purification technology of total saponins from the effective parts of Liriope spicata. Orthogonal design was used. Macroporous resin was selected to separate and purify total saponin from the effective parts of Liriope spicata. The process validation was conducted. The total saponins was determined by Ultraviolet Spectrophotometry. The optimal extraction conditions were as follows: 10 times the amount of ethanol (70%) for each occasion and hot reflux (3 x 2 h). Total saponins was purified by D101 macroporous resin. The concentration of eluting ethanol was 50% - 70%. Ethanol (70%) was selected as the best eluent. The result of process validation was consistent with the study. The process is simple and stable enough to significantly improve the extraction rate of the effective parts. The study can provide reference for the research and production of effective parts of traditional Chinese medicine such as Liriope spicata.

A novel technology coupling extraction and foam fractionation for separating the total saponins from Achyranthes bidentata.

PubMed

Ding, Linlin; Wang, Yanji; Wu, Zhaoliang; Liu, Wei; Li, Rui; Wang, Yanyan

2016-10-02

A novel technology coupling extraction and foam fractionation was developed for separating the total saponins from Achyranthes bidentata. In the developed technology, the powder of A. bidentata was loaded in a nylon filter cloth pocket with bore diameter of 180 µm. The pocket was fixed in the bulk liquid phase for continuously releasing saponins. Under the optimal conditions, the concentration and the extraction rate of the total saponins in the foamate by the developed technology were 73.5% and 416.2% higher than those by the traditional technology, respectively. The foamates obtained by the traditional technology and the developed technology were analyzed by ultraperformance liquid chromatography-mass spectrometry to determine their ingredients, and the results appeared that the developed technology exhibited a better performance for separating saponins than the traditional technology. The study is expected to develop a novel technology for cost effectively separating plant-derived materials with surface activity.

Solid-phase extraction NMR studies of chromatographic fractions of saponins from Quillaja saponaria.

PubMed

Nyberg, Nils T; Baumann, Herbert; Kenne, Lennart

2003-01-15

The saponin mixture QH-B from the tree Quillaja saponaria var. Molina was fractionated by RP-HPLC in several steps. The fractions were analyzed by solid-phase extraction NMR (SPE-NMR), a technique combining the workup by solid-phase extraction with on-line coupling to an NMR flow probe. Together with MALDI-TOF mass spectrometry and comparison with chemical shifts of similar saponins, the structures of both major and minor components in QH-B could be obtained. The procedure described is a simple method to determine the structure of components in a complex mixture. The two major fractions of the mixture were found to contain at least 28 saponins, differing in the carbohydrate substructures. Eight of these have not previously been determined. The 28 saponins formed 14 equilibrium pairs by the migration of an O-acyl group between two adjacent positions on a fucosyl residue.

Characterization and Enhanced Processing of Soluble, Oligomeric GP140 Envelope Glycoproteins Derived from Human Immunodeficiency Virus Type-1 Primary Isolates

DTIC Science & Technology

2001-01-01

purified from the bark of a South American tree called Quillaja saponaria . QS-21 has been tested in over 2,500 patients in 50 clinical trials...approved vaccines in the U.S. today (143). Up to 10% of the bark from Quillaja is composed of saponins , of which QS-21 is typically one of the more...1996. Structure/function studies on QS-21, a unique immunological adjuvant from Quillaja saponaria Adv Exp Med Biol. 404:165-72. 143. Kensil, C. R

Triterpene constituents from the seedling of Aronia melanocarpa.

PubMed

Yu, M; Li, X; Zhao, C-C; Xu, J; Zhang, P

2007-01-01

Two new triterpene saponins, 16-O-acetyl-21-O-angeloyltheasapogenol A 3-O-[beta-D-galactopyranosyl(1 --> 2)][beta-D-xylopyranosyl(1 --> 2)-alpha-L-arabinopyranosyl (1 --> 3)]-beta-D-glucopyranosiduronic acid (1) and 16,28-O-diacetyl-21-O-tigloyltheasapogenol A 3-O-[beta-D-galactopyranosyl(1 --> 2)][beta-D-xylopyranosyl(1 --> 2)-alpha-L-arabinopyranosyl (1 --> 3)]-beta-D-glucopyranosiduronic acid (2), together with four known triterpenenes, have been isolated from the dried seedling of Aronia melanocarpa, and their structures established by spectroscopic and chemical evidence.

The substances of plant origin that inhibit protein biosynthesis.

PubMed

Gałasiński, W; Chlabicz, J; Paszkiewicz-Gadek, A; Marcinkiewicz, C; Gindzieński, A

1996-01-01

Some plants were used for a long time in folk medicine as sources of anti-tumour remedies. Their effects on protein biosynthesis in vitro have been examined and described. The separate features of the peptide elongation system, isolated from tumoural cells, have been demonstrated. Some elongation factors or ribosomes have been shown to be a target site for the inhibition of protein biosynthesis caused by the substances isolated from various sources. The glycoside and caffeic acid, isolated from Melissa officinalis leaves, inhibited protein biosynthesis by direct influence the elongation factor eEF-2. The activity of this factor was also inhibited by aloin and aloeemodin. Saponin glycoside and its aglycon, isolated from Verbascum thapsiforme flowers, as well as digoxin, emetine and cepheline directly inactivated ribosomes. "Chagi" fraction, isolated from Inonotus obliquus, is responsible for the inhibitory effect caused by the aqueous tannin--less extract from this fungus. The target site for quercetin has been found to be the subunit form EF-1 alpha. It may be supposed that, the plant inhibitors of protein biosynthesis could be utilized for searching specific antitumoural preparations.

Enhanced removal of lead from contaminated soil by polyol-based deep eutectic solvents and saponin.

PubMed

Mukhopadhyay, Soumyadeep; Mukherjee, Sumona; Hayyan, Adeeb; Hayyan, Maan; Hashim, Mohd Ali; Sen Gupta, Bhaskar

2016-11-01

Deep eutectic solvents (DESs) are a class of green solvents analogous to ionic liquids, but less costly and easier to prepare. The objective of this study is to remove lead (Pb) from a contaminated soil by using polyol based DESs mixed with a natural surfactant saponin for the first time. The DESs used in this study were prepared by mixing a quaternary ammonium salt choline chloride with polyols e.g. glycerol and ethylene glycol. A natural surfactant saponin obtained from soapnut fruit pericarp, was mixed with DESs to boost their efficiency. The DESs on their own did not perform satisfactory due to higher pH; however, they improved the performance of soapnut by up to 100%. Pb removal from contaminated soil using mixture of 40% DES-Gly and 1% saponin and mixture of 10% DES-Gly and 2% saponin were above 72% XRD and SEM studies did not detect any major corrosion in the soil texture. The environmental friendliness of both DESs and saponin and their affordable costs merit thorough investigation of their potential as soil washing agents. Copyright © 2016 Elsevier B.V. All rights reserved.