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Sample records for alkaloids saponins tannins

  1. New cycloartane saponin and monoterpenoid glucoindole alkaloids from Mussaenda luteola.

    PubMed

    Mohamed, Shaymaa M; Backheet, Enaam Y; Bayoumi, Soad A; Ross, Samir A

    2016-04-01

    A new cycloartane-type saponin with unusual hydroxylation at C-17 and a unique side chain, 9 (R), 19, 22 (S), 24 (R) bicyclolanost-3β, 12α, 16β, 17α tetrol-25-one 3-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranoside (1) and two new monoterpenoid glucoindole alkaloids, 10-methoxy pumiloside (2) and the previously chemically synthesized, 10-methoxy strictosidine (3) along with other five known compounds, 7α-morroniside (4), 7-epi-loganin (5), (7β)-7-O-methylmorroniside (6), 5(S)-5-carboxystrictisidine (7) and apigenin-7-O-neohesperidoside (8) were isolated from the aerial parts of Mussaenda luteola (Rubiaceae). The structural elucidation of the isolates was accomplished by extensive (1D and 2D NMR) spectroscopic data analysis and HR-ESI-MS. Compounds 4-8 were reported for the first time from the genus Mussaenda. Interestingly, this is the first report for the occurrence of the monoterpenoid glucoindole-type alkaloids in the genus which might be useful for the chemotaxonomic evaluation of the genus Mussaenda. All isolates were evaluated for their antiprotozoal activities. Compound 7 showed good antitrypanosomal activity with IC50 and IC90 values of 13.7 and 16.6 μM compared to IC50 and IC90 values of 13.06 and 28.99 μM for the positive control DFMO, difluoromethylornithine. PMID:26969788

  2. New cycloartane saponin and monoterpenoid glucoindole alkaloids from Mussaenda luteola

    PubMed Central

    Mohamed, Shaymaa M.; Backheet, Enaam Y.; Bayoumi, Soad A.; Ross, Samir A.

    2016-01-01

    A new cycloartane-type saponin with unusual hydroxylation at C-17 and a unique side chain, 9 (R), 19, 22 (S), 24 (R) bicyclolanost-3β, 12α, 16β, 17α tetrol-25-one 3-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranoside (1) and two new monoterpenoid glucoindole alkaloids, 10-methoxy pumiloside (2) and the previously chemically synthesized, 10-methoxy strictosidine (3) along with other five known compounds, 7α-morroniside (4), 7-epi-loganin (5), (7β)-7-O-methylmorroniside (6), 5(S)-5-carboxystrictisidine (7) and apigenin-7-O-neohesperidoside (8) were isolated from the aerial parts of Mussaenda luteola (Rubiaceae). The structural elucidation of the isolates was accomplished by extensive (1D and 2D NMR) spectroscopic data analysis and HR-ESI-MS. Compounds 4–8 were reported for the first time from the genus Mussaenda. Interestingly, this is the first report for the occurrence of the monoterpenoid glucoindole-type alkaloids in the genus which might be useful for the chemotaxonomic evaluation of the genus Mussaenda. All isolates were evaluated for their antiprotozoal activities. Compound 7 showed good antitrypanosomal activity with IC50 and IC90 values of 13.7 and 16.6 µM compared to IC50 and IC90 values of 13.06 and 28.99 µM for the positive control DFMO, difluoromethylornithine. PMID:26969788

  3. Rumen fermentation and nitrogen balance of lambs fed diets containing plant extracts rich in tannins and saponins, and associated emissions of nitrogen and methane.

    PubMed

    Sliwiński, B J; Kreuzer, M; Wettstein, H R; Machmüller, Andrea

    2002-12-01

    Tannins were added to experimental diets at levels of 1 and 2 g/kg DM (hydrolysable tannins; Castanea sativa wood extract) and saponins at 2 and 30 mg/kg DM (sarsaponin; Yucca schidigera extract). These levels were far below thresholds expected to be adverse in ruminants. Effects were measured in lambs by comparison with unsupplemented control diets calculated to be either deficient (10%) or adequate in protein. The diets consisted of hay, concentrate (1:1) and extra wheat starch with increasing body weight. Ruminal pH, VFA concentration, protozoa count and apparent digestibilities of organic matter and fibre did not differ among treatments. The low tannin dose significantly decreased bacteria count compared to the high saponin dose. Saponin supplementation and the high tannin dose showed some potential to reduce ruminal ammonia concentration. This was associated with weak trends towards lower urine N excretion (only tannins) and ammonia emission from manure. Methane release was increased by the low tannin dose compared to the unsupplemented control. Diet effects on heat production were not systematic. In conclusion, the extracts rich in tannins or saponins gave only slight indications for either increased body nitrogen retention or reduced nitrogen emission. However, effects might have been larger with more pronounced dietary protein deficit. PMID:12553689

  4. Alkaloids and Saponins as Cytochrome P450 Inhibitors from Blue Cohosh (Caulophyllum thalictroides) in an In Vitro Assay

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Blue cohosh, Caulophyllum thalictriodes is a popular herb, roots and rhizomes of which have been extensively used for women’s health. Alkaloids and saponins are considered to be responsible for its pharmacological effects. In this investigation the methanolic extract of the roots of blue cohosh, alk...

  5. Analytical methods for determination of alkaloids and saponins from roots of Caulophyllum thalictroids (L) Michx using UPLC HPLC and HPTLC

    Technology Transfer Automated Retrieval System (TEKTRAN)

    A comparison study of analytical methods including HPLC, UPLC and HPTLC are presented in this paper for the determination of major alkaloid and triterpene saponins from the roots of Caulophyllum thalictroides (L.) Michx. (blue cohosh) and dietary supplements claiming to contain blue cohosh. The meth...

  6. Antibacterial, antioxidant and cytotoxic studies of total saponin, alkaloid and sterols contents of decoction of Joshanda: identification of components through thin layer chromatography.

    PubMed

    Khan, Haroon; Khan, Murad Ali; Abdullah

    2015-03-01

    The current study was aimed to assess antibacterial, antioxidant and cytotoxic activity of total saponin, alkaloid and sterol contents of Joshanda decoction followed by its constituent's analysis via thin layer chromatography (TLC). Saponins and alkaloids showed prominent antibacterial activity against Staphylococcus aureus, Bacillus subtilis, Bacillus cereus and Klebsiella pneumoniae whereas sterols only against S. aureus. Saponin and alkaloid contents of 97 and 108 µg/ml, respectively, showed prominent free radical scavenging activity against 1,1-diphenyl-2-picrylhidrazyl, with mild cytotoxicity in brine shrimp cytotoxic test. Under ultraviolet light at 254 nm, TLC of total saponins showed eight different compounds, total sterols comprising three while total alkaloids two compounds of various polarities. It is concluded that the various contents of Joshanda decoction possess outstanding susceptibility against bacteria implicating primarily upper respiratory tract infections augmented by strong antioxidant activity. PMID:23235996

  7. Short communication: assessment of the potential of cinnamaldehyde, condensed tannins, and saponins to modify milk fatty acid composition of dairy cows.

    PubMed

    Benchaar, C; Chouinard, P Y

    2009-07-01

    This study was conducted to determine whether feeding cinnamaldehyde (main component of cinnamon bark essential oil; Cinnamon cassia), condensed tannins from quebracho trees (Schinopsis balansae), or saponins from Yucca schidigera altered the milk fatty acid profile of dairy cows. For this purpose, 4 lactating cows were used in 4 x 4 Latin square design (28-d period) and fed a total mixed ration containing no additive (control), or supplemented with cinnamaldehyde (1 g/d; CIN), quebracho condensed tannin extract (150 g/d; 70% of tannins; QCT), or Yucca schidigera saponin extract (60 g/d; 10% of saponins; YSE). Results revealed no effects of feeding CIN or QCT on milk fatty acid profile. Supplementation with YSE resulted in some modifications of milk fatty acid profile as suggested by the reduced proportions of C6:0 (2.71 vs. 2.95%), C8:0 (1.66 vs. 1.89%), and trans-11 C18:1 (0.92 vs. 1.01%). Results show low potential of cinnamaldehyde, condensed tannins, and saponins to alter ruminal biohydrogenation process and modify the fatty acid profile of milk fat at the feeding rates used in this study. Further investigations are needed to determine the factors that limit the effects of these secondary metabolites on ruminal microbial populations involved in the biohydrogenation processes of unsaturated fatty acids. PMID:19528616

  8. Combinations of alkaloids affecting different molecular targets with the saponin digitonin can synergistically enhance trypanocidal activity against Trypanosoma brucei brucei.

    PubMed

    Krstin, Sonja; Peixoto, Herbenya Silva; Wink, Michael

    2015-11-01

    The flagellate Trypanosoma brucei causes sleeping sickness in humans and nagana in animals. Only a few drugs are registered to treat trypanosomiasis, but those drugs show severe side effects. Also, because some pathogen strains have become resistant, new strategies are urgently needed to combat this parasitic disease. An underexplored possibility is the application of combinations of several trypanocidal agents, which may potentiate their trypanocidal activity in a synergistic fashion. In this study, the potential synergism of mutual combinations of bioactive alkaloids and alkaloids with a membrane-active steroidal saponin, digitonin, was explored with regard to their effect on T. b. brucei. Alkaloids were selected that affect different molecular targets: berberine and chelerythrine (intercalation of DNA), piperine (induction of apoptosis), vinblastine (inhibition of microtubule assembly), emetine (intercalation of DNA, inhibition of protein biosynthesis), homoharringtonine (inhibition of protein biosynthesis), and digitonin (membrane permeabilization and uptake facilitation of polar compounds). Most combinations resulted in an enhanced trypanocidal effect. The addition of digitonin significantly stimulated the activity of almost all alkaloids against trypanosomes. The strongest effect was measured in a combination of digitonin with vinblastine. The highest dose reduction indexes (DRI) were measured in the two-drug combination of digitonin or piperine with vinblastine, where the dose of vinblastine could be reduced 9.07-fold or 7.05-fold, respectively. The synergistic effects of mutual combinations of alkaloids and of alkaloids with digitonin present a new avenue to treat trypanosomiasis but one which needs to be corroborated in future animal experiments. PMID:26349826

  9. Combinations of Alkaloids Affecting Different Molecular Targets with the Saponin Digitonin Can Synergistically Enhance Trypanocidal Activity against Trypanosoma brucei brucei

    PubMed Central

    Peixoto, Herbenya Silva

    2015-01-01

    The flagellate Trypanosoma brucei causes sleeping sickness in humans and nagana in animals. Only a few drugs are registered to treat trypanosomiasis, but those drugs show severe side effects. Also, because some pathogen strains have become resistant, new strategies are urgently needed to combat this parasitic disease. An underexplored possibility is the application of combinations of several trypanocidal agents, which may potentiate their trypanocidal activity in a synergistic fashion. In this study, the potential synergism of mutual combinations of bioactive alkaloids and alkaloids with a membrane-active steroidal saponin, digitonin, was explored with regard to their effect on T. b. brucei. Alkaloids were selected that affect different molecular targets: berberine and chelerythrine (intercalation of DNA), piperine (induction of apoptosis), vinblastine (inhibition of microtubule assembly), emetine (intercalation of DNA, inhibition of protein biosynthesis), homoharringtonine (inhibition of protein biosynthesis), and digitonin (membrane permeabilization and uptake facilitation of polar compounds). Most combinations resulted in an enhanced trypanocidal effect. The addition of digitonin significantly stimulated the activity of almost all alkaloids against trypanosomes. The strongest effect was measured in a combination of digitonin with vinblastine. The highest dose reduction indexes (DRI) were measured in the two-drug combination of digitonin or piperine with vinblastine, where the dose of vinblastine could be reduced 9.07-fold or 7.05-fold, respectively. The synergistic effects of mutual combinations of alkaloids and of alkaloids with digitonin present a new avenue to treat trypanosomiasis but one which needs to be corroborated in future animal experiments. PMID:26349826

  10. Effect of tannins and saponins in Samanea saman on rumen environment, milk yield and milk composition in lactating dairy cows.

    PubMed

    Anantasook, N; Wanapat, M; Cherdthong, A; Gunun, P

    2015-04-01

    The objective of this study was to investigate the effects of tannins and saponins in Samanea saman on rumen fermentation, milk yield and milk composition in lactating dairy cows. Four multiparous early-lactating dairy cows (Holstein-Friesian cross-bred, 75%) with an initial body weight (BW) of 405 ± 40 kg and 36 ± 8 day in milk were randomly assigned to receive dietary treatments according to a 4 × 4 Latin square design. The four dietary treatments were unsupplemented (control), supplemented with rain tree pod (S. saman) meal (RPM) at 60 g/kg, supplemented with palm oil (PO) at 20 g/kg, and supplemented with RPM at 60 g/kg and PO at 20 g/kg (RPO), of total dry matter (DM) intake. Cows were fed with concentrate diets at a ratio of concentrate to milk yield of 1:2, and chopped 30 g/kg of urea-treated rice straw was fed ad libitum. The RPM contained condensed tannins and crude saponins at 88 and 141 g/kg of DM respectively. It was found that supplementation with RPM and/or PO to dairy cows diets did not show negative effect on ruminal pH, blood urea nitrogen and milk urea nitrogen concentration (p > 0.05). However, supplementation with RPM resulted in lower ammonia nitrogen (NH3 -N) concentration (p < 0.05). In addition, propionic acid and milk production increased while acetic acid, acetic to propionic ratio, methane production, methanogens and protozoal population decreased with RPM and/or PO supplementation. Furthermore, addition of PO and RPO in the diets increased milk fat while supplementation of RPM resulted in greater milk protein and Fibrobacter succinogenes numbers (p < 0.05). The population of Ruminococcus flavefaciens and Ruminococcus albus were not affected by any treatments. The findings on the present study showed that supplementation with RPM and RPO to diets of cows improved the rumen environment and increased milk yield, content of milk protein and milk fat. PMID:24814291

  11. Simultaneous determination and characterization of tannins and triterpene saponins from the fruits of various species of Terminalia and Phyllantus emblica using a UHPLC-UV-MS method: application to triphala.

    PubMed

    Avula, Bharathi; Wang, Yan-Hong; Wang, Mei; Shen, Yun-Heng; Khan, Ikhlas A

    2013-01-01

    Terminalia species are a rich source of tannins. Many preparations of these species are used in traditional medicine and have many different ethnobotanical applications. A simple UHPLC method was developed for the simultaneous analysis of such hydrolysable tannins and triterpene saponins from the fruit rinds of different species of Terminalia (T. chebula, T. arjuna, T. bellirica) and Phyllantus emblica. A separation by LC was achieved using a reversed-phase column and a water/acetonitrile mobile phase, both containing formic acid, using a gradient system and a temperature of 40°C. Eight hydrolysable tannins (gallic acid, gallic acid methyl ester, corilagin, chebulagic acid, 1,2,3,6-tetra-O-galloyl-β-D-glucose, ellagic acid, chebulinic acid, and 1,2,3,4,6-penta-O-galloyl-β-D-glucose) and six triterpene saponins (arjunglucoside-I, arjunglucoside-III, chebuloside II, bellericoside, arjunetin, and arjunglucoside-II) could be separated within 20 minutes. The wavelength used for detection with the diode array detector was 254 and 275 nm for tannins and 205 nm for triterpene saponins. The method was validated for linearity, repeatability, limits of detection, and limits of quantification. The developed method is economical, fast, and especially suitable for quality control analysis of tannins and triterpene saponins in various plant samples and commercial products of Terminalia. PMID:23299756

  12. The quality of meat from sheep treated with tannin- and saponin-based remedies as a natural strategy for parasite control.

    PubMed

    Brogna, D M R; Tansawat, R; Cornforth, D; Ward, R; Bella, M; Luciano, G; Priolo, A; Villalba, J

    2014-02-01

    Lambs were assigned to four groups of seven and treated as follows for 12 days: control group (BP) was fed beet pulp; group T (tannin remedy) received the BP diet including 80 g/kg of quebracho extract; group S (saponin remedy) received the BP diet including 15 g/kg of quillaja extract; and group C had a free choice between T and S remedies. Lipid oxidation was lower in meat from S lambs compared to T lambs (P<0.05). Among the volatile compounds, lactate was lower in meat from S lambs compared to T animals (P=0.05). Metabolomic analysis showed that the T treatment increased ribose, fructose, glucose and sorbitol concentration in meat (P<0.05), while cholesterol was decreased by S and C treatments. The T treatment increased the concentration of C14:1 cis-9 (P<0.05). These findings indicate that treatments for parasite control containing tannins and saponins do not detrimentally affect sheep meat quality. PMID:24211542

  13. Changes of Microbial Population in the Rumen of Dairy Steers as Influenced by Plant Containing Tannins and Saponins and Roughage to Concentrate Ratio

    PubMed Central

    Anantasook, N.; Wanapat, M.; Cherdthong, A.; Gunun, P.

    2013-01-01

    The objective of this study was to investigate microbial population in the rumen of dairy steers as influenced by supplementing with dietary condensed tannins and saponins and different roughage to concentrate ratios. Four, rumen fistulated dairy steers (Bos indicus) were used in a 2×2 factorial arrangement in a 4×4 Latin square design. The main factors were two roughage to concentrate ratios (R:C, 60:40 and 40:60) and two supplementations of rain tree pod meal (RPM) (0 and 60 g/kg of total DM intake). Chopped 30 g/kg urea treated rice straw was used as a roughage source. All animals received feed according to respective R:C ratios at 25 g/kg body weight. The RPM contained crude tannins and saponins at 84 and 143 g/kg of DM, respectively. It was found that ruminal pH decreased while ruminal temperature increased by a higher concentrate ratio (R:C 40:60) (p<0.05). In contrast, total bacterial, Ruminococus albus and viable proteolytic bacteria were not affected by dietary supplementation. Numbers of fungi, cellulolytic bacteria, Fibrobactor succinogenes and Ruminococus flavefaciens were higher while amylolytic bacteria was lower when steers were fed at 400 g/kg of concentrate. The population of Fibrobactor succinogenes, was found to be higher with RPM supplementation. In addition, the use of real-time PCR technique indicated that the population of protozoa and methanogens were decreased (p<0.05) with supplementation of RPM and with an increasing concentrate ratio. Supplementation of RPM and feeding different concentrate ratios resulted in changing the rumen microbes especially, when the animals were fed at 600 g/kg of concentrate and supplemented with RPM which significantly reduced the protozoa and methanogens population. PMID:25049745

  14. Digestion, ruminal fermentation, ciliate protozoal populations, and milk production from dairy cows fed cinnamaldehyde, quebracho condensed tannin, or Yucca schidigera saponin extracts.

    PubMed

    Benchaar, C; McAllister, T A; Chouinard, P Y

    2008-12-01

    Four ruminally cannulated lactating cows were used in a 4 x 4 Latin square design (28-d periods) to determine the effects of cinnamaldehyde (CIN; 1 g/cow per day), condensed tannins from quebracho trees (QCT, containing 70% tannins, 150 g/cow per day), and saponins from Yucca schidigera extract (YSE, containing 10% saponins; 60 g/cow per day) on digestion, ruminal fermentation characteristics, protozoal populations, and milk production. Intake of dry matter was not affected by the addition of CIN or QCT, but cows fed YSE had lesser intake than cows fed the control diet (21.8 vs. 23.2 kg/d). Apparent total-tract digestibilities of dry matter, organic matter, crude protein, neutral detergent fiber, and acid detergent fiber were unaffected by dietary treatments. Supplementation with CIN, QTE, or YSE did not affect in situ ruminal degradation of soybean meal, grass silage, or corn grain. Ruminal pH (6.67), total volatile fatty acid concentration (135 mM), and molar proportions (mol/100 mol of total volatile fatty acid) of acetate (65.0), propionate (19.6), and butyrate (11.2) were similar among treatments. Ruminal NH(3)-N concentration was not changed by the addition of CIN and YSE, but tended to decrease in cows fed QCT compared with cows fed the control diet (132 vs. 160 mg/L). Total numbers of ruminal protozoa were not changed by adding CIN, QCT, or YSE in the diet (5.85 log(10)/mL). However, the number of Isotricha was greater in ruminal fluid of cows fed CIN than in ruminal fluid of cows fed the control diet (4.46 vs. 4.23 log(10)/mL). Milk production (33.1 kg/d), milk fat (4.3%), and milk protein (3.5%) remained unchanged between dietary treatments. Results of this study show that under our experimental conditions, supplementing dairy cow diets with CIN, QCT, or YSE had limited effects on digestion, ruminal fermentation characteristics, and protozoal populations. The lack of effects observed in this study suggests that these antimicrobials require administration

  15. Manipulation of ruminal fermentation and methane production by supplementation of rain tree pod meal containing tannins and saponins in growing dairy steers.

    PubMed

    Anantasook, N; Wanapat, M; Cherdthong, A

    2014-02-01

    Four rumen-fistulated dairy steers were used in a 2 × 2 factorial arrangement in a 4 × 4 Latin square design. The main factors were two roughage-to-concentrate ratios (R:C, 60:40 and 40:60) and two supplementation levels of rain tree pod meal (RPM) [0 or unsupplemented and 60 g/kg of total dry matter (DM) intake]. Chopped 30 g/kg of urea-treated rice straw was used as a roughage source. All animals received dietary according to respective R:C ratios at 25 g/kg body weight. The RPM contained condensed tannins and crude saponins at 84 and 143 g/kg of DM respectively. It was found that total volatile fatty acids (VFAs) and propionate concentrations were increased (p < 0.01), while acetate concentration, acetate-to-propionate ratio, CH4 production and protozoal numbers were decreased (p < 0.01) when steers were supplemented with RPM and 600 g/kg of concentrate. Allantoin excretion was found different by both R:C ratio and supplementation of RPM, with the highest value at R:C of 40:60 with 60 g/kg RPM (123.6 mmol/day) (p < 0.05). Allantoin absorption and microbial crude protein were increased (p < 0.05) with an increasing concentrate ratio. Moreover, efficiency of microbial protein synthesis was increased (p < 0.05) by feeding a higher ratio of concentrate (R:C 40:60) and supplementation of RPM. Based on this study, it is suggested that supplementation of RPM was beneficial for dairy cows fed on high roughage ratio, which could improved rumen fermentation by reducing fermentation gas loss, thus improving VFA profiles and thus enhancing efficiency of microbial protein synthesis. PMID:23294319

  16. Analysis of steroidal alkaloids and saponins in Solanaceae plant extracts using UPLC-qTOF mass spectrometry.

    PubMed

    Heinig, Uwe; Aharoni, Asaph

    2014-01-01

    Plants of the Solanaceae family are renowned for the production of cholesterol-derived steroidal glycosides, including the nitrogen containing glycoalkaloids and steroidal saponins. In this chapter we describe the use of UPLC (Ultra Performance Liquid Chromatography) coupled with qTOF (Quadrupole Time-of-Flight) mass spectrometry for profiling of these two large classes of semipolar metabolites. The presented method includes an optimized sample preparation protocol, a procedure for high resolution chromatographic separation and metabolite detection using the TOF mass spectrometer which provides high resolution and mass accuracy. A detailed description for non-targeted data analysis and a strategy for putative identification of steroidal glycosides from complex extracts based on interpretation of mass fragmentation patterns is also provided. The described methodology allows profiling and putative identification of multiple steroidal glycoside compounds from the assortment of Solanaceae species producing these molecules. PMID:24777797

  17. Steroidal Saponins

    NASA Astrophysics Data System (ADS)

    Sahu, N. P.; Banerjee, S.; Mondal, N. B.; Mandal, D.

    The medicinal activities of plants are generally due to the secondary metabolites (1) which often occur as glycosides of steroids, terpenoids, phenols etc. Saponins are a group of naturally occurring plant glycosides, characterized by their strong foam-forming properties in aqueous solution. The cardiac glycosides also possess this, property but are classified separately because of their specific biological activity. Unlike the cardiac glycosides, saponins generally do not affect the heart. These are classified as steroid or triterpenoid saponins depending on the nature of the aglycone. Steroidal glycosides are naturally occurring sugar conjugates of C27 steroidal compounds. The aglycone of a steroid saponin is usually a spirostanol or a furostanol. The glycone parts of these compounds are mostly oligosaccharides, arranged either in a linear or branched fashion, attached to hydroxyl groups through an acetal linkage (2, 3). Another class of saponins, the basic steroid saponins, contain nitrogen analogues of steroid sapogenins as aglycones.

  18. Does Propolis Contain Tannins?

    PubMed Central

    Mayworm, Marco A. S.; Lima, Carolina A.; Tomba, Augusto C. B.; Fernandes-Silva, Caroline C.; Salatino, Maria L. F.

    2014-01-01

    Although polyphenols have been reported as common constituents of propolis, tannins have rarely been mentioned as its constituents. Propolis samples from seven localities in Brazil were analyzed for detection of proanthocyanidins (condensed tannins) and determination of the tannin content. Positive reaction for proanthocyanidins was observed for all samples tested. The contents of tannins varied in the range 0.6–4.1%. A high degree of correlation was noted between total phenols and tannin content. Red and green propolis contained high contents of tannins, while in brown propolis the content was lower. It is suggested that the contents of tannins should be a parameter to be considered in propolis characterization. PMID:24959188

  19. Interaction between a tannin-containing legume and endophyte-infected tall fescue seed on lambs’ feeding behavior and physiology

    Technology Transfer Automated Retrieval System (TEKTRAN)

    It was hypothesized that a tannin-rich legume like sainfoin reduces the negative postingestive effects of ergot alkaloids in tall fescue. Thirty-two 3-month-old lambs were individually penned and randomly assigned to a 2X2 factorial experimental design with two legume species (1-sainfoin [SF; tannin...

  20. Vinca alkaloids.

    PubMed

    Moudi, Maryam; Go, Rusea; Yien, Christina Yong Seok; Nazre, Mohd

    2013-11-01

    Vinca alkaloids are a subset of drugs obtained from the Madagascar periwinkle plant. They are naturally extracted from the pink periwinkle plant, Catharanthus roseus G. Don and have a hypoglycemic as well as cytotoxic effects. They have been used to treat diabetes, high blood pressure and have been used as disinfectants. The vinca alkaloids are also important for being cancer fighters. There are four major vinca alkaloids in clinical use: Vinblastine (VBL), vinorelbine (VRL), vincristine (VCR) and vindesine (VDS). VCR, VBL and VRL have been approved for use in the United States. Vinflunine is also a new synthetic vinca alkaloid, which has been approved in Europe for the treatment of second-line transitional cell carcinoma of the urothelium is being developed for other malignancies. Vinca alkaloids are the second-most-used class of cancer drugs and will stay among the original cancer therapies. Different researches and studies for new vinca alkaloid applications will be carried out in this regard. PMID:24404355

  1. Vinca Alkaloids

    PubMed Central

    Moudi, Maryam; Go, Rusea; Yien, Christina Yong Seok; Nazre, Mohd.

    2013-01-01

    Vinca alkaloids are a subset of drugs obtained from the Madagascar periwinkle plant. They are naturally extracted from the pink periwinkle plant, Catharanthus roseus G. Don and have a hypoglycemic as well as cytotoxic effects. They have been used to treat diabetes, high blood pressure and have been used as disinfectants. The vinca alkaloids are also important for being cancer fighters. There are four major vinca alkaloids in clinical use: Vinblastine (VBL), vinorelbine (VRL), vincristine (VCR) and vindesine (VDS). VCR, VBL and VRL have been approved for use in the United States. Vinflunine is also a new synthetic vinca alkaloid, which has been approved in Europe for the treatment of second-line transitional cell carcinoma of the urothelium is being developed for other malignancies. Vinca alkaloids are the second-most-used class of cancer drugs and will stay among the original cancer therapies. Different researches and studies for new vinca alkaloid applications will be carried out in this regard. PMID:24404355

  2. Saponins as tool for improved targeted tumor therapies.

    PubMed

    Fuchs, H; Bachran, D; Panjideh, H; Schellmann, N; Weng, A; Melzig, M F; Sutherland, M; Bachran, C

    2009-02-01

    Saponins are plant glycosides that consist of a steroid, steroid alkaloid or triterpenoid aglycone and one or more sugar chains that are covalently linked by glycosidic binding to the aglycone. Glucose, galactose, glucuronic acid, xylose and rhamnose are commonly bound monosaccharides. Saponins are found in all organs of a variety of higher plants. Due to the great variability of their structures, diverse functions have been described for distinct saponins; including foaming and pore forming properties as well as selective removal of protozoa from the rumen. The most interesting properties are, however, favorable anti-tumorigenic effects. Several saponins inhibit tumor cell growth by cell cycle arrest and apoptosis with half maximal inhibitory concentrations of down to 0.2 microM. A drawback of saponins in tumor therapy is the non-targeted spreading throughout the whole body. Surprisingly, certain saponins were identified that drastically enhance the efficacy of targeted chimeric toxins bearing the ribosome-inactivating protein saporin as cell-killing moiety. It was demonstrated that this effect is substantially more pronounced on target cells than on non-target cells, thus not only preserving the target specificity of the chimeric toxin but also broadening the therapeutic window with simultaneous dose lowering. This review describes the role of saponins as drug in general, their use as single drug treatment in tumor therapy, their combination with conventional tumor treatment strategies and the synergistic effects with particular targeted tumor therapies that are based on recombinant proteins. PMID:19199910

  3. Tannins as Gibberellin Antagonists 1

    PubMed Central

    Corcoran, Mary Ritzel; Geissman, T. A.; Phinney, Bernard O.

    1972-01-01

    Fourteen chemically defined hydrolyzable tannins and six impure mixtures of either condensed or hydrolyzable tannins were found to inhibit the gibberellin-induced growth of light-grown dwarf pea seedlings. The highest ratio of tannins to gibberellic acid tested (1000: 1 by weight) inhibited from 80 to 95% of the induced growth for all tannins tested except for two monogalloyl glucose tannins which inhibited only 50% of the induced growth. The lowest ratio tested (10: 1) inhibited the induced growth by less than 25% except for the case of terchebin where 50% inhibition was found. The inhibition of gibberellin-induced growth was found to be completely reversed by increasing the amount of gibberellin in three cases tested. Tannins alone did not inhibit endogenous growth of either dwarf or nondwarf pea seedlings. Eight compounds related to tannins, including coumarin, trans-cinnamic acid, and a number of phenolic compounds were also tested as gibberellin antagonists. Most of these compounds showed some inhibition of gibberellin-induced growth, but less than that of the tannins. At the highest ratio (1000: 1) the greatest inhibition was 55%; at the lowest ratio (10: 1) no more than 17% was observed. These compounds did not inhibit endogenous growth, and the inhibition of gibberellin-induced growth could be reversed by increasing the amount of gibberellin in two cases tested. Six chemically defined tannins were found to inhibit hypocotyl growth induced by gibberellic acid in cucumber seedlings. Growth induced by indoleacetic acid in the same test was not inhibited. The highest ratio of tannin to promotor tested gave strong inhibition of gibberellic acid-induced growth, but actually enhanced the growth induced by indoleacetic acid. This difference in action suggests a specificity between the tannins and gibberellic acid. PMID:16657953

  4. Interaction between a tannin-containing legume and endophyte-infected tall fescue seed on lambs’ feeding behavior and physiology

    Technology Transfer Automated Retrieval System (TEKTRAN)

    It was hypothesized that a tannin-rich legume like sainfoin reduces the negative post-ingestive effects of ergot alkaloids in tall fescue. Thirty-two 4-month-old lambs were individually penned and randomly assigned to a 2X2 factorial arrangement with two legume species (1-sainfoin [SAN; ' 3% condens...

  5. Steroidal Saponins in Oat Bran.

    PubMed

    Yang, Junli; Wang, Pei; Wu, Wenbin; Zhao, Yantao; Idehen, Emmanuel; Sang, Shengmin

    2016-02-24

    Saponins are one type of widespread defense compound in the plant kingdom and have been exploited for the production of lead compounds with diverse pharmacological properties in drug discovery. Oats contain two unique steroidal saponins, avenacoside A, 1, and avenacoside B, 2. However, the chemical composition, the levels of these saponins in commercial oat products, and their health effects are still largely unknown. In this study, we directly purified 5 steroidal saponins (1-5) from a methanol extract of oat bran, characterized their structures by analyzing their MS and NMR spectra, and also tentatively identified 11 steroidal saponins (6-16) on the basis of their tandem mass spectra (MS(n), n = 2-3). Among the five purified saponins, 5 is a new compound and 4 is purified from oats for the first time. Using HPLC-MS techniques, a complete profile of oat steroidal saponins was determined, and the contents of the two primary steroidal saponins, 1 and 2, were quantitated in 15 different commercial oat products. The total levels of these two saponins vary from 49.6 to 443.0 mg/kg, and oat bran or oatmeal has higher levels of these two saponins than cold oat cereal. Furthermore, our results on the inhibitory effects of 1 and 2 against the growth of human colon cancer cells HCT-116 and HT-29 showed that both had weak activity, with 2 being more active than 1. PMID:26852819

  6. Saponins from Barringtonia acutangula.

    PubMed

    Pal, B C; Chaudhuri, T; Yoshikawa, K; Arihara, S

    1994-03-30

    Three monodesmosidic glucuronide saponins of barringtogenol C, named barringtosides A, B and C have been isolated as their methyl esters from the dried seeds of Barringtonia acutangula. On the basis of chemical and spectral evidence, the structures of these new saponins were elucidated to be as follows: barringtoside A, 3-O-beta-D-xylopyranosyl(1-->3)-[beta-D-galactopyranosyl(1-->2)]-beta-D- glucuronopyranosyl barringtogenol C; barringtoside B, 3-O-beta-D-xylopyranosyl(1-->3)-]beta-D-galactopyranosyl(1-->2)]-beta-D- glucuronopyranosyl-21-O-tigloyl-28-O-isobutyryl barringtogenol C; barringtoside C, 3-O-alpha-L-arabinopyranosyl(1-->3)-[beta-D-galactopyranosyl(1-->2 )]-beta-D - glucuronopyranosyl barringtogenol C. PMID:7764822

  7. Saponins from Fagonia glutinosa.

    PubMed

    Melek, F R; Miyase, T; el-Gindy, M R; Abdel-Khalik, S M; Ghaly, N S; el-Kady, M

    2000-10-01

    Twelve triterpenoid saponins, including six new, were isolated and identified from the aerial parts of Fagonia glutinosa. The new saponins were characterised as 3-O-[beta-D-glucopyranosyl(1-->2)][beta-D-glucopyranosyl(1-->3)]-alpha-L - arabinopyranosyl-27-hydroxy oleanolic acid 28-O-beta-D-glucopyranosyl ester, 3-O-[beta-D-glucopyranosyl(1-->3)]-alpha-L-arabinopyranosyl ursolic acid, 3-O-alpha-L-arabinopyranosyl ursolic acid 28-O-beta-D-glucopyranosyl ester, 3-O-[beta-D-xylopyranosyl(1-->2)][beta- D-glucopyranosyl(1-->3)]-alpha-L-arabinopyranosyl ursolic acid, 3-O-[beta-D-glucopyranosyl(1-->2)][beta-D- glucopyranosyl(1-->3)]-alpha-L-arabinopyranosyl ursolic acid 28-O-beta-D-glucopyranosyl ester and 3-O-[beta-D-glucopyranosyl(1-->2)][beta-D-glucopyranosyl(1-->3)]-alpha-L - arabinopyranosyl-27-hydroxy ursolic acid 28-O-beta-D-glucopyranosyl ester. The structures of the saponins were established by spectral and chemical evidences. The assignments of the NMR signals were performed by means of HOHAHA, 1H-1H COSY, ROE, HMQC and HMBC experiments. PMID:11082842

  8. Tannin (Polyphenol) Stability in Aqueous Solutions

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Understanding the chemical stability of tannins (polyphenolics) in soils is critical to understanding their biological activities and fate. We examined the stability of chemically defined tannins in aqueous solutions under conditions simulating natural and laboratory conditions. We evaluated tanni...

  9. Saponins from Fagonia arabica.

    PubMed

    Miyase, T; Melek, F R; El-Gindi, O D; Abdel-Khalik, S M; El-Gindi, M R; Haggag, M Y; Hilal, S H

    1996-03-01

    Seven new triterpenoid saponins were isolated and identified from the aerial parts of Fagonia arabica. They were characterized as 3-O-beta-D-xylopyranosyl(1-->2)-[beta-D-glucopyranosyl(1-->3)]-alpha-L- arabinopyranosyl oleanolic acid 28-O-beta-D-glucopyranoside, 3-O-beta-D-glucopyranosyl(1-->2)-[beta-D-glucopyranosyl(1-->3)]-alpha-L- arabino pyranosyl oleanolic acid 28-O-beta-D-glucopyranoside, 3-O-beta-D-xylopyranosyl(1-->2)-[beta-D-glucopyranosyl (1-->3)]-alpha- L-arabinopyranosyl oleanolic acid, 3-O-beta-D-glucopyranosyl(1-->2)-[beta-D-glucopyranosyl(1-->3)]-alpha-L- arabino pyranosyl oleanolic acid, 3-O-beta-D-xylopyranosyl(1-->2)-[beta-D-glucopyranosyl (1-->3)]-alpha-L-arabinopyranosyl 27-hydroxyoleanolic acid, 28-O-beta-D-glucopyranoside, 3-O-beta-D-xylopyranosyl(1-->2)-[beta-D-glucopyranosyl(1-->3)]-alpha-L- arabinopyranosyl ursolic acid 28-O-beta-D-glucopyranoside and 3-O-beta-D-xylopyranosyl (1-->2)-[beta-D-glucopyranosyl (1-->3)-alpha-L-arabinopyranosyl 27-hydroxyursolic acid 28-O-beta-D-glucopyranoside. The structures of the saponins were established by analyses of their 1H and 13C NMR spectra with the aid of 2D experiments. The two genins, 27-hydroxyoleanolic acid and 27-ursolic acid, are new. PMID:8728716

  10. Clematomandshurica saponin E, a new triterpenoid saponin from Clematis mandshurica.

    PubMed

    Dong, Fang-Yan; Cui, Guo-He; Zhang, Ying-Hua; Zhu, Ruo-Nan; Wu, Xiu-Juan; Sun, Ting-Ting; Wang, Wei

    2010-12-01

    A new triterpenoid saponin, clematomandshurica saponin E, together with four known saponins were isolated and characterized from the roots and rhizomes of Clematis mandshurica (Ranunculaceae), a commonly used traditional Chinese medicine with anti-inflammatory and antirheumatoid activities. On the basis of spectroscopic analysis, including HR-ESI-MS, IR, 1D, and 2D NMR spectral data and hydrolysis followed by chromatographic analysis, the structure of the new triterpenoid saponin was elucidated as 3-O-α-L-rhamnopyranosyl-(1 → 6)-β-D-glucopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 4)-β-D-ribopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl oleanolic acid 28-O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranoside. PMID:21128147

  11. Triterpenoidal saponins from Madhuca butyracea.

    PubMed

    Nigam, S K; Li, X C; Wang, D Z; Misra, G; Yang, C R

    1992-09-01

    Two new triterpenoidal saponins, butyrosides A and B, were isolated from the seeds of Madhuca butyracea, along with two known saponins, Mi-saponin A and 16 alpha-hydroxy Mi-saponin A. On the basis of chemical and spectroscopic evidence, the structures of butyrosides A and B were established to be 3-O-beta-D-glucopyranosyl protobassic acid 28-O-beta-D-apiofuranosyl(1----3)-beta-D-xylopyranosyl (----4)-alpha-L-rhamnopyranosyl(1----2)-alpha-L-arabinopyranoside and 3-O-beta-D-glucopyranosyl 16 alpha-hydroxy protobassic acid 28-O-beta-D-apiofuranosyl(1----3)-beta-D-xylopyranosyl (1----4)-alpha-L-rhamnopyranosyl(1----2)-alpha-L-arabinopyranoside , respectively. PMID:1368412

  12. Two Faces of Alkaloids

    NASA Astrophysics Data System (ADS)

    Dostál, Jirí

    2000-08-01

    Alkaloids can occur in two forms, denoted as ammonium salts and free bases. These forms differ substantially in their properties and in some cases in their structures. The article discusses and compares the salts and free bases of six well-known alkaloids: nicotine, morphine, cocaine, sanguinarine, allocryptopine, and magnoflorine. Relevance for the biological and medical uses of these compounds is emphasized.

  13. Amaryllidaceae and Sceletium alkaloids.

    PubMed

    Jin, Zhong

    2013-06-01

    Covering: July 2010 to June 2012. Previous review: Nat. Prod. Rep., 2011, 28, 1126-1142. Recent progress on the isolation, identification, biological activity and synthetic studies of structurally diverse alkaloids from plants of the family Amaryllidaceae is summarized in this review. In addition, the structurally related alkaloids isolated from Sceletium species are discussed as well. PMID:23644557

  14. Alkaloids from Chasmanthera dependens.

    PubMed

    Ohiri, F C; Verpoorte, R; Baerheim Svendsen, A

    1982-12-01

    A phytochemical investigation of the stem of Chasmanthera dependens Hochst led to the isolation and identification of five quaternary alkaloids: jatrorrhizine, columbamine, pseudocolumbamine, magnoflorine and palmatine and nine tertiary non-phenolic alkaloids: tetrahydropalmatine, liriodenine, lysicamine, oxoglaucine, glaucine, anonaine, nornuciferine, norglaucine and O,O-dimethylcorytuberine. PMID:17396979

  15. Anthocyanins influence tannin-cell wall interactions.

    PubMed

    Bautista-Ortín, Ana Belén; Martínez-Hernández, Alejandro; Ruiz-García, Yolanda; Gil-Muñoz, Rocío; Gómez-Plaza, Encarna

    2016-09-01

    The rate of tannin extraction was studied in a vinification of red grapes and the results compared with another vinification made with white grapes fermented as for typical red wine, in the presence of skins and seeds. Even though the grapes presented a quite similar skin and seed tannin content, the differences in tannin concentration between both vinifications was very large, despite the fact that the only apparent difference between the phenolic composition of both wines was the anthocyanin content. This suggests that anthocyanins play an important role in tannin extractability, perhaps because they affect the extent of the tannin-cell wall interaction, a factor that largely controls the resulting quantity of tannins in wines. To confirm this observation, the effect of anthocyanins on the tannin extractability from grape seeds and skin and on the interaction between tannins and grape cell walls suspended in model solutions were studied. The results indicated that anthocyanins favored skin and seed tannin extraction and that there is a competition for the adsorption sites between anthocyanins and tannins that increases the tannin content when anthocyanins are present. PMID:27041322

  16. Furostanol and Spirostanol Saponins from Tribulus terrestris.

    PubMed

    Wang, Zhen-Fang; Wang, Bing-Bing; Zhao, Yang; Wang, Fang-Xu; Sun, Yan; Guo, Rui-Jie; Song, Xin-Bo; Xin, Hai-Li; Sun, Xin-Guang

    2016-01-01

    Twelve new steroidal saponins, including eleven furostanol saponins, terrestrinin J-T (1-11), and one spirostanol saponin, terrestrinin U (12), together with seven known steroidal saponins 13-19 were isolated from T. terrestris. The structures of the new compounds were established on the basis of spectroscopic data, including 1D and 2D NMR and HRESIMS, and comparisons with published data. PMID:27043512

  17. Saponins as cytotoxic agents: a review

    PubMed Central

    Galanty, Agnieszka; Sobolewska, Danuta

    2010-01-01

    Saponins are natural glycosides which possess a wide range of pharmacological properties including cytotoxic activity. In this review, the recent studies (2005–2009) concerning the cytotoxic activity of saponins have been summarized. The correlations between the structure and the cytotoxicity of both steroid and triterpenoid saponins have been described as well as the most common mechanisms of action. PMID:20835386

  18. Dimeric Cinchona alkaloids.

    PubMed

    Boratyński, Przemysław J

    2015-05-01

    Nature is full of dimeric alkaloids of various types from many plant families, some of them with interesting biological properties. However, dimeric Cinchona alkaloids were not isolated from any species but were products of designed partial chemical synthesis. Although the Cinchona bark is amongst the sources of oldest efficient medicines, the synthetic dimers found most use in the field of asymmetric synthesis. Prominent examples include the Sharpless dihydroxylation and aminohydroxylation ligands, and dimeric phase transfer catalysts. In this article the syntheses of Cinchona alkaloid dimers and oligomers are reviewed, and their structure and applications are outlined. Various synthetic routes exploit reactivity of the alkaloids at the central 9-hydroxyl group, quinuclidine, and quinoline rings, as well as 3-vinyl group. This availability of reactive sites, in combination with a plethora of linker molecules, contributes to the diversity of the products obtained. PMID:25586655

  19. Tannins, Peptic Ulcers and Related Mechanisms

    PubMed Central

    de Jesus, Neyres Zinia Taveira; de Souza Falcão, Heloina; Gomes, Isis Fernandes; de Almeida Leite, Thiago Jose; de Morais Lima, Gedson Rodrigues; Barbosa-Filho, Jose Maria; Tavares, Josean Fechine; da Silva, Marcelo Sobral; de Athayde-Filho, Petrônio Filgueiras; Batista, Leonia Maria

    2012-01-01

    This review of the current literature aims to study correlations between the chemical structure and gastric anti-ulcer activity of tannins. Tannins are used in medicine primarily because of their astringent properties. These properties are due to the fact that tannins react with the tissue proteins with which they come into contact. In gastric ulcers, this tannin-protein complex layer protects the stomach by promoting greater resistance to chemical and mechanical injury or irritation. Moreover, in several experimental models of gastric ulcer, tannins have been shown to present antioxidant activity, promote tissue repair, exhibit anti Helicobacter pylori effects, and they are involved in gastrointestinal tract anti-inflammatory processes. The presence of tannins explains the anti-ulcer effects of many natural products. PMID:22489149

  20. Occurrence of halogenated alkaloids.

    PubMed

    Gribble, Gordon W

    2012-01-01

    Once considered to be isolation artifacts or chemical "mistakes" of nature, the number of naturally occurring organohalogen compounds has grown from a dozen in 1954 to >5000 today. Of these, at least 25% are halogenated alkaloids. This is not surprising since nitrogen-containing pyrroles, indoles, carbolines, tryptamines, tyrosines, and tyramines are excellent platforms for biohalogenation, particularly in the marine environment where both chloride and bromide are plentiful for biooxidation and subsequent incorporation into these electron-rich substrates. This review presents the occurrence of all halogenated alkaloids, with the exception of marine bromotyrosines where coverage begins where it left off in volume 61 of The Alkaloids. Whereas the biological activity of these extraordinary compounds is briefly cited for some examples, a future volume of The Alkaloids will present full coverage of this topic and will also include selected syntheses of halogenated alkaloids. Natural organohalogens of all types, especially marine and terrestrial halogenated alkaloids, comprise a rapidly expanding class of natural products, in many cases expressing powerful biological activity. This enormous proliferation has several origins: (1) a revitalization of natural product research in a search for new drugs, (2) improved compound characterization methods (multidimensional NMR, high-resolution mass spectrometry), (3) specific enzyme-based and other biological assays, (4) sophisticated collection methods (SCUBA and remote submersibles for deep ocean marine collections), (5) new separation and purification techniques (HPLC and countercurrent separation), (6) a greater appreciation of traditional folk medicine and ethobotany, and (7) marine bacteria and fungi as novel sources of natural products. Halogenated alkaloids are truly omnipresent in the environment. Indeed, one compound, Q1 (234), is ubiquitous in the marine food web and is found in the Inuit from their diet of whale

  1. Marine Indole Alkaloids

    PubMed Central

    Netz, Natalie; Opatz, Till

    2015-01-01

    Marine indole alkaloids comprise a large and steadily growing group of secondary metabolites. Their diverse biological activities make many compounds of this class attractive starting points for pharmaceutical development. Several marine-derived indoles were found to possess cytotoxic, antineoplastic, antibacterial and antimicrobial activities, in addition to the action on human enzymes and receptors. The newly isolated indole alkaloids of marine origin since the last comprehensive review in 2003 are reported, and biological aspects will be discussed. PMID:26287214

  2. Marine Indole Alkaloids.

    PubMed

    Netz, Natalie; Opatz, Till

    2015-08-01

    Marine indole alkaloids comprise a large and steadily growing group of secondary metabolites. Their diverse biological activities make many compounds of this class attractive starting points for pharmaceutical development. Several marine-derived indoles were found to possess cytotoxic, antineoplastic, antibacterial and antimicrobial activities, in addition to the action on human enzymes and receptors. The newly isolated indole alkaloids of marine origin since the last comprehensive review in 2003 are reported, and biological aspects will be discussed. PMID:26287214

  3. Sarpagine and related alkaloids

    PubMed Central

    Namjoshi, Ojas A.; Cook, James M.

    2016-01-01

    The sarpagine-related macroline and ajmaline alkaloids share a common biosynthetic origin, and bear important structural similarities, as expected. These indole alkaloids are widely dispersed in 25 plant genera, principally in the Apocynaceae family. Very diverse and interesting biological properties have been reported for this group of natural products. Isolation of new sarpagine-related alkaloids as well as the asymmetric synthesis of these structurally complex molecules are of paramount importance to the synthetic and medicinal chemists. A total of 115 newly isolated sarpagine-related macroline and ajmaline alkaloids, along with their physicochemical properties have been included in this chapter. A general and efficient strategy for the synthesis of these monomeric alkaloids, as well as bisindoles has been presented, which involves application of the asymmetric Pictet–Spengler reaction (>98% ee) as a key step because of the ease of scale up of the tetracyclic template. Also included in this chapter are the syntheses of the sarpagine-related alkaloids, published since the year 2000. PMID:26827883

  4. Variability in tannin content, chemistry and activity in a diverse group of tannin containing sorghum cultivars

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Tannins are large polyphenolic polymers and are known to bind proteins, limiting their digestibility. Tannins are also known for having excellent antioxidant potential. To examine the precise impact of tannin content and composition on the biological activities (protein binding, protein digestibil...

  5. Preference for tannin-containing supplements by sheep consuming endophyte-infected tall fescue hay.

    PubMed

    Bernard, M; Maughan, B; Villalba, J J

    2013-07-01

    Tannins may bind to alkaloids in endophyte-infected (E+) tall fescue and attenuate fescue toxicosis. To test this hypothesis, thirty-two 4-mo-old lambs were randomly assigned to 4 treatments (8 lambs/treatment) in a 2 by 2 factorial design that included a basal diet of tall fescue hay [E+ or endophyte-free (E-)] supplemented with (TS) or without (CS) bioactive Quebracho tannins. The concentration of ergovaline in E+ fed in 2 successive phases was 65 ± 21 µg/kg (Phase 1) and 128 ± 4 µg/kg (Phase 2). After exposure to hays and supplements, all lambs were offered choices between TS and CS and between E+ and E- hays. During Phase 1, lambs offered E+ consumed more hay than lambs offered E- (P = 0.03). Lambs on E+/TS displayed the greatest intake of hay and the least intake of TS (P < 0.05). During Phase 2, when the concentration of ergovaline increased, lambs offered E+ consumed less hay than lambs fed E- (P < 0.0001). Lambs on E+/CS consumed less hay than lambs on E-/CS (P = 0.02), but hay intake by lambs on E-/TS and E+/TS did not differ (P = 0.96). Lambs preferred CS to TS during preference tests (P < 0.0001) and lambs on E+/TS ingested the least amounts of supplement TS and the greatest amounts of supplement CS (P = 0.001). Lambs offered E+ displayed greater body temperatures than lambs offered E- in both phases (P < 0.05). When offered a choice among the 3 hays, lambs previously exposed to E+ preferred E+ (low content of ergovaline) > E- > E+ (greater content of ergovaline; P < 0.001). Thus, decreased concentrations of ergovaline increased rectal temperatures, and affected intake of and preference for tannins and fescue hay. Quebracho tannins did not attenuate the effects of E+ on body temperature and feed intake. Ingestion of E+ reduced intake of quebracho tannins, suggesting that alkaloids in E+ antagonized ingestion of condensed tannins. PMID:23658337

  6. Belladonna Alkaloid Combinations and Phenobarbital

    MedlinePlus

    Belladonna alkaloid combinations and phenobarbital are used to relieve cramping pains in conditions such as irritable bowel syndrome and ... Belladonna alkaloid combinations and phenobarbital come as a regular tablet, a slow-acting tablet, capsule, and liquid to take ...

  7. Cytotoxicity of Hymenocallis expansa alkaloids.

    PubMed

    Antoun, M D; Mendoza, N T; Ríos, Y R; Proctor, G R; Wickramaratne, D B; Pezzuto, J M; Kinghorn, A D

    1993-08-01

    From the bulbs and leaves of Hymenocallis expansa (Amaryllidaceae), three alkaloid constituents were identified: (+)-tazettine, (+)-hippeastrine, and (-)-haemanthidine. These alkaloids demonstrated significant cytotoxicity when tested against a panel of human and murine tumor cell lines. PMID:8229020

  8. Sorption of polyphenolics (tannins) to natural soils

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The plant secondary metabolites known as tannins (polyphenolics) comprise up to 40% of the dry mass of plant tissue. Tannins have potent bioactivities ranging from protein precipitation to metal binding and radical quenching, and can affect nutrient metal availability, nitrogen availability, and so...

  9. Sorption of polyphenolics (tannins) to natural soils

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Tannins enter soil systems via rainfall through the leaf canopy, leaf litter decomposition, and root exudation and decomposition. For tannins released into soils, the relative importance of sorption to soil; chemical reactions with soil minerals; and biological decomposition is unknown. Determinin...

  10. Colloidal stability of tannins: astringency, wine tasting and beyond

    NASA Astrophysics Data System (ADS)

    Zanchi, D.; Poulain, C.; Konarev, P.; Tribet, C.; Svergun, D. I.

    2008-12-01

    Tannin-tannin and tannin-protein interactions in water-ethanol solvent mixtures are studied in the context of red wine tasting. While tannin self-aggregation is relevant for the visual aspect of wine tasting (limpidity and related colloidal phenomena), tannin affinities for salivary proline-rich proteins is fundamental for a wide spectrum of organoleptic properties related to astringency. Tannin-tannin interactions are analyzed in water-ethanol wine-like solvents and the precipitation map is constructed for a typical grape tannin. The interaction between tannins and human salivary proline-rich proteins (PRP) are investigated in the framework of the shell model for micellization, known for describing tannin-induced aggregation of β-casein. Tannin-assisted micellization and compaction of proteins observed by SAXS are described quantitatively and discussed in the case of astringency.

  11. Biosynthesis of Fungal Indole Alkaloids

    PubMed Central

    Xu, Wei; Gavia, Diego J.; Tang, Yi

    2014-01-01

    This review provides a summary of recent research advances in elucidating the biosynthesis of fungal indole alkaloids. Different strategies used to incorporate and derivatize the indole/indoline moieties in various families of fungal indole alkaloids will be discussed, including tryptophan-containing nonribosomal peptides and polyketide-nonribosomal peptide hybrids; and alkaloids derived from other indole building blocks. This review also includes discussion regarding the downstream modifications that generate chemical and structural diversity among indole alkaloids. PMID:25180619

  12. Lycorine alkaloids from Hymenocallis littoralis.

    PubMed

    Lin, L Z; Hu, S F; Chai, H B; Pengsuparp, T; Pezzuto, J M; Cordell, G A; Ruangrungsi, N

    1995-11-01

    From Hymenocallis littoralis, one new alkaloid, named littoraline, together with 13 known lycorine alkaloids and one lignan, were isolated. The structure and NMR assignments of this new alkaloid were determined by 1D and 2D NMR techniques. Littoraline showed inhibitory activity of HIV reverse transcriptase, and lycorine and haemanthamine showed potent in vitro cytotoxicity. PMID:7492374

  13. Analysis of Ergot Alkaloids.

    PubMed

    Crews, Colin

    2015-06-01

    The principles and application of established and newer methods for the quantitative and semi-quantitative determination of ergot alkaloids in food, feed, plant materials and animal tissues are reviewed. The techniques of sampling, extraction, clean-up, detection, quantification and validation are described. The major procedures for ergot alkaloid analysis comprise liquid chromatography with tandem mass spectrometry (LC-MS/MS) and liquid chromatography with fluorescence detection (LC-FLD). Other methods based on immunoassays are under development and variations of these and minor techniques are available for specific purposes. PMID:26046699

  14. Analysis of Ergot Alkaloids

    PubMed Central

    Crews, Colin

    2015-01-01

    The principles and application of established and newer methods for the quantitative and semi-quantitative determination of ergot alkaloids in food, feed, plant materials and animal tissues are reviewed. The techniques of sampling, extraction, clean-up, detection, quantification and validation are described. The major procedures for ergot alkaloid analysis comprise liquid chromatography with tandem mass spectrometry (LC-MS/MS) and liquid chromatography with fluorescence detection (LC-FLD). Other methods based on immunoassays are under development and variations of these and minor techniques are available for specific purposes. PMID:26046699

  15. Salivary amylase induction by tannin-enriched diets as a possible countermeasure against tannins.

    PubMed

    da Costa, G; Lamy, E; Capela e Silva, F; Andersen, J; Sales Baptista, E; Coelho, A V

    2008-03-01

    Tannins are characterized by protein-binding affinity. They have astringent/bitter properties that act as deterrents, affecting diet selection. Two groups of salivary proteins, proline-rich proteins and histatins, are effective precipitators of tannin, decreasing levels of available tannins. The possibility of other salivary proteins having a co-adjuvant role on host defense mechanisms against tannins is unknown. In this work, we characterized and compared the protein profile of mice whole saliva from animals fed on three experimental diets: tannin-free diet, diet with the incorporation of 5% hydrolyzable tannins (tannic acid), or diet with 5% condensed tannins (quebracho). Protein analysis was performed by one-dimensional gel electrophoresis combined with Matrix-Assisted Laser Desorption Ionization-Time of Flight mass spectrometry to allow the dynamic study of interactions between diet and saliva. Since abundant salivary proteins obscure the purification and identification of medium and low expressed salivary proteins, we used centrifugation to obtain saliva samples free from proteins that precipitate after tannin binding. Data from Peptide Mass Fingerprinting allowed us to identify ten different proteins, some of them showing more than one isoform. Tannin-enriched diets were observed to change the salivary protein profile. One isoform of alpha-amylase was overexpressed with both types of tannins. Aldehyde reductase was only identified in saliva of the quebracho group. Additionally, a hypertrophy of parotid salivary gland acini was observed by histology, along with a decrease in body mass in the first 4 days of the experimental period. PMID:18253799

  16. Immunoassay of alkaloids

    NASA Astrophysics Data System (ADS)

    Volkov, S. K.

    1993-08-01

    A survey is presented of literature data concerning the development and applications of the immunochemical methods for the assay of alkaloids — one of the classes of physiologically active compounds of plant origin most widely used in medical practice. The bibliography includes 141 references.

  17. Alkaloids Toxic to Livestock

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Alkaloids are a specific group of nitrogen-containing natural metabolites that enable plants to overcome temporary or continuous threats integral to their environment, while also controlling essential functions of growth and reproduction. These compounds are probably produced primarily to control f...

  18. The Securinega alkaloids.

    PubMed

    Chirkin, Eqor; Atkatlian, William; Porée, François-Hugues

    2015-01-01

    Securinega alkaloids represent a family of plant secondary metabolites known for 50 years. Securinine (1), the most abundant and studied alkaloid of this series was isolated by Russian researchers in 1956. In the following years, French and Japanese scientists reported other Securinega compounds and extensive work was done to elucidate their intriguing structures. The homogeneity of this family relies mainly on its tetracyclic chemical backbone, which features a butenolide moiety (cycle D) and an azabicyclo[3.2.1]octane ring system (rings B and C). Interestingly, after a period of latency of 20 years, the Securinega topic reemerged as a prolific source of new natural structures and to date more than 50 compounds have been identified and characterized. The oligomeric subgroup gathering dimeric, trimeric, and tetrameric units is of particular interest. The unprecedented structure of the Securinega alkaloids was the subject of extensive synthetic efforts culminating in several efficient and elegant total syntheses. The botanical distribution of these alkaloids seems limited to the Securinega, Flueggea, Margaritaria, and Breynia genera (Phyllanthaceae). However, only a limited number of plant species have been considered for their alkaloid contents, and additional phytochemical as well as genetic studies are needed. Concerning the biosynthesis, experiments carried out with radiolabelled aminoacids allowed to identify lysine and tyrosine as the precursors of the piperidine ring A and the CD rings of securinine (1), respectively. Besides, plausible biosynthetic pathways were proposed for virosaine A (38) and B (39), flueggine A (46), and also the different oligomers flueggenine A-D (48-51), fluevirosinine A (56), and flueggedine (20). The case of nirurine (45) and secu'amamine (37) remains elusive and additional studies seem necessary to understand their mode of production. The scope of biological of activities of the Securinega alkaloids was mainly centered on the CNS

  19. Simple Indolizidine and Quinolizidine Alkaloids.

    PubMed

    Michael, Joseph P

    2016-01-01

    This review of simple indolizidine and quinolizidine alkaloids (i.e., those in which the parent bicyclic systems are in general not embedded in polycyclic arrays) is an update of the previous coverage in Volume 55 of this series (2001). The present survey covers the literature from mid-1999 to the end of 2013; and in addition to aspects of the isolation, characterization, and biological activity of the alkaloids, much emphasis is placed on their total synthesis. A brief introduction to the topic is followed by an overview of relevant alkaloids from fungal and microbial sources, among them slaframine, cyclizidine, Steptomyces metabolites, and the pantocins. The important iminosugar alkaloids lentiginosine, steviamine, swainsonine, castanospermine, and related hydroxyindolizidines are dealt with in the subsequent section. The fourth and fifth sections cover metabolites from terrestrial plants. Pertinent plant alkaloids bearing alkyl, functionalized alkyl or alkenyl substituents include dendroprimine, anibamine, simple alkaloids belonging to the genera Prosopis, Elaeocarpus, Lycopodium, and Poranthera, and bicyclic alkaloids of the lupin family. Plant alkaloids bearing aryl or heteroaryl substituents include ipalbidine and analogs, secophenanthroindolizidine and secophenanthroquinolizidine alkaloids (among them septicine, julandine, and analogs), ficuseptine, lasubines, and other simple quinolizidines of the Lythraceae, the simple furyl-substituted Nuphar alkaloids, and a mixed quinolizidine-quinazoline alkaloid. The penultimate section of the review deals with the sizable group of simple indolizidine and quinolizidine alkaloids isolated from, or detected in, ants, mites, and terrestrial amphibians, and includes an overview of the "dietary hypothesis" for the origin of the amphibian metabolites. The final section surveys relevant alkaloids from marine sources, and includes clathryimines and analogs, stellettamides, the clavepictines and pictamine, and bis

  20. Triterpenoid saponins from Fagonia indica.

    PubMed

    Shaker, K H; Bernhardt, M; Elgamal, M H; Seifert, K

    1999-08-01

    Two new triterpenoid saponins, 3-O-{[beta-D-glucopyranosyl-(1-->2)]-[alpha-L-arabinopyranosyl-(1- ->3)]- alpha-L-arabinopyranosyl}-ursolic acid-28-O-[beta-D-glucopyranosyl] ester (indicasaponin A), 3-O-{[beta-D-glucopyranosyl-(1-->2)]-[alpha-L-arabinopyranosyl-(1- ->3)]- alpha-L-arabinopyranosyl}-oleanolic acid-28-O-[beta-D-glucopyranosyl] ester (indicasaponin B) and two known triterpenoid saponins, 3-O-[beta-D-glucopyranosyl-(1-->3)-alpha-L-arabinopyranosyl]-ur solic acid-28-O-[beta-D-glucopyranosyl] ester, 3-O-[beta-D-glucopyranosyl-(1-->3)-alpha-L-arabinopyranosyl]-olean olic acid-28-O-[beta-D-glucopyranosyl] ester have been isolated from Fagonia indica. The structures were determined primarily by NMR spectroscopy. The assignment of NMR signals was performed by means of 1H-1H COSY, NOESY, ROESY, TOCSY, HMQC and HMBC experiments. PMID:10444859

  1. Further saponins from Fagonia cretica.

    PubMed

    Abdel-Khalik, S M; Miyase, T; Melek, F R; el-Ashaal, H A

    2001-03-01

    Three triterpenoid saponins including two new ones were isolated and identified from the aerial parts of Fagonia cretica. The new saponins were characterized as 3-O-[beta-D-xylopyranosyl(1-->2)alpha-L-arabinopyranosyl]27-hydroxyoleanolic acid 28-O-[beta-D-glucopyranosyl(1-->6)beta-D-glucopyranosyl]ester and 3 beta-O-[beta-D-xylopyranosyl(1-->2)alpha-L-arabinopyranosyl] olean-12-en-27-al-28-oic acid 28-O-[beta-D-glucopyranosyl(1-->6)beta-D-glycopyranosyl] ester. The structures were determined by spectral analyses. The NMR assignments were made by means of HOHAHA, 1H-1H COSY, HMQC, HMBC spectra and NOE studies. PMID:11265595

  2. Triterpenoid saponins from Symplocos lancifolia.

    PubMed

    Acebey-Castellon, Ivone Lucia; Voutquenne-Nazabadioko, Laurence; Doan Thi Mai, Huong; Roseau, Nathalie; Bouthagane, Naima; Muhammad, Dima; Le Magrex Debar, Elisabeth; Gangloff, Sophie C; Litaudon, Marc; Sevenet, Thierry; Hung, Nguyen Van; Lavaud, Catherine

    2011-02-25

    Three new bidesmosidic saponins (1-3) and a new ursane triterpenoid, 2α,3β,11α,23-tetrahydroxyurs-12-en-28-oic acid (4), along with seven known compounds, were isolated from a methanolic extract of the leaves of Symplocos lancifolia. The bidesmosidic saponins were found to possess the same sugar unit part, composed of two β-d-glucose moieties and one α-l-rhamnose moiety, linked to maslinic acid, arjunolic acid, and asiatic acid, respectively. Their structures were elucidated by interpretation of their 1D and 2D NMR spectra and completed by analysis of the HRESIMS data. The antibacterial activity of the isolated triterpenoids was evaluated against Staphylococcus aureus, Enterococcus faecalis, Escherichia coli, and Pseudomonas aeruginosa, and several showed activity against Gram-positive bacteria. PMID:21288041

  3. Steroidal saponins from Tribulus terrestris.

    PubMed

    Kang, Li-Ping; Wu, Ke-Lei; Yu, He-Shui; Pang, Xu; Liu, Jie; Han, Li-Feng; Zhang, Jie; Zhao, Yang; Xiong, Cheng-Qi; Song, Xin-Bo; Liu, Chao; Cong, Yu-Wen; Ma, Bai-Ping

    2014-11-01

    Sixteen steroidal saponins, including seven previously unreported compounds, were isolated from Tribulus terrestris. The structures of the saponins were established using 1D and 2D NMR spectroscopy, mass spectrometry, and chemical methods. They were identified as: 26-O-β-d-glucopyranosyl-(25R)-furost-4-en-2α,3β,22α,26-tetrol-12-one (terrestrinin C), 26-O-β-d-glucopyranosyl-(25R)-furost-4-en-22α,26-diol-3,12-dione (terrestrinin D), 26-O-β-d-glucopyranosyl-(25S)-furost-4-en-22α,26-diol-3,6,12-trione (terrestrinin E), 26-O-β-d-glucopyranosyl-(25R)-5α-furostan-3β,22α,26-triol-12-one (terrestrinin F), 26-O-β-d-glucopyranosyl-(25R)-furost-4-en-12β,22α,26-triol-3-one (terrestrinin G), 26-O-β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl-(25R)-furost-4-en-22α,26-diol-3,12-dione (terrestrinin H), and 24-O-β-d-glucopyranosyl-(25S)-5α-spirostan-3β,24β-diol-12-one-3-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside (terrestrinin I). The isolated compounds were evaluated for their platelet aggregation activities. Three of the known saponins exhibited strong effects on the induction of platelet aggregation. PMID:25172515

  4. Tannin rich peanut skins lack anthelmintic properties

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Gastrointestinal nematode (GIN) resistance to synthetic anthelmintics in small ruminants has led to the evaluation of feed sources containing naturally occurring bioactive secondary metabolites that lessen parasite activity. Plants rich in condensed tannins (CT) can have beneficial anthelmintic pro...

  5. Antimicrobial activity of tannins from Terminalia citrina.

    PubMed

    Burapadaja, S; Bunchoo, A

    1995-08-01

    Isolation of the fruit CH3OH extract of Terminalia citrina yielded five known tannins identified as corilagin (1) (3), punicalagin (2) (4), 1,3,6-tri-O-galloyl-beta-D-glucopyranose (3) (5), chebulagic acid (4) (6), and 1,2,3,4,6-penta-O-galloyl-beta-D-glucopyranose (5) (7) by comparison of their physical and spectral data with those of authentic samples. These tannins were tested for antimicrobial action. PMID:7480186

  6. Interaction of gut microflora with tannins in feeds

    NASA Astrophysics Data System (ADS)

    Goel, Gunjan; Puniya, A. K.; Aguilar, C. N.; Singh, Kishan

    2005-11-01

    Tannins (hydrolyzable and condensed) are water-soluble polyphenolic compounds that exert antinutritional effects on ruminants by forming complexes with dietary proteins. They limit nitrogen supply to animals, besides inhibiting the growth and activity of ruminal microflora. However, some gastrointestinal microbes are able to break tannin-protein complexes while preferentially degrading hydrolyzable tannins (HTs). Streptococcus gallolyticus, Lonepinella koalarum and Selenomonas ruminantium are the dominant bacterial species that have the ability to degrade HTs. These tanninolytic microorganisms possess tannin-degrading ability and have developed certain mechanisms to tolerate tannins in feeds. Hence, selection of efficient tanninolytic microbes and transinoculation among animals for long-term benefits become areas of intensive interest. Here, we review the effects of tannins on ruminants, the existence and significance of tannin-degrading microorganisms in diverse groups of animals and the mechanisms that tannin-degrading microorganisms have developed to counter the toxic effects of tannin.

  7. 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. PMID:27262876

  8. Antifungal Activity of C-27 Steroidal Saponins

    PubMed Central

    Yang, Chong-Ren; Zhang, Ying; Jacob, Melissa R.; Khan, Shabana I.; Zhang, Ying-Jun; Li, Xing-Cong

    2006-01-01

    As part of our search for new antifungal agents from natural resources, 22 C-27 steroidal saponins and 6 steroidal sapogenins isolated from several monocotyledonous plants were tested for their antifungal activity against the opportunistic pathogens Candida albicans, Candida glabrata, Candida krusei, Cryptococcus neoformans, and Aspergillus fumigatus. The results showed that the antifungal activity of the steroidal saponins was associated with their aglycone moieties and the number and structure of monosaccharide units in their sugar chains. Within the 10 active saponins, four tigogenin saponins (compounds 1 to 4) with a sugar moiety of four or five monosaccharide units exhibited significant activity against C. neoformans and A. fumigatus, comparable to the positive control amphotericin B. The antifungal potency of these compounds was not associated with cytotoxicity to mammalian cells. This suggests that the C-27 steroidal saponins may be considered potential antifungal leads for further preclinical study. PMID:16641439

  9. Quinolizidine alkaloids from Lupinus lanatus

    NASA Astrophysics Data System (ADS)

    Neto, Alexandre T.; Oliveira, Carolina Q.; Ilha, Vinicius; Pedroso, Marcelo; Burrow, Robert A.; Dalcol, Ionara I.; Morel, Ademir F.

    2011-10-01

    In this study, one new quinolizidine alkaloid, lanatine A ( 1), together with three other known alkaloids, 13-α- trans-cinnamoyloxylupanine ( 2), 13-α-hydroxylupanine ( 3), and (-)-multiflorine ( 4) were isolated from the aerial parts of Lupinus lanatus (Fabaceae). The structures of alkaloids 1- 4 were elucidated by spectroscopic data analysis. The stereochemistry of 1 was determined by single crystal X-ray analysis. Bayesian statistical analysis of the Bijvoet differences suggests the absolute stereochemistry of 1. In addition, the antimicrobial potential of alkaloids 1- 4 is also reported.

  10. Interaction between a tannin-containing legume and endophyte-infected tall fescue seed on lambs' feeding behavior and physiology.

    PubMed

    Villalba, J J; Spackman, C; Goff, B M; Klotz, J L; Griggs, T; MacAdam, J W

    2016-02-01

    It was hypothesized that a tannin-rich legume such as sainfoin attenuates the negative postingestive effects of ergot alkaloids in tall fescue. Thirty-two 4-mo-old lambs were individually penned and randomly assigned to a 2 × 2 factorial arrangement with 2 legume species, sainfoin (SAN; 2.9% condensed tannins) or cicer milkvetch (CIC; without tannins) and a mixed ration containing tall fescue seed (50:30:20 seed:beet pulp:alfalfa) with 2 levels of endophyte infection (endophyte-infected tall fescue seed [E+; 3,150 ug/L ergovaline] or endophyte-free tall fescue seed [E-]). For a 10-d baseline period, half of the lambs were fed SAN and half were fed CIC and all lambs had ad libitum amounts of E-. In an ensuing 10-d experimental period, the protocol was the same except half of the lambs fed SAN or CIC received E+ instead of E-. Subsequently, all lambs could choose between their respective legume and seed-containing ration and between E+ and E-. Finally, an in vitro radial diffusion assay was conducted to determine whether tannins isolated from SAN would bind to alkaloids isolated from E+. All groups consumed similar amounts of E- during baseline period ( > 0.10), but lambs ate more E- than E+ during the experimental period ( < 0.05) and lambs offered SAN ate more E+ than lambs offered CIC ( < 0.05). Groups fed E- during the baseline and experimental periods had similar rectal temperatures ( > 0.10), but lambs fed E+ had lower rectal temperatures per gram of feed ingested when supplemented with SAN than with CIC ( < 0.05). Lambs fed E+ had greater concentrations of hemoglobin and more red blood cells than lambs fed E- ( < 0.05), but plasmatic concentrations of cortisol and prolactin did not differ among treatments ( > 0.10). All lambs preferred their treatment ration over their treatment legume, but lambs in the SAN and E+ treatment ate more legume + ration than lambs in the CIC and E+ (CIC-E+; < 0.05) treatment. All lambs preferred E- over E+, but lambs in the CIC

  11. Surface shear rheology of saponin adsorption layers.

    PubMed

    Golemanov, Konstantin; Tcholakova, Slavka; Denkov, Nikolai; Pelan, Edward; Stoyanov, Simeon D

    2012-08-21

    Saponins are a wide class of natural surfactants, with molecules containing a rigid hydrophobic group (triterpenoid or steroid), connected via glycoside bonds to hydrophilic oligosaccharide chains. These surfactants are very good foam stabiliziers and emulsifiers, and show a range of nontrivial biological activities. The molecular mechanisms behind these unusual properties are unknown, and, therefore, the saponins have attracted significant research interest in recent years. In our previous study (Stanimirova et al. Langmuir 2011, 27, 12486-12498), we showed that the triterpenoid saponins extracted from Quillaja saponaria plant (Quillaja saponins) formed adsorption layers with unusually high surface dilatational elasticity, 280 ± 30 mN/m. In this Article, we study the shear rheological properties of the adsorption layers of Quillaja saponins. In addition, we study the surface shear rheological properties of Yucca saponins, which are of steroid type. The experimental results show that the adsorption layers of Yucca saponins exhibit purely viscous rheological response, even at the lowest shear stress applied, whereas the adsorption layers of Quillaja saponins behave like a viscoelastic two-dimensional body. For Quillaja saponins, a single master curve describes the data for the viscoelastic creep compliance versus deformation time, up to a certain critical value of the applied shear stress. Above this value, the layer compliance increases, and the adsorption layers eventually transform into viscous ones. The experimental creep-recovery curves for the viscoelastic layers are fitted very well by compound Voigt rheological model. The obtained results are discussed from the viewpoint of the layer structure and the possible molecular mechanisms, governing the rheological response of the saponin adsorption layers. PMID:22830458

  12. Reducing methane production by supplementation of Terminalia chebula RETZ. containing tannins and saponins.

    PubMed

    Anantasook, Nirawan; Wanapat, Metha; Gunun, Pongsatorn; Cherdthong, Anusorn

    2016-06-01

    This study investigates the effects of Terminalia chebula Retz. meal supplementation on rumen fermentation and methane (CH4 ) production by using an in vitro gas technique. The experimental design was a completely randomized design (CRD) and the dietary treatments were T. chebula supplementation at 0, 4, 8, 12, 16 and 20 mg with 0.5 g of roughage and concentrate ratio at 60:40. The results revealed that cumulative gas production (96 h of incubation) were higher (P < 0.01) with T. chebula supplementation at 12, 16 and 20 mg than other treatments. However, in vitro dry matter degradability (IVDMD) and in vitro organic matter digestibility (IVOMD) were not significantly different among treatments (P > 0.05). The NH3 -N concentrations tended to quadratically increase with increasing levels of T. chebula in the diet. In addition, total volatile fatty acids (VFA) and propionate concentrations were increased (P < 0.01), while acetate concentration, acetate-to-propionate ratio, CH4 production and protozoal populations were decreased (P < 0.01) when supplemented with T. chebula at 8, 12 and 16 mg, respectively. Based on this study, it could be concluded that supplementation of T. chebula at 12 mg could improve rumen fermentation by reducing CH4 production and protozoa populations, thus improving in vitro gas production and VFA profiles. PMID:27255184

  13. Triterpenoid saponins from Madhuca butyracea.

    PubMed

    Li, X C; Liu, Y Q; Wang, D Z; Yang, C R; Nigam, S K; Misra, G

    1994-10-01

    Further investigation of the seeds of Madhuca butyracea yielded two new triterpenoid saponins, namely butyrosides C and D whose structures were established by means of chemical and spectral analyses as 3-O-beta-D-glucuronopyranosyl protobassic acid 28-O-alpha-L-rhamnopyranosyl(1-->3)-beta-D- xylopyranosyl(1-->4)-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopy ranoside and 3-O-beta-D-glucuronopyranosyl 16 alpha-hydroxy protobassic acid 28-O-beta-D-apiofuranosyl(1-->3)-beta-D-xylopyranosyl(1-->4)-alpha -L- rhamnopyranosyl(1-->2)-alpha-L-arabinopyranoside, respectively. PMID:7765693

  14. Bioactive saponins from Dioscorea futschauensis.

    PubMed

    Liu, H W; Hu, K; Zhao, Q C; Cui, C B; Kobayashi, H; Yao, X S

    2002-08-01

    A new anti-neoplastic spirostanol saponin, (25S)-spirost-5-en-3 beta, 27-diol-3O-[alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl (1-->3)]-beta-D-glucopyranoside and three known compounds viz. prosapogenin A of dioscin, dioscin and gracilin were isolated from Dioscorea futschauensis by bioactivity-guided fractionation. Their structures were elucidated mainly by means of spectroscopic analysis. Their bioactivity against Pyricularia oryzae and cytotoxic activity on ts-FT210 cell line was evaluated. PMID:12227201

  15. Chestnut bark tannin assays and growth of chestnut blight fungus on extracted tannin.

    PubMed

    Anagnostakis, S L

    1992-08-01

    Tannins extracted from the green bark of each of two Chinese, Japanese, and American chestnut trees were assayed in a protein-binding test. Four levels of tannins were added to a buffered, minimal growth medium, and a standard, virulent strain of the chestnut blight fungus was grown. There were only slight differences in protein binding between the extracts from different species. Fungal growth was better with tannin than without, but there was no difference between species extracts in their ability to improve fungal growth rate. There was also no inhibition of blight fungus growth by any of the tree tannins, so tannin toxicity is not the reason for Asian chestnut tree resistance. PMID:24254212

  16. Dammarane saponins from Zizyphus lotus.

    PubMed

    Renault, J H; Ghedira, K; Thepenier, P; Lavaud, C; Zeches-Hanrot, M; Le Men-Olivier, L

    1997-04-01

    Four dammarane-type saponins were isolated by means of centrifugal partition chromatography from the root bark of Zizyphus lotus. Their structures were elucidated using a combination of 1D and 2D 1H and 13C NMR spectra and mass spectroscopy. One of these glycosides is the known jujuboside A. The others are three new dammarane saponins, identified as 3-O-beta-D-glucopyranosyl(1-->6)-beta-D-glucopyranosyl (1-->3)-[alpha-L-rhamnopyranosyl(1-->2)]-alpha-L-arabinopyranosyl jujubogenin = jujuboside C, 3-O-alpha-L-rhamnopyranosyl (1-->2)-[beta-D-glucopyranosyl(1-->3)]-beta-D-galactopyranosyl lotogenin = lotoside I, and 3-O-alpha-L-rhamnopyranosyl(1-->2)-[beta-D-glucopyranosyl (1-->3)]-beta-D-glucopyranosyl lotogenin = lotoside II. Lotogenin is a new dammarane derivative identified as (15R, 16R, 20R, 22R)-16 beta, 22-epoxydammar-24-ene-3 beta, 15 alpha, 16 alpha, 20 beta-tetraol. PMID:9115699

  17. Triterpenoid saponins from Fagonia cretica.

    PubMed

    Abdel Khalik, S M; Miyase, T; El-Ashaal, H A; Melek, F R

    2000-08-01

    Four new triterpenoid saponins were isolated and identified from the aerial parts of Fagonia cretica. They were characterized as 3-O-[beta-D-glucopyranosyl (1-->2)-alpha-L-arabinopyranosyl] hederagenin 28-O-beta-D-glucopyranosyl ester, 3-O-[beta-D-glucopyranosyl (1-->2)-alpha-L-arabinopyranosyl] oleanolic acid 28-O-[beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosyl] ester, 3-O-[beta-D-glucopyranosyl (1-->2)-alpha-L-arabinopyranosyl] 27-hydroxy oleanolic acid 28-O-[beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosyl] ester and 3beta-O-[beta-D-glucopyranosyl (1-->2)-alpha-L-arabinopyranosyl] olean-12-en-27-al-28-oic acid 28-O-[beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosyl] ester. The structures of the saponins were assigned by spectral analyses (FABMS, 1H, 13C NMR, 1H-1H COSY, TOCSY, HMQC and HMBC spectra) and NOE experiments. To the best of our knowledge the genin 3beta hydroxy olean-12-en-27-al-28-oic acid is new. PMID:11014278

  18. The Veratrum and Solanum alkaloids.

    PubMed

    Heretsch, Philipp; Giannis, Athanassios

    2015-01-01

    This survey on steroidal alkaloids of the Veratrum and Solanum family isolated between 1974 and 2014 includes 187 compounds and 197 references. New developments in the chemistry and biology of this family of natural products with a special focus on the medicinal relevance of the jervanine alkaloid cyclopamine are discussed. PMID:25845062

  19. Accumulation of uranium by immobilized persimmon tannin

    SciTech Connect

    Sakaguchi, Takashi; Nakajima, Akira )

    1994-01-01

    We have discovered that the extracted juice of unripe astringent persimmon fruit, designated as kakishibu or shibuol, has an extremely high affinity for uranium. To develop efficient adsorbents for uranium, we tried to immobilize kakishibu (persimmon tannin) with various aldehydes and mineral acids. Persimmon tannin immobilized with glutaraldehyde can accumulate 1.71 g (14 mEq U) of uranium per gram of the adsorbent. The uranium accumulating capacity of this adsorbent is several times greater than that of commercially available chelating resins (2-3 mEq/g). Immobilized persimmon tannin has the most favorable features for uranium recovery; high selective adsorption ability, rapid adsorption rate, and applicability in both column and batch systems. The uranium retained on immobilized persimmon tannin can be quantitatively and easily eluted with a very dilute acid, and the adsorbent can thus be easily recycled in the adsorption-desorption process. Immobilized persimmon tannin also has a high affinity for thorium. 23 refs., 13 figs., 7 tabs.

  20. Automatic alkaloid removal system.

    PubMed

    Yahaya, Muhammad Rizuwan; Hj Razali, Mohd Hudzari; Abu Bakar, Che Abdullah; Ismail, Wan Ishak Wan; Muda, Wan Musa Wan; Mat, Nashriyah; Zakaria, Abd

    2014-01-01

    This alkaloid automated removal machine was developed at Instrumentation Laboratory, Universiti Sultan Zainal Abidin Malaysia that purposely for removing the alkaloid toxicity from Dioscorea hispida (DH) tuber. It is a poisonous plant where scientific study has shown that its tubers contain toxic alkaloid constituents, dioscorine. The tubers can only be consumed after it poisonous is removed. In this experiment, the tubers are needed to blend as powder form before inserting into machine basket. The user is need to push the START button on machine controller for switching the water pump ON by then creating turbulence wave of water in machine tank. The water will stop automatically by triggering the outlet solenoid valve. The powders of tubers are washed for 10 minutes while 1 liter of contaminated water due toxin mixture is flowing out. At this time, the controller will automatically triggered inlet solenoid valve and the new water will flow in machine tank until achieve the desire level that which determined by ultra sonic sensor. This process will repeated for 7 h and the positive result is achieved and shows it significant according to the several parameters of biological character ofpH, temperature, dissolve oxygen, turbidity, conductivity and fish survival rate or time. From that parameter, it also shows the positive result which is near or same with control water and assuming was made that the toxin is fully removed when the pH of DH powder is near with control water. For control water, the pH is about 5.3 while water from this experiment process is 6.0 and before run the machine the pH of contaminated water is about 3.8 which are too acid. This automated machine can save time for removing toxicity from DH compared with a traditional method while less observation of the user. PMID:24783795

  1. 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

  2. Co-occurrence of tannin and tannin-less vacuoles in sensitive plants.

    PubMed

    Fleurat-Lessard, Pierrette; Béré, Emile; Lallemand, Magali; Dédaldéchamp, Fabienne; Roblin, Gabriel

    2016-05-01

    Vacuoles of different types frequently coexist in the same plant cell, but the duality of the tannin/tannin-less vacuoles observed in Mimosa pudica L. is rare. In this plant, which is characterized by highly motile leaves, the development and original features of the double vacuolar compartment were detailed in primary pulvini from the young to the mature leaf stage. In young pulvini, the differentiation of tannin vacuoles first occurred in the epidermis and progressively spread toward the inner cortex. In motor cells of nonmotile pulvini, tannin deposits first lined the membranes of small vacuole profiles and then formed opaque clusters that joined together to form a large tannin vacuole (TV), the proportion of which in the cell was approximately 45%. At this stage, transparent vacuole profiles were rare and small, but as the parenchyma cells enlarged, these profiles coalesced to form a transparent vacuole with a convexity toward the larger-sized tannin vacuole. When leaf motility began to occur, the two vacuole types reached the same relative proportion (approximately 30%). Finally, in mature cells displaying maximum motility, the large transparent colloidal vacuole (CV) showed a relative proportion increasing to approximately 50%. At this stage, the proportion of the tannin vacuole, occurring in the vicinity of the nucleus, decreased to approximately 10%. The presence of the condensed type of tannins (proanthocyanidins) was proven by detecting their fluorescence under UV light and by specific chemical staining. This dual vacuolar profile was also observed in nonmotile parts of M. pudica (e.g., the petiole and the stem). Additional observations of leaflet pulvini showing more or less rapid movements showed that this double vacuolar structure was present in certain plants (Mimosa spegazzinii and Desmodium gyrans), but absent in others (Albizzia julibrissin, Biophytum sensitivum, and Cassia fasciculata). Taken together, these observations strongly suggest that a

  3. Multifunctional porous solids derived from tannins

    NASA Astrophysics Data System (ADS)

    Celzard, Alain; Fierro, Vanessa; Pizzi, Antonio; Zhao, Weigang

    2013-03-01

    Tannins are extremely valuable, non toxic, wood extractives combining reactivity towards aldehydes, low cost, natural origin and easy handling. When polymerized in the presence of suitable chemicals including blowing agent, ultra lightweight rigid tannin-based foams are obtained. If pyrolyzed under inert gas, reticulated carbon foams having the same pore structure and the same density are obtained. The most remarkable features of tannin-based foams are the following: mechanical resistance similar to, or higher than, that of commercial phenolic foams, tuneable pore size and permeability, infusibility, very low thermal conductivity, cheapness, ecological character, high resistance to flame and to chemicals. Carbon foams have even better properties and are also electrically conducting. Consequently, various applications are suggested for organic foams: cores of sandwich composite panels, sound and shock absorbers and thermal insulators, whereas carbon foams can be used as porous electrodes, filters for molten metals and corrosive chemicals, catalyst supports and adsorbents.

  4. Synthesis and characterization of tannin grafted polycaprolactone.

    PubMed

    Song, Ping; Jiang, Suchen; Ren, Yajun; Zhang, Xue; Qiao, Tiankui; Song, Xiaofeng; Liu, Qimin; Chen, Xuesi

    2016-10-01

    Tannin and biodegradable polyester have attracted increasing interest for biomedical applications. To improve their compatibility, a novel tannin grafted polycaprolactone (TA-g-PCL) has been synthesized via ring-opening polymerization reaction. The structure of the product is characterized with FTIR, (1)H NMR and GPC. GPC results show that the experimental molecular weight is far less than the theoretical due to complicated stereo structure and large steric hindrance of tannic molecule, but the polydispersity of the product is narrow. At 115.76:1 of molar ratio of CL to tannin, molecular weight of the product reaches the maximum. Thermodynamics properties and dissolubility of TA-g-PCL are closely related to its molecular weight. With PCL molecular chain grows, TA-g-PCL changes from amorphous form to crystalline structure, and its dissolubility in chloroform is also enhanced significantly. PMID:27388129

  5. Comparison of the effect of two Quillaja bark saponin extracts on DPPC and DPPC/cholesterol Langmuir monolayers.

    PubMed

    Orczyk, Marta; Wojciechowski, Kamil

    2015-12-01

    The present study aims at comparing the effect of two commercially available Quillaja bark saponin (QBS) products on model Langmuir monolayers. Pure dipalmitoylphosphatidylcholine (DPPC) and mixed DPPC/cholesterol Langmuir monolayers were used as crude models of erythrocyte membranes in order to better understand a hemolytic activity of QBS. Both QBS products are mixtures of several saponins and non-saponin fractions, only few of which can be assigned an exact chemical structure, as shown by an HPLC analysis. Noticeable differences in the saponin profiles, and most importantly-in the content of non-saponin fractions (tannins and phenolic compounds) are probably responsible for their different adsorption behavior at the water/air interface. The lipids Langmuir monolayers were initially spread on pure water and compressed to surface pressure of 32.5 mN/m, which is believed to provide the lipid packing similar to that in real biological membranes. The water subphase was subsequently exchanged with the respective QBS solutions in the concentration range 5 × 10(-4) to 2 × 10(-1)wt%. In order to assess the resistance of the model lipid monolayers to QBS, a combination of surface pressure relaxation and surface dilatational rheology was employed. Both QBS are shown to penetrate the lipid layers without removing them, but their effect on the lipid layers' relaxation and viscoelastic dilational properties is different. The differences virtually disappear when cholesterol is present in the monolayer, especially for the DPPC/Cholesterol molar ratio between 10:9 and 4:1 (mol/mol). Despite several jumps of surface pressure, the lipid layers containing cholesterol can resist penetration of QBS. PMID:26413864

  6. Ethanol production performance of ozone treated tannin grain sorghum flour

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Grain sorghum lines containing tannins have been reported to exhibit increased resistance to drought, birds, mold, preharvest germination, and higher grain yield than non-tannin grain sorghum lines, but tannins have been considered an adverse factor in the utilization of sorghum as a feedstock for b...

  7. Tannin extracts abate ammonia emissions from dairy barn floors

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Feeding more tannin and less crude protein (CP) to dairy cows may have compound positive impacts on reducing NH3 emissions from dairy barns. Mixtures of feces-urine from lactating Holstein dairy cows (Bos taurus) fed four levels (g kg-1) of dietary tannin extract: 0 (0T), 4.5 (low tannin, LT), 9.0 (...

  8. Powdered hide model for vegetable tanning II. hydrolyzable tannin

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Vegetable tannages employ both condensed and hydrolyzable tannins. As part of our exploration of tanning mechanisms, we reported last year on interactions of the condensed tannin, quebracho, with powdered hide. In this study, the interactions of chestnut extract, a hydrolyzable tannin, with powdere...

  9. 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. PMID:24979221

  10. Biocatalysts from alkaloid producing plants.

    PubMed

    Kries, Hajo; O'Connor, Sarah E

    2016-04-01

    Metabolic pathways leading to benzylisoquinoline and monoterpene indole alkaloids in plants are revealing remarkable new reactions. Understanding of the enzymes involved in alkaloid biosynthesis provides access to a variety of applications in biocatalysis and bioengineering. In chemo-enzymatic settings, plant biocatalysts can transform medically important scaffolds. Additionally, synthetic biologists are taking alkaloid pathways as templates to assemble pathways in microorganisms that are tailored to the needs of medicinal chemistry. In light of these many recent discoveries, it is expected that plants will continue to be a source of novel biocatalysts for the foreseeable future. PMID:26773811

  11. 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. PMID:27457995

  12. Activity, purification, and analysis of condensed tannins

    Technology Transfer Automated Retrieval System (TEKTRAN)

    As a class of plant polyphenolic compounds contained in some forages (i.e., sanfoin, big trefoil, birdfoot trefoil), condensed tannins (CTs), also referred to as proanthocyanidins (PAs), exhibit a variety of biological effects on ruminants and on the dairy farm nitrogen cycle. Interest in CTs stems ...

  13. Science Study Aids 5: Tannin - Nature's Filter.

    ERIC Educational Resources Information Center

    Boeschen, John; Randall, John M.

    This publication is the fifth in a series of seven supplementary investigative materials for use in secondary science classes providing up-to-date research-related investigations. This unit is structured for grade levels 9 through 12. It is concerned with the removal of heavy divalent metals from water with the use of tannin-containing…

  14. Inoculation of tannin-degrading bacteria into novel hosts increases performance on tannin-rich diets.

    PubMed

    Kohl, Kevin D; Stengel, Ashley; Dearing, M Denise

    2016-06-01

    It has been hypothesized that herbivores host tannin-degrading bacteria (TDB) to overcome the toxic challenges posed by plant tannins. While TDB have been isolated from the guts of numerous mammals, their functional significance to their hosts has never been explicitly tested. We introduced TDB into lab rats, which do not host TDB, and measured host performance on tannin-rich diets. We first isolated three species of TDB, Escherichia coli, Bacillus subtilis and Enterococcus faecalis, from the guts of the desert woodrat (Neotoma lepida), which regularly feeds on tannin-rich plants. Then, we inoculated isolated TDB, as well as full woodrat microbial communities into laboratory rats. A control group was inoculated with sterilized woodrat faeces. Recipient lab rats were fed increasing concentrations of tannic acid, and we monitored tannic acid intake, body mass and liver damage as measured by serum alanine aminotransferase activity. Lab rats given TDB as isolates or full communities exhibited increased tannic acid intake, higher maintenance of body mass and lower indicators of liver damage compared with control animals. These differences were maintained when the trial was repeated after 6 weeks of feeding on tannin-free diets. Our results are the first to demonstrate that TDB significantly increase host performance on tannin-rich diets. PMID:25753857

  15. Interactions of Condensed Tannins with Saccharomyces cerevisiae Yeast Cells and Cell Walls: Tannin Location by Microscopy.

    PubMed

    Mekoue Nguela, Julie; Vernhet, Aude; Sieczkowski, Nathalie; Brillouet, Jean-Marc

    2015-09-01

    Interactions between grape tannins/red wine polyphenols and yeast cells/cell walls was previously studied within the framework of red wine aging and the use of yeast-derived products as an alternative to aging on lees. Results evidenced a quite different behavior between whole cells (biomass grown to elaborate yeast-derived products, inactivated yeast, and yeast inactivated after autolysis) and yeast cell walls (obtained from mechanical disruption of the biomass). Briefly, whole cells exhibited a high capacity to irreversibly adsorb grape and wine tannins, whereas only weak interactions were observed for cell walls. This last point was quite unexpected considering the literature and called into question the real role of cell walls in yeasts' ability to fix tannins. In the present work, tannin location after interactions between grape and wine tannins and yeast cells and cell walls was studied by means of transmission electron microscopy, light epifluorescence, and confocal microscopy. Microscopy observations evidenced that if tannins interact with cell walls, and especially cell wall mannoproteins, they also diffuse freely through the walls of dead cells to interact with their plasma membrane and cytoplasmic components. PMID:26223789

  16. Tannin-assisted aggregation of natively unfolded proteins

    NASA Astrophysics Data System (ADS)

    Zanchi, D.; Narayanan, T.; Hagenmuller, D.; Baron, A.; Guyot, S.; Cabane, B.; Bouhallab, S.

    2008-06-01

    Tannin-protein interactions are essentially physical: hydrophobic and hydrogen-bond-mediated. We explored the tannin-assisted protein aggregation on the case of β-casein, which is a natively unfolded protein known for its ability to form micellar aggregates. We used several tannins with specified length. Our SAXS results show that small tannins increase the number of proteins per micelle, but keeping their size constant. It leads to a tannin-assisted compactization of micelles. Larger tannins, with linear dimensions greater than the crown width of micelles, lead to the aggregation of micelles by a bridging effect. Experimental results can be understood within a model where tannins are treated as effective enhancers of hydrophobic attraction between specific sites in proteins.

  17. Alkaloids of Litsea wightiana1.

    PubMed

    Bhakuni, D S; Gupta, S

    1983-05-01

    Six aporphine alkaloids glaucine, boldine, norboldine, isoboldine, norcorydine and laurotetanine have been isolated from the ethanolic extract of the stems of LITSEA WIGHTIANA in which spasmolytic, hypothermic and blood pressure lowering activities have been confirmed. PMID:17404942

  18. Biosynthetic pathways of ergot alkaloids.

    PubMed

    Gerhards, Nina; Neubauer, Lisa; Tudzynski, Paul; Li, Shu-Ming

    2014-01-01

    Ergot alkaloids are nitrogen-containing natural products belonging to indole alkaloids. The best known producers are fungi of the phylum Ascomycota, e.g., Claviceps, Epichloë, Penicillium and Aspergillus species. According to their structures, ergot alkaloids can be divided into three groups: clavines, lysergic acid amides and peptides (ergopeptines). All of them share the first biosynthetic steps, which lead to the formation of the tetracyclic ergoline ring system (except the simplest, tricyclic compound: chanoclavine). Different modifications on the ergoline ring by specific enzymes result in an abundance of bioactive natural products, which are used as pharmaceutical drugs or precursors thereof. From the 1950s through to recent years, most of the biosynthetic pathways have been elucidated. Gene clusters from several ergot alkaloid producers have been identified by genome mining and the functions of many of those genes have been demonstrated by knock-out experiments or biochemical investigations of the overproduced enzymes. PMID:25513893

  19. Biosynthetic Pathways of Ergot Alkaloids

    PubMed Central

    Gerhards, Nina; Neubauer, Lisa; Tudzynski, Paul; Li, Shu-Ming

    2014-01-01

    Ergot alkaloids are nitrogen-containing natural products belonging to indole alkaloids. The best known producers are fungi of the phylum Ascomycota, e.g., Claviceps, Epichloë, Penicillium and Aspergillus species. According to their structures, ergot alkaloids can be divided into three groups: clavines, lysergic acid amides and peptides (ergopeptines). All of them share the first biosynthetic steps, which lead to the formation of the tetracyclic ergoline ring system (except the simplest, tricyclic compound: chanoclavine). Different modifications on the ergoline ring by specific enzymes result in an abundance of bioactive natural products, which are used as pharmaceutical drugs or precursors thereof. From the 1950s through to recent years, most of the biosynthetic pathways have been elucidated. Gene clusters from several ergot alkaloid producers have been identified by genome mining and the functions of many of those genes have been demonstrated by knock-out experiments or biochemical investigations of the overproduced enzymes. PMID:25513893

  20. Genotoxicity of pyrrolizidine alkaloids.

    PubMed

    Chen, Tao; Mei, Nan; Fu, Peter P

    2010-04-01

    Pyrrolizidine alkaloids (PAs) are common constituents of many plant species around the world. PA-containing plants are probably the most common poisonous plants affecting livestock and wildlife. They can inflict harm to humans through contaminated food sources, herbal medicines and dietary supplements. Half of the identified PAs are genotoxic and many of them are tumorigenic. The mutagenicity of PAs has been extensively studied in different biological systems. Upon metabolic activation, PAs produce DNA adducts, DNA cross-linking, DNA breaks, sister chromatid exchange, micronuclei, chromosomal aberrations, gene mutations and chromosome mutations in vivo and in vitro. PAs induced mutations in the cII gene of rat liver and in the p53 and K-ras genes of mouse liver tumors. It has been suggested that all PAs produce a set of (+/-)-6,7-dihydro-7-hydroxy-1-hydroxymethyl-5H-pyrrolizine-derived DNA adducts and similar types of gene mutations. The signature types of mutations are G : C --> T : A transversion and tandem base substitutions. Overall, PAs are mutagenic in vivo and in vitro and their mutagenicity appears to be responsible for the carcinogenesis of PAs. PMID:20112250

  1. Cytotoxic steroidal saponins from Agave sisalana.

    PubMed

    Chen, Pi-Yu; Chen, Chin-Hui; Kuo, Ching-Chuan; Lee, Tzong-Huei; Kuo, Yueh-Hsiung; Lee, Ching-Kuo

    2011-06-01

    Two new steroidal saponins, 8 and 10, along with 7 known steroidal sapogenins and saponins (1-7) and a furostanol saponin (9) were isolated from Agave sisalana Perrine ex Engelm. The structures of these two new compounds were identified and characterized by 1D and 2D NMR spectroscopy and mass spectrometry. In addition, acid hydrolysis and GC-FID were used to confirm the sugar moieties of 8 and 10. The cytotoxic effects of 1-10 on MCF-7, NCI-H460, and SF-268 cancer cells were evaluated, and among them, compound 10 proved to be the most cytotoxic with IC₅₀ values of 1.2, 3.8, and 1.5 µM, respectively. PMID:21243587

  2. Green synthesis of silver nanoparticles using tannins

    NASA Astrophysics Data System (ADS)

    Raja, Pandian Bothi; Rahim, Afidah Abdul; Qureshi, Ahmad Kaleem; Awang, Khalijah

    2014-09-01

    Colloidal silver nanoparticles were prepared by rapid green synthesis using different tannin sources as reducing agent viz. chestnut (CN), mangrove (MG) and quebracho (QB). The aqueous silver ions when exposed to CN, MG and QB tannins were reduced which resulted in formation of silver nanoparticles. The resultant silver nanoparticles were characterized using UV-Visible, X-ray diffraction (XRD), scanning electron microscopy (SEM/EDX), and transmission electron microscopy (TEM) techniques. Furthermore, the possible mechanism of nanoparticles synthesis was also derived using FT-IR analysis. Spectroscopy analysis revealed that the synthesized nanoparticles were within 30 to 75 nm in size, while XRD results showed that nanoparticles formed were crystalline with face centered cubic geometry.

  3. Intoxication of sheep with quebracho tannin extract.

    PubMed

    Hervás, G; Pérez, V; Giráldez, F J; Mantecón, A R; Almar, M M; Frutos, P

    2003-07-01

    This experiment was carried out to study the toxicity of quebracho tannin extract (containing 760 g of condensed tannins [CTs] per kg), with the aim of validating its use as a feed additive for improving the digestive utilization of protein-rich feeds. Four groups (Q(0), Q(1), Q(2) and Q(3)) of four sheep were dosed intra-ruminally once daily, for up to 21 days with, respectively, 0, 0.5, 1.5 or 3.0 g quebracho tannin extract/kg live-weight (LW). Feed intake, live-weight changes, plasma biochemistry, indicators of hepatic detoxification function, gross lesions and histopathology were examined. Animals in groups Q(0), Q(1) and Q(2) consumed all the offered feed. In contrast, feed intake was practically nil after 6 days of quebracho dosing in group Q(3), this being associated with a loss of 4.7+/-1.30 kg LW in 10 days (P<0.05). Sheep from groups Q(0), Q(1) and Q(2) remained healthy throughout the experiment. Ewes from group Q(3) became weak and depressed on day 5 and after 8 days of dosing remained recumbent. They were humanely killed after 10 days to avoid suffering. In general, neither gross lesions nor microscopical changes were observed in animals from groups Q(0), Q(1) and Q(2). However, Q(3) sheep showed striking lesions in the digestive tract (well-demarcated ulcers filled with necrotic material in the mucosa of the rumen and reticulum, distension of abomasum and small intestine, and dense mucous material in the caecum), and changes in plasma biochemistry. Cytochrome P-450 and glutathione concentrations were significantly reduced in Q(3) sheep (P<0.05). It is concluded that quebracho tannin extract is not toxic for ruminants, except in concentrations too high to be encountered under practical conditions. PMID:12859907

  4. Recovery of uranium from seawater by immobilized tannin

    SciTech Connect

    Sakaguchi, T.; Nakajima, A.

    1987-06-01

    Tannin compounds having multiple adjacent hydroxy groups have an extremely high affinity for uranium. To prevent the leaching of tannins into water and to improve the adsorbing characteristics of these compounds, the authors tried to immobilize tannins. The immobilized tannin has the most favorable features for uranium recovery; high selective adsorption ability to uranium, rapid adsorption rate, and applicability in both column and batch systems. The immobilized tannin can recover uranium from natural seawater with high efficiency. About 2530 ..mu..g uranium is adsorbed per gram of this adsorbent within 22 h. Depending on the concentration in seawater, an enrichment of up to 766,000-fold within the adsorbent is possible. Almost all uranium adsorbed is easily desorbed with a very dilute acid. Thus, the immobilized tannin can be used repeatedly in the adsorption-desorption process.

  5. Grape seed and apple tannins: emulsifying and antioxidant properties.

    PubMed

    Figueroa-Espinoza, Maria Cruz; Zafimahova, Andrea; Alvarado, Pedro G Maldonado; Dubreucq, Eric; Poncet-Legrand, Céline

    2015-07-01

    Tannins are natural antioxidants found in plant-based foods and beverages, whose amphiphilic nature could be useful to both stabilize emulsions and protect unsaturated lipids from oxidation. In this paper, the use of tannins as antioxidant emulsifiers was studied. The main parameters influencing the stability of emulsions (i.e. tannins structure and concentration, aqueous phase pH, and ionic strength) were identified and optimized. Oil in water emulsions stabilized with tannins were compared with those stabilized with two commercial emulsifying agents, poly(vinyl alcohol) (PVA) and polyoxyethylene hydrogenated castor oil. In optimized conditions, the condensed tannins allowed to obtain a stability equivalent to that of PVA. Tannins presented good antioxidant activity in oil in water emulsion, as measured by the conjugated autoxidizable triene (CAT) assay. PMID:25704681

  6. Dietary tannins improve lamb meat colour stability.

    PubMed

    Luciano, G; Monahan, F J; Vasta, V; Biondi, L; Lanza, M; Priolo, A

    2009-01-01

    Fourteen male Comisana lambs were divided into two groups at 45days of age: lambs fed a concentrate diet (C), or lambs fed the same concentrate with the addition of quebracho (Schinopsis lorentzii) tannins (T). Sheep were slaughtered at 105days of age. Lipid oxidation, colour coordinates, haem pigment concentration, and metmyoglobin percentages were measured on minced semimembranosus muscle (SM) over 14days of refrigerated storage in a high oxygen modified atmosphere. Tannin supplementation increased (P<0.01) a(∗) values and reduced (P<0.01) b(∗) values of the SM when compared to C. Lower hue angles (P<0.001) and metmyoglobin formation (P=0.07) were observed in lamb from T-fed compared to C-fed sheep during the 14-days storage period. Furthermore, feeding T resulted in greater (P<0.001) haem pigment concentrations in the SM during refrigerated storage; however, diet had no (P=0.28) effect on lipid oxidation. Therefore, including quebracho tannins in sheep diets can improve meat colour stability of fresh lamb during extended refrigerated storage. PMID:22063971

  7. 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. PMID:23088362

  8. Three new steroidal saponins from Helleborus thibetanus.

    PubMed

    Zhang, Hui; Su, Yan-Fang; Yang, Feng-Ying

    2016-08-01

    Three new steroidal saponins including two spirostanol glycosides (1-2) and one furostanol glycoside 1-sulphate (3) were isolated from the dried roots and rhizomes of Helleborus thibetanus. Structures of the compounds were determined on the basis of extensive use of 1-D and 2-D NMR experiments, together with HR-ESI-MS and IR measurements, as well as the results of acid hydrolysis. Compounds 1-2 represented steroidal saponins with an unusual substitution pattern, which possessed a double bond at C-25 and were glycosylated at 1-OH. PMID:26821553

  9. Steroidal saponins from Chlorophytum deistelianum.

    PubMed

    Tabopda, Turibio Kuiate; Mitaine-Offer, Anne-Claire; Paululat, Thomas; Delemasure, Stéphanie; Dutartre, Patrick; Ngadjui, Bonaventure Tchaleu; Lacaille-Dubois, Marie-Aleth

    2016-06-01

    Phytochemical investigation of the aerial parts of Chlorophytum deistelianum led to the isolation of four previously undescribed steroidal saponins called chlorodeistelianosides A-D with five known ones. Their structures were established mainly by extensive 1D and 2D NMR spectroscopic techniques and mass spectrometry as (25R)-3β-[(β-d-glucopyranosyl-(1→3)-[α-l-rhamnopyranosyl-(1→4)]-β-d-xylopyranosyl-(1→3)-[β-d-glucopyranosyl-(1→2)]-β-d-glucopyranosyl-(1→4)-β-d-galactopyranosyl)oxy]-5α-spirostan-12-one, (24S,25S)-24-[(β-d-glucopyranosyl)oxy]-3β-[(β-d-glucopyranosyl-(1→2)-[β-d-xylopyranosyl-(1→3)]-β-d-glucopyranosyl-(1→4)-β-d-galactopyranosyl)oxy]-5α-spirostan-12-one, (25R)-26-[(β-d-glucopyranosyl)oxy]-2α-hydroxy-22α-methoxy-5α-furostan-3β-yl β-d-glucopyranosyl-(1→2)-[β-d-xylopyranosyl-(1→3)]-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside, and (25R)-26-[(β-d-glucopyranosyl)oxy]-3β-[(β-d-glucopyranosyl-(1→2)-[β-d-xylopyranosyl-(1→3)]-β-d-glucopyranosyl-(1→4)-β-d-galactopyranosyl)oxy]-5α-furost-20(22)-en-12-one. Cytotoxicity of most compounds was evaluated against one human cancer cell line (SW480) and one rat cardiomyoblast cell line (H9c2). Among them, three known spirostane-type glycosides exhibited cytotoxicity on both cell lines with IC50 ranging from 8 to 10μM. PMID:27012932

  10. Ruminal biohydrogenation as affected by tannins in vitro.

    PubMed

    Vasta, Valentina; Makkar, Harinder P S; Mele, Marcello; Priolo, Alessandro

    2009-07-01

    The aim of the present work was to study the effects of tannins from carob (CT; Ceratonia siliqua), acacia leaves (AT; Acacia cyanophylla) and quebracho (QT; Schinopsis lorentzii) on ruminal biohydrogenation in vitro. The tannins extracted from CT, AT and QT were incubated for 12 h in glass syringes in cow buffered ruminal fluid (BRF) with hay or hay plus concentrate as a substrate. Within each feed, three concentrations of tannins were used (0.0, 0.6 and 1.0 mg/ml BRF). The branched-chain volatile fatty acids, the branched-chain fatty acids and the microbial protein concentration were reduced (P < 0.05) by tannins. In the tannin-containing fermenters, vaccenic acid was accumulated (+23 %, P < 0.01) while stearic acid was reduced ( - 16 %, P < 0.0005). The concentration of total conjugated linoleic acid (CLA) isomers in the BRF was not affected by tannins. The assay on linoleic acid isomerase (LA-I) showed that the enzyme activity (nmol CLA produced/min per mg protein) was unaffected by the inclusion of tannins in the fermenters. However, the CLA produced by LA-I (nmol/ml per min) was lower in the presence of tannins. These results suggest that tannins reduce ruminal biohydrogenation through the inhibition of the activity of ruminal micro-organisms. PMID:19063768

  11. Antimicrobial activity of benzylisoquinoline alkaloids.

    PubMed

    Villar, A; Mares, M; Rios, J L; Canton, E; Gobernado, M

    1987-04-01

    The antimicrobial in vitro activity of 14 benzylisoquinoline alkaloids was investigated by agar diffusion and agar dilution methods against several genera of microorganisms that included Streptococcus, Staphylococcus, Bacillus, Lysteria, Escherichia, Salmonella, Klebsiella, Pseudomonas, Enterobacter, Serratia, Shigella, Mycobacterium and Candida. Anolobine was the most active compound against grampositive bacteria with MIC90 between 12 and 50 mg/l; less active were anonaine, lysicamine and liriodenine. All the alkaloids of the noraporphine and oxoaporphine groups, with the exception of isopiline, showed activity against Mycobacterium phlei (MIC 6-25 mg/l). Candida albicans ATCC26555 was inhibited by anonaine, nornantenine and xylopine (MIC 3-12 mg/l). None of the alkaloids tested had a significant activity against gramnegative rods. The action against susceptible microorganisms was bactericidal. PMID:3615557

  12. A convenient method for saponin isolation in tumour therapy.

    PubMed

    Weng, Alexander; Jenett-Siems, Kristina; Schmieder, Peter; Bachran, Diana; Bachran, Christopher; Görick, Cornelia; Thakur, Mayank; Fuchs, Hendrik; Melzig, Matthias F

    2010-03-01

    Saponinum album (Merck), which is a crude mixture of saponins from Gypsophila paniculata L., was shown to improve the anti cancer therapy when used in vivo in combination with saporin-based targeted toxins. Unfortunately saponinum album cannot be used for further development since Merck has ceased its production in the 1990s. As pure saponins are mandatory for use in medical purposes we developed a convenient method for saponin isolation directly from the roots of Gypsophila paniculata L. The developed method is rapid, cheap and scaling up is also possible. By combining dialysis and HPLC three saponins were isolated in a one-step procedure. Chemical structures of the purified saponins were characterized by extensive one and two-dimensional NMR-spectroscopy and by using ESI-TOF-MS. The biological activities of the purified saponins were also investigated. The method presented herein enabled a rapid and cheap isolation of saponins for tumour therapy. PMID:20144565

  13. Structural analogues of diosgenyl saponins: synthesis and anticancer activity.

    PubMed

    Kaskiw, Matthew J; Tassotto, Mary Lynn; Mok, Mac; Tokar, Stacey L; Pycko, Roxanne; Th'ng, John; Jiang, Zi-Hua

    2009-11-15

    Saponins display various biological activities including anti-tumor activity. Recently intensive research has been focused on developing saponins for tumor therapies. The diosgenyl saponin dioscin is one of the most common steroidal saponins and exhibits potent anticancer activity in several human cancer cells through apoptosis-inducing pathways. In this paper, we describe the synthesis of several diosgenyl saponin analogues containing either a 2-amino-2-deoxy-beta-d-glucopyranosyl residue or an alpha-l-rhamnopyranosyl-(1-->4)-2-amino-2-deoxy-beta-d-glucopyranosyl residue with different acyl substituents on the amino group. The cytotoxic activity of these compounds was evaluated in MCF-7 breast cancer cells and HeLa cervical cancer cells. Structure-activity relationship studies show that the disaccharide saponin analogues are in general less active than their corresponding monosaccharide analogues. The incorporation of an aromatic nitro functionality into these saponin analogues does not exhibit significant effect on their cytotoxic activity. PMID:19819703

  14. Red Wine Tannin Structure-Activity Relationships during Fermentation and Maceration.

    PubMed

    Yacco, Ralph S; Watrelot, Aude A; Kennedy, James A

    2016-02-01

    The correlation between tannin structure and corresponding activity was investigated by measuring the thermodynamics of interaction between tannins isolated from commercial red wine fermentations and a polystyrene divinylbenzene HPLC column. Must and/or wine samples were collected throughout fermentation/maceration from five Napa Valley wineries. By varying winery, fruit source, maceration time, and cap management practice, it was considered that a reasonably large variation in commercially relevant tannin structure would result. Tannins were isolated from samples collected using low pressure chromatography and were then characterized by gel permeation chromatography and acid-catalyzed cleavage in the presence of excess phloroglucinol (phloroglucinolysis). Corresponding tannin activity was determined using HPLC by measuring the thermodynamics of interaction between isolated tannin and a polystyrene divinylbenzene HPLC column. This measurement approach was designed to determine the ability of tannins to hydrophobically interact with a hydrophobic surface. The results of this study indicate that tannin activity is primarily driven by molecular size. Compositionally, tannin activity was positively associated with seed tannins and negatively associated with skin and pigmented tannins. Although measured indirectly, the extent of tannin oxidation as determined by phloroglucinolysis conversion yield suggests that tannin oxidation at this stage of production reduces tannin activity. Based upon maceration time, this study indicates that observed increases in perceived astringency quality, if related to tannin chemistry, are driven by tannin molecular mass as opposed to pigmented tannin formation or oxidation. Overall, the results of this study give new insight into tannin structure-activity relationships which dominate during extraction. PMID:26766301

  15. Three new triterpene saponins from Clematis chinensis.

    PubMed

    Fu, Qiang; Zan, Ke; Zhao, Ming-Bo; Zhou, Si-Xiang; Shi, She-Po; Jiang, Yong; Tu, Peng-Fei

    2013-01-01

    Three new triterpene saponins, clematochinenosides H-J (1-3), were isolated from the roots and rhizomes of Clematis chinensis. Their structures were elucidated on the basis of spectroscopic means including 1D and 2D NMR experiments and hydrolysis products. PMID:23659476

  16. Soy Saponins: Current Research and Future Goals

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Saponins are a biologically active class of triterpenoid phytochemicals found in soybeans at concentrations similar to those of the isoflavones, and the role they may play in nutrition and health is not well understood. Research the functionality of these compounds in animals and humans has been ha...

  17. The alkaloid profiles of Lupinus sulphureus.

    PubMed

    Cook, Daniel; Lee, Stephen T; Gardner, Dale R; Pfister, James A; Welch, Kevin D; Green, Benedict T; Davis, T Zane; Panter, Kip E

    2009-02-25

    Lupines are common plants on the rangelands in the western United States. Lupines contain alkaloids that can be toxic and teratogenic causing congenital birth defects (crooked calf disease). One such lupine, Lupinus sulphureus, occurs in parts of Oregon, Washington, and British Columbia. Specimens of L. sulphureus from field collections and herbaria were evaluated taxonomically and by chemical means. A total of seven distinct alkaloid profiles and the individual alkaloids associated with each profile were identified. Each alkaloid profile was unique in its geographical distribution and its potential risk to livestock. In conclusion, taxonomic classification is not sufficient to determine risk, as chemical characterization of the alkaloids must also be performed. PMID:19182952

  18. Structural and quantitative analysis of Equisetum alkaloids.

    PubMed

    Cramer, Luise; Ernst, Ludger; Lubienski, Marcus; Papke, Uli; Schiebel, Hans-Martin; Jerz, Gerold; Beuerle, Till

    2015-08-01

    Equisetum palustre L. is known for its toxicity for livestock. Several studies in the past addressed the isolation and identification of the responsible alkaloids. So far, palustrine (1) and N(5)-formylpalustrine (2) are known alkaloids of E. palustre. A HPLC-ESI-MS/MS method in combination with simple sample work-up was developed to identify and quantitate Equisetum alkaloids. Besides the two known alkaloids six related alkaloids were detected in different Equisetum samples. The structure of the alkaloid palustridiene (3) was derived by comprehensive 1D and 2D NMR experiments. N(5)-Acetylpalustrine (4) was also thoroughly characterized by NMR for the first time. The structure of N(5)-formylpalustridiene (5) is proposed based on mass spectrometry results. Twenty-two E. palustre samples were screened by a HPLC-ESI-MS/MS method after development of a simple sample work-up and in most cases the set of all eight alkaloids were detected in all parts of the plant. A high variability of the alkaloid content and distribution was found depending on plant organ, plant origin and season ranging from 88 to 597mg/kg dried weight. However, palustrine (1) and the alkaloid palustridiene (3) always represented the main alkaloids. For the first time, a comprehensive identification, quantitation and distribution of Equisetum alkaloids was achieved. PMID:25823584

  19. Quaternary alkaloids of tinospora species.

    PubMed

    Bisset, N G; Nwaiwu, J

    1983-08-01

    The occurrence of quaternary alkaloids in TINOSPORA (and PARABAENA) species (Menispermaceae) has been studied. The main components were generally the protoberberine bases berberine and palmatine, with jatrorrhizine an occasional minor constituent, and the aporphine base magnoflorine. Choline was also often present. Only magnoflorine was detected in the PARABAENA material examined. PMID:17404996

  20. Cyclopeptide Alkaloids from Hymenocardia acida.

    PubMed

    Tuenter, Emmy; Exarchou, Vassiliki; Baldé, Aliou; Cos, Paul; Maes, Louis; Apers, Sandra; Pieters, Luc

    2016-07-22

    Four cyclopeptide alkaloids (1-4) were isolated from the root bark of Hymenocardia acida by means of semipreparative HPLC with DAD and ESIMS detection and conventional separation methods. Structure elucidation was performed by spectroscopic means. In addition to the known compound hymenocardine (1), three other alkaloids were isolated for the first time from a natural source. These included a hymenocardine derivative with a hydroxy group instead of a carbonyl group that was named hymenocardinol (2), as well as hymenocardine N-oxide (3) and a new cyclopeptide alkaloid containing an unusual histidine moiety named hymenocardine-H (4). The isolated cyclopeptide alkaloids were tested for their antiplasmodial activity and cytotoxicity. All four compounds showed moderate antiplasmodial activity, with IC50 values ranging from 12.2 to 27.9 μM, the most active one being hymenocardine N-oxide (3), with an IC50 value of 12.2 ± 6.6 μM. Compounds 2-4 were found not to be cytotoxic against MRC-5 cells (IC50 > 64.0 μM), but hymenocardine (1) showed some cytotoxicity, with an IC50 value of 51.1 ± 17.2 μM. PMID:27351950

  1. Saponins from edible legumes: chemistry, processing, and health benefits.

    PubMed

    Shi, John; Arunasalam, Konesh; Yeung, David; Kakuda, Yukio; Mittal, Gauri; Jiang, Yueming

    2004-01-01

    Demand for bean products is growing because of the presence of several health-promoting components in edible bean products such as saponins. Saponins are naturally occurring compounds that are widely distributed in all cells of legume plants. Saponins, which derive their name from their ability to form stable, soaplike foams in aqueous solutions, constitute a complex and chemically diverse group of compounds. In chemical terms, saponins contain a carbohydrate moiety attached to a triterpenoid or steroids. Saponins are attracting considerable interest as a result of their diverse properties, both deleterious and beneficial. Clinical studies have suggested that these health-promoting components, saponins, affect the immune system in ways that help to protect the human body against cancers, and also lower cholesterol levels. Saponins decrease blood lipids, lower cancer risks, and lower blood glucose response. A high saponin diet can be used in the inhibition of dental caries and platelet aggregation, in the treatment of hypercalciuria in humans, and as an antidote against acute lead poisoning. In epidemiological studies, saponins have been shown to have an inverse relationship with the incidence of renal stones. Thermal processing such as canning is the typical method to process beans. This study reviews the effect of thermal processing on the characteristics and stability of saponins in canned bean products. Saponins are thermal sensitive. During soaking and blanching, portions of saponins are dissolved in water and lost in the soaking, washing, and blanching liquors. An optimum thermal process can increase the stability and maintain the saponins in canned bean products, which is useful for assisting the food industry to improve thermal processing technology and enhance bean product quality. PMID:15117556

  2. Sheep Ingestion of Water Containing Quebracho or Black Wattle Tannin

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Ingestion of small amounts of condensed tannin by ruminants can produce valuable outcomes such as improved nitrogen use, reduced bloating and methane output, and internal parasite reduction. Many grasses and forbs have little if any condensed tannin in them. Not all livestock will consistently con...

  3. Wheat Forages Contain Variable Levels of Condensed Tannin Reactive Substances

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Even though winter wheat pasture in the southern Great Plains is considered excellent forage, devastating losses of stocker cattle can occur due to pasture bloat. Tannins are known to reduce the incidence and severity of bloat. We examined tannins in adapted wheat varieties that are commonly grazed ...

  4. Improved Characterization of Sorghum Tannins Using Size-Exclusion Chromatography

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Tannins are large polyphenolic polymers consisting of flavan-3-ol subunits that are deposited in the pigmented testa layer of sorghum kernels. Tannins have been characterized in several different species of plants using a multitude of techniques. Most of the methods are very time and resource consum...

  5. HPLC retention thermodynamics of grape and wine tannins.

    PubMed

    Barak, Jennifer A; Kennedy, James A

    2013-05-01

    The effect of grape and wine tannin structure on retention thermodynamics under reversed-phase high-performance liquid chromatography conditions on a polystyrene divinylbenzene column was investigated. On the basis of retention response to temperature, an alternative retention factor was developed to approximate the combined temperature response of the complex, unresolvable tannin mixture. This alternative retention factor was based upon relative tannin peak areas separated by an abrupt change in solvent gradient. Using this alternative retention factor, retention thermodynamics were calculated. Van't Hoff relationships of the natural log of the alternative retention factor against temperature followed Kirchoff's relationship. An inverse quadratic equation was fit to the data, and from this the thermodynamic parameters for tannin retention were calculated. All tannin fractions exhibited exothermic, spontaneous interaction, with enthalpy-entropy compensation observed. Normalizing for tannin size, distinct tannin compositional effects on thermodynamic parameters were observed. The results of this study indicate that HPLC can be valuable for measuring the thermodynamics of tannin interaction with a hydrophobic surface and provides a potentially valuable alternative to calorimetry. Furthermore, the information gathered may provide insight into understanding red wine astringency quality. PMID:23565723

  6. Tannin extracts abate ammonia emissions from simulated dairy barn floors.

    PubMed

    Powell, J M; Aguerre, M J; Wattiaux, M A

    2011-01-01

    Feeding more tannin and less crude protein (CP) to dairy cows may have synergistic impacts on reducing NH emissions from dairy barns. Three trials using lab-scale ventilated chambers with concrete floors were conducted to determine the impacts on NH emission of tannin and CP feeding, tannin feeding on urease activity in feces, and tannin application directly to the barn floor. For Trial 1, mixtures of feces and urine from lactating Holstein dairy cows () fed four levels (g kg) of dietary tannin extract [a mixture from red quebracho () and chestnut () trees]: 0 tannin (0T), 4.5 (low tannin [LT]), 9.0 (medium tannin [MT]), and 18.0 (high tannin [HT]); each fed at two levels (g kg) of dietary CP: 155 low CP (LCP) and 168 high CP (HCP) were applied to chambers. For Trial 2, urea solution was added to feces obtained from cows fed 0T, MT, and HT at HCP. For Trial 3, tannin amounts equivalent to those fed at 0T, MT, and HT were applied directly to feces-urine mixtures from 0T-HCP. For all trials, NH emissions were measured 1, 3, 6, 12, 24, 36, and 48 h after treatment application. For Trial 1, reductions in NH emission due to tannin feeding were greatest when fed at LCP: The LCP-LT and LCP-HT treatments emitted 30.6% less NH than LCP-0T, and the HCP-LT and HCP-HT treatments emitted 16.3% less NH than HCP-0T. For Trial 2, feeding tannin decreased urease activity in feces, resulting in an 11.5% reduction in cumulative NH loss. For Trial 3, the application of tannin directly to simulated barn floors also apparently decreased urease activity, resulting in an average reduction in cumulative NH emissions of 19.0%. Larger-scale trails are required to ascertain the effectiveness of tannin extracts in abating NH loss from dairy barn floors. PMID:21546676

  7. Vegetable oil thermosets reinforced by tannin-lipid formulations.

    PubMed

    Luo, Chunhua; Grigsby, Warren J; Edmonds, Neil R; Al-Hakkak, Jafar

    2013-02-01

    Totally bio-based thermosetting polymers which are comparable to synthetic polyester thermosets have been prepared from copolymerization of condensed tannin-fatty acid esters with vegetable oils. Oxidative copolymerization of tannin linoleate/acetate mixed esters with linseed oil and tung oil produced polymer films ranging from soft rubbers to rigid thermosets. Tannin incorporation into the formulations was essential for the final product to achieve necessary mechanical strength. Films had ambient modulus values between 0.12 and 1.6 GPa, with glass transition temperatures ranging from 32 to 72 °C and calculated crosslink densities of 1020-57,700 mol m⁻³. Film stiffness, T(g) and crosslink density increase with greater tannin linoeate/acetate content due mainly to this tannin component providing rigidity through polyphenolic aromatic rings and unsaturated chains as crosslinking sites. PMID:22975626

  8. Tannin-binding salivary proteins in three captive rhinoceros species.

    PubMed

    Clauss, Marcus; Gehrke, Janin; Hatt, Jean-Michel; Dierenfeld, Ellen S; Flach, Edmund J; Hermes, Robert; Castell, Johanna; Streich, W Juergen; Fickel, Joerns

    2005-01-01

    Tannin-binding salivary proteins (TBSP) are considered to be counter-defences acquired in the course of evolution by animals whose natural forage contains such tannins. As tannins mostly occur in browse material but not in grasses, it is assumed that grazers do not have a need for TBSP. Whereas it has been shown in several non-ungulate species that TBSP can be induced by dietary tannins, their presence or absence in ungulates has, so far, been shown to be a species-specific characteristic independent of dietary manipulations. We investigated saliva from three rhinoceros species from zoological gardens fed comparable, conventional zoo diets. As expected, saliva from white rhinoceroses (Ceratotherum simum, grazer) had lower tannin-binding capacities than that from black rhinoceroses (Diceros bicornis, browser). Surprisingly, however, Indian rhinoceroses (Rhinoceros unicornis), commonly regarded as grazers as well, displayed the highest tannin-binding capacities of the three species investigated. It is speculated that this discrepancy might be a result of an evolutionarily recent switch to a grass-dominated diet in Indian rhinoceroses, and that the black rhinoceros, which is closer related to the white rhinoceros than the Indian species, has evolved an inducible mechanism of TBSP production. In separate trials during which the tannin content of the diets of black rhinoceroses was increased by the addition of either tannic acid or quebracho, the tannin-binding capacity of black rhinoceros saliva was increased to levels within the same range as that of Indian rhinoceroses on the conventional diets. While induction trials in white and Indian rhinoceroses remain to be performed for a full understanding of salivary anti-tannin defence in rhinoceroses, these results are the first report of an induced salivary response to increased dietary tannin levels in an ungulate species. PMID:15664314

  9. A simple method for isolation of Gypsophila saponins for the combined application of targeted toxins and saponins in tumor therapy.

    PubMed

    Weng, Alexander; Bachran, Diana; Görick, Cornelia; Bachran, Christopher; Fuchs, Hendrik; Melzig, Matthias F

    2009-10-01

    Saponinum album (SAP) is a complex mixture of triterpene saponins from Gypsophila paniculata L. Although most of the saponins from SAP are characterized, the separation of pure saponins remains time consuming and costly, involving different chromatographic techniques. Recently it was shown that SAP drastically enhanced the cytotoxicity of a chimeric toxin consisting of the N-glycosidase saporin and human epidermal growth factor (Sap-EGF) in cell culture experiments. In view of a potential therapeutic use of the coadministration of SAP and Sap-EGF in tumor therapy, an economic and time-saving method for the isolation of pure saponins from the crude SAP mixture in high amounts is required. In this study we isolated a single saponin by a simple chromatographic method. The isolated saponin was characterized by mass spectrometry and was shown to enhance the cytotoxicity of Sap-EGF on HER14 cells. PMID:19452437

  10. New oleanene triterpenoid saponins from Madhuca longifolia.

    PubMed

    Yoshikawa, K; Tanaka, M; Arihara, S; Pal, B C; Roy, S K; Matsumura, E; Katayama, S

    2000-12-01

    Four new oleanane-type triterpene glycosides, madlongisides A-D (1-4), were isolated from the seeds of Madhuca longifolia, and their structures were elucidated on the basis of extensive NMR experiments and chemical methods. Also obtained in this investigation were the known compounds mimusopside A, Mi-saponins A, B, and C, and 3-O-beta-D-glucopyranosyl protobassic acid. PMID:11141115

  11. Potent antitrypanosomal triterpenoid saponins from Mussaenda luteola

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Five new triterpenoid saponins, heinsiagenin A 3-O-[a-L-rhamnopyranosyl-(1->2)-Beta-D-glucopyranosyl-(1->2)]-B-D-glucopyranoside (1), heinsiagenin A 3-O-[a-L-rhamnopyranosyl-(1->2)-B-D-glucopyranosyl- (1->2)]-[B-D-glucopyranosyl-(1-4)]-B-D-glucopyranoside (2). 2a-hydroxyheinsiagenin A 3-o-[a-L-rhamn...

  12. Leaf herbivory and nutrients increase nectar alkaloids.

    PubMed

    Adler, Lynn S; Wink, Michael; Distl, Melanie; Lentz, Amanda J

    2006-08-01

    Correlations between traits may constrain ecological and evolutionary responses to multispecies interactions. Many plants produce defensive compounds in nectar and leaves that could influence interactions with pollinators and herbivores, but the relationship between nectar and leaf defences is entirely unexplored. Correlations between leaf and nectar traits may be mediated by resources and prior damage. We determined the effect of nutrients and leaf herbivory by Manduca sexta on Nicotiana tabacum nectar and leaf alkaloids, floral traits and moth oviposition. We found a positive phenotypic correlation between nectar and leaf alkaloids. Herbivory induced alkaloids in nectar but not in leaves, while nutrients increased alkaloids in both tissues. Moths laid the most eggs on damaged, fertilized plants, suggesting a preference for high alkaloids. Induced nectar alkaloids via leaf herbivory indicate that species interactions involving leaf and floral tissues are linked and should not be treated as independent phenomena in plant ecology or evolution. PMID:16913940

  13. Condensed tannins increase nitrogen recovery by trees following insect defoliation.

    PubMed

    Madritch, Michael D; Lindroth, Richard L

    2015-10-01

    While the importance of plant secondary metabolites to belowground functioning is gaining recognition, the perception remains that secondary metabolites are produced for herbivore defense, whereas their belowground impacts are ecological by-products, or 'afterlife' effects. However, plants invest a significant amount of resources into production of secondary metabolites that have minimal effects on herbivore resistance (e.g. condensed tannins and insect herbivores). We show that genetically mediated variation in condensed tannin concentration is correlated with plant nitrogen recovery following a severe defoliation event. We used single-tree mesocosms labeled with (15) N to track nitrogen through both the frass and litter cycling pathways. High concentrations of leaf tannins in Populus tremuloides were correlated with (15) N recovery from frass within the same growing season and in the following growing season. Likewise, leaf tannin concentrations were also correlated with (15) N recovery from the litter of defoliated trees in the growing season following the defoliation event. Conversely, tannins were not well correlated with nitrogen uptake under conditions of nominal herbivory. Our results suggest that tannins may confer benefits in response to herbivore pressure through conserved belowground nitrogen cycling, rather than via defensive properties. Consequently, tannins may be considered as chemical mediators of tolerance rather than resistance. PMID:25952793

  14. Imidazole alkaloids from Lepidium meyenii.

    PubMed

    Cui, Baoliang; Zheng, Bo Lin; He, Kan; Zheng, Qun Yi

    2003-08-01

    Two new imidazole alkaloids (lepidiline A and lepidiline B) have been isolated from a root extract of Lepidium meyenii with the common name Maca and identified as 1,3-dibenzyl-4,5-dimethylimidazolium chloride (1) and 1,3-dibenzyl-2,4,5-trimethylimidazolium chloride (2), respectively. The structures of these two new compounds were determined by spectroscopic methods, as well as single-crystal X-ray diffraction performed on compound 1. PMID:12932133

  15. Bacterial Alkaloids Prevent Amoebal Predation.

    PubMed

    Klapper, Martin; Götze, Sebastian; Barnett, Robert; Willing, Karsten; Stallforth, Pierre

    2016-07-25

    Bacterial defense mechanisms have evolved to protect bacteria against predation by nematodes, predatory bacteria, or amoebae. We identified novel bacterial alkaloids (pyreudiones A-D) that protect the producer, Pseudomonas fluorescens HKI0770, against amoebal predation. Isolation, structure elucidation, total synthesis, and a proposed biosynthetic pathway for these structures are presented. The generation of P. fluorescens gene-deletion mutants unable to produce pyreudiones rendered the bacterium edible to a variety of soil-dwelling amoebae. PMID:27294402

  16. Effects of different tannin-rich extracts and rapeseed tannin monomers on methane formation and microbial protein synthesis in vitro.

    PubMed

    Wischer, G; Boguhn, J; Steingaß, H; Schollenberger, M; Rodehutscord, M

    2013-11-01

    Tannins, polyphenolic compounds found in plants, are known to complex with proteins of feed and rumen bacteria. This group of substances has the potential to reduce methane production either with or without negative effects on digestibility and microbial yield. In the first step of this study, 10 tannin-rich extracts from chestnut, mimosa, myrabolan, quebracho, sumach, tara, valonea, oak, cocoa and grape seed, and four rapeseed tannin monomers (pelargonidin, catechin, cyanidin and sinapinic acid) were used in a series of in vitro trials using the Hohenheim gas test, with grass silage as substrate. The objective was to screen the potential of various tannin-rich extracts to reduce methane production without a significant effect on total gas production (GP). Supplementation with pelargonidin and cyanidin did not reduce methane production; however, catechin and sinapinic acid reduced methane production without altering GP. All tannin-rich extracts, except for tara extract, significantly reduced methane production by 8% to 28% without altering GP. On the basis of these results, five tannin-rich extracts were selected and further investigated in a second step using a Rusitec system. Each tannin-rich extract (1.5 g) was supplemented to grass silage (15 g). In this experiment, nutrient degradation, microbial protein synthesis and volatile fatty acid production were used as additional response criteria. Chestnut extract caused the greatest reduction in methane production followed by valonea, grape seed and sumach, whereas myrabolan extract did not reduce methane production. Whereas chestnut extract reduced acetate production by 19%, supplementation with grape seed or myrabolan extract increased acetate production. However, degradation of fibre fractions was reduced in all tannin treatments. Degradation of dry matter and organic matter was also reduced by tannin supplementation, and no differences were found between the tannin-rich extracts. CP degradation and ammonia

  17. Tannin signatures of barks, needles, leaves, cones, and wood at the molecular level

    NASA Astrophysics Data System (ADS)

    Hernes, Peter J.; Hedges, John I.

    2004-03-01

    We analyzed 117 tissues from 77 different plant species for molecular tannin. Tannin was measured in 89 tissues (as high as 10.5 wt.% total tannin), including procyanidin (PC) tannin in 88 tissues, prodelphinidin (PD) tannin in 50, and propelargonidin (PP) tannin in 24. In addition to tannin, several flavones, flavanones, and triterpenoids were measured, the latter which yielded as much as 4.5 wt.%. Compositions varied considerably between species, including several that yielded comparatively rare tannin or triterpenoids. Conifer needles were distinguished by high yields of PD tannin overall and relative to PC tannin. Dicotyledon leaves were characterized by the presence of flavones and triterpenoids. Barks were marked by flavanones and tetracosanoic acid. Based on these trends, relationships that could be useful as geochemical parameters were developed for distinguishing needles, leaves, and barks as possible components of litter, soil, or sedimentary mixtures.

  18. Increasing the Oxidative Stress Response Allows Escherichia coli To Overcome Inhibitory Effects of Condensed Tannins

    PubMed Central

    Smith, Alexandra H.; Imlay, James A.; Mackie, Roderick I.

    2003-01-01

    Tannins are plant-derived polyphenols with antimicrobial effects. The mechanism of tannin toxicity towards Escherichia coli was determined by using an extract from Acacia mearnsii (Black wattle) as a source of condensed tannins (proanthocyanidins). E. coli growth was inhibited by tannins only when tannins were exposed to oxygen. Tannins auto-oxidize, and substantial hydrogen peroxide was generated when they were added to aerobic media. The addition of exogenous catalase permitted growth in tannin medium. E. coli mutants that lacked HPI, the major catalase, were especially sensitive to tannins, while oxyR mutants that constitutively overexpress antioxidant enzymes were resistant. A tannin-resistant mutant was isolated in which a promoter-region point mutation increased the level of HPI by 10-fold. Our results indicate that wattle condensed tannins are toxic to E. coli in aerobic medium primarily because they generate H2O2. The oxidative stress response helps E. coli strains to overcome their inhibitory effect. PMID:12788743

  19. Pyrrolizidine alkaloids in human diet.

    PubMed

    Prakash, A S; Pereira, T N; Reilly, P E; Seawright, A A

    1999-07-15

    Pyrrolizidine alkaloids are the leading plant toxins associated with disease in humans and animals. Upon ingestion, metabolic activation in liver converts the parent compounds into highly reactive electrophiles capable of reacting with cellular macromolecules forming adducts which may initiate acute or chronic toxicity. The pyrrolizidine alkaloids present a serious health risk to human populations that may be exposed to them through contamination of foodstuffs or when plants containing them are consumed as medicinal herbs. Some pyrrolizidine alkaloids (PA) adducts are persistent in animal tissue and the metabolites may be re-released and cause damage long after the initial period of ingestion. PAs are also known to act as teratogens and abortifacients. Chronic ingestion of plants containing PAs has also led to cancer in experimental animals and metabolites of several PAs have been shown to be mutagenic in the Salmonella typhimurium/mammalian microsome system. However, no clinical association has yet been found between human cancer and exposure to PAs. Based on the extensive reports on the outcome of human exposure available in the literature, we conclude that while humans face the risk of veno-occlusive disease and childhood cirrhosis PAs are not carcinogenic to humans. PMID:10415431

  20. Alkaloids from Glaucium flavum from Sardinia.

    PubMed

    Petitto, Valentina; Serafini, Mauro; Gallo, Francesca Romana; Multari, Giuseppina; Nicoletti, Marcello

    2010-07-01

    Glaucium flavum collected in Sardinia was studied using a phytochemical approach in order to evaluate its alkaloid composition and obtain a comparison with the alkaloid contents of the same species in populations of other geographic proveniences. In fact, different chemoecotypes of G. flavum have been identified, on the basis of their particular content and composition in alkaloids, in accordance with the different distribution areas. The analysis showed that Sardinian G. flavum contains a homogeneous alkaloid pattern of aporphyne type, significantly different from those reported for populations from other parts of Europe. PMID:20552526

  1. Extraction of condensed tannins from Mexican plant sources.

    PubMed

    Garcíaa, Ramiro; Aguilera, Antonio; Contreras-Esquivel, Juan C; Rodríguez, Raúl; Aguilar, Cristóbal N

    2008-01-01

    Contents of total polyphenols, condensed tannins and proanthocyanidins, and their stability to various pH values and temperatures were studied in Mexican blueberry, cuautecomate fruit, garambullo fruit, aubergine, coffee pulp and residues of black grapes. Several aqueous extracts, obtained through a one-pass-extraction process, were analyzed using liquid chromatography in order to quantify the condensed tannin (proanthocyanidin) content responsible for their antioxidant activity and colour. All tested samples included high proanthocyanidin contents demonstrating that these Mexican fruits and vegetables are good sources of natural antioxidants, and they all could be considered as excellent functional foods due to their bioactivity measured as the condensed tannin level. PMID:18386482

  2. Use of whole grain and refined flour from tannin and non-tannin sorghum (Sorghum bicolor (L.) Moench) varieties in frybread.

    PubMed

    Rose, Devin J; Williams, Emily; Mkandawire, Nyambe L; Weller, Curtis L; Jackson, David S

    2014-07-01

    Frybreads were prepared using wheat flour and wheat-sorghum composite flours (refined and whole grain; white, tannin-free and red, tannin-containing) at 0, 25, 50, and 75% sorghum flour. Hardness, volume, specific volume, color, and oil uptake were determined. Frybreads made with refined white, tannin-free sorghum were also evaluated in a sensory panel. Substitution of sorghum flour for wheat flour reduced the volume and increased the darkness of the fried dough pieces compared with wheat flour controls. Oil absorption was unaffected when using white, tannin-free sorghum. When using red, tannin-containing sorghum, oil absorption increased for refined flour and decreased for whole grain flour, suggesting that a component only present in the whole grain tannin-containing Sorghum--perhaps tannins themselves--may decrease oil uptake. Panelists rated frybreads containing up to 50% white, tannin-free sorghum flour as not significantly different from control frybreads made with refined wheat flour. PMID:23744121

  3. Effect of tannins on the in vitro growth of Clostridium perfringens.

    PubMed

    Elizondo, Ana M; Mercado, Elsa C; Rabinovitz, Bettina C; Fernandez-Miyakawa, Mariano E

    2010-10-26

    Vegetable tannins are water-soluble polyphenolic compounds of varying molecular weights that occur abundantly in nature. The diet of many free-ranging wild animals contains significant amounts of tannins. Also, commercial tannins are used in animal industry as food additives to improve animal performance. In order to further determine the capacity of tannins to inhibit the development of intestinal diseases produced by Clostridium pefringens, we evaluated here the effect of tannins from quebracho, chestnut or combinations of both on C. perfringens and their toxins. The C. perfringens (types A, B, C, D and E) growth obtained from the intestine of healthy and diseased animals was reduced in a dose-dependent manner in the presence of quebracho tannins, chestnut tannins, combinations of both or a commercial formula based in these tannins. Although the minimal inhibitory concentration of both tannins varied between isolates, no statistically significant differences were observed between isolates from healthy or sick animals. Comparative analysis showed that the concentrations of quebracho tannin inhibiting the growth of C. perfringens were higher than chestnut tannin. In fact, antibacterial effect of quebracho tannin was increased up to 20 times with the addition of 25% of chestnut tannin and 85 times with 75% of chestnut tannin. Antibacterial activity of the commercial product was up to ~50 times higher than quebracho tannin alone. Quebracho tannin showed partial bactericidal activity, whereas chestnut tannin activity was stronger. Both tannins were able to reduce the alpha toxin lecithinase activity and epsilon toxin cytotoxicity in MDCK cells. These results suggest that tannin-supplemented diet could be useful to prevent some clostridial diseases. PMID:20471759

  4. Sealing and anti-corrosive action of tannin rust converters

    SciTech Connect

    Gust, J.; Bobrowicz, J. )

    1993-01-01

    A possibility of the application of mercury porosimetry in the investigation on porosity in corrosion products of the carbon steel along with the degree of sealing by the use of tannin rust converters is presented. The effect of the atmospheric humidity on the rust conversion including the time of that conversion on the degree of rust sealing is discussed. The results of the corrosion investigation of carbon steel covered with a layer of the rust converted with tannin-containing agents are presented.

  5. Hydrolyzable and condensed tannins resistance in Clostridium perfringens.

    PubMed

    Redondo, L M; Dominguez, J E; Rabinovitz, B C; Redondo, E A; Fernández Miyakawa, M E

    2015-08-01

    Tannins added in the diet are being used to improve nutrition and health in farm animals as an alternative to antibiotic growth promoters and to control enteric clostridial diseases. However, the capacity of Clostridium perfringens to develop resistance under the selective pressure of tannins is unknown. The purpose of this study was to determine if C. perfringens possess the ability to develop resistance against tannins in comparison with antimicrobial agents. Susceptibility for 7 AGPs (antimicrobial growth promoters), 9 therapeutic antimicrobials and 2 tannin based extracts was determined for 30 C. perfringens strains isolated from poultry and cattle. Two susceptible strains were selected and cultured in presence of sub-inhibitory concentrations of tannins and AGPs for resistant sub-populations selection. Tannin resistance of C. perfringens isolates from both animal species revealed no statistically significant differences in MICs (minimum inhibitory concentration). Poultry isolates showed higher MICs to several AGPs compared with cattle isolates. All isolates were susceptible to the therapeutic antimicrobials tested, but avian isolates showed a significantly lower susceptibility to these antimicrobials which was highly correlated with an increased resistance to bacitracin and others AGPs. In-vitro selection of resistant clones suggests that C. perfringens was unable to develop resistance against tannins at least compared to AGPs like bacitracin and avilamycin. Avian origin strains, which were previously exposed to antibiotics showed higher resistance, compared to cattle origin strains. These results suggest that the evolution of resistance against tannins in C. perfringens would be more difficult and slower than to the determined AGPs. PMID:26037239

  6. 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.

  7. Two new acridone alkaloids from Glycosmis macrantha.

    PubMed

    Yahayu, Maizatul Akmal; Rahmani, Mawardi; Hashim, Najihah Mohd; Amin, Muhammad Aizat Mohd; Ee, Gwendoline Cheng Lian; Sukari, Mohd Aspollah; Akim, Abdah

    2011-01-01

    Extraction and chromatographic separation of the extracts of dried stem barks of Glycosmis macrantha lead to isolation of two new acridone alkaloids, macranthanine and 7-hydroxynoracronycine, and a known acridone, atalaphyllidine. The structures of these alkaloids were determined by detailed spectral analysis and also by comparison with reported data. PMID:21623311

  8. 27 CFR 21.99 - Brucine alkaloid.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 27 Alcohol, Tobacco Products and Firearms 1 2013-04-01 2013-04-01 false Brucine alkaloid. 21.99 Section 21.99 Alcohol, Tobacco Products and Firearms ALCOHOL AND TOBACCO TAX AND TRADE BUREAU, DEPARTMENT OF THE TREASURY ALCOHOL FORMULAS FOR DENATURED ALCOHOL AND RUM Specifications for Denaturants § 21.99 Brucine alkaloid. (a) Identification...

  9. Plant alkaloids of the polymethyleneamine series

    NASA Astrophysics Data System (ADS)

    Rogoza, Ludmila N.; Salakhutdinov, Nariman F.; Tolstikov, Genrikh A.

    2005-04-01

    The published data on the structures and biological activities of the plant alkaloids of the biogenic polymethyleneamine series, viz., putrescine (1,4-diaminobutane), spermidine (1,8-diamino-4 -azaoctane), and spermine (1,12-diamino-4,9-diazadodecane), are considered and systematised. The structures and biological activities of some synthetic analogues of these alkaloids are also presented.

  10. Glycoalkaloids and calystegine alkaloids in potatoes

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Potatoes contain two classes of alkaloids: the glycoalkaloids and the calystegines. The presence of glycoalkaloids in potatoes and their toxicity has been known for more than a century and much has been written about them. Discovery of the nortropane calystegine alkaloids is more recent, and the k...

  11. Ergot alkaloids: toxicokinetics and vascular effects

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Endophyte (Neotyphodium coenophialum)-infected tall fescue (Lolium arundinaceum) occupies nearly 15 million ha in the USA. Although this symbiosis is beneficial to the plant, it produces ergot alkaloids that are detrimental to livestock production. Livestock consuming the alkaloids elicit adverse ph...

  12. Microbial production of plant benzylisoquinoline alkaloids

    PubMed Central

    Minami, Hiromichi; Kim, Ju-Sung; Ikezawa, Nobuhiro; Takemura, Tomoya; Katayama, Takane; Kumagai, Hidehiko; Sato, Fumihiko

    2008-01-01

    Benzylisoquinoline alkaloids, such as the analgesic compounds morphine and codeine, and the antibacterial agents berberine, palmatine, and magnoflorine, are synthesized from tyrosine in the Papaveraceae, Berberidaceae, Ranunculaceae, Magnoliaceae, and many other plant families. It is difficult to produce alkaloids on a large scale under the strict control of secondary metabolism in plants, and they are too complex for cost-effective chemical synthesis. By using a system that combines microbial and plant enzymes to produce desired benzylisoquinoline alkaloids, we synthesized (S)-reticuline, the key intermediate in benzylisoquinoline alkaloid biosynthesis, from dopamine by crude enzymes from transgenic Escherichia coli. The final yield of (S)-reticuline was 55 mg/liter within 1 h. Furthermore, we synthesized an aporphine alkaloid, magnoflorine, or a protoberberine alkaloid, scoulerine, from dopamine via reticuline by using different combination cultures of transgenic E. coli and Saccharomyces cerevisiae cells. The final yields of magnoflorine and scoulerine were 7.2 and 8.3 mg/liter culture medium. These results indicate that microbial systems that incorporate plant genes cannot only enable the mass production of scarce benzylisoquinoline alkaloids but may also open up pathways for the production of novel benzylisoquinoline alkaloids. PMID:18492807

  13. Anaerobic treatment of natural tannin extracts in UASB reactors.

    PubMed

    López-Fluza, J; Omil, F; Méndez, R

    2003-01-01

    Tannin extracts are substances commonly used in leather production processes. Since most of the steps of tannery manufacturing processes are carried out in aqueous environments, the presence of these compounds in the wastewaters is important. The aim of this work is to study the feasibility of the anaerobic degradation of three natural tannin extracts in three Upflow Anaerobic Sludge Blanket (UASB) reactors, which were fed with increasing concentrations of two condensed (quebracho and wattle) and one hydrolysable tannin extract (chestnut). Concentrations of applied extracts were 100, 200, 400, 800 and 1,000 mg/l, and 5 g/l of glucose was used as cosubstrate. Reactors were operated during 210 days and their performance was evaluated from the values of total and soluble COD, total and intermediate alkalinity, volatile fatty acids, pH and UV absorption at 280 nm. COD removal efficiencies higher than 85% were achieved in all cases. However, tannin extract removal efficiencies (based on UV-280 nm absorption measurements) were significantly lower, around 20% for condensed extracts and 60% for the hydrolysable one, when the reactors operated with the highest tannin extract concentration. The operation of the reactors was stable, commonly with alkalinity ratios below 0.30. Mass balances carried out indicate that most of the COD removal efficiencies are due to the removal of the readily biodegradable organic matter (glucose), whereas the tannin extracts are hardly anaerobically biodegradable, especially condensed extracts (wattle and quebracho). PMID:14640213

  14. Molecular activities, biosynthesis and evolution of triterpenoid saponins.

    PubMed

    Augustin, Jörg M; Kuzina, Vera; Andersen, Sven B; Bak, Søren

    2011-04-01

    Saponins are bioactive compounds generally considered to be produced by plants to counteract pathogens and herbivores. Besides their role in plant defense, saponins are of growing interest for drug research as they are active constituents of several folk medicines and provide valuable pharmacological properties. Accordingly, much effort has been put into unraveling the modes of action of saponins, as well as in exploration of their potential for industrial processes and pharmacology. However, the exploitation of saponins for bioengineering crop plants with improved resistances against pests as well as circumvention of laborious and uneconomical extraction procedures for industrial production from plants is hampered by the lack of knowledge and availability of genes in saponin biosynthesis. Although the ability to produce saponins is rather widespread among plants, a complete synthetic pathway has not been elucidated in any single species. Current conceptions consider saponins to be derived from intermediates of the phytosterol pathway, and predominantly enzymes belonging to the multigene families of oxidosqualene cyclases (OSCs), cytochromes P450 (P450s) and family 1 UDP-glycosyltransferases (UGTs) are thought to be involved in their biosynthesis. Formation of unique structural features involves additional biosynthetical enzymes of diverse phylogenetic background. As an example of this, a serine carboxypeptidase-like acyltransferase (SCPL) was recently found to be involved in synthesis of triterpenoid saponins in oats. However, the total number of identified genes in saponin biosynthesis remains low as the complexity and diversity of these multigene families impede gene discovery based on sequence analysis and phylogeny. This review summarizes current knowledge of triterpenoid saponin biosynthesis in plants, molecular activities, evolutionary aspects and perspectives for further gene discovery. PMID:21333312

  15. [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. PMID:26790286

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

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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....

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

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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...

  18. Iboga-Type Alkaloids from Ervatamia officinalis.

    PubMed

    Tang, Ben-Qin; Wang, Wen-Jing; Huang, Xiao-Jun; Li, Guo-Qiang; Wang, Lei; Jiang, Ren-Wang; Yang, Ting-Ting; Shi, Lei; Zhang, Xiao-Qi; Ye, Wen-Cai

    2014-08-22

    Seven new iboga-type alkaloids, ervaoffines A-D (1-4), (7S)-3-oxoibogaine hydroxyindolenine (5), ibogaine-5,6-dione (6), and 19-epi-5-oxovoacristine (7), and 10 known alkaloids were isolated from Ervatamia officinalis. The absolute configurations of 1-7 were determined through X-ray diffraction and electronic circular dichroism (ECD) analyses. Ervaoffines A and B represent the first iboga-type pseudoindoxyl alkaloids in which the C-2 spiro carbon configuration is opposite to that of other members of this class, such as iboluteine (8). The relationship between the absolute configuration of the spiro carbons and the Cotton effect in the ECD spectrum is established for the first time for iboga-type pseudoindoxyl and oxindole alkaloids. Additionally, a plausible biogenetic pathway for these alkaloids is proposed. PMID:25093992

  19. Hydrolyzable tannins of tamaricaceous plants. V. Structures of monomeric-trimeric tannins and cytotoxicity of macrocyclic-type tannins isolated from Tamarix nilotica (1).

    PubMed

    Orabi, Mohamed A A; Taniguchi, Shoko; Sakagami, Hiroshi; Yoshimura, Morio; Yoshida, Takashi; Hatano, Tsutomu

    2013-05-24

    Three new ellagitannin monomers, nilotinins M5-M7 (1-3), a dimer, nilotinin D10 (4), and a trimer, nilotinin T1 (5), together with three known dimers, hirtellin D (7) and tamarixinins B (8) and C (9), and a trimer, hirtellin T2 (6), were isolated from Tamarix nilotica dried leaves. The structures of the tannins were elucidated by intensive spectroscopic methods and chemical conversions into known tannins. The new trimer (5) is a unique macrocyclic type whose monomeric units are linked together by an isodehydrodigalloyl and two dehydrodigalloyl moieties. Additionally, dimeric and trimeric macrocyclic-type tannins isolated from T. nilotica in this study were assessed for possible cytotoxic activity against four human tumor cell lines. Tumor-selective cytotoxicities of the tested compounds were higher than those of synthetic and natural potent cytotoxic compounds, including polyphenols, and comparable with those of 5-fluorouracil and melphalan. PMID:23675651

  20. Effect of Condensed Tannins on Bacterial Diversity and Metabolic Activity in the Rat Gastrointestinal Tract

    PubMed Central

    Smith, Alexandra H.; Mackie, Roderick I.

    2004-01-01

    The effect of dietary condensed tannins (proanthocyanidins) on rat fecal bacterial populations was ascertained in order to determine whether the proportion on tannin-resistant bacteria increased and if there was a change in the predominant bacterial populations. After 3 weeks of tannin diets the proportion of tannin-resistant bacteria increased significantly (P < 0.05) from 0.3% ± 5.5% to 25.3% ± 8.3% with a 0.7% tannin diet and to 47.2% ± 5.1% with a 2% tannin diet. The proportion of tannin-resistant bacteria returned to preexposure levels in the absence of dietary tannins. A shift in bacterial populations was confirmed by molecular fingerprinting of fecal bacterial populations by denaturing gradient gel electrophoresis (DGGE). Posttreatment samples were generally still distinguishable from controls after 3.5 weeks. Sequence analysis of DGGE bands and characterization of tannin-resistant isolates indicated that tannins selected for Enterobacteriaceae and Bacteroides species. Dot blot quantification confirmed that these gram-negative bacterial groups predominated in the presence of dietary tannins and that there was a corresponding decrease in the gram-positive Clostridium leptum group and other groups. Metabolic fingerprint patterns revealed that functional activities of culturable fecal bacteria were affected by the presence of tannins. Condensed tannins of Acacia angustissima altered fecal bacterial populations in the rat gastrointestinal tract, resulting in a shift in the predominant bacteria towards tannin-resistant gram-negative Enterobacteriaceae and Bacteroides species. PMID:14766594

  1. Two new hepaprotective saponins from Semen celosiae.

    PubMed

    Sun, Zhen-Liang; Wang, Ying; Guo, Mei-Li; Li, Yu-Xian

    2010-07-01

    Two new oleanolic acid saponins, namely celosin C (1) and celosin D (2), were isolated from the ethanol extract of Semen celosiae. Their structures were identified as celosin C (1) and celosin D (2) by spectroscopic and chemical analyses. The hepatoprotective activity of 1 and 2 with oral dose 1.0, 2.0 and 4.0 mg/kg, respectively, were investigated by carbon tetrachloride (CCl(4))-induced hepatotoxicity in mice. The results indicate that they have significant hepatoprotective effects (p<0.01). PMID:19945514

  2. Cytotoxic triterpene saponins from Clematis mandshurica.

    PubMed

    He, Yu-Xin; Li, Ling; Zhang, Kang; Liu, Zhong-Rong

    2011-12-01

    Two new triterpene saponins, mandshunosides A and B (1 and 2), were isolated from the roots and rhizomes of Clematis mandshurica. Their structures were elucidated on the basis of spectroscopic evidence and hydrolysis products. Compounds 1 and 2 showed inhibitory activities against two colorectal human cancer cells HCT 116 (IC₅₀ 2.1 μM for 1 and 2.5 μM for 2) and HT-29 (IC₅₀ 3.7 μM for 1 and 3.3 μM for 2). PMID:22115034

  3. Presence of tannins in sorghum grains is conditioned by different natural alleles of Tannin1

    PubMed Central

    Wu, Yuye; Li, Xianran; Xiang, Wenwen; Zhu, Chengsong; Lin, Zhongwei; Wu, Yun; Li, Jiarui; Pandravada, Satchidanand; Ridder, Dustan D.; Bai, Guihua; Wang, Ming L.; Trick, Harold N.; Bean, Scott R.; Tuinstra, Mitchell R.; Tesso, Tesfaye T.; Yu, Jianming

    2012-01-01

    Sorghum, an ancient old-world cereal grass, is the dietary staple of over 500 million people in more than 30 countries in the tropics and semitropics. Its C4 photosynthesis, drought resistance, wide adaptation, and high nutritional value hold the promise to alleviate hunger in Africa. Not present in other major cereals, such as rice, wheat, and maize, condensed tannins (proanthocyanidins) in the pigmented testa of some sorghum cultivars have been implicated in reducing protein digestibility but recently have been shown to promote human health because of their high antioxidant capacity and ability to fight obesity through reduced digestion. Combining quantitative trait locus mapping, meta-quantitative trait locus fine-mapping, and association mapping, we showed that the nucleotide polymorphisms in the Tan1 gene, coding a WD40 protein, control the tannin biosynthesis in sorghum. A 1-bp G deletion in the coding region, causing a frame shift and a premature stop codon, led to a nonfunctional allele, tan1-a. Likewise, a different 10-bp insertion resulted in a second nonfunctional allele, tan1-b. Transforming the sorghum Tan1 ORF into a nontannin Arabidopsis mutant restored the tannin phenotype. In addition, reduction in nucleotide diversity from wild sorghum accessions to landraces and cultivars was found at the region that codes the highly conserved WD40 repeat domains and the C-terminal region of the protein. Genetic research in crops, coupled with nutritional and medical research, could open the possibility of producing different levels and combinations of phenolic compounds to promote human health. PMID:22699509

  4. Effect of MDL-Type alkaloids on tall larkspur toxicosis

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Larkspur plants contain numerous norditerpenoid alkaloids which include the 7, 8-methylenedioxylycoctonine (MDL) -type alkaloids and the N-(methylsuccinimido) anthranoyllycoctonine (MSAL) -type alkaloids. The MSAL-type alkaloids are generally much more toxic (typically > 20x) than the MDL-type alka...

  5. Effect of MDL-type alkaloids on tall larkspur toxicosis

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Larkspur plants contain numerous norditerpenoid alkaloids which include the 7, 8-methylenedioxylycoctonine (MDL) -type alkaloids and the N-(methylsuccinimido) anthranoyllycoctonine (MSAL) -type alkaloids. The MSAL-type alkaloids are generally much more toxic (typically > 20x). Toxicity of many tal...

  6. [Vinca alkaloid and MDR1].

    PubMed

    Takigawa, Nagio; Tanimoto, Mitsune

    2008-07-01

    Vinca alkaloids inhibit microtubule formation by binding to tubulin. There are four clinically available vinca alkaloids including vincristine, vinblastine, vindesine, and vinorelbine. P-glycoprotein(P-gp)is the one of the efflux adenosine triphosphate(ATP)-binding cassette family transporters and is the encoded product of MDR1 gene. P-gp is overexpressed not only in tumor cells resistant to multiple anticancer agents but also found in normal cells such as liver, gastrointestinal tract and kidney, working as a biological defense mechanism. Single nucleotide polymorphisms for MDR1 in exon 12(1236), exon 21(2677), and exon 26(3435)have been well studied. Although C1236T and C3435T do not change the amino acid, G2677T and G2677A result in amino acid substitution of Ala893Ser and Ala893Thr, respectively. In the use of haplotypes to predict vincristine pharmacokinetics, the correlation between the haplotypes and the elimination half-life was reported. Many studies of the relationship between polymorphism/haplotype for MDR1 and pharmacodynamics including efficacy and toxicity of chemotherapy have been explored. PMID:18633246

  7. Antioxidant action of benzylisoquinoline alkaloids.

    PubMed

    Ubeda, A; Montesinos, C; Payá, M; Terencio, C; Alcaraz, M J

    1993-01-01

    The antioxidant action of a series of benzylisoquinoline alkaloids has been investigated. Laudanosoline, protopapaverine, anonaine, apomorphine, glaucine, boldine, bulbocapnine, tetrahydroberberine and stepholidine produced a dose-dependent inhibition of microsomal lipid peroxidation induced by Fe2+/ascorbate, CCl4/NADPH or by Fe3+ ADP/NADPH. Apomorphine exerted the highest inhibitory effects in the three systems of induction used, with a potency higher than propyl gallate. Laudanosoline was particularly effective in the first system, while bulbocapnine and anonaine were more potent when CCl4/NADPH or Fe3(+)-ADP/NADPH were used as inducers. Laudanosoline, protopapaverine, apomorphine, tetrahydroberberine and stepholidine were also potent inhibitors of nitroblue tetrazolium (NBT) reduction. The presence of a free hydroxyl group or preferably of a catechol group is a feature relevant for inhibition of lipid peroxidation and NBT reduction, nevertheless the antioxidant activity of benzylisoquinoline alkaloids cannot be only ascribed to the formation of phenoxy radicals and other free radical species may be formed during aporphine and tetrahydroprotoberberine oxidation. The influence of this series of compounds on the time course of lipid peroxidation suggests that some of them, like apomorphine and boldine act as chain-breaking antioxidants. PMID:8319926

  8. Steroidal saponins of Yucca schidigera Roezl.

    PubMed

    Oleszek, W; Sitek, M; Stochmal, A; Piacente, S; Pizza, C; Cheeke, P

    2001-09-01

    Eight steroidal saponins have been isolated from Yucca schidigera Roezl. trunk, and their structures were established by spectral (MS and NMR) techniques. These included three novel furostanol glycosides including 3-O-beta-D-glucopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucopyranosyl-5 beta(25R)-furostan-3 beta,22 alpha,26-triol 26-O-beta-D-glucopyranoside, 3-O-beta-D-glcopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucopyranosyl-5 beta(25R)-furost-20(22)-en-3 beta,26-diol-12-one 26-O-beta-D-glucopyranoside, 3-O-beta-D-glcopyranosyl-(1-->2)-beta-D-glucopyranosyl-5 beta(25R)-furostan-3 beta,22 alpha,26-triol 26-O-beta-D-glucopyranoside, and five known spirostanol glycosides. On the basis of the extraction efficiency, furostanol glycosides made up only 6.8% of total saponins isolated. PMID:11559144

  9. Neuroprotective Effect of Radix Trichosanthis Saponins on Subarachnoid Hemorrhage

    PubMed Central

    Chen, Ying; Sun, Haiyan; Huang, Liyong; Li, Juxiang; Zhou, Wenke; Chang, Jingling

    2015-01-01

    Redox homeostasis has been implicated in subarachnoid hemorrhage (SAH). As a result, antioxidants and/or free radical scavengers have become an important therapeutic modality. Considering that radix trichosanthis (RT) saponins exhibited strong antioxidant ability both in vivo and in vitro, the present study aimed to reveal whether the neuroprotective activities of RT saponins were mediated by p38/p53 signal pathway after SAH. An established SAH model was used and superoxide dismutase (SOD), malondialdehyde (MDA), induced nitric oxide synthase (iNOS), nitric oxide (NO), lactate dehydrogenase (LDH), p-p38, and p53 activation were detected after 48 h of SAH. The results showed that RT saponins inhibited iNOS expression to restore NO to basal level. Moreover, compared with Cu/Zn-SOD, RT saponins (2 mg/kg/d dosage) significantly increased Mn-SOD activity after SAH. Accompanied with lowered NO and elevated SOD, decreased p38 phosphorylation and p53 activities were observed, especially for RT saponins at 2 mg/kg/d dosage. In this setting, the neurological outcome was also improved with less neuronal cells damage after RT saponins pretreatment. Our findings demonstrated the beneficial effects of RT saponins in enhancing neuroprotective effects by deducing iNOS activity, normalizing SOD level, and inhibiting p-p38 and p53 expression, hence offering significant therapeutic implications for SAH. PMID:26089937

  10. Selective glycosylation of steroidal saponins by Arthrobacter nitroguajacolicus.

    PubMed

    Liu, Jing-yuan; Lu, Li; Kang, Li-ping; Liu, Yi-xun; Zhao, Yang; Xiong, Cheng-qi; Zhang, Yu-qin; Yu, Li-yan; Ma, Bai-ping

    2015-01-30

    In this study seven strains of the genus Arthrobacter were screened by biotransformation to discover glycosylating patterns on steroid saponins. A strain of Arthrobacter nitroguajacolicus (CPCC 203516) was found to have the ability of fructosylation. Crude enzyme of the strain was extracted for the further study of conversion characteristics and patterns. Sucrose was used as a non-activated sugar donor, and fifteen steroidal saponins were involved. Nine furostan saponins of the substrates were converted, and ten products were isolated and identified. Based on the HR-ESI-MS, 1D, and 2D NMR spectral data, one fructosyl was added to furostan saponins at C6-OH of 26-O-β-D-glucopyranosyl by A. nitroguajacolicus for all nine products. One product was distinguished by an additional fructosyl at the position of C6-OH on the first added fructosyl. Spirostan saponins of the substrates could not be converted. Steroidal saponins embracing a fructosyl are quite rare according to other reports based on similar studies. This study successfully converted furostan saponins into new compounds. PMID:25497335

  11. In vitro determination of the spermicidal activity of plant saponins.

    PubMed

    Primorac, M; Sekulović, D; Antonić, S

    1985-08-01

    The plant kingdom might yield an effective antifertility drug. A Mentha arvensis L. (Labiatae) fraction with uterotonic activity was isolated, and was found to be active on the nonpregnant as well as the pregnant rat uterus. According to folklore medicine, the Mexican plant Montanoa tomentosa Cerv. (zoapatle) possesses antifertility activity in women. The effect of various isolated preparations from this plant on early pregnancy were investigated in serveral rodent species including the mouse, rat hamster, and guinea pig. It was concluded that zoapatle plant extracts possess unique antifertility activity. Lin-Hsim and coworkers isolated fractions from Aristolochia molissima Hanceith contrceptive activity in female mice. Saponins of some plants were used in contraceptive formulations either as foaming agents or as spermicidal substances. Elbary and Nour investigated the spermicidal effects of saponins isolated from the following plants: Gypsophila paniculata L., Saponaria officinalis L., Enterolobium cyclocarpum, Griseb., Terminalia horrida Steud., Melilotus sicula Vitm., and Ruscus hypoglossum L. All of the saponins tested possessed spermicidal activity. Jain and coworkers isolated 2 new saponins in Pittosporum nilghrense with spermicidal effects. In this paper we have determined the spermicidal activity of saponins isolated from some Yugoslav plants, which in that aspect have not been investigated. The results are illustrated in the table. They show that all of the saponins tested were spermicidal in dependence on their nature. Saponins of Primula vulgaris Huds. and Cyclamen persicum Mill. immobilized human spermatozoa within a period of 20 s at a dilution 1:1000. Saponin of Gypsophila paniculata L. was spermicidal at dilution 1:20. These findings show that saponins isolated from some Yugoslav plants may be useful spermicides of natural origin. PMID:4080814

  12. 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. PMID:21347998

  13. Oral toxicity of Madhuca butyracea Macb. saponins to albino rats.

    PubMed

    Lalitha, T; Vishwanatha, S; Venkataraman, L V

    1990-07-01

    Saponins, isolated from M. butyracea, were assessed for their acute and subacute oral toxicity in albino rats. Acute doses of saponins caused mortalities and LD50 and LD90 values were 330 and 430 mg/kg body wt respectively. Severe diarrhoea, restlessness and histopathological changes were observed in liver and kidney. Diets containing saponins at 0,250,500 and 1000 ppm for 14 weeks did not affect food intake, growth or organ weights, but induced mild histological changes in liver and kidney and altered the serum levels of alkaline phosphatase, blood urea nitrogen, cholesterol and proteins, particularly in female rats. PMID:2272650

  14. A novel hepatoprotective saponin from Celosia cristata L.

    PubMed

    Wang, Yan; Lou, Ziyang; Wu, Qing-Bin; Guo, Mei-Li

    2010-12-01

    A new saponin, cristatain (1), together with four other saponins, celosin A (2), celosin B (3), celosin C (4) and celosin D (5) were isolated from the seeds of Celosia cristata L. (Amaranthaceae). Their structures were established by chemical and spectroscopic analyses. For the first time, the saponins were found in C. cristata L. In addition, compound 1 exhibited significant hepatoprotective effect on carbon tetrachloride (CCl(4))- and N,N-dimethylformamide (DMF)-induced hepatotoxicity in mice, which were evidenced by significant decreases in the values of asparate aminotransferase (AST), alanine aminotransferase (ALT) and alkaline phosphatase (ALP) of serum and histopathological examinations compared to controls. PMID:20804825

  15. Triterpenoid saponins from Clematis tangutica and their cardioprotective activities.

    PubMed

    Zhang, Wei; Wang, Xiaoyang; Tang, Haifeng; Wang, Minchang; Ji, Lanju; Wen, Aidong; Wang, Jianbo

    2013-01-01

    Phytochemical investigation of the whole plants of Clematis tangutica led to the isolation of three new triterpenoid saponins (1-3), together with four known saponins (4-7). Their structures were determined by extensive spectral analysis and chemical evidences. Compounds 1-7 were evaluated for their cardioprotective activities in cardiomyocytes anoxia/reoxygenation (A/R) model. The results showed that those saponins exhibited cardioprotective effects by decreasing the levels of creatine kinase-MB (CK-MB) and lactate dehydrogenase (LDH). PMID:23266737

  16. Bioactive acridone alkaloids from Swinglea glutinosa.

    PubMed

    Weniger, B; Um, B H; Valentin, A; Estrada, A; Lobstein, A; Anton, R; Maillé, M; Sauvain, M

    2001-09-01

    A new prenylated acridone alkaloid, 1,3,5-trihydroxy-2,8-bis(3-methylbut-2-enyl)-10-methyl-9-acridone (1), was isolated from the stembark of Swinglea glutinosa, along with three known acridone alkaloids, 5-hydroxynoracronycine (2), 1,3,5-trihydroxy-4-methoxy-2-(3-methylbut-2-enyl)-10-methyl-9-acridone (3), and 1,3,5-trihydroxy-4-methoxy-10-methylacridone (4). The isolated alkaloids were assessed in vitro against chloroquine-sensitive and -resistant Plasmodium falciparum strains and for cytotoxicity using HeLa cells. PMID:11575960

  17. Polycyclic Guanidine Alkaloids from Poecilosclerida Marine Sponges

    PubMed Central

    Sfecci, Estelle; Lacour, Thierry; Amade, Philippe; Mehiri, Mohamed

    2016-01-01

    Sessile marine sponges provide an abundance of unique and diversified scaffolds. In particular, marine guanidine alkaloids display a very wide range of biological applications. A large number of cyclic guanidine alkaloids, including crambines, crambescins, crambescidins, batzelladines or netamins have been isolated from Poecilosclerida marine sponges. In this review, we will explore the chemodiversity of tri- and pentacyclic guanidine alkaloids. NMR and MS data tools will also be provided, and an overview of the wide range of bioactivities of crambescidins and batzelladines derivatives will be given. PMID:27070629

  18. Tannin bark Melalauca cajuputi powell (gelam) as green corrosion inhibitor of mild steel

    NASA Astrophysics Data System (ADS)

    Talib, Nur Atiqah Abu; Zakaria, Sarani; Hua, Chia Chin; Othman, Norinsan Kamil

    2014-09-01

    Tannin was extracted from gelam bark and used to produce corrosion inhibitor for mild steel. Tannin was extracted from gelam bark using 70% aqueous acetone for 6 hour. Tannin powder was characterization using fourier transform infrared spectroscopy to analyse chemical component in tannin and Scanning electron microscope (SEM) for tannin physical structure. The tannin effect on the corrosion inhibition of mild steel has been investigated in 1Mol HCl solution for 6 hour followed ASTM. The weight loss method were applied to study the mild steel corrosion behavior in the present and absend of different concentration of tannin (250, 300, 350)ppm. Tannin act good inhibitor as corrosion inhibitor for mild steel in acid medium. Surface morphology of carbon steel with and without inhibitor was investigated by scanning electron microscopy.

  19. Tannin bark Melalauca cajuputi powell (gelam) as green corrosion inhibitor of mild steel

    SciTech Connect

    Talib, Nur Atiqah Abu; Zakaria, Sarani; Hua, Chia Chin; Othman, Norinsan Kamil

    2014-09-03

    Tannin was extracted from gelam bark and used to produce corrosion inhibitor for mild steel. Tannin was extracted from gelam bark using 70% aqueous acetone for 6 hour. Tannin powder was characterization using fourier transform infrared spectroscopy to analyse chemical component in tannin and Scanning electron microscope (SEM) for tannin physical structure. The tannin effect on the corrosion inhibition of mild steel has been investigated in 1Mol HCl solution for 6 hour followed ASTM. The weight loss method were applied to study the mild steel corrosion behavior in the present and absend of different concentration of tannin (250, 300, 350)ppm. Tannin act good inhibitor as corrosion inhibitor for mild steel in acid medium. Surface morphology of carbon steel with and without inhibitor was investigated by scanning electron microscopy.

  20. Tannin diagenesis in mangrove leaves from a tropical estuary: a novel molecular approach

    NASA Astrophysics Data System (ADS)

    Hernes, Peter J.; Benner, Ronald; Cowie, Gregory L.; Goñi, Miguel A.; Bergamaschi, Brian A.; Hedges, John I.

    2001-09-01

    Molecular-level condensed tannin analyses were conducted on a series of mangrove ( Rhizophora mangle) leaves at various stages of decomposition in a tropical estuary. Total molecular tannin yields ranged from 0.5% ash-free dry weight (AFDW) in the most highly degraded black leaves (6-7 weeks in the water) up to >7% AFDW in fresh leaves (<1 week in the water). Total tannin exhibits an intermediate lability in these leaves relative to other measured biochemicals. Leaching is an important mechanism in tannin removal from leaves as indicated by the 30% loss of measurable tannin during a leaching experiment. Condensed tannin was >80% procyanidin (PC) with the remainder being prodelphinidin (PD). PD tannin, with its higher degree of hydroxylation, proved to be more labile than PC tannin. Average chain length of condensed tannin (degree of polymerization) exhibited an initial increase in response to leaching, but later decreased in the subsequent shift toward abiotic or microbially mediated chemical reactions. Several trends point toward a possible condensation reaction in which tannin plays a role in nitrogen immobilization. These include an apparent inverse correlation between molecular tannin and nitrogen, a positive correlation between molecular tannin and percent basic amino acids, 13C-NMR data indicating transformation of tannin as opposed to remineralization, and 13C-NMR data showing loss of condensed tannin B-ring phenolic carbons coupled with preservation of A-ring phenolic carbon. In addition to condensed tannin, the molecular method used also yielded several triterpenoids. Triterpenoids accounted for up to 3.5% AFDW of the leaf material and exhibited a threefold increase between yellow senescent leaves entering the estuary and black leaves. This trend is likely due to the weakening of protective cuticular membranes during leaf decomposition, which leads to increased yields in the acidic conditions used for tannin analyses.

  1. Preference for polyethylene glycol by sheep fed a quebracho tannin diet.

    PubMed

    Villalba, J J; Provenza, F D

    2001-08-01

    Tannins decrease food intake by reducing digestion and by causing illness, whereas polyethylene glycol (PEG) attenuates the aversive effects of tannins. Our objective was to determine whether sheep recognize the benefits of ingesting substances such as PEG when consuming tannins. If so, then ingestion of PEG should be 1) PEG-specific, 2) a function of previous experience with recovery from tannin-toxicosis, and 3) dependent on the presence/absence of tannins. During conditioning, lambs in Group 1 (n = 10) were offered a meal of high-tannin food, which presumably caused malaise, and then offered PEG (molecular weight, 3,350), which presumably led to recovery from malaise. Subsequently, lambs ingested a control food (wheat straw) that did not have the "medicinal" effects of PEG in the absence of the tannin diet. In contrast, lambs in Group 2 (n = 10) ingested PEG in the absence of the tannin diet, and they ingested the tannin diet only in association with wheat straw. Ingestion of PEG and straw by both groups of lambs increased as a function of the presence of tannins in the diet (P < 0.05). However, when offered a choice among the tannin diet, PEG and straw, or when given the tannin diet and then offered a choice between PEG and straw, lambs trained to associate PEG with tannins ate more PEG than lambs that ingested PEG without tannins (P < 0.05). The responses were apparently PEG-specific; straw intake did not differ between groups of lambs during testing (P > 0.05), and differences in PEG intake disappeared in the absence of tannins (P > 0.05). In summary, our results suggest that lambs fed high-tannin diets discriminated the effects of PEG from those provided by a "nonmedicinal" food (straw). Thus, it may be possible to formulate PEG supplements that allow herbivores to self-regulate intake of PEG under extensive management conditions. PMID:11518214

  2. 27 CFR 21.99 - Brucine alkaloid.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... dissolved by hydrochloric acid when several drops of a 1 N barium chloride solution are added to 10 ml of a... Brucine alkaloid. (a) Identification test. Add a few drops of concentrated nitric acid to about 10 mg...

  3. 27 CFR 21.99 - Brucine alkaloid.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... dissolved by hydrochloric acid when several drops of a 1 N barium chloride solution are added to 10 ml of a... Brucine alkaloid. (a) Identification test. Add a few drops of concentrated nitric acid to about 10 mg...

  4. 27 CFR 21.99 - Brucine alkaloid.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... dissolved by hydrochloric acid when several drops of a 1 N barium chloride solution are added to 10 ml of a... Brucine alkaloid. (a) Identification test. Add a few drops of concentrated nitric acid to about 10 mg...

  5. 27 CFR 21.99 - Brucine alkaloid.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... dissolved by hydrochloric acid when several drops of a 1 N barium chloride solution are added to 10 ml of a... Brucine alkaloid. (a) Identification test. Add a few drops of concentrated nitric acid to about 10 mg...

  6. Molecular pharmacokinetics of catharanthus (vinca) alkaloids.

    PubMed

    Levêque, Dominique; Jehl, François

    2007-05-01

    This review focuses on the published data regarding the molecular determinants (enzymes, transporters, orphan nuclear receptors) of Catharanthus (vinca) alkaloids pharmacokinetics in humans. The clinical impact of these determinants (drug disposition, drug-drug interactions) is also discussed. PMID:17442684

  7. In vitro anticholinesterase activity of various alkaloids.

    PubMed

    Orhan, Ilkay; Naz, Qamar; Kartal, Murat; Tosun, Fatma; Sener, Bilge; Choudhary, M Iqbal

    2007-01-01

    In the current study, a number of alkaloids including retamine, cytisine, and sparteine (quinolizidine-type), yohimbine and vincamine (indole-type), scopolamine and atropine (tropane-type), colchicine (tropolone-type), allantoin (imidazolidine-type), trigonelline (pyridine-type) as well as octopamine, synephrine, and capsaicin (exocyclic amine-type) were tested in vitro for their inhibitory activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) at 1 mg/ml concentration by the Ellman method using an ELISA microplate reader. Among the alkaloids tested, only capsaicin exerted a remarkable inhibitory effect towards both AChE and BChE [(62.7 +/- 0.79)% and (75.3 +/- 0.98)%, respectively]. While the rest of the alkaloids did not show any significant inhibition against AChE, three of the alkaloids, namely retamine, sparteine, and yohimbine, exerted a noteworthy anti-BChE effect as compared to galanthamine, the reference drug. PMID:18069241

  8. Cytotoxic indole alkaloids from Tabernaemontana divaricata.

    PubMed

    Bao, Mei-Fen; Yan, Ju-Ming; Cheng, Gui-Guang; Li, Xing-Yao; Liu, Ya-Ping; Li, Yan; Cai, Xiang-Hai; Luo, Xiao-Dong

    2013-08-23

    Five new vobasinyl-ibogan-type bisindole alkaloids, tabernaricatines A-E (1-5), two new monomers, tabernaricatines F and G (6 and 7), and 24 known indole alkaloids were isolated from the aerial parts of Tabernaemontana divaricata. Alkaloids 1 and 2 are the first vobasinyl-ibogan-type alkaloids possessing a six-membered ring via an ether linkage between C-17 and C-21. All compounds except for 3 were evaluated for their cytotoxicity against five human cancer cell lines; conophylline showed significant bioactivity against HL-60, SMMC-7721, A-549, MCF-7, and SW480 cells with IC₅₀ values of 0.17, 0.35, 0.21, 1.02, and 1.49 μM, respectively. PMID:23944995

  9. Anxiolytic Activity of Diterpene Alkaloid Songorine.

    PubMed

    Nesterova, Yu V; Povet'eva, T N; Suslov, N I; Shults, E E; Ziuz'kov, G N; Aksinenko, S G; Afanas'eva, O G; Krapivin, A V; Kharina, T G

    2015-09-01

    Antianxiety action of diterpene alkaloid songorine was studied using Vogel conflict test. Songorine in a dose of 0.25 mg/kg demonstrated high anxiolytic activity comparable to that of phenazepam and produced no sedative effect. PMID:26468026

  10. Piperidine alkaloids: Human and food animal teratogens

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Piperidine alkaloids are acutely toxic to adult livestock species and produce musculoskeletal deformities in neonatal animals. These teratogenic effects include multiple congenital contracture (MCC) deformities and cleft palate in cattle, pigs, sheep, and goats. Poisonous plants containing teratogen...

  11. Steroidal Saponins from the Rhizomes of Aspidistra typica.

    PubMed

    Cui, Jiang-Ming; Kang, Li-Ping; Zhao, Yang; Zhao, Jian-Yuan; Zhang, Jie; Pang, Xu; Yu, He-Shui; Jia, De-Xian; Liu, Chao; Yu, Li-Yan; Ma, Bai-Ping

    2016-01-01

    Eleven new furostanol saponins, typaspidosides B-L (1-11), one new spirostanol saponin, typaspidoside M (12), and five known spirostanol saponins, 25S-atropuroside (13), neoaspidistrin (14), (25S)-pratioside D1 (15), 25S-aspidistrin (16) and 25S-neosibiricoside (17) were isolated from the rhizomes of Aspidistra typica Baill. The structures of the new compounds were established using 1D and 2D NMR (1H-1H COSY, HMQC, HMBC and ROESY) spectroscopy, high resolution mass spectrometry, and chemical methods. The aglycones of 1-3 (unusual furostanol saponins with opened E ring type), 9 and 10 (the methoxyl substituent at C-23 position) were found, identified from natural products for the first time. Moreover, the anti-HIV activities of the isolated steroidal glycosides were assessed, and compounds 13, 14, 16 and 17 exhibited high active against HIV-1. PMID:26937954

  12. A novel triterpenoid saponin from Polygala tenuifolia Willd.

    PubMed

    Xu, Tun-Hai; Lv, Gang; Xu, Ya-Juan; Xie, Sheng-Xiu; Zhao, Hong-Feng; Han, Dong; Si, Yun-Shan; Li, Yu; Niu, Jian-Zhao; Xu, Dong-Ming

    2008-01-01

    A new triterpenoid saponin, tenuifoside A, was isolated together with three known triterpenoid saponins 2, 3, and 4 from the roots of Polygala tenuifolia Willd. With the help of chemical and spectral analyses (IR, MS, 1D-NMR, and 2D-NMR), the structure of the new saponin was elucidated as 3-O-beta-d-glucopyranosyl presenegenin 28-O-beta-d-xylopyranosyl-(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 (1). Three known triterpenoid saponins (2-4) were identified on the basis of spectroscopic data. PMID:18696336

  13. Steroidal Saponins from the Rhizomes of Aspidistra typica

    PubMed Central

    Zhao, Yang; Zhao, Jian-Yuan; Zhang, Jie; Pang, Xu; Yu, He-Shui; Jia, De-Xian; Liu, Chao; Yu, Li-Yan; Ma, Bai-Ping

    2016-01-01

    Eleven new furostanol saponins, typaspidosides B-L (1–11), one new spirostanol saponin, typaspidoside M (12), and five known spirostanol saponins, 25S-atropuroside (13), neoaspidistrin (14), (25S)-pratioside D1 (15), 25S-aspidistrin (16) and 25S-neosibiricoside (17) were isolated from the rhizomes of Aspidistra typica Baill. The structures of the new compounds were established using 1D and 2D NMR (1H-1H COSY, HMQC, HMBC and ROESY) spectroscopy, high resolution mass spectrometry, and chemical methods. The aglycones of 1–3 (unusual furostanol saponins with opened E ring type), 9 and 10 (the methoxyl substituent at C-23 position) were found, identified from natural products for the first time. Moreover, the anti-HIV activities of the isolated steroidal glycosides were assessed, and compounds 13, 14, 16 and 17 exhibited high active against HIV-1. PMID:26937954

  14. A new steroidal saponin from Dioscorea cayenensis.

    PubMed

    Sautour, Marc; Mitaine-Offer, Anne-Claire; Miyamoto, Tomofumi; Dongmo, Alain; Lacaille-Dubois, Marie-Aleth

    2004-11-01

    The new 26-O-beta-D-glucopyranosyl-3beta,26-dihydroxy-20,22-seco-25(R)-furost-5-en-20,22-dione-3-O-alpha-L-rhamnopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->4)-[alpha-L-rhamnopyranosyl-(1-->2)]-beta-D-glucopyranoside (1), along with the known methyl protodioscin (2), asperoside (3) and prosapogenin A of dioscin (4) were isolated from the rhizomes of Dioscorea cayenensis LAM.-HOLL (Dioscoreaceae). Their structures were established mainly on the basis of 600 MHz 2D-NMR spectral data. 4 exhibited antifungal activity against the human pathogenic yeasts Candida albicans, C. glabrata and C. tropicalis (MICs of 20.8, 6.25, 25 microg/ml, respectively), whereas saponins 1-3 were inactive. PMID:15516762

  15. Total Synthesis of the Akuammiline Alkaloid Picrinine

    PubMed Central

    2015-01-01

    We report the first total synthesis of the complex akuammiline alkaloid picrinine, which was first isolated nearly five decades ago. Our synthetic approach features a concise assembly of the [3.3.1]-azabicyclic core, a key Fischer indolization reaction to forge the natural product’s carbon framework, and a series of delicate late-stage transformations to complete the synthesis. Our synthesis of picrinine also constitutes a formal synthesis of the related polycyclic alkaloid strictamine. PMID:24597784

  16. A novel alkaloid from Gaultheria nummularioides.

    PubMed

    Yang, M-F; Li, Y-Y; Li, B-G; Zhang, G-L

    2007-03-01

    A novel alkaloid, gaultherialine A (1), along with twenty-seven known compounds were isolated from the whole plants of Gaultheria nummularioides D. Don. The structure of the new alkaloid was elucidated as 7,8-dimethoxy-1-(4-methoxyphenyl)-4,5-dihydro-2H-benzo[e]indole-2-one N-oxide (1) on the basis of spectral evidence. PMID:17454316

  17. Seco-tabersonine alkaloids from Tabernaemontana corymbosa.

    PubMed

    Lim, Kuan-Hon; Thomas, Noel F; Abdullah, Zanariah; Kam, Toh-Seok

    2009-02-01

    Two seco-tabersonine alkaloids, jerantiphyllines A and B, in addition to a tabersonine hydroxyindolenine, jerantinine H, and a recently reported vincamine alkaloid 7, were isolated from the leaf extract of the Malayan Tabernaemontana corymbosa and the structures were established using NMR and MS analysis. Biomimetic conversion of jerantinines A and E to their respective vincamine and 16-epivincamine derivatives were also carried out. PMID:19217125

  18. BIAdb: A curated database of benzylisoquinoline alkaloids

    PubMed Central

    2010-01-01

    Background Benzylisoquinoline is the structural backbone of many alkaloids with a wide variety of structures including papaverine, noscapine, codeine, morphine, apomorphine, berberine, protopine and tubocurarine. Many benzylisoquinoline alkaloids have been reported to show therapeutic properties and to act as novel medicines. Thus it is important to collect and compile benzylisoquinoline alkaloids in order to explore their usage in medicine. Description We extract information about benzylisoquinoline alkaloids from various sources like PubChem, KEGG, KNApSAcK and manual curation from literature. This information was processed and compiled in order to create a comprehensive database of benzylisoquinoline alkaloids, called BIAdb. The current version of BIAdb contains information about 846 unique benzylisoquinoline alkaloids, with multiple entries in term of source, function leads to total number of 2504 records. One of the major features of this database is that it provides data about 627 different plant species as a source of benzylisoquinoline and 114 different types of function performed by these compounds. A large number of online tools have been integrated, which facilitate user in exploring full potential of BIAdb. In order to provide additional information, we give external links to other resources/databases. One of the important features of this database is that it is tightly integrated with Drugpedia, which allows managing data in fixed/flexible format. Conclusions A database of benzylisoquinoline compounds has been created, which provides comprehensive information about benzylisoquinoline alkaloids. This database will be very useful for those who are working in the field of drug discovery based on natural products. This database will also serve researchers working in the field of synthetic biology, as developing medicinally important alkaloids using synthetic process are one of important challenges. This database is available from http

  19. New furocarbazole alkaloids from Lonicera quinquelocularis.

    PubMed

    Khan, Dilfaraz; Khan, Shafiullah; Badshah, Syed; Ali, Hazrat; Ullah, Hamid; Muhammad, Zia; Woodward, Simon

    2016-01-01

    Two new furocarbazole alkaloids, 3-formyl-6,7-dimethoxy-furo[1,2]carbazole (1) and methyl-6,7-dimethoxy-furo[1,2]carbazole-3-carboxylate (2), along with two known carbazole alkaloids, 3-formyl-2-hydroxy-7-methoxycarbazole (3) and methyl 2,7-dimethoxycarbazole-3-carboxylate (4) were isolated from the ethyl acetate soluble fraction of Lonicera quinquelocularis. Their structures were established on the basis of spectroscopic analysis. PMID:26168923

  20. Triterpenoid saponins from the roots of Clematis uncinata.

    PubMed

    Li, Shuo-Guo; Huang, Xiao-Jun; Li, Man-Mei; Wang, Mei; Feng, Rui-Bing; Zhang, Wei; Li, Yao-Lan; Wang, Ying; Ye, Wen-Cai

    2014-01-01

    Eight new bisdesmosidic triterpenoid saponins, clematiunicinosides A-H (1-8), along with eleven known ones (9-19), were isolated from the roots of Clematis uncinata. Their structures were elucidated on the basis of spectroscopic analysis and chemical evidence. All the isolated saponins were tested for their cytotoxic activities on human caski cervical cancer (Caski) cells, and compounds 13, 17 and 19 exhibited inhibitory effect on Caski cells. PMID:24152568

  1. Triterpene saponins from Clematis mandshurica and their antiproliferative activity.

    PubMed

    Gong, Yi-Xia; Hua, Hui-Ming; Xu, Yong-Nan; Liu, Jian-Yu; Yu, Zong-Gui; Ma, Jing; Zhang, Hui; Jing, Yong-Kui

    2013-07-01

    Six new triterpene saponins, clematomandshurica saponins F-K (1-6), together with a known compound (7), were isolated from the roots and rhizomes of Clematis mandshurica. Their structures were elucidated on the basis of spectroscopic evidence and hydrolysis. Compounds 5-7 exhibited antiproliferative effects against PC-3 human prostate cancer cells with GI50 values of 1.29, 1.50, and 0.71 µM, respectively. PMID:23804038

  2. Kinetics of the sorption of triterpene saponin by hypercrosslinked polystyrene

    NASA Astrophysics Data System (ADS)

    Mironenko, N. V.; Brezhneva, T. A.; Selemenev, V. F.

    2013-03-01

    The kinetics of sorption of triterpene saponin by the polymer sorbent NM-200 is considered. The influence of the surface activity of glycoside on the rate of formation and structure of the adsorption layer on the sorbent's surface is established. The rate-determining step of sorption is found to be diffusion into the sorbent grain. The value of the activation energy demonstrates the determining role of dispersion forces in the interaction between triterpene saponin and the polymer sorbent MN-200.

  3. Digestive parameters in young turkeys fed yucca saponin

    SciTech Connect

    Dziuk, H.E.; Duke, G.E.; Buck, R.J.; Janni, K.A.

    1985-06-01

    Yucca saponin fed in a concentration of 63 ppm to turkey poults at 6 to 14 weeks of age did not significantly improve weight gains, feed conversion, or digestive coefficients. Compared with nonstressed control groups, saponin-fed poults did not have significantly greater average weight gains or feed intakes when stressed by crowding (3 poults per cage) or by adding ammonia to the atmosphere (30 to 35 ppm).

  4. Bactericidal effect of hydrolysable and condensed tannin extracts on Campylobacter jejuni in vitro.

    PubMed

    Anderson, Robin C; Vodovnik, Maša; Min, Byeng R; Pinchak, William E; Krueger, Nathan A; Harvey, Roger B; Nisbet, David J

    2012-07-01

    Strategies are sought to reduce intestinal colonisation of food-producing animals by Campylobacter jejuni, a leading bacterial cause of human foodborne illness worldwide. Presently, we tested the antimicrobial activity of hydrolysable-rich blackberry, cranberry and chestnut tannin extracts and condensed tannin-rich mimosa, quebracho and sorghum tannins (each at 100 mg/mL) against C. jejuni via disc diffusion assay in the presence of supplemental casamino acids. We found that when compared to non-tannin-treated controls, all tested tannins inhibited the growth of C. jejuni and that inhibition by the condensed tannin-rich mimosa and quebracho extracts was mitigated in nutrient-limited medium supplemented with casamino acids. When tested in broth culture, both chestnut and mimosa extracts inhibited growth of C. jejuni and this inhibition was much greater in nutrient-limited than in full-strength medium. Consistent with observations from the disc diffusion assay, the inhibitory activity of the condensed tannin-rich mimosa extracts but not the hydrolysable tannin-rich chestnut extracts was mitigated by casamino acid supplementation to the nutrient-limited medium, likely because the added amino acids saturated the binding potential of the condensed tannins. These results demonstrate the antimicrobial activity of various hydrolysable and condensed tannin-rich extracts against C. jejuni and reveal that condensed tannins may be less efficient than hydrolysable tannins in controlling C. jejuni in gut environments containing high concentrations of amino acids and soluble proteins. PMID:22528299

  5. Bioactive indole alkaloids isolated from Alstonia angustifolia

    PubMed Central

    Pan, Li; Terrazas, César; Muñoz Acuña, Ulyana; Ninh, Tran Ngoc; Chai, Heebyung; Carcache de Blanco, Esperanza J.; Soejarto, Djaja D.; Satoskar, Abhay R.

    2014-01-01

    Bioassay-guided fractionation was conducted on a CHCl3-soluble extract of the stem bark of Alstonia angustifolia (Apocynaceae) collected in Vietnam using the HT-29 human colon cancer cell line, and led to the isolation of a new sarpagine-type indole alkaloid (1), together with nine known alkaloids, including four macroline-derived alkaloids (2–5), a sarpagine-type alkaloid (6), and four macroline-pleiocarpamine bisindole alkaloids (7–10). The structure of the new compound (1) was determined on the basis of spectroscopic data interpretation. Compounds 1–10 were evaluated in vitro for their NF-κB (p65) inhibitory activity against the Hela cells in an ELISA assay. The new sarpagine alkaloid, N(4)-methyltalpinine (1), was found to show significant NF-κB inhibitory activity (ED50 = 1.2 µM). Furthermore, all the isolates (1–10) were evaluated in vitro for their antileishmanial activity, and compounds (1–4, 6 and 8–10) exhibited leishmaniacidal activity against promastigotes of Leishmania mexicana. PMID:25584095

  6. Evidence for the inhibition of the terminal step of ruminal alpha-linolenic acid biohydrogenation by condensed tannins.

    PubMed

    Khiaosa-Ard, R; Bryner, S F; Scheeder, M R L; Wettstein, H-R; Leiber, F; Kreuzer, M; Soliva, C R

    2009-01-01

    Effects of condensed tannins (CT), either via extract or plant-bound, and saponin extract on ruminal biohydrogenation of alpha-linolenic acid (ALA) were investigated in vitro. Grass-clover hay served as basal diet (control). The control hay was supplemented with extracts contributing either CT from Acacia mearnsii [7.9% of dietary dry matter (DM)] or saponins from Yucca schidigera (1.1% of DM). The fourth treatment consisted of dried sainfoin (Onobrychis viciifolia), a CT-containing forage legume, in an amount also providing 7.9% CT in dietary DM. All diets were supplemented with linseed oil at a level contributing 60% of total dietary ALA in all treatments. Diets were incubated for 10 d (n = 4) in the rumen simulation technique system, using the last 5 d for statistical evaluation. Fatty acids were analyzed in feed, feed residues, incubation fluid, and its effluent. Data were subjected to ANOVA considering diet and experimental run as main effects. Both CT treatments reduced ruminal fiber and crude protein degradation, and lowered incubation fluid ammonia concentration. Only the CT extract suppressed methane formation and shifted microbial populations toward bacteria at cost of protozoa. The saponin extract remained without clear effects on fermentation characteristics except for increased protozoal counts. The extent of ALA biohydrogenation was 20% less with the CT plant, but this probably resulted from reduced organic matter degradability rather than from an inhibition of biohydrogenation. After incubation analysis of incubation fluid effluent and feed residues showed a considerable proportion of the 3 biohydrogenation intermediates, cis-9, trans-11, cis-15 C18:3, trans-11, cis-15 C18:2, and trans-11 C18:1, which did not occur in the initial feeds. Only the CT-extract diet led to a different profile in the effluent compared with the control diet with trans-11 C18:1 being considerably increased at cost of C18:0. This could have been achieved by suppressing

  7. Enhancement of toxicity of saporin-based toxins by Gypsophila saponins--kinetic of the saponin.

    PubMed

    Weng, Alexander; Görick, Cornelia; Melzig, Matthias F

    2009-08-01

    Saponins are amphiphilic substances consisting of a hydrophobic backbone with one or two hydrophilic sugar units. Recently it was shown that saponinum album (SA) from Gypsophila paniculata L. enhanced cytotoxicity of a saporin-based chimeric toxin (up to 385,000-fold) as well as the toxicity of saporin (up to 100,000-fold) with N-glycosidase activity. Previously we have shown that toxicity of other N-glycosidases such as ricin A-chain, nigrin b, and toxins such as diphtheria toxin or microcystin-LR was not enhanced by SA. This points to a specific SA-dependent mechanism of toxicity enhancement on saporin and saporin-based toxins. Although the cytotoxicity enhancing effect was observed in up to 10 different cell lines, nothing is known about the kinetic of SA under cell culture conditions. Therefore SA was titrated, and the uptake respective liberation profile of SA was investigated in ECV-304 cells. Treatment of cells with [(3)H]-SA leads to an immediate uptake of saponin molecules. After cells were saturated with [(3)H]-SA, a first equilibrium (first eq.) was reached. The first eq. was disturbed by washing until a second equilibrium was reached between the activity observed within cells and that seen in the supernatant. After a further extensive washing, a small portion of saponin molecules remained durable associated with the cell. This portion was sufficient to induce a drastic toxicity enhancement on saporin indicating a long-lasting sensitization of cells against the toxin. PMID:19491365

  8. Multicomponent Therapeutics of Berberine Alkaloids

    PubMed Central

    Luo, Jiaoyang; Yan, Dan; Yang, Meihua; Dong, Xiaoping; Xiao, Xiaohe

    2013-01-01

    Although berberine alkaloids (BAs) are reported to be with broad-spectrum antibacterial and antiviral activities, the interactions among BAs have not been elucidated. In the present study, methicillin-resistant Staphylococcus aureus (MRSA) was chosen as a model organism, and modified broth microdilution was applied for the determination of the fluorescence absorption values to calculate the anti-MRSA activity of BAs. We have initiated four steps to seek the optimal combination of BAs that are (1) determining the anti-MRSA activity of single BA, (2) investigating the two-component combination to clarify the interactions among BAs by checkerboard assay, (3) investigating the multicomponent combination to determine the optimal ratio by quadratic rotation-orthogonal combination design, and (4) in vivo and in vitro validation of the optimal combination. The results showed that the interactions among BAs are related to their concentrations. The synergetic combinations included “berberine and epiberberine,” “jatrorrhizine and palmatine” and “jatrorrhizine and coptisine”; the antagonistic combinations included “coptisine and epiberberine”. The optimal combination was berberine : coptisine : jatrorrhizine : palmatine : epiberberine = 0.702 : 0.863 : 1 : 0.491 : 0.526, and the potency of the optimal combination on cyclophosphamide-immunocompromised mouse model was better than the natural combinations of herbs containing BAs. PMID:23634170

  9. Methane emission by goats consuming different sources of condensed tannins

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Twenty-four yearling Boer x Spanish wethers (7/8 Boer; initial body weight [BW] of 37.5 plus/minus 0.91 kg) were used to assess effects of different condensed tannin (CT) sources on methane emission. Diets were Kobe lespedeza (Lespedeza striata; K), K plus quebracho providing CT at 5% of dry matter...

  10. The influence of condensed tannin structure on rate of microbial mineralization and reactivity to chemical assays.

    PubMed

    Norris, Charlotte E; Preston, Caroline M; Hogg, Karen E; Titus, Brian D

    2011-03-01

    We examined how tannin structure influences reactivity in tannin assays and carbon and nitrogen mineralization. Condensed tannins from the foliage of ten tree and shrub species and from pecan shells (Carya illinoensis) had different proportions of: (a) epicatechin (cis) and catechin (trans) isomers, (b) procyanidin (PC) and prodelphinidin (PD) monomers, and (c) different chain lengths. The response of each tannin to several widely used tannin assays was determined. Although there was some variation in response to proanthocyanidin (butanol/HCl) and Folin Ciocalteu assays, we did not deduce any predictable relationship between tannin structure and response to either assay. There was little variation in protein precipitation among the different tannins. To assess biological activity, six of the tannins were incubated with forest humus for 22 days. We determined that, while PC-based tannins remained at least partly extractable for the duration of the incubation, tannins with a high proportion of PD subunits rapidly became unextractable from soil. There was a positive correlation between net nitrogen mineralization and cis chemical structure. Carbon mineralization was enhanced initially by the addition of tannins to humus, but after 22 days, a negative correlation between the proportion of cis subunits and respiration was determined. Overall, we were not able to demonstrate consistent effects of structure on either microbial mineralization or reactivity to chemical assays; such relationships remain elusive. PMID:21340461

  11. Effects of large mammalian herbivores and ant symbionts on condensed tannins of Acacia drepanolobium in Kenya.

    PubMed

    Ward, David; Young, Truman P

    2002-05-01

    Condensed tannins have been considered to be important inducible defenses against mammalian herbivory. We tested for differences in condensed tannin defenses in Acacia drepanolobium in Kenya over two years among different large mammalian herbivore treatments [total exclusion, antelope only, and megaherbivore (elephants and giraffes) + antelope] and with four different ant symbiont species on the trees. We predicted that (1) condensed tannin concentrations would be lowest in the mammal treatment with the lowest level of herbivory (total exclusion), (2) trees occupied by mutualist ants that protect the trees most aggressively would have lower levels of tannins, and (3) if chemical defense production is costly, there would be a trade-off between tannin concentrations, growth, and mechanical defenses. Mean tannin concentrations increased from total exclusion treatments to wildlife-only treatments to megaherbivore + antelope treatments. In 1997, condensed tannin concentrations were significantly lower in trees occupied by the ant Crematogaster nigriceps, the only ant species that actively removed axillary buds. Contrary to our prediction, trees occupied by ant species that protect the trees more aggressively against mammalian herbivores did not have lower overall levels of condensed tannins. There was no consistent evidence of a trade-off between tannin concentrations and growth rate, but there was a positive correlation between mean thorn length and mean tannin concentrations across species of ant inhabitants and across herbivore treatments in 1997. Contrary to our expectation, trees had higher tannin concentrations in the upper parts of the canopy where there is little herbivory by mammals. PMID:12049231

  12. Phytotoxic steroidal saponins from Agave offoyana leaves.

    PubMed

    Pérez, Andy J; Simonet, Ana M; Calle, Juan M; Pecio, Łukasz; Guerra, José O; Stochmal, Anna; Macías, Francisco A

    2014-09-01

    A bioassay-guided fractionation of Agave offoyana leaves led to the isolation of five steroidal saponins (1-5) along with six known saponins (6-11). The compounds were identified as (25R)-spirost-5-en-2α,3β-diol-12-one 3-O-{α-l-rhamnopyranosyl-(1→3)-O-β-d-glucopyranosyl-(1→2)-O-[β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-O-β-d-galactopyranoside} (1), (25R)-spirost-5-en-3β-ol-12-one 3-O-{α-l-rhamnopyranosyl-(1→3)-O-β-d-glucopyranosyl-(1→2)-O-[β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-O-β-d-galactopyranoside} (2), (25R)-spirost-5-en-3β-ol-12-one 3-O-{β-d-xylopyranosyl-(1→3)-O-β-d-glucopyranosyl-(1→2)-O-[β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-O-β-d-galactopyranoside} (3), (25R)-26-O-β-d-glucopyranosylfurost-5-en-3β,22α,26-triol-12-one 3-O-{α-l-rhamnopyranosyl-(1→3)-O-β-d-glucopyranosyl-(1→2)-O-[β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-O-β-d-galactopyranoside} (4) and (25R)-26-O-β-d-glucopyranosylfurost-5-en-3β,22α,26-triol-12-one 3-O-{β-d-xylopyranosyl-(1→3)-O-β-d-glucopyranosyl-(1→2)-O-[β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-O-β-d-galactopyranoside} (5) by comprehensive spectroscopic analysis, including one- and two-dimensional NMR techniques, mass spectrometry and chemical methods. The phytotoxicity of the isolated compounds on the standard target species Lactuca sativa was evaluated. PMID:24939800

  13. Actions of Piperidine Alkaloid Teratogens at Fetal Nicotinic Acetylcholine Receptors.

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Teratogenic alkaloids are found in many species of plants including Conium maculatum L., Nicotiana glauca, Nicotiana tabaccum, and multiple Lupinus spp. Fetal musculoskeletal defects produced by alkaloids from these plants include arthrogyropisis, scoliosis, torticollis, kyposis, lordosis, and clef...

  14. Analysis of supercooling activity of tannin-related polyphenols.

    PubMed

    Kuwabara, Chikako; Wang, Donghui; Endoh, Keita; Fukushi, Yukiharu; Arakawa, Keita; Fujikawa, Seizo

    2013-08-01

    Based on the discovery of novel supercooling-promoting hydrolyzable gallotannins from deep supercooling xylem parenchyma cells (XPCs) in Katsura tree (see Wang et al. (2012) [38]), supercooling capability of a wide variety of tannin-related polyphenols (TRPs) was examined in order to find more effective supercooling-promoting substances for their applications. The TRPs examined were single compounds including six kinds of hydrolyzable tannins, 11 kinds of catechin derivatives, two kinds of structural analogs of catechin and six kinds of phenolcarboxylic acid derivatives, 11 kinds of polyphenol mixtures and five kinds of crude plant tannin extracts. The effects of these TRPs on freezing were examined by droplet freezing assays using various solutions containing different kinds of identified ice nucleators such as the ice nucleation bacterium (INB) Erwinia ananas, the INB Xanthomonas campestris, silver iodide and phloroglucinol as well as a solution containing only unintentionally included unidentified airborne ice nucleators. Among the 41 kinds of TRPs examined, all of the hydrolyzable tannins, catechin derivatives, polyphenol mixtures and crude plant tannin extracts as well as a few structural analogs of catechin and phenolcarboxylic acid derivatives exhibited supercooling-promoting activity (SCA) with significant differences (p>0.05) from at least one of the solutions containing different kinds of ice nucleators. It should be noted that there were no TRPs exhibiting ice nucleation-enhancing activity (INA) in all solutions containing identified ice nucleators, whereas there were many TRPs exhibiting INA with significant differences in solutions containing unidentified ice nucleators alone. An emulsion freezing assay confirmed that these TRPs did not essentially affect homogeneous ice nucleation temperatures. It is thought that not only SCA but also INA in the TRPs are produced by interactions with heterogeneous ice nucleators, not by direct interaction with water

  15. Phenotypic and phylogenetic characterization of ruminal tannin-tolerant bacteria.

    PubMed

    Nelson, K E; Thonney, M L; Woolston, T K; Zinder, S H; Pell, A N

    1998-10-01

    The 16S rRNA sequences and selected phenotypic characteristics were determined for six recently isolated bacteria that can tolerate high levels of hydrolyzable and condensed tannins. Bacteria were isolated from the ruminal contents of animals in different geographic locations, including Sardinian sheep (Ovis aries), Honduran and Colombian goats (Capra hircus), white-tail deer (Odocoileus virginianus) from upstate New York, and Rocky Mountain elk (Cervus elaphus nelsoni) from Oregon. Nearly complete sequences of the small-subunit rRNA genes, which were obtained by PCR amplification, cloning, and sequencing, were used for phylogenetic characterization. Comparisons of the 16S rRNA of the six isolates showed that four of the isolates were members of the genus Streptococcus and were most closely related to ruminal strains of Streptococcus bovis and the recently described organism Streptococcus gallolyticus. One of the other isolates, a gram-positive rod, clustered with the clostridia in the low-G+C-content group of gram-positive bacteria. The sixth isolate, a gram-negative rod, was a member of the family Enterobacteriaceae in the gamma subdivision of the class Proteobacteria. None of the 16S rRNA sequences of the tannin-tolerant bacteria examined was identical to the sequence of any previously described microorganism or to the sequence of any of the other organisms examined in this study. Three phylogenetically distinct groups of ruminal bacteria were isolated from four species of ruminants in Europe, North America, and South America. The presence of tannin-tolerant bacteria is not restricted by climate, geography, or host animal, although attempts to isolate tannin-tolerant bacteria from cows on low-tannin diets failed. PMID:9758806

  16. Phenotypic and Phylogenetic Characterization of Ruminal Tannin-Tolerant Bacteria

    PubMed Central

    Nelson, Karen E.; Thonney, Michael L.; Woolston, Tina K.; Zinder, Stephen H.; Pell, Alice N.

    1998-01-01

    The 16S rRNA sequences and selected phenotypic characteristics were determined for six recently isolated bacteria that can tolerate high levels of hydrolyzable and condensed tannins. Bacteria were isolated from the ruminal contents of animals in different geographic locations, including Sardinian sheep (Ovis aries), Honduran and Colombian goats (Capra hircus), white-tail deer (Odocoileus virginianus) from upstate New York, and Rocky Mountain elk (Cervus elaphus nelsoni) from Oregon. Nearly complete sequences of the small-subunit rRNA genes, which were obtained by PCR amplification, cloning, and sequencing, were used for phylogenetic characterization. Comparisons of the 16S rRNA of the six isolates showed that four of the isolates were members of the genus Streptococcus and were most closely related to ruminal strains of Streptococcus bovis and the recently described organism Streptococcus gallolyticus. One of the other isolates, a gram-positive rod, clustered with the clostridia in the low-G+C-content group of gram-positive bacteria. The sixth isolate, a gram-negative rod, was a member of the family Enterobacteriaceae in the gamma subdivision of the class Proteobacteria. None of the 16S rRNA sequences of the tannin-tolerant bacteria examined was identical to the sequence of any previously described microorganism or to the sequence of any of the other organisms examined in this study. Three phylogenetically distinct groups of ruminal bacteria were isolated from four species of ruminants in Europe, North America, and South America. The presence of tannin-tolerant bacteria is not restricted by climate, geography, or host animal, although attempts to isolate tannin-tolerant bacteria from cows on low-tannin diets failed. PMID:9758806

  17. Identification of histatins as tannin-binding proteins in human saliva.

    PubMed Central

    Yan, Q; Bennick, A

    1995-01-01

    Tannins have a number of detrimental biological effects and these include interference with normal growth and metabolism if they are present in the feed of various animals. Proline-rich proteins (PRPs) in saliva have been shown to provide protection against tannin, but little is known about the mechanism of protection and interaction of other salivary proteins with tannin. To identify tannin-binding human salivary proteins, parotid and submandibular/sublingual saliva samples were adsorbed with tannin. PRPs, and in particular a group of low-M(r) proteins, were readily precipitated by tannin. The low-M(r) proteins were purified from parotid saliva and demonstrated to be histatins, a family of well-characterized histidine-rich salivary proteins. The ability of synthetic histatin 5, as well as an acidic PRP (PRP-1) and gelatin to precipitate quebracho condensed tannin and tannic acid was determined. At pH 7.4 histatin 5 was the most effective precipitant of both condensed tannin and tannic acid and it also precipitated the largest amount of condensed tannin at pH 3.0, but the smallest amount of tannic acid at that pH. In contrast PRP-1 showed a greater ability to precipitate both condensed tannin and tannic acid at pH 3.0 than at pH 7.4. Under most circumstances histatin 5 was therefore more effective in precipitating tannins than proteins with high proline content which generally have been recognized as strong precipitants of tannin. Pre-incubation of tannic acid with alpha-amylase inhibited the enzyme, but addition of histatin 5 or the acidic PRP PIF-s protected amylase from inhibition by tannin. Similarly salivary proteins may protect other biological activities in the digestive tract from inhibition by dietary tannin. Images Figure 1 Figure 2 Figure 3 PMID:7575474

  18. Benzylisoquinoline alkaloid biosynthesis in opium poppy.

    PubMed

    Beaudoin, Guillaume A W; Facchini, Peter J

    2014-07-01

    Opium poppy (Papaver somniferum) is one of the world's oldest medicinal plants and remains the only commercial source for the narcotic analgesics morphine, codeine and semi-synthetic derivatives such as oxycodone and naltrexone. The plant also produces several other benzylisoquinoline alkaloids with potent pharmacological properties including the vasodilator papaverine, the cough suppressant and potential anticancer drug noscapine and the antimicrobial agent sanguinarine. Opium poppy has served as a model system to investigate the biosynthesis of benzylisoquinoline alkaloids in plants. The application of biochemical and functional genomics has resulted in a recent surge in the discovery of biosynthetic genes involved in the formation of major benzylisoquinoline alkaloids in opium poppy. The availability of extensive biochemical genetic tools and information pertaining to benzylisoquinoline alkaloid metabolism is facilitating the study of a wide range of phenomena including the structural biology of novel catalysts, the genomic organization of biosynthetic genes, the cellular and sub-cellular localization of biosynthetic enzymes and a variety of biotechnological applications. In this review, we highlight recent developments and summarize the frontiers of knowledge regarding the biochemistry, cellular biology and biotechnology of benzylisoquinoline alkaloid biosynthesis in opium poppy. PMID:24671624

  19. Free the tannins: the role of grape pathogenesis-related proteins in limiting condensed tannin extraction during winemaking

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Grape-derived condensed tannins (CT) are important to the mouthfeel of red wines, but CT concentrations in red wines produced from wild Vitis species or their hybrids are often lower than corresponding wines produced from European wine grapes (V. vinifera), potentially decreasing their utility. Thes...

  20. 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

  1. Antifungal activity and mode of action of saponins from Madhuca butyracea Macb.

    PubMed

    Lalitha, T; Venkataraman, L V

    1991-06-01

    The antifungal activity of saponins isolated as a byproduct from the defatted cake of M. butyracea oil seed is reported. The inhibitory concentrations against plant pathogenic fungi ranged from 500 to 2000 ppm. Maximum sensitivity to saponins was shown by Penicillium expansum. Cephalosporium acrimonium, Helminthosporium oryzae and Trichoderma viride. The saponins caused leakage of cell components and underwent degradation by fungus, Trichoderma viride. The usefulness of saponins as antimycotic agents is discussed. PMID:1889830

  2. Monoterpenoid Indole Alkaloids from Catharanthus roseus Cultivated in Yunnan.

    PubMed

    Wang, Bei; Liu, Lu; Chen, Ying-ying; Li, Qiong; Li, Dan; Liu, Va-ping; Luo, Xiao-dong

    2015-12-01

    A new monoterpenoid indole alkaloid, 15,20-dehydro-3α-(2-oxopropyl) coronaridine (1), along with sixteen analogues (2-17) were isolated from the leaves of Catharanthus roseus cultivated in Yunnan. The new alkaloid was elucidated on the basis of extensive spectroscopic analysis, and the known alkaloids were identified by comparison with the reported spectroscopic data. Among them, alkaloid 16 was isolated from Catharanthus for the first time. PMID:26882670

  3. Simulation of the type of coralin alkaloid-DNA binding

    NASA Astrophysics Data System (ADS)

    Kulikov, K. G.; Koshlan, T. V.

    2015-05-01

    Interaction between a synthesized coralin protoberberine alkaloid and the DNA double helix of the calf's thymus in a salt solution is studied by optical absorption spectroscopy and spectropolarimetry. The dependence of the spectral characteristics of the alkaloid on a ratio between the DNA base pair concentration and the alkaloid molecule concentration is considered. The parameters of bonds between the coralin alkaloid and the DNA double helix are determined using modified McGhee-von Hippel equations.

  4. The saponin-mediated enhanced uptake of targeted saporin-based drugs is strongly dependent on the saponin structure.

    PubMed

    Bachran, Christopher; Sutherland, Mark; Heisler, Iring; Hebestreit, Philipp; Melzig, Matthias F; Fuchs, Hendrik

    2006-04-01

    Saponins are a group of plant glycosides consisting of a steroid or triterpenoid aglycone to which one or more sugar chains are attached. They exhibit cell membrane-permeabilizing properties and, thus, have been investigated for their therapeutic potential. Recently, at a non-permeabilizing concentration saponinum album from Gypsophila paniculata L. has been described to enhance the cytotoxicity of a chimeric toxin in a cell culture model. To elucidate whether this enhancing effect is also mediated by other saponins, we analyzed the ability of seven different saponins to enhance the cytotoxicity of a targeted chimeric toxin. The chimeric toxin is composed of saporin, a plant ribosome-inactivating toxin, a cleavable adapter, and human epidermal growth factor (EGF). Cytotoxicity on EGF receptor (EGFR)-bearing cells was analyzed both alone and after combined application of saponin and chimeric toxin. Only two of the tested saponins, quillajasaponin and saponinum album, enhanced cytotoxicity by more than 1,000-fold, whereas the enhancement factors of the other saponins were only approximately 10-fold. In contrast to saponinum album, quillajasaponin enhanced the cytotoxicity both on control cells lacking EGFR and on target cells, indicating that, in this case, the enhancement is not target cell receptor specific. This is also the case for some of the saponins with low enhancement factors. Saponinum album resulted in a more than 13,600-fold receptor-specific enhancement, decreasing the 50% inhibitory concentration (IC(50)) from 2.4 nM to 0.18 pM, which renders it the best option to promote saporin-3-based drug uptake while retaining specificity for the EGFR. PMID:16565437

  5. Four new dammarane saponins from Zizyphus lotus.

    PubMed

    Maciuk, Alexandre; Lavaud, Catherine; Thépenier, Philippe; Jacquier, Marie-José; Ghédira, Kamel; Zèches-Hanrot, Monique

    2004-10-01

    Five dammarane-type saponins were isolated by means of centrifugal partition chromatography from the leaves of Zizyphus lotus. Their structures were elucidated using a combination of 1D and 2D 1H and 13C NMR spectra and mass spectroscopy. One of these glycosides is the known jujuboside B (5). Three are new jujubogenin glycosides, identified as 3-O-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranosyljujubogenin-20-O-(2,3,4-O-triacetyl)-alpha-L-rhamnopyranoside (1), 3-O-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranosyljujubogenin-20-O-alpha-L-rhamnopyranoside (2), and 3-O-alpha-L-rhamnopyranosyl-(1-->2)-[(4-sulfo)-beta-D-glucopyranosyl-(1-->3)]-alpha-L-arabinopyranosyljujubogenin (3). The last is a new sulfated derivative of jujubasaponine IV, identified as 3-O-alpha-L-rhamnopyranosyl-(1-->2)-[(4-sulfo)-beta-D-glucopyranosyl-(1-->3)]-beta-D-galactopyranosyl-(20R,22R)-16beta,22:16alpha,30-diepoxydammar-24-ene-3beta,20-diol (4). PMID:15497932

  6. Saponins from three species of Mimusops.

    PubMed

    Lavaud, C; Massiot, G; Becchi, M; Misra, G; Nigam, S K

    1996-02-01

    Six saponins were isolated from the seed kernel of Mimusops elengi, M. hexandra and M. manilkara. Their structures were determined using a combination of 1H NMR, 13C NMR and mass spectroscopy. Three of them are new compounds: 3-O-(beta-D-glucuronopyranosyl) 28-O-(alpha-L-rhamnopyranosyl (1-->3) beta-D-xylopyranosyl(1-->4) [alpha-L-rhamnopyranosyl(1-->3)] alpha-L-rhamnopyranosyl(1-->2) alpha-L-arabinopyranosyl) protobassic acid, 3-O-(beta-D-glucuronopyranosly) 28-O-(alpha-L-rhamnopyranosyl(1-->3) beta-D-xylopyranosyl(1-->4) alpha-L-rhamnopyranosyl(1-->2) alpha-L-arabinopyranosyl) 16-alpha-hydroxyprotobassic acid and 3-O-(beta-D-glucopyranosyl(1-->3) beta-D-glucopyranosyl) 28-O-(alpha-L-rhamnopyranosyl(1-->3) beta-D-xylopyranosyl(1-->4) alpha-L-rhamnopyranosyl(1-->2) alpha-L-arabinopyranosyl) protobassic acid. PMID:8835462

  7. Determination and toxicity of saponins from Amaranthus cruentus seeds.

    PubMed

    Oleszek, W; Junkuszew, M; Stochmal, A

    1999-09-01

    The concentrations of four triterpene saponins present in amaranth seeds were determined with high-performance liquid chromatography. It was shown that the total concentration of saponins in seeds was 0. 09-0.1% of dry matter. In germinating seeds an increase in concentration to 0.18% was observed after 4 days of germination, which remained stable for the next 3 days and later dropped to 0.09%. Highly purified extracts from the seeds were tested for their toxicity against hamsters. The hydrophobic fraction obtained by the extraction of seeds with methylene chloride showed no toxicity; the behavior of tested animals was similar to that of the group given an equivalent dose of rapeseed oil. A crude saponin fraction, containing approximately 70% of pure saponins in the matrix, showed some toxicity; the approximate lethal dose was calculated as 1100 mg/kg of body weight. It is concluded that low contents of saponins in amaranth seeds and their relatively low toxicity guarantee that amaranth-derived products create no significant hazard for the consumer. PMID:10552705

  8. Determination of saponins in legumes by direct densitometry.

    PubMed

    Gurfinkel, D M; Rao, A V

    2002-01-30

    Research has shown that dietary saponins may have health benefits. A simple, rapid method for the determination of saponins in legumes, using densitometry, is described. Saponin preparations, after pretreatment to remove nonsaponin components, are spotted in rows on a thin-layer chromatography plate, along with soyasaponin standards. The plate, without solvent development, is directly treated with sulfuric acid and heated. Violet spots develop which have a density proportional to the amount of saponin present. The standard curve has a correlation coefficient of 0.99 and is linear over the range of 1.25 to 10 microg of soyasaponins applied. The method has a coefficient of variation of less than 3% and compares favorably with quantitative thin-layer chromatography. Using this method the saponin contents of defatted soy flour (0.58%), dried navy beans (0.32%), and dried kidney beans (0.29%) were determined, and these results were found to be consistent with previous reports in the literature. PMID:11804507

  9. 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

  10. 21 CFR 119.1 - Dietary supplements containing ephedrine alkaloids.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 2 2012-04-01 2012-04-01 false Dietary supplements containing ephedrine alkaloids... UNREASONABLE RISK § 119.1 Dietary supplements containing ephedrine alkaloids. Dietary supplements containing ephedrine alkaloids present an unreasonable risk of illness or injury under conditions of use recommended...

  11. 21 CFR 119.1 - Dietary supplements containing ephedrine alkaloids.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 2 2011-04-01 2011-04-01 false Dietary supplements containing ephedrine alkaloids... UNREASONABLE RISK § 119.1 Dietary supplements containing ephedrine alkaloids. Dietary supplements containing ephedrine alkaloids present an unreasonable risk of illness or injury under conditions of use recommended...

  12. 21 CFR 119.1 - Dietary supplements containing ephedrine alkaloids.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 2 2010-04-01 2010-04-01 false Dietary supplements containing ephedrine alkaloids... UNREASONABLE RISK § 119.1 Dietary supplements containing ephedrine alkaloids. Dietary supplements containing ephedrine alkaloids present an unreasonable risk of illness or injury under conditions of use recommended...

  13. 21 CFR 119.1 - Dietary supplements containing ephedrine alkaloids.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 2 2014-04-01 2014-04-01 false Dietary supplements containing ephedrine alkaloids... UNREASONABLE RISK § 119.1 Dietary supplements containing ephedrine alkaloids. Dietary supplements containing ephedrine alkaloids present an unreasonable risk of illness or injury under conditions of use recommended...

  14. 21 CFR 119.1 - Dietary supplements containing ephedrine alkaloids.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 2 2013-04-01 2013-04-01 false Dietary supplements containing ephedrine alkaloids... UNREASONABLE RISK § 119.1 Dietary supplements containing ephedrine alkaloids. Dietary supplements containing ephedrine alkaloids present an unreasonable risk of illness or injury under conditions of use recommended...

  15. Alkaloid profiles of Mimosa tenuiflora and associated methods of analysis

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The alkaloid contents of the leaves and seeds of M. tenuiflora collected from northeastern Brazil were studied. Alkaloids were isolated by classical acid/base extraction procedures and by cation exchange solid phase extraction. The crude alkaloid fractions were then analysed by thin layer chromatogr...

  16. Diterpenoid alkaloids from the roots of Aconitum brachypodum Diels.

    PubMed

    Yang, Li-Guo; Zhang, Ying-Jie; Xie, Jia-Ying; Xia, Wei-Jun; Zhang, Hai-Yuan; Tang, Meng-Yun; Mei, Shuang-Xi; Cui, Tao; Wang, Jing-Kun; Zhu, Zhao-Yun

    2016-09-01

    A new diterpenoid alkaloid, named bullatine H (1), along with 10 known diterpenoid alkaloids were isolated from the roots of Aconitum brachypodum Diels (Ranunculaceae). The structure of 1 was elucidated by analysis of its spectroscopic data. It should be noted that compound 1 is the first example with 11, 13-dioxygenated denudatine-type diterpenoid alkaloid isolated from Aconitum brachypodum. PMID:27268073

  17. Production, detection, and purification of clavine-type ergot alkaloids.

    PubMed

    Wallwey, Christiane; Li, Shu-Ming

    2012-01-01

    Ergot alkaloids are indole derivatives with diverse structures and biological activities. This chapter describes the procedure from fungal cultivation to purified ergot alkaloids, as exemplified by fumigaclavine A in Penicillium commune. Furthermore, useful notes for working with purified ergot alkaloids are given. PMID:23065612

  18. Antibacterial and antifungal activity of liriodenine and related oxoaporphine alkaloids.

    PubMed

    Hufford, C D; Sharma, A S; Oguntimein, B O

    1980-10-01

    Liriodenine was evaluated for its antibacterial and antifungal activity against several microorganisms. Other related oxoaporphine alkaloids also were evaluated. Attempts to prepare oxoaporphine alkaloids from N-acetylnoraporphines were unsuccessful, but an unexpected phenanthrene alkaloid was obtained. A novel N-demethylation reaction was noted when oxogaucine methiodide and liriodenine methiodide were treated with alumina. PMID:7420287

  19. Rotational Investigation of Tropane Alkaloids

    NASA Astrophysics Data System (ADS)

    Cocinero, Emilio J.; Lesarri, Alberto; Ecija, Patricia; Grabow, Jens-Uwe; Fernández, Jose A.; Castano, Fernando

    2010-06-01

    We report an investigation of the rotational spectrum of several tropane alkaloids using the new Balle-Flygare-type FT-MW spectrometer built at the University of the Basque Country. The initial work focused on the azabicycles of tropinone, scopine and scopoline, vaporized using heating methods. For tropinone the spectrum confirmed the presence of equatorial and axial conformers originated by the inversion of the N-methyl group, with the tropane motif adopting a distorted chair configuration. The determination of substitution and effective structures for the two conformers included the 13C, 15N and 18O isotopomers observed in natural abundance. The structures revealed the flexibility and structural changes associated to the N-methyl inversion, mostly a flattening at the nitrogen atom and a simultaneous rising of the carbonyl group in the axial form. The investigation of scopine gave an intense spectrum, but it was inconsistent with the structural models expected for this molecule. The carrier of the new spectrum was later identified as scopoline, generated in situ by an intramolecular reaction at the moderate temperatures of the nozzle. A single conformation was detected for scopoline, with an ether bridge seriously distorting the tropane motif. E. J. Cocinero, A. Lesarri, P. écija, J.-U. Grabow, J. A. Fernández, F. Castaño, in publication, 2010 E. J. Cocinero, A. Lesarri, P. Écija, J.-U. Grabow, J. A. Fernández, F. Castaño, Phys. Chem. Chem. Phys.,in press, 2010

  20. Correlation between the spermicidal activity and the haemolytic index of certain plant saponins.

    PubMed

    Elbary, A A; Nour, S A

    1979-01-01

    The haemolytic index, the spermicidal efficacy and the effect on the vaginal mucosa of some plant saponins were determined. It was proved that a certain correlation exists between the haemolytic index and the spermicidal efficacy of these saponins. Saponin of Gypsophila paniculata was proved to be relatively superior when used in aqueous solution or when formulated in polyethylene glycol ointment base. PMID:542490

  1. Effects of Gypsophila saponins on bacterial growth kinetics and on selection of subterranean clover rhizosphere bacteria.

    PubMed

    Fons, F; Amellal, N; Leyval, C; Saint-Martin, N; Henry, M

    2003-06-01

    Plant secondary metabolites, such as saponins, have a considerable impact in agriculture because of their allelopathic effects. They also affect the growth of soil microorganisms, especially fungi. We investigated the influence of saponins on rhizosphere bacteria in vitro and in soil conditions. The effects of gypsophila saponins on the growth kinetics of rhizosphere bacteria were studied by monitoring the absorbance of the cultures in microtiter plates. Gypsophila saponins (1%) increased the lag phase of bacterial growth. The impact of gypsophila saponins on subterranean clover rhizosphere was also investigated in a pot experiment. The addition of gypsophila saponins did not modify clover biomass but significantly increased (twofold with 1% saponins) the weight of adhering soil. The number of culturable heterotrophic bacteria of the clover rhizosphere was not affected by the addition of gypsophila saponins. Nevertheless, the phenotypical characterization of the dominant Gram-negative strains of the clover rhizosphere, using the Biolog system, showed qualitative and quantitative differences induced by 1% saponins. With the addition of saponins, the populations of Chryseomonas spp. and Acinetobacter spp., the two dominant culturable genera of control clover, were no longer detectable or were significantly decreased, while that of Aquaspirillum dispar increased and Aquaspirillum spp. became the major genus. Aquaspirillum dispar and Aquaspirillum spp. were also the dominant rhizosphere bacteria of Gypsophila paniculata, which greatly accumulates these saponins in its roots. These results suggest that saponins may control rhizosphere bacteria in soil through rhizodeposition mechanisms. PMID:14569290

  2. Components characterization of total tetraploid jiaogulan (Gynostemma pentaphylla) saponin and its cholesterol-lowering properties

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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...

  3. Formulation and in vitro absorption analysis of Rhizoma paridis steroidal saponins.

    PubMed

    Liu, Zhen; Wang, Jieyin; Gao, Wenyuan; Man, Shuli; Guo, Huimin; Zhang, Jingze; Liu, Changxiao

    2013-01-30

    Rhizoma paridis steroidal saponins (RPS) have been prepared and identified as the active compounds for antitumor activity in our previous study. However, the low oral bioavailability of the steroidal saponins restricted its using. In the present research, solid dispersion (SD) and phytosome (PHY) formulation of RPS were prepared, and the physicochemical parameters as well as the intestinal absorption in rat everted gut sac model were investigated. Seven agents were selected as the carriers of SD, and poloxamer 407 (P 407) was the most suitable one. SD reduced the particle size of saponins in the water solution, enhanced the solubility of the saponins by about 3.5 folds, and significantly improved the absorption transport of saponins from 48 to 104 μg in everted gut sac of the rat system. PHY significantly enhanced the hydrophilic of saponins but showed little effect on the absorption in small intestine. Jejunum and ileum part absorbed more absolute contents of total saponins than duodenum parts. Six saponins, the main contents of RPS, used as the index of comparing the three forms, were also further investigated in the physico-chemical properties and the absorption tests. n-Octanol/water partition coefficients of the six saponins ordered in RPS, SD and PHY were Chonglouoside H>Dioscin>Polyphyllin D>Gracillin>Paris-VII>Formosanin C. All the saponins possessed the higher absorptive characteristics in SD formulation. The absorption rate of diosgenyl saponins in intestine was more than the pennogenyl saponins. PMID:23107795

  4. 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....

  5. 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....

  6. 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....

  7. 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....

  8. 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....

  9. Ether bridge formation in loline alkaloid biosynthesis

    PubMed Central

    Pan, Juan; Bhardwaj, Minakshi; Faulkner, Jerome R.; Nagabhyru, Padmaja; Charlton, Nikki D.; Higashi, Richard M.; Miller, Anne-Frances; Young, Carolyn A.; Grossman, Robert B.; Schardl, Christopher L.

    2014-01-01

    Lolines are potent insecticidal agents produced by endophytic fungi of cool-season grasses. These alkaloids are composed of a pyrrolizidine ring system and an uncommon ether bridge linking carbons 2 and 7. Previous results indicated that 1-aminopyrrolizidine was a pathway intermediate. We used RNA interference to knock down expression of lolO, resulting in the accumulation of a novel alkaloid identified as exo-1-acetamidopyrrolizidine based on high-resolution MS and NMR. Genomes of endophytes differing in alkaloid profiles were sequenced, revealing that those with mutated lolO accumulated exo-1-acetamidopyrrolizidine but no lolines. Heterologous expression of wild-type lolO complemented a lolO mutant, resulting in the production of N-acetylnorloline. These results indicated that the non-heme iron oxygenase, LolO, is required for ether bridge formation, probably through oxidation of exo-1-acetamidopyrrolizidine. PMID:24374065

  10. An efficient synthesis of loline alkaloids

    NASA Astrophysics Data System (ADS)

    Cakmak, Mesut; Mayer, Peter; Trauner, Dirk

    2011-07-01

    Loline (1) is a small alkaloid that, in spite of its simple-looking structure, has posed surprising challenges to synthetic chemists. It has been known for more than a century and has been the subject of extensive biological investigations, but only two total syntheses have been achieved to date. Here, we report an asymmetric total synthesis of loline that, with less then ten steps, is remarkably short. Our synthesis incorporates a Sharpless epoxidation, a Grubbs olefin metathesis and an unprecedented transannular aminobromination, which converts an eight-membered cyclic carbamate into a bromopyrrolizidine. The synthesis is marked by a high degree of chemo- and stereoselectivity and gives access to several members of the loline alkaloid family. It delivers sufficient material to support a programme aimed at studying the complex interactions between plants, fungi, insects and bacteria brokered by loline alkaloids.

  11. Analysis of toxic alkaloids in body samples.

    PubMed

    Beyer, Jochen; Drummer, Olaf H; Maurer, Hans H

    2009-03-10

    Many plants contain toxic alkaloids which may be dangerous to humans. Despite the large number of poisonous plants, cases of fatal plant poisonings are relatively rare. The frequencies of poisonings and the plants involved are often regionally specific. Plant poisonings can be aggregated into three categories: unintended ingestions, intended ingestions, and poisoning due to abuse of plant material. Unintended ingestions often occur in children or from a mix-up of plants and mushrooms in adults. Intended ingestions are common in homicides and suicides. Increasingly common is the abuse of plants for hallucinogenic reasons. Toxicological analysis of such alkaloids may help in diagnosis of poisoning or abuse cases. This review describes the toxic alkaloids aconitine, atropine, coniine, colchicine, cytisine, dimethyltryptamine, harmine, harmaline, ibogaine, kawain, mescaline, scopolamine, and taxine, which are often involved in fatal and non-fatal poisonings. The paper summarizes the symptoms of the intoxications and reviews the methods of detection of their toxic constituents in biological fluids. PMID:19147309

  12. Antimicrobial hasubanalactam alkaloid from Stephania glabra.

    PubMed

    Semwal, Deepak Kumar; Rawat, Usha

    2009-03-01

    A novel hasubanalactam alkaloid, named glabradine, has been isolated from the tubers of Stephania glabra, together with three known quaternary protoberberine alkaloids, palmatine, dehydrocorydalmine and stepharanine. The structure of glabradine was assigned as 7-O-demethyl-N,O-dimethyloxostephinine, by means of rigorous spectroscopic analysis including 2 D NMR measurements. It was evaluated for antimicrobial activity against Staphylococcus aureus, S. mutans, Microsporum gypseum, M. canis and Trichophyton rubrum and displayed potent antimicrobial activity superior to those of novobiocin and erythromycin used as positive controls. PMID:19148860

  13. Evidence for functional heterogeneity both between and within four sources of condensed tannin

    SciTech Connect

    Asquith, T.N.

    1985-01-01

    Condensed tannins are polymers of flavan-3-ols that are produced by many plants in a wide variety of tissues. The ability of these compounds to actively precipitate proteins has been linked to nutritional deficiencies in many animals. Four purified tannins (quebracho, wattle, pinto bean and sorghum) were compared to chemical assays and astringency towards (/sup 14/C)-BSA. Quebracho and wattle tannins were much less astringent and had longer chain lengths that sorghum or pinto bean tannins. Quebracho tannin had a very high affinity for salivary proline-rich glycoproteins (PRPs) and pinto bean tannin alone had a measurable affinity for soybean trypsin inhibitor. This suggests that tannin/protein interactions in vivo may be very specific. Protein bound carbohydrate enhanced the binding of PRPs to tanning and conferred specificity on the interactions. Carbohydrate also increases the solubility of protein/tanning complexes, which may aid the animal in eliminating the complexes. (/sup 125/I)-labeled condensed tannin was shown to retain the ability to discriminate between high and low affinity proteins. (/sup 125/I)-labeled phenols were isolated from livers and kidneys of rats fed (/sup 125/I)-labeled tannin. The techniques described in this thesis should be widely applicable to studying in vivo functions of condensed tannins.

  14. Exploitation of dietary tannins to improve rumen metabolism and ruminant nutrition.

    PubMed

    Patra, Amlan K; Saxena, Jyotisna

    2011-01-15

    Tannins (hydrolysable and condensed tannin) are polyphenolic polymers of relatively high molecular weight with the capacity to form complexes mainly with proteins due to the presence of a large number of phenolic hydroxyl groups. They are widely distributed in nutritionally important forage trees, shrubs and legumes, cereals and grains, which are considered as anti-nutritional compounds due to their adverse effects on intake and animal performance. However, tannins have been recognised to modulate rumen fermentation favourably such as reducing protein degradation in the rumen, prevention of bloat, inhibition of methanogenesis and increasing conjugated linoleic acid concentrations in ruminant-derived foods. The inclusion of tannins in diets has been shown to improve body weight and wool growth, milk yields and reproductive performance. However, the beneficial effects on rumen modulation and animal performance have not been consistently observed. This review discusses the effects of tannins on nitrogen metabolism in the rumen and intestine, and microbial populations (bacteria, protozoa, fungi and archaea), metabolism of tannins, microbial tolerance mechanisms to tannins, inhibition of methanogenesis, ruminal biohydrogenation processes and performance of animals. The discrepancies of responses of tannins among different studies are attributed to the different chemical structures (degree of polymerisation, procyanidins to propdelphinidins, stereochemistry and C-C bonding) and concentrations of tannins, and type of diets. An establishment of structure-activity relationship would be required to explain differences among studies and obtain consistent beneficial tannin effects. PMID:20815041

  15. Dihydrofuro [2,3-b] quinolinium alkaloids in cultured cells of Ptelea trifoliata L. : Isolation of a new alkaloid, ptelecultinium.

    PubMed

    Petit-Paly, G; Montagu, M; Viel, C; Rideau, M; Chénieux, J C

    1987-07-01

    Two dihydrofuroquinoline alkaloids, ptelefolonium and another new alkaloid, ptelecultinium, have been isolated from callus strains of Ptelea trifoliata L.. Ptelecultinium was not known to occur in the mature plants. The structure of these two alkaloids were established by UV, MS and (1)H-NMR spectra. PMID:24248767

  16. [Study on pretreatment of saponin wastewater by water hyacinthy].

    PubMed

    Li, Ze-tang; Cai, He-sheng; Ma, Teng; Wang, Hai-hua

    2006-07-01

    The pretreatment of the saponin wastewater by water hyacinth (Eichhornia crassipe) was studied. With contrast experiments, the results indicate that after 8 h adsorption by the dry air cells of water hyacinth, the concentration of chlorine ion in the saponin wastewater reduce 10%, chroma reduce 97.2%, pH change from 1.09 to 1.26, COD removal efficiency is 20%. The results indicate that the pretreatment process can improve biodegradability of the saponin wastewater, the biogas rate is 1.5 multiple than before , resulting in the benefit to the follow-up biological treatment. After the adsorption, water hyacinth biogas fermenting also improvement which is used for improve the effect of fermentative. PMID:16881311

  17. Adjuvant effects of saponins on animal immune responses*

    PubMed Central

    Rajput, Zahid Iqbal; Hu, Song-hua; Xiao, Chen-wen; Arijo, Abdullah G.

    2007-01-01

    Vaccines require optimal adjuvants including immunopotentiator and delivery systems to offer long term protection from infectious diseases in animals and man. Initially it was believed that adjuvants are responsible for promoting strong and sustainable antibody responses. Now it has been shown that adjuvants influence the isotype and avidity of antibody and also affect the properties of cell-mediated immunity. Mostly oil emulsions, lipopolysaccharides, polymers, saponins, liposomes, cytokines, ISCOMs (immunostimulating complexes), Freund’s complete adjuvant, Freund’s incomplete adjuvant, alums, bacterial toxins etc., are common adjuvants under investigation. Saponin based adjuvants have the ability to stimulate the cell mediated immune system as well as to enhance antibody production and have the advantage that only a low dose is needed for adjuvant activity. In the present study the importance of adjuvants, their role and the effect of saponin in immune system is reviewed. PMID:17323426

  18. Preferences for foods varying in macronutrients and tannins by lambs supplemented with polyethylene glycol.

    PubMed

    Titus, C H; Provenza, F D; Perevolotsky, A; Silanikove, N

    2000-06-01

    Supplemental polyethylene glycol (PEG) increases intake when animals eat foods high in tannins, but little is known about how PEG affects preference for foods that vary in concentrations of macronutrients and tannin. We investigated how varying macronutrients and tannins (commercially available extracts from quebracho trees) affected food intake, and we assessed the degree to which PEG (MW 3350) affected intake of tannin-rich foods by sheep. From 0715 to 1800 daily, lambs were offered diets that varied in concentrations of macronutrients: high energy/low protein (75% barley/25% alfalfa), medium energy/medium protein (35% barley/65% alfalfa), and low energy/high protein (100% alfalfa). Preference for these diets was determined in the absence of tannin, and then, in Trials 1 to 3, tannin was added in increasing concentrations (from 5 to 20%) to the diets with high and medium levels of energy. In Trial 4, tannin (10%) also was added to the low-energy diet. Lambs were supplemented with either 50 g of PEG mixed with 50 g of ground barley or 50 g of ground barley alone from 0700 to 1715 daily; lambs always consumed all of these supplements. In the absence of added tannins, all lambs preferred high energy/low protein > medium energy/medium protein > low energy/high protein. As tannin levels increased, preference for the high- and medium-energy foods decreased, and all lambs preferred foods that were lower in tannins and higher in protein. Lambs supplemented with PEG ate more macronutrients and tannins than unsupplemented lambs, and the effect became increasingly apparent as tannin levels increased from Trials 1 to 4. We conclude that the effectiveness of supplemental PEG may be low if alternative forages are equal or superior in nutritional quality and contain fewer metabolites with adverse effects. In such cases, animals would likely prefer alternatives to high-tannin foods. PMID:10875625

  19. [Inactivated saponin vaccine against salmonellal abortion in sheep].

    PubMed

    Girginov, G; Vodas, K; Bozhilov, B

    1978-01-01

    An inactivated saponine vaccine is prepared from five highly immunogenic Salmonella abortus ovis strains, selected by means of a biological test on white rats. Saline was used as a diluent of the vaccine, with the addition of 30 per cent glycerine, 0.012 per cent saponine and 0.1 per cent propiolactone. The optimum immunization dose of 5 cm3 is injected singly subcutaneously behind the elbow, two and a half months after impregnation. The vaccine is applied on infected farms before the disease occurs. The cellular-humoral immunity, which forms 14 days after the injection, lasts 4--5 months and protects the sheep against salmonellosis abortion. PMID:571645

  20. Steroidal Saponins from the Rhizomes of Anemarrhena asphodeloides.

    PubMed

    Yang, Bing-You; Zhang, Jing; Liu, Yan; Kuang, Hai-Xue

    2016-01-01

    Four new steroid saponins 1-4 were isolated from the rhizomes of Anemarrhena asphodeloides (Asparagaceae), as well as four known saponins: anemarsaponin B (5) timosaponin D (6), timosaponin E1 (7) anemarsaponin B II (8). Their structures were established through UV and NMR as well as MS data. All the compounds were evaluated for cytotoxicity against HepG2 and SGC7901 human cancer lines. Compounds 3 and 7 displayed medium antiproliferative activities on HepG2 and SGC7901 cells, with IC50 values of 43.90 and 57.90 μM, respectively. PMID:27548119

  1. Potent antitrypanosomal triterpenoid saponins from Mussaenda luteola

    PubMed Central

    Mohamed, Shaymaa M.; Bachkeet, Enaam Y.; Bayoumi, Soad A.; Jain, Surendra; Cutler, Stephen J.; Tekwani, Babu L.; Ross, Samir A.

    2016-01-01

    Five new triterpenoid saponins, heinsiagenin A 3-O-[α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl-(1→2)]-β-d-glucopyranoside (1), heinsiagenin A 3-O-[α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl-(1→2)]-[β-d-glucopyranosyl-(1→4)]-β-d-glucopyranoside (2), 2α-hydroxyheinsiagenin A 3-O-[α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl-(1→2)]-β-d-glucopyranoside (3), 2α-hydroxyheinsiagenin A 3-O-[β-d-glucopyranosyl-(1→2)]-[β-d-glucopyranosyl-(1→4)]-β-d-glucopyranoside (4) and N-(2S, 3R, 4R-3-methyl-4-pentanolid-2-yl)-18-hydroxylanosta-8 (9), 22E, 24E-trien-27-amide-3-O-[α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl-(1→2)]-[β-d-glucopyranosyl-(1→4)]-β-d-glucopyranoside (5) were isolated from the aerial parts of Mussaenda luteola Delile (Rubiaceae). Structural elucidation was based on the analysis of spectroscopic data (1D and 2D NMR) and HR-ESI-MS. Compound 1 showed potent antitrypanosomal activity with an IC50 value of 8.80 μM. Compounds 2–4 showed highly potent antitrypanosomal activity with IC50 values ranging between (2.57–2.84 μM) and IC90 values ranging between (3.36–4.35 μM), which are 5 fold greater than the positive control DFMO (IC50 and IC90 values of 13.06 and 28.99 μM, respectively). Compounds 1 and 2 showed moderate affinity to μ-opioid receptors with Ki values of 9.936 μM and 0.872 μM, respectively compared to a Ki value of 1.958 nM for the positive control, naloxone HCl. PMID:26524249

  2. Potent antitrypanosomal triterpenoid saponins from Mussaenda luteola.

    PubMed

    Mohamed, Shaymaa M; Bachkeet, Enaam Y; Bayoumi, Soad A; Jain, Surendra; Cutler, Stephen J; Tekwani, Babu L; Ross, Samir A

    2015-12-01

    Five new triterpenoid saponins, heinsiagenin A 3-O-[α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl-(1→2)]-β-d-glucopyranoside (1), heinsiagenin A 3-O-[α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl-(1→2)]-[β-d-glucopyranosyl-(1→4)]-β-d-glucopyranoside (2), 2α-hydroxyheinsiagenin A 3-O-[α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl-(1→2)]-β-d-glucopyranoside (3), 2α-hydroxyheinsiagenin A 3-O-[β-d-glucopyranosyl-(1→2)]-[β-d-glucopyranosyl-(1→4)]-β-d-glucopyranoside (4) and N-(2S, 3R, 4R-3-methyl-4-pentanolid-2-yl)-18-hydroxylanosta-8 (9), 22E, 24E-trien-27-amide-3-O-[α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl-(1→2)]-[β-d-glucopyranosyl-(1→4)]-β-d-glucopyranoside (5) were isolated from the aerial parts of Mussaenda luteola Delile (Rubiaceae). Structural elucidation was based on the analysis of spectroscopic data (1D and 2D NMR) and HR-ESI-MS. Compound 1 showed potent antitrypanosomal activity with an IC50 value of 8.80μM. Compounds 2-4 showed highly potent antitrypanosomal activity with IC50 values ranging between (2.57-2.84μM) and IC90 values ranging between (3.36-4.35μM), which are 5 fold greater than the positive control DFMO (IC50 and IC90 values of 13.06 and 28.99μM, respectively). Compounds 1 and 2 showed moderate affinity to μ-opioid receptors with Ki values of 9.936μM and 0.872μM, respectively compared to a Ki value of 1.958nM for the positive control, naloxone HCl. PMID:26524249

  3. Separation of soybean saponins from soybean meal by a technology of foam fractionation and resin adsorption.

    PubMed

    Jiang, Jianxing; Wu, Zhaoliang; Liu, Wei; Gao, Yanfei; Guo, Shenghao; Kang, Shufang

    2016-05-18

    Foam fractionation and resin adsorption were used to recover soybean saponins from the industrial residue of soybean meal. First, a two-stage foam fractionation technology was studied for concentrating soybean saponins from the leaching liquor. Subsequently, resin adsorption was used to purify soybean saponins from the foamate in foam fractionation. The results showed that the enrichment ratio, the recovery percentage, and the purity of soybean saponins by using the two-stage foam fractionation technology could reach 4.45, 74%, and 67%, respectively. After resin adsorption and desorption, the purity of soybean saponins in the freeze-dried powder from the desorption solution was 88.4%. PMID:26030807

  4. Performance and characterization of a new tannin-based coagulant

    NASA Astrophysics Data System (ADS)

    Beltrán-Heredia, J.; Sánchez-Martín, J.; Gómez-Muñoz, C.

    2012-09-01

    Diethanolamine and formaldehyde were employed to cationize tannins from black wattle. This novel coagulant called CDF was functionally characterized in removing sodium dodecylbenzene sulfonate (anionic surfactant) and Palatine Fast Black WAN (azoic dye). Refined tannin-derived commercial coagulants exhibited similar efficiency, while CDF presented higher coagulant ability than alum, a usual coagulant agent. Low doses of CDF (ca. 100 mg L-1) were able to remove more than 70 % of surfactant and more than 85 % of dye (initial pollutant concentration of ca. 100 mg L-1) and it presented no temperature affection and worked at a relatively wide pH range. Surfactant and dye removal responded to the classical coagulant-and-adsorption models, such as Frumkin-Fowler-Guggenheim or Gu and Zhu in the case of surfactant, and Langmuir and Freundlich in the case of dye.

  5. Therapeutic Potential of Steroidal Alkaloids in Cancer and Other Diseases.

    PubMed

    Jiang, Qi-Wei; Chen, Mei-Wan; Cheng, Ke-Jun; Yu, Pei-Zhong; Wei, Xing; Shi, Zhi

    2016-01-01

    Steroidal alkaloids are a class of secondary metabolites isolated from plants, amphibians, and marine invertebrates. Evidence accumulated in the recent two decades demonstrates that steroidal alkaloids have a wide range of bioactivities including anticancer, antimicrobial, anti-inflammatory, antinociceptive, etc., suggesting their great potential for application. It is therefore necessary to comprehensively summarize the bioactivities, especially anticancer activities and mechanisms of steroidal alkaloids. Here we systematically highlight the anticancer profiles both in vitro and in vivo of steroidal alkaloids such as dendrogenin, solanidine, solasodine, tomatidine, cyclopamine, and their derivatives. Furthermore, other bioactivities of steroidal alkaloids are also discussed. The integrated molecular mechanisms in this review can increase our understanding on the utilization of steroidal alkaloids and contribute to the development of new drug candidates. Although the therapeutic potentials of steroidal alkaloids look promising in the preclinical and clinical studies, further pharmacokinetic and clinical studies are mandated to define their efficacy and safety in cancer and other diseases. PMID:25820039

  6. Pharmacokinetics of Hoasca alkaloids in healthy humans.

    PubMed

    Callaway, J C; McKenna, D J; Grob, C S; Brito, G S; Raymon, L P; Poland, R E; Andrade, E N; Andrade, E O; Mash, D C

    1999-06-01

    N,N-Dimethyltryptamine (DMT), harmine, harmaline and tetrahydroharmine (THH) are the characteristic alkaloids found in Amazonian sacraments known as hoasca, ayahuasca, and yajè. Such beverages are characterized by the presence of these three harmala alkaloids, where harmine and harmaline reversibly inhibit monoamine oxidase A (MAO-A) while tetrahydroharmine weakly inhibits the uptake of serotonin. Together, both actions increase central and peripheral serotonergic activity while facilitating the psychoactivity of DMT. Though the use of such 'teas' has be known to western science for over 100 years, little is known of their pharmacokinetics. In this study, hoasca was prepared and administered in a ceremonial context. All four alkaloids were measured in the tea and in the plasma of 15 volunteers, subsequent to the ingestion of 2 ml hoasca/kg body weight, using gas (GC) and high pressure liquid chromatographic (HPLC) methods. Pharmacokinetic parameters were calculated and peak times of psychoactivity coincided with high alkaloid concentrations, particularly DMT which had an average Tmax of 107.5 +/- 32.5 min. While DMT parameters correlated with those of harmine, THH showed a pharmacokinetic profile relatively independent of harmine's. PMID:10404423

  7. Fluorescence lifetimes of some Rauwolfia alkaloids

    NASA Astrophysics Data System (ADS)

    Hidalgo, J.; Arjona, D. Gonzalez; Roldan, E.; Sanchez, M.

    1986-03-01

    The natural fluorescence lifetimes of the following Rauwolfia alkaloids, Reserpine, Rescinnamine, Corynanthine, Yohimbine, --- Ajmalicine, Serpentine and Ajmaline, have been calculated from a modified form of the Strickler-Berg equation. The actual lifetimes were derived from the quantum yields and the calculated natural lifetimes.

  8. A novel alkaloid from Mitrephora maingayi.

    PubMed

    Yu, Rong; Li, Bo-Gang; Ye, Qi; Zhang, Guo-Lin

    2005-06-01

    A novel alkaloid, maingayinine, together with dicentrinone, dicentrinene, L-2-O-methyl-chiro-inositol, allantoin, glaucine, N-phenyl-2-naphthylamine, terephthalic acid and ayanin, was isolated from the twigs of Mitrephora maingayi Hook (Annonaceae). Their structures were established predominantly by IR, MS and NMR spectral data. PMID:15938142

  9. Ergot alkaloids decrease rumen epithelial blood flow

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Two experiments were conducted to determine if ergot alkaloids affect blood flow to the absorptive surface of the rumen of steers. Steers (n=8 total) were pair-fed alfalfa cubes at 1.5× NEM and received ground endophyte-infected tall fescue seed (E+) or endophyte-free tall fescue seed (E-) via rumen...

  10. A new indole alkaloid from Ervatamia yunnanensis.

    PubMed

    Jin, Yong-Sheng; Du, Jing-Ling; Chen, Hai-Sheng; Jin, Li; Liang, Shuang

    2010-01-01

    The stems of Ervatamia yunnanensis have afforded a new indole alkaloid, ervataine (1), whose structure was determined by spectroscopic analysis. Five known compounds, ibogaine (2) coronaridine (3), heyneanine (4), voacangine hydroxyindolenine (5) and coronaridine hydroxyindolenine (6), were also isolated. PMID:19647051

  11. The Alkaloid Profiles of Lupinus sulphureus

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Lupines are common plants found on the rangelands in the western United States. Lupines are known to contain alkaloids that can be toxic and teratogenic causing congenital birth defects (crooked calf disease). One such lupine, Lupinus sulphureus, occurs in parts of Oregon, Washington, and British ...

  12. Scope of Hydrolysable Tannins as Possible Antimicrobial Agent.

    PubMed

    Ekambaram, Sanmuga Priya; Perumal, Senthamil Selvan; Balakrishnan, Ajay

    2016-07-01

    Hydrolysable tannins (HTs) are secondary metabolites from plants, which are roughly classified into gallotannins and ellagitannins having gallic acid and ellagic acid residues respectively attached to the hydroxyl group of glucose by ester linkage. The presence of hexahydroxydiphenoyl and nonahydroxyterphenoyl moieties is considered to render antimicrobial property to HTs. HTs also show considerable synergy with antibiotics. Nevertheless, they have low pharmacokinetic property. The present review presents the scope of HTs as future antimicrobial agent. Copyright © 2016 John Wiley & Sons, Ltd. PMID:27062587

  13. α-Glucosidase inhibitory hydrolyzable tannins from Eugenia jambolana seeds.

    PubMed

    Omar, Raed; Li, Liya; Yuan, Tao; Seeram, Navindra P

    2012-08-24

    Three new hydrolyzable tannins including two gallotannins, jamutannins A (1) and B (2), and an ellagitannin, iso-oenothein C (3), along with eight known phenolic compounds were isolated from the seeds of Eugenia jambolana fruit. The structures were elucidated on the basis of spectroscopic data analysis. All compounds isolated were evaluated for α-glucosidase inhibitory effects compared to the clinical drug acarbose. PMID:22867049

  14. 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

  15. 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. PMID:26055895

  16. 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. PMID:21161787

  17. Impact of condensed tannin size as individual and mixed polymers on bovine serum albumin precipitation.

    PubMed

    Harbertson, James F; Kilmister, Rachel L; Kelm, Mark A; Downey, Mark O

    2014-10-01

    Condensed tannins composed of epicatechin from monomer to octamer were isolated from cacao (Theobroma cacao, L.) seeds and added to bovine serum albumin (BSA) individually and combined as mixtures. When added to excess BSA the amount of tannin precipitated increased with tannin size. The amount of tannin required to precipitate BSA varied among the polymers with the trimer requiring the most to precipitate BSA (1000 μg) and octamer the least (50 μg). The efficacy of condensed tannins for protein precipitation increased with increased degree of polymerisation (or size) from trimers to octamers (monomers and dimers did not precipitate BSA), while mixtures of two sizes primarily had an additive effect. This study demonstrates that astringent perception is likely to increase with increasing polymer size. Further research to expand our understanding of astringent perception and its correlation with protein precipitation would benefit from sensory analysis of condensed tannins across a range of polymer sizes. PMID:24799203

  18. Tannin profile of different Monastrell wines and its relation to projected market prices.

    PubMed

    Gómez-Plaza, Encarna; Olmos, Oscar; Bautista-Ortín, Ana Belén

    2016-08-01

    This study focuses on the differences or similarities in tannin composition and concentration in Monastrell wines from different wineries from the same geographic area and, within each winery, from wines elaborated based on different projected market prices, to determine whether there is any relationship between the wine tannin composition and the projected price. The tannin composition of the different wines, all of them analyzed at the same point during winemaking, indicated that those elaborated as premium wines presented higher phenol and tannin contents. The mean degree of polymerization of these wines was also positively related with the projected price, which agreed with the results obtained by size exclusion chromatography, that showed that wines with high projected prices had a higher proportion of polymeric tannins, suggesting that techniques favoring the extraction of skin tannins were mostly used in those wines projected as premium wines, probably looking for greater mouthfeel complexity. PMID:26988530

  19. 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.

  20. No major role for binding by salivary proteins as a defense against dietary tannins in Mediterranean goats.

    PubMed

    Hanovice-Ziony, Michal; Gollop, Nathan; Landau, Serge Yan; Ungar, Eugene David; Muklada, Hussein; Glasser, Tzach Aharon; Perevolotsky, Avi; Walker, John Withers

    2010-07-01

    We investigated whether Mediterranean goats use salivary tannin-binding proteins to cope with tannin-rich forages by determining the affinity of salivary or parotid gland proteins for tannic acid or quebracho tannin. Mixed saliva, sampled from the oral cavity, or parotid gland contents were compared to the intermediate affinity protein bovine serum albumin with a competitive binding assay. Goats that consume tannin-rich browse (Damascus) and goats that tend to avoid tannins (Mamber) were sequentially fed high (Pistacia lentiscus L.), low (vetch hay), or zero (wheat hay) tannin forages. Affinity of salivary proteins for tannins did not differ between goat breeds and did not respond to presence or absence of tannins in the diet. Proteins in mixed saliva had slightly higher affinity for tannins than those in parotid saliva, but neither source contained proteins with higher affinity for tannins than bovine serum albumin. Similarly, 3 months of browsing in a tannin-rich environment had little effect on the affinity of salivary proteins for tannin in adult goats of either breed. We sampled mixed saliva from young kids before they consumed forage and after 3 months of foraging in a tannin-rich environment. Before foraging, the saliva of Mamber kids had higher affinity for tannic acid (but not quebracho tannin) than the saliva of Damascus kids, but there was no difference after 3 months of exposure to tannin-rich browse, and the affinity of the proteins was always similar to the affinity of bovine serum albumin. Our results suggest there is not a major role for salivary tannin-binding proteins in goats. Different tendencies of goat breeds to consume tannin-rich browse does not appear be related to differences in salivary tannin-binding proteins. PMID:20559693

  1. Differentiation of tannin-containing herbal drugs by HPLC fingerprints.

    PubMed

    He, Yu; Wu, Qiaofeng; Hansen, S H; Cornett, C; Møller, C; Lai, Pingfan

    2013-03-01

    A new HPLC system coupled with multiple detectors - Diode array detector (DAD), fluorescence detector (FLD), electrochemical amperometric detector (ADC) and mass spectrometry detector (MSD) was developed for the characterization and differentiation of tannin-containing herbal drugs included in The European Pharmacopoeia. The HPLC separation system consisted of an Agilent ZORBAX Eclipse XDB C18 column and a gradient water and methanol as the mobile phase which was kept at a flow rate of 0.3 mL x min(-1). Four kinds of detectors were connected by a micro-splitter valve and simultaneously recorded the response of each analytical sample. Thirty-one samples from eight kinds of tannin-containing drugs were measured using this HPLC system and their signals from all detectors were comprehensively processed via principal component analysis (PCA). The statistic result demonstrates that thirty-one batches from different herbal drugs can be reasonably identified and systematically classified by their chemical fingerprints. The proposed multi-detector HPLC method aided by chemometrics not only offers a new pattern for the study of tannin-containing herbs, but also provides a useful foundation for quality control of herbal medicines. PMID:23556331

  2. Biomolecular Interactions of Tannin Isolated from Oenothera gigas with Liposomes.

    PubMed

    Sekowski, Szymon; Ionov, Maksim; Dubis, Alina; Mavlyanov, Saidmukhtar; Bryszewska, Maria; Zamaraeva, Maria

    2016-04-01

    We have examined the interaction between hydrolysable tannin 1-O-galloyl-4,6-hexahydroxydiphenoyl-β-D-glucose (OGβDG) with neutral liposomes as a model of cell membranes composed of three lipids: lecithin, 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) and 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC) at different mass ratios. OGβDG in the concentration range 0.5-15 µg/ml (0.4-12 µM) strongly interacts with liposomal membranes by changing their structure, surface charge and fluidity. Used OGβDG molecules decrease and increase the rigidity of hydrophilic surface and hydrophobic parts of liposomes, respectively. At higher concentrations of tannin (>15 µM), liposomes are aggregated. Fourier Transform Infra-Red (FTIR) analysis showed that mainly -OH groups from OGβDG and also PO(2-) groups from phospholipids are responsible for the interaction. Obtained data indicate the importance of membrane lipid composition in interactions between tannins and cells. PMID:26621636

  3. Anti-inflammatory Hydrolyzable Tannins from Myricaria bracteata.

    PubMed

    Liu, Jia-Bao; Ding, Ya-Si; Zhang, Ying; Chen, Jia-Bao; Cui, Bao-Song; Bai, Jin-Ye; Lin, Ming-Bao; Hou, Qi; Zhang, Pei-Cheng; Li, Shuai

    2015-05-22

    Twelve hydrolyzable tannins were obtained from the twigs of Myricaria bracteata, including two new hellinoyl-type dimers, bracteatinins D1 (1) and D2 (2); a new hellinoyl-type trimer, bracteatinin T1 (3); two known monomers, nilotinin M4 (4) and 1,3-di-O-galloyl-4,6-O-(aS)-hexahydroxydiphenoyl-β-d-glucose (5); six known dimers, tamarixinin A (6), nilotinin D8 (7), hirtellins A (10), B (9), and E (8), and isohirtellin C (11); and a known trimer, hirtellin T3 (12). The structures of the tannins were elucidated by spectroscopic data analysis and comparisons to known tannins. All compounds were evaluated as free radical scavengers using 1,1-diphenyl-2-picrylhydrazyl and hydroxy radicals and compared to the activity of BHT and Trolox. Compound 6 showed a significant anti-inflammatory effect on croton oil-induced ear edema in mice (200 mg/kg, inhibition rate 69.8%) and on collagen-induced arthritis in DBA/1 mice (20 mg/kg, inhibition rate 46.0% at day 57). PMID:25918997

  4. Characterization and Physicochemical Properties of Condensed Tannins from Acacia catechu.

    PubMed

    Duval, Antoine; Avérous, Luc

    2016-03-01

    Condensed tannins from Acacia catechu were carefully studied to determine their chemical structure and physicochemical properties. The combined use of MALDI-TOF-MS and (13)C NMR revealed that catechin and epicatechin are the predominant monomers. Most of the compounds were dimers, as confirmed by size exclusion chromatography measurements. To evaluate their potential as aromatic building block in polymer synthesis, special care was given to the characterization and quantification of the different OH groups. A detailed (31)P NMR analysis showed the predominance of catechin, with a catechin/epicatechin ratio of 4.2:1. Two distinct (1)H NMR measurements confirmed the quantification. The thermal properties were also determined: the tannins showed a high temperature of degradation (ca. 190 °C) and a high glass transition temperature (ca. 140 °C), allowing for thermal processing or chemical reactions at relatively high temperature. A. catechu tannins thus present interesting features to be used as aromatic building blocks in polymer materials. PMID:26853705

  5. Relation ofSpodoptera eridania choice to tannins and protein oflotus corniculatus.

    PubMed

    Briggs, M A

    1990-05-01

    Plant secondary compounds such as tannins may influence herbivore choice. To determine if herbivory was influenced by tannin concentration,Spodoptera eridania larvae were given a choice ofLotus corniculatus plants whose chemical profiles were altered by fertilization. Herbivores chose plants that had been grown with symbiotic nitrogen fixation as their only nitrogen source more often than fertilized plants. Choice was related to protein concentration, but not to tannin concentration. PMID:24263826

  6. Activities of Tannins--From In Vitro Studies to Clinical Trials.

    PubMed

    Sieniawska, Elwira

    2015-11-01

    Tannins are considered as valuable plant secondary metabolites providing many benefits for human health. In this review information was gathered about bioactivity in vitro and in vivo, as well as about conducted clinical trials. The literature research was based on ScienceDirect, Scopus, and Cochrane databases and presents a wide range of tested activities of tannins. The described clinical trials verify laboratory tests and show the effective health benefits taken from supplementation with tannins. PMID:26749816

  7. Tannin diagenesis in mangrove leaves from a tropical estuary: A novel molecular approach

    USGS Publications Warehouse

    Hernes, P.J.; Benner, R.; Cowie, G.L.; Goi, M.A.; Bergamaschi, B.A.; Hedges, J.I.

    2001-01-01

    Molecular-level condensed tannin analyses were conducted on a series of mangrove (Rhizophora mangle) leaves at various stages of decomposition in a tropical estuary. Total molecular tannin yields ranged from 0.5% ash-free dry weight (AFDW) in the most highly degraded black leaves (6-7 weeks in the water) up to >7% AFDW in fresh leaves (80% procyanidin (PC) with the remainder being prodelphinidin (PD). PD tannin, with its higher degree of hydroxylation, proved to be more labile than PC tannin. Average chain length of condensed tannin (degree of polymerization) exhibited an initial increase in response to leaching, but later decreased in the subsequent shift toward abiotic or microbially mediated chemical reactions. Several trends point toward a possible condensation reaction in which tannin plays a role in nitrogen immobilization. These include an apparent inverse correlation between molecular tannin and nitrogen, a positive correlation between molecular tannin and percent basic amino acids, 13C-NMR data indicating transformation of tannin as opposed to remineralization, and 13C-NMR data showing loss of condensed tannin B-ring phenolic carbons coupled with preservation of A-ring phenolic carbon. In addition to condensed tannin, the molecular method used also yielded several triterpenoids. Triterpenoids accounted for up to 3.5% AFDW of the leaf material and exhibited a threefold increase between yellow senescent leaves entering the estuary and black leaves. This trend is likely due to the weakening of protective cuticular membranes during leaf decomposition, which leads to increased yields in the acidic conditions used for tannin analyses. Copyright ?? 2001 Elsevier Science Ltd.

  8. Pyrolysis-GC/MS of charred purified condensed tannin: towards identification of tannin-derived black carbon in environmental samples

    NASA Astrophysics Data System (ADS)

    Kaal, Joeri; Nierop, Klaas G. J.; Kraal, Peter; Preston, Caroline M.

    2010-05-01

    Tannins account for a significant proportion of plant biomass and are therefore a possible source of Black C in the charred remains from wildfires. Nonetheless, in contrast with other major biocomponents such as lignin and cellulose, the thermal degradation of tannins has not been investigated in laboratory charring experiments. We used pyrolysis-GC/MS to investigate the effects of furnace charring (30 min at fixed temperatures up to 600 °C under limited oxygen supply) on the degradation of pure condensed tannin (CT) isolated from Corsican pine (Pinus nigra) needles. The experiments showed a rapid loss (at 300 °C and higher) of the pyrogallol moieties of the B-ring of prodelphinidin-type CT, due to dehydroxylation. The relative abundance of catechols (from procyanidin-type CT) decreased at 350 °C and higher temperatures. This led to the formation of phenols that were strongly enriched between 300 and 400 °C. At higher temperatures, further dehydroxylation caused a decline in contributions of phenols producing a series of monocyclic aromatics ((alkyl)benzenes) and condensation of aromatics produced polycyclic aromatic hydrocarbons (PAHs), i.e. the typical pyrolysis fingerprint of strongly charred biomass. We conclude that (i) the thermal degradation of CT can be successfully monitored by pyrolysis-GC/MS, (ii) thermal degradation of CT is characterized by dehydroxylation of phenolic groups and condensation of aromatics that increase with temperature and (iii) CT-derived Black C may be recognized by catechol enrichments at low temperatures and possibly (relative) abundance of phenol and biphenyl at higher levels of thermal breakdown. Applying the same method to natural charcoal from gorse bushfires indicated that pyrolysis-GC/MS fingerprinting may allow for tannin identification in environmental Black C samples.

  9. Condensed tannins from acacia mangium bark: Characterization by spot tests and FTIR

    NASA Astrophysics Data System (ADS)

    Bharudin, Muhammad Azizi; Zakaria, Sarani; Chia, Chin Hua

    2013-11-01

    This paper describes the adaptation and evaluation of one chemical tests for tannins characterization in acacia mangium bark. Acid butanol test developed to identify respectively condensed tannins is described. The two traditional tests used for tannin characterization namely ferric test and vanillin test were also performed and their functional also discussed. Condensed tannins were extracted from acacia mangium bark using water medium in presence of three different concentration basic reagent of NaOH(5%,10% and 15%) and were characterized by FT-IR spectrometry.

  10. Effects of tannin source and concentration from tree leaves on two species of tadpoles.

    PubMed

    Earl, Julia E; Semlitsch, Raymond D

    2015-01-01

    Vegetation in and around freshwater ecosystems can affect aquatic organisms through the production of secondary compounds, which are retained in leaves after senescence and are biologically active. Tannins can be toxic to tadpoles, but the plant source of tannins and tannin concentration have been confounded in experimental designs in previous studies. To examine the effects of the concentration and source of tannins (tree species), we examined the effects of 4 factors on tadpole survival, growth, and development: tannin source (red oak [Quercus rubra], white oak [Quercus alba], or sugar maple [Acer saccharum]); tannin concentration (including a control); diet protein level; and tadpole species (American toad [Anaxyrus americanus] and spring peepers [Pseudacris crucifer]). Tannin source and concentration affected spring peeper survival, but American toads had uniformly high survival. Spring peepers had a lower survival rate in high tannin concentrations of oak leachate but a high survival rate in both concentrations of sugar maple leachate. These differences in survival did not correspond with changes in dissolved oxygen, and no effect of dietary protein level on tadpole performance was observed. The presence of plant leachate resulted in increased tadpole growth in both species, but the mechanism for this finding is unclear. The results of the present study show that tannin concentration and source are important factors for tadpole performance, adding further evidence that plant chemistry can affect aquatic organisms. PMID:25319714

  11. Effects of tannins on digestion and detoxification activity in gray squirrels (Sciurus carolinensis).

    PubMed

    Chung-MacCoubrey, A L; Hagerman, A E; Kirkpatrick, R L

    1997-01-01

    Acorn tannins may affect food preferences and foraging strategies of squirrels through effects on acorn palatability and digestibility and squirrel physiology. Captive eastern gray squirrels (Sciurus carolinensis) were fed 100% red oak (Quercus rubra) or white oak (Quercus alba) acorn diets to determine effects on intake, digestion, and detoxification activity. Red oak acorns had higher phenol and tannin levels, which may explain the lower dry matter intakes and apparent protein digestibilities and the higher glucuronidation activities observed in squirrels. Although the white oak acorn diet had lower apparent protein digestibilities than the reference diet, it did not suppress dry matter intake for a prolonged period or stimulate glucuronidation. Negative physiological effects of a 100% red oak acorn diet suggest gray squirrels may require other foods to dilute tannin intake and provide additional nutrients. To distinguish the roles of different tannin types in the observed effects of acorn diets on squirrels, squirrels were fed rat chow containing no tannins, 4% or 8% tannic acid (hydrolyzable tannin), or 3% or 6% quebracho (condensed tannin). Apparent protein digestibilities were reduced by tannic acid and quebracho diets. Only the 8% tannic acid diet tended to increase glucuronidation. Specific effects of tannins may largely depend on tannin type, composition, and source and on other nutritional and physiological factors. PMID:9231400

  12. Synergistic inhibition of Haemonchus contortus exsheathment by flavonoid monomers and condensed tannins

    PubMed Central

    Klongsiriwet, Chaweewan; Quijada, Jessica; Williams, Andrew R.; Mueller-Harvey, Irene; Williamson, Elizabeth M.; Hoste, Hervé

    2015-01-01

    This study investigated the separate and combined anthelmintic (AH) effects of different phenolic compounds, including condensed tannins and flavonoids, all of which are known to occur in willow leaves, a potentially valuable dry season feed. A range of contrasting model tannins, which span the whole range of willow tannins, were isolated from tilia flowers, goat willow leaves, black currant leaves and red currant leaves. All together, the tested compounds represented the major tannin types (procyanidins and prodelphinidins) and flavonoid types (flavonols, flavones and flavanones). The larval exsheathment inhibition assay (LEIA) was used to assess their in vitro effects on Haemonchus contortus third stage larvae. Arbutin, vanillic acid, and taxifolin proved to be ineffective whereas naringenin, quercetin and luteolin were highly effective at 250 μM concentrations. Procyanidin (PC) tannins tended to be less active than prodelphinidin tannins (PD). Experiments with combinations of tannins and quercetin or luteolin revealed for the first time the existence of synergistic AH effects between tannins and flavonoid monomers. They also provided evidence that synergistic effects appear to occur at slightly lower concentrations of PC than PD. This suggests that the AH activity of condensed tannins can be significantly enhanced by the addition of quercetin or luteolin. This information may prove useful for plant breeding or selection and for designing optimal feed mixtures. PMID:26199861

  13. Condensed Tannins from Ficus virens as Tyrosinase Inhibitors: Structure, Inhibitory Activity and Molecular Mechanism

    PubMed Central

    Chai, Wei-Ming; Feng, Hui-Ling; Zhuang, Jiang-Xing; Chen, Qing-Xi

    2014-01-01

    Condensed tannins from Ficus virens leaves, fruit, and stem bark were isolated and their structures characterized by 13C nuclear magnetic resonance spectrometry, high performance liquid chromatography electrospray ionization mass spectrometry, and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. The results showed that the leaves, fruit, and stem bark condensed tannins were complex mixtures of homo- and heteropolymers of B-type procyanidins and prodelphinidins with degrees of polymerization up to hexamer, dodecamer, and pentadecamer, respectively. Antityrosinase activities of the condensed tannins were studied. The results indicated that the condensed tannins were potent tyrosinase inhibitors. The concentrations for the leaves, fruit, and stem bark condensed tannins leading to 50% enzyme activity were determined to be 131.67, 99.89, and 106.22 μg/ml on monophenolase activity, and 128.42, 43.07, and 74.27 μg/ml on diphenolase activity. The inhibition mechanism, type, and constants of the condensed tannins on the diphenolase activity were further investigated. The results indicated that the condensed tannins were reversible and mixed type inhibitors. Fluorescence quenching, copper interacting, and molecular docking techniques were utilized to unravel the molecular mechanisms of the inhibition. The results showed that the hydroxyl group on the B ring of the condensed tannins could chelate the dicopper irons of the enzyme. Moreover, the condensed tannins could reduce the enzyme product o-quinones into colourless compounds. These results would contribute to the development and design of antityrosinase agents. PMID:24637701

  14. Assessment of tannin variation in Tamarisk foliage across a latitudinal gradient

    USGS Publications Warehouse

    Hussey, A.M.; Kimball, B.A.; Friedman, J.M.

    2011-01-01

    Certain phenotypic traits of plants vary with latitude of origin. To understand if tannin concentration varies among populations of tamarisk (Tamarix spp.) according to a latitudinal gradient, an analytical method was adapted from an enological tannin assay. The tannin content (wet basis) of tamarisk foliage collected from 160 plants grown in a common garden ranged from 8.26 to 62.36 mg/g and was not correlated with the latitude of the original North American plant collection site. Tannins do not contribute to observed differences in herbivory observed among these tamarisk populations.

  15. Polymeric tannins significantly alter properties and in vitro digestibility of partially gelatinized intact starch granule.

    PubMed

    Amoako, Derrick B; Awika, Joseph M

    2016-10-01

    Excess calorie intake is a growing global problem. This study investigated effect of complexing partially gelatinized starch with condensed tannins on in vitro starch digestibility. Extracts from tannin and non-tannin sorghum, and cellulose control, were reacted with normal and waxy maize starch in 30% (30E) and 50% ethanol (50E) solutions at 70°C/20min. More tannins complexed with the 30E than 50E starches (mean 6.2 vs 3.5mg/g, respectively). In the 30E treatments, tannins significantly increased crystallinity, pasting temperature, peak viscosity, and slow digesting starch (from 100 to 274mg/g) in normal, but not waxy starch, suggesting intragranular cross-linking with amylose. Tannins doubled resistant starch (RS) to approx. 300mg/g in both starches. In 50E treatments, tannins made both maize starches behave like raw potato starch (>90% RS), suggesting granule surface interactions dominated. Non-tannin treatments generally behaved similar to cellulose. Condensed tannins could be used to favorably alter starch digestion profile. PMID:27132818

  16. Synergistic inhibition of Haemonchus contortus exsheathment by flavonoid monomers and condensed tannins.

    PubMed

    Klongsiriwet, Chaweewan; Quijada, Jessica; Williams, Andrew R; Mueller-Harvey, Irene; Williamson, Elizabeth M; Hoste, Hervé

    2015-12-01

    This study investigated the separate and combined anthelmintic (AH) effects of different phenolic compounds, including condensed tannins and flavonoids, all of which are known to occur in willow leaves, a potentially valuable dry season feed. A range of contrasting model tannins, which span the whole range of willow tannins, were isolated from tilia flowers, goat willow leaves, black currant leaves and red currant leaves. All together, the tested compounds represented the major tannin types (procyanidins and prodelphinidins) and flavonoid types (flavonols, flavones and flavanones). The larval exsheathment inhibition assay (LEIA) was used to assess their in vitro effects on Haemonchus contortus third stage larvae. Arbutin, vanillic acid, and taxifolin proved to be ineffective whereas naringenin, quercetin and luteolin were highly effective at 250 μM concentrations. Procyanidin (PC) tannins tended to be less active than prodelphinidin tannins (PD). Experiments with combinations of tannins and quercetin or luteolin revealed for the first time the existence of synergistic AH effects between tannins and flavonoid monomers. They also provided evidence that synergistic effects appear to occur at slightly lower concentrations of PC than PD. This suggests that the AH activity of condensed tannins can be significantly enhanced by the addition of quercetin or luteolin. This information may prove useful for plant breeding or selection and for designing optimal feed mixtures. PMID:26199861

  17. Absorption and Transport of Sea Cucumber Saponins from Apostichopus japonicus

    PubMed Central

    Li, Shuai; Wang, Yuanhong; Jiang, Tingfu; Wang, Han; Yang, Shuang; Lv, Zhihua

    2016-01-01

    The present study is focused on the intestinal absorption of sea cucumber saponins. We determined the pharmacokinetic characteristics and bioavailability of Echinoside A and Holotoxin A1; the findings indicated that the bioavailability of Holotoxin A1 was lower than Echinoside A. We inferred that the differences in chemical structure between compounds was a factor that explained their different characteristics of transport across the intestine. In order to confirm the absorption characteristics of Echinoside A and Holotoxin A1, we examined their transport across Caco-2 cell monolayer and effective permeability by single-pass intestinal perfusion. The results of Caco-2 cell model indicate that Echinoside A is transported by passive diffusion, and not influenced by the exocytosis of P-glycoprotein (P-gp, expressed in the apical side of Caco-2 monolayers as the classic inhibitor). The intestinal perfusion also demonstrated well the absorption of Echinoside A and poor absorption of Holotoxin A1, which matched up with the result of the Caco-2 cell model. The results demonstrated our conjecture and provides fundamental information on the relationship between the chemical structure of these sea cucumber saponins and their absorption characteristics, and we believe that our findings build a foundation for the further metabolism study of sea cucumber saponins and contribute to the further clinical research of saponins. PMID:27322290

  18. Lipidated Steroid Saponins from Dioscorea villosa (Wild Yam)†

    PubMed Central

    Dong, Shi-Hui; Cai, Geping; Napolitano, José G.; Nikolić, Dejan; Lankin, David C.; McAlpine, James B.; van Breemen, Richard B.; Soejarto, Djaja D.; Pauli, Guido F.; Chen, Shao-Nong

    2014-01-01

    Two groups of lipidated steroid saponins including seven new compounds (2, 3, 5, and 7–10) were isolated from the widely used botanical, wild yam (Dioscorea villosa), employing a fractionation protocol of metabolomic mining. This methodology has very recently led to the isolation of 14 diarylheptanoids from the same plant. Together with these lipidated steroid saponins, they establish additional new markers for Dioscorea villosa. The lipidation of steroids with analogue long-chain fatty acids containing different degrees of unsaturation generates entire series of compounds which are difficult to purify and analyze. The structures of the two series of lipidated steroid saponins (series A and B) were demonstrated by a combination of 1D and 2D NMR as well as GC-MS after chemical modification. Series A was determined to be a mixture of lipidated spirostanol glycosides (1–5), while series B (6–10) proved to be a mixture of five lipidated clionasterol glucosides. The latter group represents the first derivatives of clionasterol to be found in D. villosa. The discovery of this specific structural type of aliphatic esters of steroid saponins expands the characterization of the secondary metabolome of D. villosa. It also may inspire biological studies which take into account the lipophilic character and significantly altered physiochemical characteristics of these otherwise relatively polar phytoconstituents. PMID:23968665

  19. Absorption and Transport of Sea Cucumber Saponins from Apostichopus japonicus.

    PubMed

    Li, Shuai; Wang, Yuanhong; Jiang, Tingfu; Wang, Han; Yang, Shuang; Lv, Zhihua

    2016-01-01

    The present study is focused on the intestinal absorption of sea cucumber saponins. We determined the pharmacokinetic characteristics and bioavailability of Echinoside A and Holotoxin A₁; the findings indicated that the bioavailability of Holotoxin A₁ was lower than Echinoside A. We inferred that the differences in chemical structure between compounds was a factor that explained their different characteristics of transport across the intestine. In order to confirm the absorption characteristics of Echinoside A and Holotoxin A₁, we examined their transport across Caco-2 cell monolayer and effective permeability by single-pass intestinal perfusion. The results of Caco-2 cell model indicate that Echinoside A is transported by passive diffusion, and not influenced by the exocytosis of P-glycoprotein (P-gp, expressed in the apical side of Caco-2 monolayers as the classic inhibitor). The intestinal perfusion also demonstrated well the absorption of Echinoside A and poor absorption of Holotoxin A₁, which matched up with the result of the Caco-2 cell model. The results demonstrated our conjecture and provides fundamental information on the relationship between the chemical structure of these sea cucumber saponins and their absorption characteristics, and we believe that our findings build a foundation for the further metabolism study of sea cucumber saponins and contribute to the further clinical research of saponins. PMID:27322290

  20. Influence of saponins on the biodegradation of halogenated phenols.

    PubMed

    Kaczorek, Ewa; Smułek, Wojciech; Zdarta, Agata; Sawczuk, Agata; Zgoła-Grześkowiak, Agnieszka

    2016-09-01

    Biotransformation of aromatic compounds is a challenge due to their low aqueous solubility and sorptive losses. The main obstacle in this process is binding of organic pollutants to the microbial cell surface. To overcome these, we applied saponins from plant extract to the microbial culture, to increase pollutants solubility and enhance diffusive massive transfer. This study investigated the efficiency of Quillaja saponaria and Sapindus mukorossi saponins-rich extracts on biodegradation of halogenated phenols by Raoultella planticola WS2 and Pseudomonas sp. OS2, as an effect of cell surface modification of tested strains. Both strains display changes in inner membrane permeability and cell surface hydrophobicity in the presence of saponins during the process of halogenated phenols biotransformation. This allows them to more efficient pollutants removal from the environment. However, only in case of the Pseudomonas sp. OS2 the addition of surfactants to the culture improved effectiveness of bromo-, chloro- and fluorophenols biodegradation. Also introduction of surfactant allowed higher biodegradability of halogenated phenols and can shorten the process. Therefore this suggests that usage of plant saponins can indicate more successful halogenated phenols biodegradation for selected strains. PMID:27232205

  1. Cycloartane-Type Saponins from Astragalus tmoleus var. tmoleus.

    PubMed

    Avunduk, Sibel; Mitaine-Offer, Anne-Claire; Miyamoto, Tomofumi; Tanaka, Chiaki; Lacaille-Dubois, Marie-Aleth

    2016-01-01

    Five known cycloartane-type glycosides were isolated from the roots of A. tmoleus Boiss. var. tmoleus. The identification of these compounds was mainly achieved by 1D and 2D NMR spectroscopic techniques and FABMS. The results of our studies confirm that triterpene saponins with the cycloartane-type skeleton might be chemotaxonomically significant for the genus Astragalus. PMID:26996015

  2. Atropurosides A-G, new steroidal saponins from Smilacina atropurpurea.

    PubMed

    Zhang, Ying; Li, Hai-Zhou; Zhang, Ying-Jun; Jacob, Melissa R; Khan, Shabana I; Li, Xing-Cong; Yang, Chong-Ren

    2006-08-01

    Atropurosides A-G (1-7), seven new steroidal saponins, which possess new polyhydroxylated aglycones, were isolated from the rhizomes of Smilacina atropurpurea (Convallariaceae), together with a known saponin, dioscin (8). Their structures were elucidated on the basis of detailed spectroscopic analysis, including 1D and 2D NMR techniques and chemical methods. Antifungal testing of the eight compounds indicated that atropurosides B (2) and F (6) were fungicidal against Candida albicans, Candida glabrata, Cryptococcus neoformans, and Aspergillus fumigatus with minimum fungicidal concentrations (MFCs) < or = 20 microg/ml, while dioscin (8) was selectively active against C. albicans and C. glabrata (MFC < or = 5.0 microg/ml). Furthermore, the antifungal saponins 2, 6, and 8 were evaluated for their in vitro cytotoxicities in a panel of human cancer cell lines (SK-MEL, KB, BT-549, SK-OV-3, and HepG2) and non-cancerous Vero cells. All showed moderate cytotoxicities. It appears that the antifungal activity of these steroidal saponins correlates with their cytotoxicity against mammalian cells. PMID:16766007

  3. Oleanane-type triterpenoid saponins from Silene armeria.

    PubMed

    Takahashi, Nobuyuki; Li, Wei; Koike, Kazuo

    2016-09-01

    Twelve triterpenoid saponins, including seven compounds (i.e., armerosides A-G) hitherto unknown, were isolated from whole plants of Silene armeria. Their structures were established based on extensive spectroscopic analyses and chemical methods. From a biosynthetic perspective, C-23 oxidation of the sapogenin appears to be a key factor in the glycosylation pathway. PMID:27460531

  4. Steroidal saponins from fresh stems of Dracaena angustifolia

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Six new steroidal saponins (1-6), angudracanosides A-F, were isolated from fresh stems of Dracaena angustifolia, together with eight known compounds. The structures of compounds 1-6 were determined by detailed spectroscopic analyses and chemical methods. Antifungal testing of all compounds showed th...

  5. Triterpenoidal saponins: bioactive secondary metabolites from Zygophyllum coccineum L

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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...

  6. A new steroidal saponin from dragon's blood of Dracaena cambodiana.

    PubMed

    Luo, Ying; Shen, Hai-Yan; Zuo, Wen-Jian; Wang, Hui; Mei, Wen-Li; Dai, Hao-Fu

    2015-01-01

    Phytochemical study on dragon's blood of Dracaena cambodiana led to a new steroidal saponin, cambodianoside G(1), and six known ones (2-7). The structure of the new compound was elucidated on the basis of detailed spectroscopic analysis. Evaluation of antibacterial activities showed that compound 7 exhibited antibacterial activity against Staphylococcus aureus. PMID:25523446

  7. Oleanane-type Triterpene Saponins from Glochidion glomerulatum.

    PubMed

    Thu, Vu Kim; Thanga, Nguyen Van; Nhiem, Nguyen Xuan; Anh, Hoang Le Tuan; Yen, Pham Hai; Minh, Chau Van; Kiem, Phan Van; Kim, Nan Young; Park, Seon Ju; Kim, Seung Hyun

    2015-06-01

    Two new oleanane-type triterpene saponins, named glomeruloside I (1) and glomeruloside II (2), were isolated from the leaves of Glochidion glomerulatum (Miq.) Boerl. Their structures were determined by extensive spectroscopic methods, including 1D- and 2D-NMR, MS data, and chemical methods. PMID:26197505

  8. The origins of tannins and flavonoids in black-wattle barks and heartwoods, and their associated `non-tannin' components

    PubMed Central

    Saayman, H. M.; Roux, D. G.

    1965-01-01

    1. The distributions of flavonoid, carbohydrate, amino acid and imino acid components in the leaves, twig bark, stem bark, root bark and heartwoods of the black-wattle tree were compared by paper chromatography after their isolation from specific portions of the tree. 2. Wattle leaves contain mainly myricitrin, (+)-gallocatechin, an unknown myricetin glycoside and leuco-delphinidin tannins, together with smaller amounts of (+)-catechin, quercitrin and other flavonol glycosides. These are prominent in the twig bark, but decline progressively with age in the stem bark and are absent from root bark. 3. The non-phenolic components of the mature stem bark were shown to be (+)-pinitol, sucrose, glucose, fructose, l(−)-pipecolic acid, trans-4-hydroxy-l(−)-pipecolic acid, α-alanine, arginine, aspartic acid, glutamic acid, l(−)-proline, serine, a `steroid' alcohol and a long-chain β-diketone. 4. Wattle bark and heartwood `tannins' consist of the analogues of closely related prototypes with common origins in the vascular tissues of the bark. Leaf `tannins' are superimposed on the bark components mainly during the initial stages of bark growth. 5. Origins of the pipecolic acids and the transformations of carbohydrates in the sap- and heart-woods are discussed. PMID:5881667

  9. 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. PMID:21480409

  10. Preference for condensed tannins by sheep in response to challenge infection with Haemonchus contortus.

    PubMed

    Juhnke, J; Miller, J; Hall, J O; Provenza, F D; Villalba, J J

    2012-08-13

    Herbivores prefer feeds that supply required nutrients and avoid those with excess nutrients and plant secondary compounds (PSC). Nevertheless, PSC such as condensed tannins can provide beneficial medicinal effects to herbivores as they act against infective diseases such as parasitism. The objectives of this study were to determine: (1) if parasitized lambs increased preference for a tannin-rich feed after they experienced the beneficial antiparasitic effects of condensed tannins relative to parasitized lambs that did not experience such benefits, and (2) if preference for the tannin-rich feed in the former group decreased when parasite burdens subsided. Twenty two lambs were familiarized with beet pulp and beet pulp+8% quebracho tannins (beet pulp+tannins) and choices were given between the two feeds (initial preference tests). Subsequently, all animals were dosed with 10,000 L(3) stage larvae of Haemonchus contortus. Twenty-two days later, animals were exposed to beet pulp (Control group; n=11) or beet pulp+tannins (Treatment group; n=11) during 24 d. After exposure (during a parasitic infection) animals in both groups were given choices between the two feeds. Lastly, animals in both groups received an antiparasitic drench and were again given a choice between both feeds (after a parasitic infection). Lambs preferred beet pulp to beet pulp+tannins throughout the study (P<0.001) and no difference in preference for the tannin-rich feed was detected between groups during initial preference tests (P>0.05). However, during a parasitic infection, intake of and preference for the tannin-rich feed was higher for lambs that experienced the beneficial effects of condensed tannins while parasitized (Treatment) than for lambs that did not (Control) (P<0.05). When parasitic infections were terminated by chemotherapy, differences between groups disappeared (P>0.05). Preference by the Treatment group for the tannin-rich feed was lower after than during a parasite infection (P

  11. Selection of tannins by sheep in response to gastrointestinal nematode infection.

    PubMed

    Villalba, J J; Provenza, F D; Hall, J O; Lisonbee, L D

    2010-06-01

    Herbivores learn to select compounds that attenuate the aversive effects of plant secondary metabolites (PSM), but can they increase intake of PSM they typically avoid when these PSM provide medicinal effects? We hypothesized that herbivores learn to increase intake of PSM-containing feeds when experiencing a gastrointestinal parasitic infection. Ten lambs with natural gastrointestinal parasitic burdens (PB) and 10 nonparasitized lambs (NP) were offered a choice of alfalfa (Medicago sativa) and alfalfa mixed with 10% quebracho tannin (Schinopsis quebracho-colorado; alfalfa:tannins) before and after they were conditioned with the postingestive effects of tannins. Preference for alfalfa:tannins did not differ between groups before experiencing the postingestive effects of tannins (P = 0.85) or when parasite loads were terminated due to the administration of ivermectin (P = 0.18). In contrast, when tested with a parasite burden, lambs in PB consumed more alfalfa:tannins (P = 0.08), showed greater preference for alfalfa:tannins (P = 0.07), and consumed less alfalfa than lambs in NP (P = 0.06). Ingestion of tannins by lambs in PB was followed by reduced fecal egg counts (FEC; P = 0.006), and there was a direct proportional relationship between preference for alfalfa:tannins and FEC (P = 0.07). In summary, parasitized lambs increased their intake of alfalfa:tannins when they experienced a parasite burden, which suggests they self-medicated with tannins against parasites. Self-selection of PSM has implications for the quest for alternatives to chemoprophylaxis in the treatment and well-being of parasitized wild and domestic animals grazing in pasturelands and in confinement. PMID:20190171

  12. Anthelmintic effect of plant extracts containing condensed and hydrolyzable tannins on Caenorhabditis elegans and their antioxidant capacity

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Although tannin-rich forages are known to increase protein uptake and to reduce gastrointestinal nematode infections in grazing ruminants, most published research involves forages with condensed tannins (CT), while published literature lacks information on the anthelmintic capacity, nutritional bene...

  13. Toxicosis by Plant Alkaloids in Humans and Animals in Colombia.

    PubMed

    Diaz, Gonzalo J

    2015-12-01

    Due to its tropical location, chains of mountains, inter-Andean valleys, Amazon basin area, eastern plains and shores on both the Atlantic and Pacific Oceans, Colombia has many ecosystems and the second largest plant biodiversity in the world. Many plant species, both native and naturalized, are currently recognized as toxic for both animals and humans, and some of them are known to cause their toxic effects due to their alkaloid content. Among these, there are plants containing the hepatotoxic pyrrolizidine alkaloids, neurotoxins such as the indolizidine alkaloid swainsonine and the piperidine alkaloids coniine and γ-coniceine and tropane alkaloids. Unfortunately, the research in toxic plants in Colombia is not nearly proportional to its plant biodiversity and the scientific information available is only very scarce. The present review aims at summarizing the scarce information about plant alkaloid toxicosis in animals and humans in Colombia. PMID:26690479

  14. Alkaloids Isolated from Natural Herbs as the Anticancer Agents

    PubMed Central

    Lu, Jin-Jian; Bao, Jiao-Lin; Chen, Xiu-Ping; Huang, Min; Wang, Yi-Tao

    2012-01-01

    Alkaloids are important chemical compounds that serve as a rich reservoir for drug discovery. Several alkaloids isolated from natural herbs exhibit antiproliferation and antimetastasis effects on various types of cancers both in vitro and in vivo. Alkaloids, such as camptothecin and vinblastine, have already been successfully developed into anticancer drugs. This paper focuses on the naturally derived alkaloids with prospective anticancer properties, such as berberine, evodiamine, matrine, piperine, sanguinarine, and tetrandrine, and summarizes the mechanisms of action of these compounds. Based on the information in the literature that is summarized in this paper, the use of alkaloids as anticancer agents is very promising, but more research and clinical trials are necessary before final recommendations on specific alkaloids can be made. PMID:22988474

  15. Quinolizidine alkaloid biosynthesis: recent advances and future prospects

    PubMed Central

    Bunsupa, Somnuk; Yamazaki, Mami; Saito, Kazuki

    2012-01-01

    Lys-derived alkaloids, including piperidine, quinolizidine, indolizidine, and lycopodium alkaloids, are widely distributed throughout the plant kingdom. Several of these alkaloids have beneficial properties for humans and have been used in medicine. However, the molecular mechanisms underlying the biosynthesis of these alkaloids are not well understood. In the present article, we discuss recent advances in our understanding of Lys-derived alkaloids, especially the biochemistry, molecular biology, and biotechnology of quinolizidine alkaloid (QA) biosynthesis. We have also highlighted Lys decarboxylase (LDC), the enzyme that catalyzes the first committed step of QA biosynthesis and answers a longstanding question about the molecular entity of LDC activity in plants. Further prospects using current advanced technologies, such as next-generation sequencing, in medicinal plants have also been discussed. PMID:23112802

  16. Alkaloid Changes in Tobacco Seeds during Germination 1

    PubMed Central

    Weeks, W. W.; Bush, L. P.

    1974-01-01

    Nicotine, nornicotine, anabasine, and anatabine, normally found in growing and mature tobacco (Nicotiana tabacum L.) plants, were extracted and quantified from mature tobacco seeds and young tobacco seedlings. The rate of net alkaloid disappearance and accumulation in tobacco seedlings was related to phases of germination. In general, the increased rate of germination associated with higher temperatures also increased the rate of initial loss of alkaloids and the subsequent rate of accumulation of alkaloids. Maximum alkaloid accumulation in 144-hour-old seedlings cultured with 10-hour day occurred at 27 C. Following an 8-hour photoinduction period, seeds germinated in darkness accumulated greater amounts of alkaloids than seeds exposed to light each day. Seeds germinated in darkness for 96 hours, following the 8-hour photoinduction period, and then exposed to light each day accumulated the greatest amounts of alkaloids. PMID:16658655

  17. Toxicosis by Plant Alkaloids in Humans and Animals in Colombia

    PubMed Central

    Diaz, Gonzalo J.

    2015-01-01

    Due to its tropical location, chains of mountains, inter-Andean valleys, Amazon basin area, eastern plains and shores on both the Atlantic and Pacific Oceans, Colombia has many ecosystems and the second largest plant biodiversity in the world. Many plant species, both native and naturalized, are currently recognized as toxic for both animals and humans, and some of them are known to cause their toxic effects due to their alkaloid content. Among these, there are plants containing the hepatotoxic pyrrolizidine alkaloids, neurotoxins such as the indolizidine alkaloid swainsonine and the piperidine alkaloids coniine and γ-coniceine and tropane alkaloids. Unfortunately, the research in toxic plants in Colombia is not nearly proportional to its plant biodiversity and the scientific information available is only very scarce. The present review aims at summarizing the scarce information about plant alkaloid toxicosis in animals and humans in Colombia. PMID:26690479

  18. Total synthesis of the Daphniphyllum alkaloid daphenylline

    NASA Astrophysics Data System (ADS)

    Lu, Zhaoyong; Li, Yong; Deng, Jun; Li, Ang

    2013-08-01

    The Daphniphyllum alkaloids are a large class of natural products isolated from a genus of evergreen plants widely used in Chinese herbal medicine. They display a remarkable range of biological activities, including anticancer, antioxidant, and vasorelaxation properties as well as elevation of nerve growth factor. Daphenylline is a structurally unique member among the predominately aliphatic Daphniphyllum alkaloids, and contains a tetrasubstituted arene moiety mounted on a sterically compact hexacyclic scaffold. Herein, we describe the first total synthesis of daphenylline. A gold-catalysed 6-exo-dig cyclization reaction and a subsequent intramolecular Michael addition reaction, inspired by Dixon's seminal work, were exploited to construct the bridged 6,6,5-tricyclic motif of the natural product at an early stage, and the aromatic moiety was forged through a photoinduced olefin isomerization/6π-electrocyclization cascade followed by an oxidative aromatization process.

  19. New quinoline alkaloids from Ruta chalepensis.

    PubMed

    El Sayed, K; Al-Said, M S; El-Feraly, F S; Ross, S A

    2000-07-01

    The roots of Ruta chalepensis, collected from the northern Saudi desert, yielded two new quinoline alkaloids, namely, 2-¿6'-(2H-benzo[d]1' ',3' '-dioxolen-5' '-yl)hexyl¿-hydroquinolin-4-one (1) and 2-¿6'-(2H-benzo[d]1' ',3' '-dioxolen-5' '-yl)hexyl¿-4-methoxy-quinoline (2). Nine previously reported alkaloids, dictamnine, pteleine, skimmianine, rutacridone, isogravacridonechlorine, maculosidine, graveoline, graveolinine, and 4-methoxy-1-methyl-2(1H)-quinolinone, and coumarins, chalepensin, and umbelliferone were also isolated. Structure elucidations were based primarily on 1D and 2D NMR analyses and chemical transformations. Antimicrobial activity of these compounds is discussed. PMID:10924184

  20. Production of benzylisoquinoline alkaloids in Saccharomyces cerevisiae

    PubMed Central

    Hawkins, Kristy M; Smolke, Christina D

    2010-01-01

    The benzylisoquinoline alkaloids (BIAs) are a diverse class of metabolites that exhibit a broad range of pharmacological activities and are synthesized through plant biosynthetic pathways comprised of complex enzyme activities and regulatory strategies. We have engineered yeast to produce the key intermediate reticuline and downstream BIA metabolites from a commercially available substrate. An enzyme tuning strategy was implemented that identified activity differences between variants from different plants and determined optimal expression levels. By synthesizing both stereoisomer forms of reticuline and integrating enzyme activities from three plant sources and humans, we demonstrated the synthesis of metabolites in the sanguinarine/berberine and morphinan branches. We also demonstrated that a human P450 enzyme exhibits a novel activity in the conversion of (R)-reticuline to the morphinan alkaloid salutaridine. Our engineered microbial hosts offer access to a rich group of BIA molecules and associated activities that will be further expanded through synthetic chemistry and biology approaches. PMID:18690217

  1. Metabolism and ecology of purine alkaloids.

    PubMed

    Anaya, Ana Luisa; Cruz-Ortega, Rocio; Waller, George R

    2006-01-01

    In this review, the biosynthesis, catabolism, ecological significance, and modes of action of purine alkaloids particularly, caffeine, theobromine and theophylline in plants are discussed. In the biosynthesis of caffeine, progress has been made in enzymology, the amino acid sequence of the enzymes, and in the genes encoding N-methyltransferases. In addition, caffeine-deficient plants have been produced. The ecology of purine alkaloids has not proved to be particularly promising. However, advances have been made in insecticidal and allelopathic fields, and in the role of microorganisms play in the changes that these compounds undergo in the soil. Caffeine inhibits cell plate formation during telophase throughout the development of coffee plants and other species. PMID:16720319

  2. Mechanisms of growth inhibition of Phytomonas serpens by the alkaloids tomatine and tomatidine.

    PubMed

    Medina, Jorge Mansur; Rodrigues, Juliany Cola Fernandes; Moreira, Otacilio C; Atella, Geórgia; Souza, Wanderley de; Barrabin, Hector

    2015-02-01

    Phytomonas serpens are flagellates in the family Trypanosomatidae that parasitise the tomato plant (Solanum lycopersicum L.), which results in fruits with low commercial value. The tomato glycoalkaloid tomatine and its aglycone tomatidine inhibit the growth of P. serpens in axenic cultures. Tomatine, like many other saponins, induces permeabilisation of the cell membrane and a loss of cell content, including the cytosolic enzyme pyruvate kinase. In contrast, tomatidine does not cause permeabilisation of membranes, but instead provokes morphological changes, including vacuolisation. Phytomonas treated with tomatidine show an increased accumulation of labelled neutral lipids (BODYPY-palmitic), a notable decrease in the amount of C24-alkylated sterols and an increase in zymosterol content. These results are consistent with the inhibition of 24-sterol methyltransferase (SMT), which is an important enzyme that is responsible for the methylation of sterols at the 24 position. We propose that the main target of tomatidine is the sterols biosynthetic pathway, specifically, inhibition of the 24-SMT. Altogether, the results obtained in the present paper suggest a more general effect of alkaloids in trypanosomatids, which opens potential therapeutic possibilities for the treatment of the diseases caused by these pathogens. PMID:25742263

  3. Mechanisms of growth inhibition of Phytomonas serpens by the alkaloids tomatine and tomatidine

    PubMed Central

    Medina, Jorge Mansur; Rodrigues, Juliany Cola Fernandes; Moreira, Otacilio C; Atella, Geórgia; de Souza, Wanderley; Barrabin, Hector

    2015-01-01

    Phytomonas serpens are flagellates in the family Trypanosomatidae that parasitise the tomato plant (Solanum lycopersicum L.), which results in fruits with low commercial value. The tomato glycoalkaloid tomatine and its aglycone tomatidine inhibit the growth of P. serpens in axenic cultures. Tomatine, like many other saponins, induces permeabilisation of the cell membrane and a loss of cell content, including the cytosolic enzyme pyruvate kinase. In contrast, tomatidine does not cause permeabilisation of membranes, but instead provokes morphological changes, including vacuolisation. Phytomonas treated with tomatidine show an increased accumulation of labelled neutral lipids (BODYPY-palmitic), a notable decrease in the amount of C24-alkylated sterols and an increase in zymosterol content. These results are consistent with the inhibition of 24-sterol methyltransferase (SMT), which is an important enzyme that is responsible for the methylation of sterols at the 24 position. We propose that the main target of tomatidine is the sterols biosynthetic pathway, specifically, inhibition of the 24-SMT. Altogether, the results obtained in the present paper suggest a more general effect of alkaloids in trypanosomatids, which opens potential therapeutic possibilities for the treatment of the diseases caused by these pathogens. PMID:25742263

  4. Three new oxazoline alkaloids from Gymnotheca chinensis.

    PubMed

    Xiao, Shi-Ji; Guo, Da-Le; Zhang, Mao-Sheng; Chen, Fang; Ding, Li-Sheng; Zhou, Yan

    2016-08-01

    Three novel oxazoline alkaloids, 1-oxa-3-azaspiro [4.5] dec-2-ene-8-one (1), 1-oxa-3-azaspiro [4.5] dec-2, 6-diene-8-one (2), and 1-oxa-3-azaspiro [4.5] dec-10-methoxy-2, 6-diene-8-one (3) were isolated from the methanol extract of the whole plant of Gymnotheca chinensis. The chemical structures were established by means of spectroscopic analysis including one- and two-dimensional NMR spectroscopy. PMID:26949983

  5. Synthesis studies on the Melodinus alkaloid meloscine

    PubMed Central

    Feldman, Ken S.; Antoline, Joshua F.

    2012-01-01

    The pentacyclic Melodinus alkaloid (±)-meloscine was synthesized in 19 chemical steps from 2-bromobenzaldehyde through a route featuring an allenyl azide cyclization cascade to deliver the core azabicyclo[3.3.0]octane substructure. Peripheral functionalization of this core included a Tollens-type aldol condensation to set the quaternary center at C(20) and a diastereoselective ring closing metathesis to forge the tetrahydropyridine ring. PMID:23316092

  6. Synthesis and SAR of vinca alkaloid analogues.

    PubMed

    Voss, Matthew E; Ralph, Jeffery M; Xie, Dejian; Manning, David D; Chen, Xinchao; Frank, Anthony J; Leyhane, Andrew J; Liu, Lei; Stevens, Jason M; Budde, Cheryl; Surman, Matthew D; Friedrich, Thomas; Peace, Denise; Scott, Ian L; Wolf, Mark; Johnson, Randall

    2009-02-15

    Versatile intermediates 12'-iodovinblastine, 12'-iodovincristine and 11'-iodovinorelbine were utilized as substrates for transition metal based chemistry which led to the preparation of novel analogues of the vinca alkaloids. The synthesis of key iodo intermediates, their transformation into final products, and the SAR based upon HeLa and MCF-7 cell toxicity assays is presented. Selected analogues 27 and 36 show promising anticancer activity in the P388 murine leukemia model. PMID:19147348

  7. Antimicrobial alkaloids from Zanthoxylum tetraspermum and caudatum.

    PubMed

    Nissanka, A P; Karunaratne, V; Bandara, B M; Kumar, V; Nakanishi, T; Nishi, M; Inada, A; Tillekeratne, L M; Wijesundara, D S; Gunatilaka, A A

    2001-04-01

    Two benzophenanthrene alkaloids, 8-acetonyldihydronitidine and 8-acetonyldihydroavicine were isolated from Zanthoxylum tetraspermum stem bark along with liriodenine, sesamin, lichexanthone and (+)-piperitol-gamma,gamma-dimethylallylether. The species endemic to Sri Lanka, Z. caudatum, contained sesamin, savinin, liriodenine, decarine and 8-O-desmethyl-N-nornitidine. 8-Acetonyldihydronitidine and 8-acetonyldihydroavicine showed significant antibacterial activity while the former along with liriodenine was strongly antifungal. Savinin exhibited potent spermicidal activity. Both savinin and sesamin exhibited significant insecticidal activity. PMID:11324918

  8. Histamine release inhibition activity of bisbenzylisoquinoline alkaloids.

    PubMed

    Nakamura, K; Tsuchiya, S; Sugimoto, Y; Sugimura, Y; Yamada, Y

    1992-12-01

    Eleven examples of bisbenzylisoquinoline alkaloids (head-to-head; 10, head-to-tail; 1) and one half molecule type (N-methylcoclaurine), were tested by in vitro histamine release inhibition assay. The order of the potency of the inhibitory effect was ranked thus: homoaromoline, aromoline, isotetrandrine, cepharanthine, fangchinoline, obaberine, and tetrandrine. The following substances, cepharanoline, berbamine, oxyacanthine, and cycleanine (head-to-tail structure) had no inhibitory effect. N-Methylcoclaurine showed an inhibitory effect comparable to that of fangchinoline. PMID:1484888

  9. A new cytotoxic carbazole alkaloid from Clausena excavata.

    PubMed

    Taufiq-Yap, Y H; Peh, T H; Ee, G C L; Rahmani, M; Sukari, M A; Ali, A M; Muse, R

    2007-07-20

    A new carbazole alkaloid, 3-carbomethoxy-2-hydroxy-7-methoxycarbazole, Clausine-TY (1), together with two known carbazole alkaloid, Clausine-H (2) and Clausine-B (3), were isolated from the ethyl acetate extract of the stem bark of the Malaysian Clausena excavata. The structures of these compounds were elucidated by spectroscopic analyses. The new carbazole alkaloid shows significant cytotoxicity against CEM-SS cell line. PMID:17654285

  10. A potent antibacterial indole alkaloid from Psychotria pilifera.

    PubMed

    Liu, Lu; Song, Chang-Wei; Khan, Afsar; Li, Xiao-Ning; Yang, Xing-Wei; Cheng, Gui-Guang; Liu, Ya-Ping; Luo, Xiao-Dong

    2016-08-01

    A new strychnine alkaloid, 16,17,19,20-tetrahydro-2,16-dehydro-18-deoxyisostrychnine (1), and fourteen known alkaloids were isolated from the leaves of Psychotria pilifera. Their structures were identified on the basis of extensive spectroscopic analysis, as well as by comparison with the reported spectroscopic data. The new alkaloid (1) exhibited potent antibacterial activity against Escherichia coli, equivalent to cefotaxime with MIC value of 0.781 μg/ml. PMID:26963582

  11. Recent Advances in the Synthesis of Stemona Alkaloids.

    PubMed

    Liu, Xiao-Yu; Wang, Feng-Peng

    2015-06-01

    Stemona alkaloids, featuring polycyclic structures and interesting bioactivities, constitute a distinct class from the Stemonaceae family. In this review, recent advances in the synthesis of these unique alkaloids are briefly discussed, highlighting the application of novel synthetic strategies to access the core structures, as well as creative solutions to the installation of multiple stereogenic centers. The literature reviewed in this article covers the publications from 2010 to November 2014, a period that witnessed the prosperity of the synthesis of Stemona alkaloids. PMID:26197559

  12. A new monoterpenoid oxindole alkaloid from Hamelia patens micropropagated plantlets.

    PubMed

    Paniagua-Vega, David; Cerda-García-Rojas, Carlos M; Ponce-Noyola, Teresa; Ramos-Valdivia, Ana C

    2012-11-01

    Chemical studies on Hamelia patens (Rubiaceae) micropropagated plantlets allowed production of a new monoterpenoid oxindole alkaloid, named (-)-hameline (7), together with eight known alkaloids, tetrahydroalstonine (1), aricine (2), pteropodine (3), isopteropodine (4), uncarine F (5), speciophylline (6), palmirine (8), and rumberine (9). The structure of the new alkaloid was assigned on the basis of 1D and 2D NMR spectroscopy, mass spectrometry, and molecular modeling. PMID:23285803

  13. Changes in mouse whole saliva soluble proteome induced by tannin-enriched diet

    PubMed Central

    2010-01-01

    Background Previous studies suggested that dietary tannin ingestion may induce changes in mouse salivary proteins in addition to the primarily studied proline-rich proteins (PRPs). The aim of the present study was to determine the protein expression changes induced by condensed tannin intake on the fraction of mouse whole salivary proteins that are unable to form insoluble tannin-protein complexes. Two-dimensional polyacrylamide gel electrophoresis protein separation was used, followed by protein identification by mass spectrometry. Results Fifty-seven protein spots were excised from control group gels, and 21 different proteins were identified. With tannin consumption, the expression levels of one α-amylase isoform and one unidentified protein increased, whereas acidic mammalian chitinase and Muc10 decreased. Additionally, two basic spots that stained pink with Coomassie Brilliant Blue R-250 were newly observed, suggesting that some induced PRPs may remain uncomplexed or form soluble complexes with tannins. Conclusion This proteomic analysis provides evidence that other salivary proteins, in addition to tannin-precipitating proteins, are affected by tannin ingestion. Changes in the expression levels of the acidic mammalian chitinase precursor and in one of the 14 salivary α-amylase isoforms underscores the need to further investigate their role in tannin ingestion. PMID:21159160

  14. High-throughput micro plate vanillin assay for determination of tannin in sorghum grain

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Sorghum tannins are phenolic compounds that offer health promoting antioxidant properties. The conventional HCl-vanillin assay for determining tannin content is a time-consuming method for screening large sample sets as seen in association mapping panels or breeder nursery samples. The objective of ...

  15. Characterization of condensed tannins and carbohydrates in hot water bark extracts of European softwood species.

    PubMed

    Bianchi, Sauro; Kroslakova, Ivana; Janzon, Ron; Mayer, Ingo; Saake, Bodo; Pichelin, Frédéric

    2015-12-01

    Condensed tannins extracted from European softwood bark are recognized as alternatives to synthetic phenolics. The extraction is generally performed in hot water, leading to simultaneous extraction of other bark constituents such as carbohydrates, phenolic monomers and salts. Characterization of the extract's composition and identification of the extracted tannins' molecular structure are needed to better identify potential applications. Bark from Silver fir (Abies alba [Mill.]), European larch (Larix decidua [Mill.]), Norway spruce (Picea abies [Karst.]), Douglas fir (Pseudotsuga menziesii [Mirb.]) and Scots pine (Pinus sylvestris [L.]) were extracted in water at 60°C. The amounts of phenolic monomers, condensed tannins, carbohydrates, and inorganic compounds in the extract were determined. The molecular structures of condensed tannins and carbohydrates were also investigated (HPLC-UV combined with thiolysis, MALDI-TOF mass spectrometry, anion exchange chromatography). Distinct extract compositions and tannin structures were found in each of the analysed species. Procyanidins were the most ubiquitous tannins. The presence of phenolic glucosides in the tannin oligomers was suggested. Polysaccharides such as arabinans, arabinogalactans and glucans represented an important fraction of all extracts. Compared to traditionally used species (Mimosa and Quebracho) higher viscosities as well as faster chemical reactivities are expected in the analysed species. The most promising species for a bark tannin extraction was found to be larch, while the least encouraging results were detected in pine. A better knowledge of the interaction between the various extracted compounds is deemed an important matter for investigation in the context of industrial applications of such extracts. PMID:26547588

  16. Degradation of tannins in spent coffee grounds by Pleurotus sajor-caju.

    PubMed

    Wong, Y S; Wang, X

    1991-09-01

    Pleurotus sajor-caju PL27, a white rot fungus, degraded up to 87% of the tannins in spent coffee grounds as a solid substrate over 32 days. Degradation of tannins was enhanced if potato and dextrose were included. The potential nutritive value of the substrate as animal feed may be improved by this process. PMID:24425201

  17. Research observation: Hydrolyzable and condensed tannins in plants of northwest Spain forests

    USGS Publications Warehouse

    Gonzalez-Hernandez, M. P.; Karchesy, J.; Starkey, E.E.

    2003-01-01

    Tannins are secondary metabolites that may influence feeding by mammals on plants. We analyzed hydrolyzable and condensed tannins in 30 plant species consumed by livestock and deer, as a preliminary attempt to study their possible implications on browsing and grazing in forest ecosystems. Heathers (Ericaceae) and plants of the Rose (Rosaceae) family had tannins, while forbs, grasses and shrubs other than the heathers did not show astringency properties. We found the highest tannin content of all the species in Rubus sp., with the highest value around 180 mg TAE/g dry weight in spring. Potentilla erecta, Alnus glutinosa and Quercus robur were next with 57 to 44 mg TAE/g dw. Total tannins in heathers ranged from 22 to 36 mg TAE/g dw. Levels of condensed tannins were higher than hydrolyzable for most of the species. Only Betula alba, Calluna vulgaris, Pteridium aquilinum and Vaccinium myrtillus had 100% hydrolyzable tannins. Tannin content of the species changed seasonally with highest values during the growing season, corresponding to late winter or early spring, depending on the species.

  18. Research observation: Hydrolyzable and condensed tannins in plants of the northwest

    USGS Publications Warehouse

    Gonzalez-Hernandez, M. P.; Karchesy, J.; Starkey, Edward E.

    2003-01-01

    Tannins are secondary metabolites that may influence feeding by mammals on plants. We analyzed hydrolyzable and condensed tannins in 30 plant species consumed by livestock and deer, as a preliminary attempt to study their possible implications on browsing and grazing in forest ecosystems. Heathers (Ericaceae) and plants of the Rose (Rosaceae) family had tannins, while forbs, grasses and shrubs other than the heathers did not show astringency properties. We found the highest tannin content of all the species in Rubus sp., with the highest value around 180 mg TAE/g dry weight in spring. Potentilla erecta, Alnus glutinosa and Quercus robur were next with 57 to 44 mg TAE/g dw. Total tannins in heathers ranged from 22 to 36 mg TAE/g dw. Levels of condensed tannins were higher than hydrolyzable for most of the species. Only Betula alba, Calluna vulgaris, Pteridium aquilinum and Vaccinium myrtillus had 100% hydrolyzable tannins. Tannin content of the species changed seasonally with highest values during the growing season, corresponding to late winter or early spring, depending on the species.

  19. Manure ammonia and greenhouse gas emissions from beef cattle fed condensed tannins

    Technology Transfer Automated Retrieval System (TEKTRAN)

    A study was conducted to determine the effects of three levels of condensed tannins fed to 27 beef feed yard steers on ammonia and GHG emissions from manure. Condensed tannins were fed at rates of 0, 0.5 and 1.0 percent on a dry matter basis. Manure and urine were collected from two periods over 6 d...

  20. Influence of high tannin grain sorghum on gastrointestinal nematode infection in goats

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Previous studies have demonstrated that condensed tannin-rich forages such as sericea lespedeza can control gastrointestinal nematode infection (GIN) in goats. The objective of three experiments (EXP) was to determine the influence of high tannin grain sorghum on GIN in goats. Naturally infected B...

  1. TANNIN-CONTAINING ALFALFA: A WAY TO IMPROVE NITROGEN-USE AND PROFITABILITY OF DAIRY FARMS?

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Binding of condensed tannins to protein can prevent excessive proteolysis in forages during ensiling, ruminal digestion, and decay of residues in soil. Plant breeding and biotechnology efforts are underway in the U.S. and abroad to develop alfalfa and other forages with adequate levels of tannin for...

  2. EFFECTS OF TANNINS ON SOIL CARBON, CATION EXCHANGE CAPACITY, AND METAL SOLUBILITY

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Tannins sorb to soil, affect the solubility of soil nitrogen, and soil chemical processes that may be important for the formation of soil organic matter and nutrient cycling. However, studies are needed, comparing different classes of tannins and related compounds, to determine if soils have a maxi...

  3. Characterization of tannin-metal complexes by UV-visible spectrophotometry

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Tannins enter soils by plant decay and rain throughfall, but little is known of their effects on soils. Tannins may influence bioavailability and toxicity of metals by forming complexes and by mediating redox reactions. We evaluated the affinity and stoichiometry of Al(III) for a gallotannin, pent...

  4. Sorption of tannin-C by soils affects soil cation exchange capacity

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Some tannins, produced by plants, are able to sorb to soil, and thus influence soil organic matter and nutrient cycling. However, studies are needed that compare sorption of tannins to other related phenolic compounds, evaluate their effects across a broad range of soils, and determine if sorption ...

  5. [Separation of tannins in Rhubarb and its analysis by high performance liquid chromatography-mass spectrometry].

    PubMed

    Ding, Mingyu; Ni, Weiwei

    2004-11-01

    In order to investigate the pharmaceutical actions of rhubarb, a method for extracting, separating and analyzing the tannin components in rhubarb was studied. At first, a procedure for the group separation of tannins from the water-ethanol extract of rhubarb was established based on the formation of tannins-caffein precipitation. Then, a high performance liquid chromatographic (HPLC) method for the analysis of tannins in rhubarb was developed. This HPLC method is based on a reversed-phase C18 column and polar mobile-phase such as water and methanol with gradient elution, and the tannins can be well separated. Finally, the identification of the tannin components in rhubarb was carried out by high performance liquid chromatography-mass spectrometry (HPLC-MS). The structures of the main tannin components (gallic acid, catechin, the dimer, trimer, tetramer and pentamer of catechin) in rhubarb are suggested. The fragmentation laws of the tannin components are summarized. In comparing with previous methods, it is simple and without the interference of co-existed compounds. PMID:15807111

  6. SORPTION OF TANNIN AND RELATED PHENOLIC COMPOUNDS AND EFFECTS ON SOLUBLE-N IN SOIL

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Some tannins, plant-derived polyphenolic compounds, can rapidly affix to soil and affect the solubility of labile soil-N but a more complete understanding of the nature and persistence of tannin-soil interactions is needed. Forest and pasture soils from two depths were treated for 1 h with cool (23...

  7. Cattle and sheep develop preference for drinking water containing grape seed tannin

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Ingestion of small amounts of some types of condensed tannins by ruminant livestock can provide benefits to the animals, their producers and the environment. However, practical methods are needed to make these tannin more available to livestock. Results from previous trials with crude quebracho an...

  8. Use of condensed tannin extract from quebracho trees to reduce methane emissions from cattle.

    PubMed

    Beauchemin, K A; McGinn, S M; Martinez, T F; McAllister, T A

    2007-08-01

    Our objective was to determine if condensed tannin extract from quebracho trees (Schinopsis quebracho-colorado; red quebracho) could be used to reduce enteric methane emissions from cattle. The experiment was designed as a repeated 3 x 3 Latin square (4 squares) with 3 treatments (0, 1, and 2% of dietary DM as quebracho tannin extract) and 3 28-d periods. Six spayed Angus heifers (238 +/- 13.3 kg of initial BW) and 6 Angus steers (207 +/- 8.2 kg of initial BW) were each assigned to 2 squares. The measured condensed tannin content of the extract was 91%, and the basal diet contained 70% forage (DM basis). Feeding quebracho tannin extract had no effect on BW, ADG, or nutrient intakes. Furthermore, it had no effect on DM, energy, or fiber (ADF and NDF) digestibility, but apparent digestibility of CP decreased linearly (P < 0.001) by 5 and 15% with 1 and 2% quebracho tannin extract, respectively. There were no effects of quebracho tannin extract on methane emissions (g/d, g/kg of DM, % of GE intake, or % of DE intake). Feeding up to 2% of the dietary DM as quebracho tannin extract failed to reduce enteric methane emissions from growing cattle, although the protein-binding effect of the quebracho tannin extract was evident. PMID:17468433

  9. Drug Delivery Systems and Combination Therapy by Using Vinca Alkaloids

    PubMed Central

    Lee, Chun-Ting; Huang, Yen-Wei; Yang, Chih-Hui; Huang, Keng-Shiang

    2015-01-01

    Developing new methods for chemotherapy drug delivery has become a topic of great concern. Vinca alkaloids are among the most widely used chemotherapy reagents for tumor therapy; however, their side effects are particularly problematic for many medical doctors. To reduce the toxicity and enhance the therapeutic efficiency of vinca alkaloids, many researchers have developed strategies such as using liposome-entrapped drugs, chemical- or peptide-modified drugs, polymeric packaging drugs, and chemotherapy drug combinations. This review mainly focuses on the development of a vinca alkaloid drug delivery system and the combination therapy. Five vinca alkaloids (eg, vincristine, vinblastine, vinorelbine, vindesine, and vinflunine) are reviewed. PMID:25877096

  10. Evaluation of Biosynthetic Pathway and Engineered Biosynthesis of Alkaloids.

    PubMed

    Kishimoto, Shinji; Sato, Michio; Tsunematsu, Yuta; Watanabe, Kenji

    2016-01-01

    Varieties of alkaloids are known to be produced by various organisms, including bacteria, fungi and plants, as secondary metabolites that exhibit useful bioactivities. However, understanding of how those metabolites are biosynthesized still remains limited, because most of these compounds are isolated from plants and at a trace level of production. In this review, we focus on recent efforts in identifying the genes responsible for the biosynthesis of those nitrogen-containing natural products and elucidating the mechanisms involved in the biosynthetic processes. The alkaloids discussed in this review are ditryptophenaline (dimeric diketopiperazine alkaloid), saframycin (tetrahydroisoquinoline alkaloid), strictosidine (monoterpene indole alkaloid), ergotamine (ergot alkaloid) and opiates (benzylisoquinoline and morphinan alkaloid). This review also discusses the engineered biosynthesis of these compounds, primarily through heterologous reconstitution of target biosynthetic pathways in suitable hosts, such as Escherichia coli, Saccharomyces cerevisiae and Aspergillus nidulans. Those heterologous biosynthetic systems can be used to confirm the functions of the isolated genes, economically scale up the production of the alkaloids for commercial distributions and engineer the biosynthetic pathways to produce valuable analogs of the alkaloids. In particular, extensive involvement of oxidation reactions catalyzed by oxidoreductases, such as cytochrome P450s, during the secondary metabolite biosynthesis is discussed in details. PMID:27548127

  11. New Perspectives in the Chemistry of Marine Pyridoacridine Alkaloids

    PubMed Central

    Plodek, Alois; Bracher, Franz

    2016-01-01

    Secondary metabolites from marine organisms are a rich source of novel leads for drug development. Among these natural products, polycyclic aromatic alkaloids of the pyridoacridine type have attracted the highest attention as lead compounds for the development of novel anti-cancer and anti-infective drugs. Numerous sophisticated total syntheses of pyridoacridine alkaloids have been worked out, and many of them have also been extended to the synthesis of libraries of analogues of the alkaloids. This review summarizes the progress in the chemistry of pyridoacridine alkaloids that was made in the last one-and-a-half decades. PMID:26821033

  12. Plant alkaloids as drug leads for Alzheimer's disease.

    PubMed

    Ng, Yu Pong; Or, Terry Cho Tsun; Ip, Nancy Y

    2015-10-01

    Alzheimer's disease (AD) is a neurodegenerative illness associated with dementia and is most prevalent among the elderly population. Current medications can only treat symptoms. Alkaloids are structurally diverse and have been an important source of therapeutics for various brain disorders. Two US Food and Drug Administration (FDA)-approved acetylcholinesterase inhibitors for AD, galantamine and rivastigmine, are in fact alkaloids. In addition, clinical trials of four other extensively studied alkaloids-huperzine A, caffeine, nicotine, and indomethacin-have been conducted but do not convincingly demonstrate their clinical efficacy for AD. Interestingly, rhynchophylline, a known neuroprotective alkaloid, was recently discovered by in silico screening as an inhibitor of EphA4, a novel target for AD. Here, we review the pathophysiological mechanisms underlying AD, current treatment strategies, and therapeutic potential of several selected plant alkaloids in AD, highlighting their various drug targets and the key supportive preclinical and clinical studies. Future research should include more rigorous clinical studies of the most promising alkaloids, the further development of recently discovered candidate alkaloids, and the continual search for new alkaloids for relevant drug targets. It remains promising that an alkaloid drug candidate could significantly affect the progression of AD in addition to providing symptomatic relief. PMID:26220901

  13. Drug delivery systems and combination therapy by using vinca alkaloids.

    PubMed

    Lee, Chun-Ting; Huang, Yen-Wei; Yang, Chih-Hui; Huang, Keng-Shiang

    2015-01-01

    Developing new methods for chemotherapy drug delivery has become a topic of great concern. Vinca alkaloids are among the most widely used chemotherapy reagents for tumor therapy; however, their side effects are particularly problematic for many medical doctors. To reduce the toxicity and enhance the therapeutic efficiency of vinca alkaloids, many researchers have developed strategies such as using liposome-entrapped drugs, chemical- or peptide-modified drugs, polymeric packaging drugs, and chemotherapy drug combinations. This review mainly focuses on the development of a vinca alkaloid drug delivery system and the combination therapy. Five vinca alkaloids (eg, vincristine, vinblastine, vinorelbine, vindesine, and vinflunine) are reviewed. PMID:25877096

  14. Biologically active indole and bisindole alkaloids from Tabernaemontana divaricata.

    PubMed

    Kam, Toh-Seok; Pang, Huey-Shen; Lim, Tuck-Meng

    2003-04-21

    The ethanol extract of the leaves of Tabernaemontana divaricata (double flower variety) provided a total of 23 alkaloids, including the new aspidosperma alkaloids, taberhanine, voafinine, N-methylvoafinine, voafinidine, voalenine and the new bisindole alkaloid, conophyllinine in addition to the previously known, biologically active bisindole, conophylline and its congener, conofoline. The structures of the new alkaloids were established by spectroscopic methods. The preparation and characterization of the corresponding quinones of the biologically active bisindoles are also described in relation to a structure-activity study of these compounds with respect to their action in stimulating insulin expression. PMID:12929658

  15. Spectral Study of the Interaction of Myoglobin with Tannin

    NASA Astrophysics Data System (ADS)

    Grigoryan, K. R.; Sargsyan, L. S.

    2016-07-01

    The interaction of myoglobin with tannin (tannic acid) at 298.15 and 303.15 K was studied by fluorescence and absorption spectroscopy in the UV region. The physicochemical and thermodynamic binding parameters (the fluorescence quenching mechanism, the bonding constant, the number of binding sites, the type of interaction) and parameters of the formed complex were determined. It was found that binding of myoglobin with tannic acid does not lead to significant changes in the electronic state of the heme ring of myoglobin.

  16. Reduction of venom alkaloids in Solenopsis richteri×Solenopsis invicta hybrid: an attempt to identify new alkaloidal components.

    PubMed

    Chen, Li; Hu, Qiong-Bo; Fadamiro, Henry Y

    2010-11-24

    The alkaloid chemistry of the venom of hybrid fire ant, Solenopsis richteri × Solenopsis invicta, was investigated using silica gel chromatography and GC-MS techniques. In addition to most cis alkaloids of parental species, S. richteri Forel and S. invicta Buren, the cis alkaloid fraction of the body extract of hybrid fire ants also contains five significant new alkaloids. Hydrogenation of the cis alkaloid fraction yielded only five piperidines, 4', 12', 12, 20', and 20. Sodium borohydride and lithium aluminum hydride selectively reduced C═N double bond in piperideine alkaloids to give a mixture of cis and trans piperidines. However, reduction of the five new components yielded several new peaks with much longer retention times and increasing molecular weights over 30. It is evident that the chemical identities of the five new peaks are quite different from those known piperidines or piperideines found in Solenopsis fire ants. PMID:20964344

  17. New steroidal saponins from the rhizomes of Paris delavayi and their cytotoxicity.

    PubMed

    Liu, Yang; Tian, Xiangrong; Hua, Dong; Cheng, Guang; Wang, Kaixing; Zhang, Lihan; Tang, Haifeng; Wang, Minchang

    2016-06-01

    Four new furostanol saponins, named padelaosides C-F (1-4), together with four known spirostanol saponins 5-8 were isolated from the rhizomes of Paris delavayi Franchet. Their structures were elucidated on the basis of extensive spectroscopic analysis and chemical evidences. The discovery of the new compounds 1-4 extended the diversity and complexity of this furostanol saponin family. The cytotoxicity of all the saponins was evaluated for their cytotoxicity against human glioblastoma U87MG and human hepatocellular carcinoma Hep-G2 cell lines. The known spirostanol saponins 7 and 8 exhibited notable cytotoxicity against the two tumor cell lines with IC50 values of 1.13 and 3.42μM, respectively, while the new furostanol saponins 3 and 4 showed moderate cytotoxicity with IC50 values of 15.28 to 16.98μM. PMID:27118322

  18. Triterpenoid saponins from the roots of Clematis argentilucida and their cytotoxic activity.

    PubMed

    Zhao, Mei; Ma, Ning; Qiu, Feng; Hai, Wen-Li; Tang, Hai-Feng; Zhang, Yan; Wen, Ai-Dong

    2014-07-01

    The reinvestigation of the n-BuOH extract of the roots of Clematis argentilucida led to the isolation of four new oleanane-type triterpenoid saponins, 1-4, four known saponins, 5-8, first isolated from the species, together with ten saponins, 9-18, reported in the preceding papers. The structures of saponins 1-8 were elucidated by extensive spectroscopic analysis and chemical evidences. The cytotoxicity of all the saponins were evaluated against human tumor HL-60, HepG-2, and SGC-7901 cell lines. The monodesmosidic saponins 4, 7, 8, and 14-18 exhibited cytotoxic activity against the three cell lines with IC50 values in the range of 0.87-19.48 µM. PMID:25029176

  19. Endothelial cell cytotoxicity of cotton bracts tannin and aqueous cotton bracts extract

    SciTech Connect

    Johnson, C.M.; Hanson, M.N.; Rohrbach, M.S.

    1986-04-01

    Using an in vitro cytotoxicity assay based on the release of /sup 51/Cr from cultured porcine thoracic aortic and pulmonary arterial endothelial cells, we have demonstrated that cotton bracts tannin is a potent endothelial cell cytotoxin. It produces dose-dependent lethal injury to both types of endothelial cells with the aortic cells, being somewhat more sensitive to tannin-mediated injury than the pulmonary arterial cells. Cytotoxic injury to the cells was biphasic. During the first 3 hr of exposure to tannin, no lethal injury was detected. However, during this period, profound changes in morphology were observed suggesting sublethal injury to the cells preceded the ultimate toxic damage. Comparison of the cytotoxicity dose curves for aqueous bracts extracts with those for tannin demonstrated that tannin was major cytotoxin present in bracts.

  20. 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. PMID:26021881

  1. Polyethylene glycol influences selection of foraging location by sheep consuming quebracho tannin.

    PubMed

    Villalba, J J; Provenza, F D

    2002-07-01

    Tannins are a heterogeneous group of phenolic polymers that can induce detrimental effects when consumed by herbivores. Polyethylene glycol (PEG) binds to tannins and thus attenuates their negative effects. Our objective was to determine whether sheep actively seek PEG when fed tannins and thus modify their foraging location as a function of the spatial distribution of PEG. Lambs were first trained to recognize the beneficial effects of PEG by offering a meal high in quebracho tannin (QT), which presumably caused malaise, and then PEG (MW, 3,350), which presumably led to recovery from malaise. Animals were then tested in an experimental area where they could forage at two different locations that contained in Trial 1 1) PEG and QT in adjacent food boxes (PEG+QT) or 2) QT and in Trial 2 1) PEG or 2) QT. Preference for foraging locations was tested under three conditions: 1) no preload meal, 2) a meal high in quebracho tannin 1 h before testing, and 3) a basal diet high in quebracho tannin. Lambs spent more time (P = 0.012) and ate more tannin-containing food (P = 0.022) at locations where PEG was present (PEG+QT) than where it was absent (QT; Trial 1). Lambs responded to increased tannins in their bodies (Conditions 2 and 3) by reducing intake (P = 0.0001; Trial 2) at sites containing only QT and by increasing intake (P = 0.0001, Trial 1; P = 0.001, Trial 2) and foraging time (P = 0.072, Trial 1; P = 0.0001, Trial 2) at locations where PEG was available. Thus, PEG influenced foraging location by sheep consuming quebracho tannin. Accordingly, it may be possible to formulate range blocks that enable herbivores to ingest PEG in tannin-rich habitats. Strategic distribution of PEG in those habitats may attract animals to underutilized feeding sites. PMID:12162651

  2. Saponins: Anti-diabetic principles from medicinal plants - A review.

    PubMed

    Elekofehinti, Olusola Olalekan

    2015-06-01

    Diabetes mellitus (DM) represents a global health problem. It is the most common of the endocrine disorders and is characterized by chronic hyperglycemia due to relative or absolute lack of insulin secretion or insulin actions. According to the World Health Organization projections, the diabetes population is likely to increase to 300 million or more by the year 2025. Current synthetic agents and insulin used effectively for the treatment of diabetes are scarce especially in rural areas, expensive and have prominent adverse effects. Complementary and alternative approaches to diabetes management such as isolation of phytochemicals with anti-hyperglycemic activities from medicinal plants is therefore imperative. Saponins are phytochemical with structural diversity and biological activities. This paper reviews saponins and various plants from which they were isolated as well as properties that make them ideal for antidiabetic remedy. PMID:25753168

  3. Two new ursane-type triterpenoid saponins from Elsholtzia bodinieri.

    PubMed

    Zhong, Jin-Dong; Zhao, Xue-Wei; Chen, Xuan-Qin; Li, Hong-Mei; Chen, Chin-Ho; Xia, Xue-Shan; Li, Rong-Tao

    2016-06-01

    Two new ursane-type triterpenoid saponins, bodiniosides M (1) and N (2), along with three known saponins, oblonganosides I (3), pseudobuxussaponin B (4) and bodinioside A (5), were isolated from the aerial parts of Elsholtzia bodinieri. The structures of compounds 1 and 2 were characterized by spectroscopic data as well as acid hydrolysis and GC analysis as 3-O-β-D-xylopyranosyl-19α-hydroxy-23-acetoxy-urs-12(13)-en-28-oic acid 28-O-α-L-rhamnopyranosyl-(1-2)-β-D-glucopyranoside and 3-O-β-D-glucopyranosyl-2α,19α-dihydroxy-urs-12(13)-en-28,20β-lactone. Compounds 1 and 5 exhibited potent anti-HCV activities in vitro with a selective index of 6.53 and 4.41, respectively. PMID:27138284

  4. Unusual Cytotoxic Steroidal Saponins from the Gorgonian Astrogorgia dumbea.

    PubMed

    Lu, Ya-Nan; Cui, Ping; Tian, Xiao-Qing; Lou, Li-Guang; Fan, Cheng-Qi

    2016-06-01

    Three steroidal saponins, including astrogorgiosides A (1) and B (2) bearing acetamido-glucose moieties, and astrogorgioside C (3) with a 19-nor and bearing an aromatized B ring steroid aglycone, together with a known major saponin dimorphoside A (4), were obtained from the gorgonian Astrogorgia dumbea collected near Dongshan Island in East China Sea. Structures of these compounds were elucidated by in-depth spectral and chemical methods, including 2D-NMR, HR-ESI-MS spectra, and acidic hydrolysis. For the first time, acetamido-glucose moiety is being reported from a gorgonian. The B-ring aromatized steroid aglycone of compound 3 is also rare in marine natural products. Compounds 1-3 exhibited moderate cytotoxic activity with IC50 values of 26.8-45.6 µM against human tumor cells Bel-7402 and K562. PMID:27352300

  5. A saponin-detoxifying enzyme mediates suppression of plant defences

    NASA Astrophysics Data System (ADS)

    Bouarab, K.; Melton, R.; Peart, J.; Baulcombe, D.; Osbourn, A.

    2002-08-01

    Plant disease resistance can be conferred by constitutive features such as structural barriers or preformed antimicrobial secondary metabolites. Additional defence mechanisms are activated in response to pathogen attack and include localized cell death (the hypersensitive response). Pathogens use different strategies to counter constitutive and induced plant defences, including degradation of preformed antimicrobial compounds and the production of molecules that suppress induced plant defences. Here we present evidence for a two-component process in which a fungal pathogen subverts the preformed antimicrobial compounds of its host and uses them to interfere with induced defence responses. Antimicrobial saponins are first hydrolysed by a fungal saponin-detoxifying enzyme. The degradation product of this hydrolysis then suppresses induced defence responses by interfering with fundamental signal transduction processes leading to disease resistance.

  6. Trifasciatosides A-J, Steroidal Saponins from Sansevieria trifasciata.

    PubMed

    Teponno, Rémy Bertrand; Tanaka, Chiaki; Jie, Bai; Tapondjou, Léon Azefack; Miyamoto, Tomofumi

    2016-01-01

    Four previously unreported steroidal saponins, trifasciatosides A-D (1-4), three pairs of previously undescribed steroidal saponins, trifasciatosides E-J (5a, b-7a, b) including acetylated ones, together with twelve known compounds were isolated from the n-butanol soluble fraction of the methanol extract of Sansevieria trifasciata. Their structures were elucidated on the basis of detailed spectroscopic analysis, including (1)H-NMR, (13)C-NMR, (1)H-(1)H correlated spectroscopy (COSY), heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond connectivity (HMBC), total correlated spectroscopy (TOCSY), nuclear Overhauser enhancement and exchange spectroscopy (NOESY), electrospray ionization-time of flight (ESI-TOF)-MS and chemical methods. Compounds 2, 4, and 7a, b exhibited moderate antiproliferative activity against HeLa cells. PMID:27581639

  7. Qualitative and quantitative saponin contents in five sea cucumbers from the Indian ocean.

    PubMed

    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

  8. Electrophoretic mobility as a tool to separate immune adjuvant saponins from Quillaja saponaria Molina.

    PubMed

    Gilabert-Oriol, Roger; Weng, Alexander; von Mallinckrodt, Benedicta; Stöshel, Anja; Nissi, Linda; Melzig, Matthias F; Fuchs, Hendrik; Thakur, Mayank

    2015-06-20

    Quillaja saponins are used as adjuvants in animal vaccines but their application in human vaccination is still under investigation. Isolation and characterization of adjuvant saponins is very tedious. Furthermore, standardization of Quillaja saponins is critical pertaining to its application in humans. In this study, a convenient method based on agarose gel electrophoresis was developed for the separation of Quillaja saponins. Six different commercial Quillaja saponins were segregated by size/charge into numerous fractions. Each of the fractions was characterized by ESI-TOF-MS spectroscopy and thin layer chromatography. Real-time impedance-based monitoring and red blood cell lysis assay were used to evaluate cytotoxicity and hemolytic activities respectively. Two specific regions in the agarose gel (delimited by specific relative electrophoretic mobility values) were identified and characterized by exclusive migration of acylated saponins known to possess immune adjuvant properties (0.18-0.58), and cytotoxic and hemolytic saponins (0.18-0.94). In vivo experiments in mice with the isolated fractions for evaluation of adjuvant activity also correlated with the relative electrophoretic mobility. In addition to the separation of specific Quillaja saponins with adjuvant effects as a pre-purification step to HPLC, agarose gel electrophoresis stands out as a new method for rapid screening, separation and quality control of saponins. PMID:25839418

  9. 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

  10. 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. PMID:26412246

  11. Novel triterpenoid saponins from the seeds of Celosia argentea L.

    PubMed

    Wu, Qing Bin; Wang, Yan; Liang, Lin; Jiang, Qian; Guo, Mei Li; Zhang, Jun Jie

    2013-08-01

    Two new triterpenoid saponins celosin I (1) and celosin II (2) were isolated from the seeds of Celosia argentea L. (Amaranthaceae). The structures of the two new compounds were elucidated based on chemical analysis and spectral methods (IR, 1-D and 2-D NMR, ESI-MS, HR-ESI-MS). They exhibited significant hepatoprotective effect on carbon tetrachloride-induced and N,N-dimethylformamide-induced hepatotoxicity in mice. PMID:23157342

  12. Steroidal Saponins from Fresh Stems of Dracaena angustifolia

    PubMed Central

    Min, Xu; Ying-Jun, Zhang; Xing-Cong, Li; Jacob, Melissa R.; Chong-Ren, Yang

    2010-01-01

    Six new steroidal saponins (1-6), angudracanosides A-F, were isolated from fresh stems of Dracaena angustifolia (Agavaceae), together with eight known compounds. The structures of compounds 1-6 were determined by detailed spectroscopic analyses and chemical methods. Antifungal testing of all compounds showed that 6 and 7 were active against Cryptococcus neoformans with IC50s of 9.5 and 20.0 μg/mL, respectively. PMID:20718450

  13. [Isolation and identification of a saponine from Patrinia scabiosaefolia].

    PubMed

    Yan, B; Ding, L; Shen, D; Chen, Y; Pei, Y

    1999-04-01

    A saponine compound was isolated from the acetone extract of the roots and rhizomes of Patrinia scabiosaefolia Fish. ex Link. Its structure was identified by combination of chemical reaction and spectrum analysis as 3-O-alpha-L-rhamnopyranosyl-(1-2)-beta-D-xylopyranosyl oleanolic acid (giganteaside D), and part of its 13C-NMR data was revised by the 2D-NMR. The compound was found in the Patrinia for the first time. PMID:12575104

  14. Steroidal saponins from dragon's blood of Dracaena cambodiana.

    PubMed

    Shen, Hai-Yan; Zuo, Wen-Jian; Wang, Hui; Zhao, You-Xing; Guo, Zhi-Kai; Luo, Ying; Li, Xiao-Na; Dai, Hao-Fu; Mei, Wen-Li

    2014-04-01

    Six new steroidal saponins, cambodianosides A-F (1-6), together with seven known ones, were isolated from the dragon's blood of Dracaena cambodiana. The structures of 1-6 were elucidated on the basis of detailed spectroscopic analysis, including 1D and 2D NMR techniques and chemical methods. The cytotoxicities of all the isolated compounds were evaluated in vitro against three human cancer cell lines, and compounds 7, 8, and 11 showed significant inhibitory activities. PMID:24480383

  15. Systematic studies of tannin-formaldehyde aerogels: preparation and properties

    NASA Astrophysics Data System (ADS)

    Amaral-Labat, Gisele; Szczurek, Andrzej; Fierro, Vanessa; Pizzi, Antonio; Celzard, Alain

    2013-02-01

    Gelation of tannin-formaldehyde (TF) solutions was systematically investigated by changing pH and concentration of TF resin in water. In this way we constructed the TF phase diagram, from which chemical hydrogels could be described, and also synthesized thermoreversible tannin-based hydrogels. Conditions of non-gelation were also determined. Hydrogels were dried in supercritical CO2, leading to a broad range of TF aerogels. The latter were investigated for volume shrinkage, total porosity, micro-, meso- and macropore volumes, Brunauer-Emmett-Teller (BET) surface area, microscopic texture, mechanical and thermal properties. All these properties are discussed in relation to each other, leading to an accurate and self-consistent description of these bioresource-based highly porous materials. The conditions for obtaining the highest BET surface area or mesopore volume were determined and explained in relation to the preparation conditions. The highest BET surface area, 880 m2 g-1, is remarkably high for organic aerogels derived from a natural resource.

  16. Stagonospora avenae secretes multiple enzymes that hydrolyze oat leaf saponins.

    PubMed

    Morrissey, J P; Wubben, J P; Osbourn, A E

    2000-10-01

    The phytopathogenic fungus Stagonospora avenae is able to infect oat leaves despite the presence of avenacoside saponins in the leaf tissue. In response to pathogen attack, avenacosides are converted into 26-desglucoavenacosides (26-DGAs), which possess antifungal activity. These molecules are comprised of a steroidal backbone linked to a branched sugar chain consisting of one alpha-L-rhamnose and two (avenacoside A) or three (avenacoside B) beta-D-glucose residues. Isolates of the fungus that are pathogenic to oats are capable of sequential hydrolysis of the sugar residues from the 26-DGAs. Degradation is initiated by removal of the L-rhamnose, which abolishes antifungal activity. The D-glucose residues are then hydrolyzed by beta-glucosidase activity. A comprehensive analysis of saponin-hydrolyzing activities was undertaken, and it was established that S. avenae isolate WAC1293 secretes three enzymes, one alpha-rhamnosidase and two beta-glucosidases, that carry out this hydrolysis. The major beta-glucosidase was purified and the gene encoding the enzyme cloned. The protein is similar to saponin-hydrolyzing enzymes produced by three other phytopathogenic fungi, Gaeumannomyces graminis, Septoria lycopersici, and Botrytis cinerea, and is a family 3 beta-glucosidase. The gene encoding the beta-glucosidase is expressed during infection of oat leaves but is not essential for pathogenicity. PMID:11043466

  17. Steroidal Saponins from the Roots and Rhizomes of Tupistra chinensis.

    PubMed

    Li, Yuze; Wang, Xin; He, Hao; Zhang, Dongdong; Jiang, Yi; Yang, Xinjie; Wang, Fei; Tang, Zhishu; Song, Xiaomei; Yue, Zhenggang

    2015-01-01

    Two new furostanol saponins 1-2 and a new spirostanol saponin 3 were isolated together with two known furostanol saponins 4-5 from the roots and rhizomes of Tupistra chinensis. Their structures were characterized as 1β,2β,3β,4β,5β,26-hexahydroxyfurost-20(22), 25(27)-dien-5,26-O-β-d-glucopyranoside (1), 1β,2β,3β,4β,5β,6β,7α,23ξ,26-nona-hydroxyfurost- 20(22),25(27)-dien-26-O-β-d-glucopyranoside (2), (20S,22R)-spirost-25 (27)-en-1β,3β,5β- trihydroxy-1-O-β-d-xyloside (3), tupisteroide B (4) and 5β-furost-Δ25(27)-en-1β,2β,3β,4β,5β,7α, 22ξ,26-octahydroxy-6-one-26-O-β-d-glucopyranoside (5), respectively, by extensive use of spectroscopic techniques and chemical evidence. Additionally, the in vitro cytotoxic activity of 1-4 was evaluated on human A549 and H1299 tumor cell lines, and compound 3 exhibited cytotoxicity against A549 cells (IC50 86.63 ± 2.33 μmol·L-1) and H1299 cells (IC50 88.21 ± 1.34 μmol·L-1). PMID:26225948

  18. Effects of Ergot Alkaloids on Bovine Sperm Motility In Vitro

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Ergot alkaloids are synthesized by endophyte-infected (Neotyphodium coenophialum) tall fescue (Lolium arundinaceum (Schreb.) S.J. Darbyshire). Our objective was to determine direct effects of ergot alkaloids (ergotamine, dihydroergotamine and ergonovine) on the motility of bovine spermatozoa in vit...

  19. Identification of the quinolizidine alkaloids in Sophora leachiana

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Sophora is a diverse genus representing herbs, shrubs, and trees that occurs throughout the world, primarily in the northern hemisphere. Sophora species contain a variety of quinolizidine alkaloids that are toxic and potentially teratogenic. However, there are no previous reports on the alkaloid c...

  20. Tall fescue seed extraction and partial purification of ergot alkaloids

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Many substances in the tall fescue/endophyte association (Schedonorus arundinaceus/Epichloë coenophiala) have biological activity. Of these compounds only the ergot alkaloids are known to have significant mammalian toxicity and the predominant ergot alkaloids are ergovaline and ergovalinine. Because...

  1. In vitro antibacterial screening of Cryptolepis sanguinolenta alkaloids.

    PubMed

    Paulo, A; Duarte, A; Gomes, E T

    1994-10-01

    The ethanol and aqueous crude extracts and five alkaloids isolated from the roots of Crytolepis sanguinolenta (Lindl.) Schlechter were screened for antibacterial activity against 7 reference strains by the twofold serial broth microdilution assay. The ethanol extract and the alkaloids cryptolepine and cryptoheptine inhibited the growth of all strains tested except that of Pseudomonas aeruginosa. PMID:7853864

  2. New monoterpenoid alkaloids from the aerial parts of Uncaria hirsuta.

    PubMed

    Jia, Jun-Feng; Zhang, Yuan; Huang, Xiao-Jun; Zhang, Sheng-Yuan; Tian, Hai-Yan; Wang, Lei; Ye, Wen-Cai

    2014-01-01

    To investigate the chemical constituents of medicinal plant Uncaria hirsuta, three new monoterpenoid alkaloids, named hirsutanines A-C (1-3), were isolated. Their structures with absolute configurations were elucidated by means of NMR, X-ray diffraction and CD analysis. Compound 3 was the first dimeric monoterpenoid alkaloid obtained from genus Uncaria. PMID:24684175

  3. Tannin concentration enhances seed caching by scatter-hoarding rodents: An experiment using artificial ‘seeds’

    NASA Astrophysics Data System (ADS)

    Wang, Bo; Chen, Jin

    2008-11-01

    Tannins are very common among plant seeds but their effects on the fate of seeds, for example, via mediation of the feeding preferences of scatter-hoarding rodents, are poorly understood. In this study, we created a series of artificial 'seeds' that only differed in tannin concentration and the type of tannin, and placed them in a pine forest in the Shangri-La Alpine Botanical Garden, Yunnan Province of China. Two rodent species ( Apodemus latronum and A. chevrieri) showed significant preferences for 'seeds' with different tannin concentrations. A significantly higher proportion of seeds with low tannin concentration were consumed in situ compared with seeds with a higher tannin concentration. Meanwhile, the tannin concentration was significantly positively correlated with the proportion of seeds cached. The different types of tannin (hydrolysable tannin vs condensed tannin) did not differ significantly in their effect on the proportion of seeds eaten in situ vs seeds cached. Tannin concentrations had no significant effect on the distance that cached seeds were carried, which suggests that rodents may respond to different seed traits in deciding whether or not to cache seeds and how far they will transport seeds.

  4. hERG Blockade by Iboga Alkaloids.

    PubMed

    Alper, Kenneth; Bai, Rong; Liu, Nian; Fowler, Steven J; Huang, Xi-Ping; Priori, Silvia G; Ruan, Yanfei

    2016-01-01

    The iboga alkaloids are a class of naturally occurring and synthetic compounds, some of which modify drug self-administration and withdrawal in humans and preclinical models. Ibogaine, the prototypic iboga alkaloid that is utilized clinically to treat addictions, has been associated with QT prolongation, torsades de pointes and fatalities. hERG blockade as IKr was measured using the whole-cell patch clamp technique in HEK 293 cells. This yielded the following IC50 values: ibogaine manufactured by semisynthesis via voacangine (4.09 ± 0.69 µM) or by extraction from T. iboga (3.53 ± 0.16 µM); ibogaine's principal metabolite noribogaine (2.86 ± 0.68 µM); and voacangine (2.25 ± 0.34 µM). In contrast, the IC50 of 18-methoxycoronaridine, a product of rational synthesis and current focus of drug development was >50 µM. hERG blockade was voltage dependent for all of the compounds, consistent with low-affinity blockade. hERG channel binding affinities (K i) for the entire set of compounds, including 18-MC, ranged from 0.71 to 3.89 µM, suggesting that 18-MC binds to the hERG channel with affinity similar to the other compounds, but the interaction produces substantially less hERG blockade. In view of the extended half-life of noribogaine, these results may relate to observations of persistent QT prolongation and cardiac arrhythmia at delayed intervals of days following ibogaine ingestion. The apparent structure-activity relationships regarding positions of substitutions on the ibogamine skeleton suggest that the iboga alkaloids might provide an informative paradigm for investigation of the structural biology of the hERG channel. PMID:25636206

  5. 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

  6. Chromatographic behaviour of steroidal saponins studied by high-performance liquid chromatography-mass spectrometry.

    PubMed

    Kite, Geoffrey C; Porter, Elaine A; Simmonds, Monique S J

    2007-05-01

    The chromatographic behaviour of steroidal saponins found in Anemarrhena asphodeloides, Asparagus officinalis, Convallaria majalis, Digitalis purpurea and Ruscus aculeatus was studied by HPLC-MS using a C-18 reversed-phase column and aqueous acetonitrile or aqueous methanol mobile phase gradients, with or without the addition of 1% acetic acid. The behaviour was compared to that of triterpene saponins found in Aesculus hippocastanum, Centella asiatica, Panax notoginseng and Potentilla tormentilla. Inclusion of methanol in the mobile phase under acidic conditions was found to cause furostanol saponins hydroxylated at C-22 to chromatograph as broad peaks, whereas the peak shapes of the spirostanol saponins and triterpene saponins studied remained acceptable. In aqueous methanol mobile phases without the addition of acid, furostanol saponins chromatographed with good peak shape, but each C-22 hydroxylated furostanol saponin was accompanied by a second chromatographic peak identified as its C-22 methyl ether. Methanolic extracts analysed in non-acidified aqueous acetonitrile mobile phases also resolved pairs of C-22 hydroxy and C-22 methoxy furostanol saponins. The C-22 methyl ether of deglucoruscoside was found to convert to deglucoruscoside during chromatography in acidified aqueous acetonitrile, or by dissolving in water. Poor chromatography of furostanol saponins in acidified aqueous methanol is due to the interconversion of the C-22 hydroxy and C-22 methoxy forms. It is recommended that initial analysis of saponins by HPLC-MS using a C-18 stationary phase is performed using acidified aqueous acetonitrile mobile phase gradients. The existence of naturally-occurring furostanol saponins methoxylated at C-22 can be investigated with aqueous acetonitrile mobile phases and avoiding methanol in the extraction solvent. PMID:17391684

  7. Heating and reduction affect the reaction with tannins of wine protein fractions differing in hydrophobicity.

    PubMed

    Marangon, Matteo; Vincenzi, Simone; Lucchetta, Marco; Curioni, Andrea

    2010-02-15

    During the storage, bottled white wines can manifest haziness due to the insolubilisation of the grape proteins that may 'survive' in the fermentation process. Although the exact mechanism of this occurrence is not fully understood, proteins and tannins are considered two of the key factors involved in wine hazing, since their aggregation leads to the formation of insoluble particles. To better understand this complex interaction, proteins and tannins from the same unfined Pinot grigio wine were separated. Wine proteins were then fractionated by hydrophobic interaction chromatography (HIC). A significant correlation between hydrophobicity of the wine protein fractions and the haze formed after reacting with wine tannins was found, with the most reactive fractions revealing (by SDS-PAGE and RP-HPLC analyses) the predominant presence of thaumatin-like proteins. Moreover, the effects of both protein heating and disulfide bonds reduction (with dithiotreithol) on haze formation in the presence of tannins were assessed. These treatments generally resulted in an improved reactivity with tannins, and this phenomenon was related to both the surface hydrophobicity and composition of the protein fractions. Therefore, haze formation in wines seems to be related to hydrophobic interactions occurring among proteins and tannins. These interactions should occur on hydrophobic tannin-binding sites, whose exposition on the proteins can depend on both protein heating and reduction. PMID:20103151

  8. Transformation of Litchi Pericarp-Derived Condensed Tannin with Aspergillus awamori.

    PubMed

    Lin, Sen; Li, Qing; Yang, Bao; Duan, Xuewu; Zhang, Mingwei; Shi, John; Jiang, Yueming

    2016-01-01

    Condensed tannin is a ubiquitous polyphenol in plants that possesses substantial antioxidant capacity. In this study, we have investigated the polyphenol extraction recovery and 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging activity of the extracted polyphenol after litchi pericarp is treated with Aspergillus awamori, Aspergillus sojae or Aspergillus oryzae. We have further explored the activity of A. awamori in the formation of condensed tannin. The treatment of A. awamori appeared to produce the highest antioxidant activity of polyphenol from litchi pericarp. Further studies suggested that the treatment of A. awamori releases the non-extractable condensed tannin from cell walls of litchi pericarp. The total extractable tannin in the litchi pericarp residue after a six-time extraction with 60% ethanol increased from 199.92 ± 14.47-318.38 ± 7.59 μg/g dry weight (DW) after the treatment of A. awamori. The ESI-TOF-MS and HPLC-MS² analyses further revealed that treatment of A. awamori degraded B-type condensed tannin (condensed flavan-3-ol via C4-C8 linkage), but exhibited a limited capacity to degrade the condensed tannin containing A-type linkage subunits (C4-C8 coupled C2-O-C7 linkage). These results suggest that the treatment of A. awamori can significantly improve the production of condensed tannin from litchi pericarp. PMID:27420043

  9. Interference of condensed tannin in lignin analyses of dry bean and forage crops.

    PubMed

    Marles, M A Susan; Coulman, Bruce E; Bett, Kirstin E

    2008-11-12

    Legumes with high concentrations of condensed tannin (pinto bean [Phaseolus vulgaris L.], sainfoin [Onobrychis viciifolia Scop.], and big trefoil [Lotus uliginosus Hoff.]), were compared to a selection of forages, with low or zero condensed tannin (smooth bromegrass [ Bromus inermis Leyss], Lotus japonicus [Regel] K. Larsen, and alfalfa [Medicago sativa L.]), using four methods to estimate fiber or lignin. Protocols were validated by using semipurified condensed tannin polymers in adulteration assays that tested low-lignin tissue with polyphenolic-enriched samples. The effect on lignin assay methods by condensed tannin concentration was interpreted using a multivariate analysis. There was an overestimation of fiber or lignin in the presence of condensed tannin in the acid detergent fiber (ADF) and Klason lignin (KL) assays compared to that in the thioglycolic acid (TGA) and acid detergent lignin (ADL) methods. Sulfite reagents (present in TGA lignin method) or sequential acidic digests at high temperatures (ADF followed by ADL) were required to eliminate condensed tannin. The ADF (alone) and KL protocols are not recommended to screen nonwoody plants, such as forages, where condensed tannin has accumulated in the tissue. PMID:18841900

  10. The role of tannins in conventional and membrane treatment of tannery wastewater.

    PubMed

    Munz, G; De Angelis, D; Gori, R; Mori, G; Casarci, M; Lubello, C

    2009-05-30

    The role that tannins play in tannery wastewater treatment has been evaluated employing a pilot Membrane Bioreactor (MBR) plant and a full scale Conventional Activated Sludge Process (CASP) plant conducted in parallel. The proposed methodology has established the preliminary use of respirometry to examine the biodegradability of a selection of commercial products (synthetic and natural tannins); the subsequent analysis, by means of spectrophotometric reading and RP-IPC (Reverse-Phase Ion-Pair) liquid chromatography, estimates the concentrations of natural tannins and naphthalenesulfonic tanning agents in the influent and effluent samples. The results show that a consistent percentage of the Total Organic Carbon (TOC) in the effluent of the biological phase of the plants is attributable to the presence of natural and synthetic (Sulfonated Naphthalene-Formaldehyde Condensates, SNFC) tannins (17% and 14% respectively). The titrimetric tests that were aimed at evaluating the levels of inhibition on the nitrifying biomass samples did not allow a direct inhibiting effect to be associated with the concentration levels of the tannin in the effluent. Nonetheless, the reduced specific growth rates of ammonium and nitrite oxidising bacteria imply that a strong environmental pressure is present, if not necessarily due to the concentration of tannins, due to the wastewater as a whole. The differences that have emerged by comparing the two technologies (CASP and MBR), in regards to the role that tannins play in terms of biodegradability, did not appear to be significant. PMID:18835658

  11. Transformation of Litchi Pericarp-Derived Condensed Tannin with Aspergillus awamori

    PubMed Central

    Lin, Sen; Li, Qing; Yang, Bao; Duan, Xuewu; Zhang, Mingwei; Shi, John; Jiang, Yueming

    2016-01-01

    Condensed tannin is a ubiquitous polyphenol in plants that possesses substantial antioxidant capacity. In this study, we have investigated the polyphenol extraction recovery and 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging activity of the extracted polyphenol after litchi pericarp is treated with Aspergillus awamori, Aspergillus sojae or Aspergillus oryzae. We have further explored the activity of A. awamori in the formation of condensed tannin. The treatment of A. awamori appeared to produce the highest antioxidant activity of polyphenol from litchi pericarp. Further studies suggested that the treatment of A. awamori releases the non-extractable condensed tannin from cell walls of litchi pericarp. The total extractable tannin in the litchi pericarp residue after a six-time extraction with 60% ethanol increased from 199.92 ± 14.47–318.38 ± 7.59 μg/g dry weight (DW) after the treatment of A. awamori. The ESI-TOF-MS and HPLC-MS2 analyses further revealed that treatment of A. awamori degraded B-type condensed tannin (condensed flavan-3-ol via C4–C8 linkage), but exhibited a limited capacity to degrade the condensed tannin containing A-type linkage subunits (C4–C8 coupled C2–O–C7 linkage). These results suggest that the treatment of A. awamori can significantly improve the production of condensed tannin from litchi pericarp. PMID:27420043

  12. Condensed tannins in the diets of primates: a matter of methods?

    PubMed

    Rothman, Jessica M; Dusinberre, Kathy; Pell, Alice N

    2009-01-01

    To understand the ways in which condensed tannins (CT) affect primate diet selection and nutritional status, correct measurements are essential. In the majority of studies of the CT contents of primate foods, a tannin source such as "quebracho" is used to standardize CT assays, but the CT in quebracho tannin may not be similar to those in the plants of interest. We investigated how the choice of standard to calibrate CT assays affects the estimation of CT in the diets of mountain gorillas (Gorilla beringei). We purified the CT from gorilla foods and compared the actual amounts of CT in the foods with estimates produced by using the quebracho tannin. When quebracho was used, the estimates of CT contents of gorilla foods were, on average, 3.6 times the actual content of CT so that the amounts in frequently eaten gorilla foods were substantially overestimated. The overestimation for a given plant could not be predicted reliably and the ranking of plants by tannin content differed according to the standard used. Our results demonstrate that accurate measurements of CT necessitate the use of tannins purified from the plant species of interest. A reevaluation of primatology studies using interspecific comparisons of tannin content will provide new insights into primate food selection and nutritional ecology. PMID:18925644

  13. Antioxidant status of faeces of captive black rhinoceros (Diceros bicornis) in relation to dietary tannin supplementation.

    PubMed

    Clauss, M; Pellegrini, N; Castell, J C; Kienzle, E; Dierenfeld, E S; Hummel, J; Flach, E J; Streich, W J; Hatt, J-M

    2006-08-01

    In context with the frequent observations of excessive iron (Fe) storage in captive black rhinoceroses (Diceros bicornis), it has been suggested that both an excessive dietary Fe content and a lack of dietary Fe-chelating substances, such as tannins, is the underlying cause. Therefore, studies on the effects of tannin supplementation to captive diet are warranted. Six captive rhinoceroses were fed their normal zoo diet (N), and a similar diet supplemented with either tannic acid (T, hydrolysable tannin) or quebracho (Q, condensed tannins), and the total antioxidant capacity (TAC) was measured as mmol Trolox equivalents per kg fresh faeces. The TAC values on diets N (1.24 +/- 0.39 mmol/kg fresh faeces) and T (1.34 +/- 0.33 mmol/kg fresh faeces) were similar, but significantly higher on diet Q (2.32 +/- 0.61 mmol/kg fresh faeces). In contrast to expectations, faecal TAC increased with increasing faecal Fe, possibly as a result of the fact that the faecal Fe content was positively correlated to the proportion of concentrate feeds in the diet, which also contain antioxidants, such as vitamin E, in addition to Fe. Increased antioxidant status caused by the use of tannin substances could have a beneficial effect on animal health, but if tannins should be incorporated in designed diets, other tannin sources, such as grape pomace should be tested. PMID:16901277

  14. Persimmon-Tannin, an α-Amylase Inhibitor, Retards Carbohydrate Absorption in Rats.

    PubMed

    Tsujita, Takahiro

    2016-01-01

    Inhibitors of carbohydrate-hydrolyzing enzymes play an important role in controlling postprandial blood glucose levels. Thus the effect of persimmon tannin on pancreatic α-amylase and intestinal α-glucosidase has been investigated. Persimmon tannin inhibits pancreatic α-amylase and intestinal α-glucosidase in a concentration-dependent manner with the 50% inhibition concentration (IC50) for amylase, maltase and sucrase being 1.7 μg/mL, 632 μg/mL and 308 μg/mL, respectively. The effect of persimmon-tannin extract on carbohydrate absorption in rats has also been investigated. Oral administration of persimmon tannin to normal rats fed cornstarch (2 g/kg body weight) significantly suppressed the increase in blood glucose levels and the area under the curve (AUC) after starch loading in a dose-dependent manner. The effective dose of persimmon tannin required to achieve 50% suppression of the rise in blood glucose level was estimated to be 300 mg/kg body weight. Administration of persimmon tannin to rats fed maltose or sucrose delayed the increase of blood glucose level and slightly suppressed AUC, but not significantly. These results suggest that persimmon tannin retards absorption of carbohydrate and reduces post-prandial hyperglycemia mainly through inhibition of α-amylase. PMID:27465726

  15. 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. PMID:26878488

  16. Enantioselective Total Synthesis of Tricyclic Myrmicarin Alkaloids

    PubMed Central

    Movassaghi, Mohammad; Ondrus, Alison E.

    2010-01-01

    An enantioselective gram-scale synthesis of a key dihydroindolizine intermediate for the preparation of myrmicarin alkaloids is described. Key transformations in this convergent approach include a stereospecific palladium–catalyzed N-vinylation of a pyrrole with a vinyl triflate, a copper–catalyzed enantioselective conjugate reduction of a β-pyrrolyl enoate, and a regioselective Friedel-Crafts reaction. The synthesis of optically active and isomerically pure samples of (4aR)-myrmicarins 215A, 215B, and 217 in addition to their respective C4a-epimers is presented. PMID:16178549

  17. Antiproliferative Activity of Amathaspiramide Alkaloids and Analogs.

    PubMed

    Shimokawa, Jun; Chiyoda, Koji; Umihara, Hirotatsu; Fukuyama, Tohru

    2016-08-01

    Assisted by the total syntheses of all the amathaspiramides, six natural products and four synthetic intermediates with partially fluctuating structures were prepared and subjected to a growth inhibition assay in four human cancer cell lines. The results showed amathaspiramides A, C, and E had moderate antiproliferative activity. Examination of the structure-activity relationship revealed the importance of the amine or imine substructure on the pyrrolidine moiety and the 8R stereochemistry on the N-acyl hemiaminal moiety for the antiproliferative activity of amathaspiramide alkaloids. PMID:27169437

  18. The influence of dietary tannin supplementation on digestive performance in captive black rhinoceros (Diceros bicornis).

    PubMed

    Clauss, M; Castell, J C; Kienzle, E; Dierenfeld, E S; Flach, E J; Behlert, O; Ortmann, S; Streich, W J; Hummel, J; Hatt, J-M

    2007-12-01

    Free-ranging browsers such as the black rhinoceros (Diceros bicornis) consume a diet that contains tannins, whereas the diets offered to them in captivity consist mostly of items known to contain hardly any such secondary plant compounds. Tannins could have potentially beneficial effects, including the chelation of dietary iron (iron storage disease is a common problem in black rhinos). Here, we tested the acceptance, and the consequences on digestion variables, of a low-dose tannin supplementation in captive animals. Eight black rhinoceroses from three zoological institutions were used. Faecal output was quantified by total faecal collection. Diets fed were regular zoo diets supplemented with either tannic acid (T, hydrolysable tannin) or quebracho (Q, condensed tannins); overall tannin source intake increased at 5-15 g/kg dry matter (DM) in relation to regular zoo diets. Adaptation periods to the new diets were >2 months. Additional data were taken from one hitherto unpublished study. Data were compared to measurements in the same animals on their regular zoo diets. All animals accepted the new diets without hesitation. There was no influence of tannin supplementation on digestion coefficients of DM and its constituents, or faecal concentrations of short-chain fatty acids or lactate. Water intake did not increase during tannin supplementation. Should the inclusion of dietary tannin sources be an objective in the development of diets for captive rhinoceroses, moderate doses such as used in this study are unlikely to cause relevant depressions of digestive efficiency and will not interfere with bacterial fermentation in a relevant way. PMID:17988348

  19. Processing conditions analysis of Eucalyptus globulus plywood bonded with resol-tannin adhesives.

    PubMed

    Stefani, P M; Peña, C; Ruseckaite, R A; Piter, J C; Mondragon, I

    2008-09-01

    Phenol-formaldehyde resol containing mimosa tannin extract was employed to produce plywood panels with two plies from Eucalyptus globulus veneers. The effect of processing conditions and tannin content on the gelation time of the adhesive in the glue line was evaluated by dynamic-mechanical analysis (DMA). These results were related with shear strength and wood failure of glue line in the final panels. Hazardous petrochemical phenol could be partially substituted in resols in industrial applications by addition of mimosa tannin extracts. PMID:18024109

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

    Technology Transfer Automated Retrieval System (TEKTRAN)

    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...

  1. Enhancement of saporin cytotoxicity by Gypsophila saponins--more than stimulation of endocytosis.

    PubMed

    Weng, A; Bachran, C; Fuchs, H; Krause, E; Stephanowitz, H; Melzig, M F

    2009-10-30

    Saporin is a type I ribosome-inactivating protein with N-glycosidase activity. It removes adenine residues from the 28S ribosomal RNA resulting in inhibition of protein synthesis. Recently we have shown that saporin exerts no cytotoxicity on seven human cell lines. However, the combination of saporin with a special mixture of Gypsophila saponins (Soapwort saponins) from Gypsophila paniculata L. (baby's breath) rendered saporin to a potent cytotoxin comparable to viscumin, a highly toxic type II ribosome-inactivating protein. In this study we investigated whether the enhancement of the saporin-cytotoxicity by Gypsophila saponins is mediated by a saponin-triggered modulation of endocytosis, exocytosis or impaired degradation processes of his-tagged saporin ((his)saporin) in ECV-304 cells. For this purpose (his)saporin was labelled with tritium and cytotoxicity of the toxin alone and in combination with Gypsophila saponins was scrutinized. The transport and degradation processes of (his)saporin were not different in Gypsophila saponin-treated and control cells. However, after ultracentrifugation of a post-nuclear supernatant the amount of cytosolic (his)saporin was significantly higher in saponin-treated cells than in cells, which were only incubated with (his)saporin. This indicates a saponin mediated endosomal escape of saporin. PMID:19615984

  2. Multidirectional effects of triterpene saponins on cancer cells - mini-review of in vitro studies.

    PubMed

    Koczurkiewicz, Paulina; Czyż, Jarosław; Podolak, Irma; Wójcik, Katarzyna; Galanty, Agnieszka; Janeczko, Zbigniew; Michalik, Marta

    2015-01-01

    Triterpene saponins (saponosides) are found in a variety of higher plants and display a wide range of pharmacological activities, including expectorant, anti-inflamatory, vasoprotective, gastroprotective and antimicrobial properties. Recently, a potential anticancer activity of saponins has been suggested by their cytotoxic, cytostatic, pro-apoptotic and anti-invasive effects. At high concentrations (more than 100 µM) saponins exert cytotoxic and haemolytic effects via permeabilization of the cell membranes. Noteworthy, the inhibition of cancer cell proliferation, the induction of apoptosis and attenuation of cell invasiveness is observed in the presence of low saponin concentrations. Saponins might affect the expression of genes associated with malignancy. These alterations are directly related to the invasive phenotype of cancer cells and depend on "cellular context". It illustrates the relationships between the action of saponins, and the momentary genomic/proteomic status of cancer cells. Here, we discuss the hallmarks of anti-cancer activity of saponins with the particular emphasis on anti-invasive effect of diverse groups of saponins that have been investigated in relation to tumor therapy. PMID:26307770

  3. In vitro activity of CAY-1, a saponin from Capsicum frutescens, against microsporum and trichophyton species

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Dermatomycoses are among the world’s most common diseases. The incidence of dermatomycoses has increased over recent years, particularly in immunosuppressed patients. In previous studies, the saponin CAY-1, a saponin from cayenne pepper (Capsicum frutenses), has shown antifungal activities against...

  4. Triterpene saponins from Clematis chinensis and their potential anti-inflammatory activity.

    PubMed

    Fu, Qiang; Zan, Ke; Zhao, Mingbo; Zhou, Sixiang; Shi, Shepo; Jiang, Yong; Tu, Pengfei

    2010-07-23

    Seven new triterpene saponins, clematochinenosides A-G (1-7), together with 17 known saponins (8-24), were isolated from the roots and rhizomes of Clematis chinensis. Their structures were elucidated on the basis of spectroscopic evidence and hydrolysis products. Compounds 1, 3-7, and 20-24 showed inhibitory activities against COX-1 and COX-2 enzymes. PMID:20540535

  5. 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

  6. Versatile strategy for the divergent synthesis of linear oligosaccharide domain variants of Quillaja saponin vaccine adjuvants.

    PubMed

    Fernández-Tejada, Alberto; Tan, Derek S; Gin, David Y

    2015-09-21

    We describe a new, versatile synthetic approach to Quillaja saponin variants based on the natural product immunoadjuvant QS-21. This modular, divergent strategy provides efficient access to linear oligosaccharide domain variants with modified sugars and regiochemistries. This new synthetic approach opens the door to the rapid generation of diverse analogues to identify novel saponin adjuvants with improved synthetic accessibility. PMID:26243268

  7. Neurotoxic Alkaloids: Saxitoxin and Its Analogs

    PubMed Central

    Wiese, Maria; D’Agostino, Paul M.; Mihali, Troco K.; Moffitt, Michelle C.; Neilan, Brett A.

    2010-01-01

    Saxitoxin (STX) and its 57 analogs are a broad group of natural neurotoxic alkaloids, commonly known as the paralytic shellfish toxins (PSTs). PSTs are the causative agents of paralytic shellfish poisoning (PSP) and are mostly associated with marine dinoflagellates (eukaryotes) and freshwater cyanobacteria (prokaryotes), which form extensive blooms around the world. PST producing dinoflagellates belong to the genera Alexandrium, Gymnodinium and Pyrodinium whilst production has been identified in several cyanobacterial genera including Anabaena, Cylindrospermopsis, Aphanizomenon Planktothrix and Lyngbya. STX and its analogs can be structurally classified into several classes such as non-sulfated, mono-sulfated, di-sulfated, decarbamoylated and the recently discovered hydrophobic analogs—each with varying levels of toxicity. Biotransformation of the PSTs into other PST analogs has been identified within marine invertebrates, humans and bacteria. An improved understanding of PST transformation into less toxic analogs and degradation, both chemically or enzymatically, will be important for the development of methods for the detoxification of contaminated water supplies and of shellfish destined for consumption. Some PSTs also have demonstrated pharmaceutical potential as a long-term anesthetic in the treatment of anal fissures and for chronic tension-type headache. The recent elucidation of the saxitoxin biosynthetic gene cluster in cyanobacteria and the identification of new PST analogs will present opportunities to further explore the pharmaceutical potential of these intriguing alkaloids. PMID:20714432

  8. Cyclodextrin assisted nanophase determination of alkaloid salts.

    PubMed

    Csernák, Orsolya; Buvári-Barcza, Agnes; Barcza, Lajos

    2006-04-15

    The poor water solubility of the free base and the high dissociation constant (K(a)) hinder mainly the assay of alkaloid salts. We have elaborated an environment friendly method that can be carried out in aqueous media. The stability difference of the cyclodextrin (CD) complexes of free and protonated bases were used for this purpose. The base is included into the hydrophobic cavity of the CD (which serves as an apolar solvent phase on molecular level) and its solubility in water is increased. Since the base forms more stable inclusion complex than its protonated species, the pK(a) is decreased and the potentiometric titration is promoted by this way, too. Six different hydrohalide alkaloid salts have been investigated and the most appropriate CDs were chosen (depending on the size of the molecules and/or substituents). The results of the assays agree well with those obtained by the direct nonaqueous titrations. The stability constants of the inclusion complexes have been also computed. PMID:18970584

  9. Chirality and numbering of substituted tropane alkaloids.

    PubMed

    Humam, Munir; Shoul, Tarik; Jeannerat, Damien; Muñoz, Orlando; Christen, Philippe

    2011-01-01

    The strict application of IUPAC rules for the numbering of tropane alkaloids is not always applied by authors and there is hence a lot of confusion in the literature. In most cases, the notation of 3, 6/7-disubstituted derivatives has been chosen arbitrarily, based on NMR and MS data, without taking into account the absolute configuration of these two carbons. This paper discusses the problem and the relevance of CD and NMR to determine molecular configurations. We report on the use of (1)H-NMR anisochrony (Δδ) induced by the Mosher's chiral auxiliary reagents (R)-(-)- and (S)-(+)-α-methoxy-α-trifluoromethyl-phenylacetyl chlorides (MTPA-Cl), to determine the absolute configuration of (3R,6R)-3α-hydroxy-6β-senecioyloxytropane, a disubstituted tropane alkaloid isolated from the aerial parts of Schizanthus grahamii (Solanaceae). These analytical tools should help future works in correctly assigning the configuration of additional 3, 6/7 disubstituted tropane derivatives. PMID:21869748

  10. Antifungal Quinoline Alkaloids from Waltheria indica.

    PubMed

    Cretton, Sylvian; Dorsaz, Stéphane; Azzollini, Antonio; Favre-Godal, Quentin; Marcourt, Laurence; Ebrahimi, Samad Nejad; Voinesco, Francine; Michellod, Emilie; Sanglard, Dominique; Gindro, Katia; Wolfender, Jean-Luc; Cuendet, Muriel; Christen, Philippe

    2016-02-26

    Chemical investigation of a dichloromethane extract of the aerial parts of Waltheria indica led to the isolation and characterization of five polyhydroxymethoxyflavonoids, namely, oxyanin A (1), vitexicarpin (3), chrysosplenol E (4), flindulatin (5), 5-hydroxy-3,7,4'-trimethoxyflavone (6), and six quinolone alkaloids, waltheriones M-Q (2, 7, 8, 10, 11) and 5(R)-vanessine (9). Among these, compounds 2, 7, 8, 10, and 11 have not yet been described in the literature. Their chemical structures were established by means of spectroscopic data interpretation including (1)H and (13)C, HSQC, HMBC, COSY, and NOESY NMR experiments and UV, IR, and HRESIMS. The absolute configurations of the compounds were established by ECD. The isolated constituents and 10 additional quinoline alkaloids previously isolated from the roots of the plant were evaluated for their in vitro antifungal activity against the human fungal pathogen Candida albicans, and 10 compounds (7, 9, 11-16, 18, 21) showed growth inhibitory activity on both planktonic cells and biofilms (MIC ≤ 32 μg/mL). Their spectrum of activity against other pathogenic Candida species and their cytotoxicity against human HeLa cells were also determined. In addition, the cytological effect of the antifungal isolated compounds on the ultrastructure of C. albicans was evaluated by transmission electron microscopy. PMID:26848627

  11. Antifungal Indole Alkaloids from Winchia calophylla.

    PubMed

    Yang, Mei-Li; Chen, Jia; Sun, Meng; Zhang, Dong-Bo; Gao, Kun

    2016-05-01

    Ten indole alkaloids (1-10) were obtained from an antifungal extract of Winchia calophylla, of which two (2 and 4) were new. N(4)-Methyl-10-hydroxyl-desacetylakuammilin (2) was an akuammiline-type indole alkaloid. N(1)-Methyl-echitaminic acid (4) was an unusual zwitterion with a basic vincorine-type skeleton. This is the first report of 10 in W. calophylla. The structures of all of the compounds were determined based on spectroscopic data, and their bioactivities were assessed. Compound 1 showed potent activity against the plant pathogenic fungi of Penicillium italicum and Fusarium oxysporum f.sp cubens with IC50 s of 10.4 and 11.5 µM, respectively, and 3 inhibited Rhizoctonia solani with an IC50 of 11.7 µM. Compounds 2 and 4 showed weak cytotoxicity against the human leukemic cell line HL-60 in vitro with IC50 s of 51.4 and 75.3 µM, respectively. Compounds 1 and 2 displayed weak activity against acetylcholinesterase with IC50 s around 61.3 and 52.6 µM, respectively. PMID:27002397

  12. Simenoside A, a new triterpenoid saponin from Gypsophila simonii Hub.-Mor.

    PubMed

    Arslan, Idris

    2014-03-01

    Saponins are amphiphilic glycoconjugates which give soap-like foams in H2 O. A new triterpenoid saponin, simenoside A (1), based on gypsogenin aglycone, and the known saponin 2 were isolated from Gypsophila simonii Hub.-Mor. The structure of the new saponin was elucidated as 3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopyranosylgypsogenin 28-O-β-D-glucopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→2)-β-D-xylopyranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranosyl ester on the basis of extensive spectral analyses and chemical evidence. Saponins 1 and 2 were isolated from G. simonii for the first time. PMID:24634074

  13. Identification and determination of ergot alkaloids in Morning Glory cultivars.

    PubMed

    Nowak, Julia; Woźniakiewicz, Michał; Klepacki, Piotr; Sowa, Anna; Kościelniak, Paweł

    2016-05-01

    Seeds of plants from Ipomoea genera contain numerous ergot alkaloids, including psychoactive ergine and ergometrine, and are often abused as so-called "legal highs." In this work, an analytical method for determination of ergine and ergometrine, and identification of other alkaloids was developed, optimized, and validated. Three extraction techniques, ultrasound-assisted extraction in bath, or with sonotrode, and microwave-assisted extraction were evaluated, and it was concluded that ultrasonic bath is the most suitable technique for extraction of ergot alkaloids. The extraction method was later optimized using a Doehlert experimental design with response surface methodology and used together with the optimized LC-Q-TOF-MS method. The analytical procedure was validated in terms of recovery and matrix effect, repeatability, and intermediate precision. Limits of detection and quantification were 1.0 and 3.0 ng mL(-1), respectively, and were sufficient for determination of ergot alkaloids in Ipomoea seeds. The analysis revealed that from five kinds of seeds purchased from different vendors, only three contained ergot alkaloids. Concentration of alkaloids and their relative abundance was similar in samples representative for whole seeds packs; however, when single seeds were analyzed, significant discrepancies in ergine and ergometrine concentrations were detected. Graphical Abstract Identification of six ergot alkaloids and determination of ergine and ergometrine in Morning glory seeds using the ultrasound-assisted extraction followed the LC-MS analysis. PMID:26873205

  14. Effect of Holothuria leucospilota extracted saponin on maturation of mice oocyte and granulosa cells.

    PubMed

    Moghadam, Fereshteh Delghandi; Baharara, Javad; Balanezhad, Saeedeh Zafar; Jalali, Mohsen; Amini, Elaheh

    2016-01-01

    Sea cucumbers saponins are triterpenoid glycosides which exert beneficial biomedical effects. This study was performed to assess the effect of saponin extracted from sea cucumber Holothuria leucospilota (H. leucospilota) on maturation of mice oocytes and granulosa cells. The germinal vesicles oocytes were collected from 6-8 weeks old Naval Medical Research Institute (NMRI) mice ovaries, randomly divided into untreated and four experimental groups and cultured In vitro. Maturation medium was supplemented with 0, 1, 2, 4 and 8 μg/ml saponin for 12 days. The rates of maturation were recorded through morphological observation by measurement of follicle diameter during treatment. After 4 days, the effects of saponin on granulosa cells were investigated by reactive oxygen species (ROS) measurement, super oxide dismutase (SOD) activity, caspase assay and tumor necrosis factor-alpha (TNF-α) expression. The oocyte maturation rate was significantly higher in treated groups (1 μg/ml). The ROS and SOD assays demonstrated the antioxidant potential of saponin. The caspase assay exhibited that optimum concentrations of saponin (1, 2 μg/ml) reduced caspase activity in granulosa cells. Flow cytometry showed that optimum concentration of saponin promoted oocyte maturation via down regulation of TNF-α as follicular degenerative factor in nursing cells. These results proposed that maturation rate were obtained after the incorporation of 1 μg/ml sea cucumber saponin. Moreover, the extracted saponin at concentrations of 1, 2 μg/ml enhanced follicle growth which is accompanied by attenuating ROS formation, elevating SOD activity and reducing TNF-α expression in granulosa cells. But, further examinations are required to understand precise mechanisms of saponin action on oocyte and granulosa cells. PMID:27168752

  15. [Material for evaluation of notoginseng total saponin preparation induced pseudoanaphylactoid reactions].

    PubMed

    Yu, Ting-ting; Li, Jie; Zhao, Jia-wei; Zhang, Ya-xin; Li, Dan-dan; Liang, Ai-hua; Liu, Guan-ping; Gao, Shan; Gao, Yue

    2015-07-01

    The experiment is designed to explore pathological festures and material basis of pseadoanaphylactoid reaction induced by notoginseng total saponin preparation. Mouse pseadoanaphylactoid reaction was used, 50 ICR mice were randomly assigned to control group, positive medicine group, notoginseng total saponin preparation low-dose group, notoginseng total saponin preparation middle-dose group, notoginseng total saponin preparation high-dose group on average. They are treated by intravenous injection of test substance solutions containing 0.4% Evans blue (EB). 30 min later, scores of ear blue staining and quantitation of ear EB exudation were recorded. Another two experiment were repeated in the same way excluding EB, just to. detect the related cytokines in serum using ELISA. We found that the scores of pseudoanaphylactoid reaction in notoginseng total saponin preparation injection middle-dose group and high-dose group was evidently higher than that in control group, suggesting that notoginseng total saponin preparation injection may be can lead to pseadoanaphylactoid reaction. HE staining showed that pseadoanaphylactoid reaction induced by notoginseng total saponin preparation injection is related to inflammation. Histamine, VEGF and TNF-α levels in notoginseng total saponin preparation middle-dose group and high-dose group significantly increased (P < 0.05, P < 0.01) than control group and showed a dose-dependent manner as well as consistent with the degree of ear blue dye. While IL-6 and IL-10 content did not increase significantly in notoginseng total saponin preparation low-dose group and middle-dose group, but they significantly higher than control group (P < 0.05, P < 0.01) when it increased to quadrupe clinical concentrations, eight times of the clinical dose. So pseadoanaphylactoid reaction caused by notoginseng total saponin preparation may be related to histamine, VEGF, TNF-α, and it is possible that IL-6 and IL-10 can play a role when

  16. Effect of Holothuria leucospilota extracted saponin on maturation of mice oocyte and granulosa cells

    PubMed Central

    Moghadam, Fereshteh Delghandi; Baharara, Javad; Balanezhad, Saeedeh Zafar; Jalali, Mohsen; Amini, Elaheh

    2016-01-01

    Sea cucumbers saponins are triterpenoid glycosides which exert beneficial biomedical effects. This study was performed to assess the effect of saponin extracted from sea cucumber Holothuria leucospilota (H. leucospilota) on maturation of mice oocytes and granulosa cells. The germinal vesicles oocytes were collected from 6–8 weeks old Naval Medical Research Institute (NMRI) mice ovaries, randomly divided into untreated and four experimental groups and cultured In vitro. Maturation medium was supplemented with 0, 1, 2, 4 and 8 μg/ml saponin for 12 days. The rates of maturation were recorded through morphological observation by measurement of follicle diameter during treatment. After 4 days, the effects of saponin on granulosa cells were investigated by reactive oxygen species (ROS) measurement, super oxide dismutase (SOD) activity, caspase assay and tumor necrosis factor-alpha (TNF-α) expression. The oocyte maturation rate was significantly higher in treated groups (1 μg/ml). The ROS and SOD assays demonstrated the antioxidant potential of saponin. The caspase assay exhibited that optimum concentrations of saponin (1, 2 μg/ml) reduced caspase activity in granulosa cells. Flow cytometry showed that optimum concentration of saponin promoted oocyte maturation via down regulation of TNF-α as follicular degenerative factor in nursing cells. These results proposed that maturation rate were obtained after the incorporation of 1 μg/ml sea cucumber saponin. Moreover, the extracted saponin at concentrations of 1, 2 μg/ml enhanced follicle growth which is accompanied by attenuating ROS formation, elevating SOD activity and reducing TNF-α expression in granulosa cells. But, further examinations are required to understand precise mechanisms of saponin action on oocyte and granulosa cells. PMID:27168752

  17. Application of Ultrasound and Ozone for the Removal of Aqueous Tannin

    NASA Astrophysics Data System (ADS)

    Son, Younggyu; Lim, Junghyun; Cui, Mingcan; Lim, Myunghee; Kweon, Bo-Youn; Khim, Jeehyeong

    2009-07-01

    In order to investigate the enhancement of combination of ultrasound process and ozonation for the removal of aqueous tannin, tannin concentration, chemical oxygen demand (COD), and total organic carbon (TOC) were analyzed in ultrasound process, ozonation, and ultrasound/ozone process. Even though ultrasound process was not effective for the removal of aqueous in terms of tannin concentration, COD, and TOC, ultrasound process could enhance the removal efficiency significantly when it was combined with ozonation. It was also revealed that COD removal resulted in partly mineralization due to insufficient oxidation power, which was induced by ultrasound and ozone. However average oxidation state of all organics in the solution was increased cogently and as a result, biodegradability could be increased meaningfully. Therefore ultrasound/ozone process could be effective pre-treatment process to biological process for the removal of aqueous tannin.

  18. Purity assessment of condensed tannin fractions by nuclear magnetic resonance (NMR) spectroscopy

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Unambiguous investigation of condensed tannin (CT) structure-activity relationships in biological systems requires the use of highly enriched CT fractions of defined chemical purity. Purification of CTs from Sorghum bicolor, Trifolium repens, Theobroma cacao, Lespedeza cuneata, Lotus pedunculatus, a...

  19. Polyphenols, condensed tannins, and other natural products in Onobrychis viciifolia (Sainfoin).

    PubMed

    Marais, J P; Mueller-Harvey, I; Brandt, E V; Ferreira, D

    2000-08-01

    An acetone/water extract of the fodder legume Onobrychis viciifolia afforded arbutin, kaempferol, quercetin, rutin, afzelin, the branched quercetin-3-(2(G)-rhamnosylrutinoside), the amino acid L-tryptophan, the inositol (+)-pinitol, and relatively high concentrations of sucrose (ca. 35% of extractable material). Acid-catalyzed cleavage of the condensed tannins with phloroglucinol afforded catechin, epicatechin and gallocatechin as the terminal and extender units, but epigallocatechin was only present in extender units. The condensed tannins in O. viciifolia presumably consist of hetero- and homopolymers containing both procyanidin and prodelphinidin units. Comparison of data from the present study and the literature suggests that sainfoin tannins have a highly variable composition with cis:trans ratios ranging from 47:53 to 90:10 and delphinidin:cyanidin ratios from 36:64 to 93:7. The composition of terminal and extender units in sainfoin tannins seems to be cultivar specific. PMID:10956131

  20. Antiplasmodial activity of Cryptolepis sanguinolenta alkaloids from leaves and roots.

    PubMed

    Paulo, A; Gomes, E T; Steele, J; Warhurst, D C; Houghton, P J

    2000-02-01

    The roots of Cryptolepis sanguinolenta have been investigated for their chemical composition since 1931 but so far no studies on the leaves have been reported although they are used in traditional medicine in Guinea-Bissau. Two new alkaloids identified as cryptolepinoic acid (1) and methyl cryptolepinoate (2) and the known alkaloids cryptolepine (4), hydroxycryptolepine (5/5a) and quindoline (6), were isolated from the ethanolic and chlorophormic leaf extracts. Aqueous and ethanolic extracts of the leaves and roots and seven alkaloids isolated from those extracts were tested in vitro against Plasmodium falciparum K1 (multidrug-resistant strain) and T996 (chloroquine-sensitive clone). All the extracts were shown to give 90% inhibition of P. falciparum K1 growth at concentrations < 23 micrograms/ml. Cryptolepine (4) was the most active alkaloid tested with IC50 values (0.23 microM to K1; 0.059 microM to T996) comparable with chloroquine (0.26 microM to K1; 0.019 microM to T996). The indolobenzazepine alkaloid cryptoheptine (7) was the second most active with IC50 values of 0.8 microM (K1) and 1.2 microM (T996). Cryptolepinoic acid (1) showed no significant activity while its ethyl ester derivative 3 was active against P. falciparum K1 (IC50 = 3.7 microM). All the indoloquinoline alkaloids showed cross-resistance with chloroquine but not the indolobenzazepine alkaloid 7. It was noticed that alkaloids with weakly basic characteristics were active whereas other structurally related alkaloids with different acid-base profiles were inactive. These observations are in agreement with the antimalarial mechanism of action for quinolines. PMID:10705730

  1. A new hepoprotective saponin from Semen Celosia cristatae.

    PubMed

    Sun, Zhen-Liang; Gao, Gang-Long; Xia, Yin-Fang; Feng, Jing; Qiao, Zeng-Yong

    2011-06-01

    A new triterpenoid saponin, named semenoside A (1), was isolated from Semen Celosia cristatae. Its structure was elucidated on the basis of 1D, 2D NMR, HR-FAB-MS and ESI-MS techniques, and physicochemical properties. The hepatoprotective activity of semenoside A with an oral dose of 1.0, 2.0 and 4.0mg/kg, respectively, were investigated by carbon tetrachloride (CCl(4))-induced hepatotoxicity in mice. The results indicated that it had significant hepatoprotective effects (p < 0.01). PMID:21262329

  2. 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). PMID:22934688

  3. Cattle and sheep develop preference for drinking water containing grape seed tannin.

    PubMed

    Kronberg, S L; Schauer, C S

    2013-10-01

    Ingestion of small amounts of some types of condensed tannins (CTs) by ruminant livestock can provide nutritional, environmental and economic benefits. However, practical methods are needed to make these tannins more available to ruminant livestock. Results from previous trials with crude quebracho and black wattle tannin indicated that cattle and/or sheep would not preferentially drink water containing these tannins. Therefore, we conducted preference trials to determine if cattle and sheep would learn to prefer water containing purified grape seed tannin (GST) that provided up to 2% of their daily dry matter (DM) intake. After gradual exposure to increasing amounts of this tannin in water during a pre-trial period, five adult ewes and five yearling heifers fed lucerne (Medicago sativa) pellets (19% CP) were offered water and several concentrations of GST solutions for either 15 (sheep trial) or 20 days (cattle trial). We measured intake of all liquids daily. Concentrations of blood urea were also measured for heifers when they drank only tannin solutions or water. Both sheep and cattle developed preferences for water with GST in it over water alone (P < 0.01) although this preference appeared earlier in the trial for sheep than for cattle. For the sheep, mean daily intake of water alone and all tannin solutions (in total) was 0.6 and 6.1 l, respectively. For the cattle, mean daily intake of water and all tannin solutions in total was 21.8 and 20.6 l, respectively, in the first half of the trial and 10.8 and 26.1 l, respectively, in the second half of the trial. Compared with the other tannin solutions, both sheep and cattle drank more of the solution with the highest tannin concentration (2% of daily DM intake as GST) than of water on more trial days (P < 0.05). Ingestion of water with the highest concentration of GST reduced blood plasma urea concentration in the cattle by 9% to 14% (P ≤ 0.10) compared with ingestion of water alone. Results from the trials

  4. Indole Alkaloids from the Leaves of Nauclea officinalis.

    PubMed

    Fan, Long; Liao, Cheng-Hui; Kang, Qiang-Rong; Zheng, Kai; Jiang, Ying-Chun; He, Zhen-Dan

    2016-01-01

    Three new indole alkaloids, named naucleamide G (1), and nauclealomide B and C (5 and 6), were isolated from the n-BuOH-soluble fraction of an EtOH extract of the leaves of Nauclea officinalis, together with three known alkaloids, paratunamide C (2), paratunamide D (3) and paratunamide A (4). The structures with absolute configurations of the new compounds were identified on the basis of 1D and 2D NMR, HRESIMS, acid hydrolysis and quantum chemical circular dichroism (CD) calculation. According to the structures of isolated indole alkaloids, their plausible biosynthetic pathway was deduced. PMID:27455233

  5. γ-Lactam alkaloids from the flower buds of daylily.

    PubMed

    Matsumoto, Takahiro; Nakamura, Seikou; Nakashima, Souichi; Ohta, Tomoe; Yano, Mamiko; Tsujihata, Junichiro; Tsukioka, Junko; Ogawa, Keiko; Fukaya, Masashi; Yoshikawa, Masayuki; Matsuda, Hisashi

    2016-07-01

    Four new alkaloids, hemerocallisamines IV-VII, were isolated from the methanol extract of flower buds of daylily. The chemical structures of the new compounds were elucidated on the basis of chemical and physicochemical evidence. The absolute stereochemistry of the hemerocallisamines IV-VI was elucidated by the application of the modified Mosher's method, HPLC analysis, and optical rotation. In the present study, the isolated alkaloids significantly inhibited the aggregation of Aβ42 in vitro. This is the first report about bioactive alkaloids with a γ-lactam ring from daylily. In addition, isolated nucleosides showed accelerative effects on neurite outgrowth under the non-fasting condition. PMID:26849229

  6. Cyclobutane-Containing Alkaloids: Origin, Synthesis, and Biological Activities

    PubMed Central

    Sergeiko, Anastasia; Poroikov, Vladimir V; Hanuš, Lumir O; Dembitsky, Valery M

    2008-01-01

    Present review describes research on novel natural cyclobutane-containing alkaloids isolated from terrestrial and marine species. More than 60 biological active compounds have been confirmed to have antimicrobial, antibacterial, antitumor, and other activities. The structures, synthesis, origins, and biological activities of a selection of cyclobutane-containing alkaloids are reviewed. With the computer program PASS some additional biological activities are also predicted, which point toward new possible applications of these compounds. This review emphasizes the role of cyclobutane-containing alkaloids as an important source of leads for drug discovery. PMID:19696873

  7. Cytotoxic and antimalarial bisbenzylisoquinoline alkaloids from Stephania erecta.

    PubMed

    Likhitwitayawuid, K; Angerhofer, C K; Cordell, G A; Pezzuto, J M; Ruangrungsi, N

    1993-01-01

    (+)-2-N-Methyltelobine [1], a new alkaloid, together with twelve known bisbenzylisoquinolines, was isolated from the tubers of Stephania erecta. The structure determination and the complete 1H- and unambiguous 13C-nmr assignments of 1 were obtained through extensive use of several 1D and 2D nmr techniques. All alkaloids inhibited the growth of cultured Plasmodium falciparum strains D-6 and W-2 and displayed nonselective cytotoxicity with a battery of cultured mammalian cells. These data were used for the calculation of selectivity indices. Relative to known antimalarial agents, these bisbenzylisoquinoline alkaloids do not appear to be promising clinical candidates at the present time. PMID:8450319

  8. Acceleration of the rate of ethanol fermentation by addition of nitrogen in high tannin grain sorghum

    SciTech Connect

    Mullins, J.T.; NeSmith, C.C.

    1987-01-01

    In this communication, the authors show that accelerated rates of ethanol production, comparable to sorghum varieties containing low levels of tannins and to corn, can occur without the removal of the tannins. The basis of the inhibition appears to be a lack of sufficient nitrogen in the mash for protein synthesis required to support an accelerated fermentative metabolism in Saccharomyces. No inhibition of the enzymes used for starch hydrolysis was found.

  9. Tannin extracts from immature fruits of Terminalia chebula Fructus Retz. promote cutaneous wound healing in rats

    PubMed Central

    2011-01-01

    Background Tannins extracted from immature fruits of Terminalia chebula Fructus Retz. are considered as effective components promoting the process of wound healing. The objective of this study is to explore the optimal extraction and purification technology (OEPT) of tannins, while studying the use of this drug in the treatment of a cutaneous wound of rat as well as its antibacterial effects. Methods The content of tannin extracts was measured by the casein method, and antibacterial ability was studied by the micro-dilution method in vitro. In wound healing experiment, animals in group Ⅰ, Ⅱ and Ⅲ were treated with vaseline ointment, tannin extracts (tannin content: 81%) and erythromycin ointment, respectively (5 mg of ointment were applied on each wound). To evaluate the process of wound healing, selected pharmacological and biochemical parameters were applied. Results After optimal extraction and purification, content of tannin extracts was increased to 81%. Tannin extracts showed the inhibition of Staphylococcus aureus and Klebsiella Pneumonia in vitro. After excision of wounds, on days 7 and 10, the percent of wound contraction of group Ⅱ was higher than that of group Ⅰ. After being hurt with wounds, on days 3, 7, and 10, the wound healing quality of group Ⅱ was found to be better than that of group Ⅰ in terms of granulation formation and collagen organization. After wound creation, on day 3, the vascular endothelial growth factor expression of group Ⅱ was higher than that of group Ⅰ. Conclusion The results suggest that tannin extracts from dried immature fruits of Terminalia chebula Fructus Retz. can promote cutaneous wound healing in rats, probably resulting from a powerful anti-bacterial and angiogenic activity of the extracts. PMID:21982053

  10. Seed removal by scatter-hoarding rodents: the effects of tannin and nutrient concentration.

    PubMed

    Wang, Bo; Yang, Xiaolan

    2015-04-01

    The mutualistic interaction between scatter-hoarding rodents and seed plants have a long co-evolutionary history. Plants are believed to have evolved traits that influence the foraging behavior of rodents, thus increasing the probability of seed removal and caching, which benefits the establishment of seedlings. Tannin and nutrient content in seeds are considered among the most essential factors in this plant-animal interaction. However, most previous studies used different species of plant seeds, rendering it difficult to tease apart the relative effect of each single nutrient on rodent foraging behavior due to confounding combinations of nutrient contents across seed species. Hence, to further explore how tannin and different nutritional traits of seed affect scatter-hoarding rodent foraging preferences, we manipulated tannin, fat, protein and starch content levels, and also seed size levels by using an artificial seed system. Our results showed that both tannin and various nutrients significantly affected rodent foraging preferences, but were also strongly affected by seed size. In general, rodents preferred to remove seeds with less tannin. Fat addition could counteract the negative effect of tannin on seed removal by rodents, while the effect of protein addition was weaker. Starch by itself had no effect, but it interacted with tannin in a complex way. Our findings shed light on the effects of tannin and nutrient content on seed removal by scatter-hoarding rodents. We therefore, believe that these and perhaps other seed traits should interactively influence this important plant-rodent interaction. However, how selection operates on seed traits to counterbalance these competing interests/factors merits further study. PMID:25625425

  11. [Biologically active food supplements as sources of flavonoids, tannins and dietary fibers].

    PubMed

    Kosheleva, O V; Berketova, L V

    2011-01-01

    The content of some biologically active substances such as bioflavonoids, tannins and dietary fiber in various type of biologically active additive was analyzed. The results are shown that the content of bioflavonoids ranger from 26.0 to 3970.0 mg%, tannins--from 1.19 to 857.0 mg%, insoluble dietary fiber--from 4.56 to 67.89% and soluble dietary fiber from 1.0 to 66.8%. PMID:22238949

  12. Ibogan, Aspidosperman, Vincamine, and Bisindole Alkaloids from a Malayan Tabernaemontana corymbosa: Iboga Alkaloids with C-20α Substitution.

    PubMed

    Nge, Choy-Eng; Chong, Kam-Weng; Thomas, Noel F; Lim, Siew-Huah; Low, Yun-Yee; Kam, Toh-Seok

    2016-05-27

    Ten new indole alkaloids (1-10) comprising five ibogan, two aspidosperman, one vincamine, and two bisindole alkaloids, in addition to 32 known alkaloids, were isolated from the stem-bark extract of a Malayan Tabernaemontana corymbosa. The structures of these alkaloids were determined based on analysis of the NMR and MS data and, in five instances (1, 3, 5, 6, 8), confirmed by X-ray diffraction analysis. Two of the iboga alkaloids, conodusines B (2) and C (3), and the iboga-containing bisindole tabernamidine B (10) are notable for the presence of an α-substituted acetyl group at C-20 of the iboga carbon skeleton. The iboga alkaloid (+)-conodusine E (5) had MS and NMR data that were identical to those of (-)-ervatamine I, recently isolated from Ervatamia hainanensis. Establishment of the absolute configuration of (+)-conodusine E (5) was based on analysis of the ECD data, correlation with (-)-heyneanine, and X-ray analysis, which showed that (+)-5 belongs to the same enantiomeric series as exemplified by (-)-coronaridine. The configuration at C-20' of the previously reported Tabernaemontana bisindole alkaloid 19'-oxotabernamine (renamed tabernamidine B) required revision based on the present results. Several of the bisindoles showed pronounced in vitro growth inhibitory activity against drug-sensitive and vincristine-resistant KB cells. PMID:27077800

  13. Radical Scavenging Activities of Tannin Extracted from Amaranth (Amaranthus caudatus L.).

    PubMed

    Jo, Hyeon-Ju; Chung, Kang-Hyun; Yoon, Jin A; Lee, Kwon-Jai; Song, Byeong Chun; An, Jeung Hee

    2015-06-01

    This study investigates the bioactivity of tannin from amaranth (Amaranthus caudatus L.) extracts. The antioxidant activities of the extracts from amaranth leaves, flowers, and seeds were evaluated. Tannin from leaves of amaranth has been evaluated for superoxide scavenging activity by using DPPH and ABTS(+) analysis, reducing power, protective effect against H2O2-induced oxidative damage in L-132 and BNL-CL2 cells, and inhibition of superoxide radical effects on HL-60 cells. At a concentration of 100 μg/ml, tannin showed protective effects and restored cell survival to 69.2% and 41.8% for L-132 and BNL-CL2 cells, respectively. Furthermore, at the same concentration, tannin inhibited 41% of the activity of the superoxide radical on HL-60 cells and 43.4% of the increase in nitric oxide levels in RAW 264.7 cells. The expression levels of the antioxidant-associated protein SOD-1 were significantly increased in a concentration-dependent manner in RAW 264.7 cells treated with tannin from amaranth leaves. These results suggest that tannin from the leaves of Amaranthus caudatus L. is a promising source of antioxidant component that can be used as a food preservative or nutraceutical. PMID:25639718

  14. Effect of hydrolysable tannins on intestinal morphology, proliferation and apoptosis in entire male pigs.

    PubMed

    Bilić-Šobot, Diana; Kubale, Valentina; Škrlep, Martin; Čandek-Potokar, Marjeta; Prevolnik Povše, Maja; Fazarinc, Gregor; Škorjanc, Dejan

    2016-10-01

    This study aimed to evaluate the effect of hydrolysable tannin supplementation on morphology, cell proliferation and apoptosis in the intestine and liver of fattening boars. A total of 24 boars (Landrace × Large white) were assigned to four treatment groups: Control (fed commercial feed mixture) and three experimental groups fed the same diet supplemented with 1%, 2% and 3% of hydrolysable tannin-rich extract. Animals were housed individually with ad libitum access to feed and then slaughtered at 193 d of age and 122 ± 10 kg body weight. Diets supplemented with hydrolysable tannin affected the morphometric traits of the duodenum mucosa as reflected in increased villus height, villus perimeter and mucosal thickness. No effect was observed on other parts of the small intestine. In the large intestine, tannin supplementation reduced mitosis (in the caecum and descending colon) and apoptosis (in the caecum, ascending and descending colon). No detrimental effect of tannin supplementation on liver tissue was observed. The present findings suggest that supplementing boars with hydrolysable tannins at concentrations tested in this experiment has no unfavourable effects on intestinal morphology. On the contrary, it may alter cell debris production in the large intestine and thus reduce intestinal skatole production. PMID:27434497

  15. Effect of condensed tannin ingestion in sheep and goat parotid saliva proteome.

    PubMed

    Lamy, E; da Costa, G; Santos, R; Capela e Silva, F; Potes, J; Pereira, A; Coelho, A V; Baptista, E Sales

    2011-06-01

    Saliva appears as a defence mechanism, against potential negative effects of tannins, in some species of animals which have to deal with these plant secondary metabolites in their regular diets. This study was carried out to investigate changes in parotid saliva protein profiles of sheep (Ovis aries) and goats (Capra hircus), induced by condensed tannin ingestion. Five Merino sheep and five Serpentina goats were maintained on a quebracho tannin enriched diet for 10 days. Saliva was collected through catheters inserted on parotid ducts and salivary proteins were separated by two-dimensional gel electrophoresis. Matrix-assisted Laser desorption ionization - time of flight (MALDI-TOF) and liquid chromatography tandem mass spectrometry (LC-MS/MS) were used to identify the proteins whose expression levels changed after tannin consumption. Although no new proteins appeared, quebracho tannin consumption increased saliva total protein concentration and produced changes in the proteome of both species. While some proteins were similarly altered in both species parotid salivary protein profile, sheep and goats also presented species-specific differences in response to tannin consumption. PMID:20880287

  16. Identification of saponins from sugar beet (Beta vulgaris) by low and high-resolution HPLC-MS/MS.

    PubMed

    Mikołajczyk-Bator, Katarzyna; Błaszczyk, Alfred; Czyżniejewski, Mariusz; Kachlicki, Piotr

    2016-09-01

    We profiled triterpene saponins from the roots of sugar beet Beta vulgaris L. cultivars Huzar and Boryna using reversed-phase liquid chromatography combined with negative-ion electrospray ionization quadrupole mass spectrometry. We tentatively identified 26 triterpene saponins, including 17 that had not been detected previously in this plant species and 7 saponins that were tentatively identified as new compounds. All observed compounds were glycosides of five different aglycones, of which gypsogenin and norhederagenin are reported for the first time in sugar beet. Thirteen of the saponins detected in sugar beet roots were substituted with dioxolane-type (4 saponins) or acetal-type (9 saponins) dicarboxylic acids. Among the 26 detected saponins, we identified 2 groups of isomers distinguished using high-resolution mass measurements that were detected only in the Huzar cultivar of sugar beet. PMID:27423042

  17. Photofragmentation mechanisms in protonated chiral cinchona alkaloids.

    PubMed

    Kumar, Sunil; Lucas, Bruno; Fayeton, Jacqueline; Scuderi, Debora; Alata, Ivan; Broquier, Michel; Barbu-Debus, Katia Le; Lepère, Valeria; Zehnacker, Anne

    2016-08-10

    The photo-stability of protonated cinchona alkaloids is studied in the gas phase by a multi-technique approach. A multi-coincidence technique is used to demonstrate that the dissociation is a direct process. Two dissociation channels are observed. They result from the C8-C9 cleavage, accompanied or not by hydrogen migration. The branching ratio between the two photo-fragments is different for the two pseudo-enantiomers quinine and quinidine. Mass spectrometry experiments coupling UV photo-dissociation of the reactants and structural characterization of the ionic photo-products by Infra-Red Multiple Photo-Dissociation (IRMPD) spectroscopy provide unambiguous information on their structure. In addition, quantum chemical calculations allow proposing a reactive scheme and discussing it in terms of the ground-state geometry of the reactant. PMID:27477216

  18. Non-alkaloid constituents of Vinca major.

    PubMed

    Cheng, Gui-Guang; Zhao, Hai-Yun; Liu, Lu; Zhao, Yun-Li; Song, Chang-Wei; Gu, Ji; Sun, Wei-Bang; Liu, Ya-Ping; Luo, Xiao-Dong

    2016-01-01

    The present study was designed to investigate the non-alkaloid compounds from the leaves and stems of Vinca major cultivated in Yunnan Province, China. The compounds were isolated using chromatographic techniques. The structures were elucidated by 1D- and 2D-NMR spectroscopic methods in combination with UV, IR, and MS analyses. The 1, 1-diphenyl-2-picrylhydrazyl (DPPH)-scavenging activity of Compounds 1-7 were evaluated. One new iridoid glycoside (compound 1), together with 11 known compounds, were isolated from Vinca major. Compounds 1, 5, and 6 showed moderate DPPH-scavenging activity, with IC50 values being 70.6, 32.8, and 62.2 μmol·L(-1), respectively. In conclusion, compound 1 is a newly identified iridoid glycoside with moderate antioxidant activity. PMID:26850347

  19. Total Synthesis of Alkaloid 205B

    PubMed Central

    2015-01-01

    Concise and highly stereocontrolled total syntheses of racemic and enantiopure frog alkaloid 205B (1) were accomplished in 11 steps from 4-methoxypyridines 6 and 7 in overall yields of 8 and 8%, respectively. The assembly of the core of the natural product relies on a stereoselective Tsuji–Trost allylic amination reaction and a ring-closing metathesis. The synthesis features the use of an N-acylpyridinium salt reaction to introduce the first stereocenter and an unprecedented trifluoroacetic anhydride-mediated addition of an allylstannane to a vinylogous amide with complete facial selectivity. Deoxygenation of the C4 ketone proved difficult but was accomplished via a modified Barton–McCombie reaction in the presence of a catalytic amount of diphenyl diselenide. PMID:25180567

  20. Evaluation of direct phloroglucinolysis and colorimetric depolymerization assays and their applicability for determining condensed tannins in grape marc.

    PubMed

    Hixson, Josh L; Bindon, Keren A; Smith, Paul A

    2015-11-18

    To determine the optimum methods for determining condensed tannin (CT) content in grape marc, butanol-hydrochloric acid assays and phloroglucinolysis were adapted for use, applied to a range of grape marc types, and the methods compared. Porter's assay (butanol-HCl) was found to give unreliable results due to nonlinear color responses to grape skin and seed tannin concentrations, whereas the modification to include acetone (Grabber's assay) overcame this. Differences between skin and seed tannin responses highlighted the need to adequately select the correct grape tannin standard, and the formation of pH-dependent color was accounted for through acidification of blank samples. For phloroglucinolysis, the inability to remove highly bound tannins from cell wall material was highlighted, although a measure of tannins remaining post-phloroglucinolysis (Grabber's assay) showed a trend with the level of exposure to oxidative storage or processing conditions. The comparison of CT concentrations from phloroglucinolysis and Grabber's assay gave poor correlation coefficients. PMID:26551987

  1. Four triterpenoid saponins from dried roots of Gypsophila species.

    PubMed

    Frechet, D; Christ, B; du Sorbier, B M; Fischer, H; Vuilhorgne, M

    1991-01-01

    Four new triterpenoid saponins were isolated from the roots of Gypsophila paniculata and G. arrostii. Their structures were elucidated using a combination of homo- and heteronuclear 2D NMR techniques, without having recourse to chemical degradation or modification. The saponins investigated are: 3-O-beta-D-galactopyranosyl-(1----2)-[beta-D-xylopyranosyl-(1----3)]-bet a-D- glucuronopyranosyl quillaic acid 28-O-beta-D-glucopyranosyl-(1----3)-[beta-D-xylopyranosyl-(1----4)]-alph a- L-rhamnopyranosyl-(1----2)-beta-D-fucopyranoside; 3-O-beta-D-galactopyranosyl-(1----2)-[beta-D-xylopyranosyl-(1----3)]-bet a- D-glucuronopyranosyl quillaic acid 28-O-beta-D-arabinopyranosyl-(1----4)-beta-D-arabinopyranosyl++ +-(1----3)-beta-D- xylopyranosyl-(1----4)-alpha-L-rhamnopyranosyl-(1----2)-beta-D-fucopyran oside; 3-O-beta-D-glucopyranosyl-(1----2)-beta-D-glucuronopyranosyl gypsogenin 28-O-beta-D-glucopyranosyl-(1----3)-[beta-D-xylopyranosyl-(1----4)]-alph a- L-rhamnopyranosyl-(1----2)-beta-D-fucopyranoside; 3-O-beta-D-xylopyranosyl-(1----3)-[beta-D-galactopyranosyl-(1----2)]-bet a- D-glucuronopyranosyl gypsogenin 28-O-beta-D-glucopyranosyl-(1----3)-[beta-D-xylopyranosyl-(1----4)-alpha -L- rhamnopyranosyl-(1----2)-beta-D-fucopyranoside. PMID:1367588

  2. Anticonvulsant properties of saponins from Ficus platyphylla stem bark.

    PubMed

    Chindo, Ben A; Anuka, Joseph A; McNeil, Lilly; Yaro, Abdullahi H; Adamu, Simon S; Amos, Samson; Connelly, William K; Lees, George; Gamaniel, Karniyus S

    2009-03-30

    Preparations of Ficus platyphylla have been used in Nigerian traditional medicine for the management of epilepsy for many years and their efficacy is widely acclaimed among the Hausa communities of northern Nigeria. The anticonvulsant properties of the saponin rich fraction (SFG) obtained from the methanol extract of F. platyphylla stem bark were studied on pentylenetetrazole-, strychnine- and maximal electroshock seizures in mice. Effects of SFG were also examined in murine models for neurological disease and on relevant in vitro targets for anticonvulsant drugs. SFG protected mice against pentylenetetrazole- and strychnine-induced seizures; and significantly delayed the onset of myoclonic jerks and tonic seizures. SFG failed to protect mice against maximal electroshock seizures at doses tested. SFG neither abolished the spontaneous discharges induced by 4-aminopyridine in a neonatal rat brain slice model of tonic-clonic epilepsy nor could it modulate chloride currents through GABA(A) receptor channel complex in cultured cortical cells. However, it was able to non-selectively suppress excitatory and inhibitory synaptic traffic, blocked sustained repetitive firing (SRF) and spontaneous action potential firing in these cultured cells. Our results provide scientific evidence that F. platyphylla stem bark may contain psychoactive principles with potential anticonvulsant properties. SFG impaired membrane excitability; a property shared by most anticonvulsants particularly the voltage-gated sodium channel (VGSC) blocking drugs, thus supporting the isolation and development of the saponin components of this plant as anticonvulsant agents. PMID:19111909

  3. Oleanane-type triterpene saponins from Hydrocotyle nepalensis.

    PubMed

    Ma, Rui-Jing; Liu, Zhen-Hua; Zi, Cheng-Ting; Gao, Wei; Dong, Fa-Wu; Yang, Liu; Li, Jin-Yu; Zhou, Jun; Hu, Jiang-Miao

    2016-04-01

    Five new oleanane-type triterpene saponins including steganogenin 3-O-β-D-glucopyranoside (1), steganogenin 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (2), steganogenin 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside (3), chichipegenin 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (4) and chichipegenin 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside (5), along with four known oleanane-type triterpenes and triterpene saponins (6-9) were isolated from EtOH extract of the whole plant of Hydrocotyle nepalensis. To the best of our knowledge, oleanane-type triterpenes possessing skeleton with 17, 22-seco-backbone (1-3) are not common in natural products. Compound 8 was isolated as a new natural product. The structures of new compounds were elucidated by extensive spectroscopic methods and chemical evidence. Moreover, the cytotoxic activity of all the isolates against five selected human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7 and SW480) was evaluated and the results indicated that compounds 6 and 7 show stronger cytotoxic activity. PMID:26851174

  4. A new triterpenoid saponin from Clinopodium chinense (Benth.) O. Kuntze.

    PubMed

    Zeng, Biao; Liu, Guang-Da; Zhang, Bao-Bao; Wang, Shan-Shan; Ma, Rui; Zhong, Bei-Shan; He, Bai-Qiu; Liang, Yan; Wu, Fei-Hua

    2016-05-01

    A new triterpene saponin, 3β,16β,23α,28β,30β-pentahydroxyl-olean-11,13(18)-dien-3β-yl-[β-d-glucopyranosyl-(1→2)]-[β-d-glucopyranosyl-(1→3)]-β-d-fucopyranoside, was named Clinoposaponin D (1), together with six known triterpene saponins, buddlejasaponin IVb (2), buddlejasaponin IVa (3), buddlejasaponin IV (4), clinopodisides D (5), 11α,16β,23,28-Tetrahydroxyolean-12-en-3β-yl-[β-d-glucopyranosyl-(1→2)]-[β-d-glucopyranosyl-(1→3)]-β-d-fucopyranoside (6) and prosaikogenin A (7), and two known triterpenes, saikogenin A (8) and saikogenin F (9) were isolated from Clinopodium chinense (Benth.) O. Kuntze. Their structures were elucidated on the basis of 1D, 2D NMR and MS analysis. Meanwhile, the effects of all compounds on rabbit platelet aggregation and thrombin time (TT) were investigated in vitro. Compounds 4 and 7 had significant promoting effects on platelet aggregation with EC50 value at 53.4 and 12.2 μM, respectively. In addition, the highest concentration (200 μM) of compounds 2 and 9 shortened TT by 20.6 and 25.1%, respectively. PMID:26511166

  5. Respirometric Oxidative Phosphorylation Assessment in Saponin-permeabilized Cardiac Fibers

    PubMed Central

    Hughey, Curtis C.; Hittel, Dustin S.; Johnsen, Virginia L.; Shearer, Jane

    2011-01-01

    Investigation of mitochondrial function represents an important parameter of cardiac physiology as mitochondria are involved in energy metabolism, oxidative stress, apoptosis, aging, mitochondrial encephalomyopathies and drug toxicity. Given this, technologies to measure cardiac mitochondrial function are in demand. One technique that employs an integrative approach to measure mitochondrial function is respirometric oxidative phosphorylation (OXPHOS) analysis. The principle of respirometric OXPHOS assessment is centered around measuring oxygen concentration utilizing a Clark electrode. As the permeabilized fiber bundle consumes oxygen, oxygen concentration in the closed chamber declines. Using selected substrate-inhibitor-uncoupler titration protocols, electrons are provided to specific sites of the electron transport chain, allowing evaluation of mitochondrial function. Prior to respirometric analysis of mitochondrial function, mechanical and chemical preparatory techniques are utilized to permeabilize the sarcolemma of muscle fibers. Chemical permeabilization employs saponin to selectively perforate the cell membrane while maintaining cellular architecture. This paper thoroughly describes the steps involved in preparing saponin-skinned cardiac fibers for oxygen consumption measurements to evaluate mitochondrial OXPHOS. Additionally, troubleshooting advice as well as specific substrates, inhibitors and uncouplers that may be used to determine mitochondria function at specific sites of the electron transport chain are provided. Importantly, the described protocol may be easily applied to cardiac and skeletal tissue of various animal models and human samples. PMID:21403632

  6. Ergot alkaloids induce vasoconstriction of bovine foregut vasculature

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Alkaloids produced by the Neotyphodium coenophialum endophyte in association with tall fescue (Lolium arundinaceum) are imputed to cause peripheral symptoms of fescue toxicosis. We hypothesized that theses compounds could correspondingly affect foregut vasculature. The objective of this study was to...

  7. Alkaloids with Different Carbon Units from Myrioneuron faberi.

    PubMed

    Cao, Ming-Ming; Zhang, Yu; Huang, Sheng-Dian; Di, Ying-Tong; Peng, Zong-Gen; Jiang, Jian-Dong; Yuan, Chun-Mao; Chen, Duo-Zhi; Li, Shun-Lin; He, Hong-Ping; Hao, Xiao-Jiang

    2015-11-25

    Three new Myrioneuron alkaloids, myrifamines A-C (1-3), with unique skeletons were isolated from Myrioneuron faberi. The absolute configuration of 1 was confirmed by single-crystal X-ray diffraction analysis, and the stereochemistry of the other two alkaloids was determined using a combination of ROESY experiments and calculated and experimental electronic circular dichroism spectra. Myrifamine C (3) is the first example of a symmetric dimer among the Myrioneuron alkaloids. Known alkaloids myrionamide (4) and schoberine (5) were also isolated, and experimental NMR and X-ray diffraction data suggest their structural revision. Compound 2 showed significant inhibitory activity toward the hepatitis C virus in vitro, with a therapeutic index (CC50/EC50) greater than 108.7. PMID:26551513

  8. Microcalorimetry studies of the antimicrobial actions of Aconitum alkaloids*

    PubMed Central

    Shi, Yan-bin; Liu, Lian; Shao, Wei; Wei, Ting; Lin, Gui-mei

    2015-01-01

    The metabolic activity of organisms can be measured by recording the heat output using microcalorimetry. In this paper, the total alkaloids in the traditional Chinese medicine Radix Aconiti Lateralis were extracted and applied to Escherichia coli and Staphylococcus aureus. The effect of alkaloids on bacteria growth was studied by microcalorimetry. The power-time curves were plotted with a thermal activity monitor (TAM) air isothermal microcalorimeter and parameters such as growth rate constant (μ), peak-time (Tm), inhibitory ratio (I), and enhancement ratio (E) were calculated. The relationships between the concentration of Aconitum alkaloids and μ of E. coli or S. aureus were discussed. The results showed that Aconitum alkaloids had little effect on E. coli and had a potentially inhibitory effect on the growth of S. aureus. PMID:26238544

  9. Microcalorimetry studies of the antimicrobial actions of Aconitum alkaloids.

    PubMed

    Shi, Yan-bin; Liu, Lian; Shao, Wei; Wei, Ting; Lin, Gui-mei

    2015-08-01

    The metabolic activity of organisms can be measured by recording the heat output using microcalorimetry. In this paper, the total alkaloids in the traditional Chinese medicine Radix Aconiti Lateralis were extracted and applied to Escherichia coli and Staphylococcus aureus. The effect of alkaloids on bacteria growth was studied by microcalorimetry. The power-time curves were plotted with a thermal activity monitor (TAM) air isothermal microcalorimeter and parameters such as growth rate constant (μ), peak-time (Tm), inhibitory ratio (I), and enhancement ratio (E) were calculated. The relationships between the concentration of Aconitum alkaloids and μ of E. coli or S. aureus were discussed. The results showed that Aconitum alkaloids had little effect on E. coli and had a potentially inhibitory effect on the growth of S. aureus. PMID:26238544

  10. Total synthesis, biosynthesis and biological profiles of clavine alkaloids.

    PubMed

    McCabe, Stephanie R; Wipf, Peter

    2016-07-01

    This review highlights noteworthy synthetic and biological aspects of the clavine subfamily of ergot alkaloids. Recent biosynthetic insights have laid the groundwork for a better understanding of the diverse biological pathways leading to these indole derivatives. Ergot alkaloids were among the first fungal-derived natural products identified, inspiring pharmaceutical applications in CNS disorders, migraine, infective diseases, and cancer. Pergolide, for example, is a semi-synthetic clavine alkaloid that has been used to treat Parkinson's disease. Synthetic activities have been particularly valuable to facilitate access to rare members of the Clavine family and empower medicinal chemistry research. Improved molecular target identification tools and a better understanding of signaling pathways can now be deployed to further extend the biological and medical utility of Clavine alkaloids. PMID:27215547

  11. New Lycopodine-Type Alkaloids from Lycopodium carinatum.

    PubMed

    Kogure, Noriyuki; Maruyama, Moe; Wongseripipatana, Sumphan; Kitajima, Mariko; Takayama, Hiromitsu

    2016-07-01

    The structures of new lycopodine-type alkaloids, lycopocarinamines A-F, which were isolated from Lycopodium carinatum, were elucidated by spectroscopic analysis and chemical conversions. The proposed structure of lycocarinatine A was revised. PMID:27020466

  12. Analysis of rye grains and rye meals for ergot alkaloids.

    PubMed

    Lauber, U; Schnaufer, R; Gredziak, M; Kiesswetter, Y

    2005-12-01

    Due to the exceptionally hot and dry summer in 2003 the ergot of that harvest was rather small and could only be separated from normal grain with increased efforts. Based on a clean-up procedure of Wolffet al. (1) and of Kluget al. (2), a HPLC-FLD-method for the determination of 12 ergot alkaloids (6 "In"-, 6 "Inin"-forms) was established and modified. Actually reference substances are commercially available only for 5 selected alkaloids. Because of the instability of the alkaloids a new standard preparation procedure was tested and implemented. The maximum allowed impurity with ergot (0.05%=1000 μg alkaloids/kg) was exceeded in samples of harvest 2003. Except for one sample, all exceedings were detected in conventionally grown products, unlike organically grown products. PMID:23605398

  13. Arginine decarboxylase as the source of putrescine for tobacco alkaloids

    NASA Technical Reports Server (NTRS)

    Tiburcio, A. F.; Galston, A. W.

    1986-01-01

    The putrescine which forms a part of nicotine and other pyrrolidine alkaloids is generally assumed to arise through the action of ornithine decarboxylase (ODC). However, we have previously noted that changes in the activity of arginine decarboxylase (ADC), an alternate source of putrescine, parallel changes in tissue alkaloids, while changes in ODC activity do not. This led us to undertake experiments to permit discrimination between ADC and ODC as enzymatic sources of putrescine destined for alkaloids. Two kinds of evidence presented here support a major role for ADC in the generation of putrescine going into alkaloids: (a) A specific 'suicide inhibitor' of ADC effectively inhibits the biosynthesis of nicotine and nornicotine in tobacco callus, while the analogous inhibitor of ODC is less effective, and (b) the flow of 14C from uniformly labelled arginine into nicotine is much more efficient than that from ornithine.

  14. Structure-cardiac activity relationship of C19-diterpenoid alkaloids.

    PubMed

    Jian, Xi-Xian; Tang, Pei; Liu, Xiu-Xiu; Chao, Ruo-Bing; Chen, Qiao-Hong; She, Xue-Ke; Chen, Dong-Lin; Wang, Feng-Peng

    2012-06-01

    Thirty three C19-diterpenoid alkaloids, twenty-two prepared from known C19-diterpenoid alkaloids and eleven isolated from Aconitum and Delphinium spp. were evaluated for their cardiac activity in the isolated bullfrog heart assay. Among them, eleven compounds exhibited cardiac activity, with average rate of amplitude increase in the range of 16-118%. Compound 7, mesaconine (17), hypaconine (25), and beiwutinine (26) exhibited strong cardiac activities relative to the reference drug. The structure-activity relationship data acquired indicated that an alpha-hydroxyl group at C-15, a hydroxyl group at C-8, an alpha-methoxyl or hydroxyl group at C-1, and a secondary amine or N-methyl group in ring A are important structure features necessary for the cardiac activities of the aconitine-type C19-diterpenoid alkaloids without any ester groups. In addition, an alpha-hydroxyl group at C-3 is also helpful for the cardiac activity of these alkaloids. PMID:22816290

  15. A new phenanthridine alkaloid from Hymenocallis x festalis.

    PubMed

    Hohmann, J; Forgo, P; Szabó, P

    2002-12-01

    Investigation of the alkaloid fraction of the bulbs of Hymenocallis x festalis yielded a new natural product, 3-methoxy-8,9-methylenedioxy-3,4-dihydrophenanthridine (1). The structure was elucidated on the basis of spectroscopic data. PMID:12490249

  16. Pyrrolizidine alkaloid poisoning of yaks: identification of the plants involved.

    PubMed

    Winter, H; Seawright, A A; Noltie, H J; Mattocks, A R; Jukes, R; Wangdi, K; Gurung, J B

    1994-02-01

    A search was undertaken in the most eastern part of the Himalayan kingdom of Bhutan for the plants which are causing severe losses of yaks due to pyrrolizidine alkaloid poisoning. Two Senecio and three Ligularia species were found on yak pastures at altitudes between 3000 and 4000 m, including one so far underscribed Ligularia species. None was previously known to contain pyrrolizidine alkaloids. Another Senecio species was found between 2500 and 3000 m, an altitude too low for yaks to be kept but significant for other cattle. The search was supported by field chemical tests for the alkaloids and the diagnosis was later confirmed by thin layer chromatography and high pressure liquid chromatography. Two of the Senecio species had exceptionally high concentrations of pyrrolizidine alkaloids of about 0.5 per cent in the dry matter. PMID:8171783

  17. [Monomeric indole alkaloids from the aerial parts of Catharanthus roseus].

    PubMed

    Zhong, Xiang-Zhang; Wang, Guo-Cai; Wang, Ying; Zhang, Xiao-Qi; Ye, Wen-Cai

    2010-04-01

    Catharanthus roseus (L.) G. Don is a plant of the Catharanthus genus of Apocynaceae which has been reported to have therapeutic effects of detoxication and anticancer. In order to further study the alkaloid constituents of C. roseus, the aerial parts of the plant were extracted with 95% EtOH, and then treated with 2% H2SO4 and NH3H2O to obtain total alkaloids. The total alkaloids were separated and purified by column chromatography over silica gel and prepared by high performance liquid chromatography (HPLC). Their structures were elucidated on the basis of physicochemical properties and spectral data. A new alkaloid together with five known compounds were isolated and identified as vindolinine B (1), lochnericine (2), horhammericine (3), vindorosine (4), vindoline (5), and coronaridine (6). Compound 1 is a new compound and named as vindolinine B. PMID:21355212

  18. Activity of pyrrolizidine alkaloids against biofilm formation and Trichomonas vaginalis

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Crotalaria genus belongs to the subfamily Papilionoideae comprising about 600 species spread throughout tropical, neotropical and subtropical regions. In this study, seeds of Crolatalaria pallida were used to the isolation of usaramine, a pyrrolizidine alkaloid. Thus, Pseudomonas aeruginosa and Stap...

  19. Rhazinilam-Leuconolam-Leuconoxine Alkaloids from Leuconotis griffithii.

    PubMed

    Gan, Chew-Yan; Low, Yun-Yee; Thomas, Noel F; Kam, Toh-Seok

    2013-05-24

    Eight new indole alkaloids (1-8) belonging to the rhazinilam-leuconolam-leuconoxine group, in addition to 52 other alkaloids, were isolated from the stem-bark extract of Leuconotis griffithii, viz., nor-rhazinicine (1), 5,21-dihydrorhazinilam-N-oxide (2), 3,14-dehydroleuconolam (3), and leuconodines A-E (4-8). The structures of these alkaloids were determined using NMR and MS analyses and in some instances confirmed by X-ray diffraction analyses. Alkaloids 1, 5, and 7 showed only moderate to weak cytotoxicity toward KB cells (IC50 12-18 μg/mL), while 8 showed moderate activity in reversing MDR in vincristine-resistant KB cells. PMID:23647487

  20. Localization and dynamic change of saponin in vegetative organs of Polygala tenuifolia.

    PubMed

    Teng, Hong-Mei; Fang, Min-Feng; Cai, Xia; Hu, Zheng-Hai

    2009-06-01

    Anatomical, histochemical and phytochemical methods were used to investigate the structure, localization and dynamic changes of total saponin and senegenin of vegetative organs in Polygala tenuifolia Willd. Histochemical localization results showed that saponin accumulated mainly in parenchyma cells of vegetative organs. The phytochemical results also showed that the saponin accumulated in the vegetative organs of P. tenuifolia, with higher content in roots and lower content in the aerial parts that included stems and leaves. The saponin content and dry weight of the vegetative organs of P. tenuifolia had dynamic variance at the developmental stages and all reached the highest level in the post-fruit period. Hence, the roots and aerial parts should be gathered in August to make full use of the plant. As the root is the main medicinal organ of P. tenuifolia, the content of total saponin and senegenin of different aged and different parts of the root were determined. The content of total saponin and senegenin exhibited a sustained decreasing trend with increasing root age; therefore, the annual roots had high quality. The content of total saponin and senegenin in different parts of the root showed obvious variation. The content in the "skin areas" was much higher than that of xylem. The results offer a theoretical basis for determining the appropriate harvesting stage and a reasonable harvest of P. tenuifolia. PMID:19522811

  1. Miscibility of Quillaja Saponins with other Co-surfactants under Different pH Values.

    PubMed

    Reichert, Corina L; Salminen, Hanna; Leuenberger, Bruno H; Hinrichs, Jörg; Weiss, Jochen

    2015-11-01

    The miscibility behavior of mixed surfactant systems and the influence of extrinsic parameters are crucial for their application as emulsifiers. Therefore, the objective of this study was to evaluate the miscibility behavior of mixed systems composed of commercial Quillaja saponin and a co-surfactant, namely sodium caseinate, pea protein, rapeseed lecithin, or egg lecithin. These mixtures were evaluated macro- and microscopically at different concentration ratios (maximum concentration 5% w/v) at pH 3, 5, and 7 at 25 °C. The individual ingredients were also assessed for their charge properties and surface hydrophobicity. The results showed that Quillaja saponin-caseinate mixtures were miscible only at pH 7, and showed aggregation and precipitation at lower pH due to increasing electrostatic attraction forces. Rheological measurements showed that Quillaja saponin-pea protein mixtures formed gelled structures at all tested pH values mainly via association of hydrophobic patches. Quillaja saponins mixed with rapeseed lecithin were miscible at all tested pH values due to electrostatic repulsion. Quillaja saponin-egg lecithin mixtures aggregated independent of pH and concentration ratio. The microscopic analysis revealed that the lower the pH and the higher the Quillaja saponin ratio, the denser were the formed Quillaja saponin-egg lecithin aggregates. The results are summarized in ternary phase diagrams that provide a useful tool in selecting a surfactant system for food applications. PMID:26458074

  2. Inhibition of DNA-Topoisomerase I by Acylated Triterpene Saponins from Pittosporum angustifolium Lodd.

    PubMed

    Bäcker, Christian; Drwal, Malgorzata N; Preissner, Robert; Lindequist, Ulrike

    2016-04-01

    Previous phytochemical investigation of the leaves and seeds of Pittosporum angustifolium Lodd. led to the isolation and structural elucidation of polyphenols and triterpene saponins. Evaluation for cytotoxicity of isolated saponins revealed that the predominant structural feature for a cytotoxic activity are acyl substituents at the oleanane aglycon backbone. The present work reports the results of a screening of 10 selected acylated saponins for their potential to inhibit the human DNA-topoisomerase I, giving rise to IC50 values in a range of 2.8-46.5 µM. To clarify the mode of observed cytotoxic action and, moreover, to distinguish from a pure surfactant effect which is commonly accompanied with saponins, these results indicate an involvement of the topoisomerase I and its role as a possible target structure for a cytotoxic activity. In addition, computational predictions of the fitting of saponins to the topoisomerase I-DNA complex, indicate a similar binding mode to that of clinically used topoisomerase I inhibitors. Ten acylated triterpene saponins from Pittosporum angustifolium were investigated for their potential to inhibit the human DNA-topoisomerase I and computational predictions of the fitting of saponins to the topoisomerase I-DNA complex were carried out. PMID:26803837

  3. 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. PMID:25811101

  4. Immunoadjuvant and anti-inflammatory plant saponins: characteristics and biotechnological approaches towards sustainable production.

    PubMed

    de Costa, F; Yendo, A C A; Fleck, J D; Gosmann, G; Fett-Neto, A G

    2011-09-01

    Saponins can be classified as triterpenoid (C30) or steroidal (C27), based on their carbon nucleus (aglycone). Sugar residues are linked to the aglycone, conferring an amphiphilic nature on these molecules, which is relevant for their biological activities. Saponins include a large variety of molecules that find several applications in pharmacology. Saponins have been shown to display immunoadjuvant, anti-inflammatory, antiplatelet, hypocholesterolemic, antitumoral, anti-HIV, antibacterial, insecticide, fungicide and anti-leishmanial activities. Anti-inflammatory medicines are increasingly demanded to treat various forms of arthritis in aging and obese populations and to help reduce the doses and duration of conventional corticotherapy with less side effects and without immunosuppression. The vaccine market for both human and veterinary uses is close to US$ 15 billion, progressively inflated by the recurrent threat of global pandemics.This paper provides an overview of recent advances (main focus on the last five years) on plant saponins that show anti-inflammatory and/or immunoadjuvant activities: source plants, isolation procedures, mechanism of action and biotechnological approaches towards sustainable production of bioactive saponins. Special attention is given to ginseng and Quillaja saponins. Strategies based on plant cultivation, cell and tissue culture, elicitation, and metabolic engineering for improved production of saponins are described. Future directions for research in the field and strategies to overcome bottlenecks are also discussed. PMID:21762102

  5. Tyrosinase Inhibitory Effects and Antioxidative Activities of Saponins from Xanthoceras Sorbifolia Nutshell

    PubMed Central

    Zhang, Hongmei; Zhou, Quancheng

    2013-01-01

    Certain saponins are bioactive compounds with anticancer, antivirus and antioxidant activities. This paper discussed inhibitory effects of saponins from Xanthoceras Sorbifolia on tyrosinase, through the research of the rate of tyrosinase catalyzed L-DOPA oxidation. The inhibition rate of tyrosinase activity presented non-linear changes with the saponins concentration. The rate reached 52.0% when the saponins concentration was 0.96 mg/ml. Antioxidant activities of saponins from Xanthoceras Sorbifolia were evaluated by using hydroxyl and superoxide radical scavenging assays. The hydroxyl radical scavenging effects of the saponins were 15.5–68.7%, respectively at the concentration of 0.18–2.52 mg/ml. The superoxide radical scavenging activity reduced from 96.6% to 7.05% with the time increasing at the concentration of 1.44 mg/ml. All the above antioxidant evaluation indicated that saponins from Xanthoceras Sorbifolia exhibited good antioxidant activity in a concentration- dependent manner. PMID:23990897

  6. Computational Studies on Cinchona Alkaloid-Catalyzed Asymmetric Organic Reactions.

    PubMed

    Tanriver, Gamze; Dedeoglu, Burcu; Catak, Saron; Aviyente, Viktorya

    2016-06-21

    Remarkable progress in the area of asymmetric organocatalysis has been achieved in the last decades. Cinchona alkaloids and their derivatives have emerged as powerful organocatalysts owing to their reactivities leading to high enantioselectivities. The widespread usage of cinchona alkaloids has been attributed to their nontoxicity, ease of use, stability, cost effectiveness, recyclability, and practical utilization in industry. The presence of tunable functional groups enables cinchona alkaloids to catalyze a broad range of reactions. Excellent experimental studies have extensively contributed to this field, and highly selective reactions were catalyzed by cinchona alkaloids and their derivatives. Computational modeling has helped elucidate the mechanistic aspects of cinchona alkaloid catalyzed reactions as well as the origins of the selectivity they induce. These studies have complemented experimental work for the design of more efficient catalysts. This Account presents recent computational studies on cinchona alkaloid catalyzed organic reactions and the theoretical rationalizations behind their effectiveness and ability to induce selectivity. Valuable efforts to investigate the mechanisms of reactions catalyzed by cinchona alkaloids and the key aspects of the catalytic activity of cinchona alkaloids in reactions ranging from pharmaceutical to industrial applications are summarized. Quantum mechanics, particularly density functional theory (DFT), and molecular mechanics, including ONIOM, were used to rationalize experimental findings by providing mechanistic insights into reaction mechanisms. B3LYP with modest basis sets has been used in most of the studies; nonetheless, the energetics have been corrected with higher basis sets as well as functionals parametrized to include dispersion M05-2X, M06-2X, and M06-L and functionals with dispersion corrections. Since cinchona alkaloids catalyze reactions by forming complexes with substrates via hydrogen bonds and long

  7. The effects of Aconitum alkaloids on the central nervous system.

    PubMed

    Ameri, A

    1998-10-01

    Preparations of Aconitum roots are employed in Chinese and Japanese medicine for analgesic, antirheumatic and neurological indications. The recent surge in use of phytomedicine derived from traditional Chinese medicine as well as increasing concerns about possible toxic effects of these compounds have inspired a great deal of research into the mechanisms by which certain Aconitum alkaloids may act on the central nervous system. The pharmacological effects of preparations of Aconitum roots are attributed to several diterpenoid alkaloids. The main alkaloid of these plants is aconitine, a highly toxic diterpenoid alkaloid which is known to suppress the inactivation of voltage-dependent Na+ channels by binding to neurotoxin binding site 2 of the alpha-subunit of the channel protein. In this article the pharmacology of several structurally related Aconitum alkaloids is highlighted and their therapeutic vs toxic potential is discussed. Neurochemical and neurophysiological studies will be reviewed with emphasis on the effects of the alkaloids in regions of the brain that have been implicated in pain transmission and generation of epileptic activity. Considering the chemical structure of the Aconitum alkaloids as well as their mechanism of action, a subdivision in three groups becomes obvious: the first group comprises such alkaloids which possess high toxicity due to two ester boundings at the diterpene skeleton. The members of this group activate voltage-dependent sodium channels already at resting potential and inhibit noradrenaline reuptake. Activation of sodium channels and in consequence excessive depolarization with final inexcitability and suppression of pain transmission account for their antinociceptive properties. The second group comprises less toxic monoesters which have been shown to possess strong antinociceptive, antiarrhythmic and antiepileptiform properties due to a blockade of the voltage-dependent sodium channel. Electrophysiological studies have

  8. Effects of Sainfoin (Onobrychis viciifolia Scop.) Condensed Tannins on Growth and Proteolysis by Four Strains of Ruminal Bacteria.

    PubMed

    Jones, G A; McAllister, T A; Muir, A D; Cheng, K J

    1994-04-01

    Sainfoin leaf condensed tannins inhibited growth and protease activity in Butyrivibrio fibrisolvens A38 and Streptococcus bovis 45S1 but had little effect on Prevotella ruminicola B(1)4 or Ruminobacter amylophilus WP225. Tannins bound to cell coat polymers in all strains. Morphological changes in B. fibrisolvens and S. bovis implicated the cell wall as a target of tannin toxicity. PMID:16349244

  9. Application of Mössbauer spectroscopy to the study of tannins inhibition of iron and steel corrosion

    NASA Astrophysics Data System (ADS)

    Jaén, Juan A.; de Obaldía, J.; Rodríguez, M. V.

    2011-11-01

    The inhibitory effect of tannins was investigated using, among others, potentiodynamic polarizations and Mössbauer spectroscopy. These techniques confirmed that the nature, pH and concentration of tannic solution are of upmost importance in the inhibitory properties of the solutions. It is observed that at low tannin concentration or pH, both, hydrolizable and condensed tannins, effectively inhibit iron corrosion, due to the redox properties of tannins. At pH ≈ 0, Mössbauer spectra of the frozen aqueous solutions of iron(III) with the tannin solutions showed that iron is in the form of a monomeric species [Fe(H2O)6]3 + , without coordination with the functional hydroxyl groups of the tannins. The suspended material consisted of amorphous ferric oxide and oxyhydroxides, though with quebracho tannin partly resulted in complex formation and in an iron (II) species from a redox process. Other tannins, such as chestnut hydrolysable tannins, do not complex iron at this low pH. Tannins react at high concentrations or pH (3 and 5) to form insoluble blue-black amorphous complexes of mono-and bis-type tannate complexes, with a relative amount of the bis-ferric tannate generally increasing with pH. Some Fe2 + in the form of hydrated polymeric ferrous tannate could be obtained. At pH 7, a partially hydrolyzed ferric tannate complex was also formed. The latter two phases do not provide corrosion protection. Tannin solutions at natural pH react with electrodeposited iron films (approx. 6 μm) to obtain products consisting only on the catecholate mono-complex of ferric tannate. Some aspects of the mechanism of tannins protection against corrosion are discussed.

  10. Himalensines A and B, Alkaloids from Daphniphyllum himalense.

    PubMed

    Zhang, Hua; Shyaula, Sajan L; Li, Jing-Ya; Li, Jia; Yue, Jian-Min

    2016-03-01

    Chemical investigation into the alkaloidal constituents of the Nepalese Daphniphyllum himalense has returned two new compounds, himalensines A (1) and B (2), with unprecedented carbon skeletons. Structures of the two alkaloids have been characterized on the basis of spectroscopic methods, especially via 2D NMR data analysis. Himalensine B (2) showed marginal inhibitory activities against two kinases, PTP1B and IKK-β. PMID:26914844

  11. Elaboration of simplified vinca alkaloids and phomopsin hybrids.

    PubMed

    Ngo, Quoc Anh; Roussi, Fanny; Thoret, Sylviane; Guéritte, Françoise

    2010-03-01

    Nine simplified vinca alkaloids and phomospin A hybrids, in which vindoline moiety has been replaced by a simpler scaffold, have been elaborated to evaluate their activity on the inhibition of tubulin polymerization. This article deals with the synthesis of various simplified vinca alkaloids, using a stereoselective coupling of catharantine with reactive aromatic compounds and methanol as well as their subsequent condensation with a large peptide chain mimicking those of phomopsin A. Biological evaluation and molecular modeling studies are also reported. PMID:20659111

  12. Pyrrolizidine alkaloid poisoning of sheep in New South Wales.

    PubMed

    Seaman, J T

    1987-06-01

    Pyrrolizidine alkaloid poisoning of sheep in New South Wales was reviewed, based on the records of the New South Wales Department of Agriculture's Regional Veterinary Laboratories. The plant species causing significant mortalities were Echium plantagineum and Heliotropium europaeum. The syndrome of hepatogenous chronic copper poisoning was more frequently diagnosed than primary pyrrolizidine alkaloid poisoning, particularly when grazing E. plantagineum. The data indicated that adult crossbred ewes were the most commonly affected class of sheep. PMID:3632498

  13. Thalifaberidine, a cytotoxic aporphine-benzylisoquinoline alkaloid from Thalictrum faberi.

    PubMed

    Lin, L Z; Hu, S F; Zaw, K; Angerhofer, C K; Chai, H; Pezzuto, J M; Cordell, G A; Lin, J; Zheng, D M

    1994-10-01

    From Thalictrum faberi, thalifaberidine [1], a new aporphine-benzylisoquinoline alkaloid, together with four known alkaloids, thalifaramine [2], thalifaricine [3], thalifarazine [4], and thalifaronine [5], were isolated. Thalifaberidine [1] was identified as 6',8-desmethylthalifaberine, and its 1H- and 13C-nmr data were completely assigned through the use of one- and two-dimensional nmr techniques. Thalifaberidine [1], thalifaberine [6], and thalifasine [7] showed cytotoxic activity against several human cancer cell lines, as well as antimalarial activity. PMID:7528786

  14. Bioinspired Collective Syntheses of Iboga-Type Indole Alkaloids.

    PubMed

    Zhao, Gaoyuan; Xie, Xingang; Sun, Haiyu; Yuan, Ziyun; Zhong, Zhuliang; Tang, Shouchu; She, Xuegong

    2016-05-20

    We present the application of a bioinspired collective synthesis strategy in the total syntheses of seven iboga-type indole alkaloids: (±)-tabertinggine, (±)-ibogamine, (±)-ibogaine, (±)-ibogaine hydroxyindolenine, (±)-3-oxoibogaine hydroxyindolenine, (±)-iboluteine, and (±)-ervaoffines D. In particular, tabertinggine and its congeners serve as iboga precursors for the subsequent biomimetic transformations into other iboga-type alkaloids. PMID:27160167

  15. Cytotoxic indole alkaloids from the fruits of Melodinus cochinchinensis.

    PubMed

    Shao, Shun; Zhang, Hao; Yuan, Chun-Mao; Zhang, Yu; Cao, Ming-Ming; Zhang, Hai-Yuan; Feng, Yan; Ding, Xiao; Zhou, Qiang; Zhao, Qing; He, Hong-Ping; Hao, Xiao-Jiang

    2015-08-01

    Eight indole alkaloids, melosines A-H, together with 13 known alkaloids, were isolated from the fruits of Melodinus cochinchinensis. The structure elucidation of isolated secondary metabolites was based on comprehensive spectroscopic data analysis. Melosine B showed moderate cytotoxic activity against five human cancer cell lines, HL-60, SMMC-7721, A-549, MCF-7, and SW480 with IC50 values ranging from 1.6 to 8.1μM. PMID:25817833

  16. Microbial transformation of the phthalideisoquinoline alkaloid, (-)-beta-hydrastine.

    PubMed

    Herath, W H M W; Ferreira, D; Khan, I A

    2003-08-01

    The phthalideisoquinoline alkaloid (-)-beta-hydrastine is one of the main active constituents of the medicinal plant, Hydrastis canadensis, which is used in many dietary supplements intended to enhance the immune system. Treatment of hydrastine with the fermentation broth of Polyporous brumalis (ATCC 34487) as a model for mammalian metabolism, gave a new alkaloid, (1S)-hydroxyhydrastine. Structure elucidation was based primarily on NMR and chiroptical studies. PMID:12822906

  17. Cytotoxic and antimalarial bisbenzylisoquinoline alkaloids from Cyclea barbata.

    PubMed

    Lin, L Z; Shieh, H L; Angerhofer, C K; Pezzuto, J M; Cordell, G A; Xue, L; Johnson, M E; Ruangrungsi, N

    1993-01-01

    An alkaloid extract derived from the roots of Cyclea barbata demonstrated cytotoxic and antimalarial activities, and five bisbenzylisoquinoline alkaloids, (+)-tetrandrine [1], (-)-limacine [2], (+)-thalrugosine [3], (+)-homoaromoline [4], and (-)-cycleapeltine [5], were isolated as the active principles. The complete and unambiguous assignments of the 1H- and 13C-nmr data of these substances were made by 1D and 2D nmr techniques (COSY, phase-sensitive ROESY, HETCOR, and FLOCK). PMID:8450318

  18. 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. PMID:26654784

  19. Effects of Holothuroid Ichtyotoxic Saponins on the Gills of Free-Living Fishes and Symbiotic Pearlfishes.

    PubMed

    Eeckhaut, Igor; Caulier, Guillaume; Brasseur, Lola; Flammang, Patrick; Gerbaux, Pascal; Parmentier, Eric

    2015-06-01

    Several carapid fishes, known as pearlfishes, are endosymbiotic in holothuroids and asteroids. These echinoderms contain a strong concentration of saponins that are efficient membranolytic repellents to predators. We compared the effects of exposure to saponins from the sea cucumber body wall and from the Cuvierian tubules on the behavior and gill ultrastructure of pearlfishes and free-living fishes. Saponins were extracted from the body wall of two holothuroids, the Mediterranean Holothuria forskali and the tropical Bohadschia atra, and from the water surrounding the Cuvierian tubules of B. atra. Five species of carapids that live in symbiosis with holothuroids and seven species of free-living fishes were exposed to these extracts. The free-living fishes exhibited a stress response and died about 45 times faster than pearlfishes when exposed to the same quantity of saponins. Cuvierian tubules and saponins extracted from the body wall were lethal to the free-living fishes, whereas the carapids were much less sensitive. The carapids did not exhibit a stress response. The high toxicity shown by Cuvierian tubules was not explained by the nature of the saponins that were identified by mass spectrometry, but it is likely due to the higher concentration of saponins in the tubules. Histology and scanning and transmission electron microscopy of the gills of the free-living fishes and pearlfishes showed that saponins act at the level of the secondary lamellae where they induce the detachment of the epithelia, create edema at the level of the epithelia, and induce pores in the epithelial cells that lead to their destruction and the invasion of inner cells (pillar cells and red blood cells). This sequence of events happens 5 min after saponin exposure in free-living fishes and after 1 h in carapids. PMID:26124451

  20. Genetics, Genomics and Evolution of Ergot Alkaloid Diversity

    PubMed Central

    Young, Carolyn A.; Schardl, Christopher L.; Panaccione, Daniel G.; Florea, Simona; Takach, Johanna E.; Charlton, Nikki D.; Moore, Neil; Webb, Jennifer S.; Jaromczyk, Jolanta

    2015-01-01

    The ergot alkaloid biosynthesis system has become an excellent model to study evolutionary diversification of specialized (secondary) metabolites. This is a very diverse class of alkaloids with various neurotropic activities, produced by fungi in several orders of the phylum Ascomycota, including plant pathogens and protective plant symbionts in the family Clavicipitaceae. Results of comparative genomics and phylogenomic analyses reveal multiple examples of three evolutionary processes that have generated ergot-alkaloid diversity: gene gains, gene losses, and gene sequence changes that have led to altered substrates or product specificities of the enzymes that they encode (neofunctionalization). The chromosome ends appear to be particularly effective engines for gene gains, losses and rearrangements, but not necessarily for neofunctionalization. Changes in gene expression could lead to accumulation of various pathway intermediates and affect levels of different ergot alkaloids. Genetic alterations associated with interspecific hybrids of Epichloë species suggest that such variation is also selectively favored. The huge structural diversity of ergot alkaloids probably represents adaptations to a wide variety of ecological situations by affecting the biological spectra and mechanisms of defense against herbivores, as evidenced by the diverse pharmacological effects of ergot alkaloids used in medicine. PMID:25875294

  1. Genetics, genomics and evolution of ergot alkaloid diversity.

    PubMed

    Young, Carolyn A; Schardl, Christopher L; Panaccione, Daniel G; Florea, Simona; Takach, Johanna E; Charlton, Nikki D; Moore, Neil; Webb, Jennifer S; Jaromczyk, Jolanta

    2015-04-01

    The ergot alkaloid biosynthesis system has become an excellent model to study evolutionary diversification of specialized (secondary) metabolites. This is a very diverse class of alkaloids with various neurotropic activities, produced by fungi in several orders of the phylum Ascomycota, including plant pathogens and protective plant symbionts in the family Clavicipitaceae. Results of comparative genomics and phylogenomic analyses reveal multiple examples of three evolutionary processes that have generated ergot-alkaloid diversity: gene gains, gene losses, and gene sequence changes that have led to altered substrates or product specificities of the enzymes that they encode (neofunctionalization). The chromosome ends appear to be particularly effective engines for gene gains, losses and rearrangements, but not necessarily for neofunctionalization. Changes in gene expression could lead to accumulation of various pathway intermediates and affect levels of different ergot alkaloids. Genetic alterations associated with interspecific hybrids of Epichloë species suggest that such variation is also selectively favored. The huge structural diversity of ergot alkaloids probably represents adaptations to a wide variety of ecological situations by affecting the biological spectra and mechanisms of defense against herbivores, as evidenced by the diverse pharmacological effects of ergot alkaloids used in medicine. PMID:25875294

  2. Anticholinesterase inhibitory activity of quaternary alkaloids from Tinospora crispa.

    PubMed

    Yusoff, Mashitah; Hamid, Hazrulrizawati; Houghton, Peter

    2014-01-01

    Quaternary alkaloids are the major alkaloids isolated from Tinospora species. A previous study pointed to the necessary presence of quaternary nitrogens for strong acetylcholinesterase (AChE) inhibitory activity in such alkaloids. Repeated column chromatography of the vine of Tinospora crispa extract led to the isolation of one new protoberberine alkaloid, 4,13-dihydroxy-2,8,9-trimethoxydibenzo[a,g]quinolizinium (1), along with six known alkaloids-dihydrodiscretamine (2), columbamine (3), magnoflorine (4), N-formylannonaine (5), N-formylnornuciferine (6), and N-trans-feruloyltyramine (7). The seven compounds were isolated and structurally elucidated by spectroscopic analysis. Two known alkaloids, namely, dihydrodiscretamine and columbamine are reported for the first time for this plant. The compounds were tested for AChE inhibitory activity using Ellman's method. In the AChE inhibition assay, only columbamine (3) showed strong activity with IC50 48.1 µM. The structure-activity relationships derived from these results suggest that the quaternary nitrogen in the skeleton has some effect, but that a high degree of methoxylation is more important for acetylcholinesterase inhibition. PMID:24448061

  3. In situ analysis and structural elucidation of sainfoin (Onobrychis viciifolia) tannins for high-throughput germplasm screening.

    PubMed

    Gea, An; Stringano, Elisabetta; Brown, Ron H; Mueller-Harvey, Irene

    2011-01-26

    A rapid thiolytic degradation and cleanup procedure was developed for analyzing tannins directly in chlorophyll-containing sainfoin ( Onobrychis viciifolia ) plants. The technique proved suitable for complex tannin mixtures containing catechin, epicatechin, gallocatechin, and epigallocatechin flavan-3-ol units. The reaction time was standardized at 60 min to minimize the loss of structural information as a result of epimerization and degradation of terminal flavan-3-ol units. The results were evaluated by separate analysis of extractable and unextractable tannins, which accounted for 63.6-113.7% of the in situ plant tannins. It is of note that 70% aqueous acetone extracted tannins with a lower mean degree of polymerization (mDP) than was found for tannins analyzed in situ. Extractable tannins had between 4 and 29 lower mDP values. The method was validated by comparing results from individual and mixed sample sets. The tannin composition of different sainfoin accessions covered a range of mDP values from 16 to 83, procyanidin/prodelphinidin (PC/PD) ratios from 19.2/80.8 to 45.6/54.4, and cis/trans ratios from 74.1/25.9 to 88.0/12.0. This is the first high-throughput screening method that is suitable for analyzing condensed tannin contents and structural composition directly in green plant tissue. PMID:21175139

  4. Two New Highly Oxygenated Spirostanol Saponins from Paris polyphylla var. stenophylla.

    PubMed

    Jin, Ling-Yu; Lu, Ting-Xiang; Qin, Xu-Jie; Ni, Wei; Yan, Huan; Chen, Yu; Liu, Hui; He, Hong-Ping; Liu, Hai-Yang

    2016-08-01

    Phytochemical investigation of the rhizomes of Paris polyphylla var. stenophylla led to the isolation of two new highly oxygenated spirostanol saponins, named paristenosides A (1) and B (2), together with seven known compounds. Their structures were established mainly on the base of NMR spectroscopic techniques and mass spectrometry, as well as chemical methods. In addition, the cytotoxicity of the two new saponins was tested. Two new highly oxygenated spirostanol saponins, paristenosides A (1) and B (2), were isolated from the rhizomes of Paris polyphylla var. stenophylla. Their structures were established mainly based on NMR spectroscopic techniques and mass spectrometry, as well as chemical methods. PMID:27255683

  5. Triterpenoid saponins with anti-myocardial ischemia activity from the whole plants of Clematis tangutica.

    PubMed

    Zhang, Wei; Yao, Min-Na; Tang, Hai-Feng; Tian, Xiang-Rong; Wang, Min-Chang; Ji, Lan-Ju; Xi, Miao-Miao

    2013-05-01

    Four new triterpenoid saponins named clematangosides A-D (1-4) along with six known saponins (5-10) were isolated from the whole plants of Clematis tangutica. Their structures were determined by extensive spectral analysis and chemical evidences. All saponins were evaluated for their protective effects in hypoxia-induced myocardial injury model. Compounds 2-4, 6, and 10 exhibited anti-myocardial ischemia activities with ED50 values in the range of 75.77-127.22 µM. PMID:23670628

  6. Antiproliferative effects of saponins from the roots of Platycodon grandiflorum on cultured human tumor cells.

    PubMed

    Choi, Yeon Hee; Yoo, Dae Seok; Cha, Mi-Ran; Choi, Chun Whan; Kim, Young Sup; Choi, Sang-Un; Lee, Kang Ro; Ryu, Shi Yong

    2010-11-29

    Three new triterpenoid saponins, platyconic acid B lactone (1), deapio-platyconic acid B lactone (2), and deapio-platycodin D(2) (3), together with 17 known triterpenoid saponins, were isolated from a root extract of Platycodon grandiflorum. The structures of 1-3 were determined on the basis of spectroscopic data interpretation and chemical transformation. Saponins with a platycodigenin or polygalacic acid unit as a sapogenin demonstrated significant inhibitory effects on the proliferation of a small panel of cultured human tumor cells. PMID:20939516

  7. Steroidal saponins obtained by biotransformation of total furostanol glycosides from Dioscorea zingiberensis with Absidia coerulea.

    PubMed

    Pang, Xu; Wen, Di; Zhao, Yang; Xiong, Cheng-Qi; Wang, Xiao-Qin; Yu, Li-Yan; Ma, Bai-Ping

    2015-01-30

    Five new steroidal saponins (1-5) were isolated from the fermentation broth of total furostanol glycosides from tubers of Dioscorea zingiberensis C.H. Wright incubated with a fungal, Absidia coerulea AS 3.3389, along with known saponins, zingiberensis new saponin (6), deltonin (7), prosapogenin A of dioscin (8), and protobioside (9), and their structures were established by NMR spectroscopy and mass spectrometry as well as by comparison with previously reported spectral data in the literatures. The induced effects in vitro on rat platelet aggregation of all compounds were evaluated. PMID:25498025

  8. Synthesis, cytotoxicity and haemolytic activity of Pulsatilla saponin A, D derivatives.

    PubMed

    Chen, Zhong; Duan, Huaqing; Wang, Minglei; Han, Li; Liu, Yanli; Zhu, Yongming; Yang, Shilin

    2015-06-15

    The strong haemolytic activity of Pulsatilla saponin A (PSA), D (PSD) hampered their clinical development of antitumor agents. In order to solve this problem, C-28 position modification derivatives of PSA/PSD were synthesized. The cytotoxicity and haemolytic activity of these compounds were evaluated. Structure-activity relationship and structure-toxicity relationship had been observed. The mice acute toxicity of compound 11 was reduced greatly than that of PSA. This study indicates that compound 11 may represent an interesting class of potent antitumor agents from triterpenoid saponins avoiding the haemolysis problem. The present study has important significance for the development of antitumor saponins. PMID:25958248

  9. EBV DNA polymerase inhibition of tannins from Eugenia uniflora.

    PubMed

    Lee, M H; Chiou, J F; Yen, K Y; Yang, L L

    2000-06-30

    Nasopharyngeal carcinoma (NPC) is one of the high population malignant tumors among Chinese in southern China and southeast Asia. Epstein-Barr virus (EBV) is a human B lymphotropic herpes virus which is known to be closely associated with NPC. EBV DNA polymerase is a key enzyme during EBV replication and is measured by its radioactivity. The addition of phorbol 12-myristate 13-acetate to Raji cell cultures led to a large increase in EBV DNA polymerase, which was purified by sequential DEAE-cellulose, phosphocellulose and DNA-cellulose column chromatography. Four tannins were isolated from the active fractions of Eugenia uniflora L., which were tested for the inhibition of EBV DNA polymerase. The results showed the 50% inhibitory concentration (IC(50)) values of gallocatechin, oenothein B, eugeniflorins D(1) and D(2) were 26.5 62.3, 3.0 and 3.5 microM, respectively. Furthermore, when compared with the positive control (phosphonoacetic acid), an inhibitor of EBV replication, the IC(50) value was 16.4 microM. In view of the results, eugeniflorins D(1) and D(2) are the potency principles in the inhibition of EBV DNA polymerase from E. uniflora. PMID:10806300

  10. Rigidity, conformation, and solvation of native and oxidized tannin macromolecules in water-ethanol solution

    NASA Astrophysics Data System (ADS)

    Zanchi, Dražen; Konarev, Petr V.; Tribet, Christophe; Baron, Alain; Svergun, Dmitri I.; Guyot, Sylvain

    2009-06-01

    We studied by light scattering and small angle x-rays scattering (SAXS) conformations and solvation of plant tannins (oligomers and polymers) in mixed water-ethanol solutions. Their structures are not simple linear chains but contain about 6% of branching. Ab initio reconstruction reveals that monomers within a branch are closely bound pairwise. The chains are rather rigid, with the Kuhn length b =13±3 nm, corresponding to about 35 linearly bound monomers. Contribution of solvation layer to SAXS intensity varies in a nonmonotonic way with ethanol content ϕA, which is an indication of amphipathic nature of tannin molecules. Best solvent composition ϕAB is a decreasing function of polymerization degree N, in agreement with increasing water solubility of tannins with N. Polymers longer than b present a power-law behavior I ˜Q-d in the SAXS profile at high momentum transfer Q. The monotonic decrease in d with increasing ϕA (from 2.4 in water to 1.9 in ethanol) points that the tannins are more compact in water than in ethanol, presumably due to attractive intramolecular interactions in water. Tannins were then oxidized in controlled conditions similar to real biological or food systems. Oxidation does not produce any intermolecular condensation, but generates additional intramolecular links. Some oxidation products are insoluble in water rich solvent. For that reason, we identify these species as a fraction of natural tannins called "T1" in the notation of Zanchi et al. [Langmuir 23, 9949 (2007)]. Within the fraction left soluble after oxidation, conformations of polymeric tannins, despite their higher rigidity, remain sensitive to solvent composition.

  11. Condensed tannins inhibit house fly (Diptera: Muscidae) development in livestock manure.

    PubMed

    Littlefield, Kimberly A; Muir, James P; Lambert, Barry D; Tomberlin, Jeffery K

    2011-12-01

    Reducing chemical use for suppressing internal and external parasites of livestock is essential for protecting environmental health. Although plant condensed tannins are known to suppress gastro-intestinal parasites in small ruminants, no research on the effects of tannins on external arthropod populations such as the house fly, Musca domestica L., have been conducted. We examined the impact of plant material containing condensed tannins on house fly development. Prairie acacia (Acacia angustissima (Mill.), Kuntze variety hirta (Nutt.) B.L. Rob.) herbage, panicled tick-clover (Desmodium paniculatum (L.) DC.) herbage, and quebracho (Shinopsis balansae Engl.) extracts were introduced at rates of 1, 3 or 5% condensed tannins/kg beef cattle, dairy cattle, and goat manure, respectively. In a second experiment, we also introduce purified catechin at 1 or 3% of dairy manure dry matter and measured its impact on house fly development. For the house flies used in these experiments, the following was recorded: percent fly emergence (PFE), average daily gain (ADG), and average fly weight (AFW). No effects (P>0.05) in house fly development were measured in the caprine manure. Prairie acacia (20.9% condensed tannins) had no effect on house flies developing in either bovine manures. Tick clover (4.9% condensed tannins) had a negative effect on all three quantifiable variables of house fly development in the bovine manures, whereas quebracho extract (64.0% condensed tannins) at the 3 and 5% rate reduced fly emergence in beef manure and average daily gain in dairy manure. The application of purified catechin at 3%, but not 1%, reduced fly PFE, ADG, and AFW. PMID:22217775

  12. Botanical traceability of commercial tannins using the mineral profile and stable isotopes.

    PubMed

    Bertoldi, Daniela; Santato, Alessandro; Paolini, Mauro; Barbero, Alice; Camin, Federica; Nicolini, Giorgio; Larcher, Roberto

    2014-09-01

    Commercial tannins are natural polyphenolic compounds extracted from different plant tissues such as gall, the wood of different species and fruit. In the food industry they are mainly used as flavourings and food ingredients, whereas in winemaking they are classified as clarification agents for wine protein stabilisation, although colour stabilisation, metal removal, unpleasant thiol removal and rheological correction are also well-known and desired effects. Due to their particular technical properties and very different costs, the possibility of correct identification of the real botanical origin of tannins can be considered a primary target in oenology research and in fulfilling the technical and economic requirements of the wine industry. For some categories of tannins encouraging results have already been achieved by considering sugar or polyphenolic composition. For the first time this work verifies the possibility of determining the botanical origin of tannins on the basis of the mineral element profile and analysis of the (13) C/(12) C isotopic ratio. One hundred two commercial tannins originating from 10 different botanical sources (grapes, oak, gall, chestnut, fruit trees, quebracho, tea, acacia, officinal plants and tara) were analysed to determine 57 elements and the (13) C/(12) C isotopic ratio, using inductively coupled plasma mass spectrometry and isotope-ratio mass spectrometry, respectively. Forward stepwise discriminant analysis provided good discrimination between the 8 most abundant groups, with 100% correct re-classification. The model was then validated five times on subsets of 10% of the overall samples, randomly extracted, achieving satisfactory results. With a similar approach it was also possible to distinguish toasted and untoasted oak tannins as well as tannins from grape skin and grape seeds. PMID:25230175

  13. Alkaloids of Thalictrum XXVII. New hypotensive aporphine-benzylisoquinoline derived dimeric alkaloids from Thalictrum minus race B.

    PubMed

    Liao, W T; Beal, J L; Wu, W N; Doskotch, R W

    1978-01-01

    The roots of T. minus race B have yielded, in addition to adiantifoline (1) previously isolated from this source, two new related alkaloids, thaliadine (2) and thaliadanine (5). Both were assigned complete structures by spectral methods and by chemical interconversion to adiantifoline or its product. O-Desmethyladiantifoline should have structure 14, rather than the previously reported 5. All three isolated alkaloids show hypotensive activity in rabbits, and thaliadanine (5) has antimicrobial activity against Mycobacterium smegmatis. PMID:672464

  14. Biosynthesis and Regulation of Bioprotective Alkaloids in the Gramineae Endophytic Fungi with Implications for Herbivores Deterrents.

    PubMed

    Luo, Hongping; Xie, Longxiang; Zeng, Jie; Xie, Jianping

    2015-12-01

    Four kinds of bioprotective alkaloids-peramine, loline, ergot alkaloid, indole-diterpenes, produced by grass-fungal endophyte symbioses, are deterrents or toxic to vertebrate and invertebrate herbivores. Ergot alkaloids have pharmacological properties and widely are used clinically. The regulation of alkaloids biosynthesis is under intensive study to improve the yield for better agricultural and medicinal application. In this paper, we summarize the structure, related genes, regulation, and toxicity of alkaloids. We focus on the biosynthesis and the regulation network of alkaloids. PMID:26349576

  15. Astonishing diversity of natural surfactants: 6. Biologically active marine and terrestrial alkaloid glycosides.

    PubMed

    Dembitsky, Valery M

    2005-11-01

    This review article presents 209 alkaloid glycosides isolated and identified from plants, microorganisms, and marine invertebrates that demonstrate different biological activities. They are of great interest, especially for the medicinal and/or pharmaceutical industries. These biologically active glycosides have good potential for future chemical preparation of compounds useful as antioxidants, anticancer, antimicrobial, and antibacterial agents. These glycosidic compounds have been subdivided into several groups, including: acridone; aporphine; benzoxazinoid; ergot; indole; enediyne alkaloidal antibiotics; glycosidic lupine alkaloids; piperidine, pyridine, pyrrolidine, and pyrrolizidine alkaloid glycosides; glycosidic quinoline and isoquinoline alkaloids; steroidal glycoalkaloids; and miscellaneous alkaloid glycosides. PMID:16459921

  16. Elucidation of molecular diversity and body distribution of saponins in the sea cucumber Holothuria forskali (Echinodermata) by mass spectrometry.

    PubMed

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

    2009-02-01

    Sea cucumbers contain triterpene glycosides called saponins. We investigated the complex saponin mixture extracted from the common Mediterranean species Holothuria forskali. Two different body components were analyzed separately: the body wall (which protects the animal and is moreover the most important organ in terms of surface and weight) and the Cuvierian tubules (a defensive organ that can be expelled on predators in response to an attack). MALDI/MS and MALDI/MS/MS were used to detect saponins and describe their molecular structures. As isomers have been found in the Cuvierian tubules, LC/MS and LC/MS/MS were performed to identify each saponin separately. Twelve saponins have been detected in the body wall and 26 in the Cuvierian tubules. All the saponins from the body wall are also present in the Cuvierian tubules but the latter also contain 14 specific saponins. The presence of isomeric saponins complicated structure elucidation for the whole set but 16 saponins have been described tentatively. Among these, 3 had already been reported in the literature as holothurinosides A and C, and desholothurin A. Molecular structures have been proposed for the 13 others which, in the present work, have been provisionally named holothurinosides E, F, G, H, I, A(1), C(1), E(1), F(1), G(1), H(1) and I(1) and desholothurin A(1). The diversity and organ specificity of the saponins described here are much higher than what had been reported to date in any sea cucumber species. PMID:19036349

  17. 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. PMID:22507832

  18. Inhibition of hydrogen sulfide, methane, and total gas production and sulfate-reducing bacteria in in vitro swine manure by tannins, with focus on condensed quebracho tannins.

    PubMed

    Whitehead, Terence R; Spence, Cheryl; Cotta, Michael A

    2013-09-01

    Management practices from large-scale swine production facilities have resulted in the increased collection and storage of manure for off-season fertilization use. Odor and emissions produced during storage have increased the tension among rural neighbors and among urban and rural residents. Production of these compounds from stored manure is the result of microbial activity of the anaerobic bacteria populations during storage. In the current study, the inhibitory effects of condensed quebracho tannins on in vitro swine manure for reduction of microbial activity and reduced production of gaseous emissions, including the toxic odorant hydrogen sulfide produced by sulfate-reducing bacteria (SRB), was examined. Swine manure was collected from a local swine facility, diluted in anaerobic buffer, and mixed with 1 % w/v fresh feces. This slurry was combined with quebracho tannins, and total gas and hydrogen sulfide production was monitored over time. Aliquots were removed periodically for isolation of DNA to measure the SRB populations using quantitative PCR. Addition of tannins reduced overall gas, hydrogen sulfide, and methane production by greater than 90 % after 7 days of treatment and continued to at least 28 days. SRB population was also significantly decreased by tannin addition. qRT-PCR of 16S rDNA bacteria genes showed that the total bacterial population was also decreased in these incubations. These results indicate that the tannins elicited a collective effect on the bacterial population and also suggest a reduction in the population of methanogenic microorganisms as demonstrated by reduced methane production in these experiments. Such a generalized effect could be extrapolated to a reduction in other odor-associated emissions during manure storage. PMID:23149758

  19. Dietary crude protein and tannin impact dairy manure chemistry and ammonia emissions from incubated soils.

    PubMed

    Powell, J M; Aguerre, M J; Wattiaux, M A

    2011-01-01

    Excess crude protein (CP) in dairy cow diets is excreted mostly as urea nitrogen (N), which increases ammonia (NH) emissions from dairy farms and heightens human health and environmental concerns. Feeding less CP and more tannin to dairy cows may enhance feed N use and milk production, abate NH emissions, and conserve the fertilizer N value of manure. Lab-scale ventilated chambers were used to evaluate the impacts of CP and tannin feeding on slurry chemistry, NH emissions, and soil inorganic N levels after slurry application to a sandy loam soil and a silt loam soil. Slurry from lactating Holstein dairy cows (Bos taurus) fed two levels of dietary CP (low CP [LCP], 155 g kg; high CP [HCP], 168 g kg) each fed at four levels of dietary tannin extract, a mixture from red quebracho (Schinopsis lorentzii) and chestnut (Castanea sativa) trees (0 tannin [0T]; low tannin [LT], 4.5 g kg; medium tannin [MT], 9.0 g kg; and high tannin [HT], 18.0 g kg) were applied to soil-containing lab-scale chambers, and NH emissions were measured 1, 3, 6, 12, 24, 36, and 48 h after slurry application. Emissions from the HCP slurry were 1.53 to 2.57 times greater ( < 0.05) than from the LCP slurry. At trial's end (48 h), concentrations of inorganic N in soils were greater ( < 0.05) in HCP slurry-amended soils than in LCP slurry-amended soils. Emissions from HT slurry were 28 to 49% lower ( < 0.05) than emissions from 0T slurry, yet these differences did not affect soil inorganic N levels. Emissions from the sandy loam soil were 1.07 to 1.15 times greater ( < 0.05) than from silt loam soil, a result that decreased soil inorganic N in the sandy loam compared with the silt loam soil. Larger-scale and longer-term field trails are needed to ascertain the effectiveness of feeding tannin extracts to dairy cows in abating NH loss from land-applied slurry and the impact of tannin-containing slurry on soil N cycles. PMID:22031559

  20. 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. PMID:23774664