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Sample records for iridoid glucoside aucubin

  1. Iridoid glucosides from Penstemon ovatus.

    PubMed

    König, M; Seifert, K

    1995-02-01

    In addition to aucubin, 6beta-hydroxyboschnaloside, and 6-O-(8"-hydroxy-2",6"-dimethyl-2"(E), 6"(E)-octadienoyl)-6beta-hydroxyboschnaloside, the new iridoid glucoside ovatuside has been isolated from the aerial parts of Penstemon ovatus. This iridoid was shown to be 6-O-(8"-hydroxy-2",6"-dimethyl-2"(E),6"(Z)-octadienoyl)-6beta-hydroxyboschnaloside. PMID:17238062

  2. Iridoid Glucosides from Penstemon nitidus.

    PubMed

    Teborg, D; Junior, P

    1991-04-01

    From the leaves of PENSTEMON NITIDUS Dougl. (smooth blue beardtongue) besides the known iridoid glucosides cornin (syn. verbenalin), hastatoside and beta-dihydrohastatoside the new compound 10-hydroxycornin has been isolated. The structures of all compounds were established by spectroscopic means (FD-MS, (1)H-, (13)C-, 2D-NMR, and NOE). This is the first report of cornin and analogous 6-keto iridoids in scrophulariaceous plants. Up to now iridoid glucosides like these have only been found in plants belonging to the Cornaceae and its allies and to the Lamiaceae-Verbenaceae complex. PMID:17226148

  3. Iridoid Glucosides and an Acetophenone Glucoside from Penstemon whippleanus.

    PubMed

    Junior, P

    1984-10-01

    From leaves of PENSTEMON WHIPPLEANUS A. Gray three iridoid glucosides and an acetophenone glucoside have been isolated which were proved to be 10- T-cinnamoylaucubin, eurostoside, mussaenoside and picein, respectively. PMID:17340348

  4. Secoiridoid and iridoid glucosides from Syringa afghanica.

    PubMed

    Takenaka, Yukiko; Okazaki, Naoaki; Tanahashi, Takao; Nagakura, Naotaka; Nishi, Toyoyuki

    2002-04-01

    Phytochemical investigation of the dried leaves of Syringa afghanica, has led to the isolation of nine secoiridoid glucosides, safghanosides A-H and 2"-epi-frameroside, as well as an iridoid glucoside, syringafghanoside along with nineteen known compounds. The structures were elucidated by spectroscopic and chemical means. PMID:11909635

  5. [Iso-Scrophularioside, a new iridoid glucoside from Penstemon eriantherus].

    PubMed

    Junior, P

    1981-09-01

    From the aerial parts of Penstemon eriantherus Pursh a new iridoid glucoside was isolated and structurally elucidated as 10-cinnamoylaucubin mainly by spectroscopic methods ( (1)-NMR, (13)-NMR, MS). PMID:17402005

  6. Iridoid and bis-iridoid glucosides from the fruit of Gardenia jasminoides.

    PubMed

    Li, Hai-Bo; Yu, Yang; Wang, Zhen-Zhong; Dai, Yi; Gao, Hao; Xiao, Wei; Yao, Xin-Sheng

    2013-07-01

    Three new iridoid glucosides, 6?-O-trans-feruloylgenipin gentiobioside (1), 2'-O-trans-caffeoylgardoside (2), jasmigeniposide A (3), and one new bis-iridoid glucoside, jasmigeniposide B (4), along with six known analogues (5-10), were isolated from the fruit of Gardenia jasminoides. Their structures were established on the basis of spectroscopic analyses and chemical methods. Anti-virus activity of isolated compounds were evaluated in vitro and only compound 9 showed moderate inhibitory activity against H1N1 with 50% effective concentration (EC50) value of 104.36 ?M, and selective index (SI) value greater than 4.79. PMID:23567862

  7. Serrulatoloside, a New Iridoid Glucoside from Penstemon serrulatus.

    PubMed

    Junior, P

    1984-10-01

    From leaves of PENSTEMON SERRULATUS Menz. a new iridoid glucoside of unusual type in having an exo double bond at C-8 on the cyclopentane-ring has been isolated. The structure of serrulatoloside has been established by spectroscopic methods. PMID:17340346

  8. Further iridoid glucosides in the genus Manulea (Scrophulariaceae).

    PubMed

    Gousiadou, Chrysoula; Kokubun, Tetsuo; Gotfredsen, Charlotte H; Jensen, Søren R

    2015-01-01

    From Manulea altissima (Scrophulariaceae) were isolated five known secoiridoid glucosides sweroside, eustomoside, eustoside, secoxyloganin and secologanoside as well as the 4?-O-rhamnopyranosyl-feruloyl ester of adoxosidic acid, named altissimoside. Also, the caffeoyl phenylethanoid glycoside verbascoside was isolated. In addition two previously unknown terpenoid esters of 6?-hydroxy 8-epi-boschnaloside, named manucoside A and B were isolated from a formerly obtained fraction from the work-up of Manulea corymbosa. The distribution of iridoid glucosides in the Scrophulariaceae is discussed. PMID:25457503

  9. Iridoid glucosides in the endemic Picconia azorica (Oleaceae).

    PubMed

    Gousiadou, Chrysoula; Kokubun, Tetsuo; Martins, José; Gotfredsen, Charlotte H; Jensen, Søren R

    2015-07-01

    In our continued investigation of plants from the family Oleaceae we have now investigated Picconia azorica endemic to the Azores. Like most species within the family it contains the oleoside-based secoiridoid glucosides ligstroside and oleuropein as the main compounds and in addition verbascoside and echinacoside. As with the previously investigated Picconia excelsa, it also contained the carbocyclic iridoid glucosides involved in the biosynthetic pathway to the oleoside derivatives. However, while P. excelsa contained loganin esterified with some monoterpenoid acids, P. azorica contains similar esters of 7-epi-loganic acid named Picconioside A and B. In addition were found the two 7-O-E/Z-cinnamoyl esters of 7-epi-loganic acid named Picconioside C and D. PMID:25687603

  10. [Pinifolin, a new iridoid glucoside of unusual type from Penstemon pinifolius].

    PubMed

    Junior, P

    1989-02-01

    From the aerial parts of PENSTEMON PINIFOLIUS Greene, a new iridoid glucoside of unusual type has been isolated and structurally elucidated by spectroscopic means. This new compound, called pinifolin, contains a Delta (4)-instead of a Delta (3)-double bond and a methyl ether function at carbon 3 of the iridoidic skeleton. PMID:17262263

  11. [Nemoroside and nemorososide, new iridoid glucosides from Penstemon nemorosus].

    PubMed

    Junior, P

    1983-02-01

    From leaves of Penstemon nemorosus Trautv. two new esteriridoids have been isolated. Iridoidic moieties are catapol and ajugol, both esterified with 8-hydroxy-2,6-dimethyl-2,6-octadienoic acid. The structure was established by spectroscopic methods and comparison with known compounds. PMID:17405095

  12. Iridoids and phenylethanoid from Pedicularis kerneri Dalla Torre growing in Dolomites, Italy.

    PubMed

    Venditti, Alessandro; Frezza, Claudio; Serafini, Mauro; Bianco, Armandodoriano

    2016-02-01

    In this study, we report the first phytochemical analysis of polar fraction of Pedicularis kerneri Dalla Torre growing in Dolomites, Italy. Several iridoid glucosides were isolated, namely aucubin (1), monomelittoside (2), plantarenaloside (3), euphroside (4), mussaenosidic acid (5) and 8-epiloganic acid (6), showing a composition in accordance with previous study on this genus. The studied samples, collected from Dolomites, presented a chemotype already recognised in species from North America, characterised by euphroside (4) and aucubin (1) as main components, but the main character was the presence of monomelittoside (2) never reported in this genus. The identification of verbascoside (7), leucosceptoside A (9) and echinacoside (10) complete the systematic framing of this species since is ascertained the co-occurrence of phenylethanoid glycosides with iridoids in Lamiales species. PMID:26207992

  13. Geniposide, an iridoid glucoside derived from Gardenia jasminoides, protects against lipopolysaccharide-induced acute lung injury in mice.

    PubMed

    Xiaofeng, Yang; Qinren, Cai; Jingping, He; Xiao, Chu; Miaomiao, Wei; Xiangru, Feng; Xianxing, Xie; Meixia, Huo; Jing, Liu; Jingyuan, Wei; Xinxin, Ci; Hongyu, Li; Yanhong, Deng; Lanxiang, Jiang; Xuming, Deng

    2012-04-01

    Geniposide, a main iridoid glucoside component of gardenia fruit, has been shown to possess anti-inflammatory activity. However, its potential use for acute lung injury (ALI) has not yet been studied. The aim of this study was to evaluate the anti-inflammatory properties of geniposide using a mouse ALI model. ALI was induced by intranasal injection of lipopolysaccharide (LPS). Pretreatment of mice with geniposide (20, 40, or 80 mg/kg) resulted in a marked reduction in inflammatory cells and total protein concentration in the bronchoalveolar lavage fluid (BALF) of mice. Levels of inflammatory mediators, including tumour necrosis factor- ? (TNF- ?), interleukin-6 (IL-6), and interleukin-10 (IL-10), were significantly altered after treatment with geniposide. Histological studies using hematoxylin and eosin (H&E) staining demonstrate that geniposide substantially inhibited LPS-induced alveolar wall changes, alveolar haemorrhage, and neutrophil infiltration in lung tissue, with evidence of reduced myeloperoxidase (MPO) activity. In addition, we investigated potential signal transduction mechanisms that could be implicated in geniposide activity. Our results suggest that geniposide may provide protective effects against LPS-induced ALI by mitigating inflammatory responses and that the compound's mechanism of action may involve blocking nuclear factor-kappaB (NF- ?B) and mitogen-activated protein kinases (MAPK) signalling pathway activation. PMID:22354390

  14. Verbascoside derivatives and iridoid glycosides from Penstemon crandallii.

    PubMed

    Ismail, L D; el-Azizi, M M; Khalifa, T I; Stermitz, F R

    1995-08-01

    The new phenylethanoid glycosides 2-O-acetyl-3'''-O-methylverbascoside and 2,4"-di-O-acetyl-3'''-O-methylverbascoside were isolated and identified from Penstemon crandallii. The major iridoid glycoside was plantarenaloside and no aucubin type iridoids were found. This contrasted with a previous analysis of P. teucrioides, from the same Penstemon subsection, which was dominated by aucubin derivatives. PMID:7669280

  15. A Validated HPTLC-Densitometric Method for Assay of Aucubin in Vitexagnus-castusL.

    PubMed Central

    Hajimehdipoor, Homa; Shekarchi, Maryam; PiraliHamedani, Morteza; Abedi, Zahra; Zahedi, Homeyra; Shekarchi, Maral; Gohari, Ahmad Reza

    2011-01-01

    Vitexagnus-castusL. is a medicinal plant which is used in several dosage forms for women hormonal disorders and standardized according to the iridoids or flavonoids content. Aucubin, an iridoid glycoside, considered as a marker in some formulations. In this research, a thin layer chromatographic method with densitometric detection has been developed for quantitative determination of aucubin in chaste tree fruits. Chromatographic separation was performed using silica gel high performance thin-layer chromatography (HPTLC) plates with ethyl acetate-methanol-water 77 : 15 : 8 as mobile phase. Chromatograms were visualized using p-dimethylaminobenzaldehyde as reagent. Aucubin RF-value was about 0.5 and spots were scanned at 580 nm through a mercury lamp. By using this method, the amount of aucubin was found 43.5 mg/100 g of dried plant fruits. The method was validated for selectivity, linearity (r2 = 0.997, 20-100 ?g/mL), precision (intra-day < 4.9, inter-day < 7.2) and accuracy measured via determination of recovery (95-98%). The limit of detection and limit of quantization were found 6.6 and 20 ?g/mL, respectively. This methodology was found to be precise with respect to the validation parameters. It is simple and convenient and could be applicable to the routine determination of aucubin in different Vitexagnus-castusL. samples. PMID:24250405

  16. 8-epiloganic acid and 7-beta-hydroxy-8-epiiridodial glucoside.

    PubMed

    Bianco, A; Passacantilli, P; Polidori, G

    1982-09-01

    Two new iridoid glucosides, isolated from Linaria cymbalaria (Scrophulariaceae), are 8-epiloganic acid ( 1) and 7-beta-hydroxy-8-epiiridodial glucoside ( 2). Partial synthesis of 2 from 8-epiloganin ( 3) has been performed. PMID:17396936

  17. Iridoid-specific glucosyltransferase from Gardenia jasminoides.

    PubMed

    Nagatoshi, Mai; Terasaka, Kazuyoshi; Nagatsu, Akito; Mizukami, Hajime

    2011-09-16

    Iridoids are one of the most widely distributed secondary metabolites in higher plants. They are pharmacologically active principles in various medicinal plants and key intermediates in the biosynthesis of monoterpenoid indole alkaloids as well as quinoline alkaloids. Although most iridoids are present as 1-O-glucosides, the glucosylation step in the biosynthetic pathway has remained obscure. We isolated a cDNA coding for UDP-glucose:iridoid glucosyltransferase (UGT85A24) from Gardenia jasminoides. UGT85A24 preferentially glucosylated the 1-O-hydroxyl group of 7-deoxyloganetin and genipin but exhibited only weak activity toward loganetin and no activity toward 7-deoxyloganetic acid. This suggests that, in the biosynthetic pathway of geniposide, a major iridoid compound in G. jasminoides, glucosylation occurs after methylation of 7-deoxyloganetic acid. UGT85A24 showed negligible activity toward any acceptor substrates other than iridoid aglycones. Thus, UGT85A24 has a remarkable specificity for iridoid aglycones. The mRNA level of UGT85A24 overlaps with the marked increase in genipin glucosylation activity in the methyl jasmonate-treated cell cultures of G. jasminoides and is related to iridoid accumulation in G. jasminoides fruits. PMID:21799001

  18. Host dependent iridoid glycoside sequestration patterns in Cionus hortulanus.

    PubMed

    Baden, Christian Ulrich; Franke, Stephan; Dobler, Susanne

    2013-08-01

    Weevils of the genus Cionus (Curculionidae, Mecininae) sequester the iridoid glycosides (IGs) aucubin and catalpol from their host plants Scrophularia or Verbascum (Scrophulariaceae). Cionus hortulanus is the only member of the genus that feeds on both plant genera. We previously showed that sequestration patterns in C. hortulanus depend on the local host. To investigate whether IG patterns are driven by their availability in the hosts or genetic differences between populations, we collected C. hortulanus from S. nodosa in the field and reared them either on S. nodosa or on V. nigrum. The differences in IG concentrations were specific for the host plant upon which the weevils developed. Similar to monophagous species of the Cionini, individuals from S. nodosa had more aucubin than catalpol and mirrored the concentrations of their host plants. Specimens from V. nigrum, on the other hand, had higher concentrations of aucubin and of catalpol than their host. On V. nigrum, the ratio of catalpol to aucubin differed significantly between plant and beetle samples due to much higher catalpol concentrations in the weevils. Our data thus contradict genetically fixed differences between populations living on either plant but rather document the host plants' influence on the beetles' metabolism. PMID:23846185

  19. A new iridoid glycoside from Scrophularia ningpoensis.

    PubMed

    Niu, Zheng-Rui; Wang, Ru-Feng; Shang, Ming-Ying; Cai, Shao-Qing

    2009-01-01

    A new iridoid glycoside, named 6'-O-cinnamoylharpagide (1), has been isolated from the roots of Scrophularia ningpoensis (Scrophulariaceae) together with nine known compounds, harpagide (2), harpagoside (3), 8-O-feruloylharpagide (4), 8-O-(p-coumaroyl)harpagide (5), 6-O-methylcatalpol (6), aucubin (7), buergerinin B (8), teuhircoside (9) and 6-O-cinnamoyl-D-glucopyranose (10). Compound 10 was obtained as an inseparable mixture of 6-O-cinnamoyl-alpha-D-glucopyranose and 6-O-cinnamoyl-beta-D-glucopyranose at a ratio of 1 : 1, which is presumably formed by cleavage of compound 1. Their structures were elucidated on the basis of chemical and spectral analysis. PMID:19731136

  20. Two new iridoids from selected Penstemon species--antimicrobial activity.

    PubMed

    Zajdel, Sybilla M; Graikou, Konstantia; Sotiroudis, Georgios; G?owniak, Kazimierz; Chinou, Ioanna

    2013-01-01

    Eighteen secondary metabolites, belonging to three different chemical groups, were isolated from the methanolic extracts of the aerial parts of selected penstemon plants [Penstemon fruticosus (Pursh) Greene var. fruticosus, Penstemon palmeri Gray and Penstemon venustus Doug. ex Lindl.], and their structures were elucidated on the basis of spectral evidence. Six iridoid glucosides (1-6), three phenylpropanoid glucosides (13-15) and two acetophenone derivatives (16,17), obtained from P. fruticosus, five iridoids (2, 7-10), one phenylpropanoid glucoside (15) and two acetophenones (16, 18), isolated from P. palmeri while three iridoids (2, 11, 12) and three phenylpropanoids (13-15) were identified in P. venustus. Two of the iridoid glucosides (4, 5) from P. fruticosus are new natural products named accordingly as cis- and trans- forms of 10-O-p-methoxycinnamoylaucubin. All isolated compounds, as well as crude methanolic extracts, were evaluated for their antimicrobial activities against six Gram-positive and Gram-negative bacteria and three human pathogenic fungi. PMID:24004258

  1. Iridoids from Penstemon richardsonii.

    PubMed

    Gering-Ward, B; Wichtl, M

    1988-10-01

    From the leaves of PENSTEMON RICHARDSONII Dougl., four valeriana-type ester iridoids have been isolated and structurally elucidated as serrulatoloside, 10-deoxypatrinoside, serrulatoloside-aglycone, and 10-deoxypatrinoside-aglycone. PMID:17265313

  2. New iridoid diesters of glucopyranose from Linaria canadensis (L.) Dum.

    PubMed

    Mizuochi, Kouichi; Tanaka, Takashi; Kouno, Isao; Fujioka, Toshihiro; Yoshimura, Yuki; Ishimaru, Kanji

    2011-01-01

    Two new iridoid diesters of glucopyranose were isolated from the aerial part of Linaria canadensis (L.) Dum. Eight known flavones, apigenin, diosmetin, genkwanin, luteolin, luteolin 7-O-glucoside, luteolin 7-O-glucuronide, genkwanin 4'-O-rutinoside, and quercetin 7-O-rutinoside were also isolated. The chemical structures of the isolated compounds were elucidated based on the analyses of the spectroscopic data. PMID:20635154

  3. Chemotaxonomy of iridoids in Linaria vulgaris.

    PubMed

    Guiso, Marcella; Tassone, Grazia; Nicoletti, Marcello; Serafini, Mauro; Bianco, Armandodoriano

    2007-11-01

    The phytochemical analysis of the extracts of Linaria vulgaris, has allowed to underline an iridoidic pattern similar to that of the other Linaria plants, with the presence of antirrinoside, antirride, 6-beta-idrossiantirride, 10-beta-glucosilaucubina and a new iridoidic compound, whose structure was demonstrated to be that of 4-carboxy-boonein. PMID:17987503

  4. Secoiridoid glucosides with free radical scavenging activity from the leaves of Syringa dilatata.

    PubMed

    Oh, Hyuncheol; Ko, Eun-Kyoung; Kim, Do-Hoon; Jang, Kyu-Kwan; Park, Sung-Eun; Lee, Ho-Sub; Kim, Youn-Chul

    2003-04-01

    Activity-guided fractionation of the EtOAc and MeOH extract of the leaves of Syringa dilatata NAKAI furnished one free radical scavenger, the secoiridoid glucoside oleuropein together with ligstroside and an iridoid glucoside, syringopicroside. Oleuropein interacted with the stable free radical, 1,1-diphenyl-2-picrylhydrazyl (DPPH), and showed an IC(50) value of 40.4 microM. L-Ascorbic acid as a positive control showed an IC(50) value of 50.3 microM. PMID:12722154

  5. Determination of phenylethanoid glycosides and iridoid glycosides from therapeutically used Plantago species by CE-MEKC.

    PubMed

    Gonda, Sándor; Nguyen, Nhat Minh; Batta, Gyula; Gyémánt, Gyöngyi; Máthé, Csaba; Vasas, Gábor

    2013-09-01

    CE methods are valuable tools for medicinal plant quality management, screening, and analysis. Therefore, the aim of the current study was to optimize and validate a CE-MEKC method for simultaneous quantification of four chief bioactive metabolites from Plantago species. The two most important secondary metabolite groups were aimed to be separated. Different electrolyte and surfactant types were tested. Surfactant concentration, BGE pH, electrolyte concentration, and buffering capacity were optimized. The final BGE consisted of 15 mM sodium tetraborate, 20 mM TAPS, and 250 mM DOC at pH 8.50. Acceptable precision, good stability, and accuracy were achieved, with high resolution for phenylethanoid glycosides. Analytes were separated within 20 min. The method was shown to be suitable for the quantification of the iridoid glycosides aucubin and catalpol, and the phenylethanoid glycosides acteoside (verbascoside) and plantamajoside from water extracts of different samples. The method was shown to be applicable to leaf extracts of Plantago lanceolata, Plantago major, and Plantago asiatica, the main species with therapeutic applications, and a biotechnological product, plant tissue cultures (calli) of P. lanceolata. Baseline separation of the main constituents from minor peaks was achieved, regardless of the matrix type. PMID:23784714

  6. Iridoid glycoside biosynthesis in Penstemon secundiflorus. Another H-5, H-9 trans-iridoid glycoside.

    PubMed

    Krull, R E; Stermitz, F R; Franzyk, H; Jensen, S R

    1998-11-01

    Isolation and characterization of the new iridoid 10-hydroxy-(5 alpha H)-6-epidihydrocornin from Penstemon secundiflorus (Scrophulariaceae) is described. In biosynthetic experiments, deoxyloganic acid was incorporated into the trans-fused iridoid glycosides (5 alpha H)-6-epidihydrocornin and 10-hydroxy-(5 alpha H)-6-epidihydrocornin in P. secundiflorus. Formation of the trans-fused compounds is therefore a late event in the biosynthesis and does not occur during iridoid formation by cyclization of the open chain monoterpene precursor. In the same plant, 8-epideoxyloganic acid was not incorporated into the trans-iridoids. Deoxyloganic acid was also incorporated into 10-hydroxyhastatoside (which bears an 8 beta-methyl group), while 8-epideoxyloganic acid was incorporated into penstemoside (with an 8 alpha-methyl group). Thus, iridoid biosynthetic pathways leading from both deoxyloganic acid and 8-epideoxyloganic acid were found in the same plant. PMID:9862136

  7. Trans-fused iridoid glycosides from Penstemon mucronatus.

    PubMed

    Krull, R E; Stermitz, F R

    1998-12-01

    Two new trans-fused iridoid glycosides (5 alpha H)-6 alpha-8-epidihydrocornin and (5 alpha H)-6 alpha-8-hydroxy-8-epiloganin, were isolated from Penstemon mucronatus, along with cornin, penstemoside and three hastatosides. The trans-fused iridoids are only the second and third known among over 900 described cis-fused iridoid glycosides. Two pairs of iridoids, identical except for the stereochemistry at C-8, were found. Structures were determined by spectroscopic methods. PMID:9887533

  8. Eucommia ulmoides Oliver Extract, Aucubin, and Geniposide Enhance Lysosomal Activity to Regulate ER Stress and Hepatic Lipid Accumulation

    PubMed Central

    Lee, Hwa-Young; Lee, Geum-Hwa; Lee, Mi-Rin; Kim, Hye-Kyung; Kim, Nan-young; Kim, Seung-Hyun; Lee, Yong-Chul; Kim, Hyung-Ryong; Chae, Han-Jung

    2013-01-01

    Eucommia ulmoides Oliver is a natural product widely used as a dietary supplement and medicinal plant. Here, we examined the potential regulatory effects of Eucommia ulmoides Oliver extracts (EUE) on hepatic dyslipidemia and its related mechanisms by in vitro and in vivo studies. EUE and its two active constituents, aucubin and geniposide, inhibited palmitate-induced endoplasmic reticulum (ER) stress, reducing hepatic lipid accumulation through secretion of apolipoprotein B and associated triglycerides and cholesterol in human HepG2 hepatocytes. To determine how EUE diminishes the ER stress response, lysosomal and proteasomal protein degradation activities were analyzed. Although proteasomal activity was not affected, lysosomal enzyme activities including V-ATPase were significantly increased by EUE as well as aucubin and geniposide in HepG2 cells. Treatment with the V-ATPase inhibitor, bafilomycin, reversed the inhibition of ER stress, secretion of apolipoprotein B, and hepatic lipid accumulation induced by EUE or its component, aucubin or geniposide. In addition, EUE was determined to regulate hepatic dyslipidemia by enhancing lysosomal activity and to regulate ER stress in rats fed a high-fat diet. Together, these results suggest that EUE and its active components enhance lysosomal activity, resulting in decreased ER stress and hepatic dyslipidemia. PMID:24349058

  9. Anti-Inflammatory Iridoids of Botanical Origin

    PubMed Central

    Viljoen, A; Mncwangi, N; Vermaak, I

    2012-01-01

    Inflammation is a manifestation of a wide range of disorders which include; arthritis, atherosclerosis, Alzheimer’s disease, inflammatory bowel syndrome, physical injury and infection amongst many others. Common treatment modalities are usually non-steroidal anti-inflammatory drugs (NSAIDs) such as aspirin, paracetamol, indomethacin and ibuprofen as well as corticosteroids such as prednisone. These however, may be associated with a host of side effects due to non-selectivity for cyclooxygenase (COX) enzymes involved in inflammation and those with selectivity may be highly priced. Thus, there is a continuing search for safe and effective anti-inflammatory molecules from natural sources. Research has confirmed that iridoids exhibit promising anti-inflammatory activity which may be beneficial in the treatment of inflammation. Iridoids are secondary metabolites present in various plants, especially in species belonging to the Apocynaceae, Lamiaceae, Loganiaceae, Rubiaceae, Scrophulariaceae and Verbenaceae families. Many of these ethnobotanicals have an illustrious history of traditional use alluding to their use to treat inflammation. Although iridoids exhibit a wide range of pharmacological activities such as cardiovascular, hepatoprotection, hypoglycaemic, antimutagenic, antispasmodic, anti-tumour, antiviral, immunomodulation and purgative effects this review will acutely focus on their anti-inflammatory properties. The paper aims to present a summary for the most prominent iridoid-containing plants for which anti-inflammatory activity has been demonstrated in vitro and / or in vivo. PMID:22414102

  10. A new iridoid diglucoside from Harpagophytum procumbens.

    PubMed

    Tomassini, Lamberto; Serafini, Mauro; Foddai, Sebastiano; Ventrone, Antonio; Nicoletti, Marcello

    2016-01-01

    A new iridoid diglucoside has been isolated from an aqueous extract of Harpagophytum procumbens secondary roots, together with six known compounds. Its structure has been assigned as 6'-O-glucopyranosyl-8-O-trans-coumaroylharpagide by spectroscopic means. PMID:26119468

  11. Iridoid glycosyl esters from Scrophularia ningpoensis.

    PubMed

    Chen, Xin; Liu, Yun-Hai; Chen, Ping

    2007-11-01

    A new Iridoid glycosyl ester, scrophulninoside A (1), as well as the known compounds (2-3), were isolated from the n-BuOH soluble fraction of the Scrophularia ningpoensis. The structure of scrophulninoside A (1) was elucidated by spectroscopic methods. PMID:17987499

  12. Structural determinants of reductive terpene cyclization in iridoid biosynthesis.

    PubMed

    Kries, Hajo; Caputi, Lorenzo; Stevenson, Clare E M; Kamileen, Mohammed O; Sherden, Nathaniel H; Geu-Flores, Fernando; Lawson, David M; O'Connor, Sarah E

    2016-01-01

    The carbon skeleton of ecologically and pharmacologically important iridoid monoterpenes is formed in a reductive cyclization reaction unrelated to canonical terpene cyclization. Here we report the crystal structure of the recently discovered iridoid cyclase (from Catharanthus roseus) bound to a mechanism-inspired inhibitor that illuminates substrate binding and catalytic function of the enzyme. Key features that distinguish iridoid synthase from its close homolog progesterone 5?-reductase are highlighted. PMID:26551396

  13. [8-epi-Valerosidate, a new iridoid glucoside from Penstemon serrulatus.].

    PubMed

    Junior, P

    1983-03-01

    From leaves of Penstemon serrulatus Menz. a new esteriridoid has been isolated. The structure was established by spectroscopic methods (IR, MS, (13)C-NMR) and mainly (1)H-NMR-spectroscopy as 8-epivalerosidate. PMID:17404906

  14. A new iridoid from Scrophularia auriculata ssp. pseudoauriculata.

    PubMed

    Giner, R M; Villalba, M L; Recio, M C; Máñez, S; Gray, A I; Ríos, J L

    1998-09-01

    A new iridoid glycoside, scrovalentinoside (1), was isolated from the MeOH extract of the aerial parts of Scrophularia auriculata L. ssp. pseudoauriculata. The structure of the new compound 1 was elucidated as 6-O-(2", 3"-di-O-acetyl-4"-O-p-methoxy-cinnamoyl)-alpha-L-rhamnopyranosyl catalpol by spectroscopic methods. The known iridoid glycoside, scropolioside A; two saponins, verbascosaponin A and verbascosaponin; and the phenylethanoid glycoside, verbascoside, were also isolated. PMID:9748391

  15. Martynoside and the Novel Dimeric Open-Chain Monoterpene Glucoside Digipenstroside from Penstemon digitalis.

    PubMed

    Teborg, D; Junior, P

    1989-10-01

    From the leaves of PENSTEMON DIGITALIS Nutt. a novel dimeric open-chain monoterpene glucoside, digipenstroside, in addition to the known phenylpropanoid glycoside martynoside has been isolated. The structure of digipenstroside was elucidated by spectroscopic means (FD-MS, (1)H-, (13)C-, and 2D-NMR spectroscopy) as 1-(beta- D-glucopyranosyl)-8-[8''-hydroxy-2''-6''-dimethyl-oct-2''( E),6''( E)-dienoyl]-5,8-dihydroxy-2,6-dimethylocta-2( E),6( E)-dienoate. Therefore digipenstroside belongs to a new type of natural compounds, comprising of two geraniol-type monoterpenes and glucose linked by esterification. The occurrence of such compounds together with intact iridoid glycosides might be of interest from the biogenetic point of view. PMID:17262462

  16. Conversion of Substrate Analogs Suggests a Michael Cyclization in Iridoid Biosynthesis

    PubMed Central

    Lindner, Stephanie; Geu-Flores, Fernando; Bräse, Stefan; Sherden, Nathaniel H.; O’Connor, Sarah E.

    2014-01-01

    Summary The core structure of the iridoid monoterpenes is formed by a unique cyclization reaction. The enzyme that catalyzes this reaction, iridoid synthase, is mechanistically distinct from other terpene cyclases. Here we describe the synthesis of two substrate analogs to probe the mechanism of iridoid synthase. Enzymatic assay of these substrate analogs along with clues from the product profile of the native substrate strongly suggest that iridoid synthase utilizes a Michael reaction to achieve cyclization. This improved mechanistic understanding will facilitate the exploitation of the potential of iridoid synthase to synthesize new cyclic compounds from nonnatural substrates. PMID:25444551

  17. The seco-iridoid pathway from Catharanthus roseus

    PubMed Central

    Miettinen, Karel; Dong, Lemeng; Navrot, Nicolas; Schneider, Thomas; Burlat, Vincent; Pollier, Jacob; Woittiez, Lotte; van der Krol, Sander; Lugan, Raphaël; Ilc, Tina; Verpoorte, Robert; Oksman-Caldentey, Kirsi-Marja; Martinoia, Enrico; Bouwmeester, Harro; Goossens, Alain; Memelink, Johan; Werck-Reichhart, Danièle

    2014-01-01

    The (seco)iridoids and their derivatives, the monoterpenoid indole alkaloids (MIAs), form two large families of plant-derived bioactive compounds with a wide spectrum of high-value pharmacological and insect-repellent activities. Vinblastine and vincristine, MIAs used as anticancer drugs, are produced by Catharanthus roseus in extremely low levels, leading to high market prices and poor availability. Their biotechnological production is hampered by the fragmentary knowledge of their biosynthesis. Here we report the discovery of the last four missing steps of the (seco)iridoid biosynthesis pathway. Expression of the eight genes encoding this pathway, together with two genes boosting precursor formation and two downstream alkaloid biosynthesis genes, in an alternative plant host, allows the heterologous production of the complex MIA strictosidine. This confirms the functionality of all enzymes of the pathway and highlights their utility for synthetic biology programmes towards a sustainable biotechnological production of valuable (seco)iridoids and alkaloids with pharmaceutical and agricultural applications. PMID:24710322

  18. Reassessment of Melittis melissophyllum L. subsp. melissophyllum iridoidic fraction.

    PubMed

    Venditti, A; Frezza, C; Guarcini, L; Maggi, F; Bianco, A; Serafini, M

    2016-01-01

    The analysis of the polar fraction of Melittis melissophyllum L. subsp. melissophyllum led to the identification of several iridoid glycosides: monomelittoside (1), melittoside (2), harpagide (3), acetyl-harpagide (4) and ajugoside (5). Compounds 3 and 4 are considered marker compounds for the genus and, as well as compounds 1, 2 and 5, were already evidenced in a previous study on the nominal species. It was noteworthy of the presence of allobetonicoside (6) which was never reported for this genus. The isolation of 6 is very relevant because of its allose residue on the structure. Allose has been often found in the species of the subfamily Lamioideae even if it mostly regarded flavonoids considered of chemotaxonomical relevance for some correlated genera of Lamiaceae. Same as allosyl-glycosidic flavonoids, the presence of allosyl-glycosidic iridoids may also be an additional chemosystematic evidence of botanical relationships among Lamiaceae species and genera. PMID:26131916

  19. A new iridoid derivative from the roots of Scrophularia buergeriana.

    PubMed

    Wu, Xi-Min; Zhang, Liu-Qiang; Chen, Xiao-Chong; Feng, Li; Xing, Wang-Xing; Li, Yi-Ming

    2014-07-01

    Phytochemical investigation of the roots of Scrophularia buergeriana Miq. (Scrophulariaceae), resulted in the isolation of a new iridoid derivative named as buergerinin (1). Its structure was elucidated as rel-(1R, 5R, 6R)-(2-oxa-bicyclo[3.3.0]oct-7-en-6, 7-diyl)dimethoxypropane based mainly on MS and 1D and 2D NMR spectroscopic analyses. PMID:25233633

  20. [Development and research advances of iridoids from Valeriana jatamansi and their bioactivity].

    PubMed

    Zhang, Ning-ning; Ding, Guang-zhi

    2015-05-01

    Valeriana jatamansi (syn. V. wallichii), a traditional Chinese medicine recorded in Chinese Pharmacopeia (1977 and 2010 edition), has been used for treatment of a variety of conditions including sleep problems, obesity, nervous disorders, epilepsy, insanity, snake poisoning, eye trouble, and skin diseases. Also, it was used as an important substitute for the European V. officinalis, whose root preparation, popularly known as valerian, has been employed as a mild sedative for a long time. In recent years, much attention has been draw to the iridoids, one of the major bioactive constituents of V. jatamansi, leading to the discovery of a series of new iridoids with anti-tumor and neuroprotective activities. Their action machnism also has been discussed. This paper summerized the iridoids and their bioactivities from V. jatamansi in recent years, which could provide basic foundation for development and research of V. jatamansi. PMID:26390643

  1. Pensteminoside, an unusual catalpol-type iridoid from Penstemon gentianoides HBK (Plantaginaceae).

    PubMed

    Domínguez, Mariana; Marín, J Camilo; Esquivel, Baldomero; Céspedes, Carlos L

    2007-07-01

    From the MeOH and ethyl acetate extracts of aerial parts of Penstemon gentianoides HBK (Plantaginaceae) an unusual iridoid of the catalpol-type, was isolated and characterized as pensteminoside: (8-O-trans-cinnamoyl, 6-hydroxy, 1-[beta-D-glucopyranoside-6'-O-((4''-hydroxy)-cinnamoyl)]-catalpol) was isolated, along with the known iridoids: plantarelanoside and globularisicin, the flavone: luteolin and diosmetin, as well the phenylpropanoids, verbascoside and martynoside. Their structures were established by 1D and 2D NMR spectroscopic analyses. PMID:17507063

  2. Iridoid and phenylpropanoid glycosides from Scrophularia ningpoensis Hemsl. and their ?-glucosidase inhibitory activities.

    PubMed

    Hua, Jing; Qi, Jin; Yu, Bo-Yang

    2014-03-01

    A new phenylpropanoid glycoside, designated Scrophuside (1) and two new iridoid glycosides, respectively named Ningposide I (2) and Ningposide II (3), along with twelve known (4-15) iridoid and phenylpropanoid glycosides were obtained from the roots of Scrophularia ningpoensis Hemsl. by various chromatographic techniques and their structures were established through chemical methods and spectroscopic analyses. Most of the obtained compounds have been screened for ?-Glucosidase inhibitory activity, in which compounds 4, 5, 7, 11, 12, 13, and 14 show significant activity. PMID:24321577

  3. Two new phenolic glucosides from Lagerstroemia speciosa.

    PubMed

    Choi, Janggyoo; Cho, Jae Youl; Choi, Soo Jung; Jeon, Heejin; Kim, Young Dong; Htwe, Khin Myo; Chin, Young Won; Lee, Woo Shin; Kim, Jinwoong; Yoon, Kee Dong

    2015-01-01

    Two new phenolic glucosides, 1-O-benzyl-6-O-E-caffeoyl-?-d-glucopyranoside and 1-O-(7S,8R)-guaiacylglycerol-(6-O-E-caffeoyl)-?-d-glucopyranoside, were isolated from the aerial parts of Lagerstroemia speciosa, along with ten known compounds. The structures of the isolated compounds were determined based on 1D- and 2D-NMR, Q-TOF MS and optical rotation spectroscopic data. All of the compounds showed moderate inhibitory activities against nitric oxide production in lipopolysaccharide-treated RAW264.7 cells, with IC50 values of 69.5-83.3 ?M. PMID:25764490

  4. Characterization of 10-hydroxygeraniol dehydrogenase from Catharanthus roseus reveals cascaded enzymatic activity in iridoid biosynthesis.

    PubMed

    Krithika, Ramakrishnan; Srivastava, Prabhakar Lal; Rani, Bajaj; Kolet, Swati P; Chopade, Manojkumar; Soniya, Mantri; Thulasiram, Hirekodathakallu V

    2015-01-01

    Catharanthus roseus [L.] is a major source of the monoterpene indole alkaloids (MIAs), which are of significant interest due to their therapeutic value. These molecules are formed through an intermediate, cis-trans-nepetalactol, a cyclized product of 10-oxogeranial. One of the key enzymes involved in the biosynthesis of MIAs is an NAD(P)(+) dependent oxidoreductase system, 10-hydroxygeraniol dehydrogenase (Cr10HGO), which catalyses the formation of 10-oxogeranial from 10-hydroxygeraniol via 10-oxogeraniol or 10-hydroxygeranial. This work describes the cloning and functional characterization of Cr10HGO from C. roseus and its role in the iridoid biosynthesis. Substrate specificity studies indicated that, Cr10HGO has good activity on substrates such as 10-hydroxygeraniol, 10-oxogeraniol or 10-hydroxygeranial over monohydroxy linear terpene derivatives. Further it was observed that incubation of 10-hydroxygeraniol with Cr10HGO and iridoid synthase (CrIDS) in the presence of NADP(+) yielded a major metabolite, which was characterized as (1R, 4aS, 7S, 7aR)-nepetalactol by comparing its retention time, mass fragmentation pattern, and co-injection studies with that of the synthesized compound. These results indicate that there is concerted activity of Cr10HGO with iridoid synthase in the formation of (1R, 4aS, 7S, 7aR)-nepetalactol, an important intermediate in iridoid biosynthesis. PMID:25651761

  5. Three new iridoid glycosides from the fruit of gardenia jasminoides var. radicans.

    PubMed

    Qin, Fang-Min; Meng, Ling-Jie; Zou, Hui-Liang; Zhou, Guang-Xiong

    2013-01-01

    Three new iridoid glycosides, 6?-O-trans-feruloylgenipin gentiobioside (1), 2'-O-trans-p-coumaroylgardoside (2), 2'-O-trans-feruloylgardoside (3), were isolated from the fruit of Gardenia jasminoides var. radicans MAKINO (Rubiaceae). The structures of these compounds were elucidated on the basis of MS, NMR spectra analysis, glycoside hydrolysis, and sugar derivatization coupled with HPLC analysis. PMID:24088698

  6. Steryl glucoside and acyl steryl glucoside analysis of Arabidopsis seeds by electrospray ionization tandem mass spectrometry

    PubMed Central

    Schrick, Kathrin; Shiva, Sunitha; Arpin, James C.; Delimont, Nicole; Isaac, Giorgis; Tamura, Pamela; Welti, Ruth

    2013-01-01

    Establishment of sensitive methods for the detection of cellular sterols and their derivatives is a critical step in developing comprehensive lipidomics technology. We demonstrate that electrospray ionization tandem (triple quadrupole) mass spectrometry (ESI-MS/MS) is an efficient method for monitoring steryl glucosides (SGs) and acyl steryl glucosides (ASGs). Comparison of analysis of SGs and ASGs by ESI-MS/MS with analysis by gas chromatography with flame ionization detection (GC-FID) shows that the two methods yield similar molar compositions. These data demonstrate that ESI-MS/MS response per molar amount of sterol conjugate is similar among various molecular species of SGs and ASGs. Application of ESI-MS/MS to seed samples from wild-type Arabidopsis and a mutant deficient in two UDP-glucose:sterol glucosyltransferases, UGT80A2 and UGT80B1, revealed new details on the composition of sitosteryl, campesteryl and stigmasteryl glucosides and ASGs. SGs were decreased by 86% in the ugt80A2,B1 double mutant, compared to wild-type, while ASGs were reduced 96%. The results indicate that these glucosyltransferases account for much of the accumulation of the sterol conjugates in wild-type Arabidopsis seeds. PMID:21830156

  7. Malonyl isoflavone glucosides are chiefly hydrolyzed and absorbed in the colon.

    PubMed

    Yonemoto-Yano, Hiroko; Maebuchi, Motohiro; Fukui, Kensuke; Tsuzaki, Shinichi; Takamatsu, Kiyoharu; Uehara, Mariko

    2014-03-12

    Malonyl isoflavone glucosides are water-soluble derivatives of soybean hypocotyls. This study compared the hydrolysis and absorption of malonyl isoflavone glucosides and nonmalonyl isoflavone glucosides in rats. Plasma concentrations of isoflavones were measured after oral administration of malonyl isoflavone glucosides or isoflavone glucosides. After fasting, the duodenum, jejunum, ileum, and colon were excised, and homogenates were prepared. The extent of hydrolysis of each glucoside by each intestinal homogenate was measured. Plasma levels of isoflavone aglycones, such as daidzein and glycitein, were higher in rats administered malonyl isoflavone glucosides than in those administered isoflavone glucosides. The area under the curve of daidzein in plasma of rats administered malonyl isoflavone glucosides was also significantly greater than that in those administered isoflavone glucosides. A transport experiment using Caco-2 cells suggested that degradation of malonyl glucosides to aglycones is necessary for intestinal absorption. Malonyl isoflavone glucosides were hydrolyzed only in the colon, whereas hydrolysis of isoflavone glucosides occurred in the jejunum, ileum, and colon. These results indicated more effective absorption of malonyl isoflavone glucosides than of nonmalonyl isoflavone glucosides. Moreover, effective absorption of malonyl isoflavone aglycones in the colon contributed to the significant increase in plasma isoflavone levels. PMID:24524651

  8. Identification of a Saccharomyces cerevisiae Glucosidase That Hydrolyzes Flavonoid Glucosides? †

    PubMed Central

    Schmidt, Sabine; Rainieri, Sandra; Witte, Simone; Matern, Ulrich; Martens, Stefan

    2011-01-01

    Baker's yeast (Saccharomyces cerevisiae) whole-cell bioconversions of naringenin 7-O-?-glucoside revealed considerable ?-glucosidase activity, which impairs any strategy to generate or modify flavonoid glucosides in yeast transformants. Up to 10 putative glycoside hydrolases annotated in the S. cerevisiae genome database were overexpressed with His tags in yeast cells. Examination of these recombinant, partially purified polypeptides for hydrolytic activity with synthetic chromogenic ?- or ?-glucosides identified three efficient ?-glucosidases (EXG1, SPR1, and YIR007W), which were further assayed with natural flavonoid ?-glucoside substrates and product verification by thin-layer chromatography (TLC) or high-performance liquid chromatography (HPLC). Preferential hydrolysis of 7- or 4?-O-glucosides of isoflavones, flavonols, flavones, and flavanones was observed in vitro with all three glucosidases, while anthocyanins were also accepted as substrates. The glucosidase activities of EXG1 and SPR1 were completely abolished by Val168Tyr mutation, which confirmed the relevance of this residue, as reported for other glucosidases. Most importantly, biotransformation experiments with knockout yeast strains revealed that only EXG1 knockout strains lost the capability to hydrolyze flavonoid glucosides. PMID:21216897

  9. Serruloside and Serrulatoside, two New Iridoid Glycosides from Penstemon serrulatus1.

    PubMed

    Junior, P

    1984-10-01

    From leaves of PENSTEMON SERRULATUS Menz. two new iridoid glycosides have been isolated. Both glycosides have the same aglycon part, but differ in their carbohydrate moieties. The structure of serru-loside (penstemidaglucon-11- O-beta- D-ribohexos -3-uloside) and serrulatoside (penstemidaglucon-ll- O-beta-4'-desoxyaltropyranosido-6'- O-beta- D-glucopyranoside) was established by spectroscopic methods (mainly (1)H- and (13)C-NMR) and comparison with known compounds. PMID:17340343

  10. Iridoid glycosides isolated from Scrophularia dentata Royle ex Benth. and their anti-inflammatory activity.

    PubMed

    Zhang, Liuqiang; Zhu, Tiantian; Qian, Fei; Xu, Jinwen; Dorje, Gaawe; Zhao, Zhili; Guo, Fujiang; Li, Yiming

    2014-10-01

    Scrodentosides A-E (1-5), five new acylated iridoid glycosides, together with 19 known ones, were isolated from the whole plant of Scrophularia dentata Royle ex Benth. The structures of these isolated glycosides were elucidated by spectroscopic methods. Bioassay showed that compounds 7 and 11 had significant inhibitory effect against NF-?B activation with IC50 value of 43.7 ?M and 1.02 ?M respectively. PMID:25016952

  11. Iridoids and Flavonoids of Four Siberian Gentians: Chemical Profile and Gastric Stimulatory Effect.

    PubMed

    Olennikov, Daniil N; Kashchenko, Nina I; Chirikova, Nadezhda K; Tankhaeva, Larisa M

    2015-01-01

    Some Gentiana species have been used by the nomadic people of Siberia as bitter teas or appetizers to eliminate digestive disorders (dyspepsia, heartburn, nausea, etc.). We studied the most frequently used gentians: Gentiana algida, G. decumbens, G. macrophylla and G. triflora. The aim of the present study was to evaluate the phytochemical features and gastrostimulatnt activity of these four gentian herbs. Five iridoids, seven flavones and mangiferin were detected in gentian herbs after analysis by microcolumn-RP-HPLC-UV-ESI-MS. A componential phytochemical profile of the G. decumbens herb is presented for the first time, as well as information about distinct phytochemicals found in gentian herbs. HPLC quantification of the specific compounds of gentian herbs demonstrated the high content of iridoids (24.73-73.53 mg/g) and flavonoids (12.92-78.14 mg/g). The results of biological activity evaluation of four gentian decoctions demonstrated their good ability to stimulate acid-, enzyme- and mucin-forming functions of the stomach attributed to mostly by iridoids and flavonoids. In general, it can be claimed that the gentian decoctions can be used as effective and safe appetizers and are also a good source of biologically active agents. PMID:26506331

  12. Evaluation of dihydroquercetin-3-O-glucoside from Malbec grapes as copigment of malvidin-3-O-glucoside.

    PubMed

    Fanzone, Martín; González-Manzano, Susana; Pérez-Alonso, Joaquín; Escribano-Bailón, María Teresa; Jofré, Viviana; Assof, Mariela; Santos-Buelga, Celestino

    2015-05-15

    Malbec is a wine grape variety of great phenolic potential characterized for its high levels of anthocyanins and dihydroflavonols. To evaluate the possible implication of dihydroflavonols in the expression of red wine color through reactions of copigmentation or condensation, assays were carried out in wine model systems with different malvidin-3-O-glucoside:dihydroquercetin-3-O-glucoside molar ratios. The addition of increasing levels of dihydroquercetin-3-O-glucoside to a constant malvidin-3-O-glucoside concentration resulted in a hyperchromic effect associated with a darkening of the anthocyanin solutions, greater quantity of color and visual saturation, perceptible to the human eye. Copigmentation and thermodynamic measurements showed that dihydroquercetin-3-O-glucoside can act as an anthocyanin copigment, similar to other usual wine components like flavanols or phenolic acids, although apparently less efficient than flavonols. The high levels of dihydroflavonols existing in Malbec wines in relation to other non-anthocyanin phenolics should make this family of compounds particularly important to explain the color expression in Malbec young red wines. PMID:25577066

  13. Expression of cholesteryl glucoside by heat shock in human fibroblasts

    PubMed Central

    Kunimoto, Shohko; Kobayashi, Tetsuyuki; Kobayashi, Susumu; Murakami-Murofushi, Kimiko

    2000-01-01

    ABSTRACT We investigated the heat-induced alteration of glycolipids in human cultured cells, TIG-3 fibroblasts, to show the expression of steryl glucoside by heat shock. A glycolipid band was detected on a thin-layer chromatography plate in lipid extracts from TIG-3 cells exposed to high temperature (42°C) for 15 and 30 minutes, while it was hardly detectable without heat shock. Both cholesterol and glucose were almost exclusively detected by gas liquid chromatography as degradation products of the lipid. The structure of the lipid molecule was elucidated by electrospray mass spectrometry to be a cholesteryl glucoside. This is the first report to show the occurrence of a steryl glucoside in mammalian cells, and this substance is considered to have a significant role in heat shock responses in mammalian cells. PMID:10701833

  14. 21 CFR 573.660 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 6 2013-04-01 2013-04-01 false Methyl glucoside-coconut oil ester. 573.660 Section 573.660 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES... ANIMALS Food Additive Listing § 573.660 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut...

  15. 21 CFR 178.3600 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 3 2014-04-01 2014-04-01 false Methyl glucoside-coconut oil ester. 178.3600 Section 178.3600 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES... Production Aids § 178.3600 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester...

  16. 21 CFR 178.3600 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 3 2012-04-01 2012-04-01 false Methyl glucoside-coconut oil ester. 178.3600... SANITIZERS Certain Adjuvants and Production Aids § 178.3600 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester identified in § 172.816(a) of this chapter may be safely used as a...

  17. 21 CFR 573.660 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 6 2014-04-01 2014-04-01 false Methyl glucoside-coconut oil ester. 573.660 Section 573.660 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES... ANIMALS Food Additive Listing § 573.660 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut...

  18. 21 CFR 573.660 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 6 2012-04-01 2012-04-01 false Methyl glucoside-coconut oil ester. 573.660 Section 573.660 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES... ANIMALS Food Additive Listing § 573.660 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut...

  19. 21 CFR 178.3600 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 3 2013-04-01 2013-04-01 false Methyl glucoside-coconut oil ester. 178.3600... SANITIZERS Certain Adjuvants and Production Aids § 178.3600 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester identified in § 172.816(a) of this chapter may be safely used as a...

  20. 21 CFR 573.660 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... (CONTINUED) ANIMAL DRUGS, FEEDS, AND RELATED PRODUCTS FOOD ADDITIVES PERMITTED IN FEED AND DRINKING WATER OF ANIMALS Food Additive Listing § 573.660 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil... 21 Food and Drugs 6 2010-04-01 2010-04-01 false Methyl glucoside-coconut oil ester....

  1. 21 CFR 573.660 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... (CONTINUED) ANIMAL DRUGS, FEEDS, AND RELATED PRODUCTS FOOD ADDITIVES PERMITTED IN FEED AND DRINKING WATER OF ANIMALS Food Additive Listing § 573.660 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil... 21 Food and Drugs 6 2011-04-01 2011-04-01 false Methyl glucoside-coconut oil ester....

  2. 21 CFR 178.3600 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 2011-04-01 false Methyl glucoside-coconut oil ester. 178.3600 Section 178.3600...Production Aids § 178.3600 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester identified in § 172.816(a)...

  3. 21 CFR 178.3600 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 2009-04-01 true Methyl glucoside-coconut oil ester. 178.3600 Section 178.3600...Production Aids § 178.3600 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester identified in § 172.816(a)...

  4. 21 CFR 573.660 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 2013-04-01 false Methyl glucoside-coconut oil ester. 573.660 Section 573.660...Additive Listing § 573.660 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used in accordance...

  5. 21 CFR 178.3600 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 2014-04-01 false Methyl glucoside-coconut oil ester. 178.3600 Section 178.3600...Production Aids § 178.3600 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester identified in § 172.816(a)...

  6. 21 CFR 573.660 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 2010-04-01 false Methyl glucoside-coconut oil ester. 573.660 Section 573.660...Additive Listing § 573.660 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used in accordance...

  7. 21 CFR 172.816 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 2009-04-01 true Methyl glucoside-coconut oil ester. 172.816 Section 172.816...Additives § 172.816 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used in food in...

  8. 21 CFR 178.3600 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 2012-04-01 false Methyl glucoside-coconut oil ester. 178.3600 Section 178.3600...Production Aids § 178.3600 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester identified in § 172.816(a)...

  9. 21 CFR 172.816 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 2011-04-01 false Methyl glucoside-coconut oil ester. 172.816 Section 172.816...Additives § 172.816 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used in food in...

  10. 21 CFR 172.816 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 2012-04-01 false Methyl glucoside-coconut oil ester. 172.816 Section 172.816...Additives § 172.816 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used in food in...

  11. 21 CFR 573.660 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 2014-04-01 false Methyl glucoside-coconut oil ester. 573.660 Section 573.660...Additive Listing § 573.660 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used in accordance...

  12. 21 CFR 178.3600 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 2013-04-01 false Methyl glucoside-coconut oil ester. 178.3600 Section 178.3600...Production Aids § 178.3600 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester identified in § 172.816(a)...

  13. 21 CFR 172.816 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 2013-04-01 false Methyl glucoside-coconut oil ester. 172.816 Section 172.816...Additives § 172.816 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used in food in...

  14. 21 CFR 172.816 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 2014-04-01 false Methyl glucoside-coconut oil ester. 172.816 Section 172.816...Additives § 172.816 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used in food in...

  15. 21 CFR 573.660 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 2012-04-01 false Methyl glucoside-coconut oil ester. 573.660 Section 573.660...Additive Listing § 573.660 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used in accordance...

  16. 21 CFR 573.660 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 2011-04-01 false Methyl glucoside-coconut oil ester. 573.660 Section 573.660...Additive Listing § 573.660 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used in accordance...

  17. 21 CFR 172.816 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Methyl glucoside-coconut oil ester. 172.816 Section... HUMAN CONSUMPTION Multipurpose Additives § 172.816 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used in food in accordance with the following conditions: (a) It is...

  18. Sesquiterpenoid and phenolic glucoside gallates from Lagerstroemia balansae.

    PubMed

    Zhou, Yong; Chen, Hu-biao; Wang, Bin; Liang, Hong; Zhao, Yu-ying; Zhang, Qing-ying

    2011-11-01

    Three new compounds, including a sesquiterpenoid glucoside gallate, 2 Z,4 E,1' R,2' S,4' R,6' S-dihydrophaseic acid 4'-O-(6''-O-galloyl)-?-D-glucopyranoside (1), two new phenolic glucoside gallates, 4-hydroxy-3,5-dimethoxybenzoic acid 4-O-(6'-O-galloyl)-?-D-glucopyranoside (2) and 3,4-dimethoxyphenol 1-O-(6'-O-galloyl)-?-D-glucopyranoside (3), together with eight known compounds (4-11), have been isolated from the stems of Lagerstroemia balansae. Their structures were elucidated on the basis of chemical and spectroscopic evidences. PMID:21800279

  19. Studies on the constituents of Syringa species. X. Five new iridoid glycosides from the leaves of Syringa reticulata (Blume) Hara.

    PubMed

    Machida, Koichi; Kaneko, Atsuko; Hosogai, Tomokazu; Kakuda, Rie; Yaoita, Yasunori; Kikuchi, Masao

    2002-04-01

    Five new iridoid glycosides, (8Z)-ligstroside (1), (8Z)-nüzhenide (3), 6'-O-alpha-D-glucopyranosylsyringopicroside (4), 3'-O-beta-D-glucopyranosylsyringopicroside (5) and 4'-O-beta-D-glucopyranosylsyringopicroside (6) were isolated, together with a known one, (8E)-nüzhenide (2), from the leaves of Syringa reticulata. Their structures were established on the basis of chemical and spectral data. Compounds 1 and 3 are the first findings of a (8Z)-oleoside-type secoiridoid. Compound 4 is the first naturally occurring iridoid di-glycoside having an isomaltose. PMID:11963996

  20. C??-polyacetylene glucosides from Codonopsis pilosula.

    PubMed

    Jiang, Yue-Ping; Liu, Yu-Feng; Guo, Qing-Lan; Jiang, Zhi-Bo; Xu, Cheng-Bo; Zhu, Cheng-Gen; Yang, Yong-Chun; Lin, Sheng; Shi, Jian-Gong

    2015-01-01

    Seven new C14-polyacetylene glucosides codonopilodiynosides A-G (1-7) were isolated from an aqueous extract of the Codonopsis pilosula roots. Their structures were determined by spectroscopic and chemical methods as (-)-(5S,6E,12E)-tetradeca-6,12-dien-8,10-diyn-1,5,14-triol 5-O-?-D-glucopyranoside (1), (-)-(5S,6E,12E)-tetradeca-6,12-dien-8,10-diyn-1,5,14-triol 5-O-?-D-glucopyranosyl-(1? ? 2')-?-D-glucopyranoside (2), (-)-(5S,6E,12E)-tetradeca-6,12-dien-8,10-diyn-1,5,14-triol 5,14-di-O-?-D-glucopyranoside (3), (-)-(5S,6E)-tetradeca-6-en-8,10-diyn-1,5,14-triol 5-O-?-D-glucopyranoside (4), (-)-(5S,6E,12E)-tetradeca-6,12-dien-8,10-diyn-1,5-diol 5-O-?-D-glucopyranosyl-(1? ? 2')-?-D-glucopyranoside (5), (-)-(6S,4E,12E)-tetradeca-4,12-dien-8,10-diyn-1,6-diol 6-O-?-D-glucopyranosyl-(1? ? 2')-?-D-glucopyranoside (6), and (-)-(5S,6E)-tetradeca-6-en-1,5-epoxy-8,10-diyn-14-ol 14-O-?-D-glucopyranosyl-(1? ? 2')-?-D-glucopyranoside (7), respectively. The absolute configurations of 1-7 were assigned by enzymatic hydrolysis followed by isolation of glucose and aglycones (1a and 4a-7a), and subsequent comparison of specific rotation, TLC, and (1)H NMR data of the glucose with an authentic sugar sample and application of modified Mosher's method based on the MPA determination rule of ??(RS) values for 1a and 4a, and ??(S) values for 6a. The configuration of 7 was assigned by electronic circular dichroism calculations based on the quantum-mechanical time-dependent density functional theory. PMID:26009940

  1. Iridoid synthase activity is common among the plant progesterone 5?-reductase family.

    PubMed

    Munkert, Jennifer; Pollier, Jacob; Miettinen, Karel; Van Moerkercke, Alex; Payne, Richard; Müller-Uri, Frieder; Burlat, Vincent; O'Connor, Sarah E; Memelink, Johan; Kreis, Wolfgang; Goossens, Alain

    2015-01-01

    Catharanthus roseus, the Madagascar periwinkle, synthesizes bioactive monoterpenoid indole alkaloids, including the anti-cancer drugs vinblastine and vincristine. The monoterpenoid branch of the alkaloid pathway leads to the secoiridoid secologanin and involves the enzyme iridoid synthase (IS), a member of the progesterone 5?-reductase (P5?R) family. IS reduces 8-oxogeranial to iridodial. Through transcriptome mining, we show that IS belongs to a family of six C. roseus P5?R genes. Characterization of recombinant CrP5?R proteins demonstrates that all but CrP5?R3 can reduce progesterone and thus can be classified as P5?Rs. Three of them, namely CrP5?R1, CrP5?R2, and CrP5?R4, can also reduce 8-oxogeranial, pointing to a possible redundancy with IS (corresponding to CrP5?R5) in secoiridoid synthesis. In-depth functional analysis by subcellular protein localization, gene expression analysis, in situ hybridization, and virus-induced gene silencing indicate that besides IS, CrP5?R4 may also participate in secoiridoid biosynthesis. We cloned a set of P5?R genes from angiosperm plant species not known to produce iridoids and demonstrate that the corresponding recombinant proteins are also capable of using 8-oxogeranial as a substrate. This suggests that IS activity is intrinsic to angiosperm P5?R proteins and has evolved early during evolution. PMID:25578278

  2. Application of Cornelian Cherry Iridoid-Polyphenolic Fraction and Loganic Acid to Reduce Intraocular Pressure

    PubMed Central

    Szumny, Dorota; Soza?ski, Tomasz; Kucharska, Alicja Z.; Dziewiszek, Wojciech; Piórecki, Narcyz; Magdalan, Jan; Chlebda-Sieragowska, Ewa; Kupczynski, Robert; Szel?g, Adam; Szumny, Antoni

    2015-01-01

    One of the most common diseases of old age in modern societies is glaucoma. It is strongly connected with increased intraocular pressure (IOP) and could permanently damage vision in the affected eye. As there are only a limited number of chemical compounds that can decrease IOP as well as blood flow in eye vessels, the up-to-date investigation of new molecules is important. The chemical composition of the dried Cornelian cherry (Cornus mas L.) polar, iridoid-polyphenol-rich fraction was investigated. Loganic acid (50%) and pelargonidin-3-galactoside (7%) were found as the main components. Among the other constituents, iridoid compound cornuside and the anthocyans cyanidin 3-O-galactoside, cyanidin 3-O-robinobioside, and pelargonidin 3-O-robinobioside were quantified in the fraction. In an animal model (New Zealand rabbits), the influence of loganic acid and the polyphenolic fraction isolated from Cornelian cherry fruit was investigated. We found a strong IOP-hypotensive effect for a 0.7% solution of loganic acid, which could be compared with the widely ophthalmologically used timolol. About a 25% decrease in IOP was observed within the first 3 hours of use. PMID:26124854

  3. A New Benzofuran Glucoside from Ficus Tikoua Bur

    PubMed Central

    Wei, Shao-Peng; Luan, Jie-Yu; Lu, Li-Na; Wu, Wen-Jun; Ji, Zhi-Qin

    2011-01-01

    From the water-soluble portion of the methanol extract of stems of Ficus tikoua Bur., a new benzofuran glucoside, named 6-carboxyethyl-5-hydroxybenzofuran 5-O-?-d-glucopyranoside (1), together with one known benzofuran glucoside (2) were isolated. Their structures were elucidated by 1D and 2D (1H-1H COSY, HMQC, and HMBC) NMR spectroscopy and HRMS techniques. The antioxidant activities of the isolated compounds were assayed based on the scavenging activities of DPPH free radical. Compounds 1 and 2 exhibited moderate antioxidant activities, and the IC50 values were 242.8 ?g·mL?1 and 324.9 ?g·mL?1, respectively. PMID:21954336

  4. Cyanogenic glucosides in grapevine: polymorphism, identification and developmental patterns.

    PubMed

    Franks, T K; Hayasaka, Y; Choimes, S; van Heeswijck, R

    2005-01-01

    Twelve grapevine (Vitis vinifera L.) cultivars were surveyed for 'cyanide potential' (i.e. the total cyanide measured in beta-glucosidase-treated crude, boiled tissue extract) in mature leaves. Two related cultivars (Carignan and Ruby Cabernet) had mean cyanide potential (equivalent to 110 mgHCNkg-1fr.wt) ca. 25-fold greater than that of the other 10 cultivars, and so the trait is polymorphic in the species. In boiled leaf extracts of Carignan and Ruby Cabernet, free cyanide constituted a negligible fraction of the total cyanide potential because beta-glucosidase treatment was required to liberate the major cyanide fraction - which is therefore bound in glucosylated cyanogenic compound(s) (or cyanogenic glucosides). In addition, cyanide was liberated from ground leaf tissue of Ruby Cabernet but not Sultana (a cultivar with low cyanide potential). Hence, the high cyanide potential in Ruby Cabernet leaves is coupled with endogenous beta-glucosidase(s) activity and this cultivar may be considered 'cyanogenic'. A method was developed to detect and identify cyanogenic glucosides using liquid chromatography combined with tandem mass spectrometry (LC-MS/MS). Two putative cyanogenic glucosides were found in extracts from leaves of Carignan and Ruby Cabernet and were identified as the epimers prunasin and sambunigrin. Cyanide potential measured at three times over the growing season in young and mature leaves, petioles, tendrils, flowers, berries, seeds and roots of Ruby Cabernet was substantially higher in the leaves compared with all other tissues. This characterisation of cyanogenic glucoside accumulation in grapevine provides a basis for gauging the involvement of the trait in interactions of the species with its pests and pathogens. PMID:15652573

  5. The bifurcation of the cyanogenic glucoside and glucosinolate biosynthetic pathways.

    PubMed

    Clausen, Mette; Kannangara, Rubini M; Olsen, Carl E; Blomstedt, Cecilia K; Gleadow, Roslyn M; Jørgensen, Kirsten; Bak, Søren; Motawie, Mohammed S; Møller, Birger Lindberg

    2015-11-01

    The biosynthetic pathway for the cyanogenic glucoside dhurrin in sorghum has previously been shown to involve the sequential production of (E)- and (Z)-p-hydroxyphenylacetaldoxime. In this study we used microsomes prepared from wild-type and mutant sorghum or transiently transformed Nicotiana benthamiana to demonstrate that CYP79A1 catalyzes conversion of tyrosine to (E)-p-hydroxyphenylacetaldoxime whereas CYP71E1 catalyzes conversion of (E)-p-hydroxyphenylacetaldoxime into the corresponding geometrical Z-isomer as required for its dehydration into a nitrile, the next intermediate in cyanogenic glucoside synthesis. Glucosinolate biosynthesis is also initiated by the action of a CYP79 family enzyme, but the next enzyme involved belongs to the CYP83 family. We demonstrate that CYP83B1 from Arabidopsis thaliana cannot convert the (E)-p-hydroxyphenylacetaldoxime to the (Z)-isomer, which blocks the route towards cyanogenic glucoside synthesis. Instead CYP83B1 catalyzes the conversion of the (E)-p-hydroxyphenylacetaldoxime into an S-alkyl-thiohydroximate with retention of the configuration of the E-oxime intermediate in the final glucosinolate core structure. Numerous microbial plant pathogens are able to detoxify Z-oximes but not E-oximes. The CYP79-derived E-oximes may play an important role in plant defense. PMID:26361733

  6. Enzymatic Biosynthesis of Novel Resveratrol Glucoside and Glycoside Derivatives

    PubMed Central

    Pandey, Ramesh Prasad; Parajuli, Prakash; Shin, Ju Yong; Lee, Jisun; Lee, Seul; Hong, Young-Soo; Park, Yong Il; Kim, Joong Su

    2014-01-01

    A UDP glucosyltransferase from Bacillus licheniformis was overexpressed, purified, and incubated with nucleotide diphosphate (NDP) d- and l-sugars to produce glucose, galactose, 2-deoxyglucose, viosamine, rhamnose, and fucose sugar-conjugated resveratrol glycosides. Significantly higher (90%) bioconversion of resveratrol was achieved with ?-d-glucose as the sugar donor to produce four different glucosides of resveratrol: resveratrol 3-O-?-d-glucoside, resveratrol 4?-O-?-d-glucoside, resveratrol 3,5-O-?-d-diglucoside, and resveratrol 3,5,4?-O-?-d-triglucoside. The conversion rates and numbers of products formed were found to vary with the other NDP sugar donors. Resveratrol 3-O-?-d-2-deoxyglucoside and resveratrol 3,5-O-?-d-di-2-deoxyglucoside were found to be produced using TDP-2-deoxyglucose as a donor; however, the monoglycosides resveratrol 4?-O-?-d-galactoside, resveratrol 4?-O-?-d-viosaminoside, resveratrol 3-O-?-l-rhamnoside, and resveratrol 3-O-?-l-fucoside were produced from the respective sugar donors. Altogether, 10 diverse glycoside derivatives of the medically important resveratrol were generated, demonstrating the capacity of YjiC to produce structurally diverse resveratrol glycosides. PMID:25239890

  7. Antibacterial and Antiproliferative Activities of Plumericin, an Iridoid Isolated from Momordica charantia Vine

    PubMed Central

    Saengsai, Jutamas; Kongtunjanphuk, Sumonthip; Yoswatthana, Nuttawan; Kummalue, Tanawan

    2015-01-01

    Plumericin, an iridoid lactone, was isolated with relatively high yield from Momordica charantia vine using the supercritical fluid extraction (SFE) and the separation box (Sepbox) comprising dual combination of high-performance liquid chromatography and solid phase extraction. This compound showed antibacterial activity against Enterococcus faecalis and Bacillus subtilis with minimum inhibitory concentration (MIC) values better than cloxacillin. Plumericin potently inhibited proliferation of two leukemic cancer cell lines: they were acute and chronic leukemic cancer cell lines, NB4 and K562, with the effective doses (ED50) of 4.35 ± 0.21 and 5.58 ± 0.35??g/mL, respectively. In addition, the mechanism of growth inhibition in both cell lines was induced by apoptosis, together with G2/M arrest in K562 cells. PMID:25945113

  8. New anti-trypanosomal active tetracyclic iridoid isolated from Morinda lucida Benth.

    PubMed

    Suzuki, Mitsuko; Tung, Nguyen Huu; Kwofie, Kofi D; Adegle, Richard; Amoa-Bosompem, Michael; Sakyiamah, Maxwell; Ayertey, Frederick; Owusu, Kofi Baffour-Awuah; Tuffour, Isaac; Atchoglo, Philip; Frempong, Kwadwo Kyereme; Anyan, William K; Uto, Takuhiro; Morinaga, Osamu; Yamashita, Taizo; Aboagye, Frederic; Appiah, Alfred Ampomah; Appiah-Opong, Regina; Nyarko, Alexander K; Yamaoka, Shoji; Yamaguchi, Yasuchika; Edoh, Dominic; Koram, Kwadwo; Ohta, Nobuo; Boakye, Daniel A; Ayi, Irene; Shoyama, Yukihiro

    2015-08-01

    Human African trypanosomiasis (HAT), commonly known as sleeping sickness has remained a serious health problem in many African countries with thousands of new infected cases annually. Chemotherapy, which is the main form of control against HAT has been characterized lately by the viewpoints of toxicity and drug resistance issues. Recently, there have been a lot of emphases on the use of medicinal plants world-wide. Morinda lucida Benth. is one of the most popular medicinal plants widely distributed in Africa and several groups have reported on its anti-protozoa activities. In this study, we have isolated one novel tetracyclic iridoid, named as molucidin, from the CHCl3 fraction of the M. lucida leaves by bioassay-guided fractionation and purification. Molucidin was structurally elucidated by (1)H and (13)C NMR including HMQC, HMBC, H-H COSY and NOESY resulting in tetracyclic iridoid skeleton, and its absolute configuration was determined. We have further demonstrated that molucidin presented a strong anti-trypanosomal activity, indicating an IC50 value of 1.27 ?M. The cytotoxicity study using human normal and cancer cell lines indicated that molucidin exhibited selectivity index (SI) against two normal fibroblasts greater than 4.73. Furthermore, structure-activity relationship (SAR) study was undertaken with molucidin and oregonin, which is identical to anti-trypanosomal active components of Alnus japonica. Overlapping analysis of the lowest energy conformation of molucidin with oregonin suggested a certain similarities of aromatic rings of both oregonin and molucidin. These results contribute to the future drug design studies for HAT. PMID:26048790

  9. Study of chemical composition and antimicrobial activity of leaves and roots of Scrophularia ningpoensis.

    PubMed

    Li, Jing; Huang, Xiaoyan; Du, Xianjie; Sun, Wenji; Zhang, Yongmin

    2009-01-01

    Two saponins: scrokoelziside A (1), scrokoelziside B (2), one iridoid glycoside, eurostoside (3), and two flavonoids: nepitrin (4) and homoplantaginin (5), were isolated from the leaves of Scrophularia ningpoensis for the first time. Moreover, eight known compounds: cane sugar (6), harpagide (7), aucubin (8), 6-O-methylcatalpol (9), harpagoside (10), angoroside C (11), beta-sitosterol (12) and beta-sitosterol glucoside (13) were isolated from the roots of S. ningpoensis. Furthermore, the antimicrobial activity of the extracts of the leaves of S. ningpoensis and the 10 compounds (1, 2, 3, 4, 5, 7, 8, 9, 10, 11) was studied in vitro against eight reference strains of bacteria by using the disc-diffusion method and micro-well dilution assay. The extracts of leaves and scrokoelziside A are effective against beta-haemolytic streptococci but had no effect against other strains. The extract of roots and other compounds showed no activity against all bacterial strains at the test concentration. PMID:19418360

  10. Guaiane-type sesquiterpenoid glucosides from Gardenia jasminoides Ellis.

    PubMed

    Yu, Yang; Gao, Hao; Dai, Yi; Xiao, Gao-Keng; Zhu, Hua-Jie; Yao, Xin-Sheng

    2011-05-01

    Two new guaiane-type sesquiterpenoid glucosides (1 and 2) were isolated from the fruit of Gardenia jasminoides Ellis. Their structures were elucidated to be (1R,7R,10S)-11-O-?-D-glucopyranosyl-4-guaien-3-one (1) and (1R,7R,10S)-7-hydroxy-11-O-?-D-glucopyranosyl-4-guaien-3-one (2) by one- and two-dimensional NMR techniques ((1)H NMR, (13)C NMR, HSQC, HMBC and NOESY), MS, CD spectrometry and chemical methods. PMID:21491483

  11. Citrus limonin glucoside supplementation decreased biomarkers of liver disease in overweight human subjects

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Orange juice and mixtures of citrus limonoid glucosides isolated from orange juice or its byproducts demonstrated health benefits in human and animal studies. However, the risks and benefits of purified limonin glucoside (LG) in humans are unknown. Aim of this study was to determine the safety and m...

  12. Colorimetric Method for the Estimation of Total Limonoid Aglycones and Glucoside Contents in Citrus Juices

    Technology Transfer Automated Retrieval System (TEKTRAN)

    A method for estimating the total limonoid aglycone and glucoside concentrations in Citrus samples in terms of limonin and limonin glucoside equivalents is presented. The method consists of extraction followed by colorimetric quantification. The colorimetric quantification was based on the formatio...

  13. Anomericity of T-2 toxin-glucoside: masked mycotoxin in cereal crops.

    PubMed

    McCormick, Susan P; Kato, Takayuki; Maragos, Chris M; Busman, Mark; Lattanzio, Veronica M T; Galaverna, Gianni; Dall-Asta, Chiara; Crich, David; Price, Neil P J; Kurtzman, Cletus P

    2015-01-21

    T-2 toxin is a trichothecene mycotoxin produced when Fusarium fungi infect grains, especially oats and wheat. Ingestion of T-2 toxin contaminated grain can cause diarrhea, hemorrhaging, and feed refusal in livestock. Cereal crops infected with mycotoxin-producing fungi form toxin glycosides, sometimes called masked mycotoxins, which are a potential food safety concern because they are not detectable by standard approaches and may be converted back to the parent toxin during digestion or food processing. The work reported here addresses four aspects of T-2 toxin-glucosides: phytotoxicity, stability after ingestion, antibody detection, and the anomericity of the naturally occurring T-2 toxin-glucoside found in cereal plants. T-2 toxin-?-glucoside was chemically synthesized and compared to T-2 toxin-?-glucoside prepared with Blastobotrys muscicola cultures and the T-2 toxin-glucoside found in naturally contaminated oats and wheat. The anomeric forms were separated chromatographically and differ in both NMR and mass spectrometry. Both anomers were significantly degraded to T-2 toxin and HT-2 toxin under conditions that mimic human digestion, but with different kinetics and metabolic end products. The naturally occurring T-2 toxin-glucoside from plants was found to be identical to T-2 toxin-?-glucoside prepared with B. muscicola. An antibody test for the detection of T-2 toxin was not effective for the detection of T-2 toxin-?-glucoside. This anomer was produced in sufficient quantity to assess its animal toxicity. PMID:25520274

  14. Enzymatic Synthesis of Apigenin Glucosides by Glucosyltransferase (YjiC) from Bacillus licheniformis DSM 13

    PubMed Central

    Gurung, Rit Bahadur; Kim, Eun-Hee; Oh, Tae-Jin; Sohng, Jae Kyung

    2013-01-01

    Apigenin, a member of the flavone subclass of flavonoids, has long been considered to have various biological activities. Its glucosides, in particular, have been reported to have higher water solubility, increased chemical stability, and enhanced biological activities. Here, the synthesis of apigenin glucosides by the in vitro glucosylation reaction was successfully performed using a UDP-glucosyltransferase YjiC, from Bacillus licheniformis DSM 13. The glucosylation has been confirmed at the phenolic groups of C-4? and C-7 positions ensuing apigenin 4?-O-glucoside, apigenin 7-O-glucoside and apigenin 4?,7-O-diglucoside as the products leaving the C-5 position unglucosylated. The position of glucosylation and the chemical structures of glucosides were elucidated by liquid chromatography/mass spectroscopy and nuclear magnetic resonance spectroscopy. The parameters such as pH, UDP glucose concentration and time of incubation were also analyzed during this study. PMID:24170092

  15. Rapid quantification of iridoid glycosides analogues in the formulated Chinese medicine Longdan Xiegan Decoction using high-performance liquid chromatography coupled with mass spectrometry [corrected].

    PubMed

    Yang, Li; Wang, Yun; Wang, Longxing; Xiao, Hongbin; Wang, Zhengtao; Hu, Zhibi

    2009-03-13

    Longdan Xiegan Decoction (LXD) is a formulated preparation composed of 10 ingredient herbs, with iridoids as the main bioactive components. In this study, a rapid, simple and reliable method of simultaneous determination of four iridoid glycosides in LXD using high-performance liquid chromatography (HPLC) coupled with electrospray ionization mass spectrometry (MS) was first developed and validated. The four iridoid glycosides references were isolated from LXD extract and purified using a preparative HPLC chromatography. The sample preparation for quantification comprised of a simple ultrasonic extraction and the satisfactory chromatographic separation of the four structurally similar iridoid glycosides was effected in less than three minutes on a CAPCELL PAK C(18) MGII column (3 microm, 100 mm x 2.0 mm), using an elution system of 10% methanol and their concentrations in different batches of LXD and ingredient herbs were simultaneously determined by HPLC-MS/MS using a multiple reaction monitoring (MRM) mode. The method was validated with respect to the overall intra- and inter-day variation (RSD less than 8%) and the limits of quantification for the four iridoid glycosides were 35, 20, 37 and 33 ng/mL, respectively. PMID:18656203

  16. Cyanogenic allosides and glucosides from Passiflora edulis and Carica papaya.

    PubMed

    Seigler, David S; Pauli, Guido F; Nahrstedt, Adolf; Leen, Rosemary

    2002-08-01

    Leaf and stem material of Passiflora edulis (Passifloraceae) contains the new cyanogenic glycosides (2R)-beta-D-allopyranosyloxy-2-phenylacetonitrile (1a) and (2S)-beta-D-allopyranosyloxy-2-phenylacetonitrile (1b), along with smaller amounts of (2R)-prunasin (2a), sambunigrin (2b), and the alloside of benzyl alcohol (4); the major cyanogens of the fruits are (2R)-prunasin (2a) and (2S)-sambunigrin (2b). The major cyanogenic glycoside of Carica papaya (Caricaceae) is 2a; only small amounts of 2b also are present. We were not able to confirm the presence of a cyclopentenoid cyanogenic glycoside, tetraphyllin B, in Carica papaya leaf and stem materials. In detailed 1H NMR studies of 1a/b and 2a/b, differences in higher order effects in glucosides and allosides proved to be valuable for assignment of structures in this series. The diagnostic chemical shifts of cyanogenic methine and anomeric protons in 1a/b are sensitive to anisotropic environmental effects. The assignment of C-2 stereochemistry of 1a/b was made in analogy to previous assignments in the glucoside series and was supported by GLC analysis of the TMS ethers. PMID:12150815

  17. A new 5-alkylresorcinol glucoside derivative from Cybianthus magnus.

    PubMed

    Cabanillas, B; Vásquez-Ocmín, P; Zebiri, I; Rengifo, E; Sauvain, M; Le, H L; Vaisberg, A; Voutquenne-Nazabadioko, L; Haddad, M

    2016-02-01

    One new 5-alkylresorcinol glucoside (1) was isolated from leaves of Cybianthus magnus, along with 12 known compounds, isolated from four plants belonging to Myrsinaceae family (2, 3 isolated from C. magnus; 4-7, 10 and 11 isolated from Myrsine latifolia; 4, 8 and 9 isolated from Myrsine sessiflora; 6, 7, 10, 12 and 13 isolated from Myrsine congesta). Their structures were determined on the basis of spectroscopic analysis and by comparison of their spectral data with those reported in the literature. So far, only nine 5-alkylresorcinol glucosides were isolated from leaves of Grevillea robusta. Since resorcinols are known to exhibit strong cytotoxic activity, compounds 1 and 2 were tested against cell lines 3T3, H460, DU145 and MCF-7 for cytotoxicity in vitro and compounds 3-13 were tested for their antileishmanial activity. Compound 2 displayed a strong cytotoxic activity with IC50 values ranging between 22 and 100 ?M for all tested cell lines. Compounds 3-13 were not active against Leishmania amazonensis amastigotes. PMID:26181307

  18. Conversion of volatile alcohols into their glucosides in Arabidopsis

    PubMed Central

    Sugimoto, Koichi; Matsui, Kenji; Takabayashi, Junji

    2015-01-01

    Exposure of tomato plants to volatile chemicals emitted from common cutworm (Spodoptera litura)-infested conspecifics led to accumulation of the glycoside, (Z)-3-hexenyl vicianoside. Accumulation of (Z)-3-hexenyl vicianoside in the exposed plants has adverse impacts on the performance of the common cutworms. The aglycon of (Z)-3-hexenyl vicianoside is derived from airborne (Z)-3-hexenol emitted from infested plants. The ability to incorporate and convert (Z)-3-hexenol to its corresponding glycoside is widely conserved in an array of plant species. However, the specificity of this ability to discriminate between the chemical structures of different volatile alcohols remains unknown. In this study, we investigated glycosylation of several volatile alcohols in Arabidopsis (Arabidopsis thaliana). The exposure of Arabidopsis to a variety of volatile alcohols, (Z)-2-pentenol, (Z)-3-hexenol, (Z)-3-heptenol, (Z)-3-octenol, (Z)-3-nonenol, cyclohexanol, benzyl alcohol, verbenol, perillyl alcohol, myrtenol, geraniol, or linalool?led to the detection of the putative corresponding glucosides. These results suggest that Arabidopsis might convert a broad range of volatile alcohols into the corresponding glucosides. PMID:26629260

  19. In vitro COX-1 and COX-2 enzyme inhibitory activities of iridoids from Penstemon barbatus, Castilleja tenuiflora, Cresentia alata and Vitex mollis.

    PubMed

    Ramírez-Cisneros, M Ángeles; Rios, María Yolanda; Aguilar-Guadarrama, A Berenice; Rao, Praveen P N; Aburto-Amar, Rola; Rodríguez-López, Verónica

    2015-10-15

    A group of sixteen iridoids isolated from plants used as anti-inflammatory remedies in Mexican folk medicine were evaluated for their potential to inhibit cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) enzymes. From these assays, loganic acid (10) was identified as the most promising compound with both COX-1 (36.0±0.6%) and COX-2 (80.8±4.0%) inhibition at 10?M. Compound 10 shows a better inhibition against the COX-2 enzyme. Other iridoids tested in the present study showed weak or no inhibition against these enzymes. Furthermore, herein are presented key interactions of iridoid 10 with COX-1 and COX-2 enzymes through molecular docking studies. These studies suggest that 10 exhibits anti-inflammatory activity due to COX inhibition. PMID:26351040

  20. Iridoid glycoside variation in the invasive plant Dalmatian toadflax, Linaria dalmatica (Plantaginaceae), and sequestration by the biological control agent, Calophasia lunula.

    PubMed

    Jamieson, Mary A; Bowers, M Deane

    2010-01-01

    Invasive plant species can have significant ecological and economic impacts. Although numerous hypotheses highlight the importance of the chemical defenses of invasive plant species, the chemical ecology of many invasive plants has not yet been investigated. In this study, we provide the first quantitative investigation of variation in iridoid glycoside concentrations of the invasive plant Dalmatian toadflax (Linaria dalmatica). We examined variation in chemical defenses at three levels: (1) variation within and among populations; (2) variation due to phenology and/or seasonal differences; and (3) variation among plant parts (leaves, flowers, and stems). Further, we examined two biological control agents introduced to control L. dalmatica for the ability to sequester iridoid glycosides from this invasive plant. Results indicate that L. dalmatica plants can contain high concentrations of iridoid glycosides (up to 17.4% dry weight of leaves; mean = 6.28?±?0.5 SE). We found significant variation in iridoid glycoside concentrations both within and among plant populations, over the course of the growing season, and among plant parts. We also found that one biological control agent, Calophasia lunula (Lepidoptera: Noctuidae), was capable of sequestering antirrhinoside, an iridoid glycoside found in L. dalmatica, at levels ranging from 2.7 to 7.5% dry weight. A second biological control agent, Mecinus janthinus (Coleoptera: Curculionidae), a stem-mining weevil, did not sequester iridoid glycosides. The demonstrated variation in L. dalmatica chemical defenses may have implications for understanding variation in the degree of invasiveness of different populations as well as variation in the efficacy of biological control efforts. PMID:20077129

  1. Chemotaxonomic value of magastigmane glucosides of Cichorium calvum.

    PubMed

    Michalska, Klaudia; Beharav, Alex; Kisiel, Wanda

    2014-03-01

    Morphological characters and molecular analyses of Cichorium calvum and C. pumilum do not allow clear discrimination between these closely related wild species. Therefore, the aim of this study was to characterize the secondary metabolites of C. calvum and to select chemical markers which are unique to this species. From roots of C. calvum, ten sesquiterpene lactones were isolated, including seven lactucin-type guaianolides reported earlier from C. pumilum. Aerial parts also afforded secondary metabolites common to both species, along with the megastigmane glucosides staphylionoside D, saussureoside B and komaroveside A. This is the first report of the occurrence of these norisoprenoids in Cichorium species and the second record of their isolation from plants. Therefore, chemical discrimination of C. calvum is possible on the basis of its norisoprenoid composition. PMID:24689202

  2. Olive leaf components apigenin 7-glucoside and luteolin 7-glucoside direct human hematopoietic stem cell differentiation towards erythroid lineage.

    PubMed

    Samet, Imen; Villareal, Myra O; Motojima, Hideko; Han, Junkyu; Sayadi, Sami; Isoda, Hiroko

    2015-06-01

    The generation of blood cellular components from hematopoietic stem cells is important for the therapy of a broad spectrum of hematological disorders. In recent years, several lines of evidence suggested that certain nutrients, vitamins and flavonoids may have important roles in controlling the stem cell fate decision by maintaining their self-renewal or stimulating the lineage-specific differentiation. In this study, main olive leaf phytochemicals oleuropein (Olp), apigenin 7-glucoside (Api7G) and luteolin 7-glucoside (Lut7G) were investigated for their potential effects on hematopoietic stem cell differentiation using both phenotypic and molecular analysis. Oleuropein and the combination of the three compounds enhanced the differentiation of CD34+ cells into myelomonocytic cells and lymphocytes progenitors and inhibited the commitment to megakaryocytic and erythroid lineages. Treatment with Lut7G stimulated both the erythroid and the myeloid differentiation, while treatment with Api7G specifically induced the differentiation of CD34+ cells towards the erythroid lineage and inhibited the myeloid differentiation. Erythroid differentiation induced by Api7G and Lut7G treatments was confirmed by the increase in hemoglobin genes expressions (?-hemoglobin, ?-hemoglobin and ?-hemoglobin) and erythroid transcription factor GATA1 expression. As revealed by microarray analysis, the mechanisms underlying the erythroid differentiation-inducing effect of Api7G on hematopoietic stem cells involves the activation of JAK/STAT signaling pathway. These findings prove the differentiation-inducing effects of olive leaf compounds on hematopoietic stem cells and highlight their potential use in the ex vivo generation of blood cells. PMID:26299581

  3. Quantification of nitropropanoyl glucosides in karaka nuts before and after treatment.

    PubMed

    MacAskill, J J; Manley-Harris, M; Field, Richard J

    2015-05-15

    A high performance liquid chromatography (HPLC) method was developed to assay nitropropanoyl glucosides in the nuts of karaka (Corynocarpus laevigatus) a traditional food of New Zealand M?ori. Levels of glucosides, measured as 3-nitropropanoic acid, ranged from 50.25 to 138.62 g kg(-1) (5.0-13.9% w/w) and were highest in nuts from unripe drupes; these levels are higher than any previously reported. Other parts of the drupe also contained nitropropanoyl glucosides but at lower levels than the nut. Treatment procedures to remove the glucosides from the nuts varied in their efficacy with soxhlet extraction removing 98.7% and prolonged boiling and cold water extraction both removing 96%. These findings confirm the traditional methods for preparation of these nuts for consumption. PMID:25577118

  4. Shancigusins E-I, five new glucosides from the tubers of Pleione yunnanensis.

    PubMed

    Dong, Hai-ling; Liang, Han-qiao; Wang, Chun-lan; Guo, Shun-xing; Yang, Jun-Shan

    2013-06-01

    Five new glucosides, shancigusins E-I (1-5) were isolated from the tubers of Pleione yunnanensis (Rolfe) together with 18 known compounds. The structures of these compounds were determined by extensive analyses of their spectroscopic data. PMID:23616348

  5. Small intestinal hydrolysis of plant glucosides: higher glucohydrolase activities in rodents than passerine birds.

    PubMed

    Lessner, Krista M; Dearing, M Denise; Izhaki, Ido; Samuni-Blank, Michal; Arad, Zeev; Karasov, William H

    2015-09-01

    Glycosides are a major group of plant secondary compounds characterized by one or more sugars conjugated to a lipophilic, possibly toxic aglycone, which is released upon hydrolysis. We compared small intestinal homogenate hydrolysis activity of three rodent and two avian species against four substrates: amygdalin and sinigrin, two plant-derived glucosides, the sugar lactose, whose hydrolysis models some activity against flavonoid and isoflavonoid glucosides, and the disaccharide sugar maltose (from starch), used as a comparator. Three new findings extend our understanding of physiological processing of plant glucosides: (1) the capacity of passerine birds to hydrolyze plant glucosides seems relatively low, compared with rodents; (2) in this first test of vertebrates' enzymic capacity to hydrolyze glucosinolates, sinigrin hydrolytic capacity seems low; (3) in laboratory mice, hydrolytic activity against lactose resides on the enterocytes' apical membrane facing the intestinal lumen, but activity against amygdalin seems to reside inside enterocytes. PMID:26113142

  6. Iridoid and aromatic glycosides from Scrophularia ningpoensis Hemsl. and their inhibition of [Ca2+](i) increase induced by KCl.

    PubMed

    Chen, Bin; Liu, Yan; Liu, Hong-Wei; Wang, Nai-Li; Yang, Bao-Feng; Yao, Xin-Sheng

    2008-09-01

    Bioassay-guided fractionation of EtOH extract of the roots of Scrophularia ningpoensis Hemsl. resulted in the isolation of three new iridoid glycosides, i.e., 6''-O-caffeoylharpagide (1), 6''-O-feruloylharpagide (2), and 6''-O-beta-glucopyranosylharpagoside (3), and five new aromatic glycosides, i.e., 2-(3-hydroxy-4-methoxyphenyl)ethyl O-alpha-arabinopyranosyl-(1-->6)-O-alpha-rhamnopyranosyl-(1-->3)-O-beta-glucopyranoside (4), phenyl O-beta-xylopyranosyl-(1-->6)-O-beta-glucopyranoside (5), 3-methylphenyl O-beta-xylopyranosyl-(1-->6)-O-beta-glucopyranoside (6), 6-O-cinnamoyl beta-fructofuranosyl-(2-->1)-O-alpha-glucopyranosyl-(6-->1)-O-alpha-glucopyranoside (7), and 6-O-feruloyl beta-fructofuranosyl-(2-->1)-O-alpha-glucopyranosyl-(6-->1)-O-alpha-glucopyranoside (8), together with four known compounds, i.e., 6''-O-alpha-D-galactopyranosyl harpagoside (9), 6''-O-(p-coumaroyl) harpagide (10), harpagoside (11), and angoroside C (12). Activity of the isolated compounds on [Ca2+](i) increase induced by KCl was evaluated on rat cardiac myocytes using confocal laser scanning microscopy. Iridoid glycosides 1, 10, and 11, and aromatic glycosides 5 and 6 significantly inhibited the increase of [Ca2+](i) induced by KCl at 100 microM. PMID:18816525

  7. 2'-O-(8-Hydroxy-2,6-dimethyl-2(E),6(E)-octadienoyl)-dihydropenstemide, a new iridoid glycoside from Penstemon confertus.

    PubMed

    Gering-Ward, B

    1989-02-01

    A new iridoid glycoside, 2'- O-(8-hydroxy-2,6-dimethyl-2( E),6( E)-octadienoyl)-dihydropenstemide, has been isolated from PENSTEMON CONFERTUS Dougl. Its structure was elucidated by FD-mass, (1)H-NMR, and (13)C-NMR spectroscopy. PMID:17262262

  8. A study of the substance dependence effect of the ethanolic extract and iridoid-rich fraction from Valeriana jatamansi Jones in mice

    PubMed Central

    Yu, Lin; Ke-ke, Xu; Chao-yong, Chen; Rui-tong, Zhang; Ming, Lan; Shao-hua, Li; Ling-zhen, Pan; Tian-e, Zhang; Zhi-yong, Yan

    2015-01-01

    Background: Recently we found the ethanolic extract and iridoid-rich fraction from Valeriana jatamansi Jones, which is a traditional Chinese medicine exhibited anxiolytic properties. Objective: This study aims to the substance dependence effect of the ethanolic extract and iridoid-rich fraction. Materials and Methods: The study included two experiments: Mice were given orally with ethanolic extract for 12 weeks or iridoid-rich fraction for 16 weeks in experiment I and experiment II, respectively. Diazepam was used as a control drug and the normal mice groups were administered with 0.5% carboxymethyl cellulose Na in both experiments. All groups were administered twice daily. Natural withdrawal symptoms, withdrawal-induced body weight change, audiogenic tail-erection test (in experiment I), and pentylenetetrazol (PTZ)-induced convulsion test (in experiment II) were measured. Results: (1) Compared to normal group in both experiments, the diazepam-treated group exhibited obvious withdrawal symptoms of tail-erection, irritability, teeth chattering, etc; the body weight of them after withdrawal had a period of significant loss (P < 0.05 or P < 0.01); and the ratios of tail-erection and seizure in two experiments were improved significantly when mice were induced by mixer noise ringtone (experiment I) or PTZ (experiment II) (P < 0.05 or P < 0.01).(2) In experiment I and II, there were no significant differences between mice that received ethanolic extract or iridoid-rich fraction and normal group in terms of natural withdrawal symptoms and withdrawal-induced body weight change (P > 0.05); in audiogenic tail-erection test, it found that the significant difference compared with normal group was just in ethanolic extract 900 mg/kg dose group on week 8 (P < 0.05); in PTZ-induced convulsion test, mice in iridoid-rich fraction groups had a slightly tail-erection and seizure, all results of them were with no significant difference compare to normal mice (P > 0.05), while significant lower than diazepam group (P < 0.01). Conclusion: (1) The two experiments successfully established the physical dependence of diazepam by gradually increasing the dose.(2)There were just a few mice received with ethanolic extract for 12 weeks or iridoid-rich fraction for 16 weeks appearing some slight withdrawal symptoms after precipitated withdrawal, but it didn’t show significant difference compared to normal mice. Therefore, these indicated that the risks of potential drug dependence about ethanolic extract and iridoid-rich fraction were far lower than that of diazepam. PMID:26600719

  9. Low Toxicity of Deoxynivalenol-3-Glucoside in Microbial Cells

    PubMed Central

    Suzuki, Tadahiro; Iwahashi, Yumiko

    2015-01-01

    Host plants excrete a glucosylation enzyme onto the plant surface that changes mycotoxins derived from fungal secondary metabolites to glucosylated products. Deoxynivalenol-3-glucoside (DON3G) is synthesized by grain uridine diphosphate-glucosyltransferase, and is found worldwide, although information on its toxicity is lacking. Here, we conducted growth tests and DNA microarray analysis to elucidate the characteristics of DON3G. The Saccharomyces cerevisiae PDR5 mutant strain exposed to DON3G demonstrated similar growth to the dimethyl sulfoxide control, and DNA microarray analysis revealed limited differences. Only 10 genes were extracted, and the expression profile of stress response genes was similar to that of DON, in contrast to metabolism genes like SER3, which encodes 3-phosphoglycerate dehydrogenase. Growth tests with Chlamydomonas reinhardtii also showed a similar growth rate to the control sample. These results suggest that DON3G has extremely low toxicity to these cells, and the glucosylation of mycotoxins is a useful protective mechanism not only for host plants, but also for other species. PMID:25609182

  10. Hydrolytic fate of deoxynivalenol-3-glucoside during digestion

    PubMed Central

    Berthiller, Franz; Krska, Rudolf; Domig, Konrad J.; Kneifel, Wolfgang; Juge, Nathalie; Schuhmacher, Rainer; Adam, Gerhard

    2011-01-01

    Deoxynivalenol-3-?-d-glucoside (D3G), a plant phase II metabolite of the Fusarium mycotoxin deoxynivalenol (DON), occurs in naturally contaminated wheat, maize, oat, barley and products thereof. Although considered as a detoxification product in plants, the toxicity of this substance in mammals is currently unknown. A major concern is the possible hydrolysis of the D3G conjugate back to its toxic precursor mycotoxin DON during mammalian digestion. We used in vitro model systems to investigate the stability of D3G to acidic conditions, hydrolytic enzymes and intestinal bacteria, mimicking different stages of digestion. D3G was found resistant to 0.2 M hydrochloric acid for at least 24 h at 37 °C, suggesting that it will not be hydrolyzed in the stomach of mammals. While human cytosolic ?-glucosidase also had no effect, fungal cellulase and cellobiase preparations could cleave a significant portion of D3G. Most importantly, several lactic acid bacteria such as Enterococcus durans, Enterococcus mundtii or Lactobacillus plantarum showed a high capability to hydrolyze D3G. Taken together these data indicate that D3G is of toxicological relevance and should be regarded as a masked mycotoxin. PMID:21878373

  11. Interaction of cyanidin-3-O-glucoside with three proteins.

    PubMed

    Tang, Lin; Li, Shu; Bi, Hongna; Gao, Xin

    2016-04-01

    We studied the binding of cyanidin-3-O-glucoside (C3G) with bovine serum albumin (BSA), hemoglobin (Hb) and myoglobin (Mb), using multi-spectral techniques and molecular modeling. Fluorescence and time-resolved fluorescence studies suggested that C3G quenched BSA, Hb or Mb fluorescence in a static mode with binding constants of 4.159, 0.695 and 1.545×10(4)Lmol(-1) at 308K, respectively. The thermodynamic parameters represented hydrogen bonds and van der Waals forces dominated the binding. Furthermore, CD, UV-vis, and three-dimensional fluorescence spectra results indicated the secondary structures of BSA, Hb and Mb were partially destroyed by C3G with the ?-helix percentage of C3G-Hb and C3G-Mb decreased while that of C3G-BSA was increased. UV-vis spectral results showed these binding interactions partially affected the heme bands of Hb and Mb. In addition, molecular modeling analysis supported the experimental results well. The calculated results of equilibrium fraction showed that the concentration of free C3G in plasma was high enough to be stored and transported from the circulatory system to reach their target sites to provide their therapeutic effects. PMID:26593527

  12. Tetrahydroxystilbene Glucoside Attenuates Neuroinflammation through the Inhibition of Microglia Activation

    PubMed Central

    Zhang, Feng; Wang, Yan-Ying; Yang, Jun; Lu, Yuan-Fu; Liu, Jie; Shi, Jing-Shan

    2013-01-01

    Neuroinflammation is closely implicated in the pathogenesis of neurological diseases. The hallmark of neuroinflammation is the microglia activation. Upon activation, microglia are capable of producing various proinflammatory factors and the accumulation of these factors contribute to the neuronal damage. Therefore, inhibition of microglia-mediated neuroinflammation might hold potential therapy for neurological disorders. 2,3,5,4?-Tetrahydroxystilbene-2-O-?-D-glucoside (TSG), an active component extracted from Polygonum multiflorum, is reported to be beneficial for human health with a great number of pharmacological properties including antioxidant, free radical-scavenging, anti-inflammation, antilipemia, and cardioprotective effects. Recently, TSG-mediated neuroprotective effects have been well demonstrated. However, the neuroprotective actions of TSG on microglia-induced neuroinflammation are not known. In the present study, microglia BV2 cell lines were applied to investigate the anti-neuroinflammatory effects of TSG. Results showed that TSG reduced LPS-induced microglia-derived release of proinflammatory factors such as TNF?, IL-1?, and NO. Moreover, TSG attenuated LPS-induced NADPH oxidase activation and subsequent reactive oxygen species (ROS) production. Further studies indicated that TSG inhibited LPS-induced NF-?B signaling pathway activation. Together, TSG exerted neuroprotection against microglia-mediated neuroinflammation, suggesting that TSG might present a promising benefit for neurological disorders treatment. PMID:24349614

  13. Tetrahydroxystilbene glucoside attenuates neuroinflammation through the inhibition of microglia activation.

    PubMed

    Zhang, Feng; Wang, Yan-Ying; Yang, Jun; Lu, Yuan-Fu; Liu, Jie; Shi, Jing-Shan

    2013-01-01

    Neuroinflammation is closely implicated in the pathogenesis of neurological diseases. The hallmark of neuroinflammation is the microglia activation. Upon activation, microglia are capable of producing various proinflammatory factors and the accumulation of these factors contribute to the neuronal damage. Therefore, inhibition of microglia-mediated neuroinflammation might hold potential therapy for neurological disorders. 2,3,5,4'-Tetrahydroxystilbene-2-O-?-D-glucoside (TSG), an active component extracted from Polygonum multiflorum, is reported to be beneficial for human health with a great number of pharmacological properties including antioxidant, free radical-scavenging, anti-inflammation, antilipemia, and cardioprotective effects. Recently, TSG-mediated neuroprotective effects have been well demonstrated. However, the neuroprotective actions of TSG on microglia-induced neuroinflammation are not known. In the present study, microglia BV2 cell lines were applied to investigate the anti-neuroinflammatory effects of TSG. Results showed that TSG reduced LPS-induced microglia-derived release of proinflammatory factors such as TNF?, IL-1?, and NO. Moreover, TSG attenuated LPS-induced NADPH oxidase activation and subsequent reactive oxygen species (ROS) production. Further studies indicated that TSG inhibited LPS-induced NF-?B signaling pathway activation. Together, TSG exerted neuroprotection against microglia-mediated neuroinflammation, suggesting that TSG might present a promising benefit for neurological disorders treatment. PMID:24349614

  14. The ?-Glucosidases Responsible for Bioactivation of Hydroxynitrile Glucosides in Lotus japonicus1[W

    PubMed Central

    Morant, Anne Vinther; Bjarnholt, Nanna; Kragh, Mads Emil; Kjærgaard, Christian Hauge; Jørgensen, Kirsten; Paquette, Suzanne Michelle; Piotrowski, Markus; Imberty, Anne; Olsen, Carl Erik; Møller, Birger Lindberg; Bak, Søren

    2008-01-01

    Lotus japonicus accumulates the hydroxynitrile glucosides lotaustralin, linamarin, and rhodiocyanosides A and D. Upon tissue disruption, the hydroxynitrile glucosides are bioactivated by hydrolysis by specific ?-glucosidases. A mixture of two hydroxynitrile glucoside-cleaving ?-glucosidases was isolated from L. japonicus leaves and identified by protein sequencing as LjBGD2 and LjBGD4. The isolated hydroxynitrile glucoside-cleaving ?-glucosidases preferentially hydrolyzed rhodiocyanoside A and lotaustralin, whereas linamarin was only slowly hydrolyzed, in agreement with measurements of their rate of degradation upon tissue disruption in L. japonicus leaves. Comparative homology modeling predicted that LjBGD2 and LjBGD4 had nearly identical overall topologies and substrate-binding pockets. Heterologous expression of LjBGD2 and LjBGD4 in Arabidopsis (Arabidopsis thaliana) enabled analysis of their individual substrate specificity profiles and confirmed that both LjBGD2 and LjBGD4 preferentially hydrolyze the hydroxynitrile glucosides present in L. japonicus. Phylogenetic analyses revealed a third L. japonicus putative hydroxynitrile glucoside-cleaving ?-glucosidase, LjBGD7. Reverse transcription-polymerase chain reaction analysis showed that LjBGD2 and LjBGD4 are expressed in aerial parts of young L. japonicus plants, while LjBGD7 is expressed exclusively in roots. The differential expression pattern of LjBGD2, LjBGD4, and LjBGD7 corresponds to the previously observed expression profile for CYP79D3 and CYP79D4, encoding the two cytochromes P450 that catalyze the first committed step in the biosyntheis of hydroxynitrile glucosides in L. japonicus, with CYP79D3 expression in aerial tissues and CYP79D4 expression in roots. PMID:18467457

  15. Biosynthesis of cyanohydrin glucosides from unnatural nitriles in intact tissue of Passiflora morifolia and Turnera angustifolia.

    PubMed

    Jaroszewski, J W; Rasmussen, A B; Rasmussen, H B; Olsen, C E; Jørgensen, L B

    1996-06-01

    Passiflora morifolia, which under natural conditions contains cyanohydrin glucosides linamarin, lotaustralin and epilotaustralin, converted cyclopentanecarbonitrile, 2-cyclopentenecarbonitrile and 3-methylbutanenitrile into the corresponding cyanohydrin glucosides. Turnera angustifolia, which normally produces glucosides of cyclopentenone cyanohydrin, converted cyclopentanecarbonitrile, 2-methylpropanenitrile and 2-methylbutanenitrile, but not 3-methylbutanenitrile, into the corresponding cyanohydrin glucosides. Mixtures of epimers were produced when these glucosides contained chiral cyanohydrin carbon atoms. Feeding with cyclopentanecarbonitrile resulted in formation of 1-(beta-D-glucopyranosyloxy)cyclopentanecarbonitrile, a saturated analogue of deidaclin and tetraphyllin A. Neither plant utilized cyclopropanecarbonitrile as substrate. The experiments demonstrate broad substrate specificity of nitrile hydroxylases present in these plants. A novel glycoside, 2-[6-O-(beta-D-xylopyranosyl)-beta-D-glucopyranosyloxy]propane (isopropyl primeveroside), was isolated from P. morifolia. The compound represents a rare example of natural isopropyl glycoside; its characterization included assignment of all 1H and 13C NMR signals of the primeverosyl group using two-dimensional NMR methods. Biosynthesis of the isopropyl moiety of the primeveroside is unclear, but the formation of alcohols corresponding to natural cyanohydrins may be a previously unrecognized extension of the cyanohydrin biosynthesis pathway in higher plants. PMID:8768320

  16. Metabolic utilization of pyridoxine-beta-glucoside in rats: influence of vitamin B-6 status and route of administration

    SciTech Connect

    Trumbo, P.R.; Gregory, J.F. 3d.

    1988-11-01

    (3H)5'-O-(beta-D-glucopyranosyl) pyridoxine (PN-glucoside) and (14C)pyridoxine (PN) were administered orally or intraperitoneally to vitamin B-6-adequate or -deficient rats. Analysis of intestinal contents and feces indicated effective intestinal absorption of PN-glucoside relative to PN. There was greater retention of 14C than 3H in the liver and carcass regardless of the route of administration of the radiolabeled vitamins. There was no major difference in the relative distribution of 3H and 14C among the vitamin B-6 metabolites in the liver between the treatment groups, and no (3H)PN-glucoside was detected in any of the livers. For all groups, the majority of the 3H administered was detected in the urine within 24 h. Less excretion of both 3H and 14C in the urine was observed for the deficient rats. There was no major difference in the relative proportion of urinary (3H)PN-glucoside or (3H)4-PA between rats fed or injected with the radiolabeled vitamins. These results indicate that vitamin B-6 status influences the clearance of metabolites derived from PN and PN-glucoside, as well as the clearance of intact PN-glucoside. Vitamin B-6 status, however, has little or no effect on the utilization of PN-glucoside. This study also suggests that the intestine is the primary site of the limited conversion of PN-glucoside to biologically active PN in the rat.

  17. Quercetin 3-O-glucoside suppresses epidermal growth factor-induced migration by inhibiting EGFR signaling in pancreatic cancer cells.

    PubMed

    Lee, Jungwhoi; Han, Song-I; Yun, Jeong-Hun; Kim, Jae Hoon

    2015-12-01

    Pancreatic cancer is one of the most dangerous cancers and is associated with a grave prognosis. Despite increased knowledge of the complex signaling networks responsible for progression of pancreatic cancer, many challenging therapies have fallen short of expectations. In this study, we examined the anti-migratory effect of quercetin 3-O-glucoside in epidermal growth factor-induced cell migration by inhibiting EGF receptor (EGFR) signaling in several human pancreatic cancer cell lines. Treatment with quercetin, quercetin 3-O-glucoside, and quercetin 7-O-glucoside differentially suppressed epidermal growth factor-induced migration activity of human pancreatic cancer cells. In particular, quercetin 3-O-glucoside strongly inhibited the infiltration activity of pancreatic cancer cells in a dose-dependent manner. Furthermore, quercetin 3-O-glucoside exerted the anti-migratory effect even at a relatively low dose compared with other forms of quercetin. The anti-tumor effects of quercetin 3-O-glucoside were mediated by selectively inhibiting the EGFR-mediated FAK, AKT, MEK1/2, and ERK1/2 signaling pathway. Combinatorial treatment with quercetin 3-O-glucoside plus gemcitabine showed the synergistic anti-migratory effect on epidermal growth factor-induced cell migration in human pancreatic cancer cell lines. These results suggest that quercetin 3-O-glucoside has potential for anti-metastatic therapy in human pancreatic cancer. PMID:26109002

  18. Profiling of components and validated determination of iridoids in Gardenia Jasminoides Ellis fruit by a high-performance-thin-layer- chromatography/mass spectrometry approach.

    PubMed

    Coran, Silvia A; Mulas, Stefano; Vasconi, Alessio

    2014-01-17

    A novel method was set up with the aim to obtain a simultaneous cross comparative evaluation of different Gardenia Jasminoides Ellis fruits by the HPTLC fingerprint approach. The main components among the iridoid, hydroxycinnamic derivative and crocin classes were identified by TLC-MS ancillary techniques. The iridoids geniposide, gardenoside and genepin-1-?-d-gentiobioside were also quantitated by densitometric scanning at 240nm. LiChrospher HPTLC Silica gel 60 RP-18 W F254, 20cm×10cm plates with acetonitrile: formic acid 0.1% (40:60 v/v) as the mobile phase was used. The method was validated giving rise to a dependable and high throughput procedure well suited to routine applications. Iridoids were quantified in the range of 240-1140ng with RSD of repeatability and intermediate precision between 0.9-2.5% and accuracy with bias 1.6-2.6%. The method was tested on six commercial Gardenia Jasminoides fruit samples. PMID:24365117

  19. The bHLH transcription factor BIS1 controls the iridoid branch of the monoterpenoid indole alkaloid pathway in Catharanthus roseus

    PubMed Central

    Van Moerkercke, Alex; Steensma, Priscille; Schweizer, Fabian; Pollier, Jacob; Gariboldi, Ivo; Payne, Richard; Vanden Bossche, Robin; Miettinen, Karel; Espoz, Javiera; Purnama, Purin Candra; Kellner, Franziska; Seppänen-Laakso, Tuulikki; O’Connor, Sarah E.; Rischer, Heiko; Memelink, Johan; Goossens, Alain

    2015-01-01

    Plants make specialized bioactive metabolites to defend themselves against attackers. The conserved control mechanisms are based on transcriptional activation of the respective plant species-specific biosynthetic pathways by the phytohormone jasmonate. Knowledge of the transcription factors involved, particularly in terpenoid biosynthesis, remains fragmentary. By transcriptome analysis and functional screens in the medicinal plant Catharanthus roseus (Madagascar periwinkle), the unique source of the monoterpenoid indole alkaloid (MIA)-type anticancer drugs vincristine and vinblastine, we identified a jasmonate-regulated basic helix–loop–helix (bHLH) transcription factor from clade IVa inducing the monoterpenoid branch of the MIA pathway. The bHLH iridoid synthesis 1 (BIS1) transcription factor transactivated the expression of all of the genes encoding the enzymes that catalyze the sequential conversion of the ubiquitous terpenoid precursor geranyl diphosphate to the iridoid loganic acid. BIS1 acted in a complementary manner to the previously characterized ethylene response factor Octadecanoid derivative-Responsive Catharanthus APETALA2-domain 3 (ORCA3) that transactivates the expression of several genes encoding the enzymes catalyzing the conversion of loganic acid to the downstream MIAs. In contrast to ORCA3, overexpression of BIS1 was sufficient to boost production of high-value iridoids and MIAs in C. roseus suspension cell cultures. Hence, BIS1 might be a metabolic engineering tool to produce sustainably high-value MIAs in C. roseus plants or cultures. PMID:26080427

  20. The bHLH transcription factor BIS1 controls the iridoid branch of the monoterpenoid indole alkaloid pathway in Catharanthus roseus.

    PubMed

    Van Moerkercke, Alex; Steensma, Priscille; Schweizer, Fabian; Pollier, Jacob; Gariboldi, Ivo; Payne, Richard; Vanden Bossche, Robin; Miettinen, Karel; Espoz, Javiera; Purnama, Purin Candra; Kellner, Franziska; Seppänen-Laakso, Tuulikki; O'Connor, Sarah E; Rischer, Heiko; Memelink, Johan; Goossens, Alain

    2015-06-30

    Plants make specialized bioactive metabolites to defend themselves against attackers. The conserved control mechanisms are based on transcriptional activation of the respective plant species-specific biosynthetic pathways by the phytohormone jasmonate. Knowledge of the transcription factors involved, particularly in terpenoid biosynthesis, remains fragmentary. By transcriptome analysis and functional screens in the medicinal plant Catharanthus roseus (Madagascar periwinkle), the unique source of the monoterpenoid indole alkaloid (MIA)-type anticancer drugs vincristine and vinblastine, we identified a jasmonate-regulated basic helix-loop-helix (bHLH) transcription factor from clade IVa inducing the monoterpenoid branch of the MIA pathway. The bHLH iridoid synthesis 1 (BIS1) transcription factor transactivated the expression of all of the genes encoding the enzymes that catalyze the sequential conversion of the ubiquitous terpenoid precursor geranyl diphosphate to the iridoid loganic acid. BIS1 acted in a complementary manner to the previously characterized ethylene response factor Octadecanoid derivative-Responsive Catharanthus APETALA2-domain 3 (ORCA3) that transactivates the expression of several genes encoding the enzymes catalyzing the conversion of loganic acid to the downstream MIAs. In contrast to ORCA3, overexpression of BIS1 was sufficient to boost production of high-value iridoids and MIAs in C. roseus suspension cell cultures. Hence, BIS1 might be a metabolic engineering tool to produce sustainably high-value MIAs in C. roseus plants or cultures. PMID:26080427

  1. 21 CFR 178.3600 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Methyl glucoside-coconut oil ester. 178.3600 Section 178.3600 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) FOOD FOR HUMAN CONSUMPTION (CONTINUED) INDIRECT FOOD ADDITIVES: ADJUVANTS, PRODUCTION AIDS, AND SANITIZERS Certain Adjuvants and...

  2. 21 CFR 178.3600 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Methyl glucoside-coconut oil ester. 178.3600 Section 178.3600 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) FOOD FOR HUMAN CONSUMPTION (CONTINUED) INDIRECT FOOD ADDITIVES: ADJUVANTS, PRODUCTION AIDS, AND SANITIZERS Certain Adjuvants and...

  3. 21 CFR 172.816 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Methyl glucoside-coconut oil ester. 172.816 Section 172.816 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) FOOD FOR HUMAN CONSUMPTION (CONTINUED) FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION Multipurpose Additives...

  4. EVALUATION OF THE ANTIOXIDANT CAPACITY OF LIMONIN, NOMILIN AND LIMONIN GLUCOSIDE

    Technology Transfer Automated Retrieval System (TEKTRAN)

    In an effort to resolve conflicting reports of the antioxidant properties of citrus limonoids, the Antioxidant Capacity (AOC) of citrus limonoids limonin, nomilin and limonin glucoside was evaluated by the oxygen radical absorbance capacity (ORAC), Trolox equivalent antioxidant capacity (TEAC), beta...

  5. Analysis of deoxynivalenol and deoxynivalenol-3-glucoside in hard red spring wheat inoculated with Fusarium graminearum

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Deoxynivalenol (DON) is a mycotoxin which isproduced by plant pathogens such as Fusarium species. The formation of the "masked" mycotoxin deoxinyvalenol-3-glucoside (D3G) results from a defense mechanism the plant uses for detoxification. These two mycotoxins are important from the food safety poi...

  6. 21 CFR 172.816 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 3 2014-04-01 2014-04-01 false Methyl glucoside-coconut oil ester. 172.816 Section 172.816 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION Multipurpose...

  7. 21 CFR 172.816 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 3 2012-04-01 2012-04-01 false Methyl glucoside-coconut oil ester. 172.816 Section 172.816 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) FOOD FOR HUMAN CONSUMPTION (CONTINUED) FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION Multipurpose Additives...

  8. 21 CFR 172.816 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 3 2013-04-01 2013-04-01 false Methyl glucoside-coconut oil ester. 172.816 Section 172.816 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) FOOD FOR HUMAN CONSUMPTION (CONTINUED) FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION Multipurpose Additives...

  9. Effect of different exposed lights on quercetin and quercetin glucoside content in onion (Allium cepa L.)

    PubMed Central

    Ko, Eun Young; Nile, Shivraj Hariram; Sharma, Kavita; Li, Guan Hao; Park, Se Won

    2014-01-01

    Quercetin and quercetin glucosides are the major flavonols present in onion (Allium cepa L.) and are predominantly present as quercetin, quercetin-3,4?-diglucoside and quercetin-4?-glucoside. Effect of different light wavelengths on onion after harvest and storage, with fluorescent, blue, red and ultra violet light influenced the quercetin and quercetin glucosides profile. In a peeled onion, all the light treatments elevated quercetin content in bulb. Among them, particularly fluorescent light effect was more eminent which stimulates the maximum synthesis of quercetin in onion. In case of whole onion bulb, skin and pulp showed different responses to light treatment, respectively. The pulp had the highest quercetin glucosides under blue light, whereas the lowest under fluorescent light. Onion skin showed nearly opposite pattern as compared to the pulp. In particular, light treatment proved to be a better way to increase the level of quercetin content in onions which might be utilized for industrial production of bioactive compounds from onion and onion waste products. PMID:26150744

  10. CYANIDIN-3-GLUCOSIDE, A NATURAL PRODUCT DERIVED FROM BLACKBERRY, EXHIBITS CHEMOPREVENTIVE AND CHEMOTHERAPEUTIC ACTIVITY

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Epidemiological data suggest that consumption of fruits and vegetables has been associated with a lower incidence of cancer. Cyanidin-3-glucoside (C3G), a compound found in blackberry and other food products, was shown to possess chemopreventive and chemotherapeutic activity in the present study. ...

  11. Serotonin 5-O-?-Glucoside and Its N-Methylated Forms in Citrus Genus Plants.

    PubMed

    Servillo, Luigi; Giovane, Alfonso; Casale, Rosario; D'Onofrio, Nunzia; Ferrari, Giovanna; Cautela, Domenico; Balestrieri, Maria Luisa; Castaldo, Domenico

    2015-04-29

    Citrus genus is characterized by a specific presence of indole metabolites deriving from the N-methylation of tryptamine and its hydroxylated form, 5-hydroxytryptamine (serotonin), which are likely involved in plant defense mechanisms. In this study, we identified for the first time the occurrence in Citrus plants of serotonin 5-O-?-glucoside and all its N-methylated derivatives, that is, N-methylserotonin 5-O-?-glucoside, N,N-dimethylserotonin (bufotenine) 5-O-?-glucoside, and N,N,N-trimethylserotonin (bufotenidine) 5-O-?-glucoside. The identification of the glucosylated compounds was based on mass spectrometric studies, hydrolysis by glucosidase, and in some cases, comparison to authentic compounds. Beside leaves, the distribution of the glucosylated forms and their aglycones in some Citrus species was evaluated in flavedo, albedo, juice, and seeds. The simultaneous presence of serotonin and its N-methylated derivatives, together with the corresponding glucosylated forms, is consistent with the occurrence of a metabolic pathway, specific for Citrus, aimed at potentiating the defensive response to biotic stress through the optimization of the production and use of the most toxic of such metabolites. PMID:25893818

  12. Simultaneous extraction of bioactive limonoid aglycones and glucoside from Citrus aurantium L. using hydrotropy.

    PubMed

    Dandekar, Deepak V; Jayaprakasha, Guddadarangavvanahally K; Patil, Bhimanagouda S

    2008-01-01

    Citrus limonoids were demonstrated to possess potential biological activities in reducing the risk of certain diseases. Limonoids are present in citrus fruits in the form of aglycones and glucosides. At present, limonoid aglycones and limonoid glucosides are extracted in multiple steps using different solvents. In order to understand their potential bioactivity, it may be beneficial to isolate and purify these compounds using environment friendly methods. A new method of extraction and purification of limonoids was established using a hydrotrope polystyrene adsorbent resin. Extraction of aglycones and glucosides was achieved in a single step, using an aqueous solution of sodium cumene sulphonate (Na-CuS). Sour orange (Citrus aurantium L.) seed powder was extracted with 2 M Na-CuS solution at 45 degrees C for 6 h. The filtered extract was diluted with water and loaded on an SP 700 adsorbent column. The column was washed with distilled water to remove the hydrotrope and then eluted using water and methanol in different compositions to obtain three compounds. The structures of the isolated compounds were confirmed by NMR spectroscopy as deacetyl nomilinic acid glucoside (DNAG), deacetyl nomilin (DAN) and limonin (LIM). PMID:18533458

  13. Occurrence of deoxynivalenol and deoxynivalenol-3-glucoside in hard red spring wheat grown in the USA

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Deoxynivalenol (DON) is a mycotoxin found in wheat that is infected with Fusarium fungus. DON may also be converted to a type of "masked mycotoxin," named deoxynivalenol-3-glucoside (D3G), as a result of detoxification process of the plant. Both DON and D3G are known to be toxic. Due to the lack o...

  14. Effect of different exposed lights on quercetin and quercetin glucoside content in onion (Allium cepa L.).

    PubMed

    Ko, Eun Young; Nile, Shivraj Hariram; Sharma, Kavita; Li, Guan Hao; Park, Se Won

    2015-07-01

    Quercetin and quercetin glucosides are the major flavonols present in onion (Allium cepa L.) and are predominantly present as quercetin, quercetin-3,4'-diglucoside and quercetin-4'-glucoside. Effect of different light wavelengths on onion after harvest and storage, with fluorescent, blue, red and ultra violet light influenced the quercetin and quercetin glucosides profile. In a peeled onion, all the light treatments elevated quercetin content in bulb. Among them, particularly fluorescent light effect was more eminent which stimulates the maximum synthesis of quercetin in onion. In case of whole onion bulb, skin and pulp showed different responses to light treatment, respectively. The pulp had the highest quercetin glucosides under blue light, whereas the lowest under fluorescent light. Onion skin showed nearly opposite pattern as compared to the pulp. In particular, light treatment proved to be a better way to increase the level of quercetin content in onions which might be utilized for industrial production of bioactive compounds from onion and onion waste products. PMID:26150744

  15. Quercetin from shallots (Allium cepa L. var. aggregatum) is more bioavailable than its glucosides.

    PubMed

    Wiczkowski, Wieslaw; Romaszko, Jerzy; Bucinski, Adam; Szawara-Nowak, Dorota; Honke, Joanna; Zielinski, Henryk; Piskula, Mariusz K

    2008-05-01

    The lipophilic character of quercetin suggests that it can cross enterocyte membranes via simple diffusion. Therefore, it should be more bioavailable than its glucosides, which require preliminary hydrolysis or active transport for absorption. However, the published human studies show that quercetin is less bioavailable than its glucosides. Assuming that low bioavailability of quercetin aglycone provided to humans as a pure substance is the result of its low solubility in the digestive tract, we studied its bioavailability from dietary sources in which quercetin was dispersed in the food matrix. In a randomized crossover study, 9 volunteers took a single dose of either shallot flesh (99.2% quercetin glucosides and 0.8% quercetin aglycone) or dry shallot skin (83.3% quercetin aglycone and 16.7% quercetin glucosides), providing 1.4 mg quercetin per kg of body weight. Blood samples were collected before and after consumption of shallot preparations. Plasma quercetin was measured on HPLC with electrochemical detection after plasma enzymatic treatment. The maximum plasma quercetin concentration of 1.02 +/- 0.13 micromol/L was reached at 2.33 +/- 0.50 h after shallot flesh consumption compared with 3.95 +/- 0.62 micromol/L at 2.78 +/- 0.15 h after dry skin consumption. The area under the concentration-time curve after dry skin consumption was 47.23 +/- 7.53 micromol x h(-1) x L(-1) and was significantly higher than that after shallot flesh intake (22.23 +/- 2.32 micromol x h(-1) x L(-1)). When provided along with dietary sources, quercetin aglycone is more bioavailable than its glucosides in humans. Results point to the food matrix as a key factor. PMID:18424596

  16. Inhibition of the pro-inflammatory mediators' production and anti-inflammatory effect of the iridoid scrovalentinoside.

    PubMed

    Bas, Esperanza; Recio, M Carmen; Abdallah, Mohamed; Máñez, Salvador; Giner, Rosa M; Cerdá-Nicolás, Miguel; Ríos, José-Luis

    2007-04-01

    We have studied scrovalentinoside, an iridoid with anti-inflammatory properties isolated from Scrophularia auriculata ssp. pseudoauriculata, as an anti-inflammatory agent in different experimental models of delayed-type hypersensitivity. We found that scrovalentinoside reduced the edema induced by oxazolone at 0.5 mg/ear and sheep red blood cells at 10 mg/kg. The observed effect occurred during the last phase or inflammatory response; during the earlier phase or induction of the delayed-type hypersensitivity reaction, no significant activity was noted. Thus, scrovalentinoside reduced both the edema and cell infiltration in vivo and reduced lymphocyte proliferation in vitro, affecting the cycle principally during the first 48 h. Whereas cells stimulated with phytohemagglutinin changed from the G(0)/G(1) phase to the S and G(2)/M phases, when these same cells were treated with scrovalentinoside (100 microM), they remained in the G(0)/G(1) phase. Finally, scrovalentinoside inhibited the production of the pro-inflammatory mediators' TNF-alpha, IFN-gamma, IL-1beta, IL-2, IL-4, LTB(4), and NO, but had no effect on the production of the anti-inflammatory cytokine IL-10. PMID:17112695

  17. Indoline Amide Glucosides from Portulaca oleracea: Isolation, Structure, and DPPH Radical Scavenging Activity.

    PubMed

    Jiao, Ze-Zhao; Yue, Su; Sun, Hong-Xiang; Jin, Tian-Yun; Wang, Hai-Na; Zhu, Rong-Xiu; Xiang, Lan

    2015-11-25

    A polyamide column chromatography method using an aqueous ammonia mobile phase was developed for large-scale accumulation of water-soluble indoline amide glucosides from a medicinal plant, Portulaca oleracea. Ten new [oleraceins H, I, K, L, N, O, P, Q, R, S (1-10)] and four known [oleraceins A-D (11-14)] indoline amide glucosides were further purified and structurally characterized by various chromatographic and spectroscopic methods. The DPPH radical scavenging activities of oleraceins K (5) and L (6), with EC50 values of 15.30 and 16.13 ?M, respectively, were twice that of a natural antioxidant, vitamin C; the EC50 values of the 12 other indoline amides, which ranged from 29.05 to 43.52 ?M, were similar to that of vitamin C. Structure-activity relationships indicated that the DPPH radical scavenging activities of these indoline amides correlate with the numbers and positions of the phenolic hydroxy groups. PMID:26562741

  18. MAO-A inhibition profiles of some benzophenone glucosides from Gentiana verna subsp. pontica.

    PubMed

    Kaya, Duygu; Jäger, Anna K; Yalçin, Funda N; Ersöz, Tayfun

    2014-04-01

    Gentiana verna L. subsp. pontica (Soltok.) Hayek, G. pyrenaica L., and G. verna L. subsp. balcanica Pritchard from Turkey were tested for their MAO-A inhibitory effects. A photometric peroxidase linked MAO-A bioassay performed on the H20 extracts prepared from the methanolic extracts of the title plants revealed the potential effect of G. verna subsp. pontica and three benzophenone glucosides; 2,3'-dihydroxy-4-methoxy-benzophenone-6-O-beta-glucopyranoside (1), 2,4,3',4'-tetrahydroxy-benzophenone-6-O-beta-glucopyranoside (maclurin-6-O-f-glucopyranoside) (2) and 2,4,3'-trihydroxy-benzophenone-6-O-beta-glucopyranoside (3) isolated from G. verna subsp. pontica. Among the benzophenone glucosides 1 and 2 exhibited significant inhibition of MAO-A (IC50 = 31.3 +/- 4 microM and 41 +/- 4.7 microM resp.). PMID:24868869

  19. Exclusive accumulation of Z-isomers of monolignols and their glucosides in bark of Fagus grandifolia

    NASA Technical Reports Server (NTRS)

    Lewis, N. G.; Inciong, E. J.; Ohashi, H.; Towers, G. H.; Yamamoto, E.

    1988-01-01

    In addition to Z-coniferyl and Z-sinapyl alcohols, bark extracts of Fagus grandifolia also contain significant amounts of the glucosides, Z-coniferin, Z-isoconiferin (previously called faguside) and Z-syringin. The corresponding E-isomers of these glucosides do not accumulate to a detectable level. The accumulation of the Z-isomers suggests that either they are not lignin precursors or that they are reservoirs of monolignols for subsequent lignin biosynthesis; it is not possible to distinguish between these alternatives. The co-occurrence of Z-coniferin and Z-isoconiferin demonstrate that glucosylation of monolignols can occur at either the phenolic or the allylic hydroxyl groups.

  20. Unambiguous Determination of the Absolute Configuration of Dimeric Stilbene Glucosides from the Rhizomes of Gnetum africanum.

    PubMed

    Buffeteau, Thierry; Cavagnat, Dominique; Bisson, Jonathan; Marchal, Axel; Kapche, Gilbert D; Battistini, Ilaria; Da Costa, Gregory; Badoc, Alain; Monti, Jean-Pierre; Mérillon, Jean-Michel; Waffo-Téguo, Pierre

    2014-08-22

    Dimeric stilbene glucosides 1-3 [two diastereomers of (-)-gnemonoside A (1a and 1b), (-)-gnemonoside C (2), and (-)-gnemonoside D (3)] as well as a mixture of the two enantiomers of gnetin C (4) were isolated from the rhizomes of Gnetum africanum. The two enantiomers of gnetin C, (+)-4 and (-)-4, were obtained from the aglycones of 1a and 1b, respectively. The configurations of these stilbenoids were investigated by NMR and vibrational circular dichroism (VCD) experiments. The absolute configurations of (-)-1a, (-)-2, (-)-3, and (-)-4 were established as 7aS,8aS by VCD spectroscopy in combination with density functional theory calculations. The antiamyloidogenic activity of the isolated stilbenes was also evaluated versus beta-amyloid fibrils. The four glucosides of gnetin C (1a, 1b, 2, and 3) were found to be the most active compounds, with inhibition percentages of 56, 56, 58, and 54 at 10 ?M, respectively. PMID:25093453

  1. 5''-Hydroxydigipenstroside and Penstriatoside: Novel Dimeric and Trimeric Open-Chain Monoterpene Glucosides from Penstemon digitalis*.

    PubMed

    Teborg, D; Steigel, A; Junior, P

    1991-04-01

    A new dimeric open-chain monoterpene glucoside, 5''-hydroxydigipenstroside {1-beta- D-glucopyranosyl)-8-[5'',8''-dihydroxy-2'',6''-dimethyl-2''( E),6''( E)-octadienoyl]-5,8-dihydroxy-2,6-dimethyl-2( E),6( E)-octadienoate} has been isolated from leaves of PENSTEMON DIGITALIS Nutt. In addition, the novel trimeric open-chain monoterpene glucoside penstriatoside {1-(beta- D-glucopyranosyl)-8-[5'',8''-dihydroxy-2'',6''-dimethyl-2''( E),6''( E)-octadienoyl-8''-(5''',8'''-dihydroxy-2''',6'''-dimethyl-2''' ( E)6'''( E)-octadienoyl)]-5,8-dihydroxy-2,6-dimethyl-2 ( E),6( E)-octadienoate} has been encountered. The structures of both compounds have been elucidated by spectroscopic means (FD-, FAB-mass, (1)H-, (13)C-NMR, COSY, DEPT). PMID:17226149

  2. New isopimarane diterpene and new cineole type glucoside from Nepeta prattii.

    PubMed

    Hou, Zhen-Fu; Tu, Yong-Qiang; Li, Yu

    2002-04-01

    Together with sixteen known compounds, a new isopimarane diterpene (prattol) and a new cineole type glucoside were isolated from Nepeta prattii. Their structures were elucidated on the basis of spectral methods as isopimar-15-en-3 beta,8 beta,20-triol, and (1R, 2R, 4S)-1,8-epoxy-p-methan-2-O-beta-D-glucopyranosyl(1-->6)-beta- D-glucopyranoside. PMID:11998451

  3. Isolation of maltol glucoside from the floral nectar of New Zealand m?nuka (Leptospermum scoparium).

    PubMed

    Adams, Christopher J; Grainger, Megan N C; Manley-Harris, Merilyn

    2015-05-01

    Maltol glucoside (3-(?-D-glucopyranosyloxy)-2-methyl-4H-pyran-4-one), 1, was isolated from a preparation of the floral nectar from the New Zealand m?nuka tree (Leptospermum scoparium). 1 eluted just after dihydroxyacetone in HPLC of underivatized nectar and showed a UV absorbance maximum of 258 nm. The structure of 1 was confirmed by NMR and high resolution mass spectrometry. PMID:25529685

  4. Structural analysis of novel bioactive acylated steryl glucosides in pre-germinated brown rice bran.

    PubMed

    Usuki, Seigo; Ariga, Toshio; Dasgupta, Somsankar; Kasama, Takeshi; Morikawa, Keiko; Nonaka, Shota; Okuhara, Yasuhide; Kise, Mitsuo; Yu, Robert K

    2008-10-01

    Previous studies from our laboratory indicated that pre-germinated brown rice (PR) contained certain unknown bioactive lipids that activated two enzymes related to diabetes: Na+/K+ATPase and homocysteine-thiolactonase. In this paper, we report on the isolation and structural characterization of the activator lipids from PR bran as acylated steryl glucosides (ASGs). The activator lipid was isolated by silica gel column chromatography, and its chemical structure was determined by NMR, GC-MS, and tandem mass spectrometry. We demonstrated that the bioactive component consists of a mixture of acylated steryl beta-glucosides. Delta8-cholesterol and 2-hydroxyl stearic acid were identified as constituents of ASGs. The steryl glucosides (SGs) subsequent to alkaline hydrolysis lost this enzyme activator activity. Soybean-derived ASGs were not active. This activity may be quite peculiar to PR-derived ASGs. Our findings suggest that the molecular species of ASG may play an important contributing role in the anti-diabetic properties of a PR diet. PMID:18587070

  5. Regulation of gene expression: Cryptic ?-glucoside (bgl) operon of Escherichia coli as a paradigm

    PubMed Central

    Harwani, Dharmesh

    2014-01-01

    Bacteria have evolved various mechanisms to extract utilizable substrates from available resources and consequently acquire fitness advantage over competitors. One of the strategies is the exploitation of cryptic cellular functions encoded by genetic systems that are silent under laboratory conditions, such as the bgl (?-glucoside) operon of E. coli. The bgl operon of Escherichia coli, involved in the uptake and utilization of aromatic ?-glucosides salicin and arbutin, is maintained in a silent state in the wild type organism by the presence of structural elements in the regulatory region. This operon can be activated by mutations that disrupt these negative elements. The fact that the silent bgl operon is retained without accumulating deleterious mutations seems paradoxical from an evolutionary view point. Although this operon appears to be silent, specific physiological conditions might be able to regulate its expression and/or the operon might be carrying out function(s) apart from the utilization of aromatic ?-glucosides. This is consistent with the observations that the activated operon confers a Growth Advantage in Stationary Phase (GASP) phenotype to Bgl+ cells and exerts its regulation on at least twelve downstream target genes. PMID:25763016

  6. Deaminated UV filter 3-hydroxykynurenine O-beta-D-glucoside is found in cataractous human lenses.

    PubMed

    Snytnikova, Olga A; Fursova, Anjella Zh; Chernyak, Elena I; Vasiliev, Vladimir G; Morozov, Sergey V; Kolosova, Nataliya G; Tsentalovich, Yuri P

    2008-06-01

    Analysis of UV filter levels in 48 cataractous human lenses was performed with the use of HPLC. A new chromophore with the absorption maximum at 410nm and molecular mass of 369Da was detected and assigned as deaminated 3-hydroxykynurenine O-beta-D-glucoside (3OHCKAG). Cataractous lenses are characterized by the wide range of the UV filter concentrations and remarkably lower levels of UV filters and glutathione than published for the normal lenses. No correlation between the lens age and the level of UV filters has been found in cataractous lenses. PMID:18436210

  7. Total glucosides of peony attenuates experimental autoimmune encephalomyelitis in C57BL/6 mice.

    PubMed

    Huang, Qiling; Ma, Xiaomeng; Zhu, Dong Liang; Chen, Li; Jiang, Ying; Zhou, Linli; Cen, Lei; Pi, Rongbiao; Chen, Xiaohong

    2015-07-15

    Total glucosides of peony (TGP), an active compound extracted from the roots of Paeonia lactiflora Pall, has wide pharmacological effects on nervous system. Here we examined the effects of TGP on experimental autoimmune encephalomyelitis (EAE), an established model of multiple sclerosis (MS). The results showed that TGP can reduce the severity and progression of EAE in C57 BL/6 mice. In addition, TGP also down-regulated the Th1/Th17 inflammatory response and prevented the reduced expression of brain-derived neurotrophic factor and 2',3'-cyclic nucleotide 3'-phosphodiesterase of EAE. These findings suggest that TGP could be a potential therapeutic agent for MS. PMID:26025060

  8. New CuCl2-induced glucoside esters and other constituents from Portucala oleracea.

    PubMed

    Wu, Bin; Yu, Liyan; Wu, Xiaodan; Chen, Jianbo

    2012-04-01

    Two new glucoside esters 1 and 2 were produced as stress metabolites in the fresh leaves of Portulaca oleracea, in response to abiotic stress elicitation by CuCl(2). A new sugar ester (3) and two known compounds (4 and 5) were also isolated. Their structures were established by spectroscopic means. The antioxidative activities of stress metabolites and the related isolates were evaluated by DPPH assay. The results showed that new stress-driven adducts of monolignans and monoterpenes with a glucose bridge exhibited much stronger antioxidative activities than other compounds. PMID:22361155

  9. Caffeoyl glucosides from Nandina domestica inhibit LPS-induced endothelial inflammatory responses.

    PubMed

    Kulkarni, Roshan R; Lee, Wonhwa; Jang, Tae Su; Lee, JungIn; Kwak, Soyoung; Park, Mi Seon; Lee, Hyun-Shik; Bae, Jong-Sup; Na, MinKyun

    2015-11-15

    Endothelial dysfunction is a key pathological feature of many inflammatory diseases, including sepsis. In the present study, a new caffeoyl glucoside (1) and two known caffeoylated compounds (2 and 3) were isolated from the fruits of Nandina domestica Thunb. (Berberidaceae). The compounds were investigated for their effects against lipopolysaccharide (LPS)-mediated endothelial inflammatory responses. At 20?M, 1 and 2 inhibited LPS-induced hyperpermeability, adhesion, and migration of leukocytes across a human endothelial cell monolayer in a dose-dependent manner suggesting that 1 and 2 may serve as potential scaffolds for the development of therapeutic agents to treat vascular inflammatory disorders. PMID:26410076

  10. Production of unnatural glucosides of curcumin with drastically enhanced water solubility by cell suspension cultures of Catharanthus roseus.

    PubMed

    Kaminaga, Yasuhisa; Nagatsu, Akito; Akiyama, Takumi; Sugimoto, Naoki; Yamazaki, Takeshi; Maitani, Tamio; Mizukami, Hajime

    2003-12-01

    Catharanthus roseus cell suspension cultures converted exogenously supplied curcumin to a series of glucosides, none of which has been found in nature so far. The efficiency of glucosylation was dependent on culture stage of the cells and medium sucrose concentration. Methyl jasmonate and salicylic acid enhanced the glucoside formation only when they were added to the cultures prior to the addition of curcumin. The glucoside yield was 2.5 micromol/g fresh weight of the cells at an optimal culture condition. The water solubility of curcumin-4',4"-O-beta-D-digentiobioside was 0.65 mmol/ml, which was 20 million-fold higher than that of curcumin. PMID:14644434

  11. Glucosylation of Steviol and Steviol-Glucosides in Extracts from Stevia rebaudiana Bertoni

    PubMed Central

    Shibata, Hitoshi; Sonoke, Satoru; Ochiai, Hideo; Nishihashi, Hideji; Yamada, Masaharu

    1991-01-01

    To evaluate and characterize stevioside biosynthetic pathway in Stevia rebaudiana Bertoni cv Houten, two enzyme fractions that catalyze glucosylation of steviol (ent-13-hydroxy kaur-16-en-19-oic acid) and steviol-glucosides (steviol-13-O-glucopyranoside, steviolbioside and stevioside), utilizing UDP-glucose as the glucose donor, were prepared from the soluble extracts of S. rebaudiana leaves. Enzyme fraction I, passed through DEAE-Toyopearl equilibrated with 50 millimolar K-phosphate pH 7.5, catalyzed the glucosylation to steviol and 19-O-methylsteviol, but not to iso-steviol and 13-O-methylsteviol, indicating that 13-hydroxyl group of the steviol skeleton is glucosylated first from UDP-glucose to produce steviol-13-O-glucopyranoside. Enzyme fraction II, eluted from the DEAE-Toyopearl column with 0.15 molar KCI, catalyzed the glucose transfer from UDP-glucose to steviol-13-O-glucopyranoside, steviolbioside and stevioside, but not to rubusoside (13, 19-di-O-glucopyranoside) and rebaudioside A. The reaction products glucosylated from steviol-13-O-glucopyranoside, steviolbioside and stevioside were identified to be steviolbioside, stevioside and rebaudioside A, respectively. These results indicate that in the steviol-glucoside biosynthetic pathway, steviol-13-O-glucopyranoside produced from the steviol glucosylation is successively glucosylated to steviolbioside, then to stevioside producing rebaudioside A. PMID:16667943

  12. Effects on Liver Lipid Metabolism of the Naturally Occurring Dietary Flavone Luteolin-7-glucoside

    PubMed Central

    Sá, Carla; Oliveira, Ana Rita; Machado, Cátia; Azevedo, Marisa; Pereira-Wilson, Cristina

    2015-01-01

    Disruptions in whole-body lipid metabolism can lead to the onset of several pathologies such as nonalcoholic fatty liver disease (NAFLD) and cardiovascular diseases (CVDs). The present study aimed at elucidating the molecular mechanisms behind the lipid-lowering effects of the flavone luteolin-7-glucoside (L7G) which we previously showed to improve plasma lipid profile in rats. L7G is abundant in plant foods of Mediterranean diet such as aromatic plants used as herbs. Results show that dietary supplementation with L7G for one week induced the expression of peroxisome proliferator-activated receptor-alpha (PPAR-?) and of its target gene carnitine palmitoyl transferase 1 (CPT-1) in rat liver. L7G showed a tendency to decrease the hepatic expression of sterol regulatory element-binding protein-1 (SREBP-1), without affecting fatty acid synthase (FAS) protein levels. Although SREBP-2 and LDLr mRNA levels did not change, the expression of HMG CoA reductase (HMGCR) was significantly repressed by L7G. L7G also inhibited this enzyme's in vitro activity in a dose dependent manner, but only at high and not physiologically relevant concentrations. These results add new evidence that the flavone luteolin-7-glucoside may help in preventing metabolic diseases and clarify the mechanisms underlying the beneficial health effects of diets rich in fruits and vegetables. PMID:26113868

  13. Novel quercetin-3-O-glucoside eicosapentaenoic acid ester ameliorates inflammation and hyperlipidemia.

    PubMed

    Sekhon-Loodu, Satvir; Ziaullah, Ziaullah; Rupasinghe, H P Vasantha; Wang, Yanwen; Kulka, Marianna; Shahidi, Fereidoon

    2015-08-01

    Quercetin, a major flavonol, present abundantly in apples and onions, is widely studied for ameliorating metabolic syndrome abnormalities. However, quercetin is mainly present in plant food in the form of quercetin glycosides and has been reported for poor gastrointestinal absorption. The present study was designed with the purpose of imparting a lipophilic property to quercetin-3-O-glucoside (QG) by its acylation with eicosapentaenoic acid (EPA) and to study the influence of eicosapentaenoic acid ester of quercetin-3-O-glucoside (QE) on hyperlipidemia and inflammation in vivo and in vitro. QE was more effective in reducing the production of tumor necrosis factor-alpha (TNF-?), prostaglandin 2 (PGE2), cyclo-oxygenase (COX)-2 levels and nuclear expression of nuclear factor-kappa B (NF-?B) compared to the parent compounds (QG and EPA) and commercial drugs, after lipopolysaccharides (LPS) induced inflammation in THP-1 derived macrophages. Serum high-density lipoprotein (HDL)-cholesterol was significantly higher and hepatic total cholesterol concentration was lower in the rats fed high-fat diet supplemented with QE, compared to the high-fat diet with inflammation (HFL). The serum concentrations of C-reactive protein (CRP), interleukin (IL)-6, and interferon-gamma (IFN-?) were significantly lower in QE treatment group than HFL group. EPA conjugated flavonol, QE, had significant anti-inflammatory and hypolipidemic properties and may be effective for the treatment of obesity-related disorders. PMID:26165697

  14. Cyanidin-3-glucoside Inhibits ATP-induced Intracellular Free Ca2+ Concentration, ROS Formation and Mitochondrial Depolarization in PC12 Cells

    PubMed Central

    Perveen, Shazia; Yang, Ji Seon; Ha, Tae Joung

    2014-01-01

    Flavonoids have an ability to suppress various ion channels. We determined whether one of flavonoids, cyanidin-3-glucoside, affects adenosine 5'-triphosphate (ATP)-induced calcium signaling using digital imaging methods for intracellular free Ca2+ concentration ([Ca2+]i), reactive oxygen species (ROS) and mitochondrial membrane potential in PC12 cells. Treatment with ATP (100µM) for 90 sec induced [Ca2+]i increases in PC12 cells. Pretreatment with cyanidin-3-glucoside (1µ g/ml to 100µg/ml) for 30 min inhibited the ATP-induced [Ca2+]i increases in a concentration-dependent manner (IC50=15.3µg/ml). Pretreatment with cyanidin-3-glucoside (15µg/ml) for 30 min significantly inhibited the ATP-induced [Ca2+]i responses following removal of extracellular Ca2+ or depletion of intracellular [Ca2+]i stores. Cyanidin-3-glucoside also significantly inhibited the relatively specific P2X2 receptor agonist 2-MeSATP-induced [Ca2+]i responses. Cyanidin-3-glucoside significantly inhibited the thapsigargin or ATP-induced store-operated calcium entry. Cyanidin-3-glucoside significantly inhibited the ATP-induced [Ca2+]i responses in the presence of nimodipine and ?-conotoxin. Cyanidin-3-glucoside also significantly inhibited KCl (50 mM)-induced [Ca2+]i increases. Cyanidin-3-glucoside significantly inhibited ATP-induced mitochondrial depolarization. The intracellular Ca2+ chelator BAPTA-AM or the mitochondrial Ca2+ uniporter inhibitor RU360 blocked the ATP-induced mitochondrial depolarization in the presence of cyanidin-3-glucoside. Cyanidin-3-glucoside blocked ATP-induced formation of ROS. BAPTA-AM further decreased the formation of ROS in the presence of cyanidin-3-glucoside. All these results suggest that cyanidin-3-glucoside inhibits ATP-induced calcium signaling in PC12 cells by inhibiting multiple pathways which are the influx of extracellular Ca2+ through the nimodipine and ?-conotoxin-sensitive and -insensitive pathways and the release of Ca2+ from intracellular stores. In addition, cyanidin-3-glucoside inhibits ATP-induced formation of ROS by inhibiting Ca2+-induced mitochondrial depolarization. PMID:25177161

  15. A family 3 glycosyl hydrolase of Dickeya dadantii 3937 is involved in the cleavage of aromatic glucosides.

    PubMed

    Charaoui-Boukerzaza, Sana; Hugouvieux-Cotte-Pattat, Nicole

    2013-11-01

    Dickeya dadantii is a phytopathogenic bacterium secreting a large array of plant-cell-wall-degrading enzymes that participate in the infection and maceration of the host plant tissue. Sequencing of the D. dadantii 3937 genome predicted several genes encoding potential glycosidases. One of these genes, bgxA, encodes a protein classified in family 3 of glycosyl hydrolases. Inactivation of bgxA and the use of a gene fusion revealed that this gene is not essential for D. dadantii pathogenicity but that it is expressed during plant infection. The bgxA expression is induced in the presence of glycosidic or non-glycosidic aromatic compounds, notably ferulic acid, cinnamic acid, vanillic acid and salicin. The BgxA enzyme has a principal ?-d-glucopyranosidase activity and a secondary ?-d-xylopyranosidase activity (ratio 70?:?1). This enzyme activity is inhibited by different aromatic glycosides or phenolic compounds, in particular salicin, arbutin, ferulic acid and vanillic acid. Together, the induction effects and the enzyme inhibition suggest that BgxA is mostly involved in the cleavage of aromatic ?-glucosides. There is evidence of functional redundancy in the D. dadantii ?-glucoside assimilation pathway. In contrast to other ?-glucoside assimilation systems, involving cytoplasmic phospho-?-glucosidases, the cleavage of aromatic glucosides in the periplasmic space by BgxA may avoid the release of a toxic phenolic aglycone into the cytoplasm while still allowing for catabolism of the glucose moiety. PMID:24002750

  16. A Comparative Analysis of the Photo-Protective Effects of Soy Isoflavones in Their Aglycone and Glucoside Forms

    PubMed Central

    Iovine, Barbara; Iannella, Maria Luigia; Gasparri, Franco; Giannini, Valentina; Monfrecola, Giuseppe; Bevilacqua, Maria Assunta

    2012-01-01

    Isoflavones exist in nature predominantly as glucosides such as daidzin or genistin and are rarely found in their corresponding aglycone forms daidzein and genistein. The metabolism and absorption of isoflavones ingested with food is well documented, but little is known about their use as topical photo-protective agents. The aim of this study was to investigate in a comparative analysis the photo-protective effects of isoflavones in both their aglycone and glucoside forms. In human skin fibroblasts irradiated with 60 mJ/cm2 ultraviolet B (UVB), we measured the expression levels of COX-2 and Gadd45, which are involved in inflammation and DNA repair, respectively. We also determined the cellular response to UVB-induced DNA damage using the comet assay. Our findings suggest that both the isoflavone glucosides at a specific concentration and combination with an aglycone mixture exerted an anti-inflammatory and photo-protective effect that prevented 41% and 71% of UVB-induced DNA damage, respectively. The advantages of using either isoflavone glucosides or an aglycone mixture in applications in the field of dermatology will depend on their properties and their different potential uses. PMID:23211668

  17. Clarification of Reconstituted Frozen Orange Juice Concentrate by Continuous Flow Centrifugation for Limonin Glucoside Solid Phase Extraction

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The clarification of reconstituted frozen orange juice concentrate by continuous-flow centrifugation in preparation to being applied to a solid phase extraction column for the isolation of limonin glucoside has been evaluated. Clarification experiments spanning over three different flow rates (325,...

  18. Cytosolic pyridoxine-beta-D-glucoside hydrolase from porcine jejunal mucosa. Purification, properties, and comparison with broad specificity beta-glucosidase.

    PubMed

    McMahon, L G; Nakano, H; Levy, M D; Gregory, J F

    1997-12-19

    During studies of the nutritional utilization of pyridoxine 5'-beta-D-glucoside, a major form of vitamin B6 in plants, we detected two cytosolic beta-glucosidases in jejunal mucosa. As expected, one was broad specificity beta-glucosidase that hydrolyzed aryl beta-D-glycosides but not pyridoxine beta-D-glucoside. We also found a previously unknown enzyme, designated pyridoxine-beta-D-glucoside hydrolase, that efficiently hydrolyzed pyridoxine beta-D-glucoside. These were separated and purified as follows: broad specificity beta-glucosidase 1460-fold and pyridoxine-beta-D-glucoside hydrolase 36,500-fold. Purified pyridoxine-beta-D-glucoside hydrolase did not hydrolyze any of the aryl glycosides tested but did hydrolyze cellobiose and lactose. Pyridoxine-beta-D-glucoside hydrolase exhibited a pH optimum of 5.5 and apparent molecular mass of 130 kDa by SDS-polyacrylamide gel electrophoresis and 160 kDa by nondenaturing gel filtration, in contrast to 60 kDa for native and denatured broad specificity beta-glucosidase. Glucono-delta-lactone was a strong inhibitor of both enzymes. Ionic and nonionic detergents were inhibitory for each enzyme. Conduritol B epoxide, a potent inhibitor of lysosomal acid beta-glucosidase, inhibited pyridoxine-beta-D-glucoside hydrolase but not broad specificity beta-glucosidase, but both were inhibited by the mechanism-based inhibitor 2-deoxy-2-fluoro-beta-D-glucosyl fluoride. Our findings indicate major differences between these two cytosolic beta-glucosidases. Studies addressing the role of vitamin B6 nutrition in regulating the activity and its consequences regarding pyridoxine glucoside bioavailability are in progress. PMID:9405396

  19. Occurrence of Deoxynivalenol and Deoxynivalenol-3-glucoside in Hard Red Spring Wheat Grown in the USA

    PubMed Central

    Simsek, Senay; Ovando-Martínez, Maribel; Ozsisli, Bahri; Whitney, Kristin; Ohm, Jae-Bom

    2013-01-01

    Deoxynivalenol (DON) is a mycotoxin found in wheat that is infected with Fusarium fungus. DON may also be converted to a type of “masked mycotoxin”, named deoxynivalenol-3-glucoside (D3G), as a result of detoxification of the plant. In this study, DON and D3G were measured using gas chromatographic (GC) and liquid chromatography-mass spectrometry (LC-MS) in wheat samples collected during 2011 and 2012 in the USA. Results indicate that the growing region had a significant effect on the DON and D3G (p < 0.0001). There was a positive correlation between both methods (GC and LC-MS) used for determination of DON content. DON showed a significant and positive correlation with D3G during 2011. Overall, DON production had an effect on D3G content and kernel damage, and was dependent on environmental conditions during Fusarium infection. PMID:24351720

  20. Structure and cytotoxic activity of enzymatic hydrolysis products of secoiridoid glucosides, isoligustroside and isooleuropein.

    PubMed

    Kikuchi, Masafumi; Yaoita, Yasunori; Mano, Nariyasu; Kikuchi, Masao

    2011-04-01

    Hydrolysis of isoligustroside (1) and isooleuropein (2), secoiridoid glucosides, in the presence of ?-glucosidase provided 2-(4-hydroxyphenyl)methyl (2R,3S,4S)-3-formyl-3,4-dihydro-4-(2-methoxy-2-oxoethyl)-2-methyl-2H-pyran-5-carboxylate (3) and 2-(3,4-dihydroxyphenyl)methyl (2R,3S,4S)-3-formyl-3,4-dihydro-4-(2-methoxy-2-oxoethyl)-2-methyl-2H-pyran-5-carboxylate (4), respectively. The structures of 3 and 4 were elucidated on the basis of extensive spectral analyses, including 2D-NMR experiments. Compounds 3 and 4 were found to be new rearrangement products of the aglycones of 1 and 2. The cytotoxic activities of 3 and 4 were evaluated using a disease-oriented panel of 39 human cancer cell lines and showed moderate cytotoxic activity for 4, while 3 exhibited weaker activity compared to that of 4. PMID:21480510

  1. Secoiridoid glucosides and related compounds from Syringa reticulata and their antioxidant activities.

    PubMed

    Bi, Xueyan; Li, Wei; Sasaki, Tatsunori; Li, Qin; Mitsuhata, Naoko; Asada, Yoshihisa; Zhang, Qingbo; Koike, Kazuo

    2011-11-01

    A 70% EtOH extract from the bark of Syringareticulata has shown significant antioxidant activity. Chemical study on the extract resulted in the isolation of seventeen compounds (1-17), including a novel oleoside-type secoiridoid glucoside, reticuloside (1), and the structures were elucidated on the basis of extensive spectroscopic analyses. Among the isolated compounds, jaspolyoside (2), oleuropein (4) and 2-(3,4-dihydroxy)-phenylethyl-?-d-glucopyranoside (17), showed the most potent superoxide anion scavenging activity with the EC(50) values of 4.97, 2.57 and 4.97?M, respectively. The structure-activity relationship indicated that the presence of 2-(3,4-dihydroxyphenyl)-ethoxy group is important for exhibiting the activity. PMID:21955940

  2. Stability studies of ascorbic acid 2-glucoside in cosmetic lotion using surface response methodology.

    PubMed

    Huang, Wen-Ying; Lee, Pei-Chi; Huang, Ling-Kuei; Lu, Li-Ping; Liao, Wayne C

    2013-03-15

    Ascorbic acid 2-glucoside (AA-2G) has been widely used in cream and lotion types of cosmetic products. Thus, the degradation of AA-2G caused by the temperature change and pH variation was very critical for determining the bio-functionality of cosmetics. Response surface methodology (RSM) was introduced to study the influence of temperature and pH on the stability of AA-2G. The optimal condition of retaining AA-2G with the highest stability was determined to be 55.3°C and pH 6.4. The antioxidative activities of AA-2G including DPPH and ABTS free radical scavenging activities, metal chelating activity, and reducing ability were also determined. AA-2G was a good ascorbic acid derivative which could be used in cosmetic products as an active ingredient. PMID:23416010

  3. The crystal structure and physicochemical properties of L-ascorbic acid 2-glucoside.

    PubMed

    Mandai, T; Yoneyama, M; Sakai, S; Muto, N; Yamamoto, I

    1992-08-01

    The stable L-ascorbic acid glucoside produced by the action of the cyclomaltodextrin glucanotransferase (CGTase, EC 2.4.1.19) from Bacillus stearothermophilus was crystallized from an aqueous solution. Determination of the molecular structure by single crystal X-ray analysis showed the compound to be 2-O-alpha-D-glucopyranosyl-L-ascorbic acid (AA-2G). The crystals are orthorhombic, space group P2(1)2(1)2(1), with unit-cell dimensions a = 11.929 A, b = 24.351 A, and c = 4.864 A. The D-glucopyranose residue has the 4C1 conformation. These conclusions are in good agreement with those based on the 13C-NMR spectrum. The general physicochemical properties of crystalline AA-2G are reported. PMID:1423355

  4. Daphnane-type diterpenoid glucosides and further constituents of Euphorbia pilosa.

    PubMed

    Zhang, Xu-Dong; Ni, Wei; Yan, Huan; Li, Gen-Tao; Zhong, Hui-Min; Li, Yan; Liu, Hai-Yang

    2014-05-01

    Phytochemical investigation of whole plants of Euphorbia pilosa led to the isolation and identification of two new daphnane-diterpenoid glucosides, euphopilosides A and B (1 and 2, resp.), and a new ent-abietane, euphopilolide (3), together with eight known compounds. Compounds 1 and 2 are the first daphnane-type diterpenoid glycosides. Their structures were elucidated by a combination of 1D- and 2D-NMR, and MS analyses, and acid hydrolysis. Compounds 1-9 were evaluated for their in vitro cytotoxicities against five human tumor cell lines, HL-60, SMMC-7721, A-549, MCF-7, and SW-480. Compound 7 showed moderate inhibitory activity against all five cell lines. PMID:24827685

  5. Binding characteristics and protective capacity of cyanidin-3-glucoside and its aglycon to calf thymus DNA.

    PubMed

    Zhang, Chao; Guo, Xiaofei; Cai, Wenqian; Ma, Yue; Zhao, Xiaoyan

    2015-04-01

    The binding characteristics and protective capacity of cyanidin (Cy) and cyanidin-3-glucoside (C3G) to calf thymus DNA were explored for the first time. The Cy and C3G gave a bathochromic shift to the ultraviolet-visible spectra of the DNA, indicating the formation of the DNA-Cy and DNA-C3G complexes. The complexes were formed by an intercalative binding mode based on the results of the fluorescence spectra and competitive binding analysis. Meanwhile, the Cy and C3G protected the DNA from the damage induced by the hydroxyl radical. The binding capacity and protective capacity of the C3G were stronger than that of the Cy. Furthermore, the formation of the DNA-anthocyanin complexes was spontaneous when the hydrogen bond and hydrophobic force played a key role. Hence, the Cy and C3G could protect the DNA automatically from the damage induced by the hydroxyl radical. PMID:25810071

  6. Mozambioside Is an Arabica-Specific Bitter-Tasting Furokaurane Glucoside in Coffee Beans.

    PubMed

    Lang, Roman; Klade, Stefan; Beusch, Anja; Dunkel, Andreas; Hofmann, Thomas

    2015-12-01

    Sensory-guided fractionation of a roasted coffee beverage revealed a highly polar, bitter-tasting subfraction, from which the furokaurane glucoside mozambioside was isolated and identified in its chemical structure by means of HDMS and NMR spectra. Sensory evaluation revealed a bitter taste recognition threshold of 60 (±10) ?mol/L. UPLC-HDMS quantitation of raw coffee beans showed that Arabica coffees contained 396-1188 nmol/g mozambioside, whereas only traces (<5 nmol/g) were detected in Robusta coffees, thus suggesting that mozambioside can be used as an analytical marker for Arabica coffee. Roasted Arabica contained a substantially reduced concentration (232 ± 37 nmol/g), indicating partial degradation of mozambioside during coffee roasting. Mozambioside was nearly quantitatively extracted into the aqueous brew during coffee-making (86-98%). PMID:26585544

  7. Direct detection, cloning and characterization of a glucoside hydrolase from forest soil.

    PubMed

    Hua, Mei; Zhao, Shubo; Zhang, Lili; Liu, Dongbo; Xia, Hongmei; Li, Fan; Chen, Shan

    2015-06-01

    A glucoside hydrolase gene, egl01, was cloned from the soil DNA of Changbai Mountain forest by homologous PCR amplification. The deduced sequence of 517 amino acids included a catalytic domain of glycoside hydrolase family 5 and was homologous to a putative cellulase from Bacillus licheniformis. The recombinant enzyme, Egl01, was maximally active at pH 5 and 50 °C and it was stable at pH 3-9, 4-50 °C, and also stable in the presence of metal ions, organic solvents, surfactants and salt. Its activity was above 120 % in 2-3 M NaCl/KCl and over 70 % was retained in 1-4 M NaCl/KCl for 6d. Egl01 hydrolyzed carboxymethyl cellulose, beechwood xylan, crop stalk, laminarin, filter paper, and avicel but not pNPG, indicating its broad substrate specificity. These properties make this recombinant enzyme a promising candidate for industrial applications. PMID:25700816

  8. New fatty acid, aromatic ester and monoterpenic benzyl glucoside from the fruits of Withania coagulans Dunal.

    PubMed

    Ali, Abuzer; Jameel, Mohammad; Ali, Mohammed

    2015-01-01

    The fruits of Withania coagulans Dunal (family: Solanaceae) are sweet, sedative, emetic, alterative and diuretic; used to treat asthma, biliousness, strangury, wounds, dyspepsia, flatulent colic, liver complaints and intestinal infections in the indigenous system of medicine. Phytochemical investigation of the methanolic extract of W. coagulans fruits led to the isolation of a new fatty acid, an aromatic ester and a monoterpenic benzyl glucoside characterised as n-octatriacont-17-enoic acid (3), geranilan-10-olyl dihydrocinnamoate (4) and geranilan-8-oic acid-10-olyl salicyloxy-2-O-?-D-glucofuranosyl-(6??1?)-O-?-D-glucofuranosyl-6?-n-octadec-9?',11?'-dienoate (5) along with two known fatty acids, n-dotriacont-21-enoic acid (1) and n-tetratriacontanoic acid (2). The structures of isolated phytoconstituents were established on the basis of 1D and 2D NMR, FT-IR, UV, and MS data and chemical means. PMID:25674818

  9. Molecular cloning and characterization of genistein 4'-O-glucoside specific glycosyltransferase from Bacopa monniera.

    PubMed

    Ruby; Santosh Kumar, R J; Vishwakarma, Rishi K; Singh, Somesh; Khan, Bashir M

    2014-07-01

    Health related benefits of isoflavones such as genistein are well known. Glycosylation of genistein yields different glycosides like genistein 7-O-glycoside (genistin) and genistein 4'-O-glycoside (sophoricoside). This is the first report on isolation, cloning and functional characterization of a glycosyltransferase specific for genistein 4'-O-glucoside from Bacopa monniera, an important Indian medicinal herb. The glycosyltransferase from B. monniera (UGT74W1) showed 49% identity at amino acid level with the glycosyltransferases from Lycium barbarum. The UGT74W1 sequence contained all the conserved motifs present in plant glycosyltransferases. UGT74W1 was cloned in pET-30b (+) expression vector and transformed into E. coli. The molecular mass of over expressed protein was found to be around 52 kDa. Functional characterization of the enzyme was performed using different substrates. Product analysis was done using LC-MS and HPLC, which confirmed its specificity for genistein 4'-O-glucoside. Immuno-localization studies of the UGT74W1 showed its localization in the vascular bundle. Spatio-temporal expression studies under normal and stressed conditions were also performed. The control B. monniera plant showed maximum expression of UGT74W1 in leaves followed by roots and stem. Salicylic acid treatment causes almost tenfold increase in UGT74W1 expression in roots, while leaves and stem showed decrease in expression. Since salicylic acid is generated at the time of injury or wound caused by pathogens, this increase in UGT74W1 expression under salicylic acid stress might point towards its role in defense mechanism. PMID:24664316

  10. The Metabolic Fate of Deoxynivalenol and Its Acetylated Derivatives in a Wheat Suspension Culture: Identification and Detection of DON-15-O-Glucoside, 15-Acetyl-DON-3-O-Glucoside and 15-Acetyl-DON-3-Sulfate.

    PubMed

    Schmeitzl, Clemens; Warth, Benedikt; Fruhmann, Philipp; Michlmayr, Herbert; Malachová, Alexandra; Berthiller, Franz; Schuhmacher, Rainer; Krska, Rudolf; Adam, Gerhard

    2015-08-01

    Deoxynivalenol (DON) is a protein synthesis inhibitor produced by the Fusarium species, which frequently contaminates grains used for human or animal consumption. We treated a wheat suspension culture with DON or one of its acetylated derivatives, 3-acetyl-DON (3-ADON), 15-acetyl-DON (15-ADON) and 3,15-diacetyl-DON (3,15-diADON), and monitored the metabolization over a course of 96 h. Supernatant and cell extract samples were analyzed using a tailored LC-MS/MS method for the quantification of DON metabolites. We report the formation of tentatively identified DON-15-O-?-D-glucoside (D15G) and of 15-acetyl-DON-3-sulfate (15-ADON3S) as novel deoxynivalenol metabolites in wheat. Furthermore, we found that the recently identified 15-acetyl-DON-3-O-?-D-glucoside (15-ADON3G) is the major metabolite produced after 15-ADON challenge. 3-ADON treatment led to a higher intracellular content of toxic metabolites after six hours compared to all other treatments. 3-ADON was exclusively metabolized into DON before phase II reactions occurred. In contrast, we found that 15-ADON was directly converted into 15-ADON3G and 15-ADON3S in addition to metabolization into deoxynivalenol-3-O-?-D-glucoside (D3G). This study highlights significant differences in the metabolization of DON and its acetylated derivatives. PMID:26274975

  11. The Metabolic Fate of Deoxynivalenol and Its Acetylated Derivatives in a Wheat Suspension Culture: Identification and Detection of DON-15-O-Glucoside, 15-Acetyl-DON-3-O-Glucoside and 15-Acetyl-DON-3-Sulfate

    PubMed Central

    Schmeitzl, Clemens; Warth, Benedikt; Fruhmann, Philipp; Michlmayr, Herbert; Malachová, Alexandra; Berthiller, Franz; Schuhmacher, Rainer; Krska, Rudolf; Adam, Gerhard

    2015-01-01

    Deoxynivalenol (DON) is a protein synthesis inhibitor produced by the Fusarium species, which frequently contaminates grains used for human or animal consumption. We treated a wheat suspension culture with DON or one of its acetylated derivatives, 3-acetyl-DON (3-ADON), 15-acetyl-DON (15-ADON) and 3,15-diacetyl-DON (3,15-diADON), and monitored the metabolization over a course of 96 h. Supernatant and cell extract samples were analyzed using a tailored LC-MS/MS method for the quantification of DON metabolites. We report the formation of tentatively identified DON-15-O-?-D-glucoside (D15G) and of 15-acetyl-DON-3-sulfate (15-ADON3S) as novel deoxynivalenol metabolites in wheat. Furthermore, we found that the recently identified 15-acetyl-DON-3-O-?-D-glucoside (15-ADON3G) is the major metabolite produced after 15-ADON challenge. 3-ADON treatment led to a higher intracellular content of toxic metabolites after six hours compared to all other treatments. 3-ADON was exclusively metabolized into DON before phase II reactions occurred. In contrast, we found that 15-ADON was directly converted into 15-ADON3G and 15-ADON3S in addition to metabolization into deoxynivalenol-3-O-?-D-glucoside (D3G). This study highlights significant differences in the metabolization of DON and its acetylated derivatives. PMID:26274975

  12. Diversified glucosinolate metabolism: biosynthesis of hydrogen cyanide and of the hydroxynitrile glucoside alliarinoside in relation to sinigrin metabolism in Alliaria petiolata

    PubMed Central

    Frisch, Tina; Motawia, Mohammed S.; Olsen, Carl E.; Agerbirk, Niels; Møller, Birger L.; Bjarnholt, Nanna

    2015-01-01

    Alliaria petiolata (garlic mustard, Brassicaceae) contains the glucosinolate sinigrin as well as alliarinoside, a ?-hydroxynitrile glucoside structurally related to cyanogenic glucosides. Sinigrin may defend this plant against a broad range of enemies, while alliarinoside confers resistance to specialized (glucosinolate-adapted) herbivores. Hydroxynitrile glucosides and glucosinolates are two classes of specialized metabolites, which generally do not occur in the same plant species. Administration of [UL-14C]-methionine to excised leaves of A. petiolata showed that both alliarinoside and sinigrin were biosynthesized from methionine. The biosynthesis of alliarinoside was shown not to bifurcate from sinigrin biosynthesis at the oxime level in contrast to the general scheme for hydroxynitrile glucoside biosynthesis. Instead, the aglucon of alliarinoside was formed from metabolism of sinigrin in experiments with crude extracts, suggesting a possible biosynthetic pathway in intact cells. Hence, the alliarinoside pathway may represent a route to hydroxynitrile glucoside biosynthesis resulting from convergent evolution. Metabolite profiling by LC-MS showed no evidence of the presence of cyanogenic glucosides in A. petiolata. However, we detected hydrogen cyanide (HCN) release from sinigrin and added thiocyanate ion and benzyl thiocyanate in A. petiolata indicating an enzymatic pathway from glucosinolates via allyl thiocyanate and indole glucosinolate derived thiocyanate ion to HCN. Alliarinoside biosynthesis and HCN release from glucosinolate-derived metabolites expand the range of glucosinolate-related defenses and can be viewed as a third line of defense, with glucosinolates and thiocyanate forming protein being the first and second lines, respectively. PMID:26583022

  13. Identification of the new UV filter compound cysteine-L-3-hydroxykynurenine O-beta-d-glucoside in human lenses.

    PubMed

    Hains, Peter G; Mizdrak, Jasminka; Streete, Isla M; Jamie, Joanne F; Truscott, Roger J W

    2006-09-18

    UV filters protect the human lens and retina from UV light-induced damage. Here, we report the identification of a new UV filter, cysteine-l-3-hydroxykynurenine O-beta-d-glucoside, which is present in older normal human lenses. Its structure was confirmed by independent synthesis. It is likely this novel UV filter is formed in the lens by nucleophilic attack of cysteine on the unsaturated ketone derived from deamination of 3-hydroxykynurenine O-beta-d-glucoside. Quantitation studies revealed considerable variation in normal lens levels that may be traced to the marked instability of the cysteine adduct. The novel UV filter was not detected in advanced nuclear cataract lenses. PMID:16949076

  14. Cool-cultivated red leaf lettuce accumulates cyanidin-3-O-(6?-O-malonyl)-glucoside and caffeoylmalic acid.

    PubMed

    Becker, Christine; Klaering, Hans-Peter; Kroh, Lothar W; Krumbein, Angelika

    2014-03-01

    Cultivating lettuce in greenhouses at low temperatures improves its CO2-balance and may increase its content of flavonoid glycosides and phenolic acids. We cultivated 5weeks old red leaf lettuce seedlings at 20/15°C (day/night) or 12/7°C until plants reached comparable growth stages: small heads were harvested after 13 (warm) and 26 (cool)days, while mature heads were harvested after 26 (warm) or 52 (cool)days. Additionally, some plants were cultivated first cool then warm and vice versa (39days). Cool-cultivated small heads had higher concentrations of cyanidin-3-O-(6?-O-malonyl)-glucoside and caffeoylmalic acid than warm-cultivated ones but we detected no differences concerning quercetin and luteolin glycosides or di-O-caffeoyltartaric and 5-O-caffeoylquinic acid. Regarding mature heads, there were only differences concerning cyanidin-3-O-(6?-O-malonyl)-glucoside. We therefore suggest that only cyanidin-3-O-(6?-O-malonyl)-glucoside was truly responsive to temperatures alone. Previously reported contrasting effects may rather be due to comparison of different growth stages or interactive effects with radiation. PMID:24176360

  15. Overexpression of the UGT73C6 alters brassinosteroid glucoside formation in Arabidopsis thaliana

    PubMed Central

    2011-01-01

    Background Brassinosteroids (BRs) are signaling molecules that play essential roles in the spatial regulation of plant growth and development. In contrast to other plant hormones BRs act locally, close to the sites of their synthesis, and thus homeostatic mechanisms must operate at the cellular level to equilibrate BR concentrations. Whilst it is recognized that levels of bioactive BRs are likely adjusted by controlling the relative rates of biosynthesis and by catabolism, few factors, which participate in these regulatory events, have as yet been identified. Previously we have shown that the UDP-glycosyltransferase UGT73C5 of Arabidopsis thaliana catalyzes 23-O-glucosylation of BRs and that glucosylation renders BRs inactive. This study identifies the closest homologue of UGT73C5, UGT73C6, as an enzyme that is also able to glucosylate BRs in planta. Results In a candidate gene approach, in which homologues of UGT73C5 were screened for their potential to induce BR deficiency when over-expressed in plants, UGT73C6 was identified as an enzyme that can glucosylate the BRs CS and BL at their 23-O-positions in planta. GUS reporter analysis indicates that UGT73C6 shows over-lapping, but also distinct expression patterns with UGT73C5 and YFP reporter data suggests that at the cellular level, both UGTs localize to the cytoplasm and to the nucleus. A liquid chromatography high-resolution mass spectrometry method for BR metabolite analysis was developed and applied to determine the kinetics of formation and the catabolic fate of BR-23-O-glucosides in wild type and UGT73C5 and UGT73C6 over-expression lines. This approach identified novel BR catabolites, which are considered to be BR-malonylglucosides, and provided first evidence indicating that glucosylation protects BRs from cellular removal. The physiological significance of BR glucosylation, and the possible role of UGT73C6 as a regulatory factor in this process are discussed in light of the results presented. Conclusion The present study generates essential knowledge and molecular and biochemical tools, that will allow for the verification of a potential physiological role of UGT73C6 in BR glucosylation and will facilitate the investigation of the functional significance of BR glucoside formation in plants. PMID:21429230

  16. Qualitative and Quantitative Analysis of Phenolic Acids, Flavonoids and Iridoid Glycosides in Yinhua Kanggan Tablet by UPLC-QqQ-MS/MS.

    PubMed

    Lin, Yu; Xu, Wen; Huang, Mingqing; Xu, Wei; Li, Huang; Ye, Miao; Zhang, Xun; Chu, Kedan

    2015-01-01

    A simple, rapid and specific ultra-performance liquid chromatography-triple quadrupole mass spectrometry method was developed for the analysis of 29 bioactive components (10 phenolic acids, 16 flavonoids, and three iridoid glycosides) in Yinhua Kanggan tablet (YHKGT), a herbal prescription used for treating upper respiratory infections, fevers, coughs and pharyngalgia. The separation was successfully achieved using a Waters Cortecs UPLC C18 column (50 × 2.1 mm, 1.6 ?m) and gradient elution with water-0.1% formic acid and acetonitrile. Polarity switching mode was used in the optimization of multiple reaction monitoring conditions. The analytical method was validated for linearity, precision and accuracy. Calibration curves for the 29 marker compounds showed good linear regression (r > 0.9982). The limits of detection (LOD) and limits of quantification (LOQ) for the 29 analytes were in the range of 0.03-4.99 ng/mL and 0.16-14.87 ng/mL, respectively. The relative standard deviation (RSD) values of intra-day precision, inter-day precision, repeatability, and stability were less than 2.79%, 4.87%, 4.18% and 4.71%, respectively. The recoveries of the 29 marker compounds were in the range of 94.67%-104.78% (RSD ? 4.72%). These results have shown that this developed method was efficient for the quality evaluation of YHKGT. PMID:26151117

  17. Characterization of beta-glucosidases with high specificity for the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) moench seedlings.

    PubMed

    Hösel, W; Tober, I; Eklund, S H; Conn, E E

    1987-01-01

    Two beta-glucosidases exhibiting high specificity for the cyanogenic glucoside dhurrin have been purified to near homogeneity from seedlings of Sorghum bicolor. Dhurrinase 1 was isolated from shoots of seedlings grown in the dark. Dhurrinase 2 was isolated from the green shoots of young seedlings grown in the light. The two enzymes were similar in following characteristics: their optimum activity is around pH 6.2; the enzymes are stable above pH 7; they are effectively inhibited by the beta-glycosidase inhibitors nojirimycin delta-gluconolactone and 1-amino-beta-D-glucoside. On the other hand, they clearly differed in other properties, e.g., molecular weights, isoelectric points, and substrate specificity. Moreover, dithiothreitol has no effect on dhurrinase 1, but is necessary for the activity of dhurrinase 2. Preliminary investigations indicate that the two enzymes are located in different parts of the sorghum seedlings: dhurrinase 1 is found in the coleoptiles and hypocotyls; dhurrinase 2 occurs in the leaves. Dhurrin (p-hydroxy-(S)-mandelonitrile-beta-D-glucoside) and its structural analog without the hydroxyl group, sambunigrin, were the only substrates hydrolyzed at high rate, the Km values with both enzymes being 0.15 and 0.3 mM, respectively. All other cyanogenic glucosides tested, as well as synthetic substrates such as 4-nitrophenyl-beta-D-glucoside, were in general poor substrates, especially for dhurrinase 1, the enzyme isolated from coleoptile and hypocotyl tissue. Dhurrinase 1 appears to exist within the seedlings as a tetramer (Mr - 2-2.4 X 10(5)) which dissociates without loss of activity into a dimeric form (Mr = 1-1.1 X 10(5)) upon extraction and purification. There is only one monomeric subunit with Mr = 5.7 X 10(4). Isolectric focusing and chromatofocusing of purified dhurrinase 1 showed the presence of at least three isomeric forms, but their relationship to each other is not known at the present time. Dhurrinase 2 appears to be a tetrameric protein with Mr = 2.5-3 X 10(5); it also has only one monomeric subunit of Mr = 6.1 X 10(4). In contrast to many other beta-glucosidases, the dhurrinases are not glycoproteins. PMID:3101594

  18. Analysis of Deoxynivalenol and Deoxynivalenol-3-glucoside in Hard Red Spring Wheat Inoculated with Fusarium Graminearum

    PubMed Central

    Ovando-Martínez, Maribel; Ozsisli, Bahri; Anderson, James; Whitney, Kristin; Ohm, Jae-Bom; Simsek, Senay

    2013-01-01

    Deoxynivalenol (DON) is a mycotoxin affecting wheat quality. The formation of the “masked” mycotoxin deoxinyvalenol-3-glucoside (D3G) results from a defense mechanism the plant uses for detoxification. Both mycotoxins are important from a food safety point of view. The aim of this work was to analyze DON and D3G content in inoculated near-isogenic wheat lines grown at two locations in Minnesota, USA during three different years. Regression analysis showed positive correlation between DON content measured with LC and GC among wheat lines, locality and year. The relationship between DON and D3G showed a linear increase until a certain point, after which the DON content and the D3G increased. Wheat lines having higher susceptibility to Fusarium showed the opposite trend. ANOVA demonstrated that the line and location have a greater effect on variation of DON and D3G than do their interaction among years. The most important factor affecting DON and D3G was the growing location. In conclusion, the year, environmental conditions and location have an effect on the D3G/DON ratio in response to Fusarium infection. PMID:24351715

  19. Enzymatic hydrolysis of steryl glucosides, major contaminants of vegetable oil-derived biodiesel.

    PubMed

    Aguirre, Andres; Peiru, Salvador; Eberhardt, Florencia; Vetcher, Leandro; Cabrera, Rodolfo; Menzella, Hugo G

    2014-05-01

    Biodiesels are mostly produced from lipid transesterification of vegetable oils, including those from soybean, jatropha, palm, rapeseed, sunflower, and others. Unfortunately, transesterification of oil produces various unwanted side products, including steryl glucosides (SG), which precipitate and need to be removed to avoid clogging of filters and engine failures. So far, efficient and cost-effective methods to remove SGs from biodiesel are not available. Here we describe for the first time the identification, characterization and heterologous production of an enzyme capable of hydrolyzing SGs. A synthetic codon-optimized version of the lacS gene from Sulfolobus solfataricus was efficiently expressed and purified from Escherichia coli, and used to treat soybean derived biodiesel containing 100 ppm of SGs. After optimizing different variables, we found that at pH 5.5 and 87 °C, and in the presence of 0.9 % of the emulsifier polyglycerol polyricinoleate, 81 % of the total amount of SGs present in biodiesel were hydrolyzed by the enzyme. This remarkable reduction in SGs suggests a path for the removal of these contaminants from biodiesel on industrial scale using an environmentally friendly enzymatic process. PMID:24265025

  20. Pathobiochemical effect of acylated steryl-?-glucoside on aggregation and cytotoxicity of ?-synuclein

    PubMed Central

    Usuki, Seigo; Kamitani, Tetsu; Matsuo, Yasuhiro; Yu, Robert, K.

    2013-01-01

    Objective Cycad seed consumption by the native islanders of Guam is frequently associated with high rates of Amyotrophic Lateral Sclerosis-Parkinsonism Dementia Complex (ALS-PDC); furthermore, accompanying pathological examination often exhibits ?-synuclein inclusions in the neurons of the affected brain. Acylated steryl-?-glucoside (ASG) contained in cycad seeds is considered as causative environmental risk factor. We aimed to investigate whether ASG influences aggregation and cell toxicity of ?-synuclein. Methods To understand whether ASG is a causative factor in the development of ALS-PDC, soybean-derived ASG was tested for its effect on in vitro aggregation of ?-synuclein using Thioflavin-T. ASG was also tested to determine whether it modulates ?-synuclein cytotoxicity in yeast cells. In addition, we determined whether an interaction between ASG and ?-synuclein occurs in the plasma membrane or cytoplasm using three factors: GM1 ganglioside, small unilamellar vesicles, and ATP. Results In the present study, we found that ASG-mediated acceleration of ?-synuclein aggregation is influenced by the presence of ATP, but not by the presence of GM1. ASG accelerated the ?-synuclein aggregation in the cytoplasm. ASG also enhanced ?-synuclein-induced cytotoxicity in yeast cells. Conclusions This study demonstrated that ASG directly enhances aggregation and cytotoxicity of ?-synuclein, which are often observed in patients with ALS-PDC. These results, using assays that replicate cytoplasmic conditions, are consistent with the molecular mechanism that cell toxicity is caused by intracellular ?-synuclein fibril formation in neuronal cells. PMID:22124781

  1. Cyanidin 3-glucoside improves diet-induced metabolic syndrome in rats.

    PubMed

    Bhaswant, Maharshi; Fanning, Kent; Netzel, Michael; Mathai, Michael L; Panchal, Sunil K; Brown, Lindsay

    2015-12-01

    Increased consumption of dark-coloured fruits and vegetables may mitigate metabolic syndrome. This study has determined the changes in metabolic parameters, and in cardiovascular and liver structure and function, following chronic administration of either cyanidin 3-glucoside (CG) or Queen Garnet plum juice (QG) containing cyanidin glycosides to rats fed either a corn starch (C) or a high-carbohydrate, high-fat (H) diet. Eight to nine-week-old male Wistar rats were randomly divided into six groups for 16-week feeding with C, C with CG or QG, H or H with CG or QG. C or H were supplemented with CG or QG at a dose of ?8mg/kg/day cyanidin glycosides from week 8 to 16. H rats developed signs of metabolic syndrome including visceral adiposity, impaired glucose tolerance, hypertension, cardiovascular remodelling, increased collagen deposition in left ventricle, non-alcoholic fatty liver disease, increased plasma liver enzymes and increased inflammatory cell infiltration in the heart and liver. Both CG and QG reversed these cardiovascular, liver and metabolic signs. However, no intact anthocyanins or common methylated/conjugated metabolites could be detected in the plasma samples and plasma hippuric acid concentrations were unchanged. Our results suggest CG is the most likely mediator of the responses to QG but that further investigation of the pharmacokinetics of oral CG in rats is required. PMID:26477387

  2. Use of 4-heptylumbelliferyl-beta-D-glucoside to identify Gaucher's disease heterozygotes.

    PubMed

    Butcher, B A; Gopalan, V; Lee, R E; Richards, T C; Waggoner, A S; Glew, R H

    1989-10-16

    Three fluorometric beta-glucosidase assays were compared for their ability to identify Gaucher's disease heterozygotes, using leukocytes as the source of enzyme: the pH 5.5-taurocholate assay of Peters et al.; the conduritol B epoxide dependent variation of that assay; and the newly developed method described herein. While the first two procedures utilize the standard substrate 4-methylumbelliferyl-beta-D-glucopyranoside to estimate beta-glucosidase activity, the new assay uses 4-heptylumbelliferyl-beta-D-glucoside as (C7UGlc) substrate. Use of this substrate enhances the specificity of the method for lysosomal glucocerebrosidase, thereby minimizing the contribution of the nonspecific cytosolic beta-glucosidase to estimates of substrate hydrolysis. Using Student's t test for the three assays examined, the C7UGlc assay procedure was determined to have the lowest p value (p less than 0.001) and highest t value (t = 4.95) for the discrimination between the mean glucocerebrosidase value of control and obligate Gaucher heterozygote samples. The high reliability and simplicity of the C7UGlc assay lends adequate reason to favor this assay for regular clinical diagnosis of Gaucher heterozygotes. PMID:2515009

  3. Structural characterization of chromone C-glucosides in a toxic herbal remedy.

    PubMed

    Wang, Wu; Cuyckens, Filip; Van den Heuvel, Hilde; Apers, Sandra; Pieters, Luc; Steenkamp, Vanessa; Stewart, Michael J; Luyckx, Valerie A; Claeys, Magda

    2003-01-01

    Two novel compounds, 8-C-D-glucopyranosyl-7-hydroxy-5-methylchromone-2-carboxylic acid and a 2-O'-p-coumaroyl derivative thereof, were identified in a herbal tea that caused severe vomiting in a South African patient who had taken the traditional remedy to clean his stomach. For structural characterization, electrospray (ES) ionization in combination with collision-induced dissociation (CID) and tandem mass spectrometry (MS/MS) were used, as well as UV and nuclear magnetic resonance (NMR) spectroscopy. Specific ions or neutral losses generated under conditions of ES-MS/CID/MS permitted the establishment of structural features such as the free carboxyl group, the C-hexosidic part and the p-coumaroyl group. NMR spectroscopy was necessary to support the structure of the chromone-type aglycone and the glucosidic parts. Since the compounds are structurally related to aloesin and aloeresin A, which are chemotaxonomic markers of Aloe species, and have not been previously reported, we propose that they were formed by oxidative degradation during preparation of the herbal tea from an Aloe species or during its storage. PMID:12478554

  4. The Multiple Strategies of an Insect Herbivore to Overcome Plant Cyanogenic Glucoside Defence

    PubMed Central

    Pentzold, Stefan; Zagrobelny, Mika; Roelsgaard, Pernille Sølvhøj; Møller, Birger Lindberg; Bak, Søren

    2014-01-01

    Cyanogenic glucosides (CNglcs) are widespread plant defence compounds that release toxic hydrogen cyanide by plant ?-glucosidase activity after tissue damage. Specialised insect herbivores have evolved counter strategies and some sequester CNglcs, but the underlying mechanisms to keep CNglcs intact during feeding and digestion are unknown. We show that CNglc-sequestering Zygaena filipendulae larvae combine behavioural, morphological, physiological and biochemical strategies at different time points during feeding and digestion to avoid toxic hydrolysis of the CNglcs present in their Lotus food plant, i.e. cyanogenesis. We found that a high feeding rate limits the time for plant ?-glucosidases to hydrolyse CNglcs. Larvae performed leaf-snipping, a minimal disruptive feeding mode that prevents mixing of plant ?-glucosidases and CNglcs. Saliva extracts did not inhibit plant cyanogenesis. However, a highly alkaline midgut lumen inhibited the activity of ingested plant ?-glucosidases significantly. Moreover, insect ?-glucosidases from the saliva and gut tissue did not hydrolyse the CNglcs present in Lotus. The strategies disclosed may also be used by other insect species to overcome CNglc-based plant defence and to sequester these compounds intact. PMID:24625698

  5. Metabolism, excretion and avoidance of cyanogenic glucosides in insects with different feeding specialisations.

    PubMed

    Pentzold, Stefan; Zagrobelny, Mika; Bjarnholt, Nanna; Kroymann, Juergen; Vogel, Heiko; Olsen, Carl Erik; Møller, Birger Lindberg; Bak, Søren

    2015-11-01

    Cyanogenic glucosides (CNglcs) are widespread plant defence compounds releasing toxic hydrogen cyanide when hydrolysed by specific ?-glucosidases after plant tissue damage. In contrast to specialist herbivores that have mechanisms to avoid toxicity from CNglcs, it is generally assumed that non-adapted herbivores are negatively affected by CNglcs. Recent evidence, however, implies that the defence potential of CNglcs towards herbivores may not be as effective as previously anticipated. Here, performance, metabolism and excretion products of insects not adapted to CNglcs were analysed, including species with different degrees of dietary specialisation (generalists, specialists) and different feeding modes (leaf-snipping lepidopterans, piercing-sucking aphids). Insects were reared either on cyanogenic or acyanogenic plants or on an artificial cyanogenic diet. Lepidopteran generalists (Spodoptera littoralis, Spodoptera exigua, Mamestra brassicae) were compared to lepidopteran glucosinolate-specialists (Pieris rapae, Pieris brassicae, Plutella xylostella), and a generalist aphid (Myzus persicae) was compared to an aphid glucosinolate-specialist (Lipaphis erysimi). All insects were tolerant to cyanogenic plants; in lepidopterans tolerance was mainly due to excretion of intact CNglcs. The two Pieris species furthermore metabolized aromatic CNglcs to amino acid conjugates (Cys, Gly, Ser) and derivatives of these, which is similar to the metabolism of benzylglucosinolates in these species. Aphid species avoided uptake of CNglcs during feeding. Our results imply that non-adapted insects tolerate plant CNglcs either by keeping them intact for excretion, metabolizing them, or avoiding uptake. PMID:26483288

  6. Cyanidin-3-glucoside isolated from mulberry fruits protects pancreatic ?-cells against glucotoxicity-induced apoptosis.

    PubMed

    Lee, Jong Seok; Kim, Young Rae; Park, Jun Myoung; Kim, Young Eon; Baek, Nam In; Hong, Eock Kee

    2015-04-01

    The present study investigated the cytoprotective effects of cyanidin?3?glucoside (C3G), isolated from mulberry fruits, on the glucotoxicity?induced apoptosis of pancreatic ??cells to evaluate the antidiabetic effects of this compound. MIN6N pancreatic ??cells were used to investigate the cytoprotective effects of C3G. In addition, the effects of C3G on the glucotoxicity?induced apoptosis of pancreatic ??cells was evaluated using MTT assay, immunofluorescent staining, flow cytometric and western blot analyses. The pancreatic ??cells cultured under high glucose conditions exhibited distinct apoptotic features. C3G decreased the generation of intracellular reactive oxygen species, DNA fragmentation and the rate of apoptosis. C3G also prevented pancreatic ??cell apoptosis induced by high glucose conditions by interfering with the intrinsic apoptotic pathways. In addition, C3G treatment resulted in increased insulin secretion compared with treatment with high glucose only. In conclusion, the results of the present study suggested that C3G obtained from mulberry fruits may be a potential phytotherapeutic agent for the prevention of diabetes. PMID:25501967

  7. PLS-Prediction and Confirmation of Hydrojuglone Glucoside as the Antitrypanosomal Constituent of Juglans Spp.

    PubMed

    Ellendorff, Therese; Brun, Reto; Kaiser, Marcel; Sendker, Jandirk; Schmidt, Thomas J

    2015-01-01

    Naphthoquinones (NQs) occur naturally in a large variety of plants. Several NQs are highly active against protozoans, amongst them the causative pathogens of neglected tropical diseases such as human African trypanosomiasis (sleeping sickness), Chagas disease and leishmaniasis. Prominent NQ-producing plants can be found among Juglans spp. (Juglandaceae) with juglone derivatives as known constituents. In this study, 36 highly variable extracts were prepared from different plant parts of J. regia, J. cinerea and J. nigra. For all extracts, antiprotozoal activity was determined against the protozoans Trypanosoma cruzi, T. brucei rhodesiense and Leishmania donovani. In addition, an LC-MS fingerprint was recorded for each extract. With each extract's fingerprint and the data on in vitro growth inhibitory activity against T. brucei rhodesiense a Partial Least Squares (PLS) regression model was calculated in order to obtain an indication of compounds responsible for the differences in bioactivity between the 36 extracts. By means of PLS, hydrojuglone glucoside was predicted as an active compound against T. brucei and consequently isolated and tested in vitro. In fact, the pure compound showed activity against T. brucei at a significantly lower cytotoxicity towards mammalian cells than established antiprotozoal NQs such as lapachol. PMID:26035104

  8. Synthesis of ??-?mangostin-D-glucoside in supercritical carbon dioxide media.

    PubMed

    Zarena, A S; Sankar, Kadimi Udaya

    2015-10-01

    ?-Mangostin, the major xanthone constituent of mangoteen fruit pericarp, has several important pharmaceutical application but its bioavailability is restricted due to its insolubility in water. Herein, we synthesized water soluble ?-mangostin-D-glucoside by glycosylation of ?-mangostin at hydroxyl group; using amyloglucosidase (3.2.1.3) catalyzed reaction in supercritical carbon dioxide (SC-CO2) media. Response surface methodology (RSM) based on a five-variable central composite rotatable design involving 32 experiments was used to determine the effect of pressure (80-160 bar), temperature (35-75 °C), enzyme concentration (15-45 mg), buffer pH (4.0-8.0) and buffer volume (1.0-5.0 mL). Experimental data fitted the second-order polynomial equation as indicated by R(2) value of 0.94. The optimal enzymatic conversion within the experimental range of the variables reached 20.3 % at a pressure of 120 bar, temperature of 55 °C, enzyme concentration of 30 mg, buffer volume of 3 mL and pH 6.0 which is well matched with the predictive yield. PMID:26396400

  9. ABCC1, an ATP binding cassette protein from grape berry, transports anthocyanidin 3-O-Glucosides.

    PubMed

    Francisco, Rita Maria; Regalado, Ana; Ageorges, Agnès; Burla, Bo J; Bassin, Barbara; Eisenach, Cornelia; Zarrouk, Olfa; Vialet, Sandrine; Marlin, Thérèse; Chaves, Maria Manuela; Martinoia, Enrico; Nagy, Réka

    2013-05-01

    Accumulation of anthocyanins in the exocarp of red grapevine (Vitis vinifera) cultivars is one of several events that characterize the onset of grape berry ripening (véraison). Despite our thorough understanding of anthocyanin biosynthesis and regulation, little is known about the molecular aspects of their transport. The participation of ATP binding cassette (ABC) proteins in vacuolar anthocyanin transport has long been a matter of debate. Here, we present biochemical evidence that an ABC protein, ABCC1, localizes to the tonoplast and is involved in the transport of glucosylated anthocyanidins. ABCC1 is expressed in the exocarp throughout berry development and ripening, with a significant increase at véraison (i.e., the onset of ripening). Transport experiments using microsomes isolated from ABCC1-expressing yeast cells showed that ABCC1 transports malvidin 3-O-glucoside. The transport strictly depends on the presence of GSH, which is cotransported with the anthocyanins and is sensitive to inhibitors of ABC proteins. By exposing anthocyanin-producing grapevine root cultures to buthionine sulphoximine, which reduced GSH levels, a decrease in anthocyanin concentration is observed. In conclusion, we provide evidence that ABCC1 acts as an anthocyanin transporter that depends on GSH without the formation of an anthocyanin-GSH conjugate. PMID:23723325

  10. Neuroprotection by tetrahydroxystilbene glucoside in the MPTP mouse model of Parkinson's disease.

    PubMed

    Zhang, Lingling; Huang, LinHong; Chen, Liangwei; Hao, Dingjun; Chen, Jianzong

    2013-10-24

    Our in vitro experiments suggested that tetrahydroxystilbene glucoside (TSG) affords a significant neuroprotective effect against MPP?-induced damage and apoptosis in PC12 cells though activation of the PI3K/Akt pathway. This study was aimed to investigate the potential neuroprotective effect of TSG in 1-methyl-4-phenyl-1,2,3,6-tetrahydropypridine (MPTP)-treated mouse model of Parkinson's disease (PD). We found that treatment of TSG protected dopaminergic neurons by preventing MPTP-induced decreases in substantia nigra tyrosine hydroxylase (TH)-positive cells and striatal dopaminergic transporter (DAT) protein levels. Furthermore, it was also associated with increasing striatal Akt and GSK3? phosphorylation, up-regulation of the Bcl-2/BAD ratio, and inhibition of the activation of caspase-9 and caspase-3. These results showed that TSG promoted dopamine neuron survival in vivo, the PI3K/Akt signaling pathway may have mediated the protection of TSG against MPTP, suggesting that TSG treatment might represent a neuroprotective treatment for PD. PMID:23911879

  11. Proteomic analysis for anti-atherosclerotic effect of tetrahydroxystilbene glucoside in rats.

    PubMed

    Yao, Wenjuan; Fan, Wenjun; Huang, Chao; Zhong, Hui; Chen, Xiangfan; Zhang, Wei

    2013-03-01

    2,3,5,4'-tetrahydroxystilbene-2-O-?-D-glucoside (TSG) extracted from Polygonum multiflorum (a traditional Chinese medicinal herb) has been proved to exhibit significant anti-atherosclerotic activity. In this study, we firstly used proteomic analyses to investigate the molecular events occurring in the atherosclerotic rats after TSG treatment. Aortic samples were collected from the atherosclerotic rat group and the TSG-treated group, and its proteome was analyzed by two-dimensional gel electrophoresis (2-DE). Proteins showing significant changes in expression were identified and analyzed by matrix-assisted desorption/ionization time of flight mass spectrometry (MALDI-TOF-MS). As a result, 21 protein spots were found with significant differential expression after the treatment with TSG. A total of 18 spots were identified by database searching, and 17 spots matched with known proteins. Among these proteins (11 proteins up-regulated and six proteins down-regulated), five proteins were mainly involved in inflammation, cholesterol transport, cell apoptosis and adhesion. TSG treatment enhanced the expression of HSP 70, lipocortin 1 and Apo A-I, and inhibited the expression of calreticulin, vimentin. Furthermore, we randomly selected four proteins and confirmed the results of proteomic analysis by RT-PCR and western blotting. In conclusion, TSG treatment suppresses atherosclerosis by altering the expression of different proteins. Calreticulin, vimentin, HSP 70, lipocortin 1, and Apo A-I, are key proteins that may be novel molecular targets responsible for atherogenesis suppression induced by TSG treatment. PMID:23206751

  12. Effects of tetrahydroxystilbene glucoside on mouse liver cytochrome P450 enzyme expressions.

    PubMed

    Wang, Yan-Ying; Yang, Jun; Liu, Hang; Lin, Feng-Qin; Shi, Jing-Shan; Zhang, Feng

    2015-04-01

    1. To investigate the effects of tetrahydroxystilbene glucoside (TSG), the main active component of Polygonum multiflorum, on mouse liver cytochrome P450 (Cyp) enzyme protein expressions. Male mice were randomly divided into the control, TSG low (10?mg/kg) and high dose (40?mg/kg) groups. After TSG intragastrical administration for 3, 5 and 7 d, mice were sacrificed and the mouse body and liver weight were detected. The Cyp enzymes and various transcription factors such as AhR, PXR and PPAR? protein expressions in mouse livers were measured by Western blotting assay. 2. No significant difference of mouse body and liver weight between the control and TSG treatment groups was detected. Additionally, TSG decreased Cyp1a2 and Cyp2e1 protein expressions after TSG treatment for 3, 5 and 7 d, respectively. Moreover, TSG suppressed Cyp3a11 protein expression after TSG treatment for 5 and 7 d. Furthermore, TSG high dose inhibited AhR and PXR protein expressions after TSG treatment for 5 and 7 d, while both TSG low dose and high dose obviously decreased PPAR? protein level from TSG treatment for 3 d. 3. TSG has inhibitory effects on mouse liver Cyp1a2, Cyp2e1 and Cyp3a11 protein expressions through the suppression of AhR, PXR and PPAR? activation. PMID:25350237

  13. Effect of heat/pressure on cyanidin-3-glucoside ethanol model solutions

    NASA Astrophysics Data System (ADS)

    Corrales, M.; Lindauer, R.; Butz, P.; Tauscher, B.

    2008-07-01

    The stability of cyanidin-3-glucoside (Cy3gl) in 50% ethanol model solutions under heat/pressure treatments was investigated. Cy3gl was rapidly degraded when solutions were subjected to a heat/pressure treatment. The higher the pressure and the temperature used, the higher the degradation. Moreover, the degradation was increased according to increasing holding times. Parallel to the degradation of Cy3gl several hydrolytic products were formed and identified by LC-DAD/ESI-MS. The degradation of Cy3gl was well fitted to a first order reaction (R=0.99). This study pointed out the rate of susceptibility of Cy3gl in model solutions to degrade when exposed to a heat/pressure treatment and the trigger effect of high hydrostatic pressure to hydrolyse Cy3gl. By contrast, the degradation of anthocyanins in a food matrix (red grape extract solutions) was negligible after a heat/pressure process at 600MPa, 70°C during 1h (P >0.05).

  14. Maintenance of cold-preserved porcine hepatocyte function with UW solution and ascorbic acid-2 glucoside.

    PubMed

    Takesue, Michihiko; Maruyama, Masanobu; Shibata, Norikuni; Kunieda, Takemi; Okitsu, Teru; Sakaguchi, Masakiyo; Totsugawa, Toshinori; Kosaka, Yoshikazu; Arata, Akira; Ikeda, Hideaki; Matsuoka, Junji; Oyama, Toshie; Kodama, Makoto; Ohmoto, Kenji; Yamamoto, Shinichiro; Kurabayashi, Yuzuru; Yamamoto, Itaru; Tanaka, Noriaki; Kobayashi, Naoya

    2003-01-01

    Normal human hepatocytes are an ideal source of liver-targeted cell therapies, such as hepatocyte transplantation and bioartificial livers, but availability of human donor livers for liver cell isolation is severely limited. To effectively utilize scarce donor organs for cell therapies, it is of extreme importance to establish an efficient isolation technique and an effective cold preservation solution for transportation of isolated cells. A lateral segment of the liver was surgically resected from pigs weighing 10 kg and a four-step collagenase and dispase digestion was conducted. Isolated hepatocytes were subjected to 8-h cold storage on ice. The following preservation solutions were tested: 1) University of Wisconsin (UW) solution, 2) UW with 100 microg/ml of ascorbic acid-2 glucoside (AA2G), 3) 100% fetal bovine serum (FBS), and 4) Dulbecco's modified Eagle's medium (DMEM) supplemented with 100% FBS. The mean viability of porcine hepatocytes was 95.5 +/- 2.5% when isolated in three independent experiments. Viability, plating efficiency, membrane stability, and ammonia metabolic capacity of cold-preserved hepatocytes were significantly better maintained by the use of UW solution. When AA2G (100 microg/ml) was combined with UW solution, such parameters were further improved. It was explained by inhibition of caspase-3 activation and retention of ATP at high levels of hepatocytes preserved with UW solution containing AA2G. The present work demonstrates that a combination of UW solution with AA2G (100 microg/ml) would be a useful cold preservation means for the development of cell therapies. PMID:14579928

  15. Application of ascorbic acid 2-glucoside as a solubilizing agent for clarithromycin: solubilization and nanoparticle formation.

    PubMed

    Inoue, Yutaka; Yoshimura, Sachie; Tozuka, Yuichi; Moribe, Kunikazu; Kumamoto, Takuya; Ishikawa, Tsutomu; Yamamoto, Keiji

    2007-02-22

    Clarithromycin (CAM) was co-ground with l-ascorbic acid 2-glucoside (AA-2G), a newly developed food additive, to improve the solubility characteristics. The complete solubilizing effect of AA-2G was observed for the ground mixture with 1:1 molar ratio. When ground mixtures of CAM and AA-2G (2:1) were dispersed into water, not only the solubilization of CAM was observed but also nanoparticle formation with a mean particle diameter of 280 nm. The CAM particles obtained in this manner were stable in suspension for at least 7 days. Zeta potential analysis showed that positive charges on the particle surface may be contributing to the stability of the suspension. 1H NMR spectrum of CAM dissolved in a phosphate buffer (pH 5.5) showed a signal derived from the N,N-dimethylamino group at 2.73 ppm, while that of an equimolar ground mixture of CAM with AA-2G in D2O (pH 5.5) showed clearly two signals at 2.65 and 2.77 ppm derived from the splitting of the two methyl groups. The 13C NMR spectrum of the equimolar ground mixture dissolved in D2O exhibited two signals derived from N,N-dimethyl carbons of desosamine group at 37.2 and 42.3 ppm, whereas unprocessed CAM showed no resonance signal arising from those carbons. Moreover, the carbon resonance at 163 and 173 ppm arising from the ketone group in the CAM lactone ring shifted downfield to 177 and 180 ppm after the co-grinding with AA-2G. The formation of nanoparticles was only observed when CAM was co-ground with AA-2G in the molar ratio of 2:1, which might be attributable to a grinding-induced interaction in the solid-state via the ketone group in lactone ring of CAM. PMID:17055675

  16. Cyanidin-3-O-?-glucoside inhibits lipopolysaccharide-induced inflammatory response in mouse mastitis model

    PubMed Central

    Fu, Yunhe; Wei, Zhengkai; Zhou, Ershun; Zhang, Naisheng; Yang, Zhengtao

    2014-01-01

    Cyanidin-3-O-?-glucoside (C3G) (CAS number 7084-24-4), a typical anthocyanin pigment that exists in the human diet, has been reported to have anti-inflammatory properties. However, the effect of C3G on lipopolysaccharide (LPS)-induced mastitis and the molecular mechanisms have not been investigated. In this study, we detected the protective effects of C3G on a LPS-induced mouse mastitis model and investigated the molecular mechanisms in LPS-stimulated mouse mammary epithelial cells (MMECs). Our results showed that C3G could attenuate mammary histopathologic changes and myeloperoxidase activity, and inhibit TNF-?, interleukin (IL)-1?, and IL-6 production caused by LPS. Meanwhile, C3G dose-dependently inhibited TNF-? and IL-6 in LPS-stimulated MMECs. C3G suppressed LPS-induced nuclear factor-?B (NF-?B) and interferon regulatory factor 3 (IRF3) activation. Furthermore, C3G disrupted the formation of lipid rafts by depleting cholesterol. Moreover, C3G activated liver X receptor (LXR)-ABCG1-dependent cholesterol efflux. Knockdown of LXR? abrogated the anti-inflammatory effects of C3G. In conclusion, C3G has a protective effect on LPS-induced mastitis. The promising anti-inflammatory mechanisms of C3G are associated with upregulation of the LXR?-ABCG1 pathway which result in disrupting lipid rafts by depleting cholesterol, thereby suppressing toll-like receptor 4-mediated NF-?B and IRF3 signaling pathways induced by LPS. PMID:24752550

  17. Functional diversification of two UGT80 enzymes required for steryl glucoside synthesis in Arabidopsis.

    PubMed

    Stucky, Daniel F; Arpin, James C; Schrick, Kathrin

    2015-01-01

    Steryl glucosides (SG) are abundant steroid conjugates in plant membranes. Beyond structural roles in lipid bilayers, functions in sugar transport, storage, and/or signalling are predicted. UDP-glucose:sterol glucosyltransferase 80A2 (UGT80A2) and UGT80B1, which share similarity to fungal counterparts, are implicated in SG synthesis in Arabidopsis thaliana. A third related enzyme, which seems specific to the plant lineage, is encoded by UGT713B1/At5g24750. Genetic and biochemical approaches were employed to determine the role of each UGT gene in the production of specific SGs and acyl SGs (ASGs). Using direct infusion electrospray ionization tandem mass spectrometry (ESI-MS/MS), SG and acyl SG (ASG) contents of ugt80 and ugt713 mutants, and triple and double mutants were profiled in seeds. In vitro enzyme assays were performed to assay substrate preferences. Both UGT80A2 and UGT80B1, but not UGT713B1 were shown to be coordinately down-regulated during seed imbibition when SG levels decline, consistent with similar functions as UGT80 enzymes. UGT80A2 was found to be required for normal levels of major SGs in seeds, whereas UGT80B1 is involved in accumulation of minor SG and ASG compounds. Although the results demonstrate specific activities for UGT80A2 and UGT80B1, a role for UGT713B1 in SG synthesis was not supported. The data show that UGT80A2, the more highly conserved enzyme, is responsible for the bulk production of SGs in seeds, whereas UGT80B1 plays a critical accessory role. This study extends our knowledge of UGT80 enzymes and provides evidence for specialized functions for distinct classes of SG and ASG molecules in plants. PMID:25316063

  18. Functional diversification of two UGT80 enzymes required for steryl glucoside synthesis in Arabidopsis

    PubMed Central

    Stucky, Daniel F.; Arpin, James C.

    2015-01-01

    Steryl glucosides (SG) are abundant steroid conjugates in plant membranes. Beyond structural roles in lipid bilayers, functions in sugar transport, storage, and/or signalling are predicted. UDP-glucose:sterol glucosyltransferase 80A2 (UGT80A2) and UGT80B1, which share similarity to fungal counterparts, are implicated in SG synthesis in Arabidopsis thaliana. A third related enzyme, which seems specific to the plant lineage, is encoded by UGT713B1/At5g24750. Genetic and biochemical approaches were employed to determine the role of each UGT gene in the production of specific SGs and acyl SGs (ASGs). Using direct infusion electrospray ionization tandem mass spectrometry (ESI-MS/MS), SG and acyl SG (ASG) contents of ugt80 and ugt713 mutants, and triple and double mutants were profiled in seeds. In vitro enzyme assays were performed to assay substrate preferences. Both UGT80A2 and UGT80B1, but not UGT713B1 were shown to be coordinately down-regulated during seed imbibition when SG levels decline, consistent with similar functions as UGT80 enzymes. UGT80A2 was found to be required for normal levels of major SGs in seeds, whereas UGT80B1 is involved in accumulation of minor SG and ASG compounds. Although the results demonstrate specific activities for UGT80A2 and UGT80B1, a role for UGT713B1 in SG synthesis was not supported. The data show that UGT80A2, the more highly conserved enzyme, is responsible for the bulk production of SGs in seeds, whereas UGT80B1 plays a critical accessory role. This study extends our knowledge of UGT80 enzymes and provides evidence for specialized functions for distinct classes of SG and ASG molecules in plants. PMID:25316063

  19. Eriodictyol-7-O-glucoside activates Nrf2 and protects against cerebral ischemic injury

    SciTech Connect

    Jing, Xu; Ren, Dongmei; Wei, Xinbing; Shi, Huanying; Zhang, Xiumei; Perez, Ruth G.; Lou, Haiyan; Lou, Hongxiang

    2013-12-15

    Stroke is a complex disease that may involve oxidative stress-related pathways in its pathogenesis. The nuclear factor erythroid-2-related factor 2/antioxidant response element (Nrf2/ARE) pathway plays an important role in inducing phase II detoxifying enzymes and antioxidant proteins and thus has been considered a potential target for neuroprotection in stroke. The aim of the present study was to determine whether eriodictyol-7-O-glucoside (E7G), a novel Nrf2 activator, can protect against cerebral ischemic injury and to understand the role of the Nrf2/ARE pathway in neuroprotection. In primary cultured astrocytes, E7G increased the nuclear localization of Nrf2 and induced the expression of the Nrf2/ARE-dependent genes. Exposure of astrocytes to E7G provided protection against oxygen and glucose deprivation (OGD)-induced oxidative insult. The protective effect of E7G was abolished by RNA interference-mediated knockdown of Nrf2 expression. In vivo administration of E7G in a rat model of focal cerebral ischemia significantly reduced the amount of brain damage and ameliorated neurological deficits. These data demonstrate that activation of Nrf2/ARE signaling by E7G is directly associated with its neuroprotection against oxidative stress-induced ischemic injury and suggest that targeting the Nrf2/ARE pathway may be a promising approach for therapeutic intervention in stroke. - Highlights: • E7G activates Nrf2 in astrocytes. • E7G stimulates expression of Nrf2-mediated cytoprotective proteins in astrocytes. • E7G protects astrocytes against OGD-induced cell death and apoptosis. • The neuroprotective effect of E7G involves the Nrf2/ARE pathway. • E7G protects rats against cerebral ischemic injury.

  20. Plant growth inhibition by cis-cinnamoyl glucosides and cis-cinnamic acid.

    PubMed

    Hiradate, Syuntaro; Morita, Sayaka; Furubayashi, Akihiro; Fujii, Yoshiharu; Harada, Jiro

    2005-03-01

    Spiraea thunbergii Sieb. contains 1-O-cis-cinnamoyl-beta-D-glucopyranose (CG) and 6-O-(4'-hydroxy-2'-methylene-butyroyl)-1-O-cis-cinnamoyl-beta-D-glucopyranose (BCG) as major plant growth inhibiting constituents. In the present study, we determined the inhibitory activity of CG and BCG on root elongation of germinated seedlings of lettuce (Lactuca sativa), pigweed (Amaranthus retroflexus), red clover (Trifolium pratense), timothy (Phleum pratense), and bok choy (Brassica rapa var chinensis) in comparison with that of two well-known growth inhibitors, 2,4-dichlorophenoxyacetic acid (2,4-D) and (+)-2-cis-4-trans-abscisic acid (cis-ABA), as well as two related chemicals of CG and BCG, cis-cinnamic acid (cis-CA) and trans-cinnamic acid (trans-CA). The EC50 values for CG and BCG on lettuce were roughly one-half to one-quarter of the value for cis-ABA. cis-Cinnamic acid, which is a component of CG and BCG, possessed almost the same inhibitory activity of CG and BCG, suggesting that the essential chemical structure responsible for the inhibitory activity of CG and BCG is cis-CA. The cis-stereochemistry of the methylene moiety is apparently needed for high inhibitory activity, as trans-CA had an EC50 value roughly 100 times that of CG, BCG, and cis-CA. Growth inhibition by CG, BCG, and cis-CA was influenced by the nature of the soil in the growing medium: alluvial soil preserved the bioactivity, whereas volcanic ash and calcareous soils inhibited bioactivity. These findings indicate a potential role of cis-CA and its glucosides as allelochemicals for use as plant growth regulators in agricultural fields. PMID:15898503

  1. Intracellular activity of lysosomal glucosylceramidase measured with 4-nonylumbelliferyl beta-glucoside.

    PubMed

    Bieberich, E; Legler, G

    1989-08-01

    Enzymatic activity of lysosomal glucosyl-ceramidase was determined in intact murine hybridoma and macrophage cells with the synthetic substrate nonylumbeliferyl-beta-glucoside (NUG). The substrate was applied as complex with bovine serum albumin (two binding sites, Kd 2.2 +/- 0.3 microM). The transport of the artificial substrate from medium to the enzyme was explored by measurements of substrate concentrations in cellular membranes and of endocytosis rate relative to substrate hydrolysis. The results indicated that, after enrichment in the plasma membrane, the substrate is mainly transported by simple diffusion. Release of nonylumberlliferone monitored fluorimetrically after disintegration of the cells in borate buffer containing Triton X-100 at pH 9.5 showed that 10(8) cells of both cell lines hydrolysed 1-1.5 nmol substrate/min at a total concentration of 0.1 mM NUG in the medium. Substrate hydrolysis was prevented by preincubating the cells with conduritol B epoxide (CBE), a specific active site-directed inhibitor of lysosomal glucosylceramidase. The substrate concentration at the site of the enzyme and maximal activity were evaluated by the inhibiting effect of the substrate on the inactivation rate by conduritol B epoxide. The rate of inhibitor uptake measured with bromo-[3H]conduritol B epoxide was shown to be not rate-limiting for the inactivation reaction. The molar concentration of the enzyme was determined by labeling with bromo-[3H]conduritol B epoxide. Comparison of the maximal intracellular activity with that of the enzyme after disintegration and activation by taurocholate showed a 20-fold lower activity in the native environment.(ABSTRACT TRUNCATED AT 250 WORDS) PMID:2590464

  2. Dual Role of Cyanidin-3-glucoside on the Differentiation of Bone Cells.

    PubMed

    Park, K H; Gu, D R; So, H S; Kim, K J; Lee, S H

    2015-12-01

    Cyanidin-3-glucoside (C3G) is one of the major components of anthocyanin, a water-soluble phytochemical. Recent studies demonstrated the chemopreventive and chemotherapeutic activities of C3G in various conditions, including cancer, although the precise effects of C3G on osteoclast and osteoblast differentiation remain unclear. Here, we investigated the role of C3G in the differentiation of bone-associated cells and its underlying mechanism. C3G inhibited receptor activator of nuclear factor kappa-B ligand (RANKL)-mediated osteoclast differentiation and formation in a dose-dependent manner and downregulated the expression of osteoclast differentiation marker genes. Pretreatment with C3G considerably reduced the induction of extracellular signal-regulated kinase, c-Jun N-terminal kinase, and p38 mitogen-activated kinases activation by RANKL in osteoclast precursor cells. Furthermore, C3G dramatically inhibited the expression of c-Fos and nuclear factor of activated T-cells, cytoplasmic 1, which are important transcription factors for osteoclast differentiation and activation. The formation of osteoclasts in coculture of bone marrow cells and calvaria-derived osteoblasts was also inhibited by C3G treatment, although the expression of macrophage colony-stimulating factor and RANKL (master factors for osteoclast differentiation and formation) and osteoprotegerin (a decoy receptor for RANKL) on osteoblasts was unaffected. The inhibitory effect of C3G on osteoclastogenesis is therefore targeted specifically to osteoclasts but not osteoblasts. Moreover, analysis of the expression levels of osteoblast differentiation marker genes and alizarin red staining showed that osteoblast differentiation and matrix formation increased after C3G treatment. Taken together, these results strongly suggest that C3G has a dual role in bone metabolism, as an effective inhibitor of osteoclast differentiation but also as an activator of osteoblast differentiation. Therefore, C3G may be used as a potent preventive or therapeutic agent for bone-related diseases, such as osteoporosis, rheumatoid arthritis, and periodontitis. PMID:26350961

  3. Cyanidin-3-glucoside isolated from mulberry fruit protects pancreatic ?-cells against oxidative stress-induced apoptosis.

    PubMed

    Lee, Jong Seok; Kim, Young Rae; Song, In Gyu; Ha, Suk-Jin; Kim, Young Eon; Baek, Nam-In; Hong, Eock Kee

    2015-02-01

    The extract obtained from berries contains high amounts of anthocyanins, and this extract is used as a phytotherapeutic agent for different types of diseases. In this study, we examined the cytoprotective effects of cyanidin-3-glucoside (C3G) isolated from mulberry fruit against pancreatic ?-cell apoptosis caused by hydrogen peroxide (H2O2)-induced oxidative stress. The MIN6 pancreatic ?-cells were used to investigate the cytoprotective effects of C3G on the oxidative stress-induced apoptosis of cells. Cell viability was examined by MTT assay and lipid peroxidation was assayed by thiobarbituric acid (TBA) reaction. Immunofluorescence staining, flow cytometry and western blot analysis were also used to determine apoptosis and the expression of proteins associated with apoptosis. Our results revealed that H2O2 increased the rate of apoptosis by stimulating various pro-apoptotic processes, such as the generation of intracellular reactive oxygen species (ROS), lipid peroxidation, DNA fragmentation and caspase-3 activation. However, C3G reduced the H2O2-induced cell death in the MIN6N pancreatic ?-cells. In addition, we confirmed that H2O2 activated mitogen-activated protein kinases (MAPKs), such as extracellular signal-regulated kinase (ERK), c-Jun NH2-terminal kinase (JNK) and p38 MAPK. C3G inhibited the phosphorylation of ERK and p38 without inducing the phosphorylation of JNK. Furthermore, C3G regulated the intrinsic apoptotic pathway-associated proteins, such as proteins belonging to the Bcl-2 family, cytochrome c and caspase-3. Taken together, our results suggest that C3G isolated from mulberry fruit has potential for use as a phytotherapeutic agent for the prevention of diabetes by preventing oxidative stress-induced ?-cell apoptosis. PMID:25435295

  4. Trihydroxybenzoic acid glucoside as a global skin color modulator and photo-protectant

    PubMed Central

    Chajra, Hanane; Redziniak, Gérard; Auriol, Daniel; Schweikert, Kuno; Lefevre, Fabrice

    2015-01-01

    Background 3,4,5-Trihydroxybenzoic acid glucoside (THBG), a molecule produced by an original biocatalysis-based technology, was assessed in this study with respect to its skin photoprotective capacity and its skin color control property on Asian-type skin at a clinical level and on skin explant culture models. Methods The double-blinded clinical study was done in comparison to a vehicle by the determination of objective color parameters thanks to recognized quantitative and qualitative analysis tools, including Chroma-Meter, VISIA-CR™, and SIAscope™. Determination of L* (brightness), a* and b* (green–red and blue–yellow chromaticity coordinates), individual typology angle, and C* (chroma) and h* (hue angle) parameters using a Chroma-Meter demonstrated that THBG is able to modify skin color while quantification of ultraviolet (UV) spots by VISIA-CR™ confirmed its photoprotective effect. The mechanism of action of THBG molecule was determined using explant skin culture model coupled to histological analysis (epidermis melanin content staining). Results We have demonstrated that THBG was able to modulate significantly several critical parameters involved in skin color control such as L* (brightness), a* (redness), individual typology angle (pigmentation), and hue angle (yellowness in this study), whereas no modification occurs on b* and C* parameters. We have demonstrated using histological staining that THBG decrease epidermis melanin content under unirradiated and irradiated condition. We also confirmed that THBG molecule is not a sunscreen agent. Conclusion This study demonstrated that THBG controls skin tone via the inhibition of melanin synthesis as well as the modulation of skin brightness, yellowness, and redness. PMID:26648748

  5. Orcinol glucoside produces antidepressant effects by blocking the behavioural and neuronal deficits caused by chronic stress.

    PubMed

    Ge, Jin-Fang; Gao, Wen-Chao; Cheng, Wen-Ming; Lu, Wei-Li; Tang, Jie; Peng, Lei; Li, Ning; Chen, Fei-Hu

    2014-01-01

    This study focused on the antidepressant potential of orcinol glucoside (OG) and its possible mechanisms of action. We established a depressed rat model using 3 consecutive weeks of chronic unpredictable mild stress (CUMS). The antidepressant-like effect of OG was revealed using the sucrose preference test, the open field test, the forced swimming test (FST), and the tail suspension test (TST). The activity of the hypothalamic-pituitary-adrenal (HPA) axis was evaluated by detecting the serum corticosterone (CORT) concentrations and mRNA expression of corticotrophin-releasing hormone (CRH) in the hypothalamus. The protein expression levels of brain-derived neurotrophic factor (BDNF) and total phosphorylated-ERK1/2 were detected by western blot. The results showed that OG treatment (1.5, 3, or 6mg/kg) alleviated the depression-like behaviour of rats under CUMS, as indicated by the increased sucrose preference and the decreased immobility in both the FST and TST, although the rearing frequency in the open field test increased only in the group that received the lowest dose (1.5mg/kg OG). Rats that received OG treatment exhibited reduced serum CORT levels and CRH mRNA expression in the hypothalamus, suggesting that the hyperactivity of the HPA axis in CUMS rats was reversed by OG treatment. Moreover, OG treatment upregulated the protein levels of BDNF and phosphorylated-ERK1/2 in the hippocampus, even above control levels. Our findings suggest that OG improved depressive behaviour in CUMS rats by downregulating HPA axis hyperactivity and increasing BDNF expression and ERK1/2 phosphorylation in the hippocampus. PMID:23838013

  6. Shanzhiside methylester, the principle effective iridoid glycoside from the analgesic herb Lamiophlomis rotata, reduces neuropathic pain by stimulating spinal microglial ?-endorphin expression.

    PubMed

    Fan, Hui; Li, Teng-Fei; Gong, Nian; Wang, Yong-Xiang

    2016-02-01

    Lamiophlomis rotata (L. rotata, Duyiwei) is an orally available Tibetan analgesic herb widely prescribed in China. Shanzhiside methylester (SM) is a principle effective iridoid glycoside of L. rotata and serves as a small molecule glucagon-like peptide-1 (GLP-1) receptor agonist. This study aims to evaluate the signal mechanisms underlying SM anti-allodynia, determine the ability of SM to induce anti-allodynic tolerance, and illustrate the interactions between SM and morphine, or SM and ?-endorphin, in anti-allodynia and anti-allodynic tolerance. Intrathecal SM exerted dose-dependent and long-lasting (>4 h) anti-allodynic effects in spinal nerve injury-induced neuropathic rats, with a maximal inhibition of 49% and a projected ED50 of 40.4 ?g. SM and the peptidic GLP-1 receptor agonist exenatide treatments over 7 days did not induce self-tolerance to anti-allodynia or cross-tolerance to morphine or ?-endorphin. In contrast, morphine and ?-endorphin induced self-tolerance and cross-tolerance to SM and exenatide. In the spinal dorsal horn and primary microglia, SM significantly evoked ?-endorphin expression, which was completely prevented by the microglial inhibitor minocycline and p38 mitogen-activated protein kinase (MAPK) inhibitor SB203580. SM anti-allodynia was totally inhibited by the GLP-1 receptor antagonist exendin(9-39), minocycline, ?-endorphin antiserum, ?-opioid receptor antagonist CTAP, and SB203580. SM and exenatide specifically activated spinal p38 MAPK phosphorylation. These results indicate that SM reduces neuropathic pain by activating spinal GLP-1 receptors and subsequently stimulating microglial ?-endorphin expression via the p38 MAPK signaling. Stimulation of the endogenous ?-endorphin expression may be a novel and effective strategy for the discovery and development of analgesics for the long-term treatment of chronic pain. PMID:26363192

  7. Comparison of Sugars, Iridoid Glycosides and Amino Acids in Nectar and Phloem Sap of Maurandya barclayana, Lophospermum erubescens, and Brassica napus

    PubMed Central

    Lohaus, Gertrud; Schwerdtfeger, Michael

    2014-01-01

    Background Floral nectar contains sugars and amino acids to attract pollinators. In addition, nectar also contains different secondary compounds, but little is understood about their origin or function. Does nectar composition reflect phloem composition, or is nectar synthesized and/or modified in nectaries? Studies where both, the nectar as well as the phloem sap taken from the same plant species were analyzed in parallel are rare. Therefore, phloem sap and nectar from different plant species (Maurandya barclayana, Lophospermum erubescens, and Brassica napus) were compared. Methodology and Principal Findings Nectar was collected with microcapillary tubes and phloem sap with the laser-aphid-stylet technique. The nectar of all three plant species contained high amounts of sugars with different percentages of glucose, fructose, and sucrose, whereas phloem sap sugars consisted almost exclusively of sucrose. One possible reason for this could be the activity of invertases in the nectaries. The total concentration of amino acids was much lower in nectars than in phloem sap, indicating selective retention of nitrogenous solutes during nectar formation. Nectar amino acid concentrations were negatively correlated with the nectar volumes per flower of the different plant species. Both members of the tribe Antirrhineae (Plantaginaceae) M. barclayana and L. erubescens synthesized the iridoid glycoside antirrhinoside. High amounts of antirrhinoside were found in the phloem sap and lower amounts in the nectar of both plant species. Conclusions/Significance The parallel analyses of nectar and phloem sap have shown that all metabolites which were found in nectar were also detectable in phloem sap with the exception of hexoses. Otherwise, the composition of both aqueous solutions was not the same. The concentration of several metabolites was lower in nectar than in phloem sap indicating selective retention of some metabolites. Furthermore, the existence of antirrhinoside in nectar could be based on passive secretion from the phloem. PMID:24489951

  8. Use of countercurrent chromatography during isolation of 6-hydroxyluteolin-7-O-?-glucoside, a major antioxidant of Athrixia phylicoides.

    PubMed

    de Beer, Dalene; Joubert, Elizabeth; Malherbe, Christiaan J; Jacobus Brand, D

    2011-09-01

    Athrixia phylicoides, an indigenous South African herbal tea, has potential as a source of nutraceutical antioxidant extracts. Countercurrent chromatography (CCC) was employed as part of a multi-step process to isolate one of the major antioxidant compounds in A. phylicoides extracts. Antioxidant activity of the extracts was comparable to commercial nutraceutical extracts from Aspalathus linearis and Cyclopia spp. in a range of assays. The extracts were tested for radical scavenging (2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) di-ammonium radical cation (ABTS·?) scavenging, 2,2-diphenyl-1-picrylhydrazyl radical (DPPH) scavenging and oxygen radical absorbance capacity (ORAC)), ferric reducing antioxidant potential (FRAP) and iron chelating activity, as well as inhibition of microsomal lipid and linoleic acid emulsion oxidation. After extraction optimisation, the antioxidant activity of the major phenolic compounds in an A. phylicoides extract was determined using the on-line HPLC-diode-array-DPPH and -ABTS·? radical scavenging assays. Major compounds reported for the first time included chlorogenic acid, 1,3-dicaffeoylquinic acid, several hydroxycinnamic acid derivatives, including dicaffeoyl quinic acids, and an unidentified flavone-hexose. Finally, CCC was used in conjunction with liquid-liquid partitioning and semi-preparative reversed-phase HPLC to isolate 6-hydroxyluteolin-7-O-?-glucoside (a major antioxidant) and quercetagetin-7-O-?-glucoside (a minor compound present in CCC fraction containing 6-hydroxyluteolin-7-O-?-glucoside) from an A. phylicoides extract. The chemical structures of the isolated compounds were confirmed by LC high-resolution electrospray ionisation MS, as well as ¹H, ¹³C and 2D NMR spectroscopy. This is the first report of the isolation of these compounds from A. phylicoides. PMID:21236437

  9. Functional characterization, homology modeling and docking studies of ?-glucosidase responsible for bioactivation of cyanogenic hydroxynitrile glucosides from Leucaena leucocephala (subabul).

    PubMed

    Shaik, Noor M; Misra, Anurag; Singh, Somesh; Fatangare, Amol B; Ramakumar, Suryanarayanarao; Rawal, Shuban K; Khan, Bashir M

    2013-02-01

    Glycosyl hydrolase family 1 ?-glucosidases are important enzymes that serve many diverse functions in plants including defense, whereby hydrolyzing the defensive compounds such as hydroxynitrile glucosides. A hydroxynitrile glucoside cleaving ?-glucosidase gene (Llbglu1) was isolated from Leucaena leucocephala, cloned into pET-28a (+) and expressed in E. coli BL21 (DE3) cells. The recombinant enzyme was purified by Ni-NTA affinity chromatography. The optimal temperature and pH for this ?-glucosidase were found to be 45 °C and 4.8, respectively. The purified Llbglu1 enzyme hydrolyzed the synthetic glycosides, pNPGlucoside (pNPGlc) and pNPGalactoside (pNPGal). Also, the enzyme hydrolyzed amygdalin, a hydroxynitrile glycoside and a few of the tested flavonoid and isoflavonoid glucosides. The kinetic parameters K (m) and V (max) were found to be 38.59 ?M and 0.8237 ?M/mg/min for pNPGlc, whereas for pNPGal the values were observed as 1845 ?M and 0.1037 ?M/mg/min. In the present study, a three dimensional (3D) model of the Llbglu1 was built by MODELLER software to find out the substrate binding sites and the quality of the model was examined using the program PROCHEK. Docking studies indicated that conserved active site residues are Glu 199, Glu 413, His 153, Asn 198, Val 270, Asn 340, and Trp 462. Docking of rhodiocyanoside A with the modeled Llbglu1 resulted in a binding with free energy change (?G) of -5.52 kcal/mol on which basis rhodiocyanoside A could be considered as a potential substrate. PMID:23079707

  10. Chronic Exposure to Dietary Sterol Glucosides is Neurotoxic to Motor Neurons and Induces an ALS-PDC Phenotype

    PubMed Central

    Tabata, R. C.; Wilson, J. M. B.; Ly, P.; Zwiegers, P.; Kwok, D.; Van Kampen, J. M.; Cashman, N.; Shaw, C. A.

    2008-01-01

    Epidemiological studies of the Guamanian variants of amyotrophic lateral sclerosis (ALS) and parkinsonism, amyotrophic lateral sclerosis-parkinsonism dementia complex (ALS-PDC), have shown a positive correlation between consumption of washed cycad seed flour and disease occurrence. Previous in vivo studies by our group have shown that the same seed flour induces ALS and PDC phenotypes in out bred adult male mice. In vitro studies using isolated cycad compounds have also demonstrated that several of these are neurotoxic, specifically, a number of water insoluble phytosterol glucosides of which ?-sitosterol ?-d-glucoside (BSSG) forms the largest fraction. BSSG is neurotoxic to motor neurons and other neuronal populations in culture. The present study shows that an in vitro hybrid motor neuron (NSC-34) culture treated with BSSG undergoes a dose-dependent cell loss. Surviving cells show increased expression of HSP70, decreased cytosolic heavy neurofilament expression, and have various morphological abnormalities. CD-1 mice fed mouse chow pellets containing BSSG for 15 weeks showed motor deficits and motor neuron loss in the lumbar and thoracic spinal cord, along with decreased glutamate transporter labelling, and increased glial fibrillary acid protein reactivity. Other pathological outcomes included increased caspase-3 labelling in the striatum and decreased tyrosine-hydroxylase labelling in the striatum and substantia nigra. C57BL/6 mice fed BSSG-treated pellets for 10 weeks exhibited progressive loss of motor neurons in the lumbar spinal cord that continued to worsen even after the BSSG exposure ended. These results provide further support implicating sterol glucosides as one potential causal factor in the motor neuron pathology previously associated with cycad consumption and ALS-PDC. PMID:18196479

  11. A study of transglucosylation kinetic in an enzymatic synthesis of benzyl alcohol glucoside by ?-glucosidase from S. cerevisiae

    NASA Astrophysics Data System (ADS)

    Pavlovi?, M.; Dimitrijevi?, A.; Trbojevi?, J.; Milosavi?, N.; Gavrovi?-Jankulovi?, M.; Bezbradica, D.; Veli?kovi?, D.

    2013-12-01

    ?-1,4-Glucosidase from Saccharomyces cerevisiae is an enzyme which is widely used in synthesis of different drugs. Glucosidase inhibitors are studied as potential drugs for prevention of HIV and diabetes. For understanding of these processes it is very important to have insights in the transglucosylation activity of this enzyme. In this paper the kinetics of transglucosylation reaction catalyzed by this enzyme in the synthesis of benzyl alcohol glucoside was studied and all relevant kinetic constants for this system are found. It was shown one additional property of transglycosylation reactions catalyzed by glycosidases—inhibition by both, glucose acceptor and glucose donor, and mechanisms for these inhibitions were proposed.

  12. (6S)-Hydroxy-3-oxo-a-ionol glucosides from Capparis spinosa fruits hsan C alis a

    E-print Network

    Rüedi, Peter

    -a-ionol glucosides; Abscisic acid metabolites; 1 H NMR; 13 C NMR; CD spectra; Absolute configuration 1. Introduction/z 409 [M+Na]+ and 795 [2M+Na]+ ) and NMR data. The 1 H and 13 C NMR spectra (Table 1) of 1, which were (E)-olefin (H 5.94 d, J=15.5 Hz; 5.64 dd, J=15.5 and 6.4 Hz), an oxymethine proton (H 4.43 dq, J=6

  13. Synthesis of zearalenone-16-?,D-glucoside and zearalenone-16-sulfate: A tale of protecting resorcylic acid lactones for regiocontrolled conjugation

    PubMed Central

    Weber, Julia; Svatunek, Dennis; Skrinjar, Philipp; Adam, Gerhard; Krska, Rudolf; Hametner, Christian; Fröhlich, Johannes

    2014-01-01

    Summary The development of a reliable procedure for the synthesis of the 16-glucoside and 16-sulfate of the resorcylic acid lactone (RAL) type compound zearalenone is presented. Different protective group strategies were considered and applied to enable the preparation of glucosides and sulfates that are difficult to access up to now. Acetyl and p-methoxybenzyl protection led to undesired results and were shown to be inappropriate. Finally, triisopropylsilyl-protected zearalenone was successfully used as intermediate for the first synthesis of the corresponding mycotoxin glucoside and sulfate that are highly valuable as reference materials for further studies in the emerging field of masked mycotoxins. Furthermore, high stability was observed for aryl sulfates prepared as tetrabutylammonium salts. Overall, these findings should be applicable for the synthesis of similar RAL type and natural product conjugates. PMID:24991263

  14. Metabolism of monoterpenes: early steps in the metabolism of d-neomenthyl-. beta. -D-glucoside in peppermint (Mentha piperita) rhizomes

    SciTech Connect

    Croteau, R.; Sood, V.K.; Renstroem, B.; Bhushan, R.

    1984-11-01

    Previous studies have shown that the monoterpene ketone l-(G-/sup 3/H) menthone is reduced to the epimeric alcohols l-menthol and d-neomenthol in leaves of flowering peppermint (Mentha piperita L.), and that a portion of the menthol is converted to methyl acetate while the bulk of the neomenthol is transformed to neomenthyl-..beta..-D-glucoside which is then transported to the rhizome. Analysis of the disposition of l-(G)/sup 3/H)menthone applied to midstem leaves of intact flowering plants allowed the kinetics of synthesis and transport of the monoterpenyl glucoside to be determined, and gave strong indication that the glucoside was subsequently metabolized in the rhizome. Studies with d-(G-/sup 3/H)neomenthyl-..beta..-D-glucoside as substrate, using excised rhizomes or rhizome segments, confirmed the hydrolysis of the glucoside as an early step in metabolism at this site, and revealed that the terpenoid moiety was further converted to a series of ether-soluble, methanol-soluble, and water-soluble products. The conversion of menthone to the lactone, and of the lactone to more polar products, were confirmed in vivo using l-(G-/sup 3/H)menthone and l-(G-/sup 3/H)-3,4-menthone lactone as substrates. Additional oxidation products were formed in vivo via the desaturation of labeled neomenthol and/or menthone, but none of these transformations appeared to lead to ring opening of the p-menthane skeleton. Each step in the main reaction sequence, from hydrolysis of neomenthyl glucoside to lactonization of menthone, was demonstrated in cell-free extracts from the rhizomes of flowering mint plants. The lactomization step is of particular significance in providing a means of cleaving the p-methane ring to afford an acyclic carbon skeleton that can be further degraded by modifications of the well-known ..beta..-oxidation sequence. 41 references, 3 figures, 1 table.

  15. Development and validation of an LC-MS/MS analysis for simultaneous determination of delphinidin-3-glucoside, cyanidin-3-glucoside and cyanidin-3-(6-malonylglucoside) in human plasma and urine after blood orange juice administration.

    PubMed

    Giordano, Lucia; Coletta, Walter; Rapisarda, Paolo; Donati, Maria Benedetta; Rotilio, Domenico

    2007-12-01

    Blood orange juice has a high content in anthocyanins, especially represented by delphinidin-3-glucoside (D3G), cyanidin-3-glucoside (C3G) and cyanidin-3-(6-malonylglucoside) (CMG). An LC-MS/MS method for the simultaneous determination of D3G and C3G in human plasma and urine was developed and validated. After sample preparation by SPE, chromatographic separation was performed with an RP-C(18) column, using a water/methanol linear gradient. The quantitation of target compounds was determined by multiple reaction monitoring (MRM) mode, using ESI. The method showed good selectivity, sensitivity (LOD = 0.05 and 0.10 ng/mL for C3G in plasma and urine, respectively; LOD = 0.10 ng/mL for D3G in plasma and urine), linearity (0.20-200 ng/mL; r >or= 0.998), intra- and interday precision and accuracy (

  16. Fragmentation study of iridoid glycosides and phenylpropanoid glycosides in Radix Scrophulariae by rapid resolution liquid chromatography with diode-array detection and electrospray ionization time-of-flight mass spectrometry.

    PubMed

    Wu, Qian; Yuan, Quan; Liu, E-Hu; Qi, Lian-Wen; Bi, Zhi-Ming; Li, Ping

    2010-08-01

    Rapid resolution liquid chromatography (RRLC) coupled with diode array detection (DAD) and electrospray ionization time-of-flight mass spectrometry (ESI-TOF MS) method was applied to the mass spectral study of a series of naturally occurring iridoid glycosides and phenylpropanoid glycosides in Radix Scrophulariae, which provides higher speed and increased sensitivity without loss of resolution. With dynamic adjustment as the key role of the fragmentor voltage and confirmed with authentic standards, valuable structural information regarding the nature of both the glycoside skeletons was thus obtained. Most compositions were found to possess organic acid moiety such as cinnamoyl, caffeoyl and ferulyol. Besides extensive fragmentation of the carbohydrate moiety, losses of the hydroxyl and glucose residue units showed in the spectra, permitting the exploration of the skeleton and the identity of substituents in the molecule. Ten major iridoid glycosides and 10 phenylpropanoid glycosides were identified or tentatively characterized based on their retention times, UV and TOF MS data. The major fragmentation pathways of PGs in Radix Scrophulariae obtained through the MS data was schemed systematically for the first time, which provides a reference for other PGs derivatives. PMID:20017212

  17. Occurrence and fate of the norsesquiterpene glucoside ptaquiloside (PTA) in soils

    NASA Astrophysics Data System (ADS)

    Zaccone, Claudio; Cavoski, Ivana; Costi, Roberta; Sarais, Giorgia; Caboni, Pierluigi; Miano, Teodoro M.; Lattanzio, Vincenzo

    2014-05-01

    The bracken fern Pteridium aquilinum (L.) Kuhn, one of the most common plant species on Earth, produces a wide range of secondary metabolites including the norsesquiterpene glucoside ptaquiloside (PTA). This bracken constituent causes acute poisoning, blindness and cancer in animals, and can be transferred to man when bracken is utilized as food. Also milk from cows eating bracken is thought to be the vector for the transfer of PTA to humans, as well as PTA-contaminated drinking waters. Although some studies on the effect of growth conditions and soil properties on the production and mobility of PTA have been carried out (mainly in the North of Europe), results are sometimes conflicting and further investigations are needed. The aim of the present work is to study the occurrence and the fate of PTA in soils showing different physico-chemical features, collected in different pedoclimatic areas (from the South of Italy), but having the extensive ("wild") livestock farming as common denominator. The PTA content was determined in both soil and fern samples by GC-MS; both the extraction protocol and recovery were previously tested through incubation studies. Soils samples were also characterizes from the physical and chemical point of view (pH, EC, texture, total carbonates, cation exchange capacity, organic C, total N, available nutrients and heavy metal concentration) in order to correlate the possible influence of soil parameters on PTA production, occurrence and mobility. PTA concentration in soil samples was always

  18. Enzymatic Formation of Novel Ginsenoside Rg1-?-Glucosides by Rat Intestinal Homogenates.

    PubMed

    Mathiyalagan, Ramya; Kim, Young-Hoi; Kim, Yeon Ju; Kim, Myung-Kon; Kim, Min-Ji; Yang, Deok Chun

    2015-12-01

    The variation of linkage positions in ginsenosides leads to diverse pharmacological efficiencies. The hydrolysis and transglycosylation properties of glycosyl hydrolase family enzymes have a great impact on the synthesis of novel and structurally diversified compounds. In this study, six ginsenoside Rg1-?-glucosides were found to be synthesized from the reaction mixture of maltose as a donor and ginsenoside Rg1 as a sugar acceptor in the presence of rat small intestinal homogenates, which exhibit high ?-glucosidase activities. The individual compounds were purified and were identified by spectroscopy (HPLC-MS, (1)H-NMR, and (13)C-NMR) as 6-O-[?-D-glcp-(1?4)-?-D-glcp]-20-O-(?-D-glcp)-20(S)-protopanaxatriol, 6-O-?-D-glcp-20-O-[?-D-glcp-(1?6)-(?-D-glcp)]-20(S)-protopanaxatriol, 6-O-?-D-glcp-20-O-[?-D-glcp-(1?4)-(?-D-glcp)]-20(S)-protopanaxatriol, 6-O-[?-D-glcp-(1?6)-?-D-glcp]-20-O-(?-glcp)-20(S)-protopanaxatriol, 6-O-[?-D-glcp-(1?3)-?-D-glcp]-20-O-(?-D-glcp)-20(S)-protopanaxatriol, and 6-O-?-D-glcp-20-O-[?-D-glcp-(1?3)-(?-D-glcp)]-20(S)-protopanaxatriol. Among these six, 6-O-?-D-glcp-20-O-?-D-glcp-(1?6)-(?-D-glcp)-20(S)-protopanaxatriol and 6-O-?-D-glcp-(1?6)-?-D-glcp-20-O-(?-D-glcp)-20(S)-protopanaxatriol are considered to be novel compounds of alpha-ginsenosidal saponins which pharmacological activities should be further characterized. This is the first report on the enzymatic elaboration of ginsenoside Rg1 derivatives using rat intestinal homogenates. To the best of our knowledge, it is also the first to reveal the sixth and 20th positions of an unusual ?-D-glucopyranosyl-(1?6)-?-D-glucopyranosyl sugar chain with 20(S)-protopanaxatriol saponins in Panax ginseng Mayer. PMID:26411353

  19. Thinning of dermas with the increasing age may be against by tetrahydroxystilbene glucoside in mice

    PubMed Central

    Zhou, Xuanxuan; Ge, Lan; Yang, Qian; Xie, Yanhua; Sun, Jiyuan; Cao, Wei; Wang, Siwang

    2014-01-01

    Objective: To research and reveal Tetrahydroxystilbene glucoside (TSG) anti-thinning effect of dermas on skin of ageing mice. Methods: The dermal layer thickness was measured with hematoxylin-eosin (HE) staining; the levels of collagen and elastic fibers were measured with immunohistochemical staining; the levels of insulin, insulin-like growth factor-1 (IGF-1), and two receptors of insulin and IGF-1 were measured with Elisa kits; the levels of Ca2+ and P were measured with ELISA kits. Results: TSG and Polygonum multiflorum extract (PME) made thicken dermal layer thickness (P<0.01, vs. control group); promoted collagen fiber expression (P<0.01, vs. control group, 22.94% and 28.26% vs. 20.41%); reduced the levels of insulin (P<0.01, vs. control group, 2.50 ng/ml and 2.69 ng/ml vs. 3.04 ng/ml), insulin like growth factor 1 (IGF-1, P<0.01, vs. control group, 154.75 ng/ml and 155.60 ng/ml vs. 209.28 ng/ml), receptors of insulin (P<0.01, vs. control group, 0.423 ng/ml and 0.426 ng/ml vs. 0.648 ng/ml) and IGF-1 (P<0.01, vs. control group, 71.96 ng/ml and 81.68 ng/ml vs. 87.02 ng/ml) in aging mice skin; raised the levels of Ca2+ and P in serum in mice (P<0.01, vs. control group, 1.24 mol/ml and 1.30 mol/ml vs. 1.08 mol/ml; P<0.01, vs. control group, 2.00 mol/ml and 2.03 mol/ml vs. 1.197 mol/ml). Conclusion: TSG and PME showed their protections to skin aging in mice challenged with control groups. It ensured the anti-thinning effect of dermas of TSG and provided two potential factors (insulin/IGF-1 signal pathway and the level of Ca2+) related to skin senescence of aging mice. PMID:25232382

  20. Dirigent Protein-Mediated Lignan and Cyanogenic Glucoside Formation in Flax Seed: Integrated Omics and MALDI Mass Spectrometry Imaging.

    PubMed

    Dalisay, Doralyn S; Kim, Kye Won; Lee, Choonseok; Yang, Hong; Rübel, Oliver; Bowen, Benjamin P; Davin, Laurence B; Lewis, Norman G

    2015-06-26

    An integrated omics approach using genomics, transcriptomics, metabolomics (MALDI mass spectrometry imaging, MSI), and bioinformatics was employed to study spatiotemporal formation and deposition of health-protecting polymeric lignans and plant defense cyanogenic glucosides. Intact flax (Linum usitatissimum) capsules and seed tissues at different development stages were analyzed. Transcriptome analyses indicated distinct expression patterns of dirigent protein (DP) gene family members encoding (-)- and (+)-pinoresinol-forming DPs and their associated downstream metabolic processes, respectively, with the former expressed at early seed coat development stages. Genes encoding (+)-pinoresinol-forming DPs were, in contrast, expressed at later development stages. Recombinant DP expression and DP assays also unequivocally established their distinct stereoselective biochemical functions. Using MALDI MSI and ion mobility separation analyses, the pinoresinol downstream derivatives, secoisolariciresinol diglucoside (SDG) and SDG hydroxymethylglutaryl ester, were localized and detectable only in early seed coat development stages. SDG derivatives were then converted into higher molecular weight phenolics during seed coat maturation. By contrast, the plant defense cyanogenic glucosides, the monoglucosides linamarin/lotaustralin, were detected throughout the flax capsule, whereas diglucosides linustatin/neolinustatin only accumulated in endosperm and embryo tissues. A putative biosynthetic pathway to the cyanogens is proposed on the basis of transcriptome coexpression data. Localization of all metabolites was at ca. 20 ?m resolution, with the web based tool OpenMSI enabling not only resolution enhancement but also an interactive system for real-time searching for any ion in the tissue under analysis. PMID:25981198

  1. Biochemical Characterization of a Recombinant UDP-glucosyltransferase from Rice and Enzymatic Production of Deoxynivalenol-3-O-?-d-glucoside

    PubMed Central

    Michlmayr, Herbert; Malachová, Alexandra; Varga, Elisabeth; Kleinová, Jana; Lemmens, Marc; Newmister, Sean; Rayment, Ivan; Berthiller, Franz; Adam, Gerhard

    2015-01-01

    Glycosylation is an important plant defense mechanism and conjugates of Fusarium mycotoxins often co-occur with their parent compounds in cereal-based food and feed. In case of deoxynivalenol (DON), deoxynivalenol-3-O-?-d-glucoside (D3G) is the most important masked mycotoxin. The toxicological significance of D3G is not yet fully understood so that it is crucial to obtain this compound in pure and sufficient quantities for toxicological risk assessment and for use as an analytical standard. The aim of this study was the biochemical characterization of a DON-inactivating UDP-glucosyltransferase from rice (OsUGT79) and to investigate its suitability for preparative D3G synthesis. Apparent Michaelis constants (Km) of recombinant OsUGT79 were 0.23 mM DON and 2.2 mM UDP-glucose. Substrate inhibition occurred at DON concentrations above 2 mM (Ki = 24 mM DON), and UDP strongly inhibited the enzyme. Cu2+ and Zn2+ (1 mM) inhibited the enzyme completely. Sucrose synthase AtSUS1 was employed to regenerate UDP-glucose during the glucosylation reaction. With this approach, optimal conversion rates can be obtained at limited concentrations of the costly co-factor UDP-glucose. D3G can now be synthesized in sufficient quantity and purity. Similar strategies may be of interest to produce ?-glucosides of other toxins. PMID:26197338

  2. Biochemical Characterization of a Recombinant UDP-glucosyltransferase from Rice and Enzymatic Production of Deoxynivalenol-3-O-?-D-glucoside.

    PubMed

    Michlmayr, Herbert; Malachová, Alexandra; Varga, Elisabeth; Kleinová, Jana; Lemmens, Marc; Newmister, Sean; Rayment, Ivan; Berthiller, Franz; Adam, Gerhard

    2015-07-01

    Glycosylation is an important plant defense mechanism and conjugates of Fusarium mycotoxins often co-occur with their parent compounds in cereal-based food and feed. In case of deoxynivalenol (DON), deoxynivalenol-3-O-?-D-glucoside (D3G) is the most important masked mycotoxin. The toxicological significance of D3G is not yet fully understood so that it is crucial to obtain this compound in pure and sufficient quantities for toxicological risk assessment and for use as an analytical standard. The aim of this study was the biochemical characterization of a DON-inactivating UDP-glucosyltransferase from rice (OsUGT79) and to investigate its suitability for preparative D3G synthesis. Apparent Michaelis constants (Km) of recombinant OsUGT79 were 0.23 mM DON and 2.2 mM UDP-glucose. Substrate inhibition occurred at DON concentrations above 2 mM (Ki = 24 mM DON), and UDP strongly inhibited the enzyme. Cu2+ and Zn2+ (1 mM) inhibited the enzyme completely. Sucrose synthase AtSUS1 was employed to regenerate UDP-glucose during the glucosylation reaction. With this approach, optimal conversion rates can be obtained at limited concentrations of the costly co-factor UDP-glucose. D3G can now be synthesized in sufficient quantity and purity. Similar strategies may be of interest to produce ?-glucosides of other toxins. PMID:26197338

  3. A reevaluation of the epimeric and anomeric relationship of glucosides and galactosides in thermotropic liquid crystal self-assemblies.

    PubMed

    Hashim, Rauzah; Mirzadeh, Seyed M; Heidelberg, Thorsten; Minamikawa, Hiroyuki; Yoshiaki, Tanaka; Sugimura, Akhiko

    2011-12-27

    Anomers and epimers ?- and ?-gluco and -galactosides are expected to behave differently. However, recent results on a series of Guerbet glycosides have indicated similar liquid crystal clearing temperatures for pure ?-glucosides and the corresponding ?-galactosides. This observation has led to speculation on similarities in the self-assembly interactions between the two systems, attributed to the trans-configuration of the 4-OH group and the hydrophobic aglycon. Previous simulations on related bilayers systems support this hypothesis, by relating this clearing transition temperature to intralayer (sugar-sugar) hydrogen bonding. In order to confirm the hypothesis, the comparison was expanded to include the cis-configurated pair, that is, ?-gluco/?-galactoside. A set of ?-configurated Guerbet glucosides as well as octyl ?-galactoside were prepared and their thermotropic phase behavior studied. The data obtained enabled a complete comparison of the isomers of interest. While the results in general are in line with a pairing of the stereo-isomers according to the indicated cis/trans-configuration, differences within the pairs can be explained based on the direction of hydrogen bonds from a simple modeling study. PMID:22088885

  4. Long-term cultured hairy roots of chicory-a rich source of hydroxycinnamates and 8-deoxylactucin glucoside.

    PubMed

    Malarz, Janusz; Stojakowska, Anna; Kisiel, Wanda

    2013-12-01

    A 12-year-old hairy root culture of Cichorium intybus L., a callus culture of the plant as well as roots and leaves of a wild plant of chicory, and roots of two C. intybus L. var. sativum cultivars were examined in respect of their hydroxycinnamate and sesquiterpene lactone compositions and contents. Total phenolics and diphenylpicrylhydrazyl radical scavenging activity of the examined plant tissues were also analyzed. The most active in radical scavenging were extracts from the hairy roots and leaves of chicory. 3,5-Dicaffeoylquinic acid was the major antioxidant present in the hairy roots. Its content in the root biomass reached 5.5 %, calculated on a dry weight basis. 8-Deoxylactucin glucoside (crepidiaside A) was the major sesquiterpene lactone in the hairy roots. Its content reached 1.4 %, calculated on a dry weight basis, and was nearly two orders of magnitude higher than that in the roots of wild chicory plant. The glucosidic derivative of 8-deoxylactucin constituted over 85 % of the total sesquiterpene lactone content in the long-term cultured hairy roots of chicory. Aglycone of this compound was reported to possess anti-inflammatory activity. The qualitative and quantitative analyses of hydroxycinnamates in callus and hairy root cultures of C. intybus were undertaken for the first time. PMID:23975347

  5. A Versatile Family 3 Glycoside Hydrolase from Bifidobacterium adolescentis Hydrolyzes ?-Glucosides of the Fusarium Mycotoxins Deoxynivalenol, Nivalenol, and HT-2 Toxin in Cereal Matrices.

    PubMed

    Michlmayr, Herbert; Varga, Elisabeth; Malachova, Alexandra; Nguyen, Nhung Thi; Lorenz, Cindy; Haltrich, Dietmar; Berthiller, Franz; Adam, Gerhard

    2015-08-01

    Glycosylation plays a central role in plant defense against xenobiotics, including mycotoxins. Glucoconjugates of Fusarium toxins, such as deoxynivalenol-3-O-?-d-glucoside (DON-3G), often cooccur with their parental toxins in cereal-based food and feed. To date, only limited information exists on the occurrence of glucosylated mycotoxins and their toxicological relevance. Due to a lack of analytical standards and the requirement of high-end analytical instrumentation for their direct determination, hydrolytic cleavage of ?-glucosides followed by analysis of the released parental toxins has been proposed as an indirect determination approach. This study compares the abilities of several fungal and recombinant bacterial ?-glucosidases to hydrolyze the model analyte DON-3G. Furthermore, substrate specificities of two fungal and two bacterial (Lactobacillus brevis and Bifidobacterium adolescentis) glycoside hydrolase family 3 ?-glucosidases were evaluated on a broader range of substrates. The purified recombinant enzyme from B. adolescentis (BaBgl) displayed high flexibility in substrate specificity and exerted the highest hydrolytic activity toward 3-O-?-d-glucosides of the trichothecenes deoxynivalenol (DON), nivalenol, and HT-2 toxin. A Km of 5.4 mM and a Vmax of 16 ?mol min(-1) mg(-1) were determined with DON-3G. Due to low product inhibition (DON and glucose) and sufficient activity in several extracts of cereal matrices, this enzyme has the potential to be used for indirect analyses of trichothecene-?-glucosides in cereal samples. PMID:25979885

  6. Development and Validation of a Decigram-Scale Method for the Separation of Limonin from Limonin Glucoside by C-18 Flash Chromatography

    Technology Transfer Automated Retrieval System (TEKTRAN)

    A preparative method for decigram-scale polishing of limonin glucoside with regard to removing traces of limonin, the main bitter principle in Citrus, is reported. During the method development and up-scaling stages, in which sample purity, sample size, solvent amounts, and drying conditions were v...

  7. Liquid Chromatography-Electrospray Ionization Mass Spectrometry Method for the Rapid Identification of Citrus Limonoid Glucosides in Citrus Juices and Extracts

    Technology Transfer Automated Retrieval System (TEKTRAN)

    A rapid and selective liquid chromatography-electrospray ionization mass spectrometry (LC-ESI-MS) method to screen citrus samples for limonoid glucosides and estimate their relative concentrations has been developed. This method utilizes a phenyl stationary phase, whereas previous methods have reli...

  8. Determination of citrus limonoid glucosides by high performance liquid chromatography coupled to post-column reaction with Ehrlich’s Reagent

    Technology Transfer Automated Retrieval System (TEKTRAN)

    A method for the identification and quantification of citrus limonoid glucosides in juices based upon high performance liquid chromatography (HPLC) separation coupled to post-column reaction with Ehrlichs’s reagent has been developed. This method utilizes a phenyl stationary phase and an isocratic ...

  9. Cyanidin-3-O-beta-glucoside inhibits LPS-induced expression of inflammatory mediators through decreasing IkBa Phosphorylation in THP-1 Cells

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Objective and design: As a common phytochemical, cyanidin 3-O-beta-glucoside (C3G) has a role in inhibiting inflammatory mediators; however, its mechanism of action remains unclear. The purpose of this study was to explore the effect of C3G on lipopolysaccharide (LPS)-stimulated TNFa and IL-6 expres...

  10. Observation of T-2 Toxin and HT-2 Toxin Glucosides from Fusarium sporotrichioides by Liquid Chromatography Coupled to Tandem Mass Spectrometry (LC-MS/MS)

    PubMed Central

    Busman, Mark; Poling, Stephen M.; Maragos, Chris M.

    2011-01-01

    The trichothecenes produced by solid and liquid cultures of Fusarium sporotrichioides were evaluated with high performance liquid chromatography-tandem mass spectrometry (LC-MS/MS). Along with the expected T-2 toxin HT-2 toxin and neosolaniol, two additional compounds were detected, which had ions 162 m/z higher than those in the mass spectra of T-2 toxin or HT-2 toxin. Fragmentation behavior of these two compounds was similar to that of T-2 toxin and HT-2 toxin. Based on LC-MS/MS behavior, it is proposed that the two compounds are T-2 toxin 3-O-glucoside and HT-2 toxin 3-O-glucoside. Production of the two glucosides was measured in kernels from wheat and oat inoculated with F. sporotrichiodes, as well as in cultures grown in liquid media and on cracked corn or rice. Production of glucosides in wheat and oats suggest that they may also be present in naturally contaminated cereals. PMID:22295176

  11. Chemical analysis of Penstemon campanulatus (Cav.) Willd.--antimicrobial activities.

    PubMed

    Zajdel, Sybilla M; Graikou, Konstantia; G?owniak, Kazimierz; Chinou, Ioanna

    2012-03-01

    A new iridoid glucoside named 10-isovaleroyl-dihydropenstemide (1), along with nine known compounds was isolated from the aerial part of Penstemon campanulatus (Cav.) Willd. The known compounds include three iridoid glucosides, one phenylpropanoid glucoside, one monoterpene glucoside, one monoterpene lactone and three flavonoids. Their structures were elucidated on the basis of spectral evidence. Additionally four phenolic acids as well as a fatty acid were determined through GC-MS analysis. All isolated compounds and the crude extracts were assayed for their antimicrobial activities against six Gram positive and negative bacteria, as well as against three human pathogenic fungi. PMID:22155592

  12. C-Glucoside xanthone from the stem bark extract of Bersama engleriana

    PubMed Central

    Djemgou, Pierre C.; Hussien, Taha A.; Hegazy, Mohamed-Elamir F.; Ngandeu, François; Neguim, Gilles; Tane, Pierre; Mohamed, Abou-El-Hamd H.

    2010-01-01

    Background: The genus Bersama belongs to the Melianthaceae family and comprises of four species (B. swinnyi, B. yangambiensis, B. abyssinica, and B. engleriana) all of which are very high trees; the latter two detected species are found in Cameroon. Previous phytochemical investigation on B. yangambiensis, B. swinnyi, and B. abyssinica led to the isolation of triterpenes, saponins, flavonoids, and xanthones. Method: The stem bark of B. engleriana were collected in the village, Baham near Bafoussam city, Cameroon in August 2003 and identifi ed by Dr. Onana National Herbaruim, Yaound?, Cameroon. The air dried and powdered stem bark of B. engleriana (1 kg) was extracted at room temperature with CH2Cl2-MeOH (1:1) 5 L for 48 hours. The mixture of the solvent was removed by evaporation to yield 200 g of crude extract. The latter was then dissolved in CH2Cl2 to give the CH2Cl2 soluble fraction of 5 g and a remaining gum of 195 g. Part of the remaining gum (22 g) was dissolved in water and extracted four times with butanol to give 12 g of red oil; which was then separated by paper chromatography, with butanol-acetic acid-water (4:1:5), to give 3 g of orange gum; purification was carried out on HPLC with MeOH (100%) to yield 2 g of mangiferin (1) as red oil. The CH2Cl2 soluble extract was eluted on silica gel n-hexane-CH2Cl2 gradient ratio and Sephadex LH-20 (n-hexane -CH2Cl2 -MeOH, (7:4:0.5) to afford compounds swinniol (2), ?4-stigmaster-3?-ol (3), 4-methylstigmaster-5,23-dien-3?-ol(4). Results: Herein, we carried out a phytochemical study of the stem bark of B. engleriana, and we report herein the isolation and structural elucidation of mangiferin, in addition to three triterpenes, previously reported from other species of the genus.[35] The assignment of the signals of mangiferin was determined using 1H, 13C-NMR, and 2D-NMR spectral data (HMQC, COSY, HMBC). The terpenoids were identifi ed by comparison of their 1H and 13C-NMR spectra with the literature data. Fractionation of the CH2Cl2-MeOH (1:1) extract of the stem bark of B. engleriana Guike gave mangiferin (1), in addition to three previously reported triterpenes, swinniol (2), ?4-stigmaster-3?-ol (3), and 4-methylstigmaster-5,23-dien-3-?-ol (4). Conclusions: A chemical investigation of the CH2Cl2-MeOH extract of the stem bark of Bersama engleriana afforded a xanthone C-glucoside (mangiferin) and fi rst isolation of three terpenoids from this species: swinniol (2), ?4-stigmaster-3?-ol (3), and 4-methylstigmaster-5,23-dien-3-?-ol (4). The complete 1H and 13C chemical shift assignments of mangiferin were determined using 1D and 2D NMR spectroscopic data (COSY, HMQC, HMBC, DEPT). The structures of the terpenoids were determined from their 1H and 13C NMR data and compared with the literature data. PMID:21808572

  13. L-ascorbic acid- and L-ascorbic acid 2-glucoside accelerate in vivo liver regeneration and lower serum alanine aminotransaminase activity in 70% partially hepatectomized rats.

    PubMed

    Kimura, Mitsutoshi; Moteki, Hajime; Uchida, Masaki; Natsume, Hideshi; Ogihara, Masahiko

    2014-01-01

    The effects of L-ascorbic acid and its stable analogue L-ascorbic acid 2-glucoside on the restoration of liver mass and recovery of liver function after 70% partial hepatectomy (PH), were compared with other natural vitamin C analogues in rats in vivo. L-Ascorbic acid (100 mg/kg/d, intraperitoneally (i.p.))- and L-ascorbic acid 2-glucoside (50 mg/kg/d, i.p.)-treated rats showed an approximately 1.3-fold increase in the ratio of liver weight (LW) to body weight (BW), when compared to saline (as control)-, L-dehydroascorbic acid (150 mg/kg/d, i.p.)- and D-isoascorbic acid (150 mg/kg/d, i.p.)-administrated rats on day 3 after PH. Accordingly, 5-bromo-2-deoxyuridine-labeling index in the regenerating liver was significantly higher in L-ascorbic acid- and L-ascorbic acid 2-glucoside-treated rats compared with saline-, L-dehydroascorbic acid and D-isoascorbic acid-treated rats on day 1. In control rats, liver-related serum alanine aminotransferase (ALT) activity was rapidly elevated on day 1, and then decreased to near pre-operative levels on day 5 following PH. L-Ascorbic acid and L-ascorbic acid 2-glucoside significantly lowered the serum ALT on day 1 after PH compared with saline-, L-dehydroascorbic acid- and D-isoascorbic acid-administered rats. These results demonstrate that L-ascorbic acid and L-ascorbic acid 2-glucoside significantly promote the regeneration of liver mass and function with full recovery after liver injury. PMID:24818255

  14. Characterization and expression profile of two UDP-glucosyltransferases, UGT85K4 and UGT85K5, catalyzing the last step in cyanogenic glucoside biosynthesis in cassava.

    PubMed

    Kannangara, Rubini; Motawia, Mohammed S; Hansen, Natascha K K; Paquette, Suzanne M; Olsen, Carl E; Møller, Birger L; Jørgensen, Kirsten

    2011-10-01

    Manihot esculenta (cassava) contains two cyanogenic glucosides, linamarin and lotaustralin, biosynthesized from l-valine and l-isoleucine, respectively. In this study, cDNAs encoding two uridine diphosphate glycosyltransferase (UGT) paralogs, assigned the names UGT85K4 and UGT85K5, have been isolated from cassava. The paralogs display 96% amino acid identity, and belong to a family containing cyanogenic glucoside-specific UGTs from Sorghum bicolor and Prunus dulcis. Recombinant UGT85K4 and UGT85K5 produced in Escherichia coli were able to glucosylate acetone cyanohydrin and 2-hydroxy-2-methylbutyronitrile, forming linamarin and lotaustralin. UGT85K4 and UGT85K5 show broad in?vitro substrate specificity, as documented by their ability to glucosylate other hydroxynitriles, some flavonoids and simple alcohols. Immunolocalization studies indicated that UGT85K4 and UGT85K5 co-occur with CYP79D1/D2 and CYP71E7 paralogs, which catalyze earlier steps in cyanogenic glucoside synthesis in cassava. These enzymes are all found in mesophyll and xylem parenchyma cells in the first unfolded cassava leaf. In?situ PCR showed that UGT85K4 and UGT85K5 are co-expressed with CYP79D1 and both CYP71E7 paralogs in the cortex, xylem and phloem parenchyma, and in specific cells in the endodermis of the petiole of the first unfolded leaf. Based on the data obtained, UGT85K4 and UGT85K5 are concluded to be the UGTs catalyzing in?planta synthesis of cyanogenic glucosides. The localization of the biosynthetic enzymes suggests that cyanogenic glucosides may play a role in both defense reactions and in fine-tuning nitrogen assimilation in cassava. PMID:21736650

  15. Application of ESI/MS, CID/MS and tandem MS/MS to the fragmentation study of eriodictyol 7-O-glucosyl-(1-->2)-glucoside and luteolin 7-O-glucosyl-(1-->2)-glucoside

    NASA Astrophysics Data System (ADS)

    Es-Safi, Nour-Eddine; Kerhoas, Lucien; Einhorn, Jacques; Ducrot, Paul-Henri

    2005-12-01

    A mass spectrometric method based on the combined use of positive and negative electrospray ionization, collision-induced dissociation and tandem mass spectrometry has been applied to the structural characterization of the eriodictyol 7-O-glucosyl-(1-->2)-glucoside and luteolin 7-O-glucosyl-(1-->2)-glucoside. The low-energy product ion mass spectrum of [M + H]+ and [M - H]- ions showed extensive fragmentation of the diglucose moiety, loss of the glycan residue, and fragmentation of the aglycon units that permit characterization of the interglycosidic linkage and the substituents in the A- and B-rings. Both glycosides were shown to yield the 0,2X00,2X1 ion which can be considered as characteristic of the 1-->2 interglycosidic linkage in the glucoglucoside adducts, since it can not be formed in the case of other interglycosidic types. In the case of the eriodictyol diglucoside the 1, 3 fragmentation of the C-ring was observed before those involving the carbohydrates thus allowing the position determination of the diglucoside moiety on the A-ring. In the negative ion mode only the luteolin diglucoside was shown to undergo collision-induced homolytic and heterolytic cleavages of the O-glycosidic bond producing the aglycone radical-anion [Y0-H]-- and Y0- product ions, while this was not observed in the case of eriodictyol glycoside. CID MS/MS analysis of the sodiated molecules gave complementary informations for the structural characterization of the studied compounds. The B2+ fragment which is useful for establishing that the terminal carbohydrate unit is linked to another carbohydrate and not directly to the aglycone was obtained as base peak. This result is of analytical value for the differentiation of O-diglycosyl and di-O-glycosyl flavonoids.

  16. Identification of rice Os4BGlu13 as a ?-glucosidase which hydrolyzes gibberellin A4 1-O-?-d-glucosyl ester, in addition to tuberonic acid glucoside and salicylic acid derivative glucosides.

    PubMed

    Hua, Yanling; Ekkhara, Watsamon; Sansenya, Sompong; Srisomsap, Chantragan; Roytrakul, Sittiruk; Saburi, Wataru; Takeda, Ryosuke; Matsuura, Hideyuki; Mori, Haruhide; Ketudat Cairns, James R

    2015-10-01

    Gibberellin 1-O-?-d-glucose ester hydrolysis activity has been detected in rice seedling extracts, but no enzyme responsible for this activity has ever been purified and identified. Therefore, gibberellin A4 glucosyl ester (GA4-GE) ?-d-glucosidase activity was purified from ten-day rice seedling stems and leaves. The family 1 glycoside hydrolase Os4BGlu13 was identified in the final purification fraction. The Os4BGlu13 cDNA was amplified from rice seedlings and expressed as an N-terminal thioredoxin-tagged fusion protein in Escherichia coli. The purified recombinant Os4BGlu13 protein (rOs4BGlu13) had an optimum pH of 4.5, for hydrolysis of p-nitrophenyl ?-d-glucopyranoside (pNPGlc), which was the best substrate identified, with a kcat/Km of 637 mM(-1) s(-1). rOs4BGlu13 hydrolyzed helicin best among natural glycosides tested (kcat/Km of 74.4 mM(-1) s(-1)). Os4BGlu13 was previously designated tuberonic acid glucoside (TAG) ?-glucosidase (TAGG), and here the kcat/Km of rOsBGlu13 for TAG was 6.68 mM(-1) s(-1), while that for GA4-GE was 3.63 mM(-1) s(-1) and for salicylic acid glucoside (SAG) is 0.88 mM(-1) s(-1). rOs4BGlu13 also hydrolyzed oligosaccharides, with preference for short ?-(1 ? 3)-linked over ?-(1 ? 4)-linked glucooligosaccharides. The enzymatic data suggests that Os4BGlu13 may contribute to TAG, SAG, oligosaccharide and GA4-GE hydrolysis in the rice plant, although helicin or a similar compound may be its primary target. PMID:26241499

  17. Anti-inflammatory effect of the blueberry anthocyanins malvidin-3-glucoside and malvidin-3-galactoside in endothelial cells.

    PubMed

    Huang, Wu-Yang; Liu, Ya-Mei; Wang, Jian; Wang, Xing-Na; Li, Chun-Yang

    2014-01-01

    Blueberry fruits have a wide range of health benefits because of their abundant anthocyanins, which are natural antioxidants. The purpose of this study was to investigate the inhibitory effect of blueberry's two main anthocyanins (malvidin-3-glucoside and malvidin-3-galactoside) on inflammatory response in endothelial cells. These two malvidin glycosides could inhibit tumor necrosis factor-alpha (TNF-?) induced increases of monocyte chemotactic protein-1 (MCP-1), intercellular adhesion molecule-1 (ICAM-1), and vascular cell adhesion molecule-1 (VCAM-1) production both in the protein and mRNA levels in a concentration-dependent manner. Mv-3-glc at the concentration of 1 ?M could inhibit 35.9% increased MCP-1, 54.4% ICAM-1, and 44.7% VCAM-1 protein in supernatant, as well as 9.88% MCP-1 and 48.6% ICAM-1 mRNA expression (p<0.05). In addition, they could decrease I?B? degradation (Mv-3-glc, Mv-3-gal, and their mixture at the concentration of 50 ?M had the inhibition rate of 84.8%, 75.3%, and 43.2%, respectively, p<0.01) and block the nuclear translocation of p65, which suggested their anti-inflammation mechanism was mediated by the nuclear factor-kappa B (NF-?B) pathway. In general malvidin-3-glucoside had better anti-inflammatory effect than malvidin-3-galactoside. These results indicated that blueberry is good resource of anti-inflammatory anthocyanins, which can be promising molecules for the development of nutraceuticals to prevent chronic inflammation in many diseases. PMID:25153881

  18. Pteroside A2--a new illudane-type sesquiterpene glucoside from pteridium caudatum L. Maxon, and the spectrometric characterization of caudatodienone.

    PubMed

    Castillo, Uvidelio F; Wilkins, Alistair L; Lauren, Denis R; Smith, Barry L; Alonso-Amelot, Miguel

    2003-04-23

    Fractionation of an extract of Pteridium caudatum L. Maxon. (syn P. aquilinum L. Kuhn var. caudatum) which had earlier yielded the illudane-type sesquiterpene glucosides, ptaquiloside (1a), isoptaquiloside (1b), and caudatoside (1c) afforded a mixture containing 1a and two minor components. Preparative HPLC afforded ptaquiloside Z (1d) and a new pteroside glucoside (pteroside A2) (3e), which was identified using a combination of mass spectral and one- and two-dimensional NMR analyses. The (1)H and (13)C NMR and mass spectrometric characterization of caudatodienone (2b), an unstable dienone derived from the degradation of caudatoside (1c) in pyridine solution, and the GC-MS characterization of some pterosin-type degradation products produced by reacting this solution with cosolvents is also reported. PMID:12696937

  19. A flavonoid 3-O-glucoside:2?-O-glucosyltransferase responsible for terminal modification of pollen-specific flavonols in Arabidopsis thaliana

    PubMed Central

    Yonekura-Sakakibara, Keiko; Nakabayashi, Ryo; Sugawara, Satoko; Tohge, Takayuki; Ito, Takuya; Koyanagi, Misuzu; Kitajima, Mariko; Takayama, Hiromitsu; Saito, Kazuki

    2014-01-01

    Flavonol 3-O-diglucosides with a 1?2 inter-glycosidic linkage are representative pollen-specific flavonols that are widely distributed in plants, but their biosynthetic genes and physiological roles are not well understood. Flavonoid analysis of four Arabidopsis floral organs (pistils, stamens, petals and calyxes) and flowers of wild-type and male sterility 1 (ms1) mutants, which are defective in normal development of pollen and tapetum, showed that kaempferol/quercetin 3-O-?-d-glucopyranosyl-(1?2)-?-d-glucopyranosides accumulated in Arabidopsis pollen. Microarray data using wild-type and ms1 mutants, gene expression patterns in various organs, and phylogenetic analysis of UDP-glycosyltransferases (UGTs) suggest that UGT79B6 (At5g54010) is a key modification enzyme for determining pollen-specific flavonol structure. Kaempferol and quercetin 3-O-glucosyl-(1?2)-glucosides were absent from two independent ugt79b6 knockout mutants. Transgenic ugt79b6 mutant lines transformed with the genomic UGT79B6 gene had the same flavonoid profile as wild-type plants. Recombinant UGT79B6 protein converted kaempferol 3-O-glucoside to kaempferol 3-O-glucosyl-(1?2)-glucoside. UGT79B6 recognized 3-O-glucosylated/galactosylated anthocyanins/flavonols but not 3,5- or 3,7-diglycosylated flavonoids, and prefers UDP-glucose, indicating that UGT79B6 encodes flavonoid 3-O-glucoside:2?-O-glucosyltransferase. A UGT79B6-GUS fusion showed that UGT79B6 was localized in tapetum cells and microspores of developing anthers. PMID:24916675

  20. A flavonoid 3-O-glucoside:2"-O-glucosyltransferase responsible for terminal modification of pollen-specific flavonols in Arabidopsis thaliana.

    PubMed

    Yonekura-Sakakibara, Keiko; Nakabayashi, Ryo; Sugawara, Satoko; Tohge, Takayuki; Ito, Takuya; Koyanagi, Misuzu; Kitajima, Mariko; Takayama, Hiromitsu; Saito, Kazuki

    2014-09-01

    Flavonol 3-O-diglucosides with a 1?2 inter-glycosidic linkage are representative pollen-specific flavonols that are widely distributed in plants, but their biosynthetic genes and physiological roles are not well understood. Flavonoid analysis of four Arabidopsis floral organs (pistils, stamens, petals and calyxes) and flowers of wild-type and male sterility 1 (ms1) mutants, which are defective in normal development of pollen and tapetum, showed that kaempferol/quercetin 3-O-?-d-glucopyranosyl-(1?2)-?-d-glucopyranosides accumulated in Arabidopsis pollen. Microarray data using wild-type and ms1 mutants, gene expression patterns in various organs, and phylogenetic analysis of UDP-glycosyltransferases (UGTs) suggest that UGT79B6 (At5g54010) is a key modification enzyme for determining pollen-specific flavonol structure. Kaempferol and quercetin 3-O-glucosyl-(1?2)-glucosides were absent from two independent ugt79b6 knockout mutants. Transgenic ugt79b6 mutant lines transformed with the genomic UGT79B6 gene had the same flavonoid profile as wild-type plants. Recombinant UGT79B6 protein converted kaempferol 3-O-glucoside to kaempferol 3-O-glucosyl-(1?2)-glucoside. UGT79B6 recognized 3-O-glucosylated/galactosylated anthocyanins/flavonols but not 3,5- or 3,7-diglycosylated flavonoids, and prefers UDP-glucose, indicating that UGT79B6 encodes flavonoid 3-O-glucoside:2?-O-glucosyltransferase. A UGT79B6-GUS fusion showed that UGT79B6 was localized in tapetum cells and microspores of developing anthers. PMID:24916675

  1. Attempt to synthesize 2,3,5,4'-tetrahydroxystilbene derived from 2,3,5,4'-tetrahydroxystilbene-2-O-?-glucoside (THSG).

    PubMed

    Tamura, Masafumi; Koshibe, Yuhei; Kaji, Kiho; Ueda, Jun-Ya; Shirataki, Yoshiaki

    2015-01-01

    An attempt to synthesize aglycone 1 derived from 2,3,5,4'-tetrahydroxystilbene-2-O-?-glucoside (THSG) via the Wittig reaction and Mizoroki-Heck reaction is described. In the Wittig protocol, 2,3,5,4'-tetramethoxystilbene 2 was obtained. Additionally, a palladium-catalyzed Mizoroki-Heck reaction strategy yielded 2-aryl-2,3-dihydrobenzofuran 13 instead of derivative 12 in good yield. PMID:25475833

  2. The enzymatic hydrolysis of 6-acylamino-4-methylumbelliferyl-beta-D-glucosides: identification of a novel human acid beta-glucosidase.

    PubMed

    Mikhaylova, M; Wiederschain, G; Mikhaylov, V; Aerts, J M

    1996-10-01

    Fluorogenic 6-acylamino-4-methylumbelliferyl-beta-D-glucosides were found to be poor substrates for the three known human beta-glucosidases, i.e., lysosomal and non-lysosomal glucocerebrosidases and cytosolic broad-specificity beta-glucosidase. However, homogenates of human tissues and human cell types showed significant enzymatic hydrolysis of 6-ethanoylamino-4-methylumbelliferyl-beta-D-glucoside (EMGlc) due to the activity of a hitherto undescribed beta-glucosidase, called here EMGlc-ase. It was shown that the isozyme is hardly active towards 4-methylumbelliferyl-beta-D-glucoside or glucosylceramide. EMGlc-ase exhibits maximal activity at pH 4.5 and 5.0 in the absence and presence of sodium taurocholate respectively. It is a soluble lysosomal enzyme with a discrete isoelectric point of about 5.0. EMGlc-ase is not inhibited by conduritol B-epoxide, is activated by sodium taurocholate and binds strongly to Concanavalin A. This enzyme is not deficient in relation to Gaucher disease. PMID:8876629

  3. The effect of 2,3,4',5-tetrahydroxystilbene-2-O-?-D-glucoside on pressure overload-induced cardiac remodeling in rats and its possible mechanism.

    PubMed

    Xu, Xiao Le; Zhu, Qiu Yan; Zhao, Cheng; Wang, Fei; Zhou, Zhong Yin; Hu, Ya E; Zhang, Wei

    2014-02-01

    The aim of the present study was to investigate the effects of 2,3,4',5-tetrahydroxystilbene-2-O-beta-D-glucoside, an active component extracted from Polygonum multiflorum, on pressure overload-induced cardiac remodeling in rats. A rat model with cardiac remodeling was induced by abdominal aortic banding. 2,3,4',5-Tetrahydroxystilbene-2-O-beta-D-glucoside (30, 60, 120?mg/kg/day) was administered 3 days after abdominal aortic banding and continued for 30 days. The abdominal aortic banding-treated rats had significantly elevated blood pressure, left ventricular hypertrophy, and myocardial fibrosis. Left ventricular hypertrophy was characterized by an increase in the ratios of the heart and left ventricular weights to body weight, and increased myocyte cross-sectional areas, hypertrophic ventricular septum, and left ventricular posterior wall. The accumulation of myocardial interstitial perivascular collagen and elevated cardiac hydroxyproline content indicated myocardial fibrosis. The pathological changes above were attenuated by 2,3,4',5-tetrahydroxystilbene-2-O-beta-D-glucoside. Additionally, it markedly reduced collagen I and III expressions and regulated matrix metalloproteinase-2,9 and inhibitors of metalloproteinase expressions, as markers of myocardial fibrosis. Furthermore, we explored the underlying mechanisms for such effects of 2,3,4',5-tetrahydroxystilbene-2-O-beta-D-glucoside. The results showed that it significantly reduced myocardium angiotensin II, enhanced the activities of superoxide dismutase and glutathione peroxidase in serum and myocardial tissue, as well as inhibited protein expression of transforming growth factor-?1 and phosphorylation of extracellular signal-regulated kinase 1/2 and p38 mitogen-activated protein kinase in the myocardial tissue. Our results suggest that 2,3,4',5-tetrahydroxystilbene-2-O-beta-D-glucoside could prevent cardiac remodeling induced by pressure overload in rats. The underlying mechanisms may be related to a decreasing angiotensin II level, an antioxidant effect of the tested compound, suppression of transforming growth factor-?1 expression, and inhibition of extracellular signal-regulated kinase 1/2 and p38 mitogen-activated protein kinase activation. PMID:24431015

  4. ABCC1, an ATP Binding Cassette Protein from Grape Berry, Transports Anthocyanidin 3-O-Glucosides[W][OA

    PubMed Central

    Francisco, Rita Maria; Regalado, Ana; Ageorges, Agnès; Burla, Bo J.; Bassin, Barbara; Eisenach, Cornelia; Zarrouk, Olfa; Vialet, Sandrine; Marlin, Thérèse; Chaves, Maria Manuela; Martinoia, Enrico; Nagy, Réka

    2013-01-01

    Accumulation of anthocyanins in the exocarp of red grapevine (Vitis vinifera) cultivars is one of several events that characterize the onset of grape berry ripening (véraison). Despite our thorough understanding of anthocyanin biosynthesis and regulation, little is known about the molecular aspects of their transport. The participation of ATP binding cassette (ABC) proteins in vacuolar anthocyanin transport has long been a matter of debate. Here, we present biochemical evidence that an ABC protein, ABCC1, localizes to the tonoplast and is involved in the transport of glucosylated anthocyanidins. ABCC1 is expressed in the exocarp throughout berry development and ripening, with a significant increase at véraison (i.e., the onset of ripening). Transport experiments using microsomes isolated from ABCC1-expressing yeast cells showed that ABCC1 transports malvidin 3-O-glucoside. The transport strictly depends on the presence of GSH, which is cotransported with the anthocyanins and is sensitive to inhibitors of ABC proteins. By exposing anthocyanin-producing grapevine root cultures to buthionine sulphoximine, which reduced GSH levels, a decrease in anthocyanin concentration is observed. In conclusion, we provide evidence that ABCC1 acts as an anthocyanin transporter that depends on GSH without the formation of an anthocyanin-GSH conjugate. PMID:23723325

  5. Long chain fatty acid acylated derivatives of quercetin-3-o-glucoside as antioxidants to prevent lipid oxidation.

    PubMed

    Warnakulasuriya, Sumudu N; Ziaullah; Rupasinghe, H P Vasantha

    2014-01-01

    Flavonoids have shown promise as natural plant-based antioxidants for protecting lipids from oxidation. It was hypothesized that their applications in lipophilic food systems can be further enhanced by esterification of flavonoids with fatty acids. Quercetin-3-O-glucoside (Q3G) was esterified individually with six selected long chain fatty acids: stearic acid (STA), oleic acid (OLA), linoleic acid (LNA), ?-linolenic acid (ALA), eicosapentaenoic acid (EPA) and decosahexaenoic acid (DHA), using Candida antarctica B lipase as the biocatalyst. The antioxidant activity of esterified flavonoids was evaluated using lipid oxidation model systems of poly-unsaturated fatty acids-rich fish oil and human low density lipoprotein (LDL), in vitro. In the oil-in-water emulsion, Q3G esters exhibited 50% to 100% inhibition in primary oxidation and 30% to 75% inhibition in secondary oxidation. In bulk oil, Q3G esters did not provide considerable protection from lipid oxidation; however, Q3G demonstrated more than 50% inhibition in primary oxidation. EPA, DHA and ALA esters of Q3G showed significantly higher inhibition in Cu2+- and peroxyl radical-induced LDL oxidation in comparison to Q3G. PMID:25384198

  6. Total Glucosides of Danggui Buxue Tang Attenuate BLM-Induced Pulmonary Fibrosis via Regulating Oxidative Stress by Inhibiting NOX4

    PubMed Central

    Zhao, Ping; Zhou, Wen-Cheng; Li, De-Lin; Mo, Xiao-Ting; Xu, Liang; Li, Liu-Cheng; Cui, Wen-Hui; Gao, Jian

    2015-01-01

    Pulmonary fibrosis (PF) is a serious chronic lung disease with unknown pathogenesis. Researches have confirmed that oxidative stress which is regulated by NADPH oxidase-4 (NOX4), a main source of reactive oxygen species (ROS), is an important molecular mechanism underlying PF. Previous studies showed that total glucosides of Danggui Buxue Tang (DBTG), an extract from a classical traditional Chinese herbal formula, Danggui Buxue Tang (DBT), attenuated bleomycin-induced PF in rats. However, the mechanisms of DBTG are still not clear. We hypothesize that DBTG attenuates PF through regulating the level of oxidative stress by inhibiting NOX4. And we found that fibrosis indexes hydroxyproline (HYP) and type I collagen (Col-I) were lower in DBTG groups compared with the model group. In addition, the expression of transforming growth factor-?1 (TGF-?1) and expression of alpha smooth muscle actin (?-SMA) were also much more decreased than the model group. For oxidative stress indicators, DBTG blunted the decrease of superoxide dismutase (SOD) activity, total antioxidant capacity (T-AOC), and the increase in malondialdehyde (MDA), 8-iso-prostaglandin in lung homogenates. Treatment with DBTG restrained the expression of NOX4 compared to the model group. Present study confirms that DBTG inhibits BLM-induced PF by modulating the level of oxidative stress via suppressing NOX4. PMID:26347805

  7. Deoxynivalenol & Deoxynivalenol-3-Glucoside Mitigation through Bakery Production Strategies: Effective Experimental Design within Industrial Rusk-Making Technology.

    PubMed

    Generotti, Silvia; Cirlini, Martina; Malachova, Alexandra; Sulyok, Michael; Berthiller, Franz; Dall'Asta, Chiara; Suman, Michele

    2015-08-01

    In the scientific field, there is a progressive awareness about the potential implications of food processing on mycotoxins especially concerning thermal treatments. High temperatures may cause, in fact, transformation or degradation of these compounds. This work is aimed to study the fate of mycotoxins during bakery processing, focusing on deoxynivalenol (DON) and deoxynivalenol-3-glucoside (DON3Glc), along the chain of industrial rusk production. Starting from naturally contaminated bran, we studied how concentrations of DON and DON3Glc are influenced by modifying ingredients and operative conditions. The experiments were performed using statistical Design of Experiment (DoE) schemes to synergistically explore the relationship between mycotoxin reduction and the indicated processing transformation parameters. All samples collected during pilot plant experiments were analyzed with an LC-MS/MS multimycotoxin method. The obtained model shows a good fitting, giving back relevant information in terms of optimization of the industrial production process, in particular suggesting that time and temperature in baking and toasting steps are highly relevant for minimizing mycotoxin level in rusks. A reduction up to 30% for DON and DON3Glc content in the finished product was observed within an acceptable technological range. PMID:26213969

  8. Long Chain Fatty Acid Acylated Derivatives of Quercetin-3-O-Glucoside as Antioxidants to Prevent Lipid Oxidation

    PubMed Central

    Warnakulasuriya, Sumudu N.; Ziaullah; Rupasinghe, H.P. Vasantha

    2014-01-01

    Flavonoids have shown promise as natural plant-based antioxidants for protecting lipids from oxidation. It was hypothesized that their applications in lipophilic food systems can be further enhanced by esterification of flavonoids with fatty acids. Quercetin-3-O-glucoside (Q3G) was esterified individually with six selected long chain fatty acids: stearic acid (STA), oleic acid (OLA), linoleic acid (LNA), ?-linolenic acid (ALA), eicosapentaenoic acid (EPA) and decosahexaenoic acid (DHA), using Candida antarctica B lipase as the biocatalyst. The antioxidant activity of esterified flavonoids was evaluated using lipid oxidation model systems of poly-unsaturated fatty acids-rich fish oil and human low density lipoprotein (LDL), in vitro. In the oil-in-water emulsion, Q3G esters exhibited 50% to 100% inhibition in primary oxidation and 30% to 75% inhibition in secondary oxidation. In bulk oil, Q3G esters did not provide considerable protection from lipid oxidation; however, Q3G demonstrated more than 50% inhibition in primary oxidation. EPA, DHA and ALA esters of Q3G showed significantly higher inhibition in Cu2+- and peroxyl radical-induced LDL oxidation in comparison to Q3G. PMID:25384198

  9. A natural flavonoid glucoside icariin inhibits Th1 and Th17 cell differentiation and ameliorates experimental autoimmune encephalomyelitis.

    PubMed

    Shen, Ruile; Deng, Wenjing; Li, Chun; Zeng, Guangwei

    2015-02-01

    Multiple sclerosis (MS) is an autoimmune disease that is characterized by recurrent episodes of T cell-mediated immune attack on central nervous system (CNS) myelin, leading to axon damage and progressive disability. Icariin, a natural flavonoid glucoside isolated from plants in the Epimedium family, has been proved to have various pharmacological activities. However, the effect of icariin on experimental autoimmune encephalomyelitis (EAE) has never been investigated. In our current study, we found that icariin treatment leads to alleviated inflammatory infiltration and reduced blood-brain barrier leakage (BBB) of the paracellular tracer (FITC-dextran) in EAE. Mice that received icariin-treated T cells also displayed lower EAE scores and better clinical recovery from EAE. Icariin administration suppresses the frequencies of Th1 and Th17 cells in the splenocytes and lymph node cells. Icariin-treated mice also show lower frequency of Th17 cells in CNS mononuclear cells. The effect of icariin on Th1 and Th17 cell differentiation may be mediated via modulation of dendritic cells (DCs). Furthermore, icariin suppresses the proliferation of T cells and the differentiation of Th1 and Th17 cells in vitro. In conclusion, icariin ameliorates EAE and this was associated with suppressed Th1 and Th17 cell differentiation. PMID:25528476

  10. Behaviour of cyanidin-3-glucoside, ?-lactoglobulin and polysaccharides nanoparticles in bulk and oil-in-water interfaces.

    PubMed

    Oliveira, Ana; Ruiz-Henestrosa, Víctor M Pizones; von Staszewski, Mariana; Pilosof, Ana M R; Pintado, Manuela

    2015-11-01

    Particle size distributions as well the interfacial and rheological properties of the films at the oil/water interface were used to study the effect of the interacting system between ?-lactoglobulin, cyanidin-3-glucoside and pectin or chitosan in buffer solutions. The particles obtained were smaller with cy-3-gluc-?-lg-pectin and had reduced polydispersity with cy-3-gluc-?-lg-chitosan. Based on time dependent surface pressure results, ?-lg-pectin mixtures showed a slower increase at the beginning of the measurement, while ?-lg-chitosan mixtures showed no differences with ?-lg alone. Contrarily, dilatational properties increased for ternary chitosan mixtures, but they remained similar to the pure protein in ternary pectin mixtures. Cy-3-gluc interfacial properties were reduced by the presence of pectin and chitosan. The interactions between cy-3-gluc and the biopolymers that have been selected in the present work resulted in a lower content of free polyphenol, reduced antioxidant properties as well as free ?-lg. The impact of this effect was more relevant when pectin was used. PMID:26256371

  11. Anti-human rhinovirus 2 activity and mode of action of quercetin-7-glucoside from Lagerstroemia speciosa.

    PubMed

    Song, Jae Hyoung; Park, Kwi Sung; Kwon, Dur Han; Choi, Hwa Jung

    2013-04-01

    Human rhinoviruses (HRVs) are a major cause of the common cold, but there is currently, no registered clinically effective antiviral chemotherapeutic agent for treatment of diseases caused by HRVs. In this study, we examined the antiviral activity of quercetin 7-glucoside (Q7G) from Lagerstroemia speciosa against human rhinovirus 2 (HRV2) using a cytopathic effect (CPE) reduction method. Furthermore, to elucidate the action of Q7G on HRV2 multiplication in more detail, we investigated the effect of Q7G on the infection cycle of HRV2 through time-of-addition study, reverse transcription-polymerase chain reaction analysis, and effects of Q7G on the infectivity of HRV2 particles. Q7G potently showed anti-HRV2 activity by reducing the formation of a visible CPE. Q7G also inhibited virus replication in the initial stage of virus infection by indirect interaction with virus particles, and ribavirin had a relative weaker efficacy compared to Q7G. Therefore, these data suggest that Q7G exerted its anti-HRV2 effect via the inhibition of virus replication in the early stage and these findings provide important information for the utilization of Q7G for HRV2 treatment. PMID:23566054

  12. Deoxynivalenol & Deoxynivalenol-3-Glucoside Mitigation through Bakery Production Strategies: Effective Experimental Design within Industrial Rusk-Making Technology

    PubMed Central

    Generotti, Silvia; Cirlini, Martina; Malachova, Alexandra; Sulyok, Michael; Berthiller, Franz; Dall’Asta, Chiara; Suman, Michele

    2015-01-01

    In the scientific field, there is a progressive awareness about the potential implications of food processing on mycotoxins especially concerning thermal treatments. High temperatures may cause, in fact, transformation or degradation of these compounds. This work is aimed to study the fate of mycotoxins during bakery processing, focusing on deoxynivalenol (DON) and deoxynivalenol-3-glucoside (DON3Glc), along the chain of industrial rusk production. Starting from naturally contaminated bran, we studied how concentrations of DON and DON3Glc are influenced by modifying ingredients and operative conditions. The experiments were performed using statistical Design of Experiment (DoE) schemes to synergistically explore the relationship between mycotoxin reduction and the indicated processing transformation parameters. All samples collected during pilot plant experiments were analyzed with an LC-MS/MS multimycotoxin method. The obtained model shows a good fitting, giving back relevant information in terms of optimization of the industrial production process, in particular suggesting that time and temperature in baking and toasting steps are highly relevant for minimizing mycotoxin level in rusks. A reduction up to 30% for DON and DON3Glc content in the finished product was observed within an acceptable technological range. PMID:26213969

  13. Cytotoxicity of obacunone and obacunone glucoside in human prostate cancer cells involves Akt-mediated programmed cell death.

    PubMed

    Murthy, Kotamballi N Chidambara; Jayaprakasha, Guddadarangavvanahally K; Patil, Bhimanagouda S

    2015-03-01

    Obacunone and obacunone glucoside (OG) are naturally occurring triterpenoids commonly found in citrus and other plants of the Rutaceae family. The current study reports the mechanism of cytotoxicity of citrus-derived obacunone and OG on human androgen-dependent prostate cancer LNCaP cells. Both limonoids exhibited time- and dose-dependent inhibition of cell proliferation, with more than 60% inhibition of cell viability at 100 ?M, after 24 and 48 h. Analysis of fragmentation of DNA, activity of caspase-3, and cytosolic cytochrome-c in the cells treated with limonoids provided evidence for activation of programmed cell death by limonoids. Treatment of LNCaP cells with obacunone and OG resulted in dose-dependent changes in expression of proteins responsible for the induction of programmed cell death through the intrinsic pathway and down-regulation of Akt, a key molecule in cell signaling pathways. In addition, obacunone and OG also negatively regulated an inflammation-associated transcription factor, androgen receptor, and prostate-specific antigen, and activated proteins related to the cell cycle, confirming the ability of limonoids to induce cytotoxicity through multiple pathways. The results of this study provided, for the first time, an evidence of the cytotoxicity of obacunone and OG in androgen-dependent human prostate cancer cells. PMID:25592883

  14. Bioconversion of Cyanidin-3-Rutinoside to Cyanidin-3-Glucoside in Black Raspberry by Crude ?-L-Rhamnosidase from Aspergillus Species.

    PubMed

    Lim, Taehwan; Jung, Hana; Hwang, Keum Taek

    2015-11-28

    Cyanidin-3-glucoside (C3G) has been known to be more bioavailable than cyanidin-3- rutinoside (C3R), the most abundant anthocyanin in black raspberry (Rubus occidentalis). The aim of this study was to enhance the bioavailability of anthocyanins in black raspberry by cleaving L-rhamnose in C3R using crude enzyme extracts (CEEs) from Aspergillus usamii KCTC 6956, A. awamori KCTC 60380, A. niger KCCM 11724, A. oryzae KCCM 12698, and A. kawachii KCCM 32819. The enzyme activities of the CEEs were determined by a spectrophotometric method using rho-nitrophenyl-rhamnopyranoside and rho-nitrophenyl-glucopyranoside. The CEE from A. usamii had the highest ?-L-rhamnosidase activity with 2.73 U/ml at 60°C, followed by those from A. awamori and A. niger. When bioconversion of C3R to C3G in black raspberry was analyzed by HPLC-DAD, the CEEs from A. usamii and A. awamori hydrolyzed 95.7% and 95.6% of C3R to C3G, respectively, after 2 h incubation. The CEEs from A. kawachii and A. oryzae did not convert C3R to C3G in black raspberry. PMID:26165319

  15. Tetrahydroxystilbene glucoside improves TNF-?-induced endothelial dysfunction: involvement of TGF?/Smad pathway and inhibition of vimentin expression.

    PubMed

    Yao, Wenjuan; Gu, Chengjing; Shao, Haoran; Meng, Guoliang; Wang, Huiming; Jing, Xiang; Zhang, Wei

    2015-01-01

    Endothelial dysfunction plays an important role in the pathogenesis of atherogenesis. 2,3,5,4'-tetrahydroxystilbene-2-O-?-D-glucoside (TSG), an active component of the rhizome extract from Polygonum multiflorum (PM), exhibits significant anti-atherosclerotic activity. Here, we used human umbilical vein endothelial cells (HUVECs) induced by tumor necrosis factor-? (TNF-?) in vitro to investigate the cytoprotective effects of TSG on TNF-?-induced endothelial injury and the related mechanisms. Pretreatment with 50 and 100 ?M TSG markedly attenuated TNF-?-induced loss of cell viability and release of lactate dehydrogenase (LDH) and inhibited TNF-?-induced cell apoptosis. The inhibition of vimentin expression was involved in the cytoprotection afforded by TSG. Using inhibitors for PI3K and TGF? or siRNA for Akt and Smad2, we found that vimentin production in HUVECs is regulated by TGF?/Smad signaling, but not by PI3K-Akt-mTOR signaling. Meanwhile, TSG inhibited both the expression of TGF?1 and the phosphorylation of Smad2 and Smad3, and TSG suppressed the nuclear translocation of Smad4 induced by TNF-?. These results suggest that TSG protects HUVECs against TNF-?-induced cell damage by inhibiting vimentin expression via the interruption of the TGF?/Smad signaling pathway. PMID:25571766

  16. Isolation of a flavonoid, apigenin 7-O-glucoside, from Mentha longifolia (L.) Hudson subspecies longifolia and its genotoxic potency.

    PubMed

    Gulluce, Medine; Orhan, Furkan; Yanmis, Derya; Arasoglu, Tulin; Guvenalp, Zuhal; Demirezer, Lutfiye Omur

    2015-09-01

    Mentha is a medicinal and aromatic plant belonging to the Lamiaceae family, which is widely used in food, flavor, cosmetic and pharmaceutical industries. Recently, it has been found that the use of Mentha as a pharmaceutical source is based on its phytochemical constituents that have far been identified as tannins, saponins, phenolic acids and flavonoids. This study was designed to evaluate the mutagenic and antimutagenic activities of apigenin 7-O-glucoside (A7G), a flavonoid isolated from Mentha longifolia (L.) Hudson subspecies longifolia (ML). The possible antimutagenic potential of A7G was examined against mutagens ethyl methanesulfonate and acridine in an eukaryotic cell system Saccharomyces cerevisiae and sodium azide in Salmonella typhimurium TA1535 and 9-aminoacridine in S. typhimurium TA1537. According to our findings, any concentrations of the A7G used did not show mutagenic activity but exerted strong antimutagenic activities at tested concentrations. The inhibition rates for the Ames test ranged from 27.2% (S. typhimurium TA1535: 0.4 ?M/plate) to 91.1% (S. typhimurium TA1537: 0.2 ?M/plate) and for the yeast deletion assay from 4% to 57.7%. This genotoxicological study suggests that a flavonoid from ML owing to antimutagenic properties is of great pharmacological importance and might be beneficial to industries producing food additives, cosmetics and pharmaceuticals products. PMID:23377117

  17. Dissimilar Mechanisms of Cytochrome c Release Induced by Octyl Glucoside-Activated BAX and by BAX Activated with Truncated BID

    PubMed Central

    Li, Tsyregma; Brustovetsky, Tatiana; Antonsson, Bruno; Brustovetsky, Nickolay

    2009-01-01

    SUMMARY In the present study, we compared alkali-resistant BAX insertion into the outer mitochondrial membrane, mitochondrial remodeling, mitochondrial membrane potential changes, and cytochrome c (Cyt c) release from isolated brain mitochondria triggered by recombinant BAX oligomerized with 1% octyl glucoside (BAXoligo) and by a combination of monomeric BAX (BAXmono) and caspase 8-cleaved C-terminal fragment of recombinant BID (truncated BID, tcBID). We also examined whether the effects induced by BAXoligo or by BAXmono activated with tcBID depended on induction of the mitochondrial permeability transition. The results obtained in this study revealed that tcBID plus BAXmono produced BAX insertion and Cyt c release without overt changes in mitochondrial morphology. On the contrary, treatment of mitochondria with BAXoligo resulted in BAX insertion and Cyt c release, which were accompanied by gross distortion of mitochondrial morphology. The effects of BAXoligo could be at least partially suppressed by mitochondrial depolarization. The effects of tcBID plus BAXmono were insensitive to depolarization. BAXoligo produced similar BAX insertion, mitochondrial remodeling, and Cyt c release in KCl? and in N-methyl-D-glucamine-based incubation media indicating a non-essential role for K+ influx into mitochondria in these processes. A combination of cyclosporin A and ADP, inhibitors of the mitochondrial permeability transition, attenuated Cyt c release, mitochondrial remodeling, and depolarization induced by BAXoligo, but failed to influence the effects produced by tcBID plus BAXmono. Thus, our results suggest a significant difference in the mechanisms of the outer mitochondrial membrane permeabilization and Cyt c release induced by detergent-oligomerized BAXoligo and by BAX activated with tcBID. PMID:19664589

  18. Effects of milling and baking technologies on levels of deoxynivalenol and its masked form deoxynivalenol-3-glucoside.

    PubMed

    Kostelanska, Marta; Dzuman, Zbynek; Malachova, Alexandra; Capouchova, Ivana; Prokinova, Evzenie; Skerikova, Alena; Hajslova, Jana

    2011-09-14

    The co-occurrence of the major Fusarium mycotoxin deoxynivalenol (DON) and its conjugate deoxynivalenol-3-glucoside (DON-3-Glc) has been documented in infected wheat. This study reports on the fate of this masked DON within milling and baking technologies for the first time and compares its levels with those of the free parent toxin. The fractionation of DON-3-Glc and DON in milling fractions was similar, tested white flours contained only approximately 60% of their content in unprocessed wheat grains. No substantial changes of both target analytes occurred during the dough preparation process, i.e. kneading, fermentation, and proofing. However, when bakery improvers enzymes mixtures were employed as a dough ingredient, a distinct increase up to 145% of conjugated DON-3-Glc occurred in fermented dough. Some decrease of both DON-3-Glc and DON (10 and 13%, respectively, compared to fermented dough) took place during baking. Thermal degradation products of DON, namely norDON A, B, C, D, and DON-lactone were detected in roasted wheat samples and baked bread samples by means of UPLC-Orbitrap MS. Moreover, thermal degradation products derived from DON-3-Glc were detected and tentatively identified in heat-treated contaminated wheat and bread based on accurate mass measurement performed under the ultrahigh mass resolving power. These products, originating from DON-3-Glc through de-epoxidation and other structural changes in the seskviterpene cycle, were named norDON-3-Glc A, B, C, D, and DON-3-Glc-lactone analogically to DON degradation products. Most of these compounds were located in the crust of experimental breads. PMID:21797213

  19. The Human Fecal Microbiota Metabolizes Deoxynivalenol and Deoxynivalenol-3-Glucoside and May Be Responsible for Urinary Deepoxy-Deoxynivalenol

    PubMed Central

    Duncan, Gary; Richardson, Anthony J.

    2013-01-01

    Deoxynivalenol (DON) is a potent mycotoxin produced by Fusarium molds and affects intestinal nutrient absorption and barrier function in experimental and farm animals. Free DON and the plant metabolite DON-3-?-d-glucoside (D3G) are frequently found in wheat and maize. D3G is stable in the upper human gut, but some human intestinal bacteria release DON from D3G in vitro. Furthermore, some bacteria derived from animal digestive systems degrade DON to a less toxic metabolite, deepoxy-deoxynivalenol (DOM-1). The metabolism of D3G and DON by the human microbiota has not been fully assessed. We therefore conducted in vitro batch culture experiments assessing the activity of the human fecal microbiota to release DON from D3G. We also studied detoxification of DON to DOM-1 by the microbiota and its potential effect on urinary DON excretion in humans. Fecal slurry from five volunteers was spiked with DON or D3G and incubated anaerobically (from 1 h to 7 days), and mycotoxins were extracted into acetonitrile. Mycotoxins were detected in fecal extracts and urine by liquid chromatography-tandem mass spectrometry (LC-MS/MS). The fecal microbiota released DON from D3G very efficiently, with hydrolysis peaking after 4 to 6 h. The fecal microbiota from one volunteer transformed DON to DOM-1. Urine from the same volunteer also contained DOM-1 (4.7% of DON), whereas DOM-1 was not detectable in urine from other volunteers. Our results confirm that the fecal microbiota releases DON from its glycosylated form, hence increasing the toxic burden in exposed individuals. Furthermore, this is first evidence that the human fecal microbiota of one volunteer detoxifies DON, resulting in the appearance of DOM-1 in urine. PMID:23315729

  20. Molecular dynamics simulations of the lyotropic reverse hexagonal (HII) of Guerbet branched-chain ?-D-glucoside.

    PubMed

    Nguan, Hockseng; Ahmadi, Sara; Hashim, Rauzah

    2014-01-01

    Through atomistic molecular dynamic simulations using a GROMOS53a6 force field for the carbohydrate, we studied the lyotropic reverse hexagonal phase HII from a glycolipid, namely the Guerbet branched-chain ?-d-glucoside, at 14% and 22% water concentrations. Our simulations showed that at low water concentration (14%) the sugar head group overlapped extensively and protruded into the water channel. In contrast, in the 22% concentration system a water column free from the sugar headgroup ('free' water) was formed as expected for the system close to the limit of maximum hydration. In both concentrations, we found anomalous water diffusion in the xy-plane, i.e. the two-dimensional space confined by the surface of the cylinder. On the other hand, along the z-axis, the water diffusion obeyed the Einstein relation for the 22% system, while for the 14% system it was slightly anomalous. For the 22% system, the diffusion along the z-axis of the 'free' water obeyed the Einstein relation, while that of the 'bound' water is slightly anomalous. The xy-plane displacement of the 'bound' water was higher than that for the 'free' water at times longer than 200 ps, as a consequence of the exchange of water molecules between the two regions. Based on our findings, we proposed an alternative explanation to the observed spatial heterogeneity in the HII phase from probe diffusion by Penaloza et al. (Phys. Chem. Chem. Phys., 2012, 14(15), 5247-5250). We found the extent of contact with water was different at different oxygen atoms within the sugar ring. Generally, a higher probability of hydrogen bonding but a shorter lifetime was found in 22% water compared to the case of 14% water. Finally, we examined the extension and compression of the alkyl chain of a columnar. PMID:24257208

  1. Plant Food Delphinidin-3-Glucoside Significantly Inhibits Platelet Activation and Thrombosis: Novel Protective Roles against Cardiovascular Diseases

    PubMed Central

    Yang, Yan; Shi, Zhenyin; Reheman, Adili; Jin, Joseph W.; Li, Conglei; Wang, Yiming; Andrews, Marc C.; Chen, Pingguo; Zhu, Guangheng; Ling, Wenhua; Ni, Heyu

    2012-01-01

    Delphinidin-3-glucoside (Dp-3-g) is one of the predominant bioactive compounds of anthocyanins in many plant foods. Although several anthocyanin compounds have been reported to be protective against cardiovascular diseases (CVDs), the direct effect of anthocyanins on platelets, the key players in atherothrombosis, has not been studied. The roles of Dp-3-g in platelet function are completely unknown. The present study investigated the effects of Dp-3-g on platelet activation and several thrombosis models in vitro and in vivo. We found that Dp-3-g significantly inhibited human and murine platelet aggregation in both platelet-rich plasma and purified platelets. It also markedly reduced thrombus growth in human and murine blood in perfusion chambers at both low and high shear rates. Using intravital microscopy, we observed that Dp-3-g decreased platelet deposition, destabilized thrombi, and prolonged the time required for vessel occlusion. Dp-3-g also significantly inhibited thrombus growth in a carotid artery thrombosis model. To elucidate the mechanisms, we examined platelet activation markers via flow cytometry and found that Dp-3-g significantly inhibited the expression of P-selectin, CD63, CD40L, which reflect platelet ?- and ?-granule release, and cytosol protein secretion, respectively. We further demonstrated that Dp-3-g downregulated the expression of active integrin ?IIb?3 on platelets, and attenuated fibrinogen binding to platelets following agonist treatment, without interfering with the direct interaction between fibrinogen and integrin ?IIb?3. We found that Dp-3-g reduced phosphorylation of adenosine monophosphate-activated protein kinase, which may contribute to the observed inhibitory effects on platelet activation. Thus, Dp-3-g significantly inhibits platelet activation and attenuates thrombus growth at both arterial and venous shear stresses, which likely contributes to its protective roles against thrombosis and CVDs. PMID:22624015

  2. Impact of the dual defence system of Plantago lanceolata (Plantaginaceae) on performance, nutrient utilisation and feeding choice behaviour of Amata mogadorensis larvae (Lepidoptera, Erebidae).

    PubMed

    Pankoke, Helga; Gehring, René; Müller, Caroline

    2015-11-01

    Iridoid glycosides are plant defence compounds with potentially detrimental effects on non-adapted herbivores. Some plant species possess ?-glucosidases that hydrolyse iridoid glycosides and thereby release protein-denaturing aglycones. To test the hypothesis that iridoid glycosides and plant ?-glucosidases form a dual defence system, we used Plantago lanceolata and a polyphagous caterpillar species. To analyse the impact of leaf-age dependent differences in iridoid glycoside concentrations and ?-glucosidase activities on insect performance, old or young leaves were freeze-dried and incorporated into artificial diets or were provided freshly to the larvae. We determined larval consumption rates and the amounts of assimilated nitrogen. Furthermore, we quantified ?-glucosidase activities in artificial diets and fresh leaves and the amount of iridoid glycosides that larvae feeding on fresh leaves ingested and excreted. Compared to fresh leaves, caterpillars grew faster on artificial diets, on which larval weight gain correlated positively to the absorbed amount of nitrogen. When feeding fresh young leaves, larvae even lost weight and excreted only minute proportions of the ingested iridoid glycosides intact with the faeces, indicating that the hydrolysis of these compounds might have interfered with nitrogen assimilation and impaired larval growth. To disentangle physiological effects from deterrent effects of iridoid glycosides, we performed dual choice feeding assays. Young leaves, their methanolic extracts and pure catalpol reduced larval feeding in comparison to the respective controls, while aucubin had no effect on larval consumption. We conclude that the dual defence system of P. lanceolata consisting of iridoid glycosides and ?-glucosidases interferes with the nutrient utilisation via the hydrolysis of iridoid glycosides and also mediates larval feeding behaviour in a concentration- and substance-specific manner. PMID:26306994

  3. The identification of degradation products and degradation pathway of malvidin-3-glucoside and malvidin-3,5-diglucoside under microwave treatment.

    PubMed

    Zhao, Mengyao; Luo, Yinghua; Li, Yuan; Liu, Xin; Wu, Jihong; Liao, Xiaojun; Chen, Fang

    2013-12-01

    Understanding the degradation of anthocyanins (Acys) during microwave treatment is required for the application of this novel technology to fruit and vegetable processing. The pH 3.5 buffer solutions containing 50mg/l malvidin-3-glucoside (Mv-3-glu) and malvidin-3,5-diglucoside (Mv-3,5-diglu), respectively, were treated with microwaves at 700 W. In comparison, the samples were heated at 98±2 °C in a water bath. In total, nine degradation products were detected (using LC-UV/Vis-MS/MS) for each Acys after microwave treatment. Anthocyanone A, hydroxycoumarins and dihydroxy phenylacetaldehyde were characterised as the main degradation products of both Acys under microwave conditions, which were not detected in the thermal treatment. In addition, syringic acid, 2,4,6-trihydroxybenzaldehyde, coumarin glucosides and 2,6-dimethoxyphenol were found simultaneously under the microwave and thermal treatments. During the microwave treatment, hydrogen peroxide was formed and resulted in the Baeyer-Villiger-type oxidation of the Acys, which was the main degradation pathway. At the same time, the conventional thermal degradation pathway of Acys also occurred. PMID:23871085

  4. Raman spectroscopic analysis of cyanogenic glucosides in plants: development of a flow injection surface-enhanced Raman scatter (FI-SERS) method for determination of cyanide.

    PubMed

    Thygesen, Lisbeth Garbrecht; Jørgensen, Kirsten; Møller, Birger Lindberg; Engelsen, Søren Balling

    2004-02-01

    Cyanogenic glucosides were studied using Raman spectroscopy. Spectra of the crystal forms of linamarin, linustatin, neolinustatin, amygdalin, sambunigrin, and dhurrin were obtained using a Raman spectrograph microscope equipped with a 532 nm laser. The position of the signal from the C identical with N triple bond of the cyanohydrin group was influenced by the nature of the side group and was above 2240 cm(-1) for the three cyanogenic glucosides that contain a neighboring aromatic ring, and below or partially below 2240 cm(-1) for the non-aromatic cyanoglucosides. Signals from the CN bond of linamarin/lotaustralin in leaves and roots from a medium cyanogenic cassava variety were obtained in situ using a Fourier transform near-infrared (FT-NIR) Raman interferometer with a 1064 nm laser, but the signal was very weak and difficult to obtain. A spectrum containing a signal from the CN bond of dhurrin in a freeze-dried sorghum leaf was also obtained using this instrument. Surface-enhanced Raman Spectroscopy (SERS) was demonstrated to be a more sensitive method that enabled determination of the cyanogenic potential of plant tissue. The SERS method was optimized by flow injection (FI) using a colloidal gold dispersion as effluent. Potential problems and pitfalls of the method are discussed. PMID:15000716

  5. Molecular Cloning and Biochemical Characterization of a Recombinant Sterol 3-O-Glucosyltransferase from Gymnema sylvestre R.Br. Catalyzing Biosynthesis of Steryl Glucosides

    PubMed Central

    Sangwan, Rajender Singh; Asha; Mishra, B. N.; Sangwan, Neelam S.

    2014-01-01

    Gymnema sylvestre R.Br., a pharmacologically important herb vernacularly called Gur-Mar (sugar eliminator), is widely known for its antidiabetic action. This property of the herb has been attributed to the presence of bioactive triterpene glycosides. Although some information regarding pharmacology and phytochemical profiles of the plant are available, no attempts have been made so far to decipher the biosynthetic pathway and key enzymes involved in biosynthesis of steryl glucosides. The present report deals with the identification and catalytic characterization of a glucosyltransferase, catalyzing biosynthesis of steryl glycosides. The full length cDNA (2572?bp) contained an open reading frame of 2106 nucleotides that encoded a 701 amino acid protein, falling into GT-B subfamily of glycosyltransferases. The GsSGT was expressed in Escherichia coli and biochemical characterization of the recombinant enzyme suggested its key role in the biosynthesis of steryl glucosides with catalytic preference for C-3 hydroxyl group of sterols. To our knowledge, this pertains to be the first report on cloning and biochemical characterization of a sterol metabolism gene from G. sylvestre R.Br. catalyzing glucosylation of a variety of sterols of biological origin from diverse organisms such as bacteria, fungi, and plants. PMID:25250339

  6. Studies on metabolism of total glucosides of paeony from Paeoniae Radix Alba in rats by UPLC-Q-TOF-MS/MS.

    PubMed

    Cao, Wenli; Wang, Xinguo; Li, Haojie; Shi, Xuliang; Fan, Wencheng; Zhao, Shaohua; Liu, Minyan; Niu, Liying

    2015-11-01

    Total glucosides of paeony are the active constituents of Paeoniae Radix Alba. In this study, a novel strategy was proposed to find more metabolites and the differences between paeoniflorin, albiflorin and total glucosides of paeony (TGP). This strategy was characterized as follows: firstly, the animals were divided into three groups (paeoniflorin, albiflorin and TGP) to identify the source of TGP metabolites from paeoniflorin or albiflorin; secondly, a generic information-dependent acquisition scan for the low-level metabolites was triggered by the multiple mass defect filter and dynamic background subtraction; thirdly, the metabolites were identified with a combination of data-processing methods including mass defect filtering, neutral loss filtering and product ion filtering; finally, a comparative study was used in the metabolism of paeoniflorin, albiflorin and TGP. Based on the strategy, 18 metabolites of TGP, 10 metabolites of paeoniflorin and 13 metabolites of albiflorin were identified respectively. The results indicated that the hydrolysis, conjugation reaction and oxidization were the major metabolic pathways, and the metabolic sites were the glycosidic linkage, the ester bond and the benzene ring. This study is first to explore the metabolism of TGP, and these findings enhance our understanding of the metabolism and the interactions of paeoniflrin and albiflorin in TGP. Copyright © 2015 John Wiley & Sons, Ltd. PMID:26058364

  7. Hypoglycaemic effect of mollic acid glucoside, a 1alpha-hydroxycycloartenoid saponin extractive from Combretum molle R. Br. ex G. Don (Combretaceae) leaf, in rodents.

    PubMed

    Ojewole, John A O; Adewole, Stephen O

    2009-04-01

    In this study, we investigated the hypoglycaemic and antidiabetic properties of mollic acid glucoside (MAG), a 1alpha-hydroxycycloartenoid extractive from Combretum molle leaf, in rodents. Stepwise, escalated doses of MAG (5-80 mg/kg p.o.) produced dose-dependent and significant (P < 0.05-0.01) hypoglycaemic and antidiabetic effects in normal (normoglycaemic) and streptozotocin-treated diabetic rats. Experimental evidence obtained from this laboratory animal study indicates that MAG, an extractive from C. molle leaf, possesses hypoglycaemic and antidiabetic properties. These findings lend pharmacological credence to the folkloric, ethnomedical uses of the plant's leaf in the management and/or control of diabetes mellitus in some rural communities of southern Africa. PMID:19050993

  8. Radiation protection by 6-palmitoyl ascorbic acid-2-glucoside: studies on DNA damage in vitro, ex vivo, in vivo and oxidative stress in vivo.

    PubMed

    Chandrasekharan, Dhanya K; Kagiya, Tsutomu V; Nair, Cherupally Krishnan Krishnan

    2009-05-01

    A palmitoyl derivative of ascorbic acid 2-glucoside, 6-palmitoyl ascorbic acid-2-glucoside (PAsAG), which possess good antioxidant properties, is examined for radioprotection in vitro, ex vivo and in vivo models. PAsAG protected plasmid DNA from gamma-radiation induced damages under in vitro conditions. Presence of 1.6 mM PAsAG inhibited the disappearance of ccc (covalently closed circular) form of plasmid pBR322 with a dose modifying factor of 1.5. Comet assay studies on mouse spleen cells exposed to 6 Gy gamma-radiation (ex vivo) in presence and absence of PAsAG revealed that cellular DNA was effectively protected by this compound from radiation induced damages. Oral administration of 80 mg/kg body weight of PAsAG to mice 1 hour prior to 6 Gy whole body gamma-radiation exposure, efficiently protected cellular DNA in tissues such as spleen, bone marrow and blood, from radiation induced damages as indicated by alkaline comet assay. Oxidative stress in tissues such as liver and brain of mice, following whole body exposure to various doses of gamma-radiation (2-8 Gy), monitored as levels of GSH and peroxidation of lipids, were found considerably reduced when PAsAG was orally administered (80 mg/kg body weight) to the mice one hour prior to the radiation exposure. PAsAG administration improved the per cent survival of mice following exposure to 10 Gy whole body gamma-radiation. Thus PAsAG could act as a radioprotector under in vitro, ex vivo and in vivo conditions of ionizing-radiation exposure. PMID:19384055

  9. Quercetin 7-O-glucoside suppresses nitrite-induced formation of dinitrosocatechins and their quinones in catechin/nitrite systems under stomach simulating conditions.

    PubMed

    Morina, Filis; Takahama, Umeo; Yamauchi, Ryo; Hirota, Sachiko; Veljovic-Jovanovic, Sonja

    2015-01-01

    Foods of plant origin contain flavonoids. In the adzuki bean, (+)-catechin, quercetin 3-O-rutinoside (rutin), and quercetin 7-O-?-D-glucopyranoside (Q7G) are the major flavonoids. During mastication of foods prepared from the adzuki bean, the flavonoids are mixed with saliva and swallowed into the stomach. Here we investigated the interactions between Q7G and (+)-catechin at pH 2, which may proceed in the stomach after the ingestion of foods prepared from the adzuki bean. Q7G reacted with nitrous acid producing nitric oxide (?NO) and a glucoside of 2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxy-3(2H)-benzofuranone. (+)-Catechin reacted with nitrous acid producing ?NO and 6,8-dinitrosocatechin. The production of the dinitrosocatechin was partly suppressed by Q7G, and the suppression resulted in the enhancement of Q7G oxidation. 6,8-Dinitrosocatechin reacted further with nitrous acid generating the o-quinone, and the quinone formation was effectively suppressed by Q7G. In the flavonoids investigated, the suppressive effect decreased in the order Q7G?quercetin>kaempferol>quercetin 4'-O-glucoside>rutin. Essentially the same results were obtained when (-)-epicatechin was used instead of (+)-catechin. The results indicate that nitrous acid-induced formation of 6,8-dinitrosocatechins and the o-quinones can be suppressed by flavonols in the stomach, and that both a hydroxyl group at C3 and ortho-hydroxyl groups in the B-ring are required for efficient suppression. PMID:25375233

  10. Discovery of the glycogen phosphorylase-modulating activity of a resveratrol glucoside by using a virtual screening protocol optimized for solvation effects.

    PubMed

    Mavrokefalos, Nikolaos; Myrianthopoulos, Vassilios; Chajistamatiou, Aikaterini S; Chrysina, Evangelia D; Mikros, Emmanuel

    2015-04-01

    The identification of natural products that can modulate blood glucose levels is of great interest as it can possibly facilitate the utilization of mild interventions such as herbal medicine or functional foods in the treatment of chronic diseases like diabetes. One of the established drug targets for antihyperglycemic therapy is glycogen phosphorylase. To evaluate the glycogen phosphorylase inhibitory properties of an in-house compound collection consisting to a large extent of natural products, a stepwise virtual and experimental screening protocol was devised and implemented. The fact that the active site of glycogen phosphorylase is highly hydrated emphasized that a methodological aspect needed to be efficiently addressed prior to an in silico evaluation of the compound collection. The effect of water molecules on docking calculations was regarded as a key parameter in terms of virtual screening protocol optimization. Statistical analysis of 125 structures of glycogen phosphorylase and solvent mapping focusing on the active site hydration motif in combination with a retrospective screening revealed the importance of a set of 29 crystallographic water molecules for achieving high enrichment as to the discrimination between active compounds and inactive decoys. The scaling of Van der Waals radii of system atoms had an additional effect on screening performance. Having optimized the in silico protocol, a prospective evaluation of the in-house compound collection derived a set of 18 top-ranked natural products that were subsequently evaluated in vitro for their activity as glycogen phosphorylase inhibitors. Two phenolic glucosides with glycogen phosphorylase-modulating activity were identified, whereas the most potent compound affording mid-micromolar inhibition was a glucosidic derivative of resveratrol, a stilbene well-known for its wide range of biological activities. Results show the possible phytotherapeutic and nutraceutical potential of products common in the Mediterranean countries, such as red wine and Vitis products in general or green raw salads and herbal preparations, where such compounds are abundant. PMID:25875507

  11. Analgesic and antiinflammatory effects of mollic acid glucoside, a 1 alpha-hydroxycycloartenoid saponin extractive from Combretum molle R. Br. ex G. Don (Combretaceae) leaf.

    PubMed

    Ojewole, John A O

    2008-01-01

    The analgesic and antiinflammatory properties of mollic acid glucoside (MAG), a 1 alpha-hydroxycycloartenoid extract from Combretum molle leaf, have been investigated in mice and rats. The effects of graded doses of mollic acid glucoside (MAG, 5-80 mg/kg i.p.) were examined against thermally- and chemically-induced nociceptive pain in mice. Furthermore, the effects of graded doses of the plant extract (MAG, 5-80 mg/kg p.o.) were also investigated on rat paw oedema induced by subplantar injections of fresh egg albumin (0.5 mg/kg). Morphine (MPN, 10 mg/kg i.p.) and diclofenac (DIC, 100 mg/kg i.p.) were used as reference analgesic and antiinflammatory agents for comparison, respectively. Like DIC (100 mg/kg i.p.) and MPN (10 mg/kg i.p.), MAG (5-80 mg/kg i.p.) produced dose-dependent, significant (p < 0.05-0.001) analgesic effects against thermally and chemically induced nociceptive pain in mice. The extractive (MAG, 5-80 mg/kg i.p.) also significantly reduced (p < 0.05-0.001) rat paw oedema induced by subplantar injections of fresh egg albumin in a dose-related fashion. However, the extract (MAG, 5-80 mg/kg i.p.) was found to be less potent than diclofenac (DIC) as an analgesic or antiinflammatory agent. Experimental evidence obtained from this laboratory animal study indicates that the Combretum molle leaf extractive (MAG) possesses analgesic and antiinflammatory properties, and thus lend pharmacological credence to the folkloric, ethnomedical uses of the plant's leaf in the management, control and/or treatment of painful, arthritic and other inflammatory conditions in some rural communities of southern Africa. PMID:17685389

  12. Selection of penstemide and serrulatoloside producing clones in penstemon serrulatus by small-aggregate cloning.

    PubMed

    Wysoki?ska, H; Giang, N T

    1990-11-01

    A plating method is described for cultured cells of Penstemon serrulatus Menz. which allows effective cloning of aggregates consisting of less than 10 cells, on a simple synthetic medium. The obtained clones snowed high diversity with respect to their ability to produce penstemide, an ester iridoid of the Valeriana-type. Some of the clones produced higher quantities of this compound than the original cell line. The content of another iridoid glucoside of the same type, serrulatoloside, was also determined. PMID:24227059

  13. Halohydrins and polyols derived from antirrhinoside: structural revisions of muralioside and epimuralioside

    PubMed

    Franzyk; Jensen; Thale; Olsen

    1999-02-01

    Treatment of the iridoid glucoside antirrhinoside (1) with pyridinium chloride in dimethylformamide gave rise to the two possible trans-halohydrins, linarioside (4) and isolinarioside (5). Pyridinium bromide gave the two analogous bromohydrins. It is shown that the iridoid glucosides 8-epi-muralioside from Linaria arcusangeli and 7,8-epi-antirrhinoside from Linaria dalmatica are both identical with isolinarioside, and therefore, these names are redundant. The structure of muralioside isolated from Cymbalaria muralis is revised to that of its 8-epimer (8), while the structure of an isomeric, new iridoid glucoside from Paulownia tomentosa has been elucidated to be 7beta-hydroxyharpagide (3), the structure originally assigned to 8. In addition, 7alpha-hydroxyharpagide (2), the known product from the base-catalyzed hydrolytic opening of 1, has been isolated from Antirrhinum majus and thus shown to be a natural product. PMID:10075758

  14. Signal transduction pathway for L-ascorbic acid- and L-ascorbic acid 2-glucoside-induced DNA synthesis and cell proliferation in primary cultures of adult rat hepatocytes.

    PubMed

    Moteki, Hajime; Shimamura, Yuya; Kimura, Mitsutoshi; Ogihara, Masahiko

    2012-05-15

    We examined the effects of L-ascorbic acid and its analogues on DNA synthesis and cell proliferation. We also investigated the signal transduction pathways involved in the induction of mitogenesis by L-ascorbic acid and its analogues using primary cultures of adult rat hepatocytes. Following a 4-h serum-free cultivation, both L-ascorbic acid and its stable analogue, L-ascorbic acid 2-glucoside, time- and dose-dependently stimulated hepatocyte DNA synthesis and cell proliferation, with EC?? values of 6.46×10?? M and 3.34×10?? M, respectively. Dehydroascorbic acid (10?? M-10?? M) weakly stimulated hepatocyte mitogenesis, whereas isoascorbic acid (10?? M-10?? M) had no effect. Hepatocyte mitogenesis induced by L-ascorbic acid or L-ascorbic acid 2-glucoside was dose-dependently abolished by treatment with monoclonal antibodies against insulin-like growth factor (IGF)-I receptor, but not by treatment with monoclonal antibodies against insulin receptor or IGF-II receptor. Western blot analysis showed that both L-ascorbic acid and L-ascorbic acid 2-glucoside significantly stimulated IFG-I receptor tyrosine kinase activity within 3 min, and mitogen-activated protein (MAP) kinase activity within 5 min. These results demonstrate that both L-ascorbic acid and L-ascorbic acid 2-glucoside induce DNA synthesis and cell proliferation in primary cultures of adult rat hepatocytes by interacting with the IGF-I receptor site and by activating the receptor tyrosine kinase/MAP kinase pathway. PMID:22429571

  15. Stimulation of callose synthesis in vivio correlates with changes in intracellular distribution of the callose synthase activator [beta]-Furfuryl-[beta]-Glucoside

    SciTech Connect

    Ohana, P.; Benziman, M.; Delmer, D.P. )

    1993-01-01

    [beta]-Furfuryl-[beta]-glucoside (FG) has been shown to be a specific endogenous activator of higher plant callose synthase. Because glycosides such as FG are usually sequestered in vacuoles, we have proposed that activation of callose synthesis in vivo may involve a change in the compartmentation on FG and Ca[sup 2+], resulting in a synergistic activation of callose synthase. The use of suspension-cultured barley (Hordeum bulbosum L.) cells provides evidence that FG is largely sequestered in the vacuole. Furthermore, conditions that lead to induction of callose synthesis in vivo correspondingly lead to elevation of the cytoplasmic concentration of FG. These conditions include the lowering of cytoplasmic pH or elevation of cytoplasmic Ca[sup 2+]. Oligogalacturonide elicitors have also been reported to cause similar changes in cytoplasmic pH and Ca[sup 2+] concentration, and such an elicitor also causes and elevation in cytoplasmic FG coupled with stimulation of callose synthesis. These results support the concept that a relative redistribution of FG between cytoplasm and vacuole may be one of the components of the signal transduction pathway for elicitation of callose synthase in vivo. 18 refs., 1 fig., 2 tabs.

  16. Dimethylarginine Dimethylaminohydrolase/Nitric Oxide Synthase Pathway in Liver and Kidney: Protective Effect of Cyanidin 3-O-?-D-Glucoside on Ochratoxin-A Toxicity

    PubMed Central

    Sorrenti, Valeria; Di Giacomo, Claudia; Acquaviva, Rosaria; Bognanno, Matteo; Grilli, Ester; D’Orazio, Nicolantonio; Galvano, Fabio

    2012-01-01

    The aim of the present study was to evaluate the effect of long-term cyanidin 3-O-?-D-glucoside (C3G) and/or Ochratoxin A (OTA)-exposure on dimethylarginine dimethylamino hydrolase/nitric oxide synthase (DDAH/NOS) pathway in rats. The experiments were performed in rats supplemented with C3G (1 g/kg feed), OTA (200 ppb), and OTA + C3G. After 4 weeks of daily treatment, liver and kidneys were processed for eNOS, iNOS and DDAH-1 Western blotting, nitrite levels evaluation and DDAH activity determination. Results show that OTA is able to induce iNOS both in kidney and liver, whereas OTA is able to induce eNOS and DDAH-1 overexpression and DDAH activation only in kidney, resulting in increased nitrite levels. In kidney of OTA + C3G fed rats, iNOS, eNOS and DDAH-1 expression were less pronounced compared with those observed in the OTA-treated group. Coherent with the decreased iNOS, eNOS and DDAH-1 expression a decrease in nitrite levels and DDAH activity was observed in the OTA + C3G group. Results demonstrate that C3G is able to counteract the deleterious effects of chronic consumption of OTA and also suggest a possible involvement of iNOS-eNOS-DDAH impairment in OTA nephrocarcinogenity. PMID:22778905

  17. Cyanidin-3-Glucoside-Rich Extract from Chinese Bayberry Fruit Protects Pancreatic ? Cells and Ameliorates Hyperglycemia in Streptozotocin-Induced Diabetic Mice

    PubMed Central

    Sun, Chong-De; Zhang, Bo; Zhang, Jiu-Kai; Xu, Chang-Jie; Wu, Yu-Lian; Chen, Kun-Song

    2012-01-01

    Abstract Chinese bayberry fruit is a rich source of anthocyanins, especially cyanidin-3-glucoside (C3G). The present study investigated the protective effects of C3G-rich bayberry fruit extract (CRBFE) against pancreatic ? cells against oxidative stress–induced injury as well as its hypoglycemic effect in diabetic mice. Bayberry extract from “Biqi” was used for both in vitro and in vivo testing because of its high C3G content and high antioxidant capacity. Pretreatment of ? cells with CRBFE (containing 0.5??mol/L C3G) prevented cell death, increased cellular viability, and decreased mitochondrial reactive oxygen species production and cell necrosis induced by 800 or 1,200??mol/L H2O2. CRBFE dose-dependently up-regulated pancreatic duodenal homeobox 1 gene expression, contributing to increased insulin-like growth factor II gene transcript levels and insulin protein in INS-1 cells. In addition, administration of CRBFE (150??g of C3G/10?g of body weight twice per day) significantly reduced blood glucose in streptozotocin-induced diabetic ICR mice and increased the glucose tolerance in an oral glucose tolerance test (P<.05). Such results indicated that CRBFE might be useful in prevention and control of diabetes mellitus and diabetes-associated complications. PMID:22181073

  18. Antiproliferative activity of long chain acylated esters of quercetin-3-O-glucoside in hepatocellular carcinoma HepG2 cells.

    PubMed

    Sudan, Sudhanshu; Rupasinghe, Hp Vasantha

    2015-11-01

    Despite their strong role in human health, poor bioavailability of flavonoids limits their biological effects in vivo. Enzymatically catalyzed acylation of fatty acids to flavonoids is one of the approaches of increasing cellular permeability and hence, biological activities. In this study, six long chain fatty acid esters of quercetin-3-O-glucoside (Q3G) acylated enzymatically and were used for determining their antiproliferative action in hepatocellular carcinoma cells (HepG2) in comparison to precursor compounds and two chemotherapy drugs (Sorafenib and Cisplatin). Fatty acid esters of Q3G showed significant inhibition of HepG2 cell proliferation by 85 to 90% after 6?h and 24?h of treatment, respectively. The cell death due to these novel compounds was associated with cell-cycle arrest in S-phase and apoptosis observed by DNA fragmentation, fluorescent microscopy and elevated caspase-3 activity and strong DNA topoisomerase II inhibition. Interestingly, Q3G esters showed significantly low toxicity to normal liver cells than Sorafenib (P?

  19. A fragmentation study of an isoflavone glycoside, genistein-7-O-glucoside, using electrospray quadrupole time-of-flight mass spectrometry at high mass resolution

    NASA Astrophysics Data System (ADS)

    March, Raymond E.; Miao, Xiu-Sheng; Metcalfe, Chris D.; Stobiecki, Maciej; Marczak, Lukasz

    2004-03-01

    A mass spectrometric method based on the combined use of electrospray ionization, collision-induced dissociation and tandem mass spectrometry at high mass resolution has been applied to an investigation of the structural characterization of genistein-7-O-[beta]--glucoside (5,7,4'-trihydroxyisoflavone). The product ion mass spectrum of [M-H]- ions shows neutral losses of the glycan residue (162 Da) and of the glycan residue + H[radical sign] (163 Da) by rearrangement and scission, respectively, where the latter loss dominates at higher collision energies. The genistein moiety remained intact and only minor fragmentation of the glucose moiety was observed. The low-energy product ion mass spectrum of [M+H]+ ions shows extensive fragmentation of the glucose moiety, though at low ion signal intensity, loss of the glycan residue, and simple fragmentation of the genistein moiety that permits characterization of the substituents in the A and B rings. The use of elevated cone voltages permitted observation of product ion mass spectra of selected primary fragment ions. Product ion mass spectra examined at high mass resolution allowed unambiguous determination of the elemental composition of fragment ions. Fragmentation mechanisms and ion structures have been proposed.

  20. Transcriptional Profiling and Molecular Characterization of Astragalosides, Calycosin, and Calycosin-7-O-?-D-glucoside Biosynthesis in the Hairy Roots of Astragalus membranaceus in Response to Methyl Jasmonate.

    PubMed

    Tuan, Pham Anh; Chung, Eunsook; Thwe, Aye Aye; Li, Xiaohua; Kim, Yeon Bok; Mariadhas, Valan Arasu; Al-Dhabi, Naif Abdullah; Lee, Jai-Heon; Park, Sang Un

    2015-07-15

    We used the next-generation Illumina/Solexa HiSeq2000 platform on RNA analysis to investigate the transcriptome of Astragalus membranaceus hairy roots in response to 100 ?M methyl jasmonate (MeJA). In total, 77,758,230 clean reads were assembled into 48,636 transcripts (average length of 1398 bp), which were clustered into 23,658 loci (genes). Of these, 19,940 genes were annotated by BLASTx searches. In addition, DESeq analysis showed that 2127 genes were up-regulated, while 1247 genes were down-regulated by MeJA. Seventeen novel astragaloside (AST) biosynthetic genes and seven novel calycosin and calycosin-7-O-?-D-glucoside (CG) biosynthetic genes were isolated. The accumulation of ASTs, calycosin, and CG increased significantly in MeJA-treated hairy roots compared with control hairy roots. Our findings will provide a valuable resource for molecular characterization of AST, calycosin, and CG biosynthetic pathways and may lead to new approaches to maximize their production and biomass productivity in the hairy roots of A. membranaceus. PMID:26072674

  1. Validation of a RP-HPLC-DAD Method for Chamomile (Matricaria recutita) Preparations and Assessment of the Marker, Apigenin-7-glucoside, Safety and Anti-Inflammatory Effect

    PubMed Central

    Miguel, Felipe Galeti; Cavalheiro, Amanda Henriques; Spinola, Nathália Favaretto; Ribeiro, Diego Luis; Barcelos, Gustavo Rafael Mazzaron; Antunes, Lusânia Maria Greggi; Hori, Juliana Issa; Marquele-Oliveira, Franciane; Rocha, Bruno Alves; Berretta, Andresa Aparecida

    2015-01-01

    Chamomile is a medicinal plant, which presents several biological effects, especially the anti-inflammatory effect. One of the compounds related to this effect is apigenin, a flavonoid that is mostly found in its glycosylated form, apigenin-7-glucoside (APG), in natural sources. However, the affectivity and safety of this glycoside have not been well explored for topical application. In this context, the aim of this work was to develop and validate a reversed-phase high-performance liquid chromatography (RP-HPLC-DAD) method to quantify APG in chamomile preparations. Additionally, the safety and the anti-inflammatory potential of this flavonoid were verified. The RP-HPLC-DAD method was developed and validated with linearity at 24.0–36.0??g/mL range (r = 0.9994). Intra- and interday precision (RSD) were 0.27–2.66% and accuracy was 98.27–101.21%. The validated method was applied in the analysis of chamomile flower heads, glycolic extract, and Kamillen cream, supporting the method application in the quality control of chamomile preparations. Furthermore, the APG safety was assessed by MTT cytotoxicity assay and mutagenic protocols and the anti-inflammatory activity was confirmed by a diminished TNF-? production showed by mice macrophages treated with APG following LPS treatment. PMID:26421053

  2. Pharmacokinetics of 2,3,5,4'-tetrahydroxystilbene-2-O-?-D-glucoside in rat using ultra-performance LC-quadrupole TOF-MS.

    PubMed

    Zhao, Ying-Yong; Zhang, Li; Feng, Ya-Long; Chen, Dan-Qian; Xi, Zhi-Hui; Du, Xiao; Bai, Xu; Lin, Rui-Chao

    2013-03-01

    2,3,5,4'-Tetrahydroxystilbene-2-O-?-D-glucoside (THSG) from Polygoni multiflori has been demonstrated to possess a variety of pharmacological activities, including antioxidant, anti-inflammatory and hepatoprotective activities. Ultra-performance LC-quadrupole TOF-MS with MS Elevated Energy data collection technique and rapid resolution LC with diode array detection and ESI multistage MS(n) methods were developed for the pharmacokinetics, tissue distribution, metabolism, and excretion studies of THSG in rats following a single intravenous or oral dose. The three metabolites were identified by rapid resolution LC-MS(n). The concentrations of the THSG in rat plasma, bile, urine, feces, or tissue samples were determined by ultra-performance LC-MS. The results showed that THSG was rapidly distributed and eliminated from rat plasma. After the intravenous administration, THSG was mainly distributing in the liver, heart, and lung. For the rat, the major distribution tissues after oral administration were heart, kidney, liver, and lung. There was no long-term storage of THSG in rat tissues. Total recoveries of THSG within 24 h were low (0.1% in bile, 0.007% in urine, and 0.063% in feces) and THSG was excreted mainly in the forms of metabolites, which may resulted from biotransformation in the liver. PMID:23371758

  3. TSG (2,3,5,4'-Tetrahydroxystilbene-2-O- ? -D-glucoside) from the Chinese Herb Polygonum multiflorum Increases Life Span and Stress Resistance of Caenorhabditis elegans.

    PubMed

    Büchter, Christian; Zhao, Liang; Havermann, Susannah; Honnen, Sebastian; Fritz, Gerhard; Proksch, Peter; Wätjen, Wim

    2015-01-01

    2,3,5,4'-Tetrahydroxystilbene-2-O-?-D-glucoside (TSG) was isolated from Polygonum multiflorum, a plant which is traditionally used as an anti-ageing drug. We have analysed ageing-related effects of TSG in the model organism C. elegans in comparison to resveratrol. TSG exerted a high antioxidative capacity both in a cell-free assay and in the nematode. The antioxidative capacity was even higher compared to resveratrol. Presumably due to its antioxidative effects, treatment with TSG decreased the juglone-mediated induction of the antioxidative enzyme SOD-3; the induction of the GST-4 by juglone was diminished slightly. TSG increased the resistance of C. elegans against lethal thermal stress more prominently than resveratrol (50??M TSG increased mean survival by 22.2%). The level of the ageing pigment lipofuscin was decreased after incubation with the compound. TSG prolongs the mean, median, and maximum adult life span of C. elegans by 23.5%, 29.4%, and 7.2%, respectively, comparable to the effects of resveratrol. TSG-mediated extension of life span was not abolished in a DAF-16 loss-of-function mutant strain showing that this ageing-related transcription factor is not involved in the effects of TSG. Our data show that TSG possesses a potent antioxidative capacity, enhances the stress resistance, and increases the life span of the nematode C. elegans. PMID:26075030

  4. TSG (2,3,5,4?-Tetrahydroxystilbene-2-O-?-D-glucoside) from the Chinese Herb Polygonum multiflorum Increases Life Span and Stress Resistance of Caenorhabditis elegans

    PubMed Central

    Büchter, Christian; Zhao, Liang; Fritz, Gerhard; Proksch, Peter

    2015-01-01

    2,3,5,4?-Tetrahydroxystilbene-2-O-?-D-glucoside (TSG) was isolated from Polygonum multiflorum, a plant which is traditionally used as an anti-ageing drug. We have analysed ageing-related effects of TSG in the model organism C. elegans in comparison to resveratrol. TSG exerted a high antioxidative capacity both in a cell-free assay and in the nematode. The antioxidative capacity was even higher compared to resveratrol. Presumably due to its antioxidative effects, treatment with TSG decreased the juglone-mediated induction of the antioxidative enzyme SOD-3; the induction of the GST-4 by juglone was diminished slightly. TSG increased the resistance of C. elegans against lethal thermal stress more prominently than resveratrol (50??M TSG increased mean survival by 22.2%). The level of the ageing pigment lipofuscin was decreased after incubation with the compound. TSG prolongs the mean, median, and maximum adult life span of C. elegans by 23.5%, 29.4%, and 7.2%, respectively, comparable to the effects of resveratrol. TSG-mediated extension of life span was not abolished in a DAF-16 loss-of-function mutant strain showing that this ageing-related transcription factor is not involved in the effects of TSG. Our data show that TSG possesses a potent antioxidative capacity, enhances the stress resistance, and increases the life span of the nematode C. elegans. PMID:26075030

  5. Potential protection of 2,3,5,4'-tetrahydroxystilbene-2-O-?-D-glucoside against staurosporine-induced toxicity on cultured rat hippocampus neurons.

    PubMed

    Yang, Xiao-Ping; Liu, Tao-Yan; Qin, Xiao-Yan; Yu, Long-Chuan

    2014-07-25

    The present study explored the effect of 2,3,5,4'-tetrahydroxystilbene-2-O-?-d-glucoside (THSG) on the staurosporine (STS)-induced toxicity in cultured rat hippocampal neurons. The results showed that administration of 200?M of THSG significantly protected against 0.3?M of STS-induced apoptosis in cultured rat hippocampal neurons tested by methyl thiazolyl tetrazolium (MTT) and terminal deoxynucleotidyl transferase-mediated dUTP nick-end labeling (TUNEL) assays. Furthermore, when the Akt signaling pathway was blocked by LY294002, an inhibitor of Phosphatidyl Inositol 3-kinase (PI3K), the protective effects of THSG against STS-induced neurotoxicity were abrogated. We further examined the involvement of PI3K/Akt signaling pathway in THSG protection against STS-induced cytotoxicity on cultured neurons and found that administration of THSG significantly inhibited the STS-induced decreases in the content of phosphorylated AKt (p-Akt). Moreover, we found that THSG rescued the down-regulation of B cell lymphoma/lewkmia-2 (Bcl2) and pro-caspase-3 (pro-Csp3) caused by STS in the neurons. These results indicate that THSG protect the cultured rat hippocampal neurons against STS-induced cytotoxicity and the PI3K/Akt signaling and mitochondrial apoptotic pathways are involved in the THSG-induced protective effects. PMID:24887581

  6. Tetrahydroxystilbene glucoside extends mouse life span via upregulating neural klotho and downregulating neural insulin or insulin-like growth factor 1.

    PubMed

    Zhou, Xuanxuan; Yang, Qian; Xie, Yanhua; Sun, Jiyuan; Hu, Jing; Qiu, Pengcheng; Cao, Wei; Wang, Siwang

    2015-03-01

    A Chinese herb, Polygonatum multiflorum, has been reported to prolong animal life span, but the relevant molecular mechanism remains unclear. Tetrahydroxystilbene glucoside (TSG) is one main component of P. multiflorum and may contribute to extending life span of mammals. On the other hand, neuronal insulin signaling mediates the life span of mammals. Therefore, we investigated the effects of TSG on memory ability, life span, and the neural insulin signaling in the senescence-accelerated prone mouse (SAMP8). TSG improved the memory ability significantly (p < 0.01, compared with a control group). TSG prolonged the life span of SAMP8 by 17% at the most (p < 0.01, compared with a control group). TSG increased the protein level of neural klotho and reduced the levels of neural insulin, insulin-receptor, insulin-like growth factor-1, and insulin-like growth factor-1 receptor in the brain of SAMP8 (p < 0.01, compared with a control group). All these proteins are key factors of the pathways related to neural insulin/IGF-1 signaling. These findings suggest that TSG has anti-aging effects on mammals. From these results, TSG from P. multiflorum should be developed as a potential anti-age drug. PMID:25595496

  7. A novel soybean (Glycine max) gene encoding a family 3 ?-glucosidase has high isoflavone 7-O-glucoside-hydrolyzing activity in transgenic rice.

    PubMed

    Hsu, Chia-Chen; Wu, Tsung-Meng; Hsu, Yi-Ting; Wu, Chih-Wen; Hong, Chwan-Yang; Su, Nan-Wei

    2015-01-28

    A previous study demonstrated that purified Glycine max ?-glucosidase (GmBGL) could hydrolyze glucosyl isoflavone to the aglyconic form. This study reports the cloning and functional characterization of a soybean cDNA encoding the ?-glucosidase. GmBGL was isolated by use of a purified soybean N-terminal amino acid sequence and conserved sequences of ?-glucosidase genes from other plants. Sequence analysis of GmBGL revealed an open reading frame of 1884 bp encoding a polypeptide of 627 amino acids with a calculated molecular mass of 69 kDa. Phylogenetic analysis classified the GmBGL into the glycosyl hydrolase 3 family. In soybean, the GmBGL transcript was predominantly accumulated in roots and leaves. To examine the enzymatic activity and substrate specificity, GmBGL was ectopically expressed in transgenic rice. Purified GmBGL protein from transgenic rice could catalyze the hydrolysis of genistin and daidzin to produce genistein and daidzein, respectively, which confirmed GmBGL as a functional ?-glucosidase with isoflavone glucoside-hydrolyzing activity. This paper reveals that GmBGL is a key enzyme in transforming glucosyl isoflavones to aglycones in soybean, which may help in genetic manipulation of aglycone-rich soybean seeds. PMID:25569564

  8. Palmitate-induced endothelial dysfunction is attenuated by cyanidin-3-O-glucoside through modulation of Nrf2/Bach1 and NF-?B pathways.

    PubMed

    Fratantonio, D; Speciale, A; Ferrari, D; Cristani, M; Saija, A; Cimino, F

    2015-12-15

    Free fatty acids (FFA), commonly elevated in diabetes and obesity, have been shown to impair endothelial functions and cause oxidative stress, inflammation, and insulin resistance. Anthocyanins represent one of the most important and interesting classes of flavonoids and seem to play a role in preventing cardiovascular diseases. Herein, we investigated the in vitro protective effects of cyanidin-3-O-glucoside (C3G) on cell signaling pathways in human umbilical vein endothelial cells (HUVECs) exposed to palmitic acid (PA), the most prevalent saturated FFA in circulation. Our data reported a significant augmentation of free radicals and oxidative stress in HUVECs exposed to PA for 3h, while C3G pretreatment improved intracellular redox status altered by FFA. Moreover, C3G significantly inhibited NF-?B proinflammatory pathway and adhesion molecules induced by PA, and these effects were attributed to the activation of Nrf2/EpRE pathway. In fact, C3G induced Nrf2 nuclear localization and activation of cellular antioxidant and cytoprotective genes at baseline and after PA exposure in endothelial cells. Our data confirm the hypothesis that natural Nrf2 inducers, such as C3G, might be a potential therapeutic strategy to protect vascular system against various stressors preventing several pathological conditions. PMID:26422990

  9. The Role of Sodium-Dependent Glucose Transporter 1 and Glucose Transporter 2 in the Absorption of Cyanidin-3-O-?-Glucoside in Caco-2 Cells

    PubMed Central

    Zou, Tang-Bin; Feng, Dan; Song, Gang; Li, Hua-Wen; Tang, Huan-Wen; Ling, Wen-Hua

    2014-01-01

    Anthocyanins have multiple biological activities of benefit to human health. While a few studies have been conducted to evaluate the bioavailability of anthocyanins, the mechanisms of their absorption mechanism remain ill-defined. In the present study, we investigated the absorption mechanism of cyanidin-3-O-?-glucoside (Cy-3-G) in human intestinal epithelial (Caco-2) cells. Cy-3-G transport was assessed by measuring the absorptive and efflux direction. Inhibition studies were conducted using the pharmacological agents, phloridzin, an inhibitor of sodium-dependent glucose transporter 1 (SGLT1), or phloretin, an inhibitor of glucose transporter 2 (GLUT2). The results showed that phloridzin and phloretin significantly inhibited the absorption of Cy-3-G. In addition, Caco-2 cells transfected with small interfering RNA (siRNA) specific for SGLT1 or GLUT2 showed significantly decreased Cy-3-G absorption. These siRNA transfected cells also showed a significantly decreased rate of transport of Cy-3-G compared with the control group. These findings suggest that Cy-3-G absorption is dependent on the activities of SGLT1 and GLUT2 in the small intestine and that SGLT1 and GLUT2 could be a limiting step for the bioavailability of Cy-3-G. PMID:25314643

  10. Aortic Remodelling Is Improved by 2,3,5,4?-Tetrahydroxystilbene-2-O-?-D-glucoside Involving the Smad3 Pathway in Spontaneously Hypertensive Rats

    PubMed Central

    Duan, Ju; Han, Xin; Ling, Shuang; Gan, Woting; Sun, Li; Ni, Rong-Zhen; Xu, Jin-Wen

    2015-01-01

    Hypertension is a common health problem that substantially increases the risk of cardiovascular disease. The condition increases blood pressure, which causes alterations in vascular structure and leads to the development of vascular pathologies. 2,3,5,4?-Tetrahydroxystilbene-2-O-?-D-glucoside (THSG), a resveratrol analogue extracted from a Chinese medicinal plant, has been proven to have numerous vascular protection functions. This study investigated whether THSG can improve vascular remodeling, which has thus far remained unclear. Orally administering THSG to spontaneously hypertensive rats (SHRs) aged 12 weeks for 14 weeks significantly inhibited intima-media thickness in the lower parts of the aortic arch, increased the vascular diastolic rate in response to acetylcholine, and reduced remodelling-related mRNA expression, such as that of ACTA2, CCL3, COL1A2, COL3A1, TIMP1 WISP2, IGFBP1, ECE1, KLF5, MYL1 BMP4, FN1, and PAI-1. Immunofluorescence staining also showed an inhibitory effect similar to that of THSG on PAI-1 protein expression in rat aortas. Results from immunoprecipitation and a Western blot assay showed that THSG inhibited the acetylation of Smad3. A chromatin immunoprecipitation assay showed that THSG prevented Smad3 binding to the PAI-1 proximal promoter in SHR aortas. In conclusion, our results demonstrated that the inhibitory effect of THSG on aortic remodelling involved the deacetylating role of Smad3 with increasing blood flow and with constant blood pressure. PMID:26693246

  11. Enhancement by ascorbic acid 2-glucoside or repeated additions of ascorbate of mitogen-induced IgM and IgG productions by human peripheral blood lymphocytes.

    PubMed

    Tanaka, M; Muto, N; Gohda, E; Yamamoto, I

    1994-12-01

    In this study, the effect of ascorbic acid 2-glucoside (AA-2G), a stable derivative of ascorbic acid (AsA), or repeated additions of ascorbate on antibody productions by human peripheral blood lymphocytes (PBLs) was examined, and the physiological function of AsA was evaluated. When human PBLs were stimulated with Staphylococcus aureus Cowan I or pokeweed mitogen, AA-2G remarkably increased the numbers of IgM- and IgG-secreting cells which were detected by enzyme-linked immunospot assay. Although a single addition of ascorbate was without effect, the effect of AA-2G was remarkably inhibited by the addition of castanospermine, an alpha-glucosidase inhibitor; and moreover, repeated additions of AsA to the culture medium during the culture period enhanced the response to the same level as did a single addition of AA-2G. These results indicate that AsA has the ability to stimulate the immunoglobulin productions by AA-2G. The phytohemagglutinin-induced proliferative response of PBLs was also stimulated by AA-2G. The intracellular AsA content in PBLs cultured with AA-2G was maintained at relatively high levels during the culture period, whereas the content with a single dose of AsA reached nearly zero by the end of the experiment. These in vitro findings suggest that AA-2G and AsA function as potent immunostimulators of antibody production in humans and that the intracellular AsA content is a key parameter for establishing the immune response of PBLs. PMID:7723222

  12. Cyanidin-3-O-?-Glucoside and Protocatechuic Acid Exert Insulin-Like Effects by Upregulating PPAR? Activity in Human Omental Adipocytes

    PubMed Central

    Scazzocchio, Beatrice; Varì, Rosaria; Filesi, Carmelina; D’Archivio, Massimo; Santangelo, Carmela; Giovannini, Claudio; Iacovelli, Annunziata; Silecchia, Gianfranco; Volti, Giovanni Li; Galvano, Fabio; Masella, Roberta

    2011-01-01

    OBJECTIVE Insulin resistance (IR) represents an independent risk factor for metabolic, cardiovascular, and neoplastic disorders. Preventing/attenuating IR is a major objective to be reached to preserve population health. Because many insulin-sensitizing drugs have shown unwanted side effects, active harmless compounds are sought after. Dietary anthocyanins have been demonstrated to ameliorate hyperglycemia and insulin sensitivity. This study aimed at investigating whether cyanidin-3-O-?-glucoside (C3G) and its metabolite protocatechuic acid (PCA) might have a role in glucose transport activation in human omental adipocytes and 3T3-L1 cells. RESEARCH DESIGN AND METHODS In cells treated with 50 µmol/L C3G and 100 µmol/L PCA, [3H]-2-deoxyglucose uptake, GLUT4 translocation by immunoblotting, adiponectin secretion, and peroxisome proliferator–activated receptor-? (PPAR?) activation by enzyme-linked immunosorbent assay kits were evaluated. Parallel experiments were carried out in murine adipocyte 3T3-L1. To define the role of PPAR? in modulating polyphenol effects, small interfering RNA technique and PPAR? antagonist were used to inhibit transcription factor activity. RESULTS C3G and PCA increased adipocyte glucose uptake (P < 0.05) and GLUT4 membrane translocation (P < 0.01). Significant increases (P < 0.05) in nuclear PPAR? activity, as well as in adiponectin and GLUT4 expressions (P < 0.01), were also shown. It is interesting that PPAR? inhibition counteracted the polyphenol-induced adiponectin and GLUT4 upregulations, suggesting a direct involvement of PPAR? in this process. CONCLUSIONS Our study provides evidence that C3G and PCA might exert insulin-like activities by PPAR? activation, evidencing a causal relationship between this transcription factor and adiponectin and GLUT4 upregulation. Dietary polyphenols could be included in the preventive/therapeutic armory against pathological conditions associated with IR. PMID:21788573

  13. IGF-1 Induction by Acylated Steryl ?-Glucosides Found in a Pre-Germinated Brown Rice Diet Reduces Oxidative Stress in Streptozotocin-Induced Diabetes

    PubMed Central

    Usuki, Seigo; Tsai, Ying-Ying; Morikawa, Keiko; Nonaka, Shota; Okuhara, Yasuhide; Kise, Mitsuo; Yu, Robert K.

    2011-01-01

    Background The pathology of diabetic neuropathy involves oxidative stress on pancreatic ?-cells, and is related to decreased levels of Insulin-like growth factor 1 (IGF-1). Acylated steryl ?-glucoside (PR-ASG) found in pre-germiated brown rice is a bioactive substance exhibiting properties that enhance activity of homocysteine-thiolactonase (HTase), reducing oxidative stress in diabetic neuropathy. The biological importance of PR-ASG in pancreatic ?-cells remains unknown. Here we examined the effects of PR-ASG on IGF-1 and glucose metabolism in ?-cells exposed to oxidative stress. Methodology/Principal Findings In the present study, a pre-germinated brown rice (PR)-diet was tested in streptozotocin (STZ)-induced diabetic rats. Compared with diabetic rats fed control diets, the PR-diet fed rats showed an improvement of serum metabolic and neurophysiological parameters. In addition, IGF-1 levels were found to be increased in the serum, liver, and pancreas of diabetic rats fed the PR-diet. The increased IGF-1 level in the pancreas led us to hypothesize that PR-ASG is protective for islet ?-cells against the extensive injury of advanced or severe diabetes. Thus we examined PR-ASG to determine whether it showed anti-apoptotic, pro-proliferative effects on the insulin-secreting ?-cells line, INS-1; and additionally, whether PR-ASG stimulated IGF-1 autocrine secretion/IGF-1-dependent glucose metabolism. We have demonstrated for the first time that PR-ASG increases IGF-1 production and secretion from pancreatic ?-cells. Conclusion/Significance These findings suggest that PR-ASG may affect pancreatic ?-cells through the activation of an IGF-1-dependent mechanism in the diabetic condition. Thus, intake of pre-germinated brown rice may have a beneficial effect in the treatment of diabetes, in particular diabetic neuropathy. PMID:22194889

  14. Isolation and reconstitution of cytochrome P450ox and in vitro reconstitution of the entire biosynthetic pathway of the cyanogenic glucoside dhurrin from sorghum.

    PubMed Central

    Kahn, R A; Bak, S; Svendsen, I; Halkier, B A; Møller, B L

    1997-01-01

    A cytochrome P450, designated P450ox, that catalyzes the conversion of (Z)-p-hydroxyphenylacetaldoxime (oxime) to p-hydroxymandelonitrile in the biosynthesis of the cyanogenic glucoside beta-D-glucopyranosyloxy-(S)-p-hydroxymandelonitrile (dhurrin), has been isolated from microsomes prepared from etiolated seedlings of sorghum (Sorghum bicolor L. Moench). P450ox was solubilized using nonionic detergents, and isolated by ion-exchange chromatography, Triton X-114 phase partitioning, and dye-column chromatography. P450ox has an apparent molecular mass of 55 kD, its N-terminal amino acid sequence is -ATTATPQLLGGSVP, and it contains the internal sequence MDRLVADLDRAAA. Reconstitution of P450ox with NADPH-P450 oxidoreductase in micelles of L-alpha-dilauroyl phosphatidylcholine identified P450ox as a multifunctional P450 catalyzing dehydration of (Z)-oxime to p-hydroxyphenylaceto-nitrile (nitrile) and C-hydroxylation of p-hydroxyphenylacetonitrile to nitrile. P450ox is extremely labile compared with the P450s previously isolated from sorghum. When P450ox is reconstituted in the presence of a soluble uridine diphosphate glucose glucosyltransferase, oxime is converted to dhurrin. In vitro reconstitution of the entire dhurrin biosynthetic pathway from tyrosine was accomplished by the insertion of CYP79 (tyrosine N-hydroxylase), P450ox, and NADPH-P450 oxidoreductase in lipid micelles in the presence of uridine diphosphate glucose glucosyltransferase. The catalysis of the conversion of Tyr into nitrile by two multifunctional P450s explains why all intermediates in this pathway except (Z)-oxime are channeled. PMID:9414567

  15. Cyanidin-3-Glucoside inhibits UVB-induced oxidative damage and inflammation by regulating MAP kinase and NF-?B signalling pathways in SKH-1 hairless mice skin

    PubMed Central

    Pratheeshkumar, Poyil; Son, Young-Ok; Wang, Xin; Divya, Sasidharan Padmaja; Joseph, Binoy; Hitron, John Andrew; Wang, Lei; Kim, Donghern; Yin, Yuanqin; Roy, Ram Vinod; Lu, Jian; Zhang, Zhuo; Wang, Yitao; Shi, Xianglin

    2015-01-01

    Skin cancer is one of the most commonly diagnosed cancers in the United States. Exposure to ultraviolet-B (UVB) radiation induces inflammation and photocarcinogenesis in mammalian skin. Cyanidin-3-Glucoside (C3G), a member of the anthocyanin family, is present in various vegetables and fruits especially in edible berries, and displays potent antioxidant and anticarcinogenic properties. In this study, we have assessed the in vivo effects of C3G on UVB irradiation induced chronic inflammatory responses in SKH-1 hairless mice, a well-established model for UVB-induced skin carcinogenesis. Here, we show that C3G inhibited UVB-induced skin damage and inflammation in SKH-1 hairless mice. Our results indicate that C3G inhibited glutathione depletion, lipid peroxidation and myeloperoxidation in mouse skin by chronic UVB exposure. C3G significantly decreased the production of UVB-induced pro-inflammatory cytokines, such as IL-6 and TNF-?, associated with cutaneous inflammation. Likewise, UVB-induced inflammatory responses were diminished by C3G as observed by a remarkable reduction in the levels of phosphorylated MAP Kinases, Erk1/2, p38, JNK1/2 and MKK4. Furthermore, C3G also decreased UVB-induced cyclooxygenase-2 (COX-2), PGE2 and iNOS levels, which are well-known key mediators of inflammation and cancer. Treatment with C3G inhibited UVB-induced nuclear translocation of NF-?B and degradation of I?B? in mice skin. Immunofluorescence assay revealed that topical application of C3G inhibited the expression of 8-hydroxy-2?-deoxyguanosine, proliferating cell nuclear antigen, and cyclin D1 in chronic UVB exposed mouse skin. Collectively, these data indicates that C3G can provide substantial protection against the adverse effects of UVB radiation by modulating UVB-induced MAP kinase and NF-?B signaling pathways. PMID:25062774

  16. Cardiovascular effects of mollic acid glucoside, a 1?-hydroxycycloartenoid saponin extractive from Combretum molle R Br ex G Don (Combretaceae) leaf

    PubMed Central

    Ojewole, John AO

    2008-01-01

    Summary Summary The cardiovascular effects of mollic acid glucoside (MAG), a 1?-hydroxycycloartenoid saponin extractive from Combretum molle R Br ex G Don (Combretaceae) leaf, have been investigated in some experimental animal paradigms. The plant extract (MAG, 5–80 ?g/ml) produced concentration-dependent, significant (p < 0.05–0.001) negative inotropic and negative chronotropic effects on guinea pig isolated electrically driven left, and spontaneously beating right atrial muscle preparations, respectively. MAG also significantly reduced (p < 0.05–0.001) or abolished, in a concentration-dependent manner, the rhythmic, spontaneous contractions of portal veins isolated from healthy, normal Wistar rats. Like acetylcholine (ACh, 10-8–10-5 M), the plant extract (5–80 ?g/ml) produced concentration-related relaxations of rat isolated endothelium-containing thoracic aortic rings pre-contracted with noradrenaline (NA, 10-10–10-5 M). The vasorelaxant effects of MAG in the aortic rings were markedly inhibited or annulled by NG-nitro-L-arginine methyl ester (L-NAME, 10-5 M), a nitric oxide synthase inhibitor. Furthermore, MAG (2.5–40 mg/kg iv) caused dose-related, transient but significant reductions (p < 0.05–0.001) in the systemic arterial blood pressures and heart rates of anaesthetised normotensive and hypertensive rats. The results of this laboratory animal study indicate that MAG caused bradycardia, vasorelaxation and hypotension in the mammalian experimental models used. The vasorelaxant action of MAG was endothelium dependent, and was therefore possibly dependent on the synthesis and release of nitric oxide (NO). The findings of this study suggest that Combretum molle leaf may be used as a natural supplementary remedy in essential hypertension and in certain cases of cardiac dysfunctions in rural African communities. PMID:18568171

  17. Cardiovascular effects of mollic acid glucoside, a 1alpha-hydroxycycloartenoid saponin extractive from Combretum molle R Br ex G Don (Combretaceae) leaf.

    PubMed

    Ojewole, J A

    2008-01-01

    The cardiovascular effects of mollic acid glucoside (MAG), a 1alpha-hydroxycycloartenoid saponin extractive from Combretum molle R Br ex G Don (Combretaceae) leaf, have been investigated in some experimental animal paradigms. The plant extract (MAG, 5-80 microg/ml) produced concentration-dependent, significant (p < 0.05-0.001) negative inotropic and negative chronotropic effects on guinea pig isolated electrically driven left, and spontaneously beating right atrial muscle preparations, respectively. MAG also significantly reduced (p < 0.05-0.001) or abolished, in a concentration-dependent manner, the rhythmic, spontaneous contractions of portal veins isolated from healthy, normal Wistar rats. Like acetylcholine (ACh, 10-(8)-10-(5) M), the plant extract (5-80 microg/ml) produced concentration-related relaxations of rat isolated endothelium-containing thoracic aortic rings pre-contracted with noradrenaline (NA, 10-10(-10)-(5) M). The vasorelaxant effects of MAG in the aortic rings were markedly inhibited or annulled by N(G)-nitro-L-arginine methyl ester (L-NAME, 10(-5) M), a nitric oxide synthase inhibitor. Furthermore, MAG (2.5-40 mg/kg iv) caused dose-related, transient but significant reductions (p < 0.05-0.001) in the systemic arterial blood pressures and heart rates of anaesthetised normotensive and hypertensive rats. The results of this laboratory animal study indicate that MAG caused bradycardia, vasorelaxation and hypotension in the mammalian experimental models used. The vasorelaxant action of MAG was endothelium dependent, and was therefore possibly dependent on the synthesis and release of nitric oxide (NO). The findings of this study suggest that Combretum molle leaf may be used as a natural supplementary remedy in essential hypertension and in certain cases of cardiac dysfunctions in rural African communities. PMID:18568171

  18. Comparison of Anorectic and Emetic Potencies of Deoxynivalenol (Vomitoxin) to the Plant Metabolite Deoxynivalenol-3-Glucoside and Synthetic Deoxynivalenol Derivatives EN139528 and EN139544

    PubMed Central

    Wu, Wenda; Zhou, Hui-Ren; Bursian, Steven J.; Pan, Xiao; Link, Jane E.; Berthiller, Franz; Adam, Gerhard; Krantis, Anthony; Durst, Tony; Pestka, James J.

    2014-01-01

    The mycotoxin deoxynivalenol (DON) elicits robust anorectic and emetic effects in several animal species. However, less is known about the potential for naturally occurring and synthetic congeners of this trichothecene to cause analogous responses. Here we tested the hypothesis that alterations in DON structure found in the plant metabolite deoxynivalenol-3-glucoside (D3G) and two pharmacologically active synthetic DON derivatives, EN139528 and EN139544, differentially impact their potential to evoke food refusal and emesis. In a nocturnal mouse food consumption model, oral administration with DON, D3G, EN139528, or EN139544 at doses from 2.5 to 10 mg/kg BW induced anorectic responses that lasted up to 16, 6, 6, and 3 h, respectively. Anorectic potency rank orders were EN139544>DON>EN139528>D3G from 0 to 0.5 h but DON>D3G>EN139528>EN139544 from 0 to 3 h. Oral exposure to each of the four compounds at a common dose (2.5 mg/kg BW) stimulated plasma elevations of the gut satiety peptides cholecystokinin and to a lesser extent, peptide YY3–36 that corresponded to reduced food consumption. In a mink emesis model, oral administration of increasing doses of the congeners differentially induced emesis, causing marked decreases in latency to emesis with corresponding increases in both the duration and number of emetic events. The minimum emetic doses for DON, EN139528, D3G, and EN139544 were 0.05, 0.5, 2, and 5 mg/kg BW, respectively. Taken together, the results suggest that although all three DON congeners elicited anorectic responses that mimicked DON over a narrow dose range, they were markedly less potent than the parent mycotoxin at inducing emesis. PMID:25173790

  19. The effect of 2,3,4',5-tetrahydroxystilbene-2-0-?-D glucoside on neointima formation in a rat artery balloon injury model and its possible mechanisms.

    PubMed

    Xu, Xiao-le; Ling, Dan-yan; Zhu, Qiu-yan; Fan, Wen-jun; Zhang, Wei

    2013-01-01

    2,3,4',5-tetrahydroxystilbene-2-0-?-D glucoside (TSG) has been recognized to suppress the proliferation of vascular smooth muscle cells (VSMCs). The aim of the present study was to determine whether TSG inhibits neointimal hyperplasia in a rat carotid arterial balloon injury model. Balloon injury was induced in the left common carotid artery of rats. TSG (30, 60, 120 mg/kg/day) was treated from 3 days prior to, until 14 days after the induction of balloon injury. The ratio of intima-to-media was significantly reduced in the TSG-treated rats at 14 days after the induction of injury, which was associated with reduced expressions of proliferating cell nuclear antigen (PCNA), ?-smooth muscle actin (?-SMA) and platelet-derived growth factor-BB (PDGF-BB), as markers of VSMCs proliferation and migration. Additionally, TSG significantly inhibited PDGF-BB induced cell migration in cultured VSMCs. Furthermore, we explored the underlying mechanisms for such effects of TSG. The result showed that TSG markedly reduced balloon injury-induced AKT, extracellular signal-regulated kinase (ERK1/2) and nuclear factor kappaB (NF-?B) activation as well as mRNA expressions of c-myc, c-fos and c-jun, which is important signal pathway for VSMCs proliferation. And in both vivo and vitro model, TSG markedly regulated matrix metalloproteinase-2, 9 expressions and collagen I, III expressions, which are key factors in extracellular matrix for VSMCs migration. These results suggest that the anti-proliferative and anti-migrative effects of TSG on VSMCs could help to explain the beneficial effects of TSG on neointima hyperplasia induced by balloon injury. PMID:23178522

  20. Determination of free and glucosidically-bound volatiles in plants. Two case studies: L-menthol in peppermint (Mentha x piperita L.) and eugenol in clove (Syzygium aromaticum (L.) Merr. & L.M.Perry).

    PubMed

    Sgorbini, Barbara; Cagliero, Cecilia; Pagani, Alberto; Sganzerla, Marla; Boggia, Lorenzo; Bicchi, Carlo; Rubiolo, Patrizia

    2015-09-01

    This study arises from both the today's trend towards exploiting plant resources exhaustively, and the wide quantitative discrepancy between the amounts of commercially-valuable markers in aromatic plants and those recovered from the related essential oil. The study addresses the determination of both the qualitative composition and the exhaustive distribution of free and glucosidically-bound L-menthol in peppermint aerial parts (Mentha x piperita L., Lamiaceae) and of eugenol in dried cloves (Syzygium aromaticum (L.) Merr. & L.M.Perry, Myrtaceae), two plants known to provide widely ranging essential oil yields. The two markers were investigated in essential oils and residual hydrodistillation waters, before and after enzymatic hydrolysis. Their amounts were related to those in the headspace taken as reference. The results showed that the difference between marker compound in headspace and in essential oil amounted to 22.8% for L-menthol in peppermint, and 16.5% for eugenol in cloves. The aglycones solubilised in the residual hydrodistillation waters were 7.2% of the headspace reference amount for L-menthol, and 13.3% for eugenol, respectively representing 9.3% and 15.9% of their amounts in the essential oil. The amount of L-menthol from its glucoside in residual hydrodistillation waters was 20.6% of that in the related essential oil, while eugenol from its glucoside accounted for 7.7% of the amount in clove essential oil. The yield of L-menthol, after submitting the plant material to enzymatic hydrolysis before hydrodistillation, increased by 23.1%, and for eugenol the increase was 8.1%, compared to the amount in the respective conventional essential oils. This study also aimed to evaluate the reliability of recently-introduced techniques that are little applied, if at all, in this field. The simultaneous use of high-concentration-capacity sample preparation techniques (SBSE, and HS-SPME and in-solution SPME) to run quali-quantitative analysis without sample manipulation, and direct LC-MS glucoside analysis, provided cross-validation of the results. PMID:26115036

  1. Maintenance of glucose-sensitive insulin secretion of cryopreserved human islets with University of Wisconsin solution and ascorbic acid-2 glucoside.

    PubMed

    Arata, Takashi; Okitsu, Teru; Fukazawa, Takuya; Ikeda, Hideaki; Kobayashi, Kazuya; Yong, Chen; Kosaka, Yoshikazu; Narushima, Michiki; Matsuoka, Junji; Yamamoto, Itaru; Tanaka, Noriaki; Lakey, Jonathan R T; Kobayashi, Naoya

    2004-06-01

    Normal human islet cells are an ideal source for pancreas-targeted cell therapies, but the availability of human donor pancreata for islet isolation is severely limited. To effectively utilize such scarce donor organs for cell therapies, it is crucial to develop an excellent isolation, effective cryopreservation, and efficient gene transfer techniques for the transportation of isolated cells. In the present study, we investigate the effect of University of Wisconsin (UW) solution and ascorbic acid-2 glucoside (AA2G) on the cryopreservation of human islets. We also evaluate the gene transfer efficiency of a lentiviral vector expressing the E. coli LacZ gene, Lt-NLS/LacZ, in human islets. Human islets were isolated with a standard digestion method at the University of Alberta. Isolated islets were transported to Japan for 40 h and then subjected to cryopreservation experiments. The following preservation solutions were tested: UW solution with 100 micro g/mL of AA2G, UW solution, 100% fetal bovine serum (FBS), and CMRL supplemented with 10% FBS. Following three months of cryopreservation, the islets were thawed and analyzed for viability, glucose-sensitive insulin secretion, proinsulin gene expression profile, and in vivo engraftment. The islets were also subjected to monolayer formation with 804G-cell-line-derived extracellular matrix (ECM), followed by Lt-NLS/LacZ transduction. The viability, morphology, glucose-sensitive insulin secretion, proinsulin gene expression, and monolayer formation efficiency of the thawed cryopreserved islets are significantly better maintained by the use of UW solution. When AA2G (100 microg/mL) is combined with UW, such parameters are further improved. The adequate engraftment of UW + AA2G-cryopreserved human islets is achieved in the liver of nude mice. Efficient Lt-NLS/LacZ transduction is identified in monolayered islets cryopreserved with UW solution with AA2G. The present work demonstrates that the combination of UW solution with AA2G (100 microg/mL) would be a useful cryopreservation means for human islets. Human islets monolayer-cultured with 804G-derived ECM are efficiently transduced with a lentiviral vector Lt-NLS/LacZ. PMID:15153144

  2. Annexin V assay-proven anti-apoptotic effect of ascorbic acid 2-glucoside after cold ischemia/reperfusion injury in rat liver transplantation.

    PubMed

    Liu, Jie; Yagi, Takahito; Sadamori, Hiroshi; Matsukawa, Hiroyoshi; Sun, Dong-Sheng; Mitsuoka, Naoshi; Yamamura, Masao; Matsuoka, Junji; Jin, Zaishun; Yamamoto, Itaru; Tanaka, Noriaki

    2003-10-01

    Controversy exists over whether the predominant cell death of hepatocytes is due to apoptosis or necrosis after ischemia/reperfusion injury. In this study we investigated the predominant cell death of hepatocytes after cold ischemia/reperfusion injury using the Annexin V-based assay, and evaluated the anti-apoptotic effect of ascorbic acid 2-glucoside (AA-2G) added to the University of Wisconsin solution (UW solution) in rat liver transplantation. The retrieved liver was preserved in 4 UW solution for 24 h, and then transplanted orthotopically to the syngeneic Wistar recipient. The animals were divided into 2 groups, a control group (n=10), in which liver grafts were preserved in UW solution (4), and an AA-2G group (n=10), in which liver grafts were preserved in UW solution (4) with AA-2G (100 ug/ml). The serum AST level 4 h after reperfusion in the control group was significantly suppressed in the AA-2G group, and the bile production of the liver graft in the AA-2G group was well recovered. The mean survival time in the AA-2G group was significantly improved compared with that in the control group. Annexin-V and Propidium iodide staining 4 h after reperfusion showed a significantly higher percentage of viable hepatocytes in the AA-2G group compared with the control group (93.4 +/- 2.0 vs. 80.3 +- 2.1%, P<0.05). In the control group, the main cell death of hepatocytes was apoptosis (early apoptosis: 10.0 +- 4.7%, late apoptosis: 6.4 +/- 1.7%). The addition of AA-2G to the UW solution significantly inhibited both early and late apoptotic cell death 4 h after reperfusion (early apoptosis: 0.98 +/- 0.88%, late apoptosis: 2.2 +/- 1.1%). The expression of caspase 9 in the immunostaining of the liver graft was suppressed in the AA-2G group compared with in the control group. Our study using the Annexin V-based assay provided evidence that the predominant cell death of hepatocytes was apoptosis after 24 h cold ischemia/reperfusion injury in rat liver transplantation. The addition of AA-2G to the UW solution attenuated 24 h cold ischemia/reperfusion injury by inhibiting the apoptosis of hepatocytes. PMID:14679398

  3. Oral bioavailability and pharmacokinetics of elimination of 9-hydroxybenzo[a]pyrene and its glucoside and sulfate conjugates after administration to male and female American lobsters, Homarus americanus.

    PubMed

    Li, C L; James, M O

    2000-09-01

    The pharmacokinetics of [(3)H]-9-hydroxybenzo[a]pyrene (9-OH-BaP), a highly lipophilic primary metabolite of benzo(a)pyrene, were examined after intrapericardial (iv) or oral doses of 50 or 200 microg/kg to intermolt American lobsters, Homarus americanus. Combining data for all lobsters, the average terminal elimination half-life of parent 9-OH-BaP was 97.3 h after iv and 56.5 h after oral administration, considerably less than found previously for benzo(a)pyrene (720 h). The oral bioavailability of parent 9-OH-BaP, calculated from the area under the hemolymph concentration curve, was 15.9%. The low bioavailability and variable elimination rates were attributed to extensive first-pass conjugation and sequestration in the hepatopancreas. BaP-9-sulfate was the major metabolite. Hemolymph concentrations of BaP-9-sulfate increased up to one day after the dose, and then decreased, with a terminal elimination half-life of 45 h. BaP 9-beta-D-glucoside was a minor metabolite in most hemolymph and tissue samples; an exception was hemolymph from the iv high-dose group. Concentrations of 9-OH-BaP and metabolites in the edible muscle tissue were similar to those in hemolymph, and 9-OH-BaP residues at 10 to 16 days after the dose were 3 to 12 ng/g muscle. Sulfotransferase and UDP-glucosyltransferase (UGT) activities with 9-OH-BaP were found in the antennal gland, intestinal mucosa, and hepatopancreas (UGT only). Sulfatase activity with BaP-9-sulfate, found in both the hepatopancreas and the antennal gland, was thought to contribute to metabolite cycling. These studies showed that 9-OH-BaP was readily conjugated to sulfate and glucose in the lobster, and that despite their high lipophilicity, 9-OH-BaP and conjugates were excreted from the lobster hemolymph and tissues much more rapidly than benzo[a]pyrene. PMID:10966513

  4. Calycosin?7?O???D?glucoside attenuates ischemia?reperfusion injury in vivo via activation of the PI3K/Akt pathway.

    PubMed

    Ren, Min; Wang, Xudong; Du, Guoqing; Tian, Jiawei; Liu, Yujie

    2016-01-01

    The aim of the present study was to investigate the effects and mechanisms of calycosin?7?O???D?glucoside (CG) on ischemia?reperfusion (I/R) injury in vivo. Hemodynamic parameters, including ejection fraction (EF), fractional shortening (FS), left ventricular end?systolic pressure (LVESP) and left ventricular end?diastolic pressure (LVEDP) were monitored using an ultrasound system, and infarct size was measured using Evans blue/tetrazolium chloride double staining. The activities of serum creatine kinase (CK), lactate dehydrogenase (LDH) and superoxide dismutase (SOD), and the levels of malondialdehyde (MDA) were determined to assess the degree of myocardial injury and oxidative stress?induced damage. The protein expression levels of cleaved?caspase?3, cleaved?caspase?9, phosphorylated (p)?phosphatidylinositol 3?kinase (PI3K) p85, PI3K p85, p?Akt and Akt were determined using western blotting. The results demonstrated that pretreatment with high dose (H)?CG markedly improved cardiac function, as evidenced by upregulated EF, FS and LVESP, and downregulated LVEDP. In addition, administration of CG resulted in significant decreases in infarct size in the I/R+low dose?CG and I/R+H?CG groups, compared with the I/R group. The activities of CK and LDH, and the levels of MDA in the I/R+H?CG group were reduced, compared with those in the I/R group, whereas SOD activity was elevated. Treatment with CG inhibited the cleavage and activity of caspase?3 and caspase?9, and enhanced the phosphorylation of PI3K p85 and Akt. Notably, administration of the PI3K inhibitor, LY294002, markedly lowered the levels of p?PI3K p85/p?Akt, and eradicated the inhibitory effects of H?CG on infarct size, myocardial injury and oxidative stress?induced damage. Taken together, the results suggested that CG may alleviate I/R injury by activating the PI3K/Akt signaling pathway. PMID:26648122

  5. Calycosin-7-O-?-d-glucoside attenuates ischemia-reperfusion injury in vivo via activation of the PI3K/Akt pathway

    PubMed Central

    REN, MIN; WANG, XUDONG; DU, GUOQING; TIAN, JIAWEI; LIU, YUJIE

    2016-01-01

    The aim of the present study was to investigate the effects and mechanisms of calycosin-7-O-?-d-glucoside (CG) on ischemia-reperfusion (I/R) injury in vivo. Hemodynamic parameters, including ejection fraction (EF), fractional shortening (FS), left ventricular end-systolic pressure (LVESP) and left ventricular end-diastolic pressure (LVEDP) were monitored using an ultrasound system, and infarct size was measured using Evans blue/tetrazolium chloride double staining. The activities of serum creatine kinase (CK), lactate dehydrogenase (LDH) and superoxide dismutase (SOD), and the levels of malondialdehyde (MDA) were determined to assess the degree of myocardial injury and oxidative stress-induced damage. The protein expression levels of cleaved-caspase-3, cleaved-caspase-9, phosphorylated (p)-phosphatidylinositol 3-kinase (PI3K) p85, PI3K p85, p-Akt and Akt were determined using western blotting. The results demonstrated that pretreatment with high dose (H)-CG markedly improved cardiac function, as evidenced by upregulated EF, FS and LVESP, and downregulated LVEDP. In addition, administration of CG resulted in significant decreases in infarct size in the I/R+low dose-CG and I/R+H-CG groups, compared with the I/R group. The activities of CK and LDH, and the levels of MDA in the I/R+H-CG group were reduced, compared with those in the I/R group, whereas SOD activity was elevated. Treatment with CG inhibited the cleavage and activity of caspase-3 and caspase-9, and enhanced the phosphorylation of PI3K p85 and Akt. Notably, administration of the PI3K inhibitor, LY294002, markedly lowered the levels of p-PI3K p85/p-Akt, and eradicated the inhibitory effects of H-CG on infarct size, myocardial injury and oxidative stress-induced damage. Taken together, the results suggested that CG may alleviate I/R injury by activating the PI3K/Akt signaling pathway. PMID:26648122

  6. Simultaneous determination of calycosin-7-O-?-d-glucoside, calycosin, formononetin, astragaloside IV and schisandrin in rat plasma by LC-MS/MS: application to a pharmacokinetic study after oral administration of Shenqi Wuwei chewable tablets.

    PubMed

    Sun, Xuehui; Zhang, Pingping; Wu, Xiujun; Wu, Qiong; Zhang, Mengmeng; An, Ye; Shi, Guobing

    2014-08-01

    A rapid, sensitive and reliable high-performance liquid chromatography-mass spectrometry (LC-MS/MS) method was developed and validated for simultaneous quantification of the five main bioactive components, calycosin, calycosin-7-O-?-d-glucoside, formononetin, astragaloside IV and schisandrin in rat plasma after oral administration of Shenqi Wuwei chewable tablets. Plasma samples were extracted using solid-phase extraction separated on a CEC18 column and detected by MS with an electrospray ionization interface in multiple-reaction monitoring mode. Calibration curves offered linear ranges of two orders of magnitude with r > 0.995. The method had a lower limit of quantitation of 0.1, 0.02, 0.1, 1 and 0.1 ng/mL for calycosin, calycosin-7-O-?-d-glucoside, formononetin, astragaloside IV and schisandrin, respectively. Intra- and inter-day precisions (relative standard deviation) for all analytes ranged from 0.97 to 7.63% and from 3.45 to 10.89%, respectively. This method was successfully applied to the pharmacokinetic study of the five compounds in rats after oral administration of Shenqi Wuwei chewable tablets. PMID:24652759

  7. Determination of cyanidin-3-glucoside (red kernel food colour) in beverages by high performance liquid chromatography and a study of its degradation by quadruple time-of-flight mass spectrometry.

    PubMed

    Song, Jia; Li, Xiaolin; Zeng, Lu; Liu, Hailing; Xie, Mengxia

    2011-12-01

    A method for the determination of cyanidin-3-glucoside (red kernel colour, RKC) in various matrices, including carbonated soft drinks, fruit-based soft drinks, sugar confectionery and milk-based drinks, by high performance liquid chromatography (HPLC) based on UV-Vis detection (at 520 nm) have been developed. Pre-treatment procedures for various matrices have been optimised. For soft drinks, the pH values were adjusted to 2.0, and sugar confectionery and milk-based drinks were extracted with 30 and 50% methanol in 0.1% formic acid (pH ~ 2.5) aqueous solutions, respectively. The limits of detection for the established methods ranged from 0.2 mg/kg for soft drinks to 2.0 mg/kg for the sugar confectionery and milk-based drinks with the relative standard deviations lower than 7%, which satisfy the method performance requirements for quality control for the beverages. The stability of the colourant RKC under various thermal and pH conditions was investigated by quadruple time-of-flight mass spectrometry (Q-TOF-MS). The main colourant component of RKC, cyanidin-3-glucoside (Cyd-3-Glu), lost the glucose entity under thermal treatment. A new component was identified when RKC degraded under various pH conditions and a degradation pathway is proposed. The results will assist in understanding the degradation mechanism of the colourant Cyd-3-Glu. PMID:22014114

  8. Quercetin-3-glucoside increases low-density lipoprotein receptor (LDLR) expression, attenuates proprotein convertase subtilisin/kexin 9 (PCSK9) secretion, and stimulates LDL uptake by Huh7 human hepatocytes in culture

    PubMed Central

    Mbikay, Majambu; Sirois, Francine; Simoes, Sonia; Mayne, Janice; Chrétien, Michel

    2014-01-01

    Low-density lipoprotein receptor (LDLR) mediates hepatic clearance of plasma cholesterol; proprotein convertase subtilisin/kexin 9 (PCSK9) opposes this clearance by promoting LDLR degradation. The plant flavonoid quercetin-3-?-d-glucoside (Q3G) has been shown to reduce hypercholesterolemia in experimental animals. Here, we examined how it affects LDLR and PCSK9 expression as well as LDL uptake by human Huh7 hepatocytes. At low micromolar concentrations, Q3G increased LDLR expression, reduced PCSK9 secretion, and stimulated LDL uptake. It also diminished intracellular sortilin, a sorting receptor known to facilitate PCSK9 secretion. Thus, as an LDLR inducer and a PCSK9 anti-secretagogue, Q3G may represent an effective anti-cholesterolemic agent. PMID:25349780

  9. Identification and Quantification of Oxidoselina-1,3,7(11)-Trien-8-One and Cyanidin-3-Glucoside as One of the Major Volatile and Non-Volatile Low-Molecular-Weight Constituents in Pitanga Pulp

    PubMed Central

    Ehrnhöfer-Ressler, Miriam Margit; Walker, Jessica; Montenegro Brasil, Isabella; Somoza, Veronika

    2015-01-01

    The pulp of pitanga (Eugenia uniflora L.) is used to prepare pitanga juice. However, there are no reports on the identification and quantification of the main constituents in pitanga pulp. The aim of this study was to identify and quantify the major volatile and non-volatile low-molecular-weight constituents of the pulp. Isolation of volatile compounds was performed by solvent-assisted flavor evaporation technique. Characterization of the main volatile and non-volatile constituents was performed by GC-MS, LC-MS and NMR spectroscopy. For quantitative measurements, the main volatile compound needed to be isolated from pitanga pulp to obtain a commercially not available reference standard. Cyanidin-3-glucoside was determined as one of the most abundant non-volatile pulp compound yielding 53.8% of the sum of the intensities of all ions detected by LC-MS. Quantification of cyanidin-3-glucoside in pitanga pulp resulted in a concentration of 344 ± 66.4 ?g/mL corresponding to 688 ± 133 ?g/g dried pulp and 530 ± 102 ?g/g fruit. For the volatile fraction, oxidoselina-1,3,7(11)-trien-8-one was identified as the main volatile pulp constituent (27.7% of the sum of the intensities of all ions detected by GC-MS), reaching a concentration of 89.0 ± 16.9 ?g/mL corresponding to 1.34 ± 0.25 ?g/g fresh pulp and 1.03 ± 0.19 ?g/g fruit. The results provide quantitative evidence for the occurrence of an anthocyanin and an oxygenated sesquiterpene as one of the major volatile and non-volatile low-molecular-weight compounds in pitanga pulp. PMID:26394146

  10. Incorporation of an introduced weed into the diet of a native butterfly: consequences for preference, performance and chemical defense.

    PubMed

    Knerl, Angela; Bowers, M Deane

    2013-10-01

    The introduction of exotic plants, animals, and pathogens into non-native ecosystems can have profound effects on native organisms. Plantago lanceolata, narrow-leaf or ribwort plantain (Plantaginaceae), is a weed that was introduced to North America from Eurasia approximately 200 years ago and that has been incorporated into the diet of a variety of native North American herbivores. Plantain contains two iridoid glycosides, aucubin and catalpol, that can be toxic or deterrent to non-specialized herbivores or herbivores that have recently incorporated this species into their diet. Anartia jatrophae (Nymphalidae), the white peacock, feeds on plants in five families including the Plantaginaceae, and was recently observed feeding on plantain; however, the effects of feeding on this novel host plant are unknown. In this study, we performed a series of experiments to assess larval preference and performance on the introduced P. lanceolata and on a native host plant that does not contain iridoid glycosides, water hyssop, Bacopa monnieri (Plantaginaceae). We also tested whether or not white peacocks were able to sequester iridoid glycosides and compared this ability with an iridoid specialist, the buckeye, Junonia coenia (Nymphalidae). White peacocks successfully developed to the adult stage on plantain; larvae grew more slowly but pupae were heavier when compared with larvae and pupae reared on the native host plant. Larvae showed induced feeding preferences for the host plant on which they were reared. Furthermore, larvae sequestered small amounts of iridoids that were also retained in pupae and adults. These results suggest that incorporation of the introduced weed, plantain, into the diet of the white peacock may have important consequences for larval performance and preference, as well as for interactions with natural enemies. PMID:24142264

  11. Simultaneous determination of calycosin-7-O-?-D-glucoside, ononin, calycosin, formononetin, astragaloside IV, and astragaloside II in rat plasma after oral administration of Radix Astragali extraction for their pharmacokinetic studies by ultra-pressure liquid chromatography with tandem mass spectrometry.

    PubMed

    Liu, Xiao-hua; Zhao, Jian-bang; Guo, Long; Yang, Ying-lai; Hu, Fang; Zhu, Rui-juan; Feng, Shi-lan

    2014-09-01

    A sensitive and reliable ultra-pressure liquid chromatography with tandem mass spectrometry (UPLC-MS) was developed and validated for simultaneous quantification of six main bioactive components, i.e., calycosin-7-O-?-D-glucoside, ononin, calycosin, formononetin, astragaloside IV, and astragaloside II in rat plasma after oral administration of the 95 % ethanol extraction from Radix Astragali. Plasma samples were extracted with Waters Oasis(TM) HLB 1 cc (30 mg) Extraction Cartridges (SPE) separated on an UPLC™ BEH C18 column and detected by MS with electro spray ionization interface in positive selective ion monitoring mode. Calibration curves offered linear ranges of two orders of magnitude with r (2) > 0.99. The method had the lower limit quantification of 1.30, 0.73, 1.17, 2.33, 0.63, and 0.83 ng/mL for ononin, calycosin, calycosin-7-O-?-D-glucoside, formononetin, astragaloside IV, and astragaloside II, respectively, with precision less than 10 %. The RSD of intra- and inter-day variations ranged from 1.66 to 6.46 and 3.39 to 6.58 %. This developed method was applied subsequently to pharmacokinetic studies of the six compounds in rats successfully. The proposed method was for the first time to compare the pharmacokinetic difference between calycosin-7-O-?-D-glucoside and calycosin in rat plasma, so as between ononin and formononetin, and studied to the astragaloside II pharmacokinetics in rat plasma. PMID:24782060

  12. Partial amino acid sequence and mRNA analysis of cytosolic pyridoxine-beta-D-glucoside hydrolase from porcine intestinal mucosa: proposed derivation from the lactase-phlorizin hydrolase gene.

    PubMed

    Tseung, Chi-Wah; McMahon, Laura G; Vázquez, Jorge; Pohl, Jan; Gregory, Jesse F

    2004-05-15

    We have previously identified and purified a novel beta-glucosidase, designated PNGH (pyridoxine-5'-beta-D-glucoside hydrolase), from the cytosolic fraction of pig intestinal mucosal. PNGH catalyses the hydrolysis of PNG (pyridoxine-5'-beta-D-glucoside), a plant derivative of vitamin B6 that exhibits partial nutritional bioavailability in humans and animals. Preliminary amino acid sequence analysis indicated regions of close similarity of PNGH to the precursor form of LPH (lactase-phlorizin hydrolase), the beta-glucosidase localized to the brush-border membrane. We report in the present study amino acid sequence data for PNGH and results of Northern blot analyses, upon which we propose a common genomic origin of PNGH and LPH. Internal Edman sequencing of the PNGH band isolated by SDS/PAGE yielded data for 16 peptides, averaging 10.8 amino acids in length. These peptides from PNGH (approx. 140 kDa) were highly similar to sequences existing over most of the length of the >200 kDa precursor of rabbit LPH; however, we found no PNGH sequences that corresponded to approx. 350 amino acids between positions 463 and 812 of the LPH precursor, a region encoded by exon 7 of the LPH precursor gene (amino acids 568-784), and no sequences that corresponded to regions near the N-terminus. MS analysis of tryptic peptides yielded 25 peptides, averaging 15 amino acids, with masses that matched segments of the rabbit LPH precursor. Northern blot analysis of pig and human small intestinal polyadenylated mRNA using a non-specific LPH cDNA probe showed an expected approx. 6 kb transcript of the LPH precursor, but also an approx. 4 kb transcript that was consistent with the size predicted from the PNGH protein mass. Using a probe specific to the region encoded by exon 7, hybridization occurred only with the 6 kb transcript. Based on these observations, we propose that both PNGH and LPH enzymes have the same genomic origin, but differ in transcriptional and, possibly, post-translational processing. PMID:14972028

  13. Partial amino acid sequence and mRNA analysis of cytosolic pyridoxine-beta-D-glucoside hydrolase from porcine intestinal mucosa: proposed derivation from the lactase-phlorizin hydrolase gene.

    PubMed Central

    Tseung, Chi-Wah; McMahon, Laura G; Vázquez, Jorge; Pohl, Jan; Gregory, Jesse F

    2004-01-01

    We have previously identified and purified a novel beta-glucosidase, designated PNGH (pyridoxine-5'-beta-D-glucoside hydrolase), from the cytosolic fraction of pig intestinal mucosal. PNGH catalyses the hydrolysis of PNG (pyridoxine-5'-beta-D-glucoside), a plant derivative of vitamin B6 that exhibits partial nutritional bioavailability in humans and animals. Preliminary amino acid sequence analysis indicated regions of close similarity of PNGH to the precursor form of LPH (lactase-phlorizin hydrolase), the beta-glucosidase localized to the brush-border membrane. We report in the present study amino acid sequence data for PNGH and results of Northern blot analyses, upon which we propose a common genomic origin of PNGH and LPH. Internal Edman sequencing of the PNGH band isolated by SDS/PAGE yielded data for 16 peptides, averaging 10.8 amino acids in length. These peptides from PNGH (approx. 140 kDa) were highly similar to sequences existing over most of the length of the >200 kDa precursor of rabbit LPH; however, we found no PNGH sequences that corresponded to approx. 350 amino acids between positions 463 and 812 of the LPH precursor, a region encoded by exon 7 of the LPH precursor gene (amino acids 568-784), and no sequences that corresponded to regions near the N-terminus. MS analysis of tryptic peptides yielded 25 peptides, averaging 15 amino acids, with masses that matched segments of the rabbit LPH precursor. Northern blot analysis of pig and human small intestinal polyadenylated mRNA using a non-specific LPH cDNA probe showed an expected approx. 6 kb transcript of the LPH precursor, but also an approx. 4 kb transcript that was consistent with the size predicted from the PNGH protein mass. Using a probe specific to the region encoded by exon 7, hybridization occurred only with the 6 kb transcript. Based on these observations, we propose that both PNGH and LPH enzymes have the same genomic origin, but differ in transcriptional and, possibly, post-translational processing. PMID:14972028

  14. Transcriptome profiling and digital gene expression analysis of Fallopia multiflora to discover putative genes involved in the biosynthesis of 2,3,5,4'-tetrahydroxy stilbene-2-O-?-D-glucoside.

    PubMed

    Zhao, Wei; Xia, Wanxia; Li, Jiewen; Sheng, Shujing; Lei, Lei; Zhao, Shujing

    2014-08-15

    The compound 2,3,5,4'-tetrahydroxy stilbene-2-O-ß-d-glucoside (THSG) synthesized by Fallopia multiflora (F. multiflora) exhibits pharmacological potency. However, the mechanistic details of its biosynthesis pathway are still vague. To clear this ambiguity, we performed de novo transcriptome assembly and digital gene expression (DGE) profiling analyses of F. multiflora using the Illumina RNA-seq system. RNA-seq generated approximately 70 million high-quality reads that were assembled into 65,653 unigenes (mean length=750 bp), including 26,670 clusters and 38,983 singletons. A total of 48,173 (73.4%) unigenes were annotated using public protein databases with a cut-off e-value above 10(-5). Furthermore, we investigated the transcriptome difference of four different F. multiflora tissues using DGE profiling. Variations in gene expression were identified based on comparisons of transcriptomes from various parts of a high-level THSG- and a low-level THSG-producing F. multiflora plant. Clusters with similar differential expression patterns and enriched metabolic pathways with regard to the differentially expressed genes putatively involved in THSG biosynthesis were revealed for the first time. Our data provides the most comprehensive sequence resource regarding F. multiflora so far. Taken together, the results of this study considerably extend the knowledge on THSG production. PMID:24967942

  15. Chemical constituents from the fruits of Gardenia jasminoides Ellis.

    PubMed

    Yu, Yang; Feng, Xiao-Lin; Gao, Hao; Xie, Zuo-Lei; Dai, Yi; Huang, Xiao-Jun; Kurihara, Hiroshi; Ye, Wen-Cai; Zhong, Yi; Yao, Xin-Sheng

    2012-04-01

    A new lignan glucoside, (+)-(7S,8R,8'R)-lyoniresinol 9-O-?-D-(6?-O-trans-sinapoyl)glucopyranoside (1), and a new iridoid glucoside, 10-O-trans-sinapoylgeniposide (2), together with eight known compounds, were isolated from the fruits of Gardenia jasminoides Ellis. The structures of the isolates were elucidated by extensive spectroscopic studies, including UV, IR, 1D and 2D NMR, ESI-MS, HR-ESI-MS, and CD experiments. The short-term-memory-enhancement activities of some compounds were evaluated on an A? transgenic drosophila model. PMID:22245087

  16. The biosynthesis of cyanogenic glucosides in higher plants. Identification of three hydroxylation steps in the biosynthesis of dhurrin in Sorghum bicolor (L. ) Moench and the involvement of 1-ACI-nitro-2-(p-hydroxyphenyl)ethane as an intermediate

    SciTech Connect

    Halkier, B.A.; Moller, B.L. )

    1990-12-05

    N-Hydroxytyrosine, (E)- and (Z)-p-hydroxyphenyl-acetaldehyde oxime, p-hydroxyphenylacetonitrile, and p-hydroxymandelonitrile are established intermediates in the biosynthesis of the tyrosine-derived cyanogenic glucoside dhurrin. Simultaneous measurements of oxygen consumption and biosynthetic activity using a microsomal enzyme system isolated from etiolated sorghum seedlings demonstrate a requirement for three oxygen molecules in the conversion of tyrosine to p-hydroxymandelonitrile. Two oxygen molecules are consumed in the conversion of tyrosine to (E)-p-hydroxyphenylacetaldehyde oxime, indicating the existence of a previously undetected hydroxylation step in addition to that resulting in the formation of N-hydroxytyrosine. Radioactively labeled 1-nitro-2-(p-hydroxyphenyl)ethane was chemically synthesized and tested as a possible intermediate. Biosynthetic experiments demonstrate that the microsomal enzyme system metabolizes the nitro compound to the subsequent intermediates in dhurrin synthesis (Km = 0.05 mM; Vmax = 14 nmol/mg of protein/h). Low amounts of 1-nitro-2-(p-hydroxyphenyl)ethane are produced in the microsomal reaction mixtures when tyrosine is used as substrate. These data support the involvement of 1-nitro-2-(p-hydroxyphenyl)ethane or more likely its aci-nitro tautomer as an intermediate between N-hydroxytyrosine and p-hydroxyphenylacetaldehyde oxime. The conversion of (E)-p-hydroxyphenylacetaldehydeoxime to p-hydroxymandelonitrile requires a single oxygen molecule. The oxygen molecule is utilized for hydroxylation of p-hydroxyphenylacetonitrile into p-hydroxymandelonitrile. This indicates that the conversion of p-hydroxyphenylacetaldehyde oxime into p-hydroxyphenylacetonitrile proceeds by a simple dehydration reaction.

  17. Protective effects of 2,3,5,4'-tetrahydroxystilbene-2-O-?-d-glucoside in the MPTP-induced mouse model of Parkinson's disease: Involvement of reactive oxygen species-mediated JNK, P38 and mitochondrial pathways.

    PubMed

    He, Hong; Wang, Songhai; Tian, Jiyu; Chen, Lei; Zhang, Wei; Zhao, Junjie; Tang, Haifeng; Zhang, Xiaojun; Chen, Jianzong

    2015-11-15

    Parkinson's disease (PD) is characterized by the selective death of dopaminergic neurons in the substantia nigra pars compacta. Oxidative stress-induced neuron loss is thought to play a crucial role in the pathogenesis of PD. Previous work from our group suggests that 2,3,5,4'-tetrahydroxystilbene-2-O-?-d-glucoside (TSG), an active component extracted from a traditional Chinese herb, Polygonum multiflorum thunb, can attenuate 1-methyl-4-phenyl pyridium-induced apoptosis in the neuronal cell line PC12, by inhibiting reactive oxygen species generation and modulating c-Jun N-terminal kinases (JNK) activation. Here, we investigated the protective effects of TSG against 1-methyl-4-phenyl-1,2,3,6-tetrahydropypridine (MPTP)-induced loss of tyrosine hydroxylase positive cells in mice and the underlying mechanisms. The results showed that MPTP-induced loss of tyrosine hydroxylase positive cells and reactive oxygen species generation were prevented by TSG in a dose-dependent manner. The reactive oxygen species scavenger N-acetylcysteine could also mitigate reactive oxygen species generation. Moreover, JNK and P38 were activated by MPTP, but extracellular signal-regulated protein kinases phosphorylation did not change after MPTP treatment. TSG at different doses blocked the activation of JNK and P38. The protective effect of TSG was also associated with downregulation of the bax/bcl-2 ratio, reversed the release of cytochrome c and smac, and inhibited the activation of caspase-3, -6, and -9 induced by MPTP. In conclusion, our studies demonstrated that the protective effects of TSG in the MPTP-induced mouse model of PD are involved, at least in part, in controlling reactive oxygen species-mediated JNK, P38, and mitochondrial pathways. PMID:26477638

  18. 2-Nitro-3-(p-hydroxyphenyl)propionate and aci-1-nitro-2-(p-hydroxyphenyl)ethane, two intermediates in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L. ) Moench

    SciTech Connect

    Halkier, B.A.; Lykkesfeldt, J.; Moller, B.L. )

    1991-01-15

    The biosynthetic pathway for the cyanogenic glucoside dhurrin derived from tyrosine has been studied in vitro by using ({sup 18}O)oxygen and a microsomal enzyme system obtained from etiolated sorghum seedlings. The products formed were purified by HPLC and TLC, and the incorporation of ({sup 18}O)oxygen was monitored by mass spectrometry. In the presence of NADPH and ({sup 18}O)dioxygen, L-tyrosine is converted to (E)- and (Z)-p-hydroxyphenylacetaldhyde oxime with quantitative incorporation of an ({sup 18}O)oxygen atom into the oxime function. These data demonstrate that the conversion of N-hydroxytyrosine to p-hydroxyphenylacetaldehyde oxime involves additional N-hydroxylation and N-oxidation reactions giving rise to the formation of 2-nitro-3-(p-hydroxyphenyl)propionate, which by decarboxylation produces aci-1-nitro-2-(p-hydroxyphenyl)ethane. Both compounds are additional intermediates in the pathway. The two ({sup 18}O)oxygen atoms introduced by the N-hydroxylations are enzymatically distinguishable as demonstrated by the specific loss of the oxygen atom introduced by the first N-hydroxylation reaction in the subsequent conversion of aci-1-nitro-2-(p-hydroxyphenyl)ethane to (E)-p-hydroxyphenylacetaldehyde oxime. A high flux of intermediates through the microsomal enzyme system is obtained with N-hydroxytyrosine as a substrate. This renders the conversion of the aci-nitro compound rate limiting and results in its release from the active site of the enzyme system and accumulation of the tautomeric nitro compound.

  19. Hydrophilic interaction liquid chromatography coupled with tandem mass spectrometry for the quantification of uridine diphosphate-glucose, uridine diphosphate-glucuronic acid, deoxynivalenol and its glucoside: In-house validation and application to wheat.

    PubMed

    Warth, Benedikt; Siegwart, Gerald; Lemmens, Marc; Krska, Rudolf; Adam, Gerhard; Schuhmacher, Rainer

    2015-12-01

    Nucleotide sugars, the activated forms of monosaccharides, are important metabolites involved in a multitude of cellular processes including glycosylation of xenobiotics. Especially in plants, UDP-glucose is one of the most prominent members among these nucleotide-sugars, as it is involved in the formation of glucose conjugates of xenobiotics, including mycotoxins, but also holds a central role in the interconversion of energized sugars such as the formation of UDP-glucuronic acid required for cell wall biosynthesis. Here, we present the first HILIC-LC-ESI-TQ-MS/MS method for the quantification of UDP-glucose and UDP-glucuronic acid together with the Fusarium toxin deoxynivalenol (DON) and its major plant detoxification product DON-3-O-glucoside (DON-3-Glc) utilizing a polymer-based column. For sample preparation a time-effective and straightforward 'dilute and shoot' protocol was applied. The chromatographic run time was minimized to 9min including proper column re-equilibration. In-house validation of the method verified its linear range, intra- (1-7%) and interday (8-20%) precision, instrumental LODs between 0.6 and 10ngmL(-1), selectivity and moderate matrix effects with mean recoveries of 85-103%. To prove the methods applicability, we analyzed two sets of wheat extracts obtained from different cultivars grown under standardized greenhouse conditions. The results clearly demonstrated the suitability of the developed method to quantify UDP-glucose, DON and its masked form D3G in diluted wheat extracts. We observed differing concentration levels of UDP-glucose in the two wheat cultivars showing different resistance to the severe plant disease Fusarium head blight. We propose that the higher ability to detoxify DON into DON-3-Glc might be a consequence of the higher cellular UDP-glucose pool in the resistant cultivar. PMID:26554298

  20. Mechanisms of membrane protein insertion into liposomes during reconstitution procedures involving the use of detergents. 1. Solubilization of large unilamellar liposomes (Prepared by reverse-phase evaporation) by Triton X-100 octyl glucoside, and sodium cholate

    SciTech Connect

    Paternostre, M.T.; Roux, M.; Rigaud, J.L.

    1988-04-19

    The mechanisms governing the solubilization by Triton X-100, octyl glucoside, and sodium cholate of large unilamellar liposomes prepared by reverse-phase evaporation were investigated. The solubilization process is described by the three-stage model previously proposed for the detergents. In stage I, detergent monomers are incorporated into the phospholipid bilayers until they saturate the liposomes. At this point, i.e., stage II, mixed phospholipid-detergent micelles begin to form. By stage III, the lamellar to micellar transition is complete and all the phospholipids are present as mixed micelles. The turbidity of liposome preparations was systematically measured as a function of the amount of detergent added for a wide range of phospholipid concentrations. The results allowed a quantitative determination of the effective detergent to lipid molar ratios in the saturated liposomes. The monomer concentrations of the three detergents in the aqueous phase were also determined at the lamellar to micellar transitions. These transitions were also investigated by /sup 31/P NMR spectroscopy, and complete agreement was found with turbidity measurements. Freeze-fracture electron microscopy and permeability studies in the sublytic range of detergent concentrations indicated that during stage I of solubilization detergent partitioning between the aqueous phase and the lipid bilayer greatly affects the basic permeability of the liposomes without significantly changing the morphology of the preparations. A rough approximation of the partition coefficients was derived from the turbidity and permeability data. It is concluded that when performed systematically, turbidity measurements constitute a very convenient and powerful technique for the quantitative study of the liposome solubilization process by detergents.

  1. Direct comparison between genomic constitution and flavonoid contents in Allium multiple alien addition lines reveals chromosomal locations of genes related to biosynthesis from dihydrokaempferol to quercetin glucosides in scaly leaf of shallot (Allium cepa L.).

    PubMed

    Masuzaki, S; Shigyo, M; Yamauchi, N

    2006-02-01

    The extrachromosome 5A of shallot (Allium cepa L., genomes AA) has an important role in flavonoid biosynthesis in the scaly leaf of Allium fistulosum-shallot monosomic addition lines (FF+nA). This study deals with the production and biochemical characterisation of A. fistulosum-shallot multiple alien addition lines carrying at least 5A to determine the chromosomal locations of genes for quercetin formation. The multiple alien additions were selected from the crossing between allotriploid FFA (female symbol) and A. fistulosum (male symbol). The 113 plants obtained from this cross were analysed by a chromosome 5A-specific PGI isozyme marker of shallot. Thirty plants were preliminarily selected for an alien addition carrying 5A. The chromosome numbers of the 30 plants varied from 18 to 23. The other extrachromosomes in 19 plants were completely identified by using seven other chromosome markers of shallot. High-performance liquid chromatography analyses of the 19 multiple additions were conducted to identify the flavonoid compounds produced in the scaly leaves. Direct comparisons between the chromosomal constitution and the flavonoid contents of the multiple alien additions revealed that a flavonoid 3'-hydroxylase (F3'H) gene for the synthesis of quercetin from kaempferol was located on 7A and that an anonymous gene involved in the glucosidation of quercetin was on 3A or 4A. As a result of supplemental SCAR analyses by using genomic DNAs from two complete sets of A. fistulosum-shallot monosomic additions, we have assigned F3'H to 7A and flavonol synthase to 4A. PMID:16411131

  2. TSG (2,3,4’?,5-tetrahydroxystilbene 2-O-?-D-glucoside) suppresses induction of pro-inflammatory factors by attenuating the binding activity of nuclear factor-?B in microglia

    PubMed Central

    2013-01-01

    Background Induction of pro-inflammatory factors is one of the characteristics of microglia activation and can be regulated by numerous active components of Chinese traditional herbs. Suppression of pro-inflammatory factors is beneficial to alleviate microglia-mediated cell injury. The present study aims to investigate the effect and possible mechanism of 2,3,4’,5-tetrahydroxystilbene 2-O-?-D-glucoside (TSG) on LPS-mediated induction of pro-inflammatory factors in microglia. Methods Western blot, ELISA, and Hoechst 33258 were used to measure the protein expression, TNF-?/IL-6 content, and apoptotic nuclei, respectively. The mRNA level was measured by real time-PCR. Nitric oxide (NO) content, lactate dehydrogenase (LDH) content, and NF-?B binding activity were assayed by commercial kits. Results TSG reduced iNOS protein expression as well as TNF-?, IL-6, and NO content in LPS-stimulated BV-2 cells. TSG attenuated the increase in apoptotic nuclei, caspase-3 cleavage, and LDH content induced by BV-2 cell-derived conditioned medium in primary hippocampal neurons. Mechanistic studies showed that TSG reduced the mRNA level of iNOS, TNF-?, and IL-6. TSG failed to suppress I?B-? degradation, NF-?B phosphorylation and nuclear translocation, and ERK1/2, JNK, and p38 phosphorylation. TSG, however, markedly reduced the binding of NF-?B to its DNA element. Chromatin immunoprecipitation (ChIP) assays confirmed that TSG reduced NF-?B binding to the iNOS promoter. These findings were ascertained in primary microglia where the LPS-induced increase in iNOS expression, NO content, apoptotic nuclei, and NF-?B binding to its DNA element were diminished by TSG. Conclusions These studies demonstrate that TSG attenuates LPS-mediated induction of pro-inflammatory factors in microglia through reducing the binding activity of NF-?B. This might help us to further understand the pharmacological role of TSG in inflammatory response in the central nervous system. PMID:24144353

  3. 2,3,5,4'-tetrahydroxystilbene-2-O-?-D-glucoside protects human umbilical vein endothelial cells against lysophosphatidylcholine-induced apoptosis by upregulating superoxide dismutase and glutathione peroxidase.

    PubMed

    Zhao, Jing; Xu, Shouzhu; Song, Fan; Nian, Lun; Zhou, Xuanxuan; Wang, Siwang

    2014-10-01

    2,3,5,4'-Tetrahydroxystilbene-2-O-?-d-glucoside (TSG) has been shown to protect human umbilical vein endothelial cells (HUVECs) from lysophosphatidylcholine (LPC)-induced injury; however, the underlying molecular mechanism remains to be determined. The aim of this study was to investigate the protective mechanism of TSG against LPC-induced injury in HUVECs. We established a stable LPC-induced cell model by treating HUVECs with various concentrations of LPC and found 10.0 µg/mL of LPC to be optimal for inducing HUVECs injury. The effects of TSG on LPC-induced cell injury were assessed by cell counting kit-8, apoptosis assay, transmission electron microscope, and measurement of malondialdehyde (MDA), the antioxidant enzymes superoxide dismutase (SOD), reactive oxygen species (ROS), glutathione peroxidase, and mitochondrial membrane potential. The mRNA and protein levels of caspase-3, Bax, Bcl-2, PARP-1, and cytochrome C were assayed by real-time reverse transcriptase-polymerase chain reaction and immunoblotting, respectively. TSG pretreatment was able to prevent LPC-induced HUVECs injury and restore cell viability in a concentration-dependent manner. LPC treated cells showed typical apoptotic morphological changes including cytoplasmic vacuolation, swollen mitochondria, and characteristic biochemical hallmarks of apoptosis including loss of mitochondrial membrane potential, activation of caspase-3, decrease of Bcl-2, increase of PARP-1, upregulation of Bax, and release of cytochrome C, all of which were apparently inhibited by TSG pretreatment. Treatment of HUVECs with LPC led to decrease of SOD and glutathione peroxidase in addition to rapid increase of MDA and ROS levels. Pretreatment with TSG restored SOD and glutathione peroxidase levels to that of normal levels, and significantly decreased ROS and MDA levels. Our data indicate that TSG inhibits apoptosis of HUVECs mediated by LPC through blocking the mitochondrial apoptotic pathway and suggest that the mechanisms underlying the protective effects of TSG are related to the activation of SOD and glutathione peroxidase, the clearance of intracellular ROS, and reduction of lipid peroxidation. PMID:25382724

  4. A New Lignan Glucoside from Lagochilus ilicifolius

    PubMed Central

    Jing-Shi, Qian; Cheng-Gang, Zhang; Wei, Wang; Ting, Zhang; Hong, Xu; Gui-Xin, Chou

    2015-01-01

    Background: The whole herb of Lagochilus ilicifolius has been used as a folk medicine for treating hemostatic, inflammation and ulcer in China. There were only limited reports on its chemical constituents, and no reports on its pharmacology study. Objective: To isolate compounds from the whole herb of L. ilicifolius and evaluate their cytotoxic activity. Materials and Methods: The column chromatographic techniques were used for separating the constituents of the n-butanol-soluble fraction of the 95% ethanol extract from the whole plant of L. ilicifolius. The structures of one new lignan and two known lignans were elucidated on the basis of spectroscopic analyses and comparison with literature data. The cytotoxic activities of these three lignans were evaluated using the MTT-assay against PC12 cell line derived from rat adrenal pheochromocytoma. Results: The new lignan was identified as erythro-1-[(4-O-?-D-glucopyranosyl-3-methoxyl)-phenyl]-2-[(5’-methoxyl)-pinoresinol]-propane-1,3-diol (1), and two known lignans were identified as tortoside C (2) and sisymbrifolin (3). The new lignan exhibited significant cytotoxic activity against PC12 cell line with IC50 value of 1.22 ± 0.03 ?mol/L. Conclusions: A new lignan, erythro-1-[(4-O-?-D-glucopyranosyl-3-methoxyl)-phenyl]-2-[(5’-methoxyl)-pinoresinol]-propane-1,3-diol and two known lignans were isolated from the whole herbs of L. ilicifolius. The two known lignans were reported for the first time in the genus Lagochilus. Three lignans were evaluated for in vitro cytotoxic activity. The new lignan showed relatively strong cytotoxicity against PC12 cell line, while sisymbrifolin and tortoside C exibited no cytotoxicity. PMID:25709232

  5. Light and Nutrient Dependent Responses in Secondary Metabolites of Plantago lanceolata Offspring Are Due to Phenotypic Plasticity in Experimental Grasslands

    PubMed Central

    Miehe-Steier, Annegret; Roscher, Christiane; Reichelt, Michael; Gershenzon, Jonathan; Unsicker, Sybille B.

    2015-01-01

    A few studies in the past have shown that plant diversity in terms of species richness and functional composition can modify plant defense chemistry. However, it is not yet clear to what extent genetic differentiation of plant chemotypes or phenotypic plasticity in response to diversity-induced variation in growth conditions or a combination of both is responsible for this pattern. We collected seed families of ribwort plantain (Plantago lanceolata) from six-year old experimental grasslands of varying plant diversity (Jena Experiment). The offspring of these seed families was grown under standardized conditions with two levels of light and nutrients. The iridoid glycosides, catalpol and aucubin, and verbascoside, a caffeoyl phenylethanoid glycoside, were measured in roots and shoots. Although offspring of different seed families differed in the tissue concentrations of defensive metabolites, plant diversity in the mothers' environment did not explain the variation in the measured defensive metabolites of P. lanceolata offspring. However secondary metabolite levels in roots and shoots were strongly affected by light and nutrient availability. Highest concentrations of iridoid glycosides and verbascoside were found under high light conditions, and nutrient availability had positive effects on iridoid glycoside concentrations in plants grown under high light conditions. However, verbascoside concentrations decreased under high levels of nutrients irrespective of light. The data from our greenhouse study show that phenotypic plasticity in response to environmental variation rather than genetic differentiation in response to plant community diversity is responsible for variation in secondary metabolite concentrations of P. lanceolata in the six-year old communities of the grassland biodiversity experiment. Due to its large phenotypic plasticity P. lanceolata has the potential for a fast and efficient adjustment to varying environmental conditions in plant communities of different species richness and functional composition. PMID:26336100

  6. Light and Nutrient Dependent Responses in Secondary Metabolites of Plantago lanceolata Offspring Are Due to Phenotypic Plasticity in Experimental Grasslands.

    PubMed

    Miehe-Steier, Annegret; Roscher, Christiane; Reichelt, Michael; Gershenzon, Jonathan; Unsicker, Sybille B

    2015-01-01

    A few studies in the past have shown that plant diversity in terms of species richness and functional composition can modify plant defense chemistry. However, it is not yet clear to what extent genetic differentiation of plant chemotypes or phenotypic plasticity in response to diversity-induced variation in growth conditions or a combination of both is responsible for this pattern. We collected seed families of ribwort plantain (Plantago lanceolata) from six-year old experimental grasslands of varying plant diversity (Jena Experiment). The offspring of these seed families was grown under standardized conditions with two levels of light and nutrients. The iridoid glycosides, catalpol and aucubin, and verbascoside, a caffeoyl phenylethanoid glycoside, were measured in roots and shoots. Although offspring of different seed families differed in the tissue concentrations of defensive metabolites, plant diversity in the mothers' environment did not explain the variation in the measured defensive metabolites of P. lanceolata offspring. However secondary metabolite levels in roots and shoots were strongly affected by light and nutrient availability. Highest concentrations of iridoid glycosides and verbascoside were found under high light conditions, and nutrient availability had positive effects on iridoid glycoside concentrations in plants grown under high light conditions. However, verbascoside concentrations decreased under high levels of nutrients irrespective of light. The data from our greenhouse study show that phenotypic plasticity in response to environmental variation rather than genetic differentiation in response to plant community diversity is responsible for variation in secondary metabolite concentrations of P. lanceolata in the six-year old communities of the grassland biodiversity experiment. Due to its large phenotypic plasticity P. lanceolata has the potential for a fast and efficient adjustment to varying environmental conditions in plant communities of different species richness and functional composition. PMID:26336100

  7. Glycosidic monoterpenes from Linaria capraria.

    PubMed

    Bianco, Armandodoriano; Guiso, Marcella; Ballero, Mauro; Foddai, Sebastiano; Nicoletti, Marcello; Piccin, Antonella; Serafini, Mauro; Tomassini, Lamberto

    2004-06-01

    During our systematic study on the species of genus Linaria (Scrophulariaceae) present in Italy, we examined the glycosidic fraction of Linaria capraria Moris et De Not., a species endemic of Tuscany archipelago. This fraction is particularly complex and we considered in this article only the medium polarity components. In accordance with previous studies, L. capraria shows acyl derivatives of antirrhinoside 1 as specific chemotaxonomic iridoidic markers. L. capraria exhibits a complex composition, with regard to iridoidic constituents, with several chromatographic problems to be resolved. We then isolated, besides the known antirrhinoside 1, two acyl derivatives of antirrhinoside, the 6'-O-senecioyl derivative, 2, and the 6'-O-angeloyl derivative, 3. In addition a glucoside of an acyclic monoterpene, 4, was also isolated, which may be correlated to the other monoterpenic glycosides isolated from other species of Scrophulariaceae. PMID:15143834

  8. Does vegetation complexity affect host plant chemistry, and thus multitrophic interactions, in a human-altered landscape?

    PubMed

    Wäschke, Nicole; Hancock, Christine; Hilker, Monika; Obermaier, Elisabeth; Meiners, Torsten

    2015-09-01

    Anthropogenic land use may shape vegetation composition and affect trophic interactions by altering concentrations of host plant metabolites. Here, we investigated the hypotheses that: (1) plant N and defensive secondary metabolite contents of the herb Plantago lanceolata are affected by land use intensity (LUI) and the surrounding vegetation composition (=plant species richness and P. lanceolata density), and that (2) changes in plant chemistry affect abundances of the herbivorous weevils Mecinus pascuorum and Mecinus labilis, as well as their larval parasitoid Mesopolobus incultus, in the field. We determined plant species richness, P. lanceolata density, and abundances of the herbivores and the parasitoid in 77 grassland plots differing in LUI index in three regions across Germany. We also measured the N and secondary metabolite [the iridoid glycosides (IGs) aucubin and catalpol] contents of P. lanceolata leaves. Mixed-model analysis revealed that: (1) concentrations of leaf IGs were positively correlated with plant species richness; leaf N content was positively correlated with the LUI index. Furthermore: (2) herbivore abundance was not related to IG concentrations, but correlated negatively with leaf N content. Parasitoid abundance correlated positively only with host abundance over the three regions. Structural equation models revealed a positive impact of IG concentrations on parasitoid abundance in one region. We conclude that changes in plant chemistry due to land use and/or vegetation composition may affect higher trophic levels and that the manifestation of these effects may depend on local biotic or abiotic features of the landscape. PMID:25986560

  9. Photoperiod-induced geographic variation in plant defense chemistry.

    PubMed

    Reudler, J H; Elzinga, Jelmer A

    2015-02-01

    Spatial variation in chemical defense of plants can be caused by genetic, biotic, and abiotic factors. For example, many plants exhibit a latitudinal cline in chemical defense, potentially due to latitudinal variation in abiotic environmental factors such as the light regime during the growing season. In the worldwide distributed Plantago lanceolata, the levels of deterrent iridoid glycosides (IGs), aucubin and catalpol, vary geographically, including latitudinally. To examine whether latitudinal variation in photoperiod can explain part of this geographic variation, plants from the Netherlands and Finland were exposed to two different photoperiods, simulating the Dutch (middle European) and Finnish (northern European) light period during the growing season. The experiment showed that although most variation in IG content was genetic, plants from both Dutch and Finnish origin produce relatively more catalpol under a northern European than under a middle European photoperiod. Our results confirm that latitudinal effects on photoperiod can contribute to geographic variation in plant defense chemistry, which should be considered when studying latitudinal clines in plant-enemy interactions. PMID:25637332

  10. Linking Microbial Community Structure to ?-Glucosidic Function in Soil Aggregates

    SciTech Connect

    Bailey, Vanessa L.; Fansler, Sarah J.; Stegen, James C.; McCue, Lee Ann

    2013-10-01

    To link microbial community 16S structure to a measured function in a natural soil we have scaled both DNA and ?-glucosidase assays down to a volume of soil that may approach a unique microbial community. ?-glucosidase activity was assayed in 450 individual aggregates which were then sorted into classes of high or low activities, from which groups of 10 or 11 aggregates were identified and grouped for DNA extraction and pyrosequencing. Tandem assays of ATP were conducted for each aggregate in order to normalize these small groups of aggregates for biomass size. In spite of there being no significant differences in the richness or diversity of the microbial communities associated with high ?-glucosidase activities compared with the communities associated with low ?-glucosidase communities, several analyses of variance clearly show that the communities of these two groups differ. The separation of these groups is partially driven by the differential abundances of members of the Chitinophagaceae family. It may be that observed functional differences in otherwise similar soil aggregates can be largely attributed to differences in resource availability, rather than to presence or absence of particular taxonomic groups.

  11. A new eudesmane sesquiterpene glucoside from Liriope muscari fibrous roots.

    PubMed

    Zhang, Hai Ming; Wang, Gang Li; Bai, Chun Qi; Liu, Peng; Liu, Zi Mu; Liu, Qi Zhi; Wang, Yong Yan; Liu, Zhi Long; Du, Shu Shan; Deng, Zhi Wei

    2011-01-01

    The screening of several Chinese medicinal herbs for nematocidal properties showed that the ethanol extract of Liriope muscari fibrous roots possessed significant nematocidal activity against the pine wood nematode (Bursaphelenchus xylophilus). From the ethanol extract, a new constituent (1,4-epoxy-cis-eudesm-6-O-?-D-glucopyranoside) and three known glycosides [1?,6?-dihydroxy-cis-eudesm-3-ene-6-O-?-D-glucopyranoside (liriopeoside A), 1?,6?-dihydroxy-cis-eudesm-3-ene-6-O-?-D-glucopyranoside, and 1?,6?-dihydroxy-5,10-bis-epi-eudesm-4(15)-ene-6-O-? D-glucopyranoside] were isolated by bioassay-guided fractionation. The structures were elucidated by 1D and 2D NMR and MS techniques. 1,4-Epoxy-cis-eudesm-6-O-?-D-glucopyranoside possessed moderate nemato-cidal activity against B. xylophilus with a LC(50 )value of 339.76 ?g/mL, while liriopeoside A (LC(50) = 82.84 ?g/mL) and 1?,6?-dihydroxy-cis-eudesm-3-ene-6-O-?-D-glucopyranoside (LC(50) = 153.39 ?g/mL) also exhibited nematocidal activity against B. xylophilus. The crude extract of L. muscari fibrous roots exhibited nematocidal activity against the pine wood nematode with a LC(50) value of 182.56 ?g/mL. PMID:22031065

  12. Oleuropein, a non-toxic olive iridoid, is an anti-tumor agent and cytoskeleton disruptor

    SciTech Connect

    Hamdi, Hamdi K. . E-mail: hkhamdi@gmail.com; Castellon, Raquel

    2005-09-02

    Oleuropein, a non-toxic secoiridoid derived from the olive tree, is a powerful antioxidant and anti-angiogenic agent. Here, we show it to be a potent anti-cancer compound, directly disrupting actin filaments in cells and in a cell-free assay. Oleuropein inhibited the proliferation and migration of advanced-grade tumor cell lines in a dose-responsive manner. In a novel tube-disruption assay, Oleuropein irreversibly rounded cancer cells, preventing their replication, motility, and invasiveness; these effects were reversible in normal cells. When administered orally to mice that developed spontaneous tumors, Oleuropein completely regressed tumors in 9-12 days. When tumors were resected prior to complete regression, they lacked cohesiveness and had a crumbly consistency. No viable cells could be recovered from these tumors. These observations elevate Oleuropein from a non-toxic antioxidant into a potent anti-tumor agent with direct effects against tumor cells. Our data may also explain the cancer-protective effects of the olive-rich Mediterranean diet.

  13. Teucrium polium Phenylethanol and Iridoid Glycoside Characterization and Flavonoid Inhibition of Biofilm-Forming

    E-print Network

    Paré, Paul W.

    of Biofilm-Forming Staphylococcus aureus Wael A. Elmasri, Tianjiao Yang, Phat Tran, Mohamed-Elamir F. Hegazy Supporting Information ABSTRACT: The chemical composition and biofilm regulation of 15 metabolites from H-1 H COSY, HMQC, HMBC, and NOESY), and/or LC-ESIMS/MS data analyses. Inhibition of the biofilm

  14. Anti-inflammatory activity of iridoid and catechol derivatives from Eucommia ulmoides Oliver.

    PubMed

    Luo, Dan; Or, Terry C T; Yang, Cindy L H; Lau, Allan S Y

    2014-09-17

    Neuroinflammation and pro-inflammatory mediators play key roles in the pathogenesis of neurodegenerative diseases including stroke, which account for a significant burden of morbidity and mortality worldwide. Recently, the unsatisfactory pharmacotherapy and side effects of the drugs led to the development of alternative medicine for treating these diseases. Du Zhong (DZ), Eucommia ulmoides Oliver leaves, is a commonly used herb in the therapy of stroke in China. We hypothesize that the components from DZ inhibit neuroinflammation. In this study, DZ was extracted and the bioactive fractions with inhibitory effect on lipopolysaccharide (LPS)-stimulated nitric oxide (NO) production in BV-2 microglial cells were further separated using chromatography. Two purified bioactive compounds, genipin (compound C) and 4-(1,2-dimethoxyethyl)benzene-1,2-diol (compound F), were isolated and identified after spectroscopic analysis. The results showed that they inhibited LPS-stimulated NO and tumor necrosis factor-alpha (TNF-?) production. Genipin exerted its anti-inflammatory effects through PI3K/Akt signaling pathway, whereas compound F inhibited phosphorylation of p38 mitogen-activated protein kinase (MAPK). In conclusion, genipin and compound F have potential for developing into new drugs for treating neurodegenerative diseases. PMID:25065689

  15. Studies on iridoids of tissue cultures of Penstemon serrulatus: isolation and their antiproliferative properties.

    PubMed

    Wysoki?ska, H; Skrzypek, Z

    1992-01-01

    Penstemide and serrulatoloside as well as penstemide aglycone and serrulatoloside aglycone were isolated and identified in the calli and suspension cultures of Penstemon serrulatus. The influence of serrulatoloside, penstemide, and its aglycone on the spontaneous proliferation of mouse spleen lymphocytes or hepatoma cells in the Syrian hamster has been estimated in vitro. It has been found that these compounds produce a dose-dependent inhibition of [3H]-thymidine incorporation into the DNA of the examined cells. PMID:1602300

  16. Multi-Target Strategy and Experimental Studies of Traditional Chinese Medicine for Alzheimer's Disease Therapy.

    PubMed

    Li, Lin; Zhang, Lan; Yang, Cui-Cui

    2016-01-01

    Alzheimer's disease (AD) is a multifactorial complex disease. The pathogenesis of AD is very complicated, and involves the ?-amyloid (A?) cascade, tau hyperphosphorylation, neuroinflammation, oxidative stress, mitochondrial dysfunction, reduced levels of neurotrophic factors, and damage and loss of synapses as well as cholinergic neurons. The multi-target characteristics of traditional Chinese medicine (TCM) may be advantageous over single-target drugs in the treatment of complex diseases. These drugs have therefore attracted more attention in the research and development of AD therapies. This review describes advances made in experimental studies of TCM for AD treatment. It discusses research, from our group and other laboratories, on TCM compound drugs (Shenwu capsule) and approximately 10 Chinese medicinal herb extracts (tetrahydroxystilbene glucoside, epimedium flavonoid, icariin, cornel iridoid glycoside, ginsenoside, puerarin, clausenamide, huperzine A, and timosaponins). PMID:26268330

  17. An in vivo microdialysis measurement of harpagoside in rat blood and bile for predicting hepatobiliary excretion and its interaction with cyclosporin A and verapamil.

    PubMed

    Wu, Qian; Wen, Xiao-Dong; Qi, Lian-Wen; Wang, Wei; Yi, Ling; Bi, Zhi-Ming; Li, Ping

    2009-03-15

    Harpagoside, a major bioactive iridoid glucoside in genus Scrophularia, has been widely used in clinical practice for the treatment of pain in the joints and lower back for its neuroprotective and anti-inflammation activities. To investigate the pharmacokinetics and hepatobiliary excretion, an in vivo microdialysis method coupled with high performance liquid chromatography was developed to monitor the concentration of harpagoside in blood and bile. The harpagoside bile-to-blood distribution ratio (AUC(bile)/AUC(blood)) up to 986.28+/-78.46 significantly decreased to 6.41+/-0.56 or 221.20+/-18.92 after co-administration of cyclosporin A or verapamil. The results indicated that harpagoside went through concentrative elimination from the bile which was probably regulated by P-glucoprotein, providing possible clinical trials of co-administration of transporter inhibitors to decrease drug efflux, thus to enhance the curative effects. PMID:19237327

  18. Potential hepatotoxicity of geniposide, the major iridoid glycoside in dried ripe fruits of Gardenia jasminoides (Zhi-zi).

    PubMed

    Ding, Yue; Zhang, Tong; Tao, Jian-sheng; Zhang, Li-ying; Shi, Jian-rong; Ji, Guang

    2013-01-01

    The safety of geniposide, mainly focusing on its hepatotoxicity in rats, was determined by liver enzymes in serum and histopathology ultrastructural preparation. The lethal dose, 50% (LD50) of per oral geniposide was 1431.1 mg kg(-1). The acute toxicity study indicated geniposide at dose of 574 mg kg(-1) or more could cause hepatic toxicity in rats and the hepatotoxicity often appeared at 24-48 h after the oral administration. The hepatotoxicity was associated with oxidative stress with decrease of total superoxide dismutase activity and increase of malondialdehyde concentration in rats' livers. Subchronic toxicity study showed geniposide did not cause hepatotoxicity at the doses of 24.3 and 72.9 mg kg(-1) orally for 90 days in rats. Thus, acute hepatotoxicity of geniposide at high doses was likely to be linked to oxidative stress, while geniposide at normal dose of 24.3 mg kg(-1) or less did not cause hepatotoxicity even in the repeated dosing study. PMID:22456001

  19. Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part II: Iridomyrmecins

    PubMed Central

    Hilgraf, Robert; Zimmermann, Nicole; Lehmann, Lutz; Tröger, Armin

    2012-01-01

    Summary Following our earlier approach to the synthesis of dihydronepetalactones, all eight stereoisomers of trans-fused iridomyrmecins were synthesized starting from the enantiomers of limonene. Combined gas chromatography and mass spectrometry including enantioselective gas chromatography revealed that volatiles released by the endohyperparasitoid wasp Alloxysta victrix contain (4S,4aR,7S,7aR)-iridomyrmecin of 95–97% ee and stereochemically pure (4S,4aS,7R,7aS)-iridomyrmecin as a minor component. PMID:23019456

  20. Cognitive-enhancing and antioxidant activities of iridoid glycosides from Scrophularia buergeriana in scopolamine-treated mice.

    PubMed

    Jeong, Eun Ju; Lee, Ki Yong; Kim, Seung Hyun; Sung, Sang Hyun; Kim, Young Choong

    2008-06-24

    The cognitive-enhancing activities of E-harpagoside and 8-O-E-p-methoxycinnamoylharpagide (MCA-Hg) isolated from Scrophularia buergeriana were evaluated in scopolamine-induced amnesic mice by the Morris water maze and by passive avoidance tests. E-harpagoside and MCA-Hg significantly improved the impairment of reference memory induced by scopolamine in the Morris water maze test. The mean escape latency, the mean path length and swimming movement were also improved by both compounds. In passive avoidance test, E-harpagoside and MCA-Hg (2 mg/kg body weight, p.o.) significantly ameliorated scopolamine-induced amnesia by as much as 70% of the level found in normal control mice. Donepezil, an acetylcholinesterase inhibitor and the most widely used drug for AD treatment was employed as a positive control. The activity of acetylcholinesterase was inhibited significantly by E-harpagoside or MCA-Hg within the cortex and hippocampus to a level similar to that observed in mice treated with donepezil (2 mg/kg body weight, p.o.). Moreover, treatment with E-harpagoside or MCA-Hg to scopolamine-induced amnesic mice significantly decreased TBARS level which was accompanied by an increase in the activities or contents of glutathione reductase, SOD and reduced GSH. We believe these data demonstrate that E-harpagoside or MCA-Hg exerted potent cognitive-enhancing activity through both anti-acetylcholinesterase and antioxidant mechanisms. PMID:18462717

  1. Rapid characterization and determination of multiple components in Bu-Shen-Yi-Qi-Fang by high-performance liquid chromatography coupled to electrospray ionization and quadrupole time-of-flight mass spectrometry.

    PubMed

    Nurahmat, Mammat; Chen, Meixia; Luo, Qingli; Ling, Yun; Dong, Jingcheng; Huang, Chenggang

    2014-12-01

    In this study, a qualitative and quantitative analysis using high-performance liquid chromatography coupled to electrospray ionization and quadrupole time-of-flight mass spectrometry was performed for the quality control of Bu-Shen-Yi-Qi-Fang, a traditional Chinese formula used for asthma. Thirty-four compounds, including flavonoids, isoflavonoids, triterpenoid saponins, and iridoid glycosides were identified or tentatively characterized by comparing their retention times and mass spectra with those of authentic standards or literature data. Sixteen components were considered as the main bioactive constituents of Bu-Shen-Yi-Qi-Fang and they were chosen as the chemical markers in quantitative analysis, including catalpol, leonuride, calycosin-7-O-?-d-glucoside, hyperoside, acteoside, formononetin-7-O-?-D-glucoside, epimedin A, calycosin, icariin, epimedin B, epimedin C, formononetin, astragaloside IV, astragaloside II, baohuoside-I, and astragaloside I. The total run time was 20 min. It was found that the calibration curves for all analytes showed good linearity (R(2) > 0.99) within the test ranges. The relative standard deviations for intra- and inter-day precisions were below 3.9 and 11.7%, respectively. The accuracy was evaluated by the recovery test within the range of 89.20-110.71% with the relative standard deviation < 4.8%. The sample was stable for at least 48 h at 4°C. The results showed that the new approach was effective for the quality control of Bu-Shen-Yi-Qi-Fang. PMID:25216330

  2. Bitter Gentian Teas: Nutritional and Phytochemical Profiles, Polysaccharide Characterisation and Bioactivity.

    PubMed

    Olennikov, Daniil N; Kashchenko, Nina I; Chirikova, Nadezhda K; Koryakina, Lena P; Vladimirov, Leonid N

    2015-01-01

    As a result of the wide distribution of herbal teas the data on nutritional characterisation, chemical profile and biological activity of these products are required. The decoctions of Gentiana algida, G. decumbens, G. macrophylla and G. triflora herb teas were nutritionally characterized with respect to their macronutrients, demonstrating the predominance of polysaccharides and low lipid content. Gentian decoctions were also submitted to a microcolumn RP-HPLC-UV analysis of phytochemicals demonstrating a high content of iridoids (177.18-641.04 ?g/mL) and flavonoids (89.15-405.71 ?g/mL). Additionally, mangiferin was detected in samples of G. triflora tea (19.89 ?g/mL). Five free sugars (fructose, glucose, sucrose, gentiobiose, gentianose) were identified in all gentian teas studied, as well as six organic acids (malic, citric, tartaric, oxalic, succinic, quinic). Pectic polysaccharides with a high content of rhamnogalacturonans and arabinogalactans were also identified and characterized in gentian decoctions for the first time. Gentian tea decoctions and their specific compounds (gentiopicroside, loganic acid-6'-O-?-d-glucoside, isoorientin, isoorientin-4'-O-?-d-glucoside, mangiferin, water-soluble polysaccharides) showed a promising antimicrobial, anti-inflammatory and antioxidant potentials. Evidences obtained indicate the prospective use of gentian herb teas as food products and medicines. PMID:26556333

  3. Stimulation of hepatocyte growth factor production by ascorbic acid and its stable 2-glucoside.

    PubMed

    Wu, Y L; Gohda, E; Iwao, M; Matsunaga, T; Nagao, T; Takebe, T; Yamamoto, I

    1998-10-01

    Hepatocyte growth factor (HGF), a cytokine which is generally produced by mesenchymal cells, has mitogenic, motogenic and morphogenic activities in epithelial cells and it also has tumor-suppressing activities. Induction of HGF production may be involved in organ regeneration, wound healing and embryogenesis. We examined the effects of ascorbic acid (AsA), which stimulates the proliferation of fibroblasts, and its stable derivative, 2-O-alpha-D-glucopyranosyl-L-ascorbic acid (AA-2G), on HGF production by human skin fibroblasts. Basal HGF secretion was significantly stimulated by more than 0.1 mM AsA or AA-2G. Both vitamins synergistically enhanced HGF secretion stimulated by growth factors such as epidermal growth factor (EGF), platelet-derived growth factor (PDGF) and basic fibroblast growth factor (bFGF), cholera toxin and other inducers. Induction by EGF or bFGF was most markedly potentiated by the vitamins. HGF production by the KG-1 human leukemia cell line was also augmented by AsA or AA-2G. Another stable AsA derivative, ascorbic acid 2-phosphate (AA-2P) effectively promoted basal and EGF-induced HGF secretion by the fibroblasts, but ascorbic acid 2-sulfate (AA-2S) was much less effective. Intracellular AsA levels increased after the addition of AA-2G and AA-2P as well as AsA, but not after AA-2S. The effect of AA-2G was completely abrogated by the simultaneous addition of castanospermine, an alpha-glucosidase inhibitor, suggesting that the active form of AA-2G is AsA. Constitutive and EGF-induced HGF gene expression was also up-regulated after adding AsA or AA-2G to the cells. These results indicated that AsA acts alone or in synergy with several inducers to stimulate the production and gene expression of HGF in human skin fibroblasts and that the stable AsA derivative AA-2G is as effective as AsA in promoting HGF production. PMID:10984304

  4. BIOAVAILABILITY OF SOYBEAN ISOFLAVONES FROM AGLYCONE AND GLUCOSIDE FORMS IN AMERICAN WOMEN

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Even though the bioavailability of isoflavones from aglycone forms is believed to be higher than glycosides, human studies testing the bioavailability of isoflavones in Eastern and Western human subjects have been contradictory. To investigate the postprandial absorption and bioavailability of soy ...

  5. Two new naphthalene glucosides and other bioactive compounds from the carnivorous plant Nepenthes mirabilis.

    PubMed

    Thanh, Nguyen Van; Thao, Nguyen Phuong; Dat, Le Duc; Huong, Phan Thi Thanh; Lee, Sang Hyun; Jang, Hae Dong; Cuong, Nguyen Xuan; Nam, Nguyen Hoai; Kiem, Phan Van; Minh, Chau Van; Kim, Young Ho

    2015-10-01

    Two new naphthalene diglucosides named nepenthosides A (1) and B (2), together with eleven known compounds (3-13), were isolated from the carnivorous plant Nepenthes mirabilis. The structures of these compounds were elucidated based on extensive spectroscopic analysis, including 1D- and 2D-NMR, and MS. The antioxidant activities of compounds 1-13 were evaluated in terms of their peroxyl radical-scavenging (trolox equivalent, TE) and reducing capacities. All isolates showed peroxyl radical-scavenging and reducing activities at concentrations of 1.0 and 10.0 ?M. Anti-osteoporotic activities were investigated using murine osteoclastic RAW 264.7 cells. Compounds 1-7 and 9-12 significantly suppressed tartrate-resistant acid phosphatase activity down to 91.13 ± 1.18 to 42.39 ± 1.11 %, relative to the control (100 %) in nuclear factor-?B ligand (RAN?L)-induced osteoclastic RAW 264.7 macrophage cells. PMID:25724283

  6. Synthesis and Structural Characterization of Three Unique Helicobacter pylori ?-Cholesteryl phosphatidyl glucosides

    PubMed Central

    Nguyen, Huy Q.; Davis, Ryan A.; Gervay-Hague, Jacquelyn

    2014-01-01

    Steryl glycosides produced by bacteria play important biological roles in the evasion and modulation of host immunity. Step economy syntheses of three cholesteryl-6-O-phosphatidyl-?-D-glucopyranosides (?CPG) unique to H. pylori have been achieved. The approach relies upon regioselective C-6 deprotection of per-O-trimethylsilyl-?-D-cholesterylglucoside followed by phosphoramidite coupling. Global TMS ether deprotection in the presence of oxygen and subsequent deprotection of the cyano ethyl phosphoester afforded the target compounds in 16-21% overall yield starting from D-glucose. The structures of these natural products were rigorously determined using a combination of 2D NMR methods and mass spectrometry. These robust synthesis and characterization protocols provide analogues to facilitate glycolipidomic profiling and biological studies. PMID:25195783

  7. Prevention of UV-induced carcinogenesis by cyanidin-3-glucoside | Division of Cancer Prevention

    Cancer.gov

    Skip to main content Division of Cancer Prevention Search form Search Main menu Home Major Programs Research Networks Map Alliance of Glycobiologists for Detection of Cancer Barrett's Esophagus Translational Research Network (BETRNet) Cancer Prevention

  8. Acylated cyanidin 3-sophoroside-5-glucoside in purple-violet flowers of Moricandia arvensis (Brassicaceae).

    PubMed

    Tatsuzawa, Fumi; Kato, Kazuhisa; Sato, Motoki; Ito, Shun; Muraoka, Hiroki; Takahata, Yoshihito; Ogawa, Satoshi

    2015-03-01

    A new acylated anthocyanin was isolated as a major pigment, along with a known anthocyanin (Moricandia arvensis anthocyanin 1: MAA-1), from a strain of Moricandia arvensis (Code No. MOR-ARV-3) with purple-violet flowers, and identified as cyanidin 3-O-[2-O-(2-O-(4-O-(6-O-(4-O-(?-glucopyranosyl)-trans-caffeoyl)-?-glucopyranosyl)-trans-sinapoyl)-?-glucopyranoside]-5-O-[6-O-(malonyl)-?-glucopyranoside]. PMID:25924529

  9. SANS with Contrast Variation Study of the Bacteriorhodopsin-octyl Glucoside Complex

    SciTech Connect

    Heller, William T; Mo, Yiming

    2010-01-01

    Membrane proteins (MPs), which play vital roles in trans-membrane trafficking and signaling between cells and their external environment, comprise a major fraction of the expressed proteomes of many organisms. MP production for biophysical characterization requires detergents for extracting MPs from their native membrane and to solubilize the MP in solution for purification and study. In a proper detergent solution, the detergent-associated MPs retain their native fold and oligomerization state, key requirements for biophysical characterization and crystallization. SANS with contrast variation was performed to characterize BR in complex with OG to better understand the MP-detergent complex. Contrast variation makes it possible to not only probe the conformation of the entire structure but also investigate the conformation of the polypeptide chain within the BR-OG complex. The BR-OG SANS contrast variation series is not consistent with a compact structure, such as a trimeric BR complex surrounded by a belt of detergent. The data strongly suggest that the protein is partially unfolded through its association with the detergent micelles.

  10. The identification and quantification of steryl glucosides in precipitates from commercial biodiesel

    Technology Transfer Automated Retrieval System (TEKTRAN)

    There have been several experiences of the occurrence of precipitates in manufacturing facilities, transport vessels, and storage tanks containing biodiesel. In some cases these have been formed during storage at temperatures above the cloud point of the fuel. High performance liquid chromatograph...

  11. Treatment of Xerosis with a Topical Formulation Containing Glyceryl Glucoside, Natural Moisturizing Factors, and Ceramide

    PubMed Central

    Kausch, Martina; Rippke, Frank; Schoelermann, Andrea M.; Filbry, Alexander W.

    2012-01-01

    Objective: To assess the effects of Light Formulation, an oil-in-water emulsion, and Rich Formulation, a water-in-oil emulsion, for the treatment of xerosis. Design: Two double-blind, vehicle-controlled trials (both formulations); a double-blind, randomized regression study (Rich Formulation); and a single-blind tolerability study (Light Formulation). The two formulations were applied twice daily for two weeks, for five days in the regression study, and twice daily for two weeks in the tolerability study. Setting: Studies were conducted during winter in Hamburg, Germany. Participants: A total of 169 subjects were enrolled and 154 completed the studies. The majority were between 50 and 80 years of age, women, all with very dry skin. One withdrew because of an incompatibility reaction that reoccurred with the subject's own body lotion after sun exposure. Measurements: Skin hydration and skin barrier function with both formulations over two weeks, long-term moisturization effect after discontinuation of Rich Formulation, and symptom improvement and skin tolerability with Light Formulation. Results: Vehicle-controlled studies of Light and Rich Formulations demonstrated significantly improved hydration at Weeks 1 and 2 versus the untreated site and vehicles, and significantly reduced transepidermal water loss versus untreated site and basic vehicle. Both products significantly decreased visible dryness and tactile roughness. In the regression study, Rich Formulation maintained significant moisturization six days after treatment discontinuation. Light Formulation reduced symptoms of itching, burning, tightness, tingling, and feeling of dryness. Conclusion: These formulations represent a new approach for the treatment of xerosis by addressing multiple key deficiencies in skin hydration. PMID:22916312

  12. Role of 5-HT2 receptors in diabetes: Swertiamarin seco-iridoid glycoside might be a possible 5-HT2 receptor modulator.

    PubMed

    Sonawane, Rakesh Deelip; Deore, Vijaykumar B; Patil, Savita D; Patil, Chandragouda R; Surana, Sanjay J; Goyal, Ramesh K

    2015-05-15

    In the present review, we are focusing on modulators of 5-HT2 receptors, swertiamarin and their role in diabetes. These drugs possess both central and peripheral actions in various animal models of depression, diabetes and obesity. Swertiamarin and 5-HT2 antagonist are reported antidepressant, hypolipidemic and beneficial in peripheral vasculopathy. In contrast to this, 5-HT2C selective agonist decreases hyperglycemia, hyperlipidemia and insulin secretogogue by action. Selective serotonin reuptake inhibitors (SSRIs) are known antidepressant having weight gain as an adverse effect. Swertiamarin has similar pharmacological actions as 5-HT2 antagonist and 5-HT2C selective agonist. This warrants that swertiamarin might modulate 5-HT2 receptors rather than affecting the uptake of serotonin. In the light of present investigation, the mechanism of these drugs can correlate the role of central and peripheral 5-HT2 receptors in diabetes. PMID:25708274

  13. A comparison of antirrhinoside distribution in the organs of two related Plantaginaceae species with different reproductive strategies.

    PubMed

    Beninger, Clifford W; Cloutier, Renée R; Grodzinski, Bernard

    2009-11-01

    A study of two related plants (Antirrhinum majus L. and Linaria vulgaris Mill.) containing the same defensive compound (the iridoid glucoside, antirrhinoside) but with reproductive strategies that differ during ontogeny was undertaken. Young leaves are important to plants due to their higher photosynthetic rates and, therefore, should be better protected with higher concentrations of defensive compounds such as antirrhinoside. Declining concentrations of antirrhinoside as leaves aged was found for A. majus but this was generally not the case for L. vulgaris. Concentrations of antirrhinoside in root tissue were low and constant throughout ontogeny for A. majus whereas for L. vulgaris root levels of antirrhinoside were high during the period when vegetative growth is its sole means of reproduction. Antirrhinoside in L. vulgaris roots declined relative to A. majus roots during budding and flowering. During flowering, significantly less antirrhinoside and relative biomass are devoted to L. vulgaris flowers than in A. majus. While these findings are consistent with Optimal Defense Theory (ODT) further work on the distribution of antirrhinoside and the effect of insect herbivory on plant fitness in other related species is needed. PMID:19949840

  14. Hydrolysis of Oleuropein by Lactobacillus plantarum Strains Associated with Olive Fermentation

    PubMed Central

    Ciafardini, G.; Marsilio, V.; Lanza, B.; Pozzi, N.

    1994-01-01

    Oleuropein (Chemical Abstracts Service registry number 32619-42-4), a bitter-tasting secoiridoid glucoside commonly found in leaves of the olive tree as well as in olives (Olea europaea L.), was found to be hydrolyzed by the ?-glucosidase (EC 3.2.1.2.1) produced by oleuropeinolytic Lactobacillus plantarum-type strains. Three strains, designated B17, B20, and B21, were isolated from the brine of naturally ripe olives not treated with alkali. These strains were rod-shaped forms, grown at a pH 3.5 limit, and tolerated 1% oleuropein and 8% NaCl in the growth medium. The ?-glucosidase produced hydrolyzed 5-bromo-4-chloro-3-indolyl-?-d-glucopy-ranoside as well as oleuropein. The presence of 2% glucose in the medium inhibited activity by 40 to 50%, depending on the bacterial strain. Chromatographic analysis of the trimethylsilyl derivatives of the products obtained after 7 days of incubation at 30°C of strain B21 showed all the hydrolysis products of oleuropein, i.e., aglycone, iridoid monoterpen, and 3,4-dihydroxyphenylethanol (hydroxytyrosol). Oleuropein and its aglycone after 21 days of incubation decreased to trace levels with the simultaneous increase in concentration of ?-3,4-dihydroxyphenylethanol. Images PMID:16349442

  15. Antidiabetic compounds from Sarracenia purpurea used traditionally by the Eeyou Istchee Cree First Nation.

    PubMed

    Muhammad, Asim; Guerrero-Analco, Jose A; Martineau, Louis C; Musallam, Lina; Madiraju, Padma; Nachar, Abir; Saleem, Ammar; Haddad, Pierre S; Arnason, John T

    2012-07-27

    Through ethnobotanical surveys, the CIHR Team in Aboriginal Antidiabetic Medicines identified 17 boreal forest plants stemming from the pharmacopeia of the Cree First Nations of Eeyou Istchee (James Bay region of Northern Quebec) that were used traditionally against diabetes symptoms. The leaves of Sarracenia purpurea (pitcher plant), one of the identified Cree plants, exhibited marked antidiabetic activity in vitro by stimulating glucose uptake in C2C12 mouse muscle cells and by reducing glucose production in H4IIE rat liver cells. Fractionation guided by glucose uptake in C2C12 cells resulted in the isolation of 11 compounds from this plant extract, including a new phenolic glycoside, flavonoid glycosides, and iridoids. Compounds 6 (isorhamnetin-3-O-glucoside), 8 [kaempferol-3-O-(6?-caffeoylglucoside], and 11 (quercetin-3-O-galactoside) potentiated glucose uptake in vitro, which suggests they represent active principles of S. purpurea (EC(50) values of 18.5, 13.8, and 60.5 ?M, respectively). This is the first report of potentiation of glucose uptake by compounds 6 and 8, while compound 11 (isolated from Vaccinium vitis) was previously shown to enhance glucose uptake. Treatment of H4IIE liver cells with the new compound 1, 6'-O-caffeoylgoodyeroside, decreased hepatic glucose production by reducing glucose-6-phosphatase enzymatic activity (IC(50) = 13.6 ?M), which would contribute to lowering glycemia and to the antidiabetic potential of S. purpurea. PMID:22738356

  16. Nano-liquid chromatography coupled to time-of-flight mass spectrometry for phenolic profiling: a case study in cranberry syrups.

    PubMed

    Contreras, María del Mar; Arráez-Román, David; Fernández-Gutiérrez, Alberto; Segura-Carretero, Antonio

    2015-01-01

    A new method based on nano-liquid chromatography coupled to time-of-flight mass spectrometry (nano-LC-TOF-MS) using lock-mass calibration was developed to facilitate the accurate and routine characterization and quantification of phenolic compounds. Thus, it was applied to study cranberry syrups, in which, using negative ionization mode, a total of nine phenolic compounds were unequivocally identified using standards and 38 tentatively taking into account their retention time, accurate mass (errors<5 ppm) data and isotope pattern, as well as literature. Among them, 13 compounds, belonging to flavonols and iridoids conjugated with phenolic acids, were reported for first time in cranberry or cranberry based-products. The analytical method was also validated using chlorogenic acid, p-coumaric acid, (+)-catechin, (-)-epicatechin, procyanidin A2, quercetin 3-O-glucoside, quercetin 3-O-rhamnoside, quercetin, and myricetin standards. In this way, the analytical method showed adequate linearity, with R(2) above 0.99, and acceptable values of intra- and inter-day repeatability of the retention time and peak area. The detection limits and quantification were between 1.0-15.6 ng mL(-1) and 2.0-62.5 ng mL(-1), respectively. The method can be extended to characterize phenolic compounds in other food and plant matrices, and as well biological samples. PMID:25476399

  17. Transglucosylation of ascorbic acid to ascorbic acid 2-glucoside by a recombinant sucrose phosphorylase from Bifidobacterium longum.

    PubMed

    Kwon, Taeyeon; Kim, Cheong Tae; Lee, Jong-Hoon

    2007-04-01

    A novel transglycosylation reaction from sucrose to L-ascorbic acid by a recombinant sucrose phosphorylase from Bifidobacterium longum was used to produce a stable L-ascorbic acid derivative. The major product was detected by HPLC, and confirmed to be 2-O-alpha-D-glucopyranosyl-L-ascorbic acid by LC-MS/MS analysis. PMID:17216298

  18. Neutral Loss Ion Mapping Experiment Combined with Precursor Mass List and Dynamic Exclusion for Screening Unstable Malonyl Glucoside Conjugates

    NASA Astrophysics Data System (ADS)

    Yang, Min; Zhou, Zhe; Yao, Shuai; Li, Shangrong; Yang, Wenzhi; Jiang, Baohong; Liu, Xuan; Wu, Wanying; Qv, Hua; Guo, De-an

    2015-09-01

    Malonates are one type of the acylation conjugates and found abundantly in ginseng and soybean. Malonyl conjugates of ginsenosides and isoflavone glycosides were often considered as the characteristic components to evaluate various species and different forms of ginseng and soybean products because of their thermal instability. Another famous isoflavonoid-rich leguminous traditional Chinese medicine (TCM), named Puerarin lobata (Gegen), has also been reported to contain malonyl daidzin and malonyl genistin. However, the conjugates were found to present in very low amount and particularly unstable in the negative ion mode scan using LTQ Orbitrap mass spectrometry with electrospray ionization (ESI). In order to screen and characterize the malonyl conjugates in Gegen, a specific method was designed and developed combining neutral loss ion mapping (NLIM) experiment and precursor mass list (PL) triggered data dependent acquisition (DDA). Along with the activation of dynamic exclusion (DE), the method was proven to be specific and efficient for searching the malonate derivatives from Gegen. Two samples were examined by the established method. A total of 66 compounds were found, and 43 of them were malonates of isoflavone glycoside. Very few compounds were reported previously in Gegen. The results are helpful to understand the constituents of Gegen with more insight. The study not only provided a method for analyzing the malonyl conjugates from complex matrices but also explored a way to trace other low amount components in TCMs.

  19. Neutral Loss Ion Mapping Experiment Combined with Precursor Mass List and Dynamic Exclusion for Screening Unstable Malonyl Glucoside Conjugates.

    PubMed

    Yang, Min; Zhou, Zhe; Yao, Shuai; Li, Shangrong; Yang, Wenzhi; Jiang, Baohong; Liu, Xuan; Wu, Wanying; Qv, Hua; Guo, De-An

    2016-01-01

    Malonates are one type of the acylation conjugates and found abundantly in ginseng and soybean. Malonyl conjugates of ginsenosides and isoflavone glycosides were often considered as the characteristic components to evaluate various species and different forms of ginseng and soybean products because of their thermal instability. Another famous isoflavonoid-rich leguminous traditional Chinese medicine (TCM), named Puerarin lobata (Gegen), has also been reported to contain malonyl daidzin and malonyl genistin. However, the conjugates were found to present in very low amount and particularly unstable in the negative ion mode scan using LTQ Orbitrap mass spectrometry with electrospray ionization (ESI). In order to screen and characterize the malonyl conjugates in Gegen, a specific method was designed and developed combining neutral loss ion mapping (NLIM) experiment and precursor mass list (PL) triggered data dependent acquisition (DDA). Along with the activation of dynamic exclusion (DE), the method was proven to be specific and efficient for searching the malonate derivatives from Gegen. Two samples were examined by the established method. A total of 66 compounds were found, and 43 of them were malonates of isoflavone glycoside. Very few compounds were reported previously in Gegen. The results are helpful to understand the constituents of Gegen with more insight. The study not only provided a method for analyzing the malonyl conjugates from complex matrices but also explored a way to trace other low amount components in TCMs. Graphical Abstract ?. PMID:26334988

  20. Flavone C-glucosides responsible for yellow pigmentation induced by low temperature in bracts of Zantedeschia aethiopica.

    PubMed

    Nakayama, Masayoshi; Koshioka, Masaji; Kondo, Tadao; Imizu, Kiyotoshi

    2015-03-01

    We aimed to identify the main compounds responsible for low temperature-induced yellow pigmentation of the bracts of Zantedeschia aethiopica 'Wedding March'. On the basis of the area ratios estimated from absorbance at 400 nm in HPLC analyses, we identified two flavonoids, isoorientin and swertiajaponin, as such compounds. We also identified two additional flavonoids, isovitexin and swertisin, which do not contribute considerably to the yellow pigmentation. Flavonoids of Zantedeschia bracts seem to belong to the class of flavone C-glycosides. PMID:25924520

  1. Bioavailability of C-linked dihydrochalcone and flavanone glucosides in humans following ingestion of unfermented and fermented rooibos teas.

    PubMed

    Stalmach, Angélique; Mullen, William; Pecorari, Monia; Serafini, Mauro; Crozier, Alan

    2009-08-12

    High-performance liquid chromatography-mass spectrometry (HPLC-MS(n)) detected aspalathin and nothofagin, C-glycosides of apigenin and luteolin, and four eriodictyol-C-glycoside isomers in unfermented and fermented rooibos teas. The fermented drink contained 10-fold higher levels of aspalathin and nothofagin and a 4-fold lower eriodictyol-C-glycoside content than the fermented tea. The total flavonoid contents in 500 mL servings of the teas were 84 (fermented) and 159 mumol (unfermented). Following the ingestion of 500 mL of the teas by 10 volunteers, 0-24 h urine and plasma samples were collected for analysis. HPLC-MS(n) identified eight metabolites in urine. These were O-linked methyl, sulfate, and glucuronide metabolites of aspalathin and an eriodictyol-O-sulfate. The main compound excreted was an O-methyl-aspalathin-O-glucuronide (229 nmol) following ingestion of the unfermented drink and eriodictyol-O-sulfate (68 nmol) after ingestion of the fermented beverage. The overall metabolite levels excreted were 82 and 352 nmol, accounting for 0.09 and 0.22% of the flavonoids in the fermented and unfermented drinks, respectively. Most of the aspalathin metabolites were excreted within 5 h of tea consumption, suggesting absorption in the small intestine. Urinary excretion of the eriodictyol-O-sulfate occurred mainly during the 5-12 h collection period, indicative of absorption in the large intestine. Despite exhaustive searches, no flavonoid metabolites were detected in plasma. PMID:19534535

  2. An on-line method for pressurized hot water extraction and enzymatic hydrolysis of quercetin glucosides from onions.

    PubMed

    Lindahl, Sofia; Liu, Jiayin; Khan, Samiullah; Karlsson, Eva Nordberg; Turner, Charlotta

    2013-06-27

    A novel environmentally sound continuous-flow hot water extraction and enzymatic hydrolysis method for determination of quercetin in onion raw materials was successfully constructed using a stepwise optimization approach. In the first step, enzymatic hydrolysis of quercetin-3,4'-diglucoside to quercetin was optimized using a three level central composite design considering temperature (75-95°C), pH (3-6) and volume concentration of ethanol (5-15%). The enzyme used was a thermostable ?-glucosidase variant (termed TnBgl1A_N221S/P342L) covalently immobilized on either of two acrylic support-materials (Eupergit(®) C 250L or monolithic cryogel). Optimal reaction conditions were irrespective of support 84°C, 5% ethanol and pH 5.5, and at these conditions, no significant loss of enzyme activity was observed during 72 h of use. In a second step, hot water extractions from chopped yellow onions, run at the optimal temperature for hydrolysis, were optimized in a two level design with respect to pH (2.6 and 5.5), ethanol concentration (0 and 5%) and flow rate (1 and 3 mL min(-1)) Obtained results showed that the total quercetin extraction yield was 1.7 times higher using a flow rate of 3 mL min(-1) (extraction time 90 min), compared to a flow rate of 1 mL min(-1) (extraction time 240 min). Presence of 5% ethanol was favorable for the extraction yield, while a further decrease in pH was not, not even for the extraction step alone. Finally, the complete continuous flow method (84°C, 5% ethanol, pH 5.5, 3 mL min(-1)) was used to extract quercetin from yellow, red and shallot onions and resulted in higher or similar yield (e.g. 8.4±0.7 ?mol g(-1) fresh weight yellow onion) compared to a conventional batch extraction method using methanol as extraction solvent. PMID:23764443

  3. Micronesica 39(2): 297-314, 2007 Habitat Heterogeneity of Cycas micronesica Seed Chemistry

    E-print Network

    Marler, Thomas E.

    was determined in seven populations throughout Guam to determine if steryl glucosides would segregate among the heterogeneity. Seed gameto- phyte content of steryl glucosides stigmasterol -D-glucoside and sitosterol -D

  4. HORTSCIENCE 44(3):725729. 2009. Phenotypic Characteristics

    E-print Network

    Marler, Thomas E.

    , cycads, Guam, phenotypic plasticity, size, sterol, steryl glucoside Abstract. The relationship between and steryl glucoside concentration and seed content in relation to whole plant and organ size variation

  5. Geniposide alleviates inflammation by suppressing MeCP2 in mice with carbon tetrachloride-induced acute liver injury and LPS-treated THP-1 cells.

    PubMed

    Ma, Tao-Tao; Li, Xiao-Feng; Li, Wan-Xia; Yang, Yang; Huang, Cheng; Meng, Xiao-Ming; Zhang, Lei; Li, Jun

    2015-12-01

    Geniposide (GP), an iridoid glucoside extracted from Gardenia jasminoides Ellis fruits, has been used as a herbal medicine to treat liver and gall bladder disorders for many years. However the mechanism of anti-inflammatory is largely unknown. In this study, GP significantly attenuated inflammation in acute liver injury (ALI) mice model and in lipopolysaccharide (LPS)-induced THP-1 cells. It was demonstrated that GP obviously decreased the expression of Methyl-CpG binding protein 2 (MeCP2) in vivo and in vitro. Knockdown of MeCP2 with siRNA suppressed the expressions of IL-6 and TNF-?, while over-expression of MeCP2 had a proinflammatory effect on the expression of IL-6 and TNF-? in LPS-induced THP-1 cells. Mechanistically, it was indicated that GP had anti-inflammatory effects at least in part, through suppressing MeCP2. Interestingly, GP could attenuate expressions of Sonic hedgehog (Shh) and GLIS family zinc finger 1 (GLIS1) but increase Ptched1 (PTCH1) expression. Similar findings were also demonstrated at the protein level by siRNA MeCP2. Furthermore, over-expression of MeCP2 obviously increased Shh and GLIS1 expressions but reduced PTCH1 expression. Taken together, GP may serve as an effective modulator of MeCP2-hedgehog pathway (Hh)-axis during the pathogenesis of inflammation. Our findings shed light on the potential therapeutic feature of GP in recovering inflammatory diseases. PMID:26371859

  6. Geniposide, from Gardenia jasminoides Ellis, inhibits the inflammatory response in the primary mouse macrophages and mouse models.

    PubMed

    Fu, Yunhe; Liu, Bo; Liu, Jinhua; Liu, Zhicheng; Liang, Dejie; Li, Fengyang; Li, Depeng; Cao, Yongguo; Zhang, Xichen; Zhang, Naisheng; Yang, Zhengtao

    2012-12-01

    Geniposide, a main iridoid glucoside component of gardenia fruit, has been known to exhibit antibacterial, anti-inflammatory and other important therapeutic activities. The objective of this study was to investigate the protective effects of geniposide on inflammation in lipopolysaccharide (LPS) stimulated primary mouse macrophages in vitro and LPS induced lung injury model in vivo. The expression of pro-inflammatory cytokines was determined by enzyme-linked immunosorbent assay (ELISA). Nuclear factor-kappa B (NF-?B), inhibitory kappa B (I?B?) protein, p38, extracellular signal-regulated kinase (ERK), c-Jun N-terminal kinase (JNK) and Toll-like receptor 4 (TLR4) were determined by Western blot. Further analysis was carried out in mTLR4 and mMD-2 co-transfected HEK293 cells. The results showed that geniposide markedly inhibited the LPS-induced TNF-?, IL-6 and IL-1? production both in vitro and in vivo. Geniposide blocked the phosphorylation of I?B?, p65, p38, ERK and JNK in LPS stimulated primary mouse macrophages. Furthermore, geniposide inhibited the expression of TLR4 in LPS stimulated primary mouse macrophages and inhibited the LPS-induced IL-8 production in HEK293-mTLR4/MD-2 cells. In vivo study, it was also observed that geniposide attenuated lung histopathologic changes in the mouse models. These results suggest that geniposide exerts an anti-inflammatory property by down-regulating the expression of TLR4 up-regulated by LPS. Geniposide is highly effective in inhibiting acute lung injury and may be a promising potential therapeutic reagent for acute lung injury treatment. PMID:22878137

  7. A review of phytotherapy of gout: perspective of new pharmacological treatments.

    PubMed

    Ling, X; Bochu, W

    2014-04-01

    The purpose of this review article is to outline plants currently used and those with high promise for the development of anti-gout products. All relevant literature databases were searched up to 25 March 2013. The search terms were 'gout', 'gouty arthritis', 'hyperuricemia', 'uric acid', 'xanthine oxidase (XO) inhibitor', 'uricosuric', 'urate transporter 1(URAT1)' and 'glucose transporter 9 (GLUT9)'. Herbal keywords included 'herbal medicine', 'medicinal plant', 'natural products', 'phytomedicine' and 'phytotherapy'. 'antiinflammatory effect' combined with the words 'interleukin-6 (IL-6)', 'interleukin-8 (IL-8)', 'interleukin-1beta (IL-1beta)', and 'tumor necrosis factor alpha (TNF-alpha)'. XO inhibitory effect, uricosuric action, and anti-inflammatory effects were the key outcomes. Numerous agents derived from plants have anti-gout potential. In in vitro studies, flavonoids, alkaloids, essential oils, phenolic compounds, tannins, iridoid glucosides, and coumarins show the potential of anti-gout effects by their XO inhibitory action, while lignans, triterpenoids and xanthophyll are acting through their anti-inflammatory effects. In animal studies, essential oils, lignans, and tannins show dual effects including reduction of uric acid generation and uricosuric action. Alkaloids reveal inhibit uric acid generation, show anti-inflammatory effects, or a combination of the two. Phenolic compounds and flavonoids inhibit uric acid production, show uricosuric anti-inflammatory effects. In the rare human studies, colchicine from Colchicum autumnale showed anti-inflammatory effects while for other plant extracts, although revealing anti-gout potential, further phytochemical investigations are needed to identify their active constituents. Besides, the plants which give antioxidant activities are much potent in the management of gout and need to be further investigated. The current review is a detailed discussion of the potential of medicinal plants for treatment of gout. PMID:24791587

  8. Neuroprotective activities of catalpol against CaMKII-dependent apoptosis induced by LPS in PC12 cells

    PubMed Central

    Chen, Wenna; Li, Ximing; Jia, Lian-Qun; Wang, Jun; Zhang, Lin; Hou, Diandong; Wang, Junyan; Ren, Lu

    2013-01-01

    Background and Purpose Neurodegenerative diseases present progressive neurological disorder induced by cell death or apoptosis. Catalpol, an iridoid glucoside isolated from the root of Rehmannia glutinosa Libosch, is present in a wide range of plant families. Although catalpol is an effective anti-apoptotic agent in LPS-induced neurodegeneration, the underlying mechanism has not been established. Here we have identified some of the mechanisms involved the prevention by catalpol of apoptosis induced by LPS in an experimental model of neurodegeneration in vitro. Experimental Approach Apoptosis was induced by adding LPS (80 ng·mL?1) to pheochromocytoma (PC12) cells, pretreated with catalpol for 12 h. We measured intracellular reactive oxygen species (ROS), apoptosis and intracellular calcium concentration ( [Ca2+]i) by flow cytometry or laser confocal scanning microscopy. We also analysed the protein expression of Bcl-2, Bax and Ca2+-calmodulin-dependent protein kinase II (CaMKII)-dependent apoptosis signal-regulating kinase-1 (ASK-1)/JNK/p38 signalling pathway in PC12 cells by Western blot. Key Results Catalpol stimulated expression of Bcl-2 and inhibited the expression of Bax. Catalpol also attenuated the increase in Ca2+ concentration induced by LPS in PC12 cells and down-regulated CaMK phosphorylation. The CaMKII-dependent ASK-1/JNK/p38 signalling cascade was blocked by catalpol. All these changes were accompanied by a decrease of apoptosis induced by LPS in PC12 cells. Conclusions and Implications The data presented here provide new mechanistic insights into the links between the CaMKII-dependent ASK-1/JNK/p38 signalling pathway and the protective effect of catalpol on apoptosis induced by LPS in PC12 cells. PMID:23550774

  9. Promotion of IL-4- and IL-5-dependent differentiation of anti-mu-primed B cells by ascorbic acid 2-glucoside.

    PubMed

    Ichiyama, Kenji; Mitsuzumi, Hitoshi; Zhong, Ming; Tai, Akihiro; Tsuchioka, Akihiro; Kawai, Saeko; Yamamoto, Itaru; Gohda, Eiichi

    2009-02-21

    The stable ascorbic acid derivative 2-O-alpha-D-glucopyranosyl-L-ascorbic acid (AA-2G) was used to investigate the role of ascorbic acid (AA) in B cell differentiation in vitro. AA-2G is stable in a solution unlike AA but is hydrolyzed by cellular alpha-glucosidase to release AA. Mouse spleen B cells were primed for 2 days with an anti-mu antibody in the presence of interleukin (IL)-4 and IL-5 and then washed and recultured with AA-2G in the presence of IL-4 and IL-5. AA-2G, but not AA, dose-dependently increased IgM production, the greatest enhancement being 150% at concentrations of more than 0.5mM. In the absence of IL-4 and IL-5, primed B cells produced a negligible amount of IgM, and AA-2G had no effect. AA-2G-induced IgM production in the presence of IL-4 and IL-5 was inhibited by the alpha-glucosidase inhibitor castanospermine. Intracellular AA content, depleted during the priming period, increased by adding AA-2G at the start of reculture. Treatment of B cells with AA-2G resulted in an increase in the number of IgM-secreting cells, CD138-positive cells and CD45R/B220-negative cells. The number of viable cells in untreated cultures decreased gradually, but the decrease was significantly attenuated by AA-2G, resulting in about 70% more viable cells in AA-2G-treated cultures. AA-2G caused a slight but reproducible enhancement of DNA synthesis and a slight decrease in the number of cells with a sub-G1 DNA content. These results demonstrated that AA released from AA-2G enhanced cytokine-dependent IgM production in anti-mu-primed B cells and suggest that its effect is caused through promoting the differentiation of B cells to plasma cells and attenuating the gradual decrease in the number of viable cells. PMID:19201381

  10. Antiscorbutic activity of L-ascorbic acid 2-glucoside and its availability as a vitamin C supplement in normal rats and guinea pigs.

    PubMed

    Yamamoto, I; Suga, S; Mitoh, Y; Tanaka, M; Muto, N

    1990-11-01

    Bioavailability of a newly-synthesized and chemically-stable 2-O-alpha-D-glucopyranosyl-L-ascorbic acid (AA-2G) as a vitamin C supplement was investigated in rats and guinea pigs. Oral administration of AA-2G to the animals resulted in an increase of serum ascorbic acid (AA) levels. However, in these sera the intact form was not detectable by the high performance liquid chromatography (HPLC) method, indicating its hydrolysis through the process of absorption. After an intravenous injection of AA-2G, the intact form diminished rapidly from the serum, followed by prolonged and marked elevation of serum AA levels. Various tissue homogenates from rats and guinea pigs were examined for their releasing activity of AA from AA-2G. High activity was observed in kidney, small intestine and serum of rats and in small intestine and kidney of guinea pigs. These hydrolytic activities were completely inhibited by castanospermine, a specific alpha-glucosidase inhibitor, suggesting the participation of alpha-glucosidase in the in vivo hydrolysis of AA-2G. AA-2G was found to exhibit obvious therapeutic effect in scorbutic guinea pigs by its repeated oral administrations. These results indicate that AA-2G is a readily available source of vitamin C activity in vivo. PMID:2093127

  11. Radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl of ascorbic acid 2-glucoside (AA-2G) and 6-acyl-AA-2G.

    PubMed

    Fujinami, Y; Tai, A; Yamamoto, I

    2001-05-01

    The radical scavenging activity of the stable derivatives, which are O-substituted at the C-2 position of ascorbic acid (AA), against 1,1-diphenyl-2-picrylhydrazyl (DPPH) was evaluated in buffer under different pH conditions, and compared with those of AA and alpha-tocopherol. AA was shown to have 50% radical scavenging ability (EC50) at a concentration of 2.2 x 10(-5) M against 0.1 mM DPPH in 60% ethanol. Ascorbyl 6-palmitate, a lipophilic AA derivative which has a free endiol group and is therefore unstable, also showed potent radical scavenging activity with EC50 of 2.9 x 10(-5) M. A typical lipophilic antioxidant, alpha-tocopherol gave a similar EC50 value as that of AA. In contrast, ascorbyl 2,6-dipalmitate, AA 2-phosphate and AA 2-sulfate exhibited negligible scavenging activity. On the other hand, 2-O-alpha-D-glucopyranosyl-L-ascorbic acid (AA-2G) and a series of 6-O-acyl-2-O-alpha-D-glucopyranosyl-L-ascorbic acids (6-Acyl-AA-2G) themselves exhibited the radical scavenging activity of EC50: 6.1 x 10(-5) M and 4.4 x 10(-5)-5.9 x 10(-5) M, respectively, although their activities were lower than that of AA. Among 6-Acyl-AA-2G derivatives, the EC50 values tended to decrease with increasing length of their acyl carbon group. Increasing pH of the buffer resulted in decrease in the scavenging activity of all compounds tested as expected. We speculate that the difference in the radical scavenging activity of derivatives O-substituted at the C-2 position of AA may be ascribed to the linkage type of the substituent group to the endiol-lactone resonance system and the degree of dissociation of the C-3 proton. PMID:11383624

  12. Implications of low-power He-Ne laser and monochromatic red light biostimulation in the metabolism of proteins and glucosides

    NASA Astrophysics Data System (ADS)

    Onac, I.; Pop, L.; Ungur, Rodica; Giurgiu, Ioana

    2001-06-01

    We checked the changes occurring in the metabolism of proteins (seric cholinesterase, total proteins) and in the metabolism of glycosides (seric glucose) in Cavia cobaia. A simple blind study was carried out and the results were checked on the first, tenth and twentieth days of treatment. The data thus obtained were graphically represented and statistically processed according to the Duncan test. The technique and treatment doses were similar and they were compared with the data obtained from controls and environment controls. In the groups biostimulated with He-Ne laser, seric cholinesterase levels increased proportionally with the dose reaching a peak on day 10, which was not the case with the controls. Monochromatic red light caused a similar but quantitatively lower effect. The same results were obtained in the case of seric proteins as well, however, the effect did not depend on the dose and it was less significant statistically than in the case of seric cholinesterase both in laser treated and in monochromatic red light treated groups.

  13. Identification of glucoside and carboxyl-linked glucuronide conjugates of mycophenolic acid in plasma of transplant recipients treated with mycophenolate mofetil

    PubMed Central

    Shipkova, Maria; Armstrong, Victor William; Wieland, Eberhard; Niedmann, Paul Dieter; Schütz, Ekkehard; Brenner-Weiß, Gerald; Voihsel, Martin; Braun, Felix; Oellerich, Michael

    1999-01-01

    Mycophenolic acid (MPA), is primarily metabolized in the liver to 7-O-MPA-?-glucuronide (MPAG). Using RP-h.p.l.c. we observed three further MPA metabolites, M-1, M-2, M-3, in plasma of transplant recipients on MMF therapy. To obtain information on the structure and source of these metabolites: (A) h.p.l.c. fractions containing either metabolite or MPA were collected and analysed by tandem mass spectrometry; (B) the metabolism of MPA was studied in human liver microsomes in the presence of UDP-glucuronic acid, UDP-glucose or NADPH; (C) hydrolysis of metabolites was investigated using ?-glucosidase, ?-glucuronidase or NaOH; (D) cross-reactivity of each metabolite was tested in an immunoassay for MPA (EMIT). Mass spectrometry of M-1, M-2, MPA and MPAG in the negative ion mode revealed molecular ions of m/z 481, m/z 495, m/z 319 and m/z 495 respectively. Incubation of microsomes with MPA and UDP-glucose produced M-1, with MPA and UDP-glucuronic acid MPAG and M-2 were formed, while with MPA and NADPH, M-3 was observed. ?-Glucosidase hydrolysed M-1 completely. ?-Glucuronidase treatment led to a complete disappearance of MPAG whereas the amount of M-2 was reduced by approximately 30%. Only M-2 was labile to alkaline treatment. M-2 and MPA but not M-1 and MPAG cross-reacted in the EMIT assay. These results suggest that: (i) M-1 is the 7-OH glucose conjugate of MPA; (ii) M-2 is the acyl glucuronide conjugate of MPA; (iii) M-3 is derived from the hepatic CYP450 system. PMID:10204993

  14. Purification, crystallization and preliminary X-ray analysis of rice BGlu1 ?-glucosidase with and without 2-deoxy-2-fluoro-?-d-glucoside

    SciTech Connect

    Chuenchor, Watchalee; Pengthaisong, Salila; Yuvaniyama, Jirundon; Opassiri, Rodjana; Svasti, Jisnuson; Ketudat Cairns, James R.

    2006-08-01

    Rice BGlu1 ?-glucosidase was purified from recombinant E. coli and crystallized with and without the inhibitor 2-deoxy-2-fluoro-?-d-glucose. The crystals diffracted to 2.15 and 2.75 Å, respectively. Rice (Oryza sativa) BGlu1 ?-glucosidase was expressed in Escherichia coli with N-terminal thioredoxin and hexahistidine tags and purified by immobilized metal-affinity chromatography (IMAC). After removal of the N-terminal tags, cation-exchange and S-200 gel-filtration chromatography yielded a 50 kDa BGlu1 with >95% purity. The free enzyme and a complex with 2,4-dinitrophenyl-2-deoxy-2-fluoro-?-d-glucopyranoside inhibitor were crystallized by microbatch and hanging-drop vapour diffusion. Small tetragonal crystals of BGlu1 with and without inhibitor grew in 18%(w/v) PEG 8000 with 0.1 M sodium cacodylate pH 6.5 and 0.2 M zinc acetate. Crystals of BGlu1 with inhibitor were streak-seeded into 23%(w/v) PEG MME 5000, 0.2 M ammonium sulfate, 0.1 M MES pH 6.7 to yield larger crystals. Crystals with and without inhibitor diffracted to 2.15 and 2.75 Å resolution, respectively, and had isomorphous orthorhombic unit cells belonging to space group P2{sub 1}2{sub 1}2{sub 1}.

  15. Accumulation of brachycerine, an antioxidant glucosidic indole alkaloid, is induced by abscisic acid, heavy metal, and osmotic stress in leaves of Psychotria brachyceras.

    PubMed

    do Nascimento, Naíla Cannes; Menguer, Paloma Koprovski; Henriques, Amélia Teresinha; Fett-Neto, Arthur Germano

    2013-12-01

    Psychotria brachyceras Muell. Arg. produces the antioxidant monoterpene indole alkaloid (MIA) brachycerine, which, besides retaining a glucose residue, has its terpenoid moiety derived not from secologanin, but probably from epiloganin, representing a new subclass of MIAs. In this work we showed that osmotic stress agents, such as sodium chloride, sorbitol and polyethylene glycol (PEG), induced brachycerine accumulation in leaf disks of P. brachyceras. Other oxidative stress inducers, such as exposure to aluminum and silver, also increased brachycerine content. Abscisic acid (ABA) treatment was shown to increase brachycerine yield, suggesting its involvement in brachycerine induction during osmotic stress. Ascorbate peroxidase activity was induced in PEG-treated leaf disks, whereas superoxide dismutase (SOD) activity remained unaltered. Assays with specific inhibitors of the cytosolic mevalonate (MVA) and plastidic 2-C-methyl-D-erythritol 4-phosphate (MEP) pathways showed that the terpenoid moiety of brachycerine derived predominantly from the MEP pathway. These results suggest a potential involvement of brachycerine in plant defense against osmotic/oxidative stress damage, possibly contributing to detoxification of hydroxyl radical and superoxide anion as a SOD-like molecule. PMID:24045228

  16. 2,3,4',5-tetrahydroxystilbene-2-O-?-D-glucoside suppresses expression of adhesion molecules in aortic wall of dietary atherosclerotic rats and promonocytic U937 cells.

    PubMed

    Wang, Yu-Qin; Shen, Yan; Li, Feng; Wang, Chun-Hua; Zhang, Wei

    2013-01-01

    We sought to investigate whether TSG suppressed the ICAM-1/VCAM-1 expression in dietary atherosclerotic rats and in Ox-LDL-induced U937 cells. For this purpose, 60 male Sprague-Dawley rats were randomly-and-equally divided into six groups. Atherosclerosis was induced by feeding rats a hyperlipidemic diet. TSG (120, 60 or 30 mg/kg/day) was administered by oral gavage. Simvastatin (2 mg/kg/day) was administered as positive control whereas physiological saline (0.9% NaCl) served as untreated control. After 12 weeks, rats were euthanized by ethyl carbonate (1,200 mg/kg) and aortic wall samples were collected. Besides, U937 cells were stimulated for 48 h by Ox-LDL (80 ?g/mL) with and without TSG (120, 60, 30 ?g/L) or simvastatin (100 ?g/L). ICAM-1/VCAM-1 mRNA expression was determined by RT-PCR and protein expression was detected by immunohistochemistry and/or western blotting. The data show that ICAM-1/VCAM-1 mRNA/protein expression was significantly enhanced in atherosclerotic aortas compared with normal diet group. Ox-LDL-induced ICAM-1/VCAM-1 mRNA/protein expression in U937 cells. Importantly, TSG significantly inhibited ICAM-1/VCAM-1 expression in atherosclerotic aortas in a dose-dependent manner. TSG-pretreatment also inhibited ICAM-1/VCAM-1 expression in Ox-LDL-induced U937 cells. Therefore, we concluded that TSG suppressed the expression of adhesion (ICAM-1/VCAM-1) molecules both in vivo (in aortic wall of dietary atherosclerotic rats) and in vitro (U937 cells). PMID:23575939

  17. Enzymatic Synthesis of the Flavone Glucosides, Prunin and Isoquercetin, and the Aglycones, Naringenin and Quercetin, with Selective ?-L-Rhamnosidase and ?-D-Glucosidase Activities of Naringinase

    PubMed Central

    Vila-Real, Hélder; Alfaia, António J.; Bronze, M. Rosário; Calado, António R. T.; Ribeiro, Maria H. L.

    2011-01-01

    The production of flavonoid glycosides by removing rhamnose from rutinosides can be accomplished through enzymatic catalysis. Naringinase is an enzyme complex, expressing both ?-L-rhamnosidase and ?-D-glucosidase activities, with application in glycosides hydrolysis. To produce monoglycosylated flavonoids with naringinase, the expression of ?-D-glucosidase activity is not desirable leading to the need of expensive methods for ?-L-rhamnosidase purification. Therefore, the main purpose of this study was the inactivation of ?-D-glucosidase activity expressed by naringinase keeping ?-L-rhamnosidase with a high retention activity. Response surface methodology (RSM) was used to evaluate the effects of temperature and pH on ?-D-glucosidase inactivation. A selective inactivation of ?-D-glucosidase activity of naringinase was achieved at 81.5°C and pH 3.9, keeping a very high residual activity of ?-L-rhamnosidase (78%). This was a crucial achievement towards an easy and cheap production method of very expensive flavonoids, like prunin and isoquercetin starting from naringin and rutin, respectively. PMID:21941631

  18. A 7-Deoxyloganetic Acid Glucosyltransferase Contributes a Key Step in Secologanin Biosynthesis in Madagascar Periwinkle[C][W][OPEN

    PubMed Central

    Asada, Keisuke; Salim, Vonny; Masada-Atsumi, Sayaka; Edmunds, Elizabeth; Nagatoshi, Mai; Terasaka, Kazuyoshi; Mizukami, Hajime; De Luca, Vincenzo

    2013-01-01

    Iridoids form a broad and versatile class of biologically active molecules found in thousands of plant species. In addition to the many hundreds of iridoids occurring in plants, some iridoids, such as secologanin, serve as key building blocks in the biosynthesis of thousands of monoterpene indole alkaloids (MIAs) and many quinoline alkaloids. This study describes the molecular cloning and functional characterization of three iridoid glucosyltransfeases (UDP-SUGAR GLYCOSYLTRANSFERASE6 [UGT6], UGT7, and UGT8) from Madagascar periwinkle (Catharanthus roseus) with remarkably different catalytic efficiencies. Biochemical analyses reveal that UGT8 possessed a high catalytic efficiency toward its exclusive iridoid substrate, 7-deoxyloganetic acid, making it better suited for the biosynthesis of iridoids in periwinkle than the other two iridoid glucosyltransfeases. The role of UGT8 in the fourth to last step in secologanin biosynthesis was confirmed by virus-induced gene silencing in periwinkle plants, which reduced expression of this gene and resulted in a large decline in secologanin and MIA accumulation within silenced plants. Localization studies of UGT8 using a carborundum abrasion method for RNA extraction show that its expression occurs preferentially within periwinkle leaves rather than in epidermal cells, and in situ hybridization studies confirm that UGT8 is preferentially expressed in internal phloem associated parenchyma cells of periwinkle species. PMID:24104568

  19. [Dihydropenstemide from Penstemon confertus and the Preparation of epi-Dihydropenstemide from Penstemide.].

    PubMed

    Gering, B; Junior, P; Wichtl, M

    1986-10-01

    From leaves of PENSTEMON CONFERTUS Dougl. a valeriana-type ester iridoid has been isolated and structurally elucidated as dihydropenstemide by spectroscopic methods. Catalytic hydrogenation of penstemide provides a new compound, identified as 8- EPI-dihydropenstemide. PMID:17345338

  20. Penstemide and serrulatoloside production in tissue cultures of Penstemon serrulatus Menz.

    PubMed

    Wysoki?ska, H

    1990-01-01

    The contents of iridoid glycosides penstemide and serrulatoloside were determined with HPLC method in callus and cell cultures, plants regenerated with tissue culture method and in the intact plants of Penstemon serrulatus Menz. PMID:12959263

  1. Synthesis of glycosides of resveratrol, pterostilbene, and piceatannol, and their anti-oxidant, anti-allergic, and neuroprotective activities.

    PubMed

    Sato, Daisuke; Shimizu, Nobuyoshi; Shimizu, Yoshiko; Akagi, Masaaki; Eshita, Yuki; Ozaki, Shin-ichi; Nakajima, Nobuyoshi; Ishihara, Kohji; Masuoka, Noriyoshi; Hamada, Hiroki; Shimoda, Kei; Kubota, Naoji

    2014-01-01

    Resveratrol was glucosylated to its 3- and 4'-?-glucosides by cultured cells of Phytolacca americana. On the other hand, cultured P. americana cells glucosylated pterostilbene to its 4'-?-glucoside. P. americana cells converted piceatannol into its 4'-?-glucoside. The 3- and 4'-?-glucosides of resveratrol were further glucosylated to 3- and 4'-?-maltosides of resveratrol, 4'-?-maltoside of which is a new compound, by cyclodextrin glucanotransferase. Resveratrol 3-?-glucoside and 3-?-maltoside showed low 2,2-diphenyl-1-picrylhydrazyl free-radical-scavenging activity, whereas other glucosides had no radical-scavenging activity. Piceatannol 4'-?-glucoside showed the strongest inhibitory activity among the stilbene glycosides towards histamine release from rat peritoneal mast cells. Pterostilbene 4'-?-glucoside showed high phosphodiesterase inhibitory activity. PMID:25229845

  2. Terpenoids of Linaria alpina (L.) Mill. from Dolomites, Italy.

    PubMed

    Venditti, A; Serafini, M; Nicoletti, M; Bianco, A

    2015-01-01

    This paper reports the first phytochemical analysis of Linaria alpina (L.) Mill., collected in Dolomites (Italy), a species characteristic of mountain environment. Besides aucubin (4), which is rare in the subgenus Antirrhineae of Plantaginaceae, mainly acidic compounds were found, i.e. oleanolic acid (1), ursolic acid (2) maslinic acid (3) and shikimic acid (5). The pentacyclic triterpenes of L. alpina resulted in relatively high content, whereas flavonoids resulted in low content. PMID:25738749

  3. Using reversed phase high performance liquid chromatography to study the complexation of anthocyanins with ?-cyclodextrin

    NASA Astrophysics Data System (ADS)

    Deineka, V. I.; Lapshova, M. S.; Deineka, L. A.

    2014-06-01

    It is shown by means of reversed phase high performance liquid chromatography (RP HPLC) with mobile phases containing additions of ?-cyclodextrin that 5-glucosides of cyanidin and pelargonidin form stronger inclusion complexes than 3-glucosides; this is explained by the steric interference of the glucoside radical.

  4. Draft Genome Sequence of the Thermophile Thermus filiformis ATCC 43280, Producer of Carotenoid-(Di)glucoside-Branched Fatty Acid (Di)esters and Source of Hyperthermostable Enzymes of Biotechnological Interest

    PubMed Central

    Mandelli, Fernanda; Oliveira Ramires, Brenda; Couger, Matthew Brian; Paixão, Douglas A. A.; Camilo, Cesar M.; Polikarpov, Igor; Prade, Rolf

    2015-01-01

    Here, we present the draft genome sequence of Thermus ?liformis strain ATCC 43280, a thermophile bacterium capable of producing glycosylated carotenoids acylated with branched fatty acids and enzymes of biotechnological potential. PMID:25977443

  5. Anthocyanins and other flavonoids as flower pigments from eleven Centaurea species.

    PubMed

    Mishio, Tamaki; Takeda, Kosaku; Iwashina, Tsukasa

    2015-03-01

    Anthocyanins and other flavonoids were isolated from the flowers of eleven Centaurea species, C. macrocephala, C. rupestotilis and C. suaveolens, which produce yellow flowers, and C. achtarovii, C. dealbata, C. montana, C. nigra, C. scabiosa, C. simplicicaulis, C. hypoleuca and C. triumfetti, which have cyanic flowers. Four anthocyanins, cyanidin 3,5-di-O-glucoside, cyanidin 3-O-(6"-malonylglucoside)-5-O-glucoside, cyanidin 3-O-(6"-succinylglucoside)-5- O-glucoside and cyanidin glycoside, were detected in the cyanic flowers of seven Centaurea species. Of these anthocyanins, the first two were found as major anthocyanins. In the cyanic species, four other flavonoids, apigenin 7-O-glucuronide-4'-O-glucoside, malonylated apigenin 7,4'-di-O-glucoside, apigenin 7-0- glucuronide and kaempferol glycoside, were also isolated. On the other hand, nine flavonols and four flavones were isolated from the three yellow-flowered species, and identified as quercetagetin, quercetagetin 7-O-glucoside, quercetagetin 3'-methyl ether 7-O-glucoside, patuletin, patuletin 7-O-glucoside, quercetin 7-O-glucoside, kaempferol 3-methyl ether, kaempferol 3-methyl ether 4'-O-glucuronide and isorhamnetin 3-O-galactoside, and apigenin, apigenin 7- O-glucuronide, luteolin 7-O-glucoside and apigenin 6,8-di-C-glucoside (vicenin-2). Of these flavonoids, the former five flavonols are "yellow flavonols", and it was shown that their flower colors are due to these compounds. PMID:25924526

  6. Production of Hesperetin Glycosides by Xanthomonas campestris and Cyclodextrin Glucanotransferase and Their Anti-allergic Activities

    PubMed Central

    Shimoda, Kei; Hamada, Hiroki

    2010-01-01

    The production of hesperetin glycosides was investigated using glycosylation with Xanthomonas campestris and cyclodextrin glucanotransferase (CGTase). X. campestris glucosylated hesperetin to its 3'-, 5-, and 7-O-glucosides, and CGTase converted hesperetin glucosides into the corresponding maltosides. The resulting 7-O-glucoside and 7-O-maltoside of hesperetin showed inhibitory effects on IgE antibody production and on O2- generation from rat neutrophils. PMID:22254014

  7. Studies on constituents with cytotoxic activity from the stem bark of Syringa velutina.

    PubMed

    Park, H J; Lee, M S; Lee, K T; Sohn, I C; Han, Y N; Miyamoto, K

    1999-07-01

    Cytotoxic compounds, oleuropein (1) and a phenylethanoid glycoside (2) were isolated from the stem bark of Syringa velutina KOM. along with coniferylaldehyde 4-O-glucoside, syringin, ligstroside, (+)-syringaresinol 4-O-glucoside, (+)-medioresinol 4"-O-glucoside and (-)-olivil 4"-O-glucoside. Phenylethanoid glycoside (2) was identified to be 3,4-dihydroxyphenylethyl alcohol 8-O-beta-D-glucopyranoside. This compound showed the most potent cytotoxic effect on several tumor cell lines (P-388, L-1210, SNU-5 and HL-60) among eight compounds isolated in the present study. We suggest that the 3,4-dihydroxyphenylethoxy moiety of this compound contributes to cytotoxicity. PMID:10434406

  8. Phenolic compounds in blackcurrant (Ribes nigrum L.) leaves relative to leaf position and harvest date.

    PubMed

    Vagiri, Michael; Conner, Sean; Stewart, Derek; Andersson, Staffan C; Verrall, Susan; Johansson, Eva; Rumpunen, Kimmo

    2015-04-01

    Blackcurrant leaves are an essential source of phenolic compounds and this study investigated their variation relative to leaf positions and harvest date. The phenolic content varied between harvest dates, although leaf position on the shoot and interactions also played an important role. The contents of quercetin-malonyl-glucoside, kaempferol-malonyl-glucoside isomer and kaempferol-malonyl-glucoside were higher than that of the other identified phenolic compounds, whereas epigallocatechin was the lowest for all investigated leaf positions and harvest dates. The content of several of the compounds was highest in June, while quercetin-glucoside, kaempferol-glucoside and total phenols, increased towards the end of the season. Leaf position influenced the content of myricetin-malonyl-glucoside, myricetin-malonyl-glucoside isomer, quercetin-malonyl-glucoside and kaempferol-glucoside at the end of the season. Knowledge relating to the influence of ontogenetic and harvest time on the content of specific phenolic compounds might contribute in tailoring functional foods or pharmaceutical products using blackcurrant leaves as natural ingredients. PMID:25442534

  9. A comparison of flavonoid glycosides by electrospray tandem mass spectrometry

    NASA Astrophysics Data System (ADS)

    March, Raymond E.; Lewars, Errol G.; Stadey, Christopher J.; Miao, Xiu-Sheng; Zhao, Xiaoming; Metcalfe, Chris D.

    2006-01-01

    A comparison is presented of product ion mass spectra of protonated and deprotonated molecules of kaempferol-3-O-glucoside, quercitin-3-O-glucoside (isoquercitrin), quercitin-3-O-galactoside (hyperoin), apigenin-7-O-glucoside, luteolin-7-O-glucoside, genistein-7-O-glucoside, naringenin-7-O-glucoside (prunin), luteolin-4'-O-glucoside, luteolin-6-C-glucoside (homoorientin, known also as isoorientin), apigenin-8-C-glucoside (vitexin), and luteolin-8-C-glucoside (orientin) together with the product ion mass spectrum of deprotonated kaempferol-7-O-glucoside. All isomeric ions were distinguishable on the basis of their product ion mass spectra. For protonated 3-O-, 7-O-, and 4'-O-glycosides at a collision energy of 46-47 eV, homolytic cleavage of the O-glycosidic bond yielded aglycon Y+ ions, whereas in deprotonated 3-O-, 7-O-, and 4'-O-glycosides, heterolytic and homolytic cleavage of the O-glycosidic bond yielded radical aglycon (Y-H)- and aglycon (Y-) ions. In each case, fragmentation of either the glycan or the aglycon or both was observed. For 6-C- and 8-C-glycosides at a collision energy of 46-47 eV, fragmentation was restricted almost exclusively to the glycan. For luteolin-6-C-glucoside, the integrity of the aglycon structure is preserved at the expense of the glycan for which some 30 fragmentations were observed. Breakdown curves were determined as a function of collision energy for protonated and deprotonated luteolin-6-C-glucoside. An attempt has been made to rationalize the product ion mass spectra derived from C-O- and C-C-luteolin glucosides in terms of computed structures that indicate significant intramolecular hydrogen bonding and rotation of the B-ring to form a coplanar luteolin structure. It is proposed that protonated and deprotonated luteolin-6-C-glucoside may afford examples of cooperative interactive bonding that plays a major role in directing fragmentation.

  10. Secondary metabolites from Rubiaceae species.

    PubMed

    Martins, Daiane; Nunez, Cecilia Veronica

    2015-01-01

    This study describes some characteristics of the Rubiaceae family pertaining to the occurrence and distribution of secondary metabolites in the main genera of this family. It reports the review of phytochemical studies addressing all species of Rubiaceae, published between 1990 and 2014. Iridoids, anthraquinones, triterpenes, indole alkaloids as well as other varying alkaloid subclasses, have shown to be the most common. These compounds have been mostly isolated from the genera Uncaria, Psychotria, Hedyotis, Ophiorrhiza and Morinda. The occurrence and distribution of iridoids, alkaloids and anthraquinones point out their chemotaxonomic correlation among tribes and subfamilies. From an evolutionary point of view, Rubioideae is the most ancient subfamily, followed by Ixoroideae and finally Cinchonoideae. The chemical biosynthetic pathway, which is not so specific in Rubioideae, can explain this and large amounts of both iridoids and indole alkaloids are produced. In Ixoroideae, the most active biosysthetic pathway is the one that produces iridoids; while in Cinchonoideae, it produces indole alkaloids together with other alkaloids. The chemical biosynthetic pathway now supports this botanical conclusion. PMID:26205062

  11. Potential application for genipin-modified gelatin in leather processing

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Genipin is a non-toxic iridoid compound, extracted from the gardenia fruits, and, because of its low cytoxicity, is replacing both glutaraldehyde and formaldehyde as a crosslinking reagent. In prior research we had shown the potential of chemical (glutaraldehyde) and enzyme (transglutaminase) modif...

  12. Potential application for genipin-modified gelatin in leather processing

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Genipin is an iridoid compound extracted from gardenia fruits. Because of its low cytotoxicity, genipin can be used to replace both glutaraldehyde and formaldehyde as a crosslinking reagent. In recent years, research into the utilization of genipin for the modification of gelatin, particularly in ...

  13. Independently recruited oxidases from the glucose-methanol-choline oxidoreductase family enabled chemical defences in leaf beetle larvae (subtribe Chrysomelina) to evolve

    PubMed Central

    Rahfeld, Peter; Kirsch, Roy; Kugel, Susann; Wielsch, Natalie; Stock, Magdalena; Groth, Marco; Boland, Wilhelm; Burse, Antje

    2014-01-01

    Larvae of the leaf beetle subtribe Chrysomelina sensu stricto repel their enemies by displaying glandular secretions that contain defensive compounds. These repellents can be produced either de novo (iridoids) or by using plant-derived precursors (e.g. salicylaldehyde). The autonomous production of iridoids, as in Phaedon cochleariae, is the ancestral chrysomeline chemical defence and predates the evolution of salicylaldehyde-based defence. Both biosynthesis strategies include an oxidative step of an alcohol intermediate. In salicylaldehyde-producing species, this step is catalysed by salicyl alcohol oxidases (SAOs) of the glucose-methanol-choline (GMC) oxidoreductase superfamily, but the enzyme oxidizing the iridoid precursor is unknown. Here, we show by in vitro as well as in vivo experiments that P. cochleariae also uses an oxidase from the GMC superfamily for defensive purposes. However, our phylogenetic analysis of chrysomeline GMC oxidoreductases revealed that the oxidase of the iridoid pathway originated from a GMC clade different from that of the SAOs. Thus, the evolution of a host-independent chemical defence followed by a shift to a host-dependent chemical defence in chrysomeline beetles coincided with the utilization of genes from different GMC subfamilies. These findings illustrate the importance of the GMC multi-gene family for adaptive processes in plant–insect interactions. PMID:24943369

  14. TANNING POTENTIAL OF GENIPIN

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Genipin, a derivative of the iridoid glycoside geniposide in the fruit of Gardenia jasmindides Ellis, is a naturally occurring protein crosslinking agent, which is beginning to replace glutaraldehyde as a fixative for biological tissues. This study was undertaken to evaluate the potential of iridoi...

  15. CHEMICAL AND PHYSICAL EVALUATION OF THE CROSSLINKING OF BOVINE HIDE COLLAGEN BY GENIPIN

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Genipin, a derivative of the iridoid glycoside geniposide in the fruit of Gardenia jasmindides Ellis, is a naturally occurring protein crosslinking agent, which is beginning to replace glutaraldehyde as a fixative for biological tissues. In this study the potential of genipin, alone or in combinati...

  16. Phenolic Components and Antioxidant Activity of Wood Extracts from 10 Main Spanish Olive Cultivars

    E-print Network

    Adams, Robert P.

    -3 Considerable research is being conducted to find novel sources of potentially safe natural antioxidantsPhenolic Components and Antioxidant Activity of Wood Extracts from 10 Main Spanish Olive Cultivars, iridoids, secoiridoids, multivariate analysis INTRODUCTION The search for (new) natural antioxidants

  17. EFFECT OF GENIPIN ON THE THERMAL STABILITY OF HIDE POWDER

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Genipin, derived from the iridoid glycoside geniposide isolated from the fruit of Gardenia jasminoides Ellis, is a naturally occurring protein crosslinking agent. Genipin, which is not cytotoxic, is beginning to replace glutaraldehyde as a fixative for biological tissues. This study was undertaken...

  18. Multiple loss-of-function 5-O-Glucosyltransferase alleles revealed in Vitis vinifera, but not in other Vitis species

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Anthocyanins in red grapes (Vitis genus) are important components of wine and beneficial to human health. These antioxidant compounds are present in two glycosylation states: monoglucoside (3-O-glucoside) and diglucoside (3, 5-di-O-glucoside). While monoglucoside anthocyanins are present in all pigm...

  19. Stilbenes and anthocyanins reduce stress signaling in BV-2 mouse microglia

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Blueberries contain an array of phytochemicals that may decrease both inflammatory and oxidative stress. We determined if pterostilbene, resveratrol, and two anthocyanins commonly found in blueberries, delphinidin-3-O-glucoside and malvidin-3-O-glucoside, would be efficacious in protecting microglia...

  20. Flavonoids from acai (euterpe oleracea mart.) Pulp and their antioxidant and anti-inflammatory activities

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Five flavonoids, (2S,3S)-dihyrokaempferol 3-O-beta-D-glucoside (1) and its isomer (2R,3R)-dihydrokaempferol 3-O-'-D-glucoside (2) , isovitexin (3), velutin (4) and 5,4'-dihydroxy-7,3',5'-trimethoxyflavone (5), were isolated from acai (Euterpe oleracea Mart.) pulp. The structures of these compounds ...

  1. Preparative isolation of anthocyanins from Japanese purple sweet potato (Ipomoea batatas L.) varieties by high-speed countercurrent chromatography.

    PubMed

    Montilla, Elyana Cuevas; Hillebrand, Silke; Butschbach, Daniela; Baldermann, Susanne; Watanabe, Naoharu; Winterhalter, Peter

    2010-09-22

    Purple-fleshed sweet potatoes (Ipomoea batatas L.) contain a very complex anthocyanin profile due to the presence of several non-, mono-, and diacylated glucosides of cyanidin and peonidin. In this study, the anthocyanin composition of four Japanese purple sweet potato cultivars (Chiran Murasaki, Tanegashima Murasaki, Naka Murasaki, and Purple Sweet) were investigated by HPLC-DAD and ESI-MSn analyses. The HPLC chromatograms of the different cultivars show a remarkable variation of the two major pigments, cyanidin-3-(6''-caffeoylsophoroside)-5-glucoside and peonidin-3-(6''-caffeoylsophoroside)-5-glucoside, respectively. According to this, they can be categorized into two groups on the basis of the peonidin/cyanidin ratio: the cultivars Chiran Murasaki and Purple Sweet showed a high content of peonidin derivatives (peonidin type), whereas the varieties Tanegashima Murasaki and Naka Murasaki were classified as cyanidin types. By means of high-speed countercurrent chromatography (HSCCC) the nonacylated 3-sophoroside-5-glucoside of cyanidin was isolated on a preparative scale. Furthermore, it was possible to isolate the monoacylated cyanidin-3-(6''-caffeoylsophoroside)-5-glucoside as well as three diacylated major pigments, cyanidin-3-(6'',6'''-dicaffeoylsophoroside)-5-glucoside, cyanidin-3-(6''-caffeoyl-6'''-p-hydroxy-benzoylsophoroside)-5-glucoside, and peonidin-3-(6''-caffeoyl-6'''-p-hydroxybenzoyl-sophoroside)-5-glucoside. The purity and identity of the so-obtained pigments were confirmed by NMR measurements. PMID:20731350

  2. CYTOKININ GLYCOSYLTRANSFERASES: GENES, SUBSTRATES, MOLECULAR MODELS, AND TRANSGENICS

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Cytokinins occur as free bases, nucleoside, nucleotides, N-glucosides, O-glucosides, and O-xylosides. Zeatin O-glycosylation genes and enzymes were isolated and characterized. The first genes were cloned from Phaseolus and subsequently, homologs were identified in other species including maize, rice...

  3. Identification and quantification of anthocyanins in fruits from Neomitranthes obscura (DC.) N. Silveira an endemic specie from Brazil by comparison of chromatographic methodologies.

    PubMed

    Gouvêa, Ana Cristina M S; Melo, Armindo; Santiago, Manuela C P A; Peixoto, Fernanda M; Freitas, Vitor; Godoy, Ronoel L O; Ferreira, Isabel M P L V O

    2015-10-15

    Neomitranthes obscura (DC.) N. Silveira is a Brazilian fruit belonging to the Myrtaceae family that contains anthocyanins in the peel and was studied for the first time in this work. Delphinidin-3-O-galactoside, delphinidin-3-O-glucoside, cyanidin-3-O-galactoside, cyanidin-3-O-glucoside, cyanidin-3-O-arabinoside, petunidin-3-O-glucoside, pelargonidin-3-O-glucoside, peonidin-3-O-galactoside, peonidin-3-O-glucoside, cyanidin-3-O-xyloside were separated and identified by LC/DAD/MS and by co-elution with standards. Reliable quantification of anthocyanins in the mature fruits was performed by HPLC/DAD using weighted linear regression model from 0.05 to 50mg of cyaniding-3-O-glucoside L(-1) because it gave better fit quality than least squares linear regression. Good precision and accuracy were obtained. The total anthocyanin content of mature fruits was 263.6 ± 8.2 mg of cyanidin-3-O-glucoside equivalents 100 g(-1) fresh weight, which was in the same range found in literature for anthocyanin rich fruits. PMID:25952869

  4. Taxonomic Investigations on Expressed and Cryptic Phospho-?-glucosidases in Enterobacteriaceae

    PubMed Central

    Schaefler, S.; Malamy, A.

    1969-01-01

    In the Enterobacteriaceae, ?-glucosides are catabolized by a complex system formed of three permeases, with partly overlapping substrate specificities, and two hydrolytic enzymes, phospho-?-glucosidase A and B, which hydrolyze only phosphorylated ?-glucosides. Some Enterobacteriaceae such as Klebsiella-Aerobacter (Enterobacter) possess the complete system; others possess only parts of it or may have a cryptic phospho-?-glucosidase activity without permease activity. A screening test applied to strains belonging to several genera of Enterobacteriaceae showed that strains of Citrobacter, Hafnia, and Serratia exhibit a degree of similarity in phospho-?-glucosidase activity and inducibility which could be useful in their taxonomic characterization; others, such as Aerobacter aerogenes, Erwinia, and Proteus vulgaris, are more heterologous. Owing to the presence of inducible phospho-?-glucosidases A and B in Citrobacter, the fermentation of ?-methyl glucoside and the fermentation of arbutin in mixture with cellobiose could be of diagnostic value in the differentiation of Citrobacter from Salmonella. Wild-type strains of Escherichia coli, Shigella, and Salmonella are phenotypically similar in their inability to catabolize ?-glucosides, the presence of constitutive P-?-glucosidase A, and the lack of ?-glucoside permeases I and II. Their ?-glucoside-fermenting mutants show, however, a phospho-?-glucosidase and ?-glucoside permease activity which is characteristic for mutants from each genus. The differences in the phenotype of the mutants reflect probable differences in the presence of cryptic genes in the wild-type strains and could be of evolutionary significance. PMID:4897109

  5. Simultaneous determination of major type A and B trichothecenes, zearalenone and certain modified metabolites in Finnish cereal grains with a novel liquid chromatography-tandem mass spectrometric method.

    PubMed

    Nathanail, Alexis V; Syvähuoko, Jenna; Malachová, Alexandra; Jestoi, Marika; Varga, Elisabeth; Michlmayr, Herbert; Adam, Gerhard; Sieviläinen, Elina; Berthiller, Franz; Peltonen, Kimmo

    2015-06-01

    A reliable and sensitive liquid chromatography-tandem mass spectrometric method was developed for the simultaneous quantitative determination in cereals of the Fusarium mycotoxins HT-2 toxin, T-2 toxin, deoxynivalenol, nivalenol and zearalenone, as well as the modified metabolites 3-acetyl-deoxynivalenol, ?-zearalenol, ?-zearalenol, deoxynivalenol-3-glucoside, HT-2-3-glucoside, nivalenol-3-glucoside, zearalenone-14-glucoside, zearalenone-14-sulphate, zearalenone-16-glucoside, ?-zearalenol-14-glucoside and ?-zearalenol-14-glucoside. The 'dilute and shoot' approach was used for sample preparation after extraction with acetonitrile:water:acetic acid (79:20:1, v/v/v). Separation was carried out using reversed-phase liquid chromatography, and detection was performed using tandem mass spectrometry in the selected reaction monitoring mode. The method was in-house validated according to performance characteristics, established in Commission Regulation EC No 401/2006 and Commission Decision EC No 657/2002, prior to its application in a nationwide survey for the analysis of barley, oat and wheat samples (n?=?95) harvested in Finland during 2013. Deoxynivalenol and its glucosylated form were the most abundant of the analytes, being detected in 93 and 81 % of the samples, respectively. Concentrations of deoxynivalenol were unusually high in 2013, especially in oats, with some cases exceeding the maximum legislative limits for unprocessed oats placed on the market for first-stage processing. All modified mycotoxins analysed were detected, and the natural occurrence of some of these compounds (e.g. zearalenone-16-glucoside and nivalenol-3-glucoside) in barley, oats and/or wheat was documented for the first time. PMID:25935671

  6. Chemical constituents from the fruit of Gardenia jasminoides and their inhibitory effects on nitric oxide production.

    PubMed

    Peng, Kaifeng; Yang, Liguo; Zhao, Shizhe; Chen, Lixia; Zhao, Feng; Qiu, Feng

    2013-02-15

    Three new iridoid glycosides, 6"-O-trans-caffeoylgenipin gentiobioside (1), genipin 1-O-?-D-apiofuranosyl (1?6)-?-D-glucopyranoside (2), genipin 1-O-?-D-xylopyranosyl (1?6)-?-D-glucopyranoside (3), three new monocyclic monoterpenoids, jasminoside R (4), jasminoside S (5), jasminoside T (6), together with nine known iridoid glycosides (7-15) and three crocetin glycosides (16-18), were isolated from the fruit of Gardenia jasminoides. Their chemical structures were established mainly by 1D and 2D NMR techniques and mass spectrometry. Inhibitory effects of the isolated compounds on nitric oxide production in lipopolysaccaride-activated macrophages were evaluated. Compounds 8 and 18 showed strong inhibitory activity on NO production with IC(50) values of 11.14±0.67 and 5.99±0.54 ?M, respectively. PMID:23305920

  7. Immunological cost of chemical defence and the evolution of herbivore diet breadth.

    PubMed

    Smilanich, Angela M; Dyer, Lee A; Chambers, Jeffrey Q; Bowers, M Deane

    2009-07-01

    Selective pressures from host plant chemistry and natural enemies may contribute independently to driving insect herbivores towards narrow diet breadths. We used the specialist caterpillar, Junonia coenia (Nymphalidae), which sequesters defensive compounds, iridoid glycosides, from its host plants to assess the effects of plant chemistry and sequestration on the larval immune response. A series of experiments using implanted glass beads to challenge immune function showed that larvae feeding on diets with high concentrations of iridoid glycosides are more likely to have their immune response compromised than those feeding on diets low in these compounds. These results indicate that larvae feeding on plants with high concentrations of toxins might be more poorly defended against parasitoids, while at the same time being better defended against predators, suggesting that predators and parasitoids can exert different selective pressures on the evolution of herbivore diet breadth. PMID:19392713

  8. Anti-diabetic activity of active fractions of Stereospermum tetragonum DC and isolation of active principles

    PubMed Central

    Bino Kingsley, Renjit; Mishra, Manisha; Brindha, Pemaiah; Subramoniam, Appian

    2013-01-01

    Objectives To identify the active principles, determine the anti-diabetes activity of fraction of Stereospermum tetragonum root. Materials and Methods The efficacy was evaluated in streptozotocin induced type 2 diabetic rats and the anti-hyperglycemic activity was studied by glucose tolerance test. The major active compounds were isolated by solvent fractionation and chromatographic techniques and characterized with spectral data. Results The active fraction of S. tetragonum showed presence of anti-diabetes mellitus activity in type-2 diabetic rats. It did not significantly influence insulin release from cultured islets. Two active principles (active at 2 mg/kg dose) were isolated and characterized with spectral data. One of them was identified as an iridoid type glycoside and the other one was a lapachol like compound (derivative of naphthoquinone). Conclusions Two active principles from the anti-diabetes fraction of S. tetragonum root were isolated and identified as an iridoid glycoside and a naphthoquinone derivative. PMID:24023445

  9. PURIFICATION OF THE G PROTEIN-COUPLED RECEPTOR RHODOPSIN FOR STRUCTURAL STUDIES

    E-print Network

    Palczewski, Krzysztof

    , NG, nonyl--D-glucoside; PAGE, polyacrylamide gel electrophoresis; PBS, phosphate buffered saline; ROS-CHROMATOGRAPHIC PURIFICATION OF RHODOPSIN A. Stock solutions B. Precipitation of contaminant proteins C. DEAE

  10. Determination of anthocyanins and exploration of relationship between their composition and petal coloration in crape myrtle (Lagerstroemia hybrid).

    PubMed

    Zhang, Jie; Wang, Liang-Sheng; Gao, Jin-Ming; Shu, Qing-Yan; Li, Chong-Hui; Yao, Juan; Hao, Qing; Zhang, Jing-Jing

    2008-05-01

    Petal coloration and pigment components in 12 American crape myrtle cultivars (Lagerstroemia indicaxLagerstroemia fauriei) and five Chinese crape myrtle cultivars (L. indica hybrids) were studied. Color was measured by CIEL*a*b* scale and anthocyanin composition of crape myrtle was determined using high-performance liquid chromatography coupled to photodiode array detection and electrospray ionization mass spectrometry. The presence of the previously reported delphinidin 3-O-glucoside, petunidin 3-O-glucoside and malvidin 3-O-glucoside were confirmed. Cyanidin 3-O-glucoside was identified in crape myrtle for the first time. We explored the relationship between petal color and anthocyanin contents by multiple linear regression analyses. The results indicated that total flavones and flavonols were important variables and contributed to blue-enhancing in crape myrtle. Based on anthocyanins and co-pigments analysis, flower color breeding in crape myrtle towards true-red and blue were discussed. PMID:18713426

  11. PHYTOCHEMICAL CONTENT IN BLUEBERRIES IS INFLUENCED BY UV ILLUMINATION

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The levels of phytochemicals in blueberries were found to increase after illumination with UV-C light. Phytochemicals affected included resveratrol, myricetin 3-arabinoside, quercetin 3-galactoside, quercetin 3-arabinoside, quercetin derivative, kaempferol 3-glucoside, delphinidin-3-galactoside, cy...

  12. Vaccinium arboreum (Native) 4 

    E-print Network

    James R. Manhart

    2011-08-10

    and vivo. The therapeutically relevant compounds in pomegranate are pelagic acid, ellagitannins, flavonoids, and 3-glucosides/3,5-diglucosides of the anthocyanins delphinidin, cyanidin, and pelargonidin that exerted antioxidant, anti...

  13. Constituents of Kenyan Gardenia volkensii.

    PubMed

    Kinuthia, Esther W; Langat, Moses K; Mwangi, Elizabeth M; Cheplogoi, Peter K

    2012-01-01

    A new triterpenoid, 3-oxo-22alpha-hydroxy-olean-12-en-28-oic acid (1), oleanolic acid (2) and a known iridoid, 10-hydroxy-1-oxo-7-iriden-11-oic acid methyl ester (3) have been isolated from the dichloromethane extract of the dried seeds of Gardenia volkensii. Their structures were established by 1D and 2D NMR spectroscopic and MS methods. PMID:22428231

  14. Alpha-glucosidase inhibitory constituents of Linaria kurdica subsp. eriocalyx.

    PubMed

    Aydo?du, Irfan; Zihnio?lu, Figen; Karayildirim, Tamer; Gülcemal, Derya; Alanku?-Cali?kan, Ozgen; Bedir, Erdal

    2010-06-01

    Three known iridoid glycosides, antirrhide (1), antirrhinoside (2), and 5-O-beta-allosylantirrhinoside (3), and two known flavone glycosides, linariin (4"'-O-acetylpectolinarin) (4) and linarin (acacetin-7-O-beta-D-rutinoside) (5) were isolated from Linaria kurdica Boiss & Hohen. subsp. eriocalyx. The structures of the isolated compounds were established from spectroscopic evidence. Compounds 1-3 showed high inhibitory potential against alpha-glucosidase. PMID:20614804

  15. A new UV-filter compound in human lenses.

    PubMed

    Truscott, R J; Wood, A M; Carver, J A; Sheil, M M; Stutchbury, G M; Zhu, J; Kilby, G W

    1994-07-11

    A new UV-filter compound, 4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid O-glucoside, has been identified in human lenses. The structure suggests that it is derived biosynthetically from tryptophan. Quantification studies on the new compound show that it is the second-most abundant UV-filter compound in the lens with an absorption and fluorescence spectrum similar to that of 3-hydroxykynurenine glucoside. PMID:8034036

  16. Determination of sterol lipids in plant tissues by gas chromatography and Q-TOF mass spectrometry.

    PubMed

    Wewer, Vera; Dörmann, Peter

    2014-01-01

    Sterols are an abundant lipid class in the extraplastidic membranes of plant cells. In addition to free sterols, plants contain different conjugated sterols, i.e. sterol esters, sterol glucosides, and acylated sterol glucosides. Sterol lipids can be measured by gas chromatography after separation via thin-layer chromatography. Here, we describe a comprehensive technique based on the quantification of all four sterol classes by direct infusion quadrupole time-of-flight (Q-TOF) mass spectrometry. PMID:24777793

  17. Antioxidative activity of the flower of Torenia fournieri.

    PubMed

    Shindo, Kazutoshi; Saito, Etsuko; Sekiya, Miki; Matsui, Tomo; Koike, Yukiko

    2008-04-01

    The edible flower of Torenia fournieri Linden ex E. Fourn was found to possess potent antioxidative activity in a rat brain homogenate model. Bioassay-guided isolation of the active compounds from a CH(2)Cl(2)-MeOH (1:1) extract led to the isolation of acteoside (1), luteolin-7-O-beta-glucoside (2), apigenin-7-O-alpha-rhamnosyl-(1-->6)-beta-glucoside (3), and apigetrin (4). PMID:18404334

  18. Quantitative flavonoid variation accompanied by change of flower colors in Edgeworthia chrysantha, Pittosporum tobira and Wisteria floribunda.

    PubMed

    Ono, Megumi; Iwashina, Tsukasa

    2015-03-01

    The flavonoids in the flowers of Edgeworthia chrysantha, Pittosporum tobira and Wisteria floribunda were isolated and identified. Quercetin and kaempferol 3-O-glucosides and 3-O-rutinosides were found in E. chrysantha, and quercetin 3-O-rutinoside, 3-O-glucoside and 3-O-pentosylrhamnosylglucoside, kaempferol 3-O-robinobioside, 3-O-rutinoside, 3-O-glucoside and 3-O-pentosylrhamnosylglucoside, and isorhamnetin 3-O-rutinoside were isolated from P. tobira. Ten flavonoids, quercetin 3-O-sophoroside, 3-O-rutinoside, 3-O-glucoside, kaempferol 3-O-sophoroside and 3-O-glucoside, luteolin 5-O-glucoside, 7- O-glucoside and 7-O-hexoside, and apigenin 7-O-glucoside and 4'-O-hexoside were isolated from W floribunda. The major pigments of E. chrysantha were carotenoids. Their content decreased with the change in flower color to white from yellow via cream, and total flavonoid content also slightly decreased by ca. 0.8 in cream and ca. 0.9 fold in white flowers. In contrast with E. chrysantha, white flowers of P. tobira turn to cream and then yellow in which the major pigments are also carotenoids. In this species, both carotenoid and flavonoid contents are gradually increased from white to yellow flowers. Though the petal color of Wisteria floribunda is mauve, due to anthocyanin pigments, the yellow areas are due to carotenoids; these turn to white in the late flowering stage. However, their flavonoid contents were essentially the same among the yellow, cream and white spots of flags. Thus, it was shown by HPLC analysis of the flower flavonoids of E. chrysantha, P. tobira and W. floribunda, although the visible pigments such as carotenoids and anthocyanins are quantitatively varied, the quantitative variation in UV-absorbing substances, such as flavones and flavonols, differs with plant species. PMID:25924517

  19. Chemical Profiles and Protective Effect of Hedyotis diffusa Willd in Lipopolysaccharide-Induced Renal Inflammation Mice.

    PubMed

    Ye, Jian-Hong; Liu, Meng-Hua; Zhang, Xu-Lin; He, Jing-Yu

    2015-01-01

    Protective effect of Hedyotis diffusa (H. diffusa) Willd against lipopolysaccharide (LPS)-induced renal inflammation was evaluated by the productions of cytokines and chemokine, and the bioactive constituents of H. diffusa were detected by the ultra-fast liquid chromatography -diode array detector-quadrupole-time of flight mass spectrometry (UFLC-DAD-Q-TOF-MS/MS) method. As the results showed, water extract of H. diffusa (equal to 5.0 g/kg body weight) obviously protected renal tissues, significantly suppressed the productions of tumor necrosis factor-? (TNF-?), interleukin (IL)-1?, IL-6, and monocyte chemoattractant protein (MCP)-1, as well as significantly promoted the production of IL-10 in serum and renal tissues. According the chemical profiles of H. diffusa, flavonoids, iridoid glycosides and anthraquinones were greatly detected in serum from H. diffusa extract treatment mice. Two main chemotypes, including eight flavonoids and four iridoid glycosides were found in renal tissues from H. diffusa extract treatment mice. The results demonstrated that water extract of H. diffusa had protective effect on renal inflammation, which possibly resulted from the bioactive constituents consisting of flavonoids, iridoids and anthraquinones. PMID:26580602

  20. Incompatibility between plant-derived defensive chemistry and immune response of two sphingid herbivores.

    PubMed

    Lampert, Evan C; Bowers, M Deane

    2015-01-01

    Herbivorous insects use several different defenses against predators and parasites, and tradeoffs among defensive traits may occur if these traits are energetically demanding. Chemical defense and immune response potentially can interact, and both can be influenced by host plant chemistry. Two closely related caterpillars in the lepidopteran family Sphingidae are both attacked by the same specialist endoparasitoid species but have mostly non-overlapping host plant ranges that differ in secondary chemistry. Ceratomia catalpae is a specialist on Catalpa and also will feed on Chilopsis, which both produce iridoid glycosides. Ceratomia undulosa consumes members of the Oleaceae, which produce seco-iridoid glycosides. Immune response of the two species on a typical host plant species (Catalpa bignonioides for C. catalpa; Fraxinus americana for C. undulosa) was compared using a melanization assay, and did not differ. In a second experiment, the iridoid glycoside catalpol was added to the diets of both insects, and growth rate, mass, chemical defense, and immune response were evaluated. Increased dietary catalpol weakened the immune response of C. undulosa and altered the development rate of C. catalpae by prolonging the third instar and accelerating the fourth instar. Catalpol sequestration was negatively correlated with immune response of C. catalpae, while C. undulosa was unable to sequester catalpol. These results show that immune response can be negatively influenced by increasing concentrations of sequestered defensive compounds. PMID:25516226

  1. Chemical Profiles and Protective Effect of Hedyotis diffusa Willd in Lipopolysaccharide-Induced Renal Inflammation Mice

    PubMed Central

    Ye, Jian-Hong; Liu, Meng-Hua; Zhang, Xu-Lin; He, Jing-Yu

    2015-01-01

    Protective effect of Hedyotis diffusa (H. diffusa) Willd against lipopolysaccharide (LPS)-induced renal inflammation was evaluated by the productions of cytokines and chemokine, and the bioactive constituents of H. diffusa were detected by the ultra-fast liquid chromatography -diode array detector-quadrupole-time of flight mass spectrometry (UFLC-DAD-Q-TOF-MS/MS) method. As the results showed, water extract of H. diffusa (equal to 5.0 g/kg body weight) obviously protected renal tissues, significantly suppressed the productions of tumor necrosis factor-? (TNF-?), interleukin (IL)-1?, IL-6, and monocyte chemoattractant protein (MCP)-1, as well as significantly promoted the production of IL-10 in serum and renal tissues. According the chemical profiles of H. diffusa, flavonoids, iridoid glycosides and anthraquinones were greatly detected in serum from H. diffusa extract treatment mice. Two main chemotypes, including eight flavonoids and four iridoid glycosides were found in renal tissues from H. diffusa extract treatment mice. The results demonstrated that water extract of H. diffusa had protective effect on renal inflammation, which possibly resulted from the bioactive constituents consisting of flavonoids, iridoids and anthraquinones. PMID:26580602

  2. Glandular ?-glucosidases in juvenile Chrysomelina leaf beetles support the evolution of a host-plant-dependent chemical defense.

    PubMed

    Rahfeld, Peter; Haeger, Wiebke; Kirsch, Roy; Pauls, Gerhard; Becker, Tobias; Schulze, Eva; Wielsch, Natalie; Wang, Ding; Groth, Marco; Brandt, Wolfgang; Boland, Wilhelm; Burse, Antje

    2015-03-01

    Plant-feeding insects are spread across the entire plant kingdom. Because they chew externally on leaves, leaf beetle of the subtribe Chrysomelina sensu stricto are constantly exposed to life-threatening predators and parasitoids. To counter these pressures, the juveniles repel their enemies by displaying glandular secretions that contain defensive compounds. These repellents can be produced either de novo (iridoids) or by using plant-derived precursors. The autonomous production of iridoids pre-dates the evolution of phytochemical-based defense strategies. Both strategies include hydrolysis of the secreted non-toxic glycosides in the defensive exudates. By combining in vitro as well as in vivo experiments, we show that iridoid de novo producing as well as sequestering species rely on secreted ?-glucosidases to cleave the pre-toxins. Our phylogenetic analyses support a common origin of chrysomeline ?-glucosidases. The kinetic parameters of these ?-glucosidases demonstrated substrate selectivity which reflects the adaptation of Chrysomelina sensu stricto to the chemistry of their hosts during the course of evolution. However, the functional studies also showed that the broad substrate selectivity allows building a chemical defense, which is dependent on the host plant, but does not lead to an "evolutionary dead end". PMID:25596091

  3. Ergosteryl-?-glucosidase (Egh1) involved in sterylglucoside catabolism and vacuole formation in Saccharomyces cerevisiae.

    PubMed

    Watanabe, Takashi; Tani, Motohiro; Ishibashi, Yohei; Endo, Ikumi; Okino, Nozomu; Ito, Makoto

    2015-10-01

    Sterylglucosides (SGs) are composed of a glucose and sterol derivatives, and are distributed in fungi, plants and mammals. We recently identified EGCrP1 and EGCrP2 (endoglycoceramidase-related proteins 1 and 2) as a ?-glucocerebrosidase and steryl-?-glucosidase, respectively, in Cryptococcus neoformans. We herein describe an EGCrP2 homologue (Egh1; ORF name, Yir007w) involved in SG catabolism in Saccharomyces cerevisiae. The purified recombinant Egh1 hydrolyzed various ?-glucosides including ergosteryl ?-glucoside (EG), cholesteryl ?-glucoside, sitosteryl ?-glucoside, para-nitrophenyl ?-glucoside, 4-methylumberifellyl ?-glucoside and glucosylceramide. The disruption of EGH1 in S. cerevisiae BY4741 (egh1?) resulted in the accumulation of EG and fragmentation of vacuoles. The expression of EGH1 in egh1? (revertant) reduced the accumulation of EG, and restored the morphology of vacuoles. The accumulation of EG was not detected in EGH1 and UGT51(ATG26) double-disrupted mutants (ugt51?egh1?), indicating that EG was synthesized by Ugt51(Atg26) and degraded by Egh1 in vivo. These results clearly demonstrated that Egh1 is an ergosteryl-?-glucosidase that is functionally involved in the EG catabolic pathway and vacuole formation in S. cerevisiae. PMID:26116408

  4. Authentication of geographical origin and crop system of grape juices by phenolic compounds and antioxidant activity using chemometrics.

    PubMed

    Granato, Daniel; Koot, Alex; Schnitzler, Egon; van Ruth, Saskia M

    2015-03-01

    The main goal of this work was to propose an authentication model based on the phenolic composition and antioxidant and metal chelating capacities of purple grape juices produced in Brazil and Europe in order to assess their typicality. For this purpose, organic, conventional, and biodynamic grape juices produced in Brazil (n = 65) and in Europe (n = 31) were analyzed and different multivariate class-modeling and classification statistical techniques were employed to differentiate juices based on the geographical origin and crop system. Overall, Brazilian juices, regardless of the crop system adopted, presented higher contents of total phenolic compounds and flavonoids, total monomeric anthocyanins, proanthocyanidins, flavonols, flavanols, cyanidin-3-glucoside, delphinidin-3-glucoside, and malvidin-3,5-glucoside. No differences were observed for trans-resveratrol, malvidin-3-glucoside, and pelargonidin-3-glucoside between countries and among crop systems. A total of 91% of Brazilian and 97% of European juices were adroitly classified using partial least squares discriminant analysis when the producing region was considered (92% efficiency), in which the free-radical scavenging activity toward 2,2-diphenyl-1-picrylhydrazyl, content of total phenolic compounds, gallic acid, and malvidin-3-glucoside were the variables responsible for the classification. Intraregional models based on soft independent modeling of class analogy were able to differentiate organic from conventional Brazilian juices as well as conventional and organic/biodynamic European juices. PMID:25675840

  5. Phenolic composition and antioxidant activity in seed coats of 60 Chinese black soybean (Glycine max L. Merr.) varieties.

    PubMed

    Zhang, Rui Fen; Zhang, Fang Xuan; Zhang, Ming Wei; Wei, Zhen Cheng; Yang, Chun Ying; Zhang, Yan; Tang, Xiao Jun; Deng, Yuan Yuan; Chi, Jian Wei

    2011-06-01

    Phenolics in black soybean seed coat (BSSC) are considered to be responsible for the health benefits of black soybean. BSSCs of 60 Chinese varieties were examined for phenolic contents, anthocyanin profiles, and antioxidant activity. Total phenolic and condensed tannin contents ranged from 512.2 to 6057.9 mg gallic acid equivalents/100 g and from 137.2 to 1741.1 mg (+)-catechin equivalents/100 g, respectively. Six anthocyanins (delphinidin-3-glucoside, cyanidin-3-galactoside, cyanidin-3-glucoside, petunidin-3-glucoside, peonidin-3-glucoside, and malvidin-3-glucoside) were detected by HPLC. Total anthocyanin contents (TAC) were from 98.8 to 2132.5 mg/100 g, and cyanidin-3-glucoside was the most abundant anthocyanin in all varieties, with a distribution of 48.8-94.1% of TAC. Antioxidant properties detected by DPPH, FRAP, and ORAC methods all showed wide variations ranging from 4.8 to 65.3 ?g/100 mL (expressed as EC(50)), from 17.5 to 105.8 units/g, and from 42.5 to 1834.6 ?mol Trolox equivalent/g, respectively. Sixty varieties were classified into four groups by hierarchical clustering analysis, and group 4 consisting of nine varieties had the highest phytochemicals content and antioxidant activity. PMID:21548651

  6. Distribution of free and glycosylated sterols within Cycas micronesica plants

    PubMed Central

    Marler, Thomas E.; Shaw, Christopher A.

    2010-01-01

    Flour derived from Cycas micronesica seeds was once the dominant source of starch for Guam's residents. Cycad consumption has been linked to high incidence of human neurodegenerative diseases. We determined the distribution of the sterols stigmasterol and ?-sitosterol and their derived glucosides stigmasterol ?-d-glucoside and ?-sitosterol ?-d-glucoside among various plant parts because they have been identified in cycad flour and have been shown to elicit neurodegenerative outcomes. All four compounds were common in seeds, sporophylls, pollen, leaves, stems, and roots. Roots contained the greatest concentration of both free sterols, and photosynthetic leaflet tissue contained the greatest concentration of both steryl glucosides. Concentration within the three stem tissue categories was low compared to other organs. Reproductive sporophyll tissue contained free sterols similar to seeds, but greater concentration of steryl glucosides than seeds. One of the glucosides was absent from pollen. Concentration in young seeds was higher than old seeds as reported earlier, but concentration did not differ among age categories of leaf, sporophyll, or vascular tissue. The profile differences among the various tissues within these organs may help clarify the physiological role of these compounds. PMID:20157629

  7. Visualizing metabolite distribution and enzymatic conversion in plant tissues by desorption electrospray ionization mass spectrometry imaging.

    PubMed

    Li, Bin; Knudsen, Camilla; Hansen, Natascha Krahl; Jørgensen, Kirsten; Kannangara, Rubini; Bak, Søren; Takos, Adam; Rook, Fred; Hansen, Steen H; Møller, Birger Lindberg; Janfelt, Christian; Bjarnholt, Nanna

    2013-06-01

    In comparison with the technology platforms developed to localize transcripts and proteins, imaging tools for visualization of metabolite distributions in plant tissues are less well developed and lack versatility. This hampers our understanding of plant metabolism and dynamics. In this study, we demonstrate that desorption electrospray ionization mass spectrometry imaging (DESI-MSI) of tissue imprints on porous Teflon may be used to accurately image the distribution of even labile plant metabolites such as hydroxynitrile glucosides, which normally undergo enzymatic hydrolysis by specific ?-glucosidases upon cell disruption. This fast and simple sample preparation resulted in no substantial differences in the distribution and ratios of all hydroxynitrile glucosides between leaves from wild-type Lotus japonicus and a ?-glucosidase mutant plant that lacks the ability to hydrolyze certain hydroxynitrile glucosides. In wild-type, the enzymatic conversion of hydroxynitrile glucosides and the concomitant release of glucose were easily visualized when a restricted area of the leaf tissue was damaged prior to sample preparation. The gene encoding the first enzyme in hydroxynitrile glucoside biosynthesis in L. japonicus leaves, CYP79D3, was found to be highly expressed during the early stages of leaf development, and the hydroxynitrile glucoside distribution in mature leaves reflected this early expression pattern. The utility of direct DESI-MSI of plant tissue was demonstrated using cryo-sections of cassava (Manihot esculenta) tubers. The hydroxynitrile glucoside levels were highest in the outer cell layers, as verified by LC-MS analyses. The unexpected discovery of a hydroxynitrile-derived di-glycoside shows the potential of DESI-MSI to discover and guide investigations into new metabolic routes. PMID:23551340

  8. Effect of different organic farming methods on the phenolic composition of sea buckthorn berries.

    PubMed

    Heinäaho, Merja; Hagerman, Ann E; Julkunen-Tiitto, Riitta

    2009-03-11

    The effects of different organic cultivation methods on the berry phenolics of two Finnish sea buckthorn (Hippophae rhamnoides L. ssp. rhamnoides ) cultivars, 'Terhi' and 'Tytti', were studied in an experimental field at a coastal area in Merikarvia, western Finland. Cultivation methods included different fertilizers (designed for organic cultivation), mulches (organic and plastic), and land contours (flat land versus ridged beds). Two experiments were conducted: The first, a fertilization experiment, allowed for the estimation of the effects of cultivar, fertilizer, land contour, and all of their interactions. The second experiment, a mulch experiment, allowed for the estimation of the effects of mulch, land contours, and their interactions for the cultivar 'Tytti'. Berry phenolics were analyzed by high-performance liquid chromatography (HPLC) with ultraviolet (UV) detection. The results suggest that there are significant differences between the cultivars and cultivation methods. The concentrations of quercetin derivatives 1-3, isorhamnetin 3,7-diglucoside, quercetin-3-glucoside-7-rhamnoside, quercetin 3-glucoside, isorhamnetin 3-glucoside, and flavonoid derivative 3 were higher in 'Tytti' than in 'Terhi', while concentrations of isorhamnetin-glucoside 2 and 3 were higher in 'Terhi' than in 'Tytti'. Flat land increased the concentrations of isorhamnetin 3,7-diglucoside, isorhamnetin-glucoside 1, quercetin derivatives 2 and 4, and condensed tannins. Mulch did not have any significant effect on the concentrations of phenolic compounds. These results indicate that the phenolic accumulation in berries of studied sea buckthorn cultivars seems to be mainly dependent upon cultivar selection and soil structure. PMID:19219991

  9. Optimization of the Extraction of Anthocyanins from the Fruit Skin of Rhodomyrtus tomentosa (Ait.) Hassk and Identification of Anthocyanins in the Extract Using High-Performance Liquid Chromatography-Electrospray Ionization-Mass Spectrometry (HPLC-ESI-MS)

    PubMed Central

    Liu, Guo-Ling; Guo, Hong-Hui; Sun, Yuan-Ming

    2012-01-01

    Anthocyanins are naturally occurring polyphenols that impart bright color to fruits, vegetables and plants. In this study, the extraction of anthocyanins from freeze-dried fruit skin of downy rose-myrtle (Rhodomyrtus tomentosa (Ait.) Hassk var. Gangren) was optimized using response surface methodology (RSM). Using 60% ethanol containing 0.1% (v/v) hydrochloric acid as extraction solvent, the optimal conditions for maximum yields of anthocyanin (4.358 ± 0.045 mg/g) were 15.7:1 (v/w) liquid to solid ratio, 64.38 °C with a 116.88 min extraction time. The results showed good fits with the proposed model for the anthocyanin extraction (R2 = 0.9944). Furthermore, the results of high-performance liquid chromatography-electrospray ionization-mass spectrometry (HPLC-ESI-MS) analysis of the anthocyanins extracted from the fruit skin of downy rose-myrtle revealed the presence of five anthocyanin components, which were tentatively identified as delphinidin-3-glucoside, cyanidin-3-glucoside, peonidin-3-glucoside, petunidin-3-glucoside and malvidin-3-glucoside. PMID:22754365

  10. Inhibition of human GLUT1 and GLUT5 by plant carbohydrate products; insights into transport specificity

    PubMed Central

    George Thompson, Alayna M.; Iancu, Cristina V.; Nguyen, Thi Thanh Hanh; Kim, Doman; Choe, Jun-yong

    2015-01-01

    Glucose transporters GLUT1 (transports glucose) and GLUT5 (transports fructose), in addition to their functions in normal metabolism, have been implicated in several diseases including cancer and diabetes. While GLUT1 has several inhibitors, none have been described for GLUT5. By transport activity assays we found two plant products, rubusoside (from Rubus suavissimus) and astragalin-6-glucoside (a glycosylated derivative of astragalin, from Phytolacca americana) that inhibited human GLUT5. These plants are utilized in traditional medicine: R. suavissimus for weight loss and P. americana for cancer treatment, but the molecular interactions of these products are unknown. Rubusoside also inhibited human GLUT1, but astragalin-6-glucoside did not. In silico analysis of rubusoside:protein interactions pinpointed a major difference in substrate cavity between these transporters, a residue that is a tryptophan in GLUT1 but an alanine in GLUT5. Investigation of mutant proteins supported the importance of this position in ligand specificity. GLUT1W388A became susceptible to inhibition by astragalin-6-glucoside and resistant to rubusoside. GLUT5A396W transported fructose and also glucose, and maintained inhibition by rubusoside and astragalin-6-glucoside. Astragalin-6-glucoside can serve as a starting point in the design of specific inhibitors for GLUT5. The application of these studies to understanding glucose transporters and their interaction with substrates and ligands is discussed. PMID:26306809

  11. Phenylalanine derived cyanogenic diglucosides from Eucalyptus camphora and their abundances in relation to ontogeny and tissue type.

    PubMed

    Neilson, Elizabeth H; Goodger, Jason Q D; Motawia, Mohammed Saddik; Bjarnholt, Nanna; Frisch, Tina; Olsen, Carl Erik; Møller, Birger Lindberg; Woodrow, Ian E

    2011-12-01

    The cyanogenic glucoside profile of Eucalyptus camphora was investigated in the course of plant ontogeny. In addition to amygdalin, three phenylalanine-derived cyanogenic diglucosides characterized by unique linkage positions between the two glucose moieties were identified in E. camphora tissues. This is the first time that multiple cyanogenic diglucosides have been shown to co-occur in any plant species. Two of these cyanogenic glucosides have not previously been reported and are named eucalyptosin B and eucalyptosin C. Quantitative and qualitative differences in total cyanogenic glucoside content were observed across different stages of whole plant and tissue ontogeny, as well as within different tissue types. Seedlings of E. camphora produce only the cyanogenic monoglucoside prunasin, and genetically based variation was observed in the age at which seedlings initiate prunasin biosynthesis. Once initiated, total cyanogenic glucoside concentration increased throughout plant ontogeny with cyanogenic diglucoside production initiated in saplings and reaching a maximum in flower buds of adult trees. The role of multiple cyanogenic glucosides in E. camphora is unknown, but may include enhanced plant defense and/or a primary role in nitrogen storage and transport. PMID:21945721

  12. Influence of White Clover Mosaic Potexvirus Infection on the Endogenous Cytokinin Content of Bean

    PubMed Central

    Clarke, Sean Francis; McKenzie, Marian Jane; Burritt, David John; Guy, Paul Leslie; Jameson, Paula Elizabeth

    1999-01-01

    The cytokinin content in the primary leaves of bean (Phaseolus vulgaris) was monitored for 10 d after inoculation with white clover mosaic potexvirus. The cytokinins were isolated, purified, separated by high-performance liquid chromatography, and quantified by radioimmunoassay. The cytokinins detected at the time of inoculation (d 0) were: (a) the free bases, zeatin (Z), dihydrozeatin (DZ), and isopentenyladenine; (b) the riboside, DZ riboside (DZR); (c) the O-glucosides of DZ, DZR, and Z riboside; (d) the nucleotides, Z riboside-5?-monophosphate and isopentenyladenosine-5?-monophosphate; and (e) trace amounts of Z-9-glucoside and DZ-9-glucoside. During the 10 d after inoculation with white clover mosaic potexvirus, marked quantitative changes in this cytokinin profile were observed. The concentration of the free bases and DZR decreased, accompanied by an increase in the 9-glucosides and the nucleotides. Virus titer increased rapidly 3 d after inoculation, attaining a maximum level at d 5. This increase coincided with the increases in the 9-glucosides and the nucleotides. We propose that the decline in the cytokinin free bases and riboside may allow the increase of virus titer in bean and lead to the senescence of infected leaves. PMID:10364406

  13. Anthocyanins from the flowers of Nagai line of Japanese garden Iris (Iris ensata).

    PubMed

    Kitahara, Kaori; Murai, Yoshinori; Bang, Sang Woo; Kitajima, Junichi; Iwashina, Tsukasa; Kaneko, Yukio

    2014-02-01

    Six anthocyanins were isolated from the flowers of the Nagai line of Iris ensata Thunb. They were identified as petunidin and malvidin 3-O-beta-[(4"'-Z-p-coumaroyl-alpha-rhamnopyranosyl)-(1-->6)-beta-glucopyranoside]-5-O-beta-glucopyranosides (1 and 3) and their E-forms (2 and 4), and petunidin and malvidin 3-O-rutinoside-5-O-glucosides (5 and 6). Though the E-form of petunidin 3-O-[(4"'-p-coumaroylrhamnosyl)-(1-->6)-glucoside]-5-O-glucoside has been reported, its Z-form was found for the first time. The presence of Z- and E-forms of malvidin 3-O-[(4'''-p-coumaroylrhamnosyl)-(1-->6)-glucoside]-5-O-glucoside is also reported for the first time. Fifty-one cultivars of Nagai line and their wild form (I. ensata var. spontanea) were divided into four anthocyanin patterns, i.e. 1) the presence of 1-4, 2) the presence of 2 and 4, 3) the presence of 5 and 6, and 4) no anthocyanin. PMID:24689289

  14. The polyphenolic profiles of common bean (Phaseolus vulgaris L.)

    PubMed Central

    Lin, Long-Ze; Harnly, James M.; Pastor-Corrales, Marcial S.; Luthria, Devanand L.

    2013-01-01

    Based on the phenolic profiles obtained by high performance liquid chromatography-electrospray ionization mass spectrometry (HPLC-DAD-ESI/MS), 24 common bean samples, representing 17 varieties and 7 generic off-the-shelf items, belonging to ten US commercial market classes can be organized into six different groups. All of them contained the same hydroxycinnaminic acids, but the flavonoid components showed distinct differences. Black beans contained primarily the 3-O-glucosides of delphinidin, petunidin and malvidin, while pinto beans contained kaempferol and its 3-O-glycosides. Light red kidney bean contained traces of quercetin 3-O-glucoside and its malonates, but pink and dark red kidney beans contained the diglycosides of quercetin and kaempferol. Small red beans contained kaempferol 3-O-glucoside and pelargonidin 3-O-glucoside, while no flavonoids were detected in alubia, cranberry, great northern, and navy beans. This is the first report of the tentative identification of quercetin 3-O-pentosylhexoside and flavonoid glucoside malonates, and the first detailed detection of hydroxycinnamates, in common beans. PMID:25544796

  15. Inhibition of human GLUT1 and GLUT5 by plant carbohydrate products; insights into transport specificity.

    PubMed

    George Thompson, Alayna M; Iancu, Cristina V; Nguyen, Thi Thanh Hanh; Kim, Doman; Choe, Jun-yong

    2015-01-01

    Glucose transporters GLUT1 (transports glucose) and GLUT5 (transports fructose), in addition to their functions in normal metabolism, have been implicated in several diseases including cancer and diabetes. While GLUT1 has several inhibitors, none have been described for GLUT5. By transport activity assays we found two plant products, rubusoside (from Rubus suavissimus) and astragalin-6-glucoside (a glycosylated derivative of astragalin, from Phytolacca americana) that inhibited human GLUT5. These plants are utilized in traditional medicine: R. suavissimus for weight loss and P. americana for cancer treatment, but the molecular interactions of these products are unknown. Rubusoside also inhibited human GLUT1, but astragalin-6-glucoside did not. In silico analysis of rubusoside:protein interactions pinpointed a major difference in substrate cavity between these transporters, a residue that is a tryptophan in GLUT1 but an alanine in GLUT5. Investigation of mutant proteins supported the importance of this position in ligand specificity. GLUT1W388A became susceptible to inhibition by astragalin-6-glucoside and resistant to rubusoside. GLUT5A396W transported fructose and also glucose, and maintained inhibition by rubusoside and astragalin-6-glucoside. Astragalin-6-glucoside can serve as a starting point in the design of specific inhibitors for GLUT5. The application of these studies to understanding glucose transporters and their interaction with substrates and ligands is discussed. PMID:26306809

  16. Flavonoid profile and antioxidant activities of methanolic extract of Hyparrhenia hirta (L.) Stapf.

    PubMed

    Bouaziz-Ketata, Hanen; Zouari, Nabil; Ben Salah, Hichem; Rafrafi, Moez; Zeghal, Najiba

    2015-04-01

    In this study, we report isolation of flavonoids, viz., 3-O-methylquercetin, tangeritin, luteolin-7-O-glucoside, luteolin, apigenin-7-O-glucoside, apigenin-8-C-glucoside, luteolin-8-C-glucoside, luteolin-6-C-glucoside, diosmetin and catechin from the methanolic extract of Hyparrhenia hirta employing high performance liquid chromatography and liquid chromatography-electrospray ionization-tandem mass spectrometry. The total phenolic content of H. hirta extract was 105.58 ± 0.1 mg gallic acid equivalents/g of plant extract while the total flavonoid content was 45.20 ± 0.2 mg quercetin equivalents/g of plant extract and the total condensed tannin were 72.35 ± 0.7 mg catechin equivalents/g of plant extract by reference to standard curve. The antioxidant activity was assayed through the antioxidant capacity by phosphomolybdenum assay, the reducing power assay and the radical scavenging activity using 2,2-diphenyl-1-picrylhydrazyl method. The extract showed dose dependant activity in all the three assays. PMID:26011981

  17. Pre-clinical anti-inflammatory aspects of a cuisine and medicinal millennial herb: Malva sylvestris L.

    PubMed

    Prudente, Arthur S; Loddi, Alliete M V; Duarte, Márcia R; Santos, Adair R S; Pochapski, Marcia T; Pizzolatti, Moacir G; Hayashi, Sirlei S; Campos, Francinete R; Pontarolo, Roberto; Santos, Fabio A; Cabrini, Daniela A; Otuki, Michel F

    2013-08-01

    Malva sylvestris has been used since ancient times for its emollient, laxative and anti-inflammatory properties, being extensively used as salads, soups and teas. The preset study evaluated the topical anti-inflammatory action of M. sylvestris hydroalcoholic extract (HE) and its compounds in mice ear inflammation caused by 12-O-tetradecanoylphorbol-acetate in mice. The LC-MS analysis of the HE confirmed the presence of scopoletin, quercetin and malvidin 3-glucoside compounds in the HE of M. sylvestris. Topical application of the HE reduced ear oedema, polymorphonuclear cells influx (myeloperoxydase activity and histological analysis) and interleukin-1? levels in the tissue. The topical application of the compound present in the HE, malvidin 3-glucoside was also able to inhibit ear oedema and leukocytes migration. The other tested compounds, scopoletin, quercetin and malvidin 3,5-glucoside were able to prevent the formation of oedema and cell infiltration, but with less effectiveness when compared to HE and malvidin 3-glucoside. Therefore, these results consistently support the notion that M. sylvestris leaves possesses topical anti-inflammatory activity, the compound malvidin 3-glucoside seems to be major responsible for this effect, with the participation of other anti-inflammatory compounds in the extract. Thus, as recommended by population, M. sylvestris can be used as a future treatment to skin disorders. PMID:23684757

  18. Evaluation of the nutraceutical, antioxidant and cytoprotective properties of ripe pistachio (Pistacia vera L., variety Bronte) hulls.

    PubMed

    Barreca, Davide; Laganà, Giuseppina; Leuzzi, Ugo; Smeriglio, Antonella; Trombetta, Domenico; Bellocco, Ersilia

    2016-04-01

    Every year tons of pistachio hulls are separated and eliminated, as waste products, from pistachio seeds. In this study the hulls of ripe pistachios were extracted with two organic solvents (ethanol and methanol) and characterized for phenolic composition, antioxidant power and cytoprotective activity. RP-HPLC-DAD-FLU separation enabled us to identify 20 derivatives, including and by far the most abundant gallic acid, 4-hydroxybenzoic acid, protocatechuic acid, naringin, eriodictyol-7-O-glucoside, isorhamnetin-7-O-glucoside, quercetin-3-O-rutinoside, isorhamnetin-3-O-glucoside and catechin. Methanol extraction gave the highest yields for all classes of compounds and presented a higher scavenging activity in all the antioxidant assays performed. The same was found for cytoprotective activity on lymphocytes, lipid peroxidation and protein degradation. These findings highlight the strong antioxidant and cytoprotective activity of the extract components, and illustrate how a waste product can be used as a source of nutraceuticals to employ in manufacturing industry. PMID:26593519

  19. Characterization of flavonoid glycosides from rapeseed bee pollen using a combination of chromatography, spectrometry and nuclear magnetic resonance with a step-wise separation strategy.

    PubMed

    Li, Yi; Qi, Yitao; Ritho, Joan; Zhang, Yongxin; Zheng, Xiaowei; Zhou, Jinhui; Sun, Liping

    2016-01-01

    To identify the structures of flavonoid glycosides in bee pollen collected from rapeseed plants (Brassica napus L.), we utilised an approach that combined liquid chromatography-diode array detector-electrospray ionization-mass spectrometry (LC-DAD-ESI-MS) and nuclear magnetic resonance (NMR) technology with a step-wise separation strategy. We identified four constituents of high purity in rape bee pollen samples: (1) quercetin-3-O-?-D-glucosyl-(2?l)-?-glucoside, (2) kaempferol-3, 4'-di-O-?-D-glucoside, (3) 5, 7, 4'-trihydroxy-3'-methoxyflavone-3-O-?-D-sophoroside and (4) kaempferol-3-O-?-D-glucosyl-(2?l)-?-D-glucoside. This study will also provide useful reference standards for qualification and quantification of four flavonoid glycosides in natural products. PMID:25981986

  20. Characterization of alkyl polyglycosides by both reversed-phase and normal-phase modes of high-performance liquid chromatography.

    PubMed

    Czichocki, Gunther; Fiedler, Harald; Haage, Klaus; Much, Helmut; Weidner, Steffen

    2002-01-18

    Alkyl polyglycosides today represent the most important sugar surfactant. Nonionic sugar surfactants produced via different synthetic routes are mixtures of alkyl homologues, oligomers, anomers and isomers. Alkyl homologues and oligomers of alkyl mono- and diglucosides were separated by reversed-phase high-performance liquid chromatography (HPLC) with methanol-water as the mobile phase using a gradient elution. The gradient was optimized in respect to a simultaneous separation of alkyl glycosides according to their alkyl chain length and alkyl polyoxyethylene glucosides with regard to their length of the polyoxyethylene spacer. The separation of alkyl glycosides into alpha- and beta-anomers was carried out by normal-phase HPLC with isooctane-ethyl acetate (60:40, v/v)-2-propanol in the gradient mode. Light scattering detection was used. Matrix-assisted laser desorption ionization time-of-flight mass spectra of alkyl glucosides and dodecyl glucosides with oxyethylene spacer groups are presented. PMID:11833644

  1. [Separation and evaluation of antioxidant constituents from Carthamus tinctorius].

    PubMed

    Yue, Shi-Jun; Tang, Yu-Ping; Wang, Lin-Yan; Tang, Hao; Li, Shu-Jiao; Liu, Pei; Su, Shu-Lan; Duan, Jin-Ao

    2014-09-01

    Bio-active components from Carthamus tinctorius were separated on the basis of antioxidant capacities in vitro. The antioxidant capacity was investigated on the basis of the ability to scavenge DPPH radical, ABTS radical and reduce Fe3+ of different polar fractions. Furthermore, the chemical compounds were isolated from bio-active fraction, and were evaluated for the antioxidative effects. Five major components were isolated and identified from water extract as 6-hydroxykaempferol 3,6,7-tri-O-?-D-glucoside(1), 6-hydroxykaempferol 3-O-?-rutinoside-6-O-?-D-glucoside (2), 6-hydroxykaempferol 3-O-?-D-glucoside (3), hydroxysafflor yellow A (4) and anhydrosafflor yellow B (5). By evaluating and comparing the antioxidative effects of different fractions and obtained compounds, the results showed that water extract displayed significantly high antioxidative activities and 6-hydroxykaempferol glycosides and quinochalcone C-glycosides were found as main contribution for antioxidant property. PMID:25522615

  2. Taxiphyllin 6'-O-gallate, actinidioionoside 6'-O-gallate and myricetrin 2?-O-sulfate from the leaves of Syzygium samarangense and their biological activities.

    PubMed

    Samy, Mamdouh Nabil; Mamdouh, Nabil Samy; Sugimoto, Sachiko; Matsunami, Katsuyoshi; Otsuka, Hideaki; Kamel, Mohamed Salah

    2014-01-01

    Three new compounds were isolated from a MeOH extract of the leaves of Syzygium samarangense, one new cyanogenic glucoside, taxiphyllin 6'-O-gallate (1), one new megastigmane glucoside, actinidioionoside 6'-O-gallate (2), and one new sulfated flavonoid rhamnoside, myricetrin 2?-O-sulfate (3), together with 14 known compounds, lupeol (4), demethoxymatteucinol (5), cryptostrobin (6), betulinic acid (7), ?-sitosterol glucoside (8), 2R-prunasin (9), myrciaphenone A (10), 1-feruloyl-?-D-glucopyranoside (11), (3S,5R,6R,7E,9S)-3,5,6,9-tetrahydroxymegastigman-7-ene (12), guaijaverin (13), myricetin 4'-methyl ether 3-O-?-L-rhamnopyranoside (14), myricetrin (15), gallic acid (16) and actinidioionoside (17). The structures of the new compounds were determined through a combination of spectroscopic, HPLC and chemical analyses. PMID:25273060

  3. Beta-glucosidase, exo-beta-glucanase and pyridoxine transglucosylase activities of rice BGlu1.

    PubMed Central

    Opassiri, Rodjana; Hua, Yanling; Wara-Aswapati, Onnop; Akiyama, Takashi; Svasti, Jisnuson; Esen, Asim; Ketudat Cairns, James R

    2004-01-01

    The bglu1 cDNA for a beta-glucosidase cloned from rice (Oryza sativa L.) seedlings was expressed as a soluble and active protein in Escherichia coli and designated BGlu1. This enzyme hydrolysed beta-1,4-linked oligosaccharides with increasing catalytic efficiency (kcat/Km) values as the DP (degree of polymerization) increased from 2 to 6. In contrast, hydrolysis of beta-1,3-linked oligosaccharides decreased from DP 2 to 3, and polymers with a DP greater than 3 were not hydrolysed. The enzyme also hydrolysed p -nitrophenyl beta-D-glycosides and some natural glucosides but with lower catalytic efficiency than beta-linked oligosaccharides. Pyridoxine 5'-O-beta-D-glucoside was the most efficiently hydrolysed natural glycoside tested. BGlu1 also had high transglucosylation activity towards pyridoxine, producing pyridoxine 5'-O-beta-D-glucopyranoside in the presence of the glucose donor p-nitrophenyl beta-D-glucoside. PMID:14692878

  4. Phenolic compounds and antimicrobial activity of olive (Olea europaea L. Cv. Cobrançosa) leaves.

    PubMed

    Pereira, Ana Paula; Ferreira, Isabel C F R; Marcelino, Filipa; Valentão, Patricia; Andrade, Paula B; Seabra, Rosa; Estevinho, Leticia; Bento, Albino; Pereira, José Alberto

    2007-01-01

    We report the determination of phenolic compounds in olive leaves by reversed-phase HPLC/DAD, and the evaluation of their in vitro activity against several microorganisms that may be causal agents of human intestinal and respiratory tract infections, namely gram positive (Bacillus cereus, B. subtilis and Staphylococcus aureus), gram negative bacteria (Pseudomonas aeruginosa, Escherichia coli and Klebsiella pneumoniae) and fungi (Candida albicans and Cryptococcus neoformans). Seven phenolic compounds were identified and quantified: caffeic acid, verbascoside, oleuropein, luteolin 7-O-glucoside, rutin, apigenin 7-O-glucoside and luteolin 4'-O-glucoside. At low concentrations olive leaves extracts showed an unusual combined antibacterial and antifungal action, which suggest their great potential as nutraceuticals, particularly as a source of phenolic compounds. PMID:17873849

  5. Simultaneous determination of six flavonoids from Paulownia tomentosa flower extract in rat plasma by LC-MS/MS and its application to a pharmacokinetic study.

    PubMed

    Dai, Bin; Hu, Zhiqiang; Li, Haiyan; Yan, Chong; Zhang, Liwei

    2015-01-26

    A simple, rapid and sensitive liquid chromatography-tandem mass spectrometry (LC-MS/MS) method was developed and validated for simultaneous determination of six components including apigenin, quercetin, apigenin-7-O-?-D-glucoside, quercetin-3-O-?-D-glucoside, 3'-methoxyluteolin-7-O-?-D-glucoside, and tricin-7-O-?-D-glucopyranoside in rat plasma using formononetin as the internal standard (IS). The plasma samples were pretreated by a one-step liquid-liquid extraction with dichloromethane. The chromatographic separation was carried out on a ZORBAX SB-Aq column with a gradient mobile phase consisting of acetonitrile and 2mM aqueous ammonium acetate. All analytes and IS were quantitated through electrospray ionization in negative ion multiple reaction monitoring mode. The mass transitions were as follows: m/z 269.1?117.2 for apigenin, m/z 301.2?151.2 for quercetin, m/z 431.3?311.2 for apigenin-7-O-?-D-glucoside, m/z 463.2?300.2 for quercetin-3-O-?-D-glucoside, m/z 461.3?283.1 for 3'-methoxyluteolin-7-O-?-D-glucoside, m/z 491.3?313.1 for tricin-7-O-?-D-glucopyranoside, and m/z 267.2?252.2 for IS, respectively. All calibration curves exhibited good linearity with correlation coefficient (r)>0.995. The intra-day and inter-day precisions (RSD) at three QC levels were both less than 14.0% and the accuracies ranged from 89.8% to 113.8%. The extraction recoveries of six compounds ranged from 82.3% to 92.5%. The validated method was successfully applied to pharmacokinetic study of the six components in male rat plasma after oral administration of Paulownia tomentosa flower extract. PMID:25531870

  6. Multi-substrate flavonol O-glucosyltransferases from strawberry (Fragaria×ananassa) achene and receptacle

    PubMed Central

    Griesser, Markus; Vitzthum, Florian; Fink, Barbara; Bellido, Mari Luz; Raasch, Constanze; Munoz-Blanco, Juan; Schwab, Wilfried

    2008-01-01

    In an effort to characterize fruit ripening-related genes functionally, two glucosyltransferases, FaGT6 and FaGT7, were cloned from a strawberry (Fragaria×ananassa) cDNA library and the full-length open reading frames were amplified by rapid amplification of cDNA ends. FaGT6 and FaGT7 were expressed heterologously as fusion proteins in Escherichia coli and target protein was purified using affinity chromatography. Both recombinant enzymes exhibited a broad substrate tolerance in vitro, accepting numerous flavonoids, hydroxycoumarins, and naphthols. FaGT6 formed 3-O-glucosides and minor amounts of 7-O-, 4?-O-, and 3?-O-monoglucosides and one diglucoside from flavonols such as quercetin. FaGT7 converted quercetin to the 3-O-glucoside and 4?-O-glucoside and minor levels of the 7- and 3?-isomers but formed no diglucoside. Gene expression studies showed that both genes are strongly expressed in achenes of small-sized green fruits, while the expression levels were generally lower in the receptacle. Significant levels of quercetin 3-O-, 7-O-, and 4?-O-glucosides, kaempferol 3-O- and 7-O-glucosides, as well as isorhamnetin 7-O-glucoside, were identified in achenes and the receptacle. In the receptacle, the expression of both genes is negatively controlled by auxin which correlates with the ripening-related gene expression in this tissue. Salicylic acid, a known signal molecule in plant defence, induces the expression of both genes. Thus, it appears that FaGT6 and FaGT7 are involved in the glucosylation of flavonols and may also participate in xenobiotic metabolism. The latter function is supported by the proven ability of strawberries to glucosylate selected unnatural substrates injected in ripe fruits. This report presents the first biochemical characterization of enzymes mainly expressed in strawberry achenes and provides the foundation of flavonoid metabolism in the seeds. PMID:18487633

  7. Studies on the constituents of Syringa species. XII. New glycosides from the leaves of Syringa reticulata (BLUME) HARA.

    PubMed

    Machida, Koichi; Unagami, Eriko; Ojima, Hiromi; Kikuchi, Masao

    2003-07-01

    Three new glycosides, 6'-O-alpha-D-galactopyranosylsyringopicroside (1), secologanoside 7-methyl ester (2) and (+)-lariciresinol 4'-O-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranoside (3), were isolated from the leaves of Syringa reticulata. Their structures were established on the basis of chemical and spectral data. Compound 1 is the first naturally occurring iridoid di-glycoside having melibiose. Comparison of the spectral data of 2 and that previously recognized as secologanoside 7-methyl ester led to the conclusion that the recognized structure should be revised to the sodium salt of secoxyloganin (2'). PMID:12843604

  8. Anthraquinone derivatives from Heterophyllaea pustulata.

    PubMed

    Núñez Montoya, Susana C; Agnese, Alicia M; Cabrera, José L

    2006-05-01

    From the leaves of Heterophyllaea pustulata two new monomeric anthraquinones, heterophylline (1,6-dihydroxy-7-methoxy-2-methylanthraquinone, 1) and pustuline (2-hydroxy-3-methoxy-7-methylanthraquinone, 2), and one new bianthraquinone, (S)-5,5'-bisoranjidiol [(S)-5,5'-bis(1,6-dihydroxy-2-methylanthraquinone), 3], were isolated. Furthermore, the iridoid glycoside asperuloside and three known flavonoids, quercetin, isoquercitrin, and quercetin-3-O-beta-d-glucosyl-6' '-acetate, were obtained. The structures were determined by analysis of their spectroscopic data and chemical evidence. PMID:16724844

  9. Two New Compounds from Hedyotis lindleyana.

    PubMed

    Kim, Tuyen Pham Nguyen; Mai, Tram Phan Thi; Phi, Phung Nguyen Kim

    2015-07-01

    One new sodium salt of an iridoid acid, sodium 6-O-methyldeacetylasperulosidate (1) and one new heterocyclic compound, 1,3,6-trimethylpyrano[2,3- d]imidazole-2,5(1H,3H)-dione (2) were isolated from Hedyotis lindleyana Hook. (Rubiaceae), together with seven known compounds, oleanolic acid (3), ursolic acid (4), teneoside D (5), 6?-hydroxygeniposide (6), deacetylasperulosidic acid sodium salt (7), liquiritin (8), and 3,3',4'-tri-O-methylellagic acid (9). The structures were established by spectroscopic (1D, 2D NMR) and HR-ESI-MS analysis, as well as by comparison with data reported in the literature. PMID:26410995

  10. Comprehensive two-dimensional high-performance liquid chromatography system with immobilized liposome chromatography column and reversed-phase column for separation of complex traditional Chinese medicine Longdan Xiegan Decoction.

    PubMed

    Wang, Yun; Kong, Liang; Lei, Xiaoyuan; Hu, Lianghai; Zou, Hanfa; Welbeck, Ed; Bligh, S W Annie; Wang, Zhengtao

    2009-03-13

    A comprehensive two-dimensional HPLC system with an immobilized liposome chromatography (ILC) column in conjunction with an RP column (in tandem) was developed for the screening and analysis of the membrane-permeable compounds in a traditional Chinese medicine prescription Longdan Xiegan Decoction (LXD). More than 50 components in LXD were resolved using the developed separation system. Eight flavonoids and two iridoids were identified interacting with the ILC column; a system that mimics biomembranes. The results show that the developed comprehensive two-dimensional chromatography system can be used for identifying membrane permeable natural products in complex matrixes such as extracts of traditional Chinese medicine prescriptions. PMID:18585729

  11. Antibiofilm phenylethanoid glycosides from Penstemon centranthifolius.

    PubMed

    Ye, Miao; Zhao, Yun; Norman, Vanessa L; Starks, Courtney M; Rice, Stephanie M; Goering, Matt G; O'Neil-Johnson, Mark; Eldridge, Gary R; Hu, Jin-Feng

    2010-05-01

    Bioassay-guided fractionation of the antibacterial ethyl acetate-ethanol (50 : 50) extract obtained from the aerial parts of Penstemon centranthifolius led to the isolation of six phenylethanoid glycosides (1-6) and eleven iridoid glycosides (7-17). Their structures were determined on the basis of spectroscopic analysis and comparison with the literature. Among them, two phenylethanoid glycosides, 4'''-O-acetylverbascoside (1) and verbascoside (2), were found to show significant inhibition of the formation of bacterial biofilms by Escherichia coli UTI89. Compound 1 showed 77% biofilm inhibition at 2.5 microg/mL, and compound 2 showed 60% inhibition at 5 microg/mL. PMID:19827017

  12. Monoterpene pyridine alkaloids and phenolics from Scrophularia ningpoensis and their cardioprotective effect.

    PubMed

    Zhu, Ling-Juan; Hou, Yun-Long; Shen, Xiu-Yu; Pan, Xiao-Dong; Zhang, Xue; Yao, Xin-Sheng

    2013-07-01

    Scrophularianines A-C (1-3), three new unusual monoterpene pyridine alkaloids with cyclopenta [c] pyridine skeleton reported from the genus Scrophularia for the first time, together with 15 known compounds (4-18), were isolated from the extract of Scrophularia ningpoensis. Their structures were elucidated on the basis of extensive analyses of spectroscopic evidences. The biogenetic relationship between monoterpene pyridine alkaloids and iridoids was proposed preliminarily. The myocardial protective bioassay indicated that compounds 13 and 14 with a concentration of 10(-4)M exhibited significantly protective effect against H2O2-induced apoptosis in cardiomyocytes. PMID:23602903

  13. Componential Profile and Amylase Inhibiting Activity of Phenolic Compounds from Calendula officinalis L. Leaves

    PubMed Central

    Olennikov, Daniil N.; Kashchenko, Nina I.

    2014-01-01

    An ethanolic extract and its ethyl acetate-soluble fraction from leaves of Calendula officinalis L. (Asteraceae) were found to show an inhibitory effect on amylase. From the crude extract fractions, one new phenolic acid glucoside, 6?-O-vanilloyl-?-D-glucopyranose, was isolated, together with twenty-four known compounds including five phenolic acid glucosides, five phenylpropanoids, five coumarins, and nine flavonoids. Their structures were elucidated based on chemical and spectral data. The main components, isoquercitrin, isorhamnetin-3-O-?-D-glucopyranoside, 3,5-di-O-caffeoylquinic acid, and quercetin-3-O-(6??-acetyl)-?-D-glucopyranoside, exhibited potent inhibitory effects on amylase. PMID:24683352

  14. Sterylglucoside catabolism in Cryptococcus neoformans with endoglycoceramidase-related protein 2 (EGCrP2), the first steryl-?-glucosidase identified in fungi.

    PubMed

    Watanabe, Takashi; Ito, Tomoharu; Goda, Hatsumi M; Ishibashi, Yohei; Miyamoto, Tomofumi; Ikeda, Kazutaka; Taguchi, Ryo; Okino, Nozomu; Ito, Makoto

    2015-01-01

    Cryptococcosis is an infectious disease caused by pathogenic fungi, such as Cryptococcus neoformans and Cryptococcus gattii. The ceramide structure (methyl-d18:2/h18:0) of C. neoformans glucosylceramide (GlcCer) is characteristic and strongly related to its pathogenicity. We recently identified endoglycoceramidase-related protein 1 (EGCrP1) as a glucocerebrosidase in C. neoformans and showed that it was involved in the quality control of GlcCer by eliminating immature GlcCer during the synthesis of GlcCer (Ishibashi, Y., Ikeda, K., Sakaguchi, K., Okino, N., Taguchi, R., and Ito, M. (2012) Quality control of fungus-specific glucosylceramide in Cryptococcus neoformans by endoglycoceramidase-related protein 1 (EGCrP1). J. Biol. Chem. 287, 368-381). We herein identified and characterized EGCrP2, a homologue of EGCrP1, as the enzyme responsible for sterylglucoside catabolism in C. neoformans. In contrast to EGCrP1, which is specific to GlcCer, EGCrP2 hydrolyzed various ?-glucosides, including GlcCer, cholesteryl-?-glucoside, ergosteryl-?-glucoside, sitosteryl-?-glucoside, and para-nitrophenyl-?-glucoside, but not ?-glucosides or ?-galactosides, under acidic conditions. Disruption of the EGCrP2 gene (egcrp2) resulted in the accumulation of a glycolipid, the structure of which was determined following purification to ergosteryl-3?-glucoside, a major sterylglucoside in fungi, by mass spectrometric and two-dimensional nuclear magnetic resonance analyses. This glycolipid accumulated in vacuoles and EGCrP2 was detected in vacuole-enriched fraction. These results indicated that EGCrP2 was involved in the catabolism of ergosteryl-?-glucoside in the vacuoles of C. neoformans. Distinct growth arrest, a dysfunction in cell budding, and an abnormal vacuole morphology were detected in the egcrp2-disrupted mutants, suggesting that EGCrP2 may be a promising target for anti-cryptococcal drugs. EGCrP2, classified into glycohydrolase family 5, is the first steryl-?-glucosidase identified as well as a missing link in sterylglucoside metabolism in fungi. PMID:25361768

  15. Morphological control of helical solid bilayers in high-axial-ratio nanostructures through binary self-assembly.

    PubMed

    John, George; Jung, Jong Hwa; Minamikawa, Hiroyuki; Yoshida, Kaname; Shimizu, Toshimi

    2002-12-01

    Mixed molecular species of cardanyl glucoside derived from renewable resources provide nanotubes upon self-assembly in water, while the saturated homologue generated a twisted fibrous morphology. The cardanyl glucoside mixture was fractionated into four individual components in order to study their contribution to the nanotube formation. The rational control of self-assembled helical morphologies was achieved by binary self-assembling of the saturated and monoene derivatives. This method can generate a diversity of self-assembled high-axial-ratio nanostructures (HARNs), ranging from twisted ribbons and helical ribbons to nanotubes. PMID:12561322

  16. Flavonol glycosides from Calendula officinalis flowers.

    PubMed

    Vidal-Ollivier, E; Elias, R; Faure, F; Babadjamian, A; Crespin, F; Balansard, G; Boudon, G

    1989-02-01

    Seven flavonol 3- O-glycosides were isolated from the flowers of CALENDULA OFFICINALIS L. Their structures were elucidated as isorhamnetin 3- O-glucoside, rutinoside, neohesperidoside, 2 (G)-rhamnosylrutinoside, quercetin glucoside, neohesperidoside, and 2 (G)-rhamnosylrutinoside by paper and thin layer chromatography, UV, (13)C-NMR, and mass spectroscopy. The interglycosidic linkages of isorhamnetin 3- O-neohesperidoside, 2 (G)-rhamnosylrutinoside, quercetin 3- O-neohesperidoside and structural determination of quercetin 2 (G)-rhamnosylrutinoside are described for the first time in CALENDULA OFFICINALIS. PMID:17262260

  17. Constituents from the leaves of Phellodendron amurense and their antioxidant activity.

    PubMed

    Leu, Chien-Hsing; Li, Chia-Ying; Yao, Xinsheng; Wu, Tian-Shung

    2006-09-01

    Three new coumarins, phellodenols F-H (1-3) and a new glutaric acid derivative, phellodendric acid-A (4) were isolated from the leaves of Phellodendron amurense together with twenty-nine known compounds. Extensive 1D and 2D NMR experiments and other spectroscopic studies were employed to determine the structures of 1-4. The isolated compounds were screened for their antioxidant activity through DPPH (alpha,alpha-diphenyl-beta-picrylhydrazyl) radical scavenging assay. Compounds quercetin, quercetin-3-O-beta-D-glucoside, quercetin-3-O-beta-D-galactoside and kaempferol-3-O-beta-D-glucoside demonstrated significant radical scavenging activity comparable to vitamin E. PMID:16946541

  18. The metabolism of the isomeric decalones

    PubMed Central

    Elliott, T. H.; Robertson, J. S.; Williams, R. T.

    1966-01-01

    1. The metabolism of (±)-cis-1-, (±)-trans-1-, (±)-cis-2- and (±)-trans-2-decalone in the rabbit has been investigated. 2. (±)-cis-2- and (±)-trans-2-Decalone were both reduced to racemic secondary alcohols, conformationally related to the ketones administered, and possessing an equatorial hydroxyl group. These alcohols were excreted in the urine as glucuronides in amounts equal to about half the dose administered. The glucuronides were isolated both as triacetyl methyl esters and as sodium salts. The ester obtained after feeding with (±)-cis-2-decalone proved to be methyl (cis–cis-2-decalyl tri-O-acetyl-?-d-glucosid)uronate, whereas (±)-trans-2-decalone yielded methyl (trans–cis-2-decalyl tri-O-acetyl-?-d-glucosid)uronate. The sodium salts were shown to be sodium (cis–cis-2-decalyl glucosid)uronate and sodium (trans–cis-2-decalyl glucosid)uronate. 3. Enzyme hydrolysis of the sodium salts and acid hydrolysis of the esters derived from (±)-cis-2-decalone yielded (±)-cis–cis-2-decalol, and of those from (±)-trans-2-decalone yielded (±)-trans–cis-2-decalol. 4. (±)-cis-1-Decalone was reduced mainly to (?)-cis–cis-1-decalol and excreted as [(?)-cis–cis-1-decalyl glucosid]-uronic acid. A small amount of the corresponding (+)-isomer was produced, yielding [(+)-cis–cis-1-decalyl glucosid]uronic acid on isolation. Enzyme hydrolysis of these compounds gave the corresponding aglycones; both alcohols possessed an equatorial hydroxyl group. 5. (±)-trans-1-Decalone was reduced to (+)-trans–trans-1-decalol, with an equatorial hydroxyl group, and in smaller amount to (+)-trans–cis-1-decalol possessing an axial group. The former alcohol was excreted as [(+)-trans–cis-1-decalyl glucosid]uronic acid, and the latter as [(+)-trans–cis-1-decalyl glucosid]uronic acid. 6. From a knowledge of the conformations, and in some cases the absolute configurations, of the compounds administered and excreted, and by making the assumption that the coenzyme concerned in the reductions is NADH (or NADPH), an explanation of the above findings in terms of steric hindrance and thermodynamic stability is given. PMID:4381830

  19. Anti-inflammatory effects and structure elucidation of two new compounds from Astragalus membranaceus (Fisch) Bge. var. mongholicus (Bge) Hsiao

    NASA Astrophysics Data System (ADS)

    Wang, Qing-Hu; Han, Na-Ren-Chao-Ke-Tu; Dai, Na-Yin-Tai; Wang, Xiu-Lan; Ao, Wu-Li-Ji

    2014-09-01

    Phytochemical study of the ethanol extract of Astragalus membranaceus (Fisch) Bge. var. mongholicus (Bge) Hsiao resulted to the isolation of two new compounds, 1-hydroxy-5-methylolbenzol-2-O-?-D-glucoside (1) and (3R, 4R)-4,7-hydroxy-2?,3?-dimethoxyisoflavane-4?-O-?-D-glucoside (2). The structure of the isolated compounds were elucidated on the basis of the spectroscopic methods including UV, IR, ESI-MS, 1D NMR and 2D NMR techniques, and by comparison with those reported in the literature. The new compounds were investigated for its effect against inflammation induced by egg-albumin and carrageenan in rats.

  20. Identification of metabolites of geniposide in rat urine using ultra-performance liquid chromatography combined with electrospray ionization quadrupole time-of-flight tandem mass spectrometry.

    PubMed

    Han, Han; Yang, Li; Xu, Ying; Ding, Yue; Bligh, S W Annie; Zhang, Tong; Wang, Zhengtao

    2011-11-15

    Geniposide, an iridoid glycoside, is an important and characteristic compound in the fruits of Gardenia jasminoides Ellis, a commonly used medicinal herb in Chinese traditional and folk medicine for the treatment of inflammation and jaundice. However, few studies have been carried out on the metabolism of geniposide. In this study, we have established a rapid and sensitive method using ultra-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UPLC/ESI-QTOF-MS) for analysis of the metabolic profile of geniposide in rat urine after oral administration. A total of ten metabolites were detected and identified by comparing their fragmentation patterns with that of geniposide using Metabolynx™ and MassFragment™ software tools. The results revealed that the principal metabolism pathways of geniposide in rat occurred after deglycosylation of the irdoid glycoside take place and this is followed by glucuronidation and the pyran-ring cleavages. The major metabolite, the glucuronic acid conjugate of genipin as observed in vivo, was further confirmed by the in vitro enzymatic study. The results of this work have demonstrated the feasibility of the UPLC/ESI-QTOF-MS approach for rapid and reliable characterization of metabolites from iridoid compounds. PMID:22006398

  1. One-enzyme catalyzed simultaneous plant cell disruption and conversion of released glycoside to aglycone combined with in situ product separation as green one-pot production of genipin from gardenia fruit.

    PubMed

    Winotapun, Weerapath; Opanasopit, Praneet; Ngawhirunpat, Tanasait; Rojanarata, Theerasak

    2013-07-10

    A direct one-pot production of genipin, an iridoid aglycone, from crude gardenia fruit was developed. The method relied on the use of single cellulase to disrupt plant cells and to cleave off sugar molecules simultaneously, thereby enhancing the release of intracellular iridoids and converting geniposide to genipin. During the biocatalysis, eco-friendly ethyl acetate was used to extract the product, providing the partial purification and the minimization of genipin degradation. By using 10 mg/mL cellulase and 24 h-incubation at 50 °C, pH 4, combined with in situ extraction, genipin with good purity was yielded at 58.83 mg/g, which increased 12.38 and 1.72 times compared with those obtained from the procedures without either the aid of enzyme or in situ extraction, respectively. Therefore, this integrated approach is promising for the production of genipin and should be potentially applied to the preparation of other plant aglycones. PMID:23769308

  2. Fructus Gardenia (Gardenia jasminoides J. Ellis) phytochemistry, pharmacology of cardiovascular, and safety with the perspective of new drugs development.

    PubMed

    Liu, Hao; Chen, Yong-Feng; Li, Fang; Zhang, Hai-Yan

    2013-01-01

    The phytochemistry, cardiovascular pharmacology, toxicology, side effect, and further development prospects of Gardenia jasminoides J. Ellis (GJE) and its main constituents crocins and iridoid glycosides were studied. Numerous studies have confirmed that crocins and iridoid glycosides had effects of antioxidation, anti-inflammatory, anti-atherosclerosis, anti-ischemic brain injuries, anti-platelet aggregation, anti-hyperglycemia, anti-hyperlipidemia, anti-hypertension, and so on. Some of them might be related to several attractive pharmacodynamic actions of GJE such as promoting endothelium growth, protecting neurons, and inducing their differentiation. Both of them make it possible for GJE to prevent and cure thromboembolism and cardiovascular diseases well. From our own basic pharmacological research of GJE extract on several rat models, it has been known that GJE extract markedly prolonged bleeding time and inhibited platelet aggregation and thrombosis. It has significant proliferation effect on both endothelial cells and endothelial progenitor cells as well. As the mechanisms of GJE on those diseases were discussed and summarized, questions about its genetoxicity and hepatotoxicity were also discussed during its safety study to make the foundation for long-term medication and clinical research in the near future. PMID:23211013

  3. Melanogenesis inhibitory activity of monoterpene glycosides from Gardeniae Fructus.

    PubMed

    Akihisa, Toshihiro; Watanabe, Kensuke; Yamamoto, Ayako; Zhang, Jie; Matsumoto, Masahiro; Fukatsu, Makoto

    2012-08-01

    A new iridoid glycoside, 10-O-(4"-O-methylsuccinoyl)geniposide (7), and two new pyronane glycosides, jasminosides Q and R (13 and 14, resp.), along with nine known iridoid glycosides, 1-6 and 8-10, and two known pyronane glycosides, 11 and 12, were isolated from a MeOH extract of Gardeniae Fructus, the dried ripe fruit of Gardenia jasminoides (Rubiaceae). The structures of new compounds were elucidated on the basis of extensive spectroscopic analyses and comparison with literature. Upon evaluation of compounds 1-14 on the melanogenesis in B16 melanoma cells induced with ?-melanocyte-stimulating hormone (?-MSH), three compounds, i.e., 6-O-p-coumaroylgeniposide (3), 7, and 6'-O-sinapoyljasminoside (12), exhibited inhibitory effects with 21.6-41.0 and 37.5-47.7% reduction of melanin content at 30 and 50 ?M, respectively, with almost no toxicity to the cells (83.7-106.1% of cell viability at 50 ?M). PMID:22899609

  4. Interactive effects of simulated nitrogen deposition and altered precipitation patterns on plant allelochemical concentrations.

    PubMed

    Jamieson, Mary A; Quintero, Carolina; Blumenthal, Dana M

    2013-09-01

    Global environmental change alters the supply of multiple limiting resources that regulate plant primary and secondary metabolism. Through modifications in resource availability, acquisition, and allocation, global change is likely to influence plant chemical defenses, and consequently species interactions that are mediated by these compounds. While many studies focus on individual global change factors, simultaneous changes in abiotic factors may interact to influence plant allelochemicals. In this study, we examined the individual and interactive effects of nitrogen enrichment and altered precipitation patterns on chemical defense compounds (iridoid glycosides) of an invasive plant, Linaria dalmatica. Plants were grown from seed in native mixed-grass prairie for 2 years. Nitrogen and water treatments were applied in each growing season over this period. Results indicate that soil water and nitrogen availability interact to shape plant chemical defense concentrations in L. dalmatica. Nitrogen addition decreased iridoid glycoside concentrations by approximately 25% under reduced water availability, increased concentrations by 37% in ambient water plots, and had no effect on these chemical defenses for plants growing under augmented water supply. Thus, results show differing patterns of allelochemical response to nitrogen enrichment, with respect to both the magnitude and direction of change, depending on water availability. Our study demonstrates the importance of examining multiple environmental factors in order to predict potential changes in plant chemical defenses with climate change. PMID:24008867

  5. Trail Pheromone of the Argentine Ant, Linepithema humile (Mayr) (Hymenoptera: Formicidae)

    PubMed Central

    Choe, Dong-Hwan; Villafuerte, David B.; Tsutsui, Neil D.

    2012-01-01

    The Argentine ant (Linepithema humile) is recognized as one of the world's most damaging invasive species. One reason for the ecological dominance of introduced Argentine ant populations is their ability to dominate food and habitat resources through the rapid mobilization and recruitment of thousands of workers. More than 30 years ago, studies showed that (Z)-9-hexadecenal strongly attracted Argentine ant workers in a multi-choice olfactometer, suggesting that (Z)-9-hexadecenal might be the trail pheromone, or a component of a trail pheromone mixture. Since then, numerous studies have considered (Z)-9-hexadecenal as the key component of the Argentine ant trails. Here, we report the first chemical analyses of the trails laid by living Argentine ants and find that (Z)-9-hexadecenal is not present in a detectible quantity. Instead, two iridoids, dolichodial and iridomyrmecin, appear to be the primary chemical constituents of the trails. Laboratory choice tests confirmed that Argentine ants were attracted to artificial trails comprised of these two chemicals significantly more often than control trails. Although (Z)-9-hexadecenal was not detected in natural trails, supplementation of artificial dolichodial+iridomyrmecin trails with an extremely low concentraion of (Z)-9-hexadecenal did increase the efficacy of the trail-following behavior. In stark contrast with previous dogma, our study suggests that dolichodial and iridomyrmecin are major components of the Argentine ant trail pheromone. (Z)-9-hexadecenal may act in an additive manner with these iridoids, but it does not occur in detectable quantities in Argentine ant recruitment trails. PMID:23028739

  6. Borreria and Spermacoce species (Rubiaceae): A review of their ethnomedicinal properties, chemical constituents, and biological activities

    PubMed Central

    Conserva, Lucia Maria; Ferreira, Jesu Costa

    2012-01-01

    Borreira and Spermacoce are genera of Rubiaceae widespread in tropical and subtropical America, Africa, Asia, and Europe. Based on its fruits morphology they are considered by many authors to be distinct genera and most others, however, prefer to combine the two taxa under the generic name Spermacoce. Whereas the discussion is still unclear, in this work they were considered as synonyms. Some species of these genera play an important role in traditional medicine in Africa, Asia, Europe, and South America. Some of these uses include the treatment of malaria, diarrheal and other digestive problems, skin diseases, fever, hemorrhage, urinary and respiratory infections, headache, inflammation of eye, and gums. To date, more than 60 compounds have been reported from Borreria and Spermacoce species including alkaloids, iridoids, flavonoids, terpenoids, and other compounds. Studies have confirmed that extracts from Borreria and Spermacoce species as well as their isolated compounds possess diverse biological activities, including anti-inflammatory, antitumor, antimicrobial, larvicidal, antioxidant, gastrointestinal, anti-ulcer, and hepatoprotective, with alkaloids and iridoids as the major active principles. This paper briefly reviews the ethnomedicinal uses, phytochemistry, and biological activities of some isolated compounds and extracts of both genera. PMID:22654404

  7. Protective Effects of Corni Fructus against Advanced Glycation Endproducts and Radical Scavenging

    PubMed Central

    Park, Chan Hum; Tanaka, Takashi; Kim, Hyun Young; Park, Jong Cheol; Yokozawa, Takako

    2012-01-01

    We investigated the inhibition of advanced glycation endproduct (AGE) activity using the fluorescence characteristics of fractions and compounds from Corni Fructus. Corni Fructus extract and its iridoid glycoside components showed low inhibitory activities as well as the AGE inhibitor aminoguanidine. However, a low molecular weight polyphenol, 7-O-galloyl-D-sedoheptulose, and an antioxidant, trolox, showed high inhibitory activities compared with aminoguanidine under reactive conditions. The AGE-inhibiting activity of polyphenolic fractions of Corni Fructus ranged from a level comparable to Corni Fructus extract to the higher level of 7-O-galloyl-D-sedoheptulose. As well as the results of AGE-inhibiting activity, Corni Fructus extract and iridoid components showed low or no 1,1-diphenyl-2-pycrylhydrazyl (DPPH) radical-scavenging activities, whereas 7-O-galloyl-D-sedoheptulose showed a level comparable to trolox. Polyphenolic fractions of Corni Fructus quenched DPPH radicals in a concentration-dependent manner. Some fractions exerted a higher DPPH radical-scavenging activity compared with trolox and 7-O-galloyl-D-sedoheptulose. The DPPH radical-scavenging activity was significantly correlated with the AGE-inhibiting activity. These results suggest that polyphenolic fractions of Corni Fructus inhibited AGE formation by antioxidant activity including free radical scavenging. The strong DPPH radical-scavenging and AGE-inhibiting fractions included ellagitannins and polymeric proanthocyanidins. PMID:22649473

  8. De novo sequencing transcriptome of endemic Gentiana straminea (Gentianaceae) to identify genes involved in the biosynthesis of active ingredients.

    PubMed

    Zhou, Dangwei; Gao, Shan; Wang, Huan; Lei, Tianxiang; Shen, Jianwei; Gao, Jie; Chen, Shilong; Yin, Jia; Liu, Jianquan

    2016-01-01

    Gentiana straminea is a popular Tibetan medicine that has been used for thousands of years in China to treat various diseases and conditions. Although it has multiple pharmaceutical purposes and important economic plant resource in China, transcriptome and molecular base still known limited. In flowering season, samples were collected from different tissues, using the NGS Illumina. Solexa platform, about 58.85 million sequencing reads were generated and assembled de novo, yielding 78,764 high quality unigenes with an average length of 1090bp. Gene Ontology (GO), KEGG pathway mapping showed that 49,033 of these were identified as putative homologs of annotated sequences in the protein databases. Among them, candidate genes associated with iridoid, flavonoid and anthocyanin were identified. Further the key enzymes involved to iridoid and flavonoid synthesis pathway were analyzed by quantitative real-time polymerase chain reaction (qRT-PCR) on different tissues, the flower and root had the higher expression than leaves. In addition, 7591 SSR markers were identified from the unigenes of the G. straminea transcriptome. The foundation of G. straminea provided the important resource for facilitating to study molecular and functional genomics of it and related this species on the Qinghai-Tibet Plateau. PMID:26358503

  9. Antioxidant and metabolite profiling of North American and neotropical blueberries using LC-TOF-MS and multivariate analyses.

    PubMed

    Ma, Chunhui; Dastmalchi, Keyvan; Flores, Gema; Wu, Shi-Biao; Pedraza-Peñalosa, Paola; Long, Chunlin; Kennelly, Edward J

    2013-04-10

    There are many neotropical blueberries, and recent studies have shown that some have even stronger antioxidant activity than the well-known edible North American blueberries. Antioxidant marker compounds were predicted by applying multivariate statistics to data from LC-TOF-MS analysis and antioxidant assays of 3 North American blueberry species (Vaccinium corymbosum, Vaccinium angustifolium, and a defined mixture of Vaccinium virgatum with V. corymbosum) and 12 neotropical blueberry species (Anthopterus wardii, Cavendishia grandifolia, Cavendishia isernii, Ceratostema silvicola, Disterigma rimbachii, Macleania coccoloboides, Macleania cordifolia, Macleania rupestris, Satyria boliviana, Sphyrospermum buxifolium, Sphyrospermum cordifolium, and Sphyrospermum ellipticum). Fourteen antioxidant markers were detected, and 12 of these, including 7 anthocyanins, 3 flavonols, 1 hydroxycinnamic acid, and 1 iridoid glycoside, were identified. This application of multivariate analysis to bioactivity and mass data can be used for identification of pharmacologically active natural products and may help to determine which neotropical blueberry species will be prioritized for agricultural development. Also, the compositional differences between North American and neotropical blueberries were determined by chemometric analysis, and 44 marker compounds including 16 anthocyanins, 15 flavonoids, 7 hydroxycinnamic acid derivatives, 5 triterpene glycosides, and 1 iridoid glycoside were identified. PMID:23547798

  10. Liver X Receptor and Peroxisome Proliferator-Activated Receptor Agonist from Cornus alternifolia

    PubMed Central

    He, Yang-Qing; Ma, Guo-Yi; Peng, Jiang-nan; Ma, Zhan-Ying; Hamann, Mark T.

    2012-01-01

    Background Peroxisome proliferator-activated receptors (PPARs) belong to the nuclear receptors superfamily and are transcription factors activated by specific ligands. Liver X receptors (LXR) belong to the nuclear hormone receptors and have been shown to play an important role in cholesterol homeostasis. From the previous screening of several medicinal plants for potential partial PPAR? agonists, the extracts of Cornus alternifolia were found to exhibit promising bioactivity. In this paper, we report the isolation and structural elucidation of four new compounds and their potential as ligands for PPAR. Methods The new compounds were extracted from the leaves of Cornus alternifolia and fractionated by high-performance liquid chromatography. Their structures were elucidated on the basis of spectroscopic evidence and analysis of their hydrolysis products. Results Three new iridoid glycosides including an iridolactone, alternosides A-C (1–3), a new megastigmane glycoside, cornalternoside (4) and 10 known compounds, were obtained from the leaves of Cornus alternifolia. Kaempferol-3-O-?-glucopyranoside (5) exhibited potent agonistic activities for PPAR?, PPAR? and LXR with EC50 values of 0.62, 3.0 and 1.8 ? M, respectively. Conclusions We isolated four new and ten known compounds from Cornus alternifolia, and one known compound showed agonistic activities for PPAR?, PPAR? and LXR. General significance Compound 1 is the first example of a naturally occurring iridoid glycoside containing a ?-glucopyranoside moiety at C-6. PMID:22353334

  11. Scropolioside B Inhibits IL-1? and Cytokines Expression through NF-?B and Inflammasome NLRP3 Pathways

    PubMed Central

    Zhang, Liuqiang; Ling, Shuang; Duan, Ju; Qian, Fei; Li, Yiming; Xu, Jin-Wen

    2014-01-01

    Chronic inflammation is associated with various chronic illnesses including immunity disorders, cancer, neurodegeneration, and vascular diseases. Iridoids are compounds with anti-inflammatory properties. However their anti-inflammatory mechanism remains unclear. Here, we report that scropolioside B, isolated from a Tibetan medicine (Scrophularia dentata Royle ex Benth.), blocked expressions of TNF, IL-1, and IL-32 through NF-?B pathway. Scropolioside B inhibited NF-?B activity in a dose-dependent manner with IC50 values of 1.02??mol/L. However, catalpol, similar to scropolioside B, was not effective in inhibiting NF-?B activity. Interestingly, scropolioside B and catalpol decreased the expression of NLRP3 and cardiolipin synthetase at both the mRNA and protein level. Our results showed that scropolioside B is superior in inhibiting the expression, maturation, and secretion of IL-1? compared to catalpol. These observations provide further understanding of the anti-inflammatory effects of iridoids and highlight scropolioside B as a potential drug for the treatment of rheumatoid arthritis and atherosclerosis. PMID:25386048

  12. Scropolioside B inhibits IL-1? and cytokines expression through NF-?B and inflammasome NLRP3 pathways.

    PubMed

    Zhu, Tiantian; Zhang, Liuqiang; Ling, Shuang; Duan, Ju; Qian, Fei; Li, Yiming; Xu, Jin-Wen

    2014-01-01

    Chronic inflammation is associated with various chronic illnesses including immunity disorders, cancer, neurodegeneration, and vascular diseases. Iridoids are compounds with anti-inflammatory properties. However their anti-inflammatory mechanism remains unclear. Here, we report that scropolioside B, isolated from a Tibetan medicine (Scrophularia dentata Royle ex Benth.), blocked expressions of TNF, IL-1, and IL-32 through NF-?B pathway. Scropolioside B inhibited NF-?B activity in a dose-dependent manner with IC50 values of 1.02??mol/L. However, catalpol, similar to scropolioside B, was not effective in inhibiting NF-?B activity. Interestingly, scropolioside B and catalpol decreased the expression of NLRP3 and cardiolipin synthetase at both the mRNA and protein level. Our results showed that scropolioside B is superior in inhibiting the expression, maturation, and secretion of IL-1? compared to catalpol. These observations provide further understanding of the anti-inflammatory effects of iridoids and highlight scropolioside B as a potential drug for the treatment of rheumatoid arthritis and atherosclerosis. PMID:25386048

  13. Anti-inflammatory glycoterpenoids from Scrophularia auriculata.

    PubMed

    Giner, R M; Villalba, M L; Recio, M C; Máñez, S; Cerdá-Nicolás, M; Ríos, J

    2000-02-18

    The activity of the four glycoterpenoids: two saponins, verbascosaponin A and verbascosaponin, and two iridoids, scropolioside A and scrovalentinoside, isolated from Scrophularia auriculata ssp. pseudoauriculata, were studied in different models of acute and chronic inflammation. Both saponins significantly inhibited the mouse paw edema induced by carrageenan and ear edema induced by single and multiple doses of 12-O-tetradecanoylphorbol 13-acetate (TPA). Verbascosaponin A showed a potency twice as high as that of indomethacin in the acute TPA model. Verbascosaponin A and scropolioside A were active after a long latency period against ethyl phenylpropiolate edema, as are glucocorticoids. When the putative corticoid-like mechanism of the two compounds was studied, verbascosaponin A activity was notably reduced by the mRNA synthesis inhibitor, actinomycin D, while the effect of scropolioside A was partially interfered with by the anti-glucocorticoid drugs used. Both iridoids were active on the delayed type hypersensitivity reaction. They significantly reduced the inflammatory lesion and suppressed the cellular infiltration. PMID:10688990

  14. New insight into the inhibition of the inflammatory response to experimental delayed-type hypersensitivity reactions in mice by scropolioside A.

    PubMed

    Bas, Esperanza; Recio, M Carmen; Máñez, Salvador; Giner, Rosa M; Escandell, José M; López-Ginés, Concha; Ríos, José-Luis

    2007-01-26

    Scropolioside A, an iridoid isolated from Scrophularia auriculata ssp. pseudoauriculata, showed anti-inflammatory properties against different experimental models of delayed-type hypersensitivity. This iridoid reduced the oedema induced by oxazolone by 79% (72 h) at 0.5 mg/ear while reducing that induced by sheep red blood cells by 47% (18 h), 45% (24 h) and 36% (48 h) at 10 mg/kg. In vivo it reduced both oedema formation and cell infiltration whereas in vitro it reduced the proliferation of activated T-lymphocytes (IC50 of 67.74 microM). Treatment with scropolioside A (100 microM) 18 and 24 h after phytohemagglutinin stimulation increased the number of cells arrested in the subG(0) phase whereas treatment 3 h after stimulation clearly increased the number of cells that passed to the S phase. Scropolioside A also inhibited the production of prostaglandin E2, leukotriene B4, nitric oxide, interleukin-1beta, interleukin-2, interleukin-4, tumour necrosis factor-alpha and interferon-gamma, but had no effect on the production of interleukin-10. Moreover, it modified the expression of both nitric oxide synthase-2 and cyclooxygenase-2, as well as the activation of nuclear factor-kappaB in RAW 264.7 macrophages. PMID:17113578

  15. Impact of the Absence of Stem-Specific ?-Glucosidases on Lignin and Monolignols1[W

    PubMed Central

    Chapelle, Aurélie; Morreel, Kris; Vanholme, Ruben; Le-Bris, Philippe; Morin, Halima; Lapierre, Catherine; Boerjan, Wout; Jouanin, Lise; Demont-Caulet, Nathalie

    2012-01-01

    Monolignol glucosides are thought to be implicated in the lignin biosynthesis pathway as storage and/or transportation forms of cinnamyl alcohols between the cytosol and the lignifying cell walls. The hydrolysis of these monolignol glucosides would involve ?-glucosidase activities. In Arabidopsis (Arabidopsis thaliana), in vitro studies have shown the affinity of ?-GLUCOSIDASE45 (BGLU45) and BGLU46 for monolignol glucosides. BGLU45 and BGLU46 genes are expressed in stems. Immunolocalization experiments showed that BGLU45 and BGLU46 proteins are mainly located in the interfascicular fibers and in the protoxylem, respectively. Knockout mutants for BGLU45 or BGLU46 do not have a lignin-deficient phenotype. Coniferin and syringin could be detected by ultra-performance liquid chromatography-mass spectrometry in Arabidopsis stems. Stems from BGLU45 and BGLU46 mutant lines displayed a significant increase in coniferin content without any change in coniferyl alcohol, whereas no change in syringin content was observed. Other glucosylated compounds of the phenylpropanoid pathway were also deregulated in these mutants, but to a lower extent. By contrast, BGLU47, which is closely related to BGLU45 and BGLU46, is not implicated in either the general phenylpropanoid pathway or in the lignification of stems and roots. These results confirm that the major in vivo substrate of BGLU45 and BGLU46 is coniferin and suggest that monolignol glucosides are the storage form of monolignols in Arabidopsis, but not the direct precursors of lignin. PMID:22984124

  16. Water-soluble constituents of amomum seed.

    PubMed

    Kitajima, Junichi; Ishikawa, Toru

    2003-07-01

    From the water-soluble portion of the methanolic extract of the amomum seed (seed of Amomum xanthioides WALL.), which has been used as a medicine for stomachic and digestive disorders, ten compounds, including two new and three newly isolated monoterpenoid glucosides and a newly isolated octane-tetrol, were isolated. Their structures were determined by spectral investigation. PMID:12843607

  17. BIOAVAILABILITY OF CITRUS LIMONOIDS TO HUMANS

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Citrus limonoids occur in significant quantities in citrus fruit and juice as water-soluble limonoid glucosides. They have demonstrated significant anti-tumor activity in animal and cancer cell screens. In this study we examined the plasma of four groups of four healthy male and female subjects (n...

  18. Amer. J. Bot. 70(6): 912-915. 1983. HORMONAL REGULATION OF EPIPHYLLOUS BUD RELEASE AND

    E-print Network

    Rieseberg, Loren

    the notches in the leaf. This inhibiting substancewas assumed to be a hormone (Loeb, 1917).Reed (1923 in- cluded increased levels of catalase, carbohy- drases, reducing sugars and glucosides, but de-benzylamino purine (BAP), but that naphthaleneacetic acid (NAA) inhibited budding of both detached leaves

  19. [Study of screening nephroprotective bioactive substances based on triple-color fluorescence probes in Carthami flos].

    PubMed

    Lan, Xiao-Hong; Xiao, Shun; Gong, Wan; Wang, Yi; Zhao, Xiao-Ping

    2014-05-01

    In this study, an approach based on triple-color fluorescence probes was developed for screening potential nephro-protective bioactive substances. Three fluorescent probes (i. e. FDA, MTR and Hoechst 33342) were used to label HK-2 cells injured by doxorubicin hydrochloride, and cellular fluorescence images were subsequently acquired and analyzed by a cellular-fluorescence image microscopy platform. The established method was applied to screening 53 components of Carthami Flos, and three components C17, C18 and C19 were found to exhibit nephroprotective effects against doxorubicin hydrochloride induced injury on HK-2 cells. Eight compounds (i. e. hydroxysafflor yellow A, 6-hydroxykaempferol-3-O-rutinoside-6-O-glucoside, 6-hydroxykaempferol-3,6-di-O-gluco-side or 6-hydroxykaempferol-6, 7-di-O-glucoside, 6-hydroxykaempferol-3-O-rutinoside, 6-hydroxykaempferol-3-O-glucoside or 6-hydroxykaempferol-7-O-glucoside, rutin, isoquercetin, and kaempferol-3-O-rutinoside) in components C17, C18 and C19 were preliminarily identified by liquid chromatography-mass spectrometry (LC-MS). Isoquercetin, rutin, kaempferol-3-O-rutinoside, and hydroxysafflor yellow A were confirmed by comparing with reference substances, Further study indicated that these four compounds had moderate nephroprotective effects, while isoquercetin showed a significant nephroprotective effect in a dose-dependent manner. These results suggest that isoquercetin, rutin, kaempferol-3-O-rutinoside and hydroxysafflor yellow A might be the nephroprotective bioactive substances in Carthami Flos. PMID:25282899

  20. DOI: 10.1021/la9021382 97Langmuir 2010, 26(1), 97103 Published on Web 07/30/2009 pubs.acs.org/Langmuir

    E-print Network

    Wan, Xin-hua

    .acs.org/Langmuir © 2009 American Chemical Society Study on the Gel to Crystal Transition of a Novel Sugar-Appended Gelator 15, 2009 4-(40 -Ethoxyphenyl)phenyl--O-D-glucoside (1) was synthesized. A perfect crystal of 1 and then collapsed into a needlelike crystal. The crystal and the gel were characterized by X-ray diffraction, UV

  1. Saponins from Strasburgeria robusta.

    PubMed

    Um, B H; Pouplin, T; Lobstein, A; Weniger, B; Litaudon, M; Anton, R

    2001-06-01

    The isolation of three saponins, 24-hydroxytormentic acid ester glucoside (1), niga-ichigoside F1 (2) and niga-ichigoside F2 (3), from the stem bark of Strasburgeria robusta, an endemic plant from New Caledonia, is reported. PMID:11429265

  2. VOL. 241616 COMMUNICATIONS Studies on the Barks of the Family

    E-print Network

    Berry, R. Stephen

    VOL. 241616 COMMUNICATIONS Studies on the Barks of the Family Salicaceae. 11. Salireposide from the Bark of Populus tremuloides Sir: In our recent paper' on the structure of the new glucoside, tremuloidin, the presence of the gluco- side, populin, in the extract of the bark of Populus tremuloideswas

  3. Oxidation of Indole-3-acetic Acid and Oxindole-3-acetic Acid to 2,3-Dihydro-7-hydroxy-2-oxo-1H Indole-3-acetic Acid-7?-O-?-d-Glucopyranoside in Zea mays Seedlings 1

    PubMed Central

    Nonhebel, Heather M.; Bandurski, Robert S.

    1984-01-01

    Radiolabeled oxindole-3-acetic acid was metabolized by roots, shoots, and caryopses of dark grown Zea mays seedlings to 2,3-dihydro-7-hydroxy-2-oxo-1H indole-3-acetic acid-7?-O-?-d-glycopyranoside with the simpler name of 7-hydroxyoxindole-3-acetic acid-glucoside. This compound was also formed from labeled indole-3-acetic acid supplied to intact seedlings and root segments. The glucoside of 7-hydroxyoxindole-3-acetic acid was also isolated as an endogenous compound in the caryopses and shoots of 4-day-old seedlings. It accumulates to a level of 4.8 nanomoles per plant in the kernel, more than 10 times the amount of oxindole-3-acetic acid. In the shoot it is present at levels comparable to that of oxindole-3-acetic acid and indole-3-acetic acid (62 picomoles per shoot). We conclude that 7-hydroxyoxindole-3-acetic acid-glucoside is a natural metabolite of indole-3-acetic acid in Z. mays seedlings. From the data presented in this paper and in previous work, we propose the following route as the principal catabolic pathway for indole-3-acetic acid in Zea seedlings: Indole-3-acetic acid ? Oxindole-3-acetic acid ? 7-Hydroxyoxindole-3-acetic acid ? 7-Hydroxyoxindole-3-acetic acid-glucoside. PMID:11540902

  4. Clerodane and Ent-kaurane Diterpene Glycosyl and Glycoside Derivatives from the Leaves of Casearia sylvestris

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Five new clerodane diterpene glycosides caseariasides A-E (1-4) and three new ent-kaurane diterpene glucosides sylvestrisides C-E (6-8) were isolated from the leaves of Casearia sylvestris. Their structures were determined on the basis of chemical and spectroscopic analyses....

  5. Phenolic Component Profiles of Mustard Greens, Yu Choy, and 15 Other Brassica Vegetables

    PubMed Central

    Lin, Long-Ze; Harnly, James M

    2013-01-01

    A liquid chromatography–mass spectrometry (LC-MS) profiling method was used to characterize the phenolic components of 17 leafy vegetables from Brassica species other than Brassica oleracea. The vegetables studied were mustard green, baby mustard green, gai choy, baby gai choy, yu choy, yu choy tip, bok choy, bok choy tip, baby bok choy, bok choy sum, Taiwan bok choy, Shanghai bok choy, baby Shanghai bok choy, rapini broccoli, turnip green, napa, and baby napa. This work led to the tentative identification of 71 phenolic compounds consisting of kaempferol 3-O-diglucoside-7-O-glucoside derivatives, isorhamnetin 3-O-glucoside-7-O-glucoside hydroxycinnamoyl gentiobioses, hydroxycinnamoylmalic acids, and hydroxycinnamoylquinic acids. Ten of the compounds, 3-O-diacyltriglucoside-7-O-glucosides of kaempferol and quercetin, had not been previously reported. The phenolic component profiles of these vegetables were significantly different than those of the leafy vegetables from B. oleracea. This is the first comparative study of these leafy vegetables. Ten of the vegetables had never been previously studied by LC-MS. PMID:20465307

  6. ORIGINAL ARTICLE Generation of cyanogen-free transgenic cassava

    E-print Network

    Sayre, Richard

    ORIGINAL ARTICLE Generation of cyanogen-free transgenic cassava Received: 26 September 2002 / Accepted: 25 January 2003 / Published online: 18 March 2003 Ó Springer-Verlag 2003 Abstract Cassava. Cassava, however, contains potentially toxic levels of the cyanogenic glucoside, linamarin. The cyanogen

  7. Red palm oil-supplemented and biofortified gari on the carotenoid and retinyl palmitate concentrations of triacylglycerol-rich plasma of women

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Boiled biofortified cassava containing ß-carotene (BC) can increase retinyl palmitate (RP) in triacylglycerol (TAG)-rich plasma. Thus, it might alleviate vitamin A deficiency. Cassava requires extensive preparation to decrease its level of cyanogenic glucosides, which can be fatal. Garification ...

  8. Uptake of wetting method in Africa to reduce cyanide poisoning and konzo from cassava

    E-print Network

    Uptake of wetting method in Africa to reduce cyanide poisoning and konzo from cassava J. Howard Keywords: Konzo Cyanide poisoning Cyanogenic glucosides Cassava Wetting method a b s t r a c t Cassava breakdown to toxic cyanide. Cyanide ingestion from bitter cassava can cause cyanide poisoning sometimes

  9. Forward Genetics by Genome Sequencing Reveals That Rapid Cyanide Release Deters Insect Herbivory of Sorghum bicolor

    PubMed Central

    Krothapalli, Kartikeya; Buescher, Elizabeth M.; Li, Xu; Brown, Elliot; Chapple, Clint; Dilkes, Brian P.; Tuinstra, Mitchell R.

    2013-01-01

    Whole genome sequencing has allowed rapid progress in the application of forward genetics in model species. In this study, we demonstrated an application of next-generation sequencing for forward genetics in a complex crop genome. We sequenced an ethyl methanesulfonate-induced mutant of Sorghum bicolor defective in hydrogen cyanide release and identified the causal mutation. A workflow identified the causal polymorphism relative to the reference BTx623 genome by integrating data from single nucleotide polymorphism identification, prior information about candidate gene(s) implicated in cyanogenesis, mutation spectra, and polymorphisms likely to affect phenotypic changes. A point mutation resulting in a premature stop codon in the coding sequence of dhurrinase2, which encodes a protein involved in the dhurrin catabolic pathway, was responsible for the acyanogenic phenotype. Cyanogenic glucosides are not cyanogenic compounds but their cyanohydrins derivatives do release cyanide. The mutant accumulated the glucoside, dhurrin, but failed to efficiently release cyanide upon tissue disruption. Thus, we tested the effects of cyanide release on insect herbivory in a genetic background in which accumulation of cyanogenic glucoside is unchanged. Insect preference choice experiments and herbivory measurements demonstrate a deterrent effect of cyanide release capacity, even in the presence of wild-type levels of cyanogenic glucoside accumulation. Our gene cloning method substantiates the value of (1) a sequenced genome, (2) a strongly penetrant and easily measurable phenotype, and (3) a workflow to pinpoint a causal mutation in crop genomes and accelerate in the discovery of gene function in the postgenomic era. PMID:23893483

  10. Optimization of ultrasound-assisted extraction of anthocyanins from haskap berries (Lonicera caerulea L.) using Response Surface Methodology.

    PubMed

    Celli, Giovana Bonat; Ghanem, Amyl; Brooks, Marianne Su-Ling

    2015-11-01

    Haskap berries (Lonicera caerulea L.) are a rich source of bioactive molecules. As such, the extraction of anthocyanins is important for the development of many value-added products and functional food ingredients. In this paper, the ultrasound-assisted extraction (UAE) of anthocyanins from haskap berries was investigated. Significant independent variables were screened and optimized using Plackett-Burman (PB) and Box-Behnken (BB) designs, respectively. The mathematical model showed a high coefficient of determination (R(2)=0.9396) and the optimum conditions for the extraction were as follows: liquid/solid ratio 25:1 (mL/g), solvent composition of 80% ethanol, addition of 0.5% formic acid, ultrasound bath temperature of 35°C for 20 min. Under these conditions, the total anthocyanin content of 22.73 mg cyaniding 3-glucoside equivalents (C3G)/g dry weight (DW) was consistent with the predicted response of 22.45 mg C3G/g DW from the model (mean error of 1.28%). Five anthocyanins were identified in the optimized extract, namely cyanidin 3,5-diglucoside, cyanidin 3-glucoside, cyanidin 3-rutinoside, pelargonidin 3-glucoside, and peonidin 3-glucoside. Thus, UAE is a suitable technique for the extraction of anthocyanins from haskap berries. PMID:26186866

  11. J. Org. Chem. 1995,60, 2147-2152 2147 Modification of a Boronic Acid Cleft Produces a

    E-print Network

    Smith, Bradley D.

    -D-glucopyranoside through bulk, liquid organic membranes. At pH 6.3, the carrier did not significantly facilitate glucoside as chemosensors'l and carriers for membrane transport.12 1 2 To date, most Lewis acid catalysts have been prepared

  12. Identification of a new angiotensin-converting enzyme (ACE) inhibitor from Thai edible plants.

    PubMed

    Simaratanamongkol, Arunee; Umehara, Kaoru; Noguchi, Hiroshi; Panichayupakaranant, Pharkphoom

    2014-12-15

    Eight Thai edible plants were tested for their inhibitory activity against an angiotensin-converting enzyme (ACE) using an in vitro assay. The methanol extract of Apium graveolens exhibited significant ACE inhibitory activity with an IC50 value of 1.7 mg/ml, and was then subjected to an isolation procedure that resulted in identification of a pure active constituent, junipediol A 8-O-?-d-glucoside (1-?-d-glucosyloxy-2-(3-methoxy-4-hydroxyphenyl)-propane-1,3-diol) (1), which had good ACE inhibitory activity with an IC50 value of 76 ?g/ml. Another eight known compounds, isofraxidin-?-d-glucoside (2), roseoside (3), apigenin-7-O-?-d-glucoside (4), luteolin-7-O-?-d-glucoside (5), icariside D2 (6), apiin (7), chrysoeriol-7-O-?-d-apiosylglucoside (8), and 11,21-dioxo-3 ?,15 ?,24-trihydroxyurs-12-ene-24-O-?-d-glucopyranoside (9) were also identified. Although each of these five constituents (2-6) isolated from the same fraction as 1 showed no activity at concentrations of 500 ?M, together, when each was present at 300 ?g/ml, they enhanced the inhibitory activity of 500 ?M of 1 from 64% to 81%. PMID:25038653

  13. TRANSGENIC MAIZE WITH INCREASED ZEATIN O-GLUCOSYLATION

    Technology Transfer Automated Retrieval System (TEKTRAN)

    O-Glycosylation plays an important role in regulating the levels of cytokinins. O-glucosides are likely to be important in cytokinin storage and transport since they are resistant to dehydrogenases (oxidases) and can be converted back to free bases. Maize transformants harboring the bean zeatin O-gl...

  14. Phenolic component profiles of mustard greens, yu choy, and 15 other brassica vegetables.

    PubMed

    Lin, Long-Ze; Harnly, James M

    2010-06-01

    A liquid chromatography-mass spectrometry (LC-MS) profiling method was used to characterize the phenolic components of 17 leafy vegetables from Brassica species other than Brassica oleracea. The vegetables studied were mustard green, baby mustard green, gai choy, baby gai choy, yu choy, yu choy tip, bok choy, bok choy tip, baby bok choy, bok choy sum, Taiwan bok choy, Shanghai bok choy, baby Shanghai bok choy, rapini broccoli, turnip green, napa, and baby napa. This work led to the tentative identification of 71 phenolic compounds consisting of kaempferol 3-O-diglucoside-7-O-glucoside derivatives, isorhamnetin 3-O-glucoside-7-O-glucoside hydroxycinnamoyl gentiobioses, hydroxycinnamoylmalic acids, and hydroxycinnamoylquinic acids. Ten of the compounds, 3-O-diacyltriglucoside-7-O-glucosides of kaempferol and quercetin, had not been previously reported. The phenolic component profiles of these vegetables were significantly different than those of the leafy vegetables from B. oleracea. This is the first comparative study of these leafy vegetables. Ten of the vegetables had never been previously studied by LC-MS. PMID:20465307

  15. Genome wide association mapping for leaf

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Cyanogenic glucosides are natural compounds found in over 1,000 species of angiosperms that produce HCN and are deemed undesirable for agricultural use. However, these compounds are important components of primary defensive mechanisms of many plant species. One of the best-studied cyanogenic gluco...

  16. Action of an endo-?-1,3(4)-glucanase on cellobiosyl unit structure in barley ?-1,3:1,4-glucan

    E-print Network

    Kuge, Takao; Nagoya, Hiroki; Tryfona, Theodora; Kurokawa, Tsunemi; Yoshimi, Yoshihisa; Dohmae, Naoshi; Tsubaki, Kazufumi; Dupree, Paul; Tsumuraya, Yoichi; Kotake, Toshihisa

    2015-06-01

    ,3-glucosidic linkages, but it also contains minor structures such as cellobiosyl units. In the present study, we examined the action of an endo-?-1,3(4)-glucanase from Trichoderma sp. on a minor structure in barley ?-1,3:1,4-glucan. To find the minor structure...

  17. Isoflavone profiles of red clovers and their distribution in different parts harvested at different growing stages.

    PubMed

    Tsao, Rong; Papadopoulos, Yousef; Yang, Raymond; Young, J Chris; McRae, Ken

    2006-08-01

    The isoflavone compositions and concentrations in the leaf, flower, petiole, and stem of 13 red clover cultivars were studied using high-performance liquid chromatography coupled with a diode array and a mass spectrometric detector with negative electrospray ionization. Different cultivars showed significantly different concentrations of individual and total isoflavones. The leaf contained the highest overall concentration, followed by the stem, petiole, and flower. Biochanin A and formononetin were the predominant isoflavones in all cultivars and all parts, along with eight other minor aglycones, daidzein, genistein, glycitein, irilone, orobol, pratensein, pseudobaptigenin, and prunetin, and four minor malonylglycosides, genistein-7-glucoside-6' '-malonate, orobol-7-glucoside-6' '-malonate, formononetin-7-glucoside-6' '-malonate, and biochanin A-7-glucoside-6' '-malonate. The isoflavone compositions and concentrations were also found to be different between red clover parts harvested at the early bud stage and the late flowering stage. Sample storage and handling prior to analysis were also found to be important. Samples in this study were kept at -5 degrees C for a few days before being freeze-dried and were found to contain mainly the aglycones of isoflavones. This may actually be an advantage in that "natural" and more bioactive isoflavones can be obtained without using chemical hydrolysis. Findings in this study therefore provide important information for developing isoflavone-rich red clovers and for optimizing harvest timing and choosing the right part of the red clover plant. PMID:16881680

  18. Isolation and effects of citrus limonoids on cytochrome p450 inhibition, apoptotic induction and cytotoxicity on human cancer cells. 

    E-print Network

    Poulose, Shibu M.

    2007-04-25

    study, cytotoxic effects of limonoid aglycones and glucosides were assessed on human SH-SY5Y neuroblastoma and colon carcinoma (CaCo-2) cell lines and compared with the non-cancerous Chinese hamster ovary (CHO) cells. Significant (P < 0.001) cytotoxic...

  19. Diterpenoids from Casearia sylvestris

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Two highly oxygenated clerodane diterpenes casearins U (1) and V (2) and two ent-kaurane diterpene glucosides sylvestrisides A (3) and B (4) were isolated from the leaves of Casearia sylvestris, together with 13 known compounds. Their structures were established on the basis of 1D and 2D NMR spectro...

  20. Indirect Homologous Competitive Enzyme-Linked Immunosorbent Assay for the Detection of a Class of Glycosylated Dihydrochalcones

    E-print Network

    Hammock, Bruce D.

    -(2,6-dihydroxy-4-glucoside phenyl)propyl) benzoic acid, to thyroglobulin and bovine serum albumin, respectively compounds. They are present in many plants. Flavonoid patterns are normally characteristic of individual plants. They often are ubiquitous in leaves, stems, roots, and fruits and thus form an important part