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1

Synthesis and cytotoxicity of a novel iridoid glucoside derived from aucubin.  

PubMed

The novel iridoid glycoside 2 was prepared in six steps (15% overall yield) from natural aucubin (1) and fully characterized. Compound 2, which comprises the same conjugated cyclopentenone pharmacophore as known antitumor oxylipins and prostaglandins, displayed significant antiproliferative in vitro activity towards leukemia L1210 cells. The Michael addition of nucleophilic thiols to compound 2 occurred on a different position compared to classical delta7-prostaglandin A1 methyl ester. The resulting adducts 7a and 7b were fully characterized, and their MS fragmentation patterns were elucidated. PMID:17192013

Mouriès, Christine; Rakotondramasy, Vokatsoa C; Libot, Francine; Koch, Michel; Tillequin, François; Deguin, Brigitte

2005-05-01

2

Iridoid Glucosides from Penstemon nitidus.  

PubMed

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

Teborg, D; Junior, P

1991-04-01

3

Iridoid glucosides of Paederota lutea and the relationships between Paederota and Veronica.  

PubMed

In a chemical investigation of the water soluble compounds in Paederota lutea eight known iridoids were isolated together with a new one with a 8,9-double bond, namely paederotoside (10-O-benzoyl-6'-O-alpha-arabino(1-->6)-beta-glucopyranosyl arborescosidic acid) and the 6-hydroxy-flavone glucoside 4'-O-methylscutellarein 7-O-beta-glucopyranoside. The known iridoid glucosides were 8-epiloganic acid, gardoside, aucubin, catalpol and the 6-O-esters of catalpol: veronicoside, catalposide, amphicoside and verproside. The compounds isolated show that Paederota has a glycoside content almost identical to that of a general Veronica species, and this is in good agreement with the results from recent investigations of the phylogeny of Veronica and its closest relatives, where Paederota is placed as a sister-group next to Veronica. In an analysis of the iridoid glucosides from some of these relatives, it is shown that Veronica, Paederota, Picrorhiza and Veronicastrum are all characterized by containing 6-O-esters of catalpol. Some less closely related taxa namely: Lagotis, Wulfenia, Plantago, Aragoa and Globularia instead contain 10-O-esters of catalpol or aucubin. PMID:15279984

Albach, Dirk C; Gotfredsen, Charlotte Held; Jensen, Søren Rosendal

2004-07-01

4

Iridoid glucosides from the leaves and stems of Duranta erecta  

Microsoft Academic Search

From the leaves of Duranta erecta, four new iridoid glucosides, duranterectosides A, B, C and D, were isolated along with durantosides I and II, lamiide, lamiidoside and verbascoside. Duranterectoside A was also isolated from the stems together with durantosides I, II and III, and lamiidoside. The structures of the new compounds were elucidated based on the spectroscopic evidence.

Yoshio Takeda; Youko Morimoto; Takashi Matsumoto; Choei Ogimi; Eiji Hirata; Anki Takushi; Hideaki Otsuka

1995-01-01

5

Iridoid glucosides from the leaves and stems of Duranta erecta.  

PubMed

From the leaves of Duranta erecta, four new iridoid glucosides, duranterectosides A, B, C and D, were isolated along with durantosides I and II, lamiide, lamiidoside and verbascoside. Duranterectoside A was also isolated from the stems together with durantosides I, II and III, and lamiidoside. The structures of the new compounds were elucidated based on the spectroscopic evidence. PMID:7626266

Takeda, Y; Morimoto, Y; Matsumoto, T; Ogimi, C; Hirata, E; Takushi, A; Otsuka, H

1995-07-01

6

Further iridoid glucosides in the genus Manulea (Scrophulariaceae).  

PubMed

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

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

2015-01-01

7

Iridoid glucosides of the genus Veronica s.l. and their systematic significance  

Microsoft Academic Search

.  ?16 iridoid glucosides and 3 aromatic compounds were isolated from Bulgarian natural populations of Veronica L. and Pseudolysimachion Opiz species. The distribution of 11 compounds in 34 species (96 samples) was shown. Seven Veronica and Pseudolysimachion species were screened for iridoids for the first time and a phenylethanoid glycoside, calceolarioside C, was found for the\\u000a first time in the genus

R. Taskova; D. Peev; N. Handjieva

2002-01-01

8

Sequestration of glucosinolates and iridoid glucosides in sawfly species of the genus Athalia and their role in defense against ants.  

PubMed

In this study, the larval sequestration abilities and defense effectiveness of four sawfly species of the genus Athalia (Hymenoptera: Tenthredinidae) that feed as larvae either on members of the Brassicaceae or Plantaginaceae were investigated. Brassicaceae are characterized by glucosinolates (GLSs), whereas Plantaginaceae contain iridoid glucosides (IGs) as characteristic secondary compounds. Athalia rosae and A. liberta feed on members of the Brassicaceae. Larvae of A. rosae sequester aromatic and aliphatic GLSs of Sinapis alba in their hemolymph, as shown previously, but no indolic GLSs; A. liberta larvae with a narrower host range sequester aliphatic as well as indolic GLSs from their host plant Alliaria petiolata. Larvae of A. circularis and A. cordata are specialized on members of the Plantaginaceae. Athalia circularis utilizes mainly Veronica beccabunga as host plant, whereas A. cordata feeds additionally on Plantago lanceolata. Both sawfly species sequester the IGs aucubin and catalpol. In V. beccabunga, catalpol esters and carboxylated IGs also occur. The high catalpol concentrations in hemolymph of A. circularis can only be explained by a metabolization of catalpol esters and subsequent uptake of the resulting catalpol. The carboxylated IGs of the plant are excreted. The IG-sequestering sawfly species are able to accumulate much higher glucoside concentrations in their hemolymph than the GLS-sequestering species, and the concentration of IGs in hemolymph increases constantly during larval development. The defensive effectiveness of hemolymph that contains GLSs or IGs and of the respective glucosides was tested in feeding-bioassays against a potential predator, the ant Myrmica rubra (Hymenoptera: Formicidae). Hemolymph of IG-sequestering cryptic A. cordata larvae has a higher deterrence potential than hemolymph of the GLS-sequestering conspicuous A. rosae larvae. The results show that glucoside sequestration is widespread in the genus Athalia, but that the specific glucoside uptake can result in different defense effectiveness against a predator species. PMID:20127151

Opitz, Sebastian E W; Jensen, Søren R; Müller, Caroline

2010-02-01

9

Analysis of iridoid glucosides from Paederia scandens using HPLC-ESI-MS/MS.  

PubMed

Iridoid glycosides are an important class of natural products and have many biological activities. Iridoid glucosides in an extract of the plant species Paederia scandens were investigated using reversed-phase high performance liquid chromatography and electrospray quadrupole time-of-flight-type tandem mass spectrometry. The elemental composition of most of the compounds was determined by accurate mass and relative isotopic abundance (RIA) measurements. In positive ion mode, the fragmentation of [M+NH4](+) precursor ions was carried out using low energy collision-induced electrospray ionization tandem spectrometry. The neutral losses of NH3, H2O, Glc, and the side chain of the iridoid moiety were the main fragmentation patterns observed. For simple iridoid glycosides, the main differences were related to the side chains. Fragmentation of the [M-H](-)precursor ions was achieved for the compounds possibly having phenolic acid group. The connection order of the iridoid, sugar, and phenolic acid moieties, and the linkage of the 6-OH group of the sugar to the phenolic acid were unambiguously confirmed using a combination of MS/MS spectra in both positive and negative ion modes, and our previous work. For some trace dimeric iridoid glucosides, the connection order between the asperuloside and paederoside moieties was determined by the characteristic product ions; this was supported by D-labeling experiments. A total of 24 iridoid glucosides, including 14 new species, were identified or tentatively characterized based on exact mass, RIA values, tandem mass spectra, and D-labeling experiments. PMID:23466447

Wu, Zhi-Jun; Wang, Jian-Hua; Fang, Dong-Mei; Zhang, Guo-Lin

2013-04-01

10

Iridoid glucosides from Penstemon secundiflorus and P. grandiflorus: Revised structure of 10-hydroxy-8-epihastatoside  

Microsoft Academic Search

Thorough large scale investigations of Penstemon secundiflorus ssp. lavendulus and of P. grandiflorus resulted in the isolation of the new iridoid glucosides 5,6?-dihydroxyadoxoside. The structure of 10-hydroxyepihastatoside has been revised to 10-hydroxyhastatoside using a chemical correlation. Also, the known iridoids (5?H)-6-epidihydrocornin, cornin, hastatoside, 8-epihastatoside, ?-dihydrohastatoside, penstemoside, (5?H)-10-hydroxy-6-epidihydrocornin, 10-hydroxycornin and catalpol were isolated.

Henrik Franzyk; Søren Rosendal Jensen; Frank R Stermitz

1998-01-01

11

[Studies on the constituents of Ligustrum species. XIX. Structures of iridoid glucosides from the leaves of Ligustrum lucidum AIT].  

PubMed

Two new iridoid glucosides, named iso-8-epikingiside and 8-demethyl-7-ketologanin, were isolated together with 8-epikingiside, kingiside, ligustroside, 10-hydroxyligustroside, ligustaloside A and ligustaloside B from the leaves of Ligustrum lucidum AIT. (Oleaceae). The stereochemical structures of these new compounds were elucidated on the basis of spectroscopic evidence. PMID:10376004

Kikuchi, M; Kakuda, R

1999-06-01

12

Phenylethanoid and iridoid glycosides from Veronica persica.  

PubMed

A new phenylethanoid glycoside, persicoside (1) and three known phenylethanoid glycosides, acteoside (2), isoacteoside (3) and lavandulifolioside (4) were isolated from the aerial parts of Veronica persica. On the basis of spectral analyses, the structure of the new compound was elucidated to be 3,4-dihydroxy-beta-phenylethoxy-O-[beta-D-glucopyranosyl-(1-->2)]-[beta-D-glucopyranosyl-(1-->3)]-4-O-caffeoyl-beta-D-glucopyranoside. Persicoside (1) and acteoside (2) exhibited radical scavenging activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical. Beside phenylethanoid glycosides, a hexitol, dulcitol (5) and seven known iridoid glucosides, aucubin (6), veronicoside (7), amphicoside (8), 6-O-veratroyl-catalpol (9), catalposide (10), verproside (11) and verminoside (12) were isolated. PMID:12045353

Harput, U Sebnem; Saracoglu, Iclal; Inoue, Makoto; Ogihara, Yukio

2002-06-01

13

Iridoids from Phlomis umbrosa.  

PubMed

Two epimeric pairs of iridoid aglycones, named shanzhigenin methyl ester and 1-epishanzhigenin methyl ester, and 8-acetylshanzhigenin methyl ester and 8-acetyl-1-epishanzhigenin methyl ester, were isolated from Phlomis umbrosa roots, along with five known iridoid glucosides. The four iridoid aglycones are reported for the first time from a natural source. Their structures were established by spectroscopic methods, mainly 1D- and 2D-NMR spectroscopic experiments, and chemical methods. PMID:11234350

Guo, S J; Gao, L M; Cheng, D L

2001-02-01

14

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

PubMed

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 (r(2) = 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

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

2011-01-01

15

Selective sequestration of iridoid glycosides from their host plants in Longitarsus flea beetles.  

PubMed

We investigated in eight species of the flea beetles genus Longitarsus (Coleoptera, Chrysomelidae) whether the beetles take up iridoid glycosides from their host plants of the Lamiaceae, Plantaginaceae, and Scrophulariaceae. Five of the beetle species, L. australis, L. lewisii, L. melanocephalus, L. nigrofasciatus, and L. tabidus, could be shown to sequester iridoid glycosides in concentrations between 0.40 and 1.55% of their dry weight. Eight different iridoid glycosides, acetylharpagide, ajugol, aucubin, catalpol, 8-epi-loganic acid, gardoside, geniposidic acid, and harpagide could be identified in the host plants, yet only aucubin and catalpol are sequestered by the beetles. No iridoid glycosides could be detected in the beetles if neither aucubin nor catalpol were present in the host plant, as in L. minusculus on Stachys recta (acetylharpagide only) and in L. salviae on Salvia pratensis (no iridoid glycosides). In one beetle species, L. luridus, we could not detect any iridoid glycosides although its field host, Plantago lanceolata, had considerable amounts of aucubin and catalpol plus two further iridoids. The five sequestering Longitarsus species differ in their capacity to store the compounds and in their affinity for catalpol relative to aucubin. PMID:11182483

Willinger, G; Dobler, S

2001-04-01

16

Leaf variation in iridoid glycoside content of Plantago lanceolata (Plantaginaceae) and oviposition of the buckeye, Junonia coenia (Nymphalidae)  

Microsoft Academic Search

Summary Chemical analysis of each individual leaf of fivePlantago lanceolata (Plantaginaceae) plants showed that iridoid glycoside content increased from undetectable in the oldest photosynthetic leaves to over 9% dry weight in the youngest leaves. The relative proportion of the two iridoid glycosides inP. lanceolata also changed with leaf age: older leaves had significantly more aucubin, whereas the youngest leaves had

Gretchen K. Klockars; M. Deane Bowers; Barbara Cooney

1993-01-01

17

Systemic, Genotype-Specific Induction of Two Herbivore-Deterrent Iridoid Glycosides in Plantago lanceolata L. in Response to Fungal Infection by Diaporthe adunca (Rob.) Niessel  

Microsoft Academic Search

Iridoid glycosides are a group of terpenoid secondary plant compounds known to deter generalist insect herbivores. In ribwort plantain (Plantago lanceolata), the iridoid glycosides aucubin and catalpol can be induced following damage by insect herbivores. In this study, we investigated whether the same compounds can be induced following infection by the fungal pathogen Diaporthe adunca, the causal agent of a

Hamida B. Marak; Arjen Biere; Jos M. M. Van Damme

2002-01-01

18

Direct and correlated responses to selection on iridoid glycosides in Plantago lanceolata L  

Microsoft Academic Search

Plantago lanceolata L. (ribwort plantain) produces two costly terpenoid secondary plant compounds, the iridoid glycosides aucubin and catalpol. We performed an artificial selection experiment to investigate direct and correlated responses to selection on the constitutive level of iridoid glycosides in the leaves for four generations. Estimated realized heritabilities (+\\/-SE) were 0.23 +\\/- 0.07 and 0.23 +\\/- 0.04 for upward and

H. B. Marak; A. Biere; J. M. M. Van Damme

2000-01-01

19

Iridoid patterns in Galium L. and some phylogenetic considerations.  

PubMed

From 19 species of Galium, members of 6 European sections of the genus, 24 compounds were isolated, namely 16 iridoid glucosides, 2 secoiridoid glucosides and 6 triterpene saponins (the later found only in G. rivale (Sibth. & Sm. Griseb.) The iridoid content was analyzed by thin layer chromatography - densitometry. An effort was made to clarify interspecies relationships, based on the obtained results and previous data. Generally, a nearly uniform iridoid pattern in the studied species was observed. Nevertheless, some distinctions gave reason the following chemical characters to be treated as taxonomic markers: iridoids, secogalioside (characteristic of G. mollugo group), iridoids V1 and V2 (G. humifusum Bieb. and G. verum L.), 6-acetylscandoside (G. incurvum group and G. verum) and the triterpene saponins, rivalioside A and rivalioside C (characteristic of G. rivale). The studied species regarding to the iridoids could be attributed to three lines of evolutionary differentiation. One line is leading to the differentiation of G. rivale. It contains specific triterpenoids as well as iridoid acids, which show parallel development of both glyceraldehyde 3-phosphate/pyruvate and mevalonate biosynthetic routes in this species. A second line includes G. mollugo and G. incurvum species groups and the species G. humifusum and G. verum. Variety of iridoid esters, hydroxy and carboxy derivatives of iridoids and secoiridoids characterised this line. Third line comprises the remaining studied species, members of different sections and species groups. They posses a nearly identical iridoid pattern, which suggests a convergent evolution regarding to the iridoids. PMID:12064718

Mitova, Maya Iv; Anchev, Mincho E; Handjieva, Nedjalka V; Popov, Simeon S

2002-01-01

20

Host dependent iridoid glycoside sequestration patterns in Cionus hortulanus.  

PubMed

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

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

2013-08-01

21

Effects of genotype, habitat, and seasonal variation on iridoid glycoside content of Plantago lanceolata (Plantaginaceae) and the implications for insect herbivores  

Microsoft Academic Search

We investigated the effects of genotype, habitat, and seasonal variation on production of the iridoid glycosides, aucubin and catalpol, in leaves of the common weed Plantago lanceolata. Two genotypes, one each from a lawn and an adjacent abandoned hayfield population, were clonally replicated in the greenhouse, and then planted back into the two habitats. One quarter of the plants from

M. Deane Bowers; Sharon K. Collinge; Susan E. Gamble; Johanna Schmitt

1992-01-01

22

A comparison of sample preparation techniques for quantifying iridoid glycosides sequestered by lepidopteran larvae.  

PubMed

This study compared different methods of tissue preparation for extraction of iridoid glycosides sequestered by three species of lepidopteran larvae. Junonia coenia is a specialist on plant species that produce iridoid glycosides, while the arctiids Estigmene acrea and Spilosoma congrua are both polyphagous and will eat plants that produce iridoid glycosides. Larvae of all three species were reared on leaves of Plantago lanceolata, which produces two primary iridoid glycosides, aucubin and catalpol. Three methods of preparing the specimens before extraction in methanol were compared in all three species: 1) larvae were flash-frozen in liquid nitrogen, 2) larvae were macerated fresh in boiling methanol, or 3) larvae were macerated fresh in room temperature methanol. A set of J. coenia larvae was oven-dried before maceration as an additional treatment for this species only. Junonia coenia sequestered the most iridoid glycosides, while E. acrea sequestered the least, and S. congrua was intermediate. Estigmene acrea was poor at sequestering catalpol. Tissue preparation method only significantly influenced iridoid glycoside recovery from S. congrua, with maceration in room-temperature methanol being the most effective of the three methods. This study shows that treatment of insects prior to iridoid glycoside extraction can influence recovery of the compounds, and that the effects of treatment may vary among different species. PMID:21475987

Lampert, Evan C; Bowers, M Deane

2011-05-01

23

Cytotoxic iridoids from the roots of Patrinia scabra.  

PubMed

Six new iridoid glucosides, patriridosides D-I (1-6), and one new iridoid, scabrol A (7), along with 12 known non-glycosidic and glycosidic iridoids (8-19), have been isolated from an ethanolic extract of the roots of Patrinia scabra. The cytotoxic activity of the isolated compounds against human cervical carcinoma HeLa cells and gastric carcinoma MNK-45 cells was evaluated using the MTT assay. Compounds 1, 4-6, 8, and 18 showed cytotoxic activities against the MNK-45 cell line with respective IC?? values of 15.6, 8.7, 9.4, 30.9, 23.8, and 11.2 ?M, while only compound 10 showed cytotoxicity against the HeLa cell line, with an IC?? value of 24.5 ?M. PMID:23002924

Li, Ning; Di, Lei; Gao, Wen-Chao; Wang, Kai-Jin; Zu, Ling-Bo

2012-10-26

24

Two herbivore-deterrent iridoid glycosides reduce the in-vitro growth of a specialist but not of a generalist pathogenic fungus of Plantago lanceolata L  

Microsoft Academic Search

Summary.   Many secondary plant compounds are involved in defense against both insect herbivores and pathogens. Two secondary plant\\u000a compounds of Plantago lanceolata, the iridoid glycosides catalpol and its precursor aucubin, are well known for their deterrent effects on generalist and\\u000a non-adapted specialist insect herbivores. We tested the effects of these compounds on the in-vitro growth of a specialist\\u000a and generalist

Hamida B. Marak; Arjen Biere; Jos M. M. van Damme

2002-01-01

25

The interplay between toxin-releasing ?-glucosidase and plant iridoid glycosides impairs larval development in a generalist caterpillar, Grammia incorrupta (Arctiidae).  

PubMed

Herbivores with polyphagous feeding habits must cope with a diet that varies in quality. One of the most important sources of this variation in host plant suitability is plant secondary chemistry. We examined how feeding on plants containing one such group of compounds, the iridoid glycosides, might affect the growth and enzymatic activity in a polyphagous caterpillar that feeds on over 80 plant species in 50 different families. Larvae of the polyphagous arctiid, Grammia incorrupta, were reared exclusively on one of two plant species, one of which contains iridoid glycosides (Plantago lanceolata, Plantaginaceae) while the other does not (Taraxacum officinale, Asteraceae). Larval weight was measured on the two host plants, and midgut homogenates of last instar larvae were then assayed for activity and kinetic properties of ?-glucosidases, using both a standard substrate, 4-nitrophenyl-?-D-glucose (NP?Glc), and the iridoid glycoside aucubin, one of the two main iridoid glycosides in P. lanceolata. Larvae feeding on P. lanceolata weighed significantly less and developed more slowly compared to larvae on T. officinale. While the larval midgut ?-glucosidase activity determined with NP?Glc was significantly decreased when fed on P. lanceolata, aucubin was substantially hydrolyzed and the larval ?-glucosidase activity towards both substrates correlated negatively with larval weight. Our results demonstrate that host plants containing high concentrations of iridoid glycosides have a negative impact on larval development of this generalist insect herbivore. This is most likely due to the hydrolysis of plant glycosides in the larval midgut which results in the release of toxic aglycones. Linking the reduced larval weight to the toxin-releasing action of an iridoid glycoside cleaving ?-glucosidase, our results thus support the detoxification limitation hypothesis, suggesting fitness costs for the larvae feeding solely on P. lanceolata. Thus, in addition to the adaptive regulation of midgut ?-glucosidase activity, host plant switching as a behavioral adaptation might be a prerequisite for generalist herbivores that allows them to circumvent the negative effects of plant secondary compounds. PMID:22446106

Pankoke, Helga; Bowers, M Deane; Dobler, Susanne

2012-06-01

26

Anti-inflammatory activity of iridoids and verbascoside isolated from Castilleja tenuiflora.  

PubMed

Castilleja tenuiflora (Orobanchaceae) has been used in Mexican traditional medicine as a treatment for cough, dysentery, anxiety, nausea and vomiting as well as hepatic and gastrointestinal diseases. The ethanolic extract of the aerial parts of Castilleja tenuiflora was separated by silica gel column chromatography. The fractions were evaluated using the induced edema acetate 12-O-tetradecanoylphorbol (TPA) anti-inflammatory activity model. The most active fraction was subjected to medium-pressure liquid chromatography (MPLC) with UV detection at 206 and 240 nm. The following iridoids were isolated: geniposidic acid, aucubin, bartioside, 8-epi-loganin, mussaenoside, and the phenylpropanoid verbascoside. The most active iridoid was geniposidic acid, which was more active than the control (indomethacin), and the least active iridoid was mussaenoside. 8-epi-Loganin, and mussaenoside have not been previously reported to be anti-inflammatory compounds. The results of these investigations confirm the potential of Mexican plants for the production of bioactive compounds and validate the ethnomedical use of Castilleja tenuiflora-like anti-inflammatory plants. PMID:24084016

Carrillo-Ocampo, Danae; Bazaldúa-Gómez, Sugeyla; Bonilla-Barbosa, Jaime R; Aburto-Amar, Rola; Rodríguez-López, Verónica

2013-01-01

27

Hydrophilic carboxylic acids and iridoid glycosides in the juice of American and European cranberries (Vaccinium macrocarpon and V. oxycoccos), lingonberries (V. vitis-idaea), and blueberries (V. myrtillus).  

PubMed

Analysis of the hydrophilic fraction of cranberry juice by reversed-phase HPLC using an Aqua LUNA column with diode array or MS detection revealed the presence of quinic acid, malic acid, shikimic acid, and citric acid. For the first time, two iridoid glucosides were found in the juice. The two iridoid glucosides were shown to be monotropein and 6,7-dihydromonotropein by MS and NMR spectroscopy. A fast reversed-phase HPLC method for quantification of the hydrophilic carboxylic acids was developed and used for analyses of cranberry, lingonberry, and blueberry juices. The level of hydrophilic carboxylic acids in cranberries was 2.67-3.57% (w/v), in lingonberries 2.27-3.05%, and in blueberries 0.35-0.75%. In lingonberries both iridoid glucosides were present, whereas only monotropein was present in blueberries. PMID:12405790

Jensen, Heidi D; Krogfelt, Karen A; Cornett, Claus; Hansen, S Honoré; Christensen, S Brøgger

2002-11-01

28

Iridoid esters from Patrinia saniculaefolia.  

PubMed

Two new iridoids, named patridoid I (1) and patridoid II (2), were isolated from the whole plant of Patrinia saniculaefolia (Valerianaceae), together with the known one, nardostachin (3). The structures of compounds 1 and 2 were established on the basis of spectroscopic methods, including two dimensional (2D NMR) and high resolution fast atom bombardment mass spectrometry (HR-FAB-MS). PMID:12736460

An, Ren Bo; Min, Byung Sun; Na, Min Kyun; Chang, Hyeun Wook; Son, Kun Ho; Kim, Hyun Pyo; Lee, Hyeong Kyu; Bae, KiHwan; Kang, Sam Sik

2003-05-01

29

Iridoid and phenolic glycosides from Wulfenia carinthiaca.  

PubMed

Two new phenylpropanoid glycosides (2'-O-acetylplantamajoside and 2'-O, 6"-O-diacetylplantamajoside), a new iridoid glycoside (10-O-(cinnamoyl)-6'-O-(desacetylalpinosidyl)-catalpol), the two known iridoid glycosides globularin and isoscrophularioside, and the known phenylpropanoid glycoside platamajoside were isolated from the methanolic extract of the underground parts of Wulfenia carinthiaca. Structure elucidations were based on high-resolution mass spectrometry and extensive 1-D and 2-D NMR spectroscopy. PMID:12562078

Arnold, Ulrike W; Zidorn, Christian; Ellmerer, Ernst P; Stuppner, Hermann

2002-01-01

30

Eucommia ulmoides Cortex, Geniposide and Aucubin Regulate Lipotoxicity through the Inhibition of Lysosomal BAX  

PubMed Central

In this study we examined the inhibition of hepatic dyslipidemia by Eucommia ulmoides extract (EUE). Using a screening assay for BAX inhibition we determined that EUE regulates BAX-induced cell death. Among various cell death stimuli tested EUE regulated palmitate-induced cell death, which involves lysosomal BAX translocation. EUE rescued palmitate-induced inhibition of lysosomal V-ATPase, ?-galactosidase, ?-mannosidase, and acid phosphatase, and this effect was reversed by bafilomycin, a lysosomal V-ATPase inhibitor. The active components of EUE, aucubin and geniposide, showed similar inhibition of palmitate-induced cell death to that of EUE through enhancement of lysosome activity. Consistent with these in vitro findings, EUE inhibited the dyslipidemic condition in a high-fat diet animal model by regulating the lysosomal localization of BAX. This study demonstrates that EUE regulates lipotoxicity through a novel mechanism of enhanced lysosomal activity leading to the regulation of lysosomal BAX activation and cell death. Our findings further indicate that geniposide and aucubin, active components of EUE, may be therapeutic candidates for non-alcoholic fatty liver disease. PMID:24586300

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

2014-01-01

31

seco-iridoids from Calycophyllum spruceanum (Rubiaceae).  

PubMed

Three seco-iridoids 7-methoxydiderroside, 6'-O-acetyldiderroside and 8-O-tigloyldiderroside, were isolated from the wood bark of Calycophyllum spruceanum together with the known iridoids loganetin, loganin and the seco-iridoids secoxyloganin, kingiside and diderroside. Their structures were elucidated by means of NMR and MS spectral data analysis. Using NOE correlations and coupling constants, the relative stereochemistry of the new derivatives was established. 7-Methoxydiderroside, 6'-O-acetyldiderroside and the known secoxyloganin and diderroside showed in vitro activity against trypomastigote forms of Trypanosoma cruzi, with IC(50) values of 59.0, 90.2, 74,2 and 84.9 microg/mL, respectively and were compared to the standard gentian violet (IC(50) 7.5 microg/ml). PMID:12943773

Cardona Zuleta, Luz Margarita; Cavalheiro, Alberto José; Siqueira Silva, Dulce Helena; Furlan, Maysa; Marx Young, Maria Claudia; Albuquerque, Sérgio; Castro-Gamboa, Ian; da Silva Bolzani, Vanderlan

2003-09-01

32

Selective transport systems mediate sequestration of plant glucosides in leaf beetles: A molecular basis for adaptation and evolution  

PubMed Central

Chrysomeline larvae respond to disturbance and attack by everting dorsal glandular reservoirs, which release defensive secretions. The ancestral defense is based on the de novo synthesis of monoterpene iridoids. The catabolization of the host-plant O-glucoside salicin into salicylaldehyde is a character state that evolved later in two distinct lineages, which specialized on Salicaceae. By using two species producing monoterpenes (Hydrothassa marginella and Phratora laticollis) and two sequestering species (Chrysomela populi and Phratora vitellinae), we studied the molecular basis of sequestration by feeding the larvae structurally different thioglucosides resembling natural O-glucosides. Their accumulation in the defensive systems demonstrated that the larvae possess transport systems, which are evolutionarily adapted to the glycosides of their host plants. Minor structural modifications in the aglycon result in drastically reduced transport rates of the test compounds. Moreover, the ancestral iridoid-producing leaf beetles already possess a fully functional import system for an early precursor of the iridoid defenses. Our data confirm an evolutionary scenario in which, after a host-plant change, the transport system of the leaf beetles may play a pivotal role in the adaptation on new hosts by selecting plant-derived glucosides that can be channeled to the defensive system. PMID:15365181

Kuhn, Jürgen; Pettersson, Eva M.; Feld, Birte K.; Burse, Antje; Termonia, Arnaud; Pasteels, Jacques M.; Boland, Wilhelm

2004-01-01

33

Five new iridoids from Patrinia rupestris.  

PubMed

Five new iridoids, namely rupesin A-E (1-5, resp.), together with six known iridoids, 6-11, were isolated from the roots of Patrinia rupestris. Their structures were elucidated by spectroscopic methods including IR, UV, MS, and 1D- and 2D-NMR experiments, and comparison with data of known analogues. Compounds 4 and 11, compounds 1, 2, 5, 6, 8, 9, and 10, and compounds 3, 4, and 8 showed significant antibacterial activities against Bacillus subtilis, Escherichia coli, and Staphylococcus aureus, respectively. PMID:17193308

Yang, Xiu-Ping; Li, Er-Wei; Zhang, Qi; Yuan, Cheng-Shan; Jia, Zhong-Jian

2006-07-01

34

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

PubMed Central

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

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

35

Two new iridoids from Patrinia scabra.  

PubMed

From the roots of Patrinia scabra two new iridoids, 3-methylbutyric acid 7-hydroxy-7-hydroxymethyl-4-(3-methyl-butyryloxymethyl)-6-oxo-1,6,7,7a-tetrahydrocyclopenta[c]pyran-1-yl ester (1) and 6-hydroxy-7-methylhexahydrocyclopenta[c]pyran-3-one (2) have been isolated. Their structures were determined by means of NMR spectra and X-ray crystallographic analysis. PMID:15621587

Yang, Gen-Jin; Gu, Zheng-Bing; Liu, Wen-Yong; Qiu, Yan; Li, Ting-Zhao; Zhang, Wei-Dong

2004-12-01

36

Two novel iridoids from Morinda longifolia.  

PubMed

Six secondary metabolites, including two novel iridoids, longifolides A (1) and B (2), were isolated by various chromatographic methods from a methanol extract of branches and leaves of Morinda longifolia Craib. The structures of the compounds were determined on the basis of NMR spectroscopic (1H and 13C NMR, HSQC, HMBC, 1H-1H COSY, NOESY) and FTICR-MS data, as well as by comparison of them with literature values. PMID:25230486

Ban, Ninh Khac; Giang, Vu Huong; Linh, Tran My; Lien, Le Quynh; Ngoc, Ninh Thi; Dat, Le Duc; Thao, Nguyen Phuong; Nhiem, Nguyen Xuan; Cuong, Nguyen Xuan; Van Pham, Cuong; Nam, Nguyen Hoai; Regalado, Jacinto; Van Keo, Huynh; Van Kiem, Phan; Van Minh, Chau

2014-07-01

37

Phenylpropanoid glucosides from Chrozophora obliqua.  

PubMed

From the aerial parts of Chrozophora obliqua, two phenylpropanoid glucosides: 4-O-methyl guaiacylglycerol 9-O-beta-glucopyranoside (1) and 4-O-methyl guaiacylglycerol 8-O-beta-glucopyranoside (2) together with syringin, benzyl alcohol glucoside, isorhamnetin-3-O-beta-glucopyranoside-7-O-alpha-rhamnopyranoside and quercetin-3-O-beta-glucopyranoside-7-O-alpha-rhamnopyranoside have been isolated. The structures of the isolated compounds were verified by means of MS and NMR spectral analyses. PMID:11576610

Mohamed, K M

2001-10-01

38

Conversion of Substrate Analogs Suggests a Michael Cyclization in Iridoid Biosynthesis  

PubMed Central

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

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

2014-01-01

39

The seco-iridoid pathway from Catharanthus roseus.  

PubMed

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

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

40

The seco-iridoid pathway from Catharanthus roseus  

PubMed Central

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

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

41

Journal of Chemical Ecology, Vol. 29, No. 4, April 2003 (C 2003) EFFECT OF IRIDOID GLYCOSIDE CONTENT  

E-print Network

butterfly Melitaea cinxia feeds upon two host plant species in °Aland, Finland, Plantago lanceolata higher than aucubin concentrations in both host species. Plantago lanceolata individuals that were used,aucubin,catalpol,Cotesiamelitaearum,iridoidglycosides, oviposition, Melitaea cinxia, parasitism, Plantago lanceolata, Veronica spicata. INTRODUCTION Secondary

van Nouhuys, Saskya

42

Cucurbitacin glucosides from Citrullus colocynthis.  

PubMed

A new cucurbitacin glucoside 2-O-beta-D-glucopyranosyl-16alpha-20R-dihydroxy-cucurbita-1,5,23E,25(26)-tetraen-3,11,22-trione (1) has been isolated from the methanolic extract of the fruits of Citrulluscolocynthis. The structure has been assigned on the basis of spectral analysis including 1D and 2D NMR techniques. In addition 2-O-beta-D-glucopyranosyl-cucurbitacin B (arvenin I) (2) and 2,25-di-O-beta-D-glucopyranosyl-cucurbitacin L (3) are reported for the first time from this species. PMID:16644537

Nayab, Durey; Ali, Dildar; Arshad, Nuzhat; Malik, Abdul; Choudhary, M Iqbal; Ahmed, Zaheer

2006-05-10

43

Generation of primary amide glucosides from cyanogenic glucosides.  

PubMed

The cyanogenic glucoside-related compound prunasinamide, (2R)-beta-d-glucopyranosyloxyacetamide, has been detected in dried, but not in fresh leaves of the prunasin-containing species Olinia ventosa, Prunus laurocerasus, Pteridium aquilinium and Holocalyx balansae. Experiments with leaves of O. ventosa indicated a connection between amide generation and an excessive production of reactive oxygen species. In vitro, the Radziszewski reaction with H(2)O(2) has been performed to yield high amounts of prunasinamide from prunasin. This reaction is suggested to produce primary amides from cyanogenic glycosides in drying and decaying leaves. Two different benzoic acid esters which may be connected to prunasin metabolism were isolated and identified as the main constituents of chlorotic leaves from O. ventosa and P. laurocerasus. PMID:19195667

Sendker, Jandirk; Nahrstedt, Adolf

2009-02-01

44

Iridoidic pattern in endemic Sardinian plants: the case of Galium species  

Microsoft Academic Search

The monoterpenoid fractions of three endemic Galium ssp. (Rubiaceae) from Sardinia Island were examined and compared with the iridoidic pattern yet known in Galium species. This comparison evidenced theirs endemic characters. In particular, in G.corsicum and in G. glaucophyllum loganic acid was isolated and identified for the first time in Galium genus. In G. schmidii a rare iridoid is present,

Anna Maria Serrilli; Alessia Ramunno; Francesca Amicucci; Valentina Chicarella; Sabrina Santoni; Mauro Ballero; Mauro Serafini; Armandodoriano Bianco

2008-01-01

45

Dolabellane diterpene glucosides from Chrozophora obliqua.  

PubMed

Three novel dolabellane diterpene glucosides and one new dolabellane diterpenoid have been isolated from Chrozophora obliqua. Their structures were elucidated by various NMR and mass spectral techniques. PMID:7765628

Mohamed, K M; Ohtani, K; Kasai, R; Yamasaki, K

1994-09-01

46

Two new iridoids from roots of Patrinia scabra Bunge  

Microsoft Academic Search

Two new iridoids 1,3-dimethyloxy-7-hydroxymethyl-4-(3-methyl-butyryloxymethyl)-1-hydrocyclopenta-4,7-diene[c]pyran-6-one (1) and 1,3-dimethyloxy-7-hydroxymethyl-4-methyloxymethyl-1-hydrocyclopenta-4,7-diene[c]pyran-6-one (2) were isolated from the roots of Patrinia scabra Bunge. The structure elucidation of the isolated compounds was based primarily on HRESIMS, EIMS, IR, UV, 1D- and 2D-NMR analyses, including COSY, HMQC, HMBC and NOESY correlations, as well as X-ray crystallographic analysis.

R. H. Liu; W. D. Zhang; Z. B. Gu; C. Zhang; J. Su; X. K. Xu

2006-01-01

47

Two new iridoids from roots of Patrinia scabra Bunge.  

PubMed

Two new iridoids 1,3-dimethyloxy-7-hydroxymethyl-4-(3-methyl-butyryloxymethyl)-1-hydrocyclopenta-4,7-diene[c]pyran-6-one (1) and 1,3-dimethyloxy-7-hydroxymethyl-4-methyloxymethyl-1-hydrocyclopenta-4,7-diene[c]pyran-6-one (2) were isolated from the roots of Patrinia scabra Bunge. The structure elucidation of the isolated compounds was based primarily on HRESIMS, EIMS, IR, UV, 1D- and 2D-NMR analyses, including COSY, HMQC, HMBC and NOESY correlations, as well as X-ray crystallographic analysis. PMID:16753925

Liu, R H; Zhang, W D; Gu, Z B; Zhang, C; Su, J; Xu, X K

2006-07-20

48

An alternative route to cyclic terpenes by reductive cyclization in iridoid biosynthesis.  

PubMed

The iridoids comprise a large family of distinctive bicyclic monoterpenes that possess a wide range of pharmacological activities, including anticancer, anti-inflammatory, antifungal and antibacterial activities. Additionally, certain iridoids are used as sex pheromones in agriculturally important species of aphids, a fact that has underpinned innovative and integrated pest management strategies. To harness the biotechnological potential of this natural product class, the enzymes involved in the biosynthetic pathway must be elucidated. Here we report the discovery of iridoid synthase, a plant-derived enzyme that generates the iridoid ring scaffold, as evidenced by biochemical assays, gene silencing, co-expression analysis and localization studies. In contrast to all known monoterpene cyclases, which use geranyl diphosphate as substrate and invoke a cationic intermediate, iridoid synthase uses the linear monoterpene 10-oxogeranial as substrate and probably couples an initial NAD(P)H-dependent reduction step with a subsequent cyclization step via a Diels-Alder cycloaddition or a Michael addition. Our results illustrate how a short-chain reductase was recruited as cyclase for the production of iridoids in medicinal plants. Furthermore, we highlight the prospects of using unrelated reductases to generate artificial cyclic scaffolds. Beyond the recognition of an alternative biochemical mechanism for the biosynthesis of cyclic terpenes, we anticipate that our work will enable the large-scale heterologous production of iridoids in plants and microorganisms for agricultural and pharmaceutical applications. PMID:23172143

Geu-Flores, Fernando; Sherden, Nathaniel H; Courdavault, Vincent; Burlat, Vincent; Glenn, Weslee S; Wu, Cen; Nims, Ezekiel; Cui, Yuehua; O'Connor, Sarah E

2012-12-01

49

Transcriptome Analysis Reveals Putative Genes Involved in Iridoid Biosynthesis in Rehmannia glutinosa  

PubMed Central

Rehmannia glutinosa, one of the most widely used herbal medicines in the Orient, is rich in biologically active iridoids. Despite their medicinal importance, no molecular information about the iridoid biosynthesis in this plant is presently available. To explore the transcriptome of R. glutinosa and investigate genes involved in iridoid biosynthesis, we used massively parallel pyrosequencing on the 454 GS FLX Titanium platform to generate a substantial EST dataset. Based on sequence similarity searches against the public sequence databases, the sequences were first annotated and then subjected to Gene Ontology (GO) and Kyoto Encyclopedia of Genes and Genomes (KEGG) based analysis. Bioinformatic analysis indicated that the 454 assembly contained a set of genes putatively involved in iridoid biosynthesis. Significantly, homologues of the secoiridoid pathway genes that were only identified in terpenoid indole alkaloid producing plants were also identified, whose presence implied that route II iridoids and route I iridoids share common enzyme steps in the early stage of biosynthesis. The gene expression patterns of four prenyltransferase transcripts were analyzed using qRT-PCR, which shed light on their putative functions in tissues of R. glutinosa. The data explored in this study will provide valuable information for further studies concerning iridoid biosynthesis. PMID:23202979

Sun, Peng; Song, Shuhui; Zhou, Lili; Zhang, Bing; Qi, Jianjun; Li, Xianen

2012-01-01

50

Host plant iridoid-based chemical defense of an aphid, Acyrthosiphon nipponicus , against ladybird beetles  

Microsoft Academic Search

A Rubiaceae-feeding aphid,Acyrthosiphon nipponicus, is seldom attacked by the ladybird beetle,Harmonia axyridis. A potent deterrent against the beetle was isolated from the aphid and identified as paederoside, an iridoid glycoside originating in the aphid's host,Paederia scandens. The iridoid content was as high as 2% of the intact body weight, and a large portion was found in the cornicle secretion.

Ritsuo Nishida; Hiroshi Fukami

1989-01-01

51

UPLC-TOF-MS Characterization and Identification of Bioactive Iridoids in Cornus mas Fruit  

PubMed Central

Cornus mas L. is indigenous to Europe and parts of Asia. Although Cornus is widely considered to be an iridoid rich genera, only two iridoids have been previously found in this plant. The lack of information on taxonomically and biologically active iridoids prompted us to develop and optimize an analytical method for characterization of additional phytochemicals in C. mas fruit. An ultra performance liquid chromatography (UPLC) coupled with photodiode array spectrophotometry (PDA) and electrospray time-of-flight mass spectrometry (ESI-TOF-MS) was employed and mass parameters were optimized. Identification was made by elucidating the mass spectral data and further confirmed by comparing retention times and UV spectra of target peaks with those of reference compounds. Primary DNA damage and antigenotoxicity tests in E. coli PQ37 were used to screen the iridoids for biological activity. As a result, ten phytochemicals were identified, including iridoids loganic acid, loganin, sweroside, and cornuside. Nine of these were reported for the first time from C. mas fruit. The iridoids did not induce SOS repair of DNA, indicating a lack of genotoxic activity in E. coli PQ37. However, loganin, sweroside, and cornuside did reduce the amount of DNA damage caused by 4-nitroquinoline 1-oxide, suggesting potential antigenotoxic activity. PMID:24228188

West, Brett J.; Jensen, C. Jarakae

2013-01-01

52

A new iridoid compound from Patrinia rupestris (Pall.) Juss.  

PubMed

Extraction of roots of Patrinia rupestris (Pall.) Juss. gave a new iridoid compound, 1?,3?-diethyloxy-7-hydromethyl-4-(3-methyl-butyryloxymethyl)-cyclopenta-4(4a),7(7a)-diene[c]pyran-6-one (1), together with a known compound, (1?,4a?,?6?,7?,7a?)-[4a,5,6,7,7a-hexahydro-6,7-dihydroxy-1-(3-methyl-1-oxobutoxy) cyclopenta[c]pyran-4,7-diyl]bis(methylene) 3-methyl-butanoic acid ester (2). The structure of 1 was characterised by HRESIMS, IR, UV, 1-D NMR and 2-D NMR methods. Compound 2 was isolated from this genus for the first time. PMID:21790497

Qiu, Dong-Feng; Yang, Xiu-Ping; Xu, Yang-Jun; Liu, Xiao-Qing; Liu, Hong-Li; Yuan, Cheng-Shan

2011-10-01

53

Metabolization of cyanogenic glucosides in Hevea brasiliensis  

Microsoft Academic Search

Over 90% of the cyanogenic precursors ofHevea seeds is stored in the endosperm tissue. During seedling development most of the cyanogenic material is consumed to form noncyanogenic compounds. No gaseous HCN is liberated in the course of this process. The ß-glucosidase, responsible for the cleavage of cyanogenic glucosides and the key enzyme for cyanogenesis is widely distributed over all tissues.

R. Lieberei; D. Selmar; B. Biehl

1985-01-01

54

Antioxidant efficacy of iridoid and phenylethanoid glycosides from the medicinal plant Teucrium chamaedris in cell-free systems  

Microsoft Academic Search

Twelve glycosides, seven iridoids and five phenylethanoids, have been isolated from leaf and root methanolic extracts of Wall Germander (Teucrium chamaedrys), a Mediterranean species historically used as a medicinal plant. Among them, three iridoid and one phenylethanoid glycosides have been isolated and characterized for the first time. All of the structures have been elucidated on the basis of their spectral

Severina Pacifico; Brigida D’Abrosca; Maria Teresa Pascarella; Marianna Letizia; Piera Uzzo; Vincenzo Piscopo; Antonio Fiorentino

2009-01-01

55

A chemical-biological study reveals C9-type iridoids as novel heat shock protein 90 (Hsp90) inhibitors.  

PubMed

The potential of heat shock protein 90 (Hsp90) as a therapeutic target for numerous diseases has made the identification and optimization of novel Hsp90 inhibitors an emerging therapeutic strategy. A surface plasmon resonance (SPR) approach was adopted to screen some iridoids for their Hsp90 ? binding capability. Twenty-four iridoid derivatives, including 13 new natural compounds, were isolated from the leaves of Tabebuia argentea and petioles of Catalpa bignonioides. Their structures were elucidated by NMR, electrospray ionization mass spectrometry, and chemical methods. By means of a panel of chemical and biological approaches, four iridoids were demonstrated to bind Hsp90 ?. In particular, the dimeric iridoid argenteoside A was shown to efficiently inhibit the chaperone in biochemical and cellular assays. Our results disclose C9-type iridoids as a novel class of Hsp90 inhibitors. PMID:23362862

Dal Piaz, Fabrizio; Vassallo, Antonio; Temraz, Abeer; Cotugno, Roberta; Belisario, Maria A; Bifulco, Giuseppe; Chini, Maria G; Pisano, Claudio; De Tommasi, Nunziatina; Braca, Alessandra

2013-02-28

56

Unusual sesquiterpene glucosides from Amaranthus retroflexus  

Microsoft Academic Search

Implementing the phytochemical study of the weed Amaranthus retroflexus, four new sesquiterpene glucosides were isolated from the methanolic extract of the plant. The structures of these metabolites are determined on the basis of the mass spectrometry, and 1D and 2D NMR spectroscopies (DQ-COSY, TOCSY, HSQC, HSQC–TOCSY, HMBC, and NOESY). Two compounds are characterized by a new aglycone and differed from

Antonio Fiorentino; Marina DellaGreca; Brigida D'Abrosca; Annunziata Golino; Severina Pacifico; Angelina Izzo; Pietro Monaco

2006-01-01

57

Metabolically Active Glucosides in Oleaceae Seeds  

PubMed Central

The seeds of six woody species of Oleaceae representing three genera, contain high concentrations of water-soluble glucosides, with major absorption maxima below 240 nanometers. In Fraxinus americana seeds three of these compounds, designated GL-3, GL-5, and GL-6, account for almost 10% of the dry weight. They are found in the endosperm and embryo but not in the pericarp. While the level of GL-5 is not particularly influenced by the physiological state of the embryo, that of GL-3 and GL-6 decreases as a result of germination and growth during a 10-day period. As the concentrations of GL-3 and GL-6 decrease, new ultraviolet-absorbing compounds are formed. The changes in the concentration of the ultraviolet-absorbing glucosides during cold temperature after-ripening, prior to germination, are small. When germination of dormant embryos is induced with gibberellic acid, the concentrations of GL-3 and GL-6 decrease in a manner similar to that observed with nondormant embryos. In the presence of abscisic acid no losses of GL-3 and GL-6 were observed. It is suggested that GL-3 and GL-6 fulfill some definite functions in the germination and growth of F. americana embryos, and that gibberellic acid and abscisic acid can exert a regulatory effect on the metabolism of these glucosides. Images PMID:16657368

Sondheimer, E.; Blank, G. E.; Galson, Eva C.; Sheets, F. M.

1970-01-01

58

Analysis of flavonoids and iridoids in Vitex negundo by HPLC-PDA and method validation.  

PubMed

The leaves of Vitex negundo have been reported to contain various bioactive constituents including iridoids and flavonoids. This is the first report on the simultaneous determination of iridoids and flavonoids by HPLC in three different samples of V. negundo leaves collected from three regions of India. Separation of iridoids and flavonoids was accomplished by HPLC and further elaborated for their quantification in V. negundo leaves using a C-18 column with detection at 254 and 330 nm, respectively. The developed HPLC method showed good linearity (r2 > or = 0.999), high precision (RSD < 5%) and a good recovery (99.3-103.0%) of the compounds. All the validation parameters of the developed HPLC were found to be within the permissible limits according to the ICH guidelines. The developed method was robust, accurate and reliable for the quality control of V. negundo leaves. PMID:24273856

Roy, Somendu K; Bairwa, Khemraj; Grover, Jagdeep; Srivastava, Amit; Jachak, Sanjay M

2013-09-01

59

Antioxidative iridoid glycosides from the sky flower (Duranta repens Linn).  

PubMed

Phytochemical investigations were performed on the EtOAc-soluble fraction of the whole plant of the sky flower (Duranta repens) which led to the isolation of the iridoid glycosides 1-6. Their structures were elucidated by both 1D and 2D NMR spectroscopic analysis. All the compounds showed potent antioxidative scavenging activity in four different tests, with half maximal inhibitory concentration (IC(50)) values in the range 0.481-0.719 mM against DPPH radicals, 4.07-17.21 ?M for the hydroxyl radical (·OH) inhibitory activity test, 43.3-97.37 ?M in the total reactive oxygen species (ROS) inhibitory activity test, and 3.39-18.94 ?M in the peroxynitrite (ONOO(-)) scavenging activity test. Duranterectoside A (1) displayed the strongest scavenging potential with IC(50) values of (0.481 ± 0.06 mM, 4.07 ± 0.03, 43.30 ± 0.05, 3.39 ± 0.02 ?M) for the DPPH radicals, ·OH inhibitory activity test, total ROS inhibitory activity test and the ONOO(-) scavenging activity test, respectively. PMID:21299433

Ijaz, Fozia; Ul Haq, Azhar; Ahmad, Ijaz; Ahmad, Nisar; Hussain, Javid; Chen, Sibao

2011-02-01

60

Iridoidic pattern in endemic Sardinian plants: the case of Galium species.  

PubMed

The monoterpenoid fractions of three endemic Galium ssp. (Rubiaceae) from Sardinia Island were examined and compared with the iridoidic pattern yet known in Galium species. This comparison evidenced theirs endemic characters. In particular, in G.corsicum and in G. glaucophyllum loganic acid was isolated and identified for the first time in Galium genus. In G. schmidii a rare iridoid is present, 10-hydroxy-loganin, whose presence in this genus was evidenced only in G. mollugo and loganin isolated for the first time. PMID:18569700

Serrilli, Anna Maria; Ramunno, Alessia; Amicucci, Francesca; Chicarella, Valentina; Santoni, Sabrina; Ballero, Mauro; Serafini, Mauro; Bianco, Armandodoriano

2008-05-10

61

Patterns of Iridoid Glycoside Production and Induction in Plantago lanceolata and the Importance of Plant Age  

Microsoft Academic Search

Induction of allelochemicals is one way that plants efficiently deploy defenses against herbivory. In two separate experiments we investigated the time course of this inductive response and the importance of the timing of herbivory for Plantago lanceolata (Plantaginaceae). We found a localized induced response of catalpol and the ratio of catalpol to total iridoid glycosides in damaged leaves that was

Alexander Fuchs; M. Deane Bowers

2004-01-01

62

Making iridoids/secoiridoids and monoterpenoid indole alkaloids: progress on pathway elucidation.  

PubMed

Members of the Acanthaceae, Apocynaceae, Bignoniaceae, Caprifoliaceae, Gentianaceae, Labiatae, Lamiaceae, Loasaceae, Loganiaceae, Oleaceae, Plantaginaceae, Rubiaceae, Saxifragaceae, Scrophulariaceae, Valerianaceae, and Verbenaceae plant families are well known to accumulate thousands of bioactive iridoids/secoiridoids while the Apocynaceae, Loganiaceae and Rubiaceae families also accumulate thousands of bioactive monoterpenoid indole alkaloids (MIAs), mostly derived from the secologanin and tryptamine precursors. Several large-scale RNA-sequencing projects have greatly advanced the tools available for identifying candidate genes whose gene products are involved in the biosynthesis of iridoids/MIAs. This has led to the rapid comparative bioinformatics guided elucidation of several key remaining steps in secologanin biosynthesis as well as other steps in MIA biosynthesis. The availability of these tools will permit broad scale biochemical and molecular description of the reactions required for making thousands of iridoid/MIAs. This information will advance our understanding of the evolutionary and ecological roles played by these metabolites in Nature and the genes will be used for biotechnological production of useful iridoids/MIAs. PMID:24709280

De Luca, Vincenzo; Salim, Vonny; Thamm, Antje; Masada, Sayaka Atsumi; Yu, Fang

2014-06-01

63

Characterization of 10-Hydroxygeraniol Dehydrogenase from Catharanthus roseus Reveals Cascaded Enzymatic Activity in Iridoid Biosynthesis  

PubMed Central

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

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

2015-01-01

64

Characterization of 10-Hydroxygeraniol Dehydrogenase from Catharanthus roseus Reveals Cascaded Enzymatic Activity in Iridoid Biosynthesis.  

PubMed

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

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

2015-01-01

65

Influence of the stage of ripeness on the composition of iridoids and phenolic compounds in genipap (Genipa americana L.).  

PubMed

Genipap fruits, native to the Amazon region, were classified in relation to their stage of ripeness according to firmness and peel color. The influence of the part of the genipap fruit and ripeness stage on the iridoid and phenolic compound profiles was evaluated by HPLC-DAD-MS(n), and a total of 17 compounds were identified. Geniposide was the major compound in both parts of the unripe genipap fruits, representing >70% of the total iridoids, whereas 5-caffeoylquinic acid was the major phenolic compound. In ripe fruits, genipin gentiobioside was the major compound in the endocarp (38%) and no phenolic compounds were detected. During ripening, the total iridoid content decreased by >90%, which could explain the absence of blue pigment formation in the ripe fruits after their injury. This is the first time that the phenolic compound composition and iridoid contents of genipap fruits have been reported in the literature. PMID:25323434

Bentes, Adria de Sousa; Mercadante, Adriana Zerlotti

2014-11-01

66

New unusual iridoids from the leaves of noni ( Morinda citrifolia L.) show inhibitory effect on ultraviolet B-induced transcriptional activator protein-1 (AP1) activity  

Microsoft Academic Search

A novel iridoid dimer in whose structure the two iridoid units are connected by a rare ether group, together with two new unusual iridoids showing significant inhibition of UVB-induced Activator Protein-1 (AP-1) activity in cell cultures, have been isolated from the leaves of noni (Morinda citrifolia L.). Their structures were determined on the basis of detailed high-field 1D and 2D

Shengmin Sang; Guangming Liu; Kan He; Nanqun Zhu; Zigang Dong; Qunyi Zheng; Robert T Rosen; Chi-Tang Ho

2003-01-01

67

Zearalenone-16-O-glucoside: a new masked mycotoxin.  

PubMed

This paper reports the identification of a barley UDP-glucosyltransferase, HvUGT14077, which is able to convert the estrogenic Fusarium mycotoxin zearalenone into a near-equimolar mixture of the known masked mycotoxin zearalenone-14-O-?-glucoside and a new glucose conjugate, zearalenone-16-O-?-glucoside. Biocatalytical production using engineered yeast expressing the HvUGT14077 gene allowed structural elucidation of this compound. The purified zearalenone-16-O-?-glucoside was used as an analytical calibrant in zearalenone metabolization experiments. This study confirmed the formation of this new masked mycotoxin in barley seedlings as well as in wheat and Brachypodium distachyon cell suspension cultures. In barley roots, up to 18-fold higher levels of zearalenone-16-O-?-glucoside compared to the known zearalenone-14-O-?-glucoside were found. Incubation of zearalenone-16-O-?-glucoside with human fecal slurry showed that this conjugate can also be hydrolyzed rapidly by intestinal bacteria, converting the glucoside back to the parental mycotoxin. Consequently, it should be considered as an additional masked form of zearalenone with potential relevance for food safety. PMID:24386883

Kovalsky Paris, Maria Paula; Schweiger, Wolfgang; Hametner, Christian; Stückler, Romana; Muehlbauer, Gary J; Varga, Elisabeth; Krska, Rudolf; Berthiller, Franz; Adam, Gerhard

2014-02-01

68

New lignan glucosides from the stems of Tinospora sinensis.  

PubMed

Two new lignan glucosides, tinosposides A and B (1 and 2), were isolated from the stems of Tinospora sinensis collected in Hainan Island, China. Their structures were elucidated on the basis of spectroscopic analysis and chemical evidence. PMID:15133225

Li, Wei; Koike, Kazuo; Liu, Lijuan; Lin, Lianbo; Fu, Xiaowen; Chen, Yingjie; Nikaido, Tamotsu

2004-05-01

69

9,10-Dihydrophenanthrene Glucosides from Juncus effusus  

Microsoft Academic Search

Four 9,10-dihydrophenanthrene glucosides have been isolated from Juncus effusus and their structures confirmed on spectroscopic grounds and by semisynthesis. The results of a cytotoxic assay are also reported.

Marina Della Greca; Antonio Fiorentino; Antonio Molinaro; Pietro Monaco; Lucio Previtera

1995-01-01

70

Construction of artificial biosynthetic pathways for resveratrol glucoside derivatives.  

PubMed

Resveratrol, which is a polyphenolic antioxidant, is dose-dependent when used to provide health benefits, to enhance stress resistance, and to extend lifespans. However, even though resveratrol has therapeutic benefits, its clinical therapeutic effect is limited owing to its low oral bioavailability. An Escherichia coli system was developed that contains an artificial biosynthetic pathway that produces resveratrol glucoside derivatives, such as resveratrol-3-Oglucoside (piceid) and resveratrol-4'-O-glucoside (resveratroloside), from simple carbon sources. This artificial biosynthetic pathway contains a glycosyltransferase addition (YjiC from Bacillus) with resveratrol biosynthetic genes. The produced glucoside compounds were verified through the presence of a product peak(s) and also through LC/MS analyses. The strategy used in this research demonstrates the first harnessing of E. coli for de novo synthesis of resveratrol glucoside derivatives from a simple sugar medium. PMID:24561723

Choi, Oksik; Lee, Jae Kyoung; Kang, Sun-Young; Pandey, Ramesh Prasad; Sohng, Jae-Kyung; Ahn, Jong Seog; Hong, Young-Soo

2014-05-01

71

Two new cytotoxic iridoid esters from the rhizomes and roots of Patrinia heterophylla Bunge.  

PubMed

Two new iridoid esters, named patriheterdoid B, C, have been isolated from the rhizomes and roots of Patrinia heterophylla Bunge. Their structures were elucidated by extensive spectroscopic technologies. Together with patriheterdoid B, C, two known analogues have been isolated and identified by means of mass spectrometry and (1)H and (13)C NMR spectrometry. These compounds showed cytotoxic activity against SGC-7901, PC3 cell lines. PMID:23639075

Yang, Bo; Cheng, Ru-Bin; Wang, Yi-Qi; Shen, Li; Zhang, Ru-Song

2013-01-01

72

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

PubMed

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

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

2014-03-12

73

Coping with toxic plant compounds--the insect's perspective on iridoid glycosides and cardenolides.  

PubMed

Specializing on host plants with toxic secondary compounds enforces specific adaptation in insect herbivores. In this review, we focus on two compound classes, iridoid glycosides and cardenolides, which can be found in the food plants of a large number of insect species that display various degrees of adaptation to them. These secondary compounds have very different modes of action: Iridoid glycosides are usually activated in the gut of the herbivores by ?-glucosidases that may either stem from the food plant or be present in the gut as standard digestive enzymes. Upon cleaving, the unstable aglycone is released that unspecifically acts by crosslinking proteins and inhibiting enzymes. Cardenolides, on the other hand, are highly specific inhibitors of an essential ion carrier, the sodium pump. In insects exposed to both kinds of toxins, carriers either enabling the safe storage of the compounds away from the activating enzymes or excluding the toxins from sensitive tissues, play an important role that deserves further analysis. To avoid toxicity of iridoid glycosides, repression of activating enzymes emerges as a possible alternative strategy. Cardenolides, on the other hand, may lose their toxicity if their target site is modified and this strategy has evolved multiple times independently in cardenolide-adapted insects. PMID:21620425

Dobler, Susanne; Petschenka, Georg; Pankoke, Helga

2011-09-01

74

Identification of a Saccharomyces cerevisiae glucosidase that hydrolyzes flavonoid glucosides.  

PubMed

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

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

2011-03-01

75

Triacylated peonidin 3-sophoroside-5-glucosides from the purple flowers of Moricandia ramburii Webb.  

PubMed

Triacylated peonidin 3-sophoroside-5-glucosides were isolated from the purple flowers of Moricandia ramburii Webb. (Family: Brassicaceae), and determined to be peonidin 3-O-[2-O-(2-O-(trans-feruloyl)-glucosyl)-6-O-(trans-p-coumaroyl)-glucoside]-5-O-[6-O-(malonyl)-glucoside] (1), peonidin 3-O-[2-O-(2-O-(trans-feruloyl)-glucosyl)-6-O-(cis-p-coumaroyl)-glucoside]-5-O-[6-O-(malonyl)-glucoside] (2) and peonidin 3-O-[2-O-(2-O-(trans-sinapoyl)-glucosyl)-6-O-(trans-p-coumaroyl)-glucoside]-5-O-[6-O-(malonyl)-glucoside] (3), respectively, by chemical and spectroscopic methods. In addition, one known acylated cyanidin glycoside, cyanidin 3-O-[2-O-(2-O-(trans-feruloyl)-glucosyl)-6-O-(trans-p-coumaroyl)-glucoside]-5-O-[6-O-(malonyl)-glucoside] (4), was also identified in the flowers. Peonidin glycosides have not been reported hitherto in floral tissues in to Brassicaceae. PMID:22264647

Tatsuzawa, Fumi; Ito, Kanako; Muraoka, Hiroki; Namauo, Toshiharu; Kato, Kazuhisa; Takahata, Yoshihito; Ogawa, Satoshi

2012-04-01

76

A quantitative (1)H nuclear magnetic resonance (qHNMR) method for assessing the purity of iridoids and secoiridoids.  

PubMed

This paper utilized a quantitative (1)H nuclear magnetic resonance (qHNMR) method for assessing the purity of iridoids and secoiridoids. The method was fully validated, including specificity, linearity, accuracy, precision, reproducibility, and robustness. For optimization of experimental conditions, several experimental parameters were investigated, including relaxation delay (D1), scan numbers (NS) and power length (PL1). The quantification was based on the area ratios of H-3 from analytes relative to aromatic protons from 1,4-dinitrobenzene (internal standard) with methanol-d4 as solvent. Five iridoids and secoiridoids (sweroside, swertiamarin, gentiopicroside, geniposide, genipin) were analyzed. Furthermore, the results were validated by the high performance liquid chromatography coupled with ultraviolet detection (HPLC-UV) method. It can be concluded that the qHNMR method was simple, rapid, and accurate, providing a reliable and superior method for assessing the purity of iridoids and secoiridoids. PMID:25510321

Li, Zeyun; Welbeck, Edward; Yang, Li; He, Chunyong; Hu, Haijun; Song, Ming; Bi, Kaishun; Wang, Zhengtao

2015-01-01

77

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

PubMed

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

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

2015-05-15

78

Three new phenolic glucosides from the roots of Rheum palmatum.  

PubMed

A novel naphthalene glucoside, rheumone A (1), with an unprecedented skeleton containing a seven-membered lactone, and two new compounds, 1-O-phloroglucinyl-2-O-galloyl-6-O-cinnamoyl-?-D-glucoside (2) and chrysophanol 1-O-?-D-(6'-O-malonyl)glucoside (3), together with three known compounds (4-6) were isolated from the roots of Rheum palmatum. Their structures were elucidated mainly by spectroscopic analysis. These compounds were evaluated in vitro for their cytotoxicities towards human hepatocellular cancer cell lines Bel-7402 and Bel-7402/5Fu, and human gastric carcinoma cell line BGC-823. None of them showed cytotoxicity with IC(50) far beyond 50 ?M. PMID:22293484

Wang, Zhi-Wei; Wang, Jun-Song; Luo, Jun; Wei, Dan-Dan; Kong, Ling-Yi

2012-01-01

79

A new secoiridoid glucoside, amaronitidin, from the Peruvian folk medicine "Hercampuri" (Gentianella nitida).  

PubMed

A new secoiridoid glucoside designated amaronitidin (1) was isolated from the Peruvian folk medicine "Hercampuri" (Gentianella nitida) along with three known secoiridoid glucosides. Their structures were determined by extensive spectroscopic investigation. PMID:11411536

Kawahara, N; Masuda, K; Sekita, S; Satake, M

2001-06-01

80

Geniposide and its iridoid analogs exhibit antinociception by acting at the spinal GLP-1 receptors.  

PubMed

We recently discovered that the activation of the spinal glucagon-like peptide-1 receptors (GLP-1Rs) by the peptidic agonist exenatide produced antinociception in chronic pain. We suggested that the spinal GLP-1Rs are a potential target molecule for the management of chronic pain. This study evaluated the antinociceptive activities of geniposide, a presumed small molecule GLP-1R agonist. Geniposide produced concentration-dependent, complete protection against hydrogen peroxide-induced oxidative damage in PC12 and HEK293 cells expressing rat and human GLP-1Rs, but not in HEK293T cells that do not express GLP-1Rs. The orthosteric GLP-1R antagonist exendin(9-39) right-shifted the concentration-response curve of geniposide without changing the maximal protection, with identical pA2 values in both cell lines. Subcutaneous and oral geniposide dose-dependently blocked the formalin-induced tonic response but not the acute flinching response. Subcutaneous and oral geniposide had maximum inhibition of 72% and 68%, and ED50s of 13.1 and 52.7 mg/kg, respectively. Seven days of multidaily subcutaneous geniposide and exenatide injections did not induce antinociceptive tolerance. Intrathecal geniposide induced dose-dependent antinociception, which was completely prevented by spinal exendin(9-39), siRNA/GLP-1R and cyclic AMP/PKA pathway inhibitors. The geniposide iridoid analogs geniposidic acid, genipin methyl ether, 1,10-anhydrogenipin, loganin and catalpol effectively inhibited hydrogen peroxide-induced oxidative damage and formalin pain in an exendin(9-39)-reversible manner. Our results suggest that geniposide and its iridoid analogs produce antinociception during persistent pain by activating the spinal GLP-1Rs and that the iridoids represented by geniposide are orthosteric agonists of GLP-1Rs that function similarly in humans and rats and presumably act at the same binding site as exendin(9-39). PMID:24747181

Gong, Nian; Fan, Hui; Ma, Ai-Niu; Xiao, Qi; Wang, Yong-Xiang

2014-09-01

81

Teucrium polium Phenylethanol and Iridoid Glycoside Characterization and Flavonoid Inhibition of Biofilm-Forming Staphylococcus aureus.  

PubMed

The chemical composition and biofilm regulation of 15 metabolites from Teucrium polium are reported. Compounds were isolated from a CH2Cl2-MeOH extract of the aerial parts of the plant and included iridoid and phenylethanol glycosides and a monoterpenoid, together with nine known compounds. The structures were elucidated based on standard spectroscopic (UV, (1)H and (13)C NMR), 2D NMR ((1)H-(1)H COSY, HMQC, HMBC, and NOESY), and/or LC-ESIMS/MS data analyses. Inhibition of the biofilm-forming strain Staphylococcus aureus was observed with exposure to compounds 7 and 8. PMID:25524452

Elmasri, Wael A; Yang, Tianjiao; Tran, Phat; Hegazy, Mohamed-Elamir F; Hamood, Abdul N; Mechref, Yehia; Paré, Paul W

2015-01-23

82

Effect of Morinda citrifolia fruit extract and its iridoid glycosides on blood fluidity.  

PubMed

The aim of this study was to investigate the effect of Morinda citrifolia fruit on blood fluidity. M. citrifolia fruit extract (MCF-ext) was investigated for its influence on blood aggregation and fibrinolysis. MCF-ext inhibited polybrene-induced erythrocyte aggregation and thrombin activity. The fibrinolytic activity of MCF-ext, in the euglobulin lysis time test and fibrin plate assay, is reported here for the first time. One of the active compounds was an iridoid glycoside, asperulosidic acid. The results indicated that MCF-ext is a potentially useful health food which is capable of improving blood flow and preventing lifestyle-related diseases. PMID:24604344

Murata, Kazuya; Abe, Yumi; Futamura-Masuda, Megumi; Uwaya, Akemi; Isami, Fumiyuki; Deng, Shixin; Matsuda, Hideaki

2014-07-01

83

Enzymatic synthesis and characterization of novel epigallocatechin gallate glucosides  

Microsoft Academic Search

Three epigallocatechin gallate (EGCG) glucosides were synthesized by the acceptor reaction of a glucansucrase from Leuconostoc mesenteroides B-1299CB with EGCG and sucrose. After 1H, 13C, heteronuclear single quantum coherence, 1H–1H correlation spectroscopy, and heteronuclear multiple bond correlation nuclear magnetic resonance analyses, the glucosides were identified as (?)-epigallocatechin gallate 4??-O-?-d-glucopyranoside (EGCG-G1), (?)-epigallocatechin gallate 7,4??-di-O-?-d-glucopyranoside (EGCG-G2A), and (?)-epigallocatechin gallate 4?,4??-di-O-?-d-glucopyranoside (EGCG-G2B). Two

Young-Hwan Moon; Ghahyun Kim; Jin-Ha Lee; Xing-Ji Jin; Do-Won Kim; Doman Kim

2006-01-01

84

Heteroaryl- O-glucosides as novel sodium glucose co-transporter 2 inhibitors. Part 1  

Microsoft Academic Search

A series of benzo-fused heteroaryl-O-glucosides was synthesized and evaluated in SGLT1 and 2 cell-based functional assays. Indole-O-glucoside 10a and benzimidazole-O-glucoside 18 exhibited potent in vitro SGLT2 inhibitory activity.

Xiaoyan Zhang; Maud Urbanski; Mona Patel; Roxanne E. Zeck; Geoffrey G. Cox; Haiyan Bian; Bruce R. Conway; Mary Pat Beavers; Philip J. Rybczynski; Keith T. Demarest

2005-01-01

85

Chemotaxonomy of Veroniceae and its allies in the Plantaginaceae.  

PubMed

In a chemosystematic investigation of tribe Veroniceae (Plantaginaceae), representatives of Camptoloma, Sibthorpia, Veronica subg. Pentasepalae and subg. Hebe, Veronicastrum, Wulfenia, and the related Ellisiophyllum and Globularia were examined for non-flavonoid glycosides. From the 14 species studied, 28 different iridoid glucosides and 10 caffeoyl phenylethanoid glucosides (CPGs), as well as salidroside and arbutin were isolated and characterized by NMR; of these, five compounds were previously unknown. It was found that the representatives of Veroniceae, as well as Globularia, were characterized by mannitol, aucubin, catalpol and catalpol esters. Each of the three studied species of Veronica subg. Hebe contained at least one of the 6-O-catalpol esters typical for Veronica s. str. (verminoside), supporting the inclusion of Hebe in Veronica. However, their main constituents were esters of 6-O-rhamnopyranosylcatalpol; a CPG, hebeoside (2'-beta-xylopyranosyl-verbascoside) was isolated from V. (Hebe) salicifolia. The two species of Veronicastrum also contained 6-O-rhamnopyranosylcatalpol esters, including the previously unknown 2'',3''- and 3'',4''-dicinnamoyl derivatives and, in contrast to the earlier reports, they lacked 6-O-catalpol esters. The main iridoid constituents in the three investigated species of Wulfenia were 10-O-aucubin and 10-O-catalpol esters (isoscrophularioside or globularin) while baldaccioside (10-O-cinnamoyl asystasioside E) was isolated from W. baldaccii. Globularia vulgaris contained 10-O-catalpol esters (e.g., globularin) and, in addition, asperuloside together with its benzoyl analogue named besperuloside. The representatives of Sibthorpia and Ellisiophyllum were almost completely devoid of iridoids; this, however, together with the CPGs present implied a close relationship between the two genera. Camptoloma lyperiiflorum lacked hexitols but contained esters of 6-O-rhamnopyranosylcatalpol different from those found in Veroniceae but known from Buddleja, Scrophularia and Verbascum (Scrophulariaceae s. str.). PMID:16386770

Taskova, Rilka Mladenova; Gotfredsen, Charlotte Held; Jensen, Søren Rosendal

2006-02-01

86

Evaluation of anti-HIV-1 activity of a new iridoid glycoside isolated from Avicenna marina, in vitro.  

PubMed

This study was carried out to check the efficacy of methanol seed extract of Avicenna marina and its column chromatographic fractions on Peripheral Blood Mono nuclear Cells (PBMCs) toxicity and HIV-1 replication. The anti-HIV-1 activities of crude methanol extract and its fractions were performed by use of real-time polymerase chain reaction (PCR) assay and HIV-1 p24 antigen kit. A time of drug addiction approach was also done to identify target of anti-HIV compound. The activity of the extracts on CD4, CD3, CD19 and CD45 expression in lymphocytes population was performed by use of flow cytometry. The most active anti-HIV agent was detected by spectroscopic analysis as 2'-O-(4-methoxycinnamoyl) mussaenosidic acid. The apparent effective concentrations for 50% virus replication (EC50) of methanol extract and iridoid glycoside were 45 and 0.1?g/ml respectively. The iridoid glycoside also did not have any observable effect on the proportion of CD4, CD3, CD19 and CD45 cells or on the intensity of their expressions on PBMCs. In addition, the expression level of C-C chemokine receptor type 5 (CCR5) and chemokine receptor type 4 (CXCR4) on CD4(+) T cells were decreased in cells treated with this iridoid glycoside. The reduction of these two HIV coreceptors and the result of time of addition study demonstrated that this iridoid glycoside restricts HIV-1 replication on the early stage of HIV infection. PMID:25239814

Behbahani, Mandana

2014-09-16

87

Iridoid Synthase Activity Is Common among the Plant Progesterone 5?-Reductase Family.  

PubMed

Catharanthus roseus, the Madagascar periwinkle, synthesizes bioactive monoterpenoid indole alkaloids, among which 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. Characterisation 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, could 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 localisation, gene expression analysis, in situ hybridisation and virus-induced gene silencing, indicates that besides IS, CrP5?R4 may also participate in secoiridoid biosynthesis. Finally, 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:25239067

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

2014-09-19

88

Iridoid Synthase Activity Is Common among the Plant Progesterone 5?-Reductase Family.  

PubMed

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

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

89

Micellar electrokinetic capillary chromatography of limonoid glucosides from citrus seeds  

Microsoft Academic Search

This report presents the results of an investigation into the application of micellar electrokinetic capillary chromatography (MECC) for the analysis of limonoid glucosides in a citrus seed extract. MECC based on sodium dodecyl sulphate (SDS) was used to provide highly efficient separations of the closely related structures. A phosphate-borate buffer containing SDS was used to optimize the separation conditions for

Vinayagum E. Moodley; Dulcie A. Mulholland; Mark W. Raynor

1995-01-01

90

Portuloside A, a monoterpene glucoside, from Portulaca oleracea  

Microsoft Academic Search

From the methanol extract of Portulaca oleracea, a new monoterpene glucoside, portuloside A, has been isolated. The structure of portuloside A was established by spectroscopic methods and then confirmed to be (3S)-3-(3,7-dimethylocta-1,7-dien-6-onyl)-?-d-glucopyranoside by synthesis from linalool.

Naomi Sakai; Kyouko Inada; Michi Okamoto; Yoshikazu Shizuri; Yoshiyasu Fukuyama

1996-01-01

91

Solution properties of alkyl glucosides, alkyl thioglucosides and alkyl maltosides  

Microsoft Academic Search

Aqueous solutions containing sugar-based surfactants, alkyl glucosides, thioglucosides and maltosides, have been investigated in a wide concentration range, at different temperatures. Colligative properties (freezing point and vapour pressure depression), volumetric, adiabatic compressibility, surface tension and calorimetric methods were used.The results give information on the Gibbs energy of transfer from water to a micellar environment and on other thermodynamic contributions to

Antonio Capalbi; Giacomo Gente; Camillo La Mesa

2004-01-01

92

A new iridoid, verbascoside and derivatives with inhibitory activity against Taq DNA polymerase.  

PubMed

DNA polymerases are enzymes that play a crucial role in DNA metabolism such as replication, repair, transcription, recombination, and chromosome segregation during mitosis. Herein we report the isolation of a new iridoid (6-epi-catalpol, 2) and per-O-acetyl-verbascoside (11) from aerial part of Buddleja cordobensis Grisebach (Buddlejaceae). From compound 2, we have obtained eight compounds by chemical transformation. This group of compounds at a concentration of 500?M was assayed against Taq DNA polymerase. Compound 11 (per-O-acetyl-verbascoside) was the most active with an IC50 of 1.21±0.18?M; compounds 9, 2 and 8 were strong inhibitors with IC50 values of 5.57±0.70, 21.62±0.22 and 78.13±0.93?M, respectively. Compounds 11 and 9 could be a leader structures to development new anticancer chemotherapy medicines and a useful tool to investigate DNA polymerase activity. PMID:25582597

Garro, Hugo A; García, Celina; Martín, Victor S; Tonn, Carlos E; Pungitore, Carlos R

2015-02-15

93

Synthesis of novel anticancer iridoid derivatives and their cell cycle arrest and caspase dependent apoptosis.  

PubMed

Nyctanthes arbortristis Linn (Oleaceae) is widely distributed in sub-Himalayan regions and southwards to Godavari, India commonly known as Harsingar and Night Jasmine. In continuation of our drug discovery programme on Indian medicinal plants, we isolated arbortristoside-A (1) and 7-O-trans-cinnamoyl 6?-hydroxyloganin (2) from the seeds of N. Arbortristis, which exhibited moderate in vitro anticancer activity. Chemical transformation of 2 led to significant improvement in the activity in derivative 8 and 15 against HepG2 (human hepatocellular carcinoma), MCF-7 (breast adenocarcinoma) cell lines. The compounds 8 and 15 were also capable of cell cycle arrest and caspase dependent apoptosis in HepG2 cell lines. These iridoid derivatives hold promise for developing safer alternatives to the marketed drugs. PMID:24075214

Pandeti, Sukanya; Sharma, Komal; Bathula, Surendar Reddy; Tadigoppula, Narender

2014-02-15

94

New acylated salicin bis-glucosides from Viburnum veitchii.  

PubMed

The phytochemical study of aerial parts of Viburnum veitchii C.H. Wright, a deciduous species originary of Central China, led to the isolation of three salicin derivative bis-glucosides, i.e. henryoside (1), and the new structures 2'b-acetyl-3'b-(3-methylbutyryl)-henryoside (2) and 2'b,6'b-diacetyl-3'b-(3-methylbutyryl)-henryoside (3). In addition, luteolin, lonicerin, robustaflavone and eugenyl-?-D-glucopyranoside were also isolated. PMID:22950836

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

2013-01-01

95

Enzymatic Biosynthesis of Novel Resveratrol Glucoside and Glycoside Derivatives.  

PubMed

A uridine diphosphate 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. A 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 number of products formed were found to vary with the other NDP-sugar donors. Resveratrol 3-O-?-d-2-deoxyglucoside, resveratrol 3,5-O-?-d-di-2-deoxyglucoside were found to be produced while using TDP-2-deoxyglucose as donor, however, monoglycosides resveratrol 4?-O-?-d-galactoside, resveratrol 4?-O-?-d-viosaminoside, resveratrol 3-O-?-l-rhamnoside, resveratrol 3-O-?-l-fucoside were produced from respective sugar donors. Altogether ten diverse glycoside derivatives of medicinally important resveratrol were generated; demonstrating the capacity for YjiC to produce structurally diverse resveratrol glycosides. PMID:25239890

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

2014-09-19

96

Utilizing genetically engineered bacteria to produce plant-specific glucosides.  

PubMed

Plant-derived glucosides have attracted much attention due to their widespread applications. This class of products is difficult to isolate or to synthesize in pure form because of the resulting low yields. Thus, simple approaches for the generation of such glucosides would be highly beneficial. We purified and characterized a novel glucosyltransferase from plant cell suspension cultures of Rauvolfia serpentina, which showed rather low substrate specificity. We obtained its cDNA and expressed the active recombinant protein in bacteria (Escherichia coli) with excellent plant-specific glucosylation efficiencies. Compared with the plant system, the bacteria delivered the new enzyme, which was in the form of a soluble or matrix-bound enzyme, approximately 1800 times more efficiently for the synthesis of a wide range of glucosides. More importantly, the engineered E. coli strain allowed for in vivo glucosylation and release of the product into the culture medium, as shown by the formation of arbutin, which is a potent inhibitor of human melanin biosynthesis with commercial value. PMID:11505382

Arend, J; Warzecha, H; Hefner, T; Stöckigt, J

2001-09-01

97

Indole-glucosides as novel sodium glucose co-transporter 2 (SGLT2) inhibitors. Part 2  

Microsoft Academic Search

A series of indole-O-glucosides and C-glucosides was synthesized and evaluated in SGLT1 and SGLT2 cell-based functional assays. Compounds 2a and 2o were identified as potent SGLT2 inhibitors and screened in ZDF rats.

Xiaoyan Zhang; Maud Urbanski; Mona Patel; Geoffrey G. Cox; Roxanne E. Zeck; Haiyan Bian; Bruce R. Conway; Mary Pat Beavers; Philip J. Rybczynski; Keith T. Demarest

2006-01-01

98

Water-soluble constituents of caraway: carvone derivatives and their glucosides.  

PubMed

Nine monoterpenoids related to carvone and seven glucosides were isolated from the water-soluble portion of the methanolic extract of the caraway (fruit of Carum carvi L.), and their structures were clarified by spectral investigation. Among them, eight monoterpenoids and six glucosides were new. PMID:11824587

Matsumura, Tetsuko; Ishikawa, Toru; Kitajima, Junichi

2002-01-01

99

Anomericity of T-2 Toxin-glucoside: Masked Mycotoxin in Cereal Crops.  

PubMed

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

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

100

Purification and functional characterization of the first stilbene glucoside-specific ?-glucosidase isolated from Lactobacillus kimchi.  

PubMed

This study aimed to develop viable enzymes for bioconversion of resveratrol-glucoside into resveratrol. Out of 13 bacterial strains tested, Lactobacillus kimchi JB301 could completely convert polydatin into resveratrol. The purified enzyme had an optimum temperature of 30-40°C and optimum pH of pH 5.0 against polydatin. This enzyme showed high substrate specificities towards different substrates in the following order: isorhaponticin>polydatin>mulberroside A>oxyresveratrol-3-O-glucoside. Additionally, it rarely hydrolyzed astringin and desoxyrhaponticin. Based on these catalytic specificities, we suggest this enzyme be named stilbene glucoside-specific ?-glucosidase. Furthermore, polydatin extracts from Polygonum cuspidatum were successfully converted to resveratrol with a high yield (of over 99%). Stilbene glucoside-specific ?-glucosidase is the first enzyme isolated from lactic acid bacteria capable of bio-converting various stilbene glucosides into stilbene. PMID:25442950

Ko, Jin-A; Park, J Y; Kwon, H J; Ryu, Y B; Jeong, H J; Park, S J; Kim, C Y; Oh, H M; Park, C S; Lim, Y H; Kim, D; Rho, M C; Lee, W S; Kim, Y M

2014-12-01

101

Amaranthin in feather cockscombs is synthesized via glucuronylation at the cyclo-DOPA glucoside step in the betacyanin biosynthetic pathway.  

PubMed

Uridine 5'-diphosphate (UDP)-glucuronic acid: cyclo-DOPA 5-glucoside glucuronosyltransferase activity was detected in a crude extract prepared from the purple flowers of feather cockscombs. This suggests that the glucuronic acid moiety of amaranthin and its derivatives may be introduced at the cyclo-DOPA glucoside step, but not at the betanidin glucoside step. PMID:16247652

Sasaki, Nobuhiro; Abe, Yutaka; Wada, Katsuhiro; Koda, Takatoshi; Goda, Yukihiro; Adachi, Taiji; Ozeki, Yoshihiro

2005-12-01

102

Involvement of JAK/STAT signaling in the effect of cornel iridoid glycoside on experimental autoimmune encephalomyelitis amelioration in rats.  

PubMed

In the present study, we investigated the therapeutic benefit of cornel iridoid glycoside (CIG), the main component extracted from Cornus officinalis, in experimental autoimmune encephalomyelitis (EAE) rats. CIG was intragastrically administered daily after EAE initiation for 20days and reduced disease severity, incidence, disease onset and ongoing paralysis. Histopathological staining showed that CIG could reduce T cell entry to the central nervous system and microglia activation, increased brain-derived neurotrophic factor (BDNF) expression and mature oligodendrocytes, and decreased oligodendrocyte progenitor cells (OPCs). Also, CIG treatment inhibited brain JAK/STAT1/3 and reduced proinflammatory cytokines. CIG might be a novel potential therapeutic agent for multiple sclerosis (MS). PMID:25012120

Yin, Linlin; Chen, Yongyan; Qu, Zhao; Zhang, Li; Wang, Qi; Zhang, Qi; Li, Lin

2014-09-15

103

A systematic study of C-glucoside trisphosphates as myo-inositol trisphosphate receptor ligands. Synthesis of beta-C-glucoside trisphosphates based on the conformational restriction strategy.  

PubMed

Beta-C-glucoside trisphosphates having a C2 side chain (3,7-anhydro-2-deoxy-D-glycero-D-gulo-octitol 1,5,6-trisphosphate, 11) and a C3 side chain (4,8-anhydro-2,3-dideoxy-D-glycero-D-gulo-nonanitol 1,6,7-trisphosphate, 12) were designed as structurally simplified analogues of a potent D-myo-inositol 1,4,5-trisphosphate (IP3) receptor ligand, adenophostin A. Construction of the beta-C-glucosidic structure, which was the key to their synthesis, was achieved by two different methods based on the conformational restriction strategy: (1) radical cyclization with a temporary connecting silicon tether and (2) silane reduction of glyconolactols having an anomeric allyl substituent. Using these methods, the target beta-C-glycoside trisphosphates 11 and 12 were successfully synthesized. A structure-activity relationship was established on a series of C-glucoside trisphosphates, including the previously synthesized related compounds, which were a C-glycosidic analogue 3 of adenophostin A, its uracil congener 5, alpha-C-glucoside trisphosphates 7-9 having a C1, C2, or C3 side chain, and the beta-C-glucoside trisphosphates 10-12 having a C1, C2, or C3 side chain. The O-glycosidic linkage of adenophostin A and its analogues proved to be replaced by the chemically and biologically more stable C-glycosidic linkage. The alpha-C2-glucoside trisphosphate 8 stimulates Ca2+ release with a potency similar to that of IP3 in spite of its simplified structure, indicating a better fit to the receptor than the beta-C-glucoside trisphosphates and also the alpha-congeners having a shorter or longer C1 side chain, which was supported by molecular modeling using the ligand binding domain of the IP3 receptor. PMID:16539376

Terauchi, Masaru; Abe, Hiroshi; Tovey, Stephen C; Dedos, Skarlatos G; Taylor, Colin W; Paul, Michael; Trusselle, Melanie; Potter, Barry V L; Matsuda, Akira; Shuto, Satoshi

2006-03-23

104

Chemotaxonomic value of magastigmane glucosides of Cichorium calvum.  

PubMed

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

Michalska, Klaudia; Beharav, Alex; Kisiel, Wanda

2014-03-01

105

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

PubMed

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

Gering-Ward, B

1989-02-01

106

Citrifolinin A , a new unusual iridoid with inhibition of Activator Protein1 (AP1) from the leaves of noni ( Morinda citrifolia L.)  

Microsoft Academic Search

A new unusual iridoid, named citrifolinin A, showing significant inhibition of UVB-induced Activator Protein-1 (AP-1) activity in cell cultures, has been isolated from the leaves of Morinda citrifolia. Its structure was elucidated based on a detailed high-field 1D and 2D spectral analysis.

Shengmin Sang; Kan He; Guangming Liu; Nanqun Zhu; Mingfu Wang; Jin-woo Jhoo; Qunyi Zheng; Zigang Dong; Geetha Ghai; Robert T. Rosen; Chi-Tang Ho

2001-01-01

107

Simultaneous determination of iridoid glycosides and flavanoids in Lamionphlomis rotate and its herbal preparation by a simple and rapid capillary zone electrophoresis method.  

PubMed

Iridoid glycosides and flavanoids are two main effective components of Lamiophlomis rotata (Benth.) kudo. However, there is no method for simultaneous analysis of iridoid glycosides and flavanoids in L. rotata and its pharmaceutical preparations. A simple and rapid capillary zone electrophoresis (CZE) method was developed and validated for simultaneous determination of two iridoid glycosides (8-O-acetylshanzhiside methylester and 8-deoxyshanzhiside) and three flavanoids (apigenin, quercetin and luteolin) in L. rotata. Operational variables, such as the voltage, buffer concentration and pH were optimized, the final optimum separation condition was 10 mM sodium tetraborate-20 mM NaH(2) PO(4) (pH 8.5)-15% (v/v) methanol, 238 nm UV detection, 18 kV applied voltage. The linearity and the recovery of the proposed method were very satisfactory (correlation coefficients were 0.9994-0.9998 and the recoveries were 94.5-108.8% for the analytes) and the method allowed analytes in real samples to be determined within 9 min. The proposed CZE method can be used for quality control of iridoid glycosides and flavanoids in L. rotata and its herbal preparation. PMID:21548111

Lü, Wenjuan; Li, Maoxing; Chen, Yonglei; Chen, Hongli; Chen, Xingguo

2012-02-01

108

Structural characterization of new malvidin 3-glucoside-catechin aryl/alkyl-linked pigments.  

PubMed

The condensation reaction between malvidin 3-glucoside and catechin mediated by isobutyraldehyde, benzaldehyde, and isovaleraldehyde was conducted in model solutions at two pH values (1.5 and 3.2). The formation of new alkyl/aryl-linked adducts corresponding to the structures malvidin 3-glucoside-isobutylcatechin, malvidin 3-glucoside-benzylcatechin, and malvidin 3-glucoside-3-methylbutylcatechin was respectively observed from each aldehyde. The structural characterization of these new structures has been elucidated by 1D and 2D NMR, mass spectrometry, and UV-vis techniques. These new adducts showed the same lambda(max) in the visible region at 540 nm, which is bathochromically shifted 15 nm when compared with the original anthocyanin (lambda(max) = 525 nm). PMID:15315394

Pissarra, João; Lourenço, Sandra; González-Paramás, Ana M; Mateus, Nuno; Santos Buelga, Celestino; Silva, Artur M S; de Freitas, Victor

2004-08-25

109

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

PubMed

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 138.62gkg(-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

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

2015-05-15

110

Regioselective glucosidation of trans-resveratrol in Escherichia coli expressing glucosyltransferase from Phytolacca americana.  

PubMed

A glucosyltransferase (GT) of Phytolacca americana (PaGT3) was expressed in Escherichia coli and purified for the synthesis of two O-?-glucoside products of trans-resveratrol. The reaction was moderately regioselective with a ratio of 4'-O-?-glucoside: 3-O-?-glucoside at 10:3. We used not only the purified enzyme but also the E. coli cells containing the PaGT3 gene for the synthesis of glycoconjugates. E. coli cell cultures also have other advantages, such as a shorter incubation time compared with cultured plant cells, no need for the addition of exogenous glucosyl donor compounds such as UDP-glucose, and almost complete conversion of the aglycone to the glucoside products. Furthermore, a homology model of PaGT3 and mutagenesis studies suggested that His-20 would be a catalytically important residue. PMID:22048846

Ozaki, Shin-ichi; Imai, Hiroya; Iwakiri, Tomoya; Sato, Takehiro; Shimoda, Kei; Nakayama, Toru; Hamada, Hiroki

2012-03-01

111

Growth inhibitory activity of cucurbitacin glucosides isolated from Citrullus colocynthis on human breast cancer cells.  

PubMed

Our aim was to study the effects of cucurbitacin glucosides extracted from Citrullus colocynthis leaves on human breast cancer cell growth. Leaves were extracted, resulting in the identification of cucurbitacin B/E glucosides. The cucurbitacin glucoside combination (1:1) inhibited growth of ER(+) MCF-7 and ER(-) MDA-MB-231 human breast cancer cell lines. Cell-cycle analysis showed that treatment with isolated cucurbitacin glucoside combination resulted in accumulation of cells at the G(2)/M phase of the cell cycle. Treated cells showed rapid reduction in the level of the key protein complex necessary to the regulation of G(2) exit and initiation of mitosis, namely the p34(CDC2)/cyclin B1 complex. cucurbitacin glucoside treatment also caused changes in the overall cell morphology from an elongated form to a round-shaped cell, which indicates that cucurbitacin treatment caused impairment of actin filament organization. This profound morphological change might also influence intracellular signaling by molecules such as PKB, resulting in inhibition in the transmission of survival signals. Reduction in PKB phosphorylation and inhibition of survivin, an anti-apoptosis family member, was observed. The treatment caused elevation in p-STAT3 and in p21(WAF), proven to be a STAT3 positive target in absence of survival signals. Cucurbitacin glucoside treatment also induced apoptosis, as measured by Annexin V/propidium iodide staining and by changes in mitochondrial membrane potential (DeltaPsi) using a fluorescent dye, JC-1. We suggest that cucurbitacin glucosides exhibit pleiotropic effects on cells, causing both cell cycle arrest and apoptosis. These results suggest that cucurbitacin glucosides might have therapeutic value against breast cancer cells. PMID:17049494

Tannin-Spitz, Tehila; Grossman, Shlomo; Dovrat, Sara; Gottlieb, Hugo E; Bergman, Margalit

2007-01-01

112

Determination of isoflavone glucoside malonates in Trifolium pratense L. (red clover) extracts: quantification and stability studies  

Microsoft Academic Search

Isoflavones, their glucosides and their glucoside malonates were determined in red clover leaf extracts using reversed-phase LC coupled to atmospheric pressure chemical ionisation mass spectrometry (APCI-MS), UV and fluorescence detectors and the stability of the malonates was investigated. Extracts can be stored at least 1–2 weeks at ?20°C without loss of malonates. In LC-separated fractions the malonates are most stable

Eva de Rijke; Alberto Zafra-Gómez; Freek Ariese; Udo A. Th Brinkman; Cees Gooijer

2001-01-01

113

Hydrolytic fate of deoxynivalenol-3-glucoside during digestion  

PubMed Central

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

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

2011-01-01

114

Low toxicity of deoxynivalenol-3-glucoside in microbial cells.  

PubMed

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

Suzuki, Tadahiro; Iwahashi, Yumiko

2015-01-01

115

Low Toxicity of Deoxynivalenol-3-Glucoside in Microbial Cells  

PubMed Central

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

Suzuki, Tadahiro; Iwahashi, Yumiko

2015-01-01

116

O-Spiro C-aryl glucosides as novel sodium-dependent glucose co-transporter 2 (SGLT2) inhibitors  

Microsoft Academic Search

Two series of O-spiro C-aryl glucosides were synthesized and tested for inhibition of hSGLT1 and hSGLT2. 6?-O-Spiro C-aryl glucosides exhibited potent in vitro hSGLT2 inhibitory activity but 2?-O-spiro C-aryl glucosides showed no in vitro hSGLT2 inhibitory activity at a screening concentration of 1?M.

Baihua Xu; Binhua Lv; Yan Feng; Ge Xu; Jiyan Du; Ajith Welihinda; Zelin Sheng; Brian Seed; Yuanwei Chen

2009-01-01

117

Malonylglucoside conjugates of isoflavones are much less bioavailable compared with unconjugated ?-glucosidic forms in rats.  

PubMed

Despite considerable interest in the physiologic effects of isoflavones, the in vivo bioavailability of the most common isoflavone forms, malonylglucoside conjugates, has not been determined. Differences in the bioavailability of malonylglucosides compared with the nonconjugated ?-glucoside forms may explain the inconsistent findings regarding the physiologic effects of isoflavones. Therefore, our objective was to determine the effect of malonyl- conjugation on isoflavone bioavailability in an animal model. Malonylgenistin and malonyldaidzin, and their corresponding nonconjugated glucosides, were extracted from soy grits and purified using liquid chromatography. Purity of the isolated forms was confirmed by nuclear magnetic resonance analysis. Male rats were gavaged with malonylgenistin, genistin, malonyldaidzin, or daidzin at a dose of 100 ?mol/kg body weight. Blood and urine samples were collected at time intervals ranging from 0 to 48 h. Isoflavone metabolites in plasma and urine were determined using stable isotope dilution-liquid chromatography/mass spectrometry. Comparisons of pharmacokinetic variables were made between nonconjugated and conjugated glucosides and over time of plasma collection. The areas under the time-concentration curve of the metabolites in the plasma obtained after the administration of nonconjugated ?-glucosides were 1 to 6 times higher than those of their respective malonylglucosides (P ? 0.05). Additionally, maximum plasma concentration and urinary excretion of isoflavone metabolites were significantly higher (1-9 times; P ? 0.05) after the administration of nonconjugated ?-glucosides. To our knowledge, these results demonstrated, for the first time, that nonconjugated ?-glucosides are relatively more bioavailable than their respective malonylglucosides. These differences in the bioavailability of conjugated and nonconjugated ?-glucosides should be considered in future studies focused on the bioactivity of isoflavones. PMID:24647389

Yerramsetty, Vamsidhar; Gallaher, Daniel D; Ismail, Baraem

2014-05-01

118

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

PubMed Central

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

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

119

Uptake of quercetin and quercetin 3-glucoside from whole onion and apple peel extracts by Caco-2 cell monolayers.  

PubMed

Evidence suggests that regular consumption of fruits and vegetables may reduce the risk of chronic diseases, and phytochemicals from fruits and vegetables may be responsible for this health benefit. However, there is limited knowledge on the bioavailability of specific phytochemicals from whole fruits and vegetables. This study used Caco-2 cells to examine uptake of quercetin aglycon and quercetin 3-glucoside as purified compounds and from whole onion and apple peel extracts. Pure quercetin aglycon was absorbed by the Caco-2 cells in higher concentrations than quercetin 3-glucoside (p < 0.05). Caco-2 cells treated with quercetin 3-glucoside accumulated both quercetin 3-glucoside and quercetin. Caco-2 cells absorbed more onion quercetin aglycon than onion quercetin 3-glucoside (p < 0.05), and the percentage of onion quercetin absorbed was greater than that of pure quercetin, most likely due to enzymatic hydrolysis of quercetin 3-glucoside and other quercetin glucosides found in the onion by the Caco-2 cells. Caco-2 cells absorbed low levels of quercetin 3-glucoside from apple peel extracts, but quercetin aglycon absorption was not detected. Caco-2 cell homogenates demonstrated both lactase and glucosidase activities when incubated with lactose and quercetin 3-glucoside, respectively. This use of the Caco2 cell model appears to be a simple and useful system for studying bioavailability of whole food phytochemicals and may be used to assess differences in bioavailability between foods. PMID:15537334

Boyer, Jeanelle; Brown, Dan; Liu, Rui Hai

2004-11-17

120

Mechanism of biosynthesis of thio-?-d-glucuronides and thio-?-d-glucosides  

PubMed Central

1. The thio-?-d-glucosiduronic acids (thio-?-glucuronides) of o-aminothiophenol, diethyldithiocarbamic acid, p-nitrothiophenol and thiophenol are formed biosynthetically in broken- and intact-cell preparations of mouse liver. 2. For this biosynthesis to occur in homogenates or microsomal fractions, UDP-glucuronic acid was required during incubation; glucose, glucuronic acid or UDP could not replace it. UDP was a product of the reaction. 3. The biosynthetic mechanism linking glucuronic acid to thiol and carbodithioic groups therefore requires UDP-glucuronyltransferase activity and resembles that forming the various types of O-glucuronides. 4. An analogous enzymic mechanism employing UDP-glucose synthesizes the thio-?-d-glucosides of diethyldithiocarbamic acid and thiophenol in gut preparations of the mollusc Arion ater; this mechanism resembles that forming the O-glucosides. The thio-?-d-glucosides are formed also in intact cells. 5. As expected from the distribution of O-glycosides, S-glucuronides of these aglycones were not detectable with the invertebrate, nor were the S-glucosides with the vertebrate. 6. Despite their similar biosyntheses, S- and O-?-glycosides differ in susceptibility to hydrolysis by ?-glycosidases. Rat preputial-gland ?-glucuronidase hydrolysed thioglucuronides of o-aminothiophenol, diethyldithiocarbamic acid and p-nitrothiophenol, hydrolysis being inhibited by glucarolactone; the thioglucuronide of thiophenol was not hydrolysed by preputial-gland or liver ?-glucuronidase. The two S-glucosides resisted hydrolysis by ?-glucosidase from almond emulsin. PMID:4658987

Dutton, G. J.; Illing, H. P. A.

1972-01-01

121

Qualitative and quantitative analysis of iridoid glycosides in the flower buds of Lonicera species by capillary high performance liquid chromatography coupled with mass spectrometric detector  

Microsoft Academic Search

A highly sensitive and specific method, based on capillary high performances liquid chromatography coupled with single quadrupole mass spectrometry using electrospray ionization (capillary HPLC–ESI\\/MS), is proposed for the identification and quantification of iridoid glycosides in the flower buds of five Lonicera species. A Zorbax SB-C18 (0.3mm×150mm, 5?m) capillary column and a gradient elution with methanol–acetonitrile–aqueous acetate acid were utilized. The

Yue Song; Song-Lin Li; Meng-Hua Wu; Hui-Jun Li; Ping Li

2006-01-01

122

Evidence for bile acid glucosides as normal constituents in human urine.  

PubMed

A glucosyltransferase catalysing formation of bile acid glucosides was recently isolated from human liver microsomes. In order to investigate the potential occurrence of such bile acid derivatives in vivo, a method was devised for their isolation and purification from urine. Conditions were established with the aid of glucosides of radiolabelled, unconjugated glycine and taurine conjugated bile acids prepared enzymatically using human liver microsomes. Analysis by gas chromatography and mass spectrometry of methyl ester trimethylsilyl ether derivatives indicated the excretion of glucosides of nonamidated hyodeoxycholic, chenodeoxycholic, deoxycholic, ursodeoxycholic and cholic acids and of glycine and taurine conjugated chenodeoxycholic and cholic acids. Additional compounds were present giving mass spectral fragmentation patterns typical of di- and trihydroxy bile acid glycosides. Semiquantitative estimates indicated a total daily excretion of about 1 mumol. PMID:2951276

Marschall, H U; Egestad, B; Matern, H; Matern, S; Sjövall, J

1987-03-23

123

Enzymatic synthesis and characterization of arbutin glucosides using glucansucrase from Leuconostoc mesenteroides B-1299CB.  

PubMed

Two arbutin glucosides were synthesized via the acceptor reaction of a glucansucrase from Leuconostoc mesenteroides B-1299CB with arbutin and sucrose. The glucosides were purified by Bio-gel P-2 column chromatography and high-performance liquid chromatography, and the structures were elucidated as 4-hydroxyphenyl beta-isomaltoside (arbutin-G1), 4-hydroxyphenyl beta-isomaltotrioside (arbutin-G2), according to the results of (1)H, (13)C, heteronuclear single-quantum coherence, (1)H-(1)H COSY, and heteronuclear multiple-bond correlation analyses. Arbutin glucoside (4-hydroxyphenyl beta-isomaltoside) exhibited slower effects on 1,1-diphenyl-2-picrylhydrazyl radical scavenging and similar effects on tyrosinase inhibition, and increased inhibitory effect on matrix metalloproteinase-1 production induced by UVB than arbutin. PMID:17917726

Moon, Young Hwan; Nam, Seung Hee; Kang, Jin; Kim, Young-Min; Lee, Jin-Ha; Kang, Hee-Kyung; Breton, Vincent; Jun, Woo-Jin; Park, Ki-Deok; Kimura, Atsuo; Kim, Doman

2007-12-01

124

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

PubMed

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

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

2014-01-17

125

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

SciTech Connect

(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.

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

1988-11-01

126

Skin absorption and metabolism of a new vitamin E prodrug, ?-tocopherol-glucoside: in vitro evaluation in human skin models  

Microsoft Academic Search

The aim of this study was to investigate the cutaneous penetration and metabolism of the new vitamin E prodrug ?-tocopherol glucoside (?-TG), as compared to those of common vitamin E acetate, in vitro, both in reconstituted human epidermis and in viable human skin. Better diffusion was observed with ?-tocopherol acetate (?-TAc) than with ?-tocopherol glucoside in both skin models, at

Alain Mavon; Véronique Raufast; Daniel Redoulès

2004-01-01

127

Cyanidin 3-O-?-d-Glucoside Improves Bone Indices.  

PubMed

Abstract Oxidative stress (OS) promotes bone loss after menopause, and there is evidence that dietary antioxidants may reduce the level of OS in vivo. This study examined dose-dependent effects of blackberries (BBs) containing mainly cyanidin 3-O-?-d-glucoside (C3G) in preventing bone loss in an ovariectomized (Ovx) rat model. Nine-month-old female (N=38) Sprague-Dawley rats were scanned using dual-energy X-ray absorptiometry for baseline whole body, bone mineral content (BMC), and bone mineral density (BMD). One group was sham operated (Sham) and three groups were ovariectomized (Ovx). The groups and corresponding diets were Sham+control diet (n=12), Ovx+control diet (n=12), Ovx+5% BB (n=7), and Ovx+10% BB (n=7). Control diet was AIN-93M rodent diet, and the Ovx+5% BB and Ovx+10% BB were a diet modified to contain powdered, freeze-dried BB at levels of 5% and 10% (w/w). Following 100 days of treatment, whole body BMC and BMD were reassessed and bone specimens, blood, and 24-h urine samples were collected for analyses. Findings indicate that ovariectomy (Ovx) compromised whole body BMC and trabecular microarchitecture of the proximal tibia and fourth lumbar vertebra. C3G-rich BB at the level of 5% modestly protected BMDs, loss of the tibia, lumbar vertebra, and femur by 2.4%, 2.7%, and 4.3% (P<.0013; .0437; .0004), respectively. BB 5% treatment significantly prevented loss of tibial trabecular bone volume and trabecular number by 37% and 21%, respectively (P<.05), and also significantly prevented tibial trabecular separation by 22%. We conclude that C3G-rich BB treatment at the level of 5% (w/w) but not at 10% (w/w) may modestly reduce Ovx-induced bone loss evident by improved tibial, vertebral, and femoral BMD values, and tibial bone microstructural parameters. Bone protective effects may be as a result of the synergistic effects of phenolic compounds; however, further work is required to determine BBs' specific mechanisms of action. PMID:25386839

Kaume, Lydia; Gilbert, William; Smith, Breda J; Devareddy, Latha

2014-11-11

128

Arabidopsis thaliana ?-glucosidase BGLU15 attacks flavonol 3-O-?-glucoside-7-O-?-rhamnosides.  

PubMed

Kaempferol and quercetin 3-O-?-glucoside-7-O-?-rhamnoside (K3G7R and Q3G7R, respectively) are major flavonol bisglycosides accumulating in Arabidopsis thaliana with synergistic abiotic stresses (i.e., nitrogen deficiency and low temperature, NDLT). However, these molecules disappear rapidly during recovery from NDLT. Typically, catabolism of related chemicals relies on ?-glucosidase (BGLU) action. Evidence for flavonol 3-O-?-glucoside-7-O-?-rhamnoside BGLU activity is provided here. Major losses of Q3G7R and K3G7R coincided with an approximate 250% induction in flavonol 3-O-?-glucoside-7-O-?-rhamnoside BGLU activity within 2days of NDLT recovery relative to plants cultured under nitrogen sufficiency and high temperature (NSHT, control). QTOF-MS/MS established the product of Q3G7R hydrolysis in the presence of Arabidopsis cell free extracts was quercetin 7-O-?-rhamnoside. A phylogenetic analysis of the Arabidopsis glycoside hydrolase family 1 identified BGLU15 (At2g44450) and five other members that cluster with Fabaceae hydrolases known to attack isoflavones and isoflavonoids, which are structurally somewhat related to flavonol 3-O-?-glucoside-7-O-?-rhamnosides. Real time quantitative PCR analysis established a 300% higher expression of BGLU15 within 1day of the recovery from NDLT relative to control plants; lower or negligible changes in expression were evident for the remaining BGLUs. Recombinant thioredoxin-His6-tagged mature BGLU15 protein was expressed in Escherichia coli and purified to homogeneity. A comparison of a wide spectrum of ?-glucosides showed that recombinant BGLU15 preferentially hydrolyses the 3-O-?-glucosides of flavonols, but does not attack quercetin 3-O-?-rhamnoside, quercetin 3-O-?-galactoside and rutin. BGLU15 displayed the highest catalytic efficiency for Q3G7R and K3G7R yielding their respective 7-O-rhamnosides as products; flavonol 3-O-glucosides were also attacked, albeit with lower efficiency. Together, it appears the loss of flavonol 3-O-?-glucoside-7-O-?-rhamnosides in Arabidopsis is dependent upon the enzyme-mediated cleavage of the 3-O-? linked glucose moiety. PMID:25468534

Roepke, Jonathon; Bozzo, Gale G

2015-01-01

129

Enzymatic synthesis and characterization of arbutin glucosides using glucansucrase from Leuconostoc mesenteroides B1299CB  

Microsoft Academic Search

Two arbutin glucosides were synthesized via the acceptor reaction of a glucansucrase from Leuconostoc mesenteroides B-1299CB with arbutin and sucrose. The glucosides were purified by Bio-gel P-2 column chromatography and high-performance\\u000a liquid chromatography, and the structures were elucidated as 4-hydroxyphenyl ?-isomaltoside (arbutin-G1), 4-hydroxyphenyl\\u000a ?-isomaltotrioside (arbutin-G2), according to the results of 1H, 13C, heteronuclear single-quantum coherence, 1H-1H COSY, and heteronuclear multiple-bond

Young Hwan Moon; Seung Hee Nam; Jin Kang; Young-Min Kim; Jin-Ha Lee; Hee-Kyung Kang; Vincent Breton; Woo-Jin Jun; Ki-Deok Park; Atsuo Kimura; Doman Kim

2007-01-01

130

Oximes, nitriles and 2-hydroxynitriles as precursors in the biosynthesis of cyanogenic glucosides  

PubMed Central

The biosynthesis of the cyanogenic glucosides, linamarin and prunasin, was investigated in linen-flax, peach and cherry-laurel shoots. It was shown that related 2-oximino acids, aldoximes, nitriles and 2-hydroxynitriles were generally good precursors of the aglycone moiety. Studies with double-labelled compounds confirmed the retention of the oximino nitrogen atom from 2-oximinoisovaleric acid and isobutyraldoxime in the biosynthesis of linamarin. A general pathway from amino acids to cyanogenic glucosides involving N-hydroxyamino acids, aldoximes, nitriles and 2-hydroxynitriles is proposed. PMID:5131015

Tapper, B. A.; Butler, G. W.

1971-01-01

131

Characterization of Kinetic and Thermodynamic Parameters of Cyanidin-3-glucoside Methyl and Glucuronyl Metabolite Conjugates.  

PubMed

The determination of rate and equilibrium constants of anthocyanin metabolites with in vivo occurrence, cyanidin-4'-O-methyl-3-glucoside (Cy4'Me3glc) and cyanidin-7-O-glucuronyl-3-glucoside (Cy7Gluc3glc), was carried out for the first time by means of direct and reverse pH jumps. The thermodynamics and kinetics of these compounds are similar to the anthocyanin monoglucosides in particular for the analogous cyanidin-3-glucoside (Cy3glc) and peonidin-3-glucoside (Peo3glc). The rate and equilibrium constants of metabolites were also compared with malvin (malvidin 3,5-diglucoside) and with a bioinspired compound 3',4'-dihydroxy-7-O-glucopyranosyloxyflavylium (DGF). In Cy4'Me3glc and Cy7Gluc3glc the rate of hydration for a fixed pH value is slower than in DGF and the dominant species at moderately acidic solutions is the hemiketal. Oppositely, in DGF trans-chalcone is the dominant species at moderately acidic solutions. PMID:25622073

Cruz, Luís; Basílio, Nuno; Mateus, Nuno; Pina, Fernando; de Freitas, Victor

2015-02-01

132

Role of asparagine 1134 in glucosidic bond and transglycosylation specificity of reuteransucrase from Lactobacillus reuteri 121  

Microsoft Academic Search

Glucansucrases from lactic acid bacteria convert sucrose into various ?-glucans that differ greatly with respect to the glucosidic bonds present (e.g. dextran, mutan, alternan and reuteran). This study aimed to identify the structural features of the reuteransucrase from Lactobacillus reuteri 121 (GTFA) that determine its reaction specificity. We here report a detailed mutational analysis of a conserved region immediately next

Slavko Kralj; Wieger Eeuwema; Tom H. Eckhardt; Lubbert Dijkhuizen

2006-01-01

133

Ptesculentoside, a novel norsesquiterpene glucoside from the Australian bracken fern Pteridium esculentum  

Microsoft Academic Search

A novel norsesquiterpene glucoside ptesculentoside has been isolated from the Australian bracken Pteridium esculentum, together with the known bracken carcinogen ptaquiloside and lesser amounts of caudatoside. The structure of ptesculentoside is determined by analysis of 1D and 2D NMR spectra, and via its conversion into previously known pterosin G.

Mary T. Fletcher; Patrica Y. Hayes; Michael J. Somerville; James J. De Voss

2010-01-01

134

New p-menthanetriols and their glucosides from the fruit of caraway  

Microsoft Academic Search

Ten new p-menthanetriols, including eight stereoisomers of p-menthane-2,8,9-triol, and five new glucosides were isolated from the water-soluble portion of the methanol extract of the fruit of caraway (Carum carvi L.), which has been used as a spice and medicine. Their structures were clarified by spectral investigation.

Tetsuko Matsumura; Toru Ishikawa; Junichi Kitajima

2001-01-01

135

Water-soluble constituents of caraway: aromatic compound, aromatic compound glucoside and glucides  

Microsoft Academic Search

From the water-soluble portion of the methanolic extract of caraway (fruit of Carum carvi L.), an aromatic compound, an aromatic compound glucoside and a glucide were isolated together with 16 known compounds. Their structures were clarified as 2-methoxy-2-(4?-hydroxyphenyl)ethanol, junipediol A 2-O-?-d-glucopyranoside and l-fucitol, respectively.

Tetsuko Matsumura; Toru Ishikawa; Junichi Kitajima

2002-01-01

136

Water-soluble constituents of caraway: aromatic compound, aromatic compound glucoside and glucides.  

PubMed

From the water-soluble portion of the methanolic extract of caraway (fruit of Carum carvi L.), an aromatic compound, an aromatic compound glucoside and a glucide were isolated together with 16 known compounds. Their structures were clarified as 2-methoxy-2-(4'-hydroxyphenyl)ethanol, junipediol A 2-O-beta-D-glucopyranoside and L-fucitol, respectively. PMID:12377243

Matsumura, Tetsuko; Ishikawa, Toru; Kitajima, Junichi

2002-10-01

137

Rapid method for determination of anthocyanin glucosides and free delphinidin in grapes using u-HPLC.  

PubMed

A rapid method for the determination of anthocyanin glucosides and free delphinidin in food using ultra-high-performance liquid chromatography (u-HPLC) was validated through tests of precision, accuracy and linearity. The u-HPLC separation was performed on a reversed-phase C18 column (particle size 2 µm, i.d. 2 mm, length 100 mm) with a photodiode array detector. The limits of detection and quantification of the u-HPLC analyses ranged from 0.07 to 0.65 mg/kg for nine types of anthocyanin glucosides and from 0.08 to 0.26 mg/kg for delphinidin aglycone. The intra-day and inter-day precision of individual anthocyanin glucosides and delphinidin aglycone were less than 9.42%. All calibration curves showed good linearity (coefficient of determination = 0.99) within the tested ranges. The rapid and simultaneous u-HPLC method presented in this study significantly improved the speed, sensitivity and resolution of the analyses of nine types of anthocyanin glucosides and free delphidinin aglycone in grapes. PMID:23839806

Shim, You-Shin; Kim, Seunghee; Seo, Dongwon; Park, Hyun-Jin; Ha, Jaeho

2014-08-01

138

The bvr Locus of Listeria monocytogenes Mediates Virulence Gene Repression by ?-Glucosides  

PubMed Central

The ?-glucoside cellobiose has been reported to specifically repress the PrfA-dependent virulence genes hly and plcA in Listeria monocytogenes NCTC 7973. This led to the hypothesis that ?-glucosides, sugars of plant origin, may act as signal molecules, preventing the expression of virulence genes if L. monocytogenes is living in its natural habitat (soil). In three other laboratory strains (EGD, L028, and 10403S), however, the effect of cellobiose was not unique, and all fermentable carbohydrates repressed hly. This suggested that the downregulation of virulence genes by ?-glucosides is not a specific phenomenon but, rather, an aspect of a global regulatory mechanism of catabolite repression (CR). We assessed the effect of carbohydrates on virulence gene expression in a panel of wild-type isolates of L. monocytogenes by using the PrfA-dependent phospholipase C gene plcB as a reporter. Utilization of any fermentable sugar caused plcB repression in wild-type L. monocytogenes. However, an EGD variant was identified in which, as in NCTC 7973, plcB was only repressed by ?-glucosides. Thus, the regulation of L. monocytogenes virulence genes by sugars appears to be mediated by two separate mechanisms, one presumably involving a CR pathway and another specifically responding to ?-glucosides. We have identified in L. monocytogenes a 4-kb operon, bvrABC, encoding an antiterminator of the BglG family (bvrA), a ?-glucoside-specific enzyme II permease component of the phosphoenolpyruvate-sugar phosphotransferase system (bvrB), and a putative ADP-ribosylglycohydrolase (bvrC). Low-stringency Southern blots showed that this locus is absent from other Listeria spp. Transcription of bvrB was induced by cellobiose and salicin but not by arbutin. Disruption of the bvr operon by replacing part of bvrAB with an interposon abolished the repression by cellobiose and salicin but not that by arbutin. Our data indicate that the bvr locus encodes a ?-glucoside-specific sensor that mediates virulence gene repression upon detection of cellobiose and salicin. Bvr is the first sensory system found in L. monocytogenes that is involved in environmental regulation of virulence genes. PMID:10438775

Brehm, Klaus; Ripio, María-Teresa; Kreft, Jürgen; Vázquez-Boland, José-Antonio

1999-01-01

139

Mechanism of biosynthesis of thio- -D-glucuronides and thio- -D-glucosides.  

PubMed

1. The thio-beta-d-glucosiduronic acids (thio-beta-glucuronides) of o-aminothiophenol, diethyldithiocarbamic acid, p-nitrothiophenol and thiophenol are formed biosynthetically in broken- and intact-cell preparations of mouse liver. 2. For this biosynthesis to occur in homogenates or microsomal fractions, UDP-glucuronic acid was required during incubation; glucose, glucuronic acid or UDP could not replace it. UDP was a product of the reaction. 3. The biosynthetic mechanism linking glucuronic acid to thiol and carbodithioic groups therefore requires UDP-glucuronyltransferase activity and resembles that forming the various types of O-glucuronides. 4. An analogous enzymic mechanism employing UDP-glucose synthesizes the thio-beta-d-glucosides of diethyldithiocarbamic acid and thiophenol in gut preparations of the mollusc Arion ater; this mechanism resembles that forming the O-glucosides. The thio-beta-d-glucosides are formed also in intact cells. 5. As expected from the distribution of O-glycosides, S-glucuronides of these aglycones were not detectable with the invertebrate, nor were the S-glucosides with the vertebrate. 6. Despite their similar biosyntheses, S- and O-beta-glycosides differ in susceptibility to hydrolysis by beta-glycosidases. Rat preputial-gland beta-glucuronidase hydrolysed thioglucuronides of o-aminothiophenol, diethyldithiocarbamic acid and p-nitrothiophenol, hydrolysis being inhibited by glucarolactone; the thioglucuronide of thiophenol was not hydrolysed by preputial-gland or liver beta-glucuronidase. The two S-glucosides resisted hydrolysis by beta-glucosidase from almond emulsin. PMID:4658987

Dutton, G J; Illing, H P

1972-09-01

140

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

PubMed

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

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

2008-05-01

141

Involvement of Streptococcus gordonii Beta-Glucoside Metabolism Systems in Adhesion, Biofilm Formation, and In Vivo Gene Expression  

PubMed Central

Streptococcus gordonii genes involved in beta-glucoside metabolism are induced in vivo on infected heart valves during experimental endocarditis and in vitro during biofilm formation on saliva-coated hydroxyapatite (sHA). To determine the roles of beta-glucoside metabolism systems in biofilm formation, the loci of these induced genes were analyzed. To confirm the function of genes in each locus, strains were constructed with gene inactivation, deletion, and/or reporter gene fusions. Four novel systems responsible for beta-glucoside metabolism were identified, including three phosphoenolpyruvate-dependent phosphotransferase systems (PTS) and a binding protein-dependent sugar uptake system for metabolizing multiple sugars, including beta-glucosides. Utilization of arbutin and esculin, aryl-beta-glucosides, was defective in some mutants. Esculin and oligochitosaccharides induced genes in one of the three beta-glucoside metabolism PTS and in four other genetic loci. Mutation of genes in any of the four systems affected in vitro adhesion to sHA, biofilm formation on plastic surfaces, and/or growth rate in liquid medium. Therefore, genes associated with beta-glucoside metabolism may regulate S. gordonii in vitro adhesion, biofilm formation, growth, and in vivo colonization. PMID:15205427

Kiliç, Ali O.; Tao, Lin; Zhang, Yongshu; Lei, Yu; Khammanivong, Ali; Herzberg, Mark C.

2004-01-01

142

Protective effects of naringenin-7- O-glucoside on doxorubicin-induced apoptosis in H9C2 cells  

Microsoft Academic Search

Doxorubicin, a widely used chemotherapeutic agent, can give rise to severe cardiotoxicity by inducing cardiomyocyte apoptosis. Dracocephalum rupestre Hance, a Chinese traditional herb, has therapeutic potential for cardiovascular diseases. Naringenin-7-O-glucoside is the main active constituent of D. rupestre and there is increasing interest in its therapeutic applications. The aim of this study was to evaluate the effects of naringenin-7-O-glucoside on

Xiuzhen Han; Dongmei Ren; Peihong Fan; Tao Shen; Hongxiang Lou

2008-01-01

143

Involvement of Streptococcus gordonii Beta-Glucoside Metabolism Systems in Adhesion, Biofilm Formation, and In Vivo Gene Expression  

Microsoft Academic Search

Streptococcus gordonii genes involved in beta-glucoside metabolism are induced in vivo on infected heart valves during experimental endocarditis and in vitro during biofilm formation on saliva-coated hydroxyapatite (sHA). To determine the roles of beta-glucoside metabolism systems in biofilm formation, the loci of these induced genes were analyzed. To confirm the function of genes in each locus, strains were constructed with

Ali O. Kilic; Lin Tao; Yongshu Zhang; Yu Lei; Ali Khammanivong; Mark C. Herzberg

2004-01-01

144

Biosynthesis of Dehydrodiconiferyl Alcohol Glucosides: Implications for the Control of Tobacco Cell Growth 1  

PubMed Central

The dehydrodiconiferyl alcohol glucosides A and B are factors isolated from transformed Vinca rosea tumor cells that can replace the cytokinin requirement for growth of tobacco (Nicotiana tabacum) pith and callus cells in culture. These factors, present in tobacco pith cells, have their concentrations elevated approximately 2 orders of magnitude after cytokinin exposure. Biosynthesis experiments showed that these compounds are not cell wall fragments, as previously suggested, but are produced directly from coniferyl alcohol. Their synthesis is probably associated with the existing pathway for cell wall biosynthesis in both Vinca tumors and tobacco pith explants. The pathway requires only two steps, the dimerization of coniferyl alcohol by a soluble intracellular peroxidase and subsequent glycosylation. Biosynthetic experiments suggested that dehydrodiconiferyl alcohol glucoside breakdown was very slow and control of its concentration was exerted through restricted availability of coniferyl alcohol. PMID:16668635

Orr, John D.; Lynn, David G.

1992-01-01

145

Evolution of Aromatic ?-Glucoside Utilization by Successive Mutational Steps in Escherichia coli.  

PubMed

The bglA gene of Escherichia coli encodes phospho-?-glucosidase A capable of hydrolyzing the plant-derived aromatic ?-glucoside arbutin. We report that the sequential accumulation of mutations in bglA can confer the ability to hydrolyze the related aromatic ?-glucosides esculin and salicin in two steps. In the first step, esculin hydrolysis is achieved through the acquisition of a four-nucleotide insertion within the promoter of the bglA gene, resulting in enhanced steady-state levels of the bglA transcript. In the second step, hydrolysis of salicin is achieved through the acquisition of a point mutation within the bglA structural gene close to the active site without the loss of the original catabolic activity against arbutin. These studies underscore the ability of microorganisms to evolve additional metabolic capabilities by mutational modification of preexisting genetic systems under selection pressure, thereby expanding their repertoire of utilizable substrates. PMID:25448815

Zangoui, Parisa; Vashishtha, Kartika; Mahadevan, Subramony

2015-02-15

146

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

NASA Technical Reports Server (NTRS)

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.

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

1988-01-01

147

Acylated cyanidin 3-sambubioside-5-glucosides in three garden plants of the Cruciferae.  

PubMed

Seven acylated cyanidin 3-sambubioside-5-glucosides were isolated from the flowers of three garden plants in the Cruciferae. Specifically, four pigments were isolated from Lobularia maritima (L.) Desv., together with a known pigment, as well as, three pigments from Lunaria annua L., and two known pigments from Cheiranthus cheiri L. These pigments were determined to be cyanidin 3-O-[2-O-((acyl-II)-(beta-d-xylopyranosyl))-6-O-(acyl-I)-beta-d-glucopyranoside]-5-O-[6-O-(acyl-III)-beta-d-glucopyranoside], in which the acyl-I group is represented by glucosyl-p-coumaric acid, p-coumaric acid and ferulic acid, acyl-II by caffeic acid and ferulic acid, and acyl-III by malonic acid, respectively. The distribution and biosynthesis of acylated cyanidin 3-sambubioside-5-glucosides are discussed according to the variations of acylation and glucosylation at their 3-sambubiose residues. PMID:16777160

Tatsuzawa, Fumi; Saito, Norio; Shinoda, Koichi; Shigihara, Atsushi; Honda, Toshio

2006-06-01

148

Benzophenone C- and O-Glucosides from Cyclopia genistoides (Honeybush) Inhibit Mammalian ?-Glucosidase.  

PubMed

An enriched fraction of an aqueous extract prepared from the aerial parts of Cyclopia genistoides Vent. yielded a new benzophenone di-C,O-glucoside, 3-C-?-d-glucopyranosyl-4-O-?-d-glucopyranosyliriflophenone (1), together with small quantities of a known benzophenone C-glucoside, 3-C-?-d-glucopyranosylmaclurin (2). The isolated compounds showed ?-glucosidase inhibitory activity against an enzyme mixture extracted from rat intestinal acetone powder. Compound 2 exhibited significantly (p < 0.05) higher inhibitory activity (54%) than 1 (43%) at 200 ?M. In vitro tests in several cell models showed that 1 and its 3-C-monoglucosylated derivative (3-C-?-d-glucopyranosyliriflophenone) were marginally effective (p ? 0.05) in increasing glucose uptake. PMID:25419864

Beelders, Theresa; Brand, D Jacobus; de Beer, Dalene; Malherbe, Christiaan J; Mazibuko, Sithandiwe E; Muller, Christo J F; Joubert, Elizabeth

2014-12-26

149

Role of asparagine 1134 in glucosidic bond and transglycosylation specificity of reuteransucrase from Lactobacillus reuteri 121.  

PubMed

Glucansucrases from lactic acid bacteria convert sucrose into various alpha-glucans that differ greatly with respect to the glucosidic bonds present (e.g. dextran, mutan, alternan and reuteran). This study aimed to identify the structural features of the reuteransucrase from Lactobacillus reuteri 121 (GTFA) that determine its reaction specificity. We here report a detailed mutational analysis of a conserved region immediately next to the catalytic Asp1133 (putative transition-state stabilizing) residue in GTFA. The data show that Asn1134 is the main determinant of glucosidic bond product specificity in this reuteransucrase. Furthermore, mutations at this position greatly influenced the hydrolysis/transglycosylation ratio. Changes in this amino acid expands the range of glucan and gluco-oligosaccharide products synthesized from sucrose by mutant GTFA enzymes. PMID:16911522

Kralj, Slavko; Eeuwema, Wieger; Eckhardt, Tom H; Dijkhuizen, Lubbert

2006-08-01

150

Hepatoprotective activity of twelve novel 7'-hydroxy lignan glucosides from Arctii Fructus.  

PubMed

Twelve novel 7'-hydroxy lignan glucosides (1-12), including two benzofuran-type neolignans, two 8-O-4' neolignans, two dibenzylbutyrolactone lignans, and six tetrahydrofuranoid lignans, together with six known lignan glucosides (13-18), were isolated from the fruit of Arctium lappa L. (Asteraceae), commonly known as Arctii Fructus. Their structures were elucidated using spectroscopy (1D and 2D NMR, MS, IR, ORD, and UV) and on the basis of chemical evidence. The absolute configurations of compounds 1-12 were confirmed using rotating frame nuclear overhauser effect spectroscopy (ROESY), the circular dichroic (CD) exciton chirality method, and Rh2(OCOCF3)4-induced CD spectrum analysis. All of the isolated compounds were tested for hepatoprotective effects against D-galactosamine-induced cytotoxicity in HL-7702 hepatic cells. Compounds 1, 2, 7-12, and 17 showed significantly stronger hepatoprotective activity than the positive control bicyclol at a concentration of 1 × 10(-5) M. PMID:25180661

Yang, Ya-Nan; Huang, Xiao-Ying; Feng, Zi-Ming; Jiang, Jian-Shuang; Zhang, Pei-Cheng

2014-09-17

151

Identification and evaluation of flavone-glucosides isolated from barley sprouts and their inhibitory activity against bacterial neuraminidase.  

PubMed

Neuraminidase (NA) is one of the key enzymes responsible for bacterial infection and pathogenesis. This study aimed to gain deeper insights into the inhibitory effects of flavone-glucosides (1-9) isolated from barley sprouts (BS) on neuraminidase activity. The isolated compounds were identified as, lutonarin (1), saponarin (2), isoorientin (3), orientin (4), isovitexin (5), isoscoparin-7-O-[6-sinapoyl]-glucoside (6), isoscoparin-7-O-[6-feruloyl]-glucoside (7), isovitexin-7-O-[6-sinapoyl]-glucoside (8), and isovitexin-7-O-[6-feruloyl]-glucoside (9). Among them, compounds 1-5 exhibited neuraminidase-inhibitory activities in a dose-dependent manner, with IC50 values ranging from 20.1 to 32.7 ?M, in a non-competitive inhibition mode according to kinetic studies. Moreover, the individual flavone-glucoside levels differed notably, in particular, lutonarin (1) and saponarin (2) were shown to be present in the greatest amounts, according to UPLC analysis. Consequently, our results suggest that BS may be utilized as an effective NA inhibitor in human health food, additives, and feed. PMID:25522538

Park, Mi Jin; Ra, Ji-Eun; Seo, Kyung Hye; Jang, Ki-Chang; Han, Sang-Ik; Lee, Jin-Hwan; Kang, Young-Hwa; Nam, Min-Hee; Seo, Woo Duck

2014-10-01

152

Engineering of glucoside acceptors for the regioselective synthesis of ?-(1?3)-disaccharides with glycosynthases  

Microsoft Academic Search

Glycosynthase mutants obtained from Thermotogamaritima were able to catalyze the regioselective synthesis of aryl ?-d-Galp-(1?3)-?-d-Glcp and aryl ?-d-Glcp-(1?3)-?-d-Glcp in high yields (up to 90 %) using aryl ?-d-glucosides as acceptors. The need for an aglyconic aryl group was rationalized by molecular modeling calculations, which have emphasized a high stabilizing interaction of this group by stacking with W312 of the enzyme.

Zsuzanna Marton; Vinh Tran; Charles Tellier; Michel Dion; Jullien Drone; Claude Rabiller

2008-01-01

153

Interaction of kunjin virus with octyl- d-glucoside extracted Vero cell plasma membrane  

Microsoft Academic Search

Initial experiments using whole cells have shown that there were specific and saturable interactions between kunjin (KUN) virus and receptor molecules on the Vero cell surfaces. Solubilisation of Vero cell plasma membranes with octyl-d-glucoside (OG) yielded an extract which also interacted specifically with KUN virus. This was proven using electron microscopy. When the virus-OG-extract complex was exposed onto Vero cell

David Sankaran; Lionel C. L. Lau; Mah Lee Ng

1997-01-01

154

Kiwifruits ( Actinidia deliciosa ) transformed with a Vitis stilbene synthase gene produce piceid (resveratrol-glucoside)  

Microsoft Academic Search

A stilbene synthase gene was isolated from three Vitis spp. (V. vinifera, V. labrusca and V. riparia). These genes were placed under the control of the cauliflower mosaic virus 35S promoter and introduced into kiwifruit (Actinidia deliciosa) plants by Agrobacterium-mediated gene transfer. The introduced gene(s) were expressed and piceid (resveratrol-glucoside) rather than resveratrol\\u000a was produced in the leaves of the

S. Kobayashi; C. K. Ding; Y. Nakamura; I. Nakajima; R. Matsumoto

2000-01-01

155

Production of ascorbic acid glucoside by alginate-entrapped mycelia of Aspergillus niger  

Microsoft Academic Search

The mycelia of Aspergillus niger, cultivated in a medium containing 45 g l?1 maltose, 66 g l?1 yeast extract, and 5 g l?1 K2HPO4 at 30°C and 200 rpm, were used as a biocatalyst in the glucosylation of ascorbic acid. Free mycelia from 3-day-old culture,\\u000a when used in a 6-h reaction with maltose as the acyl donor, gave 16.07 g l?1 ascorbic acid glucoside corresponding

Hsin-Ju Hsieh; Kai-Yu Tung; Giridhar R. Nair; I-Ming Chu; Wen-Teng Wu

2007-01-01

156

Separation and identification of Taxifolin 3-O-glucoside isomers from Chamaecyparis obtusa (Cupressaceae).  

PubMed

Taxifolin 3-O-glucoside isomers, [(2R, 3R)-, (2R, 3S)-, (2S, 3R)- and (2S, 3S)-] were isolated from leaves of Chamaecyparis obtuse (Cupressaceae). Their structures were elucidated on the basis of UV, MS, CD, 1H- and 13C-NMR spectral data, including 2D shift correlation. It was found that the compounds could be distinguished by the use of 1H- and 13C-NMR spectral data. PMID:12462342

Sakushima, Akiyo; Ohno, Kosei; Coskun, Makusut; Seki, Koh-Ichi; Ohkura, Kazue

2002-12-01

157

Separation and Identification of Taxifolin 3- O Glucoside Isomers from Chamaecyparis Obtusa (Cupressaceae)  

Microsoft Academic Search

Taxifolin 3- O -glucoside isomers, [(2R, 3R)-, (2R, 3S)-, (2S, 3R)- and (2S, 3S)-] were isolated from leaves of Chamaecyparis obtuse (Cupressaceae). Their structures were elucidated on the basis of UV, MS, CD, 1 H- and 13 C-NMR spectral data, including 2D shift correlation. It was found that the compounds could be distinguished by the use of 1 H- and

Akiyo Sakushima; Kosei Ohno; Makusut Coskun; Koh-ichi Seki; Kazue Ohkura

2002-01-01

158

Biosynthesis of Cyanogenic Glucosides in Triglochin maritima and the Involvement of Cytochrome P450 Enzymes  

Microsoft Academic Search

The biosynthesis of the two cyanogenic glucosides, taxiphyllin and triglochinin, in Triglochin maritima (seaside arrow grass) has been studied using undialyzed microsomal preparations from flowers and fruits. Tyrosine was converted to p-hydroxymandelonitrile with Vmax and Km values of 36 nmol mg?1 g?1 fresh weight and 0.14 mM, respectively. p-Hydroxyphenylacetaldoxime and p-hydroxyphenylacetonitrile accumulated as intermediates in the reaction mixtures. Using radiolabeled

John Strikart Nielsen; Birger Lindberg Møller

1999-01-01

159

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

PubMed

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 258nm. The structure of 1 was confirmed by NMR and high resolution mass spectrometry. PMID:25529685

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

2015-05-01

160

Antitumor actions of a chromone glucoside cnidimoside A isolated from Cnidium japonicum  

Microsoft Academic Search

In a series of studies on the search for new antitumor and antimetastatic substances from the natural medicinal plants of\\u000a the Umbelliferae family, we previously reported that chalcone derivatives isolated from Angelica keisekei roots have antitumor and antimetastatic activities. In the present study, we examined the effects of a chromone glucoside\\u000a cnidimoside A isolated from Cnidium japonicum whole plants on

Yoshiyuki Kimura; Maho Sumiyoshi; Masahiko Taniguchi; Kimiye Baba

2008-01-01

161

Indoxyl sulfate, a uremic toxin, is biotransformed from indoxyl-?- d-glucoside (indican) in rats  

Microsoft Academic Search

Indican (Indoxyl-?-d-glucoside) is present in many Chinese herbs such as Isatis indigotica, Clerodendrum crytophyllum, Glehnia littoralis, Polygonum tinctorium and P. perfoliatum. This study aims to investigate whether indoxyl sulfate, a uremic toxin, would be biotransformed from indican in rats. Indican was administered intravenously and orally to Sprague–Dawley rats. The blood samples were withdrawn via cardiopuncture at specific time points and

Yu-Chi Hou; Shang-Yuan Tsai; Shu-Ling Chan; Shih-Ying Yang; Pei-Dawn Lee Chao

2008-01-01

162

Glucoside formation as a novel metabolic pathway of pantothenic acid in the dog.  

PubMed

Metabolism of pantothenic acid (PaA) in beagle dogs was investigated. The dogs excreted 12.3% of the dose in the urine within 24 hr after a single oral administration of [3H]PaA (3 mg/kg). High performance liquid chromatographic analysis of the urine showed the presence of unchanged vitamin and a major metabolite, which accounted for 60.2 and 39.8% of the urinary radioactivity respectively. Although the metabolite was hydrolyzed by treatment with beta-glucuronidase or acid phosphatase, it was found that this hydrolysis resulted from the actions of beta-glucosidase contained as a contaminant in these enzyme preparations. beta-Glucosidase completely hydrolyzed the metabolite to generate PaA and glucose. The metabolite was isolated and subjected to GC/MS and NMR analyses. It was identical to synthetic PaA beta-glucoside, 4'-O-(beta-D-glucopyranosyl)-D-pantothenic acid. It was shown by the use of dog liver microsomes that PaA underwent beta-glucosidation in the presence of uridine diphosphate glucose (UDPG). It is proposed that beta-glucosidation by UDP-glucosyltransferase is a novel metabolic pathway of PaA in the dog. PMID:3096335

Nakano, K; Sugawara, Y; Ohashi, M; Harigaya, S

1986-11-01

163

Hydrolysis of aromatic ?-glucosides by non-pathogenic bacteria confers a chemical weapon against predators.  

PubMed

Bacteria present in natural environments such as soil have evolved multiple strategies to escape predation. We report that natural isolates of Enterobacteriaceae that actively hydrolyze plant-derived aromatic ?-glucosides such as salicin, arbutin and esculin, are able to avoid predation by the bacteriovorous amoeba Dictyostelium discoideum and nematodes of multiple genera belonging to the family Rhabditidae. This advantage can be observed under laboratory culture conditions as well as in the soil environment. The aglycone moiety released by the hydrolysis of ?-glucosides is toxic to predators and acts via the dopaminergic receptor Dop-1 in the case of Caenorhabditis elegans. While soil isolates of nematodes belonging to the family Rhabditidae are repelled by the aglycone, laboratory strains and natural isolates of Caenorhabditis sp. are attracted to the compound, mediated by receptors that are independent of Dop-1, leading to their death. The ?-glucosides-positive (Bgl(+)) bacteria that are otherwise non-pathogenic can obtain additional nutrients from the dead predators, thereby switching their role from prey to predator. This study also offers an evolutionary explanation for the retention by bacteria of 'cryptic' or 'silent' genetic systems such as the bgl operon. PMID:23677347

Sonowal, Robert; Nandimath, Krithi; Kulkarni, Sucheta S; Koushika, Sandhya P; Nanjundiah, Vidyanand; Mahadevan, S

2013-07-01

164

Bioconversion of piceid to piceid glucoside using amylosucrase from Alteromonas macleodii deep ecotype.  

PubMed

Resveratrol, or its glycoside form piceid, is a dietary antioxidant polyphenolic compound, found in grapes and red wine that has been shown to have protective effects against cardiovascular disease. However, very low water solubility of the compound may limit its application in the food and pharmaceutical industries. The amylosucrase (AMAS) of Alteromonas macleodii Deep ecotype was expressed in Escherichia coli and showed high glycosyltransferase activity to produce the glucosyl piceid when piceid was used as an acceptor. The conversion yield of piceid glucoside was 35.2%. Biotransformation using culture of the E. coli harboring the amas gene increased the yield up to 70.8%. The transfer product was purified by reverse phase chromatography and recycling preparative HPLC, and the molecular structure of the piceid glucoside was determined using NMR spectroscopy. The piceid glucoside was identified as glucosyl-alpha-(1-->4)-piceid. The solubility of glucosyl piceid was 5.26 and 1.14 times higher than those of resveratrol and piceid, respectively. It is anticipated that dietary intake of this compound is more effective by enhancing the bioavailability of resveratrol in the human body because of its hydrophilic properties in the intestinal fluid. PMID:23221533

Park, Hyunsu; Kim, Jieun; Park, Ji-Hae; Baek, Nam-In; Park, Cheon-Seok; Lee, Hee-Seob; Cha, Jaeho

2012-12-01

165

[UPLC-MS/MS determination of content of three iridoids of xingnaojing oral preparation in rat brains and study on their brain pharmacokinetics].  

PubMed

To establish a UPLC-MS/MS method for the simultaneous determination of geniposide, genipin 1-O-beta-D-gentiobioside and geniposidic acid in rat brains and study the brain pharmacokinetics of the three iridoid glycosides in stroke rat after the oral administration of Xingnaojing. In this experiment, brain samples were precipitated with protein for twice. Acquity BEH C18 column was adopted, with acetonitrile-0.1% formic acid-water as the mobile phase for gradient elution. ESI source was adopted for mass spectra; multiple reaction monitoring (MRM) was conducted to detect negative ions. The time for sample analysis was 3.5 min. the results showed good linear relations among the three iridoid glycosides, with the extraction recovery between 99.6% and 114.3%, good intra- and inter-day precisions and accuracies and stability in line with the requirements. The t1/2 and MRT in the three components were similar in brains of stroke rats. Geniposide and genipin 1-O-beta-D-gentiobioside showed double peaks; where as geniposidic acid showed a single peak. In conclusion, the method is so specific, sensitive, accurate and reliable that it can be used to study the brain pharmacokinetics of Xingnaojing oral preparation. PMID:25244774

Xu, Pan; Du, Shou-Ying; Lu, Yang; Bai, Jie; Liu, Hui-Min; Du, Qiu; Chen, Zhen-Zhen; Wang, Zhen

2014-06-01

166

Cassava Plants with a Depleted Cyanogenic Glucoside Content in Leaves and Tubers. Distribution of Cyanogenic Glucosides, Their Site of Synthesis and Transport, and Blockage of the Biosynthesis by RNA Interference Technology1  

PubMed Central

Transgenic cassava (Manihot esculenta Crantz, cv MCol22) plants with a 92% reduction in cyanogenic glucoside content in tubers and acyanogenic (<1% of wild type) leaves were obtained by RNA interference to block expression of CYP79D1 and CYP79D2, the two paralogous genes encoding the first committed enzymes in linamarin and lotaustralin synthesis. About 180 independent lines with acyanogenic (<1% of wild type) leaves were obtained. Only a few of these were depleted with respect to cyanogenic glucoside content in tubers. In agreement with this observation, girdling experiments demonstrated that cyanogenic glucosides are synthesized in the shoot apex and transported to the root, resulting in a negative concentration gradient basipetal in the plant with the concentration of cyanogenic glucosides being highest in the shoot apex and the petiole of the first unfolded leaf. Supply of nitrogen increased the cyanogenic glucoside concentration in the shoot apex. In situ polymerase chain reaction studies demonstrated that CYP79D1 and CYP79D2 were preferentially expressed in leaf mesophyll cells positioned adjacent to the epidermis. In young petioles, preferential expression was observed in the epidermis, in the two first cortex cell layers, and in the endodermis together with pericycle cells and specific parenchymatic cells around the laticifers. These data demonstrate that it is possible to drastically reduce the linamarin and lotaustralin content in cassava tubers by blockage of cyanogenic glucoside synthesis in leaves and petioles. The reduced flux to the roots of reduced nitrogen in the form of cyanogenic glucosides did not prevent tuber formation. PMID:16126856

Jørgensen, Kirsten; Bak, Søren; Busk, Peter Kamp; Sørensen, Charlotte; Olsen, Carl Erik; Puonti-Kaerlas, Johanna; Møller, Birger Lindberg

2005-01-01

167

Biological activity of quercetin-3-O-glucoside, a known plant flavonoid.  

PubMed

Cytotoxic, phytotoxic, antimicrobial and antioxidant effects of quercetin 3-O-glucoside (Q3G) isolated by HPLC from aerial parts of Prangos ferulaceae was studied by MTT assay, lettuce germination assay, disk diffusion and DPPH method. Our results showed that Q3G exhibits high antioxidant effect with RC(50) of 22 microg/mL, it has low cytotoxicity and no antibacterial effects. Q3G exhibits high phytotoxic effect with IC(50) value of 282.7 microg/ml, as well. It is assumed that Q3G does not play a defense role in plants and it may act as an allelopatic agent. PMID:19621057

Razavi, Seyed Mehdi; Zahri, Saber; Zarrini, Gholamreza; Nazemiyeh, Hossein; Mohammadi, Sariyeh

2009-01-01

168

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

PubMed

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

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

2012-04-01

169

Lipid profile of Helicobacter spp.: presence of cholesteryl glucoside as a characteristic feature.  

PubMed Central

The lipid and fatty acid profiles of eight Helicobacter spp. (H. nemestrinae, H. acinonyx, H. canis, Helicobacter sp. strain CLO-3, "H. rappini" [Flexispira rappini], H. pametensis, Helicobacter sp. strain Bird-B, and Helicobacter sp. strain Bird-C) and the fatty acid profiles of five additional species (H. pylori, H. felis, H. muridarum, H. mustelae, and H. fennelliae) were analyzed and compared. A heterologous fatty acid profile was observed among the Helicobacter spp., and on that basis the species could be divided into two groups. Group A had 19-carbon cyclopropane fatty acid (19:0cyc) and tetradecanoic acid (14:0) as the major fatty acids, and group B characteristically lacked the 19:0cyc and had hexadecanoic acid (16:0) and octadecenoic (18:1) acids as the major fatty acids. The species of group A are primarily gastric colonizers, and those of group B are primarily intestinal colonizers. Seven of the eight species studied showed the unusual and characteristic presence of cholesteryl glucosides (CGs), and most of these seven showed a very large amount (9.7 to 27.4% of the weight of total extractable lipid). The types of CGs and their distribution in different species were as follows: cholesteryl-6-O-acyl-alpha-D-glucopyranoside (cholesteryl-6-O-tetradecanoyl-alpha-D-glucopyranoside in H. nemestrinae and mainly cholesteryl-6-O-dodecanoyl-alpha-D-glucopyranoside in "H. rappini"), cholesteryl-alpha-D-glucopyranoside (H. nemestrinae, H. acinonyx, H. canis, Helicobacter sp. strain CLO-3, and "H. rappini"), and cholesteryl-6-O-phosphatidyl-alpha-D-glucopyranoside (H. nemestrinae, H. acinonyx, H. canis, and Helicobacter sp. strain CLO-3). Besides this, we could also detect cholesteryl acyl glucoside in H. acinonyx, cholesteryl glucoside in Helicobacter sp. strains Bird-B and -C, and cholesteryl phosphatidyl glucoside in "H. rappini" and Helicobacter sp. strain Bird-C. A selective accumulation of free cholesterol was observed in the neutral lipid fractions. On the basis of the detection of CGs in 11 of the 13 species studied so far, the presence of CGs appears to be a characteristic feature of the genus Helicobacter. In view of this and also because of a simple and rapid detection method described herein, the CGs can be used as a valuable chemotaxonomic marker. PMID:8606185

Haque, M; Hirai, Y; Yokota, K; Mori, N; Jahan, I; Ito, H; Hotta, H; Yano, I; Kanemasa, Y; Oguma, K

1996-01-01

170

Specific accumulation and revised structures of acridone alkaloid glucosides in the tips of transformed roots of Ruta graveolens.  

PubMed

The root tips of Ruta graveolens (common rue) show strong autofluorescence of acridone alkaloids, which are characteristic secondary metabolites of this plant. To study the specific distribution and accumulation of acridone alkaloids in various root segments of Ruta graveolens, root material was harvested from genetically transformed root cultures and extracts were investigated by chromatographic techniques and HPLC-(1)H NMR spectroscopy. The cells of the elongation and differentiation zones contained acridone glucosides and large amounts of acridone alkaloids, mainly rutacridone. Gravacridondiol glucoside was identified as the dominant secondary compound of the root tips and its structure revised by means of spectroscopic methods. In addition, minor acridones, including the structurally revised gravacridontriol glucoside and unknown natural products, were found in the root tip. PMID:15110689

Kuzovkina, Inna; Al'terman, Irina; Schneider, Bernd

2004-04-01

171

Differential Performance of a Specialist and Two Generalist Herbivores and Their Parasitoids on Plantago lanceolata  

E-print Network

on Plantago lanceolata Joanneke H. Reudler & Arjen Biere & Jeff A. Harvey & Saskya van Nouhuys Received: 28 the effects of the concentration of the two main iridoid glycosides (IGs) in Plantago lanceolata, aucubin-diapause larval and pupal mortality on its local Finnish P. lanceolata than on Dutch genotypes. This could

van Nouhuys, Saskya

172

Development and Evaluation of Monoclonal Antibodies for the Glucoside of T-2 Toxin (T2-Glc)  

PubMed Central

The interactions between fungi and plants can yield metabolites that are toxic in animal systems. Certain fungi are known to produce sesquiterpenoid trichothecenes, such as T-2 toxin, that are biotransformed by several mechanisms including glucosylation. The glucosylated forms have been found in grain and are of interest as potential reservoirs of T-2 toxin that are not detected by many analytical methods. Hence the glucosides of trichothecenes are often termed “masked” mycotoxins. The glucoside of T-2 toxin (T2-Glc) was linked to keyhole limpet hemocyanin and used to produce antibodies in mice. Ten monoclonal antibody (Mab)-producing hybridoma cell lines were developed. The Mabs were used in immunoassays to detect T2-Glc and T-2 toxin, with midpoints of inhibition curves (IC50s) in the low ng/mL range. Most of the Mabs demonstrated good cross-reactivity to T-2 toxin, with lower recognition of HT-2 toxin. One of the clones (2-13) was further characterized with in-depth cross-reactivity and solvent tolerance studies. Results suggest Mab 2-13 will be useful for the simultaneous detection of T-2 toxin and T2-Glc. PMID:23877196

Maragos, Chris M.; Kurtzman, Cletus; Busman, Mark; Price, Neil; McCormick, Susan

2013-01-01

173

Isoarnottinin 4'-glucoside, a glycosylated coumarin from Prangos uloptera, with biological activity.  

PubMed

Coumarins are a well-known group of natural products distributed in the plant kingdom especially in the family Apiaceae with various biological activities. Isoarnottinin 4'-glucoside is a simple glycosylated coumarin found previously in a few genera of Apiaceae, and its biological activities have not been previously described in details. In the present paper, the compound was isolated from Prangos uloptera (Apiaceae) leaves using HPLC techniques. Antimicrobial, phytotoxic and cytotoxic activities of the compound were evaluated by disk diffusion, lettuce assay and MTT method. Our results indicated that the compound has high antibacterial effect against Erwinia carotovora, a common plant pathogen with MIC value of 100 microg/mL. The compound also exhibited significant phytotoxic activity against lettuce and modest cytotoxic activity against HeLa cell line with IC50 of 0 .84 mg/mL. It could be concluded that isoamottinin 4'-glucoside may play phytoalexin or allelopathic role for plant and may be a candidate for an antibacterial agent or a bioherbicide. PMID:21717896

Razavi, Seyed Mehdi; Zarrini, Gholamreza; Rad, Farah Gholami

2011-01-01

174

Biosynthesis of cyanogenic glucosides: in vitro analysis of the glucosylation step.  

PubMed

The last step in the biosynthesis of cyanogenic glucosides, the glucosylation of the cyanohydrin intermediate, has been investigated in detail using Triglochin maritima seedlings. The glucosyltransferase activity is not associated with membranes and appears to be a "soluble" enzyme. The cyanohydrin intermediate, which is formed by hydroxylation of 4-hydroxyphenylacetonitrile by a membrane-bound enzyme, is free to equilibrate in the presence of the glucosyltransferase and UDPG, because it can be trapped very efficiently. This indicates that this intermediate is not channeled (unlike some of the other intermediates), although it is probably the most labile of all of them. The glucosyltransferase of T. maritima responsible for the glucosylation of the cyanohydrin was separated from another glucosyltransferase, which used 4-hydroxybenzylalcohol as a substrate, and purified over 200-fold. It catalyzed the glucose transfer from UDPG to only 4-hydroxymandelonitrile and 3,4-dihydroxymandelonitrile, giving rise to the respective cyanogenic glucosides. Although the activities with these two substrates behaved differently in certain respects (e.g., extent of inactivation during purification and difference in activation by higher salt concentrations), most of the data acquired favor the view that only one enzyme in T. maritima is responsible for the glucosylation of both substrates. PMID:6230992

Hösel, W; Schiel, O

1984-02-15

175

Ultraperformance liquid chromatography tandem mass spectrometry determination of cyanogenic glucosides in Trifolium species.  

PubMed

Cyanogenic glucosides were analyzed by ultra-high-performance liquid chromatography combined with mass spectrometry in 88 Trifolium species grown at the same site. On the basis of the occurrence of cyanogenic glucosides and the linamarin/lotaustralin ratio species could be grouped into five clusters. Cluster C1 included 37 species, which did not contain cyanogens. Cluster C2 (22 species) included plants containing only lotaustralin. In clusters C3 (14 species), C4 (13 species), and C5 (2 species) both linamarin and lotaustralin were present but at different ratios. In C3 and C4 the linamarin/lotaustralin ratio was below 1, whereas in cluster C5 the ratio was much higher. Generally, the total content of cyanogens was below 500 ?g/g dry matter. Only in Trifolium repens var. biasoletti and Trifolium montanum extremely high cyanogen concentrations were observed. There was no general rule of occurrence of cyanogens. Samples of the same species from different countries accumulated cyanogens or could be free of these compounds. PMID:24476020

Muzashvili, Tamar; Moniuszko-Szajwaj, Barbara; Pecio, Lukasz; Oleszek, Wieslaw; Stochmal, Anna

2014-02-26

176

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

PubMed Central

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

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

2014-01-01

177

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

PubMed

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

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

2013-11-01

178

Absorption of toxic beta-glucosides produced by plants and their effect on tissue trehalases from insects.  

PubMed

Trehalases present in body wall, Malpighian tubules, fat body, midgut and haemolymph from Tenebrio molitor (Coleoptera), Musca domestica (Diptera), Spodoptera frugiperda and Diatraea saccharalis (Lepidoptera) were assayed in the presence and absence of toxic beta-glucosides produced by plants or their aglycones. The glucosides used were phlorizin, amygdalin, prunasin and the aglycone mandelonitrile. In addition, T. molitor and S. frugiperda trehalases were assayed with and without esculin. More than 60% of total trehalase activity was found in the midgut of these insects. As a rule, trehalases present in each insect were inhibited by at least two of the glucosides. Prunasin was the best inhibitor in tissues with highest trehalase activity. S. frugiperda beta-glucosidases were not able to hydrolyze esculin. Nevertheless, their larval midguts absorb the intact glucoside that is recovered from the fat body, Malpighian tubules and mainly from haemolymph. Mature larvae fed on a diet containing 3 mM (0.1%) esculin have 0.2 mM esculin in their haemolymph, and weigh 60% of control larvae. In vitro, haemolymph trehalase activity is abolished by 0.5 mM esculin. This inhibition may play a role in the decrease of body weight and in animal survival. S. frugiperda larvae reared in 0.1% amygdalin-containing diet present higher trehalase activity in tissues than the larvae reared in 0.1% esculin-containing diet. Higher trehalase activity should be the reason why the S. frugiperda development is not impaired by 1% dietary amygdalin, in contrast to what is observed when insects are reared in 0.1% esculin. The data suggest that many plant beta-glucosides are toxic because they inhibit trehalase, a key enzyme controlling glucose availability in insects. PMID:16458033

Silva, Maria C P; Terra, Walter R; Ferreira, Clélia

2006-03-01

179

Cloning and biochemical analysis of ?-glucoside utilization (bgl) operon without phosphotransferase system in Pectobacterium carotovorum subsp. carotovorum LY34.  

PubMed

?-Glucosidases are widespread in bacteria and involved in the metabolism of various carbohydrate substrates. Studying of ?-glucoside utilization (bgl) operons on operon of Pectobacterium carotovorum subsp. carotovorum LY34 (Pcc LY34) will help us understanding how ?-glucoside utilization (bgl) operon can cooperate with other systems in bacterium caused soft-rot disease. Pcc LY34 causes soft-rot disease in plants and expresses multiple enzymatic forms of ?-glucosidases. To fully explore the ?-glucoside utilization system in Pcc LY34, we have isolated a bgl operon from a genomic library for screening of ?-glucosidase activities. Sequence analysis of a 3050bp cloned DNA fragment (accession number AY870655) shows two open reading frames (bglY and bglK) that are predicted to encode proteins of 474 and 278 amino acid residues, respectively. Pair wise similarity analysis suggests BglY is a beta-glucosidase (a member of glycosyl hydrolase family 1) and BglK is a transcriptional antiterminator protein. bglY promoter region contains an inverted repeat sequence similar to transcriptional terminator. Different from other four ?-glucoside utilization operons of Pcc LY34 strain, BglY contains signal peptide sequences as extracellular ?-glucosidase. Comparisons of five ?-glucoside utilization operons of Pcc LY34 strain showed that bglYK operon does not have phosphotransferase system domain which are responsible for sugar transportation. BglY shares 33-44% identity with other four ?-glucosidases of Pcc LY34 strain. Enzyme assay showed that purified BglY enzyme hydrolyzed salicin, arbutin, pNPG, and MUG, and exhibited maximal activity at pH 7.0 and 40°C. This activity was enhanced Mg(2+). Site-directed mutagenesis revealed E166 and E371 are critical of BglY's ?-glucosidase activity. PMID:22502871

An, Chang Long; Kim, Min Keun; Kang, Tae Ho; Kim, Jungho; Kim, Hoon; Yun, Han Dae

2012-09-01

180

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

PubMed

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

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

2014-05-01

181

Potential applications of glucosyltransferases in terpene glucoside production: impacts on the use of aroma and fragrance.  

PubMed

The detection of glucoconjugated forms of monoterpene alcohols in rose petals in the late 1960s opened the new field of nonvolatile aroma precursors in flavor research. It is now well established that odorless glycosides represent a significant pool of aroma precursors in plants where they act as preformed but inactivated defense or attractive chemicals. Technical improvements in the separation and identification of plant secondary metabolites have provided a multitude of chemical structures, but functional characterization of glycosyltransferases that catalyze their formation lags behind. As technical efforts and costs for DNA sequencing dramatically dropped during the last decade, the number of plant genome sequences increased significantly, thus providing opportunities to functionally characterize the glycosyltransferase gene families in plants. These studies yielded the first glycosyltransferase genes that encode efficient biocatalysts for the production of monoterpene glucosides. They have applications in the food, feed, chemical, cosmetic, and pharmaceutical industries as slow release aroma chemicals. PMID:25431013

Schwab, Wilfried; Fischer, Thilo C; Giri, Ashok; Wüst, Matthias

2015-01-01

182

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

PubMed Central

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

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

2013-01-01

183

Indoxyl sulfate, a uremic toxin, is biotransformed from indoxyl-beta-D-glucoside (indican) in rats.  

PubMed

Indican (Indoxyl-beta-D-glucoside) is present in many Chinese herbs such as Isatis indigotica, Clerodendrum crytophyllum, Glehnia littoralis, Polygonum tinctorium and P. perfoliatum. This study aims to investigate whether indoxyl sulfate, a uremic toxin, would be biotransformed from indican in rats. Indican was administered intravenously and orally to Sprague-Dawley rats. The blood samples were withdrawn via cardiopuncture at specific time points and the serum concentrations of indican and indoxyl sulfate were assayed by HPLC method. The results showed that indican was rapidly and extensively metabolized to indoxyl sulfate either given intravenously or orally. Indoxyl sulfate showed markedly higher systemic exposure than indican. Because indoxyl sulfate is a harmful uremic toxin, we suggest that the content of indican in the aforementioned medicinal plants be quantitated and well controlled to ensure the safety for clinical use. PMID:18619995

Hou, Yu-Chi; Tsai, Shang-Yuan; Chan, Shu-Ling; Yang, Shih-Ying; Chao, Pei-Dawn Lee

2008-09-01

184

Synthesis, characterisation and antioxidant features of procyanidin B4 and malvidin-3-glucoside stearic acid derivatives.  

PubMed

The acylation of procyanidin B4 with a saturated fatty acid chloride containing 18 carbon atoms was studied in order to obtain procyanidin B4 3-O-di-stearic acid conjugate. This compound was structurally characterised by mass spectrometry and 1D and 2D NMR techniques. Derivatization of malvidin-3-glucoside using stearoyl chloride in acetonitrile was also performed yielding mono-, di- and tri-stearic ester derivatives. The novel derivatives obtained revealed significant antioxidant activity, although lower than the respective precursors. However, the chemical modification of anthocyanins and procyanidins (water soluble pigments) to more lipophilic compounds has the advantage of increased bioavailability in biological matrices, and to potentiate their application in food matrices and cosmetic products. PMID:25529709

Cruz, Luis; Fernandes, Virgínia C; Araújo, Paula; Mateus, Nuno; de Freitas, Victor

2015-05-01

185

Biosynthesis of cyanogenic glucosides in Triglochin maritima and the involvement of cytochrome P450 enzymes.  

PubMed

The biosynthesis of the two cyanogenic glucosides, taxiphyllin and triglochinin, in Triglochin maritima (seaside arrow grass) has been studied using undialyzed microsomal preparations from flowers and fruits. Tyrosine was converted to p-hydroxymandelonitrile with V(max) and K(m) values of 36 nmol mg(-1) g(-1) fresh weight and 0.14 mM, respectively. p-Hydroxyphenylacetaldoxime and p-hydroxyphenylacetonitrile accumulated as intermediates in the reaction mixtures. Using radiolabeled tyrosine as substrate, the radiolabel was easily trapped in p-hydroxyphenylacetaldoxime and p-hydroxyphenylacetonitrile when these were added as unlabeled compounds. p-Hydroxyphenylacetaldoxime was the only product obtained using microsomes prepared from green leaves or dialyzed microsomes prepared from flowers and fruits. These data contrast earlier reports (Hösel and Nahrstedt, Arch. Biochem. Biophys. 203, 753-757, 1980; and Cutler et al., J. Biol. Chem. 256, 4253-4258, 1981) where p-hydroxyphenylacetaldoxime was found not to accumulate. All steps in the conversion of tyrosine to p-hydroxymandelonitrile were found to be catalyzed by cytochrome P450 enzymes as documented by photoreversible carbon monoxide inhibition, inhibition by antibodies toward NADPH-cytochrome P450 oxidoreductase, and by cytochrome P450 inhibitors. We hypothesize that cyanogenic glucoside synthesis in T. maritima is catalyzed by multifunctional cytochrome P450 enzymes similar to CYP79A1 and CYP71E1 in Sorghum bicolor except that the homolog to CYP71E1 in T. maritima exhibits a less tight binding of p-hydroxyphenylacetonitrile, thus permitting the release of this intermediate and its conversion into triglochinin. PMID:10415119

Nielsen, J S; Moller, B L

1999-08-01

186

Luteolin and luteolin-7-O-glucoside from dandelion flower suppress iNOS and COX2 in RAW264.7 cells  

Microsoft Academic Search

Both reactive oxygen- and nitrogen-derived reactive species play important roles in physiological and pathophysiological conditions. Flavones, luteolin and luteolin-7-O-glucoside along with a rich plant source of both flavones, namely dandelion (Taraxacum officinale) flower extract were studied for antioxidant activity in different in vitro model systems. In this current study, luteolin and luteolin-7-O-glucoside at concentrations lower than 20 µM, significantly (p

Chun Hu; David D. Kitts

2004-01-01

187

PREPARATIVE SEPARATION OF AXIFOLIN-3-GLUCOSIDE, HYPEROSIDE AND AMYGDALIN FROM PLANT EXTRACTS BY HIGH-SPEED COUNTERCURRENT CHROMATOGRAPHY  

PubMed Central

High-speed countercurrent chromatography (HSCCC) was successfully used to isolate three bioactive compounds, i.e., amygdalin from bitter almond and taxifolin-3-glucoside and quercetin-3-galactoside (hyperoside) from water extract of Agrimonia pilosa Ledeb, respectively. From 1 g of the crude extract 65 mg of amygdalin was isolated at 97% purity using a two-phase solvent system composed of ethyl acetate-n-butanol-water (5:2:5, v/v) by preparative HSCCC. From a 400 mg amount of crude extract of Agrimonia pilosa Ledeb, 11 mg of taxifolin-3-glucoside and 8 mg of hyperoside were isolated at 96% purity using a two-phase solvent system composed of ethyl acetate-methanol-water (25:1:25, v/v) similarly by preparative HSCCC. The final structural identification was performed by MS, 1H-NMR and 13C-NMR Spectra. PMID:20046896

Wei, Yun; Xie, Qianqian; Ito, Yoichiro

2009-01-01

188

PREPARATIVE SEPARATION OF AXIFOLIN-3-GLUCOSIDE, HYPEROSIDE AND AMYGDALIN FROM PLANT EXTRACTS BY HIGH-SPEED COUNTERCURRENT CHROMATOGRAPHY.  

PubMed

High-speed countercurrent chromatography (HSCCC) was successfully used to isolate three bioactive compounds, i.e., amygdalin from bitter almond and taxifolin-3-glucoside and quercetin-3-galactoside (hyperoside) from water extract of Agrimonia pilosa Ledeb, respectively. From 1 g of the crude extract 65 mg of amygdalin was isolated at 97% purity using a two-phase solvent system composed of ethyl acetate-n-butanol-water (5:2:5, v/v) by preparative HSCCC. From a 400 mg amount of crude extract of Agrimonia pilosa Ledeb, 11 mg of taxifolin-3-glucoside and 8 mg of hyperoside were isolated at 96% purity using a two-phase solvent system composed of ethyl acetate-methanol-water (25:1:25, v/v) similarly by preparative HSCCC. The final structural identification was performed by MS, (1)H-NMR and (13)C-NMR Spectra. PMID:20046896

Wei, Yun; Xie, Qianqian; Ito, Yoichiro

2009-01-01

189

Inhibitory effects of a new iridoid, patridoid II and its isomers, on nitric oxide and TNF-alpha production in cultured murine macrophages.  

PubMed

Patridoids I, II and IIA, are new iridoids isolated from the whole plants of Patrinia saniculaefolia. These compounds were examined by assessing their effects on the production of tumor necrosis factor-alpha (TNF-alpha) as well as by investigating the expression of two enzymes, inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2), in the lipopolysaccharide (LPS)-stimulated murine macrophage-like cell line, Raw 264.7. Among them, patridoid II consistently inhibited nitric oxide (NO) and TNF-alpha production in a dose-dependent manner, with IC (50) values of 14.1 and 17.6 microM, respectively. Western Blotting probed with specific anti-iNOS antibodies showed that the decrease in the quantity of the NO product was accompanied by a decrease in the iNOS protein level. However, all three patridoids did not affect the COX-2 protein expression level in the LPS-stimulated macrophages. In addition, the C-5 isomer of patridoid II, patridoid I, only slightly affected the production of NO. Moreover, the C-3 isomer of patridoid II, patridoid IIA, did not inhibit proinflammatory cytokines and NO production. These results suggest that the orientations of the C-3 and C-5 methoxy groups in the patridoids have a significant role in the expression of their biological activity. PMID:14648401

Ju, Hye Kyung; Moon, Tae Chul; Lee, Eunkyung; Baek, Suk-Hwan; An, Ren-Bo; Bae, KiHwan; Son, Kun Ho; Kim, Hyun Pyo; Kang, Sam Sik; Lee, Sung Ho; Son, Jong Keun; Chang, Hyeun Wook

2003-10-01

190

Overexpression of the UGT73C6 alters brassinosteroid glucoside formation in Arabidopsis thaliana  

PubMed Central

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

2011-01-01

191

Protective effects of total glucosides of paeony and the underlying mechanisms in carbon tetrachloride-induced experimental liver injury  

PubMed Central

Introduction We explored the protective effects of total glucosides of paeony (TGP) and the underlying mechanisms in carbon tetrachloride (CCl4)-induced experimental liver injury in mice. Material and methods Chronic liver damage was induced by intraperitoneal injection of CCl4 (0.5 µl/g) three times per week for 8 weeks. Mice also received 25, 50 or 100 mg/kg TGP. Liver sections were stained with haematoxylin/eosin. Serum amino transferases, lipid peroxidation and tumour necrosis factor-? (TNF-?) levels were determined using commercial assays. Quantitative real-time polymerase chain reaction was used to determine the changes in hepatic TNF-?, COX-2, iNOS and HO-1 expression. Protein levels of nitric oxide synthase, cyclooxygenase-2, haem oxygenase-1 and cytochrome P450 2E1 were determined by western blotting. Results Histological results showed that TGP improved the CCl4-induced changes in liver structure and alleviated lobular necrosis. The increases in serum protein and hepatic mRNA expression of TNF-? induced by CCl4 treatment were suppressed by TGP. Total glucosides of paeony also attenuated the increase the expression in iNOS and CYP2E1 but augmented the increase in HO-1.The mRNA and protein expression levels of inducible HO-1 increased significantly after CCl4 treatment. Conclusions Total glucosides of paeony protects hepatocytes from oxidative damage induced by CCl4. Total glucosides of paeony may achieve these effects by enhancing HO-1 expression and inhibiting the expression of proinflammatory mediators. PMID:22291795

Qin, Ying; Tian, Ya-ping

2011-01-01

192

Chemical studies on an endemic Philippine plant: sulfated glucoside and seco-A-ring triterpenoids from Dillenia philippinensis.  

PubMed

The leaves of the endemic Philippine plant, Dillenia philippinensis yielded 11 compounds including one new sulfated glucoside and a new seco-A-ring oleanane-type triterpenoid. The molecular structures of these compounds were elucidated by means of NMR, MS and other spectroscopic techniques, as well as by comparison with literature data. Anti-Leishmania activity and cytotoxic activity against A549 human lung adenocarcinoma cells were also examined. PMID:21372426

Macahig, Rene Angelo Sarmiento; Matsunami, Katsuyoshi; Otsuka, Hideaki

2011-01-01

193

The inhibitory effect and mechanism of luteolin 7-glucoside on rat aortic vascular smooth muscle cell proliferation  

Microsoft Academic Search

The abnormal proliferation of aortic vascular smooth muscle cells (VSMCs) plays a central role in the pathogenesis of atherosclerosis\\u000a and restenosis after angioplasty and possibly also in the development of hypertension. The present study was designed to examine\\u000a the inhibitory effects and the mechanism of luteolin 7-glucoside (L7G) on the platelet-derived growth factor (PDGF)-BB-induced\\u000a proliferation of VSMCs. L7G significantly inhibited

Tack-Joong Kim; Jin-Ho Kim; Yong-Ri Jin; Yeo-Pyo Yun

2006-01-01

194

Effect of Treatment with Cyanidin-3-O-?-D-Glucoside on Rat Ischemic/Reperfusion Brain Damage  

PubMed Central

This study investigated the effect of cyanidin-3-O-?-glucoside on an experimental model of partial/transient cerebral ischemia in the rats in order to verify the effectiveness of both pre- and posttreatments. Cyanidin-3-O-?-glucoside-pretreated rats were injected with 10?mg/Kg i.p. 1?h before the induction of cerebral ischemia; in posttreated rats, the same dosage was injected during reperfusion (30?min after restoring blood flow). Cerebral ischemia was induced by bilateral clamping of common carotid arteries for 20?min. Ischemic rats were sacrificed immediately after 20?min ischemia; postischemic reperfused animals were sacrificed after 3 or 24?h of restoring blood flow. Results showed that treatment with cyanidin increased the levels of nonproteic thiol groups after 24?h of postischemic reperfusion, significantly reduced the lipid hydroperoxides, and increased the expression of heme oxygenase and ?-glutamyl cysteine synthase; a significant reduction in the expression of neuronal and inducible nitric oxide synthases and the equally significant increase in the endothelial isoform were observed. Significant modifications were also detected in enzymes involved in metabolism of endogenous inhibitors of nitric oxide. Most of the effects were observed with both pre- and posttreatments with cyanidin-3-O-?-glucoside suggesting a role of anthocyanin in both prevention and treatment of postischemic reperfusion brain damage. PMID:23008739

Di Giacomo, Claudia; Acquaviva, Rosaria; Santangelo, Rosa; Sorrenti, Valeria; Vanella, Luca; Li Volti, Giovanni; D'Orazio, Nicolantonio; Vanella, Angelo; Galvano, Fabio

2012-01-01

195

Hemisynthesis and structural and chromatic characterization of delphinidin 3-O-glucoside-vescalagin hybrid pigments.  

PubMed

During red wine maturation in the presence of oak wood, reactions involving anthocyanins and ellagitannins might affect wine organoleptic properties such as color and astringency. In this work, the condensation reaction between myrtillin (delphinidin 3-O-glucoside) and vescalagin has been performed to determine the behavior of this anthocyanin in this kind of reaction and to assess the possible impact of such a reaction in wine color modulation. Two different hybrid pigments have been hemisynthetized and characterized by HPLC-DAD-MS and NMR spectroscopy. These pigments have been identified as 1-deoxyvescalagin-(1??8)-myrtillin (major) and 1-deoxyvescalagin-(1??6)-myrtillin (minor). The minor pigment could be formed both by the condensation reaction and by a regioisomerization process from the major pigment. Moreover, the chromatic properties of these pigments have been studied and compared to those of myrtillin. The hybrid pigments showed an important bathochromic shift (ca. 20 nm) in the maximum absorbance wavelength and lower molar absorption coefficients. PMID:24215431

García-Estévez, Ignacio; Jacquet, Rémi; Alcalde-Eon, Cristina; Rivas-Gonzalo, Julián C; Escribano-Bailón, M Teresa; Quideau, Stéphane

2013-11-27

196

Hopantenic acid beta-glucoside as a new urinary metabolite of calcium hopantenate in dogs.  

PubMed

The metabolism of calcium hopantenate (HOPA) was studied in beagle dogs. After oral administration of 14C-labeled HOPA, 25.5% of the administered radioactivity was excreted in the urine within 24 hr, mostly in the form of unchanged drug. The only metabolite, accounting for 4.2% of the radioactivity in the urine, was isolated by HPLC. The metabolite was hydrolyzed by the treatment of beta-glucuronidase (Helix pomatia), acid phosphatase, or beta-glucosidase. These enzyme activities were not inhibited by treatment with D-glucaric acid 1,4-lactone or PO4(3-), but with D-gluconic acid 1,5-lactone, demonstrating that the metabolite is a glucose conjugate. The compound was identified as HOPA-glucoside, 4'-O-(beta-D-glucopyranosyl)-D-hopantenic acid, by GC/MS analyses after derivatization of the metabolite and the synthetic compound. This is the first reported instance of glucose conjugation to a non-acidic hydroxyl group in the metabolism of xenobiotics in mammals. PMID:2877836

Nakano, K; Ando, H; Sugawara, Y; Ohashi, M; Harigaya, S

1986-01-01

197

Enzymatic synthesis of piceid glucosides using maltosyltransferase from Caldicellulosiruptor bescii DSM 6725.  

PubMed

Piceid is widely used in food, cosmetics, and pharmaceuticals because of its therapeutic benefits. However, the use of piceid as a drug is limited because of its low solubility. To increase solubility, we synthesized piceid glucosides using maltosyltransferase from Caldicellulosiruptor bescii. The MTase gene was cloned and expressed in Escherichia coli. The enzyme had a unique transfer specificity to the transfer of maltosyl units. Four piceid transglycosylation products were present and identified by thin-layer chromatography and recycling preparative high-performance liquid chromatography. The major product was purified by C(18) and gel filtration chromatography, and its molecular structure was determined using nuclear magnetic resonance spectroscopy to be ?-D-maltosyl-(1?4)-piceid. The solubility of maltosyl piceid was 8.54 × 10(3) and 1.86 × 10(3) times those of natural resveratrol and piceid, respectively, suggesting that the transglycosylation greatly increased the water solubility. This suggests that dietary intake of this compound can enhance the bioavailability of resveratrol in the human body. PMID:22823185

Park, Hyunsu; Kim, Jieun; Choi, Kyoung-Hwa; Hwang, Sungmin; Yang, Sung-Jae; Baek, Nam-In; Cha, Jaeho

2012-08-22

198

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

PubMed

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

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

2013-10-24

199

Souring and breakdown of cyanogenic glucosides during the processing of cassava into akyeke.  

PubMed

The population and composition of the lactic acid bacteria microbiota as well as the content of cyanogenic glucosides occurring at various stages of fermentation and subsequent processing of cassava roots into akyeke, a steamed sour cassava meal, were investigated. The number of lactic acid bacteria and percentage titratable acidity increased during 5 days of fermentation, but decreases were observed in the subsequent operations of 'washing' the dough with water followed by partial drying and steaming. In field and laboratory samples, Lactobacillus plantarum accounted for 59.3% and 52.3%, Lactobacillus brevis 23.3% and 22.8% and Leuconostoc mesenteroides subsp. cremoris 14.5% and 15.8%, respectively, of all lactic acid bacteria isolated at various stages of fermentation and processing. A reduction of about 98% occurred in the total cyanogens (CN) content of cassava roots during processing, from 69.3 to 1.4 and 110.3 to 2.8 mg CN equivalent/kg dry weight for laboratory and field samples of akyeke, respectively. PMID:15135588

Obilie, Eric Mantey; Tano-Debrah, Kwaku; Amoa-Awua, Wisdom Kofi

2004-05-15

200

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

PubMed

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

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

2015-04-01

201

Protective effect of tetrahydroxystilbene glucoside on cardiotoxicity induced by doxorubicin in vitro and in vivo  

PubMed Central

Aim: To test the effect of 2,3,5,4?-tetrahydroxystilbene-2-O-?-D-glucoside (THSG) on doxorubicin (DOX)-induced cardiotoxicity. Methods: We used neonate rat cardiomyocytes and an acute mouse model of DOX-induced cardiotoxicity to examine the protective effect of THSG. Results: In the mouse model, administration of THSG significantly reduced DOX-induced cardiotoxicity, including animal mortality, histopathological changes, and levels of serum creatine kinase (CK) and lactate dehydrogenase (LDH). Moreover, THSG was able to attenuate the increased malondialdehyde (MDA) and decreased reduced glutathione (GSH) caused by DOX. In in vitro studies, THSG 10?300 ?mol/L ameliorated DOX-induced cardiomyocyte apoptosis in a concentration-dependent manner. Further studies showed that THSG inhibited reactive oxygen species (ROS) generation and prevented DOX-induced loss of mitochondrial membrane potential, caspase-3 activation and upregulation of Bax protein expression. We observed a protective response against damage after DOX treatment. The level of Bcl-2 protein was increased. Additionally, THSG inhibited a DOX-induced [Ca2+] increase. Conclusion: These results showed that THSG protected against DOX-induced cardiotoxicity by decreasing ROS generation and intracellular [Ca2+] and by inhibiting apoptotic signaling pathways. PMID:19890356

Zhang, Shao-hui; Wang, Wen-quan; Wang, Jia-ling

2009-01-01

202

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

NASA Astrophysics Data System (ADS)

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).

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

2008-07-01

203

A Natural Flavonoid Glucoside, Icariin, Regulates Th17 and Alleviates Rheumatoid Arthritis in a Murine Model  

PubMed Central

Rheumatoid arthritis (RA) is a chronic autoimmune inflammatory disease that causes deformity of the joints and physical disability. Icariin, a natural flavonoid glucoside isolated from plants in the Epimedium family, has been proven to have various pharmacological activities. A recent study showed that icariin suppressed cartilage and bone degradation in mice of collagen-induced arthritis. However, the mechanism needs to be further investigated. In our current study, we found that icariin reduced the arthritis score and the incidence of arthritis compared with that in mice treated with water. Icariin inhibits the expression of various osteoclastogenic markers, such as ?3 integrin, cathepsin K, and MMP9 in vitro. Icariin treatment in mice with CIA also resulted in less number of Th17 cells and decreased ratio of CD4+IL-17+ cells. The alleviated arthritis score and incidence of arthritis and reduced serum levels of IgG2a induced by icariin were abolished with additional IL-17 administration. Furthermore, icariin inhibited STAT3 activation in T cells and STAT3 inhibitor resulted in decreased IL-17 production and alleviated RA. In conclusion, icariin decreases Th17 cells and suppresses the production of IL-17, which contributes to the alleviated rheumatoid arthritis, through the inhibition of STAT3 activation. PMID:25374443

Chi, Liqun; Gao, Wenyuan; Shu, Xiangrong; Lu, Xin

2014-01-01

204

A natural flavonoid glucoside, icariin, regulates Th17 and alleviates rheumatoid arthritis in a murine model.  

PubMed

Rheumatoid arthritis (RA) is a chronic autoimmune inflammatory disease that causes deformity of the joints and physical disability. Icariin, a natural flavonoid glucoside isolated from plants in the Epimedium family, has been proven to have various pharmacological activities. A recent study showed that icariin suppressed cartilage and bone degradation in mice of collagen-induced arthritis. However, the mechanism needs to be further investigated. In our current study, we found that icariin reduced the arthritis score and the incidence of arthritis compared with that in mice treated with water. Icariin inhibits the expression of various osteoclastogenic markers, such as ?3 integrin, cathepsin K, and MMP9 in vitro. Icariin treatment in mice with CIA also resulted in less number of Th17 cells and decreased ratio of CD4(+)IL-17(+) cells. The alleviated arthritis score and incidence of arthritis and reduced serum levels of IgG2a induced by icariin were abolished with additional IL-17 administration. Furthermore, icariin inhibited STAT3 activation in T cells and STAT3 inhibitor resulted in decreased IL-17 production and alleviated RA. In conclusion, icariin decreases Th17 cells and suppresses the production of IL-17, which contributes to the alleviated rheumatoid arthritis, through the inhibition of STAT3 activation. PMID:25374443

Chi, Liqun; Gao, Wenyuan; Shu, Xiangrong; Lu, Xin

2014-01-01

205

[A new monoterpenoid glucoside from the twigs of Chamaecyparis obtusa var. breviramea f. crippsii].  

PubMed

To investigate the chemical constituents of Chamaecyparis obtusa var. breviramea f. crippsii, various column chromatography and spectroscopic methods were used for the isolation and elucidation of compounds. One new monoterpenoid glucoside, (4S)-4-isopropylcyclohex-l-enecarboxylic acid 4-O-beta-D-glucopyranoside (1), together with five known compounds, (4R)-p-menth-l-ene-7, 8-diol 7-O-beta-D-glucopyranoside (2), skimmin (3), 7-[[6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-2H-1-benzopyran-2-one (4), stigmast-4-en-3-one (5) and 1, 4-benzenedicarboxylic acid 1-butyl-4-(2-methylpropyl) ester (6) were isolated and identified from the twigs of this plant. All compounds were isolated from this plant for the first time. The methanol extract of this plant showed cytotoxicity on cancer cell lines A549, BGC-823, Du145 and MDA-MB-231 with IC50 values of 0.94, 1.07, 0.95 and 0.96 microg x mL(-1), respectively. Yet, compounds 1, 2 and 3 showed no cytotoxicity on cancer cell lines HeLa, BGC-823 and A549. PMID:23227547

Xu, Jian; Zhang, Yu-Mei; Chen, Ke-Li; Tan, Ning-Hua; Liu, Yi-Mei

2012-09-01

206

Excited state proton transfer dynamics of an eminent anticancer drug, ellipticine, in octyl glucoside micelle.  

PubMed

Photophysics and proton transfer dynamics of an eminent anticancer drug, ellipticine (EPT), have been investigated inside a biocompatible octyl-?-D-glucoside (OBG) micellar medium using steady state and time-resolved fluorescence spectroscopic techniques. EPT exists as protonated form in aqueous solution of pH 7. When EPT molecules are encapsulated in OBG micelles, protonated form is converted to neutral form in the ground state due to the hydrophobic effect of the micellar environment. Interestingly, steady state fluorescence results indicate the existence of both neutral and protonated forms of EPT in the excited state, even though neutral molecules are selectively excited, and it is attributed to the conversion of neutral to protonated form of EPT by the excited state proton transfer (ESPT) process. A clear isoemissive point in the time-resolved area normalized emission spectra (TRANES) further supports the excited state conversion of neutral to protonated form of EPT. Notably, this kind of proton transfer dynamics is not observed in other conventional micelles, such as, SDS, Triton-X and CTAB. Therefore, the observed ESPT dynamics is believed to be an outcome of combined effects of the local dielectric constant felt by EPT and the local proton concentration at the OBG micellar surface. PMID:24931633

Gavvala, Krishna; Koninti, Raj Kumar; Sengupta, Abhigyan; Hazra, Partha

2014-07-28

207

Apoptosis induced by one new podophyllotoxin glucoside in human carcinoma cells.  

PubMed

4-Demethyl-picropodophyllotoxin 7'-O-beta-D-glucopyranoside (4DPG), a new podophyllotoxin glucoside, was isolated from the rhizomes of Sinopodophyllum emodi (Wall.) Ying and showed cytotoxic effects in human carcinoma cells. Among the target cells (HeLa, A2 and SH-SY5Y), the cytotoxic effects of 4DPG showed dose- and time-dependency. Furthermore, the cervical carcinoma cell line, HeLa, was more sensitive to 4DPG. Flow cytometric analysis demonstrated the presence of apoptotic cells with low DNA content, a decrease of cell population at the G1 phase, and a concomitant increase of cell population at the G2/M phase. 4DPG also caused DNA fragmentation in HeLa cells. Treatment with 0.1 microM 4DPG increased p53 expression and Bax/Bcl-2 ratio in HeLa cells, as well as in A2 cells. These results suggested that 4DPG-induced apoptosis might be through a p53-dependent pathway. PMID:15923073

Zhang, Qiu-Ying; Jiang, Min; Zhao, Chang-Qi; Yu, Miao; Zhang, Hui; Ding, Yu-Jia; Zhai, Yong-Gong

2005-08-15

208

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

PubMed Central

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

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

2014-01-01

209

Investigation of coco-glucoside as a novel intestinal permeation enhancer in rat models.  

PubMed

Due to instability in the GI tract and low intestinal permeability, peptides invariably have oral bioavailabilities below 1% and this has prevented the development of oral formulations. A mild plant-derived natural alkyl polyglycoside (APG), coco-glucoside (CG), was studied for its capacity to enable rat intestinal permeation of the paracellular sugar marker, fluorescein isothiocyanate-dextran 4000 (FD4), across isolated rat jejunal and colonic mucosae mounted in Ussing chambers, as well as the polypeptide, salmon calcitonin (sCT) following intra-intestinal instillations in rats. 0.1% (w/v) CG enabled a 2.9-fold increase in the apparent permeability coefficient (Papp) of FD4 over the basal Papp across colonic mucosae, but it was without effect in jejunal mucosae. In situ intestinal instillations revealed that although sCT was absorbed across rat colonic loops to a greater extent than jejunal, CG still improved sCT absolute bioavailability (F) from both segments. Histopathology of rat intestinal mucosae following exposure to CG indicated only minor perturbation with adequate maintenance of secretory function. High content analysis (HCA) on Caco-2 showed that acute and chronic exposure to a range of concentrations of CG did not cause sub-lethal damage at concentrations at which it was effective as an enhancer. Overall, CG increased bioavailability of sCT across rat jejunal and colonic loops without indication of tissue damage. Thus, CG has potential as a safe and effective intestinal enhancer for oral delivery of proteins and peptides. PMID:25445305

Aguirre, Tanira A S; Rosa, Mónica; Guterres, Sílvia S; Pohlmann, Adriana R; Coulter, Ivan; Brayden, David J

2014-10-31

210

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

SciTech Connect

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.

Jing, Xu [Department of Pharmacology, School of Medicine, Shandong University, Jinan 250012 (China); Ren, Dongmei [Department of Natural Product Chemistry, Key Lab of Chemical Biology of Ministry of Education, Shandong University, Jinan 250012 (China); Wei, Xinbing; Shi, Huanying; Zhang, Xiumei [Department of Pharmacology, School of Medicine, Shandong University, Jinan 250012 (China); Perez, Ruth G. [Health Science Center, Paul L. Foster School of Medicine, Texas Tech University, El Paso, TX, 79905 (United States); Lou, Haiyan, E-mail: louhaiyan@sdu.edu.cn [Department of Pharmacology, School of Medicine, Shandong University, Jinan 250012 (China); Lou, Hongxiang [Department of Natural Product Chemistry, Key Lab of Chemical Biology of Ministry of Education, Shandong University, Jinan 250012 (China)

2013-12-15

211

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

PubMed

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

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

2015-02-01

212

Phenylethanoid glucosides from in vitro propagated plants and callus cultures of Plantago lanceolata.  

PubMed

The well-known medicinal plant Plantago lanceolata L. (ribwort plantain) was effectively propagated by direct organogenesis from segments of leaves and roots using MS medium supplemented with IAA (11.42 microM), kinetin (9.29 microM) for multiplication and IAA (5.71 microM) for rooting. The plantlets were successfully hardened (80 %) and transferred to field cultivation (100 %). Two lines of callus tissue, derived from leaves and roots, were obtained on MS medium without NH (4)NO (3) and supplemented with 2,4-D (4.52 microM) and kinetin ( 0.46 microM). From plant materials--leaf rosettes from in vitro, leaves from plants in field cultivation obtained by micropropagation, root-derived callus and leaf-derived callus--sixteen phenylethanoid glucosides representing nine different structures were isolated and identified by spectral methods (1D and 2D NMR) as known for the species: lavandulifolioside ( 1), plantamajoside ( 2,) acteoside ( 3); new for the species: leucosceptoside A ( 4), martynoside ( 5), desrhamnosylisoacteoside ( 6), plantainoside D ( 7), desrhamnosylacteoside ( 8) and - 2-(4-hydroxyphenyl)ethyl beta- D-glucopyranosyl-(1-->3)-4- O- trans- and cis- p-coumaroyl-beta- D-glucopyranoside ( 9)--the latter also being found for the first time in nature and named lancetoside. Only plantamajoside ( 2) and acteoside ( 3) were common to all plant materials, the former was the main constituent of calli (1.19 - 2.84 % of dry weight), while the latter was the main constituent of the leaves (1.78 - 10.43 % of dry weight). Flavonoids were present only in plants of field cultivation. PMID:15386192

Budzianowska, Anna; Skrzypczak, Lutos?awa; Budzianowski, Jaromir

2004-09-01

213

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

PubMed

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

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

2005-03-01

214

Identification and characterization of a new beta-glucoside utilization system in Bacillus subtilis.  

PubMed Central

A new catabolic system in Bacillus subtilis involved in utilization of beta-glucosidic compounds has been investigated. It consists of five genes encoding phosphotransferase system (PTS) enzyme II (licB and licC) and enzyme IIA (licA), a presumed 6-phospho-beta-glucosidase (licH), as well as a putative regulator protein (licR). The genes map around 334 degrees of the B. subtilis chromosome, and their products are involved in the uptake and utilization of lichenan degradation products. These five genes are organized in two transcriptional units. A weak promoter precedes gene licR, and transcription is obviously terminated at a secondary structure immediately downstream of the reading frame, as shown by Northern RNA blot analysis. Genes licB, licC, licA, and licH constitute an operon. Initiation of transcription at the promoter in front of this operon presumably requires activation by the gene product of licR. The LicR protein shows an unusual domain structure, i.e., similarities to (i) the conserved transcriptional antiterminator BgIG family signature and (ii) PTS enzyme II. Using RNA techniques and transcriptional lacZ fusions, we have shown that the expression of the licBCAH operon is inducible by products of lichenan hydrolysis, lichenan and cellobiose. The presence of excess glucose prevents the induction of this operon, indicating the control by carbon catabolite repression. Moreover, the expression of the operon requires the general PTS components and seems to be negatively controlled by the specific lic PTS enzymes. PMID:8990303

Tobisch, S; Glaser, P; Krüger, S; Hecker, M

1997-01-01

215

Targeting RNA by Small Molecules: Comparative Structural and Thermodynamic Aspects of Aristololactam-?-D-glucoside and Daunomycin Binding to tRNAphe  

PubMed Central

Background Interaction of aristololactam-?-D-glucoside and daunomycin with tRNAphe was investigated using various biophysical techniques. Methodology/Principal Findings Absorption and fluorescence studies revealed that both the compounds bind tRNAphe non-cooperatively. The binding of daunomycin was about one order of magnitude higher than that of aristololactam-?-D-glucoside. Stronger binding of the former was also inferred from fluorescence quenching data, quantum efficiency values and circular dichroic results. Results from isothermal titration calorimetry experiments suggested that the binding of both compounds was predominantly entropy driven with a smaller but favorable enthalpy term that increased with temperature. A large favorable electrostatic contribution to the binding of daunomycin to tRNAphe was revealed from salt dependence data and the dissection of the free energy values. The electrostatic component to the free energy change for aristololactam-?-D-glucoside-tRNAphe interaction was smaller than that of daunomycin. This was also inferred from the slope of log K versus [Na+] plots. Both compounds enhanced the thermal stability of tRNAphe. The small heat capacity changes of -47 and -99 cal/mol K, respectively, observed for aristololactam-?-D-glucoside and daunomycin, and the observed enthalpy-entropy compensation phenomenon confirmed the involvement of multiple weak noncovalent interactions. Molecular aspects of the interaction have been revealed. Conclusions/Significance This study presents the structural and eneregetic aspects of the binding of aristololactam-?-D-glucoside and daunomycin to tRNAphe. PMID:21858023

Das, Abhi; Bhadra, Kakali; Suresh Kumar, Gopinatha

2011-01-01

216

Contribution of C-glucosidic ellagitannins to Lythrum salicaria L. influence on pro-inflammatory functions of human neutrophils.  

PubMed

The herb Lythrum salicaria L. (Lythraceae) is used in traditional medicine to treat diseases with an inflammatory background, such as haemorrhoidal disease, dysentery, chronic intestinal catarrh, eczema, varicose veins, periodontosis and gingivitis. Because these diseases are closely associated with an excessive inflammatory response of stimulated neutrophils, the influence of aqueous extract and isolated C-glucosidic ellagitannins (dimeric salicarinins A, B and C, vescalagin, castalagin) on their pro-inflammatory functions was examined. Lythrum salicaria aqueous extract was shown to modulate lipopolysaccharide (LPS)-triggered production of IL-8 (at 20 ?g/mL, 16.6 ± 4.2 % inhibition) but had no influence on MMP-9 production. It was active towards cytochalasin A/f-MLP- stimulated elastase release (at 20 ?g/mL, 21.5 ± 3.9 % inhibition), myeloperoxidase release (at 1 ?g/mL, 26.5 ± 5.4 % inhibition) and f-MLP- and PMA-induced reactive oxygen species production (at 20 ?g/mL, 67.0 ± 3.9 and 66.5 ± 1.9 % inhibition, respectively). The extract was also shown to inhibit expression of integrin CD11b on the neutrophil surface without influencing selectin CD62L shedding. Dose-dependent inhibition of hyaluronidase activity was observed with IC50 = 10.1 ± 1.2 ?g/mL. The main C-glucosidic ellagitannins were shown to be responsible for all these activities with more significant participation attributable to dimeric salicarinins A, B, C. This study has demonstrated potent activity of aqueous extract on stimulated neutrophils; this enhanced response is known to cause pathological changes in skin and mucosa tissues. These observations support and explain the traditional use of the herb Lythrum salicaria to treat certain diseases with an inflammatory background. C-glucosidic ellagitannins, especially dimeric salicarinins, are the factors responsible for these effects. PMID:25349049

Piwowarski, Jakub P; Kiss, Anna K

2015-01-01

217

[Studies on the structure of a new isocoumarin glucoside of the root sprouts of Agrimonia pilosa Ledeb].  

PubMed

Trans-p-hydroxycinnamic esters VI and an isocoumarin glucoside VII were isolated from the benzene and acetone extracts of the root sprouts of Agrimonia pilosa Ledeb. On the basis of physicochemical properties, spectral data (UV, IR, NMR, MS, CI-MS-MS), GC and chemical degradation, VI was elucidated as trans-p-hybroxycinnamic esters of n-C22, n-C24-32, n-C34, alcohols, VII was elucidated as agrimonolide-6-Q-beta-D-glucopyranoside. VII and trans-p-hydroxycinnamic esters of n-C29-32 and n-C34 alcohols are new compounds. PMID:2618681

Pei, Y H; Li, X; Zhu, T R

1989-01-01

218

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

PubMed

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

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

2014-01-01

219

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

PubMed Central

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

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

2014-01-01

220

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

PubMed Central

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

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

2014-01-01

221

Formation of bile acid glucosides by a sugar nucleotide-independent glucosyltransferase isolated from human liver microsomes.  

PubMed

A heat-labile protein has been detected in microsomes from human liver which catalyzes the formation of glucosides of the bile acids chenodeoxycholic, deoxycholic, and ursodeoxycholic acids. This glucosyltransferase activity has been purified about 900-fold from human liver microsomes, resulting in homogeneity as determined by sodium dodecyl sulfate gel electrophoresis. The subunit molecular weight was calculated to be about 56,000. The enzyme was separated from bile acid UDP-glucuronosyltransferase [UDP-glucuronate beta-D-glucuronosyltransferase (acceptor-unspecific), EC 2.4.1.17] during purification and does not catalyze the formation of bile acid glucuronides. The purified glucosyltransferase utilizes lipophilic alkyl beta-D-glucopyranosides as artificial donor substrates and dolichyl phosphoglucose as natural donor for the transfer of glucose to bile acids and does not exhibit bile acid conjugating activity in the presence of sugar nucleotides such as UDP-glucose. The apparent Km values estimated for various alkyl beta-D-glucopyranosides decreased with increasing alkyl chain length from 680 X 10(-6) M for hexyl beta-D-glucopyranoside to 20 X 10(-6) M as estimated for decyl and dodecyl beta-D-glucopyranoside. The results suggest that a glucoside-conjugation pathway of bile acids exists in humans. This conjugation is catalyzed by a sugar nucleotide-independent glucosyltransferase and is therefore distinct from the known mechanisms of glycoside conjugation. PMID:6239286

Matern, H; Matern, S; Gerok, W

1984-11-01

222

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

PubMed Central

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

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

2010-01-01

223

A putative ?-glucoside transporter gene BbAGT1 contributes to carbohydrate utilization, growth, conidiation and virulence of filamentous entomopathogenic fungus Beauveria bassiana.  

PubMed

Carbohydrate transporters are critical players mediating nutrient uptake during saprophytic and pathogenic growth for most filamentous fungi. For entomopathogenic fungi, such as Beauveria bassiana, assimilation of ?-glucosides, in particular, trehalose, the major carbohydrate constituent of the insect haemolymph, has been hypothesized to represent an important ability for infectious growth within the insect hemocoel. In this study, a B. bassiana ?-glucoside transporter homolog was identified and genetically characterized via generation of a targeted gene disruption mutant. Trehalose utilization was compromised in the mutant strain. In addition, inactivation of the ?-glucoside transporter resulted in decreased conidial germination, growth, and yield on various carbohydrates (?-glucosides, monosaccharides and polyols) as compared to the wild-type strain. Insect bioassays revealed decreased mean lethal mortality time using both topical and intrahemocoel injection assays, although final mortality levels were comparable in both the mutant and wild type. Gene expression profiles showed altered expression of other putative transporters in the knockout mutant as compared to the wild type. These results highlighted complex sugar utilization and responsiveness in B. bassiana and the potential role for trehalose assimilation during fungal pathogenesis of insects. PMID:23499939

Wang, Xiu-Xiu; Ji, Xiao-Ping; Li, Jing-Xin; Keyhani, Nemat O; Feng, Ming-Guang; Ying, Sheng-Hua

2013-06-01

224

Protective role of malvidin-3-glucoside on peroxynitrite-induced damage in endothelial cells by counteracting reactive species formation and apoptotic mitochondrial pathway.  

PubMed

The health-promoted benefits of anthocyanins, including vascular protective effects and antiatherogenic properties, have now been recognized, but the involved molecular mechanisms have not been well elucidated. Following our previous work on cytoprotective mechanisms of some anthocyanins against apoptosis triggered by peroxynitrite in endothelial cells, here we investigated the protective role of malvidin-3-glucoside, a major dietary anthocyanin, on such deleterious process, by exploring the interference on cellular reactive species formation and on apoptotic mitochondrial pathway. Preincubation of cells with 25 ?M malvidin-3-glucoside protected efficiently endothelial cells from peroxynitrite-promoted apoptotic death, an effect which may be partially mediated by its ability to decrease the formation of reactive species after cell aggression, as assessed by the dichlorodihydrofluorescein diacetate assay and by carbonyl groups formation. Moreover, malvidin-3-glucoside inhibited mitochondrial apoptotic signaling pathways induced by peroxynitrite, by counteracting mitochondrial membrane depolarization, the activation of caspase-3 and -9, and the increase in the expression of the proapoptotic Bax protein. Altogether, our data expands our knowledge about the molecular mechanisms underlying the vascular protection afforded by malvidin-3-glucoside, and anthocyanins in general, in the context of prevention of endothelial dysfunction and atherosclerosis. PMID:22792413

Paixão, Joana; Dinis, Teresa C P; Almeida, Leonor M

2012-01-01

225

Transepithelial permeability studies of flavan-3-ol-C-glucosides and procyanidin dimers and trimers across the Caco-2 cell monolayer.  

PubMed

In this study the permeability of two flavanol-C-glucosides (FCglcs) and five dimeric and trimeric flavan-3-ols, namely, procyanidins (PCs), was investigated with the human colon carcinoma cell line (Caco-2) model. These compounds can be found especially in cocoa, and they are of great interest due to their assumed beneficial health effects. Transepithelial electrical resistance (TEER) and capacitance were measured online with a CellZscope device prior to and during the whole experiment to guarantee the maintenance of the barrier properties. The transport experiments with pure, single compounds (50-300 ?M) from apical to basolateral side showed slight permeation of PCs A2, B2, and B5 and cinnamtannin B1 (CB1) as well as (-)-catechin-6-C-glucoside (C6Cglc) and (-)-catechin-8-C-glucoside (C8Cglc) of about 0.02-0.2% after 24 h. Transport of PC C1 could not be detected. Inhibition of P-glycoprotein (Pgp) increased the permeation of PC B2 and CB1 to the basolateral side, which indicates that Pgp counteracts the transport of these compounds. Metabolites (epicatechin, 3'- and 4'-O-epicatechin) in very small amounts were detectable only for PC B2. These are the first data concerning the permeability of flavan-3-ol-C-glucosides across the Caco-2 cell monolayer. PMID:23885956

Hemmersbach, Sarah; Brauer, Susanne S; Hüwel, Sabine; Galla, Hans-Joachim; Humpf, Hans-Ulrich

2013-08-21

226

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...

227

Renal effects of a novel endogenous natriuretic agent xanthurenic acid 8-o-?-d-glucoside in rats  

PubMed Central

Xanthurenic acid 8-o-?-d-glucoside is an endogenous derivative of tryptophan metabolism, isolated from urine of patients with chronic renal disease. This compound was suggested previously to act as a natriuretic hormone based on its ability to block short circuit currents in a frog skin assay and to induce a sustained natriuresis when injected into rats (C. D. Cain et al., Proc. Natl. Acad. Sci. USA 2007: 17873–17878). The present communication describes the effects of the compound on renal clearance and hemodynamic parameters in male Sprague–Dawley rats maintained on a normal salt (0.4–0.5%) diet. Intravenous administration of synthetic xanthurenic acid 8-o-?-d-glucoside in two consecutive incremental doses (6.3 and 31.5 nmol) resulted in a significant increase (P < 0.05), in urine flow (43.91 ± 6.31 ?L/min vs. 10.54 ± 2.21 ?L/min), absolute rate of sodium excretion (3.99 ± 0.95 ?Eq/min vs. 1.15 ± ?Eq/min), and percentage sodium excretion (1.63 ± 0.46% vs. 0.37 ± 0.12%, peak response vs. baseline, respectively). The natriuretic/diuretic effect was associated also with a significant increase in potassium excretion. These effects were not related to changes in renal hemodynamics or in arterial blood pressure. Pretreatment with the sodium channel blocker, amiloride, completely abolished the natriuretic and kaluretic actions of the compound. Administration of the xanthurenic acid derivative caused a dose-related increase in urinary nitrite/nitrate excretion. Moreover, under chronic nitric oxide blockade by l-NG-Nitro-Arginine-Methyl-Esther (l-NAME) sodium excretion was similar in rats treated or untreated with the compound. Our data demonstrate that xanthurenic acid 8-o-?-d-glucoside has significant diuretic/natriuretic and kaluretic properties. An intact amiloride-sensitive sodium channel is required for the renal effects of the compound. The data further suggest that the natriuretic effect is mediated in part by a nitric oxide-dependent mechanism. PMID:24400157

Hoffman, Aaron; Okun-Gurevich, Marina; Ovcharenko, Elena; Goltsman, Ilia; Karram, Tony; Cain, Cristopher; Abassi, Zaid; Winaver, Joseph

2013-01-01

228

A novel UDP-Glc-specific glucosyltransferase catalyzing the biosynthesis of 6-O-glucosides of bile acids in human liver microsomes.  

PubMed

Two active site-directed photoaffinity analogs, 5-[beta-32P]azido-UDP-glucuronic acid and 5-[beta-32P]azido-UDP-glucose, were used for the characterization of UDP-sugar-utilizing enzymes in human liver microsomes. Both compounds were recognized by human microsomal proteins: major photolabeled bands of 50-56 kDa were detected. Both photoincorporations were competitively decreased by increasing concentrations of either UDP-Glc or UDP-GlcUA, indicating a high affinity for both nucleotides. The patterns of photoaffinity labeling in the 50-56-kDa range by the two probes were significantly different, indicating the presence of different UDP-GlcUA- and UDP-Glc-specific enzymes of similar molecular mass. The presence of a UDP-Glc-dependent transferase was confirmed by the identification of an enzymatic activity catalyzing the formation of glucosides of the 6 alpha-hydroxylated bile acid hyodeoxycholic acid (3 alpha, 6 alpha-diOH (HDCA)) in the presence of UDP-Glc. The specific activity of 1.5-3.2 nmol/min/mg of protein was similar to that of 6 alpha-glucuronidation of HDCA. The apparent Km for UDP-Glc estimated with HDCA was 280 microM, and the formation of HDCA glucosides was strongly inhibited by UDP-GlcUA (apparent Ki = 7 microM). Evidence is presented that HDCA-specific UDP-glucuronosyltransferase (clone UGT2B4) expressed in V79 cells is not involved in glucosidation of HDCA and is not photolabeled with 5-[beta-32P]azido-UDP-Glc. Rigorous structure identification of the biosynthetic product proved that HDCA was glucosidated at the 6-position. Thus, this UDP-Glc-dependent activity catalyzing the biosynthesis of 6-O-glucosides of 6 alpha-hydroxylated bile acids represents a new pathway in the metabolism of these bile acids. PMID:8325887

Radominska, A; Little, J; Pyrek, J S; Drake, R R; Igari, Y; Fournel-Gigleux, S; Magdalou, J; Burchell, B; Elbein, A D; Siest, G

1993-07-15

229

Copigmentation of malvidin-3-O-glucoside with five hydroxybenzoic acids in red wine model solutions: experimental and theoretical investigations.  

PubMed

In the present research, the copigmentations of malvidin-3-O-glucoside with five hydroxybenzoic cofactors (p-hydroxybenzoic acid, protocatechuic acid, gallic acid, vanillic acid, and syringic acid) were investigated. The influence of the concentration of these cofactors and the reaction temperature was examined. The equilibrium constant (K), stoichiometric ratio (n) and the thermodynamic parameters (?G°, ?H°, ?S°) related to the copigmentation were also reported here. Theoretical calculations were performed to identify the relative arrangement between the pigment and cofactors in the copigmentation complexes. Besides, the comparison of the relative binding free energies (??Gbinding) derived from the theoretical calculations and experimental data were made, and the binding strength of these copigmentation complexes was discussed with the interaction energies (?E). AIM analysis was also used to explore the main driving forces contributing to the copigmentation. In the comparison of the five studied cofactors, syringic acid had a stronger copigmentation effect than the other four phenolic acids investigated. PMID:25306339

Zhang, Bo; Liu, Rui; He, Fei; Zhou, Pan-Pan; Duan, Chang-Qing

2015-03-01

230

Cytotoxicity and apoptosis induced by a new podophyllotoxin glucoside in human hepatoma (HepG2) cells.  

PubMed

4-Demethylepipodophyllotoxin 7'-O-beta-D-glucopyranoside (4' DPG), a new podophyllotoxin glucoside with a chemical structure similar to that of 4-demethylpicropodophyllotoxin 7'-O-beta-D-glucopyranoside (4DPG), was isolated from the rhizomes of Sinopodophyllum emodi (Wall.) Ying (Berberidaceae). Like 4DPG and etoposide (VP-16), 4' DPG displayed dose- and time-dependent cytotoxic effects in HepG2 cells. Flow cytometric analysis demonstrated the presence of apoptotic cells and DNA fragmentation after HepG2 cells were exposed to 4' DPG (1 micromol/L). In addition, 4' DPG-driven apoptotic events were associated with upregulation of Bax and downregulation of Bcl-2. These results suggest that 4' DPG has prominent cytotoxic activity and induces apoptosis by increasing the ratio of Bax to Bcl-2 in HepG2 cells. PMID:20555416

Liu, Yanfeng; Zhao, Changqi; Li, Hongxing; Yu, Miao; Gao, Jiali; Wang, Lei; Zhai, Yonggong

2010-04-01

231

[beta-Glucosidases specific for the cyanogenic glucoside triglochinin from Alocasia macrorrhiza Schott: further characterization of properties (author's transl)].  

PubMed

All beta-glucosidases extracted and separated from a plant of Alocasia macrorrhiza are almost entirely specific for triglochinin. The hexameric beta-glucosidase has been shown to dissociate in dimers without any alteration of activity. Reaggregation could only be demonstrated using bifunctional reagents like glutaraldehyde. Treatments of beta-glucosidase with various chemicals (e. g. glutaraldehyde, dodecyl sulfate) decreased the activity for triglochinin more than the activity for 4-nitrophenyl glucoside. On the other hand, specific reagents like bromocondurite or p-chloromercuribenzoate caused identical inactivations measured with various substrates. It seems possible that the different beta-glucosidases splitting triglochinin arose during purification from the hexameric form which occurs in the plant. PMID:411729

Hösel, W; Klewitz, O

1977-08-01

232

In vitro and in vivo study of cucurbitacins-type triterpene glucoside from Citrullus colocynthis growing in Saudi Arabia against hepatocellular carcinoma.  

PubMed

Chromatographic investigation of fruits obtained from Citrullus colocynthis, growing in Saudi Arabia, led to isolation of two compounds; Cucurbitacin E glucoside (Cu E, 1), and Cucurbitacin I glucoside (Cu I, 2). The chemical structures of 1 and 2, were elucidated by spectroscopic analyses include; 1D ((1)H and (13)C) and 2D (COSY, HMQC and HMBC) NMR and ESI-MS spectroscopy. The in vitro cytotoxic activity against hepatoma cell line (HepG2) and mice-bearing tumor of Ehrlich's ascites carcinoma (EAC) of the compounds were estimated. Both compounds had potent inhibitory activity on HepG2 with IC(50) 3.5 and 2.8 nmol/mL, respectively. In addition to these activities, the in vivo study employing EAC, showed the capability of both compounds to prolong the survival time, life span and normalize the biochemical parameters of the infected mice with EAC. PMID:22245841

Ayyad, Seif-Eldin N; Abdel-Lateff, Ahmed; Alarif, Walied M; Patacchioli, Francesca R; Badria, Farid A; Ezmirly, Saleh T

2012-03-01

233

Structural identification of novel glucoside and glucuronide metabolites of (?)-epigallocatechin-3-gallate in mouse urine using liquid chromatography/electrospray ionization tandem mass spectrometry  

PubMed Central

(?)-Epigallocatechin-3-gallate (EGCG), the most abundant and most biologically active polyphenolic compound in tea, has been proposed to have many health beneficial effects. The metabolic fate of EGCG, however, is not well understood. In the present study, we identified a novel EGCG metabolite, 7-O-?-D-glucopyranosyl-EGCG-4?-O-?-D-glucupyranoside, in a mouse urine sample using liquid chromatography/electrospray ionization tandem mass spectrometry. The structure of this metabolite was confirmed by analyzing the MSn (n = 1–4) spectra as well as comparing the MS/MS spectra of its product ions with those from EGCG and EGCG-4?-O-?-D-glucupyranoside standards. To our knowledge, this is the first report of the identification of a glucoside metabolite of EGCG in mammals. Our results indicate that glucosidation represents a novel pathway in the metabolism of EGCG in mice. PMID:18951414

Sang, Shengmin; Yang, Chung S.

2010-01-01

234

Differential cell-protective function of two resveratrol (trans-3,5,4'-trihydroxystilbene) glucosides against oxidative stress.  

PubMed

Resveratrol (trans-3,5,4'-trihydroxystilbene; RSV), a natural polyphenol, exerts a beneficial effect on health and diseases. RSV targets and activates the NAD(+)-dependent protein deacetylase SIRT1; in turn, SIRT1 induces an intracellular antioxidative mechanism by inducing mitochondrial superoxide dismutase (SOD2). Most RSV found in plants is glycosylated, and the effect of these glycosylated forms on SIRT1 has not been studied. In this study, we compared the effects of RSV and two glycosyl RSVs, resveratrol-3-O-?-d-glucoside (3G-RSV; polydatin/piceid) and resveratrol-4'-O-?-d-glucoside (4'G-RSV), at the cellular level. In oxygen radical absorbance capacity and 2,2-diphenyl-1-picrylhydrazyl radical scavenging assays, the antioxidant activity of 3G-RSV was comparable to that of RSV, whereas the radical-scavenging efficiency of 4'G-RSV was less than 50% of that of RSV. However, 4'G-RSV, but not 3G-RSV, induced SIRT1-dependent histone H3 deacetylation and SOD2 expression in mouse C2C12 skeletal myoblasts; as with RSV, SIRT1 knockdown blunted these effects. RSV and 4'G-RSV, but not 3G-RSV, mitigated oxidative stress-induced cell death in C2C12 cells and primary neonatal rat cardiomyocytes. RSV and 4'G-RSV inhibited C2C12 cell proliferation, but 3G-RSV did not. RSV was found in both the intracellular and extracellular fractions of C2C12 cells that had been incubated with 4'G-RSV, indicating that 4'G-RSV was extracellularly deglycosylated to RSV, which was then taken up by the cells. C2C12 cells did not deglycosylate 3G-RSV. Our results point to 4'G-RSV as a useful RSV prodrug with high water solubility. These data also show that the in vitro antioxidative activity of these molecules did not correlate with their ability to protect cells from oxidative stress-induced apoptosis. PMID:23042952

Hosoda, Ryusuke; Kuno, Atsushi; Hori, Yusuke S; Ohtani, Katsuki; Wakamiya, Nobutaka; Oohiro, Azusa; Hamada, Hiroki; Horio, Yoshiyuki

2013-01-01

235

Enhanced catalytic efficiency in quercetin-4'-glucoside hydrolysis of Thermotoga maritima ?-glucosidase A by site-directed mutagenesis.  

PubMed

Te-BglA and Tm-BglA are glycoside hydrolase family 1 ?-glucosidases from Thermoanaerobacter ethanolicus JW200 and Thermotoga maritima, respectively, with 53% sequence identity. However, Te-BglA could more effectively hydrolyze isoflavone glucosides to their aglycones than could Tm-BglA, possibly due to the difference in amino acid residues around their glycone binding pockets. Site-directed mutagenesis was used to replace the amino acid residues of Tm-BglA with the corresponding residues of Te-BglA, generating three single mutants (F221L, N223L, and G224T), as well as the corresponding three double mutants (F221L/N223L, F221L/G224T, and N223L/G224T) and one triple mutant (F221L/N223L/G224T). The seven mutants have been purified, characterized, and compared to the wild-type Tm-BglA. The effects of the mutations on kinetics, enzyme activity, and substrate specificity were determined. All mutants showed pH-activity curves narrower on the basic side and wider on the acid side and had similar optimal pH and stability at pH 6.5-8.3. They were more stable up to 85 °C, but G224T displayed higher optimal temperature than Tm-BglA. Seven mutants indicated an obvious increase in catalytic efficiency toward p-nitrophenyl ?-D-glucopyranoside (pNPG) but an increase or not change in K(m). All mutants showed a decrease in catalytic efficiency of isoflavonoid glycosides and were not changed for F221L and lost for N223L in enzymatic hydrolysis on quercetin glucosides. Contrarily, G224T resulted in a dramatic increase conversion of Q4' (35.5%) and Q3,4' (28.6%) in accord with an increased turnover number (k(cat), 1.4×) and catalytic efficiency (k(cat)/K(m), 2.2×) as well as a decrease in K(m) (0.24) for Q4'. Modeling showed that G224T mutation at position 224 may enhance the interaction between G224T and 5-OH and 3-OH on the quercetin backbone of Q4'. PMID:24933681

Sun, Huihui; Xue, Yemin; Lin, Yufei

2014-07-16

236

Molecular Characterization of a Novel Glucosyltransferase from Lactobacillus reuteri Strain 121 Synthesizing a Unique, Highly Branched Glucan with ?-(1?4) and ?-(1?6) Glucosidic Bonds  

Microsoft Academic Search

Lactobacillus reuteri strain 121 produces a unique, highly branched, soluble glucan in which the majority of the linkages are of the ?-(1?4) glucosidic type. The glucan also contains ?-(1?6)-linked glucosyl units and 4,6-disubstituted ?-glucosyl units at the branching points. Using degenerate primers, based on the amino acid sequences of conserved regions from known glucosyltransferase (gtf) genes from lactic acid bacteria,

S. Kralj; G. H. van Geel-Schutten; H. Rahaoui; R. J. Leer; E. J. Faber; M. J. E. C. van der Maarel; L. Dijkhuizen

2002-01-01

237

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

PubMed Central

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

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

2014-01-01

238

ortho-Substituted C-aryl glucosides as highly potent and selective renal sodium-dependent glucose co-transporter 2 (SGLT2) inhibitors  

Microsoft Academic Search

A series of 2-substituted C-aryl glucosides have been synthesized and evaluated for inhibition of hSGLT1 and hSGLT2. Introduction of an appropriate ortho substituent at the proximal phenyl ring adjacent to the glycosidic bond was found to improve SGLT2 inhibitory activity and dramatically increase selectivity for hSGLT2 over hSGLT1. Selected compounds were investigated for in vivo efficacy.

Baihua Xu; Yan Feng; Binhua Lv; Ge Xu; Lili Zhang; Jiyan Du; Kun Peng; Min Xu; Jiajia Dong; Wenbin Zhang; Ting Zhang; Liangcheng Zhu; Haifeng Ding; Zelin Sheng; Ajith Welihinda; Brian Seed; Yuanwei Chen

2010-01-01

239

Identification, properties, and genetic control of UDP-glucose: Cyanidin3-rhamnosyl-(1?6)-glucoside-5- O -glucosyltransferase isolated from petals of the red campion (Silene dioica)  

Microsoft Academic Search

An enzyme catalyzing the transfer of the glucosyl moiety of UDP-glucose to the 5-hydroxyl group of cyanidin-3-rhamnosyl-(1?6)-glucoside has been demonstrated in petal extracts of Silene dioica plants. This glucosyltransferase activity was not detectable in green parts of these plants. The enzyme activity is controlled by a single dominant gene M; no glucosyltransferase activity could be demonstrated in petals of m\\/m

John Kamsteeg; Jan van Brederode; Gerrit van Nigtevecht

1978-01-01

240

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

PubMed Central

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

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

2014-01-01

241

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

PubMed

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

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

2014-01-01

242

Spectrophotometric study of the copigmentation of malvidin 3-O-glucoside with p-coumaric, vanillic and syringic acids.  

PubMed

Anthocyanins are a natural source of pigments in plants and their processed food products have become attractive and excellent candidates to replace the synthetic colourants due to their characteristic intense colours and associated health benefits. The intermolecular copigmentation between anthocyanins and other colourless compounds has been reported to be an important way to enhance and stabilise the colour intensity of aqueous solutions. In the present work we report the equilibrium constant, stoichiometric ratio and the thermodynamic parameters (?G°, ?H° and ?S°) related to the intermolecular copigmentation reactions of the anthocyanin malvidin 3-O-glucoside with one hydroxycinnamic acid (p-coumaric acid) and two O-methylated hydroxybenzoic acids (vanillic and syringic acid). Different factors which affect their interactions such as copigment concentration, pH and temperature of the medium are examined at two pH levels (pH=2.50 and 3.65) corresponding to those of the major food mediums where these reactions take place (fruit juices, wine, jams etc.). PMID:23993528

Malaj, Naim; De Simone, Bruna Clara; Quartarolo, Angelo Domenico; Russo, Nino

2013-12-15

243

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

PubMed

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

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

2015-02-01

244

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

PubMed Central

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

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

245

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

PubMed

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

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

2013-02-13

246

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

PubMed

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 48h. 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

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

2015-03-01

247

The Requirement of Sterol Glucoside for Pexophagy in Yeast Is Dependent on the Species and Nature of Peroxisome Inducers  

PubMed Central

Sterol glucosyltransferase, Ugt51/Atg26, is essential for both micropexophagy and macropexophagy of methanol-induced peroxisomes in Pichia pastoris. However, the role of this protein in pexophagy in other yeast remained unclear. We show that oleate- and amine-induced peroxisomes in Yarrowia lipolytica are degraded by Atg26-independent macropexophagy. Surprisingly, Atg26 was also not essential for macropexophagy of oleate- and amine-induced peroxisomes in P. pastoris, suggesting that the function of sterol glucoside (SG) in pexophagy is both species and peroxisome inducer specific. However, the rates of degradation of oleate- and amine-induced peroxisomes in P. pastoris were reduced in the absence of SG, indicating that P. pastoris specifically uses sterol conversion by Atg26 to enhance selective degradation of peroxisomes. However, methanol-induced peroxisomes apparently have lost the redundant ability to be degraded without SG. We also show that the P. pastoris Vac8 armadillo repeat protein is not essential for macropexophagy of methanol-, oleate-, or amine-induced peroxisomes, which makes PpVac8 the first known protein required for the micropexophagy, but not for the macropexophagy, machinery. The uniqueness of Atg26 and Vac8 functions under different pexophagy conditions demonstrates that not only pexophagy inducers, such as glucose or ethanol, but also the inducers of peroxisomes, such as methanol, oleate, or primary amines, determine the requirements for subsequent pexophagy in yeast. PMID:17079731

Nazarko, Taras Y.; Polupanov, Andriy S.; Manjithaya, Ravi R.; Sibirny, Andriy A.

2007-01-01

248

Deoxynivalenol, deoxynivalenol-3-glucoside, and enniatins: the major mycotoxins found in cereal-based products on the Czech market.  

PubMed

Fusarium toxins, Alternaria toxins, and ergot alkaloids represent common groups of mycotoxins that can be found in cereals grown under temperate climatic conditions. Because most of them are chemically and thermally stable, these toxic fungal secondary metabolites might be transferred from grains into the final products. To get information on the commensurate contamination of various cereal-based products collected from the Czech retail market in 2010, the occurrence of "traditional" mycotoxins such as groups of A and B trichothecenes and zearalenone, less routinely determined Alternaria toxins (alternariol, alternariol monomethyl ether and altenuene), ergot alkaloids (ergosine, ergocryptine, ergocristine, and ergocornine) and "emerging" mycotoxins (enniatins A, A1, B, and B1 and beauvericin) were monitored. In a total 116 samples derived from white flour and mixed flour, breakfast cereals, snacks, and flour, only trichothecenes A and B and enniatins were found. Deoxynivalenol was detected in 75% of samples with concentrations ranging from 13 to 594 ?g/kg, but its masked form, deoxynivalenol-3-?-d-glucoside, has an even higher incidence of 80% of samples, and concentrations ranging between 5 and 72 ?g/kg were detected. Nivalenol was found only in three samples at levels of 30 ?g/kg. For enniatins, all of the samples investigated were contaminated with at least one of four target enniatins. Enniatin A was detected in 97% of samples (concentration range of 20-2532 ?g/kg) followed by enniatin B with an incidence in 91% of the samples (concentration range of 13-941 ?g/kg) and enniatin B1 with an incidence of 80% in the samples tested (concentration range of 8-785 ?g/kg). Enniatin A1 was found only in 44% of samples at levels ranging between 8 and 851 ?g/kg. PMID:22070284

Malachova, Alexandra; Dzuman, Zbynek; Veprikova, Zdenka; Vaclavikova, Marta; Zachariasova, Milena; Hajslova, Jana

2011-12-28

249

A semiquinone glucoside derivative provides protection to male reproductive system of the mice against gamma radiation toxicity.  

PubMed

Present investigation was carried out to evaluate the radioprotective efficacy of a novel Semiquinone glucoside derivative (SQGD), isolated from Bacillus sp. INM-1, in the male reproductive system of BALB/c mice. Animals were administered 50 mg/kg b.wt. (i.p.) SQGD 2 h before whole body ?-irradiation (10 Gy). Radiation-induced cellular toxicity and its modulation by SQGD pretreatment was evaluated in the mice testes by quantitative histological and protein expression analysis. SQGD pretreatment protects irradiated mice from radiation-induced testicular atrophy and germ cells degeneration, which may lead to emptiness of seminiferous tubules. Significant decrease in P53 and P21((Cip/WAF-1)) expression was observed in the irradiated mice pretreated (2 h) by SQGD at 6 h compared with only irradiated mice. However, contrary to P53, expressions of P21 at latter time, that is, 24-72 h was found to be increased significantly in the irradiated mice pretreated by SQGD. Significant increase in the intact PARP-1 protein expression were observed in the testes of the mice pretreated by SQGD 2 h before irradiation at 24-72 h compared with the only irradiated mice, whereas significant increase in PARP-1 cleaved fragment was noticed at 24 h. Similarly, significant increase in NF-kB and BCL-2/BAX expressions ratio was noticed in SQGD-treated mice (± irradiation) compared with irradiated mice, suggested a role of SQGD in the activation of prosurvival signaling in the testicular germinal cells population of the irradiated mice and thus contributed to protection against lethal ?-irradiation. PMID:22730153

Patel, Dev Dutt; Bansal, Deen Dayal; Mishra, Saurabh; Arora, Rajesh; Sharma, Rakesh Kumar; Jain, Swatantra Kumar; Kumar, Raj

2014-05-01

250

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

PubMed Central

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

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

251

[Glucosidases specific for the cyanogenic glucoside triglochinin. Purification and characterization of beta-glucosidases from Alocasia macrorrhiza Schott].  

PubMed

beta-Glucosidases have been isolated from Alocasia macrorrhiza plants. The enzymes are highly specific for the hydrolysis of the cyanogenic glucoside triglochinin endogenous to this plant. Upon chromatography of protein extracts on cation exchange resins and Sephadex G-200, separation into various enzymatically active bands was observed. The main fractions possess molecular weights of approximately 310000 and 105 000, as shown by preparative ultracentrifugation in a linear saccharose gradient. The beta-glucosidases are composed of subunits (molecular weight 55 000 to 60 000), as revealed by sodium dodecylsulfate gel electrophoresis. The result of alkaline disc electrophoresis and isoelectric focusing in polyacrylamide gel suggest that the beta-glucosidase fraction with molecular weight 105 000 is a dissociation product of the 310 000 molecular-weight species. The isoelectric points of the various beta-glocusidase bands, obtained by isoelectric focusing, vary between pH 4.5 and 5.0. The beta-glucosidases show a pronounced specificity for triglochinin. The Km for this substrate (3 times 10(-5) M) is 50 to 100-fold lower than for all other substrates hydrolyzed. Of the other cyanogenic glycosides, only those with an aromatic aglycone, (S)-configuration at the asymmetric carbon atom of the aglycone and glucose as sugar moiety were hydrolyzed to a measurable extent. The pH optimum of the enzyme reaction is 5.5, the temperature optimum around 50 degrees C. Cu2 ions and glucono-1,5-lactone inhibit beta-glucosidase activity approximately 50% at a concentration of 5 times 10(-4) M, while Hg2,Ag and p-chloromercuribenzoate show the same percent inhibition at 5 times 10(-7) M. Lipophilic solvents (ethanol, ethylene glycol monomethylether) activate the beta-glucosidase activity, preferentially by influencing the V values of the enzymes. PMID:240769

Hösel, W; Nahrstedt, A

1975-08-01

252

Regulation of the putative bglPH operon for aryl-beta-glucoside utilization in Bacillus subtilis.  

PubMed

The expression of the putative operon bglPH of Bacillus subtilis was studied by using bglP'-lacZ transcriptional fusions. The bglP gene encodes an aryl-beta-glucoside-specific enzyme II of the phosphoenolpyruvate sugar:phosphotransferase system, whereas the bglH gene product functions as a phospho-beta-glucosidase. Expression of bglPH is regulated by at least two different mechanisms: (i) carbon catabolite repression and (ii) induction via an antitermination mechanism. Distinct deletions of the promoter region were created to determine cis-acting sites for regulation. An operatorlike structure partially overlapping the -35 box of the promoter of bglP appears to be the catabolite-responsive element of this operon. The motif is similar to that of amyO and shows no mismatches with respect to the consensus sequence established as the target of carbon catabolite repression in B. subtilis. Catabolite repression is abolished in both ccpA and ptsH1 mutants. The target of the induction by the substrate, salicin or arbutin, is a transcriptional terminator located downstream from the promoter of bglP. This structure is very similar to that of transcriptional terminators which regulate the induction of the B. subtilis sacB gene, the sacPA operon, and the Escherichia coli bgl operon. The licT gene product, a member of the BglG-SacY family of antitermination proteins, is essential for the induction process. Expression of bglP is under the negative control of its own gene product. The general proteins of the phosphoenolpyruvate-dependent phosphotransferase system are required for bglP expression. Furthermore, the region upstream from bglP, which reveals a high AT content, exerts a negative regulatory effect on bglP expression. PMID:7559347

Krüger, S; Hecker, M

1995-10-01

253

A semiquinone glucoside derivative isolated from Bacillus sp. INM-1 provides protection against 5-fluorouracil-induced immunotoxicity.  

PubMed

Abstract 5-Fluorouracil (5-FU) is a widely used anti-cancer agent; however, it induces immunosuppression in patients undergoing a chemotherapy regime. The mode of action by which 5-FU induces immunosuppression is primarily via inhibition of hematopoietic growth factors. In the present study, immunoprotective effects of a semiquinone glucoside derivative (SQGD), a bacterial metabolite isolated from Bacillus sp. INM-1, were evaluated in a model of 5-FU-induced immunotoxicity in C57Bl/6 male mice. The evaluation was done by analyzing G-CSF, GM-CSF, and M-CSF expression in the serum, spleen, and bone marrow cells of the mice at different timepoints after 5-FU treatment. Mice received a single intraperitoneal injection of either 5-FU (75?mg/kg) alone, SQGD (50?mg/kg) alone, or SQGD 2?h prior to the 5-FU treatment. Control mice received saline vehicle only. The results demonstrated that 5-FU treatment significantly inhibited G-CSF, GM-CSF, and M-CSF expression in all three sites at all timepoints from 6-72?h post 5-FU. In SQGD treated mice, up-regulation of factor expression was observed in each compartment, and significantly so most often after 12?h. SQGD treatment prior to 5-FU administration to the mice significantly increased in all sites evaluated - relative to values in both control mice and 5-FU only-treated mice - G-CSF, M-CSF, and GM-CSF expression at almost every timepoint. The present findings suggest that SQGD provides protection against 5-FU-induced immunotoxicity in mice and could protect bone marrow progenitor cells against the effects of cytotoxic drugs used for treatment of cancer. The findings also suggested to us that SQGD is a potential immunomodulator and could protect hematopoiesis against toxic assault caused by anti-cancer drugs in the clinical setting. PMID:24512327

Mishra, Saurabh; Malhotra, Poonam; Gupta, Ashutosh K; Singh, Praveen K; Javed, Saleem; Kumar, Raj

2015-01-01

254

Translation Efficiency of Antiterminator Proteins Is a Determinant for the Difference in Glucose Repression of Two ?-Glucoside Phosphotransferase System Gene Clusters in Corynebacterium glutamicum R ?  

PubMed Central

Corynebacterium glutamicum R has two ?-glucoside phosphoenolpyruvate, carbohydrate phosphotransferase systems (PTS) encoded by bglF and bglF2 located in the respective clusters, bglF-bglA-bglG and bglF2-bglA2-bglG2. Previously, we reported that whereas ?-glucoside-dependent induction of bglF is strongly repressed by glucose, glucose repression of bglF2 is very weak. Here, we reveal the mechanism behind the different effects of glucose on the two bgl genes. Deletion of the ribonucleic antiterminator sequence and transcriptional terminator located upstream of the translation initiation codon of bglF markedly relieved the glucose repression of a bglF-lacZ fusion, indicating that glucose affects the antitermination mechanism that is responsible for the ?-glucoside-dependent induction of the bglF cluster. The glucose repression of bglF mRNA was also relieved by introducing a multicopy plasmid carrying the bglG gene encoding an antiterminator of the bglF cluster. Moreover, replacement of the GUG translation initiation codon of bglG with AUG was effective in relieving the glucose repression of bglF and bglG. Inversely, expression of bglF2 and bglG2 was subject to strict glucose repression in a mutant strain in which the AUG translation initiation codon of bglG2 encoding antiterminator of the bglF2 cluster was replaced with GUG. These results suggest that the translation initiation efficiency of the antiterminator proteins, at least in part, determines whether the target genes are subject to glucose repression. We also found that bglF expression was induced by glucose in the BglG-overexpressing strains, which may be explained by the ability of BglF to transport glucose. PMID:21075922

Tanaka, Yuya; Teramoto, Haruhiko; Inui, Masayuki; Yukawa, Hideaki

2011-01-01

255

Combining high-performance liquid chromatography with on-line microdialysis sampling for the simultaneous determination of ascorbyl glucoside, kojic acid, and niacinamide in bleaching cosmetics  

Microsoft Academic Search

We have used on-line microdialysis sampling coupled with high-performance liquid chromatography and UV–vis detection to simultaneously determine the contents of ascorbyl glucoside (AA-2G), kojic acid (KA), and niacinamide (VitB3) in commercial bleaching cosmetics. Our results indicate that AA-2G, KA, and VitB3 separated well within 4.5min on a reverse-phase Hypersil Fluophase PFP column when eluting with 0.020M phosphate buffer solution in

Cheng-Hui Lin; Hsin-Lung Wu; Yeou-Lih Huang

2007-01-01

256

Molecular cloning and biochemical characterization of a recombinant sterol 3-O-glucosyltransferase from Gymnema sylvestre R.Br. catalyzing biosynthesis of steryl glucosides.  

PubMed

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

Tiwari, Pragya; Sangwan, Rajender Singh; Asha; Mishra, B N; Sabir, Farzana; Sangwan, Neelam S

2014-01-01

257

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

PubMed Central

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

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

2014-01-01

258

Cloning and Expression of Cytochrome P450 Enzymes Catalyzing the Conversion of Tyrosine to p-Hydroxyphenylacetaldoxime in the Biosynthesis of Cyanogenic Glucosides in Triglochin maritima1  

PubMed Central

Two cDNA clones encoding cytochrome P450 enzymes belonging to the CYP79 family have been isolated from Triglochin maritima. The two proteins show 94% sequence identity and have been designated CYP79E1 and CYP79E2. Heterologous expression of the native and the truncated forms of the two clones in Escherichia coli demonstrated that both encode multifunctional N-hydroxylases catalyzing the conversion of tyrosine to p-hydroxyphenylacetaldoxime in the biosynthesis of the two cyanogenic glucosides taxiphyllin and triglochinin in T. maritima. This renders CYP79E functionally identical to CYP79A1 from Sorghum bicolor, and unambiguously demonstrates that cyanogenic glucoside biosynthesis in T. maritima and S. bicolor is catalyzed by analogous enzyme systems with p-hydroxyphenylacetaldoxime as a free intermediate. This is in contrast to earlier reports stipulating p-hydroxyphenylacetonitrile as the only free intermediate in T. maritima. l-3,4-Dihydroxyphenyl[3-14C]Ala (DOPA) was not metabolized by CYP79E1, indicating that hydroxylation of the phenol ring at the meta position, as required for triglochinin formation, takes place at a later stage. In S. bicolor, CYP71E1 catalyzes the subsequent conversion of p-hydroxyphenylacetaldoxime to p-hydroxymandelonitrile. When CYP79E1 from T. maritima was reconstituted with CYP71E1 and NADPH-cytochrome P450 oxidoreductase from S. bicolor, efficient conversion of tyrosine to p-hydroxymandelonitrile was observed. PMID:10759528

Nielsen, John Strikart; Møller, Birger Lindberg

2000-01-01

259

Cloning and expression of cytochrome P450 enzymes catalyzing the conversion of tyrosine to p-hydroxyphenylacetaldoxime in the biosynthesis of cyanogenic glucosides in Triglochin maritima.  

PubMed

Two cDNA clones encoding cytochrome P450 enzymes belonging to the CYP79 family have been isolated from Triglochin maritima. The two proteins show 94% sequence identity and have been designated CYP79E1 and CYP79E2. Heterologous expression of the native and the truncated forms of the two clones in Escherichia coli demonstrated that both encode multifunctional N-hydroxylases catalyzing the conversion of tyrosine to p-hydroxyphenylacetaldoxime in the biosynthesis of the two cyanogenic glucosides taxiphyllin and triglochinin in T. maritima. This renders CYP79E functionally identical to CYP79A1 from Sorghum bicolor, and unambiguously demonstrates that cyanogenic glucoside biosynthesis in T. maritima and S. bicolor is catalyzed by analogous enzyme systems with p-hydroxyphenylacetaldoxime as a free intermediate. This is in contrast to earlier reports stipulating p-hydroxyphenylacetonitrile as the only free intermediate in T. maritima. L-3,4-Dihydroxyphenyl[3-(14)C]Ala (DOPA) was not metabolized by CYP79E1, indicating that hydroxylation of the phenol ring at the meta position, as required for triglochinin formation, takes place at a later stage. In S. bicolor, CYP71E1 catalyzes the subsequent conversion of p-hydroxyphenylacetaldoxime to p-hydroxymandelonitrile. When CYP79E1 from T. maritima was reconstituted with CYP71E1 and NADPH-cytochrome P450 oxidoreductase from S. bicolor, efficient conversion of tyrosine to p-hydroxymandelonitrile was observed. PMID:10759528

Nielsen, J S; Møller, B L

2000-04-01

260

Genetic engineering of plant secondary metabolism. Accumulation of 4-hydroxybenzoate glucosides as a result of the expression of the bacterial ubiC gene in tobacco.  

PubMed Central

The ubiC gene of Escherichia coli encodes chorismate pyruvatelyase, an enzyme that converts chorismate into 4-hydroxybenzoate (4HB) and is not normally present in plants. The ubiC gene was expressed in Nicotiana tabacum L. plants under control of a constitutive plant promoter. The gene product was targeted into the plastid by fusing it to the sequence for the chloroplast transit peptide of the small subunit of ribulose-1,5-bisphosphate carboxylase/oxygenase. Transgenic plants showed high chorismate pyruvate-lyase activity and accumulated 4HB as beta-glucosides, with the glucose attached to either the hydroxy or the carboxyl function of 4HB. The total content of 4HB glucosides was approximately 0.52% of dry weight, which exceeded the content of untransformed plants by at least a factor of 1000. Feeding experiments with [1,7-13C2]shikimic acid unequivocally proved that the 4HB that was formed in the transgenic plants was not derived from the conventional phenylpropanoid pathway but from the newly introduced chorismate pyruvate-lyase reaction. PMID:8883391

Siebert, M; Sommer, S; Li, S M; Wang, Z X; Severin, K; Heide, L

1996-01-01

261

Simultaneous determination of two iridoid glycosides, two anthraquinones and four flavonoid glycosides of Zhi-Zi-Da-Huang decoction in rat plasma by UFLC-MS/MS: application to a comparative pharmacokinetic study in normal and cholestatic liver injury rats.  

PubMed

A selective, sensitive and reliable ultra fast liquid chromatography-tandem mass spectrometry (UFLC-MS/MS) method has been developed for the simultaneous determination of two iridoid glycosides (geniposide and genipin gentiobioside), two anthraquinones (rhein and emodin) and four flavonoid glycosides (isonaringin, naringin, hesperidin and neohesperidin), the major active ingredients of Zhi-Zi-Da-Huang decoction (ZZDHD), in rat plasma using paeoniflorin as internal standard (IS). After liquid-liquid extraction with ethyl acetate-isopropanol (1:1, v/v), separation was achieved on a Shim-pack XR-ODS C18 column (75 mm×3.0 mm, 2.2 ?m) using gradient elution with a mobile phase consisting of water (containing 0.1% formic acid) and acetonitrile at a flow rate of 0.4 mL/min. Detection was performed on 4000 QTRAP mass spectrometry equipped with turbo ion spray source in the negative ionization and multiple reaction monitoring (MRM) mode. The intra- and inter-day precisions (as relative standard deviation) were less than 11.4%, and accuracy (as relative error) was within ± 10.0%. The lower limits of quantification (LLOQ) were 4.0, 0.5, 2.0, 0.1, 1.0, 2.0, 1.0, 2.0 ng/mL for geniposide, genipin gentiobioside, rhein, emodin, isonaringin, naringin, hesperidin and neohesperidin, respectively. The extraction recoveries of the analytes and IS from rat plasma were all more than 86.0%. The method was fully validated and applied to compare the pharmacokinetic profiles of the analytes in normal and cholestatic liver injury (CLI) rats after oral administration of ZZDHD. Results showed that there were remarkable differences in pharmacokinetic properties of the analytes between normal and CLI group. PMID:24793084

Zhu, Heyun; Bi, Kaishun; Han, Fei; Guan, Jiao; Tang, Zheng; Chen, Kelin; Zhao, Longshan; Li, Qing; Yin, Ran; Hou, Xiaohong

2014-06-01

262

Plant Community Diversity Influences Allocation to Direct Chemical Defence in Plantago lanceolata  

PubMed Central

Background Forecasting the consequences of accelerating rates of changes in biodiversity for ecosystem functioning requires a mechanistic understanding of the relationships between the structure of biological communities and variation in plant functional characteristics. So far, experimental data of how plant species diversity influences the investment of individual plants in direct chemical defences against herbivores and pathogens is lacking. Methodology/Principal Findings We used Plantago lanceolata as a model species in experimental grasslands differing in species richness and composition (Jena Experiment) to investigate foliar concentrations of the iridoid glycosides (IG), catalpol and its biosynthetic precursor aucubin. Total IG and aucubin concentrations decreased, while catalpol concentrations increased with increasing plant diversity in terms of species or functional group richness. Negative plant diversity effects on total IG and aucubin concentrations correlated with increasing specific leaf area of P. lanceolata, suggesting that greater allocation to light acquisition reduced the investment into these carbon-based defence components. In contrast, increasing leaf nitrogen concentrations best explained increasing concentrations of the biosynthetically more advanced IG, catalpol. Observed levels of leaf damage explained a significant proportion of variation in total IG and aucubin concentrations, but did not account for variance in catalpol concentrations. Conclusions/Significance Our results clearly show that plants growing in communities of varying species richness and composition differ in their defensive chemistry, which may modulate plant susceptibility to enemy attack and consequently their interactions with higher trophic level organisms. PMID:22174766

Mraja, Anne; Unsicker, Sybille B.; Reichelt, Michael; Gershenzon, Jonathan; Roscher, Christiane

2011-01-01

263

Luteolin and luteolin-7-O-glucoside inhibit lipopolysaccharide-induced inflammatory responses through modulation of NF-?B/AP-1/PI3K-Akt signaling cascades in RAW 264.7 cells.  

PubMed

Luteolin is a flavonoid found in abundance in celery, green pepper, and dandelions. Previous studies have shown that luteolin is an anti-inflammatory and anti-oxidative agent. In this study, the anti-inflammatory capacity of luteolin and one of its glycosidic forms, luteolin-7-O-glucoside, were compared and their molecular mechanisms of action were analyzed. In lipopolysaccharide (LPS)-activated RAW 264.7 cells, luteolin more potently inhibited the production of nitric oxide (NO) and prostaglandin E2 as well as the expression of their corresponding enzymes (inducible NO synthase (iNOS) and cyclooxygenase-2 (COX-2) than luteolin-7-O-glucoside. The molecular mechanisms underlying these effects were investigated to determine whether the inflammatory response was related to the transcription factors, nuclear factor (NF)-?B and activator protein (AP)-1, or their upstream signaling molecules, mitogen-activated protein kinases (MAPKs) and phosphoinositide 3-kinase (PI3K). Luteolin attenuated the activation of both transcription factors, NF-?B and AP-1, while luteolin-7-O-glucoside only impeded NF-?B activation. However, both flavonoids inhibited Akt phosphorylation in a dose-dependent manner. Consequently, luteolin more potently ameliorated LPS-induced inflammation than luteolin-7-O-glucoside, which might be attributed to the differentially activated NF-?B/AP-1/PI3K-Akt pathway in RAW 264.7 cells. PMID:24353826

Park, Chung Mu; Song, Young-Sun

2013-12-01

264

Luteolin and luteolin-7-O-glucoside inhibit lipopolysaccharide-induced inflammatory responses through modulation of NF-?B/AP-1/PI3K-Akt signaling cascades in RAW 264.7 cells  

PubMed Central

Luteolin is a flavonoid found in abundance in celery, green pepper, and dandelions. Previous studies have shown that luteolin is an anti-inflammatory and anti-oxidative agent. In this study, the anti-inflammatory capacity of luteolin and one of its glycosidic forms, luteolin-7-O-glucoside, were compared and their molecular mechanisms of action were analyzed. In lipopolysaccharide (LPS)-activated RAW 264.7 cells, luteolin more potently inhibited the production of nitric oxide (NO) and prostaglandin E2 as well as the expression of their corresponding enzymes (inducible NO synthase (iNOS) and cyclooxygenase-2 (COX-2) than luteolin-7-O-glucoside. The molecular mechanisms underlying these effects were investigated to determine whether the inflammatory response was related to the transcription factors, nuclear factor (NF)-?B and activator protein (AP)-1, or their upstream signaling molecules, mitogen-activated protein kinases (MAPKs) and phosphoinositide 3-kinase (PI3K). Luteolin attenuated the activation of both transcription factors, NF-?B and AP-1, while luteolin-7-O-glucoside only impeded NF-?B activation. However, both flavonoids inhibited Akt phosphorylation in a dose-dependent manner. Consequently, luteolin more potently ameliorated LPS-induced inflammation than luteolin-7-O-glucoside, which might be attributed to the differentially activated NF-?B/AP-1/PI3K-Akt pathway in RAW 264.7 cells. PMID:24353826

Park, Chung Mu

2013-01-01

265

New beta-glucoside (bgl) genes in Bacillus subtilis: the bglP gene product has both transport and regulatory functions similar to those of BglF, its Escherichia coli homolog.  

PubMed

The Bacillus subtilis sacY and sacT genes encode antiterminator proteins, similar to the Escherichia coli bglG gene product and required for transcription of sucrose metabolism genes. A Tn10 insertion into bglP (formerly sytA) has been previously identified as restoring sucrose utilization to a strain with deletions of both sacY and sacT. The nucleotide sequence of bglP showed a high degree of homology with the E. coli bglF gene (BglF is a beta-glucoside permease of the phosphotransferase system and also acts as a negative regulator of the BglG antiterminator). Complementation studies of an E. coli strain with a deletion of the bgl operon showed that BglP was a functional beta-glucoside permease. In B. subtilis, bglP complemented in trans both the bglP::Tn10 original insertion and a phenotypically similar bglP deletion. Disruption of licT abolished the suppressor phenotype in a bglP mutant. LicT is a recently identified third B. subtilis antiterminator of the BglG/SacY family. These observations indicated that BglP was also a negative regulator of LicT. Both LicT and BglP seem to be involved in the induction by beta-glucosides of an operon containing at least two genes, bglP itself and bglH, encoding a phospho-beta-glucosidase. Other beta-glucoside genes homologous to bglP and bglH have been recently described in B. subtilis. Thus, B. subtilis possesses several sets of beta-glucoside genes, like E. coli, but these genes do not appear to be cryptic. PMID:7883710

Le Coq, D; Lindner, C; Krüger, S; Steinmetz, M; Stülke, J

1995-03-01

266

Phenanthrenes, 9,10-dihydrophenanthrenes, bibenzyls with their derivatives, and malate or tartrate benzyl ester glucosides from tubers of Cremastra appendiculata.  

PubMed

Eleven previously unknown compounds and 23 known compounds, including 20 phenanthrene or 9,10-dihydrophenanthrene derivatives, five bibenzyls, seven malate or tartrate benzyl ester glucosides, adenosine and gastrodin were isolated from tubers of Cremastra appendiculata. Among the obtained compounds, two are the first isolated dimers with one phenanthrene or bibenzyl unit connected to C-3 of 2,3,4,5-tetrahydro-phenanthro[2,1-b]furan moiety. In addition, 33 of these compounds were evaluated in vitro for their cytotoxic activity against two cancer cell lines. Among the compounds examined, one compound showed moderate cytotoxic activity, while five showed weak cytotoxic activity against the A549 cell line. PMID:23820314

Wang, Yang; Guan, Shu-Hong; Meng, Yu-Hui; Zhang, Yi-Bei; Cheng, Chun-Ru; Shi, Yang-Yang; Feng, Rui-Hong; Zeng, Feng; Wu, Zhi-Yuan; Zhang, Jing-Xian; Yang, Min; Liu, Xuan; Li, Qing; Chen, Xiao-Hui; Bi, Kai-Shun; Guo, De-An

2013-10-01

267

Natural variation in maize aphid resistance is associated with 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one glucoside methyltransferase activity.  

PubMed

Plants differ greatly in their susceptibility to insect herbivory, suggesting both local adaptation and resistance tradeoffs. We used maize (Zea mays) recombinant inbred lines to map a quantitative trait locus (QTL) for the maize leaf aphid (Rhopalosiphum maidis) susceptibility to maize Chromosome 1. Phytochemical analysis revealed that the same locus was also associated with high levels of 2-hydroxy-4,7-dimethoxy-1,4-benzoxazin-3-one glucoside (HDMBOA-Glc) and low levels of 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one glucoside (DIMBOA-Glc). In vitro enzyme assays with candidate genes from the region of the QTL identified three O-methyltransferases (Bx10a-c) that convert DIMBOA-Glc to HDMBOA-Glc. Variation in HDMBOA-Glc production was attributed to a natural CACTA family transposon insertion that inactivates Bx10c in maize lines with low HDMBOA-Glc accumulation. When tested with a population of 26 diverse maize inbred lines, R. maidis produced more progeny on those with high HDMBOA-Glc and low DIMBOA-Glc. Although HDMBOA-Glc was more toxic to R. maidis than DIMBOA-Glc in vitro, BX10c activity and the resulting decline of DIMBOA-Glc upon methylation to HDMBOA-Glc were associated with reduced callose deposition as an aphid defense response in vivo. Thus, a natural transposon insertion appears to mediate an ecologically relevant trade-off between the direct toxicity and defense-inducing properties of maize benzoxazinoids. PMID:23898034

Meihls, Lisa N; Handrick, Vinzenz; Glauser, Gaetan; Barbier, Hugues; Kaur, Harleen; Haribal, Meena M; Lipka, Alexander E; Gershenzon, Jonathan; Buckler, Edward S; Erb, Matthias; Köllner, Tobias G; Jander, Georg

2013-06-01

268

Simultaneous determination of major type B trichothecenes and deoxynivalenol-3-glucoside in animal feed and raw materials using improved DSPE combined with LC-MS/MS.  

PubMed

A simple and reliable method for simultaneous determination of deoxynivalenol-3-glucoside and major type B trichothecenes (deoxynivalenol, nivalenol, fusarenon X, 3-acetyldeoxynivalenol, 15-acetyldeoxynivalenol and deepoxy-deoxynivalenol) in animal feed and raw materials has been developed and validated in this study. The method was based on an improved dispersive solid-phase extraction (DSPE) followed by analysis using high performance liquid chromatography coupled to tandem mass spectrometry (HPLC-MS/MS). Also, matrix-matched calibration curve (R(2)>0.99) was employed to minimize matrix effects and ensure accurate quantification. The recoveries during sample preparation process (including extraction and clean-up) ranged from 79.03% to 118.39%, with intra-day and inter-day relative standard deviation lower than 20% for all the analytes. The limit of quantification ranged from 5.0 ?g/kg for deoxynivalenol to 13.6 ?g/kg for fusarenon X. The validated method was successfully applied to the analysis of animal feed and corn. The pilot study showed that 37 out of 41 samples were contaminated with deoxynivalenol-3-glucoside at the levels of 6.0-121.0 ?g/kg. Most of the type B trichothecenes were also found with the exception of fusarenon X, at the contaminated levels of 10.0-1,382 ?g/kg. To the best of our knowledge, this was the first scientific report on the co-occurrence of masked deoxynivalenol and type B trichothecenes in animal feed and raw materials. PMID:24935763

Zhao, Zhiyong; Rao, Qinxiong; Song, Suquan; Liu, Na; Han, Zheng; Hou, Jiafa; Wu, Aibo

2014-07-15

269

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

PubMed

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

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

2015-01-24

270

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

PubMed

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

Franzyk; Jensen; Thale; Olsen

1999-02-01

271

C-Aryl glucosides substituted at the 4?-position as potent and selective renal sodium-dependent glucose co-transporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes  

Microsoft Academic Search

A series of C-aryl glucosides with various substituents at the 4?-position of the distal aryl ring have been synthesized and evaluated for inhibition of hSGLT1 and hSGLT2. Introduction of alkyl or alkoxy substituents at the 4?-position was found to improve SGLT2 potency, whereas introduction of a hydrophilic group at this position was deleterious. Compounds with alkoxy-, cycloalkoxy- or cycloalkenyloxy-ethoxy scaffolds

Baihua Xu; Yan Feng; Huawei Cheng; Yanli Song; Binhua Lv; Yuelin Wu; Congna Wang; Shengbin Li; Min Xu; Jiyan Du; Kun Peng; Jiajia Dong; Wenbin Zhang; Ting Zhang; Liangcheng Zhu; Haifeng Ding; Zelin Sheng; Ajith Welihinda; Jacques Y. Roberge; Brian Seed; Yuanwei Chen

2011-01-01

272

Identification of Candida dubliniensis Based on Temperature and Utilization of Xylose and a-Methyl-D-Glucoside as Determined with the API 20C AUX and Vitek YBC Systems  

Microsoft Academic Search

To have a better understanding of the role of Candida dubliniensis in clinical infections, it is essential that microbiology laboratories can identify this species rapidly and accurately in clinical specimens. C. dubliniensis has been reported to lack the ability to utilize xylose (XYL) and a-methyl-D-glucoside (MDG) and to grow poorly or not at all at 45°C, whereas Candida albicans isolates

A. C. GALES; M. A. PFALLER; A. K. HOUSTON; S. JOLY; D. J. SULLIVAN; D. C. COLEMAN; D. R. SOLL

1999-01-01

273

Cyanidin 3-glucoside attenuates obesity-associated insulin resistance and hepatic steatosis in high-fat diet-fed and db\\/db mice via the transcription factor FoxO1  

Microsoft Academic Search

Obesity is a major risk factor for the development of type 2 diabetes, and both conditions are now recognized to possess significant inflammatory components underlying their pathophysiologies. Here, we hypothesized that cyanidin 3-glucoside (C3G), a typical anthocyanin reported to possess potent anti-inflammatory properties, would ameliorate obesity-associated inflammation and metabolic disorders, such as insulin resistance and hepatic steatosis in mouse models

Honghui Guo; Min Xia; Tangbin Zou; Wenhua Ling; Ruimin Zhong; Weiguo Zhang

274

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  

Microsoft Academic Search

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

Marie Therese Paternostre; Michel Roux; Jean Louis Rigaud

1988-01-01

275

Synergistic effect of apple extracts and quercetin 3-beta-d-glucoside combination on antiproliferative activity in MCF-7 human breast cancer cells in vitro.  

PubMed

Breast cancer is the most frequently diagnosed cancer in women. An alternative strategy to reduce the risk of cancer is through dietary modification. Although phytochemicals naturally occur as complex mixtures, little information is available regarding possible additive, synergistic, or antagonistic interactions among compounds. The antiproliferative activity of apple extracts and quercetin 3-beta-d-glucoside (Q3G) was assessed by measurement of the inhibition of MCF-7 human breast cancer cell proliferation. Cell cytotoxicity was determined by the methylene blue assay. The two-way combination of apple plus Q3G was conducted. In this two-way combination, the EC(50) values of apple extracts and Q3G were 2- and 4-fold lower, respectively, than those of apple extracts and Q3G alone. The combination index (CI) values at 50 and 95% inhibition rates were 0.76 +/- 0.16 and 0.42 +/- 0.10, respectively. The dose-reduction index (DRI) values of the apple extracts and Q3G to achieve a 50% inhibition effect were reduced by 2.03 +/- 0.55 and 4.28 +/- 0.39-fold, respectively. The results suggest that the apple extracts plus Q3G combination possesses a synergistic effect in MCF-7 cell proliferation. PMID:19694432

Yang, Jun; Liu, Rui Hai

2009-09-23

276

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

PubMed Central

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

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

2012-01-01

277

Delphinidin-3-Glucoside Protects against Oxidized Low-Density Lipoprotein-Induced Mitochondrial Dysfunction in Vascular Endothelial Cells via the Sodium-Dependent Glucose Transporter SGLT1  

PubMed Central

Delphinidin-3-glucoside (Dp) is a member of a family of bioactive compounds known as anthocyanins that occur naturally in pigmented plants and are known to ameliorate oxidative stress. Previous studies have showed that Dp decreased oxidative stress in vascular endothelial cells, however, the underlying mechanisms remain largely unknown. In the present study, we showed that pretreatment with Dp significantly suppressed oxidized low-density lipoprotein (oxLDL)-induced cell proliferation inhibition and apoptosis in primary human umbilical vein endothelial cells (HUVECs). Also, Dp pretreatment attenuated oxLDL-induced mitochondrial dysfunction via decreased reactive oxygen species (ROS) and superoxide anion generation, thereby repressing mitochondrial membrane potential and closing mitochondrial permeability transition pore. Furthermore, in vitro and in vivo data showed that Dp was transported into endothelial cells in a temperature, concentration, and time-dependent manner via the sodium-dependent glucose transporter (SGLT1). Suppression of SGLT1 by its substrate glucose, its inhibitor phlorizin or SGLT1 siRNA blocked Dp transportation. Repression of SGLT1 significantly inhibited Dp function of ameliorating mitochondrial dysfunction induced by pro-apoptotic factors (Apoptosis-inducing factor, Cytochrome c, Caspase-3 and Bax/Bcl-2 ratio). Taken together, our data indicate that Dp protects VECs via the SGLT1-ROS-mitochodria pathway. This new insight may help to elucidate the molecular mechanisms underlying the vascular protection afforded by Dp, and anthocyanins in general, in the context of prevention of endothelial dysfunction and atherosclerosis. PMID:23874689

Chen, Ming-liang; Chen, Chun-ye; Chang, Hui; Zhang, Ting; Wang, Li; Zhu, Jun-dong; Zhang, Qian-yong; Mi, Man-tian

2013-01-01

278

Delphinidin-3-glucoside protects against oxidized low-density lipoprotein-induced mitochondrial dysfunction in vascular endothelial cells via the sodium-dependent glucose transporter SGLT1.  

PubMed

Delphinidin-3-glucoside (Dp) is a member of a family of bioactive compounds known as anthocyanins that occur naturally in pigmented plants and are known to ameliorate oxidative stress. Previous studies have showed that Dp decreased oxidative stress in vascular endothelial cells, however, the underlying mechanisms remain largely unknown. In the present study, we showed that pretreatment with Dp significantly suppressed oxidized low-density lipoprotein (oxLDL)-induced cell proliferation inhibition and apoptosis in primary human umbilical vein endothelial cells (HUVECs). Also, Dp pretreatment attenuated oxLDL-induced mitochondrial dysfunction via decreased reactive oxygen species (ROS) and superoxide anion generation, thereby repressing mitochondrial membrane potential and closing mitochondrial permeability transition pore. Furthermore, in vitro and in vivo data showed that Dp was transported into endothelial cells in a temperature, concentration, and time-dependent manner via the sodium-dependent glucose transporter (SGLT1). Suppression of SGLT1 by its substrate glucose, its inhibitor phlorizin or SGLT1 siRNA blocked Dp transportation. Repression of SGLT1 significantly inhibited Dp function of ameliorating mitochondrial dysfunction induced by pro-apoptotic factors (Apoptosis-inducing factor, Cytochrome c, Caspase-3 and Bax/Bcl-2 ratio). Taken together, our data indicate that Dp protects VECs via the SGLT1-ROS-mitochodria pathway. This new insight may help to elucidate the molecular mechanisms underlying the vascular protection afforded by Dp, and anthocyanins in general, in the context of prevention of endothelial dysfunction and atherosclerosis. PMID:23874689

Jin, Xin; Yi, Long; Chen, Ming-liang; Chen, Chun-ye; Chang, Hui; Zhang, Ting; Wang, Li; Zhu, Jun-dong; Zhang, Qian-yong; Mi, Man-tian

2013-01-01

279

Phosphorylation of Akt Mediates Anti-Inflammatory Activity of 1-p-Coumaroyl ?-D-Glucoside Against Lipopolysaccharide-Induced Inflammation in RAW264.7 Cells  

PubMed Central

Hydroxycinnamic acids have been reported to possess numerous pharmacological activities such as antioxidant, anti-inflammatory, and anti-tumor properties. However, the biological activity of 1-p-coumaroyl ?-D-glucoside (CG), a glucose ester derivative of p-coumaric acid, has not been clearly examined. The objective of this study is to elucidate the anti-inflammatory action of CG in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells. In the present study, CG significantly suppressed LPS-induced excessive production of pro-inflammatory mediators such as nitric oxide (NO) and PGE2 and the protein expression of iNOS and COX-2. CG also inhibited LPS-induced secretion of pro-inflammatory cytokines, IL-1? and TNF-?. In addition, CG significantly suppressed LPS-induced degradation of I?B. To elucidate the underlying mechanism by which CG exerts its anti-inflammatory action, involvement of various signaling pathways were examined. CG exhibited significantly increased Akt phosphorylation in a concentration-dependent manner, although MAPKs such as Erk, JNK, and p38 appeared not to be involved. Furthermore, inhibition of Akt/PI3K signaling pathway with wortmannin significantly, albeit not completely, abolished CG-induced Akt phosphorylation and anti-inflammatory actions. Taken together, the present study demonstrates that Akt signaling pathway might play a major role in CG-mediated anti-inflammatory activity in LPS-stimulated RAW264.7 macrophage cells. PMID:24634601

Vo, Van Anh; Lee, Jae-Won; Kim, Ji-Young; Park, Jun-Ho; Lee, Hee Jae; Kim, Sung-Soo; Kwon, Yong-Soo

2014-01-01

280

Regional intestinal absorption of FITC-dextran 4,400 with nanoparticles based on beta-sitosterol beta-D-glucoside in rats.  

PubMed

Nanoparticles (NP) are potential carriers for drug delivery to the targeted intestine. NP based on beta-sitosterol beta-D-glucoside (Sit-G) enhanced the colon-specific absorption of FITC-dextran 4,400 (FD-4), because the concentration-dependent increase of bioavailability appeared in only the colon. In a permeation study, the absorption enhancement in the colon was suppressed in the following conditions: (1) the addition of Sit-G NP to serosa; (2) a permeation study at 4 degrees C; (3) the addition of endocytosis inhibitor, cytochalasin B. NP based on sitosterol, the aglycon of Sit-G, did not increase the FD-4 colonic permeation. The addition of Sit-G NP to the mucosal side induced a decrease of transepithelial resistance (TEER), but this phenomenon was suppressed by an inhibitor of Na(+)-dependent specific glucose transporter, phrolidzin, which did not affect FD-4 permeation. These findings suggested that absorption enhancement by Sit-G NP may not be due to opening of a tight junction, but might be related to endocytosis via glucose residue of Sit-G. PMID:12532381

Nakamura, Koji; Takayama, Kozo; Nagai, Tsuneji; Maitani, Yoshie

2003-02-01

281

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

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

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

2014-01-01

282

Malvidin-3-O-? glucoside, major grape anthocyanin, inhibits human macrophage-derived inflammatory mediators and decreases clinical scores in arthritic rats.  

PubMed

Polyphenolic anthocyanins are major colorful compounds in red fruits, known to prevent cardiovascular and other diseases. Grape polyphenols are a mixture of various molecules and their exact contribution to above bioactivities remains to be clarified. In the present study, we first analyzed the effect of purified grape-derived compounds on human peripheral blood mononuclear cell (PBMC) survival, proliferation, as well as for their ability to inhibit the activation of human normal macrophages. Data indicated that malvidin-3-O-? glucoside (Mal?g), the major grape anthocyanin, is bioactive with no toxicity on human PBMC. Mal?g decreased the transcription of genes encoding inflammatory mediators, confirmed by the inhibition of TNF?, IL1, IL-6 and iNOS-derived nitric oxide (NO) secretion from activated macrophages. As Mal?g also inhibited inflammatory response of rat macrophages, we investigated the anti-inflammatory potential of Mal?g in chronic rat adjuvant-induced arthritis (AIA). Mal?g significantly diminished inflammatory cachexia and arthritic paw scores in AIA rats at both therapeutic and preventive levels. In vivo effects of Mal?g correlated with down-regulation of NO generation from AIA rats' peritoneal macrophages ex vivo. These data indicate that Mal?g, major grape anthocyanin, is a potent anti-inflammatory agent in vitro and in vivo, without detectable toxic effect. PMID:23796750

Decendit, Alain; Mamani-Matsuda, Maria; Aumont, Virginie; Waffo-Teguo, Pierre; Moynet, Daniel; Boniface, Katia; Richard, Emmanuel; Krisa, Stéphanie; Rambert, Jérôme; Mérillon, Jean-Michel; Mossalayi, M D

2013-11-15

283

Total Glucosides of Paeony Capsule Plus Compound Glycyrrhizin Tablets for the Treatment of Severe Alopecia Areata in Children: A Randomized Controlled Trial  

PubMed Central

Total glucosides of paeony capsule (TGPC) and compound glycyrrhizin tablets (CGT) are plant extracts of glycosides. We conducted this study to examine the efficacy and safety of TGPC plus CGT for severe alopecia areata in children. 117 subjects were randomly allocated into TGPC plus CGT group or CGT group. For consecutive 12 months, subjects were given oral TGPC and CGT or oral CGT alone. The outcome measures included score of alopecia areata severity, effective rate, and adverse events observed in the 3rd, 6th, and 12th month. We found that the scores of alopecia areata severity of both groups were significantly reduced, and the scores of treatment group were lower than those of control group; for effective rate, there was no statistical difference between the two groups in the 3rd month, while in the 6th and 12th months the treatment group was superior compared with control group; the incidence rate of adverse events between the two groups was not statistically different, and no severe adverse events were observed. In conclusion, TGPC plus CGT appears effective and safe for severe alopecia areata in children. PMID:24204391

Yang, Dingquan; Zhang, Yuming; Jin, Yueli; Gan, Chaonan; Bai, Yanping

2013-01-01

284

A Novel Soybean (Glycine max) Gene Encoding a Family 3 ?-Glucosidase Has High Isoflavone 7-O-Glucoside-Hydrolyzing Activity in Transgenic Rice.  

PubMed

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

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

2015-01-28

285

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

PubMed Central

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

Ojewole, John AO

2008-01-01

286

Cucurbitacin L 2-O-?-Glucoside Demonstrates Apoptogenesis in Colon Adenocarcinoma Cells (HT-29): Involvement of Reactive Oxygen and Nitrogen Species Regulation  

PubMed Central

Emerging evidence suggests that reactive oxygen (ROS) and nitrogen (RNS) species can contribute to diverse signalling pathways of inflammatory and tumour cells. Cucurbitacins are a group of highly oxygenated triterpenes. Many plants used in folk medicine to treat cancer have been found to contain cucurbitacins displaying potentially important anti-inflammatory actions. The current study was designed to investigate the anti-ROS and -RNS effects of cucurbitacin L 2-O-?-glucoside (CLG) and the role of these signaling factors in the apoptogenic effects of CLG on human colon cancer cells (HT-29). This natural cucurbitacin was isolated purely from Citrullus lanatus var. citroides (Cucurbitaceae). The results revealed that CLG was cytotoxic to HT-29. CLG increased significantly (P < 0.05) RNA and protein levels of caspase-3 in HT-29 cells when verified using a colorimetric assay and realtime qPCR, respectively. The results showed that lipopolysaccharide/interferon-gamma (LPS/INF-?) increased nitrous oxide (NO) production inR AW264.7macrophages, whereas N(G)-nitro-L-argininemethyl ester (L-NAME) and CLG curtailed it. This compound did not reveal any cytotoxicity on RAW264.7 macrophages and human normal liver cells (WRL-68) when tested using the MTT assay. Findings of ferric reducing antioxidant power (FRAP) and oxygen radical absorption capacity (ORAC) assays demonstrate the antioxidant properties of CLG. The apoptogenic property of CLG on HT-29 cells is thus related to inhibition of reactive nitrogen and oxygen reactive species and the triggering of caspase-3-regulated apoptosis. PMID:22685485

Abdelwahab, Siddig Ibrahim; Hassan, Loiy Elsir Ahmed; Abdul Majid, Amin M. S.; Yagi, Sakina M. Ahmed; Mohan, Syam; Elhassan Taha, Manal Mohamed; Ahmad, Syahida; Chuen, Cheah Shiau; Narrima, Putri; Rais, Mohd Mustafa; Syam, Suvitha; Moharam, Bushra Abdulkarim; Hadi, A. Hamid A.

2012-01-01

287

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

PubMed Central

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

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

2011-01-01

288

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

PubMed Central

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

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

289

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

PubMed

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

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

2014-10-01

290

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

PubMed

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

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

2014-11-01

291

Development and validation of a liquid chromatography/linear ion trap mass spectrometry method for the quantitative determination of deoxynivalenol-3-glucoside in processed cereal-derived products.  

PubMed

Cereal-based food can be frequently contaminated by the presence of mycotoxins derived from Fusarium fungus, and, in particular, by deoxynivalenol (DON). Nowadays, analytical strategies for the detection of DON are well developed, but there are gaps for what concerns a correct identification, quantification and toxicological evaluation of the respective metabolites, mainly related to detoxifying actions via plant metabolism or to processing technologies and also referred to as "masked" mycotoxins. Here, we report the development of a liquid chromatography/linear ion trap mass spectrometry method capable of determining deoxynivalenol-3-glucoside (DON-3G), which is the main known DON metabolite, in different processed cereal-derived products. Samples were extracted with a mixture of methanol/water (80:20; v/v) and cleaned up using immunoaffinity columns. Chromatographic separation was performed using a core-shell C(18) column with an aqueous acetic acid/methanol mixture as the mobile phase under gradient conditions. The method was in-house validated on a bread matrix as follows: matrix-matched linearity (r(2)>0.99) was established in the range of 10-200 ?g kg(-1); trueness expressed as recovery was close to 90%; good intermediate precision (overall RSD<9%) and adequate detection quantitation limits (4 and 11 ?g kg(-1), respectively) were achieved. Furthermore, applying a metrology approach based on intralaboratory data, the estimated measurement expanded uncertainty was determined to be equal to 29%. The reliability of the method was finally demonstrated in bread, cracker, biscuit and minicake commodities, resulting in relatively low levels of DON-3G, which were not higher than 30 ?g kg(-1). PMID:23194564

Suman, M; Bergamini, E; Catellani, D; Manzitti, A

2013-02-15

292

Impact of Cyanidin-3-Glucoside on Glycated LDL-Induced NADPH Oxidase Activation, Mitochondrial Dysfunction and Cell Viability in Cultured Vascular Endothelial Cells  

PubMed Central

Elevated levels of glycated low density lipoprotein (glyLDL) are frequently detected in diabetic patients. Previous studies demonstrated that glyLDL increased the production of reactive oxygen species (ROS), activated NADPH oxidase (NOX) and suppressed mitochondrial electron transport chain (mETC) enzyme activities in vascular endothelial cells (EC). The present study examined the effects of cyanidin-3-glucoside (C3G), a type of anthocyanin abundant in dark-skinned berries, on glyLDL-induced ROS production, NOX activation and mETC enzyme activity in porcine aortic EC (PAEC). Co-treatment of C3G prevented glyLDL-induced upregulation of NOX4 and intracellular superoxide production in EC. C3G normalized glyLDL-induced inhibition on the enzyme activities of mETC Complex I and III, as well as the abundances of NADH dehydrogenase 1 in Complex I and cytochrome b in Complex III in EC. Blocking antibody for the receptor of advanced glycation end products (RAGE) prevented glyLDL-induced changes in NOX and mETC enzymes. Combination of C3G and RAGE antibody did not significantly enhance glyLDL-induced inhibition of NOX or mETC enzymes. C3G reduced glyLDL-induced RAGE expression with the presence of RAGE antibody. C3G prevented prolonged incubation with the glyLDL-induced decrease in cell viability and the imbalance between key regulators for cell viability (cleaved caspase 3 and B cell Lyphoma-2) in EC. The findings suggest that RAGE plays an important role in glyLDL-induced oxidative stress in vascular EC. C3G may prevent glyLDL-induced NOX activation, the impairment of mETC enzymes and cell viability in cultured vascular EC. PMID:23443099

Xie, Xueping; Zhao, Ruozhi; Shen, Garry X.

2012-01-01

293

Molecular Characterization of a Novel Glucosyltransferase from Lactobacillus reuteri Strain 121 Synthesizing a Unique, Highly Branched Glucan with ?-(1?4) and ?-(1?6) Glucosidic Bonds  

PubMed Central

Lactobacillus reuteri strain 121 produces a unique, highly branched, soluble glucan in which the majority of the linkages are of the ?-(1?4) glucosidic type. The glucan also contains ?-(1?6)-linked glucosyl units and 4,6-disubstituted ?-glucosyl units at the branching points. Using degenerate primers, based on the amino acid sequences of conserved regions from known glucosyltransferase (gtf) genes from lactic acid bacteria, the L. reuteri strain 121 glucosyltransferase gene (gtfA) was isolated. The gtfA open reading frame (ORF) was 5,343 bp, and it encodes a protein of 1,781 amino acids with a deduced Mr of 198,637. The deduced amino acid sequence of GTFA revealed clear similarities with other glucosyltransferases. GTFA has a relatively large variable N-terminal domain (702 amino acids) with five unique repeats and a relatively short C-terminal domain (267 amino acids). The gtfA gene was expressed in Escherichia coli, yielding an active GTFA enzyme. With respect to binding type and size distribution, the recombinant GTFA enzyme and the L. reuteri strain 121 culture supernatants synthesized identical glucan polymers. Furthermore, the deduced amino acid sequence of the gtfA ORF and the N-terminal amino acid sequence of the glucosyltransferase isolated from culture supernatants of L. reuteri strain 121 were the same. GTFA is thus responsible for the synthesis of the unique glucan polymer in L. reuteri strain 121. This is the first report on the molecular characterization of a glucosyltransferase from a Lactobacillus strain. PMID:12200277

Kralj, S.; van Geel-Schutten, G. H.; Rahaoui, H.; Leer, R. J.; Faber, E. J.; van der Maarel, M. J. E. C.; Dijkhuizen, L.

2002-01-01

294

Total glucosides of paeony inhibit the inflammatory responses of mice with allergic contact dermatitis by restoring the balanced secretion of pro-/anti-inflammatory cytokines.  

PubMed

The present study aimed to investigate the regulation exerted by the total glucosides of paeony (TGP) on the production of interleukin-2 (IL-2), IL-4, IL-10 and IL-17 in the serum and lymphocytes of mice with allergic contact dermatitis (ACD). ACD in mice was induced by the repeated application of 2,4-dinitrochlorobenzene (DNCB) to their skins. The mice were orally administered TGP (35, 70, and 140mg/kg/d) and prednisone (Pre, 5mg/kg/d) from day 1 to day 7 after immunization. The inflammatory responses were evaluated by ear swelling and histological examination. Thymocyte proliferation was assayed by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H tetrazolium bromide assay. The cytokine production in the serum and lymphocytes supernatant was measured by enzyme-linked immunosorbent assay. The results indicated that the topical application of DNCB to the skin provoked obvious inflammatory responses. The oral administration of TGP (70 and 140mg/kg/d) and Pre (5mg/kg/d) significantly inhibited skin inflammation, decreased the thymus and spleen indices, and inhibited thymocyte proliferation in mice treated with DNCB. Further study indicated that TGP increased IL-4 and IL-10 production but decreased the production of IL-2 and IL-17 in the serum and lymphocyte supernatant. The correlation analysis suggested significantly positive correlations between IL-2 and IL-17 production and the severity of skin inflammation, whereas negative correlations were obtained for IL-4 and IL-10 production and skin inflammation. In summary, these results suggest that the therapeutic effects of TGP on ACD may result from its regulation of the imbalanced secretion of IL-2/IL-4 and IL-10/IL-17. PMID:25556068

Wang, Chun; Yuan, Jun; Wu, Hua-Xun; Chang, Yan; Wang, Qing-Tong; Wu, Yu-Jing; Zhou, Peng; Yang, Xiao-Dan; Yu, Jun; Wei, Wei

2015-02-01

295

Simultaneous determination of vitexin-4''-O-glucoside, vitexin-2''-O-rhamnoside, rutin and vitexin from hawthorn leaves flavonoids in rat plasma by UPLC-ESI-MS/MS.  

PubMed

A sensitive and accurate ultra-performance liquid chromatography electrospray ionization tandem mass spectrometry (UPLC-ESI-MS/MS) method was developed and validated for the simultaneous determination of vitexin-4''-O-glucoside (VGL), vitexin-2''-O-rhamnoside (VRH), rutin (RUT) and vitexin (VIT) in rat plasma after intravenous administration of hawthorn leaves flavonoids (HLF). Following protein precipitation by methanol, the analytes were separated on an ACQUITY UPLC BEH C(18) column packed with 1.7 microm particles by gradient elution using a mobile phase composed of acetonitrile and water (containing 0.1% formic acid) at a flow rate of 0.20 mL/min. The analytes and diphenhydramine (internal standard, IS) were detected in the multiple reaction monitoring (MRM) mode by means of an electrospray ionization (ESI) interface (m/z 292.96 for vitexin-4''-O-glucoside, m/z 293.10 for vitexin-2''-O-rhamnoside, m/z 299.92 for rutin, m/z 310.94 for vitexin and m/z 166.96 for IS). The calibration curve was linear over the range 10-40,000 ng/mL for vitexin-4''-O-glucoside, 10-50,000 ng/mL for vitexin-2''-O-rhamnoside, 8-1000 ng/mL for rutin and 16-2000 ng/mL for vitexin. The intra- and inter-run precisions (relative standard deviation, RSD) of these analytes were all within 15% and the accuracy (the relative error, RE) ranged from -10% to 10%. The stability experiment indicated that the four analytes in rat plasma samples and plasma extracts under anticipated conditions were stable. The developed method was applied for the first time to pharmacokinetic studies of the four bioactive compounds of hawthorn leaves flavonoids following a single intravenous administration of 20 mg/kg in rats. PMID:20570577

Zhang, Wenjun; Xu, Ming; Yu, Chaoqun; Zhang, Guofeng; Tang, Xing

2010-07-01

296

On the chemical constituents of Dipsacus asper.  

PubMed

Bioassay-guided fractionation of 95% EtOH extract from the roots of Dipsacus asper lead to the isolation of some phenolic acids (caffeic acid, 2,6-dihydroxycinnamic acid, vanillic acid, 2'-O-caffeoyl-D-glucopyranoside ester, and caffeoylquinic acid) as the major active components, and five new iridoid glucoside dimers (1-5) and one new iridoid glucoside monomer (6), other known iridoid glycosides loganin, cantleyoside, triplostoside A, lisianthioside, 6'-O-beta-D-apiofuranosyl sweroside, as well as triterpenoids oleanic acid and akebiasaponin D. The structures of new compounds 1-6 were determined as dipsanosides C (1), D (2), E (3), F (4), G (5), and 3'-O-beta-D-glucopyranosyl sweroside (6) by spectroscopic, including 1D and 2D NMR techniques, and chemical methods. PMID:18057739

Tian, Xiao-Yan; Wang, Ying-Hong; Liu, Hong-Yue; Yu, Shi-Shan; Fang, Wei-Shuo

2007-12-01

297

Discovery of Ipragliflozin (ASP1941): a novel C-glucoside with benzothiophene structure as a potent and selective sodium glucose co-transporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes mellitus.  

PubMed

A series of C-glucosides with various heteroaromatics has been synthesized and its inhibitory activity toward SGLTs was evaluated. Upon screening several compounds, the benzothiophene derivative (14a) was found to have potent inhibitory activity against SGLT2 and good selectivity versus SGLT1. Through further optimization of 14a, a novel benzothiophene derivative (14h; ipragliflozin, ASP1941) was discovered as a highly potent and selective SGLT2 inhibitor that reduced blood glucose levels in a dose-dependent manner in diabetic models KK-A(y) mice and STZ rats. PMID:22507206

Imamura, Masakazu; Nakanishi, Keita; Suzuki, Takayuki; Ikegai, Kazuhiro; Shiraki, Ryota; Ogiyama, Takashi; Murakami, Takeshi; Kurosaki, Eiji; Noda, Atsushi; Kobayashi, Yoshinori; Yokota, Masayuki; Koide, Tomokazu; Kosakai, Kazuhiro; Ohkura, Yasufumi; Takeuchi, Makoto; Tomiyama, Hiroshi; Ohta, Mitsuaki

2012-05-15

298

Maintenance of glucose-sensitive insulin secretion of cryopreserved human islets with University of Wisconsin solution and ascorbic acid-2 glucoside.  

PubMed

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

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

299

Plasma pharmacokinetics and urinary excretion of isoflavones after ingestion of soy products with different aglycone/glucoside ratios in South Korean women  

PubMed Central

Asian populations are thought to receive significant health benefits from traditional diets rich in soybeans due to high isoflavone contents. However, available epidemiologic data only weakly support this hypothesis. The present study was carried out to assess the pharmacokinetics of isoflavones in South Korean women after ingestion of soy-based foods. Twenty-six healthy female volunteers (20-30 y old) consumed three different soy products (i.e., isogen, soymilk, and fermented soybeans) with different aglycone/glucoside ratios. Plasma and urine isoflavone concentrations were measured by high-performance liquid chromatography (HPLC) after ingestion of one of the soy products. Pharmacokinetic parameters were determined using the WinNonlin program. The area under the curve (AUC) for plasma daidzein levels of the soymilk group (2,101 ± 352 ng · h/mL) was significantly smaller than those of the isogen (2,628 ± 573 ng · h/mL) and fermented soybean (2,593 ± 465 ng · h/mL) groups. The maximum plasma concentration (Cmax) of daidzein for the soymilk group (231 ± 44 ng/mL) was significantly higher than those of the isogen (160 ± 32 ng/mL) and fermented soybean (195 ± 35 ng/mL) groups. The half-lives of daidzein and genistein in the soymilk group (5.9 and 5.6 h, respectively) were significantly shorter than those in the individuals given isogen (9.6 and 8.5 h, respectively) or fermented soybean (9.5 and 8.2 h, respectively). The urinary recovery rates of daidzein and genistein were 42% and 17% for the isogen group, 46% and 23% for the fermented soybean group, and 33% and 22% for the soymilk group. In conclusion, our data indicated that soy products containing high levels of isoflavone aglycone are more effective for maintaining plasma isoflavone concentrations. Additional dose-response, durational, and interventional studies are required to evaluate the ability of soy-based foods to increase the bioavailability of isoflavones that positively affect human health. PMID:24133619

Chang, Youngeun

2013-01-01

300

Contents of all forms of vitamin B6, pyridoxine-?-glucoside and 4-pyridoxic acid in mature milk of Japanese women according to 4-pyridoxolactone-conversion high performance liquid chromatography.  

PubMed

The contents of six vitamin B6 forms, pyridoxine-?-glucoside, and 4-pyridoxic acid in mature milk of 20 Japanese lactating women consuming ordinary Japanese foods were determined by a 4-pyridoxolactone-conversion HPLC method. These compounds were determined with the average recovery rate of 83.9% or more. The average total content of vitamin B6 forms was 1.01 ± 0.32 (µmol/L). Pyridoxal and pyridoxal 5'-phosphate were found in all of the samples, and their average contents were 0.71 ± 0.28 (µmol/L) and 0.16 ± 0.07 (µmol/L), respectively. Pyridoxamine, pyridoxine, pyridoxamine 5'-phosphate, pyridoxine 5'-phosphate, and pyridoxine-?-glucoside were found in 15, 14, 13, 9, and 7 samples, respectively. The presence of pyridoxine 5'-phosphate was for the first time found in human milk. A method for the determination of 4-pyridoxic acid, which is the excretion form of vitamin B6, was modified to quantitate it by isocratic HPLC. 4-Pyridoxic acid was found in all samples, and its average content was 0.094 ± 0.040 (µmol/L), which was only 12% of its content in cow (Holstein) milk. The total content of vitamin B6 forms, and predominant presence of pyridoxal among other vitamin B6 forms in the Japanese women's milk samples shared similar characteristics with American women's milk samples. PMID:23535534

Yagi, Toshiharu; Iwamoto, Saya; Mizuseki, Rie; Furuya, Michi; Nakayama, Kazuko

2013-01-01

301

Identification, properties, and genetic control of UDP-glucose: cyanidin-3-rhamnosyl-(1 leads to 6)-glucoside-5-O-glucosyltransferase isolated from petals of the red campion (Silene dioica).  

PubMed

An enzyme catalyzing the transfer of the glucosyl moiety of UDP-glucose to the 5-hydroxyl group of cyanidin-3-rhamnosyl-(1 leads to 6)-glucoside has been demonstrated in petal extracts of Silene dioica plants. This glucosyltransferase activity was not detectable in green parts of these plants. The enzyme activity is controlled by a single dominant gene M; no glucosyltransferase activity could be demonstrated in petals of m/m plants. The enzyme was purified eightyfold by PVP and Sephadex G50 chromatography. The glucosyltransferase had a pH optimum of 7.4, had a molecular weight of about 55,000, was stimulated by divalent metal ions, and had a "true Km" values of 0.5 x 10(-3) M for UDP-glucose and 3.6 x 10(-3) M for cyanidin-3-rhamnosylglucoside. Pelargonidin-3-rhamnosylglucoside also could serve as acceptor. The enzyme did not catalyze the glucosylation of the 5-hydroxyl group of cyanidin-3-glucoside, although in petals of M/- n/n mutants cyanidin-3,5-diglucoside is present. ADP-glucose could not serve as a glucosyl donor. PMID:751641

Kamsteeg, J; van Brederode, J; van Nigtevecht, G

1978-12-01

302

Aglycone specificity of Thermotoga neapolitana ?-glucosidase 1A modified by mutagenesis, leading to increased catalytic efficiency in quercetin-3-glucoside hydrolysis  

PubMed Central

Background The thermostable ?-glucosidase (TnBgl1A) from Thermotoga neapolitana is a promising biocatalyst for hydrolysis of glucosylated flavonoids and can be coupled to extraction methods using pressurized hot water. Hydrolysis has however been shown to be dependent on the position of the glucosylation on the flavonoid, and e.g. quercetin-3-glucoside (Q3) was hydrolysed slowly. A set of mutants of TnBgl1A were thus created to analyse the influence on the kinetic parameters using the model substrate para-nitrophenyl-?-D-glucopyranoside (pNPGlc), and screened for hydrolysis of Q3. Results Structural analysis pinpointed an area in the active site pocket with non-conserved residues between specificity groups in glycoside hydrolase family 1 (GH1). Three residues in this area located on ?-strand 5 (F219, N221, and G222) close to sugar binding sub-site +2 were selected for mutagenesis and amplified in a protocol that introduced a few spontaneous mutations. Eight mutants (four triple: F219L/P165L/M278I, N221S/P165L/M278I, G222Q/P165L/M278I, G222Q/V203M/K214R, two double: F219L/K214R, N221S/P342L and two single: G222M and N221S) were produced in E. coli, and purified to apparent homogeneity. Thermostability, measured as Tm by differential scanning calorimetry (101.9°C for wt), was kept in the mutated variants and significant decrease (?T of 5 - 10°C) was only observed for the triple mutants. The exchanged residue(s) in the respective mutant resulted in variations in KM and turnover. The KM-value was only changed in variants mutated at position 221 (N221S) and was in all cases monitored as a 2-3 × increase for pNPGlc, while the KM decreased a corresponding extent for Q3. Turnover was only significantly changed using pNPGlc, and was decreased 2-3 × in variants mutated at position 222, while the single, double and triple mutated variants carrying a mutation at position 221 (N221S) increased turnover up to 3.5 × compared to the wild type. Modelling showed that the mutation at position 221, may alter the position of N291 resulting in increased hydrogen bonding of Q3 (at a position corresponding to the +1 subsite) which may explain the decrease in KM for this substrate. Conclusion These results show that residues at the +2 subsite are interesting targets for mutagenesis and mutations at these positions can directly or indirectly affect both KM and turnover. An affinity change, leading to a decreased KM, can be explained by an altered position of N291, while the changes in turnover are more difficult to explain and may be the result of smaller conformational changes in the active site. PMID:21345211

2011-01-01

303

Nucleotide sequences of the arb genes, which control beta-glucoside utilization in Erwinia chrysanthemi: comparison with the Escherichia coli bgl operon and evidence for a new beta-glycohydrolase family including enzymes from eubacteria, archeabacteria, and humans.  

PubMed Central

The phytopathogenic bacterium Erwinia chrysanthemi, unlike other members of the family Enterobacteriaceae, is able to metabolize the beta-glucosides, arbutin, and salicin. A previous genetic analysis of the E. chrysanthemi arb genes, which mediate beta-glucoside metabolism, suggested that they were homologous to the Escherichia coli K-12 bgl genes. We have now determined the nucleotide sequence of a 5,065-bp DNA fragment containing three genes, arbG, arbF, and arbB. Deletion analysis, expression in minicell systems, and comparison with sequences of other proteins suggest that arbF and arbB encode a beta-glucoside-specific phosphotransferase system-dependent permease and a phospho-beta-glucosidase, respectively. The ArbF amino acid sequence shares 55% identity with that of the E. coli BglF permease and contains most residues thought to be important for a phosphotransferase. One change, however, was noted, since BglF Arg-625, presumably involved in phosphoryl transfer, was replaced by a Cys residue in ArbF. An analysis of the ArbB sequence led to the definition of a protein family which contained enzymes classified as phospho-beta-glucosidases, phospho-beta-galactosidases, beta-glucosidases, and beta-galactosidases and originating from gram-positive and gram-negative bacteria, archebacteria, and mammals, including humans. An analysis of this family allowed us (i) to speculate on the ways that these enzymes evolved, (ii) to identify a glutamate residue likely to be a key amino acid in the catalytic activity of each protein, and (iii) to predict that domain II of the human lactate-phlorizin hydrolase, which is involved in lactose intolerance, is catalytically nonactive. A comparison between the untranslated regions of the E. chrysanthemi arb cluster and the E. coli bgl operon revealed the conservation of two regions which, in the latter, are known to terminate transcription under noninducing conditions and be the target of the BglG transcriptional antiterminator under inducing conditions. ArbG was found to share a high level of similarity with the BglG antiterminator as well as with Bacillus subtilis SacT and SacY antiterminators, suggesting that ArbG functions as an antiterminator in regulating the expression of the E. chrysanthemi arb genes. Images PMID:1732212

el Hassouni, M; Henrissat, B; Chippaux, M; Barras, F

1992-01-01

304

Biosynthesis of the Cyanogenic Glucosides Linamarin and Lotaustralin in Cassava: Isolation, Biochemical Characterization, and Expression Pattern of CYP71E7, the Oxime-Metabolizing Cytochrome P450 Enzyme1[OA  

PubMed Central

Cassava (Manihot esculenta) is a eudicotyledonous plant that produces the valine- and isoleucine-derived cyanogenic glucosides linamarin and lotaustralin with the corresponding oximes and cyanohydrins as key intermediates. CYP79 enzymes catalyzing amino acid-to-oxime conversion in cyanogenic glucoside biosynthesis are known from several plants including cassava. The enzyme system converting oxime into cyanohydrin has previously only been identified in the monocotyledonous plant great millet (Sorghum bicolor). Using this great millet CYP71E1 sequence as a query in a Basic Local Alignment Search Tool-p search, a putative functional homolog that exhibited an approximately 50% amino acid sequence identity was found in cassava. The corresponding full-length cDNA clone was obtained from a plasmid library prepared from cassava shoot tips and was assigned CYP71E7. Heterologous expression of CYP71E7 in yeast afforded microsomes converting 2-methylpropanal oxime (valine-derived oxime) and 2-methylbutanal oxime (isoleucine-derived oxime) to the corresponding cyanohydrins, which dissociate into acetone and 2-butanone, respectively, and hydrogen cyanide. The volatile ketones were detected as 2.4-dinitrophenylhydrazone derivatives by liquid chromatography-mass spectrometry. A KS of approximately 0.9 ?m was determined for 2-methylbutanal oxime based on substrate-binding spectra. CYP71E7 exhibits low specificity for the side chain of the substrate and catalyzes the conversion of aliphatic and aromatic oximes with turnovers of approximately 21, 17, 8, and 1 min?1 for the oximes derived from valine, isoleucine, tyrosine, and phenylalanine, respectively. A second paralog of CYP71E7 was identified by database searches and showed approximately 90% amino acid sequence identity. In tube in situ polymerase chain reaction showed that in nearly unfolded leaves, the CYP71E7 paralogs are preferentially expressed in specific cells in the endodermis and in most cells in the first cortex cell layer. In fully unfolded leaves, the expression is pronounced in the cortex cell layer just beside the epidermis and in specific cells in the vascular tissue cortex cells. Thus, the transcripts of the CYP71E7 paralogs colocalize with CYP79D1 and CYP79D2. We conclude that CYP71E7 is the oxime-metabolizing enzyme in cyanogenic glucoside biosynthesis in cassava. PMID:21045121

Jørgensen, Kirsten; Morant, Anne Vinther; Morant, Marc; Jensen, Niels Bjerg; Olsen, Carl Erik; Kannangara, Rubini; Motawia, Mohammed Saddik; Møller, Birger Lindberg; Bak, Søren

2011-01-01

305

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

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

Mbikay, Majambu; Sirois, Francine; Simoes, Sonia; Mayne, Janice; Chrétien, Michel

2014-01-01

306

Purification from Fusobacterium mortiferum ATCC 25557 of a 6-phosphoryl-O-alpha-D-glucopyranosyl:6-phosphoglucohydrolase that hydrolyzes maltose 6-phosphate and related phospho-alpha-D-glucosides.  

PubMed

6-Phosphoryl-O-alpha-D-glucopyranosyl:6-phosphoglucohydrolase (6-phospho-alpha-glucosidase) has been purified from Fusobacterium mortiferum ATCC 25557. p-Nitrophenyl-alpha-D-glucopyranoside 6-phosphate (pNP alpha Glc6P) served as the chromogenic substrate for detection and assay of enzyme activity. The O2-sensitive, metal-dependent phospho-alpha-glucosidase was stabilized during purification by inclusion of dithiothreitol and Mn2+ ion in chromatography buffers. Various 6-phosphoryl-O-alpha-linked glucosides, including maltose 6-phosphate, pNP alpha Glc6P, trehalose 6-phosphate, and sucrose 6-phosphate, were hydrolyzed by the enzyme to yield D-glucose 6-phosphate and aglycone moieties in a 1:1 molar ratio. 6-Phospho-alpha-glucosidase (M(r) of approximately 49,000; pI of approximately 4.9) is activated by Fe2+, Mn2+, Co2+, and Ni2+, and the maximum rate of pNP alpha Glc6P hydrolysis occurs at 40 degrees C within the pH range 7.0 to 7.5. The sequence of the first 32 amino acids of 6-phospho-alpha-glucosidase exhibits 67% identity (90% similarity) to that deduced for the N terminus of a putative phospho-beta-glucosidase (designated ORF f212) encoded by glvG in Escherichia coli. Western blots involving highly specific polyclonal antibody against 6-phospho-alpha-glucosidase and spectrophotometric analyses with pNP alpha Glc6P revealed only low levels of the enzyme in glucose-, mannose-, or fructose-grown cells of F. mortiferum. Synthesis of 6-phospho-alpha-glucosidase increased dramatically during growth of the organism on alpha-glucosides, such as maltose, alpha-methylglucoside, trehalose, turanose, and palatinose. PMID:7730284

Thompson, J; Gentry-Weeks, C R; Nguyen, N Y; Folk, J E; Robrish, S A

1995-05-01

307

Influence of biotransformation of luteolin, luteolin 7-O-glucoside, 3',4'-dihydroxyflavone and apigenin by cultured rat hepatocytes on antioxidative capacity and inhibition of EGF receptor tyrosine kinase activity.  

PubMed

Flavonoids are known as biologically active compounds. Although this has been shown by several in vivo studies, it is still elusive whether their metabolites exert similar activities. Herein we investigated the biotransformation of four different flavonoids, 3',4'-dihydroxyflavone, apigenin, luteolin and luteolin 7-O-glucoside, by cultured rat hepatocytes using a combination of enzymatic deconjugation, HPLC separation and high-resolution mass spectrometry. These flavonoids were chosen because they are active components of many plants, e. g., artichokes. All flavonoids showed rather complex metabolite patterns dominated by phase II metabolites, mainly sulfates, methyl sulfates and methyl glucuronides, but also of combined glucuronide and sulfate conjugates. Phase I metabolism by hydroxylation was rendered likely only for apigenin to form luteolin. When culture media containing the flavonoids and their metabolites were assayed for antioxidative capacity by the DPPH assay, only compounds with hydroxy groups in position 3' and 4' of the B ring were active. Thus, during metabolism of (inactive) apigenin a strong increase in the antioxidative effect was observed while that of the other three flavonoids decreased with time. Determination of EGF receptor tyrosine kinase activity likewise revealed strong inhibition in the presence of a catechol group at ring B. However, in this case the situation was much more complex resulting in a significant increase of the inhibitory activity of 3',4'-dihydroxyflavone and apigenin, but not of luteolin and luteolin 7-O-glucoside during 22 h of incubation. These results show that the biotransformation of flavonoids is very complex and may result not only in a loss but also in a gain of biological activity depending on the individual structural features. PMID:16732514

Schlupper, Doreen; Giesa, Sabine; Gebhardt, Rolf

2006-06-01

308

Incorporation of an introduced weed into the diet of a native butterfly: consequences for preference, performance and chemical defense.  

PubMed

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

Knerl, Angela; Bowers, M Deane

2013-10-01

309

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

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

Liu, Xiao-hua; Zhao, Jian-bang; Guo, Long; Yang, Ying-lai; Hu, Fang; Zhu, Rui-juan; Feng, Shi-lan

2014-09-01

310

The biosynthesis of cyanogenic glucosides in higher plants. The (E)- and (Z)-isomers of p-hydroxyphenylacetaldehyde oxime as intermediates in the biosynthesis of dhurrin in Sorghum bicolor (L. ) Moench  

SciTech Connect

The biosynthesis of the tyrosine-derived cyanogenic glucoside dhurrin has been studied with a microsomal preparation obtained from etiolated seedlings of sorghum. The biosynthetic pathway involves tyrosine, N-hydroxytyrosine, and p-hydroxyphenylacetaldehyde oxime as early intermediates. The use of deuterium-labeled tyrosine and mass spectrometric analyses demonstrate that the alpha-hydrogen atom of tyrosine is retained in the conversion of tyrosine to p-hydroxyphenylacetaldehyde oxime. This excludes p-hydroxyphenylpyruvic acid oxime as intermediate in the pathway. A high pressure liquid chromatography method was developed to separate the (E)- and (Z)-isomers of p-hydroxyphenylacetaldehyde oxime. The microsomal enzyme system was found to produce initially the (E)-isomer of p-hydroxyphenylacetaldehyde oxime. An isomerase then converts the (E)-isomer to the (Z)-isomer, which is the isomer preferentially utilized by the microsomal enzyme system in the subsequent biosynthetic reactions. The (E)-isomer produced in situ is more efficiently converted to the (Z)-isomer than exogenously added (E)-isomer and may thus be metabolically channeled.

Halkier, B.A.; Olsen, C.E.; Moller, B.L. (Royal Veterinary and Agricultural Univ., Frederiksberg C (Denmark))

1989-11-25

311

4'''-Acetylvitexin-2''-O-rhamnoside, isoorientin, orientin, and 8-methoxykaempferol-3-O-glucoside as markers for the differentiation of Crataegus monogyna and Crataegus pentagyna from Crataegus laevigata (Rosaceae).  

PubMed

In our chemotaxonomic investigation of pharmaceutically relevant Crataegus species, the qualitative and quantitative flavonoid fingerprint of Crataegus monogyna and C. pentagyna is presented. Six flavonoids were identified as vitexin-2''-O-rhamnoside (1), vitexin (2), isovitexin (3), rutin (4), hyperoside (5), and isoquercitrin (6). Besides the verification of the main compounds isoorientin (7) and orientin (8) in C. pentagyna, further four flavonoids were isolated and identified as isoorientin-2''-O-rhamnoside (9), orientin-2''-O-rhamnoside (10), isovitexin-2''-O-rhamnoside (11), and 8-methoxykaempferol-3-O-glucoside (12) by means of 1D- and 2D-NMR, MS, and UV analyses. Compound 12 was isolated for the first time from C. pentagyna. In contrast to C. pentagyna, C. monogyna samples were predominated by 4'''-acetylvitexin-2''-O-rhamnoside (13), which was missing in C. pentagyna. Hence, 13 represents an interesting compound for chemotaxonomy of C. monogyna, whereas the main flavonoids 7, 8, and 12 could be proposed as markers for C. pentagyna. The absence of 7, 8, 12, and 13 in C. laevigata offers an appropriate tool for additional differentiation from C. monogyna and C. pentagyna, and for sample identification and quality control of the three main Crataegus species used in European phytotherapy. PMID:18081102

Prinz, Sonja; Ringl, Alexandra; Huefner, Antje; Pemp, Enne; Kopp, Brigitte

2007-12-01

312

[Chemical and biological evaluation of the effect of plant extracts against Plasmodium berghei].  

PubMed

Extracts from thirteen species of plants were evaluated by "in vivo" antimalarial test against plasmodium berghei effects. Significant activities were observed in the ethyl acetate and aqueous extracts, elaborated of Cedrela tonduzii leaves, Trichilia havanensis and Trichilia americana barks, Neurolaena lobata and Gliricidia sepium leaves and Duranta repens fruits. Compounds identified include flavanoids, coumarins, mellilotic acid and iridoids which some kind of biodynamic activity has previously been reported. The flavone quercetin 1 purified from C. tonduzii gave strong antimalarial activity, however, its respective glucosides (quercetin 3-glucoside 2 y robinine 7) showed little significant activity. PMID:9246360

Castro, O; Barrios, M; Chinchilla, M; Guerrero, O

1996-08-01

313

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

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.

Halkier, B.A.; Lykkesfeldt, J.; Moller, B.L. (Royal Veterinary and Agricultural Univ., Copenhagen (Denmark))

1991-01-15

314

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

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.

Halkier, B.A.; Moller, B.L. (Royal Veterinary and Agricultural Univ., Copenhagen (Denmark))

1990-12-05

315

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

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

Masuzaki, S; Shigyo, M; Yamauchi, N

2006-02-01

316

Cyanidin 3-glucoside attenuates obesity-associated insulin resistance and hepatic steatosis in high-fat diet-fed and db/db mice via the transcription factor FoxO1.  

PubMed

Obesity is a major risk factor for the development of type 2 diabetes, and both conditions are now recognized to possess significant inflammatory components underlying their pathophysiologies. Here, we hypothesized that cyanidin 3-glucoside (C3G), a typical anthocyanin reported to possess potent anti-inflammatory properties, would ameliorate obesity-associated inflammation and metabolic disorders, such as insulin resistance and hepatic steatosis in mouse models of diabesity. Male C57BL/6J obese mice fed a high-fat diet for 12 weeks and genetically diabetic db/db mice at an age of 6 weeks received dietary C3G supplementation (0.2%) for 5 weeks. We found that dietary C3G lowered fasting glucose levels and markedly improved the insulin sensitivity in both high-fat diet fed and db/db mice as compared with unsupplemented controls. White adipose tissue messenger RNA levels and serum concentrations of inflammatory cytokines (tumor necrosis factor-?, interleukin-6, and monocyte chemoattractant protein-1) were reduced by C3G, as did macrophage infiltration in adipose tissue. Concomitantly, hepatic triglyceride content and steatosis were alleviated by C3G. Moreover, C3G treatment decreased c-Jun N-terminal kinase activation and promoted phosphorylation and nuclear exclusion of forkhead box O1 after refeeding. These findings clearly indicate that C3G has significant potency in antidiabetic effects by modulating the c-Jun N-terminal kinase/forkhead box O1 signaling pathway and the related inflammatory adipocytokines. PMID:21543211

Guo, Honghui; Xia, Min; Zou, Tangbin; Ling, Wenhua; Zhong, Ruimin; Zhang, Weiguo

2012-04-01

317

A 3D-RISM-SCF method with dual solvent boxes for a highly polarized system: application to 1,6-anhydrosugar formation reaction of phenyl ?- and ?-D-glucosides under basic conditions.  

PubMed

One of the difficulties in application of the usual reference interaction site model self-consistent field (RISM-SCF) method to a highly polarized and bulky system arises from the approximate evaluation of electrostatic potential (ESP) with pure point charges. To improve this ESP evaluation, the ESP near a solute is directly calculated with a solute electronic wavefunction, that distant from a solute is approximately calculated with solute point charges, and they are connected with a switching function. To evaluate the fine solvation structure near the solute by incorporating the long-range solute-solvent Coulombic interaction with low computational cost, we introduced the dual solvent box protocol; one small box with the fine spacing is employed for the first and the second solvation shells and the other large box with the normal spacing is employed for long-range solute-solvent interaction. The levoglucosan formation from phenyl ?- and ?-d-glucosides under basic conditions is successfully inspected by this 3D-RISM-SCF method at the MP2 and SCS-MP2 levels, though the 1D-RISM-SCF could not be applied to this reaction due to the presence of highly polarized and bulky species. This 3D-RISM-SCF calculation reproduces the experimentally reported higher reactivity of the ?-anomer. The 3D-RISM-SCF-calculated activation free energy for the ?-anomer is closer to the experimental value than the PCM-calculated one. Interestingly, the solvation effect increases the difference in reactivity between these two anomers. The reason is successfully elucidated with 3D-RISM-SCF-calculated microscopic solvation structure and decomposition analysis of solute-solvent interaction. PMID:23525092

Aono, Shinji; Hosoya, Takashi; Sakaki, Shigeyoshi

2013-05-01

318

Indole alkaloids and other constituents of Rauwolfia serpentina.  

PubMed

From the dried roots of Rauwolfia serpentina were isolated five new indole alkaloids, N(b)-methylajmaline (1), N(b)-methylisoajmaline (2), 3-hydroxysarpagine (3), yohimbinic acid (4), isorauhimbinic acid (5), a new iridoid glucoside, 7-epiloganin (6), and a new sucrose derivative, 6'-O-(3,4,5-trimethoxybenzoyl)glomeratose A (7), together with 20 known compounds. The structures of the new compounds were determined by spectroscopic and chemical means. The inhibitory activities of the selected alkaloids on topoisomerase I and II and their cytotoxicity against the human promyelocytic leukemia (HL-60) cell lines were assessed. PMID:15974606

Itoh, Atsuko; Kumashiro, Tomoko; Yamaguchi, Machiko; Nagakura, Naotaka; Mizushina, Yoshiyuki; Nishi, Toyoyuki; Tanahashi, Takao

2005-06-01

319

Anomericity of trichothecene glucosides; Masked mycotoxins in cereal crops  

Technology Transfer Automated Retrieval System (TEKTRAN)

T-2 toxin is a trichothecene mycotoxin produced when the fungus Fusarium infects small grains, especially oats. Ingestion of T-2 toxin contaminated grain can cause diarrhea, hemorrhaging, and feed refusal. Cereal crops infected with mycotoxin-producing fungi form toxin glycosides, sometimes called m...

320

Linking Microbial Community Structure to ?-Glucosidic Function in Soil Aggregates  

SciTech Connect

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.

Bailey, Vanessa L.; Fansler, Sarah J.; Stegen, James C.; McCue, Lee Ann

2013-10-01

321

Two new podophyllotoxin glucosides from Sinopodophyllum emodi (Wall.) Ying.  

PubMed

Two new aryltetralin-type lignans, isopodophyllotoxin 7'-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside (1) and 4-demethyl-picropodophyllotoxin 7'-O-beta-D-glucopyranoside (2), along with eight known podophyllotoxin derivatives: 4-demethyl-podophyllotoxin 7'-O-beta-D-glucopyranoside (3), podophyllotoxin 7'-O-beta-D-glucopyranoside (4), deoxypodophyllotoxin (5), picropodophyllotoxin (6), podophyllotoxin (7), 4-demethyl-picropodophyllotoxin (8), 4-demethyl-podophyllotoxin (9), and 4-demethyl-deoxypodophyllotoxin (10), were isolated from the roots and rhizomes of Sinopodophyllum emodi (Wall.) Ying (Berberidaceae). Their structures were identified based on NMR spectral data and chemical evidence. PMID:11411537

Zhao, C; Huang, J; Nagatsu, A; Ogihara, Y

2001-06-01

322

Effects of Herbivore Damage and Nutrient Level on Induction of Iridoid Glycosides in Plantago lanceolata  

Microsoft Academic Search

Damage by larvae of the buckeye butterfly (Junonia coenia) resulted in removal of 15–25% of Plantago lanceolata leaf area. Plants grown under high nutrients were larger than those grown under low nutrients. Twenty-eight days after herbivory, plants grown under high nutrients were still larger than those grown under low nutrients, and plants exposed to herbivores were significantly smaller than those

Karolyn Darrow; M. Deane Bowers

1999-01-01

323

Phenological and population variation in iridoid glycosides of Plantago lanceolata (Plantaginaceae)  

Microsoft Academic Search

Relatively little is known about the natural variation in the secondary plant chemistry, or the potential sources of this variation, in Plantago lanceolata (Plantaginaceae) (Narrow-leafed plantain). To assess this chemical variation, P. lanceolata plants were collected monthly from five field populations located in Boulder County, Colorado, over the course of one growing season (July through October). There were significant effects

Karolyn Darrow; M. Deane Bowers

1997-01-01

324

Oleuropein, a non-toxic olive iridoid, is an anti-tumor agent and cytoskeleton disruptor  

SciTech Connect

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.

Hamdi, Hamdi K. [H2RC Corporation, 1920 E. Katella Avenue, Suite U, Orange, CA 92867 (United States)]. E-mail: hkhamdi@gmail.com; Castellon, Raquel [H2RC Corporation, 1920 E. Katella Avenue, Suite U, Orange, CA 92867 (United States)

2005-09-02

325

New Bisabolane-Type Sesquiterpenes from the Aerial Parts of Lippia dulcis.  

PubMed

Two new bisabolane-type sesquiterpenes, lippidulcine A (3) and epilippidulcine A (4), have been isolated from the aerial parts of Lippia dulcis TREV. along with five known flavonoids, cirsimaritin (5), salvigenin (6), eupatorin (7), 5-hydroxy-6,7,3',4'-tetramethoxyflavone (8) and 5,3'-dihydroxy-6,7,4',5'-tetramethoxyflavone (9), three known phenylethanoid glycosides, decaffeoylverbascoside (10), acteoside (11) and isoacteoside (12), and two known iridoid glucosides, 8-epiloganin (13) and lamiide (14). Their chemical structures have been determined on the basis of spectroscopic data. Among them, 5, 7, and 9 exhibited almost the same activity as that of alpha-tocopherol, and 10-12 were identified as stronger antioxidants than alpha-tocopherol using the ferric thiocyanate method. PMID:16141591

Ono, Masateru; Morinaga, Hiroaki; Masuoka, Chikako; Ikeda, Tsuyoshi; Okawa, Masafumi; Kinjo, Junei; Nohara, Toshihiro

2005-09-01

326

Antinociceptive and anti-inflammatory activities of Phlomis umbrosa Turcz extract.  

PubMed

Phlomis umbrosa Turcz has been used as the traditional medicine for thousands of years in China. In this paper, the acetic acid-induced writhing test, the hot plate test, the carrageenan-induced paw edema test, the xylene-induced ear swelling test, and the acetic acid-induced Evans blue leakage and leukocyte infiltration test were used to investigate the antinociceptive and anti-inflammatory activities of the aqueous extract of this plant (25, 50 and 100mg/kg i.p.). Good dose-dependent effects were obtained in most of these tests, except in the hot plate test and the acetic acid-induced Evans blue leakage test. TLC and HPLC analyses showed iridoid glucosides were the main compositions of this extract. These findings suggested that the aqueous extract of P. umbrosa has significant antinociceptive and anti-inflammatory activities. PMID:21406221

Shang, Xiaofei; Wang, Jinhui; Li, Maoxing; Miao, Xiaolou; Pan, Hu; Yang, Yaoguang; Wang, Yu

2011-06-01

327

Differential performance of a specialist and two generalist herbivores and their parasitoids on Plantago lanceolata.  

PubMed

The ability to cope with plant defense chemicals differs between specialist and generalist species. In this study, we examined the effects of the concentration of the two main iridoid glycosides (IGs) in Plantago lanceolata, aucubin and catalpol, on the performance of a specialist and two generalist herbivores and their respective endoparasitoids. Development of the specialist herbivore Melitaea cinxia was unaffected by the total leaf IG concentration in its host plant. By contrast, the generalist herbivores Spodoptera exigua and Chrysodeixis chalcites showed delayed larval and pupal development on plant genotypes with high leaf IG concentrations, respectively. This result is in line with the idea that specialist herbivores are better adapted to allelochemicals in host plants on which they are specialized. Melitaea cinxia experienced less post-diapause larval and pupal mortality on its local Finnish P. lanceolata than on Dutch genotypes. This could not be explained by differences in IG profiles, suggesting that M. cinxia has adapted in response to attributes of its local host plants other than to IG chemistry. Development of the specialist parasitoid Cotesia melitaearum was unaffected by IG variation in the diet of its host M. cinxia, a response that was concordant with that of its host. By contrast, the development time responses of the generalist parasitoids Hyposoter didymator and Cotesia marginiventris differed from those of their generalist hosts, S. exigua and C. chalcites. While their hosts developed slowly on high-IG genotypes, development time of H. didymator was unaffected. Cotesia marginiventris actually developed faster on hosts fed high-IG genotypes, although they then had short adult longevity. The faster development of C. marginiventris on hosts that ate high-IG genotypes is in line with the "immunocompromized host" hypothesis, emphasizing the potential negative effects of toxic allelochemicals on the host's immune response. PMID:21691810

Reudler, Joanneke H; Biere, Arjen; Harvey, Jeff A; van Nouhuys, Saskya

2011-07-01

328

Cognitive-enhancing and antioxidant activities of iridoid glycosides from Scrophularia buergeriana in scopolamine-treated mice.  

PubMed

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

Jeong, Eun Ju; Lee, Ki Yong; Kim, Seung Hyun; Sung, Sang Hyun; Kim, Young Choong

2008-06-24

329

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

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

Nurahmat, Mammat; Chen, Meixia; Luo, Qingli; Ling, Yun; Dong, Jingcheng; Huang, Chenggang

2014-12-01

330

21 CFR 172.816 - Methyl glucoside-coconut oil ester.  

Code of Federal Regulations, 2011 CFR

...0 Saponification number: 178-190 (b) It is used or intended for use as follows: (1) As an aid in crystallization of sucrose and dextrose at a level not to exceed the minimum quantity required to produce its intended...

2011-04-01

331

21 CFR 172.816 - Methyl glucoside-coconut oil ester.  

Code of Federal Regulations, 2010 CFR

...0 Saponification number: 178-190 (b) It is used or intended for use as follows: (1) As an aid in crystallization of sucrose and dextrose at a level not to exceed the minimum quantity required to produce its intended...

2010-04-01

332

Development and evaluation of monoclonal antibodies for the glucoside of T-2 toxin (T2-Glc)  

Technology Transfer Automated Retrieval System (TEKTRAN)

The interactions between fungi and plants can yield metabolites that are toxic in animal systems. Certain fungi are known to produce sesquiterpenoid trichothecenes, such as T-2 toxin, that are biotransformed by several mechanisms including glucosylation. The glucosylated forms have been found in gra...

333

Enzymatic glucosylation: sucrose glucosyltransferases and glucosidases in O- and S-glucoside synthesis  

Microsoft Academic Search

Glycosylation is considered as a useful method for improving chemical properties like solubility and volatility of compounds with interesting organoleptic or physiological properties. The aim of the research described in this thesis was to explore the enzymatic glycosylation of aglycones (nonsaccharide acceptor molecules). The initial focus is on the glucosylation of aromatic alcohols by non-Leloir glucosyltransferases like sucrose glucosyltransferases.Several streptococcal

G. H. Meulenbeld

2001-01-01

334

Leuconostoc mesenteroides glucansucrase synthesis of flavonoid glucosides by acceptor reactions in aqueous-organic solvents  

Microsoft Academic Search

The enzymatic glucosylation of luteolin was attempted using two glucansucrases: the dextransucrase from Leuconostoc mesenteroides NRRL B-512F and the alternansucrase from L. mesenteroides NRRL B-23192. Reactions were carried out in aqueous-organic solvents to improve luteolin solubility. A molar conversion of 44% was achieved after 24h of reaction catalysed by dextransucrase from L. mesenteroides NRRL B-512F in a mixture of acetate

Anne Bertrand; Sandrine Morel; François Lefoulon; Yves Rolland; Pierre Monsan; Magali Remaud-Simeon

2006-01-01

335

Treatment of Xerosis with a Topical Formulation Containing Glyceryl Glucoside, Natural Moisturizing Factors, and Ceramide  

PubMed Central

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

Kausch, Martina; Rippke, Frank; Schoelermann, Andrea M.; Filbry, Alexander W.

2012-01-01

336

Synthesis and antimicrobial activity of some S-beta-D-glucosides of 4-mercaptopyrimidine.  

PubMed

5-Acetyl-2-aryl-6-methyl-4-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosylmercapto)pyramidines 3a-c were obtained by the reaction of 5-acetyl-2-aryl-6-methyl-pyrimidine thiol 1a-c with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide (2) in aq. KOH/acetone. The reaction of 1a-c with peracetylated galactose 5 and peracetylated ribose 8 under MW irradiation gave 5-acetyl-2-aryl-6-methyl-4-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosylmercapto)pyrimidine 6a-c and 5-acetyl-2-aryl-6-methyl-4-(2,3,5-tri-O-acetyl-beta-D-ribofuranosylmercapto)pyrimidines 9a-c. The deprotection of 3a-c, 6a-c, and 9a-c in the presence of methanol and TEA/H(2)O yielded the deprotected products 4a-c, 7a-c, and 10a-c. The structures of the compounds were confirmed by using IR, (1)H, (13)C spectra and microanalysis. Selected members of these compounds were screened for antimicrobial activity. PMID:20183622

Moustafa, A H; Morsy, H A; Assy, M G; Haikal, A Z

2009-09-01

337

Enhanced adsorption of alkyl glucosides on the silica/water interface by addition of amine oxides.  

PubMed

The effect of adding a small amount of dodecyl dimethylamine oxide (DDAO) on adsorption on silica from an aqueous solution of dodecyl maltoside (C12G2) has been investigated. The C12G2 itself does not adsorb significantly on silica at any concentration. DDAO on the other hand readily adsorbs in a bilayer-like structure at concentrations approaching the critical micelle concentration (cmc), but the adsorbed amount at the concentrations it has been applied in these mixtures is small. In contrast, by combination of the two surfactants, significant adsorption is observed at concentrations where the adsorption of the pure DDAO, as well as pure C12G2, is very low. We thus see a strong enhancement of the adsorption from the mixed system. The adsorption is suggested to be a two-step process, where individual DDAO molecules first adsorb to the silica surface through electrostatic interactions, and then C12G2 adsorbs at the hydrophobic sites the DDAO tails constitute through hydrophobic bonding. A minimum concentration of DDAO is required to induce adsorption from a solution with constant C12G2 concentration. This concentration is lower for C12G2 solutions below and equal to cmcC12G2 than above cmcC12G2. In addition, the total adsorbed amount shows a maximum around cmcC12G2 of the mixture for a solution with low DDAO contents. Both these effects are explained by incorporation of DDAO in the mixed micelles above cmc(mix), which leads to a desorption of DDAO from the surface. PMID:15779947

Matsson, Maria K; Kronberg, Bengt; Claesson, Per M

2005-03-29

338

21 CFR 178.3600 - Methyl glucoside-coconut oil ester.  

Code of Federal Regulations, 2010 CFR

...172.816(a) of this chapter may be safely used as a processing aid (filter aid) in the manufacture of starch, including industrial starch-modified complying with § 178.3520, intended for use as a component of articles that contact...

2010-04-01

339

21 CFR 178.3600 - Methyl glucoside-coconut oil ester.  

Code of Federal Regulations, 2011 CFR

...172.816(a) of this chapter may be safely used as a processing aid (filter aid) in the manufacture of starch, including industrial starch-modified complying with § 178.3520, intended for use as a component of articles that contact...

2011-04-01

340

Aspects on the Biosynthesis of the Cyanogenic Glucoside Triglochinin in Triglochin maritima1.  

PubMed

The incorporation of L-[U- (14)C]phenylalanine, L-[U- (14)C]tyrosine and [U- (14)C]4-hydroxyphenylacetonitrile into triglochinin and taxiphyllin, the latter a possible precursor of the former, was studied in seedlings of TRIGLOCHIN MARITIMA L. The nitrile was by far the best substrate; incorporation of the amino acids was poor. Environmental factors such as light and humidity act differently on production of both compounds which also show a wide variation in individual seedlings. Quantitative evaluation of the specific activities indicate that taxiphyllin cannot be regarded as a precursor of triglochinin and that the two compounds are probably synthesized by two, at least mainly independent, pathways. PMID:17340339

Nahrstedt, A; Kant, J D; Hösel, W

1984-10-01

341

Molecular Modeling Studies of Thiophenyl C-Aryl Glucoside SGLT2 Inhibitors as Potential Antidiabetic Agents  

PubMed Central

A QSAR study on thiophenyl derivatives as SGLT2 inhibitors as potential antidiabetic agents was performed with thirty-three compounds. Comparison of the obtained results indicated the superiority of the genetic algorithm over the simulated annealing and stepwise forward-backward variable method for feature selection. The best 2D QSAR model showed satisfactory statistical parameters for the data set (r2 = 0.8499, q2 = 0.8267, and pred_r2 = 0.7729) with four descriptors describing the nature of substituent groups and the environment of the substitution site. Evaluation of the model implied that electron-rich substitution position improves the inhibitory activity. The good predictive 3D-QSAR models by k-nearest neighbor (kNN) method for molecular field analysis (MFA) have cross-validated coefficient q2 value of 0.7663 and predicted r2 value of 0.7386. The results have showed that thiophenyl groups are necessary for activity and halogen, bulky, and less bulky groups in thiophenyl nucleus enhanced the biological activity. These studies are promising for the development of novel SGLT2 inhibitor, which may have potent antidiabetic activity. PMID:25574393

Sharma, Mukesh C.; Sharma, Smita

2014-01-01

342

Novel glucoalkaloids from Rauwolfia cell cultures--acetylrauglucine and related glucosides.  

PubMed

From cell suspension cultures of Rauwolfia serpentina grown in an optimized production medium for the glucoalkaloid raucaffricine, a novel glucoalkaloid was isolated and identified as 17-O-acetyl-21-O-beta-D-glucopyranosyl-ajmaline (acetylrauglucine). This alkaloid is formed in very small amounts (less than 5 x 10(-4)%). The biogenetically related N alpha-demethylated base (acetyl-nor-rauglucine) and the deacetyl product rauglucine have also been detected in culture extracts. In addition 21(R)-(beta-D-glucopyranosyl)-hydroxy-sarpagan-17-al has been isolated and identified as an artifact which originates from raucaffricine. PMID:3223033

Ruyter, C M; Schübel, H; Stöckigt, J

1988-01-01

343

Leuconostoc mesenteroides glucansucrase synthesis of flavonoid glucosides by acceptor reactions in aqueous-organic solvents.  

PubMed

The enzymatic glucosylation of luteolin was attempted using two glucansucrases: the dextransucrase from Leuconostoc mesenteroides NRRL B-512F and the alternansucrase from L. mesenteroides NRRL B-23192. Reactions were carried out in aqueous-organic solvents to improve luteolin solubility. A molar conversion of 44% was achieved after 24h of reaction catalysed by dextransucrase from L. mesenteroides NRRL B-512F in a mixture of acetate buffer (70%)/bis(2-methoxyethyl) ether (30%). Two products were characterised by nuclear magnetic resonance (NMR) spectroscopy: luteolin-3'-O-alpha-d-glucopyranoside and luteolin-4'-O-alpha-d-glucopyranoside. In the presence of alternansucrase from L. mesenteroides NRRL B-23192, three additional products were obtained with a luteolin conversion of 8%. Both enzymes were also able to glucosylate quercetin and myricetin with conversion of 4% and 49%, respectively. PMID:16530175

Bertrand, Anne; Morel, Sandrine; Lefoulon, François; Rolland, Yves; Monsan, Pierre; Remaud-Simeon, Magali

2006-05-22

344

Sesquiterpene Glucosides from Anti-leukotriene B4 Release Fraction of Taraxacum Officinale  

Microsoft Academic Search

Chemical examination of the MeOH extract of the root of Taraxacum officinale, which exhibited inhibitory activity on the formation of leukotriene B4 from activated human neutrophils, has resulted in the isolation of 14-O-?-D-glucosyl-11,13-dihydro-taraxinic acid (1) and 14-O-?-D-glucosyl-taraxinic acid (2). The absolute stereostructure of 1 has been established by X-ray chrystallographic examination.

Yoshiki Kashiwada; Koichiro Takanaka; Harumi Tsukada; Yoshihisa Miwa; Toru Taga; Shigeo Tanaka; Yasumasa Ikeshiro

2001-01-01

345

Effect of water content on the acid-base equilibrium of cyanidin-3-glucoside.  

PubMed

Laser Flash Photolysis was employed to measure the deprotonation and reprotonation rate constants of cyanidin 3-monoglucoside (kuromanin) in water/methanol mixtures. It was found that the deprotonation rate constant kd decreases with decreasing water content, reflecting the lack of free water molecules around kuromanin, which may accommodate and stabilize the outgoing protons. On the other hand, the reprotonation rate constant, kp, increases with the decrease in water concentration from a value of kp=2×10(10)lmol(-1)s(-1) in water up to kp=6×10(10)lmol(-1)s(-1) at 5.6M water concentration in the mixture. The higher value of kp at lower water concentrations reflects the fact that the proton is not freely escaping the solvation shell of the molecule. The deprotonation rate constant decreases with decreasing water content, reflecting the lack of free water molecules around kuromanin that can accommodate the outgoing protons. Overall, the acidity constant of the flavylium cation decreases with the decrease in water concentration from pKa values of 3.8 in water to approximately 4.8 in water-depleted media, thus shifting the equilibrium towards the red-coloured form, AH(+), at low water contents. The presence, or lack, of water, will affect the colour shade (red to blue) of kuromanin. This is relevant for its role as an intrinsic food component and as a food pigment additive (E163). PMID:25442581

Coutinho, Isabel B; Freitas, Adilson; Maçanita, António L; Lima, J C

2015-04-01

346

Catalpol ameliorates sodium taurocholate-induced acute pancreatitis in rats via inhibiting activation of nuclear factor kappa B.  

PubMed

Catalpol, an iridoid glucoside extracted from the traditional Chinese herbal medicine, Rehmannia glutinosa, is reported to exert neuroprotective, anti-inflammatory, anti-tumor and anti-apoptotic effects. The main aim of the present study was to investigate whether catalpol ameliorates experimental acute pancreatitis (AP) induced by sodium taurocholate (STC). AP was induced in rats via retrograde injection of 4% STC (0.1 mL/100 g) into the biliopancreatic duct. Rats were pre-treated with saline or catalpol (50 mg/kg) 2 h before STC injection. At 12, 24 and 48 h after injection, the severity of AP was evaluated using biochemical and morphological analyses. Pretreatment with catalpol led to a significant reduction in serum amylase and lipase activities, pancreatic histological damage, myeloperoxidase (MPO) activity, interleukin (IL)-1?, IL-6 and TNF-? levels, and activation of nuclear factor kappa B (NF-?B). Moreover, administration of catalpol increased the viability of pancreatic acinar cells and inhibited NF-?B expression in vitro. Our results collectively support the potential of catalpol as a highly effective therapeutic agent for treatment of AP. PMID:25000266

Xiao, Wen Qin; Yin, Guo Jian; Fan, Yu Ting; Qiu, Lei; Cang, Xiao Feng; Yu, Ge; Hu, Yan Ling; Xing, Miao; Wu, De Qing; Wang, Xing Peng; Hu, Guo Yong; Wan, Rong

2014-01-01

347

Specioside ameliorates oxidative stress and promotes longevity in Caenorhabditis elegans.  

PubMed

Specioside (6-O-coumaroylcatalpol) is an iridoid glucoside which possesses multifunctional activities viz. analgesic, antidyspeptic, astringent, liver stimulating and wound healing properties. The present study for the first time delineates stress alleviating and lifespan prolonging action of specioside (SPC), isolated from Stereospermum suaveolens in the free living, multicellular nematode model Caenorhabditis elegans. A strong correlation between lifespan extension and stress modulation in adult worms was established in a dose dependent manner. The dietary intake of this phytomolecule elevated juglone induced oxidative and heat induced thermal stress tolerance in C. elegans. On evaluation, it was found that 25?M dose of SPC significantly extended lifespan by 15.47% (P?0.0001) with reduction in stress level. Furthermore, SPC enhanced mean survival in mev-1 mutant suggesting its oxidative stress reducing potential. Furthermore, SPC augmented stress modulatory enzymes superoxide dismutase (SOD) and catalase (CAT) level in C. elegans. Altogether, these findings broaden current perspectives concerning stress alleviating potentials of SPC and have implications in development of therapeutics for curing age related disorders. PMID:25619942

Asthana, Jyotsna; Yadav, A K; Pant, Aakanksha; Pandey, Swapnil; Gupta, M M; Pandey, Rakesh

2015-03-01

348

Mining for treatment-specific and general changes in target compounds and metabolic fingerprints in response to herbivory and phytohormones in Plantago lanceolata.  

PubMed

Induction studies focusing on target metabolites may not reveal metabolic changes occurring in plants after various challenges. By contrast, metabolic fingerprinting can be a powerful tool to find patterns that are either treatment-specific or general and was therefore used to depict plant responses after various challenges. Plants of Plantago lanceolata were challenged by mechanical damage, specialist herbivores (aphids or sawfly larvae), generalist herbivores (Lepidopteran caterpillars) or phytohormones (jasmonic or salicylic acid). After 3 d of treatment, local and systemic leaves were analyzed for characteristic target metabolites (iridoid glucosides and verbascoside) by gas chromatography coupled with mass spectrometry (GC-MS) and for metabolic fingerprints by liquid chromatography coupled with time of flight mass spectrometry (LC-TOF-MS). Whereas only marginal changes in target metabolite concentrations were found, metabolic fingerprints were substantially affected especially by generalist and phytohormone treatments. By contrast, mechanical damage and specialist herbivory caused fewer changes. Responses to generalists partly overlapped with the changes caused by jasmonic acid, but many additional peaks were up-regulated. Furthermore, many peaks were co-induced by jasmonic and salicylic acid. The surprisingly high co-induction of peaks by both phytohormones suggests that the signaling pathways regulate a set of common targets. Furthermore, only metabolic fingerprinting could reveal that herbivores induce additional species-specific pathways beyond these phytohormone responses. PMID:21592133

Sutter, Rabea; Müller, Caroline

2011-09-01

349

Catalpol Ameliorates Sodium Taurocholate-Induced Acute Pancreatitis in Rats via Inhibiting Activation of Nuclear Factor Kappa B  

PubMed Central

Catalpol, an iridoid glucoside extracted from the traditional Chinese herbal medicine, Rehmannia glutinosa, is reported to exert neuroprotective, anti-inflammatory, anti-tumor and anti-apoptotic effects. The main aim of the present study was to investigate whether catalpol ameliorates experimental acute pancreatitis (AP) induced by sodium taurocholate (STC). AP was induced in rats via retrograde injection of 4% STC (0.1 mL/100 g) into the biliopancreatic duct. Rats were pre-treated with saline or catalpol (50 mg/kg) 2 h before STC injection. At 12, 24 and 48 h after injection, the severity of AP was evaluated using biochemical and morphological analyses. Pretreatment with catalpol led to a significant reduction in serum amylase and lipase activities, pancreatic histological damage, myeloperoxidase (MPO) activity, interleukin (IL)-1?, IL-6 and TNF-? levels, and activation of nuclear factor kappa B (NF-?B). Moreover, administration of catalpol increased the viability of pancreatic acinar cells and inhibited NF-?B expression in vitro. Our results collectively support the potential of catalpol as a highly effective therapeutic agent for treatment of AP. PMID:25000266

Xiao, Wen Qin; Yin, Guo Jian; Fan, Yu Ting; Qiu, Lei; Cang, Xiao Feng; Yu, Ge; Hu, Yan Ling; Xing, Miao; Wu, De Qing; Wang, Xing Peng; Hu, Guo Yong; Wan, Rong

2014-01-01

350

Antidiabetic compounds from Sarracenia purpurea used traditionally by the Eeyou Istchee Cree First Nation.  

PubMed

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

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

351

Nano-liquid chromatography coupled to time-of-flight mass spectrometry for phenolic profiling: A case study in cranberry syrups.  

PubMed

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<5ppm) 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 1.0-15.6ngmL(-1) and 2.0-62.5ngmL(-1), respectively. The method can be extended to characterize phenolic compounds in other food and plant matrices, and as well biological samples. PMID:25476399

Contreras, María Del Mar; Arráez-Román, David; Fernández-Gutiérrez, Alberto; Segura-Carretero, Antonio

2015-01-15

352

Hydrolysis of Oleuropein by Lactobacillus plantarum Strains Associated with Olive Fermentation  

PubMed Central

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

Ciafardini, G.; Marsilio, V.; Lanza, B.; Pozzi, N.

1994-01-01

353

Developing transgenic wheat and barley that exhibit resistance to Fusarium graminearum via glucoside conjugation of trichothecene mycotoxins  

Technology Transfer Automated Retrieval System (TEKTRAN)

Fusarium graminearum infection of wheat and barley results in production of trichothecene mycotoxins including deoxynivalenol (DON) and nivalenol (NIV). These mycotoxins result in increased fungal virulence and reduce grain quality. Numerous transcriptomic studies have been conducted by our lab on t...

354

[Studies on the structure of a new flavanonol glucoside of the root-sprouts of Agrimonia pilosa Ledeb].  

PubMed

Three compounds were isolated from benzene and acetone extracts of the root-sprouts of Agrimonia pilosa Ledeb. On the basis of physicochemical properties, spectroscopy (UV, IR, NMR, MS, CD, GC) and chemical degradation, two known compounds were identified as palmitic acid (VIII) and daucosterol (IX), one new compound was elucidated as (2S,3S)-(-)-taxifolin-3-O-beta-D-glucopyranoside (X). PMID:2281787

Pei, Y H; Li, X; Zhu, T R; Wu, L J

1990-01-01

355

New dammarane-type glucosides as potential activators of AMP-activated protein kinase (AMPK) from Gynostemma pentaphyllum.  

PubMed

AMP-activated protein kinase (AMPK) is a key sensor and regulator of glucose, lipid, and energy metabolism throughout the body. Activation of AMPK improves metabolic abnormalities associated with metabolic diseases including obesity and type-2 diabetes. The oriental traditional medicinal herbal plant, Gynostemma pentaphyllum, has shown a wide range of beneficial effects on glucose and lipid metabolism. In this study, we found that G. pentaphyllum contains two novel dammarane-type saponins designated as damulin A (1), 2?,3?,12?-trihydroxydammar-20(22)-E,24-diene-3-O-[?-D-glucopyranosyl-(1?2)-?-D-glucopyranoside], and damulin B (2), 2?,3?,12?-trihydroxydammar-20,24-diene-3-O-[?-D-glucopyranosyl-(1?2)-?-D-glucopyranoside], that strongly activate AMPK in cultured L6 myotube cells. Damulins A and B also increased ?-oxidation and glucose uptake with increasing GluT4 translocation to the plasma membrane in L6 myotube cells. Taken together our results indicate that activation of AMPK by damulins A and B may contribute to beneficial effect of G. pentaphyllum on glucose and lipid metabolism. PMID:21978948

Nguyen, Phi Hung; Gauhar, Rehman; Hwang, Seung Lark; Dao, Trong Tuan; Park, Dong Chan; Kim, Ji Eun; Song, Hebok; Huh, Tae Lin; Oh, Won Keun

2011-11-01

356

Transglucosylation of ascorbic acid to ascorbic acid 2-glucoside by a recombinant sucrose phosphorylase from Bifidobacterium longum  

Microsoft Academic Search

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-?-d-glucopyranosyl-l-ascorbic acid by LC-MS\\/MS analysis.

Taeyeon Kwon; Cheong Tae Kim; Jong-Hoon Lee

2007-01-01

357

An on-line method for pressurized hot water extraction and enzymatic hydrolysis of quercetin glucosides from onions.  

PubMed

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

Lindahl, Sofia; Liu, Jiayin; Khan, Samiullah; Karlsson, Eva Nordberg; Turner, Charlotta

2013-06-27

358

Atomistic simulation studies of the ?/?-glucoside and galactoside in anhydrous bilayers: effect of the anomeric and epimeric configurations.  

PubMed

Fully atomistic molecular dynamics simulation studies of thermotropic bilayers were performed using a set of glycosides namely n-octyl-?-D-glucopyranoside (?-C8Glc), n-octyl-?-D-glucopyranoside (?-C8Glc), n-octyl-?-D-galactopyranoside (?-C8Gal), and n-octyl-?-D-galactopyranoside (?-C8Gal) to investigate the stereochemical relationship of the epimeric/anomeric quartet liner glycolipids with the same octyl chain group. The results showed that, the anomeric stereochemistry or the axial/equatorial orientation of C1-O1 (?/?) is an important factor controlling the area and d-spacing of glycolipid bilayer systems in the thermotropic phase. The head group tilt angle and the chain ordering properties are affected by the anomeric effect. In addition, the L(C) phase of ?-C8Gal, is tilting less compared to those in the fluid L(?). The stereochemistry of the C4-epimeric (axial/equatorial) and anomeric (?/?) centers simultaneously influence the inter-molecular hydrogen bond. Thus, the trend in the values of the hydrogen bond for these glycosides is ?-C8Gal?>??-C8Glc?>??-C8Glc?>??-C8Gal. The four bilayer systems showed anomalous diffusion behavior with an observed trend for the diffusion coefficients; and this trend is ?-C8Gal?>??-C8Glc?>??-C8Gal?>??-C8Glc. The "bent" configuration of the ?-anomer results in an increase of the hydrophobic area, chain vibration and chain disorganization. Since thermal energy is dispensed more entropically for the chain region, the overall molecular diffusion decreases. PMID:24623320

Ahmadi, Sara; Manickam Achari, Vijayan; Nguan, Hockseng; Hashim, Rauzah

2014-03-01

359

Regulators of cell division in plant tissues. XXX. Cytokinin metabolism in relation to radish cotyledon expansion and senescence  

Microsoft Academic Search

Kinetic studies of formation of glucosides of 6-benzylaminopurine (BAP) in excised radish cotyledons indicated that the 3-,\\u000a 7-, and 9-glucosides (N-glucosides) were each formed directly from BAP. The 7- and 9-glucosides of BAP and the 7-glucoside\\u000a of zeatin exhibited great stability in the cotyledons, but the 3-glucoside was converted to free BAP and to the 7- and 9-glucosides\\u000a of BAP.

D. S. Letham; B. I. Gollnow

1985-01-01

360

Fractionation of phenolic compounds from a purple corn extract and evaluation of antioxidant and antimutagenic activities  

E-print Network

Qualitative and quantitative analysis of anthocyanins and other phenolic compounds from a purple corn extract was performed. The purple corn extract had cyanidin-3-glucoside, pelargonidin-3-glucoside, peonidin-3-glucoside and its respective acylated...

Pedreschi, Romina Paola

2005-08-29

361

Deglycosylation of flavonoid and isoflavonoid glycosides by human small intestine and liver ?-glucosidase activity  

Microsoft Academic Search

Flavonoid and isoflavonoid glycosides are common dietary phenolics which may be absorbed from the small intestine of humans. The ability of cell-free extracts from human small intestine and liver to deglycosylate various (iso)flavonoid glycosides was investigated. Quercetin 4?-glucoside, naringenin 7-glucoside, apigenin 7-glucoside, genistein 7-glucoside and daidzein 7-glucoside were rapidly deglycosylated by both tissue extracts, whereas quercetin 3,4?-diglucoside, quercetin 3-glucoside, kaempferol

Andrea J Day; M. Susan DuPont; Saxon Ridley; Mike Rhodes; Michael J. C Rhodes; Michael R. A Morgan; Gary Williamson

1998-01-01

362

Journal of Chemical Ecology, Vol. 31, No. 2, February 2005 (C 2005) DOI: 10.1007/s10886-005-1341-1  

E-print Network

-005-1341-1 EFFECTS OF QUANTITATIVE VARIATION IN ALLELOCHEMICALS IN Plantago lanceolata ON DEVELOPMENT OF A GENERALIST quantitative variation in allelochemicals (iridoid glycosides) in ribwort plantain, Plantago lanceolata--Chemical defense, iridoid glycosides, Melitaea cinxia, multi- trophic interactions, Plantago lanceolata, Spodoptera

Helsinki, University of

363

Fusicoccin A, a Phytotoxic Carbotricyclic Diterpene Glucoside of Fungal Origin, Reduces Proliferation and Invasion of Glioblastoma Cells by Targeting Multiple Tyrosine Kinases1  

PubMed Central

Glioblastoma multiforme (GBM) is a deadly cancer that possesses an intrinsic resistance to pro-apoptotic insults, such as conventional chemotherapy and radiotherapy, and diffusely invades the brain parenchyma, which renders it elusive to total surgical resection. We found that fusicoccin A, a fungal metabolite from Fusicoccum amygdali, decreased the proliferation and migration of human GBM cell lines in vitro, including several cell lines that exhibit varying degrees of resistance to pro-apoptotic stimuli. The data demonstrate that fusicoccin A inhibits GBM cell proliferation by decreasing growth rates and increasing the duration of cell division and also decreases two-dimensional (measured by quantitative video microscopy) and three-dimensional (measured by Boyden chamber assays) migration. These effects of fusicoccin A treatment translated into structural changes in actin cytoskeletal organization and a loss of GBM cell adhesion. Therefore, fusicoccin A exerts cytostatic effects but low cytotoxic effects (as demonstrated by flow cytometry). These cytostatic effects can partly be explained by the fact that fusicoccin inhibits the activities of a dozen kinases, including focal adhesion kinase (FAK), that have been implicated in cell proliferation and migration. Overexpression of FAK, a nonreceptor protein tyrosine kinase, directly correlates with the invasive phenotype of aggressive human gliomas because FAK promotes cell proliferation and migration. Fusicoccin A led to the down-regulation of FAK tyrosine phosphorylation, which occurred in both normoxic and hypoxic GBM cell culture conditions. In conclusion, the current study identifies a novel compound that could be used as a chemical template for generating cytostatic compounds designed to combat GBM. PMID:23544164

Bury, Marina; Andolfi, Anna; Rogister, Bernard; Cimmino, Alessio; Mégalizzi, Véronique; Mathieu, Véronique; Feron, Olivier; Evidente, Antonio; Kiss, Robert

2013-01-01

364

Observation of T-2 and HT-2 glucosides from Fusarium sporotrichioides by liquid chromatography coupled to tandem mass spectrometry (LC-MS/MS)  

Technology Transfer Automated Retrieval System (TEKTRAN)

Cultures of Fusarium sporotrichioides were extracted and subjected to evaluation by high performance liquid chromatography – tandem mass spectrometry (LC-MS/MS). Along with the expected T-2 and HT-2 toxins, compounds 162 m/z higher than the toxins were observed. Fragmentation behavior of the larger ...

365

Quantitation of multiple mycotoxins and cyanogenic glucosides in cassava samples from Tanzania and Rwanda by an LC-MS/MS-based multi-toxin method.  

PubMed

A multi-mycotoxin method based on liquid chromatography/tandem mass spectrometry (LC-MS/MS) was used for a mycotoxin survey in 627 samples of processed cassava collected from different districts across Tanzania and Rwanda after the method performance for this matrix had been determined. Matrix effects as well as extraction efficiencies were found to be similar to most other previously investigated matrices with the exception of distinct matrix effects in the negative ionisation mode for early eluting compounds. Limits of detection were far below the regulatory limits set in the European Union for other types of commodities. Relative standard deviations were generally lower than 10% as determined by replicates spiked on two concentration levels. The sample-to-sample variation of the apparent recoveries was determined for 15 individually spiked samples during three different analytical sequences. The related standard deviation was found to be lower than 15% for most of the investigated compounds, thus confirming the applicability of the method for quantitative analysis. The occurrence of regulated mycotoxins was lower than 10% (with the exception of zearalenone) and the related limits were exceeded only in few samples, which suggests that cassava is a comparatively safe commodity as regards mycotoxins. The most prevalent fungal metabolites were emodin, kojic acid, beauvericin, tryptophol, 3-nitropropionic acid, equisetin, alternariol methylether, monocerin, brevianamide F, tenuazonic acid, zearalenone, chrysophanol, monilifomin, enniatins, apicidin and macrosporin. The related concentrations exceeded 1 mg kg(-1) only in few cases. However, extremely high levels of cyanogenic plant toxins, which had been previously added to the method, were observed in few samples, pointing out the need for improved post-harvest management to decrease the levels of these compounds. PMID:25350522

Sulyok, M; Beed, F; Boni, S; Abass, A; Mukunzi, A; Krska, R

2014-11-14

366

Natural variation in maize aphid resistance is associated with 2,4-Dihydroxy-7-Methoxy-1,4-Benzoxazin-3-One Glucoside Methyltransferase activity  

Technology Transfer Automated Retrieval System (TEKTRAN)

Plants differ greatly in their susceptibility to insect herbivory, suggesting both local adaptation and resistance tradeoffs. We used maize (Zea mays) recombinant inbred lines to map a quantitative trait locus (QTL) for the maize leaf aphid (Rhopalosiphum maidis) susceptibility to maize Chromosome 1...

367

The maltodextrin transport system and metabolism in Lactobacillus acidophilus NCFM and production of novel alpha-glucosides through reverse phosphorolysis by maltose phosphorylase.  

PubMed

A gene cluster involved in maltodextrin transport and metabolism was identified in the genome of Lactobacillus acidophilus NCFM, which encoded a maltodextrin-binding protein, three maltodextrin ATP-binding cassette transporters and five glycosidases, all under the control of a transcriptional regulator of the LacI-GalR family. Enzymatic properties are described for recombinant maltose phosphorylase (MalP) of glycoside hydrolase family 65 (GH65), which is encoded by malP (GenBank: AAV43670.1) of this gene cluster and produced in Escherichia coli. MalP catalyses phosphorolysis of maltose with inversion of the anomeric configuration releasing beta-glucose 1-phosphate (beta-Glc 1-P) and glucose. The broad specificity of the aglycone binding site was demonstrated by products formed in reverse phosphorolysis using various carbohydrate acceptor substrates and beta-Glc 1-P as the donor. MalP showed strong preference for monosaccharide acceptors with equatorial 3-OH and 4-OH, such as glucose and mannose, and also reacted with 2-deoxy glucosamine and 2-deoxy N-acetyl glucosamine. By contrast, none of the tested di- and trisaccharides served as acceptors. Disaccharide yields obtained from 50 mmbeta-Glc 1-P and 50 mm glucose, glucosamine, N-acetyl glucosamine, mannose, xylose or l-fucose were 99, 80, 53, 93, 81 and 13%, respectively. Product structures were determined by NMR and ESI-MS to be alpha-Glcp-(1-->4)-Glcp (maltose), alpha-Glcp-(1-->4)-GlcNp (maltosamine), alpha-Glcp-(1-->4)-GlcNAcp (N-acetyl maltosamine), alpha-Glcp-(1-->4)-Manp, alpha-Glcp-(1-->4)-Xylp and alpha-Glcp-(1-->4)- L-Fucp, the three latter being novel compounds. Modelling using L. brevis GH65 as the template and superimposition of acarbose from a complex with Thermoanaerobacterium thermosaccharolyticum GH15 glucoamylase suggested that loop 3 of MalP involved in substrate recognition blocked the binding of candidate acceptors larger than monosaccharides. PMID:19919544

Nakai, Hiroyuki; Baumann, Martin J; Petersen, Bent O; Westphal, Yvonne; Schols, Henk; Dilokpimol, Adiphol; Hachem, Maher A; Lahtinen, Sampo J; Duus, Jens Ø; Svensson, Birte

2009-12-01

368

BglF, the Escherichia coli b-Glucoside Permease and Sensor of the bgl System: Domain Requirements of the Different Catalytic Activities  

Microsoft Academic Search

phosphorylates them. BglF is composed of two hydrophilic domains, IIA bgl and IIB bgl , and a membrane-bound domain, IIC bgl , which are covalently linked in the order IIBCA bgl . Cys-24 in the IIB bgl domain is essential for all the phosphorylation and dephosphorylation activities of BglF. We have investigated the domain require- ment of the different functions

QING CHEN; ORNA AMSTER-CHODER

1999-01-01

369

Promotion of IL-4- and IL-5-dependent differentiation of anti-mu-primed B cells by ascorbic acid 2-glucoside.  

PubMed

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

Ichiyama, Kenji; Mitsuzumi, Hitoshi; Zhong, Ming; Tai, Akihiro; Tsuchioka, Akihiro; Kawai, Saeko; Yamamoto, Itaru; Gohda, Eiichi

2009-02-21

370

The Safety and Pharmacokinetics of Cyanidin-3-Glucoside after 2-Week Administration of Black Bean Seed Coat Extract in Healthy Subjects  

PubMed Central

We analyzed the pharmacokinetics of C3G on data from twelve subjects, after 2-week multiple dosing of black bean (Phaseolus vulgaris, Cheongjakong-3-ho) seed coat extract, using the mixed effect analysis method (NONMEM, Ver. 6.2), as well as the conventional non-compartmental method. We also examined the safety and tolerability. The PK analysis used plasma concentrations of the C3G on day 1 and 14. There was no observed accumulation of C3G after 2-week multiple dosing of black bean seed coat extract. The typical point estimates of PK were CL (clearance)=3,420 l/h, V (volume)=7,280 L, Ka (absorption constant)=9.94 h-1, ALAG (lag time)=0.217 h. The black bean seed coat extract was well tolerated and there were no serious adverse events. In this study, we confirmed that a significant amount of C3G was absorbed in human after given the black bean seed coat extract. PMID:22915990

Jeon, Sangil; Han, Seunghoon; Lee, Jongtae; Hong, Taegon

2012-01-01

371

Cloning and Expression of Cytochrome P450 Enzymes Catalyzing the Conversion of Tyrosine to p-Hydroxyphenylacetaldoxime in the Biosynthesis of Cyanogenic Glucosides in Triglochin maritima  

Microsoft Academic Search

Two cDNA clones encoding cytochrome P450 enzymes belong- ing to the CYP79 family have been isolated from Triglochin mari- tima. The two proteins show 94% sequence identity and have been designated CYP79E1 and CYP79E2. Heterologous expression of the native and the truncated forms of the two clones in Escherichia coli demonstrated that both encode multifunctional N-hydroxylases cat- alyzing the conversion

John Strikart Nielsen; Birger Lindberg Møller

2000-01-01

372

Accumulation of brachycerine, an antioxidant glucosidic indole alkaloid, is induced by abscisic acid, heavy metal, and osmotic stress in leaves of Psychotria brachyceras.  

PubMed

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

do Nascimento, Naíla Cannes; Menguer, Paloma Koprovski; Henriques, Amélia Teresinha; Fett-Neto, Arthur Germano

2013-12-01

373

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

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

Vila-Real, Hélder; Alfaia, António J.; Bronze, M. Rosário; Calado, António R. T.; Ribeiro, Maria H. L.

2011-01-01

374

4'-Demethyl-deoxypodophyllotoxin glucoside isolated from Podophyllum hexandrum exhibits potential anticancer activities by altering Chk-2 signaling pathway in MCF-7 breast cancer cells.  

PubMed

We investigated the root of Podophyllum hexandrum as a potential source of lead bioactive metabolites with anticancer activity. The present study led to the isolation of six known aryltetralin-type lignans designated as 4'-demethyl-deoxypodophyllotoxin (1), podophyllotoxin (2), 4'-demethyl-podophyllotoxin (3), podophyllotoxin-4-O-?-d-glucopyranoside (4), 4'-demethyl-deoxypodophyllotoxin-4-O-?-d-glucopyranoside (5), 4'-demethyl-podophyllotoxin-4-O-?-d-glucopyranoside (6), along with three known flavones Kaempferol (7), Quercetin (8), Astragalin (9) from the root of P. hexandrum. Compounds (1-9) exhibited the remarkable cytotoxic potential in diverse cancer cell lines. 5 therapeutic potential was extensively studied first time which exhibiting antiproliferative and ROS generating activity than its non-glycoside analogue 1. Furthermore, 5 augmented the apoptotic cascades in MCF-7 breast cancer cells, viz. nuclear condensation, membrane blebbing, probably by destabilizing the micro-tubular protein tubulin. Strikingly, our docking study and in vitro assays demonstrate that 5 binds to and modulate checkpoint kinase-2, a key cell cycle regulatory protein in normal and cancer cells. PMID:25446499

Zilla, Mahesh K; Nayak, Debasis; Amin, Hina; Nalli, Yedukondalu; Rah, Bilal; Chakraborty, Souneek; Kitchlu, Surender; Goswami, Anindya; Ali, Asif

2014-10-18

375

Identification of isoflavone conjugates in red clover ( Trifolium pratense) by liquid chromatography–mass spectrometry after two-dimensional solid-phase extraction  

Microsoft Academic Search

A high-performance liquid chromatography–mass spectrometry (LC–MS) combined with a two-dimensional solid-phase extraction (2D-SPE) enabled the identification of fourteen isoflavone glycoside malonates (daidzin-6?-O-malonate, genistin-6?-O-malonate, orobol-7-O-?-d-glucoside-6?-O-malonate, 3-methylorobol-7-O-?-d-glucoside-6?-O-malonate, calycosin-7-O-?-d-glucoside-6?-O-malonate, pratensein-7-O-?-d-glucoside-6?-O-malonate, pseudobaptigenin-7-O-?-d-glucoside-6?-O-malonate, formononetin-7-O-?-d-glucoside-6?-O-malonate, irilone-4?-O-?-d-glucoside-6?-O-malonate, afrormosin-7-O-?-d-glucoside-6?-O-malonate, biochanin A-7-O-?-d-glucoside-6?-O-malonate, texasin-7-O-?-d-glucoside-6?-O-malonate, 5,7,2?-trihydroxy-6-methoxyisoflavone-7-O-?-d-glucoside-6?-O-malonate, prunetin-4?-O-?-d-glucoside-6?-O-malonate) and six acetyl glycosides (daidzin-6?-O-acetate, formononetin-7-O-?-d-glucoside-6?-O-acetate, pseudobaptigenin-7-O-?-d-glucoside-6?-O-acetate, irilone-4?-O-?-d-glucoside-6?-O-acetate, biochanin A-7-O-?-d-glucoside-6?-O-acetate and prunetin-4?-O-?-d-glucoside-6?-O-acetate) isolated from red clover (Trifolium pratense). Eight isoflavone glycoside malonates and six

Bo?ivoj Klejdus; Dagmar Vitamvásová-Št?rbová; Vlastimil Kubá?

2001-01-01

376

5- O-glucosyldihydroflavones from the leaves of Helicia cochinchinensis  

Microsoft Academic Search

From the leaves of Helicia cochinchinensis, collected on Okinawa Island, seven phenolic glucosides and two terpenic glucosides were isolated. Five of the phenolic glucosides were previously known, being identified with p-coumaric and ferulic acids glucosyl esters, rhodioloside, helicidiol, and naringenin 5-O-?-d-glucopyranoside. The structures of two other phenolic glucosides, named heliciosides A and B, were elucidated to be 5-O-?-d-glucosides of 3-hydroxyflavanone,

Ken-Ichi Morimura; Asuka Gatayama; Reiki Tsukimata; Katsuyoshi Matsunami; Hideaki Otsuka; Eiji Hirata; Takakazu Shinzato; Mitsunori Aramoto; Yoshio Takeda

2006-01-01

377

A 7-Deoxyloganetic Acid Glucosyltransferase Contributes a Key Step in Secologanin Biosynthesis in Madagascar Periwinkle[C][W][OPEN  

PubMed Central

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

Asada, Keisuke; Salim, Vonny; Masada-Atsumi, Sayaka; Edmunds, Elizabeth; Nagatoshi, Mai; Terasaka, Kazuyoshi; Mizukami, Hajime; De Luca, Vincenzo

2013-01-01

378

[Dihydropenstemide from Penstemon confertus and the Preparation of epi-Dihydropenstemide from Penstemide.].  

PubMed

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

Gering, B; Junior, P; Wichtl, M

1986-10-01

379

Leaf chemistry and foliage avoidance by the thrips Frankliniella occidentalis and Heliothrips haemorrhoidalis in glasshouse collections.  

PubMed

Observational studies on foliage avoidance by the polyphagous thrips species Frankliniella occidentalis (Pergande) and Heliothrips haemorrhoidalis (Bouché) (Thysanoptera: Thripidae) identified six non-host species (Allagopappus dichotomus (Asteraceae), Gardenia posoquerioides (Rubiaceae), Plectranthus aff. barbatus, Plectranthus strigosus, Plectranthus zuluensis (Lamiaceae), and Sclerochiton harveyanus (Acanthaceae) among plants growing within a major glasshouse botanical collection. The effects of sequentially obtained acetone and aqueous methanol leaf extracts on mortality in first instar Frankliniella occidentalis were assessed. The acetone leaf extract of Sclerochiton harveyanus, which had the highest activity against the thrips, yielded four new iridoids, sclerochitonosides A-C, and sclerochitonoside B 4'-methyl ether. Mortality of F. occidentalis was increased on exposure to all four iridoids, and the most active iridoid was sclerochitonoside A (8-epiloganic acid 4'-hydroxyphenylethyl ester). Choice experiments demonstrated that this compound did not significantly deter H. haemorrhoidalis from treated leaf surfaces. The significance of iridoids in the defense mechanism of plants against thrips is discussed. PMID:21331569

Brown, Alison S Scott; Veitch, Nigel C; Simmonds, Monique S J

2011-03-01

380

Flavonoids of Helichrysum compactum and their antioxidant and antibacterial activity  

Microsoft Academic Search

From the capitula of Helichrysum compactum, the flavonoids apigenin, kaempferol, luteolin, naringenin, 3,5-dihydroxy-6,7,8-trimethoxyflavone, kaempferol-3-O-glucoside, luteolin-7-O-glucoside and luteolin-4?,7-di-O-glucoside and from the leafy stems apigenin, kaempferol, luteolin, quercetin, apigenin-7-O-glucoside, luteolin-7-O-glucoside, and quercetin-3-O-glucoside were isolated. Extracts of the capitula of H. compactum show antioxidant activity by inhibition of lipid peroxidation and also show antibacterial activity.

Sevda Süzgeç; Ali H. Meriçli; Peter J. Houghton; Bayhan Çubukçu

2005-01-01

381

Chemical variation within and between individuals of Plantago lanceolata (Plantaginaceae)  

Microsoft Academic Search

Variation in concentrations of leaf nitrogen and iridoid glycosides was examined in replicate plants of five genotypes ofPlantago lanceolata (Plantaginaceae) grown in an experimental garden. Nitrogen concentration and iridoid glycoside concentration were affected by leaf age. New leaves had nitrogen concentrations 1.7 to 2.7 times higher than mature leaves. Catalpol concentration was highest in new and intermediate-aged leaves. The concentration

M. Deane Bowers; Nancy E. Stamp

1992-01-01

382

Synthesis of glycosides of resveratrol, pterostilbene, and piceatannol, and their anti-oxidant, anti-allergic, and neuroprotective activities.  

PubMed

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

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

383

Flavonoids from Algerian endemic Centaurea microcarpa and their chemotaxonomical significance.  

PubMed

Six flavonoids, namely 6-methoxykaempferol (1), 6-methoxykaempferol 7-O-glucoside (2), kaempferol 7-O-glucoside (3), 6-methoxyluteolin (4), patuletin 7-O-glucoside (5), and hispidulin 7-O-glucoside (6), were isolated from a n-butanolic fraction of Centaurea microcarpa Coss et Dur. flowers. This work describes for the first time the phytochemical composition of this endemic Algerian plant. PMID:22224272

Louaar, Souheila; Achouri, Amel; Lefahal, Mostefa; Laouer, Hocine; Medjroubi, Kamel; Duddeck, Helmut; Akkal, Salah

2011-11-01

384

Anthocyanin synthesis in a white flowering mutant of Petunia hybrida  

Microsoft Academic Search

In flower buds of the white flowering mutant W19 of Petunia hybrida four biologically active dihydroflavonol intermediates-dihydroquercetin-7-glucoside, dihydroquercetin-4'-glucoside, dihydroquercetin, and dihydrokaempferol-7-glucoside-are accumulated. When dihydroquercetin was supplied to in vitro cultured corollas of the white flowering mutant W18, a mixture of cyanidin and delphinidin glycosides was produced, cyanidin-3-glucoside being the major pigment. The quantity of dihydroquercetin accumulated in W19 is very

K. F. F. Kho; A. C. Bolsman-Louwen; J. C. Vuik; G. J. H. Bennink

1977-01-01

385

Furanoflavonoid glycosides from Pongamia pinnata fruits.  

PubMed

Pongamia pinnata fruits afforded three new furanoflavonoid glucosides, pongamosides A-C (1-3), and a new flavonol glucoside, pongamoside D (4). The structures of these compounds were established on the basis of spectroscopic studies. This is the first time that furanoflavone glucosides have been found as naturally occurring compounds. PMID:15081295

Ahmad, Ghufran; Yadav, Prem P; Maurya, Rakesh

2004-04-01

386

Flavone glycosides from Mentha longifolia  

Microsoft Academic Search

In addition to isoorientin, vicenin-2, hypolaetin, lucenin-1, luteolin 7-O-glucoside and 7-O-neohesperidoside, the aerial parts of Mentha longifolia yielded three new flavonoids, identified as tricetin 7-O-methylether 3?-O glucoside 5?-O-rhamnoside (1), tricetin 3?-O glucoside 5?-O-rhamnoside (2) and tricetin 3?-O-rhamnosyl-(1?4)-rhamnoside (3).

M. Sharaf; M. A. El-Ansari; N. A. M. Saleh

1999-01-01

387

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.)  

Microsoft Academic Search

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\\u000a formation. The multiple

S. Masuzaki; M. Shigyo; N. Yamauchi

2006-01-01

388

The anthocyanin cyanidin-3-O-?-glucoside, a flavonoid, increases hepatic glutathione synthesis and protects hepatocytes against reactive oxygen species during hyperglycemia: Involvement of a cAMP-PKA-dependent signaling pathway.  

PubMed

Enhanced oxidative stress due to high glucose contributes to pathological changes in diabetes-related liver complications. Reducing oxidative stress may alleviate these pathogenic processes. Anthocyanin, a natural antioxidant, has been reported to reduce intracellular reactive oxygen species (ROS) levels but the mechanism of this reduction is not fully understood. The glutathione (GSH) antioxidant system is critical for counteracting oxidative stress-induced intracellular injury. In this study, we evaluated the mechanism of the anthocyanin-mediated regulation of GSH synthesis and reduction in intracellular ROS levels. We observed that treatment of human HepG2 cells with the anthocyanin C3G significantly reduced ROS levels induced by high glucose. C3G incubation increased glutamate-cysteine ligase expression, which in turn mediated the reduction in ROS levels. However, the upregulation of glutamate-cysteine ligase catalytic subunit (Gclc) expression by C3G occurred independent of the Nrf1/2 transcription factors. Notably, the cAMP-response element binding protein (CREB) was identified as the target transcription factor involved in the C3G-mediated upregulation of Gclc expression. C3G increased phosphorylation of CREB through protein kinase A (PKA) activation, which induced a CREB-mediated upregulation of Gclc transcription. In vivo, treatment with C3G increased the GSH synthesis in the liver of diabetic db/db mice through PKA-CREB-dependent induction of Gclc expression. Finally, oxidative stress determined by lipid peroxidation, neutrophil infiltration, and hepatic steatosis was attenuated in C3G-treated db/db mice. Our results demonstrate that the anthocyanin C3G has an effect of activating GSH synthesis through a novel antioxidant defense mechanism against excessive ROS production, contributing to the prevention of hyperglycemia-induced hepatic oxidative damage. PMID:22085656

Zhu, Wei; Jia, Qianju; Wang, Yun; Zhang, Yuhua; Xia, Min

2012-01-15

389

Flavonoids from the Japanese monotypic genus, Nipponanthemum.  

PubMed

Foliar flavonoids of Nipponanthemum, which is a monotypic genus and consists of only one Japanese endemic species, N. nipponicum, were isolated for the first time. Fifteen flavonoids, i.e. six glycosides, quercetin 3,7-di-O-glucoside, vicenin-2, quercetin 3-O-glucoside, luteolin 7-O-glucoside, kaempferol 3-O-glucoside and apigenin 7-O-glucoside, and nine aglycones, luteolin, nepetin, quercetin 3-methyl ether, axillarin, apigenin, hispidulin, chrysoeriol, jaceosidin and sudachitin were identified. Of these compounds, the flavonoid aglycones existed on the leaf surface. PMID:22978216

Uehara, Ayumi; Iwashina, Tsukasa

2012-08-01

390

Glycosides from the aerial parts of Patrinia villosa.  

PubMed

An investigation of the Korean medicinal plant Patrinia villosa (THUNB.) JUSS. (Valerianaceae) led to the isolation of two new flavonoid glycosides, patrivilosides 1 (1) and 2 (2), a new iridoid glycoside, patrinovalerosidate (3), and two new saponins, patrinovilosides A (4) and B (5), along with six known compounds including three flavonoid glycosides and three iridoid glycosides. The structures of the new compounds were elucidated based on analysis of their one dimensional (1D)- and 2D-NMR spectra along with their mass spectrometric data and the results of acid hydrolysis. PMID:23800854

Lee, Joo Young; Kim, Ju Sun; Kim, Yeong Shik; Kang, Sam Sik

2013-01-01

391

Phenolics of Moringa oleifera leaves.  

PubMed

Five flavonol glycosides characterised as kaempferide 3-O-(2'',3''-diacetylglucoside), kaempferide 3-O-(2''-O-galloylrhamnoside), kaempferide 3-O-(2''-O-galloylrutinoside)-7-O-alpha-rhamnoside, kaempferol 3-O-[beta-glucosyl-(1 --> 2)]-[alpha-rhamnosyl-(1 --> 6)]-beta-glucoside-7-O-alpha-rhamnoside and kaempferol 3-O-[alpha-rhamnosyl-(1 --> 2)]-[alpha-rhamnosyl-(1 --> 4)]-beta-glucoside-7-O-alpha-rhamnoside together with benzoic acid 4-O-beta-glucoside, benzoic acid 4-O-alpha-rhamnosyl-(1 --> 2)-beta-glucoside and benzaldehyde 4-O-beta-glucoside have been isolated from methanolic extract of Moringa oleifera leaves. Also obtained from the same extract were known compounds, kaempferol 3-O-alpha-rhamnoside, kaempferol, syringic acid, gallic acid, rutin and quercetin 3-O-beta-glucoside. Their structures were determined using spectroscopic methods as well as comparison with data from known compounds. PMID:17365690

Manguro, Lawrence Onyango Arot; Lemmen, Peter

2007-01-01

392

Flavonoids of Arctostaphylos uva-ursi (Ericaceae)  

Microsoft Academic Search

Résumé Dans trois variétés d'Arctostaphylos uva-ursi, j'ai trouvé les flavanoides suivants: arabinoside-3, glucoside-3, galactoside-3, diglucoside-3, rutinoside-3, rhamnoside-3, glucoside-7-quercetine and arabinoside-3, glucoside-3-myricetine. J'ai déduit une corrélation entre la distribution limitée de certains d'entre ces flavonoides et les localités, en Amérique du Nord qui ont échappé a la glaciation.

K. E. Denford

1973-01-01

393

Enzymatic glycosidations in dry media on mineral supports  

Microsoft Academic Search

Preparation of 4-hydroxybutyl-?-D-glucoside was achieved by reversed hydrolysis from glucose using almond-?-glucosidase impregnated on mineral supports, while 4-hydroxybutyl-?-D-glucoside was obtained from glucose or by one-pot starch hydrolysis followed by glucosidation catalysed by ?-amylase (amyloglucosidase) from Rhizopus mold on celites. The influence of the support nature and of water activity were investigated in order to shift the equilibrium towards glycosidation.

Mirjana Gelo-Pujic; Eryka Guibé-Jampel; André Loupy

1997-01-01

394

Inhibition of lipid peroxidation and the active oxygen radical scavenging effect of anthocyanin pigments isolated from Phaseolus vulgaris L  

Microsoft Academic Search

No attention has been paid to anthocyanin pigments from the viewpoint of inhibitors of lipid peroxidation and scavengers of active oxygen radicals; therefore, we investigated the antioxidative, radical scavenging, and inhibitory effects on lipid peroxidation by UV light irradiation of three anthocyanin pigments, pelargonidin 3-O-?-d-glucoside (P3G), cyanidin 3-O-?-d-glucoside (C3G), and delphinidin 3-O-?-d-glucoside (D3G), isolated from the Phaseolus vulgaris L. seed

Takanori Tsuda; Kaoru Shiga; Katsumi Ohshima; Shunro Kawakishi; Toshihiko Osawa

1996-01-01

395

Flavonolglykoside des Beifuß (Artemisia vulgaris L.), Estragon (Artemisia dracunculus L.) und Wermut (Artemisia absinthium L.)  

Microsoft Academic Search

Summary The following flavonol 3-O-glycosides of the leaves of mugwort (A), tarragon (B) and absinth (C) have been isolated by preparative paper and thin-layer chromatography: kaempferol 3-rhamnoglucoside in B, quercetin 3-glucoside in A and C, quercetin 3-rhamnoglucoside (rutin) in A, B and C, isorhamnetin 3-glucoside and 3-rhamnoglucoside in C and probably in A, patuletin 3-glucoside and 3-rhamnoglucoside in B and

Bernd Hoffmann; Karl Herrmann

1982-01-01

396

Microbiology (1997), 143, 179185 Printed in Great Britain Bacteriophage T4 development depends on the  

E-print Network

by pretreatment with low penicillin (Pn) concentrations; it was directly proportional to total cellular surface). ................................................................................................................................................. Abbreviations: -MG, methyl -D-glucoside; Pn, penicillin; PSS, protein- synthesizing system. Phage

Zaritsky, Arieh

397

Phenolic compounds in blackcurrant (Ribes nigrum L.) leaves relative to leaf position and harvest date.  

PubMed

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

Vagiri, Michael; Conner, Sean; Stewart, Derek; Andersson, Staffan C; Verrall, Susan; Johansson, Eva; Rumpunen, Kimmo

2015-04-01

398

Microfluidic Glycosyl Hydrolase Screening for Biomass-to-Biofuel Conversion  

E-print Network

to enzymatic saccharification. The hydrolysis involves synergistic action by endoglucanases (EC 3-glucose. Endoglucanases randomly hydrolyze accessible intramolecular -1,4-glucosidic bonds of cellulose chains and produce

Singh, Anup

399

Montamine, a unique dimeric indole alkaloid, from the seeds of  Centaurea montana (Asteraceae), and its in vitro cytotoxic activity against the CaCo2 colon cancer cells  

Microsoft Academic Search

Reversed-phase HPLC analysis of the methanol extract of the seeds of Centaurea montana afforded a flavanone, montanoside (4), six epoxylignans, berchemol (7), berchemol 4?-O-?-d-glucoside (5), pinoresinol (10), pinoresinol 4-O-?-d-glucoside (8), pinoresinol 4,4?-di-O-?-d-glucoside (6), pinoresinol 4-O-apiose-(1?2)-?-d-glucoside (9), two quinic acid derivatives, trans-3-O-p-coumaroylquinic acid (1), cis-3-O-p-coumaroylquinic acid (2), and eight indole alkaloids, tryptamine (3), N-(4-hydroxycinnamoyl)-5-hydroxytryptamine (11), cis-N-(4-hydroxycinnamoyl)-5-hydroxytryptamine (12), centcyamine (16), cis-centcyamine (17),

Mohammad Shoeb; Stephen M. MacManus; Marcel Jaspars; Jioji Trevidu; Lutfun Nahar; Paul Kong-Thoo-Lin; Satyajit D. Sarker

2006-01-01

400

Further constituents from the bark of Tabebuia impetiginosa.  

PubMed

Further study on the constituents from the bark of Tabebuia impetiginosa (Mart. ex DC) Standley afforded twelve compounds, consisting of four iridoid glycosides, one phenylethanoid glycoside, five phenolic glycosides, and one lignan glycoside, along with seven known compounds. The structures of these compounds were determined based on the interpretation of their NMR and MS measurements and by chemical evidence. PMID:15721952

Warashina, Tsutomu; Nagatani, Yoshimi; Noro, Tadataka

2005-03-01

401

Fitness costs of chemical defense in Plantago lanceolata L.: effects of nutrient and competition stress  

Microsoft Academic Search

Fitness costs of defense are often invoked to explain the maintenance of genetic variation in levels of chemical defense compounds in natural plant populations. We investigated fitness costs of iridoid glycosides (IGs), terpenoid compounds that strongly deter generalist insect herbivores, in ribwort plantain (Plantago lanceolata L.) using lines that had been artificially selected for high and low leaf IG concentrations

Hamida B. Marak; Arjen Biere; Jos M. M. Van Damme

2003-01-01

402

Effects of Quantitative Variation in Allelochemicals in Plantago lanceolata on Development of a Generalist and a Specialist Herbivore and their Endoparasitoids  

Microsoft Academic Search

Studies in crop species show that the effect of plant allelochemicals is not necessarily restricted to herbivores, but can extend to (positive as well as negative) effects on performance at higher trophic levels, including the predators and parasitoids of herbivores. We examined how quantitative variation in allelochemicals (iridoid glycosides) in ribwort plantain, Plantago lanceolata, affects the development of a specialist

Jeffrey A. Harvey; Saskya Van Nouhuys; Arjen Biere

2005-01-01

403

Independently recruited oxidases from the glucose-methanol-choline oxidoreductase family enabled chemical defences in leaf beetle larvae (subtribe Chrysomelina) to evolve.  

PubMed

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

Rahfeld, Peter; Kirsch, Roy; Kugel, Susann; Wielsch, Natalie; Stock, Magdalena; Groth, Marco; Boland, Wilhelm; Burse, Antje

2014-08-01

404

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...

405

A comparison of flavonoid glycosides by electrospray tandem mass spectrometry  

NASA Astrophysics Data System (ADS)

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.

March, Raymond E.; Lewars, Errol G.; Stadey, Christopher J.; Miao, Xiu-Sheng; Zhao, Xiaoming; Metcalfe, Chris D.

2006-01-01

406

Chemical analysis of flavonoid constituents of the seagrass Halophila stipulacea: First finding of malonylated derivatives in marine phanerogams  

Microsoft Academic Search

The flavonoid fraction from the butanol extract of a Mediterranean sample of the seagrass Halophila stipulacea was chemically analyzed. A new malonylated flavone glucoside, genkwanin-4?-O-(6“-malonyl-glucopyranoside) (3), was isolated together with known flavone glucosides 4-9, previously reported only from terrestrial sources. The structure of 3 was established by means of spectroscopic techniques, mainly NMR methods.

Fatma Bitam; Maria Letizia Ciavatta; Marianna Carbone; Emiliano Manzo; Ernesto Mollo; Margherita Gavagnin

2010-01-01

407

Quercetin from Shallots (Allium cepa L. var. aggregatum) Is More Bioavailable Than  

Microsoft Academic Search

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 bioavailabilityofquercetinaglyconeprovidedtohumansasapuresubstanceistheresultofitslowsolubilityinthedigestive tract,westudieditsbioavailabilityfromdietarysourcesinwhichquercetinwasdispersedinthefoodmatrix.Inarandomized crossover study, 9 volunteers took a single dose

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

408

Sensitivity of the fungus Cytospora persoonii to the flavonoids of Prunus cerasus  

Microsoft Academic Search

Bioassays compared mycelial growth of Cytospora persoonii on flavonoid glucosides and aglycones from resistant Prunus cerasus. Apart from the fact that flavonoid aglycones were more toxic than the corresponding glucosides, there was a difference in fungal reaction depending on the flavonoid type. The fungus was much more sensitive to changes in the concentration of the flavanone aglycones than to those

Martin Geibel

1995-01-01

409

An analysis of the costs and benefits of the cyanogenic system in Trifolium repens L  

Microsoft Academic Search

The effect of the cyanogenic glucosides linamarin and lotaustralin and their hydrolyzing enzyme linamarase was studied in a B2 generation segregating for the genes Ac and Li. Plants containing the glucosides are protected against grazing by snails both in the seedling stage and as adult plants. In seedlings, however, there is a direct effect on survival, whereas in adult plants

P. Kakes

1989-01-01

410

Glycosylation of artepillin C with cultured plant cells of Phytolacca americana.  

PubMed

Biotransformation of artepillin C was investigated using cultured plant cells as biocatalysts. Artepillin C was converted into its 4- and 9-beta-D-glucosides, and 4,9-beta-D-diglucoside by cultured cells of Phytolacca americana. In contrast, cultured lpomoea batatas cells glucosylated artepillin C to only its 4- and 9-beta-D-glucosides. PMID:25026721

Shimoda, Kei; Kubota, Naoji; Uesugi, Daisuke; Hamadab, Hiroki

2014-05-01

411

Host plant influence on the composition of the defensive secretion of Chrysomela vigintipunctata larvae (Coleoptera: Chrysomelidae)  

Microsoft Academic Search

Phenolic glucosides from willow leaves are used by Chrysomela vigintipunctata larvae as precursors of salicylaldehyde produced in the defensive secretion. When these larvae were fed on different Salix species with high to moderate phenolic glucoside content (S. purpurea, S. myrsinifolia, S. fragilis), their defensive secretion mainly contained salicylaldehyde and only traces of other constituents (benzaldehyde and phenylethanol). The volume of

Philippe Soetens; Jacques M Pasteels; Désiré Daloze; Michel Kaisin

1998-01-01

412

Liquid chromatography–electrospray ionization mass spectrometry study of the flavonoids of the roots of Astragalus mongholicus and A. membranaceus  

Microsoft Academic Search

High-performance liquid chromatography–electrospray ionization mass spectrometry has been applied to analyze the flavonoids of Huangqi, the roots of Astagalus mongholicus and A. membranaceus. Eight flavonoids were identified as calycosin-7-O-?-d-glucoside, calycosin-7-O-?-d-glucoside-6?-O-malonate (2), ononin, (6aR,11aR)-3-hydroxy-9,10-dimethoxypterocarpan-3-O-?-d-glucoside, calycosin, (3R)-7,2?-dihydroxy-3?,4?-dimethoxyisoflavan-7-O-?-d-glucoside, formononetin-7-O-?-d-glucoside-6?-O-malonate and formononetin by direct comparison with the isolated standards from Huangqi. The existence of (6aR,11aR)-3-hydroxy-9,10-dimethoxypterocarpan, (3R)-7,2?-dihydroxy-3?,4?-dimethoxyisoflavan, astrapterocarpanglucoside-6?-O-malonate and astraisoflavanglucoside-6?-O-malonate was detected. This is the

Long-Ze Lin; Xian-Guo He; Michael Lindenmaier; Gary Nolan; Jie Yang; Michael Cleary; Sheng-Xiang Qiu; Geoffrey A Cordell

2000-01-01

413

Phenol homeostasis is ensured in vanilla fruit by storage under solid form in a new chloroplast-derived organelle, the phenyloplast  

PubMed Central

A multiple cell imaging approach combining immunofluorescence by confocal microscopy, fluorescence spectral analysis by multiphotonic microscopy, and transmission electron microscopy identified the site of accumulation of 4-O-(3-methoxybenzaldehyde) ?-d-glucoside, a phenol glucoside massively stockpiled by vanilla fruit. The glucoside is sufficiently abundant to be detected by spectral analysis of its autofluorescence. The convergent results obtained by these different techniques demonstrated that the phenol glucoside accumulates in the inner volume of redifferentiating chloroplasts as solid amorphous deposits, thus ensuring phenylglucoside cell homeostasis. Redifferentiation starts with the generation of loculi between thylakoid membranes which are progressively filled with the glucoside until a fully matured organelle is obtained. This peculiar mode of storage of a phenolic secondary metabolite is suspected to occur in other plants and its generalization in the Plantae could be considered. This new chloroplast-derived organelle is referred to as a ‘phenyloplast’. PMID:24683183

Conéjéro, Geneviève

2014-01-01

414

Structural characterisation and antioxidant activity evaluation of phenolic compounds from cold-pressed Perilla frutescens var. arguta seed flour.  

PubMed

A total of 11 phenolic compounds, as well as sucrose (12) and tryptophan (13), were isolated from cold-pressed Perilla frutescens var. arguta seed flour using column chromatography, and their chemical structures were identified as 3'-dehydroxyl-rosmarinic acid-3-o-glucoside (1), rosmarinic acid-3-o-glucoside (2), rosmarinic acid (3), rosmarinic acid methyl ester (4), luteolin (5), luteolin-5-o-glucoside (6), apigenin (7), caffeic acid (8), caffeic acid-3-o-glucoside (9), vanillic acid (10) and cimidahurinine (11) using NMR and time-of-flight mass spectrometry. Of these components, compound 1 is novel, and this is the first report of compounds 10 and 11 in perilla seeds. HPLC quantification combined with antioxidant activity evaluation revealed that rosmarinic acid and rosmarinic acid-3-o-glucoside were the dominant phenolic antioxidants with strong antioxidant activities. PMID:24996318

Zhou, Xiao-Jing; Yan, Lin-Lin; Yin, Pei-Pei; Shi, Ling-Ling; Zhang, Jing-Hua; Liu, Yu-Jun; Ma, Chao

2014-12-01

415

New Flavonoid Glycosides from Arnicae Flos DAB 91.  

PubMed

Five flavonoid glycosides were identified from flowers of Arnica montana, ten from A. CHAMISSONIS subsp. FOLIOSA var. INCANA. The structures were established on the basis of acid hydrolysis and spectral data (UV, NMR, MS) as the 7-beta-glucosides of pectolinarigenin, apigenin, and chrysoeriol; luteolin 3'- O-beta-glucoside; the 3-beta-glucuronides of kaempferol, isorhamnetin, and 6-methoxykaempferol; the 3,7-di-beta-glucosides of quercetin and patuletin; the 3-beta-glucosides of betuletol and quercetagetin 6,3',4'-trimethyl ether; and the 7-[6''- O-(2-methylbutyryl)]=glucosides of luteolin and eupafolin. The latter four are new natural compounds. Differences between these two ARNICA species are discussed. PMID:17226484

Merfort, I; Wendisch, D

1992-08-01

416

Quantitative analysis of beta-d-glucopyranoside of 3-methyl-4-hydroxyoctanoic acid, a potential precursor to cis-oak lactone, in oak extracts using liquid chromatography-tandem mass spectrometry based stable isotope dilution analysis.  

PubMed

The beta-D-glucopyranoside of 3-methyl-4-hydroxyoctanoic acid (glucoside), exists in oak wood and is a potential precursor to cis-oak lactone. A method for the quantification of the glucoside in extracts of oak wood using liquid chromatography-tandem mass spectrometry was developed. The [(2)H(4)]-labeled analogue of the glucoside was synthesized and used as internal standard for the method which was subsequently applied to the analysis of extracts of both American and French oak woods. The concentration of the glucoside in the extracts varied widely from less than 0.1 up to approximately 50 microg/g-oak wood. The method allowed for the quantification of the glucoside as a potential oak lactone precursor in oak woods for the first time. PMID:19026418

Fudge, Anthea L; Elsey, Gordon M; Hayasaka, Yoji; Wilkinson, Kerry L

2008-12-26

417

Anthocyanin profile of Korean cultivated kidney bean (Phaseolus vulgaris L.).  

PubMed

This investigation was conducted to determine the structures and amounts of anthocyanins obtained from seed coats of kidney bean (Phaseolus vulgaris L.) cultivated in Korea. Anthocyanins in the seed coat of kidney bean were extracted with 1% HCl/20% CH(3)OH, and the crude anthocyanin extracts were purified by semipreparative HPLC. Five major anthocyanins were isolated, and their chemical structures were identified by spectroscopic methods (UV-vis, LC/ES-MS, and 1H and 13C NMR). The structures of these five anthocyanins were elucidated as cyanidin 3,5-diglucoside, delphinidin 3-glucoside, cyanidin 3-glucoside, petunidin 3-glucoside, and pelargonidin 3-glucoside. Using RP-HPLC with photodiode array detection, each of the five anthocyanins was separated within 12 min by using a gradient elution. It was proved that the application of RP-HPLC could be an excellent method for determining the composition and contents of anthocyanins in kidney bean. The preponderance of pelargonidin 3-glucoside and delphinidin 3-glucoside are observed in red and black kidney beans, respectively. However, in this study, it is reported for the first time that the contents and composition of anthocyanins in speckled seed depend on the classes of speckle color. The contents of cyanidin 3,5-diglucoside, delphinidin 3-glucoside, cyanidin 3-glucoside, petunidin 3-glucoside, pelargonidin 3-glucoside, and total anthocyanins in seed coats of 16 kidney beans cultivated in Korea were in the ranges of 0-0.04, 0-2.61, 0-0.12, 0-0.17, 0-0.59 and 0-2.78 mg/g of dried seed coats, respectively. PMID:14611168

Choung, Myoung-Gun; Choi, Byoung-Rourl; An, Young-Nam; Chu, Yong-Ha; Cho, Young-Son

2003-11-19

418

Specific poly-phenolic compounds in cell culture of Vitis vinifera L. cv. Gamay Fréaux.  

PubMed

Cell cultures established from plants represent an attractive alternative to whole plants for effective production of bioactive secondary metabolites. Cell culture from Vitis vinifera L. cv. Gamay Fréaux accumulated high amounts of hydroxycinnamic acid derivatives and anthocyanins. Two new compounds were identified: 3-O-glucosylresveratrol, a stilbene derivative, abundant in cell suspension culture, and a hydroxyphenol, 4-(3,5-dihydroxyphenyl)-phenol, abundant in callus culture. The major anthocyanin monoglucosides present in cell suspension culture were cyanidin 3-O-glucoside and peonidin 3-O-glucoside, and the major cinnamoyl derivatives were cyanidin 3-O-p-coumaryl glucoside and peonidin 3-O-p-coumaryl glucoside. Three minor anthocyanin compounds were found in V. vinifera cell culture: delphinidin 3-O-glucoside, petunidin 3-O-glucoside, and delphinidin 3-O-pcoumaryl glucoside. Anthocyanin levels of cell suspension cultures increased significantly--about eight fold--after 4-day cultivation in new medium. Salicylic acid at a concentration of 50 ?M did not enhance anthocyanin accumulation in cell suspension culture, and similar levels of jasmonic acid significantly reduced the anthocyanin content. PMID:21061087

Mewis, Inga; Smetanska, Iryna M; Müller, Carsten T; Ulrichs, Christian

2011-05-01

419

Constituents from the bark of Tabebuia impetiginosa.  

PubMed

The bark of Tabebuia impetiginosa afforded nineteen glycosides, consisting of four iridoid glycosides, two lignan glycosides, two isocoumarin glycosides, three phenylethanoid glycosides and eight phenolic glycosides. Their structures were determined using both spectroscopic and chemical methods. Iridoid glycosides, phenylethanoid glycosides and lignan glycosides had ajugol, osmanthuside H and secoisolariciresinol 4-O-beta-D-glucopyranoside as their structural elements, respectively, whereas the aglycone moieties of the isocoumarin glycosides were considered to be (-)-6-hydroxymellein. Phenolic glycosides had 4-methoxyphenol, 2,4-dimethoxyphenol, 3,4-dimethoxyphenol, 3,4,5-trimethoxyphenol and vanillyl 4-hydroxybenzoate as each aglycone moiety. Additionally, the sugar chains of these isocoumarin glycosides and phenolic glycosides were concluded to be beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside as well as those of osmanthuside H and above phenylethanoid glycosides. PMID:15280007

Warashina, Tsutomu; Nagatani, Yoshimi; Noro, Tadataka

2004-07-01

420

Effects of Increased UVB radiation on plant-insect interactions: Plantago lanceolata and Junonia coenia  

SciTech Connect

Seeds of P. lanceolata were collected from a local population and 4 replicates of 42 maternal families were grown for 90 days in the greenhouse with at two levels of supplemental UVB radiation (6 and 12 kJ day[sup [minus]1] BE[sub 300]). Higher UVB radiation increased leaf hair density and decreased plant size during early growth; family identity affected these also. Leaves excised from a subset of the plants were fed to ultimate instar larvae of J. coenia and assayed for iridoids. Increased UVB radiation did not alter the iridoid content of the leaves or the growth of the larvae. In a separate experiment, P. lanceolata growing under the two levels of UVB irradiation were infested with neonate larvae and larval growth was monitored. Larval growth was not markedly altered by enhanced UVB. These findings suggest that increased UVB is unlikely to alter the suitability of P. lanceolata as a host for J. coenia.

McCloud, E.S.; Berenbaum, M.R. (Univ. of Illinois, Urbana (United States))

1993-06-01

421

Evolution of juice anthocyanins during ripening of new selected pomegranate (Punica granatum) clones  

Microsoft Academic Search

For five new clones of pomegranate, cultivated under homogeneous conditions, changes in juice anthocyanin contents during\\u000a ripening were studied. Six anthocyanin pigments were found to be responsible for the red color of pomegranate juice. These\\u000a were quantitatively and qualitatively analyzed by high-performance liquid chromatography and identified as delphinidin 3-glucoside\\u000a and 3,5-diglucoside, cyanidin 3-glucoside and 3,5-diglucoside and pelargonidin 3-glucoside and 3,5-diglucoside.

F. Hernández; P. Melgarejo; F. A. Tomás-Barberán; F. Artés

1999-01-01

422

Uptake of [2-(14)C] mevalonic acid by lipid and glycoside sterols.  

PubMed

D. L. [2-(14)C] mevalonic acid was fed to Digitalis purpurea flowering plants and the 4-4'-dimethyl and phytosterol fractions isolated at time intervals from the glucoside and lipid portions of the plant extract. The incorporation of mevalonic acid was determined in both the aerial parts and the roots over a period of 35 days. In the aerial parts the uptake of radioactivity was rapid in the cycloartenol and lipid phytosterol fractions, but less so in the glucoside phytosterols. In the roots the glucoside phytosterols incorporation of label was considerably more rapid than in the lipid fraction. PMID:24458121

Evans, F J

1974-06-01

423

Microphynolides A and B, new spiro-?-lactone glycosides from Thymelaea microphylla.  

PubMed

Two new spiro-?-lactone glycosides named microphynolide A (1) and microphynolide B (2), together with twelve known compounds including five biflavonoids namely neochamaejasmin A, neochamaejasmin B, daphnodorin B, genkwanol A and stelleranol, one bis-coumarin daphnoretin, two lignans called pinoresinol and matairesinol, one flavonoid glucoside, tiliroside, a sinapyl alcohol glucoside, syringin, and two phytosterols, ?-sitosterol and ?-sitosterol-3-O-glucoside, were isolated from ethyl acetate extracts of the aerial parts and roots of the plant Thymelaea microphylla Coss. and Dur. All the isolated compounds were characterised by using spectroscopic methods and comparison with the literature data. PMID:25076123

Ghanem, Hasna; Haba, Hamada; Marcourt, Laurence; Benkhaled, Mohammed; Wolfender, Jean-Luc

2014-01-01

424

Fossil Record and Age of the Asteridae  

Microsoft Academic Search

The Asteridae is a group of some 80,000 species of flowering plants characterized by their fused corollas and iridoid compounds.\\u000a Recent phylogenetic analyses have helped delimit the group and have identified four main clades within it; Cornales, Ericales,\\u000a Lamiids and Campanulids, with the last two collectively known as the Euasteridae. A search for the oldest fossils representing\\u000a asterids yielded a

Marcela Martínez-Millán

2010-01-01

425

Phytochemical investigation and antioxidant activity of Duranta repens.  

PubMed

The ethylacetate fraction of the methanol extract of Duranta repens L. (Verbenaceae) showed radicalscavenging activity in the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. Three compounds were isolated from this fraction, i.e. the phenylethanoid glycoside acteoside, the iridoid lamiide and the saponin pseudo-ginsenoside-RT1. Acteoside showed an IC50 of 3.05 +/- 0.09 microg/mL in the DPPH assay, while lamiide and pseudo-ginsenoside-RT1 were not active. PMID:16372377

Shahat, Abdelaaty A; Nazif, Naglaa M; Abousetta, Lobna M; Ibrahim, Nabaweia A; Cos, Paul; Van Miert, Sabine; Pieters, Luc; Vlietinck, Arnold J

2005-12-01

426

Effects of ?-glucosidase hydrolyzed products of harpagide and harpagoside on cyclooxygenase-2 (COX2) in vitro  

Microsoft Academic Search

Harpagide (1) and harpagoside (2) are two iridoid glycosides existing in many medicinal plants. Although they are believed to be the main bioactive compounds related to the anti-inflammatory efficacy of these plants, the mechanisms of their anti-inflammatory activities remain unclear. The results of our present study showed that 1 and 2 had no effects on inhibitions of cyclooxygenase (COX)-1\\/2 enzyme

Liuqiang Zhang; Li Feng; Qi Jia; Jinwen Xu; Rui Wang; Zhengtao Wang; Yingchun Wu; Yiming Li

2011-01-01

427

Modulation of cytochrome P-450-dependent monooxygenases, glutathione and glutathione S-transferase in rat liver by geniposide from gardenia jasminoides  

Microsoft Academic Search

Geniposide is an iridoid glycoside extracted from the fruits of Gardenia jasminoides, which are used as a food colorant and as a traditional Chinese medicine for treatment of hepatic and inflammatory diseases. The effects of geniposide and G. jasminoides fruit crude extract on liver cytochrome P-450 (P-450)-dependent monooxygenases, glutathione and glutathione S-transferase were investigated using rats treated orally with the

J.-J. Kang; H.-W. Wang; T.-Y. Liu; Y.-C. Chen; T.-H. Ueng

1997-01-01

428

To be or not to be convergent in salicin-based defence in chrysomeline leaf beetle larvae: evidence from Phratora vitellinae salicyl alcohol oxidase.  

PubMed

Glandular chemical defence relying on the action of salicylaldehyde is characteristic for Chrysomela leaf beetle larvae. The salicylaldehyde precursor salicin, sequestered from salicaceous host plants, is deglucosylated and the aglycon further oxidized by a salicyl alcohol oxidase (SAO) to the respective aldehyde. SAOs, key enzymes in salicin-based glandular chemical defence, were previously identified and shown to be of a single evolutionary origin in Chrysomela species. We here identified and characterized SAO of Phratora vitellinae, the only species outside the genus Chrysomela that produce salicylaldehyde as a defensive compound. Although Chrysomela and Phratora are not closest relatives, their SAOs share glucose-methanol-choline oxidoreductase (GMC) affiliation, a specific GMCi subfamily ancestor, glandular tissue-specific expression and almost identical gene architectures. Together, this strongly supports a single origin of SAOs of both Chrysomela and Phratora. Closely related species of Chrysomela and P. vitellinae use iridoids as defensive compounds, which are like salicylaldehyde synthesized by the consecutive action of glucosidase and oxidase. However, we elucidated SAO-like sequences but no SAO proteins in the glandular secretion of iridoid producers. These findings support a different evolutionary history of SAO, related genes and other oxidases involved in chemical defence in the glandular system of salicylaldehyde and iridoid-producing leaf beetle larvae. PMID:21429930

Kirsch, Roy; Vogel, Heiko; Muck, Alexander; Vilcinskas, Andreas; Pasteels, Jacques M; Boland, Wilhelm

2011-11-01

429

Bignoniaceae metabolites as semiochemicals.  

PubMed

Members of the family Bignoniaceae are mostly found in tropical and neo-tropical regions in America, Asia and Africa, although some of them are cultivated in other regions as ornamentals. Species belonging to this family have been extensively studied in regard to their pharmacological properties (as extracts and isolated compounds). The aim of this review is to summarize the reported scientific evidence about the chemical properties as well as that of the extracts and isolated compounds from species of this family, focusing mainly in insect-plant interactions. As it is known, this family is recognized for the presence of iridoids which are markers of oviposition and feeding preference to species which have became specialist feeders. Some herbivore species have also evolved to the point of been able to sequester iridoids and use them as defenses against their predators. However, iridoids also exhibit anti-insect properties, and therefore they may be good lead molecules to develop botanical pesticides. Other secondary metabolites, such as quinones, and whole extracts have also shown potential as anti-insect agents. PMID:20948497

Castillo, Lucía; Rossini, Carmen

2010-01-01

430

Glandular ?-glucosidases in juvenile Chrysomelina leaf beetles support the evolution of a host-plant-dependent chemical defense.  

PubMed

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

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

431

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...

432

The synthesis of safranal  

E-print Network

Introduction: Safranal is a cyclic monoterpene which occurs naturally in the saffron plant as a glucoside, picrocrocin. In 1922 Winterstein and TeleCzky obtained safranal by hydrolysis of picrocrocin, but its structure ...

Nelson, David A. (David Alan), 1931-

1953-01-01