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1

Pharmacokinetic Study of an Iridoid Glucoside: Aucubin  

Microsoft Academic Search

Aucubin, a promising hepatoprotecting iridoid glucoside, was given intravenously (iv), orally (po), intraperitoneally (ip), and hepatoportally (pv) to rats. A linear pharmacokinetic behavior was obtained after iv administration of 40–400 mg\\/kg of aucubin. The half-life of aucubin in the postdistributive phase (t1\\/2,ß), total-body plasma clearance (CLt), and volume of distribution (Vdss) were 42.5 min, 7.2 ml\\/min\\/kg, and 346.9 ml\\/kg, respectively,

Nan-Joo Suh; Chang-Koo Shim; Min Hwa Lee; Shin Keun Kim; Il-Moo Chang

1991-01-01

2

A novel series of cytotoxic iridoid glucosides derived from aucubin: Design, synthesis and structure–activity relationships  

Microsoft Academic Search

Five new unsaturated iridolactones 3–7 related to natural cytotoxic oxylipins, Tei 9826, and iridolactone 2, were prepared by parallel synthesis from natural aucubin. It was found that perpivaloyl iridoid glucosides 2, 3, and 4 were markedly cytotoxic against both L1210 and KB-3-1 cell lines.

Vokatsoa C. Rakotondramasy; Christine Mouriès; Xavier Cachet; Abdelhak Neghra; Missam El Mourabet; François Tillequin; Michel Koch; Brigitte Deguin

2010-01-01

3

X-ray crystal structure of iridoid glucoside aucubin and its aglycone  

Microsoft Academic Search

X-ray diffraction analyses of iridoid glycoside aucubin (1) and its aglycone aucubigenin (2) are reported. It was found that crystals of 1 are orthorhombic, with P212121 space group, both cyclopentane ring and pyran ring adopt envelope conformations, and the Glc moiety is in the 4C1 conformation. Crystals of 2 are monoclinic, with space group P21, the cyclopentane and pyran rings

Yang Li; Ye Zhao; Yong-min Zhang; Min-juan Wang; Wen-ji Sun

2009-01-01

4

Iridoid glucosides in Plantago alpina and P. Altissima  

Microsoft Academic Search

Two species of Plantago, namely P. Alpina and P. altissima were investigated. From the former, nine iridoid glucosides and verbascoside were isolated. Together with the known iridoids gardoside, geniposidic acid, 8-epi-loganic acid, mussaenosidic acid, aucubin, monomelittoside and melittoside, two new glucosides were found: 10-O-acetylgeniposidic acid and alpinoside, another compound with a 10-O-acetyl group. From P. altissima verbascoside and isoverbascoside were

Søren Rosendal Jensen; Carl Erik Olsen; Knud Rahn; Jon Holbech Rasmussen

1996-01-01

5

Phytotoxic Iridoid Glucosides from the Roots of Verbascum thapsus  

Microsoft Academic Search

The iridoid glucosides lateroside 1, harpagoside 2, ajugol 3, and aucubin 4 were isolated from an ethanolic extract of the roots of the weed Verbascum thapsus that exhibits antigermination activity on seeds of barley (Hordeum vulgare). Bioassays indicated that at 3 mM concentration, compounds 1, 2, and 4 showed moderate inhibition of seed germination. These compounds also reduced root length

F. Pardo; F. Perich; R. Torres; F. Delle Monache

1998-01-01

6

Mechanism of covalent adduct formation of aucubin to proteins  

Microsoft Academic Search

The iridoid glucoside aucubin can irreversibly bind to proteins through the formation of its aglycone. In view of a possible involvement of these protein adducts in the toxicity of aucubin, we investigated the mechanism of binding of aucubin to proteins. [3H]aucubin in itself did not result in binding to protein whereas it covalently bound to rat serum albumin as a

Dong-Hyun Kim; Bok-Ryang Kim; Ji-Yeon Kim; Yo-Chan Jeong

2000-01-01

7

Iridoid Glucosides and an Acetophenone Glucoside from Penstemon whippleanus.  

PubMed

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

Junior, P

1984-10-01

8

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

Microsoft Academic Search

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-?-arabino(1?6)-?-glucopyranosyl arborescosidic acid) and the 6-hydroxy-flavone glucoside 4?-O-methylscutellarein 7-O-?-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

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

2004-01-01

9

Iridoids in roots of Pedicularis chinensis  

Microsoft Academic Search

Four new iridoids, the glucosides 3?-butoxy-3,4-dihydroaucubin, 6-O-butyl-aucubin and 6-O-butyl-epiaucubin, together with pedicularis-lactone were isolated from roots of pedicularis chinensis. In addition, the known glucosides aucubin and bartsioside and a known iridoid lactone were also isolated. The compounds were identified mainly by spectral evidence.

Yang Li; Wang Changzeng; Jia Zhongjian

1995-01-01

10

Lantanoside, a monocyclic C 10 iridoid glucoside from viburnum lantana  

Microsoft Academic Search

A new monocyclic C10 iridoid glucoside was isolated from the leaves of Viburnum lantana, together with the two known glucosides, dihydropenstemide and betulalbuside A. The structure of the new compound, lantanoside, was established from extensive 1H and 13C NMR, 1D and 2D homo-and heteronuclear correlation experiments.

Heinz Rüegger; Anthony D. Wright; Otto Sticher

1995-01-01

11

Benzoxazinoids and iridoid glucosides from four Lamium species.  

PubMed

A new class of compounds for the plant family Lamiaceae, benzoxazinoids, was found in Lamium galeobdolon. From the aerial parts of the species were isolated the new 2-O-beta-D-glucopyranosyl-6-hydroxy-2H-1,4-benzoxazin-3(4H)-one (6-hydroxy blepharin) together with four known benzoxazinoids, DHBOA-Glc, blepharin, DIBOA, DIBOA-Glc, as well as harpagide, 8-O-acetyl-harpagide and salidroside. Eight known iridoid glucosides, 24-epi-pterosterone and verbascoside were isolated from Lamium amplexicaule, L. purpureum and L. garganicum. The iridoids, 5-deoxylamiol and sesamoside, as well as the phytoecdysone, 24-epi-pterosterone, were found for the first time for the genus Lamium. The phytochemical data are discussed from a systematic and evolutionary point of view. PMID:14630008

Alipieva, Kalina I; Taskova, Rilka M; Evstatieva, Ljubka N; Handjieva, Nedjalka V; Popov, Simeon S

2003-12-01

12

Inhibitory Potencies of Several Iridoids on Cyclooxygenase1, Cyclooxygnase-2 Enzymes Activities, Tumor Necrosis Factor-? and Nitric Oxide Production In Vitro  

Microsoft Academic Search

To verify the anti-inflammatory potency of iridoids, seven iridoid glucosides (aucubin, catalpol, gentiopicroside, swertiamarin, geniposide, geniposidic acid and loganin) and an iridoid aglycone (genipin) were investigated with in vitro testing model systems based on inhibition of cyclooxygenase (COX)-1\\/-2 enzymes, the tumor necrosis factor-a (TNF-a) formation and nitric oxide (NO) production. The hydrolyzed-iridoid products (H-iridoid) with b-gludosidase treatment only showed inhibitory

Kyoung Sik Park; Bong Hyun Kim; Il-Moo Chang

2010-01-01

13

Benzoxazinoids and iridoid glucosides from four Lamium species  

Microsoft Academic Search

A new class of compounds for the plant family Lamiaceae, benzoxazinoids, was found in Lamium galeobdolon. From the aerial parts of the species were isolated the new 2-O-?-d-glucopyranosyl-6-hydroxy-2H-1,4-benzoxazin-3(4H)-one (6-hydroxy blepharin) together with four known benzoxazinoids, DHBOA-Glc, blepharin, DIBOA, DIBOA-Glc, as well as harpagide, 8-O-acetyl-harpagide and salidroside. Eight known iridoid glucosides, 24-epi-pterosterone and verbascoside were isolated from Lamium amplexicaule, L. purpureum

Kalina I Alipieva; Rilka M Taskova; Ljubka N Evstatieva; Nedjalka V Handjieva; Simeon S Popov

2003-01-01

14

Chlorinated iridoid glucosides from Veronica longifolia and their antioxidant activity.  

PubMed

From Veronica longifolia were isolated three chlorinated iridoid glucosides, namely, asystasioside E (6) and its 6-O-esters 6a and 6b, named longifoliosides A and B, respectively. The structures of 6a and 6b were proved by analysis of their spectroscopic data and by conversion to the catalpol ester verproside (5a) or to catalpol (5), respectively. The configuration of the previously known vanilloyl analogue, urphoside B, was shown to be the 6?-epimer (6c) of the structure originally reported. Longifoliosides A (6a) and B (6b) were found to exhibit radical-scavenging activity against nitric oxide, superoxide, and 2,2-diphenyl-1-picrylhydrazyl radicals. PMID:20806928

Jensen, Søren R; Gotfredsen, Charlotte H; Harput, U Sebnem; Saracoglu, Iclal

2010-09-24

15

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

16

Caeruleosides A and B, bis-iridoid glucosides from Lonicera caerulea  

Microsoft Academic Search

Two new bis-iridoid glucosides, named caeruleosides A and B, were isolated from the leaves of Lonicera caerulea. Their structures have been determined by chemical methods and by 1D and 2D NMR analysis. The compounds consist of secologanin attached through acetal bonds to C-4? and C-6? of the sugar part of loganin and sweroside, respectively.

Koichi Machida; Junko Asano; Masao Kikuchi

1995-01-01

17

Studies on the possible mechanisms of protective activity against ?-amanitin poisoning by aucubin  

Microsoft Academic Search

Aucubin, an iridoid glucoside, was investigated to determine whether it has a stimulating effect on ?-amanitin excretion in\\u000a ?-amanitin intoxicated rats, and whether there is binding activity to calf thymus DNA. High-performance liquid chromatography\\u000a (HPLC) analysis of ?-amanitin in rat urine allowed quantitative measurement of the ?-amanitin concentration with a detection\\u000a limit of 50 ng\\/ml. In this system, a group

Dong Hee Lee; In Goo Cho; Moon Soo Park; Ki-Nam Kim; Il-Moo Chang; Woongchon Mar

2001-01-01

18

Coumarin glycosides and iridoid glucosides with neuroprotective effects from Hydrangea paniculata.  

PubMed

Five new coumarin glycosides, umbelliferone 7-O-sophoroside (1), umbelliferone 7-O-?-D-glucopyranosyl(1???3)-?-D-glucopyranoside (2), umbelliferone 7-O-?-D-glucopyranosyl(1???3)-[?-D-apiofuranosyl(1???6)]-?-D-glucopyranoside (3), umbelliferone 7-O-?-D-glucopyranosyl(1???2)-?-D-apiofuranosyl(1???6)-?-D-glucopyranoside (4), and umbelliferone 7-O-?-D-glucopyranosyl(1???5)-?-D-apiofuranosyl(1???6)-?-D-glucopyranoside (5), and two new iridoid glucosides, 7-O-E-isoferuloyl loganic acid (6) and 7-O-?-D-glucopyranosyl loganin (7), together with eight known compounds (8-15) were isolated from the stems of Hydrangea paniculata. Their structures were established by spectroscopic analysis and chemical methods. At 10?µM, compounds 1, 3, 5, 6, 8, 9, and 13 showed neuroprotective effects against serum deprivation-induced PC12 cell damage. PMID:23047248

Shi, Jing; Li, Chuang-Jun; Yang, Jing-Zhi; Yuan, Yu-He; Chen, Nai-Hong; Zhang, Dong-Ming

2012-11-01

19

Neuroprotection of aucubin in primary diabetic encephalopathy  

Microsoft Academic Search

Hippocampal neuronal apoptosis accompanied by impairment of cognitive function occurs in primary diabetic encephalopathy.\\u000a In this study, we investigated the neuroprotective mechanism of the iridoid glycoside, aucubin, using rats (n=8). Diabetes mellitus was induced in the rats by intraperitoneal (i.p.) injection of streptozotocin (60 mg\\/kg body weight).\\u000a After 65 d, half of the DM rats were administered aucubin (5 mg\\/kg;

HongYu Xue; LiJi Jin; Lei Jin; Peng Zhang; DanQing Li; YanQiu Xia; YaNan Lu; YongPing Xu

2008-01-01

20

LC–ESI-MS analysis of iridoid glucosides in Lamium species  

Microsoft Academic Search

An LC–ESI-MS analysis was performed to determine the iridoid composition of Lamium album, Lamium amplexicaule, Lamium garganicum, Lamium maculatum, and Lamium purpureum. Nine iridoids known to occur in these species, lamalbid, sesamoside, lamiol, 5-deoxylamiol, shanzhiside methyl ester, caryoptoside, penstemoside, lamioside, and barlerin, could be detected. Confident identification of the individual compounds was achieved by a combination of HPLC retention times,

Kalina Alipieva; Tetsuo Kokubun; Rilka Taskova; Ljuba Evstatieva; Nedjalka Handjieva

2007-01-01

21

Verbascoside derivatives and iridoid glycosides from Penstemon crandallii  

Microsoft Academic Search

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

Lotfy D. Ismail; Mohamed M. El-Azizi; Taha I. Khalifa; Frank R. Stermitz

1995-01-01

22

Isolation of aucubin and catalpol from Melitaea cinxia larvae and quantification by micellar electrokinetic capillary chromatography  

Microsoft Academic Search

Two iridoid glycosides, aucubin and catalpol, were extracted from Melitaea cinxia larvae with hot, dilute aqueous SDS solution and then separated and quantified by micellar electrokinetic capillary chromatography. Solutions of pure aucubin and catalpol were used to optimise the separation. The extraction method was developed for a mixture of 80 larvae and single larvae were then analysed with the optimised

Johanna Suomi; Heli Sirén; Susanne K Wiedmer; Marja-Liisa Riekkola

2001-01-01

23

Aucubin Promotes Neurite Outgrowth in Neural Stem Cells and Axonal Regeneration in Sciatic Nerves  

PubMed Central

Aucubin is an iridoid glycoside with a wide range of biological activities, including anti-inflammatory, anti-microbial, anti-algesic as well as anti-tumor activities. Recently, it has been shown that aucubin prevents neuronal death in the hippocampal CA1 region in rats with diabetic encephalopathy. In addition, it has protective effects on H2O2-induced apoptosis in PC12 cells. We have shown here that aucubin promotes neuronal differentiation and neurite outgrowth in neural stem cells cultured primarily from the rat embryonic hippocampus. We also investigated whether aucubin facilitates axonal elongation in the injured peripheral nervous system. Aucubin promoted lengthening and thickness of axons and re-myelination at 3 weeks after sciatic nerve injury. These results indicate that administration of aucubin improved nerve regeneration in the rat model of sciatic nerve injury, suggesting that aucubin may be a useful therapeutic compound for the human peripheral nervous system after various nerve injuries.

Kim, Yong Min; Sim, U-Cheol; Shin, Yongsung

2014-01-01

24

Separation and purification of water-soluble iridoid glucosides by high speed counter-current chromatography combined with macroporous resin column separation.  

PubMed

Four iridoid glucosides, shanzhiside methyl ester, phloyoside II, chlorotuberside, and penstemonoside, were isolated and purified from an herbal medicinal plant for the first time by high-speed counter-current chromatography (HSCCC) using a two-phase solvent system composed of ethyl acetate-n-butanol-water (5:14:12, v/v/v). A total of 37mg of shanzhiside methyl ester, 29mg of phloyoside II, 27mg of chlorotuberside, and 21mg of penstemonoside with the purity of 99.2%, 98.5%, 97.3%, and 99.3%, respectively, were obtained in one-step separation within 4h from 150mg of crude extract. To the best of our knowledge, this is the first report of separation and purification of iridoid glucosides from natural sources by HSCCC. The chemical structures of all the four compounds were identified by ESI-MS, (1)H NMR, and (13)C NMR. PMID:23981483

Yue, Hui-Lan; Zhao, Xiao-Hui; Wang, Qi-Lan; Tao, Yan-Duo

2013-10-01

25

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

26

Euphydryas anicia (Lepidoptera: Nymphalidae) utilization of iridoid glycosides from Castilleja and Besseya (Scrophulariaceae) host plants  

Microsoft Academic Search

Iridoid glycosides were found to be sequestered by natural populations ofEuphydryas anicia after ingestion from the host plantsBesseya alpina, B. plantaginea, andCastilleja integra. Both major iridoids ofB. alpina, cataipol and aucubin, were found in butterfly populations where this was the only host plant. The catalpol-aucubin ratio was higher in the butterflies than in the host plant. AnE. anicia population which

Frank R. Stermitz; Dale R. Gardner; Francois J. Odendaal; Paul R. Ehrlich

1986-01-01

27

The iridoid glucoside secologanin is derived from the novel triose phosphate\\/pyruvate pathway in a Catharanthus roseus cell culture  

Microsoft Academic Search

Secologanin is the iridoid building block of the majority of the terpenoid indole alkaloids. In the biosynthesis of secologanin, mevalonate was considered to be the exclusive precursor of isopentenyl diphosphate. After [1-13C]glucose feeding to a cell culture of Catharanthus roseus, its incorporation into secologanin was studied by 13C NMR spectroscopy. The data showed that the novel triose phosphate\\/pyruvate and not

Adriana Contin; Robert van der Heijden; Alfons W. M Lefeber; Robert Verpoorte

1998-01-01

28

Veronica: Iridoids and cornoside as chemosystematic markers  

Microsoft Academic Search

The iridoid glucoside, ajugol, and the phenylethanoid glucoside, cornoside, have been isolated from species of Veronica (Plantaginaceae) for the first time. The presence of these compounds has been screened in 18 plant accessions belonging to 15 species of Veronica (Plantaginaceae), by isolation or NMR spectroscopy of crude extracts. In addition, the distribution of iridoids in the genus has been reviewed,

Søren Rosendal Jensen; Dirk C. Albach; Takao Ohno; Renée J. Grayer

2005-01-01

29

Extraction of iridoid glycosides and their determination by micellar electrokinetic capillary chromatography.  

PubMed

Several methods for the extraction of two iridoid glycosides, catalpol and aucubin, from the plant matrix (Veronica longifolia leaves) were compared. Pressurized hot water extraction and hot water extraction were the most efficient isolation techniques for both. Pressurized liquid extraction and maceration with various organic solvents were also tested. Relative to the amounts extracted with hot water, ethanol extracted only 22% of catalpol and 25% of aucubin and pressurized hot water extracted 83% of catalpol and 92% of aucubin. The lowest relative standard deviations, 22% for catalpol and 8% for aucubin, were achieved with hot water extraction (13 repetitions), and the highest relative standard deviations, 76% for catalpol and 73% for aucubin, with pressurized liquid extraction (five repetitions). A fast capillary electrophoretic method was developed for the quantitative determination of catalpol and aucubin. PMID:10677081

Suomi, J; Sirén, H; Hartonen, K; Riekkola, M L

2000-01-28

30

Verbascoside Derivatives and Iridoid Glycosides from Verbascum Undulatum  

Microsoft Academic Search

On further phytochemical investigation of the aerial parts of Verbascum undulatum, a new iridoid glycoside, 6-O-[3-O-(trans-feruloyl)-?-L-rhamnopyranosyl] aucubin (1) and a new verbascoside derivative, 6-O-acetyl-martynoside (2) were isolated. These structures were determined by spectral methods, mainly by 1D and 2D NMR spectroscopy.

P. Magiatis; S. Mitaku; E. Tsitsa; A. L. Skaltsounis; C. Harvala

1998-01-01

31

Iridoid glycosides of Chelone glabra (Scrophulariaceae) and their sequestration by larvae of a sawfly, Tenthredo grandis (Tenthredinidae)  

Microsoft Academic Search

Analysis ofChelone glabra (Scrophulariaceae) by gas chromatography showed that leaves of this plant contained primarily the iridoid glycoside catalpol, and in a few individuals some aucubin was also detected. There was no difference in the iridoid glycoside content of damaged compared to undamaged plants, nor was there a difference between plants collected from a population in Leverett, Massachusetts, and those

M. Deane Bowers; Kenneth Boockvar; Sharon K. Collinge

1993-01-01

32

Variation in iridoid glycosides in a population of Plantago patagonica Jacq. (Plantaginaceae) in Colorado  

Microsoft Academic Search

Plantago patagonica from plants grown in a greenhouse and from a field population in Boulder, Colorado, were sampled for iridoid glycosides. Both aucubin and catalpol were found in P. patagonica, however, not all individual plants contained detectable amounts of both these compounds. Plants grown in the greenhouse (n=8) contained means of 0.26% (±0.04 S.E.) aucubin and 0.23% (±0.05 S.E.) catalpol,

M. Deane Bowers

1996-01-01

33

Iridoid glycosides from Alonsoa meridionalis.  

PubMed

A new iridoid glucoside has been isolated from the Chilean native Alonsoa meridionalis (L.f.) Kuntze. Its structure has been assigned as 6'-O-?-d-glucopyranosyl-8-O-acetylharpagide (1) by using spectroscopic methods. Harpagoside (2), laterioside (3) and verbascoside (4) were also identified. PMID:24735384

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

2014-01-01

34

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

35

Capillary high-performance liquid chromatography with mass spectrometry for simultaneous determination of major flavonoids, iridoid glucosides and saponins in Flos Lonicerae  

Microsoft Academic Search

Flos Lonicerae, a traditional herbal medicine, has been used in China to treat some inflammatory disease. Several different classes of compounds have been separated from the herb to assess their pharmacological activities. Among these classes, flavonoids, iridoid glycosides and saponins have been well studied and may be responsible for its clinical application. Therefore, quality control of Flos Lonicerae is an

Jun Chen; Yue Song; Ping Li

2007-01-01

36

Occurrence of iridoid glycosides in in vitro cultures and intact plants of Scrophularia nodosa L  

Microsoft Academic Search

Shoot, root, and callus cultures of Scrophularia nodosa L. (Scrophulariaceae) were established and cultivated in vitro. Iridoid glycosides, such as harpagoside, aucubin, and catalpol\\u000a were identified by LC-ESI-MS and their contents determined by HPLC. For comparison intact plants of S. nodosa were analysed. In shoot cultures slightly lower amounts of detectable iridoid glycosides (4.36% dry weight) were determined\\u000a than in

Katja Sesterhenn; Melanie Distl; Michael Wink

2007-01-01

37

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

38

Extraction of iridoid glycosides and their determination by micellar electrokinetic capillary chromatography  

Microsoft Academic Search

Several methods for the extraction of two iridoid glycosides, catalpol and aucubin, from the plant matrix (Veronica longifolia leaves) were compared. Pressurized hot water extraction and hot water extraction were the most efficient isolation techniques for both. Pressurized liquid extraction and maceration with various organic solvents were also tested. Relative to the amounts extracted with hot water, ethanol extracted only

Johanna Suomi; Heli Sirén; Kari Hartonen; Marja-Liisa Riekkola

2000-01-01

39

Iridoid and megastigmane glycosides from Phlomis aurea  

Microsoft Academic Search

From the leaves of Phlomis aurea, two new iridoids of unique structures named 3-epiphlomurin (1) and phlomurin (2), a new megastigmane glucoside phlomuroside (3) and a new benzyl alcohol glycoside having the structure benzyl alcohol-O-?-xylopyranosyl-(1?2)-?-glucopyranoside (4) have been isolated together with four known iridoids auroside, lamiide, 8-epiloganin and ipolamiide, two known phenolic glycosides acteoside (verbascoside) and syringin, one known phenylethanoid

Mohamed S. Kamel; Khaled M. Mohamed; Hashim A. Hassanean; Kazuhiro Ohtani; Ryoji Kasai; Kazuo Yamasaki

2000-01-01

40

INHIBITION OF TNF-? AND IL6 PRODUCTION BY AUCUBIN THROUGH BLOCKADE OF NF-?B ACTIVATION IN RBL-2H3 MAST CELLS  

Microsoft Academic Search

Antigen (Ag)-stimulated mast cells induce synthesis and production of cytokines including tumor necrosis factor (TNF)-? and interleukin (IL)-6 with proinflammatory and immune regulatory properties. Expression of TNF-? and IL-6 was regulated by a transcription factor, nuclear factor (NF)-?B. The iridoid glycoside, aucubin, has been found as a natural constituent of many traditional oriental medicinal plants. We studied the effect of

Hyun-Ja Jeong; Hyun-Na Koo; Ho-Jeong Na; Mi-Sun Kim; Seung-Heon Hong; Jung-Woo Eom; Kyung-Suk Kim; Tae-Yong Shin; Hyung-Min Kim

2002-01-01

41

Determination of iridoid glycosides in larvae and adults of butterfly Melitaea cinxia by partial filling micellar electrokinetic capillary chromatography—electrospray ionisation mass spectrometry  

Microsoft Academic Search

.  The iridoid glycosides, methyl catalpol, asperuloside, verbenalin, cinnamoyl catalpol, catalpol and aucubin, were studied from both larvae and adults of butterfly Melitaea cinxia. Special emphasis in the study was put on finding a correlation between the iridoid glycoside content in butterflies and plants. An optimised partial filling micellar electrokinetic capillary chromatographic–electrospray ionisation mass spectrometric (PF-MECC-ESI-MS) method was employed for the

Johanna Suomi; Heli Sirén; Matti Jussila; Susanne K. Wiedmer; Marja-Liisa Riekkola

2003-01-01

42

Inhibition of P-450 by aucubin: is the biological activity of aucubin due to its glutaraldehyde-like aglycone?  

Microsoft Academic Search

The inhibition of ethoxy coumarin O-deethylase (ECOD) activity by aucubin and its aglycone was examined in a microsomal system and in freshly isolated hepatocytes. Aucubin was found to be inactive but the aglycone was found to be a potent time-dependent inhibitor of ECOD activity in both systems. The close structural similarity between the aglycone of aucubin and glutaraldehyde suggests a

Andrew Bartholomaeus; Jonna Ahokas

1995-01-01

43

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

44

Zur Biosynthese des Verbenalins und Aucubins  

Microsoft Academic Search

Summary Verbena officinalis specifically incorporates 2-14C labelled mevalonic acid in the formation of the aglycone moiety of verbenalin (2). In aucubin (6), isolated fromVerbascum thapsus, the incorporation rate is very low and the main part of the activity is located in the sugar moiety.

J. E. S. Hüni; H. Hiltebrand; H. Schmid; D. Gröger; S. Johne; K. Mothes

1966-01-01

45

Simultaneous Analysis of a Mixture of Iridoids in Water Extracts of Plantago asiatica L. by LC  

Microsoft Academic Search

A simple liquid chromatographic method using an ultraviolet detector was developed for the simultaneous quantification of\\u000a a mixture of iridoid glycosides, catalpol, aucubin, and geniposidic acid. By adding a minute amount of trifluoroacetic acid\\u000a into the conventional aqueous acetonitrile mobile phase, the unstable resolution arising from the tautomeric rearrangements\\u000a in the carboxylic group at the 11 position of geniposidic acid

Bong-Hyun Kim; Nam-Kyung Lee; Il-Moo Chang

2009-01-01

46

Unexpected secoiridoid glucosides from Manulea corymbosa.  

PubMed

From an extract of Manulea corymbosa were isolated four known secoiridoid glucosides (1-4), 10 new monoterpenoid esters of secologanol, namely, manuleosides A-I (5-11, 13, and 14) and dimethyl rhodanthoside A (12), and four new phenylpropanoid esters of carbocyclic iridoid glucosides, manucorymbosides I-IV (15-18). Also, the caffeoyl phenylethanoid glycoside verbascoside was isolated. The presence of secoiridoids apparently derived from loganic acid in the family Scrophulariaceae is unprecedented and greatly unexpected. PMID:24328160

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

2014-03-28

47

Further flavonol and iridoid glycosides from Ajuga remota aerial parts  

Microsoft Academic Search

Five new iridoid glycosides characterised as 6-keto-8-acetylharpagide (1), 6,7-dehydro-8-acetylharpagide (2), 7,8-dehydroharpagide (3), 8-acetylharpagide-6-O-?-glucoside (4), harpagide-6-O-?-glucoside (5) together with three flavonol glycosides, myricetin 3-O-rutinoside-4?-O-rutinoside (6), myricetin 3-O-rutinoside-3?-O-rutinoside (7) and isorhamnetin 3-O-rutinoside-7-O-rutinoside-4?-O-?-glucoside (8) have been isolated from the aerial parts of Ajuga remota. Also isolated were two known compounds ajugarin IV and ajugarin V. Their structures were established using spectroscopic methods including

LAWRENCE ONYANGO AROT Manguro; JOSEPH ACHOLA Ogur; DENNIS MAGIO Okora; SAMUEL OTIENO Wagai; PETER Lemmen

2007-01-01

48

Iridoidal glycosides from Jasminum sambac  

Microsoft Academic Search

Besides a known trimeric iridoidal glycoside, sambacoside A, five new oligomeric iridoidal glycosides, molihuasides A-E were isolated from the flowers of Jasminum sambac. Their structures were determined by spectral and chemical evidence. Among them, molihuasides A and C-E are new dimeric iridoidal glycosides and molihuaside B is a new trimeric iridoidal glycoside.

Ying-Jun Zhang; Yu-Qing Liu; Xiang-Yu Pu; Chong-Ren Yang

1995-01-01

49

Flavonol and iridoid glycosides of Ajuga remota aerial parts  

Microsoft Academic Search

Six flavonol glycosides characterised as myricetin 3-O-?-rhamnosyl-(1??2?)-?-rhamnoside-3?-O-?-rhamnoside, 5?-O-methylmyricetin 3-O-[?-rhamnosyl (1??2?)][?-rhamnosyl (1???4?)]-? -glucoside-3?-O-?-glucoside, 5?-O-methylmyricetin 3-O-?-rhamnosyl (1??2?)-?-rhamnoside 3?-O-?-galactoside, kaemferol 3-O-rutinoside-7-O-rutinoside, myricetin 3-O-rutinoside-3?-O-?-rhamnoside, myricetin 3-O-?-glucosyl (1??2?)-?-glucoside-4?-O-?-glucoside together with two iridoid glycosides identified as 6,8-diacetylharpagide and 6,8-diacetylharpagide-1-O-?-(3?,4?-di-O-acetylglucoside) have been isolated from extract of Ajuga remota aerial parts. Also isolated from the same extract were known compounds; kaempferol 3-O-?-rhamnoside, quercetin 3-O-?-glucoside, quercetin 3-O-rutinoside, 8-acetylharpagide, ajugarin

Lawrence O. Arot Manguro; Samuel Otieno Wagai; Peter Lemmen

2006-01-01

50

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

51

A caffeoyl phenylethanoid glycoside from plantago myosuros  

Microsoft Academic Search

From Plantago myosuros, the iridoid glucoside, aucubin was isolated, together with the caffeoyl phenylethanoid glycosides, plantalloside and verbascoside. Plantalloside is a new verbascoside analogue with a ?-allopyranosyl moiety. The structure was elucidated by NMR spectroscopy.

Henrik Franzyk; Tommy Lykke Husum; Søren Rosendal Jensen

1998-01-01

52

Iridoid glycosides of Cornus canadensis  

Microsoft Academic Search

The iridoid glycosides scandoside, scandoside methyl ester, monotropein, and galioside were found in Cornus canadensis from several widely distributed collection sites. Cornin and hastatoside were isolated from C. nuttallii. No iridoids were found in C. stolonifera, that instead yielded cornoside and halleridone, also independent of collection location. The results were compared with previous studies and current phylogenetic work on the

Frank R Stermitz; Robert E Krull

1998-01-01

53

Effects of iridoids on lipoxygenase and hyaluronidase activities and their activation by beta-glucosidase in the presence of amino acids.  

PubMed

Enzyme inhibitory activities of 14 iridoids previously obtained from two Malaysian medicinal plants, Saprosma scortechinii and Rothmannia macrophylla, were evaluated in vitro using soybean lipoxygenase and bovine testis hyaluronidase. Most of the iridoids, including asperulosidic acid, paederosidic acid, and an epimeric mixture of gardenogenins A and B, did not show any effect on the enzyme activities, except for the bis-iridoids, which inhibited the lipoxygenase activity with their IC(50) values of approximately 1.3 times that of a known inhibitor, fisetin. Structural modification of asperulosidic acid and paederosidic acid through enzymatic hydrolysis by beta-glucosidase resulted in their inhibition towards the enzyme activities, and these activities were enhanced by the presence of some amino acids (lysine, leucine or glutamic acid) or ammonium acetate. Mixtures of gardenogenins A and B; isomers of non-glucosidic iridoids, incubated with amino acid or ammonium acetate did not show any inhibitory effect on the enzyme activities during the 6 h incubation period, except for lysine where spontaneous reaction between the iridoids and amino acid resulted in the inhibition of lipoxygenase activity. The results from these biomimetic reactions suggested that the iridoid aglycons and the intermediates formed by these reactive species could inhibit the enzyme activities, and thus substantiate previous reports that the formation of iridoidal aglycons is a prerequisite for the iridoid glycosides to demonstrate some of the biological activities. In addition, the results also indicated that it is worthwhile to further explore these intermediates as potential anti-inflammatory agents. PMID:12612446

Ling, Sui-Kiong; Tanaka, Takashi; Kouno, Isao

2003-03-01

54

Chemotaxonomy of iridoids in Linaria vulgaris.  

PubMed

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

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

2007-11-01

55

Chemotaxonomy of iridoids in Linaria vulgaris  

Microsoft Academic Search

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

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

2007-01-01

56

Antioxidant and pancreas-protective effect of aucubin on rats with streptozotocin-induced diabetes  

Microsoft Academic Search

Oxidative stress has been suggested as a contributory factor in development and complication of diabetes. The aim of the present study was to determine the protective effect of aucubin on lipid peroxidation and activities of antioxidant defense systems and to conduct immunohistochemical evaluation of pancreas in streptozotocin-induced diabetic rats. Lipid peroxidation was determined by assessing the concentration of malondialdehyde and

Lei Jin; Hong-Yu Xue; Li-Ji Jin; Shu-Ying Li; Yong-Ping Xu

2008-01-01

57

Aucubin modulates Bcl2 family proteins expression and inhibits caspases cascade in H 2 O 2 -induced PC12 cells  

Microsoft Academic Search

In this study, the effect of aucubin on H2O2-induced apoptosis was studied by using a rat pheochromocytoma (PC12) cell line. We have analyzed the apoptosis of H2O2-induced PC12 cells, H2O2-induced apoptosis appeared to correlate with lower Bcl-2 expression, higher Bax expression and sequential activation of caspase-3\\u000a leading to cleavage of poly-ADP-ribose polymerase (PARP). Aucubin not only inhibited lower Bcl-2 expression,

Hong Yu Xue; Dong Yan Niu; Gui Zhen Gao; Qiu Ye Lin; Li Ji Jin; Yong Ping Xu

2011-01-01

58

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

2004-01-01

59

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

60

Megastigmane glucosides from Stachys byzantina  

Microsoft Academic Search

From the aerial parts of Stachys byzantina, two new megastigmane glucosides, byzantionosides A and B, were isolated, together with the known glycosides, icariside B2, blumeol C glucoside, (6R, 9R)- and (6R, 9S)-3-oxo-?-ionol glucosides and verbascoside. The structures of the new compounds have been elucidated by spectroscopic means.

Yoshio Takeda; Hongjie Zhang; Toshiya Masuda; Gisho Honda; Hideaki Otsuka; Ekrem Sezik; Erdem Yesilada; Handong Sun

1997-01-01

61

Andrographidine G, a new flavone glucoside from Andrographis paniculata.  

PubMed

A new flavone glucoside, andrographidine G (1), was isolated from Andrographis paniculata together with 13 known compounds, including flavonoids, diterpenoids, and iridoids. The structure of 1 was established by spectroscopic and spectrometric techniques, including HR-ESI-TOF-MS, 1D and 2D NMR, and chemical methods. The known compounds were identified as andrographidine A (2), (2R)-5-hydroxy-7,8-dimethoxyflavanone-5-O-beta-D-glucopyranoside (3), acanthoside B (4), neoandrographiside (5), andropanoside (6), andrographiside (7), andrographolide (8), 14-deoxy-11,12-didehydroandrographiside (9), 14-deoxy-11,12-didehydroandrographolide (10), procumbide (11), procumboside (12), 6-epi-8-O-acetylharpagide (13), and curvifloruside F (14). PMID:23678804

Hapuarachchi, Swarna D; Ali, Zulfiqar; Abe, Naohito; Sugandhika, Suresh T; Sandun, Senerath T P; Khan, Ikhlas A

2013-03-01

62

Anti-Inflammatory Iridoids of Botanical Origin  

PubMed Central

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

Viljoen, A; Mncwangi, N; Vermaak, I

2012-01-01

63

The experimental study of Cortex Eucommiae on meridian tropsim: The distribution study of aucubin in rat tissues  

Microsoft Academic Search

Meridian tropism (MT) theory is a core principle of traditional Chinese medicine (TCM) theories and plays an essential role in instructing clinical pharmacy. The scientific explanation of MT theory will certainly further promote the reasonable, effective application of TCM. In view of the MT of Cortex Eucommiae (CE), aucubin (AU), the effective component of CE, was appointed and observed its

Ye Zhao; Yang Li; Xiang Wang; Wenji Sun

2008-01-01

64

Inhibitory Effect of Aucubin Isolated from Eucommia ulmoides against UVB-Induced Matrix Metalloproteinase-1 Production in Human Skin Fibroblasts  

Microsoft Academic Search

Of 30 herbal plants tested, the methanol extracts of Eucommia ulmoides (52%), Evodia officinalis (45%), and Pleuropterus multiflorus (41%) each showed a potent inhibitory effect on the matrix metalloprotei- nase-1 (MMP-1) production in ultraviolet B (UVB)- irradiated human fibroblasts. Aucubin was isolated as the MMP-1 inhibitor from E. ulmoides, and significantly suppressed the production of MMP-1 by nearly 57% compared

Jin-Nyoung HO; Yoo-Hyun LEE; Yun-Dong LEE; Woo-Jin JUN; Hye-Kyung KIM; Bum-Shik HONG; Dong-Hoon SHIN; Hong-Yon CHO

2005-01-01

65

Verbascoside B — A minor iridoid of Verbascum georgicum  

Microsoft Academic Search

By preparative PC of the previously purified total iridoid material followed by chromatography on a column of silica, a new\\u000a minor iridoid — verbascoside B (I) — has been isolated in the form of an amorphous substance with [?]D ?108 ± 4 (c 0.12; methanol). The structure of (I), corresponding to 6-?-L-rhamnopyranosyldecinnamoylglobularinin, has been\\u000a shown on the basis of a

L. S. Arutyunyan; É. Yu. Agababyan; V. A. Mnatsakanyan

1983-01-01

66

Distribution of iridoids in different populations of Physostegia virginiana and some remarks on iridoids from Avicennia officinalis and Scrophularia ningpoensis  

Microsoft Academic Search

Two subspecies of Physostegia virginiana from seven different origins were investigated for iridoid glycosides. The plant material included the authentic sources of ‘deoxyloganic acid’, isolated in 1970 by one of the authors. This substance has now been identified as a 2.6:1 mixture of 7-deoxy-8-epiloganic acid and 10-deoxygeniposidic acid. Additionally, we isolated 14 known compounds and three new iridoids: stegioside I

Robert Nass; Horst Rimpler

1996-01-01

67

Three pyrone glucosidic derivatives from Conyza albida.  

PubMed

Three new pyrone glucosidic derivatives, together with the known pyromeconic acid glucoside, three acytelenes and two eudesmanes, were obtained from the aerial parts of Conyza albida. The structures were elucidated by high field NMR spectroscopy. PMID:12143010

Ahmed, Ahmed A; Mohamed, Abou El-Hamd; Tzakou, Olga; Gani, Anastasia; Yannitsaros, Artemios; El-Maghraby, Mohamed A; Hassan, Mohamed E; Zeller, Klaus-Peter

2002-07-01

68

A Comparison of Sample Preparation Techniques for Quantifying Iridoid Glycosides Sequestered by Lepidopteran Larvae  

Microsoft Academic Search

This study compared different methods of tissue preparation for extraction of iridoid glycosides sequestered by three species\\u000a 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

Evan C. Lampert; M. Deane Bowers

2011-01-01

69

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

70

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, Raphael; Ilc, Tina; Verpoorte, Robert; Oksman-Caldentey, Kirsi-Marja; Martinoia, Enrico; Bouwmeester, Harro; Goossens, Alain; Memelink, Johan; Werck-Reichhart, Daniele

2014-01-01

71

Studies of mammalian glucoside conjugation  

PubMed Central

The mammalian glucoside-conjugation pathway was studied by using p-nitrophenol as the model substrate and mouse liver microsomal preparations as the source of enzyme. The microsomal preparations supplemented with UDP-glucose glucosylated p-nitrophenol; p-nitrophenyl glucoside was identified by chromatography in six solvent systems. The unsolubilized glucosyltransferase of fresh microsomal preparations did not follow the usual Michaelis–Menten kinetics and was easily inhibited by many steroids. All the steroids tested inhibited glucosylation of p-nitrophenol to a greater degree than glucuronidation of p-nitrophenol when assayed in the same microsomal preparations. The steroids inhibited glucosylation with the following decreasing effectiveness: pregnan-3?-ol-20?-one (3?-hydroxypregnan-20-?-one)>oestradiol-17? 3-methyl ether>oestradiol-17?>oestriol>pregnane-3?,20?-diol>oestrone. Pregnan-3?-ol-20?-one, pregnane-3?,20?-diol and oestrone had negligible effect on glucuronidation. PMID:4725039

Gessner, T.; Jacknowitz, A.; Vollmer, C. A.

1973-01-01

72

Iridoid glycosides and glycosidic constituents from Eriophyton wallichii Benth.  

PubMed

C?-iridoid glycosides, wallichiisides A-C, and four dimers, wallichiisides D-G, together with 13 known glycosidic compounds, were isolated from whole plants of Eriophyton wallichii Benth. Their structures were elucidated by spectroscopic methods and comparison with literature values. Four of these compounds showed moderate DPPH free radical scavenging activity. PMID:21601897

Fan, Qiu-Ling; Tan, Chang-Heng; Liu, Jing; Zhao, Ming-Ming; Han, Fu-Sen; Zhu, Da-Yuan

2011-10-01

73

Cucurbitacin glucosides from Citrullus colocynthis  

Microsoft Academic Search

A new cucurbitacin glucoside 2-O-?-D-glucopyranosyl-16?-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-?-D-glucopyranosyl-cucurbitacin B (arvenin I) (2) and 2,25-di-O-?-D-glucopyranosyl-cucurbitacin L (3) are reported for the first time from this species.

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

2006-01-01

74

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

75

A new isoflavone glucoside from Pterocarpus santalinus.  

PubMed

A new isoflavone glucoside (1) together with the known santal has been isolated from the heartwood of Pterocarpus santalinus. Based on spectral methods, the structure of the new compound was elucidated as 4',5-dihydroxy 7-O-methyl isoflavone 3'-O-beta-D-glucoside. PMID:11256696

Krishnaveni, K S; Srinivasa Rao, J V

2000-01-01

76

Enzymatic Synthesis of Novel Phloretin Glucosides  

PubMed Central

A UDP-glycosyltransferase from Bacillus licheniformis was exploited for the glycosylation of phloretin. The in vitro glycosylation reaction confirmed the production of five phloretin glucosides, including three novel glucosides. Consequently, we demonstrated the application of the same glycosyltransferase for the efficient whole-cell biocatalysis of phloretin in engineered Escherichia coli. PMID:23542617

Pandey, Ramesh Prasad; Li, Tai Feng; Kim, Eun-Hee; Yamaguchi, Tokutaro; Park, Yong Il; Kim, Joong Su

2013-01-01

77

Antioxidative iridoid glycosides and phenolic compounds from Veronica peregrina  

Microsoft Academic Search

Eight iridoid glycosides and four phenolic compounds were isolated from the EtOAc soluble fraction of Veronica peregrina MeOH extract as the radical scavengers for antioxidant activity. The compounds were identified as protocatechuic acid (1), luteolin (2), veronicoside (3), minecoside (4), specioside (5), amphicoside (6), catalposide (7), 6-O-cis-p-coumaroyl catalpol (8), p-hydroxy benzoic acid methyl ester (9), verproside (10), verminoside (11), and

Jong Hwan Kwak; Hyun Jung Kim; Kwang Ho Lee; Se Chan Kang; Ok Pyo Zee

2009-01-01

78

A mutagenic new iridoid in the water extract of catalpae fructus.  

PubMed

A mutagenic principle in the water extract from Catalpae Fructus (originated from Catalpa ovata G. DON) (Bignoniaceae) was isolated and characterized as a new iridoid named catalpin. The iridoid exhibited mutagenic activity towards Salmonella typhimurium strain TA100 in the presence and absence of rat liver homogenate (S9) mix in Ames' test. PMID:2692858

Nozaka, T; Watanabe, F; Ishino, M; Morimoto, I; Kondoh, H; Koyama, K; Natori, S

1989-10-01

79

Effect of Iridoid Glycoside Content on Oviposition Host Plant Choice and Parasitism in a Specialist Herbivore  

Microsoft Academic Search

The Glanville fritillary butterfly Melitaea cinxia feeds upon two host plant species in Å land, Finland, Plantago lanceolataand Veronica spicata, both of which produce iridoid glycosides. Iridoids are known to deter feeding or decrease the growth rate of many generalist insect herbivores, but they often act as oviposition cues to specialist butterflies and are feeding stimulants to their larvae. In

Marko Nieminen; Johanna Suomi; Saskya Van Nouhuys; Pauliina Sauri; Marja-Liisa Riekkola

2003-01-01

80

EFFECT OF IRIDOID GLYCOSIDE CONTENT ON OVIPOSITION HOST PLANT CHOICE AND PARASITISM IN A SPECIALIST HERBIVORE  

Microsoft Academic Search

Abstract—The Glanville fritillary butterfly Melitaea cinxiafeeds upon two host plant species in ? Aland, Finland, Plantago lanceolataand Veronica spicata, both of which produce iridoid glycosides. Iridoids are known,to deter feeding or de- crease the growth rate of many generalist insect herbivores, but they often act as oviposition cues to specialist butterflies and are feeding stimulants to their larvae. In this

MARKO NIEMINEN; JOHANNA SUOMI; SASKYA VAN NOUHUYS; PAULIINA SAURI; MARJA-LIISA RIEKKOLA

2003-01-01

81

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

Microsoft Academic Search

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

Gunther Willinger; Susanne Dobler

2001-01-01

82

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

83

Four new bis-iridoids isolated from the traditional Tibetan herb Pterocephalus hookeri.  

PubMed

Pterocenoids A-E (1-4), which Pterocenoids A(1) is one novel dimer containing a pyridine monoterpene alkaloid; and Pterocenoids B-E (2-4) are rare arranged non-glycosidic bis-iridoids were isolated from Pterocephlus hookeri. The structures of the compounds were established by 1D and 2D NMR spectroscopy and mass spectrometry. All bis-iridoids isolated from P. hookeri were found to possess secoiridoid/iridoid subtype skeletons. Hence, bis-iridoids can be regarded as the chemotaxonomic markers of P. hookeri. The origins of the new bis-iridoids (1-4) were postulated and their activities of inhibition of the NF-?B pathway were assayed and compounds 1-3 showed moderate activity in inhibiting NF-?B. PMID:25065705

Wu, Ying-Chun; Guo, Chen-Xu; Zhu, Yuan-Zhang; Li, Yi-Ming; Guo, Fu-Jiang; Zhu, Guo-Fu

2014-10-01

84

Quassinoid glucosides from seeds of Brucea amarissima.  

PubMed

Quassinoid glucosides, javanicosides I, J, K and L, were isolated from the seeds of Brucea amarissima (Lour.) Desv. ex B. A. Gomes (Simaroubaceae), along with two known quassinoids, i.e. bruceins D and E, and seven known quassinoid glucosides, yadanziosides B, C, E, I and K, bruceoside B and yadanzigan. Their structures were elucidated by analysis of the spectral data and chemical evidence. PMID:15541747

Kim, Ik Hwi; Hitotsuyanagi, Yukio; Takeya, Koichi

2004-12-01

85

Fate of iridoid glycosides in different life stages of the Buckeye, Junonia coenia (Lepidoptera: Nymphalidae)  

Microsoft Academic Search

The buckeye butterfly,Junonia coenia (Lepidoptera: Nymphalidae), specializes on plants that contain iridoid glycosides. To determine the fate of these compounds in larvae, pupae, and adults of this species, we reared larvae on artificial diets with and without iridoid glycosides, and on leaves of a host plant,Plantago lanceolata (Plantaginaceae). Quantification by gas chromatography showed that newly molted third-, fourth-, and fifth-instar

M. Deane Bowers; Sharon K. Collinge

1992-01-01

86

Determination of Iridoid Glycosides from Four Turkish Lamium Species by HPLC-ESI\\/MS  

Microsoft Academic Search

An HPLC-ESI\\/MS method that enables fast detection and identification of iridoid glycosides is described. Eleven iridoid glycosides known to occur in the genus Lamium -lamalbide, sesamoside, 6- ?-OH ipolamiide, shanzhiside methyl ester, dehydropenstemoside, barlerin (= 8-O-acetylshanzhiside methyl ester), 6-O-syringyl-8-O-acetylshanzhiside methyl ester, lamerioside, lamiide, eriobioside, and ipolamiide, were identified by means of their retention time and ESI\\/MS data. This method was

Turk J Chem; Erhan PALASKA

87

Androechin, a new chalcone glucoside from Andrographis echioides.  

PubMed

A new chalcone glucoside, androechin, and a known flavone glucoside, echioidinin 5-O-glucoside, were isolated from the whole plant of Andrographis echioides. Androechin was characterized as 2,2',6'-trihydroxy-4'-methoxychalcone 2'-O-beta-D-glucopyranoside by spectral and chemical studies. PMID:11355769

Jayaprakasam, B; Gunasekar, D; Rao, K V; Blond, A; Bodo, B

2001-01-01

88

Androechin, A New Chalcone Glucoside from Andrographis Echioides  

Microsoft Academic Search

A new chalcone glucoside, androechin, and a known flavone glucoside, echioidinin 5-O-glucoside, were isolated from the whole plant of Andrographis echioides. Androechin was characterized as 2,2?,6?-trihydroxy-4?-methoxychalcone 2?-O-?-D-glucopyranoside by spectral and chemical studies.

B. Jayaprakasam; D. Gunasekar; K. V. Rao; A. Blond; B. Bodo

2001-01-01

89

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

90

Comparison of pharmacokinetic behavior of two iridoid glycosides in rat plasma after oral administration of crude Cornus officinals and its jiuzhipin by high performance liquid chromatography triple quadrupole mass spectrometry combined with multiple reactions monitoring mode  

PubMed Central

Objective: The present study examined the pharmacokinetic profiles of two iridoid glycosides named morroniside and loganin in rat plasma after oral administration of crude and processed Cornus officinals. Materials and Methods: A rapid, selective and specific high-performance liquid chromatography/electrospray ionization tandem mass spectrometry with multiple reactions monitoring mode was developed to simultaneously investigate the pharmacokinetic profiles of morroniside and loganin in rat plasma after oral administration of crude C. officinals and its jiuzhipin. Results: The morroniside and loganin in crude and processed C. officinals could be simultaneously determined within 7.4 min. Linear calibration curves were obtained over the concentration ranges of 45.45-4800 ng/mL for all the analytes. The intra-and inter-day precisions relative standard deviation was lesser than 2.84% and 4.12%, respectively. Conclusion: The pharmacokinetic parameters of two iridoid glucosides were also compared systematically between crude and processed C. officinals. This paper provides the theoretical proofs for further explaining the processing mechanism of Traditional Chinese Medicines. PMID:24914290

Chen, Xiaocheng; Cao, Gang; Jiang, Jianping

2014-01-01

91

Castanospermine-glucosides as selective disaccharidase inhibitors.  

PubMed

Castanospermine (CS) is a potent but non-selective inhibitor of many glycohydrolases including the intestinal disaccharidases. Several CS-glucosides were synthesized to investigate the effect of an attached glucopyranosyl residue on the potency and selectivity of CS toward inhibition of intestinal disaccharidases. 8 alpha-glucosyl-CS and 7 alpha-glucosyl-CS were nearly as potent against sucrase activity as CS (IC50 values = 30, 40, and 20 nM respectively) but were 1/50 or less as potent as CS against lactase and trehalase activities. 8 beta-glucosyl-CS was 1/20 to 1/140 as potent as CS and 1 alpha-glucosyl-CS was 1/57 to 1/1500 as potent as CS against disaccharidase activities. 1 alpha-glc-CS was less selective than CS, whereas the other CS-glucosides were more selective. 7 alpha-glc-CS and 8 alpha-glc-CS were the most sucrase selective and were particularly ineffective against trehalase and lactase activities. 8 beta-glc-CS was similar to CS except for relatively weaker trehalase inhibition. In summary, selectivity toward certain disaccharidases was achieved by glucosylation of CS hydroxyls. However, a simple structural comparison of the CS-glucoside to a disaccharide substrate did not reliably predict which disaccharidase would be more inhibited by the CS-glucoside. PMID:2337410

Rhinehart, B L; Robinson, K M; King, C H; Liu, P S

1990-05-15

92

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

93

Lignan, phenylpropanoid and iridoid glycosides from Pedicularis torta  

Microsoft Academic Search

Six new lignan glucosides, tortosides A-F were isolated from whole plants of Pedicularis torta, along with 11 known compounds, (+)dihydrodehydrodiconiferyl alcohol-4-O-?-l-rhamnopyranoside, (+)-dihydrodehydrodiconiferyl alcohol-4-O-?-d-glucopyranoside, (+)-dihydrodehydrodiconiferyl alcohol-9-O-?-d-glucopyranoside, (+)-dehydrodiconiferyl alcohol-4-O-?-d-glucopyranoside, cistanosides C and D, verbascoside, 8-epiloganin, gardoside methyl ester, shanzhiside methyl ester and loganic acid. On the basis of spectral and chemical evidence, tortosides A-F were determined to be epi-syringaresinol-4?-O-?-d-glucopyranoside, 5,5?-dimethoxylariciresinol-4?-O-?-d-glucopyranoside, 5?,5?-demethylsyringaresinol-4?-O-?-d-glucopyranoside, (+)-dehydrodiconiferyl

Wang Changzeng; Jia Zhongjian

1997-01-01

94

Antioxidative iridoid glycosides and phenolic compounds from Veronica peregrina.  

PubMed

Eight iridoid glycosides and four phenolic compounds were isolated from the EtOAc soluble fraction of Veronica peregrina MeOH extract as the radical scavengers for antioxidant activity. The compounds were identified as protocatechuic acid (1), luteolin (2), veronicoside (3), minecoside (4), specioside (5), amphicoside (6), catalposide (7), 6-O-cis-p-coumaroyl catalpol (8), p-hydroxy benzoic acid methyl ester (9), verproside (10), verminoside (11), and chrysoeriol 7-glucuronide (12) by spectroscopic analysis. All compounds except for 1 and 2 were isolated for the first time from this plant. The antioxidant activity was evaluated by the ORAC(Oxygen Radical Absorbance Capacity) assay, which measures scavenging activity against peroxy radicals induced by 2,2'-azobis (2-methoxypropion-amidine) dihydrochloride, and the ORAC value is expressed as relative trolox equivalent. Compounds 2, 4, 5, 6, 8, and 12 exhibited potent antioxidant activity, and compounds 1, 11 had similar activity with trolox, whereas the other compounds showed weaker activity than trolox. PMID:19280150

Kwak, Jong Hwan; Kim, Hyun Jung; Lee, Kwang Ho; Kang, Se Chan; Zee, Ok Pyo

2009-02-01

95

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

96

A new acylated isoflavone glucoside from Pterocarpus santalinus.  

PubMed

Phytochemical investigation on the constituents of heartwood of Pterocarpus santalinus resulted in the isolation of a new acylated isoflavone glucoside. The structure of the new compound was elucidated on the basis of spectral studies as 4',5-dihydroxy-7-O-methyl isoflavone 3'-O-D-(3''-E-cinnamoyl)glucoside. PMID:10993243

Krishnaveni, K S; Srinivasa Rao, J V

2000-09-01

97

Hirtionosides A-C, gallates of megastigmane glucosides, 3-hydroxyoctanoic acid glucosides and a phenylpropanoid glucoside from the whole plants of Euphorbia hirta.  

PubMed

From the 1-BuOH-soluble fraction of a MeOH extract of Euphorbia hirta, collected in the Okinawa islands, three new megastigmane glucoside gallates, named hirtionosides A-C, 3-hydroxyoctanoic acid glucosides and a phenylpropanoid glucoside were isolated along with 15 known compounds. The structures of the new compounds were elucidated by detailed analysis of physical data, including one- and two-dimensional NMR spectra, and those of known compounds were determined by comparison of physico-chemical data with those reported in the literature. The absolute structures of the megastigmanes were determined by comparison of NMR data and Cotton effects in the CD spectra. The modified Mosher's method was applied to determine the absolute structure of the chiral center in 3-hydroxyoctanoic acid. The DPPH radical-scavenging properties of megastigmane glucoside gallates were assayed and, as expected, they showed moderate activity. PMID:22836810

Nomoto, Yuya; Sugimoto, Sachiko; Matsunami, Katsuyoshi; Otsuka, Hideaki

2013-04-01

98

[Simultaneous determination of five iridoids in gentianae macrophyllae radix and their local variety by HPLC].  

PubMed

This study aims to establish a new method for quality evaluation of Gentianae Macrophyllae Radix by simultaneous determination of five iridoids (loganic acid, 6'-O-beta-D-glucopyranosylgentiopicroside, swertiamarin, gentiopicroside, sweroside), and to detect five iridoids in the root of eight species (Gentiana macrophylla, G. straminea, G. crassicaulis, G. dahurica, G. robusta, G. waltonii, G. lhassica, and G. tibetica). The separation was carried out on a Shiseido SPOLAR C18 (4.6 mm x 250 mm, 5 microm) column eluted with mobile phase of water containing 0.04% formic acid (A) and acetonitrile (B) in a gradient program. The flow rate was 0.8 mL x min(-1). The detect wavelength was set at 240 nm. The column temperature was kept at 30 degrees C. The volume of injection was 5 microL. The five iridoids were well separated with ideal linear correlations. The average recoveries were 97.35% - 106.23%. All the five iridoids were detected in the root of eight species. The contents of same species changed in a somewhat wider range. The contents in root of G. dahurica were lower than that in other species. PMID:25204153

Wu, Jin-Rong; Wu, Li-Hong; Zhao, Zhi-Li; Wang, Zheng-Tao

2014-02-01

99

Habitat climate-dependent gardenieae iridoid productivity revealed through callus induction  

Microsoft Academic Search

Secondary metabolite production in plant cell cultures has long been one of the main targets for the development of new medicinal resources. Contrary to the general observations of reduced productivity in undifferentiated plant cell cultures, we have succeeded in enhancing the productivity of iridoid monoterpenes in the callus and cell suspension cultures not only of Gar- denia jasminoides Ellis (1),

S. Ueda; Y. Iwahashi

1991-01-01

100

A new iridoid from Guettarda grazielae M.R.V. Barbosa (Rubiaceae)  

Microsoft Academic Search

Chromatographic fractionation of the chloroform extracts from the stem bark and stems of Guettarda grazielae resulted in the isolation of a new iridoid (guettardodiol, 1) and the secoiridoid sarracenin (2), described for the first time in this genus. The structural elucidation of these compounds was based on spectroscopic analyses (IR, MS as well as 1-D and 2-D NMR experiments).

Fabyanne S. Moura; Gerson S. Lima; Mario R. Meneghetti; Rosangela P. Lyra Lemos; Lucia M. Conserva

2011-01-01

101

A new sesquiterpene glucoside from Lysionotus pauciflorus.  

PubMed

A new acorane sesquiterpene glucoside, 1R,3S,4R,5R,10R-3,10-dihydroxyacoronene-3-O-beta-D-gluc-oside (1), was isolated from the EtOAc-soluble partition of the ethanol extract of Lysionotus pauciflorus, together with six known compounds, namely p-hydroxybenzoic acid (2), vanillic acid (3). caffeic acid (4). beta-hydroxypropiosyringone (5), alpha,beta-dihydroxypropiosyringone (6), and lyoniresinol (7). The structure of the new compound was elucidated on the basis of spectroscopic methods, including 1D and 2D NMR, and high-resolution MS analysis. The absolute configuration of 1 was determined from CD spectra. When evaluated against several bacterial and fungal strains, and human cancer cell lines, compound 1 and its aglycone were inactive. PMID:25233587

Wen, Yaya; Du, Hongjian; Tu, Yanbei; Luo, Wei; Li, Qin; Li, Yanfang; Liang, Bing

2014-08-01

102

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

103

Studies on the constituents of Catalpa species. IX. Iridoids from the fallen leaves of Catalpa ovata G. Don.  

PubMed

Two new iridoids, 6-O-trans-p-coumaroyl-7-deoxyrehmaglutin A (1) and 6-O-cis-p-coumaroyl-7-deoxyrehmaglutin A (2), were isolated from the fallen leaves of Catalpa ovata G. DON. together with six artifact iridoids (3-8). Their structures were established by spectral analysis. In addition, the scavenging effects of the principal compounds isolated from this plant on 1,1-diphenyl-2-picrylhydrazyl radical-scavenging activity were examined. PMID:15133219

Machida, Koichi; Hishinuma, Erika; Kikuchi, Masao

2004-05-01

104

Rigenolide A, a new secoiridoid glucoside with a cyclobutane skeleton, and three new acylated secoiridoid glucosides from Gentiana rigescens Franch.  

PubMed

Rigenolide A (1), a new secoiridoid glucoside with a cyclobutane skeleton and three new acylated secoiridoid glucosides, 2'-(2,3-dihydroxybenzoyl)-gentiopicroside (2), 2'-(2,3-dihydroxybenzoyl)-swertiamarin (3), 3'-(2,3-dihydroxybenzoyl)-sweroside (4), along with two noriridoids (7 and 8) and two known secoiridoid glucosides (5 and 6), were isolated from Gentiana rigescens Franch. The structures of new compounds were elucidated by extensive spectroscopic analyses. The isolated compounds were evaluated for DPPH free-radical scavenging activity. PMID:23994629

Suyama, Yoshihiro; Kurimoto, Shin-ichiro; Kawazoe, Kazuyoshi; Murakami, Kotaro; Sun, Han-Dong; Li, Shun-Lin; Takaishi, Yoshihisa; Kashiwada, Yoshiki

2013-12-01

105

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

PubMed

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

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

2014-10-01

106

Analysis of eleven iridoid glycosides by micellar electrokinetic capillary chromatography (MECC) and screening of plant samples by partial filling (MECC)–electrospray ionisation mass spectrometry  

Microsoft Academic Search

Of ammonium, lithium and sodium salts of dodecyl sulfate studied as surfactants in the separation of iridoid glycosides by micellar electrokinetic capillary chromatography (MECC), the last one gave the best results. Eleven neutral iridoid glycosides were separated by MECC with sodium dodecyl sulfate as surfactant, and the water–micelle partition coefficients of the compounds were calculated. The separation system was coupled

Johanna Suomi; Susanne K Wiedmer; Matti Jussila; Marja-Liisa Riekkola

2002-01-01

107

Unique cholesteryl glucosides in Helicobacter pylori: composition and structural analysis.  

PubMed Central

A chloroform-methanol-extracted lipid of Helicobacter pylori was studied. Three kinds of glycolipids, accounting for about 25% (wt/wt) of the total lipid, were detected and identified to be cholesteryl glucosides. The structures of two of them were determined to be cholesteryl-alpha-D-glucopyranoside and cholesteryl-6-O-tetrade-canoyl-alpha-D-glucopyranoside, and the plausible structure of the third one was identified as cholesteryl-6-O-phosphatidyl-alpha-D-glucopyranoside. Cholesteryl glucosides are very rare in animals and bacteria. Furthermore, those in H. pylori had an alpha-glycosidic linkage, which is rather unusual for natural glycosides, and a phosphate-linked cholesteryl glycoside like the cholesteryl-6-O-phosphatidyl-alpha-D-glucopyranoside has not been reported previously. As the cholesterol glucosides were detected in strains obtained from diverse geographical locations, the presence of cholesteryl glucosides in H. pylori is a very unique and a characteristic feature of the species. These findings add a new facet to the physiology and biochemistry, especially the cholesterol and glucose metabolism, of H. pylori. Furthermore, the cholesteryl glucosides of H. pylori showed hemolytic activities. PMID:7665522

Hirai, Y; Haque, M; Yoshida, T; Yokota, K; Yasuda, T; Oguma, K

1995-01-01

108

Analysis of eleven iridoid glycosides by micellar electrokinetic capillary chromatography (MECC) and screening of plant samples by partial filling (MECC)-electrospray ionisation mass spectrometry.  

PubMed

Of ammonium, lithium and sodium salts of dodecyl sulfate studied as surfactants in the separation of iridoid glycosides by micellar electrokinetic capillary chromatography (MECC), the last one gave the best results. Eleven neutral iridoid glycosides were separated by MECC with sodium dodecyl sulfate as surfactant, and the water-micelle partition coefficients of the compounds were calculated. The separation system was coupled via a coaxial sheath flow electrospray interface to a mass spectrometer, and the partial filling technique was used in the on-line analysis. Seven plant species belonging to five genera (Plantago, Veronica, Melampyrum, Succisa and Valeriana) were screened for the iridoid glycosides by the new method that was developed. The findings confirmed those of an earlier study on five of the iridoid glycosides. Some new iridoid glycosides were found in Plantago lanceolata, Veronica spicata and V. chamaedrys. PMID:12350101

Suomi, Johanna; Wiedmer, Susanne K; Jussila, Matti; Riekkola, Marja-Liisa

2002-09-13

109

Anti-HBV active flavone glucosides from Euphorbia humifusa Willd.  

PubMed

Thirteen flavone glucosides from the herb of Euphorbia humifusa were isolated and elucidated. Among them, five compounds including apigenin-7-O-?-D-glucopyranoside (2), apigenin-7-O-(6''-O-galloyl)-?-D-glucopyranoside (3), luteolin-7-O-?-D-glucopyranoside (7), luteolin-7-O-(6''-O-trans-feruloyl)-?-D-glucopyranoside (8) and luteolin-7-O-(6''-O-coumaroyl)-?-D-glucopyranoside (9) showed anti-HBV activity in vitro. The structure-activity relationship showed that the parent structure was closely relevant to the anti-HBV activity of these compounds (agigenin>luteolin>quercetin). It was found that the number of glucoside in the structure may significantly influence their activities (flavone monoglucoside>flavone diglucoside) and cytotoxicity (flavone>flavone monoglucoside>flavone diglucoside). In addition, the substitution of acyl group on glucoside may be important to keep the anti-HBV activities of these compounds (galloyl>feruloyl>coumaroyl). PMID:20450964

Tian, Ying; Sun, Li-Min; Liu, Xi-Qiao; Li, Bin; Wang, Qiong; Dong, Jun-Xing

2010-10-01

110

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

Microsoft Academic Search

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

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

2007-01-01

111

Metabolism of conjugated sterols in eggplant. Part 2. Phospholipid : steryl glucoside acyltransferase  

Microsoft Academic Search

A membrane-bound phospholipid : steryl glucoside acyltransferase from Solanum melongena leaves was partially purified and its specificity and molecular as well as kinetic properties were defined. Among the steryl glycosides tested (e.g. typical plant steryl glucosides, steryl galacto - sides and cholesteryl xyloside) the highest activity was found with cholesteryl glucoside, but some structurally related compounds such as sito- and

Anna Potocka; Jan Zimowski

112

21 CFR 573.660 - Methyl glucoside-coconut oil ester.  

Code of Federal Regulations, 2011 CFR

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

2011-04-01

113

21 CFR 178.3600 - Methyl glucoside-coconut oil ester.  

Code of Federal Regulations, 2012 CFR

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

2012-04-01

114

21 CFR 172.816 - Methyl glucoside-coconut oil ester.  

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

2014-04-01

115

21 CFR 172.816 - Methyl glucoside-coconut oil ester.  

Code of Federal Regulations, 2013 CFR

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

2013-04-01

116

21 CFR 172.816 - Methyl glucoside-coconut oil ester.  

Code of Federal Regulations, 2012 CFR

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

2012-04-01

117

21 CFR 573.660 - Methyl glucoside-coconut oil ester.  

Code of Federal Regulations, 2012 CFR

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

2012-04-01

118

21 CFR 178.3600 - Methyl glucoside-coconut oil ester.  

Code of Federal Regulations, 2011 CFR

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

2011-04-01

119

21 CFR 573.660 - Methyl glucoside-coconut oil ester.  

Code of Federal Regulations, 2013 CFR

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

2013-04-01

120

21 CFR 178.3600 - Methyl glucoside-coconut oil ester.  

Code of Federal Regulations, 2013 CFR

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

2013-04-01

121

21 CFR 573.660 - Methyl glucoside-coconut oil ester.  

Code of Federal Regulations, 2010 CFR

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

2010-04-01

122

21 CFR 573.660 - Methyl glucoside-coconut oil ester.  

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

2014-04-01

123

21 CFR 172.816 - Methyl glucoside-coconut oil ester.  

Code of Federal Regulations, 2010 CFR

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

2010-04-01

124

21 CFR 172.816 - Methyl glucoside-coconut oil ester.  

Code of Federal Regulations, 2011 CFR

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

2011-04-01

125

21 CFR 178.3600 - Methyl glucoside-coconut oil ester.  

Code of Federal Regulations, 2010 CFR

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

2010-04-01

126

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

127

Carotenoids and cyanogenic glucosides in saskatoon berries ( Amelanchier alnifolia Nutt.)  

Microsoft Academic Search

The levels of carotenoids (lutein, zeaxanthin and beta-carotene) and cyanogenic glucosides (prunasin and amygdalin) were determined in saskatoon berries of five cultivars, picked at four stages of maturity, at four locations in Manitoba and Alberta, Canada. Lutein was found to be the predominant carotenoid in all the samples analyzed, and in mature (purple) berries ranged from a low value of

G. Mazza; T. Cottrell

2008-01-01

128

Phenolic glucosides from Dendrobium aurantiacum var. denneanum and their bioactivities.  

PubMed

A new 8,4'-oxyneolignane glucoside 1 has been isolated from the stems of Dendrobium aurantiacum var. denneanum together with six known phenolic glucosides 2?7. The structure of the new compound, including its absolute configuration, was determined by spectroscopic and chemical methods as (?)-(7S,8R,7'E)-4-hydroxy-3,3',5,5'-tetramethoxy-8,4'-oxyneolign-7'-ene-7,9,9'-triol 7,9'-bis-O-?-D-glucopyranoside (1). In the in vitro assays, compound 1 and (?)-syringaresinol-4,4'-bis-O-?-D-glucopyranoside (2) showed evident activity against glutamate-induced neurotoxicity in PC12 cells. Shashenoside I (4) showed a selective cytotoxic activity with the IC?? value of 4.17 ?M against the acute myeloid leukemia cell line MV4-11, while it was inactive against 10 other human tumor cell lines. PMID:23702921

Xiong, Liang; Cao, Zhi-Xing; Peng, Cheng; Li, Xiao-Hong; Xie, Xiao-Fang; Zhang, Ting-Mo; Zhou, Qin-Mei; Yang, Lian; Guo, Li

2013-01-01

129

A New Benzofuran Glucoside from Ficus Tikoua Bur  

PubMed Central

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

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

2011-01-01

130

Supinaionosides A and B: megastigmane glucosides and supinanitrilosides A-F: hydroxynitrile glucosides from the whole plants of Euphorbia supina RAFINESQUE.  

PubMed

From whole plants of Euphorbia supina, two new megastigmane glucosides, named supinaionosides A and B (1, 2), six new hydroxynitrile glucosides, named supinanitrilosides A-F (3-8), and six known compounds were isolated. The structures of the new compounds were elucidated on the basis of spectroscopic and chemical evidence. PMID:19652410

Cai, Wen-Hu; Matsunami, Katsuyoshi; Otsuka, Hideaki

2009-08-01

131

Iridoid glycoside-based quantitative chromatographic fingerprint analysis: A rational approach for quality assessment of Indian medicinal plant Gambhari ( Gmelina arborea)  

Microsoft Academic Search

A sensitive, selective and robust qualitative and quantitative densitometric high-performance thin layer chromatographic method was developed and validated for the determination of iridoid glycoside in the aerial part of Gambhari (Gmelina arborea). Iridoid gycoside 6-O-(2?,3?-dibenzoyl)-?-l-rhamnopyranosylcatalpol (IG) was used as a chemical marker for the standardization of G. arborea plant extracts. The separation was performed on aluminum Kieselgel 60F254 TLC plates

Akhilesh K. Yadav; N. Tiwari; P. Srivastava; Subhash C. Singh; K. Shanker; Ram K. Verma; Madan M. Gupta

2008-01-01

132

Crude glycerol glucoside esters of cottonseed oil: Preliminary cost analysis  

Microsoft Academic Search

Glycerol glucoside esters prepared by transglycosylation of starch and glycerol, followed by interesterification with esters\\u000a of cottonseed oil fatty acids, are well suited for use in the steadily growing food emulsifier market. They offer formulators\\u000a and processors a wide range of compositions and physical properties for achieving more effective emulsification without increase\\u000a in cost. Process flowsheets, capital costs, manufacturing costs,

K. M. Decossas; R. O. Feuge; J. L. White

1978-01-01

133

Prenylated xanthone glucosides from Ural's lichen Umbilicaria proboscidea  

Microsoft Academic Search

Two new compounds isolated from an extract of a Central Asian lichen [Umbilicaria proboscidea (L.) Schrader=Syn.: Gyrophora proboscidea (L.) Ach.] are glucosides with mono- and di-prenylated xanthones as the aglycones and a saccharide moiety from two glucoses linked at C-7. The structures were elucidated on the basis of extensive spectroscopic analysis (1D and 2D NMR, MS, IR and UV) and

Tomáš ?ezanka; Jitka Jáchymová; Valery M. Dembitsky

2003-01-01

134

Prenylated xanthone glucosides from Ural's lichen Umbilicaria proboscidea.  

PubMed

Two new compounds isolated from an extract of a Central Asian lichen [Umbilicaria proboscidea (L.) Schrader=Syn.: Gyrophora proboscidea (L.) Ach.] are glucosides with mono- and di-prenylated xanthones as the aglycones and a saccharide moiety from two glucoses linked at C-7. The structures were elucidated on the basis of extensive spectroscopic analysis (1D and 2D NMR, MS, IR and UV) and by hydrolysis. PMID:12560034

Rezanka, Tomás; Jáchymová, Jitka; Dembitsky, Valery M

2003-02-01

135

Preparative isolation and purification of iridoid glycosides from Fructus Corni by high-speed countercurrent chromatography  

PubMed Central

Using a two-phase solvent system composed of dichloromethane–methanol–n-butanol–water–acetic acid (5:5:3:4:0.1, v/v/v/v/v), high-speed countercurrent chromatography was successfully performed for isolation and purification of three iridoid glycosides from Fructus Corni for the first time. From 100 mg of a crude extract of Fructus Corni 7.9 mg of sweroside, 13.1 mg of morroniside, and 10.2 mg of loganin were obtained in less than 3 h with purities of 92.3, 96.3 and 94.2%, respectively. These target compounds were identified by ESI-MS, 1H NMR and 13C NMR. PMID:24899790

Liang, Jinru; He, Jiao; Zhu, Sha; Zhao, Wenna; Zhang, Yongmin; Ito, Yoichiro; Sun, Wenji

2012-01-01

136

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

137

HSCCC Separation of a Stilbene Glucoside from Polygonum Multiflorum  

Microsoft Academic Search

High-speed countercurrent chromatography (HSCCC) was applied to the separation and purification of 2,3,5,4?-tetrahydroxy stilbene-2-O-D-glucoside from dried roots (2.7g) of Polygonum multiflorum. The ethanol extract (240 mg) was first separated with the solvent system composed of ethyl acetate-ethanol-water at a volume ratio of 10:1:10 and the obtained fraction was repurified with the solvent system at the modified volume ratio of 50:1:50.

Xueli Cao; Yu Tian; Tianyou Zhang; Pingniang Shen; Lianhua Zhu; Yoichiro Ito

1998-01-01

138

Cytotoxic naphthoquinones and plumbagic acid glucosides from Plumbago zeylanica.  

PubMed

Two plumbagic acid glucosides, 3'-O-beta-glucopyranosyl plumbagic acid and 3'-O-beta-glucopyranosyl plumbagic acid methylester along with five naphthoquinones (plumbagin, chitranone, maritinone, elliptinone and isoshinanolone), and five coumarins (seselin, 5-methoxyseselin, suberosin, xanthyletin and xanthoxyletin) were isolated from the roots of Plumbago zeylanica. All coumarins were not previously found in this plant. Cytotoxicity of these compounds to various tumor cells lines was evaluated, and plumbagin significantly suppressed growth of Raji, Calu-1, HeLa, and Wish tumor cell lines. PMID:12560036

Lin, Lie-Chwen; Yang, Ling-Ling; Chou, Cheng-Jen

2003-02-01

139

Two new cyanogenic glucosides from the leaves of Hydrangea macrophylla.  

PubMed

Chemical investigation of the ethanol extract of the aerial parts of Hydrangea macrophylla collected in the Sichuan Province of China resulted in the isolation of two new cyanogenic glucosides. Their structures were elucidated as [(2R)-2-?-D-glucopyranosyloxy)-2-(3,4-dimethoxy-phenyl)] acetonitrile (1) and {(2R)-2-[?-D-glucopyranosyl(1-->6)?-D-glucopyranosyloxy]-2-(3-hydroxy-4-methoxy-phenyl)}acetonitrile (2) on the basis of extensive spectroscopic analysis (1D, 2D NMR and HRESIMS) and chemical studies. PMID:22569418

Yang, Chun-Juan; Wang, Zhi-Bin; Zhu, Da-Ling; Yu, Ying; Lei, Yin-Ting; Liu, Yan

2012-01-01

140

New ?-glucosides of caffeoyl quinic acid from the leaves of Moringa oleifera Lam.  

PubMed

Two new caffeoyl quinic acid ?-glucosides, together with three known caffeoyl quinic acids and five known flavonoid glucosides, were isolated from the leaves of Moringa oleifera Lam. The structures of the new compounds were elucidated as 4-O-(4'-O-?-D-glucopyranosyl)-caffeoyl quinic acid (1) and 4-O-(3'-O-?-D-glucopyranosyl)-caffeoyl quinic acid (2) by spectroscopic analyses. PMID:21748486

Kashiwada, Yoshiki; Ahmed, Fakhruddin Ali; Kurimoto, Shin-ichiro; Kim, Sang-Yong; Shibata, Hirofumi; Fujioka, Toshihiro; Takaishi, Yoshihisa

2012-01-01

141

Microbiology (2000), 146, 20392049 Printed in Great Britain Analysis of the -glucoside utilization (bgl)  

E-print Network

80 360 0683. e-mail: mahi!serc.iisc.ernet.in Department of Molecular Reproduction, Development Enterobacteriaceae exhibit substantial differences in their ability to utilize - glucosides such as salicin, arbutin in -glucoside utilization in Escherichia coli (Prasad & Schaefler, 1974; Kricker & Hall, 1987; Parker & Hall

Mahadevan, S.

142

A pair of new atropisomeric cupressuflavone glucosides isolated from Juniperus communis var. depressa  

Microsoft Academic Search

A pair of new atropisomers, (M)- and (P)-cupressuflavone 4?-O-?-d-glucoside, were isolated from Juniperus communis var. depressa, and their absolute structures and axial configurations were determined using 2D NMR and circular dichroism. These are the first reported stable (M)- and (P)-isomers of cupressuflavone glucosides isolated from natural sources.

Yuka Inatomi; Naoki Iida; Hiroko Murata; Akira Inada; Jin Murata; Frank A. Lang; Munekazu Iinuma; Toshiyuki Tanaka; Tsutomu Nakanishi

2005-01-01

143

Glucosides of Coumarinic and o-Coumaric Acids in the Tonka Bean  

Microsoft Academic Search

The beta -glucosides of coumarinic and o-coumaric acids were detected in extracts of cotyledons, exocarps, and seedling leaves of the tonka bean. The existence of these compounds and the presence of a beta -glucosidase having specificity for coumarinyl glucoside suggest that the tonka bean synthesizes coumarin by a pathway similar to the one found in sweetclover.

F. A. Haskins; H. J. Gorz

1963-01-01

144

Glucosides of coumarinic and o-coumaric acids in the tonka bean.  

PubMed

The beta-glucosides of coumarinic and o-coumaric acids were detected in extracts of cotyledons, exocarps, and seedling leaves of the tonka bean. The existence of these compounds and the presence of a beta-glucosidase having specificity for coumarinyl glucoside suggest that the tonka bean synthesizes coumarin by a pathway similar to the one found in sweetclover. PMID:13960882

HASKINS, F A; GORZ, H J

1963-02-01

145

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

PubMed Central

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

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

2013-01-01

146

Oviposition Cues for a Specialist Butterfly–Plant Chemistry and Size  

Microsoft Academic Search

The oviposition choice of an insect herbivore is based on a complex set of stimuli and responses. In this study, we examined\\u000a the effect of plant secondary chemistry (the iridoid glycosides aucubin and catalpol) and aspects of size of the plant Plantago lanceolata, on the oviposition behavior of the specialist butterfly Melitaea cinxia. Iridoid glycosides are known to deter feeding

J. H. Reudler Talsma; A. Biere; J. A. Harvey; S. van Nouhuys

2008-01-01

147

Distribution of GA20-13-O-glucoside and reconversion of [17-D2]GA20-13-O-glucoside in caryopses of Hordeum vulgare L. cv. Himalaya  

Microsoft Academic Search

The distribution of GA20 and GA20-13-O-glucoside was examined in mature caryopses of Hordeum vulgare L. cv. Himalaya. It was shown by GC-MS that GA20-13-O-glucoside is localized mainly in the embryo-containing part of the grain. In order to study the reconversion of GA20-13-O-glucoside during early germination, the glucoside pool of cv. Himalaya was [17-D2]-labelled by feeding [17-D2]GA20. The metabolites of [17-D2]GA20-13-O-glucoside

B. Senns; P. Fuchs; G. Schneider

1999-01-01

148

Cornel Iridoid Glycoside Attenuates Tau Hyperphosphorylation by Inhibition of PP2A Demethylation  

PubMed Central

Aim. The aim of the present study was to investigate the effect of cornel iridoid glycoside (CIG) on tau hyperphosphorylation induced by wortmannin (WT) and GF-109203X (GFX) and the underlying mechanisms. Methods. Human neuroblastoma SK-N-SH cells were preincubated with CIG (50, 100, and 200?µg/ml, resp.) for 24 h and then exposed to 10?µM WT and 10?µM GFX for 3 h after washing out CIG. Immunohistochemistry was used to observe the microtubular cytoskeleton of the cultured cells. Western blotting was used to measure the phosphorylation level of tau protein, glycogen synthase kinase 3? (GSK-3?), and protein phosphatase 2A (PP2A). The activity of PP2A was detected by a biochemical assay. Results. Preincubation of CIG significantly attenuated the WT/GFX-induced tau hyperphosphorylation at the sites of Thr205, Thr212, Ser214, Thr217, Ser396, and PHF-1 and improved the damage of morphology and microtubular cytoskeleton of the cells. CIG did not prevent the decrease in p-AKT-ser473 and p-GSK-3?-ser9 induced by WT/GFX. However, CIG significantly elevated the activity of PP2A by reducing the demethylation of PP2A catalytic subunit (PP2Ac) at Leu309 and the ratio of PME-1/LCMT in the WT/GFX-treated cells. The results suggest that CIG may be beneficial to the treatment of AD. PMID:24454482

Yang, Cui-cui; Kuai, Xue-xian; Li, Ya-li; Zhang, Li; Yu, Jian-chun; Li, Lin; Zhang, Lan

2013-01-01

149

Fragmentation patterns study of iridoid glycosides in Fructus Gardeniae by HPLC-Q/TOF-MS/MS.  

PubMed

Iridoid glycosides (IGs), the major constituents in Fructus Gardeniae, have demonstrated various pharmacological activities, but there is no systematic chemical profile of IGs in Fructus Gardeniae in the published literature until now. Therefore, it is imperative that a rapid and sensitive high-performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry (HPLC-Q/TOF-MS/MS) method is established for comprehensive characterization of IGs in Fructus Gardeniae. Firstly, the fragmentation patterns of six known IGs were investigated and proposed and further concluded the diagnostic fragment ions and characteristic fragmentation pathways. Then, based on the summarized fragmentation patterns and the known compounds in the literatures, the other IGs in Fructus Gardeniae were identified successively. As a result, a total of 20 IGs were identified, of which three pairs of epimers were structurally characterized and differentiated. More importantly, one compound, the isoshanzhiside methyl ester, was tentatively identified as a new compound. The results of this study demonstrate the superiority of HPLC-MS with a high-resolution mass spectrometer for the rapid and sensitive structural elucidation of the multiple groups of constituents in Fructus Gardeniae. Copyright © 2014 John Wiley & Sons, Ltd. PMID:24782425

Fu, Zhiwen; Xue, Rui; Li, Zhixiong; Chen, Mingcang; Sun, Zhaolin; Hu, Yiyang; Huang, Chenggang

2014-12-01

150

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

PubMed

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

Jamieson, Mary A; Bowers, M Deane

2010-01-01

151

Biological activity of a phloroglucinol glucoside derivative from Conyza aegyptiaca.  

PubMed

The phloroglucinol glucoside derivative [2,4-dihydroxy-6-(beta-D-glucopyranosyloxy)phenyl]-butan-1-one (1), roseoside (2), and kaempferol-3-O-beta-D-glucopyranoside (3) were isolated from the aerial parts of Conyza aegyptiaca (L.). To the best of our knowledge, this is the first isolation of compounds 1-3 from C. aegyptiaca. Their structures were determined by spectroscopic techniques including, IR, HR-EIMS, and extensive 500 MHz 1D- and 2D-NMR analyses (1H, 13C NMR, DEPT, 1H-1H COSY, HMQC and HMBC experiments). The antioxidant activity of 1, using the DPPH assay, was investigated; in addition, 1 was investigated against different types of cell lines, including Hep-G2, HCT-116, and RAW 264.7 for its cytotoxic effects. Also, this is the first report on the activity of 1. PMID:19791502

Mahmoud, Ahmed A; Al-Shihry, Shar S; Hegazy, Mohamed-Elamir F

2009-01-01

152

The cyanogenic glucoside composition of Zygaena filipendulae (Lepidoptera: Zygaenidae) as effected by feeding on wild-type and transgenic lotus populations with variable cyanogenic glucoside profiles.  

PubMed

Zygaena larvae sequester the cyanogenic glucosides linamarin and lotaustralin from their food plants (Fabaceae) as well as carry out de novo biosynthesis of these compounds. In this study, Zygaena filipendulae were reared on wild-type Lotus corniculatus and wild-type and transgenic L. japonicus plants with differing content and ratios of the cyanogenic glucosides linamarin and lotaustralin and of the cyanoalkenyl glucosides rhodiocyanoside A and D. LC-MS analyses, free choice feeding experiments and developmental studies were used to examine the effect of varying content and ratios of these secondary metabolites on the feeding preferences, growth and development of Z. filipendulae. Larvae reared on cyanogenic L. corniculatus developed faster compared to larvae reared on L. japonicus although free choice feeding trials demonstrated that the latter plant source was the preferred food plant. Larvae reared on acyanogenic L. corniculatus showed decelerated development. Analysis of different life stages and tissues demonstrate that Z. filipendulae strive to maintain certain threshold content and ratios of cyanogenic glucosides regardless of the composition of the food plants. Despite this, the ratios of cyanogenic glucosides in Z. filipendulae remain partly affected by the ratio of the food plant due to the high proportion of sequestering that takes place. PMID:17175442

Zagrobelny, Mika; Bak, Søren; Ekstrøm, Claus Thorn; Olsen, Carl Erik; Møller, Birger Lindberg

2007-01-01

153

Qualitative and quantitative determination of ten iridoids and secoiridoids in Gentiana straminea Maxim. by LC-UV-ESI-MS.  

PubMed

A simple and accurate HPLC-UV/MS method was developed for the simultaneous determination of ten iridoids and secoiridoids in the roots of Gentiana straminea Maxim. Separations were performed on a Kromasil-C18 column by gradient elution using methanol and water containing phosphoric acid. Analytes were identified by HPLC coupled with ESI-MS experiments. The chromatographic method was validated for selectivity, linearity, precision, limit of detection, limit of quantification, accuracy, and stability. The developed assay could be considered as a suitable quality control method for G. straminea and other "Qinjiao" herbs. PMID:21698511

Wei, Shihu; Zhang, Peicheng; Feng, Xizhi; Kodama, Hiroyuki; Yu, Changyuan; Chen, Guang

2012-01-01

154

Response of generalist and specialist insects to qualitative allelochemical variation  

Microsoft Academic Search

We examined the effects of a set of four biosynthetically related iridoid glycosides, aucubin, catalpol, loganin, and asperuloside, on larvae of a generalist,Lymantria dispar (Lymantriidae), the gypsy moth, and an adapted specialist, the buckeye,Junonia coenia (Nymphalidae). In general,L. dispar grew and survived significantly less well on artificial diets containing iridoid glycoside, compared to a control diet without iridoid glycosides. In

M. Deane Bowers; Gillian M. Puttick

1988-01-01

155

21 CFR 178.3600 - Methyl glucoside-coconut oil ester.  

...INDIRECT FOOD ADDITIVES: ADJUVANTS, PRODUCTION AIDS, AND SANITIZERS Certain Adjuvants and Production Aids § 178.3600 Methyl glucoside-coconut...chapter may be safely used as a processing aid (filter aid) in the manufacture of...

2014-04-01

156

Thesinine-4'-O-beta-D-glucoside the first glycosylated plant pyrrolizidine alkaloid from Borago officinalis.  

PubMed

The glycosylated pyrrolizidine alkaloid, thesinine-4'-O-beta-D-glucoside, has been isolated from the aqueous methanol extract of dried, defatted seeds of Borago officinalis (Boraginaceae). The structure was established by means of spectroscopic and chemical analysis. PMID:12031432

Herrmann, Martina; Joppe, Holger; Schmaus, Gerhard

2002-06-01

157

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

158

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

159

New acetophenone glucosides isolated from extracts of Helichrysum italicum with antiinflammatory activity.  

PubMed

Three new acetophenone glucosides (4-6), three known aglycons (1-3), and a benzo-gamma-pyrone glucoside (7) were isolated from the CH(2)Cl(2), EtOAc, and BuOH extracts from the aerial parts of Helichrysum italicum. All the compounds tested showed antiinflammatory activity in a 12-O-tetradecanoylphorbol 13-acetate (TPA)-induced mouse ear edema test, and the ID(50) value of compound 2, the most active compound, was determined. PMID:11678669

Sala, A; Recio, M C; Giner, R M; Máñez, S; Ríos, J L

2001-10-01

160

(6 S)Hydroxy3-oxo-?-ionol glucosides from Capparis spinosa fruits  

Microsoft Academic Search

Two new (6S)-hydroxy-3-oxo-?-ionol glucosides, together with corchoionoside C ((6S,9S)-roseoside) and a prenyl glucoside, were isolated from mature fruits of Capparis spinosa. The structures were established on the basis of spectroscopic, chiroptic and chemical evidence. In addition, the 13C-resonance of C-9 was found to be of particular diagnostic value in assigning the absolute configuration at that center in ionol glycosides. The

?hsan Çal??; Ay?e Kuruüzüm-Uz; Piergiorgio A. Lorenzetto; Peter Rüedi

2002-01-01

161

New ?-glucosides of caffeoyl quinic acid from the leaves of Moringa oleifera Lam  

Microsoft Academic Search

Two new caffeoyl quinic acid ?-glucosides, together with three known caffeoyl quinic acids and five known flavonoid glucosides,\\u000a were isolated from the leaves of Moringa oleifera Lam. The structures of the new compounds were elucidated as 4-O-(4?-O-?-d-glucopyranosyl)-caffeoyl quinic acid (1) and 4-O-(3?-O-?-d-glucopyranosyl)-caffeoyl quinic acid (2) by spectroscopic analyses.

Yoshiki KashiwadaFakhruddin; Fakhruddin Ali Ahmed; Shin-ichiro Kurimoto; Sang-Yong Kim; Hirofumi Shibata; Toshihiro Fujioka; Yoshihisa Takaishi

162

Identification of glucosides in green beans of Vanilla planifolia Andrews and kinetics of vanilla ?-glucosidase  

Microsoft Academic Search

Natural vanilla is extracted from the fruits of Vanilla planifolia. In the overall vanilla aroma, minor compounds p-cresol, creosol, guaiacol and 2-phenylethanol have a high impact. This is shown by GC-Olfactometry analysis of cured vanilla beans. The presence of ?-D-glucosides of these compounds was investigated, in order to determine if these compounds are derived from glucosides or if they are

Mark J. W. Dignum; Rob van der Heijden; Josef Kerler; Chris Winkel; Rob Verpoorte

2004-01-01

163

Succinyl-coenzyme A: Anthocyanidin 3-glucoside succinyltransferase in flowers of Centaurea cyanus  

Microsoft Academic Search

The acyltransferase from blue flowers of Centaurea cyanus containing succinylated cyanidin 3,5-diglucosides catalysed the transfer of the succinyl moiety from succinyl-CoA to 3-glucosides of cyanidin and pelargonidin, but not to 3,5-diglucosides. Similar results were obtained using the enzyme from pink flowers containing succinylated pelargonidin 3,5-diglucosides. The enzyme also catalysed these anthocyanidin 3-glucosides to malonylate at nearly the same rate as

Masa-atu Yamaguchi; Tatsunori Maki; Takako Ohishi; Ikuo Ino

1995-01-01

164

A monoterpene glucoside and three megastigmane glycosides from Juniperus communis var. depressa.  

PubMed

A new monoterpene glucoside (1) and three new natural megastigmane glycosides (2-4) were isolated along with a known megastigmane glucoside (5) from twigs with leaves of Juniperus communis var. depressa (Cupressaceae) collected in Oregon, U.S.A., and their structures were determined on the basis of spectral and chemical evidence. In addition, the antibacterial activities of the isolated components against Helicobacter pylori were also investigated. PMID:15997135

Nakanishi, Tsutomu; Iida, Naoki; Inatomi, Yuka; Murata, Hiroko; Inada, Akira; Murata, Jin; Lang, Frank A; Iinuma, Munekazu; Tanaka, Toshiyuki; Sakagami, Yoshikazu

2005-07-01

165

Cyanidin-3-Glucoside Ameliorates Ethanol Neurotoxicity in the Developing Brain  

PubMed Central

Ethanol exposure induces neurodegeneration in the developing central nervous system (CNS). Fetal Alcohol Spectrum Disorders (FASD) are caused by ethanol exposure during pregnancy and are the most common nonhereditary cause of mental retardation. It is important to identify agents that provide neuroprotection against ethanol neurotoxicity. Multiple mechanisms have been proposed for ethanol-induced neurodegeneration, and oxidative stress is one of the most important mechanisms. Recent evidence indicates that glycogen synthase kinase 3? (GSK3?) is a potential mediator of ethanol-mediated neuronal death (Luo, 2009). Cyanidin-3-glucoside (C3G), a member of the anthocyanin family, is a potent natural antioxidant. Our previous study suggested that C3G inhibited GSK3? activity in neurons (Chen et al., 2009). Using a third trimester equivalent mouse model of ethanol exposure, we tested the hypothesis that C3G can ameliorate ethanol-induced neuronal death in the developing brain. Intraperitoneal injection of C3G reduced ethanol-meditated caspase-3 activation, neurodegeneration and microglial activation in the cerebral cortex of seven-day-old mice. C3G blocked ethanol-mediated GSK3? activation by inducing the phosphorylation at serine 9 while reducing the phosphorylation at tyrosine 216. C3G also inhibited ethanol-stimulated expression of malondialdehyde (MDA) and p47phox, indicating that C3G alleviated ethanol-induced oxidative stress. These results provide important insight into the therapeutic potential of C3G. PMID:21671257

Ke, Zunji; Liu, Ying; Wang, Xin; Fan, Zhiqin; Chen, Gang; Xu, Mei; Bower, Kimberley A.; Frank, Jacqueline A.; Ou, Xiaoming; Shi, Xianglin; Luo, Jia

2011-01-01

166

Analysis of the mushroom nephrotoxin orellanine and its glucosides.  

PubMed

Orellanine is a nephrotoxin found in various Cortinaceae mushroom species. Unintentional consumption after these species were confused with edible mushrooms such as Cantharellus tubaeformis has caused several casualties. In this work, a quantitative HPLC-ESI-MS/MS method for total orellanine in Cortinarius rubellus, spiked blood plasma, and a mushroom stew prepared from C. tubaeformis with the addition of a single specimen of C. rubellus is presented. The existence of mono- and diglucosylated orellanine in C. rubellus was also proven, although quantitative analysis could not be obtained for the glucosides due to rapid hydrolyzation to orellanine in the extract. Extraction with 3 M HCl or water mainly yielded orellanine, while MeOH or acidified MeOH mainly extracted mono- and diglucosylated orellanine. The highest recovery of total orellanine was obtained with 3 M HCl, which was subsequently used for quantitative analysis. A C?? HPLC column and low pH in the eluents retained all these toxins. Orellanine could be detected at a 4.9 ng/mL level in all extracts, which is well below the threshold for acute toxic effects. Additionally, the fragmentation pattern of orellanine upon electrospray MS/MS was probed. The method described is useful for two important applications. First, it allows quantitative analysis of processed food products that may be contaminated by orellanine from Cortinaceae mushrooms. Second, orellanine is currently being evaluated as a potential cure of metastatic renal cancer, and this work provides a method for monitoring orellanine at low concentrations within the therapeutic interval in blood serum. PMID:23046414

Herrmann, Anders; Hedman, Heidi; Rosén, Johan; Jansson, Daniel; Haraldsson, Börje; Hellenäs, Karl-Erik

2012-10-26

167

Metabolism of the masked mycotoxin deoxynivalenol-3-glucoside in pigs.  

PubMed

Plants can metabolize the Fusarium mycotoxin deoxynivalenol (DON) by forming the masked mycotoxin deoxynivalenol-3-?-D-glucoside (D3G). D3G might be cleaved during digestion, thus increasing the total DON burden of an individual. Due to a lack of in vivo data, D3G has not been included in the various regulatory limits established for DON so far. The aim of our study was to contribute to the risk assessment of D3G by determination of its metabolism in pigs. Four piglets received water, D3G (116 ?g/kg b.w.) and the equimolar amount of DON (75 ?g/kg b.w.) by gavage on day 1, 5 and 9 of the experiment, respectively. Additionally, 15.5 ?g D3G/kg b.w. were administered intravenously on day 13. Urine and feces were collected for 24 h and analyzed for DON, D3G, deoxynivalenol-3-glucuronide (DON-3-GlcA), deoxynivalenol-15-GlcA (DON-15-GlcA) and deepoxy-deoxynivalenol (DOM-1) by UHPLC-MS/MS. After oral application of DON and D3G, in total 84.8±9.7% and 40.3±8.5% of the given dose were detected in urine, respectively. The majority of orally administered D3G was excreted in form of DON, DON-15-GlcA, DOM-1 and DON-3-GlcA, while urinary D3G accounted for only 2.6±1.4%. In feces, just trace amounts of metabolites were found. Intravenously administered D3G was almost exclusively excreted in unmetabolized form via urine. Data indicate that D3G is nearly completely hydrolyzed in the intestinal tract of pigs, while the toxin seems to be rather stable after systemic absorption. Compared to DON, the oral bioavailability of D3G and its metabolites seems to be reduced by a factor of up to 2, approximately. PMID:24968060

Nagl, Veronika; Woechtl, Bettina; Schwartz-Zimmermann, Heidi Elisabeth; Hennig-Pauka, Isabel; Moll, Wulf-Dieter; Adam, Gerhard; Berthiller, Franz

2014-08-17

168

Sequestration, tissue distribution and developmental transmission of cyanogenic glucosides in a specialist insect herbivore.  

PubMed

Considering the staggering diversity of bioactive natural products present in plants, insects are only able to sequester a small number of phytochemicals from their food plants. The mechanisms of how only some phytochemicals are sequestered and how the sequestration process takes place remains largely unknown. In this study the model system of Zygaena filipendulae (Lepidoptera) and their food plant Lotus corniculatus is used to advance the knowledge of insect sequestration. Z. filipendulae larvae are dependent on sequestration of the cyanogenic glucosides linamarin and lotaustralin from their food plant, and have a much lower fitness if reared on plants without these compounds. This study investigates the fate of the cyanogenic glucosides during ingestion, sequestration in the larvae, and in the course of insect ontogeny. To this purpose, double-labeled linamarin and lotaustralin were chemically synthesized carrying two stable isotopes, a (2)H labeled aglucone and a (13)C labeled glucose moiety. In addition, a small amount of (14)C was incorporated into the glucose residue. The isotope-labeled compounds were applied onto cyanogenic L. corniculatus leaves that were subsequently presented to the Z. filipendulae larvae. Following ingestion by the larvae, the destiny of the isotope labeled cyanogenic glucosides was monitored in different tissues of larvae and adults at selected time points, using radio-TLC and LC-MS analyses. It was shown that sequestered compounds are taken up intact, contrary to earlier hypotheses where it was suggested that the compounds would have to be hydrolyzed before transport across the gut. The uptake from the larval gut was highly stereo selective as the ?-glucosides were retained while the ?-glucosides were excreted and recovered in the frass. Sequestered compounds were rapidly distributed into all analyzed tissues of the larval body, partly retained throughout metamorphosis and transferred into the adult insect where they were distributed to all tissues. During subsequent mating, isotope labeled cyanogenic glucosides were transferred from the male to the female in the nuptial gift. PMID:24269868

Zagrobelny, Mika; Olsen, Carl Erik; Pentzold, Stefan; Fürstenberg-Hägg, Joel; Jørgensen, Kirsten; Bak, Søren; Møller, Birger Lindberg; Motawia, Mohammed Saddik

2014-01-01

169

Metabolism of sitosteryl beta-D-glucoside and its nutritional effects in rats  

SciTech Connect

(4-14C)Sitosteryl beta-D-glucoside, intragastrically administered to rats, was not absorbed by the intestinal mucosa. At three hr after the application, radioactivity was concentrated almost exclusively in the digesta of stomach, small intestine as well as cecum and colon, whereas only low proportions of radioactively labeled compounds were found in the various tissues of the gastrointestinal tract. Minor proportions of labeled metabolites of (4-14C)sitosteryl beta-D-glucoside, such as sitosterol and sitosteryl esters, were formed in the small intestine in vivo and in slices of small intestine in vitro. In the tissues of cecum and colon as well as the digesta derived from them, high proportions of labeled coprositostanol, i.e. 24 alpha-ethyl-5 beta-cholestan-3 beta-ol, that obviously had been formed by bacterial degradation of the substrate were detected. The feeding of sitosteryl beta-D-glucoside (0.5 g/kg body weight X day) over a period of four weeks did not alter significantly body weights or organ weights of rats. Analyses of steryl lipids of the various organs and tissues confirmed the findings obtained with the radioactive substrate: neither sitosteryl beta-D-glucoside nor sitosterol or sitosteryl esters derived therefrom had been transported in appreciable amounts to organs and tissues outside the alimentary canal during the feeding period. Minor proportions of unmetabolized sitosteryl beta-D-glucoside were detected in the tissues of stomach and intestine, whereas large proportions of the substrate were found in feces of rats that had received the sitosteryl beta-D-glucoside-containing diet; coprositostanol was found in feces of these animals in high proportions as well.

Weber, N.

1988-01-01

170

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

Microsoft Academic Search

Catharanthus roseus cell suspension cultures converted exogenously supplied curcumin to a series of glucosides, none of which has been found in nature so far. The efficiency of glucosylation was dependent on culture stage of the cells and medium sucrose concentration. Methyl jasmonate and salicylic acid enhanced the glucoside formation only when they were added to the cultures prior to the

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

2003-01-01

171

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

E-print Network

(6S)-Hydroxy-3-oxo-a-ionol glucosides from Capparis spinosa fruits I . hsan C¸ alis¸ a , Ays¸ e)-roseoside) and a prenyl glucoside, were isolated from mature fruits of Capparis spinosa. The structures were established Science Ltd. All rights reserved. Keywords: Capparis spinosa; Capparidaceae; (6S)-Hydroxy-3-oxo

Rüedi, Peter

172

Carvyl- and Dihydrocarvyl-?-D-Glucosides in Spearmint (Studies on Terpene Glycosides in Mentha Plants, Part II)  

Microsoft Academic Search

Dihydrocarvyl-, Neodihydrocarvyl-; trans-carvyl-, cis-carvyl-and 3-octyl-?-D-glucosides were extracted from the aboveground plant material of Mentha gentilis f. cardiaca (Sm.) Briq. (Scotch spearmint) for the first time. The structures of these compounds were confirmed by comparing their retention times on gas chromatography and MS data with those of synthesized glucosides.

Sumio Shimizu; Hisao Shibata; Denei Karasawa; Toshio Kozaki

1990-01-01

173

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

174

(6S)-Hydroxy-3-oxo-alpha-ionol glucosides from Capparis spinosa fruits.  

PubMed

Two new (6S)-hydroxy-3-oxo-alpha-ionol glucosides, together with corchoionoside C ((6S,9S)-roseoside) and a prenyl glucoside, were isolated from mature fruits of Capparis spinosa. The structures were established on the basis of spectroscopic, chiroptic and chemical evidence. In addition, the 13C-resonance of C-9 was found to be of particular diagnostic value in assigning the absolute configuration at that center in ionol glycosides. The alpha-ionol derivatives are metabolites of (+)-(S)-abscisic acid. PMID:11830166

Cali?, Ihsan; Kuruüzüm-Uz, Ay?e; Lorenzetto, Piergiorgio A; Rüedi, Peter

2002-02-01

175

Triacylated cyanidin 3-(3 X-glucosylsambubioside)-5-glucosides from the flowers of Malcolmia maritima  

Microsoft Academic Search

Three acylated cyanidin 3-(3X-glucosylsambubioside)-5-glucosides (1–3) and one non-acylated cyanidin 3-(3X-glucosylsambubioside)-5-glucoside (4) were isolated from the purple-violet or violet flowers and purple stems of Malcolmia maritima (L.) R. Br (the Cruciferae), and their structures were determined by chemical and spectroscopic methods. In the flowers of this plant, pigment 1 was determined to be cyanidin 3-O-[2-O-(2-O-(trans-sinapoyl)-3-O-(?-d-glucopyranosyl)-?-d-xylopyranosyl)-6-O-(trans-p-coumaroyl)-?-d-glucopyranoside]-5-O-[6-O-(malonyl)-(?-d-glucopyranoside) as a major pigment, and a

Fumi Tatsuzawa; Norio Saito; Kenjiro Toki; Koichi Shinoda; Atsushi Shigihara; Toshio Honda

2008-01-01

176

A 1,5- cis-guaianolide glucoside from flowers of Arnica mollis  

Microsoft Academic Search

The novel sesquiterpene lactone glucoside 2?-O-?-d-glucopyranosyl-4?-hydroxy-1?,5?,11?-H-guai-10(14)-en-12,8?- olide(=2?-hydroxy-11?,13-dihydro-1-epi-inuviscolide-2?-O-?-d-glucopyranoside) was isolated from flowerheads of Arnica mollis. Its structural elucidation was carried out by NMR spectroscopy (1H and 13C NMR, 1H?1H COSY, HMBC, HMQC and 1H?1H NOESY) and mass spectrometry (DCI). Additionally, the lignan (+)-pinoresinol-4?-?-d-glucopyranoside and benzyl-?-glucoside were isolated and identified.

Irmgard Merfort; Günter Willuhn; Detlef Wendisch; Daniel Gondol

1996-01-01

177

Iridoid Glycoside Variation in the Invasive Plant Dalmatian Toadflax, Linaria dalmatica (Plantaginaceae), and Sequestration by the Biological Control Agent, Calophasia lunula  

Microsoft Academic Search

Invasive plant species can have significant ecological and economic impacts. Although numerous hypotheses highlight the importance\\u000a of the chemical defenses of invasive plant species, the chemical ecology of many invasive plants has not yet been investigated.\\u000a In this study, we provide the first quantitative investigation of variation in iridoid glycoside concentrations of the invasive\\u000a plant Dalmatian toadflax (Linaria dalmatica). We

Mary A. Jamieson; M. Deane Bowers

2010-01-01

178

The chemical nature of the antibacterial substance present in Aucuba japonica thunbg  

Microsoft Academic Search

Résumé 1o La substance antibactérielle des feuilles d'Aucuba japonica est identifiée comme étant l'aucubigénine. Ce furane substitué se forme à partir de la ?-glucoside aucubine sous l'action d'un enzyme hydrolytique.

J. E. Rombouts; J. Links

1956-01-01

179

Structural determination of a nivalenol glucoside and development of an analytical method for the simultaneous determination of nivalenol and deoxynivalenol, and their glucosides, in wheat.  

PubMed

Trichothecene mycotoxins such as nivalenol and deoxynivalenol frequently contaminate foodstuffs. Recently, several trichothecene glucosides have been found in trichothecene-contaminated foods, and information about their chemistry, toxicity, and occurrence is required. In this study, a glucoside of nivalenol was isolated from nivalenol-contaminated wheat and was identified as nivalenol-3-O-?-D-glucopyranoside. Analytical methods using a multifunctional column or an immunoaffinity column have been developed for the simultaneous determination of nivalenol, nivalenol-3-O-?-D-glucopyranoside, deoxynivalenol, and deoxynivalenol-3-O-?-D-glucopyranoside in wheat. The methods were validated in a single laboratory, and recovery from wheat samples spiked at four levels ranged between 86.4 and 103.5% for the immunoaffinity column cleanup. These mycotoxins in contaminated wheat samples were quantitated by the validated method. Nivalenol-3-O-?-D-glucopyranoside was detected in the nivalenol-contaminated wheat, and the percentage of nivalenol-3-O-?-D-glucopyranoside to nivalenol ranged from 12 to 27%. This result indicates that the analytical method developed in this study is useful for obtaining data concerning the state and level of food contamination by nivalenol, deoxynivalenol, and their glucosides. PMID:24433151

Yoshinari, Tomoya; Sakuda, Shohei; Furihata, Kazuo; Furusawa, Hiroko; Ohnishi, Takahiro; Sugita-Konishi, Yoshiko; Ishizaki, Naoto; Terajima, Jun

2014-02-01

180

A new phenolic glucoside from an Uzbek medicinal plant, Origanum tyttanthum.  

PubMed

A new phenolic glucoside was isolated from the aerial parts of Origanum tyttanthum, an Uzbek medicinal plant, together with 12 known compounds. The structure of the new compound was elucidated as 4-O-beta-D-glucopyranosylbenzyl-3'-hydroxyl-4'-methoxybenzoate (1) based on the spectral and chemical evidence. PMID:18404346

Takeda, Yoshio; Tomonari, Maki; Arimoto, Shihoko; Masuda, Toshiya; Otsuka, Hideaki; Matsunami, Katsuyoshi; Honda, Gisho; Ito, Michiho; Takaishi, Yoshihisa; Kiuchi, Fumiyuki; Khodzhimatov, Olimjon K; Ashurmetov, Ozodbek A

2008-01-01

181

Fate of dietary pyridoxine-beta-glucoside in the lactating rat  

SciTech Connect

(/sup 3/H)5'-O-(beta-D-glucopyranosyl) pyridoxine (PN-glucoside) and (/sup 14/C)pyridoxine (PN) were orally administered to lactating rats. Milk was collected from the dam, and the stomach contents and liver were collected from the suckling pups 24 and 48 h after administration. Analysis of the isotopic ratio (/sup 3/H//sup 14/C) in the milk and stomach contents indicated that the secretion of /sup 3/H in the milk was 20-25% as great as the secretion of /sup 14/C. The only labeled form of /sup 3/H and /sup 14/C in the stomach contents was pyridoxal phosphate (PLP), indicating that PN-glucoside was hydrolyzed to PN and subsequently metabolized prior to secretion by the mammary gland. The isotopic ratio in the livers of the pups was similar to that of the stomach contents. Furthermore, the relative distribution of the two isotopes among the hepatic metabolites of the pups was similar. The results of this study indicate that intact PN-glucoside is not secreted in milk, although vitamin B-6 derived from the limited hydrolysis and metabolism of PN-glucoside is delivered to the mammary gland for secretion.

Trumbo, P.R.; Gregory, J.F. III

1989-01-01

182

Diptoindonesin A, a new C-glucoside of epsilon-viniferin from Shorea seminis (Dipterocarpaceae).  

PubMed

A new C-glucoside of epsilon-viniferin, named diptoindonesin A (1), was isolated from the ethyl acetate extract of the tree bark of Shorea seminis, together with the known stilbene oligomers (-)-ampelopsin A (2), (-)-alpha-viniferin (3), and (-)-hopeaphenol (4). The structure of 1 was determined from spectroscopic evidence. PMID:12385874

Aminah, Nanik S; Achmad, Sjamsul A; Aimi, Norio; Ghisalberti, Emilio L; Hakim, Euis H; Kitajima, Mariko; Syah, Yana M; Takayama, Hiromitsu

2002-10-01

183

Vitamin B6 Status Indicators Decrease in Women Consuming a Diet High in Pyridoxine Glucoside1\\  

Microsoft Academic Search

Previous research has shown that the pyridoxine glucoside (PNG) form of vitamin B-6 has a reduced bioavailability compared with pyridoxine, but its effect on vitamin B-6 status has not been assessed. Following an 8-d adjustment period, nine women con sumed diets containing a high or low amount of PNG for 18 d each, in a crossover design. The high and

CHRISTINE M. HANSEN; JAMES E. LEKLEM; LORRAINE T. MILLER

184

Isoptaquiloside and caudatoside, illudane-type sesquiterpene glucosides from Pteridium aquilinum var. caudatum  

Microsoft Academic Search

Ptaquiloside and two new illudane-type sesquiterpene glycosides were isolated from Pteridium aquilinum var. caudatum. One- and two-dimensional NMR analyses revealed the new glucosides to be isoptaquiloside and caudatoside. Four pterosins, A, B, K and Z, were also isolated from a base-acid treated extract.

Uvidelio F. Castillo; Alistair L. Wilkins; Denis R. Lauren; Barry L. Smith; Neale R. Towers; Miguel E. Alonso-Amelot; Ramon Jaimes-Espinoza

1997-01-01

185

Kaempferol 7- O-rhamnoside-4?- O-glucoside from Pteridium aquilinum  

Microsoft Academic Search

A new flavonol glycoside from aerial parts of Pteridium aquilinum was identified as kaempferol 7-O-rhamnoside-4?-O-glucoside by chemical and spectral methods. In addition a mixture of quercetin 3-O-fructoside and isoquercitrin was found in this plant material.

Filippo Imperato

1998-01-01

186

Helicobacter pylori Cholesteryl ?-Glucosides Contribute to Its Pathogenicity and Immune Response by Natural Killer T Cells  

PubMed Central

Approximately 10–15% of individuals infected with Helicobacter pylori will develop ulcer disease (gastric or duodenal ulcer), while most people infected with H. pylori will be asymptomatic. The majority of infected individuals remain asymptomatic partly due to the inhibition of synthesis of cholesteryl ?-glucosides in H. pylori cell wall by ?1,4-GlcNAc-capped mucin O-glycans, which are expressed in the deeper portion of gastric mucosa. However, it has not been determined how cholesteryl ?-glucosyltransferase (?CgT), which forms cholesteryl ?-glucosides, functions in the pathogenesis of H. pylori infection. Here, we show that the activity of ?CgT from H. pylori clinical isolates is highly correlated with the degree of gastric atrophy. We investigated the role of cholesteryl ?-glucosides in various aspects of the immune response. Phagocytosis and activation of dendritic cells were observed at similar degrees in the presence of wild-type H. pylori or variants harboring mutant forms of ?CgT showing a range of enzymatic activity. However, cholesteryl ?-glucosides were recognized by invariant natural killer T (iNKT) cells, eliciting an immune response in vitro and in vivo. Following inoculation of H. pylori harboring highly active ?CgT into iNKT cell-deficient (J?18?/?) or wild-type mice, bacterial recovery significantly increased in J?18?/? compared to wild-type mice. Moreover, cytokine production characteristic of Th1 and Th2 cells dramatically decreased in J?18?/? compared to wild-type mice. These findings demonstrate that cholesteryl ?-glucosides play critical roles in H. pylori-mediated gastric inflammation and precancerous atrophic gastritis. PMID:24312443

Ito, Yuki; Vela, Jose Luis; Matsumura, Fumiko; Hoshino, Hitomi; Tyznik, Aaron; Lee, Heeseob; Girardi, Enrico; Zajonc, Dirk M.; Liddington, Robert; Kobayashi, Motohiro; Bao, Xingfeng; Bugaytsova, Jeanna; Boren, Thomas; Jin, Rongsheng; Zong, Yinong; Seeberger, Peter H.; Nakayama, Jun; Kronenberg, Mitchell; Fukuda, Minoru

2013-01-01

187

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

188

GC-MS quantification of gibberellin A 20-13- O-glucoside and gibberellin A 8-2- O-glucoside in developing barley caryopses  

Microsoft Academic Search

Gibberellin A20-13-O-glucoside (GA20-13-O-Glc) and GA8-2-O-Glc were identified by GC-MS as permethylated derivatives in mature grains of both barley varieties Hordeum vulgare L. cv. Himalaya and cv. Salome.Changes of the pool size of these GA conjugates together with those of the parent GA20 and GA8 were estimated during seed ripening by internal standard quantification. The pools of GA20 and GA8 were

Bianca Senns; Petra Fuchs; Gernot Schneider

1998-01-01

189

Effects and mechanisms of total glucosides of paeony on joint damage in rat collagen-induced arthritis  

Microsoft Academic Search

Objective and design: To investigate the therapeutic effects and mechanisms of total glucosides of paeony (TGP), an effective compound of Chinese traditional herbal medicine (CTM), on collagen -induced arthritis (CIA) in rats.

L. Zhu; W. Wei; Y.-Q. Zheng; X.-Y. Jia

2005-01-01

190

Lipase-catalyzed direct and regioselective acylation of flavonoid glucoside for mechanistic investigation of stable plant pigments  

Microsoft Academic Search

One-step and regioselective acylation of flavonoid glucosides was achieved by lipase-catalyzed transesterification in dry organic media. For example, isoquercitrin (quercetin 3-O-glucoside), one of the flavonol monoglucosides, was converted efficiently to the corresponding aromatic acid ester (isoquercitrin 6?-O-cinnamate) by a lipase with vinyl cinnamate as an acyl donor. The method described, which is the first allowing the direct synthesis of aromatic

Nobuyoshi Nakajima; Kohji Ishihara; Toshiyuki Itoh; Tsutomu Furuya; Hiroki Hamada

1999-01-01

191

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

192

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

PubMed

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

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

2014-04-01

193

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

194

Effective catalytic conversion of cellulose into high yields of methyl glucosides over sulfonated carbon based catalyst.  

PubMed

An amorphous carbon based catalyst was prepared by sulfonation of the bio-char obtained from fast pyrolysis (N(2) atm; ? 550°C) of biomass. The sulfonated carbon catalyst contained high acidity of 6.28 mmol/g as determined by temperature programmed desorption of ammonia of sulfonated carbon catalyst and exhibited high catalytic performance for the hydrolysis of cellulose. Amorphous carbon based catalyst containing -SO(3)H groups was successfully tested and the complete conversion of cellulose in methanol at moderate temperatures with high yields ca. ? 90% of ?, ?-methyl glucosides in short reaction times was achieved. The methyl glucosides formed in methanol are more stable for further conversion than the products formed in water. The carbon catalyst was demonstrated to be stable for five cycles with slight loss in catalytic activity. The utilization of bio-char as a sulfonated carbon catalyst provides a green and efficient process for cellulose conversion. PMID:22776237

Dora, Sambha; Bhaskar, Thallada; Singh, Rawel; Naik, Desavath Viswanatha; Adhikari, Dilip Kumar

2012-09-01

195

A new flavone xyloside and two new flavan-3-ol glucosides from Juniperus communis var. depressa.  

PubMed

A new flavone xyloside, 1, and two new flavan-3-ol glucosides, 3 and 4, were isolated together with three known flavones, 2, 11, and 12, five known flavans, 5-9, and a known dihydrochalcone, 10, from the stems and leaves of Juniperus communis var. depressa (Cupressaceae) collected in Oregon, U.S.A., and their structures were determined on the basis of spectral evidence. A novel flavone nucleus such as that in 1 is seldom found in nature today, and new methylcatechin glucosides 3 and 4 are also rare in nature. In addition, we investigated the inhibitory activity of individual components, i.e., 8-11, and others, that were abundantly isolated from the same plant material for the Maillard reaction. PMID:17256732

Iida, Naoki; Inatomi, Yuka; Murata, Hiroko; Inada, Akira; Murata, Jin; Lang, Frank A; Matsuura, Nobuyasu; Nakanishi, Tsutomu

2007-01-01

196

Effect of the phytoestrogen, genistein-8-C-glucoside, on Chinese hamster ovary cells in vitro  

Microsoft Academic Search

Genistein-8-C-glucoside (G8CG) belongs to isoflavones, which are a subclass of flavonoids, a large group of polyphenolic compounds widely distributed in plants. A number of studies on flavonoids show their cardioprotective and antiosteoporosis properties in in vitro and in vivo models. As a phytoestrogen, genistein has recently generated interest as a potential anticancer and antiatherogenic agent. Several flavonoids are known as

Agata Rucinska; Sergej Kirko; Teresa Gabryelak

2007-01-01

197

Effects and mechanisms of glucosides of chaenomeles speciosa on collagen-induced arthritis in rats  

Microsoft Academic Search

Effects of glucosides of chaenomeles speciosa (GCS)—a Chinese traditional herbal medicine (CTM) on inflammatory and immune responses and its mechanisms in collagen-induced arthritis (CIA) rat were studied. Hind paw volumes of rats were measured by volume meter; lymphocyte proliferation, interleukin-1, interleukin-2, TNF-? level was determined by 3-(4,5-2dimethylthiazal-2yl)2,5-diphenyltetrazoliumbromide (MTT) assay; cAMP level in synoviocytes was analyzed by competitive protein binding assay

Qun Chen; Wei Wei

2003-01-01

198

Developmental fate of the cyanogenic glucoside linamarin in Costa Rican wild lima bean seeds  

Microsoft Academic Search

WHEN a seed germinates, we expect the defensive secondary compounds it contains to be transferred intact to the growing seedling, or variously decomposed to produce resources for the growing seedling. The seeds of wild indigenous Costa Rican lima beans (Phaseolus lunatus L.) contain about 3.45% fresh weight of linamarin1, a cyanogenic glucoside that can enzymatically decompose to produce 0.37% fresh

D. O. Clegg; E. E. Conn; D. H. JANZEN

1979-01-01

199

Formation of glucoside conjugate of acetaminophen by fungi separated from soil  

Microsoft Academic Search

Summary  The phase II metabolite of acetaminophen in filamentous fungi and actinomycetes separated from soil was investigated. Fifty-four\\u000a filamentous fungi and twenty-seven actinomycetes were screened to transform acetaminophen. The metabolites of acetaminophen\\u000a were assayed using liquid chromatography-tandem mass spectrometry. The only metabolite was subject to enzymatic hydrolysis\\u000a to confirm its structure. Acetaminophen was converted into glucoside conjugate, by filamentous fungi JX1-60,

H. H. Huang; L. H. Lin; P. Zhang; X. L. Qi; D. F. Zhong

2006-01-01

200

Cyanidin-3-Glucoside Suppresses Cytokine-Induced Inflammatory Response in Human Intestinal Cells: Comparison with 5-Aminosalicylic Acid  

PubMed Central

The potential use of polyphenols in the prevention and treatment of chronic inflammatory diseases has been extensively investigated although the mechanisms involved in cellular signaling need to be further elucidated. Cyanidin-3-glucoside is a typical anthocyanin of many pigmented fruits and vegetables widespread in the human diet. In the present study, the protection afforded by cyanidin-3-glucoside against cytokine-triggered inflammatory response was evaluated in the human intestinal HT-29 cell line, in comparison with 5-aminosalicylic acid, a well-established anti-inflammatory drug, used in inflammatory bowel disease. For this purpose, some key inflammatory mediators and inflammatory enzymes were examined. Our data showed that cyanidin-3-glucoside reduced cytokine-induced inflammation in intestinal cells, in terms of NO, PGE2 and IL-8 production and of iNOS and COX-2 expressions, at a much lower concentration than 5-aminosalicylic acid, suggesting a higher anti-inflammatory efficiency. Interestingly, cyanidin-3-glucoside and 5-aminosalicylic acid neither prevented IkB-? degradation nor the activation of NF-kB, but significantly reduced cytokine-induced levels of activated STAT1 accumulated in the cell nucleus. In addition, we established that phosphorylated p38 MAPK was not involved in the protective effect of cyanidin-3-glucoside or 5-aminosalicylic acid. Taking into account the high concentrations of dietary anthocyanins potentially reached in the gastrointestinal tract, cyanidin-3-glucoside may be envisaged as a promising nutraceutical giving complementary benefits in the context of inflammatory bowel disease. PMID:24039842

Serra, Diana; Paixao, Joana; Nunes, Carla; Dinis, Teresa C. P.; Almeida, Leonor M.

2013-01-01

201

Repellent activity of catmint, Nepeta cataria, and iridoid nepetalactone isomers against Afro-tropical mosquitoes, ixodid ticks and red poultry mites  

Microsoft Academic Search

The repellent activity of the essential oil of the catmint plant, Nepeta cataria (Lamiaceae), and the main iridoid compounds (4aS,7S,7aR) and (4aS,7S,7aS)-nepetalactone, was assessed against (i) major Afro-tropical pathogen vector mosquitoes, i.e. the malaria mosquito, Anopheles gambiae s.s. and the Southern house mosquito, Culex quinquefasciatus, using a World Health Organisation (WHO)-approved topical application bioassay (ii) the brown ear tick, Rhipicephalus

Michael A. Birkett; Ahmed Hassanali; Solveig Hoglund; Jan Pettersson; John A. Pickett

2011-01-01

202

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

J?rgensen, Kirsten; Bak, S?ren; Busk, Peter Kamp; S?rensen, Charlotte; Olsen, Carl Erik; Puonti-Kaerlas, Johanna; M?ller, Birger Lindberg

2005-01-01

203

Isolation and purification of iridoid glycosides from Gardenia jasminoides Ellis by isocratic reversed-phase two-dimensional preparative high-performance liquid chromatography with column switch technology.  

PubMed

A two-dimensional column-switching system without sample loop trapping, where two columns were switched directly via a six-port two-position switching valve, was successfully applied for the first time to the isolation and purification of six iridoid glycosides including geniposide, gardenoside, shanzhiside, scandoside methyl ester, deacetyl-asperulosidic acid methyl ester and genipin-1-beta-D-gentiobioside from Gardenia jasminoides Ellis, a plant used in the traditional Chinese medicine. The introduction of the six-port switching valve instead of sample loop assured 100% recovery from the first dimension to the second, and the injection volumes of the second dimension could reach 20 ml. In this mode of operation, the sample size of the two-dimensional approach was more than 1.3 times that of conventional gradient methods with even less solvent consumption. And the simultaneous operations of the two dimensions allowed the cycle time to be less than 19 min, compared with that (90 min) in the gradient elution single-dimension mode of operation. All of the six isolated iridoid glycosides were isolated at high purities of over 99% with approximately 96% recoveries. PMID:17851143

Zhou, Tingting; Zhao, Weiquan; Fan, Guorong; Chai, Yifeng; Wu, Yutian

2007-10-15

204

Effect of the phytoestrogen, genistein-8-C-glucoside, on Chinese hamster ovary cells in vitro.  

PubMed

Genistein-8-C-glucoside (G8CG) belongs to isoflavones, which are a subclass of flavonoids, a large group of polyphenolic compounds widely distributed in plants. A number of studies on flavonoids show their cardioprotective and antiosteoporosis properties in in vitro and in vivo models. As a phytoestrogen, genistein has recently generated interest as a potential anticancer and antiatherogenic agent. Several flavonoids are known as antioxidants and scavengers of free oxygen radicals. In the current investigation we used glycosylated genistein (genistein-8-C-glucoside) from flowers of lupine (Lupinus luteus L.). Many authors have found that the action of genistein is not so simple, although many reports conducted in vitro have demonstrated that it is cytotoxic and genotoxic. Therefore, the cytotoxic and genotoxic effects of this compound in Chinese hamster ovary cells (line CHO) were studied. A colorimetric MTT assay to assess cytotoxicity and a Comet assay for the detection of DNA damage were used. Apoptosis was determined by the Hoechst 33258/propidium iodide staining technique. We have also demonstrated antioxidant properties of G8CG. The level of reactive oxygen species generated by G8CG alone and/or H2O2 was evaluated with fluorescence probes: dichlorofluorescein-diacetate (DCFDA) by flow cytometry. The cells were exposed to various concentrations of genistein-8-C-glucoside (1-290 microM) and hydrogen peroxide (10-130 microM) and the effect of G8CG alone or in combination with H2O2 was determined. The results reveal that G8CG at concentrations higher than 10 microM significantly reduced cell viability, induced apoptosis and DNA damage. However at lower concentrations (5 and 7.5 microM), G8CG showed antioxidant properties, but had no cytotoxic or genotoxic activity. PMID:17601753

Rucinska, Agata; Kirko, Sergej; Gabryelak, Teresa

2007-11-01

205

Oviposition Cues for a Specialist ButterflyPlant Chemistry and Size  

E-print Network

Oviposition Cues for a Specialist Butterfly­Plant Chemistry and Size J. H. Reudler Talsma & A of an insect herbivore is based on a complex set of stimuli and responses. In this study, we examined the effect of plant secondary chemistry (the iridoid glycosides aucubin and catalpol) and aspects of size

van Nouhuys, Saskya

206

Drybonioside, a new glucoside from the Drynaria bonii H. Christ Rhizomes.  

PubMed

Drynaria bonii H. Christ, a Vietnam traditional medicinal plant, is used for the treatment of osteoporosis, bone fractures, tinnitus, etc. (Ho PH. 2002. Vietnamese plants. Hanoi: Publisher of Young; Loi DT. 2004. Medicinal plants and remedy of Vietnam. Hanoi: Publisher of Medicine). Based on column chromatography, a new glucoside named drybonioside (5) and four known compounds ?-tocopherol (1), 24-methylencycloartan-3?-ol (2), triphyllol (3) and ethyl ?-d-fructopyranoside (4) were isolated and identified from hexane and methanol extracts of D. bonii. The structures of new compound were elucidated on the basis of NMR and MS spectroscopic analysis. PMID:25299239

Pham, Thi Nhat Trinh; Mai, Dinh Tri; Huynh, Thi My Nuong; Le, Tien Dung

2015-01-01

207

Colon-specific delivery of dexamethasone from a glucoside prodrug in the guinea pig.  

PubMed

Dexamethasone-beta-D-glucoside is a potential prodrug for colonic delivery of the antiinflammatory agent, dexamethasone. The ability of this prodrug to deliver dexamethasone selectively to the colon depends not only on its being slowly absorbed from the alimentary canal, but also on its having chemical and enzymatic stability in the stomach and small intestine. Once reaching the large bowel, it should be quantitatively hydrolyzed to release the active agent. The potential of dexamethasone-beta-D-glucoside for colon-specific delivery of dexamethasone is assessed by determining the rates of its hydrolysis down the alimentary canal of the guinea pig, an animal in which an inflammatory bowel disease model has been developed. The hydrolytic activity is examined in tissues and luminal contents of the stomach, proximal and distal segments of the small intestine, cecum, and colon. For the tissues, the greatest hydrolytic activity is in the proximal small intestine, while the stomach, cecum, and colon have only moderate activity. In contrast, the contents of the cecum and colon show greater activity than the contents of the small intestine and stomach. The luminal contents retained beta-glucosidase activity even after repeated centrifugation and resuspension in a buffer. The activity was unaffected by homogenization. These observations suggest that hydrolytic activity is associated with enzymes located on the surface of luminal cells. The movement and hydrolysis of dexamethasone-beta-D-glucoside down the gastrointestinal tract of the guinea pig are also examined. About 20 to 30% of an oral dose appears to reach the cecum. Here the prodrug is rapidly hydrolyzed to the active drug. From intravenous administration of the prodrug and drug, it is apparent that dexamethasone-beta-D-glucoside is poorly absorbed in the gastrointestinal tract (bioavailability, less than 1%). There is a ninefold selective advantage for delivery of dexamethasone in cecal tissues in the guinea pig under the conditions of this experiment. Thus, there is a potential for a decrease in the usual dose and a concomitant reduction in the systemic exposure to dexamethasone. Because humans have much less glucosidase activity in the small intestine, even greater site-selective delivery to the cecum and colon is expected. PMID:1871038

Tozer, T N; Rigod, J; McLeod, A D; Gungon, R; Hoag, M K; Friend, D R

1991-04-01

208

Phytochemical and Antimicrobial Studies of Methyl Angolensate and Luteolin-7-O-glucoside Isolated from Callus Cultures of Soymida febrifuga  

PubMed Central

Soymida febrifuga (Roxb.) A. Juss. is an indigenous lofty deciduous medicinal tree, monotypic genus endemic to India. Hexane, ethyl acetate and methanol extracts of Soymida febrifuga root callus were tested for their phytochemical constituents and antimicrobial activity. Among them, ethyl acetate extract was found to be most effective, which on subjection to silica gel column chromatography led to the separation and isolation of methyl angolensate and luteolin-7-O-glucoside. Structures were determined by Nuclear Magnetic Resonance and Liquid Chromatographic Mass Spectroscopic methods. Further studies indicated that methyl angolensate and luteolin-7-O-glucoside had an anti-bacterial effect against Bacillus subtilis and Salmonella typhimurium, respectively. In addition to that methyl angolensate had an anti-fungal activity against Aspergillus niger while luteolin-7-O-glucoside inhibited Alternaria alternata. PMID:23675053

Chiruvella, Kishore K.; Mohammed, Arifullah; Dampuri, Gayathri; Ghanta, Rama Gopal; Raghavan, Sathees C.

2007-01-01

209

A novel type of highly effective nonionic gemini alkyl O-glucoside surfactants: a versatile strategy of design.  

PubMed

A novel type of highly effective gemini alkyl glucosides has been rationally designed and synthesized. The gemini surfactants have been readily prepared by glycosylation of the gemini alkyl chains that are synthesized with regioselective ring-opening of ethylene glycol epoxides by the alkyl alcohols. The new gemini alkyl glucosides exhibit significantly better surface activity than the known results. Then rheological, DLS, and TEM studies have revealed the intriguing self-assembly behavior of the novel gemini surfactants. This study has proved the effectiveness of the design of gemini alkyl glucosides which is modular, extendable, and synthetically simple. The new gemini surfactants have great potential as nano carriers in drug and gene delivery. PMID:23806002

Liu, Songbai; Sang, Ruocheng; Hong, Shan; Cai, Yujing; Wang, Hua

2013-07-01

210

Efficient synthesis of gluco-oligosaccharides and alkyl-glucosides by transglycosylation activity of ?-glucosidase from Sclerotinia sclerotiorum  

Microsoft Academic Search

An extracellular ?-glucosidase (?-glu x) from Sclerotinia sclerotiorum was used as catalyst for the synthesis of gluco-oligosaccharides (GOSs) and alkyl-glucosides. The purified ?-glu x was not\\u000a regiospecific for ?(1?4) linkages in either hydrolysis or transglycosylation catalysed-reactions. It efficiently synthesized\\u000a GOSs from cellobiose, gentiobiose and methyl ?-d-glucoside by transglycosylation. At optimal conditions, 119 mg\\/ml of GOSs (?\\u000a ?33%) were formed over 9 h

Issam Smaali; Thierry Maugard; Ferid Limam; Marie-Dominique Legoy; Nejib Marzouki

2007-01-01

211

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

PubMed

Glycosynthase mutants obtained from Thermotogamaritima were able to catalyze the regioselective synthesis of aryl beta-D-Galp-(1-->3)-beta-D-Glcp and aryl beta-D-Glcp-(1-->3)-beta-D-Glcp in high yields (up to 90 %) using aryl beta-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. Unfortunately, the deprotection of the aromatic group of the disaccharides was not possible without partial hydrolysis of the glycosidic bond. The replacement of aryl groups by benzyl ones could offer the opportunity to deprotect the anomeric position under very mild conditions. Assuming that benzyl acceptors could preserve the stabilizing stacking, benzyl beta-d-glucoside firstly assayed as acceptor resulted in both poor yields and poor regioselectivity. Thus, we decided to undertake molecular modeling calculations in order to design which suitable substituted benzyl acceptors could be used. This study resulted in the choice of 2-biphenylmethyl beta-D-glucopyranoside. This choice was validated experimentally, since the corresponding beta-(1-->3) disaccharide was obtained in good yields and with a high regioselectivity. At the same time, we have shown that phenyl 1-thio-beta-D-glucopyranoside was also an excellent substrate leading to similar results as those obtained with the O-phenyl analogue. The NBS deprotection of the S-phenyl group afforded the corresponding disaccharide quantitatively. PMID:18828996

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

2008-11-24

212

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

213

Chemical constituents of Chinese natural medicine, morindae radix, the dried roots of morinda officinalis how.: structures of morindolide and morofficinaloside.  

PubMed

A new iridoid lactone, morindolide, and a new iridoid glucoside, morofficinaloside, have been isolated from a Chinese natural medicine, Morindae Radix, the dried root of Morinda officinalis How. together with a number of known compounds: five anthraquinones, four iridoid glucosides, a monoterpene glycoside, two sterols, an ursane-type triterpene, and a lactone compound. The chemical structures of the new compounds were determined on the basis of chemical and physicochemical evidence. PMID:7586069

Yoshikawa, M; Yamaguchi, S; Nishisaka, H; Yamahara, J; Murakami, N

1995-09-01

214

Determination of quercetin and its glucosides in onion by electrochemical methods.  

PubMed

Quercetin (Q), quercetin-3,4'-diO-beta-glucoside (Q3,4'G), quercetin-3-O-beta-glucoside (Q3G) and quercetin-4'-O-beta-glucoside (Q4'G) were determined in onion bulbs (Allium cepa) by HPLC with amperometric detection after analysis of the hydrodynamic voltammograms of flavonoid standards within the potential range of 50-1000 mV and by cyclic voltammetry (CV) method. The hydrodynamic voltammetric profiles of flavonoids showed that the peak current of Q, Q3G, Q4'G and Q3,4'G increased rapidly when the applied potential exceeded +450 mV (vs. SCE). High sensitivity and low background current were observed at the applied potential of +950 mV (vs. SCE). The lower limits of detection (LOD) were determined at signal-to-noise ratio of 3 and showed the following values: 8.05x10(-8)M (Q), 1.08x10(-7) M (Q3G), 1.22x10(-7) M (Q4'G) and 2.6x10(-7) M (Q3,4'G). The data provided by HPLC-UV-MS confirmed the presence of Q, Q3G, Q4'G and Q3,4'G in 80% methanol extracts of lyophilised onion bulbs. The CV method was applied for the qualitative assessment of onion flavonoids followed by the determination of anodic peak potential (E(a)) of the standards. The qualitative analysis of onion flavonoids was based on the anodic peak current (I(a)) of the extracts after external standards addition. The recorded cyclic voltammograms of the above flavonoid standards showed that all four compounds had well-defined oxidation waves with peak potentials of 310, 390, 482 and 800 mV (vs. Ag/AgCl) for Q, Q3G, Q4'G and Q3,4'G in 50 mM acetate-acetic buffer (pH 5.5) in 80% methanol, respectively. The study proved applicability of the CV method for identifying Q, Q3G, Q4'G and Q3,4'G in onion. PMID:18486637

Zieli?ska, D; Nagels, L; Pisku?a, M K

2008-06-01

215

Cardenolide analogues. 14. Synthesis and biological activity of glucosides of C17 beta-modified derivatives of digitoxigenin.  

PubMed

An improved method for the synthesis of cardiac glycosides was used to prepare 3 beta-glucosides of digitoxigenin derivatives in which the 17 beta side chain was CH=CHX (X = COOH, CONH2, COCH3, CN, or COOR). We compared the inotropic activity of the compounds with that of digitoxigenin glucoside using guinea pig left atria. All compounds were active except for the acid (7) and the amide (8). The inactivity of the amide, in spite of its favorable shape and high capacity for forming intermolecular hydrogen bonds, is incompatible with some previous structure-activity relationship theories. Of the active genins, glucosidation enhanced activity by a factor of about 2. All glucosides, including those with high potency, showed rapid onset and offset of action. The stepwise fall in potency that occurred when the ester group (CH=CHCOOR) was increased in bulk supported previous suggestions that the portion of the digitalis receptor that interacts with the C17 side chain lies within a cleft. PMID:7143360

Smith, P; Brown, L; Boutagy, J; Thomas, R

1982-10-01

216

Ptaquiloside Z, a new toxic unstable sesquiterpene glucoside from the neotropical bracken fern pteridium aquilinum var. caudatum  

Microsoft Academic Search

Reversed-phase HPLC fractionation, monitored by brine shrimp bioassay, led to the isolation of a new illudane-type sesquiterpene glucoside, ptaquiloside Z (2), as well as the known bracken carcinogen ptaquiloside (1), from a bioactive aqueous extract of the neotropical bracken fern Pteridium aquilinum var. caudatum (Pteridaceae). The structure of ptaquiloside Z (2) was confirmed by spectroscopic analyses and chemical degradation. Both

Uvidelio Francisco Castillo; Makoto Ojika; Miguel Alonso-Amelot; Youji Sakagami

1998-01-01

217

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

PubMed

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

2013-12-01

218

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

PubMed

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

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

1992-08-01

219

Isolation of new flavan-3-ol and lignan glucoside from Loropetalum chinense and their antimicrobial activities.  

PubMed

Phytochemical and antimicrobial activity study on the ethanol extract of the leaves and stems of Loropetalum chinense led to the isolation of a new flavan-3-ol compounds, 8-[1-(3,4-dihydroxyphenyl)-3-methoxy-3-oxopropyl]-catechin (loropetaliside A) (1) and a new lignan glucoside, 1-(5-hydroxy-3-methoxyphenyl)-2-(2-?-glucopyranosyl-4-hydroxy-5-(1-(E)propen-3-ol)-phenyl)-propane-3-ol (loropetaliside B) (3) and several known compounds manglieside D (2), quercetin (4), kaempferol-3-O-D-glucopyranoside (5), quercetin-3-O-?-L-rhamnoside (6) and tiliroside (7). Their structures were elucidated on the basis of extensive spectroscopic analysis. PMID:23954178

Zhang, Qinghua; Fan, Dan; Xiong, Bingjian; Kong, Lingbao; Zhu, Xiangdong

2013-10-01

220

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-Martinez, Maribel; Ozsisli, Bahri; Whitney, Kristin; Ohm, Jae-Bom

2013-01-01

221

Triacylated cyanidin 3-(3X-glucosylsambubioside)-5-glucosides from the flowers of Malcolmia maritima.  

PubMed

Three acylated cyanidin 3-(3(X)-glucosylsambubioside)-5-glucosides (1-3) and one non-acylated cyanidin 3-(3(X)-glucosylsambubioside)-5-glucoside (4) were isolated from the purple-violet or violet flowers and purple stems of Malcolmia maritima (L.) R. Br (the Cruciferae), and their structures were determined by chemical and spectroscopic methods. In the flowers of this plant, pigment 1 was determined to be cyanidin 3-O-[2-O-(2-O-(trans-sinapoyl)-3-O-(beta-D-glucopyranosyl)-beta-D-xylopyranosyl)-6-O-(trans-p-coumaroyl)-beta-D-glucopyranoside]-5-O-[6-O-(malonyl)-(beta-D-glucopyranoside) as a major pigment, and a minor pigment 2 was determined to be the cis-p-coumaroyl isomer of pigment 1. In the stems, pigment 3 was determined to be cyanidin 3-O-[2-O-(2-O-(trans-sinapoyl)-3-O-(beta-D-glucopyranosyl)-beta-D-xylopyranosyl)-6-O-(trans-p-coumaroyl)-beta-d-glucopyranoside]-5-O-(beta-D-glucopyranoside) as a major anthocyanin, and also a non-acylated anthocyanin, cyanidin 3-O-[2-O-(3-O-(beta-D-glucopyranosyl)-beta-D-xylopyranosyl)-beta-D-glucopyranoside]-5-O-(beta-D-glucopyranoside) was determined to be a minor pigment (pigment 4). In this study, it was established that the acylation-enzymes of malonic acid has important roles for the acylation of 5-glucose residues of these anthocyanins in the flower-tissues of M. maritima; however, the similar enzymatic reactions seemed to be inhibited or lacking in the stem-tissues. PMID:17928016

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

2008-02-01

222

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

PubMed

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

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

2014-07-01

223

Glucose and Glucose Esters in the Larval Secretion of Chrysomela Lapponica ; Selectivity of the Glucoside Import System from Host Plant Leaves  

Microsoft Academic Search

Larvae of Chrysomela lapponica (Coleoptera: Chrysomelidae) sequester characteristic O-glucosides from the leaves of their food plants, namely Betula and\\/or Salix The present study focuses on birch-feeding larvae of C. lapponica from the Altai region in East Kazakhstan. As in other sequestering leaf beetle larvae, the compounds are transported intact\\u000a via different membrane barriers into the defensive system, followed by glucoside

Karla Tolzin-Banasch; Enkhmaa Dagvadorj; Ulrike Sammer; Maritta Kunert; Roy Kirsch; Kerstin Ploss; Jacques M. Pasteels; Wilhelm Boland

2011-01-01

224

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

225

Phaseoloidin, a homogentisic acid glucoside from Nicotiana attenuata trichomes, contributes to the plant's resistance against lepidopteran herbivores.  

PubMed

Plant trichomes are known for their capability to produce and store secondary metabolites that protect plants from biotic and abiotic stresses. (1)H NMR studies on intact individual trichomes located on the leaf surface of Nicotiana attenuata revealed the presence of two major secondary metabolites: nicotine, the signature metabolite of the genus, and phaseoloidin, a homogentisic acid glucoside. This glucoside was reported originally from the seeds of Entada phaseoloides, and this is the first report of its occurrence in a Solanaceous plant. Artificial diet feeding bioassays with Manduca sexta and Spodoptera littoralis larvae, two important herbivores of N. attenuata, revealed that the ingestion of phaseoloidin negatively influenced caterpillar performance. This effect was more pronounced for the generalist, S. littoralis, than for the specialists, M. sexta. PMID:21904938

Weinhold, Alexander; Shaker, Kamel; Wenzler, Michael; Schneider, Bernd; Baldwin, Ian T

2011-10-01

226

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

PubMed

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

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

2013-12-01

227

Proanthocyanidin profile of cowpea (Vigna unguiculata) reveals catechin-O-glucoside as the dominant compound.  

PubMed

Proanthocyanidin (PA) profile and content can have important nutritional and health implications on plant foods. Six diverse cowpea phenotypes (black, red, green, white, light-brown and golden-brown) were investigated for PA composition using normal-phase HPLC and reversed-phase UPLC-TQD-MS. Catechin and (epi)afzelechin were the major flavan-3-ol units. Unusual composition was observed in all cowpea phenotypes with significant degrees of glycosylation in the monomers and dimers. The PA content of cowpea (dry basis) ranged between 2.2 and 6.3 mg/g. Monomeric flavan-3-ols were the largest group of PA (36-69%) in cowpea, with catechin-7-O-glucoside accounting for most (about 88%) of the monomers. The oligomers with degree of polymerization (DP) 2-4 ranged from 0.41 to 1.3 mg/g (15-20%), whereas DP>10 polymers accounted for only 13.5% of PA. Future studies that highlight the impact of the unusual cowpea PA profile on nutritional and bioactive properties of this important legume are warranted. PMID:23561075

Ojwang, Leonnard O; Yang, Liyi; Dykes, Linda; Awika, Joseph

2013-08-15

228

Structural characterization of inclusion complexes between cyanidin-3-O-glucoside and ?-cyclodextrin.  

PubMed

Inclusion complex formation between the multiple equilibrium forms of cyanidin-3-O-glucoside (cy3glc) and ?-cyclodextrin (?-CD) was investigated using a combined approach of NMR spectroscopy and Molecular Dynamics simulation. Diffusion ordered NMR spectroscopy (DOSY) and study of nuclear Overhauser effects (NOE) were used to determine the selective intermolecular interactions and structure of these complexes in aqueous solution. The observed chemical shift displacements of resonance signals of protons from the interior of ?-CD cavity and protons belonging to the hemiketal (B) and cis-chalcone forms (Cc), the diffusion measurements using DOSY and the NOE studies have anticipated the formation of an inclusion complex between these two forms and ?-CD. The analysis of the NMR spectral data has shown no evidence of internal interaction between ?-CD and the flavylium cation (AH(+)) or trans-chalcone (Ct) forms of cy3glc. The hemiketal formed a 1:1 inclusion complex with ?-cyclodextrin in which the pyranic C ring is deeply included inside the ?-CD cavity while B ring lies on the plane of the wider rim of ?-CD. The structure of the complexes was also clarified through a theoretical approach by Molecular Dynamics simulation. PMID:24507282

Fernandes, Ana; Ivanova, Galya; Brás, Natércia F; Mateus, Nuno; Ramos, Maria J; Rangel, Maria; de Freitas, Victor

2014-02-15

229

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

230

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

231

Salicylic acid and salicylic acid glucoside in xylem sap of Brassica napus infected with Verticillium longisporum  

PubMed Central

Salicylic acid (SA) and its glucoside (SAG) were detected in xylem sap of Brassica napus by HPLC–MS. Concentrations of SA and SAG in xylem sap from the root and hypocotyl of the plant, and in extracts of shoots above the hypocotyl, increased after infection with the vascular pathogen Verticillium longisporum. Both concentrations were correlated with disease severity assessed as the reduction in shoot length. Furthermore, SAG levels in shoot extracts were correlated with the amount of V. longisporum DNA in the hypocotyls. Although the concentration of SAG (but not SA) in xylem sap of infected plants gradually declined from 14 to 35 days post infection, SAG levels remained significantly higher than in uninfected plants during the whole experiment. Jasmonic acid (JA) and abscisic acid (ABA) levels in xylem sap were not affected by infection with V. longisporum. SA and SAG extend the list of phytohormones potentially transported from root to shoot with the transpiration stream. The physiological relevance of this transport and its contribution to the distribution of SA in plants remain to be elucidated. PMID:19449088

Ratzinger, Astrid; Riediger, Nadine; von Tiedemann, Andreas

2009-01-01

232

Salicylic acid and salicylic acid glucoside in xylem sap of Brassica napus infected with Verticillium longisporum.  

PubMed

Salicylic acid (SA) and its glucoside (SAG) were detected in xylem sap of Brassica napus by HPLC-MS. Concentrations of SA and SAG in xylem sap from the root and hypocotyl of the plant, and in extracts of shoots above the hypocotyl, increased after infection with the vascular pathogen Verticillium longisporum. Both concentrations were correlated with disease severity assessed as the reduction in shoot length. Furthermore, SAG levels in shoot extracts were correlated with the amount of V. longisporum DNA in the hypocotyls. Although the concentration of SAG (but not SA) in xylem sap of infected plants gradually declined from 14 to 35 days post infection, SAG levels remained significantly higher than in uninfected plants during the whole experiment. Jasmonic acid (JA) and abscisic acid (ABA) levels in xylem sap were not affected by infection with V. longisporum. SA and SAG extend the list of phytohormones potentially transported from root to shoot with the transpiration stream. The physiological relevance of this transport and its contribution to the distribution of SA in plants remain to be elucidated. PMID:19449088

Ratzinger, Astrid; Riediger, Nadine; von Tiedemann, Andreas; Karlovsky, Petr

2009-09-01

233

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 S?lvh?j; M?ller, Birger Lindberg; Bak, S?ren

2014-01-01

234

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

235

The first total synthesis of cytopiloyne, an anti-diabetic, polyacetylenic glucoside.  

PubMed

The first total synthesis of cytopiloyne 1, a novel bioactive polyacetylenic glucoside isolated from the extract of Bidens pilosa, is described. The structure of cytopiloyne was determined to be 2-?-D-glucopyranosyloxy-1-hydroxytrideca-5,7,9,11-tetrayne by using various spectroscopic methods, but the chirality of the polyyne moiety was unknown. Herein, the convergent synthesis of two diastereomers of cytopiloyne by starting from commercially available 4-(2-hydroxyethyl)-2,2-dimethyl-1,3-diozolane is described. The synthetic sequence involved two key steps: stereoselective glycosylation of the glucosyl trichloroacetimidate with 1-[(4-methoxybenzyl)oxy]hex-5-yn-2-ol to give the desired ?-glycoside and the construction of the glucosyl tetrayne skeleton by using a palladium/silver-catalyzed cross-coupling reaction to form the alkyne-alkyne bond, the first such use of this reaction. Comparison between the observed and published characterization data showed the 2R isomer to be the natural product cytopiloyne. PMID:21681841

Kumar, Chidambaram Ramesh; Tsai, Chi-Hui; Chao, Yu-Sheng; Lee, Jinq-Chyi

2011-07-25

236

Cytopiloyne, a novel polyacetylenic glucoside from Bidens pilosa, functions as a T helper cell modulator.  

PubMed

An extract of Bidens pilosa, an anti-diabetic Asteraceae plant, has recently been reported to modulate T cell differentiation and prevent the development of non-obese diabetes (NOD) in NOD mice. In this paper, a novel bioactive polyacetylenic glucoside, cytopiloyne (1), was identified from the Bidens pilosa extract using ex vivo T cell differentiation assays based on a bioactivity-guided fractionation and isolation procedure. Its structure was elucidated as 2beta-D-glucopyranosyloxy-1-hydroxytrideca-5,7,9,11-tetrayne by various spectroscopic methods. Functional studies showed that cytopiloyne was able to inhibit the differentiation of naïve T helper (Th0) cells into type I T helper (Th1) cells but to promote the differentiation of Th0 cells into type II T helper (Th2) cell. Accordingly, cytopiloyne also suppressed IFN-gamma expression and promoted IL-4 expression in mouse splenocytes ex vivo. These results suggest that cytopiloyne functions as a T cell modulator that may directly contribute to the ethnopharmacological effect of Bidens pilosa extract on preventing diabetes. Moreover, cytopiloyne can serve as an index compound for quality control of lot-to-lot extract preparations of Bidens pilosa. PMID:17101254

Chiang, Yi-Ming; Chang, Cicero Lee-Tian; Chang, Shu-Lin; Yang, Wen-Chin; Shyur, Lie-Fen

2007-04-01

237

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

PubMed

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

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

2013-03-01

238

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

239

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

PubMed

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

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

2014-05-01

240

Subcellular Localization of the Cyanogenic Glucoside of Sorghum by Autoradiography 1  

PubMed Central

The use of microautoradiography at the electron microscopic level indicates that the vacuole is the site of accumulation of the cyanogenic glucoside of Sorghum bicolor. When a specific biosynthetic precursor of dhurrin, p-hydroxy[3,5-3H]phenylacetaldoxime, was used, 90% of the tritium label was recovered in the vacuoles of tissue prepared for microautoradiography. l-[3,5-3H]Tyrosine and d-[1-3H(N)]glucose, nonspecific precursors of dhurrin, of differing solubilities and biosynthetic capacity, were also fed to the shoots. The data obtained from these controls indicated that the high recovery of label in the vacuole of aldoxime-fed shoots was not indicative simply of the size of the vacuole, nor was it a result of movement of labeled compounds during preparation of the tissue for electron microscopy. The problem of movement of these labeled compounds during dehydration of tissue was dramatically reduced by chemical dehydration in 2,2-dimethoxypropane in less than 30 minutes rather than with routine dehydration in acetone or alcohol series for 24 hours. Images PMID:16659911

Saunders, James A.; Conn, Eric E.; Lin, Chin Ho; Stocking, C. Ralph

1977-01-01

241

Expression of a zeatin-O-glucoside-degrading beta-glucosidase in Brassica napus.  

PubMed Central

A beta-glucosidase was purified from seeds of Brassica napus L. (oilseed rape). The 130-kD native enzyme consisted of a disulfide-linked dimer of 64-kD monomers. Internal amino acid sequences were used to construct degenerate primers for polymerase chain reaction-mediated cloning of cDNA for the enzyme. One nearly full-length and one partial beta-glucosidase-encoding cDNA clone were isolated and sequenced. Southern hybridization showed that beta-glucosidase is encoded by a small gene family in B. napus. Northern hybridization showed that the genes are expressed in the seed, with a low degree of expression in other tissues. In the seed, the expression started at 30 days after pollination (DAP), with the highest expression at 40 DAP. The size of the transcript was approximately 1900 nucleotides. In situ hybridization to developing seeds of B. napus showed that the beta-glucosidase expression started at 30 DAP around the provascular tissue in the embryo axis. In the cotyledons, mRNA initially accumulated around the provascular tissues but was detected first at 35 DAP. At 40 DAP, expression occurred in most parts of the seed. In situ hybridization also detected beta-glucosidase mRNA in shoots, young roots, and the basal part of the hypocotyls. Zeatin-O-glucoside was identified as a natural substrate for B. napus beta-glucosidase. PMID:7659745

Falk, A; Rask, L

1995-01-01

242

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

PubMed Central

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

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

2013-01-01

243

454 pyrosequencing based transcriptome analysis of Zygaena filipendulae with focus on genes involved in biosynthesis of cyanogenic glucosides  

PubMed Central

Background An essential driving component in the co-evolution of plants and insects is the ability to produce and handle bioactive compounds. Plants produce bioactive natural products for defense, but some insects detoxify and/or sequester the compounds, opening up for new niches with fewer competitors. To study the molecular mechanism behind the co-adaption in plant-insect interactions, we have investigated the interactions between Lotus corniculatus and Zygaena filipendulae. They both contain cyanogenic glucosides which liberate toxic hydrogen cyanide upon breakdown. Moths belonging to the Zygaena family are the only insects known, able to carry out both de novo biosynthesis and sequestration of the same cyanogenic glucosides as those from their feed plants. The biosynthetic pathway for cyanogenic glucoside biosynthesis in Z. filipendulae proceeds using the same intermediates as in the well known pathway from plants, but none of the enzymes responsible have been identified. A genomics strategy founded on 454 pyrosequencing of the Z. filipendulae transcriptome was undertaken to identify some of these enzymes in Z. filipendulae. Results Comparisons of the Z. filipendulae transcriptome with the sequenced genomes of Bombyx mori, Drosophila melanogaster, Tribolium castaneum, Apis mellifera and Anopheles gambiae indicate a high coverage of the Z. filipendulae transcriptome. 11% of the Z. filipendulae transcriptome sequences were assigned to Gene Ontology categories. Candidate genes for enzymes functioning in the biosynthesis of cyanogenic glucosides (cytochrome P450 and family 1 glycosyltransferases) were identified based on sequence length, number of copies and presence/absence of close homologs in D. melanogaster, B. mori and the cyanogenic butterfly Heliconius. Examination of biased codon usage, GC content and selection on gene candidates support the notion of cyanogenesis as an "old" trait within Ditrysia, as well as its origins being convergent between plants and insects. Conclusion Pyrosequencing is an attractive approach to gain access to genes in the biosynthesis of bio-active natural products from insects and other organisms, for which the genome sequence is not known. Based on analysis of the Z. filipendulae transcriptome, promising gene candidates for biosynthesis of cyanogenic glucosides was identified, and the suitability of Z. filipendulae as a model system for cyanogenesis in insects is evident. PMID:19954531

2009-01-01

244

Potential role for gut microbiota in cell wall digestion and glucoside detoxification in Tenebrio molitor larvae.  

PubMed

Tenebrio molitor larvae were successfully reared free of cultivatable gut lumen bacteria, yeasts and fungi using two approaches; aseptic rearing from surface sterilized eggs and by feeding larvae with antibiotic-containing food. Insects were reared on a rich-nutrient complete diet or a nutrient-poor refractory diet. A comparison of digestive enzyme activities in germ free and conventional insects containing a gut microbiota did not reveal gross differences in enzymes that degrade cell walls from bacteria (lysozyme), fungi (chitinase and laminarinase) and plants (cellulase and licheninase). This suggested that microbial-derived enzymes are not an essential component of the digestive process in this insect. However, more detailed analysis of T. molitor midgut proteins using an electrophoretic separation approach showed that some digestive enzymes were absent and others were newly expressed in microbiota-free larvae. Larvae reared in antibiotic-containing refractory wheat bran diet performed poorly in comparison with controls. The addition of saligenin, the aglycone of the plant glucoside salicin, has more deleterious effects on microbiota-free larvae than on the conventionally reared larvae, suggesting a detoxifying role of midgut microbiota. Analysis of the volatile organic compounds released from the faecal pellets of the larvae shows key differences in the profiles from conventionally reared and aseptically reared larvae. Pentadecene is a semiochemical commonly found in other beetle species. Here we demonstrate the absence of pentadecene from aseptically reared larvae in contrast to its presence in conventionally reared larvae. The results are discussed in the light of the hypothesis that microbial products play subtle roles in the life of the insect, they are involved in the digestion of refractory food, detoxification of secondary plant compounds and modify the volatile profiles of the insect host. PMID:16600286

Genta, Fernando A; Dillon, Rod J; Terra, Walter R; Ferreira, Clélia

2006-06-01

245

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; Kruger, S; Hecker, M

1997-01-01

246

Specificity of binding of beta-glucoside activators of ryegrass (1-->3)-beta-glucan synthase and the synthesis of some potential photoaffinity activators.  

PubMed Central

Structure-activity relationships among glycoside activators of ryegrass (Lolium multiflorum) (1-->3)-beta-glucan synthase were investigated using a number of natural and synthetic glycosides, including some carrying photoaffinity functions. There is an absolute requirement for a beta-D-glycosyl moiety in the activator, both S- and N-glucosides are active, and the position of the glucosidic linkage in beta-glucose disaccharides has a significant effect on the affinity of binding. However, the binding requirement does not extend beyond a single beta-D-glucosyl residue, and beta-D-oligoglucosides are less effective than disaccharides. The nature of the aglycon has a major influence on the binding affinity. Hydrophobic aglycons lower the concentration required for half-maximal stimulation of the enzyme obtained from an Eadie-Hofstee plot of kinetic data (Ka) for activation, but charge aglycons increase Ka. Relative to methyl-beta-D-glucoside and cellobiose (Ka 1.1 mM), the most potent compounds tested were N-[4-(benzoyl)benzoyl]-beta-D-glucosylamine and 2'-[4-azidosalicylamino]ethyl-1-thio-beta-D-glucoside with K(a)s of approximately 30 microM. The latter also was tested for its potential to specifically label the beta-glucoside-binding site on the synthase, but under the conditions used the binding was found to be nonspecific. PMID:8756503

Ng, K; Johnson, E; Stone, B A

1996-01-01

247

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

PubMed Central

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

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

2008-01-01

248

Ptaquiloside Z, a new toxic unstable sesquiterpene glucoside from the neotropical bracken fern Pteridium aquilinum var. caudatum.  

PubMed

Reversed-phase HPLC fractionation, monitored by brine shrimp bioassay, led to the isolation of a new illudane-type sesquiterpene glucoside, ptaquiloside Z (2), as well as the known bracken carcinogen ptaquiloside (1), from a bioactive aqueous extract of the neotropical bracken fern Pteridium aquilinum var. caudatum (Pteridaceae). The structure of ptaquiloside Z (2) was confirmed by spectroscopic analyses and chemical degradation. Both compounds exhibited similar toxicity (LC50 62.5 micrograms/ml at 24 h and LC50 7.8 micrograms/ml at 48 h) toward brine shrimp. PMID:9881114

Castillo, U F; Ojika, M; Alonso-Amelot, M; Sakagami, Y

1998-11-01

249

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

NASA Astrophysics Data System (ADS)

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

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

2013-12-01

250

Iridoid and secoiridoid glycosides in a hybrid complex of bush honeysuckles (Lonicera spp., Caprifolicaceae): implications for evolutionary ecology and invasion biology.  

PubMed

Interspecific hybridization among non-native plant species can generate genotypes that are more reproductively successful in the introduced habitat than either parent. One important mechanism that may serve as a stimulus for the evolution of invasiveness in hybrids is increased variation in secondary metabolite chemistry, but still very little is known about patterns of chemical trait introgression in plant hybrid zones. This study examined the occurrence of iridoid and secoiridoid glycosides (IGs), an important group of plant defense compounds, in three species of honeysuckle, Lonicera morrowii A. Gray, Lonicera tatarica L., and their hybrid Lonicera×bella Zabel. (Caprifoliaceae), all of which are considered invasive in various parts of North America. Hybrid genotypes had a diversity of IGs inherited from both parent species, as well as one component not detected in either parent. All three species were similar in that overall concentrations of IGs were significantly higher in fruits than in leaves, and several compounds that were major components of fruits were never found in leaves. However, specific patterns of quantitative distribution among leaves, unripe fruits, and ripe fruits differed among the three species, with a relatively higher allocation to fruits in the hybrid species than for either parent. These patterns likely have important consequences for plant interactions with antagonistic herbivores and pathogens as well as mutualistic seed dispersers, and thus the potential invasiveness of hybrid and parental species in their introduced range. Methods established here for quantitative analysis of IGs will allow for the exploration of many compelling research questions related to the evolutionary ecology and invasion biology of these and other related species in the genus Lonicera. PMID:23228598

Whitehead, Susan R; Bowers, M Deane

2013-02-01

251

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

PubMed Central

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

Lohaus, Gertrud; Schwerdtfeger, Michael

2014-01-01

252

Isolation of a reduced form of cyanidin 3-O-?-D-glucoside from immature black soybean (Glycine max (L.) Merr.) and its reducing properties.  

PubMed

5,7,3',4'-Tetrahydroxyflav-2-en-3-ol 3-O-?-D-glucoside was isolated from the seed coats of immature black soybeans (Glycine max (L.) Merr.). This compound is a reduced form of cyanidin 3-O-?-D-glucoside (cyanidin 3-G) which was obtained by reaction with hydrochloric acid. The molecule has reducing activity for a tetrazolium derivative (WST-1) in the presence of 1-methoxy-5-methylphenazinium methylsulfate (1-methoxy PMS) in a similar manner to NADH. The seed coats of immature black soybeans also contain epicatechin as a major constituent, while cyanidin 3-G and procyanidin B2 are present at lower concentrations. Immature brown soybeans did not contain 5,7,3',4'-tetrahydroxyflav-2-en-3-ol 3-O-?-D-glucoside, but did contain both epicatechin and procyanidin B2. Immature yellow soybeans contained none of them. PMID:23985492

Fukami, Harukazu; Yano, Yoshihisa; Iwashita, Takashi

2013-01-01

253

Tetra-acylated cyanidin 3-sophoroside-5-glucosides from the flowers of Iberis umbellata L. (Cruciferae).  

PubMed

The structures of 11 acylated cyanidin 3-sophoroside-5-glucosides (pigments 1-11), isolated from the flowers of Iberis umbellata cultivars (Cruciferae), were elucidated by chemical and spectroscopic methods. Pigments 1-11 were acylated with malonic acid, p-coumaric acid, ferulic acid, sinapic acid and/or glucosylhydroxycinnamic acids. Pigments 1-11 were classified into four groups by the substitution patterns of the linear acylated residues at the 3-position of the cyanidin. In the first group, pigments 1-3 were determined to be cyanidin 3-O-[2-O-(2-O-(acyl)-beta-glucopyranosyl)-6-O-(trans-p-coumaroyl)-beta-glucopyranoside]-5-O-[6-O-(malonyl)-beta-glucopyranoside], in which the acyl moiety varied with none for pigment 1, ferulic acid for pigment 2 and sinapic acid for pigment 3. In the second one, pigments 4-6 were cyanidin 3-O-[2-O-(2-O-(acyl)-beta-glucopyranosyl)-6-O-(4-O-(beta-glucopyranosyl)-trans-p-coumaroyl)-beta-glucopyranoside]-5-O-[6-O-(malonyl)-beta-glucopyranoside], in which the acyl moiety varied with none for pigment 4, ferulic acid for pigment 5 and sinapic acid for pigment 6. In the third one, pigments 7-9 were cyanidin 3-O-[2-O-(2-O-(acyl)-beta-glucopyranosyl)-6-O-(4-O-(6-O-(trans-feruloyl)-beta-glucopyranosyl)-trans-p-coumaroyl)-beta-glucopyranoside]-5-O-[6-O-(malonyl)-beta-glucopyranoside], in which the acyl moiety varied with none for pigment 7, ferulic acid for pigment 8, and sinapic acid for pigment 9. In the last one, pigments 10 and 11 were cyanidin 3-O-[2-O-(2-O-(acyl)-beta-glucopyranosyl)-6-O-(4-O-(6-O-(4-O-(beta-glucopyranosyl)-trans-feruloyl)-beta-glucopyranosyl)-trans-p-coumaroyl)-beta-glucopyranoside]-5-O-[6-O-(malonyl)-beta-glucopyranoside], in which acyl moieties were none for pigment 10 and ferulic acid for pigment 11. The distribution of these pigments was examined in the flowers of four cultivars of I. umbellata by HPLC analysis. Pigment 1 acylated with one molecule of p-coumaric acid was dominantly observed in purple-violet cultivars. On the other hand, pigments (9 and 11) acylated with three molecules of hydroxycinnamic acids were observed in lilac (purple-violet) cultivars as major anthocyanins. The bluing effect and stability on these anthocyanin colors were discussed in relation to the molecular number of hydroxycinnamic acids in these anthocyanin molecules. PMID:18514755

Saito, Norio; Tatsuzawa, Fumi; Suenaga, Eri; Toki, Kenjiro; Shinoda, Koichi; Shigihara, Atsushi; Honda, Toshio

2008-12-01

254

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

NASA Astrophysics Data System (ADS)

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

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

2014-05-01

255

An LC-MS method for simultaneous determination of five iridoids from Zhi-zi-chi Decoction in rat brain microdialysates and tissue homogenates: towards an in depth study for its antidepressive activity.  

PubMed

Zhi-zi-chi Decoction has been clinically utilized for the treatment of depression for more than thousand years. In order to investigate the possible bioactive components that could pass through the blood brain barrier (BBB) and the mechanism of antidepressant, a sensitive LC-MS method was developed to detect the ingredients (geniposide, scandoside methyl ester, gardenoside, deacetyl asperulosidic acid methyl ester and genipin-1-?-gentiobioside) in rat brain microdialysates and tissue homogenates samples (hippocampus, hypothalamus, premotor cortex, striatum, oblongata and cerebellum). Method development and validation are described in terms of calibration curves, extraction yield, lower limit of quantification (LLOQ), precision, accuracy, intra- and inter-day variability, which are in accordance with the requirements. Microdialysis in hippocampus demonstrated that the five iridoids possessed complete pharmacokinetic process while brain tissue homogenate method testified the distribution regularity in brain. The work clarified that the five iridoids, as antidepressant ingredients, could pass through the BBB, distribute targeted and possess complete pharmacokinetics in brain. These observations, along with the large database of rat brain microdialysates and tissue homogenates data, could enable future efforts aimed to improve our understanding of the relationship between bioactive ingredients and clinical therapy of depression. PMID:25049209

Qu, Kankan; Zhao, Longshan; Luo, Xinyi; Zhang, Chenning; Hou, Pengyi; Bi, Kaishun; Chen, Xiaohui

2014-08-15

256

Glucose and glucose esters in the larval secretion of Chrysomela lapponica; selectivity of the glucoside import system from host plant leaves.  

PubMed

Larvae of Chrysomela lapponica (Coleoptera: Chrysomelidae) sequester characteristic O-glucosides from the leaves of their food plants, namely Betula and/or Salix The present study focuses on birch-feeding larvae of C. lapponica from the Altai region in East Kazakhstan. As in other sequestering leaf beetle larvae, the compounds are transported intact via different membrane barriers into the defensive system, followed by glucoside cleavage and subsequent transformations of the plant-derived aglycones. Unlike previous studies with model compounds, we studied the sequestration of phytogenic precursors by analyzing the complex pattern of glucosides present in food plant Betula rotundifolia (39 compounds) and compared this composition with the aglycones present as butyrate esters in the defensive secretion. In addition to the analytic approach, the insect's ability, to transport individual glucosides was tested by using hydrolysis-resistant thioglucoside analogs, applied onto the leaf surface. The test compounds reach the defensive system intact and without intermediate transformation. No significant difference of the transport capacity and selectivity was observed between larvae of birch-feeding population from Kazakhstan, and previous results for larvae of birch-feeding population from the Czech Republic or willow-feeding populations. Overall, the transport of the phytogenic glucosides is highly selective and highly efficient, since only minor compounds of the spectrum of phytogenic glucoside precursors contribute to the limited number of aglycones utilized in the defensive secretion. Interestingly, salicortin 44 and tremulacin 60 were found in the leaves, but no aldehyde or esters of salicylalcohol. Surprisingly, we observed large amounts of free glucose, together with small amounts of 6-O-butyrate esters of glucose (27a/b and 28a/b). PMID:21301937

Tolzin-Banasch, Karla; Dagvadorj, Enkhmaa; Sammer, Ulrike; Kunert, Maritta; Kirsch, Roy; Ploss, Kerstin; Pasteels, Jacques M; Boland, Wilhelm

2011-02-01

257

Analysis of the metabolites of isorhamnetin 3-O-glucoside produced by human intestinal flora in vitro by applying ultraperformance liquid chromatography/quadrupole time-of-flight mass spectrometry.  

PubMed

Isorhamnetin 3-O-glucoside, which is widely contained in many vegetables and rice, is expected to be metabolized by intestinal microbiota after digestion, which brings about the profile of its pharmacological effect. However, little is known about the interactions between this active ingredient and the intestinal flora. In this study, the preculture bacteria and GAM (general anaerobic medium) broth with isorhamnetin 3-O-glucoside were mixed for 48 h of incubation. Ultraperformance liquid chromatography/quadrupole time-of-flight mass spectrometry was used for analysis of the metabolites of isorhamnetin 3-O-glucoside in the corresponding supernatants of fermentation. The parent and five metabolites were found and preliminarily identified on the basis of the chromatograms and characteristics of their protonated ions. Four main metabolic pathways, including deglycosylation, demethoxylation, dehydroxylation, and acetylation, were summarized to explain how the metabolites were converted. Acetylated isorhamnetin 3-O-glucoside and kaempferol 3-O-glucoside were detected only in the sample of Escherichia sp. 12, and quercetin existed only in the sample of Escherichia sp. 4. However, the majority of bacteria could metabolize isorhamnetin 3-O-glucoside to its aglycon isorhamnetin, and then isorhamnetin was degraded to kaempferol. The metabolic pathway and the metabolites of isorhamnetin 3-O-glucoside yielded by different isolated human intestinal bacteria were investigated for the first time. The results probably provided useful information for further in vivo metabolism and active mechanism research on isorhamnetin 3-O-glucoside. PMID:24601527

Du, Le-yue; Zhao, Min; Xu, Jun; Qian, Da-wei; Jiang, Shu; Shang, Er-xin; Guo, Jian-ming; Duan, Jin-ao

2014-03-26

258

Isolation of Spinasterol and its Glucoside from Cell Suspension Cultures of Saponaria officinalis: 13C-NMR Spectral Data and Batch Culture Production.  

PubMed

Spinasterol and spinasteryl glucoside have been isolated as the exclusive sterols from cell suspension cultures of SAPONARIA OFFICINALIS and identified by MS, (1)H-NMR and (13)C-NMR spectral data. This result confirms the taxonomical vicinity of this plant to Chenopodiaceae and Amaranthaceae where Delta (7)-sterols were also described to be present. With more than 44% of total sterol content, the spinasteryl glucoside content is higher than in most of the common plants. This shows a particularly active glycosylation process probably in relation with the biosynthesis of saponosides. PMID:17340524

Henry, M; Chantalat-Dublanche, I

1985-08-01

259

Hexaconazole induces antioxidant protection and apigenin-7-glucoside accumulation in Matricaria chamomilla plants subjected to drought stress.  

PubMed

In this experiment, the possibility of enhancing the water deficit stress tolerance of chamomile (Matricaria chamomilla L.) during two growth stages by the exogenous application of hexaconazole (HEX) was investigated. To improve water deficit tolerance, HEX was applied in three concentrations during two different stages (50 and 80 days after sowing). After HEX applications, the plants were subjected to water deficit stress. Although all HEX concentrations improved the water deficit stress tolerance in chamomile plants, the application of 15 mg L(-1) provided better protection when compared to the other concentration. The exogenous application of HEX provided significant protection against water deficit stress compared to non-HEX-treated plants, significantly affecting the morphological characteristics and aspects of productivity, the relative water, protein and proline contents; non-enzymatic and enzymatic antioxidants; and the flower's apigenin-7-glucoside content. These results suggest that the HEX-induced tolerance to water deficit stress in chamomile was related to the changes in growth variables, antioxidants and the apigenin-7-glucoside content. PMID:21208683

Hojati, Mostafa; Modarres-Sanavy, Seyed Ali Mohammad; Ghanati, Faezeh; Panahi, Mehdi

2011-05-15

260

Microorganisms and nematodes increase levels of secondary metabolites in roots and root exudates of Plantago lanceolata  

Microsoft Academic Search

Plant secondary metabolites play an important role in constitutive and inducible direct defense of plants against their natural\\u000a enemies. While induction of defense by aboveground pathogens and herbivores is well-studied, induction by belowground organisms\\u000a is less explored. Here, we examine whether soil microorganisms and nematodes can induce changes in levels of the secondary\\u000a metabolites aucubin and catalpol (iridoid glycosides, IG)

Susanne Wurst; Roel Wagenaar; Arjen Biere; Wim H. van der Putten

2010-01-01

261

Effect of pH on the complexation of kaempferol-4'-glucoside with three ?-cyclodextrin derivatives: isothermal titration calorimetry and spectroscopy study.  

PubMed

The utilization of kaempferol and its glycosides in food and pharmaceutical industries could be improved by the formation of inclusion complexes with cyclodextrins at different pH. This study explores the complexation of kaempferol-4'-glucoside with sulfobutyl ether-?-cyclodextrin (SBE-?-CD), hydroxypropyl-?-cyclodextrin (HP-?-CD), and methylated-?-cyclodextrin (M-?-CD) in phosphate buffer solutions of different pH using isothermal titration calorimetry, UV-vis absorption and proton nuclear magnetic resonance spectroscopy at 298.2 K. Experimental results showed that kaempferol-4'-glucoside binds with the three ?- cyclodextrins in the same 1:1 stoichiometry. The rank order of stability constants is SBE-?-CD > HP-?-CD > M-?-CD at the same pH level and pH 6.0 > pH 7.4 > pH 9.0 for the same cyclodextrin. The binding of kaempferol-4'-glucoside with the three ?-cyclodextrin derivatives is synergistically driven by enthalpy and entropy at pH 6.0 and enthalpy-driven at pH 7.4 and 9.0. The possible inclusion mode was that in the cavity of ?-CD is included the planar benzopyranic-4-one part of the kaempferol-4'-glucoside. PMID:24308546

Zheng, Yan; Dong, Li-Na; Liu, Min; Chen, Aiju; Feng, Shangcai; Wang, Bingquan; Sun, Dezhi

2014-01-01

262

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

PubMed Central

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

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

2011-01-01

263

Malvidin-3-glucoside protects endothelial cells up-regulating endothelial NO synthase and inhibiting peroxynitrite-induced NF-kB activation.  

PubMed

Anthocyanins are the most abundant flavonoid constituents of fruits and vegetables and several epidemiological studies suggest that the consumption of these compounds protect against several diseases, including vascular disorders. Previously, we have reported that anthocyanins are able to counteract peroxynitrite-induced apoptotic effects in endothelial cells through inhibition of several crucial signaling cascades, upstream and downstream of mitochondria. Following these studies, here we investigated possible effects of malvidin-3-glucoside, one of the main dietary anthocyanins, on NO bioavailability and on peroxynitrite-induced NF-kB activation in the same cell model. Our results show that treatment of bovine arterial endothelial cells with malvidin-3-glucoside up-regulated eNOS mRNA, leading to the enhancement of eNOS activity and NO production, an effect even greater when cells were further stimulated with peroxynitrite. On the other hand, in these activated endothelial cells, malvidin-3-glucoside suppressed pro-inflammatory mediators, namely iNOS expression/NO biosynthesis, COX-2 expression and IL-6 production, through inhibition of NF-kB activation. These findings suggest a potential role of malvidin-3-glucoside in NO balance and in inhibition of pro-inflammatory signaling pathways, supporting its benefits in cardiovascular health and pointing to anthocyanins as a promising tool for development of functional foods and nutraceuticals to improve endothelial function. PMID:22959858

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

2012-09-30

264

Detection of Type A Trichothecene Di-Glucosides Produced in Corn by High-Resolution Liquid Chromatography-Orbitrap Mass Spectrometry  

PubMed Central

The existence of di-glucosylated derivative of T-2 toxin in plant (corn powder) was confirmed for the first time in addition to that of HT-2 toxin. These masked mycotoxins (mycotoxin glucosides) were identified as T-2 toxin-di-glucoside (T2GlcGlc) and HT-2 toxin-di-glucoside (HT2GlcGlc) based on accurate mass measurements of characteristic ions and fragmentation patterns using high-resolution liquid chromatography-Orbitrap mass spectrometric (LC-Orbitrap MS) analysis. Although the absolute structure of T2GlcGlc was not clarified, two glucose molecules were suggested to be conjugated at 3-OH position in tandem when considering the structure of T-2 toxin. On the other hand, the specification of the structure seems to be more complicated in the case of HT2GlcGlc, since HT-2 toxin has two possible positions (at 3-OH and 4-OH) to be glusocylated. In addition, 15-monoacetoxyscirpenol-glucoside (MASGlc) was also detected in the identical sample. PMID:23524332

Nakagawa, Hiroyuki; Sakamoto, Shigeru; Sago, Yuki; Nagashima, Hitoshi

2013-01-01

265

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

PubMed

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

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

2014-01-01

266

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

267

Isolation of cyanidin 3-glucoside from blue honeysuckle fruits by high-speed counter-current chromatography.  

PubMed

Blue honeysuckle fruits are rich in anthocyanins with many beneficial effects such as reduction of the risk of cardiovascular diseases, diabetes and cancers. High-speed counter-current chromatography (HSCCC) was used for the separation of anthocyanin on a preparative scale from blue honeysuckle fruit crude extract with a biphasic solvent system composed of tert-butyl methyl ether/n-butanol/acetonitrile/water/trifluoroacetic acid (2:2:1:5:0.01, v/v) for the first time in this paper. Each injection of 100 mg crude extract yielded 22.8 mg of cyanidin 3-glucoside (C3G) at 98.1% purity. The compound was identified by means of electro-spray ionisation mass (ESI/MS) and (1)H and (13)C nuclear magnetic resonance (NMR) spectra. PMID:24444952

Chen, Liang; Xin, Xiulan; Lan, Rong; Yuan, Qipeng; Wang, Xiaojie; Li, Ye

2014-01-01

268

The first crystal structure of an alkaline metal salt of thioglucose: potassium 1-thio-?-D-glucoside monohydrate.  

PubMed

In the crystal structure of the title hydrated salt, poly[(?(2)-aqua)(?(4)-1-sulfido-?-D-glucoside)potassium], [K(C(6)H(11)O(5)S)(H(2)O)](n) or K(+)·C(6)H(11)O(5)S(-)·H(2)O, each thioglucoside anion coordinates to four K(+) cations through three of its four hydroxy groups, forming a three-dimensional polymeric structure. The negatively charged thiolate group in each anion does not form an efficient coordination bond with a K(+) cation, but forms intermolecular hydrogen bonds with four hydroxy groups, which appears to sustain the polymeric structure. The Cremer-Pople parameters for the thioglucoside ligand (Q = 0.575, ? = 8.233° and ? = 353.773°) indicate a slight distortion of the pyranose ring. PMID:23221249

Yoshinari, Nobuto; Kitani, Naoki; Konno, Takumi

2012-12-01

269

Beta-glucoside permease represses the bgl operon of Escherichia coli by phosphorylation of the antiterminator protein and also interacts with glucose-specific enzyme III, the key element in catabolite control.  

PubMed Central

The beta-glucoside (bgl) operon of Escherichia coli is subject to both positive control by transcriptional termination/antitermination and negative control by the beta-glucoside-specific transport protein, an integral membrane protein known as enzyme IIBgl. Previous results led us to speculate that enzyme IIBgl exerts its negative control by phosphorylating and thereby inactivating the antiterminator protein, BglG. Specifically, our model postulated that the transport protein enzyme IIBgl exhibits protein-phosphotransferase activity in the absence of beta-glucosides. We now present biochemical evidence that the phosphorylation of protein BglG does indeed occur in vivo and that it is accompanied by the loss of antitermination activity. BglG persists in the phosphorylated state in the absence of beta-glucosides but is rapidly dephosphorylated when beta-glucosides become available for transport. Our data also suggested specific interactions between the beta-glucoside transport protein and the glucose-specific enzyme III (enzyme IIIGlc), a component of glucose transport and a key element in regulation of catabolite repression. These observations indicate that enzyme IIIGlc may, in conjunction with enzyme IIBgl, modulate the transport of beta-glucosides and the phosphorylation of the antiterminator protein. In the absence of both sugars, when the catabolite-controlled promoter of the operon is derepressed, enzyme IIIGlc may mediate tight repression of antitermination. Images PMID:2195546

Schnetz, K; Rak, B

1990-01-01

270

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

271

Biologically relevant lyotropic liquid crystalline phases in mixtures of n-octyl-?-D-glucoside and water. Determination of the phase diagram by fluorescence spectroscopy  

PubMed Central

When mixed with water, n-octyl-?-D-glucoside forms self-assembled nanostructures, several of which are liquid crystalline and all of which depend on the water/glucoside ratio and temperature. For practical use of these phases, a detailed understanding of the conditions under which they exist (i.e., the isobaric phase diagram) is required. We use the fluorescence of the dye molecule prodan as a new approach to probe the phases formed in these mixtures. The prodan fluorescence signal depends on the polarity of its environment and thus the phase(s) in which the dye exists. Visual inspection of the total fluorescence signal can qualitatively determine the phases present, including co-existing phases. Temperature-induced phase changes are also detected from variations observed in the prodan fluorescence spectrum. The sensitivity of this new technique allows the single and multiple phase regions to be mapped carefully for the first time. PMID:22385304

Karukstis, Kerry K.; Duim, Whitney C.; Van Hecke, Gerald R.; Hara, Nagiko

2012-01-01

272

Isolation, structural elucidation, MS profiling, and evaluation of triglyceride accumulation inhibitory effects of benzophenone C-glucosides from leaves of Mangifera indica L.  

PubMed

Seventy percent ethanol-water extract from the leaves of Mangifera indica L. (Anacardiaceae) was found to show an inhibitory effect on triglyceride (TG) accumulation in 3T3-L1 cells. From the active fraction, six new benzophenone C-glucosides, foliamangiferosides A(3) (1), A(4) (2), C(4) (3), C(5) (4), C(6) (5), and C(7) (6) together with 11 known benzophenone C-glucosides (7-17) were obtained. In this paper, isolation, structure elucidation (1-6), and MS fragment cleavage pathways of all 17 isolates were studied. 1-6 showed inhibitory effects on TG and free fatty acid accumulation in 3T3-L1 cells at 10 ?M. PMID:23368644

Zhang, Yi; Han, Lifeng; Ge, Dandan; Liu, Xuefeng; Liu, Erwei; Wu, Chunhua; Gao, Xiumei; Wang, Tao

2013-02-27

273

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

PubMed

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

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

2003-04-23

274

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

275

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

276

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

277

Assessment of extraction parameters on antioxidant capacity, polyphenol content, epigallocatechin gallate (EGCG), epicatechin gallate (ECG) and iriflophenone 3-C-?-glucoside of agarwood (Aquilaria crassna) young leaves.  

PubMed

The effects of ethanol concentration (0%-100%, v/v), solid-to-solvent ratio (1:10-1:60, w/v) and extraction time (30-180 min) on the extraction of polyphenols from agarwood (Aquilaria crassna) were examined. Total phenolic content (TPC), total flavonoid content (TFC) and total flavanol (TF) assays and HPLC-DAD were used for the determination and quantification of polyphenols, flavanol gallates (epigallocatechin gallate--EGCG and epicatechin gallate--ECG) and a benzophenone (iriflophenone 3-C-?-glucoside) from the crude polyphenol extract (CPE) of A. crassna. 2,2'-Diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity was used to evaluate the antioxidant capacity of the CPE. Experimental results concluded that ethanol concentration and solid-to-solvent ratio had significant effects (p<0.05) on the yields of polyphenol and antioxidant capacity. Extraction time had an insignificant influence on the recovery of EGCG, ECG and iriflophenone 3-C-?-glucoside, as well as radical scavenging capacity from the CPE. The extraction parameters that exhibited maximum yields were 40% (v/v) ethanol, 1:60 (w/v) for 30 min where the TPC, TFC, TF, DPPH, EGCG, ECG and iriflophenone 3-C-?-glucoside levels achieved were 183.5 mg GAE/g DW, 249.0 mg QE/g DW, 4.9 mg CE/g DW, 93.7%, 29.1 mg EGCG/g DW, 44.3 mg ECG/g DW and 39.9 mg iriflophenone 3-C-?-glucoside/g DW respectively. The IC50 of the CPE was 24.6 mg/L. PMID:25153858

Tay, Pei Yin; Tan, Chin Ping; Abas, Faridah; Yim, Hip Seng; Ho, Chun Wai

2014-01-01

278

Permeabilization of Microbacterium oxylans shifts the conversion of puerarin from puerarin-7-O-glucoside to puerarin-7-O-fructoside.  

PubMed

The main product of the conversion of puerarin by unpermeabilized cells of bacterium Microbacterium oxydans CGMCC 1788 was puerarin-7-O-glucoside (241 +/- 31.9 microM). Permeabilization with 40% ethanol could not increase conversion yield, whereas it resulted in change of main product; a previous trace product became a main product (213 +/- 48.0 microM) which was identified as a novel puerarin-7-O-fructoside by electrospray ionization time-of-flight MS, (13)C NMR, (1)H NMR, and GC-MS analysis of sugar composition, and puerarin-7-O-glucoside became a trace product (14.8 +/- 5.4 microM). However, the extract from cells of M. oxydans CGMCC 1788 permeabilized with ethanol converted puerarin to form 113.9 +/- 27.7 microM puerarin-7-O-glucoside and 187.8 +/- 29.5 microM puerarin-7-O-fructoside under the same conditions. When unpermeabilized intact cells were recovered and used repeatedly for the conversion of puerarin, with increase of reuse times, the yield of puerarin-7-O-glucoside gradually decreased, whereas the yield of puerarin-7-O-fructoside increased gradually in the conversion mixture. The main product of the conversion of puerarin by the tenth recycled unpremerbilized cells was puerarin-7-O-fructoside (288.4 +/- 24.0 microM). Therefore, the change of permeability of cell membrane of bacterium M. oxydans CGMCC 1788 contributed to the change of conversion of the product's composition. PMID:19943046

Yu, Cigang; Xu, Haidong; Huang, Guodong; Chen, Ting; Liu, Guiyou; Chai, Nan; Ji, Yin; Wang, Siyuan; Dai, Yijun; Yuan, Sheng

2010-04-01

279

GC-MS identification of GA 20 -13- O -glucoside formed from GA 20 in normal plants and dwarf-1 mutants of Zea mays L  

Microsoft Academic Search

After feeding GA20 to excised seedlings ofZea mays L. normals (N) and dwarf-1 mutants (d1), GA20-13-O-glucoside (9) was identified by HPLC and by GC-MS of its permethylated derivative. The glucosylation rate of GA20 was found to be higher in the dwarf-1 mutant (26%) than in the normal plant (3.6%). This article includes a GC-MS study in which diagnostic fragments from

G. Schneider; J. Schmidt; B. O. Phinney

1987-01-01

280

cDNA cloning and functional characterization of flavonol 3- O-glucoside-6?- O-malonyltransferases from flowers of Verbena hybrida and Lamium purpureum  

Microsoft Academic Search

Complementary DNAs coding for two flavonol 3-O-glucoside malonyltransferases, Vh3MaT1 and Lp3MaT1, were cloned from flowers of Verbena hybrida and Lamium purpureum, respectively, expressed in Escherichia coli cells, and functionally characterized. The cloning strategy took full advantage of the specific conservation of a sequence (–Tyr–Phe–Gly–Asn–Cys–, termed motif 2) in the anthocyanin-specific members of the versatile acyltransferase (VAT) family. Both of the

Hirokazu Suzuki; Toru Nakayama; Shiro Nagae; Masa-Atsu Yamaguchi; Takashi Iwashita; Yuko Fukui; Tokuzo Nishino

2004-01-01

281

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

Microsoft Academic Search

A mass spectrometric method based on the combined use of electrospray ionization, collision-induced dissociation and tandem mass spectrometry at high mass resolution has been applied to an investigation of the structural characterization of genistein-7-O-?-d-glucoside (5,7,4?-trihydroxyisoflavone). The product ion mass spectrum of [M?H]? ions shows neutral losses of the glycan residue (162Da) and of the glycan residue + H (163Da) by

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

2004-01-01

282

Iriflophenone-3-C-glucoside from Cyclopia genistoides: isolation and quantitative comparison of antioxidant capacity with mangiferin and isomangiferin using on-line HPLC antioxidant assays.  

PubMed

The benzophenone, iriflophenone-3-C-glucoside, was isolated from Cyclopia genistoides using a combination of fluid-fluid extraction, high performance counter-current chromatography (HPCCC) and semi-preparative high performance liquid chromatography (HPLC). The microplate oxygen radical absorbance capacity (ORAC) assay, with fluorescein as probe, was adapted for use in an on-line HPLC configuration. The method was validated using a mixture of authentic standards including iriflophenone-3-C-glucoside, and the xanthones, mangiferin and isomangiferin. Trolox (6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid) was included in the mixture for calculation of Trolox equivalent antioxidant capacity (TEAC) values. Using the on-line HPLC-ORAC assay, as well as 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS(+)) on-line assays, the antioxidant activity of iriflophenone-3-C-glucoside and isomangiferin was demonstrated for the first time. Iriflophenone-3-C-glucoside presented no radical scavenging ability against DPPH, but scavenged ABTS(+) and peroxyl radicals (TEACABTS of 1.04 and TEACORAC of 3.61). Isomangiferin showed slightly lower antioxidant capacity than mangiferin against DPPH (TEACDPPH of 0.57 vs. 0.62), but higher capacity against ABTS(+) (TEACABTS of 1.82 vs. 1.67) and peroxyl radical (TEACORAC of 4.14 vs. 3.69) than mangiferin. The on-line HPLC-ORAC assay was shown to be more sensitive for radical scavengers, but at the same time less selective for rapid radical scavengers than the DPPH assay. PMID:24566268

Malherbe, Christiaan J; Willenburg, Elize; de Beer, Dalene; Bonnet, Susan L; van der Westhuizen, Jan H; Joubert, Elizabeth

2014-03-01

283

Effects of baking on cyanidin-3-glucoside content and antioxidant properties of black and yellow soybean crackers.  

PubMed

Black soybean is a potential functional food ingredient with high anthocyanin content, but the ability to maintain anthocyanin content under dry heat processing has not been reported. This study investigated the effects of soybean seed coat colour and baking time-temperature combinations on the extractable antioxidant properties of a soy cracker food model. Crackers prepared with black soybeans had significantly higher TPC, total isoflavones, and peroxyl, hydroxyl, and ABTS(+) radical scavenging abilities than their yellow counterparts, at all time-temperature combinations. Cyanidin-3-glucoside (C3G) was detected only in black soybean crackers, and all baking treatments significantly decreased C3G. The greatest losses occurred at the low temperature×long time and high temperature×short time, the smallest loss with moderate temperature×short/medium time. The high temperature treatment altered phenolic acid and isoflavone profiles; however, total isoflavones were unaffected. Overall results suggest that moderate baking temperature at minimal time may best preserve anthocyanin and other phenolics in baked black soybean crackers. PMID:23790899

Slavin, Margaret; Lu, Yingjian; Kaplan, Nicholas; Yu, Liangli Lucy

2013-11-15

284

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

285

Synthesis and characterization of ampelopsin glucosides using dextransucrase from Leuconostoc mesenteroides B-1299CB4: glucosylation enhancing physicochemical properties.  

PubMed

Novel ampelopsin glucosides (AMPLS-Gs) were enzymatically synthesized and purified using a Sephadex LH-20 column. Each structure of the purified AMPLS-Gs was determined by nuclear magnetic resonance, and the ionic product of AMPLS-G1 was observed at m/z 505 (C??H??O??·Na)? using matrix-assisted laser desorption ionization time-of-flight mass spectrometry. AMPLS-G1 was identified as ampelopsin-4'-O-?-D-glucopyranoside. The optimum condition for AMPLS-G1, determined using response surface methodology, was 70 mM ampelopsin, 150 mM sucrose, and 1 U/mL dextransucrase, which resulted in an AMPLS-G1 yield of 34 g/L. The purified AMPLS-G1 displayed 89-fold increased water solubility and 14.5-fold browning resistance compared to those of AMPLS and competitive inhibition against tyrosinase with a K(i) value of 40.16 ?M. This value was smaller than that of AMPLS (K(i)=62.56 ?M) and much smaller than that of ?-arbutin (K(i)=514.84 ?M), a commercial active ingredient of whitening cosmetics. These results indicate the potential of AMPLS and AMPLS-G1 as superior ingredients for functional cosmetics. PMID:23040385

Woo, Hye-Jin; Kang, Hee-Kyoung; Nguyen, Thi Thanh Hanh; Kim, Go-Eun; Kim, Young-Min; Park, Jun-Seong; Kim, Duwoon; Cha, Jaeho; Moon, Young-Hwan; Nam, Seung-Hee; Xia, Yong-mei; Kimura, Atsuo; Kim, Doman

2012-12-10

286

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, Agnes; Burla, Bo J.; Bassin, Barbara; Eisenach, Cornelia; Zarrouk, Olfa; Vialet, Sandrine; Marlin, Therese; Chaves, Maria Manuela; Martinoia, Enrico; Nagy, Reka

2013-01-01

287

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

288

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

PubMed

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

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

2013-04-01

289

Repellent activity of catmint, Nepeta cataria, and iridoid nepetalactone isomers against Afro-tropical mosquitoes, ixodid ticks and red poultry mites.  

PubMed

The repellent activity of the essential oil of the catmint plant, Nepeta cataria (Lamiaceae), and the main iridoid compounds (4aS,7S,7aR) and (4aS,7S,7aS)-nepetalactone, was assessed against (i) major Afro-tropical pathogen vector mosquitoes, i.e. the malaria mosquito, Anopheles gambiae s.s. and the Southern house mosquito, Culex quinquefasciatus, using a World Health Organisation (WHO)-approved topical application bioassay (ii) the brown ear tick, Rhipicephalus appendiculatus, using a climbing repellency assay, and (iii) the red poultry mite, Dermanyssus gallinae, using field trapping experiments. Gas chromatography (GC) and coupled GC-mass spectrometry (GC-MS) analysis of two N. cataria chemotypes (A and B) used in the repellency assays showed that (4aS,7S,7aR) and (4aS,7S,7aS)-nepetalactone were present in different proportions, with one of the oils (from chemotype A) being dominated by the (4aS,7S,7aR) isomer (91.95% by GC), and the other oil (from chemotype B) containing the two (4aS,7S,7aR) and (4aS,7S,7aS) isomers in 16.98% and 69.83% (by GC), respectively. The sesquiterpene hydrocarbon (E)-(1R,9S)-caryophyllene was identified as the only other major component in the oils (8.05% and 13.19% by GC, respectively). Using the topical application bioassay, the oils showed high repellent activity (chemotype A RD(50)=0.081 mg cm(-2) and chemotype B RD(50)=0.091 mg cm(-2)) for An. gambiae comparable with the synthetic repellent DEET (RD(50)=0.12 mg cm(-2)), whilst for Cx. quinquefasciatus, lower repellent activity was recorded (chemotype A RD(50)=0.34 mg cm(-2) and chemotype B RD(50)=0.074 mg cm(-2)). Further repellency testing against An. gambiae using the purified (4aS,7S,7aR) and (4aS,7S,7aS)-nepetalactone isomers revealed overall lower repellent activity, compared to the chemotype A and B oils. Testing of binary mixtures of the (4aS,7S,7aR) and (4aS,7S,7aS) isomers across a range of ratios, but all at the same overall dose (0.1 mg), revealed not only a synergistic effect between the two, but also a surprising ratio-dependent effect, with lower activity for the pure isomers and equivalent or near-equivalent mixtures, but higher activity for non-equivalent ratios. Furthermore, a binary mixture of (4aS,7S,7aR) and (4aS,7S,7aS) isomers, in a ratio equivalent to that found in chemotype B oil, was less repellent than the oil itself, when tested at two doses equivalent to 0.1 and 0.01 mg chemotype B oil. The three-component blend including (E)-(1R,9S)-caryophyllene at the level found in chemotype B oil had the same activity as chemotype B oil. In a tick climbing repellency assay using R. appendiculatus, the oils showed high repellent activity comparable with data for other repellent essential oils (chemotype A RD(50)=0.005 mg and chemotype B RD(50)=0.0012 mg). In field trapping assays with D. gallinae, addition of the chemotype A and B oils, and a combination of the two, to traps pre-conditioned with D. gallinae, all resulted in a significant reduction of D. gallinae trap capture. In summary, these data suggest that although the nepetalactone isomers have the potential to be used in human and livestock protection against major pathogen vectors, intact, i.e. unfractionated, Nepeta spp. oils offer potentially greater protection, due to the presence of both nepetalactone isomers and other components such as (E)-(1R,9S)-caryophyllene. PMID:21056438

Birkett, Michael A; Hassanali, Ahmed; Hoglund, Solveig; Pettersson, Jan; Pickett, John A

2011-01-01

290

Cyanidin-3-Glucoside inhibits ethanol-induced invasion of breast cancer cells overexpressing ErbB2  

PubMed Central

Background Ethanol is a tumor promoter. Both epidemiological and experimental studies suggest that ethanol may enhance the metastasis of breast cancer cells. We have previously demonstrated that ethanol increased the migration/invasion of breast cancer cells expressing high levels of ErbB2. Amplification of ErbB2 is found in 20-30% of breast cancer patients and is associated with poor prognosis. We sought to identify agents that can prevent or ameliorate ethanol-induced invasion of breast cancer cells. Cyanidin-3-glucoside (C3G), an anthocyanin present in many vegetables and fruits, is a potent natural antioxidant. Ethanol exposure causes the accumulation of intracellular reactive oxygen species (ROS). This study evaluated the effect of C3G on ethanol-induced breast cancer cell migration/invasion. Results C3G attenuated ethanol-induced migration/invasion of breast cancer cells expressing high levels of ErbB2 (BT474, MDA-MB231 and MCF7ErbB2) in a concentration dependent manner. C3G decreased ethanol-mediated cell adhesion to the extracellular matrix (ECM) as well as the amount of focal adhesions and the formation of lamellipodial protrusion. It inhibited ethanol-stimulated phosphorylation of ErbB2, cSrc, FAK and p130Cas, as well as interactions among these proteins. C3G abolished ethanol-mediated p130Cas/JNK interaction. Conclusions C3G blocks ethanol-induced activation of the ErbB2/cSrc/FAK pathway which is necessary for cell migration/invasion. C3G may be beneficial in preventing/reducing ethanol-induced breast cancer metastasis. PMID:21034468

2010-01-01

291

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

PubMed

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

Nguan, Hockseng; Ahmadi, Sara; Hashim, Rauzah

2014-01-01

292

Reduced hepatotoxicity by total glucosides of paeony in combination treatment with leflunomide and methotrexate for patients with active rheumatoid arthritis.  

PubMed

Combination use of methotrexate (MTX) and leflunomide (LEF) has been proved effective in the treatment of active rheumatoid arthritis (RA). However, previous trials have documented that both are associated with increased incidence of liver toxicity. As active compounds extracted from the roots of the traditional Chinese herb Paeonia lactiflora Pall, total glucosides of paeony (TGP) have been shown to have anti-inflammatory, hepatoprotective and immuno-regulatory activities, without evident toxicity or side effects. In this 24-week, open label, randomized multicenter clinical trial, we investigated the efficacy of TGP and the protective effect on hepatotoxicity in the combination treatment with LEF and MTX for patients with active RA. A total of 204 patients with active RA (DAS28>3.2) recruited from 3 regional referral centers were enrolled and received MTX and LEF combination therapy (MTX 10 mg/week plus LEF 20 mg/day) with or without TGP for up to 24 weeks by randomization. Hepatotoxicity was defined as an increase of at least 1.5-fold the upper limits of normal (ULN) of alanine aminotransferase (ALT) or aspartate aminotransferase (AST). Significantly less frequent hepatotoxicity was observed in patients with TGP than those without (9.5% vs 34.8%, p < 0.001) at 12 weeks. The proportion of patients whose ALT or AST levels were > 1.5 to ?2 times and >2 to ?3 times the ULN were lower in TGP group than the control (1.9% vs 10.1%, 2.9% vs 12.4%, p < 0.05 respectively). More patients in the TGP group achieved a European League Against Rheumatism (EULAR) good response or moderate response at 12 weeks, although there is no statistical significance. Similar results were observed at 24 weeks. Our preliminary study demonstrates the hepatoprotective and additive role of TGP in combination with MTX and LEF in the treatment of active RA. PMID:23415907

Chen, Zhu; Li, Xiang-Pei; Li, Zhi-Jun; Xu, Liang; Li, Xiao-Mei

2013-03-01

293

Cyanidin-3-O-?-glucoside ameliorates lipopolysaccharide-induced acute lung injury by reducing TLR4 recruitment into lipid rafts.  

PubMed

Cyanidin-3-O-?-glucoside (C3G), a typical anthocyanin pigment that exists in the human diet, has been reported to have anti-inflammatory properties. The aim of this study was to detect the effect of C3G on LPS-induced acute lung injury and to investigate the molecular mechanisms. Acute lung injury was induced by intratracheal administration of LPS in mice. Alveolar macrophages from mice were stimulated with LPS and were treated with C3G. Our results showed that C3G attenuated lung histopathologic changes, myeloperoxidase (MPO) activity, TNF-?, IL-1? and IL-6 production in LPS-induced acute lung injury model. In vitro, C3G dose-dependently inhibited TNF-?, IL-1?, IL-6, IL-10 and IFN-? production, as well as NF-?B and IRF3 activation in LPS-stimulated alveolar macrophages. Furthermore, C3G disrupted the formation of lipid rafts by depleting cholesterol and inhibited TLR4 translocation into lipid rafts. Moreover, C3G activated LXR?-ABCG1-dependent cholesterol efflux. Knockout of LXR? abrogated the anti-inflammatory effects of C3G. In conclusion, C3G has a protective effect on LPS-induced acute lung injury. The promising anti-inflammatory mechanisms of C3G is associated with up-regulation of the LXR?-ABCG1 pathway which result in disrupting lipid rafts by depleting cholesterol and reducing translocation of TLR4 to lipid rafts, thereby suppressing TLR4 mediated inflammatory response. PMID:24841888

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

2014-07-15

294

Chemotaxonomy of Veroniceae and its allies in the Plantaginaceae  

Microsoft Academic Search

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,

Rilka Mladenova Taskova; Charlotte Held Gotfredsen; Søren Rosendal Jensen

2006-01-01

295

Inhibition of TNF-alpha, IL-1beta, and IL-6 productions and NF-kappa B activation in lipopolysaccharide-activated RAW 264.7 macrophages by catalposide, an iridoid glycoside isolated from Catalpa ovata G. Don (Bignoniaceae).  

PubMed

Catalposide, the major iridoid glycoside isolated from the stem bark of Catalpa ovata G. Don (Bignoniaceae), was found to inhibit the productions of tumor necrosis factor-alpha (TNF-alpha), interleukin-1beta (IL-1beta), and interleukin-6 (IL-6), and the activation of nuclear factor kappaB (NF-kappaB) in RAW 264.7 macrophages activated with lipopolysaccharide (LPS). Catalposide also inhibited the expressions of TNF-alpha, IL-1beta, and IL-6 genes and the nuclear translocation of p65 subunit of NF-kappaB in LPS-activated RAW 264.7 cells. Flow cytometric analysis revealed that catalposide suppressed the binding of FITC-conjugated LPS to CD14 on the surface of cells, probably resulting in the inhibitory effects on TNF-alpha, IL-1beta, and IL-6 productions and NF-kappaB activation. These findings suggest that catalposide could be an attractive candidate for adjunctive therapy in gram-negative bacterial infections. PMID:12349954

An, S J; Pae, H O; Oh, G S; Choi, B M; Jeong, S; Jang, S I; Oh, H; Kwon, T O; Song, C E; Chung, H T

2002-07-01

296

Chemical constituents from the leaves of Hydrangea macrophylla var. thunbergii (III): Absolute stereostructures of hydramacrosides A and B, secoiridoid glucoside complexes with inhibitory activity on histamine release.  

PubMed

Following the characterization of dihydroisocoumarin constituents, two secoiridoid glucoside complexes, called hydramacrosides A and B, were isolated from the leaves of Hydrangea macrophylla Seringe var. thunbergii Makino. The absolute stereostructures of hydramacrosides A and B were elucidated on the basis of chemical and physicochemical evidence, which included the application of the 13C-NMR glycosylation shift rule of 1,1'-disaccharides and the modified Mosher's method. Hydramacrosides A and B exhibited an inhibitory effect on histamine release from rat mast cells induced by an antigen-antibody reaction. PMID:10748718

Matsuda, H; Shimoda, H; Uemura, T; Ueda, T; Yamahara, J; Yoshikawa, M

1999-12-01

297

Plantagiolides I and J, two new withanolide glucosides from Tacca plantaginea with nuclear factor-kappaB inhibitory and peroxisome proliferator-activated receptor transactivational activities.  

PubMed

A novel withanolide glucoside, plantagiolide I (1), a new withanolide glucoside, plantagiolide J (2), and six known compounds (3-8) were isolated from the whole plant of Tacca plantaginea. Their structures were determined by spectroscopic and chemical methods. Compound 3 significantly inhibited tumor necrosis factor alpha (TNF?)-induced nuclear factor-kappaB (NF-?B) transcriptional activity in HepG2 cells in a dose-dependent manner, with IC(50) values of 9.0?µM. Compounds 1-8 enhanced the transcriptional activity of peroxisome proliferator-activated receptors (PPARs) in a dose-dependent manner, with EC(50) values ranging from 1.6 to 49.7?µM. In addition, the transactivational effects of compounds 1-8 on three individual PPAR subtypes, including PPAR?, ?(?), and ? were evaluated. Compounds 1-8 significantly activated the transcriptional activity of PPAR?(?), with EC(50) values in a ranging from 4.1 to 29.6?µM. These results provide scientific support for the use of T. plantaginea and its components for the prevention and treatment of inflammatory and metabolic diseases. PMID:23207631

Quang, Tran Hong; Ngan, Nguyen Thi Thanh; Minh, Chau Van; Kiem, Phan Van; Yen, Pham Hai; Tai, Bui Huu; Nhiem, Nguyen Xuan; Thao, Nguyen Phuong; Anh, Hoang Le Tuan; Luyen, Bui Thi Thuy; Yang, Seo Young; Kim, Young Ho

2012-01-01

298

Separation of patuletin-3-O-glucoside, astragalin, quercetin, kaempferol and isorhamnetin from Flaveria bidentis (L.) Kuntze by elution-pump-out high-performance counter-current chromatography.  

PubMed

Flaveria bidentis (L.) Kuntze is an annual alien weed of Flaveria Juss. (Asteraceae) in China. Bioactive compounds, mainly flavonol glycosides and flavones from F. bidentis (L.) Kuntze, have been studied in order to utilize this invasive weed, Analytical high-performance counter-current chromatography (HPCCC) was successfully used to separate patuletin-3-O-glucoside, a mixture of hyperoside (quercetin-3-O-galactoside) and 6-methoxykaempferol-3-O-galactoside, astragalin, quercetin, kaempferol and isorhamnetin using two runs with different solvent system. Ethyl acetate-methanol-water (10:1:10, v/v) was selected by analytical HPCCC as the optimum phase system for the separation of patuletin-3-O-glucoside, a mixture of hyperoside and 6-methoxykaempferol-3-O-galactoside, and astragalin. A Dichloromethane-methanol-water (5:3:2, v/v) was used for the separation of quercetin, kaempferol and isorhamnetin. The separation was then scaled up: the crude extract (ca 1.5 g) was separated by preparative HPCCC, yielding 12 mg of patuletin-3-O-glucoside at a purity of 98.3%, yielding 9 mg of a mixture of hyperoside and 6-methoxykaempferol-3-O-galactoside constituting over 98% of the fraction, and 16 mg of astragalin (kaempferol-3-O-glucoside) at a purity of over 99%. The pump-out peaks are isorhanetin (98% purity), kaemferol (93% purity) and quercitin (99% purity). The chemical structure of patuletin-3-O-glucoside and astragalin were confirmed by MS and ¹H, ¹³C NMR. PMID:21329934

Wei, Yun; Xie, Qianqian; Fisher, Derek; Sutherland, Ian A

2011-09-01

299

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

PubMed

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

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

2009-05-01

300

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

301

Linkage mapping, molecular cloning and functional analysis of soybean gene Fg2 encoding flavonol 3-O-glucoside (1 ? 6) rhamnosyltransferase.  

PubMed

There are substantial genotypic differences in the levels of flavonol glycosides (FGs) in soybean leaves. The first objective of this study was to identify and locate genes responsible for FG biosynthesis in the soybean genome. The second objective was to clone and verify the function of these candidate genes. Recombinant inbred lines (RILs) were developed by crossing the Kitakomachi and Koganejiro cultivars. The FGs were separated by high performance liquid chromatography (HPLC) and identified. The FGs of Koganejiro had rhamnose at the 6?-position of the glucose or galactose bound to the 3-position of kaempferol, whereas FGs of Kitakomachi were devoid of rhamnose. Among the 94 RILs, 53 RILs had HPLC peaks classified as Koganejiro type, and 41 RILs had peaks classified as Kitakomachi type. The segregation fitted a 1:1 ratio, suggesting that a single gene controls FG composition. SSR analysis, linkage mapping and genome database survey revealed a candidate gene in the molecular linkage group O (chromosome 10). The coding region of the gene from Koganejiro, designated as GmF3G6?Rt-a, is 1,392 bp long and encodes 464 amino acids, whereas the gene of Kitakomachi, GmF3G6?Rt-b, has a two-base deletion resulting in a truncated polypeptide consisting of 314 amino acids. The recombinant GmF3G6?Rt-a protein converted kaempferol 3-O-glucoside to kaempferol 3-O-rutinoside and utilized 3-O-glucosylated/galactosylated flavonols and UDP-rhamnose as substrates. GmF3G6?Rt-b protein had no activity. These results indicate that GmF3G6?Rt encodes a flavonol 3-O-glucoside (1 ? 6) rhamnosyltransferase and it probably corresponds to the Fg2 gene. GmF3G6?Rt was designated as UGT79A6 by the UGT Nomenclature Committee. PMID:24072327

Rojas Rodas, Felipe; Rodriguez, Tito O; Murai, Yoshinori; Iwashina, Tsukasa; Sugawara, Satoko; Suzuki, Makoto; Nakabayashi, Ryo; Yonekura-Sakakibara, Keiko; Saito, Kazuki; Kitajima, Junichi; Toda, Kyoko; Takahashi, Ryoji

2014-02-01

302

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

303

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

304

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

PubMed

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

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

2012-05-15

305

The evolutionary appearance of non-cyanogenic hydroxynitrile glucosides in the Lotus genus is accompanied by the substrate specialization of paralogous ?-glucosidases resulting from a crucial amino acid substitution.  

PubMed

Lotus japonicus, like several other legumes, biosynthesizes the cyanogenic ?-hydroxynitrile glucosides lotaustralin and linamarin. Upon tissue disruption these compounds are hydrolysed by a specific ?-glucosidase, resulting in the release of hydrogen cyanide. Lotus japonicus also produces the non-cyanogenic ?- and ?-hydroxynitrile glucosides rhodiocyanoside A and D using a biosynthetic pathway that branches off from lotaustralin biosynthesis. We previously established that BGD2 is the only ?-glucosidase responsible for cyanogenesis in leaves. Here we show that the paralogous BGD4 has the dominant physiological role in rhodiocyanoside degradation. Structural modelling, site-directed mutagenesis and activity assays establish that a glycine residue (G211) in the aglycone binding site of BGD2 is essential for its ability to hydrolyse the endogenous cyanogenic glucosides. The corresponding valine (V211) in BGD4 narrows the active site pocket, resulting in the exclusion of non-flat substrates such as lotaustralin and linamarin, but not of the more planar rhodiocyanosides. Rhodiocyanosides and the BGD4 gene only occur in L. japonicus and a few closely related species associated with the Lotus corniculatus clade within the Lotus genus. This suggests the evolutionary scenario that substrate specialization for rhodiocyanosides evolved from a promiscuous activity of a progenitor cyanogenic ?-glucosidase, resembling BGD2, and required no more than a single amino acid substitution. PMID:24861854

Lai, Daniela; Abou Hachem, Maher; Robson, Fran; Olsen, Carl Erik; Wang, Trevor L; Møller, Birger L; Takos, Adam M; Rook, Fred

2014-07-01

306

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

307

Prunin- and hesperetin glucoside-alkyl (C4-C18) esters interaction with Jurkat cells plasma membrane: consequences on membrane physical properties and antioxidant capacity.  

PubMed

Prunin (P)- and hesperetin glucoside (HG)-alkyl esters are lipid-soluble compounds with antimicrobial and antioxidant capacities in vitro. The effects of P- and HG-alkyl (C4-C18) esters (0.1-100?M) on human leukemia T (Jurkat) cells viability and plasma membrane fluidity were evaluated. After 1h of exposure, cell viability was not affected in the range 0.1-10?M. The decrease of cell viability found at 100?M concentration depended on the length of the alkyl chain and reached a maximum with C6-C12 derivatives. At this concentration, cell hyperpolarization and shrinkage were also observed. Cell plasma membrane fluidity was not affected, regardless the depths of the membrane level evaluated, but mild changes in plasma membrane hydration were found. Esterification did not affect the antioxidant capacity of P and HG (0.1-10?M) against 1mM H2O2. When exposed to 1mM AAPH, P-alkyl esters retained P antioxidant capacity, but HG-derivatives acted as pro-oxidants. Together, present experimental evidences suggest that short term exposures to 0.1-10?M concentrations of P- and HG-alkyl (C4-C18) esters can be considered safe for cultured human cells, and further studies are required to investigate their long term effects, as well their safety for human consumption. PMID:23354392

Céliz, Gustavo; Alfaro, Federico F; Cappellini, Cecilia; Daz, Mirta; Verstraeten, Sandra V

2013-05-01

308

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

309

Beta-D-glucoside protects against advanced glycation end products (AGEs)-mediated diabetic responses by suppressing ERK and inducing PPAR gamma DNA binding.  

PubMed

Accumulation of advanced glycation end products (AGEs), due to excessive amounts of 3- or 4-carbon sugars derived from glucose; cause multiple consequences in diabetic patients and older persons. The transcription factor, peroxisome proliferator-activated receptor gamma (PPAR?), is down regulated in the diabetic condition. Drugs targeting PPAR? were developed for diabetes therapy. We found that AGE inhibited PPAR? activity in different cell types induced by PPAR? activators, like troglitazone, rosiglitazone, oleamide, and anandamide. AGE induced translocation of PPAR? from nucleus to cytoplasm, increased on activation of ERK in cells. Antioxidants that inhibit AGE-induced NF-?B activation by preventing ROI generation were unable to protect AGE-mediated decrease in PPAR? activity. Only mangiferin, a ?-D-glucoside, prevented AGE-mediated decrease in PPAR? activity and inhibited phosphorylation of ERK and cytoplasmic translocation of PPAR?. Mangiferin interacts with PPAR? and enhanced its DNA binding activity as predicted by in silico and shown by in vitro DNA-binding activity. Overall, the data suggest that (i) mangiferin inhibited AGE-induced ERK activation thereby inhibited PPAR? phosphorylation and cytoplasmic translocation; (ii) mangiferin interacts with PPAR? and enhances its DNA-binding ability. With these dual effects, mangiferin can be a likely candidate for developing therapeutic drug against diabetes. PMID:23058985

Mahali, Sidhartha K; Manna, Sunil K

2012-12-15

310

Elucidation of the Final Reactions of DIMBOA-Glucoside Biosynthesis in Maize: Characterization of Bx6 and Bx71[W][OA  

PubMed Central

Benzoxazinoids were identified in the early 1960s as secondary metabolites of the grasses that function as natural pesticides and exhibit allelopathic properties. Benzoxazinoids are synthesized in seedlings and stored as glucosides (glcs); the main aglucone moieties are 2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one (DIBOA) and 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (DIMBOA). The genes of DIBOA-glc biosynthesis have previously been isolated and the enzymatic functions characterized. Here, the enzymes for conversion of DIBOA-glc to DIMBOA-glc are identified. DIBOA-glc is the substrate of the dioxygenase BENZOXAZINLESS6 (BX6) and the produced 2,4,7-trihydroxy-2H-1,4-benzoxazin-3-(4H)-one-glc is metabolized by the methyltransferase BX7 to yield DIMBOA-glc. Both enzymes exhibit moderate Km values (below 0.4 mm) and kcat values of 2.10 s?1 and 0.25 s?1, respectively. Although BX6 uses a glucosylated substrate, our localization studies indicate a cytoplasmic localization of the dioxygenase. Bx6 and Bx7 are highest expressed in seedling tissue, a feature shared with the other Bx genes. At present, Bx6 and Bx7 have no close relatives among the members of their respective gene families. Bx6 and Bx7 map to the cluster of Bx genes on the short arm of chromosome 4. PMID:18192444

Jonczyk, Rafal; Schmidt, Holger; Osterrieder, Anne; Fiesselmann, Andreas; Schullehner, Katrin; Haslbeck, Martin; Sicker, Dieter; Hofmann, Diana; Yalpani, Nasser; Simmons, Carl; Frey, Monika; Gierl, Alfons

2008-01-01

311

Cyanidin 3-O-Glucoside Reduces Helicobacter pylori VacA-Induced Cell Death of Gastric KATO III Cells through Inhibition of the SecA Pathway  

PubMed Central

Two key virulence factors of Helicobacter pylori are the secreted virulent proteins of vacuolating toxin A (VacA) and cytotoxin associated protein A (CagA) which lead to damages of gastric epithelial cells. We previously identified that the cyanidin 3-O-glucoside (C3G) inhibits the secretion of both VacA and CagA. In the current report, we show that C3G inhibits VacA secretion in a dose-dependent manner by inhibiting secretion system subunit protein A (SecA) synthesis. As SecA is involved in translocation of bacterial proteins, we predicted that inhibition of the SecA pathway by C3G should decrease H. pylori-induced cell death. To test this hypothesis, the human gastric cell line KATO III cells were co-cultured with H. pylori 60190 (VacA+/CagA+) and C3G. We found that C3G treatment caused a decrease in activation of the pro-apoptotic proteins caspase-3/-8 in H. pylori-infected cells leading to a decrease in cell death. Our data suggest that consumption of foods containing anthocyanin may be beneficial in reducing cell damage due to H. pylori infection. PMID:24904230

Kim, Sa-Hyun; Woo, Hyunjun; Park, Min; Rhee, Ki-Jong; Moon, Cheol; Lee, Dongsup; Seo, Woo Duck; Kim, Jong Bae

2014-01-01

312

Inhibition of Carrageenan-Induced Acute Inflammation in Mice by Oral Administration of Anthocyanin Mixture from Wild Mulberry and Cyanidin-3-Glucoside  

PubMed Central

Anthocyanins are flavonoids which demonstrated biological activities in in vivo and in vitro models. Here in the anti-inflammatory properties of an anthocyanin-enriched fraction (AF) extracted from wild mulberry and the cyanidin-3-glucoside (C3G), the most abundant anthocyanin in diet, were studied in two acute inflammation experimental models, in the peritonitis and in the paw oedema assays, both of which were induced by carrageenan (cg) in mice. In each trial, AF and C3G (4?mg/100?g/animal) were orally administered in two distinct protocols: 30?min before and 1?h after cg stimulus. The administration of both AF and C3G suppresses the paw oedema in both administration times (P < 0.05). In the peritonitis, AF and C3G reduced the polymorphonuclear leukocytes (PMN) influx in the peritoneal exudates when administered 1?h after cg injection. AF was more efficient reducing the PMN when administered 30?min before cg. Both AF and C3G were found to suppress mRNA as well as protein levels of COX-2 upregulated by cg in both protocols, but the inhibitory effect on PGE2 production in the peritoneal exudates was observed when administered 30 min before cg (P < 0.05). Our findings suggest that AF and C3G minimize acute inflammation and they present positive contributions as dietary supplements. PMID:23484081

Hassimotto, Neuza Mariko Aymoto; Moreira, Vanessa; do Nascimento, Neide Galvao; Souto, Pollyana Cristina Maggio de Castro; Teixeira, Catarina; Lajolo, Franco Maria

2013-01-01

313

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

314

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

315

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

316

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

PubMed Central

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

Kahn, R A; Bak, S; Svendsen, I; Halkier, B A; M?ller, B L

1997-01-01

317

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

PubMed

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

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

1994-12-01

318

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

319

Transcriptional regulation of de novo biosynthesis of cyanogenic glucosides throughout the life-cycle of the burnet moth Zygaena filipendulae (Lepidoptera).  

PubMed

The six-spotted burnet moth Zygaena filipendulae (Lepidoptera) utilize the two cyanogenic glucosides (CNglcs) linamarin and lotaustralin as deterrents against predators throughout the entire life cycle. CNglcs can be hydrolyzed and bioactivated by ?-glucosidases, resulting in the release of toxic hydrogen cyanide. CNglcs are retained through metamorphosis, probably involved in mating communication, and transferred during mating from the male to the female as a nuptial gift. CNglcs can be biosynthesized de novo by Z. filipendulae larvae, but may also be sequestered from their food plant Lotus corniculatus (Fabaceae). These two strategies are tightly linked and adjusted according to the CNglc content and composition of the food plant in order to balance CNglc homeostasis in the larva. In this study, the amounts of CNglcs and transcript levels of the biosynthetic genes were monitored in all life-stages and tissues of Z. filipendulae. During pupation, transcription of the biosynthetic genes is turned off and the CNglc content slowly declines. In females but not males, transcription of the biosynthetic genes is re-activated at the end of pupation. Eggs and embryos do not biosynthesize CNglcs de novo, but are endowed with CNglcs following eclosion of the female. Similarly to larvae, de novo biosynthesis in female adults takes place in the integument from which CNglcs are then transported to other organs. This study demonstrates that Z. filipendulae has evolved the ability to adjust the production of CNglcs throughout its life-cycle for optimal utilization in defense and possibly other metabolic functions, while at the same time avoiding intoxication. PMID:24727026

Fürstenberg-Hägg, Joel; Zagrobelny, Mika; Olsen, Carl Erik; Jørgensen, Kirsten; Møller, Birger Lindberg; Bak, Søren

2014-06-01

320

Effects of temperature, salt, and deuterium oxide on the self-aggregation of alkylglycosides in dilute solution. 1. n-nonyl-beta-D-glucoside.  

PubMed

The influence of salt, temperature, and deuterium oxide on the self-aggregation of n-nonyl-beta-D-glucoside (beta-C9G1) in dilute solution has been investigated by static and dynamic light scattering, neutron scattering, and tensiometry. Scattering data show that the micelles can be described as relatively stiff, elongated structures with a circular cross section. With a decrease of temperature, the micelles grow in one dimension, which makes it surprising that the critical micelle concentration (cmc) shows a concomitant increase. On the other hand, substitution of D2O for H2O causes a large increase in micelle size at low temperatures, without any appreciable effect on cmc. With increasing temperature, the deuterium effect on the micelle size diminishes. The effects of salt on the micelle size and cmc were found to follow the Hofmeister series. Thus, at constant salt concentration, the micelle size decreased according to the sequence SO4(2-) > Cl- > Br- > NO3- > I- > SCN-, whereas the effect on cmc displays the opposite trend. Here, I- and SCN are salting-in anions. Similarly, the effects of cations decrease with increasing polarizability in the sequence Li+ > Na+ > K+ > Cs+. At high ionic strength, the systems separate into two micellar phases. The results imply that the size of beta-C9G1 micelles is extremely sensitive to changes in the headgroup size. More specifically, temperature and salt effects on effective headgroup size, including intermolecular interactions and water ofhydration, are suggested to be more decisive for the micelle morphology than the corresponding effects on unimer solubility. PMID:15803725

Ericsson, Caroline A; Söderman, Olle; Garamus, Vasil M; Bergström, Magnus; Ulvenlund, Stefan

2004-02-17

321

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

322

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

323

Enhancement of neurite outgrowth in PC12 cells stimulated with cyclic AMP and NGF by 6-acylated ascorbic acid 2-O-alpha-glucosides (6-Acyl-AA-2G), novel lipophilic ascorbate derivatives.  

PubMed

It has been shown that ascorbate (AsA) and its stable derivative, ascorbic acid 2-O-alpha-glucoside (AA-2G), do not elicit neurite outgrowth in PC12 cells. However, these ascorbates are synergistically enhanced by both dibutyryl cyclic AMP (Bt(2)cAMP)- and nerve growth factor (NGF)-induced neurite outgrowth in this model. In the present study, the effects of a series of novel lipophilic ascorbate derivatives, 6-acylated ascorbic acid 2-O-alpha-glucosides (6-Acyl-AA-2G), on neurite outgrowth induced by Bt(2)cAMP and NGF were examined in PC12 cells. We found that all the tested acylated ascorbate derivatives enhanced neurite formation induced by both agents in a dose-dependent manner. Of the 6-Acyl-AA-2G derivatives, 6-octanoyl ascorbic acid 2-O-alpha-glucoside (6-Octa-AA-2G) enhanced the Bt(2)cAMP-induced phosphorylated MAPK p44 and p42 expression. A alpha-glucosidase inhibitor, castanospermine, completely abrogated the promotion of neurite outgrowth and MAPK expression by 6-Octa-AA-2G. Addition of 6-Octa-AA-2G (0.5 mM) to PC12 cells caused a rapid and significant increase in intracellular AsA content, which reached a maximum and was maintained from 12 to 24 h after the culture. These findings suggest that 6-Acyl-AA-2G is rapidly hydrolyzed to AsA within the cell and enhances neurite differentiation through the interaction with the inducer-activated MAPK pathway. PMID:12612444

Zhou, Xiaohua; Tai, Akihiro; Yamamoto, Itaru

2003-03-01

324

Effects of phyllodulcin, hydrangenol, and their 8-O-glucosides, and thunberginols A and F from Hydrangea macrophylla SERINGE var. thunbergii MAKINO on passive cutaneous anaphylaxis reaction in rats.  

PubMed

We examined the antiallergic effects of phyllodulcin, hydrangenol, and their 8-O-glucosides, and thunberginols A and F isolated from the processed leaves (Hydrangeae Dulcis Folium) and dried leaves of Hydrangea macrophylla SERINGE var. thunbergii MAKINO using the passive cutaneous anaphylaxis (PCA) reaction. With the exception of phyllodulcin, these constituents were found to significantly inhibit the PCA reaction. Although thunberginol A showed the most potent inhibitory effect, hydrangenol was considered to be the principal antiallergic component in the processed leaves, after taking into account their contents. PMID:10480329

Matsuda, H; Shimoda, H; Yamahara, J; Yoshikawa, M

1999-08-01

325

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

326

Annexin V assay-proven anti-apoptotic effect of ascorbic acid 2-glucoside after cold ischemia/reperfusion injury in rat liver transplantation.  

PubMed

Controversy exists over whether the predominant cell death of hepatocytes is due to apoptosis or necrosis after ischemia/reperfusion injury. In this study we investigated the predominant cell death of hepatocytes after cold ischemia/reperfusion injury using the Annexin V-based assay, and evaluated the anti-apoptotic effect of ascorbic acid 2-glucoside (AA-2G) added to the University of Wisconsin solution (UW solution) in rat liver transplantation. The retrieved liver was preserved in 4 UW solution for 24 h, and then transplanted orthotopically to the syngeneic Wistar recipient. The animals were divided into 2 groups, a control group (n=10), in which liver grafts were preserved in UW solution (4), and an AA-2G group (n=10), in which liver grafts were preserved in UW solution (4) with AA-2G (100 ug/ml). The serum AST level 4 h after reperfusion in the control group was significantly suppressed in the AA-2G group, and the bile production of the liver graft in the AA-2G group was well recovered. The mean survival time in the AA-2G group was significantly improved compared with that in the control group. Annexin-V and Propidium iodide staining 4 h after reperfusion showed a significantly higher percentage of viable hepatocytes in the AA-2G group compared with the control group (93.4 +/- 2.0 vs. 80.3 +- 2.1%, P<0.05). In the control group, the main cell death of hepatocytes was apoptosis (early apoptosis: 10.0 +- 4.7%, late apoptosis: 6.4 +/- 1.7%). The addition of AA-2G to the UW solution significantly inhibited both early and late apoptotic cell death 4 h after reperfusion (early apoptosis: 0.98 +/- 0.88%, late apoptosis: 2.2 +/- 1.1%). The expression of caspase 9 in the immunostaining of the liver graft was suppressed in the AA-2G group compared with in the control group. Our study using the Annexin V-based assay provided evidence that the predominant cell death of hepatocytes was apoptosis after 24 h cold ischemia/reperfusion injury in rat liver transplantation. The addition of AA-2G to the UW solution attenuated 24 h cold ischemia/reperfusion injury by inhibiting the apoptosis of hepatocytes. PMID:14679398

Liu, Jie; Yagi, Takahito; Sadamori, Hiroshi; Matsukawa, Hiroyoshi; Sun, Dong-Sheng; Mitsuoka, Naoshi; Yamamura, Masao; Matsuoka, Junji; Jin, Zaishun; Yamamoto, Itaru; Tanaka, Noriaki

2003-10-01

327

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

328

Determination of cyanidin-3-glucoside (red kernel food colour) in beverages by high performance liquid chromatography and a study of its degradation by quadruple time-of-flight mass spectrometry.  

PubMed

A method for the determination of cyanidin-3-glucoside (red kernel colour, RKC) in various matrices, including carbonated soft drinks, fruit-based soft drinks, sugar confectionery and milk-based drinks, by high performance liquid chromatography (HPLC) based on UV-Vis detection (at 520 nm) have been developed. Pre-treatment procedures for various matrices have been optimised. For soft drinks, the pH values were adjusted to 2.0, and sugar confectionery and milk-based drinks were extracted with 30 and 50% methanol in 0.1% formic acid (pH ~ 2.5) aqueous solutions, respectively. The limits of detection for the established methods ranged from 0.2 mg/kg for soft drinks to 2.0 mg/kg for the sugar confectionery and milk-based drinks with the relative standard deviations lower than 7%, which satisfy the method performance requirements for quality control for the beverages. The stability of the colourant RKC under various thermal and pH conditions was investigated by quadruple time-of-flight mass spectrometry (Q-TOF-MS). The main colourant component of RKC, cyanidin-3-glucoside (Cyd-3-Glu), lost the glucose entity under thermal treatment. A new component was identified when RKC degraded under various pH conditions and a degradation pathway is proposed. The results will assist in understanding the degradation mechanism of the colourant Cyd-3-Glu. PMID:22014114

Song, Jia; Li, Xiaolin; Zeng, Lu; Liu, Hailing; Xie, Mengxia

2011-12-01

329

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

330

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

J?rgensen, Kirsten; Morant, Anne Vinther; Morant, Marc; Jensen, Niels Bjerg; Olsen, Carl Erik; Kannangara, Rubini; Motawia, Mohammed Saddik; M?ller, Birger Lindberg; Bak, S?ren

2011-01-01

331

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

332

Novel oxidation products of cyanidin 3-O-glucoside with 2,2'-azobis-(2,4-dimethyl)valeronitrile and evaluation of anthocyanin content and its oxidation in black rice.  

PubMed

The radical oxidation mechanism of anthocyanin derivatives was investigated by the reaction of cyanidin 3-O-glucoside in the presence of radical initiator 2,2'-azobis-(2,4-dimethyl)valeronitrile (AMVN) in EtOH and aqueous CH3CN. Six different oxidation products were isolated, depending on the solvent employed. These products were identified using NMR spectroscopy and multistep derivatisation reactions. Of the products obtained, two novel oxidised anthocyanin derivatives were isolated from black rice under prolonged storage. A radical reaction mechanism is proposed on the basis of these reaction products. Quantification of oxidised anthocyanins in black rice is demonstrated as a method to verify freshness of the rice. PMID:24594178

Kamiya, Haruna; Yanase, Emiko; Nakatsuka, Shin-Ichi

2014-07-15

333

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.

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

2014-01-01

334

Enzymatic bioconversion of citrus hesperidin by Aspergillus sojae naringinase: enhanced solubility of hesperetin-7-O-glucoside with in vitro inhibition of human intestinal maltase, HMG-CoA reductase, and growth of Helicobacter pylori.  

PubMed

Hesperetin-7-O-glucoside (Hes-7-G) was produced by the enzymatic conversion of hesperidin by Aspergillus sojae naringinase due to the removal of the terminal rhamnose. Extracts from orange juice and peel containing the hesperidin were so treated by this enzyme that the hesperidin could also be converted to Hes-7-G. The solubility of Hes-7-G in 10% ethanol was enhanced 55- and 88-fold over those of hesperidin and hesperetin, respectively, which may make Hes-7-G more bioavailable. Hes-7-G was 1.7- and 2.4-fold better than hesperidin and hesperetin, respectively, in the inhibition of human intestinal maltase. Hes-7-G was more potent by 2- and 4-fold than hesperidin in the inhibition of human HMG-CoA reductase. Additionally, Hes-7-G exhibited more effective inhibition of the growth of Helicobacter pylori than hesperetin, while its effectiveness was similar to that of hesperidin. Therefore, the results suggest that bioconverted Hes-7-G is more effective and bioavailable than hesperidin, as it has enhanced inhibitory and solubility properties. PMID:22980799

Lee, Young-Su; Huh, Ji-Young; Nam, So-Hyun; Moon, Sung-Kwon; Lee, Soo-Bok

2012-12-15

335

A new isoflavone glycitein 7-O-beta-D-glucoside 4''-O-methylate, isolated from Cordyceps militaris grown on germinated soybeans extract, inhibits EGF-induced mucus hypersecretion in the human lung mucoepidermoid cells.  

PubMed

A new isoflavone glycitein 7-O-beta-d-glucoside 4''-O-methylate (CGLM) has been isolated recently from Cordyceps militaris grown on germinated soybean extract and has antioxidant activity. In the present study, CGLM was investigated for its suppression of airway mucous hyper-secretion in epidermal growth factor (EGF)-treated human lung mucoepidermoid cells. NCI-H292 cells were treated with CGLM for 1?h, followed by EGF treatment for 24?h. The decrease in cyclooxygenase-2 (COX-2) production was correlated with reduced levels of protein and mRNA of inducible matrix metalloproteinase 9 (MMP-9) and also MUC5AC gene expression. CGLM directly inhibited down-regulated NF-?B activity, and significantly inhibited the phosphorylation of p38 and ERK1/2 (p42/p44) in NCI-H292 cells. These results suggest that CGLM protects NCI-H292 cells from EGF-induced damage by down-regulation of COX-2, MMP-9 and MUC5AC gene expression, mediated via blocking the NF-kappa-B and p38/ERK MAPK pathways. PMID:22407817

Kim, Jung-Hee; Park, Dong Ki; Lee, Choong Hwan; Yoon, Do-Young

2012-12-01

336

Cyanidin 3-glucoside protects 3T3-L1 adipocytes against H2O2- or TNF-alpha-induced insulin resistance by inhibiting c-Jun NH2-terminal kinase activation.  

PubMed

Anthocyanins are naturally occurring plant pigments and exhibit an array of pharmacological properties. Our previous study showed that black rice pigment extract rich in anthocyanin prevents and ameliorates high-fructose-induced insulin resistance in rats. In present study, cyanidin 3-glucoside (Cy-3-G), a typical anthocyanin most abundant in black rice was used to examine its protective effect on insulin sensitivity in 3T3-L1 adipocytes exposed to H(2)O(2) (generated by adding glucose oxidase to the medium) or tumor necrosis factor alpha (TNF-alpha). Twelve-hour exposure of 3T3-L1 adipocytes to H(2)O(2) or TNF-alpha resulted in the increase of c-Jun NH(2)-terminal kinase (JNK) activation and insulin receptor substrate 1 (IRS1) serine 307 phosphorylation, concomitantly with the decrease in insulin-stimulated IRS1 tyrosine phosphorylation and cellular glucose uptake. Blocking JNK expression using RNA interference efficiently prevented the H(2)O(2)- or TNF-alpha-induced defects in insulin action. Pretreatment of cells with Cy-3-G reduced the intracellular production of reactive oxygen species, the activation of JNK, and attenuated H(2)O(2)- or TNF-alpha-induced insulin resistance in a dose-dependent manner. In parallel, N-acetyl-cysteine, an antioxidant compound, did not exhibit an attenuation of TNF-alpha-induced insulin resistance. Taken together, these results indicated that Cy-3-G exerts a protective role against H(2)O(2)- or TNF-alpha-induced insulin resistance in 3T3-L1 adipocytes by inhibiting the JNK signal pathway. PMID:18179781

Guo, Honghui; Ling, Wenhua; Wang, Qing; Liu, Chi; Hu, Yan; Xia, Min

2008-03-15

337

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

338

Mechanisms of membrane protein insertion into liposomes during reconstitution procedures involving the use of detergents. 1. Solubilization of large unilamellar liposomes (Prepared by reverse-phase evaporation) by Triton X-100 octyl glucoside, and sodium cholate  

SciTech Connect

The mechanisms governing the solubilization by Triton X-100, octyl glucoside, and sodium cholate of large unilamellar liposomes prepared by reverse-phase evaporation were investigated. The solubilization process is described by the three-stage model previously proposed for the detergents. In stage I, detergent monomers are incorporated into the phospholipid bilayers until they saturate the liposomes. At this point, i.e., stage II, mixed phospholipid-detergent micelles begin to form. By stage III, the lamellar to micellar transition is complete and all the phospholipids are present as mixed micelles. The turbidity of liposome preparations was systematically measured as a function of the amount of detergent added for a wide range of phospholipid concentrations. The results allowed a quantitative determination of the effective detergent to lipid molar ratios in the saturated liposomes. The monomer concentrations of the three detergents in the aqueous phase were also determined at the lamellar to micellar transitions. These transitions were also investigated by /sup 31/P NMR spectroscopy, and complete agreement was found with turbidity measurements. Freeze-fracture electron microscopy and permeability studies in the sublytic range of detergent concentrations indicated that during stage I of solubilization detergent partitioning between the aqueous phase and the lipid bilayer greatly affects the basic permeability of the liposomes without significantly changing the morphology of the preparations. A rough approximation of the partition coefficients was derived from the turbidity and permeability data. It is concluded that when performed systematically, turbidity measurements constitute a very convenient and powerful technique for the quantitative study of the liposome solubilization process by detergents.

Paternostre, M.T.; Roux, M.; Rigaud, J.L.

1988-04-19

339

A Comparison of Antirrhinoside Distribution in the Organs of Two Related Plantaginaceae Species with Different Reproductive Strategies  

Microsoft Academic Search

A study of two related plants (Antirrhinum majus L. and Linaria vulgaris Mill.) containing the same defensive compound (the iridoid glucoside, antirrhinoside) but with reproductive strategies that\\u000a differ during ontogeny was undertaken. Young leaves are important to plants due to their higher photosynthetic rates and,\\u000a therefore, should be better protected with higher concentrations of defensive compounds such as antirrhinoside. Declining

Clifford W. Beninger; Renée R. Cloutier; Bernard Grodzinski

2009-01-01

340

Costs and benefits of iridoid glycosides in multitrophic systems  

Microsoft Academic Search

Because plants cannot run away from their attackers, move to more favourable locations or hide, they have to be able to tolerate, adapt and\\/or defend themselves. Plants have evolved an enormous array of mechanical and chemical defences against herbivores. One can distinguish three types of defence strategies: direct defences that directly affect the herbivores, indirect defences that attract the enemies

J. H. Talsma

2007-01-01

341

Linking microbial community structure to ?-glucosidic function in soil aggregates  

PubMed Central

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 observed that functional differences in otherwise similar soil aggregates can be largely attributed to differences in resource availability, rather than to the presence or absence of particular taxonomic groups. PMID:23719152

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

2013-01-01

342

Linking microbial community structure to ?-glucosidic function in soil aggregates.  

PubMed

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 observed that functional differences in otherwise similar soil aggregates can be largely attributed to differences in resource availability, rather than to the presence or absence of particular taxonomic groups. PMID:23719152

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

2013-10-01

343

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

344

Two new sesquiterpene glucosides from the leaves of Nicotiana tabacum.  

PubMed

Two new sesquiterpene glycosides, 11R,12-dihydroxy-6(7)-spirovetiven-8-one-9-O-beta-D-glucopyranoside (1) and rishitin M1-13-O-beta-D-glucopyranoside (2), have been isolated from the leaves of Nicotiana tabacum. Their structures were established by spectroscopic methods including (1)H, (13)C, and 2D NMR. The absolute configuration of the side chain in compound 1 was determined as R by NOESY and NOE difference spectra. PMID:20183306

Feng, Xin; Wang, Jun-Song; Luo, Jun; Kong, Ling-Yi

2009-07-01

345

Induction of apoptosis in human pancreatic MiaPaCa-2 cells through the loss of mitochondrial membrane potential (??m) by Gentiana kurroo root extract and LC-ESI-MS analysis of its principal constituents.  

PubMed

The objective of the current study was to evaluate the methanolic root extract of Gentiana kurroo for antioxidant and antiproliferative activities as well as to study the effect of the extract on the induction of apoptosis in human pancreatic cancer cell line (MiaPaCa-2). The extract exerted significant antioxidant activity as verified by DPPH, hydroxyl radical, lipid peroxidation and protective oxidative DNA damage assays. The results were comparable to standard antioxidants like ?-tocopherol, catechin and BHT used in such experiments. Antioxidant potential of G. kurroo may be attributed to the presence of high phenolic and flavonoid content (73±1.02 and 46±2.05 mg/g extract respectively). The anti-proliferative property of Gentiana kurroo root extract was determined by sulphorhodamine B (SRB) assay against Human colon cancer cell line (HCT-116), Lung carcinoma cell line (A-549), Pancreatic cancer cell line (MiaPaCa-2), Lung cancer cell line (HOP-62) and acute monocytic leukaemia cell line (THP-1). G. kurroo root extract inhibited cancer cell growth depending upon the cell line used and in a dose dependent manner. The extract induced potent apoptotic effects in MiaPaCa-2 cells. The population of apoptotic cells increased from 11.4% in case of control to 49.6% at 100 ?g/ml of G. kurroo root extract. The extract also induced a remarkable decrease in mitochondrial membrane potential (??m) leading to apoptosis of cancer cells used. The main chemical constituents identified by the liquid chromatography-tandem mass spectrometry (LC-ESI-MSMS) were found to be iridoid glucosides (iridoids and secoiridoids), xanthones and flavonoids. Iridoid glucosides are the bitter principles of Gentiana species. Loganic acid, Sweroside, Swertiamarin, Gentiopicroside, Gentisin, Isogentisin, Gentioside, Norswertianolin, Swertianolin, 4?-O-?-D-glucosyl-6'-O-(4-O-?-D-glucosylcaffeoyl)-linearoside and Swertisin were the principal compounds present in the methanol root extract of G. kurroo. PMID:23453831

Wani, Bilal A; Ramamoorthy, D; Rather, Manzoor A; Arumugam, N; Qazi, Asif Khurshid; Majeed, Rabiya; Hamid, Abid; Ganie, Showkat A; Ganai, Bashir A; Anand, Rajneesh; Gupta, Ajai P

2013-06-15

346

Factors affecting the contents of iridoid oleuropein in olive leaves (Olea europaea L.).  

PubMed

In this study, for the first time, the impact of the genetic factor on the contents of oleuropein in olive leaves was not only evaluated but the influence exerted by the color/age of leaves (green, green-yellowish, and yellow) and the collecting period (spring or autumn) was also evaluated. A repetitive high-resolution gas chromatographic quantitation method and an accurate high-performance liquid chromatographic method were developed. These analytical methods gave results showing a highly linear relationship. Samples of olive leaves were taken from seven major Italian olive cultivars, such as Dritta, Leccino, Caroleo, Coratina, Castiglionese, Nebbio, and Grossa di Cassano. Such a vegetal raw material could actually be exploited for recovering oleuropein, considered to be a high-added value molecule. This could be converted into hydrxytyrosol, a compound known to possess strong bioactive properties. Olive leaves showed considerable contents of oleuropein, which with some cultivars were even higher with respect to those present in the corresponding olive fruits (reported in the literature). The amounts of oleuropein in the collected leaves were markedly modified by the color/age and genetic factors, whereas meaningless variations were ascribable to the quantitation method and the collecting period factors. Various chemometrics, applied to the obtained analytical data, appeared to be effective in discriminating the samples on the basis of the above-examined experimental factors, thus confirming how these should be taken into account in future industrial recovery of oleuropein from olive leaves. PMID:16417301

Ranalli, Alfonso; Contento, Stefania; Lucera, Lucia; Di Febo, Moira; Marchegiani, Donato; Di Fonzo, Vittoria

2006-01-25

347

Identification of TLC markers and quantification by HPLC-MS of various constituents in noni fruit powder and commercial noni-derived products.  

PubMed

The composition of noni (Morinda citrifolia) products has been investigated. TLC profiles of several commercial juices and capsules were compared. 3-Methyl-1,3-butanediol was identified as a typical marker in noni juices. The presence of sorbic acid (E200) was detected in one juice declared as additive free. Quantitative data have been obtained by HPLC-MS. A method for the quantification of characteristic noni constituents, such as iridoid glucosides, scopoletin, rutin, fatty acid glucosides, and anthraquinones, was developed and validated. The separation was performed on a C18 column with a gradient of acetonitrile in water containing 0.1% formic acid. Detection was carried out with ESI-MS in the negative ion mode. Significant differences were observed between the products. Asperulosidic acid, deacetylasperulosidic acid, and rutin were present in all samples analyzed, but their concentrations differed considerably between the products. Fatty acid glucosides, noniosides B and C, were present in capsules and most juices. Scopoletin was mainly found in juices. The anthraquinone alizarin, which has been reported from roots and leaves, was not detected in the samples investigated. PMID:17696360

Potterat, Olivier; Felten, Roger Von; Dalsgaard, Petur W; Hamburger, Matthias

2007-09-01

348

Acylated flavone glycosides from Veronica.  

PubMed

A survey of the flavonoid glycosides of selected taxa in the genus Veronica yielded two new acylated 5,6,7,3',4'-pentahydroxyflavone (6-hydroxyluteolin) glycosides and two unusual allose-containing acylated 5,7,8,4'-tetrahydroxyflavone (isoscutellarein) glycosides. The new compounds were isolated from V. liwanensis and V. longifolia and identified using NMR spectroscopy as 6-hydroxyluteolin 4'-methyl ether 7-O-alpha-rhamnopyranosyl(1"'-->2")[6"-O-acetyl-beta-glucopyranoside] and 6-hydroxyluteolin 7-O-(6"-O-(E)-caffeoyl)-beta-glucopyranoside, respectively. Isoscutellarein 7-O-(6"'-O-acetyl)-beta-allopyranosyl(1"'-->2")-beta-glucopyranoside was obtained from both V. intercedens and V. orientalis and its 4'-methyl ether from V. orientalis only. Complete 1H and 13C NMR spectral assignments are presented for both isoscutellarein glycosides. Two iridoid glucosides new to the genus Veronica (melittoside and globularifolin) were also isolated from V. intercedens. PMID:14599528

Albach, Dirk C; Grayer, Renée J; Jensen, Søren Rosendal; Ozgökce, Fevzi; Veitch, Nigel C

2003-12-01

349

Hedyotis diffusa water extract diminished the cytotoxic effects of chemotherapy drugs against human breast cancer MCF7 cells.  

PubMed

Hedyotis diffusa is a Chinese herbal medicine widely used in combination with other herbal medicines such as Scutellaria barbata to treat various types of cancer. Late-stage and recurrent cancer patients usually use H. diffusa during chemotherapy in expecting to achieve additive or synergistic therapeutic effects. Several classes of active ingredients, including anthraquinones, iridoid glucosides and stigmasterols. have been isolated and characterized from H. diffusa. In the current study, we isolated alkaloid/flavonoid from H diffusa and showed that the crude alkaloid/flavonoid extract rather than its three major components possessed antitumor activity against human breast cancer cell line MCF7. Co-administration of H. diffusa water extract diminished the cytotoxicities of chemotherapy drugs doxorubicin, cyclophosphamide and docetaxel towards the MCF7 cells, implicating that H. diffusa should not be used during breast cancer chemotherapy. PMID:25026725

Dong, Qiulin; Ling, Binbing; Gao, Bosong; Maley, Jason; Sammynaiken, Ramaswami; Yang, Jian

2014-05-01

350

Phytochemical analysis, biological evaluation and micromorphological study of Stachys alopecuros (L.) Benth. subsp. divulsa (Ten.) Grande endemic to central Apennines, Italy.  

PubMed

Stachys alopecuros subsp. divulsa (Lamiaceae), a perennial herb endemic to central Italy growing on mountain pastures, was investigated for the first time for the content of secondary metabolites, for the micromorphology and histochemistry of glandular trichomes, and for the biological activity of the volatile oil, namely cytotoxic, antioxidant and antimicrobial. The plant showed the molecular pattern of iridoids, among which a new iridoid diglycoside (4'-O-?-D-galactopyranosyl-teuhircoside) was detected, together with a sterol glucoside and a phenylethanoid glycoside. The essential oil from the flowering aerial parts was characterized by a high proportion of sesquiterpene hydrocarbons (65.1%), with (E)-caryophyllene (33.2%) as the most abundant, while other main components were germacrene D (7.6%), ?-humulene (6.4%) and the oxygenated cis-sesquisabinene hydrate (10.2%). Taken together, polar and apolar chemical profiles support the classification of the species within the section Betonica of the genus Stachys. Micromorphological study revealed three types of glandular hairs secreting different classes of compounds, with type A peltate hairs producing the bulk of the essential oil. MTT assay revealed the potential of the volatile oil in inhibiting A375, HCT116 and MDA-MB 231 tumor cells (IC?? values below 20 ?g/ml). PMID:23827382

Venditti, Alessandro; Bianco, Armandodoriano; Nicoletti, Marcello; Quassinti, Luana; Bramucci, Massimo; Lupidi, Giulio; Vitali, Luca Agostino; Petrelli, Dezemona; Papa, Fabrizio; Vittori, Sauro; Lucarini, Domenico; Maleci Bini, Laura; Giuliani, Claudia; Maggi, Filippo

2013-10-01

351

Genetic transformation of Harpagophytum procumbens by Agrobacterium rhizogenes : iridoid and phenylethanoid glycoside accumulation in hairy root cultures  

Microsoft Academic Search

A genetic transformation method using Agrobacterium rhizogenes was developed for Harpagophytum procumbens. The influence of three factors on hairy root formation was tested: bacterial strains (A4 and ATCC 15834), various types\\u000a of explants and acetosyringone (AS) (200 ?M). The highest frequency of transformation (over 50% of explants forming roots\\u000a at the infected sites after 6 weeks of culture on Lloyd and McCown

Renata Gr?bkowska; Aleksandra Królicka; Wojciech Mielicki; Marzena Wielanek; Halina Wysoki?ska

2010-01-01

352

Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part I: Dihydronepetalactones  

PubMed Central

Summary Starting from the enantiomers of limonene, all eight stereoisomers of trans-fused dihydronepetalactones were synthesized. Key compounds were pure stereoisomers of 1-acetoxymethyl-2-methyl-5-(2-hydroxy-1-methylethyl)-1-cyclopentene. The stereogenic center of limonene was retained at position 4a of the target compounds and used to stereoselectively control the introduction of the other chiral centers during the synthesis. Basically, this approach could also be used for the synthesis of enantiomerically pure trans-fused iridomyrmecins. Using synthetic reference samples, the combination of enantioselective gas chromatography and mass spectrometry revealed that volatiles released by the endohyperparasitoid wasp Alloxysta victrix contain the enantiomerically pure trans-fused (4R,4aR,7R,7aS)-dihydronepetalactone as a minor component, showing an unusual (R)-configured stereogenic center at position 7. PMID:23019455

Zimmermann, Nicole; Hilgraf, Robert; Lehmann, Lutz; Ibarra, Daniel

2012-01-01

353

Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part II: Iridomyrmecins  

PubMed Central

Summary Following our earlier approach to the synthesis of dihydronepetalactones, all eight stereoisomers of trans-fused iridomyrmecins were synthesized starting from the enantiomers of limonene. Combined gas chromatography and mass spectrometry including enantioselective gas chromatography revealed that volatiles released by the endohyperparasitoid wasp Alloxysta victrix contain (4S,4aR,7S,7aR)-iridomyrmecin of 95–97% ee and stereochemically pure (4S,4aS,7R,7aS)-iridomyrmecin as a minor component. PMID:23019456

Hilgraf, Robert; Zimmermann, Nicole; Lehmann, Lutz; Troger, Armin

2012-01-01

354

Transport of Glucose, Gluconate, and Methyl ?-D-Glucoside by Pseudomonas aeruginosa  

PubMed Central

Glucose transport by Pseudomonas aeruginosa was studied. These studies were enhanced by the use of a mutant, strain PAO 57, which was unable to grow on glucose but which formed the inducible glucose transport system when grown in media containing glucose or other inducers such as 2-deoxy-d-glucose. Both PAO 57 and parental strain PAO transported glucose with an apparent Km of 7 ?M. Free glucose was concentrated intracellularly by P. aeruginosa PAO 57 over 200-fold above the external level. These data constitute direct evidence that glucose is transported via active transport by P. aeruginosa. Various experimental data clearly indicated that P. aeruginosa PAO transported methyl ?-d-glucose (?-MeGlc) via the glucose transport system. The apparent Km of ?-MeGlc transport was 7 mM which indicated a 1,000-fold lower affinity of the glucose transport system for ?-MeGlc than for glucose. While only unchanged ?-MeGlc was detected intracellularly in P. aeruginosa, ?-MeGlc was actually concentrated intracellularly less than 2-fold over the external level. Membrane vesicles of P. aeruginosa PAO retained transport activity for gluconate. This solute was concentrated intravesicularly several-fold over the external level. A component of the glucose transport system is believed to have been lost during vesicle preparation since glucose per se was not transported. Instead; glucose was converted to gluconate by membrane-associated glucose dehydrogenase and gluconate was then transported into the vesicles. Although this may constitute an alternate system for glucose transport, it is not a necessary prerequisite for glucose transport by intact cells since P. aeruginosa PAO 57, which lacks glucose dehydrogenase, was able to transport glucose at a rate equal to the parental strain. PMID:4205195

Guymon, L. F.; Eagon, R. G.

1974-01-01

355

Structural aspects of acylated plant pigments: stabilization of flavonoid glucosides and interpretation of their functions  

Microsoft Academic Search

The enzymatic synthesis of acylated isoquercitrins was accomplished by the lipase-catalyzed transesterification with carboxylic acid vinyl esters as acyl donors in an organic solvent. The introduction of an acyl group into isoquercitrin improved its thermostability and light-resistivity. In particular, isoquercitrin p-coumarate was the most stable of all the acylated isoquercitrins tested.

Kohji Ishihara; Nobuyoshi Nakajima

2003-01-01

356

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

357

New withanolide, acyl and menthyl glucosides from fruits of Withania coagulans Dunal.  

PubMed

The fruits of Withania coagulans Dunal (family: Solanaceae) are sweet, sedative, emetic, alterative and diuretic; used to treat asthma, biliousness, strangury, wounds, dyspepsia, flatulent colic, liver complaints and intestinal infections. Phytochemical investigation of the fruits yielded a withanolide tetraglucoside identified as (20S, 22R)-5alpha, 20alpha-diacetoxy-6beta-hydroxy- 1-oxowitha-2,24-dienolide-6-beta-D-glucopyranosyl-(6' --> 1")-beta-D-glucopyranosyl-(6" --> 1''')-beta-D-glucopyranosyl-(6''' --> 1''''-beta-D-glucopyranoside), a capryloyl hexaglucoside formulated as n-octanoyl-beta-D-glucopyranosyl-(6a --> 1b)-beta-D-glucopyranosyl-(6b --> c)-beta-D-glucopyranosyl-(6c --> 1d)-beta-D-glucopyranosyl-(6d --> 1e)-glucopyranosyl-(6e --> 1f)-glucopyranoside and a menthyl tetraglucoside characterized as menthol-O-alpha-L-glucopyranosyl-(2a --> 1b)-O-alpha-L-glucopyranosyl-(2b --> 1c)-O-alpha-L-glucopyranosyl-(2c --> 1d)-O-alpha-L-glucopyranoside along with three fatty acid esters, n-nonacosanyl linolenate, n-octacosanyl linolenate and n-heptacosanyl linolenate. The structures of the isolated phytoconstituents have been established on the basis of spectral data analysis and chemical means. PMID:25265822

Ali, Abuzer; Jameel, Mohd; Ali, Mohammed

2014-01-01

358

Isolation and identification of phenolic glucosides from thermally treated olive oil byproducts.  

PubMed

A liquid phase rich in bioactive compounds, such as phenols and sugars, is obtained from olive oil waste by novel thermal treatment. Two groups of fractions with common characteristics were obtained and studied after thermal treatment, acid hydrolysis, and separation by ultrafiltration, chromatography, and finally Superdex Peptide HR. In the first group, which eluted at the same time as oligosaccharides with a low DP (4-2), an oleosidic secoiridoid structure conjugated to a phenolic compound (hydroxytyrosol) was identified as oleuropeinic acid, and three possible structures were detected. In the second group, glucosyl structures formed by hydroxytyrosol and one, two, or three units of glucose or by tyrosol and glucose have been proposed. Verbascoside, a heterosidic ester of caffeic acid, in which hydroxytyrosol is linked to rhamnose-glucose or one of its isomers was also identified. Neutral oligosaccharides bound to a phenol-containing compound could be antioxidant-soluble fibers with bioactive properties. PMID:23323788

Rubio-Senent, Fátima; Lama-Muñoz, Antonio; Rodríguez-Gutiérrez, Guillermo; Fernández-Bolaños, Juan

2013-02-13

359

ABC transporter functions as a pacemaker for sequestration of plant glucosides in leaf beetles  

PubMed Central

Plant-herbivore interactions dominate the planet’s terrestrial ecology. When it comes to host–plant specialization, insects are among the most versatile evolutionary innovators, able to disarm multiple chemical plant defenses. Sequestration is a widespread strategy to detoxify noxious metabolites, frequently for the insect’s own benefit against predation. In this study, we describe the broad-spectrum ATP-binding cassette transporter CpMRP of the poplar leaf beetle, Chrysomela populi as the first candidate involved in the sequestration of phytochemicals in insects. CpMRP acts in the defensive glands of the larvae as a pacemaker for the irreversible shuttling of pre-selected metabolites from the hemolymph into defensive secretions. Silencing CpMRP in vivo creates a defenseless phenotype, indicating its role in the secretion process is crucial. In the defensive glands of related leaf beetle species, we identified sequences similar to CpMRP and assume therefore that exocrine gland-based defensive strategies, evolved by these insects to repel their enemies, rely on ABC transporters as a key element. DOI: http://dx.doi.org/10.7554/eLife.01096.001 PMID:24302568

Strauss, Anja S; Peters, Sven; Boland, Wilhelm; Burse, Antje

2013-01-01

360

Synthesis and Structural Characterization of Three Unique Helicobacter pylori ?-Cholesteryl Phosphatidyl Glucosides.  

PubMed

Steryl glycosides produced by bacteria play important biological roles in the evasion and modulation of host immunity. Step-economical syntheses of three cholesteryl-6-O-phosphatidyl-?-D-glucopyranosides (?CPG) unique to Helicobacter pylori have been achieved. The approach relies upon regioselective deprotection of per-O-trimethylsilyl-?-D-cholesterylglucoside at C6 followed by phosphoramidite coupling. Global TMS ether deprotection in the presence of oxygen and subsequent deprotection of the cyano ethyl phosphoester afforded the target compounds in 16-21?% overall yield starting from D-glucose. The structures of these natural products were determined using a combination of 2D NMR methods and mass spectrometry. These robust synthesis and characterization protocols provide analogues to facilitate glycolipidomic profiling and biological studies. PMID:25195783

Nguyen, Huy Q; Davis, Ryan A; Gervay-Hague, Jacquelyn

2014-12-01

361

Formation of glucoside conjugates during biotransformation of dibenzofuran by Penicillium canescens SBUG-M 1139.  

PubMed

Penicillium canescens oxidises dibenzofuran (DBF) to produce monohydroxylated derivatives and other more hydrophilic metabolites. These substances are water-soluble but unstable in organic solvents such as ethyl acetate, acetone or dichloromethane. Both extraction with ethyl acetate and enzymatic treatment of the aqueous culture filtrate with beta-glucuronidase led to decay of the hydrophilic metabolites and indicated these products to be glycoside conjugates. The glycosyl residue was identified as glucose both by liquid chromatography and by the use of glucose oxidase. The conjugate pattern formed was the same in type and amount, independent of the carbon source used for cultivation of the fungus. Clearly, DBF transformation in P canescens occurred in two phases: first the conversion to 2-, 3-, and 4-hydroxydibenzofuran (phase I), followed by the formation of the corresponding glucosyl conjugates (phase II). In contrast, 2,3-dihydroxydibenzofuran added to the cultures was transformed by ring cleavage producing a muconic acid-like dead-end product. PMID:11759691

Hammer, E; Schoefer, L; Schäfer, A; Hundt, K; Schauer, F

2001-10-01

362

ABC transporter functions as a pacemaker for sequestration of plant glucosides in leaf beetles.  

PubMed

Plant-herbivore interactions dominate the planet's terrestrial ecology. When it comes to host-plant specialization, insects are among the most versatile evolutionary innovators, able to disarm multiple chemical plant defenses. Sequestration is a widespread strategy to detoxify noxious metabolites, frequently for the insect's own benefit against predation. In this study, we describe the broad-spectrum ATP-binding cassette transporter CpMRP of the poplar leaf beetle, Chrysomela populi as the first candidate involved in the sequestration of phytochemicals in insects. CpMRP acts in the defensive glands of the larvae as a pacemaker for the irreversible shuttling of pre-selected metabolites from the hemolymph into defensive secretions. Silencing CpMRP in vivo creates a defenseless phenotype, indicating its role in the secretion process is crucial. In the defensive glands of related leaf beetle species, we identified sequences similar to CpMRP and assume therefore that exocrine gland-based defensive strategies, evolved by these insects to repel their enemies, rely on ABC transporters as a key element. DOI: http://dx.doi.org/10.7554/eLife.01096.001. PMID:24302568

Strauss, Anja S; Peters, Sven; Boland, Wilhelm; Burse, Antje

2013-01-01

363

Cytopiloyne, a polyacetylenic glucoside, prevents type 1 diabetes in nonobese diabetic mice.  

PubMed

Some polyacetylenes from the plant Bidens pilosa have been reported to treat diabetes. In this study, we report that the cytopiloyne from B. pilosa, which is structurally different from the above-mentioned polyacetylenes and inhibits CD4(+) T cell proliferation, effectively prevents the development of diabetes in nonobese diabetic mice as evidenced by a normal level of blood glucose and insulin and normal pancreatic islet architecture. Cytopiloyne also suppresses the differentiation of type 1 Th cells but promotes that of type 2 Th cells, which is consistent with it enhancing GATA-3 transcription. Also, long-term application of cytopiloyne significantly decreases the level of CD4(+) T cells inside pancreatic lymph nodes and spleens but does not compromise total Ab responses mediated by T cells. Coculture assays imply that this decrease in CD4(+) T cells involves the Fas ligand/Fas pathway. Overall, our results suggest that cytopiloyne prevents type 1 diabetes mainly via T cell regulation. PMID:17513748

Chang, Cicero Lee-Tian; Chang, Shu-Lin; Lee, Yi-Mei; Chiang, Yi-Ming; Chuang, Da-Yung; Kuo, Hui-Kai; Yang, Wen-Chin

2007-06-01

364

Potential role for gut microbiota in cell wall digestion and glucoside detoxification in Tenebrio molitor larvae  

Microsoft Academic Search

Tenebrio molitor larvae were successfully reared free of cultivatable gut lumen bacteria, yeasts and fungi using two approaches; aseptic rearing from surface sterilized eggs and by feeding larvae with antibiotic-containing food. Insects were reared on a rich-nutrient complete diet or a nutrient-poor refractory diet. A comparison of digestive enzyme activities in germ free and conventional insects containing a gut microbiota

Fernando A. Genta; Rod J. Dillon; Walter R. Terra; Clélia Ferreira

2006-01-01

365

Revision of the structures of citrifolinin A, citrifolinoside, yopaaoside A, yopaaoside B, and morindacin, iridoids from Morinda citrifolia L. and Morinda coreia Ham.  

PubMed

[Structure: see text] Citrifolin A was revised to dehydromethoxygaertneroside (2). Citrifolinoside and yopaaoside A were found to be identical, and their structures were revised to the new structure dehydroepoxymethoxygaertneroside (5). Yopaaoside B was revised to citrifolinoside A (9), and morindacin was revised to borreriagenin (11). PMID:17078712

Schripsema, Jan; Caprini, Geisa P; Dagnino, Denise

2006-11-01

366

[Simultaneous determination of five groups of components in qingkailing injection by high performance liquid chromatography with photo diode array detector and evaporative light scattering detector].  

PubMed

A method was established for the simultaneous quantification of nine components of five different structural types in Qingkailing injection. High performance liquid chromatography coupled with a photo diode array detector and an evaporative light scattering detector (HPLC-DAD-ELSD) was employed in the determination. Four monitoring wavelengths of 240, 254, 280 and 330 nm were set to determine nucleosides (uridine and adenosine), iridoid glucoside (geniposide), flavone glycoside (baicalin) and organic acids (chlorogenic acid and caffeic acid) respectively, and a combined evaporative light scattering detector was used to detect three steroid compounds (cholic acid, ursodesoxycholic acid and hyodeoxycholic acid). The proposed method permitted the simultaneous separation and determination of five groups of compounds in Qingkailing injection, and acceptable validation results of the precision, repeatability, stability and accuracy tests were achieved. The method was applied to the analysis of 19 Qingkailing injection samples from three different plants, and the results indicated that the method could be used as a convenient and reliable method in the multi-component determination and quality control of traditional Chinese medicines. PMID:16350790

Yan, Shikai; Xin, Wenfeng; Luo, Guoan; Wang, Yiming; Cheng, Yiyu

2005-09-01

367

Protective effects of Eucommia ulmoides Oliv. bark and leaf on amyloid ?-induced cytotoxicity.  

PubMed

The objectives of this study were to investigate the protective effects of Eucommia ulmoides Oliv. (EUO) bark and leaf against cytotoxicity induced by amyloid-? peptide (A?) and to explore their active components. The PC-12 cells injury mediated by A?(25-35) was employed to assess the neuroprotective effects of EUO bark, EUO leaf and various compounds. Intracellular Ca(2+) determination, MTT reduction assay, lactate dehydrogenase leakage evaluation and HO33258/PI staining were used to quantitatively or qualitatively evaluate cell viability and injury. The organic solvents partition and the macroporous resin separation were also applied to tracing the active constituents of EUO bark. Moreover, the effects of 8 compounds (3 iridoid glucoside, 3 phenylpripanoids and 2 flavonoids) were tested to identify the active compounds of EUO leaf. The results demonstrated that the water extracts of EUO barks and leaves, geniposidic acid and chlorogenic acid could efficiently protect PC-12 cells against the cytotoxicity of A?(25-35). This research suggests that EUO may represent a potential treatment strategy for Alzheimer's disease. Meanwhile, geniposidic acid and chlorogenic acid are the major active constituents of EUO barks and leaves, respectively. PMID:21784025

Zhou, Yongqiang; Liang, Min; Li, Weize; Li, Kai; Li, Ping; Hu, Yuzhu; Yang, Zhonglin

2009-11-01

368

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

369

A comparison of antirrhinoside distribution in the organs of two related Plantaginaceae species with different reproductive strategies.  

PubMed

A study of two related plants (Antirrhinum majus L. and Linaria vulgaris Mill.) containing the same defensive compound (the iridoid glucoside, antirrhinoside) but with reproductive strategies that differ during ontogeny was undertaken. Young leaves are important to plants due to their higher photosynthetic rates and, therefore, should be better protected with higher concentrations of defensive compounds such as antirrhinoside. Declining concentrations of antirrhinoside as leaves aged was found for A. majus but this was generally not the case for L. vulgaris. Concentrations of antirrhinoside in root tissue were low and constant throughout ontogeny for A. majus whereas for L. vulgaris root levels of antirrhinoside were high during the period when vegetative growth is its sole means of reproduction. Antirrhinoside in L. vulgaris roots declined relative to A. majus roots during budding and flowering. During flowering, significantly less antirrhinoside and relative biomass are devoted to L. vulgaris flowers than in A. majus. While these findings are consistent with Optimal Defense Theory (ODT) further work on the distribution of antirrhinoside and the effect of insect herbivory on plant fitness in other related species is needed. PMID:19949840

Beninger, Clifford W; Cloutier, Renée R; Grodzinski, Bernard

2009-11-01

370

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

371

Quercetin4?-glucoside: a physiological inhibitor of the activities of dominant glutathione S -transferases in onion ( Allium cepa L.) bulb  

Microsoft Academic Search

The onion (Allium\\u000a cepa L.) bulb has a high level of glutathione S-transferase (GST) activity, and it is a rich source of sulfur compounds as well as flavonoids. To investigate interactions\\u000a between onion bulb GSTs and metabolites, we separated onion bulb GSTs (GSTa and GSTb as minor GSTs and GSTc, GSTd and GSTe\\u000a as dominant GSTs) by DEAE-cellulose chromatography. In

Toshisada Suzuki; Goro Takada; Masayuki Fujita

2009-01-01

372

Bioavailability of C-linked dihydrochalcone and flavanone glucosides in humans following ingestion of unfermented and fermented rooibos teas.  

PubMed

High-performance liquid chromatography-mass spectrometry (HPLC-MS(n)) detected aspalathin and nothofagin, C-glycosides of apigenin and luteolin, and four eriodictyol-C-glycoside isomers in unfermented and fermented rooibos teas. The fermented drink contained 10-fold higher levels of aspalathin and nothofagin and a 4-fold lower eriodictyol-C-glycoside content than the fermented tea. The total flavonoid contents in 500 mL servings of the teas were 84 (fermented) and 159 mumol (unfermented). Following the ingestion of 500 mL of the teas by 10 volunteers, 0-24 h urine and plasma samples were collected for analysis. HPLC-MS(n) identified eight metabolites in urine. These were O-linked methyl, sulfate, and glucuronide metabolites of aspalathin and an eriodictyol-O-sulfate. The main compound excreted was an O-methyl-aspalathin-O-glucuronide (229 nmol) following ingestion of the unfermented drink and eriodictyol-O-sulfate (68 nmol) after ingestion of the fermented beverage. The overall metabolite levels excreted were 82 and 352 nmol, accounting for 0.09 and 0.22% of the flavonoids in the fermented and unfermented drinks, respectively. Most of the aspalathin metabolites were excreted within 5 h of tea consumption, suggesting absorption in the small intestine. Urinary excretion of the eriodictyol-O-sulfate occurred mainly during the 5-12 h collection period, indicative of absorption in the large intestine. Despite exhaustive searches, no flavonoid metabolites were detected in plasma. PMID:19534535

Stalmach, Angélique; Mullen, William; Pecorari, Monia; Serafini, Mauro; Crozier, Alan

2009-08-12

373

Benzophenone C-glucosides and gallotannins from mango tree stem bark with broad-spectrum anti-viral activity.  

PubMed

The high mutation rate of RNA viruses has resulted in limitation of vaccine effectiveness and increased emergence of drug-resistant viruses. New effective antivirals are therefore needed to control of the highly mutative RNA viruses. The n-butanol fraction of the stem bark of Mangifera indica exhibited inhibitory activity against influenza neuraminidase (NA) and coxsackie virus 3C protease. Bioassay guided phytochemical study of M. indica stem bark afforded two new compounds including one benzophenone C-glycoside (4) and one xanthone dimer (7), together with eleven known compounds. The structures of these isolated compounds were elucidated on the basis of spectroscopic evidences and correlated with known compounds. Anti-influenza and anti-coxsackie virus activities were evaluated by determining the inhibition of anti-influenza neuraminidase (NA) from pandemic A/RI/5+/1957 H2N2 influenza A virus and inhibition of coxsackie B3 virus 3C protease, respectively. The highest anti-influenza activity was observed for compounds 8 and 9 with IC50 values of 11.9 and 9.2?M, respectively. Compounds 8 and 9 were even more potent against coxsackie B3 virus 3C protease, with IC50 values of 1.1 and 2.0?M, respectively. Compounds 8 and 9 showed weak cytotoxic effect against human hepatocellular carcinoma and human epithelial carcinoma cell lines through MTT assay. PMID:24613627

Abdel-Mageed, Wael M; Bayoumi, Soad A H; Chen, Caixia; Vavricka, Christopher J; Li, Li; Malik, Ajamaluddin; Dai, Huanqin; Song, Fuhang; Wang, Luoqiang; Zhang, Jingyu; Gao, George F; Lv, Yali; Liu, Lihong; Liu, Xueting; Sayed, Hanaa M; Zhang, Lixin

2014-04-01

374

Characterization of Microemulsion Systems Formed by a Mixed 1,3Dioxolane Ethoxylate\\/Octyl Glucoside Surfactant System  

Microsoft Academic Search

The phase behavior of microemulsion systems containing water (or 1.0 wt% NaClaq), isooctane, and the binary surfactant system consisting of n-octyl-?-d-glucopyranoside, C8?G1, and the acid-cleavable alkyl ethoxylate, 4-CH3O (CH2CH2O)7.2, 2-(CH2)12CH3, 2-(CH2)CH3, 1,3-dioxolane, or “cyclic ketal” (“CK-2,13”), was determined. Large temperature-insensitive one, two, and three-phase microemulsion-phase\\u000a regions were obtained when equal masses of the two surfactants were employed, suggesting that C8?G1

Mayson H. Alkhatib; Douglas G. Hayes; Volker S. Urban

2009-01-01

375

Preparative isolation and purification of two benzoxazinoid glucosides from Acanthus ilicifolius L. by high-speed counter-current chromatography  

Microsoft Academic Search

The first preparative separation of two benzoxazinoids, (2R)-2-O-?-d-glucopyranosyl-2H-1,4-benzoxazin-3(4H)-one (HBOA-Glc) and (2R)-2-O-?-d-glucopyranosyl-4-hydroxy-2H-1,4-benzoxazin-3(4H)-one (DIBOA-Glc), by means of high-speed counter-current chromatography (HSCCC) from the n-butanol extract of Acanthus ilicifolius L. is presented. The two-phase solvent system containing ethyl acetate–n-butanol–0.5%NH4OH (2:3:5, v\\/v\\/v, system B) was selected for the one-step HSCCC separation of HBOA-Glc and DIBOA-Glc according to the partition coefficient values (K) for target

Hao Yin; Si Zhang; Xiongming Luo; Yonghong Liu

2008-01-01

376

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

377

Transglucosylation of ascorbic acid to ascorbic acid 2-glucoside by a recombinant sucrose phosphorylase from Bifidobacterium longum.  

PubMed

A novel transglycosylation reaction from sucrose to L-ascorbic acid by a recombinant sucrose phosphorylase from Bifidobacterium longum was used to produce a stable L-ascorbic acid derivative. The major product was detected by HPLC, and confirmed to be 2-O-alpha-D-glucopyranosyl-L-ascorbic acid by LC-MS/MS analysis. PMID:17216298

Kwon, Taeyeon; Kim, Cheong Tae; Lee, Jong-Hoon

2007-04-01

378

Characterization of Microemulsion Systems Formed by a Mixed 1,3-Dioxolane Ethoxylate / Octyl Glucoside Surfactant System  

SciTech Connect

The phase behavior of microemulsion systems containing water (or 1.0 wt% NaCl{sub aq}), isooctane, and the binary surfactant system consisting of n-octyl-{beta}-D-glucopyranoside, C{sub 8}{beta}G{sub 1}, and the acid-cleavable alkyl ethoxylate, 4-CH{sub 3}O (CH{sub 2}CH{sub 2}O){sub 7.2}, 2-(CH{sub 2}){sub 12}CH{sub 3}, 2-(CH{sub 2})CH{sub 3}, 1,3-dioxolane, or 'cyclic ketal' ('CK-2,13'), was determined. Large temperature-insensitive one, two, and three-phase microemulsion-phase regions were obtained when equal masses of the two surfactants were employed, suggesting that C{sub 8}{beta}G{sub 1} reduces the temperature sensitivity of CK-2,13's ethoxylate group. Addition of C{sub 8}{beta}G{sub 1} to CK-2,13 greatly improves the latter's low efficiency, evidenced by the formation of a three-phase microemulsion system for surfactant concentrations at low fractions of total surfactants for systems with equal mass ratios of water to oil and CK-2,13 to C{sub 8}{beta}G{sub 1}. Analysis of the phase diagrams also suggests that CK-2,13 and C{sub 8}{beta}G{sub 1} impart hydrophobic and hydrophilic character, respectively, to the surfactant mixture, and that addition of salt further increases the hydrophilicity of C{sub 8}{beta}G{sub 1}, presumably because of the salting-in of the latter. Analysis of small-angle neutron scattering data revealed that the mixed surfactant system formed spherical oil-in-water microemulsions, and that increasing the CK-2,13 fraction among the surfactants reduced the critical microemulsion concentration but slightly increased the nanodroplet size.

Alkhatib, Mayson H [University of Alabama, Huntsville; Hayes, Douglas G [ORNL; Urban, Volker S [ORNL

2009-01-01

379

Search for constituents with neurotrophic factor-potentiating activity from the medicinal plants of paraguay and Thailand.  

PubMed

20 medicinal plants of Paraguay and 3 medicinal plants of Thailand were examined on nerve growth factor (NGF)-potentiating activities in PC12D cells. The trail results demonstrated that the methanol extracts of four plants, Verbena littoralis, Scoparia dulcis, Artemisia absinthium and Garcinia xanthochymus, markedly enhanced the neurite outgrowth induced by NGF from PC12D cells. Furthermore, utilizing the bioactivity-guided separation we successfully isolated 32, 4 and 5 constituents from V. littoralis, S. dulcis and G. xanthochymus, respectively, including nine iridoid and iridoid glucosides (1-9), two dihydrochalcone dimers (10 and 11), two flavonoids and three flavonoid glycosides (12-16), two sterols (17 and 18), ten triterpenoids (19-28), five xanthones (29-33), one naphthoquinone (34), one benzenepropanamide (35), four phenylethanoid glycosides (36-39) and two other compounds (40 and 41). Among which, 15 compounds (1-4, 10-11, 14-18, 29-31 and 34) were new natural products. The results of pharmacological trails verified that littoralisone (1), gelsemiol (5), 7a-hydroxysemperoside aglucone (6), verbenachalcone (10), littorachalcone (11), stigmast-5-ene 3beta,7alpha,22alpha-triol (18), ursolic acid (19), 3beta-hydroxyurs-11-en-28,13beta-olide (24), oleanolic acid (25), 2alpha,3beta-dihydroxyolean-12-en-28-oic acid (26), 1,4,5,6-tetrahydroxy-7,8-di(3-methylbut-2-enyl)xanthone (29), 1,2,6-trihydroxy-5-methoxy-7-(3-methylbut-2-enyl)xanthone (30), 1,3,5,6-tetrahydroxy-4,7,8-tri(3-methyl-2-butenyl)xanthone (31), 12b-hydroxy-des-D-garcigerrin A (32), garciniaxanthone E (33) and (4R)-4,9-dihydroxy-8-methoxy-alpha-lapachone (34) elicited marked enhancement of NGF-mediated neurite outgrowth in PC12D cells. These substances may contribute to the basic study and the medicinal development for the neurodegenerative disorder. PMID:15235225

Li, Yushan; Ohizumi, Yasushi

2004-07-01

380

Neuroprotective activities of catalpol against CaMKII-dependent apoptosis induced by LPS in PC12 cells  

PubMed Central

Background and Purpose Neurodegenerative diseases present progressive neurological disorder induced by cell death or apoptosis. Catalpol, an iridoid glucoside isolated from the root of Rehmannia glutinosa Libosch, is present in a wide range of plant families. Although catalpol is an effective anti-apoptotic agent in LPS-induced neurodegeneration, the underlying mechanism has not been established. Here we have identified some of the mechanisms involved the prevention by catalpol of apoptosis induced by LPS in an experimental model of neurodegeneration in vitro. Experimental Approach Apoptosis was induced by adding LPS (80 ng·mL?1) to pheochromocytoma (PC12) cells, pretreated with catalpol for 12 h. We measured intracellular reactive oxygen species (ROS), apoptosis and intracellular calcium concentration ( [Ca2+]i) by flow cytometry or laser confocal scanning microscopy. We also analysed the protein expression of Bcl-2, Bax and Ca2+-calmodulin-dependent protein kinase II (CaMKII)-dependent apoptosis signal-regulating kinase-1 (ASK-1)/JNK/p38 signalling pathway in PC12 cells by Western blot. Key Results Catalpol stimulated expression of Bcl-2 and inhibited the expression of Bax. Catalpol also attenuated the increase in Ca2+ concentration induced by LPS in PC12 cells and down-regulated CaMK phosphorylation. The CaMKII-dependent ASK-1/JNK/p38 signalling cascade was blocked by catalpol. All these changes were accompanied by a decrease of apoptosis induced by LPS in PC12 cells. Conclusions and Implications The data presented here provide new mechanistic insights into the links between the CaMKII-dependent ASK-1/JNK/p38 signalling pathway and the protective effect of catalpol on apoptosis induced by LPS in PC12 cells. PMID:23550774

Chen, Wenna; Li, Ximing; Jia, Lian-Qun; Wang, Jun; Zhang, Lin; Hou, Diandong; Wang, Junyan; Ren, Lu

2013-01-01

381

[Flavonoids in Arabis Caucasica Willd. (Cruciferae). Part I. Heterozygote similar to quercetin and isorhamnetin].  

PubMed

From flowering herb of Arabis caucasica Willd. have been isolated crystalline flavonoid compounds. They have been identified as quercetin 3-glucoside, isorhamnetin 3-glucoside, quercetin 3-beta-glucoside-7-alpha-rhamnoside and isorhamnetin 3-beta-glucoside-7-alpha-rhamnoside. As chromatographically homogenous, in amorphous form have been isolated: quercetin 3-diglucoside-7-glucoside and isorhamnetin 3-diglucoside-7-glucoside. PMID:16092411

Mat?awska, I; Sikorska, M; Kowalewski, Z

1992-01-01

382

Identification of Antidiabetic Effect of Iridoid Glycosides and Low Molecular Weight Polyphenol Fractions of Corni Fructus, a Constituent of Hachimi-jio-gan, in Streptozotocin-Induced Diabetic Rats  

Microsoft Academic Search

In our previous study, Corni Fructus (Cornus officinalis SIEB. et ZUCC.), a component crude drug of the Chi- nese prescription Hachimi-jio-gan, was reported to reduce glucotoxicities, up-regulate renal function, and conse- quently ameliorate glycation-associated renal damage as well as Hachimi-jio-gan. Based upon these facts, we prepared Corni Fructus fractions and evaluated which fraction contained the effective components against dia- betes,

Noriko Yamabe; Ki Sung Kang; Yosuke Matsuo; Takashi Tanaka; Takako Yokozawa

2007-01-01

383

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

384

cDNA cloning of glycosyltransferases from Chinese wolfberry ( Lycium barbarum L.) fruits and enzymatic synthesis of a catechin glucoside using a recombinant enzyme (UGT73A10)  

Microsoft Academic Search

To obtain glycosyltransferases that are useful for structural and functional modification of bioactive compounds by glycosylation, an array of cDNAs encoding plant secondary product glycosyltransferases (PSPGs) were cloned from Chinese wolfberry (Lycium barbarum L.) fruits. The cloning strategy was based on high sequence conservation of the C-terminal region of PSPGs. Nine of these cDNAs were heterologously expressed in Escherichia coli,

Akio Noguchi; Nobuhiro Sasaki; Masahiro Nakao; Harukazu Fukami; Seiji Takahashi; Tokuzo Nishino; Toru Nakayama

2008-01-01

385

Comparative Analyses of Two Thermophilic Enzymes Exhibiting both ?-1,4 Mannosidic and ?-1,4 Glucosidic Cleavage Activities from Caldanaerobius polysaccharolyticus? †  

PubMed Central

The hydrolysis of polysaccharides containing mannan requires endo-1,4-?-mannanase and 1,4-?-mannosidase activities. In the current report, the biochemical properties of two endo-?-1,4-mannanases (Man5A and Man5B) from Caldanaerobius polysaccharolyticus were studied. Man5A is composed of an N-terminal signal peptide (SP), a catalytic domain, two carbohydrate-binding modules (CBMs), and three surface layer homology (SLH) repeats, whereas Man5B lacks the SP, CBMs, and SLH repeats. To gain insights into how the two glycoside hydrolase family 5 (GH5) enzymes may aid the bacterium in energy acquisition and also the potential application of the two enzymes in the biofuel industry, two derivatives of Man5A (Man5A-TM1 [TM1 stands for truncational mutant 1], which lacks the SP and SLH repeats, and Man5A-TM2, which lacks the SP, CBMs, and SLH repeats) and the wild-type Man5B were biochemically analyzed. The Man5A derivatives displayed endo-1,4-?-mannanase and endo-1,4-?-glucanase activities and hydrolyzed oligosaccharides with a degree of polymerization (DP) of 4 or higher. Man5B exhibited endo-1,4-?-mannanase activity and little endo-1,4-?-glucanase activity; however, this enzyme also exhibited 1,4-?-mannosidase and cellodextrinase activities. Man5A-TM1, compared to either Man5A-TM2 or Man5B, had higher catalytic activity with soluble and insoluble polysaccharides, indicating that the CBMs enhance catalysis of Man5A. Furthermore, Man5A-TM1 acted synergistically with Man5B in the hydrolysis of ?-mannan and carboxymethyl cellulose. The versatility of the two enzymes, therefore, makes them a resource for depolymerization of mannan-containing polysaccharides in the biofuel industry. Furthermore, on the basis of the biochemical and genomic data, a molecular mechanism for utilization of mannan-containing nutrients by C. polysaccharolyticus is proposed. PMID:20562312

Han, Yejun; Dodd, Dylan; Hespen, Charles W.; Ohene-Adjei, Samuel; Schroeder, Charles M.; Mackie, Roderick I.; Cann, Isaac K. O.

2010-01-01

386

LC-MS/APCI identification of glucoside esters and diesters of astaxanthin from the snow alga Chlamydomonas nivalis including their optical stereoisomers.  

PubMed

HPLC methods (LC-MS/APCI and chiral HPLC) were used for the identification of astaxanthin derivatives from the red snow alga Chlamydomonas nivalis collected in Austrian Alps, Slovak High Tatra Mountains and Bulgarian Pirin. We observed a striking difference in the composition of astaxanthin optical isomers in C. nivalis collected in geographically distinct regions. Furthermore, algae from the Pirin Mountains differed in the dominance of astaxanthin diglucoside diesters, suggesting an alternative strategy to enhance cell viability at low temperatures. PMID:23398889

?ezanka, Tomáš; Nedbalová, Linda; Kolouchová, Irena; Sigler, Karel

2013-04-01

387

Implications of low-power He-Ne laser and monochromatic red light biostimulation in the metabolism of proteins and glucosides  

Microsoft Academic Search

We checked the changes occurring in the metabolism of proteins (seric cholinesterase, total proteins) and in the metabolism of glycosides (seric glucose) in Cavia cobaia. A simple blind study was carried out and the results were checked on the first, tenth and twentieth days of treatment. The data thus obtained were graphically represented and statistically processed according to the Duncan

I. Onac; L. Pop; Rodica Ungur; Ioana Giurgiu

2001-01-01

388

Verbascoside and luteolin-5- O- ?- d-glucoside isolated from Halleria lucida L. exhibit antagonistic anti-oxidant properties in vitro  

Microsoft Academic Search

The purpose of this investigation was to determine and characterise the anti-oxidant activity of the methanol extract of the leaves of Halleria lucida utilizing the DPPH (2,2-diphenyl-1-picrylhydrazyl) assay. The methanol extract of the leaves of H. lucida displayed promising anti-oxidant activity with an IC50 value of 8.49±0.12 ?g\\/ml and was subsequently subjected to activity-guided fractionation resulting in the isolation of a

Y. Frum; A. M. Viljoen; F. R. Van Heerden

2007-01-01

389

Radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl of ascorbic acid 2-glucoside (AA-2G) and 6-acyl-AA-2G.  

PubMed

The radical scavenging activity of the stable derivatives, which are O-substituted at the C-2 position of ascorbic acid (AA), against 1,1-diphenyl-2-picrylhydrazyl (DPPH) was evaluated in buffer under different pH conditions, and compared with those of AA and alpha-tocopherol. AA was shown to have 50% radical scavenging ability (EC50) at a concentration of 2.2 x 10(-5) M against 0.1 mM DPPH in 60% ethanol. Ascorbyl 6-palmitate, a lipophilic AA derivative which has a free endiol group and is therefore unstable, also showed potent radical scavenging activity with EC50 of 2.9 x 10(-5) M. A typical lipophilic antioxidant, alpha-tocopherol gave a similar EC50 value as that of AA. In contrast, ascorbyl 2,6-dipalmitate, AA 2-phosphate and AA 2-sulfate exhibited negligible scavenging activity. On the other hand, 2-O-alpha-D-glucopyranosyl-L-ascorbic acid (AA-2G) and a series of 6-O-acyl-2-O-alpha-D-glucopyranosyl-L-ascorbic acids (6-Acyl-AA-2G) themselves exhibited the radical scavenging activity of EC50: 6.1 x 10(-5) M and 4.4 x 10(-5)-5.9 x 10(-5) M, respectively, although their activities were lower than that of AA. Among 6-Acyl-AA-2G derivatives, the EC50 values tended to decrease with increasing length of their acyl carbon group. Increasing pH of the buffer resulted in decrease in the scavenging activity of all compounds tested as expected. We speculate that the difference in the radical scavenging activity of derivatives O-substituted at the C-2 position of AA may be ascribed to the linkage type of the substituent group to the endiol-lactone resonance system and the degree of dissociation of the C-3 proton. PMID:11383624

Fujinami, Y; Tai, A; Yamamoto, I

2001-05-01

390

Antiscorbutic activity of L-ascorbic acid 2-glucoside and its availability as a vitamin C supplement in normal rats and guinea pigs.  

PubMed

Bioavailability of a newly-synthesized and chemically-stable 2-O-alpha-D-glucopyranosyl-L-ascorbic acid (AA-2G) as a vitamin C supplement was investigated in rats and guinea pigs. Oral administration of AA-2G to the animals resulted in an increase of serum ascorbic acid (AA) levels. However, in these sera the intact form was not detectable by the high performance liquid chromatography (HPLC) method, indicating its hydrolysis through the process of absorption. After an intravenous injection of AA-2G, the intact form diminished rapidly from the serum, followed by prolonged and marked elevation of serum AA levels. Various tissue homogenates from rats and guinea pigs were examined for their releasing activity of AA from AA-2G. High activity was observed in kidney, small intestine and serum of rats and in small intestine and kidney of guinea pigs. These hydrolytic activities were completely inhibited by castanospermine, a specific alpha-glucosidase inhibitor, suggesting the participation of alpha-glucosidase in the in vivo hydrolysis of AA-2G. AA-2G was found to exhibit obvious therapeutic effect in scorbutic guinea pigs by its repeated oral administrations. These results indicate that AA-2G is a readily available source of vitamin C activity in vivo. PMID:2093127

Yamamoto, I; Suga, S; Mitoh, Y; Tanaka, M; Muto, N

1990-11-01

391

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

392

Characterization of the recombinant cellobiase from celG gene in the beta-glucoside utilization gene operon of Pectobacterium carotovorum subsp. carotovorum LY34  

Microsoft Academic Search

A third cel operon containing celE, celF, and celG genes was isolated from Pectobacterium carotovorum subsp. carotovorum LY34 (Pcc LY34) genomic DNA using a cosmid library. The amino acid sequences of CelE and CelF shared high sequence identity with the cellobiose-specific PTS enzymes IIB and IIC, respectively. CelF contained the disaccharide binding region essential for acquiring cellobiose molecules. The amino

Su Young Hong; Kye Man Cho; Yong Hee Kim; Sun Joo Hong; Yong Un Cho; Hoon Kim; Han Dae Yun

2007-01-01

393

Histochemical detection of alpha-D-glucosidases and their molecular forms with 5-Br-4-Cl-3-indoxyl-alpha-D-glucoside.  

PubMed

5-Br-4-Cl-3-Indoxyl-alpha-D-gluco(pyrano)side was found to be the most suitable synthetic substrate for the demonstration of alpha-D-glucosidases in situ. Using an azoindoxyl procedure with hexazotized pararosaniline or new fuchsine at pH 5 in freeze-dried celloidine-mounted cryostat sections acid alpha-D-glucosidase (EC 3.2.1.20) was shown for the first time in lysosomes of many cells of fetal and adult rat, mouse, guinea-pig, marmoset and human organs. At pH 6.5, in chloroform-acetone pretreated cryostat sections plasma membrane alpha-D-glucosidases were shown in the brush border of enterocytes of the small and large intestine, in the brush border of proximal renal tubule cells and in the stereocilia of the epididymal duct. In an indigogenic procedure with ferricyanide/ferrocyanide as redox catalysator plasma membrane alpha-D-glucosidases were depicted as well as with the azo-indoxyl method; the demonstration of the acid alpha-D-glucosidase was inferior to that achieved with the azo-indoxyl procedure. Using tetrazolium salts as capture reagent intracellular localization was unsatisfactory. In enterocytes, a localization in the Golgi apparatus was shown by the azo-indoxyl procedure only. Analytical isoelectric focusing revealed organ-dependent differences of plasma membrane and lysosomal alpha-D-glucosidases. Compared with the already existing methods the azo-indoxyl and indigogenic procedures are by far the most suitable techniques. PMID:3106270

Gossrau, R; Lojda, Z; Ruhnke, M

1987-01-01

394

?-Glucosidase activity in fetal bovine serum renders the plant glucoside, hypoxoside, cytotoxic toward B16-F10BL6 mouse melanoma cells  

Microsoft Academic Search

Summary  By usingp-nitrophenyl-?-d-glucopyranoside as substrate, ?-glucosidase activity was observed in fetal bovine serum (FBS). This activity could be inhibited\\u000a by heat inactivation of the serum. Gel chromatography of FBS indicated the presence of ?-glucosidase activity with an apparent\\u000a molecular mass of 29 kDa. In McCoy’s 5A medium supplemented with non-heat inactivated FBS, the diglucoside hypoxoside ([E]-1,5-bis[4??-d-glucopyranosyloxy-3?-hydroxyphenyl]pent-4-en-1-yne) showed cytotoxicity toward B16-F10-BL-6 mouse

E. J. Theron; C. F. Albrecht; P. B. Kruger; K. Jenkins; M. J. Van der Merwe

1994-01-01

395

Earthworms and Litter Distribution Affect Plant-Defensive Chemistry  

Microsoft Academic Search

Studies on plant-defensive chemistry have mainly focused on plants in direct interaction with aboveground and occasionally belowground herbivores and pathogens. Here we investigate whether decomposers and the spatial distribution of organic residues in soil affect plant-defensive chemistry. Litter concentrated in a patch (vs. homogeneously mixed into the soil) led to an increase in the aucubin content in shoots of Plantago

Susanne Wurst; Dereje Dugassa-Gobena; Stefan Scheu

2004-01-01

396

Polar constituents of celery seed  

Microsoft Academic Search

From the water-soluble portion of the methanol extract of celery seed (fruit of Apium graveolens L.) five sesquiterpenoid glucosides (celerioside A–E) and three phthalide glycosides (celephtalide A–C) were isolated together with six aromatic compound glucosides, two norcarotenoid glucosides and a lignan glucoside. Their structures were determined by spectral investigations.

Junichi Kitajima; Toru Ishikawa; Mitsuru Satoh

2003-01-01

397

A 7-deoxyloganetic acid glucosyltransferase contributes a key step in secologanin biosynthesis in Madagascar periwinkle.  

PubMed

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

2013-10-01

398

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

399

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

400

Anthocyanins from flowers of Cichorium intybus.  

PubMed

From the blue perianth segments of Cichorium intybus we isolated four anthocyanins. The pigments were identified as delphinidin 3,5-di-O-(6-O-malonyl-beta-D-glucoside) and delphinidin 3-O-(6-O-malonyl-beta-D-glucoside)-5-O-beta-D-glucoside and the known compounds were delphinidin 3-O-beta-D-glucoside-5-O-(6-O-malonyl-beta-D-glucoside) and delphinidin 3,5-di-O-beta-D-glucoside. In addition 3-O-p-coumaroyl quinic acid has been identified. PMID:12031425

Nørbaek, Rikke; Nielsen, Karina; Kondo, Tadao

2002-06-01

401

Chemical markers in Veronica sect. Hebe. II  

Microsoft Academic Search

In a continued chemosystematic investigation of the water-soluble compounds in Veronica sect. Hebe, four additional species were investigated. In comparison to other, Northern Hemisphere (NH) species of Veronica, those belonging to the New Zealand species in sect. Hebe are apparently more variable in chemical content. In addition to the compounds characteristic for NH Veronica, namely mannitol, aucubin, catalpol and 6-O-esters

Palle Pedersen; Charlotte Held Gotfredsen; Steven J. Wagstaff; Søren Rosendal Jensen

2007-01-01

402

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

2014-07-01

403

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

404

Quercetin triglycoside from Capparis spinosa  

Microsoft Academic Search

In addition to rutin, quercetin 3-O-glucoside and quercetin 3-O-glucoside-7-O-rhamnoside, the methanolic extract of the aerial parts of Capparis spinosa yielded the new flavonoid quercetin 3-O-[6??-?-l-rhamnosyl-6?-?-d-glucosyl]-?-d-glucoside (1).

M. Sharaf; M. A. El-Ansari; N. A. M. Saleh

2000-01-01

405

Quercetin triglycoside from Capparis spinosa.  

PubMed

In addition to rutin, quercetin 3-O-glucoside and quercetin 3-O-glucoside-7-O-rhamnoside, the methanolic extract of the aerial parts of Capparis spinosa yielded the new flavonoid quercetin 3-O-[6'"-alpha-L-rhamnosyl-6"-beta-D-glucosyl]-beta-D-glucoside (1). PMID:11449469

Sharaf, M; el-Ansari, M A; Saleh, N A

2000-02-01

406

Using reversed phase high performance liquid chromatography to study the complexation of anthocyanins with ?-cyclodextrin  

NASA Astrophysics Data System (ADS)

It is shown by means of reversed phase high performance liquid chromatography (RP HPLC) with mobile phases containing additions of ?-cyclodextrin that 5-glucosides of cyanidin and pelargonidin form stronger inclusion complexes than 3-glucosides; this is explained by the steric interference of the glucoside radical.

Deineka, V. I.; Lapshova, M. S.; Deineka, L. A.

2014-06-01

407

Flavonol glycosides of Warburgia ugandensis leaves  

Microsoft Academic Search

Four new flavonol glycosides: kaempferide 3-O-?-xylosyl (1?2)-?-glucoside, kaempferol 3-O-?-rhamnoside-7,4?-di-O-?-galactoside, kaempferol 3,7,4?-tri-O-?-glucoside and quercetin 3-O-[?-rhamnosyl (1?6)] [?-glucosyl (1?2)]-?-glucoside-7-O-?-rhamnoside, were characterized from a methanolic leaf extract of Warburgia ugandensis. The known flavonols: kaempferol, kaempferol 3-rhamnoside, kaempferol 3-rutinoside, myricetin, quercetin 3-rhamnoside, kaempferol 3-arabinoside, quercetin 3-glucoside, quercetin, kaempferol 3-rhamnoside-4?-galactoside, myricetin 3-galactoside and kaempferol 3-glucoside were also isolated. Structures were established by spectroscopic and chemical

Lawrence O. Arot Manguro; Ivar Ugi; Peter Lemmen; Rudolf Hermann

2003-01-01

408

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

409

Quantification of flavonoids in black rice by liquid chromatography-negative electrospray ionization tandem mass spectrometry.  

PubMed

Systematic identification and structural characterization of flavonoids and their glycosides in bran extracts of seven Thai black rice varieties were performed by sequential uses of reversed-phase HPLC with a photodiode array detector and a combined electrospray ionization tandem mass spectrometer. Eleven flavonoids were detected, and six of these were found for the first time in rice bran. These were taxifolin-7-O-glucoside, myricetin-7-O-glucoside, isorhamnetin-3-O-acetylglucoside, isorhamnetin-7-O-rutinoside, 5,6,3',4',5'-pentahydroxyflavone-7-O-glucoside, and 5,3',4',5'-tetrahydroxyflavanone-7-O-glucoside. The quantitative results revealed that different rice varieties possessed flavonoids in different concentrations. The most abundant glycoside derivative of flavonoids widely distributed among the rice varieties was monoglucoside, such as quercetin-3-O-glucoside, isorhamnetin-3-O-glucoside, and isorhamnetin-3-O-glucoside. PMID:23121250

Sriseadka, Tinakorn; Wongpornchai, Sugunya; Rayanakorn, Mongkon

2012-11-28

410

Flavone C-glycoside, phenolic acid, and nitrogen contents in leaves of barley subject to organic fertilization treatments.  

PubMed

From the leaves of barley, Hordeum vulgare, one new flavone C-glucoside and three known flavone glucosides were isolated and characterized by (1)H and (13)C NMR and MALDI-TOF-MS. The novel flavone C-glucoside was isovitexin 7-O-beta-[6' "-O-(E)-p-coumaroyl]glucoside (6' "-coumaroylsaponarin), and the known compounds were isovitexin 7-O-beta-[6' "-O-(E)-feruloyl]glucoside, isoorientin 7-O-beta-[6' "-O-(E)-feruloyl]glucoside, and tricin 7-O-beta-glucoside. The sum of all the flavone glycosides and soluble phenolic acids in the leaves decreased with increased rate of plant nutrients given in animal manure and with increased crop yield. All of the major phenylpropanoids showed the same general response to nutrient level. The concentration of nitrogen in the leaves was not directly related to nutrient application or to contents of phenylpropanoids. PMID:12537462

Nørbaek, R; Aaboer, D B F; Bleeg, I S; Christensen, B T; Kondo, T; Brandt, K

2003-01-29

411

Hemolytic action and surface activity of triterpene saponins from Anchusa officinalis L. Part 21: On the costituents of Boraginaceae.  

PubMed

Relationship between chemical structure, hemolytic action and surface activity of five glucosides of oleanolic acid were studied. Monodesmosidic saponins are more hemolytic than bisdesmosidic. The hemolytic activity of monodesmosides decreased with the length and the branching of the glucosidic chain. Surface activity is major in bisdesmosides. This property increases with the length of the glucosidic chain in monodesmosides. Increase of hemolytic action is accompanied by a decrease of surface activity. PMID:7433502

Romussi, G; Cafaggi, S; Bignardi, G

1980-08-01

412

Flavonoid glycosides of spore-bearing stems of Equisetum arvense  

Microsoft Academic Search

In an extract of spore-bearing stems ofEquisetum arvense L. (field horsetail) saponaretin, apigenin 5-glucoside, luteolin 5-glucoside, kaempferol 3-sophoroside, quercetin 3-glucoside, 4-hydroxy-6-(2-hydroxyethyl)-2,2,5,7-tetramethylindanone, and a compound of ketonic nature, isolated previously from an extract of the herbage of the field horsetail, have been identified by high-performance liquid chromatography. The characteristics of the chromatographic behavior of glycosylated flavones under the conditions of reversed-phase

A. I. Syrchina; V. G. Gorokhova; N. A. Tyukavkina; V. A. Babkin; M. G. Voronkov

1980-01-01

413

Hepatoprotective and free radical scavenging activities of phenolic petrosins and flavonoids isolated from Equisetum arvense  

Microsoft Academic Search

Hepatoprotective activity-guided fractionation of the MeOH extract of Equisetum arvense L. (Equisetaceae) resulted in the isolation of two phenolic petrosins, onitin (1) and onitin-9-O-glucoside (2), along with four flavonoids, apigenin (3), luteolin (4), kaempferol-3-O-glucoside (5), and quercetin-3-O-glucoside (6). Among these, compounds 1 and 4 exhibited hepatoprotective activities on tacrine-induced cytotoxicity in human liver-derived Hep G2 cells, displaying EC50 values of

Hyuncheol Oh; Do-Hoon Kim; Jung-Hee Cho; Youn-Chul Kim

2004-01-01

414

Production of Hesperetin Glycosides by Xanthomonas campestris and Cyclodextrin Glucanotransferase and Their Anti-allergic Activities  

PubMed Central

The production of hesperetin glycosides was investigated using glycosylation with Xanthomonas campestris and cyclodextrin glucanotransferase (CGTase). X. campestris glucosylated hesperetin to its 3'-, 5-, and 7-O-glucosides, and CGTase converted hesperetin glucosides into the corresponding maltosides. The resulting 7-O-glucoside and 7-O-maltoside of hesperetin showed inhibitory effects on IgE antibody production and on O2- generation from rat neutrophils. PMID:22254014

Shimoda, Kei; Hamada, Hiroki

2010-01-01

415

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

416

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

417

Hepatoprotective coumarins and secoiridoids from Hydrangea paniculata.  

PubMed

Three new coumarin glucosides (1, 3, 4), and a new secoiridoid glucoside (2), together with one known secoiridoid glucoside (5), were isolated from the stems of Hydrangea paniculata. Their structures were elucidated on the basis of spectroscopic methods, including extensive NMR, MS and CD spectra. At 10 ?M, compounds 1-5 showed hepatoprotective activities against DL-galactosamine-induced toxicity in HL-7702 cells. PMID:24811324

Shi, Jing; Li, Chuang-Jun; Yang, Jing-Zhi; Ma, Jie; Wang, Chao; Tang, Jia; Li, Yan; Chen, Hui; Zhang, Dong-Ming

2014-07-01

418

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

419

76 FR 64974 - Commerce in Explosives; List of Explosive Materials (2011R-18T)  

Federal Register 2010, 2011, 2012, 2013

...nitroisobutametriol trinitrate]. Nitrate explosive mixtures. Nitrate sensitized with gelled nitroparaffin. Nitrated carbohydrate explosive. Nitrated glucoside explosive. Nitrated polyhydric alcohol explosives. Nitric acid and a nitro aromatic...

2011-10-19

420

78 FR 64246 - Commerce in Explosives; List of Explosives Materials  

Federal Register 2010, 2011, 2012, 2013

...nitroisobutametriol trinitrate]. Nitrate explosive mixtures. Nitrate sensitized with gelled nitroparaffin. Nitrated carbohydrate explosive. Nitrated glucoside explosive. Nitrated polyhydric alcohol explosives. Nitric acid and a nitro aromatic...

2013-10-28

421

77 FR 58410 - Commerce in Explosives; List of Explosive Materials (2012R-10T)  

Federal Register 2010, 2011, 2012, 2013

...nitroisobutametriol trinitrate]. Nitrate explosive mixtures. Nitrate sensitized with gelled nitroparaffin. Nitrated carbohydrate explosive. Nitrated glucoside explosive. Nitrated polyhydric alcohol explosives. Nitric acid and a nitro aromatic...

2012-09-20

422

75 FR 70291 - Commerce in Explosives; List of Explosive Materials (2010R-27T)  

Federal Register 2010, 2011, 2012, 2013

...nitroisobutametriol trinitrate]. Nitrate explosive mixtures. Nitrate sensitized with gelled nitroparaffin. Nitrated carbohydrate explosive. Nitrated glucoside explosive. Nitrated polyhydric alcohol explosives. Nitric acid and a nitro aromatic...

2010-11-17

423

75 FR 1085 - Commerce in Explosives; List of Explosive Materials (2009R-18T)  

Federal Register 2010, 2011, 2012, 2013

...nitroisobutametriol trinitrate]. Nitrate explosive mixtures. Nitrate sensitized with gelled nitroparaffin. Nitrated carbohydrate explosive. Nitrated glucoside explosive. Nitrated polyhydric alcohol explosives. Nitric acid and a nitro aromatic...

2010-01-08

424

Baccharane glycosides from seeds of Impatiens balsamina.  

PubMed

From the seeds of Impatiens balsamina have been isolated four rare baccharane glycosides, hosenkosides L-O. The structures of all isolates were secured by the use of 2D NMR techniques (1H-1H COSY, HMQC, HMBC, ROESY) and chemical derivatization. Hosenkosides L and M are hosenkol A 3-O-sambubiosyl-28-O-glucoside and 3-O-sambubiosyl-26-O-glucosyl-28-O-glucoside, respectively. Hosenkoside N is hosenkol C 3-O-glucosyl-28-O-glucoside. Hosenkoside O is hosenkol D 3-O-sophorosyl-28-O-glucoside. PMID:7765763

Shoji, N; Umeyama, A; Yoshikawa, K; Nagai, M; Arihara, S

1994-11-01

425

Screening of Catharanthus roseus secondary metabolites by high-performance liquid chromatography  

Microsoft Academic Search

Two direct HPLC analytical methods for the screening of the major indole alkaloids of Catharanthus roseus hairy roots and their iridoid precursors have been developed. Photodiode array and fluorescence detection were performed. The separation was achieved on a reversed-phase C18 column. The first method allowed the separation of catharanthine, serpentine, tabersonine, vindoline, vinblastine, and vincristine in 20 min. Ajmalicine, tryptophan,

C. Tikhomiroff; M. Jolicoeur

2002-01-01

426

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

427

Chemical relationships of Polypremum procumbens, Tetrachondra hamiltonii and Peltanthera floribunda  

Microsoft Academic Search

Polypremum procumbens (Buddlejaceae) was found to contain sorbitol, cornoside, salidroside and conandroside. One collection of Peltanthera floribunda (Buddlejaceae) contained verbascoside, two others the cornoside-derived rengyolone (=halleridone). From Tetrachondra hamiltonii (Tetrachondraceae) was isolated sorbitol, cornoside and verbascoside. Iridoids were not found in any of the taxa. The taxonomic significance of the different chemical constituents is discussed, and the data demonstrate a

Søren Rosendal Jensen

2000-01-01

428

Phenylethanoid glycosides from Lippia javanica  

Microsoft Academic Search

Lippia javanica (N.L.Burm.) Spreng. is an aromatic, multipurpose medicinal plant from which a number of volatile compounds have been identified, together with toxic triterpenoids and iridoid glycosides. Two additional phenylethanoid glycosides, verbascoside and isoverbascoside, were isolated from L. javanica and characterized. High performance liquid chromatography analyses of polar extracts of three other Lippia species (L. scaberrima, L. rehmannii and L.

D. K. Olivier; E. A. Shikanga; S. Combrinck; R. W. M. Krause; T. Regnier; T. P. Dlamini

2010-01-01

429

Catalpol protects dopaminergic neurons from LPS-induced neurotoxicity in mesencephalic neuron-glia cultures  

Microsoft Academic Search

Inflammation plays an important role in the pathogenesis of Parkinson's disease (PD). Microglia, the resident immune cells in the central nervous system, are pivotal in the inflammatory reaction. Activated microglia can induce expression of inducible nitric-oxide synthase (iNOS) and release significant amounts of nitric oxide (NO) and TNF-?, which can damage the dopaminergic neurons. Catalpol, an iridoid glycoside, contained richly

Yuan-Yuan Tian; Li-Jia An; Lan Jiang; Yan-Long Duan; Jun Chen; Bo Jiang

2006-01-01

430

2001 The Society for the Study of Evolution. All rights reserved. Evolution, 55(3), 2001, pp. 522537  

E-print Network

defense. I investigate the evolutionary history of host-plant use in the tribe Melitaeini by testing three times inde- pendently. The results show that the evolution of host-plant use in melitaeines has considering host-plant chemistry. Key words. Asteridae, host-plant use, iridoid glycosides, Lepidoptera

Wahlberg, Niklas

431

Rehmannia glutinosa: Review of botany, chemistry and pharmacology  

Microsoft Academic Search

Rehmannia glutinosa, a widely used traditional Chinese herb, belongs to the family of Scrophulariaceae, and is taken to nourish Yin and invigorate the kidney in traditional Chinese medicine (TCM) and has a very high medicinal value. In recent decades, a great number of chemical and pharmacological studies have been done on Rehmannia glutinosa. More than 70 compounds including iridoids, saccharides,

Ru-Xue Zhang; Mao-Xing Li; Zheng-Ping Jia

2008-01-01

432

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

433

Glucosylation of taxifolin with cultured plant cells.  

PubMed

Cultured plant cells of Eucalyptus perriniana glucosylated taxifolin to its 3'- and 7-O-beta-D-glucosides and 3',7-O-beta-D-diglucoside. On the other hand, taxifolin was converted into 3'- and 7-O-beta-D-glucosides by cultured cells of Nicotiana tabacum and Catharanthus roseus. PMID:23980419

Shimoda, Kei; Kubota, Naoji; Hamada, Manabu; Sugamoto, Masahiro; Ishihara, Kohji; Hamada, Hatsuyuki; Hamada, Hiroki

2013-07-01

434

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

435

Bioavailability Is Improved by Enzymatic Modification of the Citrus Flavonoid Hesperidin in Humans: A Randomized, Double-Blind, Crossover Trial1  

Microsoft Academic Search

Hesperidin is the predominant polyphenol consumed from citrus fruits and juices. However, hesperidin is proposed to have limited bioavailability due to the rutinoside moiety attached to the flavonoid. The aim of this study was to demonstrate in human subjects that the removal of the rhamnose group to yield the corresponding flavonoid glucoside (i.e., hesperetin-7-glucoside) will improve the bioavailability of the

Inge Lise; F. Nielsen; Winnie S. S. Chee; Lea Poulsen; Elizabeth Offord-Cavin; Salka E. Rasmussen; Hanne Frederiksen; Marc Enslen; Denis Barron; Marie-Noelle Horcajada; Gary Williamson

436

New spermidine alkaloids from Capparis spinosa roots  

Microsoft Academic Search

Three new spermidine alkaloids capparispine (1), capparispine 26-O-?-d-glucoside (2) and cadabicine 26-O-?-d-glucoside hydrochloride (3) were isolated from the roots of Capparis spinosa. Their structures were established on the basis of spectroscopic analysis, including 1D and 2D NMR experiments (1H–1H COSY, HSQC, HMBC).

Xiao Pu Fu; Tao Wu; Miriban Abdurahim; Zhen Su; Xue Ling Hou; Haji Akber Aisa; Hankui Wu

2008-01-01

437

Characterization of anthocyanins and anthocyanidins in purple-fleshed sweetpotatoes by HPLC-DAD/ESI-MS/MS.  

PubMed

Purple-fleshed sweetpotatoes (PFSP) can be a healthy food choice for consumers and a potential source for natural food colorants. This study aimed to identify anthocyanins and anthocyanidins in PFSP, and to evaluate the effect of thermal processing on these polyphenolic compounds. Freeze-dried powder of raw and steamed samples of three PFSP varieties were extracted with acidified methanol using a Dionex ASE 200 accelerated solvent extractor. Seventeen anthocyanins were identified by HPLC-DAD/ESI-MS/MS for Stokes Purple and NC 415 varieties with five major compounds: cyanidin 3-caffeoylsophoroside-5-glucoside, peonidin 3-caffeoylsophoroside-5-glucoside, cyanidin 3-caffeoyl-p-hydroxybenzoylsophoroside-5-glucoside, peonidin 3-caffeoyl-p-hydroxybenzoyl-sophoroside-5-glucoside, and peonidin-caffeoyl-feruloylsophoroside-5-glucoside. Okinawa variety showed 12 pigments with 3 major peaks identified as cyanidin 3-caffeoylsophoroside-5-glucoside, cyanidin 3-(6'',6'''-dicaffeoylsophoroside)-5-glucoside and cyanidin 3-(6''-caffeoyl-6'''-feruloylsophoroside)-5-glucoside. Steam cooking had no significant effect on total anthocyanin content or the anthocyanin pigments. Cyanidin and peonidin, which were the major anthocyanidins in the acid hydrolyzed extracts, were well separated and quantified by HPLC with external standards. Cyanidin and peonidin, which contribute to the blue and red hues of PFSP, can be simply quantified by HPLC after acid hydrolysis of the anthocyanins. PMID:20017481

Truong, Van-Den; Deighton, Nigel; Thompson, Roger T; McFeeters, Roger F; Dean, Lisa O; Pecota, Kenneth V; Yencho, G Craig

2010-01-13

438

A New Flavonol Tetraglycoside from Myrsine Africana Leaves  

Microsoft Academic Search

A new flavonol glycoside, quercetin 3 - glucosyl (1?? - 4?) rhamnoside - 7 -rhamnosyl (1?? - 6??) glucoside (1) together with known flavonol glycosides, quercetin 3 -rhamnoside (2), quercetin 3 - glucoside (3) and myricetin 3 - galactoside (4) have been isolated from methanolic extract of Myrsine africana leaves and identified on the basis of their spectral data.

Lawrence O. A. Manguro; Jacob Ogweno Midiwo; Wolgang Kraus

1996-01-01

439

VOL. 241616 COMMUNICATIONS Studies on the Barks of the Family  

E-print Network

crystalline fractions isolated from the bark of P. tremuloidesl by means of paper chromatography indicated glucoside fractions ob- tained from the bark of P. tremuloidesby means of paper chromatography the Bark of Populus tremuloides Sir: In our recent paper' on the structure of the new glucoside

Berry, R. Stephen

440

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

441

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

Conejero, Genevieve

2014-01-01

442

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

443

Constituents of Gardenia volkensii: their brine shrimp lethality and DPPH radical scavenging properties  

Microsoft Academic Search

The seeds and the pulp of Gardenia volkensii yielded one new iridiod, namely 4-(2N-gardenamide)n-butanoic acid, together with the known iridoids genipin and genipin gentiobioside, the pterocarpin medicarpin, coumarins, phenylpropanoids, benzenoids and triterpenes. The structures of these were determined on the basis of spectroscopic data and by comparison of obtained data with those from literature. The fruit extracts of this plant

Bernard F. Juma; Runner R. T. Majinda

2007-01-01

444

d-galactose administration induces memory loss and energy metabolism disturbance in mice: Protective effects of catalpol  

Microsoft Academic Search

The neuroprotective effects of catalpol, an iridoid glycoside isolated from the fresh rehmannia roots, on the behavior and brain energy metabolism in senescent mice induced by d-galactose were assessed. Except control group, mice were subcutaneously injected with d-galactose (150mg\\/kg body weight) for 6 weeks. From the fifth week, drug group mice were treated with catalpol (2.5, 5, 10mg\\/kg body weight)

Xiu-li Zhang; Li-jia An; Yong-ming Bao; Jing-yun Wang; Bo Jiang

2008-01-01

445

Isolation of chemical constituents from the aerial parts of Verbascum thapsus and their antiangiogenic and antiproliferative activities  

Microsoft Academic Search

Phytochemical investigation of Verbascum thapsus led to the isolation and identification of one new iridoid compound named verbathasin A, along with ten known compounds.\\u000a The structure and relative stereochemistry of verbathasin A were elucidated by analysis of spectroscopic data. All the isolates\\u000a except 10-deoxyeucommiol and ajugol were tested for antiangiogenic and antiproliferative activities, and compounds luteolin\\u000a and 3-O-fucopyranosylsaikogenin F showed

Yan-Li Zhao; Si-Feng Wang; Yang Li; Qiu-Xia He; Ke-Chun Liu; Yong-Ping Yang; Xiao-Li Li

2011-01-01

446

Isolation of chemical constituents from the aerial parts of Verbascum thapsus and their antiangiogenic and antiproliferative activities.  

PubMed

Phytochemical investigation of Verbascum thapsus led to the isolation and identification of one new iridoid compound named verbathasin A, along with ten known compounds. The structure and relative stereochemistry of verbathasin A were elucidated by analysis of spectroscopic data. All the isolates except 10-deoxyeucommiol and ajugol were tested for antiangiogenic and antiproliferative activities, and compounds luteolin and 3-O-fucopyranosylsaikogenin F showed promising antiproliferative activities, with an obvious effect of inducing apoptosis of A549 lung cancer cells. PMID:21656353

Zhao, Yan-Li; Wang, Si-Feng; Li, Yang; He, Qiu-Xia; Liu, Ke-Chun; Yang, Yong-Ping; Li, Xiao-Li

2011-05-01

447

Chemotaxonomy and evolution of Plantago L  

Microsoft Academic Search

In continuation of our investigations of the genus Plantago L. (Plantaginaceae), sixteen species were investigated with respect to water-soluble glycosides. The iridoids auroside, strictoloside and globularicisin, as well as poliumoside, 3-[(4-ß-D-glucopyranosyloxy)phenyl]propionic acid and 2-[4-(ß-D-glucopyranosyloxy)phenyl]acetic acid were isolated from Plantago for the first time. The latter compound has not previously been isolated as a natural product. Sorbitol was the main carbohydrate

N. Rønsted; H. Franzyk; P. Mølgaard; J. W. Jaroszewski; S.