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1

Iridoid glucosides from Plantago cornuti, Plantago major and Veronica cymbalaria  

Microsoft Academic Search

The new iridoid glucoside from the rare ?8,9 type, 10-acetoxymajoroside, was isolated from Plantago cornuti and P. major along with known iridoids. The main constituents in V. cymbalaria were the known catalpol, amphicoside and verproside together with alpinoside, aucubin, 6-O-veratroylcatalpol and verminoside. The iridoid alpinoside with a 8,9-double bond was found for the first time in genus Veronica.

Rilka Taskova; Nedjalka Handjieva; Ljubka Evstatieva; Simeon Popov

1999-01-01

2

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

3

Iridoid Glucosides from Penstemon nitidus.  

PubMed

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

Teborg, D; Junior, P

1991-04-01

4

Secoiridoid Glucosides and Iridoids From Jasminum Odoratissimum  

Microsoft Academic Search

Two new secoiridoid glucosides, trans- 10-(cinnamoyloxy) oleoside dimethylester (methyl jasminoside) and cis-10-(cinnamoyloxy) oleoside monomethyl ester, and two new iridoids, 1?-and 1?-, 7-dehydrologanetin, together with the known iridoid jasminoside were isolated from leaves of Jasminum odoratissimum. the structures of these compounds have been characterised on the basis of spectroscopic evidence.

José A. Pérez; José M. Hemández; Hermelo López; Juan M. Trujillo

1999-01-01

5

Sesinoside, a new iridoid glucoside from sesame (Sesamum indicum) seedlings.  

PubMed

A new iridoid glucoside, sesinoside (1), was isolated from the seedlings of Sesamum indicum. The structure of 1 was elucidated by spectroscopic analyses and by methanolysis of 1, which produced the known compounds, phlorigidosides C (2) and (6Z)-foliamenthic acid methyl ester (3). This is the first report of an iridoid glucoside with 3. PMID:25532274

Takase, Ryo; Hasegawa, Tsuyoshi; Yamada, Kosumi; Hasegawa, Koji; Shigemori, Hideyuki

2014-11-01

6

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

PubMed

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

Junior, P

1981-09-01

7

An iridoid glucoside and the related aglycones from Cornus florida.  

PubMed

A new iridoid glucoside, cornusoside A (1), and four new natural product iridoid aglycones, cornolactones A-D (2-5), together with 10 known compounds were isolated from the leaves of Cornus florida. The structures of compounds 1-5 were established by interpretation of their spectroscopic data. Cornolactone B (3) is the first natural cis-fused tricyclic dilactone iridoid containing both a five- and a six-membered lactone ring. A biosynthesis pathway is proposed for cornolactones C (4) and D (5), the C-6 epimers of compounds 1-3. PMID:25141901

He, Yangqing; Peng, Jiangnan; Hamann, Mark T; West, Lyndon M

2014-09-26

8

Further iridoid glucosides in the genus Manulea (Scrophulariaceae).  

PubMed

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

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

2015-01-01

9

Acylated iridoid glucosides from Veronica anagallis-aquatica  

Microsoft Academic Search

Three new (1–3) and four known iridoid glucosides (4–7) as well as a known phenylethanoid glycoside (8) were isolated from the aerial parts of Veronica anagallis-aquatica and their structures were determined as 6?-O-benzoyl-8-epiloganic acid named aquaticoside A (1), 6?-O-p-hydroxybenzoyl-8-epiloganic acid named aquaticoside B (2), 6?-O-benzoyl-gardoside named aquaticoside C (3), veronicoside (4), catalposide (5), verproside (6), verminoside (7) and martynoside (8)

U. Sebnem Harput; Mehtap Varel; Akito Nagatsu; Iclal Saracoglu

2004-01-01

10

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

11

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

12

Acylated iridoid glucosides from Veronica anagallis-aquatica.  

PubMed

Three new (1-3) and four known iridoid glucosides (4-7) as well as a known phenylethanoid glycoside (8) were isolated from the aerial parts of Veronica anagallis-aquatica and their structures were determined as 6'-O-benzoyl-8-epiloganic acid named aquaticoside A (1), 6'-O-p-hydroxybenzoyl-8-epiloganic acid named aquaticoside B (2), 6'-O-benzoyl-gardoside named aquaticoside C (3), veronicoside (4), catalposide (5), verproside (6), verminoside (7) and martynoside (8) on the basis of 1D and 2D NMR spectral analysis. PMID:15279985

Harput, U Sebnem; Varel, Mehtap; Nagatsu, Akito; Saracoglu, Iclal

2004-07-01

13

Iridoids from Globularia dumulosa.  

PubMed

Two new iridoids, 10-O-benzoylglobularigenin (1) and dumuloside (2) were isolated from the aerial parts of Globularia dumulosa together with seven known iridoid glucosides, davisioside (3), aucubin (4), melampyroside (5), catalpol (6), 10-O-benzoylcatalpol (7), alpinoside (8) and deacetylalpinoside (9). Three phenylethanoid glycosides, verbascoside, decaffeoyl-verbascoside, leucosceptoside A and three flavone glucosides, pectolinarigenin 7-O-beta-D-glucopyranoside, nepetin 7-O-B-D-glucopyranoside, demethoxycentaureidin 7-O-beta-D-glucopyranoside were also isolated and characterized. The structure elucidation of the isolated compounds was performed by spectroscopic (UV, IR, HR-MALDIMS, 1D- and 2D NMR) methods. PMID:12710725

Kirmizibekmez, Hasan; Akbay, Pinar; Sticher, Otto; Cali?, Ihsan

2003-01-01

14

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

Microsoft Academic Search

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

Henrik Franzyk; Søren Rosendal Jensen; Frank R Stermitz

1998-01-01

15

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

16

The iridoid glucoside, antirrhinoside, from Antirrhinum majus L. has differential effects on two generalist insect herbivores.  

PubMed

The iridoid glucoside, antirrhinoside, is constitutively distributed throughout Antirrhinum majus L. in a manner consistent with its possible role as an allelochemical, but there is no evidence that it has a defensive function with respect to insect herbivory. To address this question, two generalist herbivores, Lymantria dispar L. (gypsy moth) and Trichoplusia ni Hübner (cabbage looper) were chosen for feeding trials on excised whole leaves of A. majus and in artificial diet assays. In leaf excision feeding trials, fourth instar gypsy moth rejected, without sampling, the leaves of A. majus regardless of what node the leaf was excised from. In contrast, fourth instar cabbage looper readily fed on the excised leaves, and antirrhinoside was not found in their bodies or feces (frass) as determined by thin layer and high-pressure liquid chromatography. In the leaf and diet assays, a second major leaf iridoid in A. majus, antirrhide, was found in both cabbage looper and gypsy moth frass. In diet feeding assays, the growth of gypsy moth and cabbage looper were not inhibited by methanol extracts, iridoid fractions, or pure antirrhinoside at concentrations of 0.6% in diet, but cabbage looper growth was enhanced. At an antirrhinoside concentration of 3.3% in diet, gypsy moth growth was reduced, whereas cabbage looper growth again increased significantly relative to the control. It is likely that antirrhinoside functions as defense against herbivory for one generalist insect herbivore but also, at low concentrations, enhances the growth of another. PMID:18414950

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

2008-05-01

17

Euphydryas anicia (Lepidoptera: Nymphalidae) utilization of iridoid glycosides fromCastilleja andBesseya (Scrophulariaceae) host plants.  

PubMed

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 uses bothB. plantaginea andC. integra as host plants was found to sequester cataipol as well as another iridoid, macfadienoside. Macfadienoside was the major iridoid ofC. integra, while catalpol esters were the major iridoids ofB. plantaginea. Although it was a major sequestered iridoid, catalpol was a minor constituent in both host plants. The macfadienoside-catalpol ratio in the butterflies from this population was highly variable, and there appeared to be both sex and individual variation in host plant and/or iridoid glucoside utilization byE. anicia. Although other iridoids were present in the host plants, none was sequestered in more than trace amounts. PMID:24307124

Stermitz, F R; Gardner, D R; Odendaal, F J; Ehrlich, P R

1986-06-01

18

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

19

Aucubin promotes neurite outgrowth in neural stem cells and axonal regeneration in sciatic nerves.  

PubMed

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. PMID:25258571

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

2014-09-01

20

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. PMID:25258571

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

2014-01-01

21

Aquaticol, a bis-sesquiterpene and iridoid glucosides from Veronica anagallis-aquatica.  

PubMed

Aquaticol, an unusual bis-sesquiterpene was isolated from the medicinal plant Veronica anagallis-aquatica, in addition to 11 known compounds, aucubin, geniposidic acid, mussaenoside, catalposide, verproside, amphicoside, catalpol, boschnaloside, shanzhiside methyl ester, sitosterol and beta-stigmast-4-en-6 beta-ol-3-one. The structure of aquaticol was determined by spectroscopic means and by X-ray crystallographic analysis. PMID:10821060

Su, B N; Yang, L; Gao, K; Jia, Z J

2000-04-01

22

Bioassay-guided isolation of iridoid glucosides with antinociceptive and anti-inflammatory activities from Veronica anagallis-aquatica L.  

PubMed

Extracts obtained from the herbs of various Veronica species are used as folk remedy worldwide for the treatment of various inflammatory ailments including rheumatism. In vivo anti-inflammatory and antinociceptive activities of Veronica anagallis-aquatica L. aerial parts were investigated. Methanolic extract of the plant was shown to possess significant inhibitory activity against carrageenan-induced hind paw edema model and of p-benzoquinone-induced writhings in mice. Through bioassay-guided fractionation and isolation procedures eight compounds, aquaticoside A (1), aquaticoside B (2), aquaticoside C (3), veronicoside (4), catalposide (5), verproside (6), verminoside (7) and martynoside (8) were isolated and their structures were elucidated by spectral techniques. Catapol derivative iridoid glucosides, verproside (6) and catalposide (5), were found to possess potent antinociceptive and anti-inflammatory activities, per os without inducing any apparent acute toxicity as well as gastric damage. Results of the present study supported the utilization of the plant in Turkish folk medicine. PMID:16019176

Küpeli, Esra; Harput, U Sebnem; Varel, Mehtap; Yesilada, Erdem; Saracoglu, Iclal

2005-11-14

23

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

24

Verbascoside derivatives and iridoid glycosides from Penstemon crandallii.  

PubMed

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

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

1995-08-01

25

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

PubMed Central

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

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

2011-01-01

26

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

27

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

28

Fate of Host-Plant Iridoid Glycosides in Lepidopteran Larvae of Nymphalidae and Arcthdae  

Microsoft Academic Search

We compared the ability of larvae of six lepidopteran species to sequester iridoid glycosides. All larvae were fed on a common host plant, Plantago lanceolata, which contains two iridoid glycosides, aucubin and catalpol. Four species of arctiids were examined: Pyrrharctia isabella, Spilosoma congrua, Spilosoma latipennis, and Spilosoma virginica. For comparison, we also examined two nymphalid species, one of which, Junonia

M. Deane Bowers; Nancy E. Stamp

1997-01-01

29

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

Microsoft Academic Search

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

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

1993-01-01

30

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

31

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

Microsoft Academic Search

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

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

2000-01-01

32

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

33

The hydrolysed products of iridoid glycosides can enhance imatinib mesylate-induced apoptosis in human myeloid leukaemia cells.  

PubMed

Several studies have demonstrated that deregulated activation of signal transducer and activator of transcription 3 (STAT3) has been associated with survival, proliferation, chemoresistance and angiogenesis of tumour cells. Thus, inhibition of STAT3 expression could be a potent therapeutic approach for cancer treatment. Using several leukaemia cell lines, the effect of the hydrolysed-catalpol (H-catalpol) and hydrolysed-aucubin (H-aucubin) products on the STAT3 signalling pathway, inhibition of BCR-ABL activation, cellular proliferation and potentiation of imatinib mesylate-induced apoptosis was investigated. We found that iridoid glycosides (catalpol and aucubin) did not exert any cytotoxicity in the tumour cells, whereas both H-catalpol and H-aucubin exhibited significant cytotoxic effects on K562 human myeloid leukaemia cells. Indeed, H-catalpol and H-aucubin down-regulated BCR-ABL phosphorylation and inhibited constitutive STAT3 activation through abrogating upstream JAK2 and c-Src and constitutive STAT5 activation leading to apoptosis through caspase-3 activation. Hydrolysed-catalpol enhanced the apoptosis induced by imatinib mesylate and this correlated with down-regulation of gene products that mediate cell proliferation (cyclin D1), and cell survival (Bcl-2, Bcl-xL and survivin); all known to be regulated by the STAT3. Overall, our results provide novel insight into the role of hydrolysed iridoids in potentially treating leukaemia through the modulation of STAT3 signalling pathway. Copyright © 2015 John Wiley & Sons, Ltd. PMID:25583173

Kim, Min-Beom; Kim, Chulwon; Chung, Won-Seok; Cho, Jae-Heung; Nam, Dongwoo; Kim, Sung-Hoon; Ahn, Kwang Seok

2015-03-01

34

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

35

Host plant utilization and iridoid glycoside sequestration byEuphydryas anicia (Lepidoptera: Nymphalidae).  

PubMed

The iridoid glycoside content of individual adultEuphydryas anicia butterflies from two Colorado populations was quantitatively determined. At one site (Red Hill), larval host plants wereCastilleja integra andBesseya plantaginea, while at the other site (Cumberland Pass) a single host plant,B. alpina, was used. At Red Hill, macfadienoside and catalpol were sequestered, while at Cumberland Pass, catalpol and aucubin were sequestered. Artificial diet studies showed that larvae hydrolyzed a major iridoid ofB. plantaginea, 6-isovanilIylcatalpol, to catalpol (which was sequestered) and isovanillic acid (which was excreted). Large year-to-year and individual variation in butterfly iridoid content was established as was a female-male difference in macfadienoside vs. catalpol content. Larval host plant distributions and numbers were determined at Red Hill for two years and compared with changes in butterfly populations and sequestered iridoids. PMID:24277236

Gardner, D R; Stermitz, F R

1988-12-01

36

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

37

Host plant utilization and iridoid glycoside sequestration by Euphydryas anicia (Lepidoptera: Nymphalidae)  

Microsoft Academic Search

The iridoid glycoside content of individual adultEuphydryas anicia butterflies from two Colorado populations was quantitatively determined. At one site (Red Hill), larval host plants wereCastilleja integra andBesseya plantaginea, while at the other site (Cumberland Pass) a single host plant,B. alpina, was used. At Red Hill, macfadienoside and catalpol were sequestered, while at Cumberland Pass, catalpol and aucubin were sequestered. Artificial

Dale R. Gardner; Frank R. Stermitz

1988-01-01

38

[Iridoid glycosides from buds of Jasminum officinale L. var. grandiflorum].  

PubMed

The study on the buds of Jasminum officinale L. var. grandiflorum was carried out to look for anti-HBV constituents. The isolation and purification were performed by HPLC and chromatography on silica gel, polyamide and Sephadex LH-20 column. The structures were elucidated on the basis of physicochemical properties and spectral analysis. Six iridoid glycosides were identified as jasgranoside B (1), 6-O-methy-catalpol (2), deacetyl asperulosidic acid (3), aucubin (4), 8-dehydroxy shanzhiside (5), and loganin (6). Jasgranoside B (1) is a new compound. Compounds 2-6 were isolated from Jasminum officinale L. var. grandiflorum for the first time. PMID:22242454

Zhao, Gui-qin; Yin, Zhi-feng; Liu, Yu-cui; Li, Hong-bo

2011-10-01

39

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

PubMed

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

Lampert, Evan C; Bowers, M Deane

2011-05-01

40

Influence of iridoid glycoside containing host plants on midgut ?-glucosidase activity in a polyphagous caterpillar, Spilosoma virginica Fabricius (Arctiidae).  

PubMed

Iridoid glycosides are secondary plant compounds that have deterrent, growth reducing or even toxic effects on non-adapted herbivorous insects. To investigate the effects of iridoid glycoside containing plants on the digestive metabolism of a generalist herbivore, larvae of Spilosoma virginica (Lepidoptera: Arctiidae) were reared on three plant species that differ in their secondary plant chemistry: Taraxacum officinale (no iridoid glycosides), Plantago major (low iridoid glycoside content), and P. lanceolata (high iridoid glycoside content). Midguts of fifth instar larvae were assayed for the activity and kinetic properties of ?-glucosidase using different substrates. Compared to the larvae on T. officinale, the ?-glucosidase activity of larvae feeding on P. lanceolata was significantly lower measured with 4-nitrophenyl-?-d-glucopyranoside. Using the iridoid glycoside aucubin as a substrate, we did not find differences in the ?-glucosidase activity of the larvae reared on the three plants. Heat inactivation experiments revealed the existence of a heat-labile and a more heat-stable ?-glucosidase with similar Michaelis constants for 4-nitrophenyl-?-d-glucopyranoside. We discuss possible mechanisms leading to the observed decrease of ?-glucosidase activity for larvae reared on P. lanceolata and its relevance for generalist herbivores in adapting to iridoid glycoside containing plant species and their use as potential host plants. PMID:20727899

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

2010-12-01

41

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

42

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

43

Iridoid glycosides from Thunbergia grandiflora  

Microsoft Academic Search

The novel iridoid glycosides, isounedoside and grandifloric acid, were isolated from Thunbergia grandiflora. Grandifloric acid contains C-10 as a carboxylic acid group, the presence of which was predicted by recent iridoid biosynthesis studies carried out within T. alata. Isounedoside contains a rare 6,7-epoxide functional group. A revision in some of the NMR spectral assignments for the known iridoid glycoside alatoside

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

1996-01-01

44

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

PubMed

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

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

2012-06-01

45

Systemic, genotype-specific induction of two herbivore-deterrent iridoid glycosides in Plantago lanceolata L. in response to fungal infection by Diaporthe adunca (Rob.) Niessel.  

PubMed

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 stalk disease in P. lanceolata. Significant induction of aucubin and catalpol was observed in two of the three plant genotypes used in this study following inoculation with the pathogen. In one of the genotypes, induction occurred within 6 hr after inoculation, and no decay was observed within 8 days. The highest level of induction was observed in reproductive tissues (spikes and stalks) where infection took place. In these tissues, iridoid glycoside levels in infected plants were, on average, 97% and 37% higher than the constitutive levels in the corresponding control plants, respectively. Significant induction was also observed in leaves (24%) and roots (17%). In addition to significant genotypic variation in the level of induction, we found genetic variation for the tissue-specific pattern of induction, further broadening the scope for evolutionary fine-tuning of induced responses. Recent studies have revealed a negative association between iridoid glycoside levels in P. lanceolata genotypes and the amount of growth and reproduction of D. adunca that these genotypes support. However, for the three genotypes used in the present study, differences in resistance were not related to their constitutive or induced levels of iridoid glycosides, suggesting that additional resistance mechanisms are important in this host-pathogen system. We conclude that iridoid glycosides in P. lanceolata can be induced both by arthropods and pathogenic micro-organisms. Pathogen infection could, therefore, potentially enhance resistance to generalist insect herbivores in this species. PMID:12564791

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

2002-12-01

46

Role of plant ?-glucosidases in the dual defense system of iridoid glycosides and their hydrolyzing enzymes in Plantago lanceolata and Plantago major.  

PubMed

The typical defense compounds of Plantaginaceae are the iridoid glycosides, which retard growth and/or enhance mortality of non-adapted herbivores. In plants, glycosidic defense compounds and hydrolytic enzymes often form a dual defense system, in which the glycosides are activated by the enzymes to exert biological effects. Yet, little is known about the activating enzymes in iridoid glycoside-containing plants. To examine the role of plant-derived ?-glucosidases in the dual defense system of two common plantain species, Plantago lanceolata and Plantago major, we determined the concentration of iridoid glycosides as well as the ?-glucosidase activity in leaves of different age. To investigate the presence of other leaf metabolites potentially involved in plant defense, we used a metabolic fingerprinting approach with ultra-high performance liquid chromatography coupled with time-of-flight-mass spectrometry. According to the optimal defense hypothesis, more valuable parts such as young leaves should be better protected than less valuable parts. Therefore, we expected that both, the concentrations of defense compounds as well as the ?-glucosidase activity, should be highest in younger leaves and decrease with increasing leaf age. Both species possessed ?-glucosidase activity, which hydrolyzed aucubin, one of the two most abundant iridoid glycosides in both plant species, with high activity. In line with the optimal defense hypothesis, the ?-glucosidase activity in both Plantago species as well as the concentration of defense-related metabolites such as iridoid glycosides correlated negatively to leaf age. When leaf extracts were incubated with bovine serum albumin and aucubin, SDS-PAGE revealed a protein-denaturing effect of the leaf extracts of both plantain species, suggesting that iridoid glycosides and plant ?-glucosidase interact in a dual defense system. PMID:23773298

Pankoke, Helga; Buschmann, Torsten; Müller, Caroline

2013-10-01

47

Iridoid glycosides from Thunbergia grandiflora.  

PubMed

The novel iridoid glycosides, isounedoside and grandifloric acid, were isolated from Thunbergia grandiflora. Grandifloric acid contains C-10 as a carboxylic acid group, the presence of which was predicted by recent iridoid biosynthesis studies carried out within T. alata. Isounedoside contains a rare 6,7-epoxide functional group. A revision in some of the NMR spectral assignments for the known iridoid glycoside alatoside was also made. PMID:8688191

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

1996-07-01

48

Iridoids from Symphoricarpos albus  

Microsoft Academic Search

Twelve compounds including secologanin, loganin, the aglycon of loganin, and a new iridoid called glucologanin were isolated\\u000a from fruit of common snowberry Symphoricarpos albus (L.) Blake. The structure of glucologanin was confirmed using PMR and mass spectroscopy and chemical transformations. 2?,3?,4?,6?,7-Penta-O-acetylloganin and 2?,3?,4?,6?-tetra-O-acetylloganin were synthesized.

I. F. Makarevich; S. N. Kovalenko; T. D. Gusarova; Yu. I. Gubin

2009-01-01

49

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

50

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

PubMed Central

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

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

2014-01-01

51

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

PubMed Central

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

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

2004-01-01

52

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

Microsoft Academic Search

Two saponins: scrokoelziside A (1), scrokoelziside B (2), one iridoid glycoside, eurostoside (3), and two flavonoids: nepitrin (4) and homoplantaginin (5), were isolated from the leaves of Scrophularia ningpoensis for the first time. Moreover, eight known compounds: cane sugar (6), harpagide (7), aucubin (8), 6-O-methylcatalpol (9), harpagoside (10), angoroside C (11), ?-sitosterol (12) and ?-sitosterol glucoside (13) were isolated from

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

2009-01-01

53

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

PubMed

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

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

2013-09-01

54

A rapid and sensitive determination of aucubin in rat plasma by liquid chromatography-tandem mass spectrometry and its pharmacokinetic application.  

PubMed

A sensitive, accurate, rapid and robust LC-MS-MS method for the quantification of aucubin, a major bioactive constituent of Aucuba japonica, Eucommia ulmoides and Plantago asiatica, was established and validated in rat plasma. Plasma samples were simply precipitated by adding methanol and the supernatant was chromatographed by a Diamonsil® C(18)(2) column with the mobile phase comprising a mixture of 10?mm ammonium acetate in methanol and that in water with the ratio of 50:50 (v/v). Quantification of aucubin was performed by mass spectrometry in the multiple-reaction monitoring mode with positive atmospheric ionization at m/z 364???149 for aucubin, and m/z 380???165 for catalpol (IS), respectively. The retention time was 2.47 and 2.44?min for aucubin and the IS, respectively. The calibration curve (10.0-30,000?ng/mL) was linear (r² ?>?0.99) and the lower limit of quantification was 10.0?ng/mL in the rat plasma sample. The method showed satisfactory results such as sensitivity, specificity, precision, accuracy, recovery, freeze-thaw and long-term stability. This simple LC-MS method was successfully applied in a pharmacokinetic study carried out in Sprague-Dawley rats after oral administration of aucubin at a single dose of 50?mg/kg. Herein the pharmacokinetic study of aucubin is reported for the first time. PMID:22113886

Xu, Wei; Deng, Zhipeng; Guo, Hong; Ling, Peixue

2012-09-01

55

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

PubMed

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

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

1998-11-01

56

Formation of bilirubin glucoside.  

PubMed

1. Rat liver microsomal preparation can effect the transglucosylation from UDP-glucose to bilirubin in the presence of Mg(2+). 2. Other nucleotides, namely CDP-glucose, ADP-glucose and GDP-glucose, were not active as glucosyl donors. 3. Only trace amounts of galactose, galacturonic acid and N-acetylglucosamine were conjugated to bilirubin when their respective UDP derivatives were used in the reaction mixture. 4. The azobilirubin glucosides produced by coupling with p-diazobenzenesulphonic acid and diazotized ethyl anthranilic acid were separable from the corresponding azobilirubin glucuronides by t.l.c. 5. The glucoside was, however, hydrolysed by both beta-glucosidase and various preparations of beta-glucuronidase; azobilirubin and glucose were liberated in the process. 6. Kinetic studies showed that the effects of pH and Mg(2+) on the two conjugating systems were similar. 7. The specific activities of hepatic bilirubin UDP-glucosyltransferase, expressed as mug of bilirubin ;equivalents' conjugated/h per mg of protein, are respectively 1.7 and 2.4 for male and female rats. 8. The K(m) values for bilirubin and UDP-glucose are 5.7x10(-5)m and 1.6x10(-3)m respectively. 9. The glucoside and glucuronide conjugations of bilirubin are discussed in relation to the availability of the conjugating agents and aglycone in the liver. PMID:5144254

Wong, K P

1971-12-01

57

Trans-fused Iridoid GlycosidEs from Penstemon Mucronatus  

Microsoft Academic Search

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

Robert E. Krull; Frank R. Stermitz

1998-01-01

58

Trans-fused iridoid glycosides from Penstemon mucronatus.  

PubMed

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

Krull, R E; Stermitz, F R

1998-12-01

59

Two new iridoids from Verbena officinalis L.  

PubMed

Two new iridoids, 3-(5-(methoxycarbonyl)-2-oxo-2H-pyran-3-yl)butanoic acid, named verbeofflin I (1), and 7-hydroxydehydrohastatoside (2), were isolated from the aerial part of Verbena officinalis L, along with three known iridoids, verbenalin (3), 3,4-dihydroverbenalin (4), hastatoside (5) by means of various column chromatography steps. The structures of these compounds were elucidated through analysis of their spectroscopic data obtained using 1D and 2D NMR and MS techniques. Verbeofflin I (1) is the new class of secoiridoid in the family Verbenaceae. PMID:25045888

Shu, Jicheng; Chou, Guixin; Wang, Zhengtao

2014-01-01

60

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

61

Neolignan glucosides from Jasminum urophyllum  

Microsoft Academic Search

A novel neolignan-secoiridoid glucoside, jasurolignoside, and a new neolignan, urolignoside, have been isolated from Jasminum urophyllum. Their structures were elucidated on the basis of 2D-NMR and chemical methods.

Ya-Ching Shen; Pei-Wen Hsieh; Yao-Haur Kuo

1998-01-01

62

Iridoids and lignans from Valeriana jatamansi.  

PubMed

Thirteen new iridoids including seven iridolactones, jatamanins A-M (1-13), and a new lignan, (+)-9'-isovaleroxylariciresinol (14), together with seven known iridoids and 13 lignans were obtained from whole plants of Valeriana jatamansi. Structures of the new compounds were determined by spectroscopic and crystallographic methods, and the absolute configuration of compound 1 was assigned by application of the modified Mosher method. Jatamanins H (8) and I (9) are iridolactones with an unusual C-8-C-11 oxygen bridge, forming a cage-like structure. (+)-9'-Isovaleroxylariciresinol (14) showed significant in vitro cytotoxicity against PC-3M and HCT-8 cell lines, with IC(50) values of 8.1 and 5.3 microM, respectively. PMID:20151678

Lin, Sheng; Chen, Tao; Liu, Xiao-Hua; Shen, Yun-Heng; Li, Hui-Liang; Shan, Lei; Liu, Run-Hui; Xu, Xi-Ke; Zhang, Wei-Dong; Wang, Hui

2010-04-23

63

Iridoids from the roots of Valeriana jatamansi.  

PubMed

Two new iridoids, jatamanvaltrates N (1) and O (2), together with four known compounds (3-6), were isolated from the roots of Valeriana jatamansi. Their structures and relative configurations were elucidated by spectroscopic methods (IR, ESI-MS, HR-ESI-MS, 1D, and 2D NMR) and by comparison of their NMR spectral data with those of related compounds. All the isolated compounds were evaluated for their neuroprotective effects, and only compound 1 showed weak neuroprotective activities. PMID:22263587

Xu, Jing; Guo, Ping; Fang, Ling-Zhi; Li, Yu-Shan; Guo, Yuan-Qiang

2012-01-01

64

Iridoids and sesquiterpenoids from the roots of Valeriana officinalis.  

PubMed

Two new iridoids, volvaltrates A and B (1 and 2), and three new sesquiterpenoids, E-(-)-3beta,4beta-epoxyvalerenal (3), E-(-)-3beta,4beta-epoxyvalerenyl acetate (4), and mononorvalerenone (5), together with five known iridoids and two known sesquiterpenoids were isolated from the roots of Valeriana officinalis. The structures and relative configurations of 1-5 were elucidated by spectroscopic evidence. Compound 1 was an unusual iridoid with an oxygen bridge connecting C-3 and C-10, forming a cage-like structure, and compound 5 was a mononorsesquiterpenoid. PMID:19691292

Wang, Peng-Cheng; Hu, Jiang-Miao; Ran, Xin-Hui; Chen, Zhong-Quan; Jiang, He-Zhong; Liu, Yu-Qing; Zhou, Jun; Zhao, You-Xing

2009-09-01

65

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

66

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

E-print Network

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

van Nouhuys, Saskya

67

Conversion of Substrate Analogs Suggests a Michael Cyclization in Iridoid Biosynthesis  

PubMed Central

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

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

2014-01-01

68

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

69

The seco-iridoid pathway from Catharanthus roseus  

PubMed Central

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

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

2014-01-01

70

Host plant influences on iridoid glycoside sequestration of generalist and specialist caterpillars.  

PubMed

The effect of diet on sequestration of iridoid glycosides was examined in larvae of three lepidopteran species. Larvae were reared upon Plantago major, or P. lanceolata, or switched from one to the other in the penultimate instar. Junonia coenia is a specialist on iridoid glycoside-producing plants, whereas the arctiids, Spilosoma congrua and Estigmene acrea, are both polyphagous and eat iridoid-producing plants. All species sequestered iridoids. The specialist J. coenia sequestered from three to seven times the amounts sequestered by the two generalist species. Junonia coenia iridoid glycoside content depended on diet, and they sequestered from 5 to 15% dry weight iridoid glycosides. Estigmene acrea iridoid glycoside sequestration was relatively low, around 2% dry weight and did not vary with diet. Spilosoma congrua sequestration varied with diet and ranged from approximately 3 to 6% dry weight. PMID:20809144

Lampert, Evan C; Bowers, M Deane

2010-10-01

71

Iridoids and sesquiterpenoids from the roots of Valeriana jatamansi Jones.  

PubMed

Three new iridoids, jatamanvaltrates R-S (1-2) and jatamanin Q (3), as well as three new sesquiterpenoids, valeriananoids D-E (4, 5) and clovane-2?-isovaleroxy-9?-ol (6), together with nine known compounds were isolated from the roots of Valeriana jatamansi Jones. Compound 2 was the first reported iridoid with fatty acid esters in the Valerianaceae family. The structures of new compounds were established on the basis of extensive spectroscopic analysis. Moreover, all the isolates were evaluated for inhibitory activity on acetylcholinesterase (AChE). PMID:25665939

Dong, Fa-Wu; Liu Yang; Wu, Zhi-Kun; Wei-Gao; Zi, Chen-Ting; Dan Yang; Luo, Huai-Rong; Jun Zhou; Hu, Jiang-Miao

2015-04-01

72

A secoiridoid glucoside from Jasminum odoratissimum  

Microsoft Academic Search

A new secoiridoid glucoside, 10-acetoxyoleoside dimethyl ester, together with the known 10-hydroxyoleoside dimethyl ester was isolated from leaves of Jasminum odoratissimum. The structures of these compounds have been characterized on the basis of spectroscopic evidence.

Juan M. Trujillo; José M. Hernández; José A. Pérez; Hermelo López; Ignacio Frías

1996-01-01

73

Sesquiterpene lactone glucosides from Sonchus asper  

Microsoft Academic Search

From the methanolic extract of the roots of Sonchus asper, two new sesquiterpene glucosides, together with two known sesquiterpene glucosides and a known aglycone were isolated. Structures were identified as 11?,13-dihydrourospermal A, 15-O-?-D-glucopyranosyl-11?,13-dihydrourospermal A, 15-O-?-D-glucopyranosylurospermal A, 15-O-[6?-(p-hydroxyphenylacetyl)]-?-D-glucopyranosylurospermal A and 14-O-methylacetal-15-O-[6?-(p-hydroxyphenylacetyl)]-?-D-glucopyranosylurospermal A, by spectroscopic means.

Amr M. Helal; Norio Nakamura; Hesham El-Askary; Masao Hattori

2000-01-01

74

Sesquiterpene lactone glucosides from Sonchus asper.  

PubMed

From the methanolic extract of the roots of Sonchus asper, two new sesquiterpene glucosides, together with two known sesquiterpene glucosides and a known aglycone were isolated. Structures were identified as 11beta,13-dihydrourospermal A, 15-O-beta-D-glucopyranosyl-11beta,13-dihydrourospermal A, 15-O-beta-D-glucopyranosylurospermal A, 15-O-[6'-(p-hydroxyphenylacetyl)]-beta-D-glucopyranosylurosperm al A and 14-O-methylacetal-15-O-[6'-(p-hydroxyphenylacetyl)]-beta-D-+ ++glucopyranosylurospermal A, by spectroscopic means. PMID:10731026

Helal, A M; Nakamura, N; El-Askary, H; Hattori, M

2000-02-01

75

Bioassay-guided isolation of iridoid glucosides with antinociceptive and anti-inflammatory activities from Veronica anagallis-aquatica L  

Microsoft Academic Search

Extracts obtained from the herbs of various Veronica species are used as folk remedy worldwide for the treatment of various inflammatory ailments including rheumatism. In vivo anti-inflammatory and antinociceptive activities of Veronica anagallis-aquatica L. aerial parts were investigated. Methanolic extract of the plant was shown to possess significant inhibitory activity against carrageenan-induced hind paw edema model and of p-benzoquinone-induced writhings

Esra Küpeli; U. Sebnem Harput; Mehtap Varel; Erdem Yesilada; Iclal Saracoglu

2005-01-01

76

Five new iridoids from roots of Salvia digitaloides.  

PubMed

Five new iridoids, salvialosides A-E (compounds 1-5), together with fifty known compounds were isolated from the roots of Salvia digitaloides. The structures of the new compounds were completely elucidated using a combination of 2D NMR techniques (COSY, NOESY, HMQC and HMBC) and HR-ESI-MS analyses. The known compounds were identified by comparison of their spectroscopic and physical data with those reported in the literature. PMID:25268712

Wu, Shwu-Jen; Chan, Yu-Yi

2014-01-01

77

A new iridoid derivative from the roots of Scrophularia buergeriana.  

PubMed

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

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

2014-07-01

78

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

79

Three new iridoids from the roots of Valeriana jatamansi.  

PubMed

Three new iridoids, valeriandoids D-F (1-3), have been isolated from the roots of Valeriana jatamansi. Structure elucidation, especially the positions of the acyloxy groups, and complete (1)H- and (13)C-NMR assignments of these new compounds were carried out using one- and two-dimensional NMR measurements, including (1)H- and (13)C-NMR, DEPT-135, (1)H-(1)H COSY, HMQC, HMBC, and HR-ESI-MS experiments. PMID:22331424

Xu, Jing; Guo, Yuanqiang; Jin, Da-qing; Zhao, Peng; Guo, Ping; Yamakuni, Tohru; Ohizumi, Yasushi

2012-10-01

80

Iridoid glycoside sequestration by two aposematic Penstemon -feeding geometrid larvae  

Microsoft Academic Search

The iridoid glycoside catalpol was found to be sequestered by larvae ofMeris alticola feeding onPenstemon virgatus and by larvae ofNeoterpes graefiaria which utilizeP. barbatus. The strikingly similar larval patterns of these two ennomine geometrids were previously considered to be disruptive, but predator-based Mullerian mimicry is equally likely to be involved. The cryptic adult moths generally contain only small amounts of

Frank R. Stermitz; Dale R. Gardner; Noel McFarland

1988-01-01

81

Aromatic compound glucosides, alkyl glucoside and glucide from the fruit of anise  

Microsoft Academic Search

From the polar portion of the methanolic extract of the fruit of anise (Pimpinella anisum L.), which has been used as a spice and medicine since antiquity, four aromatic compound glucosides, an alkyl glucoside and a glucide were isolated together with 24 known compounds. The structures of the new compounds were clarified as (E)-3-hydroxyanethole ?-d-glucopyranoside, (E)-1?-(2-hydroxy-5-methoxyphenyl)propane ?-d-glucopyranoside, 3-hydroxyestragole ?-d-glucopyranoside, methyl

Eiko Fujimatu; Toru Ishikawa; Junichi Kitajima

2003-01-01

82

Five trimeric secoiridoid glucosides from Jasminum polyanthum  

Microsoft Academic Search

Investigation of the crude drug “Ye su xin”, the dried flowers of Jasminum polyanthum, has led to the isolation of five new secoiridoid glucosides, oleopolyanthosides A and B, and jaspolyoleosides A, B, and C. The structures of the new compounds were elucidated by spectroscopic and chemical means.

Yukiko Takenaka; Takao Tanahashi; Naotaka Nagakura

1998-01-01

83

Oligomeric secoiridoid glucosides from Jasminum abyssinicum  

Microsoft Academic Search

From the root bark of Jasminum abyssinicum (Oleaceae) collected in Congo was isolated tree oligomeric secoiridoid glucosides named craigosides A–C. The three compounds are esters of a cyclopentanoid monoterpene with an iridane skeleton, esterified with three, two and two, respectively, units of oleoside 11-methyl ester. The structures were elucidated by spectroscopic methods and chemical correlations.

Francesca Romana Gallo; Giovanna Palazzino; Elena Federici; Raffaella Iurilli; Franco Delle Monache; Kusamba Chifundera; Corrado Galeffi

2006-01-01

84

Oligomeric secoiridoid glucosides from Jasminum abyssinicum.  

PubMed

From the root bark of Jasminum abyssinicum (Oleaceae) collected in Congo was isolated tree oligomeric secoiridoid glucosides named craigosides A-C. The three compounds are esters of a cyclopentanoid monoterpene with an iridane skeleton, esterified with three, two and two, respectively, units of oleoside 11-methyl ester. The structures were elucidated by spectroscopic methods and chemical correlations. PMID:16376958

Gallo, Francesca Romana; Palazzino, Giovanna; Federici, Elena; Iurilli, Raffaella; Monache, Franco Delle; Chifundera, Kusamba; Galeffi, Corrado

2006-03-01

85

Cytogenetic activity of the coumarin glucoside seseloside  

SciTech Connect

The cytogenetic effect of the coumarin glucoside seseloside on plant objects was studied. It was established that low concentrations of the preparation (from 1 x 10/sup -5/ to 1 x 10/sup -3/ ..mu..g/ml) inhibit both spontaneous and radiation-induced mutagenesis. The effect of high concentrations (10 and 100 ..mu..g/ml) causes a mutagenic effect.

Arshava, E.A.

1986-05-01

86

Stability of Limonin Glucoside in Beverage Matrices  

Technology Transfer Automated Retrieval System (TEKTRAN)

Limonin glucoside, a highly oxygenated triterpenoid secondary metabolite found in significant quantities in Citrus and reported to possess multiple health-promoting properties, is being considered for incorporation into beverages as a functional component. In preparation of a multi-week human study...

87

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

88

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

89

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

90

New Lignans and Iridoid Glycosides from Dipsacus asper Wall.  

PubMed

Six new compounds, including four new lignans, dipsalignan A (1), B-D (3-5), and two new bis-iridoid glycoside dimmers, dipsanosides M (7) and N (8), together with two known compounds (2) and (6), have been isolated from the roots of Dipsacus asper Wall. Their structures were established on the basis of spectroscopic data (MS, 1D, 2D NMR, and CD) and chemical methods. All the isolated compounds were tested against human immunodeficiency virus-1 (HIV-1) integrase inhibition activities, and only compounds 1, 2, 7, and 8 displayed weak activities. PMID:25635380

Sun, Xinguang; Ma, Guoxu; Zhang, Dawei; Huang, Wenhua; Ding, Gang; Hu, Huagang; Tu, Guangzhong; Guo, Baolin

2015-01-01

91

Isolation and neuroprotective activities of acylated iridoids from Valeriana jatamansi.  

PubMed

Three new iridoids, jatairidoids A-C (1-3, resp.), have been isolated from the roots of Valeriana jatamansi (V. wallichii). Their structures were elucidated by spectroscopic methods (IR, ESI-MS, HR-ESI-MS, 1D- and 2D-NMR). Compounds 1 and 2 are C(3)-epimers. The three compounds were evaluated for their neuroprotective effects against MPP(+)-induced neuronal cell death in human dopaminergic neuroblastoma SH-SY5Y cells. All the isolates exhibited moderate neuroprotective effects. PMID:22782884

Xu, Jing; Guo, Yuanqiang; Xie, Chunfeng; Jin, Da-Qing; Gao, Jie; Gui, Liping

2012-07-01

92

Two New Phenolic Glucosides from Lagerstroemia speciosa.  

PubMed

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

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

2015-01-01

93

Cucurbitacin glucosides: Antioxidant and free-radical scavenging activities  

Microsoft Academic Search

The cucurbitacins are of great interest because of the wide range of biological activities they exhibit in plants and animals. We studied the antioxidant properties of cucurbitacin B + E glucosides (cucurbitacin glucoside combination, CGC) and their direct free-radical scavenging properties, using ESR spectroscopy. Antioxidant activity was measured by the ability of the CGC to reduce preformed ABTS•+ into its

Tehila Tannin-Spitz; Margalit Bergman; Shlomo Grossman

2007-01-01

94

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

Microsoft Academic Search

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

Ritsuo Nishida; Hiroshi Fukami

1989-01-01

95

Iridoid glycoside sequestration by Thessalia leanira (Lepidoptera: Nymphalidae) feeding on Castilleja integra (Scrophulariaceae)  

Microsoft Academic Search

A small population of a polyvoltine checkerspot butterfly,Thessalia leanira fulvia (also known asChlosyne leanira ssp.fulvia), was found to useCastilleja integra as a larval food plant at a localized site (Burnt Mill) southwest of Pueblo, Colorado. Field-captured adult butterflies contained the major iridoid glycosides (catalpol and macfadienoside) of theCastilleja. The content of a third iridoid glycoside, methyl shanzhiside, was also relatively

Elliott W. Mead; Tommaso A. Foderaro; Dale R. Gardner; Frank R. Stermitz

1993-01-01

96

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

PubMed

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

Deng, Shixin; West, Brett J; Jensen, C Jarakae

2013-01-01

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

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

PubMed

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

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

2014-02-01

99

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

PubMed Central

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

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

2013-01-01

100

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

101

Isobiflorin, a chromone C-glucoside from cloves ( Eugenia caryophyllata)  

Microsoft Academic Search

The polyoxygenated chromone C-glucoside, isobiflorin (5,7-dihydroxy-2-methylchromone-8-C-?-d-glucopyranoside), and biflorin were isolated from an ethanolic extract of cloves (Eugenia caryophyllata), and characterized by chemical and spectral analysis.

Yongwen Zhang; Yuwu Chen

1997-01-01

102

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

103

Acylated iridoids from the roots of Valeriana officinalis var. latifolia.  

PubMed

Phytochemical investigation of the roots of Valeriana officinalis var. latifolia resulted in the isolation and characterization of six new acylated iridoids, (5S,7S,8S,9S)-7-hydroxy-8-isovaleroyloxy-??,¹¹-dihyronepetalactone (1), (5S,7S,8S,9S)-7-hydroxy-10-isovaleroyloxy-??,¹¹-dihyronepetalactone (2), (5S,8S,9S)-10-isovaleroyloxy-??,¹¹-dihyronepetalactone (3), (5S,6S,8S,9R)-6-isovaleroyloxy-??,¹¹-1,3-diol (4), (5S,6S,8S,9R)-1,3-isovaleroxy-?4,11-1,3-diol (5), and (5S,6S,8S,9R)-3-isovaleroxy-6-isovaleroyloxy-??,¹¹-1,3-diol (6). Their structures were determined mainly by 1D and 2D?NMR spectroscopic techniques. We also report herein for the first time the single crystal X-ray structure of compound 1. In addition, the cytotoxic activities of compounds 1-6 were evaluated against A549 (human lung adenocarcinoma), HCT116 (human colon carcinoma), SK-BR-3 (human breast carcinoma), and HepG2 (human hepatoma) cell lines. Compound 6 showed weak cell growth inhibition of A549, HCT116, SK-BR-3, and HepG2 cells. PMID:22872588

Han, Zhu-zhen; Yan, Zhao-hui; Liu, Qing-xin; Hu, Xian-qing; Ye, Ji; Li, Hui-liang; Zhang, Wei-dong

2012-10-01

104

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

105

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

PubMed

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

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

2014-03-01

106

Isolation, structural elucidation, and neuroprotective effects of iridoids from Valeriana jatamansi.  

PubMed

Two new iridoids, jatadoids A (1) and B (2), and two known compounds (3 and 4) were isolated from Valeriana jatamansi. Their structures were elucidated on the basis of extensive spectroscopic analyses (IR, ESI-MS, HR-ESI-MS, 1D and 2D NMR). Compound 1 possessed an isovaleroxy group at the C-3 position that has previously been unreported in the class of iridoids. Four compounds were evaluated and compounds 1 and 3 showed moderate neuroprotective effects against MPP+-induced neuronal cell death in human dopaminergic neuroblastoma SH-SY5Y cells. PMID:22785467

Xu, Jing; Li, Yushan; Guo, Yuanqiang; Guo, Ping; Yamakuni, Tohru; Ohizumi, Yasushi

2012-01-01

107

Iridoid glycoside sequestration by two aposematicPenstemon-feeding geometrid larvae.  

PubMed

The iridoid glycoside catalpol was found to be sequestered by larvae ofMeris alticola feeding onPenstemon virgatus and by larvae ofNeoterpes graefiaria which utilizeP. barbatus. The strikingly similar larval patterns of these two ennomine geometrids were previously considered to be disruptive, but predator-based Mullerian mimicry is equally likely to be involved. The cryptic adult moths generally contain only small amounts of catalpol, having left most of the bitter iridoid in the pupal case and in the meconium excreted after eclosion. OneNeoterpes female did contain considerable catalpol in the abdomen, presumably in the eggs. PMID:24275990

Stermitz, F R; Gardner, D R; McFarland, N

1988-02-01

108

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

PubMed

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

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

2015-05-15

109

A divergent approach to the diastereoselective synthesis of several ant-associated iridoids.  

PubMed

The ant-associated iridoids nepetalactol, actinidine, dolichodial, isoiridomyrmecin, and dihydronepetalactone were prepared from citronellal using a divergent approach. Key features include a three-step synthesis of the individual antipodes of actinidine by a novel tandem cycloaddition/pyridine formation and a facile diastereoselective synthesis of both enantiomers of dolichodial. PMID:20222691

Beckett, Joel S; Beckett, James D; Hofferberth, John E

2010-04-01

110

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

111

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

PubMed

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

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

2014-06-01

112

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

Microsoft Academic Search

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

Alexander Fuchs; M. Deane Bowers

2004-01-01

113

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

PubMed Central

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

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

2015-01-01

114

Glochiflavanosides A-D: flavanol glucosides from the leaves of Glochidion zeylanicum (Gaertn) A. Juss.  

PubMed

From the leaves of Glochidion zeylanicum collected in Okinawa, four flavanol glucosides, named as glochiflavanosides A-D were isolated along with known flavone C-glucosides, vitexin and isoorientin. Their structures were elucidated by spectroscopic analyses. PMID:11456105

Otsuka, H; Hirata, I; Shinzato, T; Takeda, Y

2001-07-01

115

Importance of phenolic glucosides in host selection of shoot galling sawfly, Euura amerinae , on Salix pentandra  

Microsoft Academic Search

The effects of phenolic glucosides on the oviposition behavior ofEuura amerinae L. (Hymenoptera: Tenthredinidae) were tested in multiple oviposition experiments using different shoot length categories ofSalix pentandra L. (with different amounts of phenolic glucosides) and in experiments with pure phenolic glucosides (salidroside, arbutin, salicin, 90% salicortin, 90% 2?-O-acetylsalicortin) or composite total fractions of phenolic glucosides from three willow species (S.

Jari Kolehmainen; Heikki Roininen; Riitta Julkunen-Tiitto; Jorma Tahvanainen

1994-01-01

116

Naphthohydroquinone glucosides of Drosera rotundifolia and D. intermedia from in vitro cultures  

Microsoft Academic Search

Rossoliside (7-methylhydrojuglone 4-O-glucoside) was isolated from Drosera rotundifolia, together with hydroplumbagin 4-O-glucoside, from D. intermedia, both of which were produced by in vitro micropropagation. Hydroplumbagin glucoside released the corresponding 1,4-naphthoquinone (plumbagin) more rapidly than rossoliside (7-methyljuglone). These glucosides can be detected in plant extracts by reversed-phase TLC and appearance of the corresponding free quinones after treatment with ?-glucosidase.

Jaromir Budzianowski

1996-01-01

117

New seco-anthraquinone glucosides from Rumex nepalensis.  

PubMed

Investigation of the N-BuOH extract of the roots of Rumex nepalensis afforded two new seco-anthraquinone glucosides, nepalensides A and B, along with nine known compounds, torachrysone ( 3), rumexoside, orientaloside, orcinol glucoside, aloesin, lyoniresinol 3 alpha- O- beta- D-glucopyranoside, (-)-epicatechin-3- O-gallate, (3,5-dimethoxy-4-hydroxyphenol)-1- O- beta- D-(6- O-galloyl) glucose, and (-)-epicatechin. Their structures were elucidated on the basis of spectroscopic methods. The possible formation of nepalensides A and B is briefly discussed. PMID:19291613

Mei, Renqiang; Liang, Hengxing; Wang, Junfeng; Zeng, Linhong; Lu, Qing; Cheng, Yongxian

2009-08-01

118

Characterization of diterpenoid glucosides in roasted puer coffee beans.  

PubMed

Five new diterpenoid glucosides, named mascaroside I (1), mascaroside II (2), paniculoside VI (3), cofaryloside I (4), and villanovane I (5), along with seven known ent-kaurane diterpenoid glucosides (6-12) were isolated from acetone extracts of the roasted coffee beans of Coffea arabica var. yunnanensis. Their structures were established by extensive spectroscopic analysis including 1D and 2D NMR (HSQC, HMBC, COSY, and ROESY) and by comparison with published data. Cytotoxicities evaluation of the isolates showed that they were inactive against HL-60, SMMC-7721, A-549, MCF-7, and SW480 cells. PMID:24605833

Shu, Yi; Liu, Jie-Qing; Peng, Xing-Rong; Wan, Luo-Sheng; Zhou, Lin; Zhang, Tao; Qiu, Ming-Hua

2014-03-26

119

Biosynthesis of the Nitrile Glucosides Rhodiocyanoside A and D and the Cyanogenic Glucosides Lotaustralin and Linamarin in Lotus japonicus1  

PubMed Central

Lotus japonicus was shown to contain the two nitrile glucosides rhodiocyanoside A and rhodiocyanoside D as well as the cyanogenic glucosides linamarin and lotaustralin. The content of cyanogenic and nitrile glucosides in L. japonicus depends on plant developmental stage and tissue. The cyanide potential is highest in young seedlings and in apical leaves of mature plants. Roots and seeds are acyanogenic. Biosynthetic studies using radioisotopes demonstrated that lotaustralin, rhodiocyanoside A, and rhodiocyanoside D are derived from the amino acid l-Ile, whereas linamarin is derived from Val. In silico homology searches identified two cytochromes P450 designated CYP79D3 and CYP79D4 in L. japonicus. The two cytochromes P450 are 94% identical at the amino acid level and both catalyze the conversion of Val and Ile to the corresponding aldoximes in biosynthesis of cyanogenic glucosides and nitrile glucosides in L. japonicus. CYP79D3 and CYP79D4 are differentially expressed. CYP79D3 is exclusively expressed in aerial parts and CYP79D4 in roots. Recombinantly expressed CYP79D3 and CYP79D4 in yeast cells showed higher catalytic efficiency with l-Ile as substrate than with l-Val, in agreement with lotaustralin and rhodiocyanoside A and D being the major cyanogenic and nitrile glucosides in L. japonicus. Ectopic expression of CYP79D2 from cassava (Manihot esculenta Crantz.) in L. japonicus resulted in a 5- to 20-fold increase of linamarin content, whereas the relative amounts of lotaustralin and rhodiocyanoside A/D were unaltered. PMID:15122013

Forslund, Karin; Morant, Marc; Jørgensen, Bodil; Olsen, Carl Erik; Asamizu, Erika; Sato, Shusei; Tabata, Satoshi; Bak, Søren

2004-01-01

120

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

121

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

Microsoft Academic Search

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

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

2003-01-01

122

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

123

Elaeagnoside, chymotrypsin inhibiting steroidal glucoside from Elaeagnus orientalis  

Microsoft Academic Search

Elaeagnoside (1), a new steroidal glucoside, has been isolated from the chloroform fraction of Elaeagnus orientalis along with ?-sitosterol and 12-hydroxy-8,10-octadecadienoic acid. The structure of 1 has been elucidated with the help of chemical and spectral studies. It showed significant inhibitory activity against the enzyme chymotrypsin.

Muhammad Ayaz; Muhammad Riaz; Abdul Malik; Ejaz Ahmad; Itrat Fatima; Muhammad Arif Lodhi; Muhammad Iqbal Chaudhary

2009-01-01

124

Kinetics of active alpha-glucoside transport in Saccharomyces cerevisiae.  

PubMed

alpha-Glucosides are the most abundant fermentable sugars in the industrial applications of Saccharomyces cerevisiae, and the active transport across the plasma membrane is the rate-limiting step for their metabolism. In this report we performed a detailed kinetic analysis of the active alpha-glucoside transport system(s) present in a wild-type strain, and in strains with defined alpha-glucoside permeases. Our results indicate that the wild-type strain harbors active transporters with high and low affinity for maltose and trehalose, and low-affinity transport systems for maltotriose and alpha-methylglucoside. The maltose permease encoded by the MAL21 gene showed a high affinity (K(m) approximately 5 mM) for maltose, and a low affinity (K(m) approximately 90 mM) for trehalose. On the other hand, the alpha-glucoside permease encoded by the AGT1 gene had a high affinity (K(m) approximately 7 mM) for trehalose, a low affinity (K(m) approximately 18 mM) for maltose and maltotriose, and a very low affinity (K(m) approximately 35 mM) for alpha-methylglucoside. PMID:12702465

Stambuk, B U; de Araujo, P S

2001-04-01

125

Ring B aromatic norpimarane glucoside from a Xylaria sp.  

PubMed

A novel 20-norpimarane glucoside, xylopimarane (1), together with the known sphaeropsidin C (2) and clonostachydiol (3), was isolated from the fungus Xylaria sp. BCC 4297. Compound 1 exhibited cytotoxicity to cancer cell lines KB, MCF-7, and NCI-H187 with respective IC(50) values of 1.0, 13, and 65 ?M. PMID:21226484

Isaka, Masahiko; Yangchum, Arunrat; Auncharoen, Patchanee; Srichomthong, Kitlada; Srikitikulchai, Prasert

2011-02-25

126

Antioxidant constituents from rhubarb: structural requirements of stilbenes for the activity and structures of two new anthraquinone glucosides  

Microsoft Academic Search

The methanolic extracts from five kinds of rhubarb were found to show scavenging activity for DPPH radical and O2?. Two new anthraquinone glucosides were isolated from the rhizome of Rheum undulatum L. together with two anthraquinone glucosides, a naphthalene glucoside, and 10 stilbenes. In the screening test for radical scavenging activity of rhubarb constituents, stilbenes and a naphthalene glucoside showed

Hisashi Matsuda; Toshio Morikawa; Iwao Toguchida; Ji-Young Park; Shoichi Harima; Masayuki Yoshikawa

2001-01-01

127

Pyridine monoterpene alkaloid formation from iridoid glycosides. A novel PMTA dimer from geniposide.  

PubMed

New pyridine monoterpene alkaloids (PMTAs) have been synthesized from the iridoid glycosides 8-epi-loganin, cornin, and antirrinoside by treatment with beta-glucosidase and aqueous NH4-OAc. The PMTA from antirrinoside contained an 8-alpha-OAc group from the opened 7,8-epoxide moiety. Treatment of genipin, the aglycone of geniposide, with HCl(g) and NH3(g) yielded the PMTA racemigerine, a known plant isolate, in which the C=C-CH2OH side chain was converted to C=C-CH3. Reaction of geniposide with beta-glucosidase and aqueous NH4OAc led to oligomeric alkaloids, but at high dilution a dimer was obtained whose structure was formally that of a Diels-Alder adduct between racemigerine and a dihydropyridine. These biomimetic semisyntheses were analyzed in terms of reaction mechanisms and the relative paucity of known plant PMTAs in comparison with the multitudinous occurrence of their presumed iridoid glycoside precursors. PMID:8984152

Frederiksen, S M; Stermitz, F R

1996-01-01

128

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

129

Iridoids from the roots of Valeriana jatamansi and their biological activities.  

PubMed

A new iridoid, jatamandoid A (1), and four known analogues (2-5) were isolated from the roots of Valeriana jatamansi. Their structures were elucidated on the basis of extensive spectroscopic analysis (IR, ESI-MS, HR-ESI-MS, 1-D and 2-D NMR). Five compounds were evaluated and compounds 1, 2 and 5 showed moderate neuroprotective effects against MPP(+)-induced neuronal SH-SY5Y cell death. PMID:22115452

Xu, Jing; Guo, Ping; Guo, Yuanqiang; Fang, Lingzhi; Li, Yushan; Sun, Zhanping; Gui, Liping

2012-11-01

130

Iridoids from the roots of Valeriana jatamansi and their neuroprotective effects.  

PubMed

Three new iridoids, valeriandoids A-C (1-3), together with three known analogues (4-6), were isolated from the roots of Valeriana jatamansi. Their structures and relative configurations were elucidated by spectroscopic methods (IR, ESIMS, HRESIMS, 1D and 2D NMR) and by comparison of their NMR data with those of related compounds. All the isolated compounds were evaluated for their neuroprotective effects and compounds 1, 3, 4 and 6 showed moderate neuroprotective effects. PMID:21807076

Xu, Jing; Zhao, Peng; Guo, Yuanqiang; Xie, Chunfeng; Jin, Da-Qing; Ma, Yonggang; Hou, Wenbin; Zhang, Tiejun

2011-10-01

131

Iridoid glycoside sequestration byThessalia leanira (Lepidoptera: Nymphalidae) feeding onCastilleja integra (Scrophulariaceae).  

PubMed

A small population of a polyvoltine checkerspot butterfly,Thessalia leanira fulvia (also known asChlosyne leanira ssp.fulvia), was found to useCastilleja integra as a larval food plant at a localized site (Burnt Mill) southwest of Pueblo, Colorado. Field-captured adult butterflies contained the major iridoid glycosides (catalpol and macfadienoside) of theCastilleja. The content of a third iridoid glycoside, methyl shanzhiside, was also relatively high in the collected butterflies even though most individualCastilleja plants at Burnt Mill contained little or no methyl shanzhiside. Only a few plants, restricted to a small area, did contain appreciable methyl shanzhiside. Most of the plants that lacked the ester methyl shanzhiside contained shanzhiside, the corresponding free carboxylic acid.Thessalia larvae did not normally methylate the acid to produce methyl shanzhiside. Larvae that stopped feeding at an early instar, but yet survived several weeks, did contain major amounts of methyl shanzhiside. It is suggested that only larvae that overwinter or otherwise enter diapause convert shanzhiside to methyl shanzhiside. TheCastilleja food plant also contained iridoids other than catalpol and macfadienoside, sometimes in major amounts, but these were never found in larvae, pupae, or butterflies. PMID:24249134

Mead, E W; Foderaro, T A; Gardner, D R; Stermitz, F R

1993-06-01

132

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

133

Stereochemistry of megastigmane glucosides from Glochidion zeylanicum and Alangium premnifolium.  

PubMed

From Glochidion zeylanicum, two megastigmane glucosides, 3- and 9-O-beta-D-glucopyranosides of (3S,5R,6R,7E,9S)-megastigman-7-ene-3,5,6,9-tetrol (1 and 2, respectively), were isolated. Their structures were different from those of kiwiionoside (3) and actinidioionoside (4), isolated from Actinidia chinensis and Actinidia polygama, respectively, in the stereochemistry at the 9-positions. Alangionosides E (5) and O (6), isolated from the leaves of Alangium premnifolium, are also megastigmane glucosides, and the latter is closely related to 1 and actinidioionoside (4). However, the absolute configurations of the 9-position remained to be determined. They were analyzed to be R by means of a modified Mosher's method. Alangionoside E (5) is identical with corchoionoside A in all aspects. The name of corchoionoside A must be retained thereafter. PMID:12620329

Otsuka, Hideaki; Hirata, Eiji; Shinzato, Takakazu; Takeda, Yoshio

2003-03-01

134

Anthocyanins with 4?-glucosidation from red onion, Allium cepa  

Microsoft Academic Search

The anthocyanins, cyanidin 3-O-(3?-O-?-glucopyranosyl-6?-O-malonyl-?-glucopyranoside)-4?-O-?-glucopyranoside, cyanidin 7-O-(3?-O-?-glucopyranosyl-6?-O-malonyl-?-glucopyranoside)-4?-O-?-glucopyranoside, cyanidin 3,4?-di-O-?-glucopyranoside, cyanidin 4?-O-?-glucoside, peonidin 3-O-(6?-O-malonyl-?-glucopyranoside)-5-O-?-glucopyranoside and peonidin 3-O-(6?-O-malonyl-?-glucopyranoside) have been isolated in minor amounts from pigmented scales of red onion, Allium cepa, in addition to six known anthocyanins. The structures were established mainly by extensive use of 2D NMR spectroscopy and electrospray LC–MS. With exception of cyanidin 4?-glucoside and cyanidin 3,4?-diglucoside reported from

Torgils Fossen; Rune Slimestad; Øyvind M Andersen

2003-01-01

135

Synthesis and characterization of hydroquinone glucoside using Leuconostoc mesenteroides dextransucrase  

Microsoft Academic Search

We synthesized a hydroquinone glucoside (HG) as a potential skin-whitening agent using Leuconostoc mesenteroides (B-1299CB BF563) dextransucrase with hydroquinone (HQ) as an acceptor and sucrose as a donor. The product was purified using butanol partitioning and silica gel column chromatography. The structure of the purified HG was determined by nuclear magnetic resonance and the ionic product was observed at m\\/z

Eun-Seong Seo; Jin Kang; Jin-Ha Lee; Go-Eun Kim; Ghahyun J. Kim; Doman Kim

2009-01-01

136

Iridoid glycoside content ofEuphydryas anicia (Lepidoptera: Nymphalidae) and its major hostplant,Besseya plantaginea (Scrophulariaceae), at a high plains colorado site.  

PubMed

The checkerspot butterfly,Euphydryas anicia, utilizes mainlyBesseya plantaginea and only occasionallyCastilleja integra as a larval hostplant at Michigan Hill, a few kilometers from a site whereC. integra is used by over 90% of the butterflies. TheB. plantaginea leaves that are consumed contain 9-22% iridoid glycosides, composed mainly of catalpol and catalpol esters, while larvae from the same plants contain 6-18% iridoids, mainly catalpol and no esters. Field-collected adult butterflies contain 0.5-4.3% iridoids. Laboratory-reared adults secrete iridoids in the meconium upon eclosion and retain similar amounts. The adult and meconium iridoid content is considerably lower than in the larvae, and metabolism in the pupal stage may be occurring. PMID:24264906

L'empereur, K M; Stermitz, F R

1990-01-01

137

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

PubMed

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

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

2015-01-01

138

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

139

Phytotoxic cis-cinnamoyl glucosides from Spiraea thunbergii.  

PubMed

Spiraea thunbergii Sieb. was found to contain 1-O-cis-cinnamoyl-beta-D-glucopyranose and 6-O-(4'-hydroxy-2'-methylene-butyroyl)-1-O-cis-cinnamoyl-beta-D-glucopyranose as major plant growth inhibitory constituents along with related compounds of lower phytotoxicity including 6-O-(trans-cinnamoyl)-1-O-(4"-hydroxy-3"-methyl-furan-2"-one)-beta-D-glucopyranose, 6-O-(4'-hydroxy-2'-methylene-butyroyl)-1-O-trans-cinnamoyl-beta-D-glucopyranose, and 1-O-trans-cinnamoyl-beta-D-glucopyranose. The former three compounds were cinnamoyl glucosides. PMID:15016569

Hiradate, Syuntaro; Morita, Sayaka; Sugie, Hajime; Fujii, Yoshiharu; Harada, Jiro

2004-03-01

140

?-Hydroxynitrile glucosides from the seeds of Prinsepia utilis.  

PubMed

?-Hydroxynitrile glucosides (prinsepicyanosides A-E) were isolated alongside 11 known compounds from seeds of Prinsepia utilis Royle. Their structures were determined by detailed analysis of NMR and MS spectroscopic data. The relative configuration of prinsepicyanoside C was established by Cu-K? X-ray crystallography. Prinsepicyanoside A, osmaronin, and 4-(hydroxylmethyl)-5H-furan-2-one exhibited borderline antibacterial activity against Salmonella gallinarum, Vibrio parahaemolyticus, and Vibrio cholera with MIC values of 30.1, 20.7, and 22.8?g/mL, respectively. PMID:24952469

Guan, Bin; Li, Tao; Xu, Xi-Ke; Zhang, Xu-Feng; Wei, Pan-Lei; Peng, Cheng-Cheng; Fu, Jian-Jun; Zeng, Qi; Cheng, Xiang-Rong; Zhang, Shou-De; Yan, Shi-Kai; Jin, Hui-Zi; Zhang, Wei-Dong

2014-09-01

141

Teucrium polium phenylethanol and iridoid glycoside characterization and flavonoid inhibition of biofilm-forming Staphylococcus aureus.  

PubMed

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

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

2015-01-23

142

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

PubMed

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

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

2014-07-01

143

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

PubMed

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

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

2015-01-21

144

Octyl glucoside induced formation of the molten globule-like state of glutamate dehydrogenase.  

PubMed

The interaction between n-octyl-beta-D-glucopyranoside (octyl glucoside) and bovine liver glutamate dehydrogenase (GDH) was studied using techniques including equilibrium dialysis, UV-spectrophotometry, circular dichroism (CD), fluorescence energy transfer and extrinsic spectrofluorometry in 50 mM sodium phosphate buffer solution (pH 7.6). The equilibrium dialysis experiment showed a higher binding of octyl glucoside to GDH that induces up to 80% enzyme inhibition in 20 mM octyl glucoside solution. The CD study indicated that GDH retains its secondary structure in the presence of octyl glucoside, but loses a degree of its tertiary structure by acquiring a more extended tertiary structure. Measurement of the binding of a hydrophobic fluorescent probe, 1-anilino-naphthalene-8-sulfonate (ANS), to GDH revealed that the binding of ANS to GDH is increased in the presence of octyl glucoside, a finding that may be interpreted in terms of the increment of surface hydrophobic patch(es) of GDH because of its binding to octyl glucoside. Fluorescence energy transfer studies also showed more binding of the reduced coenzyme (NADH) to GDH and the Lineweaver-Burk plots (with respect to NADH) indicate the existence of substrate inhibition in the presence of octyl glucoside. These observations are aimed at explaining the formation of the molten globule-like structure of GDH, which is induced by a non-ionic detergent such as octyl glucoside. PMID:11686930

Ghobadi, S; Safarian, S; Moosavi-Movahedi, A A; Ranjbar, B

2001-11-01

145

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

146

The synthesis of analogs of shuangkangsu, a novel natural cycloperoxide glucoside from Lonicera japonica Thunb.  

PubMed

Four novel optically pure cycloperoxide glucosides 9a, 9b, 10a, and 10b, analogs of shuangkangsu--a natural product with unusual skeleton and antivirus activity from the buds of Lonicera japonica Thunb, were firstly synthesized by employing peroxidation and glucosidation reactions from phthalaldehyde or 4,5-dichloro phthalaldehyde and glucose. PMID:19219731

Tang, Yan-Bo; Huang, Long-Jiang; Li, Di-Zao; Zhang, Qing-Jian; Chen, Ruo-Yun; Yu, De-Quan

2009-01-01

147

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

148

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

PubMed

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

Behbahani, Mandana

2014-11-01

149

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

PubMed

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

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

2015-01-01

150

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

PubMed

Catharanthus roseus, the Madagascar periwinkle, synthesizes bioactive monoterpenoid indole alkaloids, among which the anti-cancer drugs vinblastine and vincristine. The monoterpenoid branch of the alkaloid pathway leads to the secoiridoid secologanin and involves the enzyme iridoid synthase (IS), a member of the progesterone 5?-reductase (P5?R) family. IS reduces 8-oxogeranial to iridodial. Through transcriptome mining, we show that IS belongs to a family of six C. roseus P5?R genes. Characterisation of recombinant CrP5?R proteins demonstrates that all but CrP5?R3 can reduce progesterone, and thus can be classified as P5?Rs. Three of them, namely CrP5?R1, CrP5?R2 and CrP5?R4, could also reduce 8-oxogeranial, pointing to a possible redundancy with IS (corresponding to CrP5?R5) in secoiridoid synthesis. In depth functional analysis by subcellular protein localisation, gene expression analysis, in situ hybridisation and virus-induced gene silencing, indicates that besides IS, CrP5?R4 may also participate in secoiridoid biosynthesis. Finally, we cloned a set of P5?R genes from angiosperm plant species not known to produce iridoids and demonstrate that the corresponding recombinant proteins are also capable of using 8-oxogeranial as a substrate. This suggests that 'IS activity' is intrinsic to angiosperm P5?R proteins and has evolved early during evolution. PMID:25239067

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

2014-09-19

151

Effect of the temperature and the exclusion of UVB radiation on the phenolics and iridoids in Menyanthes trifoliata L. leaves in the subarctic.  

PubMed

The long-term effects of UVB exclusion and temperature on the methanol extractable (ME) phenolics (flavonoids, phenolic acids) and iridoids of Menyanthes trifoliata L. (Mt) leaves were studied in northern Finland (68 degrees N) using wooden frames covered with filters for UVB exclusion (polyester filter), control (cellulose acetate filter) and ambient (no filter) conditions. Analysis of ambient plots showed no effect of the daily mean temperature (2sigma = 1.58 degrees C) on the leaf ME compound content and composition, but minimum temperatures decreased the flavonol content. UVB exclusion did not affect the total ME compound content but significantly decreased the proportion of flavonols concomitantly with an increase in iridoids. Due to its high iridoid content, Mt appears as an interesting model plant for studying the iridoid biosynthesis and its regulation under stress conditions. PMID:19615800

Martz, Françoise; Turunen, Minna; Julkunen-Tiitto, Riitta; Lakkala, Kaisa; Sutinen, Marja-Liisa

2009-12-01

152

Analysis of interaction property of calycosin-7-O-?-D-glucoside with human gut microbiota.  

PubMed

Calycosin-7-O-?-d-glucoside as the major isoflavonoids in Astragali Radix has been investigated intensively and has been reported to possess a wide range of pharmacological properties. However, the route and metabolites of calycosin-7-O-?-d-glucoside by human intestinal bacteria are not well understood and its metabolites may accumulate to exert physiological effects. Therefore, the objective of this study was to screen the ability of the bacteria to metabolize calycosin-7-O-?-d-glucoside and assess the effect of this compound on the intestinal bacteria. Finally, five strains including Bacteroides sp.13, and sp.58, Clostridium sp.21-2, Veillonella sp.43-1, and Bacillus sp.46 were isolated from human intestinal bacteria and were studied their abilities to convert calycosin-7-O-?-d-glucoside. A total of six metabolites were identified in human incubated solution by ultra performance liquid chromatography/quadrupole time-of-flight mass spectrometry (UPLC-Q-TOF-MS). The results indicated that hydrolysis, demethylation, dehydroxylation and acetylation were the major metabolism of calycosin-7-O-?-d-glucoside. On the other hand, different strains of intestinal bacteria have varying degrees of growth sensitivity to calycosin-7-O-?-d-glucoside. Growth of certain pathogenic bacteria such as Enterobacter, Enterococcus, Clostridium and Bacteroides was significantly repressed by calycosin-7-O-?-d-glucoside, while commensal probiotics such as Lactobacillus, Bifidobacterium were less severely affected. This indicates that calycosin-7-O-?-d-glucoside exert significant effects on the intestinal environment by modulation of the intestinal bacterial population. Our observation provided further evidence for the importance of intestinal bacteria in the metabolism, absorption and potential activity of calycosin-7-O-?-d-glucoside in human health and diseases. PMID:24922599

Zhang, Wei; Jiang, Shu; Qian, Dawei; Shang, Er-Xin; Duan, Jin-Ao

2014-07-15

153

Iridoid glycoside content of Euphydryas anicia (Lepidoptera: Nymphalidae) and its major hostplant, Besseya plantaginea (Scrophulariaceae), at a high plains colorado site  

Microsoft Academic Search

The checkerspot butterfly,Euphydryas anicia, utilizes mainlyBesseya plantaginea and only occasionallyCastilleja integra as a larval hostplant at Michigan Hill, a few kilometers from a site whereC. integra is used by over 90% of the butterflies. TheB. plantaginea leaves that are consumed contain 9–22% iridoid glycosides, composed mainly of catalpol and catalpol esters, while larvae from the same plants contain 6–18% iridoids,

Karen M. L'Empereur; Frank R. Stermitz

1990-01-01

154

Urinary Excretion of Cyanidin Glucosides and Glucuronides in Healthy Humans After Elderberry Juice Ingestion.  

PubMed

In a pilot study with 6 females and 1 male, the metabolism of various cyanidin glucosides after oral administration of elderberry juice was investigated. The anthocyanin metabolites were detected in urinary excretion. After ingestion of a bolus quantity of $3.57$ g total anthocyanins in a $150$ mL elderberry juice concentrate, $0.053$ % of the administered dose was excreted in urine as glucosidically bound cyanidins within the first 5 hours. Only $0.003$ % of the ingested anthocyanin glucosides was excreted as cyanidin glucuronide, suggesting that this conversion step might be of minor importance in urinary excretion. PMID:15577200

Bitsch, Roland; Netzel, Michael; Sonntag, Susanne; Strass, Gabriele; Frank, Thomas; Bitsch, Irmgard

2004-01-01

155

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

PubMed

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

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

2009-01-01

156

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

PubMed

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

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

2015-02-15

157

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

158

Analysis of Secoiridoid Glucosides in Jasminum lanceolarium Roxb. by HPLC-MS  

Microsoft Academic Search

AimTo develop high performance liquid chromatography-electrospray ionization-mass spectrometry (HPLC-ESI-MS) for the analysis and identification of secoiridoid glucosides in Jasminum lanceolarium Roxb.

Jia-Ming SUN; Hui ZHANG; Jun-Shan YANG

2009-01-01

159

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

160

Thesinine-4?- O-?- d-glucoside the first glycosylated plant pyrrolizidine alkaloid from Borago officinalis  

Microsoft Academic Search

The glycosylated pyrrolizidine alkaloid, thesinine-4?-O-?-d-glucoside, has been isolated from the aqueous methanolic extract of dried seeds of Borago officinalis (Boraginaceae). The structure was established by means of spectroscopic and chemical analyses.

Martina Herrmann; Holger Joppe; Gerhard Schmaus

2002-01-01

161

Scale-up of pseudo solid-phase enzymatic synthesis of alpha-methyl glucoside acrylate.  

PubMed

The successful scale-up of the enzymatic synthesis of alpha-methyl glucoside acrylate from laboratory-scale (milliliter) to pilot-scale (liter) was examined. Specifically, Candida antarctica lipase B (Novozym 435) was used as a biocatalyst to produce alpha-methyl glucoside acrylate via the transesterification of alpha-methyl glucoside (MG) with vinyl acrylate (VA) using acetone as a solvent. This is a pseudo-solid-phase synthesis; only a fraction of the alpha-methyl glucoside and the product are soluble in acetone. Molecular sieves were used to remove traces of water in the reaction medium and to increase enzyme stability by removing the acetaldehyde by-product. A general method was also developed to purify and recover the monoacrylate product from unreacted sugar and undesired diester by a simple crystallization and precipitation process. PMID:17590927

Li, Yanzi; Rethwisch, David G

2002-07-01

162

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

PubMed

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

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

2015-05-15

163

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

Microsoft Academic Search

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

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

2001-01-01

164

Accumulation of peonidin 3-glucoside enhanced by osmotic stress in grape (Vitis vinifera L.) cell suspension  

Microsoft Academic Search

Cell cultures of grapes, Vitis vinifera L. cv Gamay Fréaux were grown under different conditions of external osmotic potential induced by an increase of sucrose concentration or by the addition of mannitol to the culture medium. Addition of 82 mM mannitol or increasing sucrose concentration to 132 mM had similar effects on repressing growth. Cyanidin 3-glucoside, peonidin 3-glucoside and peonidin

Chi Bao Do; François Cormier

1991-01-01

165

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

166

New Facile Syntheses of Monolignols Glucosides; p- Glucocoumaryl Alcohol, Coniferin and Syringin  

Microsoft Academic Search

The monolignols glucosides p-glucocoumaryl alcohol, coniferin and syringin, have been found in cambial sap of gymnospermous trees (Freudenberg and Harkin 1963) and some species of angiospermous trees (Terazawa et al. 1984). Coniferin has been shown to bean effective precursor of lignin biosynthesis in pine (Freudenberg et al. 1955). When three kinds of monolignols glucosides labeled with,C or,H were administered to

Noritsugu Terashima; Sally A. Ralph; Lawrence L. Landucci

1996-01-01

167

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

168

Iridoid glycoside metabolism and sequestration byPoladryas minuta (Lepidoptera: Nymphalidae) feeding onPenstemon virgatus (Scrophulariaceae).  

PubMed

A bivoltine checkerspot butterfly,Poladryas minuta, is aPenstemon specialist, not known to utilize any other plant genus for oviposition and larval feeding. At several intermontane plains sites of central Colorado, the butterfly utilizesPenstemon virgatus as its sole host plant. Analysis of the host plant showed it to contain three cinnamyl-type catalpol esters (scutellarioside-II, globularin, globularicisin) and catalpol. The host plant contained an average of 10% dry weight iridoids, but some variation among individual plants and leaves within plants was noted. Field-collected butterflies contained 2.1-8.7% dry weight catalpol, but no other iridoids. Adults from larvae fedP. virgatus in the lab contained 4.2-9.0% dry weight catalpol and excreted large amounts of catalpol in the meconium. No catalpol was found in the larval frass. Larvae did not consume three alternate iridoid-containing host-plant species, and most eventually died rather than feed on the alternate plants. Larvae did consume small amounts of artificial diets containing the alternate species andP. virgatus, but most went into diapause and some died. Survival was good on artificial diet containing 10% dry weight of the iridoid esters fromP. virgatus. Only catalpol was found in pupae and adults, but it was absent from the larval frass. The cinnamic-type acids expected from larval hydrolysis of the esters were not found in larval frass, pupae, or adults. These results are contrasted with those found for another checkerspot,Euphydryas anicia, which consumes a different host-plant species but was present at one of the same sites withPoladryas minuta. PMID:24263821

L'empereur, K M; Stermitz, F R

1990-05-01

169

Processing of iridoid glycoside antirrinoside from Maurandya antirrhiniflora (Scrophulariaceae) by Meris paradoxa (Geometridae) and Lepipolys species (Noctuidae)  

Microsoft Academic Search

The iridoid glycoside antirrinoside was found to be sequestered by highly aposematic larvae of the geometrid mothMeris paradoxa and two noctuid mothLepipolys species feeding onMaurandya antirrhiniflora (Scrophulariaceae), a natural food plant from southern Arizona. The antirrinoside content of leaves and petioles being consumed, eariy-instar larvae, late-instar larvae, larval frass, regurgitant, reflex-bleeding emission (Meris paradoxa), cocoons, pupae, meconium emitted upon eclosion,

Christie A. Boros; Frank R. Stermitz; Noel McFarland

1991-01-01

170

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

PubMed

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

Suzuki, Tadahiro; Iwahashi, Yumiko

2015-01-01

171

Hydrolytic fate of deoxynivalenol-3-glucoside during digestion.  

PubMed

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

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

2011-10-30

172

Low Toxicity of Deoxynivalenol-3-Glucoside in Microbial Cells  

PubMed Central

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

Suzuki, Tadahiro; Iwahashi, Yumiko

2015-01-01

173

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

PubMed Central

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

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

2008-01-01

174

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

PubMed

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

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

2004-11-17

175

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

PubMed

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 acid esters of flavonoid glucosides, can be applied to the acylation of other glucosides, including naringin, rutin, callistephin, and chrysanthemin. PMID:16232434

Nakajima, N; Ishihara, K; Itoh, T; Furuya, T; Hamada, H

1999-01-01

176

In vitro effects of cholesterol ?-D-glucoside, cholesterol and cycad phytosterol glucosides on respiration and reactive oxygen species generation in brain mitochondria.  

PubMed

The cluster of neurodegenerative disorders in the western Pacific termed amyotrophic lateral sclerosis-parkinsonism dementia complex (ALS-PDC) has been repeatedly linked to the use of seeds of various species of cycad. Identification and chemical synthesis of the most toxic compounds in the washed cycad seeds, a variant phytosteryl glucosides, and even more toxic cholesterol ?-D-glucoside (CG), which is produced by the human parasite Helicobacter pylori, provide a possibility to study in vitro the mechanisms of toxicity of these compounds. We studied in detail the effects of CG on the respiratory activities and generation of reactive oxygen species (ROS) by nonsynaptic brain and heart mitochondria oxidizing various substrates. The stimulatory effects of CG on respiration and ROS generation showed strong substrate dependence, suggesting involvement of succinate dehydrogenase (complex II). Maximal effects on ROS production were observed with 1 ?mol CG/1 mg mitochondria. At this concentration the cycad toxins ?-sitosterol-?-D-glucoside and stigmasterol-?-D-glucoside had effects on respiration and ROS production similar to CG. However, poor solubility precluded full concentration analysis of these toxins. Cholesterol, stigmasterol and ?-sitosterol had no effect on mitochondrial functions studied at concentrations up to 100 ?mol/mg protein. Our results suggest that CG may influence mitochondrial functions through changes in the packing of the bulk membrane lipids, as was shown earlier by Deliconstantinos et al. (Biochem Cell Biol 67:16-24, 1989). The neurotoxic effects of phytosteryl glucosides and CG may be associated with increased oxidative damage of neurons. Unlike heart mitochondria, in activated neurons mitochondria specifically increase ROS production associated with succinate oxidation (Panov et al., J Biol Chem 284:14448-14456, 2009). PMID:20938651

Panov, Alexander; Kubalik, Nataliya; Brooks, Benjamin R; Shaw, Christopher A

2010-10-01

177

The synthesis and antitumor activity of twelve galloyl glucosides.  

PubMed

Twelve galloyl glucosides 1-12, showing diverse substitution patterns with two or three galloyl groups, were synthesized using commercially available, low-cost D-glucose and gallic acid as starting materials. Among them, three compounds, methyl 3,6-di-O-galloyl-?-D-glucopyranoside (9), ethyl 2,3-di-O-galloyl-?-D-glucopyranoside (11) and ethyl 2,3-di-O-galloyl-?-D-glucopyranoside (12), are new compounds and other six, 1,6-di-O-galloyl-?-D-glucopyranose (1), 1,4,6-tri-O-galloyl-?-D-glucopyranose (2), 1,2-di-O-galloyl-?-D-glucopyranose (3), 1,3-di-O-galloyl-?-D-glucopyranose (4), 1,2,3-tri-O-galloyl-?-D-glucopyranose (6) and methyl 3,4,6-tri-O-galloyl-?-D-glucopyranoside (10), were synthesized for the first time in the present study. In in vitro MTT assay, 1-12 inhibited human cancer K562, HL-60 and HeLa cells with inhibition rates ranging from 64.2% to 92.9% at 100 ?g/mL, and their IC50 values were determined to be varied in 17.2-124.7 ?M on the tested three human cancer cell lines. In addition, compounds 1-12 inhibited murine sarcoma S180 cells with inhibition rates ranging from 38.7% to 52.8% at 100 ?g/mL in the in vitro MTT assay, and in vivo antitumor activity of 1 and 2 was also detected in murine sarcoma S180 tumor-bearing Kunming mice using taxol as positive control. PMID:25633333

Li, Chang-Wei; Dong, Hua-Jin; Cui, Cheng-Bin

2015-01-01

178

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

PubMed

Deoxynivalenol-3-?-D-glucoside (D3G), a plant metabolite of the Fusarium mycotoxin deoxynivalenol (DON), might be hydrolyzed in the digestive tract of mammals, thus contributing to the total dietary DON exposure of individuals. Yet, D3G has not been considered in regulatory limits set for DON for foodstuffs due to the lack of in vivo data. The aim of our study was to evaluate whether D3G is reactivated in vivo by investigation of its metabolism in rats. Six Sprague-Dawley rats received water, DON (2.0 mg/kg body weight (b.w.)) and the equimolar amount of D3G (3.1 mg/kg b.w.) by gavage on day 1, 8 and 15, respectively. Urine and feces were collected for 48 h and analyzed for D3G, DON, deoxynivalenol-glucuronide (DON-GlcA) and de-epoxy deoxynivalenol (DOM-1) by a validated LC-tandem mass spectrometry (MS/MS) based biomarker method. After administration of D3G, only 3.7±0.7% of the given dose were found in urine in the form of analyzed analytes, compared to 14.9±5.0% after administration of DON, and only 0.3±0.1% were detected in the form of urinary D3G. The majority of administered D3G was recovered as DON and DOM-1 in feces. These results suggest that D3G is little bioavailable, hydrolyzed to DON during digestion, and partially converted to DOM-1 and DON-GlcA prior to excretion. Our data indicate that D3G is of considerably lower toxicological relevance than DON, at least in rats. PMID:22884771

Nagl, Veronika; Schwartz, Heidi; Krska, Rudolf; Moll, Wulf-Dieter; Knasmüller, Siegfried; Ritzmann, Mathias; Adam, Gerhard; Berthiller, Franz

2012-09-18

179

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

PubMed Central

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

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

1972-01-01

180

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. PMID:24782425

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

2014-12-01

181

Identification of an N-Glucoside of cis-Zeatin from Potato Tuber Sprouts.  

PubMed

A compound was isolated from potato (Solanum tuberosum L. cv Bintje) tuber sprouts by immunoaffinity chromatography with antibodies against the cytokinins zeatin riboside and isopentenyladenosine. Analysis by ultraviolet spectroscopy and gas chromatography-mass spectrometry of derivatives identified the compound as a 9-glucoside of 6-[(Z)-4-hydroxy-3-methyl-2-butenylamino]purine (cis-zeatin). N-glucosides have often been reported as metabolites of other cytokinins, but to our knowledge, they have never before been found for cis-zeatin. The finding gives proof that cis-zeatin, a modified base in tRNA, also exists as a free substance in plants, since the glucoside, unlike other tRNA-free cis-zeatins described earlier by others, cannot arise by enzymatic degradation of tRNA during plant extraction. PMID:12228609

Nicander, B.; Bjorkman, P. O.; Tillberg, E.

1995-10-01

182

Identification of an N-Glucoside of cis-Zeatin from Potato Tuber Sprouts.  

PubMed Central

A compound was isolated from potato (Solanum tuberosum L. cv Bintje) tuber sprouts by immunoaffinity chromatography with antibodies against the cytokinins zeatin riboside and isopentenyladenosine. Analysis by ultraviolet spectroscopy and gas chromatography-mass spectrometry of derivatives identified the compound as a 9-glucoside of 6-[(Z)-4-hydroxy-3-methyl-2-butenylamino]purine (cis-zeatin). N-glucosides have often been reported as metabolites of other cytokinins, but to our knowledge, they have never before been found for cis-zeatin. The finding gives proof that cis-zeatin, a modified base in tRNA, also exists as a free substance in plants, since the glucoside, unlike other tRNA-free cis-zeatins described earlier by others, cannot arise by enzymatic degradation of tRNA during plant extraction. PMID:12228609

Nicander, B.; Bjorkman, P. O.; Tillberg, E.

1995-01-01

183

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

184

2-methylnaphthazarin 5- O-glucoside from the methanol extracts of in vitro cultures of Drosera species  

Microsoft Academic Search

The methanol extracts of Drosera rotundifolia and D. spathulata obtained by in vitro micropropagation yielded the new pigment 2-methylnaphthazarin (5,8-dihydroxy-2-methyl-1,4-naphthoquinone) 5-O-glucoside, which is an artefact formed from rossoliside (7-methylhydrojuglone 4-O-glucoside) during extraction with methanol.

Jaromir Budzianowski

1997-01-01

185

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

PubMed

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

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

2014-11-11

186

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

187

Capillary electrophoresis for simultaneous determination of emodin, chrysophanol, and their 8-beta-D-glucosides.  

PubMed

The simultaneous separation and determination of the major anthraquinones, emodin, chrysophanol, and their glucosides, of Rumex japonicus HOUTT., and emodin and emodin glucoside, of Cassia tora L., Rhamnus purshiana DC., Polygonum multiflorum THUNB., and P. cuspidatum SIEB. et ZUCC., were achieved by cyclodextrin modified capillary zone electrophoresis. The running electrolyte used in this method was 0.005 M alpha-cyclodextrin in 0.03 M borate buffer (pH 10.5) containing 10% acetonitrile, with an applied voltage of 20 kV. PMID:12672996

Koyama, Junko; Morita, Izumi; Kawanishi, Kazuko; Tagahara, Kiyoshi; Kobayashi, Norihiro

2003-04-01

188

Neuroprotective activity of galloylated cyanogenic glucosides and hydrolysable tannins isolated from leaves of Phyllagathis rotundifolia.  

PubMed

The galloylated cyanogenic glucosides based on prunasin (1-7), gallotannins (8-14), ellagitannins (15-17), ellagic acid derivatives (18, 19) and gallic acid (20) isolated from the leaves of Phyllagathis rotundifolia (Melastomataceae) were investigated for their neuroprotective activity against hydrogen peroxide (H(2)O(2))-induced oxidative damage in NG108-15 hybridoma cell line. Among these compounds, the gallotannins and ellagitannins exhibited remarkable neuroprotective activities against oxidative damage in vitro as compared to galloylated cyanogenic glucosides and ellagic acid derivatives in a dose-dependent manner. They could be explored further as potential natural neuroprotectors in various remedies of neurodegenerative diseases. PMID:22093753

Tan, Hooi Poay; Wong, Daniel Zin Hua; Ling, Sui Kiong; Chuah, Cheng Hock; Kadir, Habsah Abdul

2012-01-01

189

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

PubMed

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

Roepke, Jonathon; Bozzo, Gale G

2015-01-01

190

Degradation of the Isoflavone Biochanin A and Its Glucoside Conjugates by Ascochyta rabiei  

PubMed Central

Strains of Ascochyta rabiei which are pathogenic to chickpea (Cicer arietinum L.) readily catabolized the main chickpea isoflavone biochanin A (5,7-dihydroxy-4?-methoxyisoflavone). 3?-Hydroxylation and O-demethylation reactions led to the isoflavones pratensein, genistein, and orobol, which were rapidly further degraded. Dihydrogenistein and p-hydroxyphenylacetic acid were also identified as catabolites. Biochanin A-7-O-glucoside was degraded, leading to aglycone and pratensein. Biochanin A-7-O-glucoside-6?-O-malonate, the main phenolic constituent of chickpea, was very slowly degraded without subsequent accumulation of catabolites. PMID:16346840

Kraft, Birgit; Barz, Wolfgang

1985-01-01

191

Isolation and purification of flavonoid glucosides from Radix Astragali by high-speed counter-current chromatography.  

PubMed

High-speed counter-current chromatography methods, combined with resin chromatography were applied to the separation and purification of flavonoid glycosides from the Chinese medicinal herb, Radix Astragali. Five flavonoid glycosides, namely calycosin-7-O-beta-d-glucoside, ononin, (6aR, 11aR)-9,10-dimethoxypterocarpan-3-O-beta-d-glucoside, (3R)-2'-hydroxy-3',4'-dimethoxyisoflavan-7-O-beta-d-glucoside and calycosin-7-O-beta-d-glucoside-6''-O-acetate, were obtained. Among them, calycosin-7-O-beta-d-glucoside-6''-O-acetate was preparatively separated from Radix Astragali for the first time. Their structures were identified by ESI-MS, (1)H NMR, (13)C NMR, and 2D NMR. PMID:19213616

Xiao, Weihua; Han, Lujia; Shi, Bo

2009-03-15

192

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

PubMed

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

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

2014-09-15

193

Spiraeosides A and B, two new diterpenoid glucosides from Spiraea japonica var. ovalifolia.  

PubMed

Two new atisane-type diterpenoid glucosides, spiraeosides A (1) and B (2), were isolated from the aerial parts of Spiraea japonica L. f. var. ovalifolia. Their structures were characterized based on spectral analysis, and the structure of 1 was further confirmed by single-crystal X-ray diffraction. PMID:19350486

Zuo, Guoying; He, Hongping; Shen, Yuemao; Xu, Xiaojie; Wang, Zheming; Yan, Chunhua; Hao, Xiaojiang

2009-10-01

194

Glochidionolactones A-F: butenolide glucosides from leaves of Glochidion zeylanicum (GAERTN) A. JUSS.  

PubMed

From the leaves of Glochidion zeylanicum, six new butenolide glucoside, named glochidionolactones A-F, were isolated along with a known related compound, phyllanthurinolactone. The structures of glochidionolactones A-D and F were elucidated mainly by spectroscopic analyses. The absolute stereochemistry of glochidionolactone E was established by X-ray crystallographic analysis. PMID:10783076

Otsuka, H; Hirata, E; Takushi, A; Shinzato, T; Takeda, Y; Bando, M; Kido, M

2000-04-01

195

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

Microsoft Academic Search

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

Tetsuko Matsumura; Toru Ishikawa; Junichi Kitajima

2002-01-01

196

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

Microsoft Academic Search

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

Tetsuko Matsumura; Toru Ishikawa; Junichi Kitajima

2001-01-01

197

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

Technology Transfer Automated Retrieval System (TEKTRAN)

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

198

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

Technology Transfer Automated Retrieval System (TEKTRAN)

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

199

Colorimetric determination of active alpha-glucoside transport in Saccharomyces cerevisiae.  

PubMed

Fermentation of alpha-glucosides (maltose, maltotriose) by Saccharomyces cerevisiae cells is a critical phase in the processes of brewing and breadmaking. Utilization of alpha-glucosides requires the active transport of the sugar across the cell membrane and, subsequently, its hydrolysis by cytoplasmic glucosidases. Although transport activities are usually assayed using radiolabeled substrates, we have developed a simple, cheap and reliable colorimetric assay for the determination of alpha-glucoside uptake using p-nitrophenyl-alpha-D-glucopyranoside (pNPalphaG) as substrate. Our results show that pNPalphaG is actively transported by S. cerevisiae cells by a H+-symport mechanism, which depends on the electrochemical proton gradient across the plasma membrane. pNPalphaG uptake is mediated by the AGT1 alpha-glucoside permease, which has a high affinity (Km=3 mM) for this chromogenic substrate. This simple colorimetric uptake assay can be used to analyze the expression and regulation of the AGT1 permease in S. cerevisiae cells. PMID:11438190

Hollatz, C; Stambuk, B U

2001-09-01

200

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

Technology Transfer Automated Retrieval System (TEKTRAN)

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

201

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

Microsoft Academic Search

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

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

2001-01-01

202

Effect of the temperature and the exclusion of UVB radiation on the phenolics and iridoids in Menyanthes trifoliata L. leaves in the subarctic  

Microsoft Academic Search

The long-term effects of UVB exclusion and temperature on the methanol extractable (ME) phenolics (flavonoids, phenolic acids) and iridoids of Menyanthes trifoliata L. (Mt) leaves were studied in northern Finland (68°N) using wooden frames covered with filters for UVB exclusion (polyester filter), control (cellulose acetate filter) and ambient (no filter) conditions. Analysis of ambient plots showed no effect of the

Françoise Martz; Minna Turunen; Riitta Julkunen-Tiitto; Kaisa Lakkala; Marja-Liisa Sutinen

2009-01-01

203

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

204

Cycad toxins, Helicobacter pylori and parkinsonism: cholesterol glucosides as the common denomenator.  

PubMed

Understanding sporadic cases of age-dependent neurodegenerative diseases such as parkinsonism requires the evaluation of potential environmental factors. Amyotrophic lateral sclerosis-parkinsonism dementia complex (ALS-PDC), a neurological disorder in which features of parkinsonism are present and for which no consistent genetic explanation has been found, has been linked to the consumption of cycad (Cycas micronesica). Similarly, epidemiological evidence suggests an association between parkinsonism and gastric ulcer caused by Helicobacter pylori infection. While common immunological and inflammatory changes have been proposed to account for the link between parkinsonism and H. pylori infection, we propose an alternate explanation based on our work on the "cycad theory" of ALS-PDC. Recent experiments in our laboratory have identified several sterol glucosides in cycad that have neurotoxic properties in vitro and that appear to be linked to the development of neurodegenerative disease in vivo. Specifically, mice fed cycad display behavioural symptoms of parkinsonism such as reduced gait length, as well as neuropathological signs such as a loss of striatal dopaminergic (DAergic) terminals and an upregulation of the dopamine D2 receptor. These cycad-derived sterol glucosides are structurally similar to cholesterol glucosides that account for a significant part pf the lipid profile of H. pylori. We hypothesize that cholesterol glucosides arising from H. pylori infection may act as neurotoxins, promoting the degeneration of the DAergic neurons affected in parkinsonism, in a similar reaction to that which is thought to link cycad consumption and ALS-PDC. This hypothesis will be tested in future studies that will include exposing mice to purified sterol or cholestorol glucosides derived from cycad and comparing these mice behaviourally and neuropathologically to ones chronically infected with H. pylori. PMID:16488551

Schulz, J D; Hawkes, E L; Shaw, C A

2006-01-01

205

Analysis of Ginkgo biloba for the presence of ginkgotoxin and ginkgotoxin 5'-glucoside.  

PubMed

Hot water extracts of Ginkgo biloba seeds were analyzed for the presence of ginkgotoxin (4'-O-methylpyridoxine) by reversed-phase liquid chromatography (LC) using methanol-0.05M KH2PO4 (1 + 9, v/v) adjusted to pH 3 as mobile phase. Detection was by fluorescence (excitation 280 nm, emission 370 nm). A straight line calibration curve was obtained for the 10-100 ng injected. After addition of beta-glucosidase (37 degrees C/h), an earlier eluting peak disappeared and the ginkgotoxin peak increased. The identity of the ginkgotoxin was confirmed by LC/MS and LC/MS/MS. LC/MS/MS also confirmed the 5'-glucoside by comparison with the 3-glucoside. This is the first identification of a glucoside of ginkgotoxin in Ginkgo biloba. An unknown compound of MW 267 also observed in the Ginkgo biloba seed extract was shown not to be 3,5'-diacetylginkgotoxin by its different LC retention time. Extraction of ground Ginkgo biloba seeds with boiling water in a Soxhlet for 2 x 2 h yielded a total of 179 microg/g of free ginkgotoxin. The concentration in powder from Ginkgo biloba capsules was several times lower than this (17-64 microg/g) in 3 samples but higher in another (457 microg/g). Canned ginkgo seeds (white nuts) contained no detectable free ginkgotoxin but the glucoside was present. Different extraction times were studied: 0.5 h gave only 52 microg/g free ginkgotoxin in the ginkgo seeds. However, boiling an extract for 4 h showed about 15% loss of ginkgotoxin and its glucoside. PMID:11128132

Scott, P M; Lau, B P; Lawrence, G A; Lewis, D A

2000-01-01

206

Genetic screening identifies cyanogenesis-deficient mutants of Lotus japonicus and reveals enzymatic specificity in hydroxynitrile glucoside metabolism.  

PubMed

Cyanogenesis, the release of hydrogen cyanide from damaged plant tissues, involves the enzymatic degradation of amino acid-derived cyanogenic glucosides (alpha-hydroxynitrile glucosides) by specific beta-glucosidases. Release of cyanide functions as a defense mechanism against generalist herbivores. We developed a high-throughput screening method and used it to identify cyanogenesis deficient (cyd) mutants in the model legume Lotus japonicus. Mutants in both biosynthesis and catabolism of cyanogenic glucosides were isolated and classified following metabolic profiling of cyanogenic glucoside content. L. japonicus produces two cyanogenic glucosides: linamarin (derived from Val) and lotaustralin (derived from Ile). Their biosynthesis may involve the same set of enzymes for both amino acid precursors. However, in one class of mutants, accumulation of lotaustralin and linamarin was uncoupled. Catabolic mutants could be placed in two complementation groups, one of which, cyd2, encoded the beta-glucosidase BGD2. Despite the identification of nine independent cyd2 alleles, no mutants involving the gene encoding a closely related beta-glucosidase, BGD4, were identified. This indicated that BGD4 plays no role in cyanogenesis in L. japonicus in vivo. Biochemical analysis confirmed that BGD4 cannot hydrolyze linamarin or lotaustralin and in L. japonicus is specific for breakdown of related hydroxynitrile glucosides, such as rhodiocyanoside A. By contrast, BGD2 can hydrolyze both cyanogenic glucosides and rhodiocyanosides. Our genetic analysis demonstrated specificity in the catabolic pathways for hydroxynitrile glucosides and implied specificity in their biosynthetic pathways as well. In addition, it has provided important tools for elucidating and potentially modifying cyanogenesis pathways in plants. PMID:20453117

Takos, Adam; Lai, Daniela; Mikkelsen, Lisbeth; Abou Hachem, Maher; Shelton, Dale; Motawia, Mohammed Saddik; Olsen, Carl Erik; Wang, Trevor L; Martin, Cathie; Rook, Fred

2010-05-01

207

Tricin 7-glucoside protects against experimental cerebral ischemia by reduction of NF-?B and HMGB1 expression.  

PubMed

There have been several studies of nuclear factor-?B (NF-?B) and high-mobility group box1 (HMGB1) associated with the pathophysiology of cerebral ischemia. Tricin 7-glucoside, a major bioactive compound extracted from Sedum sarmentosum Bunge. The objectives of this study were to determine the effects of Tricin 7-glucoside on a cultured neuronal cell line, SH-SY5Y in vitro and experimental ischemic stroke in vivo. For oxygen-glucose deprivation (OGD) and tumor necrosis factor-? (TNF-?) stimulated SH-SY5Y cell line in vitro, SH-SY5Y cells were incubated with Tricin 7-glucoside. For in vivo experiment, rats were subjected to middle cerebral artery occlusion (MACO) for 1h, then followed by reperfusion for 23 h. Treatment of SH-SY5Y cells with Tricin 7-glucoside reduced the OGD-induced apoptosis and cytotoxicity, blocked TNF-?-induced NF-?B and I?B-? phosphorylation, and decreased HMGB1 expression. At doses higher than 50mg/kg, Tricin 7-glucoside produced a significant neuroprotective potential in rats with ischemia and reperfusion (I/R). Tricin 7-glucoside (100mg/kg) demonstrated significant neuroprotective activity even after delayed administration at 2h and 4h after I/R. Tricin 7-glucoside 100mg/kg attenuated histopathological damage, decreased brain edema, inhibited NF-?B activation and reduced HMGB1 expression. These data show that Tricin 7-glucoside protects brain against I/R injury with a favorable therapeutic time-window by alleviating cerebral I/R injury and attenuating blood-brain barrier (BBB) breakdown, and its protective effects may involve HMGB1 and NF-?B signaling pathway. PMID:22085682

Jiang, Wang-Lin; Xu, Yong; Zhang, Shu-Ping; Zhu, Hai-Bo; Hou, Jian

2012-01-23

208

The enzymatic hydrolysis of 6-acylamino-4-methylumbelliferyl-?- d-glucosides: identification of a novel human acid ?-glucosidase  

Microsoft Academic Search

Fluorogenic 6-acylamino-4-methylumbelliferyl-?-d-glucosides were found to be poor substrates for the three known human ?-gluco-sidases, i.e., lysosomal and non-lysosomal glucocerebrosidases and cytosolic broad-specificity ?-glucosidase. However, homogenates of human tissues and human cell types showed significant enzymatic hydrolysis of 6-ethanoylamino-4-methylumbelliferyl-?-d-glucoside (EMGlc) due to the activity of a hitherto undescribed ?-glucosidase, called here EMGlc-ase. It was shown that the isozyme is hardly active

Margarita Mikhaylova; Gherman Wiederschain; Valery Mikhaylov; Johannes M. F. G. Aerts

1996-01-01

209

Microwave-Assisted Synthesis of 2(1H)-Pyridones and Their Glucosides as Cell Proliferation Inhibitors  

Microsoft Academic Search

A new series of substituted 2(1H)-pyridones (4a–i) and their glucosides (5, 6a–e) were prepared as potential agents against leukemia (HL-60) cells. Glucosides (5,6a–e) were synthesized using three independent methods. Microwave protocol as an ecologically new method was used to synthesize the target compounds. Structures of the new products were confirmed using one- and two-dimensional NMR spectroscopy. In vitro exposure of

Shaikha S. Al-Neyadi; Ahmed H. Hassan; Ibrahim M. Abdou

2011-01-01

210

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

211

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

PubMed Central

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

Orr, John D.; Lynn, David G.

1992-01-01

212

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

NASA Technical Reports Server (NTRS)

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

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

1988-01-01

213

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

PubMed

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

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

2014-08-01

214

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

PubMed

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

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

2014-10-01

215

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

216

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

PubMed

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

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

2015-05-01

217

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

Microsoft Academic Search

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

John Strikart Nielsen; Birger Lindberg Møller

1999-01-01

218

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

Microsoft Academic Search

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

Yoshiyuki Kimura; Maho Sumiyoshi; Masahiko Taniguchi; Kimiye Baba

2008-01-01

219

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

Microsoft Academic Search

Previous studies from our laboratory indicated that pre-germinated brown rice (PR) contained certain un- known bioactive lipids that activated two enzymes related to diabetes: Na1\\/K1ATPase and homocysteine-thiolactonase. In this paper, we report on the isolation and structural char- acterization of the activator lipids from PR bran as acylated steryl glucosides (ASGs). The activator lipid was isolated by silica gel column

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

2008-01-01

220

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

PubMed Central

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

Harwani, Dharmesh

2014-01-01

221

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

PubMed Central

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

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

2013-01-01

222

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 technology.  

PubMed

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

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

2005-09-01

223

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

PubMed Central

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

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

2005-01-01

224

A Fourth Escherichia Coli Gene System with the Potential to Evolve ?-Glucoside Utilization  

PubMed Central

Escherichia coli K12 is being used to study the potential for adaptive evolution that is present in the genome of a single organism. Wild-type E. coli K12 do not utilize any of the ?-glucoside sugars arbutin, salicin or cellobiose. It has been shown that mutations at three cryptic loci allow utilization of these sugars. Mutations in the bgl operon allow inducible growth on arbutin and salicin while cel mutations allow constitutive utilization of cellobiose as well as arbutin and salicin. Mutations in a third cryptic locus, arbT, allow the transport of arbutin. A salicin(+) arbutin(+) cellobiose(+) mutant has been isolated from a strain which is deleted for the both the bgl and cel operons. Because the mutant utilized salicin and cellobiose as well as arbutin, it is unlikely that it is the result of a mutation in arbT. A second step mutant exhibited enhanced growth on salicin and a third step mutant showed better growth on cellobiose. A fourfold level of induction in response to arbutin and a twofold level of induction in response to salicin was observed when these mutants were assayed on the artificial substrate p-nitrophenyl-?-D-glucoside. Although growth on cellobiose minimal medium can be detected after prolonged periods of time, these strains are severely inhibited by cellobiose in liquid medium. This system has been cloned and does not hybridize to either bgl or cel specific probes. We have designated this gene system the sac locus. The sac locus is a fourth set of genes with the potential for evolving to provide ?-glucoside utilization. PMID:3042507

Parker, L. L.; Hall, B. G.

1988-01-01

225

[Extinguishment of harmful algae by organo-clay modified by alkyl glucoside quaternary ammonium compound].  

PubMed

Systematic study of the sorption behavior of alkyl glucoside quaternary ammonium compound (AGQAC) on kaolin and bentonite showed that the isotherms of its sorption can be described very well by the Langmuir isotherm. The rate of alkyl glucoside quaternary ammonium compound sorption on kaolin and bentonite was very fast, it could reach equilibration in one or two minutes, and its saturate sorption amount was much enough to be used to modify clays. Then the influence of alkyl glucoside quaternary ammonium compound on the growth of Prorocentrum donghaiense, Amphidinium carterae, Scrippsiella trochoidea were studied, it was found that when its concentration was below 0.4 mg/L, 0.5 mg/L, 0.8 mg/L it just restrained the growth of the algae, but when the concentration was above 0.6 mg/L, 0.75 mg/L, 1.2 mg/L it could cumber the algae's growth and even made them die after three days. When it was used combined with clays the concentration below 5 mg/L could enhance the algal removal efficiency of 50 mg/L clay from about 20% to above 90%, so it could decrease the concentration of crude clays in removing algal blooms. Meanwhile, the kinetics of red tide organism coagulation with clay was studied, the effects of different kinds and concentrations of clays, the second component added in clays were examined. Results showed that adding the second component in clay was the most efficient method to improve the algal removal efficiency. PMID:17326420

Wu, Ping; Yu, Zhi-Ming; Song, Xiu-Xian

2006-11-01

226

Nitrile-Containing Phenolic Glucosides from the Leaves of Glochidion acuminatum.  

PubMed

From the EtOAc-soluble fraction of a MeOH extract of the leaves of Glochidion acuminatum, six new compounds along with five known ones were isolated. The structures of the new compounds were elucidated to be two gallates, a p-hydroxybenzoate and an (S)-2-(4-hydroxycyclohex-1-en-1-yl)acetate of a nitrile-containing phenolic glucoside, methyl 2-(2-hydroxyphenyl)acetate ?-D-glucopyranoside, and (S)-methyl 2-[4-sulfooxycyclohex-1-en-1-yl]acetate on the basis of spectroscopic evidence. PMID:25743194

Yamashita-Higuchi, Yukiko; Sugimoto, Sachiko; Matsunami, Katsuyoshi; Inagaki, Masanori; Otsuka, Hideaki; Takeda, Yoshio

2015-01-01

227

Glochidionionosides A-D: megastigmane glucosides from leaves of Glochidion zeylanicum (Gaertn.) A. Juss.  

PubMed

Five megastigmane glucosides were isolated from the leaves of Glochidion zeylanicum. One of them was a known compound, blumenol C O-beta-D-glucopyranoside (1), and the structures of the four new compounds, glochidionionosides A-D (2-5), were mainly elucidated by spectroscopic methods, including a modified Mosher's method. The absolute configurations of the six-membered ring of glochidionionoside D (5) were deduced by beta-D-glucopyranosylation-induced shift trends in the (13)C-NMR spectra and confirmed by X-ray analysis as its p-bromobenzoate (5b), and the axis chirality of C-7 was determined to be R. PMID:12612412

Otsuka, Hideaki; Kijima, Hidehiko; Hirata, Eiji; Shinzato, Takakazu; Takushi, Anki; Bando, Masahiko; Takeda, Yoshio

2003-03-01

228

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, Ðinh Tri; Huynh, Thi My Nuong; Le, Tien Dung

2015-01-01

229

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

230

Coniferyl alcohol metabolism in conifers -- I. Glucosidic turnover of cinnamyl aldehydes by UDPG: coniferyl alcohol glucosyltransferase from pine cambium.  

PubMed

UDPG: coniferyl alcohol glucosyltransferase (CAGT; EC 2.4.1.111) isolated from cambial tissues of Pinus strobus was able to convert cinnamyl aldehydes as well as dihydroconiferyl alcohol into their corresponding 4-O-beta-D-glucosides in vitro. Cinnamyl aldehydes were glucosylated with comparable efficiency to coniferyl alcohol, the physiological substrate for CAGT. Seasonal patterns of CAGT activity for aldehydes were similar to those of coniferyl alcohol. Formation of cinnamyl aldehyde and additional monolignol glucosides indicates that precursor flux and availability for lignification is likely greater than previously recognized. PMID:11430981

Steeves, V; Förster, H; Pommer, U; Savidge, R

2001-08-01

231

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

PubMed

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

Hösel, W; Schiel, O

1984-02-15

232

Anticancer effect of ursolic acid stearoyl glucoside in chemically induced hepatocellular carcinoma.  

PubMed

Hepatocellular carcinoma is one of the leading causes of death in cancer and yet no drug has proven to be a successful candidate for its treatment in advanced stages. Ursolic acid stearoyl glucoside (UASG) is a newly discovered triterpene in Lantana camara and there lies a possibility that it possess anti-hepatocellular carcinoma property. In the present study, we induced hepatocellular carcinoma in Wistar rats by diethylnitrosamine (DENA) and treated it with ursolic acid stearoyl glucoside. The ability to treat hepatocellular carcinoma was measured by comparing biochemical serum markers such as serum alanine aminotransferase, serum aspartate aminotransferase, serum alkaline phosphatase, and the specific marker for hepatocellular carcinoma, alpha fetoprotein. The histological studies of the livers were also performed. The results have shown significant elevated levels of these parameters as compared to normal control and the drug receiving groups have shown significant reduction in these marker levels. Histopathological studies also indicated the reduced liver damage in drug-treated groups. It was noted that a significant and dose-dependent reversal of DENA-diminished activity of antioxidant enzymes like superoxide dismutase, catalase, glutathione peroxidase, glutathione transferase, and the reduced DENA-elevated level of lipid peroxidation (LPO) with a marked change. UASG significantly suppressed free radical formation by scavenging the hydroxyl radicals. It also modulates the levels of LPO and markedly increases the endogenous antioxidant enzymes level in DENA-induced hepatocellular carcinogenesis. PMID:23512248

Kazmi, Imran; Narooka, Anil Raj; Afzal, Muhammad; Singh, Rajbala; Al-Abbasi, Fahad A; Ahmad, Aftab; Anwar, Firoz

2013-12-01

233

Biosynthesis of Mustard Oil Glucosides: Sodium Phenylacetothiohydroximate and Desulfobenzylglucosinolate, Precursors of Benzylglucosinolate in Tropaeolum majus.  

PubMed

The biosynthesis of the mustard oil glucoside, benzylglucosinolate, was studied in Tropaeolum majus L. A number of labeled compounds were administered to plant shoots and the incorporation of tracer into benzylglucosinolate, isolated as the crystalline tetramethyl-ammonium salt, was measured. In order of decreasing efficiency of conversion into benzyl-glucosinolate the compounds fed were S-(beta-d-glucopyranosyl)phenylacetothiohydroximic acid (desulfobenzylglucosinolate), sodium phenylacetothiohydroximate, dl-phenylalanine, d-glucose, and sodium-d-1-glucopyranosyl mercaptide (1-thioglucose). The results are consistent with the hypothesis that the thioglucosyl group of benzylglucosinolate is derived by glucosylation of phenylacetothiohydroximate and not from 1-thioglucose. The results also suggest that benzylglucosinolate is formed by sulfation of desulfobenzylglucosinolate as the final step in its biosynthesis.A method for the isolation of a number of glucosinolates (mustard oil glucosides) is described which utilizes anion exchange chromatography on diethylaminoethyl (DEAE) cellulose. Potassium allylglucosinolate, tetramethylammonium benzylglucosinolate, potassium 2-hydroxy-2-phenylethylglucosinolate and potassium 2-phenylethylglucosinolate were obtained on recrystallization of the glucosinolate fraction eluted from the column. PMID:16657104

Underhill, L E; Wetter, L R

1969-04-01

234

Processing of iridoid glycoside antirrinoside fromMaurandya antirrhiniflora (Scrophulariaceae) byMeris paradoxa (Geometridae) andLepipolys species (Noctuidae).  

PubMed

The iridoid glycoside antirrinoside was found to be sequestered by highly aposematic larvae of the geometrid mothMeris paradoxa and two noctuid mothLepipolys species feeding onMaurandya antirrhiniflora (Scrophulariaceae), a natural food plant from southern Arizona. The antirrinoside content of leaves and petioles being consumed, eariy-instar larvae, late-instar larvae, larval frass, regurgitant, reflex-bleeding emission (Meris paradoxa), cocoons, pupae, meconium emitted upon eclosion, and adult moths was determined. Larvae, other than the earliest instars, did not excrete antirrinoside in the frass, but sequestered it in amounts of 3-11 % of the dry weight. Small amounts of antirrinoside remained in various pupal or cocoon parts and some was emitted in the meconium upon eclosion. The total antirrinoside accounted for was, however, considerably below that expected based upon the remarkably high 20% content of the leaves and petioles being consumed. The adult cryptic moths of both species contained little or no antirrinoside. This is the first report of a natural food plant and larval stages forM. paradoxa and a previously undescribedLepipolys species. It is also the first report of antirrinoside sequestration and utilization by insects. PMID:24259172

Boros, C A; Stermitz, F R; McFarland, N

1991-06-01

235

Freezing and melting behavior of an octyl ?-D-glucoside-water binary system--inhibitory effect of octyl ?-D-glucoside on ice crystal formation.  

PubMed

Phase transition behavior of lyotropic liquid crystals of an octyl ?-D-glucoside (OG)-water binary system during ice freezing and melting was studied by differential scanning calorimetry (DSC) and polarizing optical microscopy (POM). Not the thermotropic, but the lyotropic phase transition due to the change of OG concentration during ice freezing and melting was observed. The concentration-temperature phase diagram of the binary system was constructed. Melting temperature of ice, T(m), lyotropic phase transition temperature, T(tr), and glass transition temperatures of unfrozen phases in the absence and presence of ice, T(g) and T(g)', were shown in the phase diagram. The phase diagram indicated that the OG aqueous system was concentrated to ca. 90-92 wt% by ice freezing and exhibited glass transition at T(g)'. An observation of the concentration-gradient specimen by the cryo-POM showed the evidence of the inhibitory effects of OG on nucleation and growth of ice crystals in the extremely high OG concentration system in which the lamellar liquid crystalline phase was formed. This study provided the importance of the influence of concentration change by ice freezing on the behaviour of the sugar-based surfactant-water system under low temperature conditions. PMID:23133837

Ogawa, Shigesaburo; Asakura, Kouichi; Osanai, Shuichi

2012-12-21

236

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

Technology Transfer Automated Retrieval System (TEKTRAN)

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

237

Anti-diabetic potential of ursolic acid stearoyl glucoside: a new triterpenic gycosidic ester from Lantana camara.  

PubMed

A new stearoyl glucoside of ursolic acid, urs-12-en-3?-ol-28-oic acid 3?-D-glucopyranosyl-4'-octadecanoate and other compounds were isolated from the leaves of Lantana camara L. The structure of this new glycoside was elucidated and established by standard spectroscopic methods. In streptozotocin-induced diabetic rats it showed significant reduction in blood glucose level. PMID:22051701

Kazmi, Imran; Rahman, Mahfoozur; Afzal, Muhammad; Gupta, Gaurav; Saleem, Shakir; Afzal, Obaid; Shaharyar, Md Adil; Nautiyal, Ujjwal; Ahmed, Sayeed; Anwar, Firoz

2012-01-01

238

Two novel aromatic glucosides, marylaurencinosides D and E, from the fresh flowers of Cymbidium Great Flower 'Marylaurencin'.  

PubMed

Two novel aromatic glucosides, named marylaurencinosides D (1) and E (2), were isolated from the fresh flowers of Cymbidium Great Flower 'Marylaurencin'. In addition, eight known aromatic compounds (3-10) were isolated. These structures were determined on the basis of NMR experiments as well as chemical evidence. PMID:24448888

Yoshikawa, Kazuko; Okahuji, Mariko; Iseki, Kanako; Ito, Takuya; Asakawa, Yoshinori; Kawano, Sachiko; Hashimoto, Toshihiro

2014-04-01

239

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

240

The glucosyltransferase UGT72E2 is responsible for monolignol 4-O-glucoside production in Arabidopsis thaliana.  

PubMed

The phenylpropanoid pathway in plants leads to the synthesis of a wide range of soluble secondary metabolites, many of which accumulate as glycosides. In Arabidopsis, a small cluster of three closely related genes, UGT72E1-E3, encode glycosyltransferases shown to glucosylate several phenylpropanoids in vitro, including monolignols, hydroxycinnamic acids and hydroxycinnamic aldehydes. The role of these genes in planta has now been investigated through genetically downregulating the expression of individual genes or silencing the entire cluster. Analysis of these transgenic Arabidopsis plants showed that the levels of coniferyl and sinapyl alcohol 4-O-glucosides that accumulate in light-grown roots were significantly reduced. A 50% reduction in both glucosides was observed in plants in which UGT72E2 was downregulated, whereas silencing the three genes led to a 90% reduction, suggesting some redundancy of function within the cluster. The gene encoding UGT72E2 was constitutively overexpressed in transgenic Arabidopsis to determine whether increased glucosylation of monolignols could influence flux through the soluble phenylpropanoid pathway. Elevated expression of UGT72E2 led to increased accumulation of monolignol glucosides in root tissues and also the appearance of these glucosides in leaves. In particular, coniferyl alcohol 4-O-glucoside accumulated to massive amounts (10 micromol g(-1) FW) in root tissues of these plants. Increased glucosylation of other phenylpropanoids also occurred in plants overexpressing this glycosyltransferase. Significantly changing the pattern of glycosides in the leaves also led to a pronounced change in accumulation of the hydroxycinnamic ester sinapoyl malate. The data demonstrate the plasticity of phenylpropanoid metabolism and the important role that glucosylation of secondary metabolites can play in cellular homeostasis. PMID:16995900

Lanot, Alexandra; Hodge, Denise; Jackson, Rosamond G; George, Gilu L; Elias, Luisa; Lim, Eng-Kiat; Vaistij, Fabián E; Bowles, Dianna J

2006-10-01

241

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

PubMed

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

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

2015-05-01

242

Pharmacokinetics of vitexin-4?-O-glucoside in rats after intravenous application.  

PubMed

Vitexin-4?-O-glucoside (VOG), being a main component in the leaves of Crataegus pinnatifida Bge. var. major, was isolated and then three different doses (20, 40, and 60 mg/kg) of VOG were administered intravenously to rats. To study its pharmacokinetics, a simple and rapid HPLC method was developed using hesperidin as internal standard and the relative parameters were calculated by both compartmental and non-compartmental approach. The results showed that VOG fitted a two-compartment open model. The values of AUC increased proportionally within the range of 20-60 mg/kg. Additionally, ? half-life, ? half-life, (a)CL, MRT(0?t ), MRT(0?? ), and terminal half-life of VOG in rats showed significant differences between 20 mg/kg and other doses. Thereby, VOG presented a dose-dependent pharmacokinetics in the range of 20-60 mg/kg and non-linear pharmacokinetics at lower dose. PMID:22058050

Ying, Xi Xiang; Wang, Fei; Cheng, Zhong Zhe; Zhang, Wen Jie; Li, Hai Bo; Du, Yang; Liu, Xun; Wang, Si Yuan; Kang, Ting Guo

2012-06-01

243

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

244

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

PubMed

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

Nielsen, J S; Moller, B L

1999-08-01

245

Comprehensive two-dimensional liquid chromatography tandem diode array detector (DAD) and accurate mass QTOF-MS for the analysis of flavonoids and iridoid glycosides in Hedyotis diffusa.  

PubMed

The analysis of chemical constituents in Chinese herbal medicines (CHMs) is a challenge because of numerous compounds with various polarities and functional groups. Liquid chromatography coupled with quadrupole time-of-flight (QTOF) mass spectrometry (LC/MS) is of particular interest in the analysis of herbal components. One of the main attributes of QTOF that makes it an attractive analytical technique is its accurate mass measurement for both precursor and product ions. For the separation of CHMs, comprehensive two-dimensional chromatography (LCxLC) provides much higher resolving power than traditional one-dimensional separation. Therefore, a LCxLC-QTOF-MS system was developed and applied to the analysis of flavonoids and iridoid glycosides in aqueous extracts of Hedyotis diffusa (Rubiaceae). Shift gradient was applied in the two-dimensional separation in the LCxLC system to increase the orthogonality and effective peak distribution area of the analysis. Tentative identification of compounds was done by accurate mass interpretation and validation by UV spectrum. A clear classification of flavonol glycosides (FGs), acylated FGs, and iridoid glycosides (IGs) was shown in different regions of the LCxLC contour plot. In total, five FGs, four acylated FGs, and three IGs were tentatively identified. In addition, several novel flavonoids were found, which demonstrates that LCxLC-QTOF-MS detection also has great potential in herbal medicine analysis. PMID:25171829

Li, Duxin; Schmitz, Oliver J

2015-01-01

246

Plant chemical defense against herbivores and pathogens: generalized defense or trade-offs?  

Microsoft Academic Search

Plants are often attacked by multiple enemies, including pathogens and herbivores. While many plant secondary metabolites show specific effects toward either pathogens or herbivores, some can affect the performance of both these groups of natural enemies and are considered to be “generalized defense compounds”. We tested whether aucubin and catalpol, two iridoid glycosides present in ribwort plantain ( Plantago lanceolata),

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

2004-01-01

247

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

E-print Network

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

van Nouhuys, Saskya

248

Morphine glucuronidation and glucosidation represent complementary metabolic pathways that are both catalyzed by UDP-glucuronosyltransferase 2B7: kinetic, inhibition, and molecular modeling studies.  

PubMed

Morphine 3-?-D-glucuronide (M3G) and morphine 6-?-D-glucuronide (M6G) are the major metabolites of morphine in humans. More recently, morphine-3-?-d-glucoside (M-3-glucoside) was identified in the urine of patients treated with morphine. Kinetic and inhibition studies using human liver microsomes (HLM) and recombinant UGTs as enzyme sources along with molecular modeling were used here to characterize the relationship between morphine glucuronidation and glucosidation. The M3G to M6G intrinsic clearance (C(Lint)) ratio (?5.5) from HLM supplemented with UDP-glucuronic acid (UDP-GlcUA) alone was consistent with the relative formation of these metabolites in humans. The mean C(Lint) values observed for M-3-glucoside by incubations of HLM with UDP-glucose (UDP-Glc) as cofactor were approximately twice those for M6G formation. However, although the M3G-to-M6G C(Lint) ratio remained close to 5.5 when human liver microsomal kinetic studies were performed in the presence of a 1:1 mixture of cofactors, the mean C(Lint) value for M-3-glucoside formation was less than that of M6G. Studies with UGT enzyme-selective inhibitors and recombinant UGT enzymes, along with effects of BSA on morphine glycosidation kinetics, were consistent with a major role of UGT2B7 in both morphine glucuronidation and glucosidation. Molecular modeling identified key amino acids involved in the binding of UDP-GlcUA and UDP-Glc to UGT2B7. Mutagenesis of these residues abolished morphine glucuronidation and glucosidation. Overall, the data indicate that morphine glucuronidation and glucosidation occur as complementary metabolic pathways catalyzed by a common enzyme (UGT2B7). Glucuronidation is the dominant metabolic pathway because the binding affinity of UDP-GlcUA to UGT2B7 is higher than that of UDP-Glc. PMID:24459244

Chau, Nuy; Elliot, David J; Lewis, Benjamin C; Burns, Kushari; Johnston, Martin R; Mackenzie, Peter I; Miners, John O

2014-04-01

249

Identification, amounts, and kinetics of extraction of C -glucosidic ellagitannins during wine aging in oak barrels or in stainless steel tanks with oak chips  

Microsoft Academic Search

The C-glucosidic ellagitannins are found in wine as a result of its aging in oak barrels or in stainless steel tanks with oak chips.\\u000a Once dissolved in this slightly acidic solution, the C-glucosidic ellagitannins vescalagin can react with nucleophilic entities present in red wine, such as ethanol, catechin,\\u000a and epicatechin, to generate condensed hybrid products such as the ?-1-O-ethylvescalagin and

Michaël Jourdes; Julien Michel; Cédric Saucier; Stéphane Quideau; Pierre-Louis Teissedre

250

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

Microsoft Academic Search

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

Chun Hu; David D. Kitts

2004-01-01

251

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

PubMed

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

Wei, Yun; Xie, Qianqian; Ito, Yoichiro

2009-01-01

252

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

253

Coniferyl alcohol metabolism in conifers — I. Glucosidic turnover of cinnamyl aldehydes by UDPG: coniferyl alcohol glucosyltransferase from pine cambium  

Microsoft Academic Search

UDPG: coniferyl alcohol glucosyltransferase (CAGT; EC 2.4.1.111) isolated from cambial tissues of Pinus strobus was able to convert cinnamyl aldehydes as well as dihydroconiferyl alcohol into their corresponding 4-O-?-d-glucosides in vitro. Cinnamyl aldehydes were glucosylated with comparable efficiency to coniferyl alcohol, the physiological substrate for CAGT. Seasonal patterns of CAGT activity for aldehydes were similar to those of coniferyl alcohol.

Valerie Steeves; Hartmut Förster; Ulrich Pommer; Rodney Savidge

2001-01-01

254

The mechanism of vitexin-4?-O-glucoside protecting ECV-304 cells against tertbutyl hydroperoxide induced injury  

Microsoft Academic Search

The aim of this article is to investigate the mechanism of vitexin-4?-O-glucoside (VOG) protecting ECV-304 cells against tertbutyl hydroperoxide (TBHP)-induced injury. ECV-304 cell viability was measured by MTT assay. Apoptosis was determined by terminal deoxynucleotidyl transferase-mediated dUTP nick end-labelling (TUNEL) assay. Cellular morphological changes were observed using phase contrast microscopy. The change of relative mitochondrial transmembrane potential in the ECV-304

Hai-bo Li; Xi-xiang Ying; Jia Lu

2010-01-01

255

LC determination and pharmacokinetic study of vitexin-4?-O-glucoside in rat plasma after oral administration  

Microsoft Academic Search

A simple and specific high-performance liquid chromatography (HPLC) method was developed for the pharmacokinetic study of vitexin-4?-O-glucoside (VOG) in rats after oral administration. The plasma samples were deproteinised with methanol after the addition of an internal standard, hesperidin. HPLC analysis was performed on a Diamonsil C18 analytical column, using methanol ?0.5% aqueous phosphoric acid (45:55, v\\/v) as the mobile phase

Xun Liu; Dong Wang; Wenjie Zhang; Nan Wang; Siyuan Wang; Haibo Li; Xixiang Ying; Tingguo Kang

2011-01-01

256

LC determination and pharmacokinetic study of vitexin-4?-O-glucoside in rat plasma after oral administration  

Microsoft Academic Search

A simple and specific high-performance liquid chromatography (HPLC) method was developed for the pharmacokinetic study of vitexin-4?-O-glucoside (VOG) in rats after oral administration. The plasma samples were deproteinised with methanol after the addition of an internal standard, hesperidin. HPLC analysis was performed on a Diamonsil C18 analytical column, using methanol ?0.5% aqueous phosphoric acid (45:55, v\\/v) as the mobile phase

Xun Liu; Dong Wang; Wenjie Zhang; Nan Wang; Siyuan Wang; Haibo Li; Xixiang Ying; Tingguo Kang

2012-01-01

257

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

PubMed Central

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

Qin, Ying; Tian, Ya-ping

2011-01-01

258

Protective effects of cyanidin-3- O-glucoside from blackberry extract against peroxynitrite-induced endothelial dysfunction and vascular failure  

Microsoft Academic Search

Anthocyanins are a group of naturally occurring phenolic compounds as colorants in several plants, flowers and fruits. These pigments have a great importance as quality indicators, as chemotaxonomic markers and antioxidants.The content of blackberry (Rubus species) juice was investigated by HPLC\\/ESI\\/MS using narrow bore HPLC columns. Using this method we demonstrated that cyanidin-3-O-glucoside represents about 80% of the total anthocyanin

Ivana Serraino; Laura Dugo; Paola Dugo; Luigi Mondello; Emanuela Mazzon; Giovanni Dugo; Achille Patrizio Caputi; Salvatore Cuzzocrea

2003-01-01

259

Overexpression of the UGT73C6 alters brassinosteroid glucoside formation in Arabidopsis thaliana  

PubMed Central

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

2011-01-01

260

Growth of Azospirillum irakense KBC1 on the Aryl ?-Glucoside Salicin Requires either salA or salB  

PubMed Central

The rhizosphere nitrogen-fixing bacterium Azospirillum irakense KBC1 is able to grow on pectin and ?-glucosides such as cellobiose, arbutin, and salicin. Two adjacent genes, salA and salB, conferring ?-glucosidase activity to Escherichia coli, have been identified in a cosmid library of A. irakense DNA. The SalA and SalB enzymes preferentially hydrolyzed aryl ?-glucosides. A ?(salA-salB) A. irakense mutant was not able to grow on salicin but could still utilize arbutin, cellobiose, and glucose for growth. This mutant could be complemented by either salA or salB, suggesting functional redundancy of these genes in salicin utilization. In contrast to this functional homology, the SalA and SalB proteins, members of family 3 of the glycosyl hydrolases, show a low degree of amino acid similarity. Unlike SalA, the SalB protein exhibits an atypical truncated C-terminal region. We propose that SalA and SalB are representatives of the AB and AB? subfamilies, respectively, in glycosyl hydrolase family 3. This is the first genetic implication of this ?-glucosidase family in the utilization of ?-glucosides for microbial growth. PMID:10321999

Faure, Denis; Desair, Jos; Keijers, Veerle; Bekri, My Ali; Proost, Paul; Henrissat, Bernard; Vanderleyden, Jos

1999-01-01

261

Autophagy-related pathways and specific role of sterol glucoside in yeasts.  

PubMed

Recently, we showed that the requirement of sterol glucoside (SG) during pexophagy in yeasts is dependent on the species and the nature of peroxisome inducers. Atg26, the enzyme that converts sterol to SG, is essential for degradation of very large methanol-induced peroxisomes, but only partly required for degradation of smaller-sized oleate- and amine-induced peroxisomes in Pichia pastoris. Moreover, oleate- and amine-induced peroxisomes of another yeast, Yarrowia lipolytica, are degraded by an Atg26-independent mechanism. The same is true for degradation of oleate-induced peroxisomes in Saccharomyces cerevisiae. Here, we review our findings on the specificity of Atg26 function in pexophagy and extend our observations to the role of SG in the cytoplasm to vacuole targeting (Cvt) pathway and bulk autophagy. The results presented here and elsewhere indicate that Atg26 might increase the efficacy of all autophagy-related pathways in P. pastoris, but not in other yeasts. Recently, it was shown that P. pastoris Atg26 (PpAtg26) is required for elongation of the pre-autophagosomal structure (PAS) into the micropexophagic membrane apparatus (MIPA) during micropexophagy. Therefore, we speculate that SG might facilitate elongation of any double membrane from the PAS and this enhancer function of SG becomes essential when extremely large double membranes are formed. PMID:17329963

Nazarko, Taras Y; Farré, Jean-Claude; Polupanov, Andriy S; Sibirny, Andriy A; Subramani, Suresh

2007-01-01

262

Cyanidin-3-glucoside, a natural product derived from blackberry, exhibits chemopreventive and chemotherapeutic activity.  

PubMed

Epidemiological data suggest that consumption of fruits and vegetables has been associated with a lower incidence of cancer. Cyanidin-3-glucoside (C3G), a compound found in blackberry and other food products, was shown to possess chemopreventive and chemotherapeutic activity in the present study. In cultured JB6 cells, C3G was able to scavenge ultraviolet B-induced *OH and O2-* radicals. In vivo studies indicated that C3G treatment decreased the number of non-malignant and malignant skin tumors per mouse induced by 12-O-tetradecanolyphorbol-13-acetate (TPA) in 7,12-dimethylbenz[a]anthracene-initiated mouse skin. Pretreatment of JB6 cells with C3G inhibited UVB- and TPA-induced transactivation of NF-kappaB and AP-1 and expression of cyclooxygenase-2 and tumor necrosis factor-alpha. These inhibitory effects appear to be mediated through the inhibition of MAPK activity. C3G also blocked TPA-induced neoplastic transformation in JB6 cells. In addition, C3G inhibited proliferation of a human lung carcinoma cell line, A549. Animal studies showed that C3G reduced the size of A549 tumor xenograft growth and significantly inhibited metastasis in nude mice. Mechanistic studies indicated that C3G inhibited migration and invasion of A549 tumor cells. These finding demonstrate for the first time that a purified compound of anthocyanin inhibits tumor promoter-induced carcinogenesis and tumor metastasis in vivo. PMID:16618699

Ding, Min; Feng, Rentian; Wang, Shiow Y; Bowman, Linda; Lu, Yongju; Qian, Yong; Castranova, Vincent; Jiang, Bing-Hua; Shi, Xianglin

2006-06-23

263

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

PubMed Central

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

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

2014-01-01

264

Vesicle-micelle transition of phosphatidylcholine and octyl glucoside elucidated by cryo-transmission electron microscopy.  

PubMed Central

Vesicle-micelle transition structures of egg phosphatidylcholine (PC) and octyl glucoside (OG) mixtures were observed in the vitrified hydrated state by cryo-transmission electron microscopy (cryo-TEM) and correlated with the macroscopic and molecular changes previously associated with micellization monitored by 90 degrees light scattering and resonance energy transfer between fluorescent lipid probes. Several distinct structural changes occurred as OG was added to the PC vesicles. First, the average vesicle size decreased from 160 nm to less than 66 nm with no apparent change or decrease in optical density (OD). Then, associated with a small rise in OD, samples with open vesicles were observed coexisting with pieces of lamellae and long cylindrical micelles; more micelles were seen at higher [OG]. This mixture of vesicles and cylindrical micelles occurred in the region of the phase diagram previously attributed to vesicle opening, and possibly vesicle size increase. At higher [OG], small spheroidal micelles coexisting with cylindrical micelles correlated with a decrease in OD and changes in the fluorescence signal. At high [OG] when the solution appeared clear, spheroidal micelles were the dominant structure. By using cryo-TEM, a technique which preserves the original microstructure of fluid systems and provides direct images at 1 nm resolution, we have elucidated the vesicle-micelle transition and identified intermediates not known previously in the PC/OG system. Images FIGURE 1 FIGURE 2 FIGURE 4 FIGURE 6 FIGURE 7 FIGURE 8 PMID:2819233

Vinson, P K; Talmon, Y; Walter, A

1989-01-01

265

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

266

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

PubMed

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

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

2015-04-01

267

The plant oncogene rolC is responsible for the release of cytokinins from glucoside conjugates.  

PubMed Central

The rolC gene of Agrobacterium rhizogenes, which drastically affects growth and development of transgenic plants, codes for a cytokinin-beta-glucosidase. Indeed, rolC protein expressed in Escherichia coli as a fusion protein hydrolyses cytokinin glucosides, thus liberating free cytokinins. Furthermore, beta-glucosidase activity present in E. coli extracts expressing the rolC protein was inhibited by affinity-purified antibodies specific for the rolC protein. Finally, rolC proteins expressed in transgenic plants were shown to be responsible for cytokinin-beta-glucosidase activity. Morphological and phytohormonal analysis, performed on transgenic plants that are somatic mosaics for the expression of the rolC gene, extend and confirm our interpretation that the developmental, physiological and morphological alterations caused by rolC expression in transgenic plants are primarily due to a modification of the cytokinin balance. These observations shed new light on the control of growth and differentiation in plants by growth factors. Images PMID:1915268

Estruch, J J; Chriqui, D; Grossmann, K; Schell, J; Spena, A

1991-01-01

268

Effects of iriflophenone 3-C-?-glucoside on fasting blood glucose level and glucose uptake  

PubMed Central

Background: One of the biological activities of agar wood (Aquilaria sinensis Lour., Thymelaeaceae), is anti-hyperglycemic activity. The methanolic extract (ME) was proven to possess the fasting blood glucose activity in rat and glucose uptake transportation by rat adipocytes. Objective: To determine the decreasing fasting blood glucose level of constituents affordable for in vivo test. If the test was positive, the mechanism which is positive to the ME, glucose transportation, will be performed. Materials and Methods: The ME was separated by column chromatography and identified by spectroscopic methods. Mice was used as an animal model (in vivo), and rat adipocytes were used for the glucose transportation activity (in vitro). Result: Iriflophenone 3-C-?-glucoside (IPG) was the main constituent, 3.17%, and tested for the activities. Insulin and the ME were used as positive controls. The ME, IPG and insulin lowered blood glucose levels by 40.3, 46.4 and 41.5%, respectively, and enhanced glucose uptake by 152, 153, and 183%, respectively. Conclusion: These findings suggest that IPG is active in lowering fasting blood glucose with potency comparable to that of insulin. PMID:25709215

Pranakhon, Ratree; Aromdee, Chantana; Pannangpetch, Patchareewan

2015-01-01

269

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

270

Enhancement of volatile aglycone recovery facilitated by acid hydrolysis of glucosides from Nicotiana flower species.  

PubMed

Four different Nicotiana flowers (Nicotiana alata (alata), Nicotiana sylvestris (Sy), Nicotiana suaveolens (Su), and Nicotiana tabacum cv. Flue-Cured (FC)) from farms in Virginia and North Carolina were harvested and promptly quenched with liquid nitrogen and hand-ground prior to analysis. Each Nicotiana flower was pre-extracted with hexane to remove unbound volatiles. Fifteen standard compounds that were thought to be in the pre-extract were employed to aid in GC-MS identification and quantification. Glucosides were then chromatographically isolated and next hydrolyzed via 2 M sulfuric acid for 24 h at 75 °C. For each flower, the products of hydrolysis were extracted in tandem with hexane and dichloromethane (DCM) prior to analysis by GC-MS. The mixture of hexane and DCM extracts of the flowers after hydrolysis were then analyzed for each of 15 external standards via GC-MS to determine the concentration of any isolated flower-derived aglycone. Quantitative results for each of the possible 15 free volatile compounds extracted before and after hydrolysis were compared. Benzyl alcohol, phenethyl alcohol, and cis-3-hexenol were found in all Nicotiana both before and after acid hydrolysis. Enormous increases in the mass of benzyl alcohol and phenethyl alcohol were obtained with all flowers as a result of acid hydrolysis. With selected Nicotiana flowers, significant increases were observed for eugenol and cinnamaldehyde. The significant increases observed in cinnamaldehyde and eugenol upon mild acid hydrolysis strongly indicate that this approach could be a viable alternative process for the production scale isolation of these important natural flavor compounds. PMID:23101882

Coleman, William M; Dube, Michael F; Gerardi, Anthony R; Ashraf-Khorassani, Mehdi; Taylor, Larry T

2012-11-21

271

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

SciTech Connect

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

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

2013-12-15

272

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

PubMed

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

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

2003-01-01

273

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

PubMed Central

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

Stucky, Daniel F.; Arpin, James C.

2015-01-01

274

Maltotriose Utilization by Industrial Saccharomyces Strains: Characterization of a New Member of the ?-Glucoside Transporter Family  

PubMed Central

Maltotriose utilization by Saccharomyces cerevisiae and closely related yeasts is important to industrial processes based on starch hydrolysates, where the trisaccharide is present in significant concentrations and often is not completely consumed. We undertook an integrated study to better understand maltotriose metabolism in a mixture with glucose and maltose. Physiological data obtained for a particularly fast-growing distiller's strain (PYCC 5297) showed that, in contrast to what has been previously reported for other strains, maltotriose is essentially fermented. The respiratory quotient was, however, considerably higher for maltotriose (0.36) than for maltose (0.16) or glucose (0.11). To assess the role of transport in the sequential utilization of maltose and maltotriose, we investigated the presence of genes involved in maltotriose uptake in the type strain of Saccharomyces carlsbergensis (PYCC 4457). To this end, a previously constructed genomic library was used to identify maltotriose transporter genes by functional complementation of a strain devoid of known maltose transporters. One gene, clearly belonging to the MAL transporter family, was repeatedly isolated from the library. Sequence comparison showed that the novel gene (designated MTY1) shares 90% and 54% identity with MAL31 and AGT1, respectively. However, expression of Mty1p restores growth of the S. cerevisiae receptor strain on both maltose and maltotriose, whereas the closely related Mal31p supports growth on maltose only and Agt1p supports growth on a wider range of substrates, including maltose and maltotriose. Interestingly, Mty1p displays higher affinity for maltotriose than for maltose, a new feature among all the ?-glucoside transporters described so far. PMID:16151085

Salema-Oom, Madalena; Valadão Pinto, Vera; Gonçalves, Paula; Spencer-Martins, Isabel

2005-01-01

275

Total glucosides of paeony prevents juxta-articular bone loss in experimental arthritis  

PubMed Central

Background Total glucosides of paeony (TGP) is a biologically active compound extracted from Paeony root. TGP has been used in rheumatoid arthritis therapy for many years. However, the mechanism by which TGP prevents bone loss has been less explored. Methods TGP was orally administered for 3 months to New Zealand rabbits with antigen-induced arthritis (AIA). Digital x-ray knee images and bone mineral density (BMD) measurements of the subchondral knee bone were performed before sacrifice. Chondrocytes were observed using transmission electron microscopy (TEM). Histological analysis and mRNA expression of receptor activator of nuclear factor-B ligand (RANKL) and osteoprotegerin (OPG) were evaluated in joint tissues. Results The BMD value in TGP rabbits was significantly higher compared with that seen in the AIA model rabbits. In addition, the subchondral bone plate was almost completely preserved by TGP treatment, while there was a decrease in bone plate integrity in AIA rabbits. There was less damage to the chondrocytes of the TGP treated group. Immunohistochemical examination of the TGP group showed that a higher percentage of TGP treated chondrocytes expressed OPG as compared to the chondrocytes isolated from AIA treated animals. In contrast, RANKL expression was significantly decreased in the TGP treated group compared to the AIA group. In support of the immunohistochemistry data, the expression of RANKL mRNA was decreased and OPG mRNA expression was enhanced in the TGP group when compared to that of the AIA model group. Conclusion These results reveal that TGP suppresses juxta-articular osteoporosis and prevents subchondral bone loss. The decreased RANKL and increased OPG expression seen in TGP treated animals could explain how administration of TGP maintains higher BMD. PMID:23870279

2013-01-01

276

Antiobesity potential of ursolic acid stearoyl glucoside by inhibiting pancreatic lipase.  

PubMed

The present study was designed to evaluate the hypolipidemic effect of ursolic acid stearoyl glucoside (UASG) in high-fat diet-induced obesity. Two in vivo experiments such as high-fat diet-induced obesity mice model and lipid emulsion tolerance test in normal rats were performed. In vitro inhibition of pancreatic lipase activity was further measured to substantiate the results. In high-fat diet-induced obesity mice model, female Swiss mice were fed a high fat diet (HFD; 40% fat) with or without 1 or 2% of UASG or 0.012% orlistat for nine weeks. In lipid emulsion tolerance test male Wister rats were orally administered, lipid emulsion with or without 500 or 1000 mg/kg of UASG and the plasma triglycerides were measured from 0.5 to 5 h. Consumption of HFD containing UASG to mice for nine weeks exhibited significant reduction in lipid parameters, body weight, parametrial adipose tissue weight, liver triglyceride (TG) and different organ weight compared to HFD fed control. Further it was noted the improvement in insulin resistance induced by the HFD alone group. Furthermore, consumption of an HFD containing 1 or 2% of UASG significantly increased the fecal content and fecal triglyceride compared with the HFD group. Pre-treatment with UASG inhibited the elevated plasma triglyceride level after the oral administration of the lipid emulsion to rats. Further, UASG significantly inhibits activity of pancreatic lipase at a concentration of 2.5 mg/ml. Data obtained from the results indicated that UASG prevent high-fat diet-induced obesity in mice possibly by inhibiting pancreatic lipase activity. PMID:23500199

Kazmi, Imran; Afzal, Muhammad; Rahman, Shakilur; Iqbal, Muzaffar; Imam, Faisal; Anwar, Firoz

2013-06-01

277

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

PubMed

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

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

2015-02-01

278

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

PubMed

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

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

2014-11-01

279

Luteolin and luteolin-7-O-glucoside strengthen antioxidative potential through the modulation of Nrf2/MAPK mediated HO-1 signaling cascade in RAW 264.7 cells.  

PubMed

It has been understood that glycosidic forms of flavonoids were hydrolyzed by gut bacteria and absorbed as aglycones. However, several reports suggested that glycosides were partly absorbed without hydrolysis and remained biologically active. In this study, we evaluated the antioxidative potential of luteolin and luteolin-7-O-glucoside, glycosidic form of luteolin, against the oxidative damage and compared their antioxidative mechanisms in RAW 264.7 cells. Heme oxygenase-1 (HO-1), one of the phase II enzymes showing an antioxidative activity, was potently induced by luteolin and luteolin-7-O-glucoside treatment, which was in accordance with the translocated nuclear factor-erythroid 2 p45-related factor 2 (Nrf2) into nucleus. Moreover, luteolin and the luteolin-7-O-glucoside activated HO-1 expression by p38 and c-Jun NH2-terminal kinase (JNK) regulation. In order to identify the antioxidation potential by HO-1, tert-butyl hydroperoxide (t-BHP)-induced oxidative damage was applied and ameliorated by luteolin and the luteolin-7-O-glucoside treatment in a dose dependent manner, which was confirmed by HO-1 selective inhibitor and inducer, tin protoporphyrin (SnPP) and cobalt protoporphyrin (CoPP), respectively. Consequently, luteolin and luteolin-7-O-glucoside potently strengthen the HO-1-mediated antioxidative potential through the modulation of the Nrf2/MAPK signaling pathways. PMID:24361407

Song, Young Sun; Park, Chung Mu

2014-03-01

280

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

281

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

PubMed

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

Piwowarski, Jakub P; Kiss, Anna K

2015-01-01

282

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

PubMed

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

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

2013-02-01

283

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

PubMed

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

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

1989-01-01

284

Hypolipidemic and antioxidant effects of hydroxycinnamic acids, quercetin, and cyanidin 3-glucoside in hypercholesterolemic erythrocytes (in vitro study)  

Microsoft Academic Search

Objective  Four polyphenols: ferulic acid and p-coumaric acid (hydroxycinnamic acids), quercetin (flavonol) and cyanidin 3-glucoside (anthocyanin) were selected, and their\\u000a antioxidant properties and their influence on cholesterol concentration in hypercholesterolemic and normal erythrocytes were\\u000a investigated.\\u000a \\u000a \\u000a \\u000a \\u000a Methods  To determine the effect of phenolic compounds, we prospectively studied cholesterol concentration, lipid peroxidation and\\u000a membranes fluidity. Whole-blood and isolated erythrocytes (2% hematocrit) were incubated for

Piotr Duchnowicz; Marlena Broncel; Anna Pods?dek; Maria Koter-Michalak

285

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

286

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

PubMed

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

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

2014-01-01

287

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

PubMed Central

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

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

2014-01-01

288

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

289

Effects of total glucosides of peony on immunological hepatic fibrosis in rats  

PubMed Central

AIM: To study the effects of total glucosides of peony (TGP) on immunological hepatic fibrosis induced by human albumin in rats. METHODS: Sixty adult male Sprague-Dawley rats were randomly divided into: Normal group, model group, TGP (60 and 120 mg/kg) treatment groups and colchicines (0.1 mg/kg) treatment group. On the day before the rats were killed, those in TGP or colchicine groups received TGP or colchicine as above from the first day of tail vein injection of human albumin. The rats in normal and model groups were only administered with the same volume of vehicle. At the end of the 16th wk, rats in each group were killed. Blood and tissue specimens were taken. Levels of alanine aminotransferase (ALT), aspartate aminotr-ansferase (AST), nitric oxide (NO), content of malondi-aldehyde (MDA), activity of superoxide dismutase (SOD) and glutathione peroxidase (GSH-px), were measured by biochemical methods. Serum procollagen type III (PC III) and laminin (LN) were determined by radioimmunoassay. Liver collagen level was determined by measuring hydroxyproline content in fresh liver samples. Hepatic tissue sections were stained with hematoxylin-eosin and examined under a light microscope. RESULTS: Histological results showed that TGP improved the human albumin-induced alterations in the liver structure, alleviated lobular necrosis and significantly lowered collagen content. The antifibrotic effect of TGP was also confirmed by decreased serum content of LN and PCIII in TGP-treated group. Moreover, the treatment with TGP effectively reduced the hydroxyproline content in liver homogenates. However, the level of ALT and AST increased in fibrotic rat but had no significance compared with normal control, whereas the ratio of A/G decreased without significance. TGP had no effect on level of ALT, AST and the ratio of A/G. Furthermore, TGP treatment significantly blocked the increase in MDA and NO, asso-ciated with a partial elevation in liver total antioxidant capacity including SOD and GSH-px. CONCLUSION: TGP has beneficial effects on hepatic fibrosis in rats by inhibition of collagen synthesis and decreasing oxidative stress. PMID:15810078

Wang, Hua; Wei, Wei; Wang, Ni-Ping; Wu, Cheng-Yi; Yan, Shang-Xue; Yue, Li; Zhang, Ling-Ling; Xu, Shu-Yun

2005-01-01

290

?-Furfuryl-?-Glucoside: An Endogenous Activator of Higher Plant UDP-Glucose:(1-3)-?-Glucan Synthase 1  

PubMed Central

In a recent paper (P Ohana, DP Delmer, JC Steffens, DE Matthews, R Mayer, M Benziman [1991] J Biol Chem 266: 13472-13475), we described the purification and structural characterization of ?-furfuryl-?-glucoside (FG), an endogenous activator of plant UDP-glucose:(1?3)-?-glucan (callose) synthase. In the present report, we provide evidence that FG specifically stimulates callose synthase. The effects of FG on the kinetic properties of callose synthase were studied, and we ascertained that FG, or at least a very similar compound, is present in other plant systems. Chemically synthesized ?-furfuryl-?-glucoside also stimulates callose synthase, exhibiting a slightly higher Ka of 80 micromolar, compared with 50 micromolar for FG. In addition, we have identified and partially characterized an enzyme that catalyzes the synthesis of FG using ?-furfuryl alcohol and UDP-glucose as substrates. A model for the regulation of callose synthesis in vivo, involving changes in intracellular compartmentation of FG and Ca2+, is proposed. ImagesFigure 4 PMID:16668699

Ohana, Patricia; Delmer, Deborah P.; Volman, Gail; Steffens, John C.; Matthews, David E.; Benziman, Moshe

1992-01-01

291

Intestinal SGLT1-mediated absorption and metabolism of benzyl ?-glucoside contained in Prunus mume: carrier-mediated transport increases intestinal availability  

Microsoft Academic Search

The intestinal absorption of benzyl ?-glucoside (BNZ?glc) contained in the fruit of Prunus mume SIEB. et ZUCC. (Rosaceae), which is traditionally used as a medicinal food in Japan, was studied in rat intestines. BNZ?glc was absorbed from the mucosal to serosal sides. Its metabolite, benzyl alcohol (BAL), was also detected on both the mucosal and serosal sides. In the presence

Takashi Mizuma; Maya Nakamura; Hiroji Ina; Toshio Miyazaki; Masahiro Hayashi

2005-01-01

292

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

Technology Transfer Automated Retrieval System (TEKTRAN)

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

293

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

294

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

NASA Astrophysics Data System (ADS)

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

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

2005-12-01

295

Oviposition Cues for a Specialist Butterfly–Plant Chemistry and Size  

PubMed Central

The oviposition choice 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 of the plant Plantago lanceolata, on the oviposition behavior of the specialist butterfly Melitaea cinxia. Iridoid glycosides are known to deter feeding or decrease the growth rate of generalist insect herbivores, but can act as oviposition cues and feeding stimulants for specialized herbivores. In a previous observational study of M. cinxia in the field, oviposition was associated with high levels of aucubin. However, this association could have been the cause (butterfly choice) or consequence (plant induction) of oviposition. We conducted a set of dual- and multiple-choice experiments in cages and in the field. In the cages, we found a positive association between the pre-oviposition level of aucubin and the number of ovipositions. The association reflects the butterfly oviposition selection rather than plant induction that follows oviposition. Our results also suggest a threshold concentration below which females do not distinguish between levels of iridoid glycosides. In the field, the size of the plant appeared to be a more important stimulus than iridoid glycoside content, with bigger plants receiving more oviposition than smaller plants, regardless of their secondary chemistry. Our results illustrate that the rank of a cue used for oviposition may be dependent on environmental context. PMID:18612691

Biere, A.; Harvey, J. A.; van Nouhuys, S.

2008-01-01

296

Identification, amounts, and kinetics of extraction of C-glucosidic ellagitannins during wine aging in oak barrels or in stainless steel tanks with oak chips.  

PubMed

The C-glucosidic ellagitannins are found in wine as a result of its aging in oak barrels or in stainless steel tanks with oak chips. Once dissolved in this slightly acidic solution, the C-glucosidic ellagitannins vescalagin can react with nucleophilic entities present in red wine, such as ethanol, catechin, and epicatechin, to generate condensed hybrid products such as the ?-1-O-ethylvescalagin and the flavano-ellagitannins (acutissimin A/B and epiacutissimin A/B), respectively. During this study, we first monitored the extraction kinetic and the evolution of the eight major oak-derived C-glucosidic ellagitannins in red wines aged in oak barrels or in stainless steel tank with oak chips. Their extraction rates appeared to be faster during red wine aging in stainless steel tanks with oak chips. However, their overall concentrations in wines were found higher in the wine aged in barrels. The formation rates of the vescalagin-coupled derivatives were also estimated for the first time under both red wine aging conditions (i.e., oak barrels or stainless steel tanks with oak chips). As observed for the oak-native C-glucosidic ellagitannins, the concentrations of these vescalagin derivatives were higher in the red wine aged in oak barrels than in stainless steel tanks with oak chips. Despite these differences, their relative composition was similar under both red wine aging conditions. Finally, the impact of the oak chips size and toasting level on the C-glucosidic ellagitannins concentration in wine was also investigated. PMID:21479542

Jourdes, Michaël; Michel, Julien; Saucier, Cédric; Quideau, Stéphane; Teissedre, Pierre-Louis

2011-09-01

297

Structures of eremophilane-type sesquiterpene glucosides, alticolosides A-G, from the Far Eastern endemic Ligularia alticola Worosch.  

PubMed

Seven eremophilane-type sesquiterpene glucosides, alticolosides A-G, have been isolated from aerial parts of the endemic Far Eastern species Ligularia alticola Worosch. (Family Asteraceae) along with two known compounds, monoterpenoid glycoside (4S)-?-terpineol 8-O-?-d-glucopyranoside and norditerpenoid glycoside 7(8)-dihydro-?-ionone 3-O-?-d-glucopyranoside. Alticoloside D was identified with the earlier known 8-O-(?-d-glucopyranosyl)-2-oxo-eremophila-1(10),8,11-triene, but the stereostructure of the latter was revised on the basis of ROESY and CD data. All the glycosides are derivatives of new eremophilane-type aglycones, differing from known eremophilanes in details of planar and/or stereo structures except for the aglycone of alticoloside E. PMID:25481409

Silchenko, Alexandra S; Kalinovsky, Anatoly I; Ponomarenko, Ludmila P; Avilov, Sergey A; Andryjaschenko, Pelageya V; Dmitrenok, Pavel S; Gorovoy, Peter G; Kim, Natalia Yu; Stonik, Valentin A

2015-03-01

298

Different spectroscopic and molecular modeling studies on the interaction between cyanidin-3-O-glucoside and bovine serum albumin.  

PubMed

Anthocyanin is one of the flavonoid phytopigments that shows strong antioxidant activity. The cyanidin-3-O-glucoside (C3G) is one of the principal types of anthocyanins. To understand the interaction between C3G and bovine serum albumin (BSA), fluorescence spectroscopy, ultraviolet-visible absorption, Fourier transform infrared spectroscopy, circular dichroism and molecular modeling techniques were used. Binding constant (K(a)) and the number of binding sites (n) were calculated. The quenching mechanism of fluorescence of BSA by C3G was discussed. The results studied by Fourier transform infrared spectroscopy and circular dichroism experiments indicate that the secondary structures of the protein have been changed by the interaction of C3G with BSA. The result of molecular modeling confirmed that the C3G bound to the site I (sub-domain IIA) of BSA, and that the hydroxyl groups in the B ring of C3G took part in the binding with BSA. PMID:23723132

Tang, Lin; Zhang, Dong; Xu, Shanhua; Zuo, Huijun; Zuo, Chunlin; Li, Yufei

2014-03-01

299

Validated HPLC method for simultaneous estimation of khellol glucoside, khellin and visnagin in Ammi visnaga L. fruits and pharmaceutical preparations.  

PubMed

Tea bags including fruits of Ammi visnaga L. are used in Egypt as remedy for the treatment of kidney stones. Our study focuses on developing simple and rapid method utilising HPLC for quantitative estimation of khellol glucoside (KG), khellin (KH) and visnagin (VS) simultaneously. Their concentrations were determined in A. visnaga L. fruits at different developmental stages and in pharmaceutical formulations together with following up them during shelf life. Separation was accomplished using HPLC. Perfect resolution between KG, KH and VS was possible through using a mobile phase consisting of water:methanol:tetrahydrofuran (50:45:5, v/v/v). Peaks were detected at 245 nm. The suggested method for the determination of KG, KH and VS was successful in determining the analytes of interest without any interference of other compounds and matrix. All validation parameters were satisfactory and the procedure was relatively easy and fast as extracts are evaluated without previous steps of purification. PMID:25111086

Badr, Jihan M; Hadad, Ghada M; Nahriry, Khaled; Hassanean, Hashem A

2015-04-01

300

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

301

The mechanism of vitexin-4''-O-glucoside protecting ECV-304 cells against tertbutyl hydroperoxide induced injury.  

PubMed

The aim of this article is to investigate the mechanism of vitexin-4''-O-glucoside (VOG) protecting ECV-304 cells against tertbutyl hydroperoxide (TBHP)-induced injury. ECV-304 cell viability was measured by MTT assay. Apoptosis was determined by terminal deoxynucleotidyl transferase-mediated dUTP nick end-labelling (TUNEL) assay. Cellular morphological changes were observed using phase contrast microscopy. The change of relative mitochondrial transmembrane potential in the ECV-304 cells was analysed with rhodamine 123 staining. Lipid peroxidation was measured by the HPLC method. The results showed that 128 µmol L(-1) VOG could effectively protect ECV-304 cells against cytotoxicity induced by TBHP. VOG protected TBHP-treated ECV-304 cells from death, significantly decreased MDA production, and increased superoxide dismutase (SOD) activity and mitochondrial membrane potential (??). Taken together, VOG protects against TBHP-induced ECV-304 cell injury partially through resuming mitochondrial function. PMID:20419557

Li, Hai-bo; Ying, Xi-xiang; Lu, Jia

2010-11-01

302

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

PubMed

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

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

2014-01-01

303

Structural characterization and identification of iridoid glycosides, saponins, phenolic acids and flavonoids in Flos Lonicerae Japonicae by a fast liquid chromatography method with diode-array detection and time-of-flight mass spectrometry.  

PubMed

A fast liquid chromatography method with diode-array detection (DAD) and time-of-flight mass spectrometry (TOF-MS) has been developed for analysis of constituents in Flos Lonicerae Japonicae (FLJ), a traditional Chinese medicine derived from the flower bud of Lonicera japonica. The chromatographic analytical time decreased to 25 min without sacrificing resolution using a column packed with 1.8-microm porous particles (4.6 x 50 mm), three times faster than the performance of conventional 5.0-microm columns (4.6 x 150 mm). Four major groups of compounds previously isolated from FLJ were structurally characterized by DAD-TOF-MS: iridoid glycosides showed maximum UV absorption at 240 nm; phenolic acids at 217, 242, and 326 nm; flavonoids at 255 and 355 nm; while saponins had no absorption. In electrospray ionization (ESI)-TOF-MS experiments, elimination of a glucose unit (162 Da), and successive losses of H(2)O, CH(3)OH and CO, were generally observed in iridoid glycosides; saponins were characterized by a series of identical aglycone ions; phenolic acids typically generated a base peak at [M-H-caffeoyl](-) by loss of a caffeic acid unit (162 Da) and several marked quinic acid moiety ions; cleavage of the glycosidic bond (loss of 162 or 308 Da), subsequent losses of H(2)O, CO, RDA and C-ring fragmentation were the most possible fragmentation pathways for flavonoids. By accurate mass measurements within 4 ppm error for each molecular ion and subsequent fragment ions, as well as the 'full mass spectral' information of TOF-MS, a total of 41 compounds including 13 iridoid glycosides, 11 phenolic acids, 7 saponins, and 10 flavonoids were identified in a methanolic extract of FLJ. PMID:19725056

Qi, Lian-Wen; Chen, Chun-Yun; Li, Ping

2009-10-01

304

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

305

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

306

Iridoid Glycosides Fraction of Folium syringae Leaves Modulates NF-?B Signal Pathway and Intestinal Epithelial Cells Apoptosis in Experimental Colitis  

PubMed Central

Background and Aims Iridoid glycosides (IG), the major active fraction of F. syringae leaves has been demonstrated to have strong anti-inflammatory properties to ulcerative colitis (UC) in our previous study. The aim of this study was to investigate whether IG modulates the inflammatory response in experimental colitis at the level of NF-?B signal pathway and epithelial cell apoptosis. Methods UC in rats was induced by administration with dextran sulfate sodium (DSS) in drinking water. The inflammatory damage was assessed by disease activity index (DAI), macroscopic findings, histology and myeloperoxidase (MPO) activity. The effect of IG on pro-inflammatory cytokines TNF-?, IL-8, COX-2 and regulatory peptide TGF-?1 was measured. Epithelial cell apoptosis and the protein and mRNA expressions of Fas/FasL, Bcl-2/Bax, caspase-3, NF-?B p65, I?B?, p-I?B? and IKK? were detected by TUNEL method, immunohistochemistry, Western blotting and real-time quantitative PCR, respectively. Results IG significantly ameliorated macroscopic damage and histological changes, reduced the activity of MPO, and strongly inhibited epithelial cell apoptosis. Moreover, IG markedly depressed TNF-?, IL-8, COX-2 and TGF-?1 levels in the colon tissues in a dose-dependent manner. Furthermore, IG significantly blocked of NF-?B signaling by inhibiting I?B? phosphorylation/degradation and IKK? activity, down-regulated the protein and mRNA expressions of Fas/FasL, Bax and caspase-3, and activated Bcl-2 in intestinal epithelial cells. Conclusions These results demonstrated for the first time that IG possessed marked protective effects on experimental colitis through inhibition of epithelial cell apoptosis and blockade of NF-?B signal pathway. PMID:21931839

Liu, Xin; Wang, Jian Ming

2011-01-01

307

Design, synthesis and in vivo anti-hyperglycemic activity of gem-dimethyl-bearing C-glucosides as SGLT2 inhibitors  

Microsoft Academic Search

A series of gem-dimethyl-bearing C-glucosides were designed and synthesized as SGLT2 inhibitors, with anhydrous aluminum chloride-mediated Friedel-Crafts alkylation to construct the gem-dimethyl functionality being the key step. The in vivo anti-hyperglycemic activity was evaluated with mice oral glucose tolerance test (OGTT), and all the synthesized compounds showed significant but less potent anti-hyperglycemic activity than the positive control dapagliflozin.

Wen Jing Zhao; Yong Heng Shi; Gui Long Zhao; Yu Li Wang; Hua Shao; Li Da Tang; Jian Wu Wang

2011-01-01

308

Growth of Azospirillum irakense KBC1 on the Aryl b-Glucoside Salicin Requires either salA or salB  

Microsoft Academic Search

The rhizosphere nitrogen-fixing bacterium Azospirillum irakense KBC1 is able to grow on pectin and b-gluco- sides such as cellobiose, arbutin, and salicin. Two adjacent genes, salA and salB, conferring b-glucosidase ac- tivity to Escherichia coli, have been identified in a cosmid library of A. irakense DNA. The SalA and SalB en- zymes preferentially hydrolyzed aryl b-glucosides. A D(salA-salB) A. irakense

DENIS FAURE; JOS DESAIR; VEERLE KEIJERS; PAUL PROOST; BERNARD HENRISSAT; JOS VANDERLEYDEN

1999-01-01

309

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

PubMed Central

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

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

2014-01-01

310

Protection by tetrahydroxystilbene glucoside against cerebral ischemia: involvement of JNK, SIRT1, and NF-?B pathways and inhibition of intracellular ROS\\/RNS generation  

Microsoft Academic Search

Many natural polyphenolic compounds have been shown to attenuate reactive oxygen\\/nitrogen species (ROS\\/RNS) formation and protect against ischemia\\/reperfusion injury both in vitro and in vivo. 2,3,5,4?-tetrahydroxystilbene-2-O-?-d-glucoside (TSG), an active component of the rhizome extract from Polygonum multiflorum, exhibits antioxidative and anti-inflammatory effects. Here, we used an in vitro ischemic model of oxygen–glucose deprivation followed by reperfusion (OGD-R) and an in

Ting Wang; Jun Gu; Peng-Fei Wu; Fang Wang; Zhe Xiong; Yuan-Jian Yang; Wen-Ning Wu; Ling-Dan Dong; Jian-Guo Chen

2009-01-01

311

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

312

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

PubMed Central

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

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

2014-01-01

313

Tetrahydroxystilbene Glucoside Improves TNF-?-Induced Endothelial Dysfunction: Involvement of TGF?/Smad Pathway and Inhibition of Vimentin Expression.  

PubMed

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

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

2015-01-01

314

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

315

Predicting the preferred conformations of luteolin-4'-O-?-D-glucoside in gas phase: a comparison of two computational approaches.  

PubMed

A tree-step computational approach has been applied to determine the lowest-energy conformers of luteolin-4'-O-?-D-glucoside (L4'G). Fifty-seven starting structures of the L4'G have been built, and then by performing with density functional theory (DFT) optimizations and second-order Møller-Plesset (MP2) calculations, the preferred conformations of L4'G are predicted. In order to test the accuracy of the computational approach, a hybrid Monte-Carlo multiple minimum (MCMM)/quantum mechanical (QM) approach is applied to determine the favorable conformers of L4'G. The alternative classification is employed to put similar conformations into the same catalogue according to the dihedral angles among the luteolin rings, glycosidic dihedral angles, and the orientations of hydroxyl and hydroxymethyl groups. The low-energy conformations are located after the optimizations at the HF/6-31G(d) and B3LYP/6-311+G(d) levels. Compared with the hybrid MCMM/QM approach, the tree-step computational approach not only remains accurate but also saves a lot of computing resources. PMID:23748558

Li, Yongzhi; Liu, Xiuhua; Chen, Dong; Wei, Zhichao; Liu, Bo

2013-09-01

316

The ?-Glucoside (bgl) Operon of Escherichia coli Is Involved in the Regulation of oppA, Encoding an Oligopeptide Transporter  

PubMed Central

We report that the bgl operon of Escherichia coli, encoding the functions necessary for the uptake and metabolism of aryl-?-glucosides, is involved in the regulation of oligopeptide transport during stationary phase. Global analysis of intracellular proteins from Bgl-positive (Bgl+) and Bgl-negative (Bgl?) strains revealed that the operon exerts regulation on at least 12 downstream target genes. Of these, oppA, which encodes an oligopeptide transporter, was confirmed to be upregulated in the Bgl+ strain. Loss of oppA function results in a partial loss of the growth advantage in stationary-phase (GASP) phenotype of Bgl+ cells. The regulatory effect of the bgl operon on oppA expression is indirect and is mediated via gcvA, the activator of the glycine cleavage system, and gcvB, which regulates oppA at the posttranscriptional level. We show that BglG destabilizes the gcvA mRNA in vivo, leading to reduced expression of gcvA in the stationary phase. Deletion of gcvA results in the downregulation of gcvB and upregulation of oppA and can partially rescue the loss of the GASP phenotype seen in ?bglG strains. A possible mechanism by which oppA confers a competitive advantage to Bgl+ cells relative to Bgl? cells is discussed. PMID:22020646

Harwani, Dharmesh; Zangoui, Parisa

2012-01-01

317

Combined multispectroscopic and molecular docking investigation on the interaction between delphinidin-3-O-glucoside and bovine serum albumin.  

PubMed

Anthocyanin is one of the flavonoid phytopigments with specific health benefits. The interaction between delphinidin-3-O-glucoside (D3G) and bovine serum albumin (BSA) was investigated by fluorescence spectroscopy, synchronous fluorescence spectroscopy, three-dimensional fluorescence spectroscopy, ultraviolet-visible absorption spectroscopy, circular dichroism spectroscopy and molecular modeling. D3G effectively quenched the intrinsic fluorescence of BSA via static quenching. The number of binding sites and binding constant Ka were determined, and the hydrogen bonds and van der Waals forces played major roles in stabilizing the D3G-BSA complex. The distance r between donor and acceptor was obtained as 2.81 nm according to Förster's theory. In addition, the effects of pH and metal ions on the binding constants were discussed. The results studied by synchronous fluorescence, three-dimensional fluorescence and circular dichroism experiments indicated that the secondary structures of the protein has been changed by the addition of D3G and the ?-helix content of BSA decreased (from 56.1% to 52.4%). Furthermore, the study of site marker competitive experiments and molecular modeling indicated that D3G could bind to site I of BSA, which was in the large hydrophobic cavity of subdomain IIA. Copyright © 2014 John Wiley & Sons, Ltd. PMID:24891226

Zuo, Huijun; Tang, Lin; Li, Shu; Huang, Junwei

2015-02-01

318

The ?-glucoside (bgl) operon of Escherichia coli is involved in the regulation of oppA, encoding an oligopeptide transporter.  

PubMed

We report that the bgl operon of Escherichia coli, encoding the functions necessary for the uptake and metabolism of aryl-?-glucosides, is involved in the regulation of oligopeptide transport during stationary phase. Global analysis of intracellular proteins from Bgl-positive (Bgl(+)) and Bgl-negative (Bgl(-)) strains revealed that the operon exerts regulation on at least 12 downstream target genes. Of these, oppA, which encodes an oligopeptide transporter, was confirmed to be upregulated in the Bgl(+) strain. Loss of oppA function results in a partial loss of the growth advantage in stationary-phase (GASP) phenotype of Bgl(+) cells. The regulatory effect of the bgl operon on oppA expression is indirect and is mediated via gcvA, the activator of the glycine cleavage system, and gcvB, which regulates oppA at the posttranscriptional level. We show that BglG destabilizes the gcvA mRNA in vivo, leading to reduced expression of gcvA in the stationary phase. Deletion of gcvA results in the downregulation of gcvB and upregulation of oppA and can partially rescue the loss of the GASP phenotype seen in ?bglG strains. A possible mechanism by which oppA confers a competitive advantage to Bgl(+) cells relative to Bgl(-) cells is discussed. PMID:22020646

Harwani, Dharmesh; Zangoui, Parisa; Mahadevan, S

2012-01-01

319

LC determination and pharmacokinetic study of vitexin-4?-O-glucoside in rat plasma after oral administration.  

PubMed

A simple and specific high-performance liquid chromatography (HPLC) method was developed for the pharmacokinetic study of vitexin-4?-O-glucoside (VOG) in rats after oral administration. The plasma samples were deproteinised with methanol after the addition of an internal standard, hesperidin. HPLC analysis was performed on a Diamonsil C(18) analytical column, using methanol -0.5% aqueous phosphoric acid (45:55, v/v) as the mobile phase with ultraviolet detection at 330?nm. The calibration curve was linear over the range of 5-450?µg?mL(-1) in rat plasma. The average extraction recovery of VOG was 98.74%?±?0.44%, and the relative standard deviations of the intra- and inter-day precisions were not greater than 4.1% and 2.0%, respectively. The validated method was successfully applied during a pharmacokinetic study in rats after oral administration of VOG at different doses, and all the results indicated that the pharmacokinetics of VOG in rats obeyed nonlinear processes. PMID:21834625

Liu, Xun; Wang, Dong; Zhang, Wenjie; Wang, Nan; Wang, Siyuan; Li, Haibo; Ying, Xixiang; Kang, Tingguo

2012-01-01

320

Cholesteryl Glucoside Stimulates Activation of Protein Kinase B/Akt in the Motor Neuron-Derived NSC34 Cell Line.  

PubMed

Steryl glycosides and related compounds are commonly found in the environment and have been associated with neurodegenerative changes in vulnerable individuals. However, their mechanisms of action in mammalian cells have not been well investigated. In the present study the effects of cholesterol glucoside (CG), a variant form of steryl glycoside, was investigated in the motor neuron-derived NSC34 cell line. Prolonged treatment with CG was found to induce cell death in a dose- and time-dependent manner. However, transient exposure of CG preconditioned NSC34 cells for stress from serum deprivation. To study the signaling pathways activated by CG, we employed the Kinetworks™ KPSS 1.3 Phospho-site Screen to track the phosphorylation level of at least 35 diverse signaling proteins. The survival protein kinase B (PKB/Akt) displayed a 2-fold increase in phosphorylation at its Ser-473 activation site following CG stimulation. Akt signaling was important for conferring cytoprotection against serum deprivation-induced stress. Inhibition of phosphatidylinositol 3-kinase (PI3K), which indirectly triggers Akt stimulation, completely abolished CG preconditioning against serum deprivation. Our findings revealed that there may be a PI3K-independent pathway which also mediated Akt Ser-473 phosphorylation. Improved understanding of the mechanisms of action of CG should provide insights to the how other members of the steryl glycoside family induce toxicity in the mouse model of ALS-PDC, and how cells respond to these toxins. PMID:20936097

Ly, Philip T T; Pelech, Steven; Shaw, Christopher A

2008-01-01

321

Total glucosides of paeony inhibits Th1/Th17 cells via decreasing dendritic cells activation in rheumatoid arthritis.  

PubMed

Total glucoside of paeony (TGP), an active compound extracted from paeony root, has been used in therapy for rheumatoid arthritis (RA). Th1 and Th17 cells are now believed to play crucial roles in the lesions of RA. However, the molecular mechanism of TGP in inhibition of Th1 and Th17 cells remains unclear. In this study, we found that TGP treatment significantly decreased percentage and number of Th1 and Th17 cells in collagen induced arthritis (CIA) mice. Consistently, treatment with TGP decreased expression of T-bet and ROR?t as well as phosphorylation of STAT1 and STAT3. In particular, TGP treatment inhibited dendritic cells (DCs) maturation and reduced production of IL-12 and IL-6. Moreover, TGP-treatment RA patients showed shank population of matured DCs and IFN-?-, IL-17-producing cells. Taken together, our results demonstrated that TGP inhibited maturation and activation of DCs, which led to impaired Th1 and Th17 differentiation in vivo. PMID:23399842

Lin, Jinpiao; Xiao, Lianbo; Ouyang, Guilin; Shen, Yu; Huo, Rongfen; Zhou, Zhou; Sun, Yue; Zhu, Xianjin; Zhang, Jie; Shen, Baihua; Li, Ningli

2012-12-01

322

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

PubMed Central

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

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

2013-01-01

323

Structural elements responsible for the glucosidic linkage-selectivity of a glycoside hydrolase family 13 exo-glucosidase.  

PubMed

Glycoside hydrolase family 13 contains exo-glucosidases specific for ?-(1?4)- and ?-(1?6)-linkages including ?-glucosidase, oligo-1,6-glucosidase, and dextran glucosidase. The ?-(1?6)-linkage selectivity of Streptococcus mutans dextran glucosidase was altered to ?-(1?4)-linkage selectivity through site-directed mutations at Val195, Lys275, and Glu371. V195A showed 1300-fold higher kcat/Km for maltose than wild-type, but its kcat/Km for isomaltose remained 2-fold higher than for maltose. K275A and E371A combined with V195A mutation only decreased isomaltase activity. V195A/K275A, V195A/E371A, and V195A/K275A/E371A showed 27-, 26-, and 73-fold higher kcat/Km for maltose than for isomaltose, respectively. Consequently, the three residues are structural elements for recognition of the ?-(1?6)-glucosidic linkage. PMID:25728274

Saburi, Wataru; Rachi-Otsuka, Hiroaki; Hondoh, Hironori; Okuyama, Masayuki; Mori, Haruhide; Kimura, Atsuo

2015-03-24

324

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

PubMed

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

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

2011-12-28

325

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

326

Octyl glucoside extracts GTP-binding regulatory proteins from rat brain "synaptoneurosomes" as large, polydisperse structures devoid of beta gamma complexes and sensitive to disaggregation by guanine nucleotides.  

PubMed Central

GTP-binding regulatory proteins are generally purified from cholate-extracted membranes in the form of heterotrimers (G proteins) consisting of a GTP-binding subunit (alpha protein) complexed with a tightly interacted heterodimer termed beta gamma. In this study we extracted the proteins from rat brain "synaptoneurosomes" using the neutral detergent 1-octyl beta-D-glucopyranoside (octyl glucoside). Using specific antibodies for detection by immunoblotting and sucrose gradients for analyzing hydrodynamic properties, we found that each species of alpha protein (alpha subunits of stimulatory, inhibitory, and brain GTP-binding proteins) exhibited a broad range (4 S to greater than 12 S) of polydisperse structures with peak values (5 S to 7 S) considerably greater than that of heterotrimeric G proteins. The beta subunit proteins, for example, appeared as a homogeneous peak at 4.4 S within which only a fraction of the total alpha proteins can be associated. Incubation of octyl glucose extracts at 30 degrees C rapidly sedimented the alpha proteins but not the beta proteins. Incubation at 30 degrees C with guanosine 5'[gamma-thio]triphosphate (10-100 microM) prevented rapid sedimentation. Hydrodynamic analysis revealed that all alpha proteins were converted to approximately 4 S structures by the actions of guanosine 5'-[gamma-thio]triphosphate without change in the hydrodynamic properties of the beta proteins. Extraction of the membranes with sodium cholate instead of octyl glucoside resulted in complete loss of the large, polydisperse structures of the alpha proteins; the S values were approximately 4 S, in the range for beta proteins. These findings suggest that the transducing GTP-binding proteins in synaptoneurosomes exist as polydisperse, possibly multimer, structures of various size that are stable in octyl glucoside but destroyed by cholate. The polydisperse structures are not associated with beta gamma complexes and are sensitive to the disaggregating effects of guanosine 5'-[gamma-thio]triphosphate. Images PMID:2117281

Nakamura, S; Rodbell, M

1990-01-01

327

Liposomes as protective agents of stratum corneum against octyl glucoside: a study based on high-resolution, low-temperature scanning electron microscopy.  

PubMed

The ability of phosphatidylcholine (PC) liposomes to protect pig stratum corneum (SC) against the action of the nonionic surfactant octyl glucoside (OG) was investigated "in vitro" using double-layer coating for high-resolution, low-temperature scanning electron microscopy. This technique has been useful in preventing drying artifacts in the study of biological materials. The treatment of SC with OG led to a perturbation mainly in the corneocytes. However, the incubation of the tissue with liposomes prior to the OG treatment resulted in a progressive decrease in these perturbations and, consequently, in the progressive protection of the SC against the action of the surfactant. PMID:10936462

López, O; Cócera, M; Walther, P; Wehrli, E; Coderch, L; Parra, J L; de la Maza, A

2001-02-01

328

Genetic transformation of Gentiana macrophylla with Agrobacterium rhizogenes: growth and production of secoiridoid glucoside gentiopicroside in transformed hairy root cultures.  

PubMed

Hairy root cultures of Gentiana macrophylla were established by infecting the different explants four Agrobacterium rhizogenes strains namely A(4)GUS, R1000, LBA 9402 and ATCC11325, and hairy root lines were established with A. rhizogenes strain R1000 in 1/2 MS + B(5) medium. Initially, 42 independent hairy root clones were maintained and seven clones belongs to different category were evaluated for growth, morphology, integration and expression of Ri T-DNA genes, and alkaloid contents in dry root samples. On the basis of total root elongation, lateral root density and biomass accumulation on solid media, hairy root clones were separated into three categories. PCR and Southern hybridization analysis revealed both left and right T-DNA integration in the root clones and RT-PCR analysis confirmed the expression of hairy root inducible gene. GUS assay was also performed to confirm the integration of left T-DNA. The accumulation of considerable amounts of the root-specific secoiridoid glucosides gentiopicroside was observed in GM1 (T +/L and T +/R) and the GM2 (T +/L and T -/R DNA) type clones in considerably higher amount whether as two T -/L but T +/R callus-type clones (GM3) accumulated much less or only very negligible amounts of gentiopicroside. Out of four media composition the 1/2 MS + B(5) vitamin media was found most suitable. We found that initial establishment of root cultures largely depends on root:media ratio. Maximum growth rate was recorded in 1:50 root:media ratio. The maximum biomass in terms of fresh weight (33-fold) was achieved in 1/2 MS + B(5) media composition after 35 days in comparison to sixfold increase in control. The biomass increase was most abundant maximum from 15 to 30 days. Influence of A. rhizogenes strains and Ri plasmid of hairy root induction, the possible role of the T(L)-DNA and T(R)-DNA genes on growth pattern of hairy root, initial root inoculum:media ratio and effect of media composition is discussed. PMID:16972092

Tiwari, Rajesh Kumar; Trivedi, Mala; Guang, Zhang Chun; Guo, Guang-Qin; Zheng, Guo-Chang

2007-02-01

329

Survey of deoxynivalenol and its conjugates deoxynivalenol-3-glucoside and 3-acetyl-deoxynivalenol in 374 beer samples.  

PubMed

Beer is one of the most popular beverages worldwide. Malted cereal grains are among the basic ingredients and hence mycotoxin contamination might occur. Previous studies reported the presence of the Fusarium mycotoxins deoxynivalenol (DON) and 3-acetyl-deoxynivalenol (3ADON), as well as of the masked mycotoxin deoxynivalenol-3-glucoside (D3G) in beer. In the present survey, 374 beer samples from 38 countries with a focus on Austrian (156) and German (64) beers were analysed for the presence of D3G, DON and 3ADON. Beers were assigned to the following six categories: pale (217), wheat (46), dark (47), bock (20), nonalcoholic beers (19) and shandies (25). In total, 348 and 289 beers (93 and 77%, respectively) contained D3G and DON at the levels above the limit of detection, whereas 3ADON was not detected in any of the samples. Average concentrations of all beers were 6.9 µg L(-1) for D3G and 8.4 µg L(-1) in the case of DON. Nonalcoholic beers and shandies showed the lowest contaminations, 1.5 and 3.2 µg L(-1) for D3G and 2.7 and 4.4 µg L(-1) for DON, respectively. In bock beers characterised by a higher gravity, a significant trichothecene load of 14.8 µg L(-1) D3G and 12.4 µg L(-1) DON was found. The highest contamination (81 µg L(-1) D3G, 89 µg L(-1) DON) was detected in a pale beer from Austria, underlining the importance of this study for food safety. The molar D3G to DON ratio ranged between 0.11 and 1.25 and was 0.56 on average. Concluding, the average contamination of beer is not of toxicological concern for moderate beer drinkers. However, in the case of heavy beer drinkers, beer consumption may considerably contribute to the overall intake of DON, which might even lead to exceeding the maximum tolerable limits established for this Fusarium toxin. PMID:23025486

Varga, Elisabeth; Malachova, Alexandra; Schwartz, Heidi; Krska, Rudolf; Berthiller, Franz

2013-01-01

330

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

PubMed

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

Nielsen, J S; Møller, B L

2000-04-01

331

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

PubMed Central

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

Nielsen, John Strikart; Møller, Birger Lindberg

2000-01-01

332

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

PubMed

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

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

2014-01-01

333

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

PubMed Central

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

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

2014-01-01

334

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

PubMed Central

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

Park, Chung Mu

2013-01-01

335

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

PubMed

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

Park, Chung Mu; Song, Young-Sun

2013-12-01

336

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

337

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

338

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

PubMed

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

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

2015-01-01

339

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

Microsoft Academic Search

The mechanisms governing the solubilization by Triton X-100, octyl glucoside, and sodium cholate of large unilamellar liposomes prepared by reverse-phase evaporation were investigated. The solubilization process is described by the three-stage model previously proposed for the detergents. In stage I, detergent monomers are incorporated into the phospholipid bilayers until they saturate the liposomes. At this point, i.e., stage II, mixed

Marie Therese Paternostre; Michel Roux; Jean Louis Rigaud

1988-01-01

340

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

341

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

PubMed

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

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

2014-07-25

342

Effect of 2,3,5,4'-tetrahydroxystilbene-2-O-beta-D-glucoside on lipoprotein oxidation and proliferation of coronary arterial smooth cells.  

PubMed

To investigate the effects of 2,3,5,4'-tetrahydroxystilbene-2-O-beta-D-glucoside (THSG), a compound extracted from the root of Polygonum multiflorum Thunb, on lipoprotein (LDL and VLDL) oxidation, proliferation and nitric oxide (NO) content of coronary arterial smooth cells (CASMCs) induced by LDL, VLDL, ox-LDL and ox-VLDL. The oxidation level of lipoprotein was determined by thiobabituric acid (TBA) method and agarose gel electrophoresis. The proliferative degree was determined by 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyl tetrazolium bromide (MTT) method. The NO content was assayed by nitrate reductase method. (1)THSG (0.1 - 100 mumol L(- 1)) could dose-dependently prevent lipoprotein from oxidation induced by Cu(2 + ) and CASMCs. (2)THSG (0.1 - 100 micromol L(- 1)) inhibited porcine CASMCs proliferation elicited by LDL, VLDL, ox-LDL and ox-VLDL. (3)THSG (0.1 - 100 micromol L(- 1)) counterpoised the decrease of NO content in CASMCs evoked by LDL, VLDL, ox-LDL and ox-VLDL. As compared with control, it was found that the threshold concentration of THSG, which significantly exerted the actions mentioned above, were at the concentration of 1 micromol.L(- 1) (P < 0.01). In conclusion, THSG possesses the antagonistic effects on oxidation of lipoprotein, proliferation and decrease of NO content of CASMCs, which partially explain the mechanism of anti-atherosclerosis of Polygonum multiflorum Thunb. PMID:17701557

Liu, Qi-Li; Xiao, Jun-Hua; Ma, Rong; Ban, Yi; Wang, Jia-Ling

2007-01-01

343

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

PubMed

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

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

2013-11-15

344

Intestinal SGLT1-mediated absorption and metabolism of benzyl beta-glucoside contained in Prunus mume: carrier-mediated transport increases intestinal availability.  

PubMed

The intestinal absorption of benzyl beta-glucoside (BNZ beta glc) contained in the fruit of Prunus mume SIEB. et ZUCC. (Rosaceae), which is traditionally used as a medicinal food in Japan, was studied in rat intestines. BNZ beta glc was absorbed from the mucosal to serosal sides. Its metabolite, benzyl alcohol (BAL), was also detected on both the mucosal and serosal sides. In the presence of phloridzin (Na(+)/glucose cotransporter (SGLT1) inhibitor) or in the absence of Na+ (driving force), BNZ beta glc absorption was significantly decreased. Transport clearance of BNZ beta glc across the brush border membrane decreased as its concentration increased. These results indicate that BNZ beta glc is transported by SGLT1. Metabolic clearance of BNZ beta glc also decreased as its concentration increased. The amount ratio of BNZ beta glc to BAL on the serosal side increased with the increase of BNZ beta glc concentration. The intestinal availability of BNZ beta glc was lower in the absence of Na+ than in the presence of Na+, indicating that the SGLT1-mediated transport of BNZ beta glc increases intestinal availability by decreasing the intestinal extraction ratio. This neutraceutical study concluded that intestinal carrier-mediated transport across the brush border membrane improves the intestinal availability of nutritionally, pharmacologically or physiologically active compounds that undergo intestinal metabolism (first-pass effect). PMID:15716003

Mizuma, Takashi; Nakamura, Maya; Ina, Hiroji; Miyazaki, Toshio; Hayashi, Masahiro

2005-03-11

345

Development and validation of an HPTLC method for apigenin 7-O-glucoside in chamomile flowers and its application for fingerprint discrimination of chamomile-like materials.  

PubMed

Brewed tea of chamomile flowers (Matricaria recutita L.) (Asteraceae) has been extensively consumed for centuries due to either its pleasant taste or medicinal purposes. On the other hand, the major problem is difficulty in distinguishing the genuine specimen when supplying chamomile through nature-picking. Consequently flowers of other Asteraceae members resembling to chamomile in appearance may frequently be practiced by lay people or marketed in spice shops or bazaars. Evidently detection of such adulterations plays a vital role in terms of public health to avoid risk of toxicity (i.e. pyrazolidin alkaloids) and ineffective treatments (lack or insufficient concentration of the active constituents). This work presents either development and validation of a high performance thin-layer chromatographic (HPTLC) method for apigenin 7-O-glucoside which is one of the active markers in chamomile flowers or its application for the fingerprint discrimination of chamomile-like materials i.e. Anthemis spp., Bellis spp., Chrysanthemum sp. and Tanacetum sp. gathered by local people assuming as chamomile. Separation was performed on the silica gel 60 NH2 F254s HPTLC plates using the developing solvent system of ethyl acetate-formic acid-acetic acid-water (30:1.5:1.5:3, v/v/v/v). The proposed HPTLC method may also be a leading guide for the quality assessment of chamomile tea products on the market. PMID:25575175

Guzelmeric, Etil; Vovk, Irena; Yesilada, Erdem

2015-03-25

346

Determination of iriflophenone 3-C-?-d-glucoside from Aquilaria spp. by an indirect competitive enzyme-linked immunosorbent assay using a specific polyclonal antibody.  

PubMed

Polyclonal antibody against iriflophenone 3-C-?-d-glucoside (IP3G), a major compound from the leaves of Aquilaria spp., was produced for the development of an enzyme-linked immunosorbent assay (ELISA). The results showed that the antibodies were specific for IP3G. The produced antibody has low cross reactivity with iriflophenone 3,5-C-?-d-diglucopyranoside (13%), genkwanin 5-O-?-primeveroside (3.55%) and no cross reactivity found in other compounds. The range of ELISA assay extends from 100 to 1560 ng/mL with coefficient of variation (CV) 1.19% to 2.07% for intra-assay and 3.76% to 7.15% for inter-assay precision levels. The recovery rates of IP3G in the leaves of Aquilaria spp. were in the range of 96.0% to 99.0% with CV 4.50% to 5.32%. A correlation between ELISA and high-performance liquid chromatography methods was obtained when analysis of IP3G in the plant samples (R(2) = 0.9321). These results suggest that the developed ELISA method can be applied to determine IP3G content with high specificity, rapidity, and simplicity. The developed immunosorbent assay in this study provides a useful tool for the analysis of IP3G in plant samples and products. PMID:23924405

Putalun, Waraporn; Yusakul, Gorawit; Saensom, Paritad; Sritularak, Boonchoo; Tanaka, Hiroyuki

2013-09-01

347

High Expression of ?-glucosidase in Bifidobacterium bifidum BGN4 and Application in Conversion of Isoflavone Glucosides during Fermentation of Soy Milk.  

PubMed

In spite of the reported probiotic effects, Bifidobacterium bifidum BGN4 (BGN4) showed no ?-glucosidase activity and failed to biotransform isoflavone glucosides into the more bioactive alycones during soy milk fermentation. To develop isoflavone biotransforming BGN4, we constructed the recombinant B. bifidum BGN4 strain (B919G) by cloning the structural ?-glucosidase gene from B. lactis AD011 (AD011) using the expression vector with constitutively active promoter 919 from BGN4. As a result, B919G highly expressed ?-glucosidase and showed higher ?-glucosidase activity and heat stability than the source strain of ?-glucosidase gene, AD011. The biotransformation of daidzin and genistin compounds using the crude enzyme extract from B919G was completed within 4 h, and the bioconversion of daidzin and genistin in soy milk during fermentation with B919G also occurred within 6 h, which was much faster and higher than AD011. The incorporation of ?-glucosidase producing Bifidobacterium strain in soy milk could lead to a production of fermented soy milk with elevated amount of bioavailable forms of isoflavones as well as the indigenous probiotic effects of the Bifidobacterium strain. PMID:25348696

You, Hyun Ju; Ahn, Hyung Jin; Kim, Jin Yong; Wu, Qian Qian; Ji, Geun Eog

2014-10-28

348

Cyanidin-3-O-?-glucoside regulates fatty acid metabolism via an AMP-activated protein kinase-dependent signaling pathway in human HepG2 cells  

PubMed Central

Background Hepatic metabolic derangements are key components in the development of fatty liver disease. AMP-activated protein kinase (AMPK) plays a central role in controlling hepatic lipid metabolism through modulating the downstream acetyl CoA carboxylase (ACC) and carnitine palmitoyl transferase 1 (CPT-1) pathway. In this study, cyanidin-3-O-?-glucoside (Cy-3-g), a typical anthocyanin pigment was used to examine its effects on AMPK activation and fatty acid metabolism in human HepG2 hepatocytes. Results Anthocyanin Cy-3-g increased cellular AMPK activity in a calmodulin kinase kinase dependent manner. Furthermore, Cy-3-g substantially induced AMPK downstream target ACC phosphorylation and inactivation, and then decreased malonyl CoA contents, leading to stimulation of CPT-1 expression and significant increase of fatty acid oxidation in HepG2 cells. These effects of Cy-3-g are largely abolished by pharmacological and genetic inhibition of AMPK. Conclusion This study demonstrates that Cy-3-g regulates hepatic lipid homeostasis via an AMPK-dependent signaling pathway. Targeting AMPK activation by anthocyanin may represent a promising approach for the prevention and treatment of obesity-related nonalcoholic fatty liver disease. PMID:22243683

2012-01-01

349

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

350

Microarray Analysis of mRNA and MicroRNA Expression Profile Reveals the Role of ?-Sitosterol-D-glucoside in the Proliferation of Neural Stem Cell  

PubMed Central

Neural stem cells (NSCs) are self-regenerating cells, but their regenerative capacity is limited. The present study was conducted to investigate the effect of ?-sitosterol-D-glucoside (BSSG) on the proliferation of hippocampal NSCs and to determine the corresponding molecular mechanism. Results of CCK-8 assay showed that BSSG significantly increased NSC proliferation and the effectiveness of BSSG was similar to that of basic fibroblast growth factor and epidermal growth factor. mRNA expression profiling showed that 960 genes were differentially expressed after NSCs were treated with BSSG. Among the 960 genes, IGF1 is considered as a key regulatory gene that functionally promotes NSC proliferation. MicroRNA (miRNA) expression profiling indicated that 30 and 84 miRNAs were upregulated and downregulated, respectively. miRNA-mRNA relevance analysis revealed that numerous mRNAs including IGF1 mRNA were negatively regulated by miRNAs with decreased expression, thereby increasing the corresponding mRNA expression. The increased expression of IGF1 protein was validated by ELISA. Picropodophyllin (PPP, an inhibitor of IGF-1R) inhibition test confirmed that the proliferation-enhancing effect depended on IGF1. This study provided information about BSSG as an efficient and inexpensive growth factor alternative, of which the effect is closely involved in IGF1. PMID:24391673

Jiang, Li-hua; Yang, Nian-yun; Yuan, Xiao-lin; Zou, Yi-jie; Jiang, Ze-qun; Zhao, Feng-ming; Chen, Jian-ping; Wang, Ming-yan; Lu, Da-xiang

2013-01-01

351

Downregulation of a Pathogen-Responsive Tobacco UDP-Glc:Phenylpropanoid Glucosyltransferase Reduces Scopoletin Glucoside Accumulation, Enhances Oxidative Stress, and Weakens Virus Resistance  

PubMed Central

Plant UDP-Glc:phenylpropanoid glucosyltransferases (UGTs) catalyze the transfer of Glc from UDP-Glc to numerous substrates and regulate the activity of compounds that play important roles in plant defense against pathogens. We previously characterized two tobacco salicylic acid– and pathogen-inducible UGTs (TOGTs) that act very efficiently on the hydroxycoumarin scopoletin and on hydroxycinnamic acids. To identify the physiological roles of these UGTs in plant defense, we generated TOGT-depleted tobacco plants by antisense expression. After inoculation with Tobacco mosaic virus (TMV), TOGT-inhibited plants exhibited a significant decrease in the glucoside form of scopoletin (scopolin) and a decrease in scopoletin UGT activity. Unexpectedly, free scopoletin levels also were reduced in TOGT antisense lines. Scopolin and scopoletin reduction in TOGT-depleted lines resulted in a strong decrease of the blue fluorescence in cells surrounding TMV lesions and was associated with weakened resistance to infection with TMV. Consistent with the proposed role of scopoletin as a reactive oxygen intermediate (ROI) scavenger, TMV also triggered a more sustained ROI accumulation in TOGT-downregulated lines. Our results demonstrate the involvement of TOGT in scopoletin glucosylation in planta and provide evidence of the crucial role of a UGT in plant defense responses. We propose that TOGT-mediated glucosylation is required for scopoletin accumulation in cells surrounding TMV lesions, where this compound could both exert a direct antiviral effect and participate in ROI buffering. PMID:12034899

Chong, Julie; Baltz, Rachel; Schmitt, Corinne; Beffa, Roland; Fritig, Bernard; Saindrenan, Patrick

2002-01-01

352

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 Galvão; Souto, Pollyana Cristina Maggio de Castro; Teixeira, Catarina; Lajolo, Franco Maria

2013-01-01

353

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

PubMed

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

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

2015-03-01

354

Cyanidin-3-O-glucoside modulates intracellular redox status and prevents HIF-1 stabilization in endothelial cells in vitro exposed to chronic hypoxia.  

PubMed

The term hypoxia refers to conditions characterized by a relative restriction of oxygen supply. It is usually associated to a paradoxical overproduction of reactive oxygen species (ROS) and to the activation of several transcription factors, including HIF-1?, which in turn trigger angiogenic and apoptotic response. In this study we have investigated the mechanisms by which the anthocyanin cyanidin-3-O-glucoside (C3G) modulates hypoxia induced response in human endothelial cells (HUVECs). In fact, hypoxia induces an increase of ROS generation in HUVECs paralleled by a loss of antioxidant cellular capacity. According to the observed increase of HO-1 mRNA expression, pretreatment of C3G to HUVEC reduces the entity of oxidative stress thanks to the activation of cellular antioxidant response. C3G also attenuates HIF-1? protein accumulation conditions supporting the hypothesis of a major role of oxidative stress in the presence of low oxygen. Furthermore, the increased expression of angiogenesis and apoptosis markers (MMP-2 and caspase-3) due to HIF-1? activation by hypoxia is reduced in C3G pretreated cells. Overall, our data suggest that the modulation of intracellular redox status induced by C3G may be an important protective mechanism against endothelial damage in hypoxic conditions. PMID:24518827

Anwar, S; Speciale, A; Fratantonio, D; Cristani, M; Saija, A; Virgili, F; Cimino, F

2014-04-21

355

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

356

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

357

Comparative study on the excretion of vitexin-4''-O-glucoside in mice after oral and intravenous administration by using HPLC.  

PubMed

The aim of the present study was to characterize the excretion of pure vitexin-4"-O-glucoside (VOG) in mice following oral and intravenous administration at a dose of 30 mg/kg. A sensitive and specific HPLC method with hespridin as internal standard, a Diamonsil C18 column protected with a KR C18 guard column and a mixture consisting of methanol-acetonitrile-tetrahydrofuran-0.1% glacial acetic acid (6:2:18:74, v/v/v/v) as mobile phase was developed and validated for quantitative analysis in biological samples. VOG could be excreted as prototype in excreta including urine and feces after both routes of administration, and the cumulative excretion of VOG was 24.31?±?11.10% (17.97?±?5.59% in urinary excretion; 6.34?±?5.51% in fecal excretion) following oral dosing and 5.66?±?3.94% (4.78?±?3.13% in urinary excretion; 0.88?±?0.81% in fecal excretion) following intravenous dosing. The results showed that the elimination of VOG after the two routes was fairly low, which meant that VOG was metabolized as other forms and the elimination after oral dosing was almost 4.3-fold that after intravenous dosing. For both routes of administration, VOG excreted as prototype in urine was much more than that in feces, nearly 2.83-fold for oral administration and 5.43-fold for intravenous administration, which should be attributed to enterohepatic circulation. Taken together, renal excretion was the dominant path of elimination of VOG for oral and intravenous administration in mice and biliary excretion contributed less. PMID:23760836

Cai, Shuang; Chen, Yinghui; Zhang, Wenjie; Ying, Xixiang

2013-11-01

358

Total glucosides of paeony inhibit the proliferation of fibroblast-like synoviocytes through the regulation of G proteins in rats with collagen-induced arthritis.  

PubMed

The aim of this study was to investigate the expression of G proteins in fibroblast-like synoviocytes (FLSs) from rats with collagen-induced arthritis (CIA) and to determine the effect of total glucosides of paeony (TGP). CIA rats were induced with chicken type II collagen (CCII) in Freund's complete adjuvant. The rats with experimental arthritis were randomly separated into five groups and then treated with TGP (25, 50, and 100mg/kg) from days 14 to 35 after immunization. The secondary inflammatory reactions were evaluated through the polyarthritis index and histopathological changes. The level of cyclic adenosine monophosphate (cAMP) was measured by radioimmunoassay. The FLS proliferation response was determined by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. The toxin-catalyzed ADP-ribosylation of G proteins was performed through autoradiography. The results show that TGP (25, 50, and 100mg/kg) significantly decreased the arthritis scores of CIA rats and improved the histopathological changes. TGP inhibited the proliferation of FLSs and increased the level of cAMP. Moreover, the FLS proliferation and the level of G?i expression were significantly increased, but the level of G?s expression was decreased after stimulation with IL-1? (10ng/ml) in vitro. TGP (12.5 and 62.5?g/ml) significantly inhibited the FLS proliferation and regulated the balance between G?i and G?s. These results demonstrate that TGP may exert its anti-inflammatory effects through the suppression of FLS proliferation, which may be associated with its ability to regulate the balance of G proteins. Thus, TGP may have potential as a therapeutic agent for the treatment of rheumatoid arthritis. PMID:24161745

Jia, Xiao-Yi; Chang, Yan; Sun, Xiao-Jing; Wu, Hua-Xun; Wang, Chun; Xu, Hong-Mei; Zhang, Lei; Zhang, Ling-Ling; Zheng, Yong-Qiu; Song, Li-Hua; Wei, Wei

2014-01-01

359

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

PubMed

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

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

2010-07-01

360

Oral bioavailability and pharmacokinetics of elimination of 9-hydroxybenzo[a]pyrene and its glucoside and sulfate conjugates after administration to male and female American lobsters, Homarus americanus.  

PubMed

The pharmacokinetics of [(3)H]-9-hydroxybenzo[a]pyrene (9-OH-BaP), a highly lipophilic primary metabolite of benzo(a)pyrene, were examined after intrapericardial (iv) or oral doses of 50 or 200 microg/kg to intermolt American lobsters, Homarus americanus. Combining data for all lobsters, the average terminal elimination half-life of parent 9-OH-BaP was 97.3 h after iv and 56.5 h after oral administration, considerably less than found previously for benzo(a)pyrene (720 h). The oral bioavailability of parent 9-OH-BaP, calculated from the area under the hemolymph concentration curve, was 15.9%. The low bioavailability and variable elimination rates were attributed to extensive first-pass conjugation and sequestration in the hepatopancreas. BaP-9-sulfate was the major metabolite. Hemolymph concentrations of BaP-9-sulfate increased up to one day after the dose, and then decreased, with a terminal elimination half-life of 45 h. BaP 9-beta-D-glucoside was a minor metabolite in most hemolymph and tissue samples; an exception was hemolymph from the iv high-dose group. Concentrations of 9-OH-BaP and metabolites in the edible muscle tissue were similar to those in hemolymph, and 9-OH-BaP residues at 10 to 16 days after the dose were 3 to 12 ng/g muscle. Sulfotransferase and UDP-glucosyltransferase (UGT) activities with 9-OH-BaP were found in the antennal gland, intestinal mucosa, and hepatopancreas (UGT only). Sulfatase activity with BaP-9-sulfate, found in both the hepatopancreas and the antennal gland, was thought to contribute to metabolite cycling. These studies showed that 9-OH-BaP was readily conjugated to sulfate and glucose in the lobster, and that despite their high lipophilicity, 9-OH-BaP and conjugates were excreted from the lobster hemolymph and tissues much more rapidly than benzo[a]pyrene. PMID:10966513

Li, C L; James, M O

2000-09-01

361

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

PubMed Central

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

Chang, Youngeun

2013-01-01

362

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

363

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

PubMed

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

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

2013-01-01

364

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

365

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

PubMed Central

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

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

2011-01-01

366

The presence of CYP79 homologues in glucosinolate-producing plants shows evolutionary conservation of the enzymes in the conversion of amino acid to aldoxime in the biosynthesis of cyanogenic glucosides and glucosinolates.  

PubMed

A cDNA encoding CYP79B1 has been isolated from Sinapis alba. CYP79B1 from S. alba shows 54% sequence identity and 73% similarity to sorghum CYP79A1 and 95% sequence identity to the Arabidopsis T42902, assigned CYP79B2. The high identity and similarity to sorghum CYP79A1, which catalyses the conversion of tyrosine to p-hydroxyphenylacetaldoxime in the biosynthesis of the cyanogenic glucoside dhurrin, suggests that CYP79B1 similarly catalyses the conversion of amino acid(s) to aldoxime(s) in the biosynthesis of glucosinolates. Within the highly conserved 'PERF' and the heme-binding region of A-type cytochromes, the CYP79 family has unique substitutions that define the family-specific consensus sequences of FXP(E/D)RH and SFSTG(K/R)RGC(A/I)A, respectively. Sequence analysis of PCR products generated with CYP79B subfamily-specific primers identified CYP79B homologues in Tropaeolum majus, Carica papaya, Arabidopsis, Brassica napus and S. alba. The five glucosinolate-producing plants identified a CYP79B amino acid consensus sequence KPERHLNECSEVTLTENDLRFISFSTGKRGC. The unique substitutions in the 'PERF' and the heme-binding domain and the high sequence identity and similarity of CYP79B1, CYP79B2 and CYP79A1, together with the isolation of CYP79B homologues in the distantly related Tropaeolaceae, Caricaceae and Brassicaceae within the Capparales order, show that the initial part of the biosynthetic pathway of glucosinolates and cyanogenic glucosides is catalysed by evolutionarily conserved cytochromes P450. This confirms that the appearance of glucosinolates in Capparales is based on a cyanogen 'predisposition'. Identification of CYP79 homologues in glucosinolate-producing plants provides an important tool for tissue-specific regulation of the level of glucosinolates to improve nutritional value and pest resistance. PMID:9862490

Bak, S; Nielsen, H L; Halkier, B A

1998-11-01

367

Cyanidin-3-glucoside inhibits glutamate-induced Zn(2+) signaling and neuronal cell death in cultured rat hippocampal neurons by inhibiting Ca(2+)-induced mitochondrial depolarization and formation of reactive oxygen species.  

PubMed

Cyanidin-3-glucoside (C3G), a member of the anthocyanin family, is a potent natural antioxidant. However, effects of C3G on glutamate-induced [Zn(2+)]i increase and neuronal cell death remain unknown. We studied the effects of C3G on glutamate-induced [Zn(2+)]i increase and cell death in cultured rat hippocampal neurons from embryonic day 17 maternal Sprague-Dawley rats using digital imaging methods for Zn(2+), Ca(2+), reactive oxygen species (ROS), mitochondrial membrane potential and a MTT assay for cell survival. Treatment with glutamate (100µM) for 7min induces reproducible [Zn(2+)]i increase at 35min interval in cultured rat hippocampal neurons. The intracellular Zn(2+)-chelator TPEN markedly blocked glutamate-induced [Zn(2+)]i increase, but the extracellular Zn(2+) chelator CaEDTA did not affect glutamate-induced [Zn(2+)]i increase. C3G inhibited the glutamate-induced [Zn(2+)]i response in a concentration-dependent manner (IC50 of 14.1±1.1µg/ml). C3G also significantly inhibited glutamate-induced [Ca(2+)]i increase. Two antioxidants such as Trolox and DTT significantly inhibited the glutamate-induced [Zn(2+)]i response, but they did not affect the [Ca(2+)]i responses. C3G blocked glutamate-induced formation of ROS. Trolox and DTT also inhibited the formation of ROS. C3G significantly inhibited glutamate-induced mitochondrial depolarization. However, TPEN, Trolox and DTT did not affect the mitochondrial depolarization. C3G, Trolox and DTT attenuated glutamate-induced neuronal cell death in cultured rat hippocampal neurons, respectively. Taken together, all these results suggest that cyanidin-3-glucoside inhibits glutamate-induced [Zn(2+)]i increase through a release of Zn(2+) from intracellular sources in cultured rat hippocampal neurons by inhibiting Ca(2+)-induced mitochondrial depolarization and formation of ROS, which is involved in neuroprotection against glutamate-induced cell death. PMID:25721794

Yang, Ji Seon; Perveen, Shazia; Ha, Tae Joung; Kim, Seong Yun; Yoon, Shin Hee

2015-05-01

368

Simultaneous determination of calycosin-7-O-?-D-glucoside, ononin, calycosin, formononetin, astragaloside IV, and astragaloside II in rat plasma after oral administration of Radix Astragali extraction for their pharmacokinetic studies by ultra-pressure liquid chromatography with tandem mass spectrometry.  

PubMed

A sensitive and reliable ultra-pressure liquid chromatography with tandem mass spectrometry (UPLC-MS) was developed and validated for simultaneous quantification of six main bioactive components, i.e., calycosin-7-O-?-D-glucoside, ononin, calycosin, formononetin, astragaloside IV, and astragaloside II in rat plasma after oral administration of the 95 % ethanol extraction from Radix Astragali. Plasma samples were extracted with Waters Oasis(TM) HLB 1 cc (30 mg) Extraction Cartridges (SPE) separated on an UPLC™ BEH C18 column and detected by MS with electro spray ionization interface in positive selective ion monitoring mode. Calibration curves offered linear ranges of two orders of magnitude with r (2) > 0.99. The method had the lower limit quantification of 1.30, 0.73, 1.17, 2.33, 0.63, and 0.83 ng/mL for ononin, calycosin, calycosin-7-O-?-D-glucoside, formononetin, astragaloside IV, and astragaloside II, respectively, with precision less than 10 %. The RSD of intra- and inter-day variations ranged from 1.66 to 6.46 and 3.39 to 6.58 %. This developed method was applied subsequently to pharmacokinetic studies of the six compounds in rats successfully. The proposed method was for the first time to compare the pharmacokinetic difference between calycosin-7-O-?-D-glucoside and calycosin in rat plasma, so as between ononin and formononetin, and studied to the astragaloside II pharmacokinetics in rat plasma. PMID:24782060

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

2014-09-01

369

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

PubMed

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

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

2007-12-01

370

Molecular mechanisms of luteolin-7-O-glucoside-induced growth inhibition on human liver cancer cells: G2/M cell cycle arrest and caspase-independent apoptotic signaling pathways  

PubMed Central

Luteolin-7-O-glucoside (LUT7G), a flavone subclass of flavonoids, has been found to increase anti-oxidant and anti-inflammatory activity, as well as cytotoxic effects. However, the mechanism of how LUT7G induces apoptosis and regulates cell cycles remains poorly understood. In this study, we examined the effects of LUT7G on the growth inhibition of tumors, cell cycle arrest, induction of ROS generation, and the involved signaling pathway in human hepatocarcinoma HepG2 cells. The proliferation of HepG2 cells was decreased by LUT7G in a dose-dependent manner. The growth inhibition was due primarily to the G2/M phase arrest and ROS generation. Moreover, the phosphorylation of JNK was increased by LUT7G. These results suggest that the anti-proliferative effect of LUT7G on HepG2 is associated with G2/M phase cell cycle arrest by JNK activation. [BMB Reports 2013; 46(12): 611-616] PMID:24257119

Hwang, Yu-Jin; Lee, Eun-Ju; Kim, Haeng-Ran; Hwang, Kyung-A

2013-01-01

371

Transcriptome profiling and digital gene expression analysis of Fallopia multiflora to discover putative genes involved in the biosynthesis of 2,3,5,4'-tetrahydroxy stilbene-2-O-?-D-glucoside.  

PubMed

The compound 2,3,5,4'-tetrahydroxy stilbene-2-O-ß-d-glucoside (THSG) synthesized by Fallopia multiflora (F. multiflora) exhibits pharmacological potency. However, the mechanistic details of its biosynthesis pathway are still vague. To clear this ambiguity, we performed de novo transcriptome assembly and digital gene expression (DGE) profiling analyses of F. multiflora using the Illumina RNA-seq system. RNA-seq generated approximately 70 million high-quality reads that were assembled into 65,653 unigenes (mean length=750 bp), including 26,670 clusters and 38,983 singletons. A total of 48,173 (73.4%) unigenes were annotated using public protein databases with a cut-off e-value above 10(-5). Furthermore, we investigated the transcriptome difference of four different F. multiflora tissues using DGE profiling. Variations in gene expression were identified based on comparisons of transcriptomes from various parts of a high-level THSG- and a low-level THSG-producing F. multiflora plant. Clusters with similar differential expression patterns and enriched metabolic pathways with regard to the differentially expressed genes putatively involved in THSG biosynthesis were revealed for the first time. Our data provides the most comprehensive sequence resource regarding F. multiflora so far. Taken together, the results of this study considerably extend the knowledge on THSG production. PMID:24967942

Zhao, Wei; Xia, Wanxia; Li, Jiewen; Sheng, Shujing; Lei, Lei; Zhao, Shujing

2014-08-15

372

Esculetin and esculin (esculetin 6-O-glucoside) occur as inclusions and are differentially distributed in the vacuole of palisade cells in Fraxinus ornus leaves: a fluorescence microscopy analysis.  

PubMed

The location of individual coumarins in leaves of Fraxinus ornus acclimated at full solar irradiance was estimated using their specific UV- and fluorescence spectral features. Using a combination of UV-induced fluorescence and blue light-induced fluorescence of tissues stained with diphenylborinic acid 2-amino-ethylester, in wide field or confocal laser scanning microscopy, we were able to visualize the distribution of esculetin and esculetin 6-O-glucoside (esculin) in palisade cells. Coumarins are not uniformly distributed in the cell vacuole, but accumulate mostly in the adaxial portion of palisade cells. Our study indeed shows, for the first time, that coumarins in palisade cells accumulate as vacuolar inclusions, as previously reported in the pertinent literature only for anthocyanins. Furthermore, esculetin and esculin have a different vacuolar distribution: esculetin largely predominates in the first 15 ?m from the adaxial epidermis. This leads to hypothesize for esculetin and esculin different transport mechanisms from the endoplasmic reticulum to the vacuole as well as potentially different roles in photoprotection. Our study open to new experiments aimed at exploring the mechanisms that deliver coumarins to the vacuole using different fluorescence signatures of coumarin aglycones and coumarin glycosides. PMID:25063983

Tattini, Massimiliano; Di Ferdinando, Martina; Brunetti, Cecilia; Goti, Andrea; Pollastri, Susanna; Bellasio, Chandra; Giordano, Cristiana; Fini, Alessio; Agati, Giovanni

2014-11-01

373

Plant chemical defense against herbivores and pathogens: generalized defense or trade-offs?  

PubMed

Plants are often attacked by multiple enemies, including pathogens and herbivores. While many plant secondary metabolites show specific effects toward either pathogens or herbivores, some can affect the performance of both these groups of natural enemies and are considered to be "generalized defense compounds". We tested whether aucubin and catalpol, two iridoid glycosides present in ribwort plantain (Plantago lanceolata), confer in vivo resistance to both the generalist insect herbivore Spodoptera exigua and the biotrophic fungal pathogen Diaporthe adunca using plants from P. lanceolata lines that had been selected for high- and low-leaf iridoid glycoside concentrations for four generations. The lines differed approximately three-fold in the levels of these compounds. Plants from the high-selection line showed enhanced resistance to both S. exigua and D. adunca, as evidenced by a smaller lesion size and a lower fungal growth rate and spore production, and a lower larval growth rate and herbivory under both choice and no-choice conditions. Gravimetric analysis revealed that the iridoid glycosides acted as feeding deterrents to S. exigua, thereby reducing its food intake rate, rather than having post-ingestive toxic effects as predicted from in vitro effects of hydrolysis products. We suggest that the bitter taste of iridoid glycosides deters feeding by S. exigua, whereas the hydrolysis products formed after tissue damage following fungal infection mediate pathogen resistance. We conclude that iridoid glycosides in P. lanceolata can serve as broad-spectrum defenses and that selection for pathogen resistance could potentially result in increased resistance to generalist insect herbivores and vice versa, resulting in diffuse rather than pairwise coevolution. PMID:15146326

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

2004-08-01

374

Direct comparison between genomic constitution and flavonoid contents in Allium multiple alien addition lines reveals chromosomal locations of genes related to biosynthesis from dihydrokaempferol to quercetin glucosides in scaly leaf of shallot (Allium cepa L.).  

PubMed

The extrachromosome 5A of shallot (Allium cepa L., genomes AA) has an important role in flavonoid biosynthesis in the scaly leaf of Allium fistulosum-shallot monosomic addition lines (FF+nA). This study deals with the production and biochemical characterisation of A. fistulosum-shallot multiple alien addition lines carrying at least 5A to determine the chromosomal locations of genes for quercetin formation. The multiple alien additions were selected from the crossing between allotriploid FFA (female symbol) and A. fistulosum (male symbol). The 113 plants obtained from this cross were analysed by a chromosome 5A-specific PGI isozyme marker of shallot. Thirty plants were preliminarily selected for an alien addition carrying 5A. The chromosome numbers of the 30 plants varied from 18 to 23. The other extrachromosomes in 19 plants were completely identified by using seven other chromosome markers of shallot. High-performance liquid chromatography analyses of the 19 multiple additions were conducted to identify the flavonoid compounds produced in the scaly leaves. Direct comparisons between the chromosomal constitution and the flavonoid contents of the multiple alien additions revealed that a flavonoid 3'-hydroxylase (F3'H) gene for the synthesis of quercetin from kaempferol was located on 7A and that an anonymous gene involved in the glucosidation of quercetin was on 3A or 4A. As a result of supplemental SCAR analyses by using genomic DNAs from two complete sets of A. fistulosum-shallot monosomic additions, we have assigned F3'H to 7A and flavonol synthase to 4A. PMID:16411131

Masuzaki, S; Shigyo, M; Yamauchi, N

2006-02-01

375

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

376

2-Nitro-3-(p-hydroxyphenyl)propionate and aci-1-nitro-2-(p-hydroxyphenyl)ethane, two intermediates in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L. ) Moench  

SciTech Connect

The biosynthetic pathway for the cyanogenic glucoside dhurrin derived from tyrosine has been studied in vitro by using ({sup 18}O)oxygen and a microsomal enzyme system obtained from etiolated sorghum seedlings. The products formed were purified by HPLC and TLC, and the incorporation of ({sup 18}O)oxygen was monitored by mass spectrometry. In the presence of NADPH and ({sup 18}O)dioxygen, L-tyrosine is converted to (E)- and (Z)-p-hydroxyphenylacetaldhyde oxime with quantitative incorporation of an ({sup 18}O)oxygen atom into the oxime function. These data demonstrate that the conversion of N-hydroxytyrosine to p-hydroxyphenylacetaldehyde oxime involves additional N-hydroxylation and N-oxidation reactions giving rise to the formation of 2-nitro-3-(p-hydroxyphenyl)propionate, which by decarboxylation produces aci-1-nitro-2-(p-hydroxyphenyl)ethane. Both compounds are additional intermediates in the pathway. The two ({sup 18}O)oxygen atoms introduced by the N-hydroxylations are enzymatically distinguishable as demonstrated by the specific loss of the oxygen atom introduced by the first N-hydroxylation reaction in the subsequent conversion of aci-1-nitro-2-(p-hydroxyphenyl)ethane to (E)-p-hydroxyphenylacetaldehyde oxime. A high flux of intermediates through the microsomal enzyme system is obtained with N-hydroxytyrosine as a substrate. This renders the conversion of the aci-nitro compound rate limiting and results in its release from the active site of the enzyme system and accumulation of the tautomeric nitro compound.

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

1991-01-15

377

The biosynthesis of cyanogenic glucosides in higher plants. Identification of three hydroxylation steps in the biosynthesis of dhurrin in Sorghum bicolor (L. ) Moench and the involvement of 1-ACI-nitro-2-(p-hydroxyphenyl)ethane as an intermediate  

SciTech Connect

N-Hydroxytyrosine, (E)- and (Z)-p-hydroxyphenyl-acetaldehyde oxime, p-hydroxyphenylacetonitrile, and p-hydroxymandelonitrile are established intermediates in the biosynthesis of the tyrosine-derived cyanogenic glucoside dhurrin. Simultaneous measurements of oxygen consumption and biosynthetic activity using a microsomal enzyme system isolated from etiolated sorghum seedlings demonstrate a requirement for three oxygen molecules in the conversion of tyrosine to p-hydroxymandelonitrile. Two oxygen molecules are consumed in the conversion of tyrosine to (E)-p-hydroxyphenylacetaldehyde oxime, indicating the existence of a previously undetected hydroxylation step in addition to that resulting in the formation of N-hydroxytyrosine. Radioactively labeled 1-nitro-2-(p-hydroxyphenyl)ethane was chemically synthesized and tested as a possible intermediate. Biosynthetic experiments demonstrate that the microsomal enzyme system metabolizes the nitro compound to the subsequent intermediates in dhurrin synthesis (Km = 0.05 mM; Vmax = 14 nmol/mg of protein/h). Low amounts of 1-nitro-2-(p-hydroxyphenyl)ethane are produced in the microsomal reaction mixtures when tyrosine is used as substrate. These data support the involvement of 1-nitro-2-(p-hydroxyphenyl)ethane or more likely its aci-nitro tautomer as an intermediate between N-hydroxytyrosine and p-hydroxyphenylacetaldehyde oxime. The conversion of (E)-p-hydroxyphenylacetaldehydeoxime to p-hydroxymandelonitrile requires a single oxygen molecule. The oxygen molecule is utilized for hydroxylation of p-hydroxyphenylacetonitrile into p-hydroxymandelonitrile. This indicates that the conversion of p-hydroxyphenylacetaldehyde oxime into p-hydroxyphenylacetonitrile proceeds by a simple dehydration reaction.

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

1990-12-05

378

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

379

Three secoiridoid glucosides from Jasminum lanceolarium  

Microsoft Academic Search

Three new secoiridoid glycosides, jaslanceosides C-E, in addition to jaslanceosides A and B, 10-hydroxyoleoside dimethyl ester and jasminoside were isolated from the leaves and stems of Jasminum lanceolarium. The structures of these compounds were elucidated on the basis of spectral analysis and chemical correlation with known compounds.

Ya-Ching Shen; Shao-Ling Lin; Chyh-Chung Chein

1997-01-01

380

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

381

Screening of common Plantago species in Hungary for bioactive molecules and antioxidant activity.  

PubMed

Five species of Plantago genus, namely P. lanceolata, P. major, P. media, P. altissima and P. maritima were screened for iridoid content (CE-MEKC), total caffeoyl phenylethanoid glycoside (CPG) content and antioxidant activity (CUPRAC assay). The five species could be distinguished by TLC pattern analysis in a single run in a system commonly used for quality management of P. lanceolata leaves, as shown by cluster analysis of major bands; with the exception, that P. altissima and P. lanceolata did not show enough pattern difference to be fully separated. P. maritima was shown to have the highest antioxidant capacity (0.42 ?mol ascorbic acid equivalent (AAE)/g DW), and the highest level of CPGs (4.29%). P. altissima was shown to be chemically indistinguishable from P. lanceolata with repsect to iridoid content (aucubin 0.55 ± 0.04%, 0.68 ± 0.23%, catalpol 0.66 ± 0.13% and 0.89 ± 0.22%, respectively), CPG content (2.40 ± 0.38% and 2.54 ± 0.56%, respectively) and antioxidant capacity (0.2206 ± 0.0290 and 0.2428 ± 0.0191 ?mol AAEAC/g DW). The presented data show the potency of medicinal use of Hungarian wild populations of the studied five species, especially in the case of P. maritima, and that P. altissima can be a potential replacement of P. lanceolata in herbal mixtures. PMID:21565762

Gonda, S; Tóth, L; Parizsa, P; Nyitrai, M; Vasas, G

2010-01-01

382

[Chemical constituents from Callicarpa nudiflora and their cytotoxic activities].  

PubMed

The chemical consitituents from cytotoxic fraction of the Callicarpa nudiflora extract were isolated and purified by a combination of HP-20 macroporous resin, silica gel and Sephadex LH-20 column chromatographies. The structures were elucidated on the basis of the spectroscopic data and comparison of their spectroscopic data with reported data. The cytotoxicity was evaluated by the MTT assay. The 50% and 70% EtOH elutions of EtOH-extract showed significant cytotoxic activities, leading to the isolation of twelve compounds, which were identified as luteoloside(1), lutedin-4'-O-?-D-glucoside(2), 6-hydroxyluteolin-7-O-?-glucoside(3), lutedin-7-O-neohesperidoside(4), rhoifolin (5), luteolin-7, 4'-di-O-glucoside (6), forsythoside B (7), acteoside (8), alyssonoside (9), catalpol(10), nudifloside(11), and leonuride(12). Compounds 3-6, 10 and 12 were isolated from this genus for the first time, and compound 9 was isolated from this plant for the first time. The cytotoxicity assay demonstrated that flavonoids 1-6, in various concentrations, showed monolithic proliferation inhibitory activities against Hela, A549 and MCF-7 cell lines. Compounds 3, 5 and iridoid glycoside 11 possessed higher cytotoxicacivities. In short, flavonoids are the main components of cytotoxic extract from C. nudiflora, while phenylethanoid glycosides are the predominant ingredient but inactive to cancer cell lines. In addition, the minor iridoid glycoside expressed weak cytotoxic activity. PMID:25509294

Ma, Yan-Chun; Zhang, Min; Xu, Wen-Tong; Feng, Shi-Xiu; Lei, Ming; Yi, Bo

2014-08-01

383

Antiinflammatory activity and chemical composition of extracts of Verbena officinalis.  

PubMed

In an attempt to locate the biologically active fraction(s) of the plant Verbena officinalis Linn. (Verbenaceae), a preliminary screening of successive petroleum ether, chloroform and methanol extracts of aerial parts for antiinflammatory activity using carrageenan paw oedema model was carried out. All three extracts were found to exhibit antiinflammatory activity with the chloroform extract being the most active. Chemical investigations of petroleum ether and chloroform extracts led to the isolation of beta-sitosterol, ursolic acid, oleanolic acid, 3-epiursolic acid, 3-epioleanolic acid, and minor triterpenoids of derivatives of ursolic acid and oleanolic acids. Chromatographic purification of the methanol extract yielded two iridoid glucosides, verbenalin and hastatoside, a phenylpropanoid glycoside, verbascoside and beta-sitosterol-D-glucoside. PMID:10960904

Deepak, M; Handa, S S

2000-09-01

384

Hemiterpene glucosides and other constituents from Spiraea canescens.  

PubMed

Five glycosides, 2-(trans-cinnamoyloxy-methyl)-1-butene-4-O-beta-D-glucopyranoside (1), 4-(6'-O-trans-cinnamoyl)-(2-hydroxymethyl-4-hydroxy-butenyl-beta-D-glucopyranoside (2), 6''-O-trans-p-coumaroyl-(4-hydroxybenzoyl)-beta-D-glucopyranoside (3), 6'-O-(4-methoxy-trans-cinnamoyl) alpha/beta-D-glucopyranose (4) 6'-O-(4''-methoxy-trans-cinnamoyl)-kaempferol-3-beta-D-glucopyranoside (7) along with six known compounds, (+)-isolariciresinol 3a-O-beta-D-glucopyranoside (8) (+)-lyoniresinol 3a-O-beta-D-glucopyranoside (9), apigenin 7-O-beta-D-glucopyranoside (10), quercetin 3-O-beta-D-glucopyranoside (11), 6'-O-cinnamoyl-alpha/beta-D-glucopyranose (6) 6'-O-p-coumaroyl-alpha/beta-D-glucopyranose (5) were isolated from the whole plant of Spiraea canescens. Some of these compounds showed potent radical scavenging activity in relevant non-physiological assays. Their structures were determined by NMR spectroscopic and CID mass spectrometric techniques. PMID:19747701

Choudhary, M Iqbal; Naheed, Nadra; Abbaskhan, Ahmed; Ali, Sajjad; Atta-ur-Rahman

2009-01-01

385

Hispidulin and nepetin 4?-glucosides from Cirsium oligophyllum  

Microsoft Academic Search

Two flavone glycosides, hispidulin 4?-O-?-d-glucopyranoside and nepetin 4?-O-?-d-glucopyranoside, were isolated from the leaves of Cirsium oligophyllum and identified on the basis of their 1H and 13C NMR, FAB-MS, UV spectra and characterization of their hydrolysates; hispidulin 7,4?-glycoside, vicenin-2, hispidulin and nepetin were also isolated.

Tsukasa Iwashina; Koji Kamenosono; Tatsuya Ueno

1999-01-01

386

Lessons learned from metabolic engineering of cyanogenic glucosides  

Microsoft Academic Search

Plants produce a plethora of secondary metabolites which constitute a wealth of potential pharmaceuticals, pro-vitamins, flavours,\\u000a fragrances, colorants and toxins as well as a source of natural pesticides. Many of these valuable compounds are only synthesized\\u000a in exotic plant species or in concentrations too low to facilitate commercialization. In some cases their presence constitutes\\u000a a health hazard and renders the

Anne Vinther Morant; Kirsten Jørgensen; Bodil Jørgensen; Winnie Dam; Carl Erik Olsen; Birger Lindberg Møller; Søren Bak

2007-01-01

387

A new eudesmane sesquiterpene glucoside from Liriope muscari fibrous roots.  

PubMed

The screening of several Chinese medicinal herbs for nematocidal properties showed that the ethanol extract of Liriope muscari fibrous roots possessed significant nematocidal activity against the pine wood nematode (Bursaphelenchus xylophilus). From the ethanol extract, a new constituent (1,4-epoxy-cis-eudesm-6-O-?-D-glucopyranoside) and three known glycosides [1?,6?-dihydroxy-cis-eudesm-3-ene-6-O-?-D-glucopyranoside (liriopeoside A), 1?,6?-dihydroxy-cis-eudesm-3-ene-6-O-?-D-glucopyranoside, and 1?,6?-dihydroxy-5,10-bis-epi-eudesm-4(15)-ene-6-O-? D-glucopyranoside] were isolated by bioassay-guided fractionation. The structures were elucidated by 1D and 2D NMR and MS techniques. 1,4-Epoxy-cis-eudesm-6-O-?-D-glucopyranoside possessed moderate nemato-cidal activity against B. xylophilus with a LC(50 )value of 339.76 ?g/mL, while liriopeoside A (LC(50) = 82.84 ?g/mL) and 1?,6?-dihydroxy-cis-eudesm-3-ene-6-O-?-D-glucopyranoside (LC(50) = 153.39 ?g/mL) also exhibited nematocidal activity against B. xylophilus. The crude extract of L. muscari fibrous roots exhibited nematocidal activity against the pine wood nematode with a LC(50) value of 182.56 ?g/mL. PMID:22031065

Zhang, Hai Ming; Wang, Gang Li; Bai, Chun Qi; Liu, Peng; Liu, Zi Mu; Liu, Qi Zhi; Wang, Yong Yan; Liu, Zhi Long; Du, Shu Shan; Deng, Zhi Wei

2011-01-01

388

A new alternariol glucoside from fungus Alternaria alternate cib-137.  

PubMed

A new secondary metabolite, 2-O-methylalternariol 4-O-?-[4-methoxyl-glucopyranoside] (1), together with four known compounds alternariol methyl ether (2), altenuene (3), isoaltenuene (4) and 2-(2'S-hydroxypropyl)-5-methyl-7-hydroxychromone (5), was isolated from the fungus Alternaria alternate cib-137. Its structure was elucidated on the basis of spectroscopic data. Compounds 3 and 4 demonstrated moderate activity against Staphylococcus aureus. PMID:25520187

Xu, Guo-Bo; Pu, Xiang; Bai, Huan-Huan; Chen, Xiao-Zhen; Li, Guo-You

2015-05-01

389

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

390

Sonication-assisted Agrobacterium rhizogenes-mediated transformation of Verbascum xanthophoeniceum Griseb. for bioactive metabolite accumulation.  

PubMed

An efficient protocol for the establishment of transformed root culture of Verbascum xanthophoeniceum using sonication-assisted Agrobacterium rhizogenes-mediated transformation is reported. Only 10 days after the inoculation with A. rhizogenes ATCC 15834 and 45 s ultrasound exposure, hairy roots appeared on 75% of the Verbascum leaves. Ten hairy root lines were isolated, although only half of them were free of bacterial contamination and started growing when excised from mother explants. The transgenic nature of the most vigorously growing hairy root clones (VX1 and VX6) was confirmed by polymerase chain reaction. Under submerged cultivation both hairy root clones accumulated high biomass amounts (12.8 and 14.3 g L(-1), respectively) and significant amounts of bioactive phenylethanoid glycoside verbascoside (over 6-times more than in mother plant leaves). LC-APCI-MS analyses confirmed verbascoside accumulation in hairy root clones along with three other phenylethanoid glycosides (forsythoside B, leucosceptoside B and martynoside) and an iridoid glycoside aucubin. This is the first report on the induction of hairy roots of Verbascum plants. PMID:21184229

Georgiev, Milen I; Ludwig-Müller, Jutta; Alipieva, Kalina; Lippert, Annemarie

2011-05-01

391

Photoperiod-induced geographic variation in plant defense chemistry.  

PubMed

Spatial variation in chemical defense of plants can be caused by genetic, biotic, and abiotic factors. For example, many plants exhibit a latitudinal cline in chemical defense, potentially due to latitudinal variation in abiotic environmental factors such as the light regime during the growing season. In the worldwide distributed Plantago lanceolata, the levels of deterrent iridoid glycosides (IGs), aucubin and catalpol, vary geographically, including latitudinally. To examine whether latitudinal variation in photoperiod can explain part of this geographic variation, plants from the Netherlands and Finland were exposed to two different photoperiods, simulating the Dutch (middle European) and Finnish (northern European) light period during the growing season. The experiment showed that although most variation in IG content was genetic, plants from both Dutch and Finnish origin produce relatively more catalpol under a northern European than under a middle European photoperiod. Our results confirm that latitudinal effects on photoperiod can contribute to geographic variation in plant defense chemistry, which should be considered when studying latitudinal clines in plant-enemy interactions. PMID:25637332

Reudler, J H; Elzinga, Jelmer A

2015-02-01

392

Anti-inflammatory activity of iridoid and catechol derivatives from Eucommia ulmoides Oliver.  

PubMed

Neuroinflammation and pro-inflammatory mediators play key roles in the pathogenesis of neurodegenerative diseases including stroke, which account for a significant burden of morbidity and mortality worldwide. Recently, the unsatisfactory pharmacotherapy and side effects of the drugs led to the development of alternative medicine for treating these diseases. Du Zhong (DZ), Eucommia ulmoides Oliver leaves, is a commonly used herb in the therapy of stroke in China. We hypothesize that the components from DZ inhibit neuroinflammation. In this study, DZ was extracted and the bioactive fractions with inhibitory effect on lipopolysaccharide (LPS)-stimulated nitric oxide (NO) production in BV-2 microglial cells were further separated using chromatography. Two purified bioactive compounds, genipin (compound C) and 4-(1,2-dimethoxyethyl)benzene-1,2-diol (compound F), were isolated and identified after spectroscopic analysis. The results showed that they inhibited LPS-stimulated NO and tumor necrosis factor-alpha (TNF-?) production. Genipin exerted its anti-inflammatory effects through PI3K/Akt signaling pathway, whereas compound F inhibited phosphorylation of p38 mitogen-activated protein kinase (MAPK). In conclusion, genipin and compound F have potential for developing into new drugs for treating neurodegenerative diseases. PMID:25065689

Luo, Dan; Or, Terry C T; Yang, Cindy L H; Lau, Allan S Y

2014-09-17

393

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

Microsoft Academic Search

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

Karolyn Darrow; M. Deane Bowers

1997-01-01

394

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

Microsoft Academic Search

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

Karolyn Darrow; M. Deane Bowers

1999-01-01

395

Iridoid glycoside metabolism and sequestration by Poladryas minuta (Lepidoptera: Nymphalidae) feeding on Penstemon virgatus (Scrophulariaceae)  

Microsoft Academic Search

A bivoltine checkerspot butterfly,Poladryas minuta, is aPenstemon specialist, not known to utilize any other plant genus for oviposition and larval feeding. At several intermontane plains sites of central Colorado, the butterfly utilizesPenstemon virgatus as its sole host plant. Analysis of the host plant showed it to contain three cinnamyl-type catalpol esters (scutellarioside-II, globularin, globularicisin) and catalpol. The host plant contained

Karen M. L'empereur; Frank R. Stermitz

1990-01-01

396

Compounds from the Fruits of the Popular European Medicinal Plant Vitex agnus-castus in Chemoprevention via NADP(H):Quinone Oxidoreductase Type 1 Induction  

PubMed Central

As part of our continuing efforts in the search for potential biologically active compounds from medicinal plants, we have isolated 18 compounds including two novel nitrogen containing diterpenes from extracts of the fruits of Vitex agnus-castus. These isolates, along with our previously obtained novel compound vitexlactam A (1), were evaluated for potential biological effects, including cancer chemoprevention. Chemically, the nitrogenous isolates were found to be two labdane diterpene alkaloids, each containing an ?, ?-unsaturated ?-lactam moiety. Structurally, they were elucidated to be 9?-hydroxy-13(14)-labden-16,15-amide (2) and 6?-acetoxy-9?-hydroxy-13(14)-labden-15,16-amide (3), which were named vitexlactams B and C, respectively. The 15 known isolates were identified as vitexilactone (4), rotundifuran (5), 8-epi-manoyl oxide (6), vitetrifolin D (7), spathulenol (8), cis-dihydro-dehydro-diconiferylalcohol-9-O-?-D-glucoside (9), luteolin-7-O-glucoside (10), 5-hydroxy-3,6,7,4?-tetramethoxyflavone (11), casticin (12), artemetin (13), aucubin (14), agnuside (15), ?-sitosterol (16), p-hydroxybenzoic acid (17), and p-hydroxybenzoic acid glucose ester (18). All compound structures were determined/identified on the basis of 1D and/or 2D NMR and mass spectrometry techniques. Compounds 6, 8, 9, and 18 were reported from a Vitex spieces for the first time. The cancer chemopreventive potentials of these isolates were evaluated for NADP(H):quinone oxidoreductase type 1 (QR1) induction activity. Compound 7 demonstrated promising QR1 induction effect, while the new compound vitexlactam (3) was only slightly active. PMID:23662135

Li, Shenghong; Qiu, Shengxiang; Yao, Ping; Sun, Handong; Fong, Harry H. S.; Zhang, Hongjie

2013-01-01

397

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

PubMed

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

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

2011-07-01

398

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

399

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; Tröger, Armin

2012-01-01

400

Sesquiterpene Glucosides from Anti-leukotriene B4 Release Fraction of Taraxacum Officinale  

Microsoft Academic Search

Chemical examination of the MeOH extract of the root of Taraxacum officinale, which exhibited inhibitory activity on the formation of leukotriene B4 from activated human neutrophils, has resulted in the isolation of 14-O-?-D-glucosyl-11,13-dihydro-taraxinic acid (1) and 14-O-?-D-glucosyl-taraxinic acid (2). The absolute stereostructure of 1 has been established by X-ray chrystallographic examination.

Yoshiki Kashiwada; Koichiro Takanaka; Harumi Tsukada; Yoshihisa Miwa; Toru Taga; Shigeo Tanaka; Yasumasa Ikeshiro

2001-01-01

401

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

402

?-Glucoside Activators of Mung Bean UDP-Glucose: ?-Glucan Synthase 1  

PubMed Central

Heat-stable activators of membranous ?-glucan synthase have been isolated from the supernatant fraction of crude mung bean (Vigna radiata) extracts by DEAE-cellulose and silica-gel chromatography. One of the activators has been partially purified and characterized on the basis of susceptibility to various enzymes and by analysis of the products formed upon total acid hydrolysis, alkaline-methanolysis, and ?-glucosidase digestion. This activator has the characteristics of a 1,2-dioleoyl diglyceride containing ?-linked glucose residue(s) at the C-3 position. When expressed per mole of glucosyl residues, the maximal Ka value of the activator is estimated to be 25 micromolar. Both the intact glucosyl and fatty acid moiety are essential to the stimulatory effect of the activator. PMID:16666038

Callaghan, Theresa; Ross, Peter; Weinberger-Ohana, Patricia; Garden, Gwenn; Benziman, Moshe

1988-01-01

403

Isolation of lignan glucosides and neolignan sulfate from the leaves of Glochidion zeylanicum (Gaertn) A. Juss.  

PubMed

Six lignan and neolignan derivatives (1-6) were isolated from the n-BuOH-soluble fraction of a MeOH extract of the leaves of Glochidion zeylanicum. On the basis of spectral data, their structures were elucidated to be (+)-isolarisiresinol 3a-O-beta-glucopyranoside (1), dihydrodehydrodiconiferyl alcohol 4-, 9- and 9'-O-beta-D-glucopyranosides (2-4, respectively), (+)-isolarisiresinol 2a-O-beta-D-glucopyranoside (5), and dihydrodehydrodiconiferyl alcohol 9-O-sulfate (6), and 5 and 6 were new compounds. PMID:10923846

Otsuka, H; Hirata, E; Shinzato, T; Takeda, Y

2000-07-01

404

Effects of hydroquinone and its glucoside derivatives on melanogenesis and antioxidation: Biosafety as skin whitening agents  

Microsoft Academic Search

Background and objectiveThe biosafety of hydroquinone and its derivatives as skin whitening agent remains controversial. Here, we investigated the effects of hydroquinone, arbutin, and deoxyarbutin (d-arb) on melanogenesis and antioxidation using cultured melan-a melanocytes in the presence or absence of ultraviolet A (UVA)-induced oxidative stress and determined whether d-arb enables to be an alterative to hydroquinone and arbutin for skin

Zhi-Ming Hu; Qiong Zhou; Tie-Chi Lei; Shen-Feng Ding; Shi-Zheng Xu

2009-01-01

405

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

PubMed Central

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

Sharma, Mukesh C.; Sharma, Smita

2014-01-01

406

Effect of water content on the acid-base equilibrium of cyanidin-3-glucoside.  

PubMed

Laser Flash Photolysis was employed to measure the deprotonation and reprotonation rate constants of cyanidin 3-monoglucoside (kuromanin) in water/methanol mixtures. It was found that the deprotonation rate constant kd decreases with decreasing water content, reflecting the lack of free water molecules around kuromanin, which may accommodate and stabilize the outgoing protons. On the other hand, the reprotonation rate constant, kp, increases with the decrease in water concentration from a value of kp = 2 × 10(10) l mol(-1) s(-1) in water up to kp = 6 × 10(10) l mol(-1) s(-1) at 5.6M water concentration in the mixture. The higher value of kp at lower water concentrations reflects the fact that the proton is not freely escaping the solvation shell of the molecule. The deprotonation rate constant decreases with decreasing water content, reflecting the lack of free water molecules around kuromanin that can accommodate the outgoing protons. Overall, the acidity constant of the flavylium cation decreases with the decrease in water concentration from pKa values of 3.8 in water to approximately 4.8 in water-depleted media, thus shifting the equilibrium towards the red-coloured form, AH(+), at low water contents. The presence, or lack, of water, will affect the colour shade (red to blue) of kuromanin. This is relevant for its role as an intrinsic food component and as a food pigment additive (E163). PMID:25442581

Coutinho, Isabel B; Freitas, Adilson; Maçanita, António L; Lima, J C

2015-04-01

407

SANS with contrast variation study of the bacteriorhodopsin-octyl glucoside complex  

NASA Astrophysics Data System (ADS)

Membrane proteins (MPs), which play vital roles in trans-membrane trafficking and signalling between cells and their external environment, comprise a major fraction of the expressed proteomes of many organisms. MP production for biophysical characterization requires detergents for extracting MPs from their native membrane and to solubilize the MP in solution for purification and study. In a proper detergent solution, the detergent-associated MPs retain their native fold and oligomerization state, key requirements for biophysical characterization and crystallization. SANS with contrast variation was performed to characterize BR in complex with OG to better understand the MP-detergent complex. Contrast variation makes it possible to not only probe the conformation of the entire structure but also investigate the conformation of the polypeptide chain within the BR-OG complex. The BR-OG SANS contrast variation series is not consistent with a compact structure, such as a trimeric BR complex surrounded by a belt of detergent. The data strongly suggest that the protein is partially unfolded through its association with the detergent micelles.

Mo, Yiming; Heller, William T.

2010-11-01

408

SANS with Contrast Variation Study of the Bacteriorhodopsin-octyl Glucoside Complex  

SciTech Connect

Membrane proteins (MPs), which play vital roles in trans-membrane trafficking and signaling between cells and their external environment, comprise a major fraction of the expressed proteomes of many organisms. MP production for biophysical characterization requires detergents for extracting MPs from their native membrane and to solubilize the MP in solution for purification and study. In a proper detergent solution, the detergent-associated MPs retain their native fold and oligomerization state, key requirements for biophysical characterization and crystallization. SANS with contrast variation was performed to characterize BR in complex with OG to better understand the MP-detergent complex. Contrast variation makes it possible to not only probe the conformation of the entire structure but also investigate the conformation of the polypeptide chain within the BR-OG complex. The BR-OG SANS contrast variation series is not consistent with a compact structure, such as a trimeric BR complex surrounded by a belt of detergent. The data strongly suggest that the protein is partially unfolded through its association with the detergent micelles.

Heller, William T [ORNL; Mo, Yiming [ORNL

2010-01-01

409

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

PubMed

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

Nahrstedt, A; Kant, J D; Hösel, W

1984-10-01

410

Cinnamoyl glucosides of catechin and dimeric procyanidins from young leaves of Inga umbellifera (Fabaceae)  

E-print Network

of Utah, 257 S 1400 E, Salt Lake City, UT 84112-0840, USA b Smithsonian Tropical Research Institute Nicaragua to central Brazil where it is frequently encountered in non-flooding moist forests (Pennington

Coley, Phyllis

411

21 CFR 573.660 - Methyl glucoside-coconut oil ester.  

Code of Federal Regulations, 2011 CFR

...conditions: (a) The additive meets the specifications prescribed in § 172.816 of this chapter. (b) It is used as a surfactant in molasses intended for use in animal feed at a level not to exceed 320 parts per...

2011-04-01

412

21 CFR 573.660 - Methyl glucoside-coconut oil ester.  

Code of Federal Regulations, 2014 CFR

...conditions: (a) The additive meets the specifications prescribed in § 172.816 of this chapter. (b) It is used as a surfactant in molasses intended for use in animal feed at a level not to exceed 320 parts per...

2014-04-01

413

21 CFR 172.816 - Methyl glucoside-coconut oil ester.  

Code of Federal Regulations, 2014 CFR

...crystallization of sucrose and dextrose at a level not to exceed the minimum quantity required to produce its intended effect. (2) As a surfactant in molasses at a level not to exceed 320 parts per million in the...

2014-04-01

414

21 CFR 573.660 - Methyl glucoside-coconut oil ester.  

Code of Federal Regulations, 2012 CFR

...conditions: (a) The additive meets the specifications prescribed in § 172.816 of this chapter. (b) It is used as a surfactant in molasses intended for use in animal feed at a level not to exceed 320 parts per...

2012-04-01

415

21 CFR 172.816 - Methyl glucoside-coconut oil ester.  

Code of Federal Regulations, 2011 CFR

...of sucrose and dextrose at a level not to exceed the minimum quantity required to produce its intended effect. (2) As a surfactant in molasses at a level not to exceed 320 parts per million in the...

2011-04-01

416

21 CFR 573.660 - Methyl glucoside-coconut oil ester.  

Code of Federal Regulations, 2013 CFR

...conditions: (a) The additive meets the specifications prescribed in § 172.816 of this chapter. (b) It is used as a surfactant in molasses intended for use in animal feed at a level not to exceed 320 parts per...

2013-04-01

417

21 CFR 172.816 - Methyl glucoside-coconut oil ester.  

Code of Federal Regulations, 2010 CFR

...of sucrose and dextrose at a level not to exceed the minimum quantity required to produce its intended effect. (2) As a surfactant in molasses at a level not to exceed 320 parts per million in the...

2010-04-01

418

21 CFR 172.816 - Methyl glucoside-coconut oil ester.  

Code of Federal Regulations, 2013 CFR

...of sucrose and dextrose at a level not to exceed the minimum quantity required to produce its intended effect. (2) As a surfactant in molasses at a level not to exceed 320 parts per million in the...

2013-04-01

419

21 CFR 573.660 - Methyl glucoside-coconut oil ester.  

Code of Federal Regulations, 2010 CFR

...conditions: (a) The additive meets the specifications prescribed in § 172.816 of this chapter. (b) It is used as a surfactant in molasses intended for use in animal feed at a level not to exceed 320 parts per...

2010-04-01

420

21 CFR 172.816 - Methyl glucoside-coconut oil ester.  

Code of Federal Regulations, 2012 CFR

...of sucrose and dextrose at a level not to exceed the minimum quantity required to produce its intended effect. (2) As a surfactant in molasses at a level not to exceed 320 parts per million in the...

2012-04-01

421

BIOAVAILABILITY OF SOYBEAN ISOFLAVONES FROM AGLYCONE AND GLUCOSIDE FORMS IN AMERICAN WOMEN  

Technology Transfer Automated Retrieval System (TEKTRAN)

Even though the bioavailability of isoflavones from aglycone forms is believed to be higher than glycosides, human studies testing the bioavailability of isoflavones in Eastern and Western human subjects have been contradictory. To investigate the postprandial absorption and bioavailability of soy ...

422

Constituents of Chrysothamnus viscidiflorus Ahmed A. Ahmed a,*, Mohamed-Elamir F. Hegazy b  

E-print Network

ketoalcohol derivatives and one coumarin glucoside. The structures of two previously reported compounds, 1b; Sesquiterpenoid glucoside; Coumarin glucoside; Anti-cancer activity 1. Introduction Green rabbitbrush

Paré, Paul W.

423

12-hydroxyjasmonic acid glucoside is a COI1-JAZ-independent activator of leaf-closing movement in Samanea saman.  

PubMed

Jasmonates are ubiquitously occurring plant growth regulators with high structural diversity that mediate numerous developmental processes and stress responses. We have recently identified 12-O-?-D-glucopyranosyljasmonic acid as the bioactive metabolite, leaf-closing factor (LCF), which induced nyctinastic leaf closure of Samanea saman. We demonstrate that leaf closure of isolated Samanea pinnae is induced upon stereospecific recognition of (-)-LCF, but not by its enantiomer, (+)-ent-LCF, and that the nonglucosylated derivative, (-)-12-hydroxyjasmonic acid also displays weak activity. Similarly, rapid and cell type-specific shrinkage of extensor motor cell protoplasts was selectively initiated upon treatment with (-)-LCF, whereas flexor motor cell protoplasts did not respond. In these bioassays related to leaf movement, all other jasmonates tested were inactive, including jasmonic acid (JA) and the potent derivates JA-isoleucine and coronatine. By contrast, (-)-LCF and (-)-12-hydroxyjasmonic acid were completely inactive with respect to activation of typical JA responses, such as induction of JA-responsive genes LOX2 and OPCL1 in Arabidopsis (Arabidopsis thaliana) or accumulation of plant volatile organic compounds in S. saman and lima bean (Phaseolus lunatus), generally considered to be mediated by JA-isoleucine in a COI1-dependent fashion. Furthermore, application of selective inhibitors indicated that leaf movement in S. saman is mediated by rapid potassium fluxes initiated by opening of potassium-permeable channels. Collectively, our data point to the existence of at least two separate JA signaling pathways in S. saman and that 12-O-?-D-glucopyranosyljasmonic acid exerts its leaf-closing activity through a mechanism independent of the COI1-JAZ module. PMID:21228101

Nakamura, Yoko; Mithöfer, Axel; Kombrink, Erich; Boland, Wilhelm; Hamamoto, Shin; Uozumi, Nobuyuki; Tohma, Kentaro; Ueda, Minoru

2011-03-01

424

Cyanidin3Glucoside inhibits ethanol-induced invasion of breast cancer cells overexpressing ErbB2  

Microsoft Academic Search

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

Mei Xu; Kimberly A Bower; Siying Wang; Jacqueline A Frank; Gang Chen; Min Ding; Shiow Wang; Xianglin Shi; Zunji Ke; Jia Luo

2010-01-01

425

Lignan and neolignan glucosides, and tachioside 2'-O-4''-O-methylgallate from the leaves of Glochidion rubrum.  

PubMed

Thirteen compounds (1-13) were isolated from a MeOH extract of leaves of Glochidion rubrum. The structures of four new compounds were elucidated to be (-)-isolariciresinol 2a-O-beta-D-glucopyranoside (1), (7R,8S)- and (7R,8R)-4,7,9,9'-tetrahydroxy-3,3'-dimethoxy-8-O-4'-neolignan 7-O-beta-D-glucopyranosides (2 and 3, respectively), and tachioside 2'-O-4''-O-methylgallate (4) on detailed inspection of one- and two-dimensional NMR spectral data. PMID:19506993

Cai, Wen-Hu; Matsunami, Katsuyoshi; Otsuka, Hideaki; Shinzato, Takakazu; Takeda, Yoshio

2009-10-01

426

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

427

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

PubMed

Three compounds were isolated from benzene and acetone extracts of the root-sprouts of Agrimonia pilosa Ledeb. On the basis of physicochemical properties, spectroscopy (UV, IR, NMR, MS, CD, GC) and chemical degradation, two known compounds were identified as palmitic acid (VIII) and daucosterol (IX), one new compound was elucidated as (2S,3S)-(-)-taxifolin-3-O-beta-D-glucopyranoside (X). PMID:2281787

Pei, Y H; Li, X; Zhu, T R; Wu, L J

1990-01-01

428

Clinica Chin&a Acta, 184 (1989) 235-242 Use of 4-heptylumbelliferyl-/?-D-glucoside  

E-print Network

for lysosomal glucocerebrosidase, thereby minimizing the contribution of the nonspecific cytosolic P the ability of the bile salt sodium taurocholate to activate lysosomal glucocerebrosidase while inhibiting April 1989; accepted 1 May 1989) Key words: Gaucher's disease; Glucocerebrosidase; Heterozygote

Gopalan, Venkat

1989-01-01

429

Hydrolysis of a naturally occurring beta-glucoside by a broad-specificity beta-glucosidase from liver.  

PubMed Central

We have isolated from guinea-pig liver a broad-specificity beta-glucosidase of unknown function that utilizes as its substrate non-physiological aryl glycosides (e.g. 4-methylumbelliferyl beta-D-glucopyranoside, p-nitrophenyl beta-D-glucopyranoside). The present paper documents that this enzyme can be inhibited by various naturally occurring glycosides, including L-picein, dhurrin and glucocheirolin. In addition, L-picein, which acts as a competitive inhibitor of the broad-specificity beta-glucosidase (Ki 0.65 mM), is also a substrate for this enzyme (Km 0.63 mM; Vmax. 277,000 units/mg). Heat-denaturation, kinetic competition studies, chromatographic properties and pH optima all argue strongly that the broad-specificity beta-glucosidase is responsible for the hydrolysis of both the non-physiological aryl glycosides and L-picein. This paper demonstrates that beta-glucosidase can catalyse the hydrolysis of a natural glycoside, and may provide a key to understanding the function of this enigmatic enzyme. A possible role in the metabolism of xenobiotic compounds is discussed. PMID:3099756

LaMarco, K L; Glew, R H

1986-01-01

430

The beneficial effect of total glucosides of paeony on psoriatic arthritis links to circulating Tregs and Th1 cell function.  

PubMed

Total glycosides of peony (TGP) is a natural immuno-modulatory drug extracted from traditional Chinese herb peony. It has been approved by State Food and Drug Administration for the treatment of rheumatoid arthritis. However, data of TGP effect on psoriatic arthritis (PsA) is still scarce. In this study, 19 patients with PsA received 12-week treatment of TGP, and clinical efficacy in joint manifestations was evaluated by DAS28 at weeks 0, 4, 8 and 12. Peripheral percentages of Tregs, Th1, Th2 and NK cells were analyzed, and serum Th1-type cytokines (IL-12, IFN-? and TNF-?), Th2-type cytokines (IL-4, IL-5 and IL-10) as well as pro-inflammatory factors (IL-2, IL-6 and IL-8) were concomitantly examined. Six patients (32%) exhibited ?25% decrease of DAS28 (responders). Interestingly, all responders displayed a continuous decrease in Treg and Th1 numbers during TGP treatment, concomitant with significant decreases in Th1-type cytokine levels. Serum IL-6 also showed a significant decline in responders. Non-responders lacked these sequential alterations. Thus, TGP merits further consideration as a promising therapeutic option for PsA. The result indicated that recovery of Tregs and Th1 may serve as prognostic markers to assess responsiveness to TGP treatment in PsA. PMID:23610010

Wang, Yi Na; Zhang, Yu; Wang, Yan; Zhu, Ding Xian; Xu, Li Qin; Fang, Hong; Wu, Wei

2014-03-01

431

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

432

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

433

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

434

Specioside ameliorates oxidative stress and promotes longevity in Caenorhabditis elegans.  

PubMed

Specioside (6-O-coumaroylcatalpol) is an iridoid glucoside which possesses multifunctional activities viz. analgesic, antidyspeptic, astringent, liver stimulating and wound healing properties. The present study for the first time delineates stress alleviating and lifespan prolonging action of specioside (SPC), isolated from Stereospermum suaveolens in the free living, multicellular nematode model Caenorhabditis elegans. A strong correlation between lifespan extension and stress modulation in adult worms was established in a dose dependent manner. The dietary intake of this phytomolecule elevated juglone induced oxidative and heat induced thermal stress tolerance in C. elegans. On evaluation, it was found that 25?M dose of SPC significantly extended lifespan by 15.47% (P?0.0001) with reduction in stress level. Furthermore, SPC enhanced mean survival in mev-1 mutant suggesting its oxidative stress reducing potential. Furthermore, SPC augmented stress modulatory enzymes superoxide dismutase (SOD) and catalase (CAT) level in C. elegans. Altogether, these findings broaden current perspectives concerning stress alleviating potentials of SPC and have implications in development of therapeutics for curing age related disorders. PMID:25619942

Asthana, Jyotsna; Yadav, A K; Pant, Aakanksha; Pandey, Swapnil; Gupta, M M; Pandey, Rakesh

2015-03-01

435

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

436

Evolutionary advantage and molecular modes of action of multi-component mixtures used in phytomedicine.  

PubMed

Plants use complex mixtures of secondary compounds (SM) of different structural classes to protect themselves against herbivores, bacteria, fungi and viruses. These complex mixtures may contain SM, which are specific for a single target (monotarget SM). A majority of SM, however, can interfere with several targets (multitarget SM) in a pleiotropic fashion. The composition of such extracts appears to be optimised, since the components are not only additive but apparently synergistic in their bioactivity. Synergism can be achieved by inhibiting the xenobiotics inactivating activities of animals and microbes (MDR, CYP), by facilitating the uptake of polar SM across biomembranes and/or by affecting several important organs in animals concomitantly. Phytotherapy employs equally complex extracts of medicinal plants. Arguments were put together that the utilisation of complex mixtures with pleiotropic agents presents a unique therapeutic approach with many advantages over monotarget compounds. Mixtures of multitarget SM, used in phytotherapy include phenolics, tannins, mono- and sequiterpenes, saponins, iridoid glucosides and anthraquinones, but only few of them alkaloids or other toxic monotarget SM.Multitarget effects are caused by SM, which can modulate the three-dimensional structure of proteins (and thus their function), by interfering with DNA/RNA (especially gene expression) or membrane permeability. In addition, complex extracts may contain synergists, which can inhibit MDR, cytochrome P450 or enhance absorption and thus bioavailability of active metabolites. The molecular modes of action are reviewed for the main groups of secondary metabolites. PMID:19075616

Wink, Michael

2008-12-01

437

Nano-liquid chromatography coupled to time-of-flight mass spectrometry for phenolic profiling: a case study in cranberry syrups.  

PubMed

A new method based on nano-liquid chromatography coupled to time-of-flight mass spectrometry (nano-LC-TOF-MS) using lock-mass calibration was developed to facilitate the accurate and routine characterization and quantification of phenolic compounds. Thus, it was applied to study cranberry syrups, in which, using negative ionization mode, a total of nine phenolic compounds were unequivocally identified using standards and 38 tentatively taking into account their retention time, accurate mass (errors<5 ppm) data and isotope pattern, as well as literature. Among them, 13 compounds, belonging to flavonols and iridoids conjugated with phenolic acids, were reported for first time in cranberry or cranberry based-products. The analytical method was also validated using chlorogenic acid, p-coumaric acid, (+)-catechin, (-)-epicatechin, procyanidin A2, quercetin 3-O-glucoside, quercetin 3-O-rhamnoside, quercetin, and myricetin standards. In this way, the analytical method showed adequate linearity, with R(2) above 0.99, and acceptable values of intra- and inter-day repeatability of the retention time and peak area. The detection limits and quantification were between 1.0-15.6 ng mL(-1) and 2.0-62.5 ng mL(-1), respectively. The method can be extended to characterize phenolic compounds in other food and plant matrices, and as well biological samples. PMID:25476399

Contreras, María del Mar; Arráez-Román, David; Fernández-Gutiérrez, Alberto; Segura-Carretero, Antonio

2015-01-01

438

Catalpol Inhibited the Proliferation of T24 Human Bladder Cancer Cells by Inducing Apoptosis Through the Blockade of Akt-Mediated Anti-apoptotic Signaling.  

PubMed

Catalpol is an iridoid glucoside extracted from the traditional Chinese medicinal plant called Rehmannia glutinosa, and it is reported to possess a variety of pharmacological activities. The goal of this research was to explore the effect of catalpol on the human bladder cancer cells T24. The cells were treated for different durations with various concentrations of catalpol. Then the viability, mobility, and invasiveness of the cells were determined by MTT assay and flow cytometry, respectively. Catalpol was found to significantly suppress the proliferation, migration, and invasiveness of T24 bladder cancer cells in a dose- and time-dependent manner. The results also revealed that catalpol promoted apoptosis and caused the cell-cycle arrest at G2/M phase. Furthermore, the catalpol-mediated apoptosis was found to involve the modulation of PI3K/Akt pathway and inhibit the expression of anti-apoptotic B cell lymphoma-2 (Bcl-2) family proteins. Also, the expressions of Bcl-2 proapoptotic effectors, Bcl-2-associated X protein, and Bcl-2 associated death promoter were up-regulated in the cells treated with catalpol. The enzymes involved in the ultimate process of apoptosis, active caspase-3 and poly ADP ribose polymerase were elevated, and the latter was observed to be cleaved, indicating that catalpol-accelerated cell apoptosis involved a caspase-dependent pathway. These results suggest that catalpol might serve to be a promising therapeutic agent for the treatment of human bladder cancer. PMID:25388838

Jin, Di; Cao, Ming; Mu, Xin; Yang, Guoliang; Xue, Wei; Huang, Yiran; Chen, Haige

2014-11-12

439

Analgesic activity of catalpol in rodent models of neuropathic pain, and its spinal mechanism.  

PubMed

Neuropathic pain is a major health issue that represents considerable social and economic burden worldwidely. In this study, we investigated the potential of catalpol, an iridoid glucoside of Rehmannia glutinosa Steud, to alleviate neuropathic pain. The potential analgesic effects of catalpol were evaluated by chronic constriction injury (CCI) and lumbar 5 spinal nerve ligation (L5 SNL) model. In addition, we explored whether catalpol altered the degree of microglia activation and neuroinflammation in rat spinal cord after CCI induction. Repeated administration of catalpol (1, 5, 25, and 125 mg/kg) reversed mechanical allodynia induced by CCI and L5 SNL in a dose-dependent manner in rats. Levels of activated microglia, activated NF-?B, and proinflammatory cytokines (IL-1?, IL-6, TNF-?) in lumber spinal cord were elevated in rats following CCI induction, and catalpol significantly inhibited these effects. Our results demonstrated that catalpol produces significant antinociceptive action in rodent behavioral models of neuropathic pain and that this effect is associated with modulation of neuroinflammation in spinal cord. PMID:24980862

Wang, Yingbin; Zhang, Rongzhi; Xie, Jianqin; Lu, Jianzhong; Yue, Zhongjin

2014-12-01

440

How insects overcome two-component plant chemical defence: plant ?-glucosidases as the main target for herbivore adaptation.  

PubMed

Insect herbivory is often restricted by glucosylated plant chemical defence compounds that are activated by plant ?-glucosidases to release toxic aglucones upon plant tissue damage. Such two-component plant defences are widespread in the plant kingdom and examples of these classes of compounds are alkaloid, benzoxazinoid, cyanogenic and iridoid glucosides as well as glucosinolates and salicinoids. Conversely, many insects have evolved a diversity of counteradaptations to overcome this type of constitutive chemical defence. Here we discuss that such counter-adaptations occur at different time points, before and during feeding as well as during digestion, and at several levels such as the insects’ feeding behaviour, physiology and metabolism. Insect adaptations frequently circumvent or counteract the activity of the plant ?-glucosidases, bioactivating enzymes that are a key element in the plant’s two-component chemical defence. These adaptations include host plant choice, non-disruptive feeding guilds and various physiological adaptations as well as metabolic enzymatic strategies of the insect’s digestive system. Furthermore, insect adaptations often act in combination, may exist in both generalists and specialists, and can act on different classes of defence compounds. We discuss how generalist and specialist insects appear to differ in their ability to use these different types of adaptations: in generalists, adaptations are often inducible, whereas in specialists they are often constitutive. Future studies are suggested to investigate in detail how insect adaptations act in combination to overcome plant chemical defences and to allow ecologically relevant conclusions. PMID:25165798

Pentzold, Stefan; Zagrobelny, Mika; Rook, Fred; Bak, Søren

2014-08-01