Isolation and Characterization of Novel Stilbene Derivatives from Riesling Wine

Baderschneider, Beate; Winterhalter, Peter

doi:10.1021/jf991348k

Cited by 88 publications

(48 citation statements)

References 22 publications

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“…30) 2-b-glucopyranosyloxyphenanthrene-4,6-diol (9), 31) paucifloroside A (11), 23) cis-(Ϫ)-eviniferin (12), 32) upunoside D (13), 33) balanocarpol (14), 34) melanoxylin A (15), 35) malibatol (16), 36) (Ϫ)-ampelopsin F (17), 37) pauciflorol B (18), 23) vaticanol C (20), 38) hemsleyanols C (21) and D (22), 39) pauciflorol C (23), 23) vateriaphenol B (24), 4) nepalensinol G (25), 40) stenophyllol A (26), 41) vaticanol B (27), 38) vaticasides B (28) and C (29), 42) and upunaphenol F (30). 43) The other known compounds were identified to be flavonols [kaempferol 3-O-rhamnoside (31), 44) kaempferol 3-O-rhamnopyranosyl-(1→2)-rhamnopyranoside (32), and quercitrin (33) 45) ], diterpenes [columbin (34) 46) and palmarin (35) 47) ], bergenin (36), 11) and syringin (37).…”

Section: Chemical Constituents In the Leaves Of Vateria Indicamentioning

confidence: 99%

“…The various structures are dependent upon the skeletal variation and the stereoisomers. Comprehensive investigation of the chemical constituents in the leaves of V. indica resulted in the isolation and characterization of a new resveratrol tetramer [vateriaphenol F (1)] and two new O-glucosides of resveratrol oligomers [vateriosides A (2) and B (4)], along with a new natural compound (3), and 33 known compounds [resveratrol derivatives , flavonols (31)(32)(33), diterpenes (34,35), an isocoumarin (36), and a phenylpropanoid (37)]. The structures of the new compounds (1, 2, 4) were elucidated by 2D NMR techniques such as 1 H-1 H correlation spectroscopy (COSY), 13 C-1 H COSY, and heteronuclear multiple bond connectivity (HMBC).…”

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Chemical Constituents in the Leaves of Vateria indica

Ito

Masuda

Abe

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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Regular ArticleDipterocarpaceaeous plants have been known to have an abundance of stilbene oligomers that have a blocking unit of resveratrol. The woody plant Vateria indica LINN. (Dipterocarpaceae) is distributed in India and Sri Lanka, and the resin has been used as a traditional medicine for sore throat, chronic bronchitis, rheumatism, and diarrhea.1) The stem of the genus Vateria is known to produce biologically active compounds such as oligostilbenoids and monoterpenes. [2][3][4][5][6] Our previous study demonstrated that the leaves also contain stilbene derivatives in high quantity. 6) Recently, the bioactivities of stilbenoids isolated from Dipterocarpaceaeous plants have been reported to have antimicrobial activites, 7,8) antitumor activities, [9][10][11] and regulation of endoplasmic reticulum stress. H COSY, and heteronuclear multiple bond connectivity (HMBC). Stereostructures were proposed by analysis of nuclear Overhauser effect spectroscopy (NOESY), differential rotating frame Overhauser enhancement (ROE), and ROESY spectra, as well as high-resolution (HR) FAB-MS and electrospray ionization (ESI)-MS analysis and circular dichroism (CD) spectroscopic properties. Vateriaphenol F (1) has a unique C 2 -symmetric structure. Results and DiscussionVateriaphenol F (1) and vaterioside A (2) were purified from an acetone extract of V. indica by open column chromatography on DMS, octadecyl silica (ODS), Silica gel, and Sephadex LH-20, as well as HPLC. Vaterioside B (4) was purified from MeOH extract by repeated chromatography.Vateriaphenol F (1) ([a] D 25 Ϫ136°), obtained as a pale-yellow solid, showed positive reaction to Gibbs reagent. The structure is composed of four resveratrol units (A-D; resveratrol A unit: i.e., between rings A 1 and A 2 via carbons C-7a and C-8a). A detailed elucidation was carried out as follows. The molecular formula was assigned to C 56 H 44 O 13 by HR-ESI-MS that showed a pseudomolecular ion [MϩNa] ϩ at m/z 947.2670, indicating 35 degrees of unsaturation. In the 1 H-and 13 C-NMR spectra at rt, some signals due to ring A 2 were broadened in various solvents. In the 1 H-NMR spectrum in acetone-d 6 at Ϫ30°C, the signals due to Pharmacognosy, Gifu Pharmaceutical University; 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan: b Institute of Microbial Chemistry, Tokyo; 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan: and c Survey of Medicinal Plant Unit, Central Council for Research in Ayurveda and Siddha; Tirunelveli-627002, Tamil Nadu, India. Received June 23, 2010; accepted July 15, 2010; published online July 16, 2010 Comprehensive re-investigation of the chemical constituents in the leaves of Vateria indica (Dipterocarpaceae) resulted in the isolation of a novel resveratrol dimeric dimer having a C 2 -symmetric structure, vateriaphenol F (1), and two new O-glucosides of resveratrol oligomers, vateriosides A (2) (resveratrol dimer) and B (4) (resveratrol tetramer), along with a new natural compound (3) and 33 known compounds including 26 resveratrol derivatives. The absolu...

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Section: Chemical Constituents In the Leaves Of Vateria Indicamentioning

confidence: 99%

mentioning

confidence: 99%

Chemical Constituents in the Leaves of Vateria indica

Ito

Masuda

Abe

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…For example, it is more active than resveratrol in inducing the relaxation of rat thoracic aorta preparations, has greater in vitro antioxidant activity, is a more potent inhibitor of platelet-derived growth factor-induced cell proliferation, and induces nitric oxide generation in vascular smooth muscle cells (VSMCs) (34)(35)(36). A number of reports on the modulatory effect of resveratrol on ion channel receptors have been published (15,16), however, to date, no reports on the modulatory effects of trans-ε-viniferin have been published.…”

Section: Discussionmentioning

confidence: 99%

“…The suppression of β-amyloid (Aβ) fibril formation is considered to be an important target for the treatment of Alzheimer's Disease (AD) and ε-viniferin, the dimer of resveratrol, and resveratrol glucoside (at concentrations of 5 -10 μM) have been reported to inhibit both fragment Aβ (25)(26)(27)(28)(29)(30)(31)(32)(33)(34)(35) and full length (Aβ (1-40) and Aβ (1-42)) peptide aggregation in vitro (12,13). trans-ε-viniferin isolated from Vitis amurensis, at a concentration of 5 μM, also protects cultured cortical neuronal cells from glutamate-induced neurotoxicity (14).…”

Section: Introductionmentioning

confidence: 99%

The Differential Effects of Resveratrol and trans-ε-Viniferin on the GABA-Induced Current in GABAA Receptor Subtypes Expressed in Xenopus Laevis Oocytes

Groundwater

Hamid

et al. 2015

J Pharm Pharm Sci

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-Purpose:The natural products resveratrol and trans-ε-viniferin have been reported to have many beneficial effects, which include the enhancement of cognition and memory. There have been no studies which have reported the effects of these compounds on the different GABAA receptor subtypes and this study aimed to address this. Methods: The effects of both resveratrol, and its dimer, trans-ε-viniferin, have been investigated on different GABAA receptor subtypes expressed in Xenopus laevis oocytes, using the twoelectrode voltage clamp technique. Results: Resveratrol induced a current of 22 ± 3.53 nA in the α1β2γ2L subtype of the GABAA receptor (but not in the α5β3γ2L and α2β2γ2L subtypes) when applied alone. It also positively modulated the GABA-induced current (IGABA) in α1β2γ2L receptors, in a dose-dependent manner (EC50 58.24 μM). The effects of resveratrol were not sensitive to the benzodiazepine antagonist flumazenil. trans-ε-Viniferin exhibited a different pattern of activity to resveratrol; it alone had no effect on any of the subtypes, but it did negatively modulate the GABA-induced current (IGABA) in all three subtypes. The greatest inhibition was found in the α1β2γ2L subtype (IC50 5.79 μM), with the inhibition in the α2β2γ2L (IC50 of 19.08 μM) and α5β3γ2L (IC50 of 21.05 μM) subtypes being similar. The effects of trans-ε-viniferin in α1β2γ2L and α2β2γ2L receptors were also not sensitive to the benzodiazepine antagonist flumazenil while, in the α5β3γ2L subtype the effect was not sensitive to the inverse agonist L-655,708, indicating different binding sites for this molecule. Conclusions: The results of the present study indicate that both resveratrol and trans-ε-viniferin modulate the GABA-induced current in different ways, and that trans-ε-viniferin may be a lead compound for the discovery of agents which selectively inhibit the GABA-induced current in α1-containing subtypes.

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“…The stilbenes identified in wine include, additional to the wellstudied aglycones trans-and cis-resveratrol, their corresponding 3-O-β-Dglucosylated derivatives trans-and cis-piceid, a few resveratrol dimers (ε-viniferin, δ-viniferin) and trimers (α-viniferin), but also a few less frequently studied stilbene derivatives. The latter are mono-stilbene 2,4,6-trihydroxyphenanthrene-2-Oglucoside, two isomeric resveratrol-2-C-glucosides, four dimeric stilbenes glucosides (cis-and trans-ε-viniferin diglucoside, pallidol glucoside, and pallidol diglucoside), and trans-astringin (3,5,3',4'-tetrahydroxystilbene-3-O-β-glucoside) Ribeiro de Lima et al, 1999;Baderschneider and Winterhalter, 2000). It is likely that some of these compounds occur only in grapes (and therefore in wine) that have been attacked by plant pathogens, resulting in a phytoalexin response in the grapevine.…”

Section: Stilbenes In Winementioning

confidence: 99%