E-Viniferin

Resveratrol fraas-dehydrodimer frans-S-Viniferin frans-e-Viniferin... 

Yitrac X, Bornet A, Yanderlinde R, Vails JM, Richard T, Delaunay J-C, Merillon J-M, Teissedre P-L. 2005. Determination of stilbenes (8-viniferin, trans-astringin, trans-piceid, cis- and trans-resveratrol, e-viniferin) in Brazilian wines. J Agric Food Chem 53 5664-5669. 

Numerous stilbenes such as e-viniferin (Landrault et al. 2002) and 5-viniferin, two resveratrol dehydrodimers (Vitrac et al. 2005), the resveratrol dimer pallidol (Vitrac et al. 2001), a-viniferin, a trimer of resveratrol (Pryce and Langcake 1977)... 

Trans-conflgured stilbenes such as /rani-resveratrol, /rani-pterostilbene and /ran -e-viniferin show two characteristic bands corresponding to high absorbances from 308 to 336 nm and from 281 to 313 nm. Cis-configured stilbenes like cis-resveratrol, c/x-pterostilbene and c/x-e-viniferin exhibit a UV maximum at 285nm (Jeandet et al. 1997). 

Vitrac, X., Bomet, A., Vanderlinde, R., Vails, J., Richard, T., Delaunay, J.-C., MeriUon, J.-M., Teissedre, P.-L. (2005). Determination of stilbenes (5-viniferin, trani-astringin, trans-friceid, cis- and trani-resveratrol, e-viniferin) in Brazilian wines. J. Agric. Food Chem., 53, 5664-5669. 

Viniferin (446) occurs in Dipterocarpaceae, C5rperaceae, Gnetaceae and Leguminosae, whereas (+)-e-viniferin (445), only in Vitaceae. The relationship between enantiomers that exist in some plants of Dipterocarpaceae and Vitaceae (e.g. ampelopsins A, F, and H, hopeaphenol and isohopeaphenol) can be reasonably explained from the results of their biosynthesis [208]. 

A series of vitisins have been isolated and identified by Niwa et al. Phytochemical investigation on Vitis coignetiae resulted in the isolation of e-viniferin diol (533, dimer), tetramers (+)-vitisin A (698), (-)-vitisin B... 

Laevifonol (761) is an e-viniferin-ascorbic acid hybrid compound, possessing a five-membered lactone ring, isolated from the heartwood of Shorea laeviforia [265]. The stem bark of Shorea hemsleyana yielded shorealactone (762), the structure and absolute configuration of which was determined by means of 2D NMR techniques and X-ray analysis of its 4-bromobenzoyl derivative [340]. H-7a and H-8a in laevifonol (761) were presented as cis. However, the authors did not provide evidence to support this. So, considering their similar NMR data and [a]o values [-200° (c 0.1, MeOH) for 762 and -124° (c 0.496, MeOH) for 761], we suggest that compounds 761 and 762 are the same compound. 

The oxidation of resveratrol (1) by the COX-1 peroxidase led to the formation of two major products namely cw-e-viniferin (447) and trans-i/-viniferin. Identity of these viniferins was established by HPLC and LC/UV/MS, and the mechanism of viniferin formation from resveratrol (1) was investigated [257]. Combined with the work of Niwa et al, we conclude the plausible biosynthesis of stilbeneoligomers in the Vitaceae family is fairly clear (see Schemes 1 and 2). 

The retrosynthesis of Aara-e-viniferin (445) by Thomas et al. indicated that the y-butyrolactone (823) was a key intermediate, which later converted from the corresponding stilbene by manganese triacetate-mediated oxidative lactonization (Scheme 18) [407]. In subsequent papers, they described the FeCb-promoted tandem pericyclic synthesis of catechol analogs of restrytisol C. 3,4-Dimethoxy-12-acetoxy stilbene (824), which was synthesized by Heck coupling, was treated with FeCb to give the unnatural stilbene dimers 585 and 586 (Scheme 19) [288]. 

Gnetin E, parthenocissin A (552), e-viniferin (from roots of Cyphostemma bainesii), a-viniferin (635), hemsleyanols B and D (633, 674), vaticanol B (690) and davidiol A (652) (from barks of Shorea hemsleyana) were... 

Many other c5 otoxic oligostilbenes have been found in the systemic screen [254, 473-475]. The noteworthy ones include gnemonol G (546), gnetin I [473], the acetate of (-)-ampelopsin A, (-)-hopeaphenol (715) [271,474] and suffruticosol B (590) [475]. tra 5-e-Viniferin (445), gnetin H and suffhiticosol B (590) also strongly suppressed HL-60 cell proliferation and induced DNA damage [475]. 

Some stilbenoids from the roots of Vitis thunbergii, such as vitisinols B, C, D (772, 773, 576), (+)-e-viniferin (445), (-)-viniferal (771), ampelopsin C and (+)-vitisin C (700), displayed strong free radicalscavenging activities (ICsos 2.8 to 6.6 //M) [245]. The antioxidant capacity of tra s-e-viniferin (445) has also been evaluated and compared with those of resveratrol (1) and s)mthetic stilhene derivatives [504]. 

An efficient asymmetric synthesis of substituted methyl 2-aryl-dihydrobenzo[h]furan-3-carlx)xylate was achieved by a rhodium-catalyzed C-H bond activation route in an excellent yield, and the generated product was an intermediate applicable to the total synthesis of (+)-lithospermic acid <0 A13496>. A similar type of framework existing in ( )-E-viniferin was m e through a biomimetic transformation by a T1(N03)3-mediated oxidative dimerization of resveratrol <05T10285>. 

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