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Unusual stilbene glucosides from Vitis vinifera roots

Authors :
Tristan Richard
Iris Aja
Grégory Da Costa
Eric Pedrot
Marie-Laure Iglesias
Antonio Palos Pinto
Josep Valls
Nassima Chaher
M. Begoña Ruiz-Larrea
Jean-Michel Mérillon
Djebbar Atmani
José Ignacio Ruiz Sanz
Source :
OENO One, Vol 53, Iss 3 (2019)
Publication Year :
2019
Publisher :
International Viticulture and Enology Society, 2019.

Abstract

Aim: Stilbenes are well-known phytoalexins present in vine and wine. Stilbene glucosides have been identified in wine; however, other than piceid, these compounds have never been reported to be present in the woody parts of grapevine. The aims of this study were to investigate the presence of stilbene glucosides in the woody parts of the vine and to evaluate their cytotoxic activity, in comparison with that of resveratrol, in human hepatoma HepG2 cells. Methods and results: Stilbene glucosides were isolated from a Vitis vinifera root extract. The extract was partitioned with ethyl acetate and fractionated by polyamide gel column chromatography. Pure compounds were obtained by semipreparative high-performance liquid chromatography. These were then identified by mass spectrometry and nuclear magnetic resonance (NMR) analyses, including analysis of two-dimensional NMR spectra. In addition to resveratrol, five stilbene glucosides were found: resveratroloside, resveratrol rutinoside, trans-ε-viniferin diglucoside, cis-ε-viniferin diglucoside and piceid. Of these, the first four showed cytotoxic effects against HepG2 cells when the crystal violet assay was used to determine cell viability. Conclusion: In addition to resveratrol and piceid, this is the first report of the presence of four glucosylated derivatives of resveratrol (resveratroloside, resveratrol rutinoside, and trans- and cis-ε-viniferin diglucosides) in the woody parts of vine. These compounds showed significant cytotoxicity against HepG2 cells. Significance and impact of the study: Stilbenes are well-known biological compounds. Grapevine is one of the main sources of this family of polyphenols. Other than piceid, stilbene glucosides have been identified in wine but never in the woody parts of vine. This is the first study in which five glucosylated derivatives of resveratrol were isolated from woody parts of vine. They were also shown to exert antiproliferative effects in human hepatoma HepG2 cells.

Details

Language :
English
ISSN :
24941271
Volume :
53
Issue :
3
Database :
Directory of Open Access Journals
Journal :
OENO One
Publication Type :
Academic Journal
Accession number :
edsdoj.743d46fde41b58e2b784d3da686da
Document Type :
article
Full Text :
https://doi.org/10.20870/oeno-one.2019.53.3.2462