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Clinical Chemistry 43: 1092-1093, 1997;
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(Clinical Chemistry. 1997;43:1092-1093.)
© 1997 American Association for Clinical Chemistry, Inc.

Letters

Antioxidant Activity of the Stilbene Astringin, Newly Extracted from Vitis vinifera Cell Cultures

Jean-Michel Mérillon1, Bernard Fauconneau2, Pierre Waffo Teguo1, Laurence Barrier2, Joseph Vercauteren1 and François Huguet2

1 Groupe d'Etude des Substances Naturelles à Intérêt Thér., EA 491, Faculty of Pharmacy, Bordeaux, France ,
2 Centre d'Etudes et de Recherche sur les Xénobiot. , EA 1223, Faculty of Pharmacy, Poitiers, France


To the Editor:

Numerous epidemiological studies in France have shown a strong negative correlation between moderate red wine consumption and the incidence of cardiovascular disease (1)(2). Compared with other alcoholic beverages, red wine contains a much higher content of phenolic constituents. Frankel et al. (3) have shown that total phenolic compounds extracted from red wine inhibit the oxidation of human low-density lipoprotein (LDL) in vitro, which may provide an explanation for the "French paradox." In fact, increasing evidence suggests that oxidized LDL might be responsible for promoting atherogenesis.

Miller and Rice-Evans (4) examined a variety of red wines for total antioxidant activity and, based on the data of Frankel et al. (5) for the composition of wine, suggested that unidentified compounds must contribute to this total.

With the help of Vitis vinifera cell suspension obtained from Gamay Teinturier vine-plant, we isolated and characterized stilbenes (cis- and trans-piceid and trans-resveratrol) and anthocyanins (malvidin-3-O-ß-glucoside and peonidin-3-O-ß-glucoside) by spectrometric methods. Furthermore, we found evidence of production of astringin (a stilbene), which has never been reported as a constituent of Vitis vinifera and of wines (6)(7). Here, we report our study the antioxidant potency of these compounds isolated from Vitis vinifera cells by measuring the inhibition of lipid peroxidation induced by Cu2+ (IC50 = concentration at which one-half of the induced peroxidation is inhibited) in fresh human LDL preparation; we determined this by measuring the production of thiobarbituric acid-reactive substances (8). The lack of interference from the coloration of anthocyanins is verified by HPLC assays.

The IC50 of trans-resveratrol (Table 1 ) is of similar magnitude to that previously reported (9). The activity of the cis-isomer is 7 times weaker, probably because of its nonplanar conformation.


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  		Table 1. IC50 values obtained with phenolic substances.

Astringin (3-OH-trans-piceid) is 6 times more potent than trans-piceid, which confirms the major importance of catechol structure in antioxidant effect, as described for flavonoids. On the other hand, the conjugation of an OH group with a sugar decreased the antioxidant potential, according to the IC50 values of trans-resveratrol vs trans-piceid and astringinin vs astringin. The antioxidant activities of anthocyanins are similar to those of trans-resveratrol and astringin.

These data support previous work (3) suggesting that an array of phenolic substances in red wine may, because of their antioxidant properties, exert a protective effect against atherogenesis during a long period of moderate intake of red wine. We know little about the absorption, in vivo metabolism, and pharmacokinetics of phenols in wine. Consequently, we plan to produce 13C-labeled versions of these compounds to study both their absorption in human volunteers and their plasma antioxidant activity.


Acknowledgments

Research support was provided by the Region Aquitaine (grant no. 95 03 03 003) and the O.N.I. VINS, France. We thank R. Pontcharraud and A. Decendit for technical assistance and cell suspension maintenance, respectively.


Footnotes

*Author for correspondence


References

  1. Renaud S, De Lorgeril M. Wine, alcohol, platelets, and the French paradox for coronary heart disease. Lancet 1992;339:1523-1526. [ISI][Medline] [Order article via Infotrieve]
  2. Goldberg DM, Hahn SE, Parkes JG. Beyond alcohol: beverage consumption and cardiovascular mortality. Clin Chim Acta 1995;237:155-187. [ISI][Medline] [Order article via Infotrieve]
  3. Frankel EN, Kanner J, German JB, Parks E, Kinsella JE. Inhibition of oxidation of human low-density lipoprotein by phenolic substances in red wine. Lancet 1993;341:454-457. [ISI][Medline] [Order article via Infotrieve]
  4. Miller NJ, Rice-Evans CA. Antioxidant activity of resveratrol in red wine [Letter]. Clin Chem 1995;12:1789.
  5. Frankel EN, Waterhouse AL, Teissedre PL. Principal phenolic phytochemicals in selected California wines and their antioxidant activity in inhibiting oxidation of human low-density lipoproteins. J Agric Food Chem 1995;43:890-894.
  6. Waffo Teguo P, Decendit A, Vercauteren J, Deffieux G, Mérillon JM. trans-Resveratrol-3-O-ß-glucoside (piceid) in cell suspension cultures of Vitis vinifera. Phytochemistry 1996;42:1591-1593.
  7. Waffo Teguo P, Decendit A, Krisa S, Deffieux G, Vercauteren J, Mérillon JM. The accumulation of stilbene glycosides in Vitis vinifera cell suspension cultures. J Nat Prod 1996;59:1189-1191.
  8. Buege JA, Aust SD. Microsomal lipid peroxidation. Methods Enzymol 1978;52:302-310. [Medline] [Order article via Infotrieve]
  9. Frankel EN, Waterhouse AL, Kinsella JE. Inhibition of human LDL oxidation by resveratrol. Lancet 1993;341:1103-1104. [ISI][Medline] [Order article via Infotrieve]



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