746
L. Camont et al. / Biochimie 94 (2012) 741e747
ꢀ
Scheme 3. Proposed mechanism of PCT radical secondary reaction, leading to oxidation end-products.
probably co-eluted in our experimental conditions e i.e. protocol
based on reversed-phase chromatographic separation e that is
the reason why only one peak was detected (Fig. 3). The way of PCT
evolution would appear as the main reaction way of RVT oxidation
since the three products formed e i.e., PCT, 3,4-DHBA and 3,5-DHBA
References
ꢀ
[1] B. Fauconneau, P. Waffo-Teguo, F. Huguet, L. Barrier, A. Decendit, J.M. Merillon,
Comparative study of radical scavenger and antioxidant properties of phenolic
compounds from Vitis vinifera cell cultures using in vitro tests, Life Sci. 61
(1997) 2103e2110.
[
[
[
[
[
2] J.A. Baur, D.A. Sinclair, Therapeutic potential of resveratrol: the in vivo
evidence, Nat. Rev. Drug Discov. 5 (2006) 493e506.
3] S. Renaud, M. de Lorgeril, Wine, alcohol, platelets, and the French paradox for
coronary heart disease, Lancet 339 (1992) 1523e1526.
e account for 85% of the total amount of the oxidation products
ꢀ
(
Table 1). Moreover, the addition of molecular oxygen on PCT is
ꢀ
ꢀ
likely faster than the biradical reaction between PCT and RVT since
4] S. Pervaiz, Resveratrol: from grapevines to mammalian biology, FASEB J. 17
3
,4- and 3,5-DHBA are preferentially formed.
(2003) 1975e1985.
5] S. Das, D.K. Das, Resveratrol:
a
therapeutic promise for cardiovascular
diseases, Recent Pat. Cardiovasc. Drug Discov. 2 (2007) 133e138.
5
. Conclusion
6] G.D. Norata, P. Marchesi, S. Passamonti, A. Pirillo, F. Violi, A.L. Catapano, Anti-
inflammatory and anti-atherogenic effects of cathechin, caffeic acid and trans-
resveratrol in apolipoprotein E deficient mice, Atherosclerosis 191 (2007)
The aim of this study was to propose a comprehensive scheme
ꢀ
ꢀ
ꢁ
265e271.
of the reaction mechanisms of the direct scavenging of HO and O
2
[
7] H.J. Kim, E.J. Chang, S.H. Cho, S.K. Chung, H.D. Park, S.W. Choi, Antioxidative
activity of resveratrol and its derivatives isolated from seeds of Paeonia lac-
tiflora, Biosci. Biotechnol. Biochem. 66 (2002) 1990e1993.
radicals generated by water gamma radiolysis, thanks to a quanti-
tative analysis (determination of the radiolytic yields) of the
disappearance of trans-RVT and of the concomitant formation of
trans-RVT-derived oxidation products previously identified by mass
[
8] S. Ozgova, J. Hermanek, I. Gut, Different antioxidant effects of polyphenols on
lipid peroxidation and hydroxyl radicals in the NADPH-, Fe-ascorbate- and Fe-
microsomal systems, Biochem. Pharmacol. 66 (2003) 1127e1137.
ꢀ
ꢁ
spectrometry. Whereas O
2
radicals seemed to poorly initiate
[9] B. Olas, B. Wachowicz, I. Majsterek, J. Blasiak, A. Stochmal, W. Oleszek, Anti-
ꢀ
0
0
0
oxidation of trans-RVT, HO radicals quantitatively reacted with
trans-RVT, via a dismutation mechanism. Two reaction pathways
involving HO -induced trans-RVT primary radicals have been
oxidant properties of trans-3,3 ,5,5 -tetrahydroxy-4 -methoxystilbene against
modification of variety of biomolecules in human blood cells treated with
platinum compounds, Nutrition 22 (2006) 1202e1209.
ꢀ
[
10] B. Olas, P. Nowak, J. Kolodziejczyk, M. Ponczek, B. Wachowicz, Protective
effects of resveratrol against oxidative/nitrative modifications of plasma
proteins and lipids exposed to peroxynitrite, J. Nutr. Biochem. 17 (2006)
proposed to explain the formation of the oxidation end-products of
trans-RVT. We have shown that piceatannol (PCT) and 3,5-
dihydroxybenzoic acid (3,5-DHBA) accounted for w85% of the
oxidized trans-RVT, whereas 3,5-dihydroxybenzaldehyde (3,5-
DHB) and para-hydroxybenzaldehyde (PHB) accounted for w15%.
These results help understand the direct radical scavenging of
trans-RVT, property involved in the beneficial antioxidant effect of
this natural polyphenol.
96e102.
[
[
11] B. Tadolini, C. Juliano, L. Piu, F. Franconi, L. Cabrini, Resveratrol inhibition of
lipid peroxidation, Free Radic. Res. 33 (2000) 105e114.
12] Y.J. Cai, J.G. Fang, L.P. Ma, L. Yang, Z.L. Liu, Inhibition of free radical-induced
peroxidation of rat liver microsomes by resveratrol and its analogues, Bio-
chim. Biophys. Acta 1637 (2003) 31e38.
[13] L. Belguendouz, L. Fremont, A. Linard, Resveratrol inhibits metal ion-
dependent and independent peroxidation of porcine low-density lipopro-
teins, Biochem. Pharmacol. 53 (1997) 1347e1355.
[
14] L. Belguendouz, L. Fremont, M.T. Gozzelino, Interaction of transresveratrol
with plasma lipoproteins, Biochem. Pharmacol. 55 (1998) 811e816.
15] L. Fremont, L. Belguendouz, S. Delpal, Antioxidant activity of resveratrol and
alcohol-free wine polyphenols related to LDL oxidation and polyunsaturated
fatty acids, Life Sci. 64 (1999) 2511e2521.
Acknowledgements
[
The authors are indebted to Dr. Averbeck for the use of the
gamma irradiator facility (Institut Curie, Paris, France). Laurent
Camont was the recipient of a fellowship from the Ministère de
l’Enseignement Supérieur et de la Recherche.
[
16] P. Brito, L.M. Almeida, T.C. Dinis, The interaction of resveratrol with ferryl-
myoglobin and peroxynitrite; protection against LDL oxidation, Free Radic.
Res. 36 (2002) 621e631.
[17] D. Pietraforte, L. Turco, E. Azzini, M. Minetti, On-line EPR study of free radicals
induced by peroxidase/H(2)O(2) in human low-density lipoprotein, Biochim.
Biophys. Acta 1583 (2002) 176e184.
Appendix. Supplementary data
[18] H. Berrougui, G. Grenier, S. Loued, G. Drouin, A. Khalil, A new insight into
resveratrol as an atheroprotective compound: inhibition of lipid peroxidation
and enhancement of cholesterol efflux, Atherosclerosis 207 (2009) 420e427.
[19] L. Camont, F. Collin, C. Marchetti, D. Jore, M. Gardes-Albert, D. Bonnefont-
Rousselot, Liquid chromatographic/electrospray ionization mass spectrometric