TY - JOUR
T1 - Peroxyl-radical-scavenging activity of garlic
T2 - 2-Propenesulfenic acid versus allicin
AU - Galano, Annia
AU - Francisco-Marquez, Misaela
PY - 2009/12/10
Y1 - 2009/12/10
N2 - The OOH radical reactions with allicin and its Cope elimination products (2-propenesulfenic acid and thioacrolein) in aqueous solution have been studied. The CBS-QB3 quantum chemistry method has been used, with geometries and frequencies at BHandHLYP/6-311++G(d,p) level and conventional transition state theory. 2-Propenesulfenic acid is predicted to be over 1000 times more reactive toward OOH radical than allicin (2.60 x 107 vs 7.38 x 103 L mol-1 s-1, at 298 K). Accordingly, our results strongly support the novel suggestion by Vaidya et al. (Angew. Chem., Int. Ed. 2009, 48, 157) that the active ingredient responsible for the free radical scavenging activity of garlic is actually 2-propenesulfenic acid and not allicin. In addition, direct reaction branching ratios and product distribution for the three studied reactions are proposed for the first time
AB - The OOH radical reactions with allicin and its Cope elimination products (2-propenesulfenic acid and thioacrolein) in aqueous solution have been studied. The CBS-QB3 quantum chemistry method has been used, with geometries and frequencies at BHandHLYP/6-311++G(d,p) level and conventional transition state theory. 2-Propenesulfenic acid is predicted to be over 1000 times more reactive toward OOH radical than allicin (2.60 x 107 vs 7.38 x 103 L mol-1 s-1, at 298 K). Accordingly, our results strongly support the novel suggestion by Vaidya et al. (Angew. Chem., Int. Ed. 2009, 48, 157) that the active ingredient responsible for the free radical scavenging activity of garlic is actually 2-propenesulfenic acid and not allicin. In addition, direct reaction branching ratios and product distribution for the three studied reactions are proposed for the first time
UR - http://www.scopus.com/inward/record.url?scp=71549115165&partnerID=8YFLogxK
U2 - 10.1021/jp907906h
DO - 10.1021/jp907906h
M3 - Artículo
SN - 1520-6106
VL - 113
SP - 16077
EP - 16081
JO - Journal of Physical Chemistry B
JF - Journal of Physical Chemistry B
IS - 49
ER -