S-Alk(en)yl-Cysteine Sulfoxides in Allium Species Are Excellent Acrolein Scavengers: Implications for Secondary Antioxidants in Plants

Abstract

Reactive carbonyl species (RCS), such as acrolein (Acr), are generated through the degradation of lipid peroxides and exert cytotoxic effects. To identify natural RCS scavengers, we examined 80% ethanol extracts from 46 angiosperm species for Acr-trapping activity using an HPLC-based assay. Strong activities were observed in several taxa, including garlic, spinach, avocado, broccoli, and lotus. In garlic, the active metabolite was identified as S-allyl-L-cysteine sulfoxide (alliin), a characteristic Allium amino acid. Alliin and its S-(1E)-propenyl and S-methyl derivatives (isoalliin and methiin, respectively) trapped up to two Acr molecules at the amino group and exhibited higher activities than known scavengers such as carnosine and epigallocatechin gallate. These findings highlight S-alk(en)yl-L-cysteine sulfoxides as potent secondary antioxidants and suggest that structurally diverse RCS scavengers remain to be discovered in plants.