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A scalable biomimetic synthesis of resveratrol dimers and systematic evaluation of their antioxidant activities.

ABSTRACT: An efficient synthetic route to the resveratrol oligomers quadrangularin?A and pallidol is reported. It features a scalable biomimetic oxidative dimerization that proceeds in excellent yield and with complete regioselectivity. A systematic evaluation of the natural products and their synthetic precursors as radical-trapping antioxidants has revealed that, contrary to popular belief, this mode of action is unlikely to account for their observed biological activity.

SUBMITTER: Matsuura BS

PROVIDER: S-EPMC4457443 | biostudies-literature | 2015 Mar

REPOSITORIES: biostudies-literature

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A scalable biomimetic synthesis of resveratrol dimers and systematic evaluation of their antioxidant activities.

Matsuura Bryan S BS Keylor Mitchell H MH Li Bo B Lin YuXuan Y Allison Shelby S Pratt Derek A DA Stephenson Corey R J CR

Angewandte Chemie (International ed. in English) 20150204 12

An efficient synthetic route to the resveratrol oligomers quadrangularin A and pallidol is reported. It features a scalable biomimetic oxidative dimerization that proceeds in excellent yield and with complete regioselectivity. A systematic evaluation of the natural products and their synthetic precursors as radical-trapping antioxidants has revealed that, contrary to popular belief, this mode of action is unlikely to account for their observed biological activity. ...[more]

PMID: 25650836

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