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Paper | Regular issue | Vol 83, No. 3, 2011, pp.571-580
Published online, 12th January, 2011
DOI: 10.3987/COM-10-12116
Resveratrol Dimers with an Oxabicyclo Ring in Vatica albiramis

Naohito Abe, Tetsuro Ito, Masayoshi Oyama, Ryuichi Sawa, Yoshikazu Takahashi, and Munekazu Iinuma*

*Laboratory of Pharmacognosy, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan

Abstract

Investigation of the chemical constituents in the stem of Vatica albiramis (Dipterocarpaceae) resulted in the isolation of six stilbenoid derivatives, albiraminols C (1) and D (5), vatalbinosides G (2)–I (4), and J (6). We determined their structures by spectroscopic analysis including two- dimensional NMR, comparison of the NMR data based on isomerism, and computer-aided molecular modeling. Compounds 1–5 had two resveratrol units and are the first instance of resveratrol derivatives bearing an oxabicyclo[3.2.2]nonadiene ring system. Compound 6 is the oxidative product of 2 bearing a carbonyl group.