Resveratrol Tetramers with a C6-C3 or a C1 Unit from Upuna borneensis

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Investigation of the chemical constituents in the stem of Upuna borneensis (Dipterocarpaceae) resulted in the isolation of three new resveratrol derivatives, upunaphenols L (1), M (2) (resveratrol tetramers with a C6–C3 unit) and N (3) (resveratrol tetramer with a C1 unit). The structures have the same partial structure as vaticanol B (4). Upunaphenols L and M are new complex polyphenol compounds, lignostilbene. Their structures were determined by spectroscopic analysis including two dimensional NMR. Upunaphenol M was found to be an artifact generated by silica gel catalyzed methanolysis of 1.

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