Studies on the Constituents of Anodendron affine DURCE. V. Isolation and Structure of Two New Constituents

Abstract

Two new constituents were isolated from the ether extract of the stems of Anodendron affine DURCE by using the silica gel chromatography. One of them (C₁₂H₁₄O₃, mp 99-100°) was elucidated as 4-hydroxy-3-(3-methyl-2-butenyl)benzoic acid (I) from its spectrometric data and by comparison with authentic samples. The other (C₁₂H₁₄O₄ mp 212-214°), named anodendroic acid, was assumed to be 2-(1-hydroxy-1-methylethyl)-2, 3-dihydrobenzofuran-5-carboxylic acid (II) on the basis of its ultraviolet, infrared, and nuclear magnetic resonance spectra. Compounds VI and XIII were respectively synthesized via the route (I-IV-V-VI and VII-VIII-IX-XIII) shown in Chart 1. The methyl ester of anodendroic acid was consistent with VI.