Abstract

EROSA-REJON, Gilda J.; YAM-PUC, Alejandro; PENA-RODRIGUEZ, Luis M.  and  STERNER, Olov. Pulcaffeate, a Trimeric Caffeic Acid Derivative from Bourreria pulchra. J. Mex. Chem. Soc [online]. 2023, vol.67, n.3, pp.182-186.  Epub Apr 22, 2024. ISSN 1870-249X.  https://doi.org/10.29356/jmcs.v67i3.1985.

The trimeric caffeic acid derivative pulcaffeate (1) was isolated from the organic crude extract of the roots of Bourreria pulchra (Boraginaceae). The biosynthesis of 1 appears to involve an intramolecular Diels-Alder reaction between a cyclohexa-1,3-diene intermediate, generated by the oxidation of the aromatic ring of a cinnamic acid unit, and the conjugated double bond of a caffeic acid unit. The structure of the new metabolite was elucidated through a detailed analysis of its 1H and 13C NMR spectroscopic data. This is the first report of a trimeric metabolite occurring in B. pulchra.

Keywords : Boraginaceae; cinnamic acid; caffeic acid; intramolecular cycloaddition; Diels-Alder reaction.