Identification of the iridoid glucoside theveside in Lantana camara (Verbenaceae), and determination of its structure and stereochemistry by means of N.M.R.

Abstract

The iridoid glucoside theveside has been isolated from the leaves and stems of three taxa of Lantana camara (Verbenaceae), where it occurs as the sodium salt. Elucidation of the structure was primarily from ¹H and ¹³C n.m.r. spectra. The stereochemistry of the molecule was established from ¹H homonuclear decoupling and Overhauser enhancement experiments. Theveside may now be fully described by the systematic name [1S- (1α,4aα,7aα)]-1-(β-D-glucosyloxy)-4a-hydroxy-7-(hydroxy-methyl)- 1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid. Theveside, already found in two members of the Apocynaceae, is previously unreported in the Verbenaceae.