Schistosomiasis Suppressing Deoxyphorbol Esters from Euphorbia cauducifolia L. Latex

Abstract

The molluscicidal activity of E. cauducifolia L. latex, extracted in various organic solvents, was tested against Biomphalaria glabrata snails, using Bayluscide as a control. The ethyl acetate extract was found to be the most active and in bioassay guided HPLC fractionation yielded eight (1–8) compounds. The structure and relative configuration of the isolates were established through spectroscopic (UV, IR, ¹H, ¹³C NMR, 2D NMR, HSQC, HMQC, HMBC, COSY-45°, TOCSY, HOHAHA, HOESY, ROESY, NOESY, SECSY, and NOE) techniques and mass measurements. These were named as: 13-acetoxy-20-O-angeloyl-12-deoxyphorbol (1), 13-O-[N-(2-aminobenzoyl)]anthraniloyl-20-acetoxy-12-deoxyphorbol (2), 13,20-O-dibezoyl-12-deoxyphorbol (3), 13,20-O-diangeloyl-12-deoxyphorbol (4), 13-O-angeloyl-20-O-[N-(2-aminobenzoyl)]anthraniloyl-12-deoxyphorbol (5), 13-O-tigloyl-20-O-[N-(2-aminobenzoyl)]anthraniloyl-12-deoxyphorbol (6), 13-O-benzoyl-20-O-[N-(2-aminobenzoyl)]anthraniloyl-12-deoxyphorbol (7), and 13-O-hexanoyl-20-O-[N-(2-aminobenzoyl)]anthraniloyl-12-deoxyphorbol (8). The literature reveals that all of the isolates were new natural metabolites and active against mollusks. Compounds 1 and 2, which were esterified at C-13 with acetoxy or N-(2-aminobenzoyl) anthraniloyloxy, showed twice the activity of the control while others (3–8) were equipotent.

Key words

schistosomiasis - Euphorbia cauducifolia L. - Euphorbiaceae - 2D‐NMR - 12‐deoxyphorbol esters - molluscicidal activity

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