Bioactive saponins from Microsechium helleri and Sicyos bulbosus

Eleven oleanane-type saponins (1-11) have been isolated from Microsechium helleri and Sicyos bulbosus roots and were evaluated for their antifeedant, nematicidal and phytotoxic activities. Saponins {3-O-beta-D-glucopyranosyl (1 -> 3)-beta-D-glucopyranosyl-2 beta,3 beta,16 alpha,23-tetrahydroxyolean-12-en-28-oic acid 28-O-alpha-L-rhamnopyranosyl-(1 -> 3)-beta-D-xylopyranosyl-(1 -> 4)-[beta-D-xylopyranosyl-(1 -> 3)]-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranoside} (1), and (3-O-beta-D-glucopyranosyl-2 beta,3 beta,16 alpha,23-tetrahydroxyolean-12-en-28-oic acid 28-O-alpha-L-rhamnopyranosyl-(1 -> 3)-beta-D-xylopyranosyl-(1 -> 4)-(beta-D-xylopyranosyl-(1 -> 3)]-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranoside) (2) were also isolated from M. helleri roots together with the two known compounds 3 and 4. Seven known structurally related saponins (5-11) were isolated from S. bulbosus roots. The structures of these compounds were established as bayogenin and polygalacic glycosides using one- and-two-dimensional NMR spectroscopy and mass spectrometry. Compounds 7, 10, bayogenin (12) and polygalacic acid (13) showed significant (p < 0.05) postingestive effects on Spodoptera littoralis larvae, compounds 5-11 and 12 showed variable nematicidal effects on Meloydogyne javanica and all tested saponins had variable phytotoxic effects on several plant species (Lycopersicum esculentum, Lolium perenne and Lactuca sativa). These are promising results in the search for natural pesticides from the Cucurbitaceae family. (C) 2011 Elsevier Ltd. All rights reserved.