Bioactive humulene derivatives from Asteriscus vogelii

The bioactive fractions obtained from the extract of Asteriscus vagelii afforded a new humulene derivative, the 8-oxo-6,7,9,10-tetrahydrohumulen-1,12-olide (1), in addition to the known asteriscunolides A (2), C (3) and D (4), and the acids 8-oxo-alpha -humula-6Z,9Z-dien-12-oic acid (5), 8-oxo-alpha -humula-6E,9Z-dien-12-oic acid (6) and 8-oxo-alpha -humula-6E,9E-dien-12-oic acid (7), characterized as their methyl esters. Evaluation of their phytotoxic and cytotoxic activities was accomplished. Compounds 3 and 4 gave the highest inhibition of plant cell cultures and of the plant Lemna paucicostata. Compound 4 was also the most active against P-338 lymphoma in mice, A-549 carcinoma of human lung, HT-29 carcinoma of human colon and MEL-28 human melanoma. (C) 2001 Elsevier Science Ltd. All rights reserved.