ABSTRACT
From Culcasia scandens P. Beauv., carota-4(5), 11(12)-diene (isodaucene), carota-3(4), 11(12)-dien-5-one, a new epoxide, 4,5-epoxy-carota-11(12)-ene (isodaucene epoxide) and beta-caryophyllene epoxide were isolated. The structures were established spectroscopically. Epoxidation of isodaucene with m-CPBA confirmed the structure and stereochemistry of the new epoxide.
Subject(s)
Araceae/chemistry , Sesquiterpenes/chemistry , Epoxy Compounds/chemistry , Molecular Structure , Polycyclic SesquiterpenesABSTRACT
Cytotoxic activity against the P388 cell line was seen in a crude extract of the New Zealand shrub Lophomyrtus bullata(Myrtaceae). Bioactivity-guided isolation led to a compound with NMR spectra complicated by the presence of two isomers. These crystallised together and an X-ray structure showed them to be stereoisomeric hybrids of triketone, phloroglucinol and bullatenone units. NMR measurements on the mixed isomers, as well as a cyclic ether produced from them by acid catalysed dehydration, were consistent with these structures. The natural products, named bullataketals A and B, have cytotoxic activity against the P388 cell line (IC(50) 1 microg ml(-1)), and antimicrobial activity against Bacillus subtilis.
