ABSTRACT
A phytochemical study of an extract from transformed root cultures of Nepeta teydea, induced by Agrobacterium rhizogenes, led to the isolation of the following new compounds: the sesquiterpene (-)-cinalbicol, the diterpene teydeadione (6,11,14-trihydroxy-12-methoxy-abieta-5,8,11,13,15-penten-7-one), a degraded C23-triterpene (teydealdehyde) and three fatty acid esters of lanosta-7,24-dien-3ß-ol. The propyl ester of rosmarinic acid was also isolated for the first time from a natural source. In addition, two dehydroabietane diterpenes, eight triterpenes and eighteen known phenolic compounds were obtained. The antifeedant, cytotoxic and phytotoxic activities of the isolated compounds have also been investigated.
Subject(s)
Culture Techniques , Nepeta/chemistry , Plant Extracts/chemistry , Plant Extracts/toxicity , Plant Roots/chemistry , Animals , CHO Cells , Cricetinae , Cricetulus , Cytotoxins/chemistry , Cytotoxins/isolation & purification , Cytotoxins/toxicity , Insecticides/chemistry , Insecticides/isolation & purification , Nepeta/growth & development , Plant Extracts/isolation & purification , Plant Roots/growth & development , SpodopteraABSTRACT
Biotransformation of 8ß-hydroxy-african-4(5)-en-3-one angelate by the fungus Mucor plumbeus afforded as main products 6α,8ß-dihydroxy-african-4(5)-en-3-one 8ß-angelate and 1α,8ß-dihydroxy-african-4(5)-en-3-one 8ß-angelate, which had been obtained, together with the substrate, from transformed root cultures of Bethencourtia hermosae. This fact shows that the enzyme system involved in these hydroxylations in both organisms, the fungus and the plant, acts with the same regio- and stereospecificity. In addition another twelve derivatives were isolated in the incubation of the substrate, which were identified as the (2'R,3'R)- and (2'S,3'S)-epoxy derivatives of the substrate and of the 6α- and 1α-hydroxy alcohols, the 8ß-(2'R,3'R)- and 8ß-(2'S,3'S)-epoxyangelate of 8ß,15-dihydroxy-african-4(5)-en-3-one, the hydrolysis product of the substrate, and three isomers of 8ß-hydroxy-african-4(5)-en-3-one 2ξ,3ξ-dihydroxy-2-methylbutanoate. The insect antifeedant effects of the pure compounds were tested against chewing and sucking insect species along with their selective cytotoxicity against insect (Sf9) and mammalian (CHO) cell lines.
Subject(s)
Mucor/chemistry , Sesquiterpenes/chemistry , Asteraceae/chemistry , Biotransformation/drug effects , Molecular Structure , Plant Roots/metabolismABSTRACT
A chemical study of Bethencourtia hermosae, aerial parts and in vitro root cultures, transformed by Agrobacterium rhizogenes, afforded the hitherto unreported sesquiterpenes ceratopicanol angelate (1), 8ß-hydroxy-african-4(5)-en-3-one tiglate (4), 8ß-hydroxy-african-4(5)-en-3-one 3'-angeloxy-2'-methylbutanoate (5), 1α,8ß-dihydroxy-african-4(5)-en-3-one 8ß-angelate (7) and 6α,8ß-dihydroxy-african-4(5)-en-3-one 8ß-angelate (8). In addition, 8ß-hydroxy-african-4(5)-en-3-one (6) was isolated for the first time from a natural source, along with the rare sesquiterpenoid senecrassidiol (10) and two jacaranone derivatives 14 and 16. Known pyrrolizidine alkaloids, together with previously unreported hermosine (23), have also been isolated from this plant. The insect antifeedant activities of the extracts and compounds were studied together with their cytotoxic effects against insect (Sf9) and mammalian (CHO) cell lines.
