title: Biotransformation of an africanane sesquiterpene by the fungus Mucor plumbeus.
abstract: Biotransformation of 8β-hydroxy-african-4(5)-en-3-one angelate by the fungus Mucor plumbeus afforded as main products 6α,8β-dihydroxy-african-4(5)-en-3-one 8β-angelate and 1α,8β-dihydroxy-african-4(5)-en-3-one 8β-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 8β-(2'R,3'R)- and 8β-(2'S,3'S)-epoxyangelate of 8β,15-dihydroxy-african-4(5)-en-3-one, the hydrolysis product of the substrate, and three isomers of 8β-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.
authors.affiliation: Instituto de Productos Naturales and Agrobiología, CSIC, Avda. Astrof. F. Sánchez, 3, 38206, La Laguna, Tenerife, Canary Islands, Spain. Electronic address: bmfraga@ipna.csic.es.
authors.forename: Braulio M
authors.initials: BM
authors.lastname: Fraga
authors.affiliation: Instituto de Productos Naturales and Agrobiología, CSIC, Avda. Astrof. F. Sánchez, 3, 38206, La Laguna, Tenerife, Canary Islands, Spain. Electronic address: celisa@ipna.csic.es.
authors.forename: Carmen E
authors.initials: CE
authors.lastname: Díaz
authors.affiliation: Instituto de Productos Naturales and Agrobiología, CSIC, Avda. Astrof. F. Sánchez, 3, 38206, La Laguna, Tenerife, Canary Islands, Spain.
authors.forename: Leonardo J
authors.initials: LJ
authors.lastname: Amador
authors.affiliation: Instituto de Productos Naturales and Agrobiología, CSIC, Avda. Astrof. F. Sánchez, 3, 38206, La Laguna, Tenerife, Canary Islands, Spain.
authors.forename: Matías
authors.initials: M
authors.lastname: Reina
authors.affiliation: Instituto Universitario de Bioorgánica "Antonio González", Universidad de La Laguna, Tenerife, Spain.
authors.forename: Matías
authors.initials: M
authors.lastname: López-Rodriguez
authors.affiliation: Instituto de Ciencias Agrarias, CSIC, Serrano 113, 28016, Madrid, Spain.
authors.forename: Azucena
authors.initials: A
authors.lastname: González-Coloma
mesh_terms: D019659:Asteraceae / Q000737:chemistry; D001711:Biotransformation / Q000187:drug effects; D015394:Molecular Structure; D009089:Mucor / Q000737:chemistry*; D018517:Plant Roots / Q000378:metabolism; D012717:Sesquiterpenes / Q000737:chemistry*
chemical_list: D012717:Sesquiterpenes
keywords: Africanane; Biotransformations; Cytotoxic effects; Insect antifeedants; Mucor plumbeus; Sesquiterpenes