title: On the biotransformation of ent-trachylobane to ent-kaur-11-ene diterpenes.
abstract: The microbiological transformation of trachinodiol (1) by the fungus Mucor plumbeus afforded the corresponding 1α, 2α, 3α, and 17-hydroxy derivatives (2-4 and 6), respectively. 7β,16α,18-Trihydroxy-ent-kaur-11-ene (sicanatriol) (5) was also obtained in this feeding. The biotransformation of 1 to give 5 by this fungus may occur by enzymatic abstraction of a hydrogen atom, allylic to the cyclopropane ring, and subsequent cleavage of this ring. This route is similar to that postulated by us in plants of the genus Sideritis, where ent-trachylobane and ent-kaur-11-ene diterpenes coexist. This study confirms that hydroxylation of diterpenes by M. plumbeus occurs preferably at ring A carbons.
authors.affiliation: Instituto de Productos Naturales y Agrobiología, CSIC, Avenida Astrofisico F. Sánchez 3, 38206-La Laguna, Tenerife, Canary Islands, Spain. bmfraga@ipna.csic.es
authors.forename: Braulio M
authors.initials: BM
authors.lastname: Fraga
authors.forename: Victoria
authors.initials: V
authors.lastname: Gonzalez-Vallejo
authors.forename: Ricardo
authors.initials: R
authors.lastname: Guillermo
mesh_terms: D001711:Biotransformation; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism*; D015394:Molecular Structure; D009089:Mucor / Q000378:metabolism; D031365:Sideritis; D013237:Stereoisomerism
chemical_list: C562186:7beta,16alpha,18-trihydroxy-ent-kaur-11-ene; D004224:Diterpenes