title: Stereo and regioselective microbial reduction of the clerodane diterpene 3,12-dioxo-15,16-epoxy-4-hydroxycleroda-13(16),14-diene.
abstract: The biotransformation of the clerodane diterpene, 3,12-dioxo-15,16-epoxy-4-hydroxy-cleroda-13(16),14-diene (1), obtained from Croton micans var. argyroglossum (Baill.) Mill., was investigated for the first time. Whole cells of Cunninghamella echinulata and Rhizopus stolonifer were used as enzymatic systems, and with both fungi the only biotransformation product obtained was the new ent-neo-clerodane diterpene (3R,4S,5S,8S,9R,10S)-3,4-dihydroxy-15,16-epoxy-12-oxo-cleroda-13(16),14-diene (2a). The absolute stereochemistry of 2a was inferred by comparison of its optical rotation with those of the chemical reduction product of 1 and its quasienantiomer 2c.
authors.forename: Jair
authors.initials: J
authors.lastname: Mafezoli
authors.forename: Maria C F
authors.initials: MC
authors.lastname: Oliveira
authors.forename: José R
authors.initials: JR
authors.lastname: Paiva
authors.forename: Antônio H
authors.initials: AH
authors.lastname: Sousa
authors.forename: Mary A S
authors.initials: MA
authors.lastname: Lima
authors.forename: José N Silva
authors.initials: JN
authors.lastname: Júnior
authors.forename: Francisco G
authors.initials: FG
authors.lastname: Barbosa
authors.forename: E M Kithsiri
authors.initials: EM
authors.lastname: Wijeratne
authors.forename: A A Leslie
authors.initials: AA
authors.lastname: Gunatilaka
mesh_terms: D029802:Croton / Q000737:chemistry; D020093:Cunninghamella / Q000378:metabolism*; D045785:Diterpenes, Clerodane / Q000737:chemistry* / Q000378:metabolism*; D015394:Molecular Structure; D012233:Rhizopus / Q000378:metabolism*
chemical_list: C000591501:3,12-dioxo-15,16-epoxy-4-hydroxycleroda-13(16),14-diene; D045785:Diterpenes, Clerodane