title: Oxidation and glucose conjugation of synthetic abietane diterpenes by Cunninghamella sp. II. Novel routes to the family of diterpenes from Tripterygium wilfordii.
abstract: Abietane diterpenes from the perennial herb, Tripterygium wilfordii, have been shown to possess antiinflammatory activity. To obtain novel analogues of these diterpenes, two synthetic diterpenes, isotriptophenolide [1] (12,19-dihydroxy-18(4-->3)abeo-abieta-3,8,11,13-tetraen++ +-18-oic acid lactone) and triptophenolide [3] (14,19-dihydroxy-18(4-->3)abeo-abieta-3,8,11,13-tetraen++ +-18-oic acid lactone) were incubated with the filamentous fungi, Cunningbamella echinulata and C. elegans. The structures of the metabolites were then determined by spectroscopic methods. Both species of Cunninghamella glucosidated 1 at C-12 to yield 2. When incubated with triptophenolide [3], C. elegans and C. echinulata produced hydroxylated [6] and glucosylated [7] metabolites. In addition to B-ring hydroxylation, aromatic hydroxylation at ring C was also observed. Both species hydroxylated 3 to yield the dihydrodiol 4 which autooxidized to the quinone 5.
authors.affiliation: Department of Biological Sciences, Simon Fraser University, Burnaby, British Columbia, Canada.
authors.forename: R
authors.initials: R
authors.lastname: Milanova
authors.forename: K
authors.initials: K
authors.lastname: Han
authors.forename: M
authors.initials: M
authors.lastname: Moore
mesh_terms: D001711:Biotransformation; D002240:Carbohydrate Sequence; D004224:Diterpenes / Q000138:chemical synthesis / Q000302:isolation & purification / Q000378:metabolism*; D005947:Glucose / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009090:Mucorales / Q000378:metabolism; D010084:Oxidation-Reduction; D010946:Plants, Medicinal / Q000737:chemistry*
chemical_list: D004224:Diterpenes; D005947:Glucose