Biotransformation of the diterpenes epicandicandiol and candicandiol by Mucor plumbeus.
The microbiological transformation of the diterpene epicandicandiol (1) with Mucor plumbeus gave foliol (3), sideritriol (5), and 7beta,16alpha,17,18-tetrahydroxy-ent-kaurane (7), while the incubation of candicandiol (2) gave 7alpha,9beta,18-trihydroxy-ent-kaur-16-ene (10), canditriol (11), and 7alpha,16alpha,17,18-tetrahydroxy-ent-kaurane (12). Thus, the main difference observed in both feedings, resulting from the spatial change in the orientation of the 7-hydroxyl, from axial in the substrate 1 to equatorial in 2, was the formation of a 3alpha- and a 9beta-hydroxylated derivative, respectively.
Fraga
Braulio M
BM
Instituto de Productos Naturales y Agrobiología, PO Box 195, CSIC, 38206-La Laguna, Tenerife, Canary Islands, Spain. bmfraga@ipna.csic.es
Alvarez
Laura
L
Suárez
Sergio
S
D001711:Biotransformation; D004224:Diterpenes / Q000737:chemistry / Q000378:metabolism*; D006900:Hydroxylation; D015394:Molecular Structure; D009089:Mucor / Q000737:chemistry*; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism
D004224:Diterpenes; C476659:candicandiol; C476658:epicandicandiol