OXIDATION AND GLUCOSE CONJUGATION OF SYNTHETIC ABIETANE DITERPENES BY CUNNINGHAMELLA SP .2. NOVEL ROUTES TO THE FAMILY OF DITERPENES FROM TRIPTERYGIUM-WILFORDII

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, Cunninghamella 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.