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

Abietane diterpenes from the perennial herb, Tripterygium wilfordii, h ave been shown to possess antiinflammatory activity. To obtain novel a nalogues of these diterpenes, two synthetic diterpenes, isotriptopheno lide [1] roxy-18(4-->3)abeo-abieta-3,8,11,13-tetraen-18-oic acid lacto ne) and triptophenolide xy-18(4-->)3)abeo-abieta-3-,8,11,13-tetraen-18 -oic acid lactone) were incubated with the filamentous fungi, Cunningh amella echinulata and C. elegans. The structures of the metabolites we re then determined by spectroscopic methods. Both species of Cunningha mella glucosidated 1 at C-12 to yield 2. When incubated with triptophe nolide [3], C. elegans and C, echinulata produced hydroxylated [6] and glucosylated [7] metabolites. In addition to B-ring hydroxylation, ar omatic hydroxylation at ring C was also observed. Both species hydroxy lated 3 to yield the dihydrodiol 4 which autooxidized to the quinone 5 .