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Communication | Special issue | Vol 44, No. 1, 1997, pp.95-104
Published online, 1st January, 1970
DOI: 10.3987/COM-96-S25
Studies with Plant Cell Cultures of the Chinese Herbal Plant, Tripterygium wilfordii. Synthesis and Biotransformation of Diterpene Analogues

James P. Kutney,* Kang Han, Francisco Kuri-Brena, Radka K. Milanova, and Malcolm Roberts

*Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, B.C. V6T 1Z1, Canada


Synthetic routes to a series of diterpene analogues from dehydroabietic acid (1) are presented. These synthetic compounds are then utilized as substrates in biotransformation experiments with the cells of a stable cell line (coded as TRP4a) of the Chinese herbal plant, Tripterygium wilfordii. The enzyme-catalyzed conversions of the substrate, isotriptophenolide (12), afford a series of novel diterpene analogues to be evaluated in pharmacological screening programs as antineoplastic and immunosuppressive agents. Of particular interest are the quinone epoxides (14) and (15) for comparison with the highly active diterpene triepoxides, triptolide and tripdiolide. Some screening data obtained with the latter compounds and relating to their anticancer and immunosuppressive activity are also presented.