Microbial Transformations of Natural Antitumor Agents: O-Demethylation of Vindoline by Sepedonium chrysospermum
作者： G.-S. Wu , T. Nabih , L. Youel , W. Peczynska-Czoch , J. P. Rosazza
DOI: 10.1128/AAC.14.4.601
关键词:
摘要: Vindoline (1a) was transformed to O-demethylvindoline (1b) by Sepedonium chrysospermum ATCC 13378 in 33% yield. Thin-layer and high-pressure liquid chromatographic methods distinguished 1b from previously reported microbial metabolites of vindoline. The structural proof based on its mass spectral fragmentation pattern chemical nuclear magnetic resonance properties.
sci-hub.se 参考文章(10)
M.A. Rahim, Charles J. Sih, Mechanisms of steroid oxidation by microorganisms. XI. Enzymatic cleavage of the pregnane side chain. Journal of Biological Chemistry. ,vol. 241, pp. 3615- 3623 ,(1966) , 10.1016/S0021-9258(18)99875-3
Marvin Gorman, Norbert Neuss, Gordon H. Svoboda, Albert J. Barnes, Nancy J. Cone, A Note on the Alkaloids of Vinca rosea Linn. (Catharanthus roseus G. Don.) II.**Lilly Research Laboratories and Organic Chemical Development, Eli Lilly and Co., Indianapolis, Ind. Journal of the American Pharmaceutical Association (Scientific ed.). ,vol. 48, pp. 256- 257 ,(1959) , 10.1002/JPS.3030480419
Patrick J. Davis, John P. Rosazza, Microbial transformations of natural antitumor agents. 2. Studies with d-tetrandrine and laudanosine. Journal of Organic Chemistry. ,vol. 41, pp. 2548- 2551 ,(1976) , 10.1021/JO00877A009
N. Neuss, D. S. Fukuda, G. E. Mallett, D. R. Brannon, L. L. Huckstep, Vinca alkaloids. XXXII. Microbiological conversions of vindoline, a major alkaloid from Vinca rosea L. Helvetica Chimica Acta. ,vol. 56, pp. 2418- 2426 ,(1973) , 10.1002/HLCA.19730560725
M. Tin‐Wa, Shen‐Kai Lin, E.H. Taylor, Microbial transformation of aspidospermine Journal of Pharmaceutical Sciences. ,vol. 64, pp. 2021- 2022 ,(1975) , 10.1002/JPS.2600641231
Norbert Neuss, D. S. Fukuda, D. R. Brannon, L. L. Huckstep, Vinca alkaloids XXXIV. Preparation of des-Na-methyl-vindoline by microbiological conversion of vindoline, a major alkaloid from Vinca roseaL† Helvetica Chimica Acta. ,vol. 57, pp. 1891- 1893 ,(1974) , 10.1002/HLCA.19740570644
Ronald E. Betts, David E. Walters, John P. Rosazza, Microbial transformations of antitumor compounds. 1. Conversion of acronycine to 9-hydroxyacronycine by Cunninghamella echinulata. Journal of Medicinal Chemistry. ,vol. 17, pp. 599- 602 ,(1974) , 10.1021/JM00252A006
T. Nabih, P. J. Davis, J. F. Caputo, J. P. Rosazza, Microbial transformations of natural antitumor agents. 3. Conversion of thalicarpine to (+)-hernandalinol by Streptomyces punipalus Journal of Medicinal Chemistry. ,vol. 20, pp. 914- 917 ,(1977) , 10.1021/JM00217A010
John P. Rosazza, Marianne Kammer, Leisa Youel, Robert V. Smith, Paul W. Erhardt, Duyen H. Truong, Steven W. Leslie, Microbial models of mammalian metabolism O-demethylations of papaverine. Xenobiotica. ,vol. 7, pp. 133- 143 ,(1977) , 10.3109/00498257709036245
J. P. Rosazza, D. R. Wiese, P. J. Davis, Microbial transformations of natural antitumor agents. IV. Formation of N-(2)-nor-d-tetrandrine by Cunninghamella blakesleeana (ATCC 8688a). Lloydia. ,vol. 40, pp. 239- 246 ,(1977)