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Communication | Regular issue | Vol 27, No. 3, 1988, pp.629-637
Published online, 1st January, 1970
DOI: 10.3987/COM-87-4411
Alkaloid Production in Catharanthus roseus (L.) G. Don Cell Cultures. XVI. Biotransformation of 3’,4’-Anhydrovinblastine with Catharanthus roseis Cell Cultures and Enzyme Systems

James Peter Kutney,* Bruno Botta, Camille Andre Boulet, Carlos Alberto Buschi, Lewis Siu Leung Choi, Jerzy Golinski, Maria Gumulka, Gary Maxwell Hewitt, Gin Lee, Michael McHuge, Jun Nakano, Tamotsu Nikaido, Jun-ichi Onodera, Ileana Perez, Philip Salisbury, Mahatam Singh, Roger Suen, and Hiroki Tsukamoto

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

Abstract

Employing cell cultures of Catharanthus roseus and enzyme systems derived from such cultures, a detailed study of the biotransformation of 3’,4’-anhydrovinblestine (3) is described. It is shown that enzymatic conversion of 3 to the isolated end products, the bisindole alkaloids leurosine (4), vinblastine (5), catharine (6), vinamidine (7) and hydroxyvinamidine (8) proceeds initially to the same dihydropyridinium intermediate (9) obtained when the monomeric alkaloids catharanthine (1) and vindoline (2) are enzymatically coupled. These data establish that the overall biosynthetic pathway to the bisindole alkaloids proceeds from 1 and 2 to the initially formed 9 and the latter, under enzymatically controlled oxidation-reduction, affords the alkaloids 3-8. However, when 3 is incubated as substrate, the enzymes are capable of utilizing and converting It into the alkaloids 4-8. In summary, 3 is not a direct biosynthetic precursor of 4-8.