1355-31-3Relevant articles and documents
ALKALOID PRODUCTION IN CATHARANTHUS ROSEUS (L.) G. DON CELL CULTURES. XVI. BIOTRANSFORMATION OF 3',4'-ANHYDROVINBLASTINE WITH CATHARANTHUS ROSEUS CELL CULTURES AND ENZYME SYSTEMS
Kutney, James Peter,Botta, Bruno,Boulet, Camille Andre,Buschi, Carlos Alberto,Choi, Lewis Siu Leung,et al.
, p. 629 - 638 (2007/10/02)
Employing cell cultures of Catharanthus roseus and enzyme systems derived from such cultures, a detailed study of the biotransformation of 3',4'-anhydrovinblastine (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.
