Streptomyces albogriseolus

Vindoline [2182-14-1] (45), a monomeric Vinca alkaloid intermediate important in the synthesis of antineoplastic alkaloids, is selectively converted in good yield to 0-desmethylvindoline [68687-22-9] (46) by cultures of Sepedonium chrysospermum (17,25), whereas Streptomyces albogriseolus removes only the A[-methyl group to give (47) (91) (see Chemotherapeutics, anticancer). 

Streptomyces albogriseolus as a Potential Bioremediation Agent for Sulfosulfuron... 

Keywords Bioremediation Streptomyces albogriseolus Sulfosulfuron Degradation Environment. 

Rosazza et al. (52) have proposed the mechanism shown in Fig. 6 for the formation of both dihydrovindoline ether and its dimer from vindoline. This mechanism, which proposes an intermediate enamine-immonium ion species 54-55 produced by N-oxidation, followed by intramolecular attack of the C-l 6 hydroxyl oxygen, also accounts for the formation of 3-acetonyldihydro-vindoline ether 42 from vindoline by Streptomyces albogriseolus (49). Reduction of the immonium ion 55 thus leads directly to dihydrovindoline ether, whereas its capture by acetoacetate or the enamine 54 (79) leads to 42 and 45, respectively. 

Transformations of the dimeric alkaloid vinblastine (46) by Streptomyces species have been reported which involve N-demethylation (51), aromatic hydroxylation (55), and intramolecular ether formation (53). With Streptomyces albogriseolus, N-demethylation occurs in an undisclosed yield to produce 47 (51). The same organism in the hands of the same workers is also reported to lead to the formation of vinblastine ether (50) in low yield, along... 

Na-Desmethylvindoline (8—10%) is found among the products of the microbiological conversion of vindoline by means of Streptomyces albogriseolus ... 

When incubated with Streptomyces albogriseolus, vindoline (101) afforded yet another new product whose mass spectrum indicated an additional 56 mu (C3H4O) in comparison with 11-methoxycathovaline (104). This mass was found in the piperidine ring, which now appeared at m/e 178 (corresponding to m/e 122 in vindoline). The C-15 proton was observed as a multiplet at 4.06 ppm confirming a C-14 methylene. 

Kikuchi, Y., Date, M., Yokoyama, K., Umezawa, Y. et al. (2003) Secretion of active-form Streptoverticillium mobaraense transglutaminase by Corynebacterium glutamicum processing of the pro-transglutaminase by a cosecreted subtilisin-like protease from Streptomyces albogriseolus. Appl. Environ. Microbiol., 69, 358-366. 

Class Actinobacteria Subclass Actinobacteridae Order Actinomycetales Suborder Streptomycineae Family Streptomycetaceae Streptomyces albogriseolus m Van Zyl (1985)... 

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