Discovery of a Tambjamine Gene Cluster in Streptomyces Suggests Convergent Evolution in Bipyrrole Natural Product Biosynthesis.
作者: Neil L Grenade ; Dragos S Chiriac ; A R Ola Pasternak ; Jonathan L Babulic ; Bronwyn E Rowland ; Graeme W Howe ; Avena C Ross
While bacterial natural products are a valuable source of therapeutics, the molecules produced by most biosynthetic gene clusters remain unknown. Tambjamine YP1, produced by Pseudoalteromonas tunicata, is partially derived from fatty acids siphoned from primary metabolism. A structurally similar tambjamine produced by Streptomyces, BE-18591, had not been linked to a gene cluster. Using enzymes putatively implicated in the construction of these two tambjamines, we used sequence similarity networks and gene knockout experiments to identify the biosynthetic gene cluster responsible for the production of tambjamine BE-18591 in Streptomyces albus. Despite the structural similarities between YP1 and BE-18591, the biosynthesis of the alkylamine tails of these molecules differs significantly, with the S. albus gene cluster putatively encoding a dedicated system for the construction of the fatty acid precursor to BE-18591. These different pathways in Pseudoalteromonas and Streptomyces suggest that evolutionary convergence is operative, with similar selective pressures leading to the emergence of structurally similar tambjamine natural products using different biosynthetic logic.
2010-05-01·Chemistry & Biodiversity3区 · 化学
Antimicrobial and Cytotoxic Activities of Synthetically Derived Tambjamines C and E - J, BE-18591, and a Related Alkaloid from the Marine Bacterium Pseudoalteromonas tunicata
3区 · 化学
作者: Pinkerton, David M. ; Banwell, Martin G. ; Garson, Mary J. ; Kumar, Naresh ; Odorico de Moraes, Manoel ; Cavalcanti, Bruno C. ; Barros, Francisco W. A. ; Pessoa, Claudia
In the first comprehensive biological assessment of the tambjamine class of marine alkaloids, synthetically derived samples of compounds 1-9 have been subjected to evaluation as antimicrobial agents and screened for their cytotoxic effects on various human cancer cell lines. Most were strongly active against the fungus Malassezia furfur (>amphotericin B) and showed considerable, but non-selective, antiproliferative activity against both human cancer and normal cell lines. Tambjamines I and J (6 and 7, resp.) displayed significant apoptosis-inducing effects.
2007-11-22·Organic Letters1区 · 化学
Total Syntheses of Tambjamines C, E, F, G, H, I and J, BE-18591, and a Related Alkaloid from the Marine Bacterium Pseudoalteromonas tunicata
1区 · 化学
作者: Pinkerton, David M. ; Banwell, Martin G. ; Willis, Anthony C.
The acetate salts of tambjamines C, E, and F (2-4, respectively), as well as those of the related alkaloids BE-18591 (5) and 6, have been prepared by treatment of bipyrrole aldehyde 16 with the relevant amine in the presence of acetic acid. The 5'-bromo-analogue, 30, of compound 16 has also been prepared and used to obtain the acetate salts of tambjamines G, H, I, and J (8-11 respectively).