New Teleocidin-Related Metabolites, (-)-7-Geranylindolactam-V and Blastmycetin F, from Streptoverticillium blastmyceticum

Journal of Natural Products
1994.0

Abstract

Two new teleocidin-related metabolites, (-)-7-geranylindolactam-V [2] and blastmycetin F [3], were isolated from fermentation broths of the actinomycete Streptoverticillium blastmyceticum NA34-17, and their structures were determined by spectroscopic methods. Compound 2 bound strongly to phorbol ester receptors in a mouse epidermal particulate fraction, suggesting that it is a potent in vivo tumor promoter comparable to teleocidins A-1 [4] and B-4 [5]. The teleocidins (1-5) are unusual indole alkaloids containing a nine-membered lactam ring and a complex monoterpenoid moiety, which act as potent skin tumor promoters (6). Several teleocidin-producing organisms (actinomycetes and blue-green algae) have been previously reported (7,8). Among these organisms, the actinomycete Streptoverticillium blastmyceticum NA34-17 (9,10) is unique in producing (-)-indolactam-V [1] (11) in quantity, in addition to minor components. In previous publications we have reported the isolation of several teleocidin-related compounds from this actinomycete (12-15), which have contributed to research on structure-activity relationships (16,17), metabolism in mammals (18), and teleocidin biosynthesis (19,20). Our continuing research aim to discover new teleocidin-related compounds has resulted in the isolation of (-)-7-geranylindolactam-V [2] and blastmycetin F [3] from S. blastmyceticum. This paper describes the isolation, structural determination, and biological activities of these new metabolites.

Knowledge Graph

Similar Paper

New Teleocidin-Related Metabolites, (-)-7-Geranylindolactam-V and Blastmycetin F, from Streptoverticillium blastmyceticum
Journal of Natural Products 1994.0
New Teleocidin-Related Metabolites, (-)-7-Geranylindolactam-V and Blastmycetin F, from Streptoverticillium blastmyceticum
Journal of Natural Products 1994.0
Structure and tumor-promoting activity of new teleocidin-related metabolites (blastmycetins) from Streptoverticillium blastmyceticum.
Agricultural and Biological Chemistry 1988.0
Structure and tumor-promoting activity of new teleocidin-related metabolites (blastmycetins) from Streptoverticillium blastmyceticum.
Agricultural and Biological Chemistry 1988.0
Structure of blastmycetin E, a new teleocidin-related compound, from streptoverticillium blastmyceticum
Tetrahedron Letters 1989.0
New teleocidin metabolites from Streptoverticillium blastmyceticum.
Agricultural and Biological Chemistry 1985.0
Isolation of blastmycetin D, a possible precursor of teleocidins, from Streptoverticillium blastmyceticum.
Agricultural and Biological Chemistry 1987.0
Isolation and biological activities of N13-desmethyl analogues of tumor promoter teleocidin from Streptoverticillium blastmyceticum.
Agricultural and Biological Chemistry 1988.0
Isolation of Blastmycetin D, a Possible Precursor of Teleocidins, from<i>Streptoverticillium blastmyceticum</i>
Agricultural and Biological Chemistry 1987.0
Isolation of (-)-14-<i>O</i>-Malonylindolactam-V as a Possible Precursor of (-)-Indolactam-V and (-)-14-<i>O</i>-Acetylindolactam-V from<i>Streptomyces blastmyceticum</i>
Bioscience, Biotechnology, and Biochemistry 1999.0