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J Org Chem. 1998 Oct 2;63(20):6900-6904.

Brasilicardin A. A Novel Tricyclic Metabolite with Potent Immunosuppressive Activity from Actinomycete Nocardiabrasiliensis.

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Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan, Research Center for Pathogenic Fungi and Microbial Toxicoses, Chiba University, Chiba 260-8673, Japan, Research Laboratory, Higeta Shoyu Co., Ltd., Chiba 288-8680, Japan, Cancer Research Institute, Kanazawa University, Kanazawa 920-0934, Japan, and Osaka University of Pharmaceutical Sciences, Takatsuki 569-1094, Japan.


A novel tricyclic metabolite, brasilicardin A (1), with potent immunosuppressive activity has been isolated from the cultured broth of the actinomycete Nocardia brasiliensis IFM 0406, and the structure including absolute stereochemistry was established on the basis of spectroscopic data, chemical means, and X-ray analysis. Brasilicardin A (1) is the first tricyclic compound consisting of an anti/syn/anti-perhydrophenanthrene skeleton with a rhamnose, an N-acetylglucosamine, and an amino acid moiety.


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