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Cladionol A, a Polyketide Glycoside from Marine-Derived Fungus <i>Gliocladium</i> Species

Yuu KasaiGraduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan, and Research Center for Pathogenic Fungi and Microbial Toxicoses, Chiba University, Chiba 260-0856, JapanKazusei KomatsuGraduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan, and Research Center for Pathogenic Fungi and Microbial Toxicoses, Chiba University, Chiba 260-0856, JapanHideyuki ShigemoriGraduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan, and Research Center for Pathogenic Fungi and Microbial Toxicoses, Chiba University, Chiba 260-0856, JapanMasashi TsudaGraduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan, and Research Center for Pathogenic Fungi and Microbial Toxicoses, Chiba University, Chiba 260-0856, JapanYuzuru MikamiGraduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan, and Research Center for Pathogenic Fungi and Microbial Toxicoses, Chiba University, Chiba 260-0856, JapanJun’ichi KobayashiGraduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan, and Research Center for Pathogenic Fungi and Microbial Toxicoses, Chiba University, Chiba 260-0856, Japan

2005en

ABI

Annotatsiya

A new polyketide glycoside, cladionol A (1), was isolated from the cultured broth of a fungus Gliocladium sp., which was separated from sea grass Syringodium isoetifolium, and the structure was elucidated by spectroscopic data. The relative stereochemistry of C-2-C-3 was assigned by mainly J-based configuration analysis, while those of two sugar units were elucidated to be beta-mannopyranoside and arabitol on the basis of NOESY data and/or 1H-1H couplings. Furthermore, the absolute configuration of the mannose moiety was determined as the D-form on the basis of chiral HPLC analysis of a benzoyl derivative of the acid hydrolysate of 1. Cladionol A (1) exhibited modest cytotoxicity.

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DOI: 10.1021/np050046b

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