Cladionol A, a Polyketide Glycoside from Marine-Derived Fungus Gliocladium Species

• Published in: Journal of natural products (Washington, D.C.) Vol. 68; no. 5; pp. 777 - 779
• Main Authors: Kasai, Yuu, Komatsu, Kazusei, Shigemori, Hideyuki, Tsuda, Masashi, Mikami, Yuzuru, Kobayashi, Jun'ichi
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 01-05-2005; Glendale, AZ American Society of Pharmacognosy
• Subjects: Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents; anticarcinogenic activity; Antineoplastic Agents - chemistry; Antineoplastic Agents - isolation & purification; Antineoplastic Agents - pharmacology; Applied microbiology; arabitol; Biological and medical sciences; chemical structure; Chemotherapic agents; cladionol; cultured cells; cytotoxicity; Drug Screening Assays, Antitumor; Fundamental and applied biological sciences. Psychology; Gliocladium; Gliocladium - chemistry; glycosides; Glycosides - chemistry; Glycosides - isolation & purification; Glycosides - pharmacology; glycosidic linkages; humans; Japan; mannopyranoside; Marine; mice; Microbiology; Models, Molecular; Molecular Structure; polyketides; spectral analysis; stereochemistry; Syringodium isoetifolium; Asia; Japan; Aldose; Trienic compound; Relative configuration; Cytotoxicity; Fungi; Marine environment; Polyketide; Ester; Alditol; Microbial origin; Absolute configuration; Isolation; Glycoside; Fungi Imperfecti; Polyol; Gliocladium; Thallophyta; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np050046b

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 β-mannopyranoside and arabitol on the basis of NOESY data and/or 1H−H 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.