Mangicols: structures and biosynthesis of A new class of sesterterpene polyols from a marine fungus of the genus Fusarium.

Abstract

A marine fungal isolate, tentatively identified as Fusarium heterosporum, has been found to produce a series of structurally novel sesterterpene polyols, the mangicols A-G (4-10). The structures of the new compounds, including the stereochemistry of mangicol A, were assigned by interpretation of spectral data derived from both natural products and synthetic derivatives. The mangicols, which possess unprecedented spirotricyclic skeletal components, show only weak to modest cytotoxicities toward a variety of cancer cell lines in in vitro testing. Mangicols A and B, however, showed significant antiinflammatory activity in the PMA (phorbol myristate acetate)-induced mouse ear edema model. A biosynthetic pathway for the neomangicol and mangicol carbon skeletons is proposed on the basis of the incorporation of appropriate radiolabeled precursors.

• Authors: M K Renner, P R Jensen, W Fenical
• Journal: The Journal of organic chemistry (J Org Chem) Vol. 65 Issue 16 Pg. 4843-52 (Aug 11 2000) ISSN: 0022-3263 [Print] United States
• PMID: 10956462 (Publication Type: Journal Article, Research Support, U.S. Gov't, P.H.S.)

Chemical References

• Anti-Inflammatory Agents
• Sesquiterpenes
• Sesterterpenes
• Terpenes
• mangicol A
• mangicol B
• Tetradecanoylphorbol Acetate

Topics

• Animals
• Anti-Inflammatory Agents (chemistry, therapeutic use)
• Ear
• Edema (chemically induced, drug therapy)
• Fusarium (chemistry)
• Mice
• Models, Chemical
• Models, Molecular
• Sesquiterpenes (chemistry, therapeutic use)
• Sesterterpenes
• Stereoisomerism
• Structure-Activity Relationship
• Terpenes (chemistry)
• Tetradecanoylphorbol Acetate