Characterization of 6-epi-3-Anhydroophiobolin B from Cochliobolus heterostrophus

• Published in: Journal of natural products (Washington, D.C.) Vol. 62; no. 6; pp. 895 - 897
• Main Authors: Shen, Xiaoyu, Krasnoff, Stuart B, Lu, Shun-Wen, Dunbar, Chuck D, O'Neal, James, Turgeon, B. Gillan, Yoder, Olen C, Gibson, Donna M, Hamann, Mark T
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.06.1999; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: 6-epi-3-anhydroophiobolin B; Animals; Antibiotics, Antineoplastic - isolation & purification; Antibiotics, Antineoplastic - pharmacology; antimalarial properties; Antimalarials - isolation & purification; Antimalarials - pharmacology; Ascomycota - chemistry; Biological and medical sciences; Bridged Bicyclo Compounds - isolation & purification; Bridged Bicyclo Compounds - pharmacology; chemical constituents of plants; chemical structure; Chemistry, Medicinal; Chromatography, High Pressure Liquid; Cochliobolus heterostrophus; cytotoxic compounds; Drug Screening Assays, Antitumor; General pharmacology; Humans; Inhibitory Concentration 50; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Medical sciences; ophiobolin A; ophiobolins; ophiogolins; Pharmacognosy. Homeopathy. Health food; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Plant Sciences; Plasmodium falciparum - drug effects; Science & Technology; sesterterpenoids; spectral analysis; terpenoids; Tumor Cells, Cultured; SORGHICOLA; METABOLITES; SESTERTERPENOIDS; OPHIOBOLIN-A; Antineoplastic agent; Terpenoid; Pharmacognosy; Epimer; Alcohol; Cytotoxicity; Cochliobolus heterostrophus; Aldehyde; Ketone; In vitro; Biological activity; Spiran; Fungi; Plant origin; Isolation; Ascomycetes; Sesterterpenes; Tumor cell; Thallophyta; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np980462e

The new sesterterpenoid 6-epi-3-anhydroophiobolin B (1) and six known ophiobolins were isolated from the extracts of the fungus Cochliobolus heterostrophus race O. The structure of 6-epi-3-anhydroophiobolin B was deduced from analysis of spectral data and the structural characterization of dehydration and dimerization products. Ophiobolin A (2) showed potent activity in cytotoxicity assays and marginal activity in antimalarial assays.