Antimalarial halorosellinic acid from the marine fungus Halorosellinia oceanica

• Published in: Bioorganic & medicinal chemistry letters Vol. 11; no. 15; pp. 1965 - 1969
• Main Authors: Chinworrungsee, Maneekarn, Kittakoop, Prasat, Isaka, Masahiko, Rungrod, Amporn, Tanticharoen, Morakot, Thebtaranonth, Yodhathai
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 06.08.2001; Elsevier
• Subjects: Animals; Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents; Antimalarials - chemical synthesis; Antimalarials - pharmacology; Applied microbiology; Biological and medical sciences; Cytochalasins - chemical synthesis; Cytochalasins - pharmacology; Fundamental and applied biological sciences. Psychology; Fungi - chemistry; General aspects; Humans; Inhibitory Concentration 50; Isocoumarins; KB Cells; Microbial Sensitivity Tests; Microbiology; Mycobacteriaceae - drug effects; Ochratoxins - chemical synthesis; Ochratoxins - pharmacology; Plasmodium falciparum - drug effects; Sesterterpenes; Succinates - chemical synthesis; Succinates - pharmacology; Terpenes - chemical synthesis; Terpenes - pharmacology; Thailand; Asia; Antineoplastic agent; Antimalarial; Cytotoxicity; Fungi; Marine environment; Plasmodium falciparum; Carboxylic acid; Parasiticid; Bacteria; Dicarboxylic acid; Ascomycetes; Antituberculous agent; Thallophyta; Human; Protozoa; Terpenoid; Apicomplexa; Diol; Pharmacognosy; In vitro; Biological activity; Cell line; Mycobacterium tuberculosis; Mycobacteriales; KB cell line; Plant origin; Mycobacteriaceae; Isolation; Actinomycetes; Antibacterial agent; Sesterterpenes; Ethylenic compound; Glycol; Structural analysis
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/S0960-894X(01)00327-4

Three known compounds, 2-hexylidene-3-methylsuccinic acid ( 1), cytochalasin Q ( 2), and 5-carboxymellein ( 3), together with two new derivatives, 2-hexylidene-3-methylsuccinic acid 4-methyl ester ( 4) and an ophiobolane sesterterpene named halorosellinic acid ( 5), were isolated from culture broth of the marine fungus Halorosellinia oceanica BCC 5149. Compounds 1– 3 exhibited moderate cytotoxicity against KB and BC-1 cell lines with IC 50 values of 1–13 μg/mL, while compounds 2, 3, 5, and 6 showed antimalarial activity with respective IC 50 values of 17, 4, 13, and 19 μg/mL. Halorosellinic acid ( 5) possessed only weak antimycobacterial activity with the minimum inhibitory concentration of 200 μg/mL. Two new metabolites ( 4 and 5) were isolated from the marine fungus Halorosellinia oceanica. The opiobolane sesterterpene 5 exhibited moderate antimalarial and weak antimycobacterial activities.