Isariotins E and F, Spirocyclic and Bicyclic Hemiacetals from the Entomopathogenic Fungus Isaria tenuipes BCC 12625

• Published in: Journal of natural products (Washington, D.C.) D.C.), 2009-04, Vol.72 (4), p.756-759
• Main Authors: Bunyapaiboonsri, Taridaporn, Yoiprommarat, Seangaroon, Intereya, Kamolphan, Rachtawee, Pranee, Hywel-Jones, Nigel L, Isaka, Masahiko
• Format: Article
• Language: English
• Subjects: Animals; Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents; antimalarials; Antimalarials - chemistry; Antimalarials - isolation & purification; Antimalarials - pharmacology; antineoplastic agents; Antineoplastic Agents - chemistry; Antineoplastic Agents - isolation & purification; Antineoplastic Agents - pharmacology; Antitubercular Agents - chemistry; Antitubercular Agents - isolation & purification; Antitubercular Agents - pharmacology; Applied microbiology; bioactive properties; Biological and medical sciences; Bridged Bicyclo Compounds, Heterocyclic - chemistry; Bridged Bicyclo Compounds, Heterocyclic - isolation & purification; Bridged Bicyclo Compounds, Heterocyclic - pharmacology; Candida albicans - drug effects; Cercopithecus aethiops; chemical structure; cytotoxicity; Drug Screening Assays, Antitumor; entomopathogenic fungi; Epoxy Compounds - chemistry; Epoxy Compounds - isolation & purification; ethers; extracts; Fundamental and applied biological sciences. Psychology; General aspects; Heterocyclic Compounds, Bridged-Ring - chemistry; Heterocyclic Compounds, Bridged-Ring - isolation & purification; Humans; Hypocreales - chemistry; Inhibitory Concentration 50; isariotin E; isariotin F; isolation; Microbiology; Molecular Structure; Mycobacterium tuberculosis - drug effects; Paecilomyces; Parasitic Sensitivity Tests; Plasmodium falciparum; Plasmodium falciparum - drug effects; secondary metabolites; Spiro Compounds - chemistry; Spiro Compounds - isolation & purification; Spiro Compounds - pharmacology; spirocyclic hemiacetals; Thailand; TK-57-164A; Vero Cells
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np800702c

New spirocyclic and bicyclic hemiacetals, isariotins E (1) and F (2), together with TK-57-164A (3) were isolated from the entomopathogenic fungus Isaria tenuipes BCC 12625. The absolute configuration of 3 was addressed by application of the modified Mosher’s method. Isariotin F (2) exhibited activity against the malaria parasite Plasmodium falciparum K1 with an IC50 value of 5.1 μM and cytotoxic activities against cancer cell lines (KB, BC, and NCI-H187) and nonmalignant (Vero) cells with respective IC50 values of 15.8, 2.4, 1.6, and 2.9 μM.