Aspergilloxide, a novel sesterterpene epoxide from a marine-derived fungus of the genus Aspergillus.
[structure: see text]. A new sesterterpene epoxide-diol, aspergilloxide (1), was isolated from the extract of a cultured marine-derived fungus (strain CNM-713) identified as an undescribed member of the genus Aspergillus. The structure of 1 was determined by interpretation of NMR data and by chemical methods. The absolute stereochemistry of aspergilloxide was assigned by application of the modified Mosher method. The carbon skeleton of 1 represents a new addition to the architectural diversity of the sesterterpenoid (C25) class of secondary metabolites.
Cueto
Mercedes
M
Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California at San Diego, La Jolla, California 92093-0204, USA.
Jensen
Paul R
PR
Fenical
William
W
D000107:Acetylation; D000903:Antibiotics, Antineoplastic / Q000737:chemistry* / Q000494:pharmacology; D001230:Aspergillus / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D004852:Epoxy Compounds / Q000737:chemistry* / Q000494:pharmacology; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D013729:Terpenes / Q000737:chemistry* / Q000494:pharmacology; D014407:Tumor Cells, Cultured
D000903:Antibiotics, Antineoplastic; D004852:Epoxy Compounds; D013729:Terpenes; C457039:aspergilloxide