title: Chlorinated Dehydrocurvularins and Alterperylenepoxide A from Alternaria sp. AST0039, a Fungal Endophyte of Astragalus lentiginosus.
abstract: Investigation of Alternaria sp. AST0039, an endophytic fungus obtained from the leaf tissue of Astragalus lentiginosus, led to the isolation of (-)-(10E,15S)-4,6-dichloro-10(11)-dehydrocurvularin (1), (-)-(10E,15S)-6-chloro-10(11)-dehydrocurvularin (2), (-)-(10E,15S)-10(11)-dehydrocurvularin (3), and alterperylenepoxide A (4) together with scytalone and α-acetylorcinol. Structures of 1 and 4 were established from their spectroscopic data, and the relative configuration of 4 was determined with the help of nuclear Overhauser effect difference data. All metabolites were evaluated for their cytotoxic activity and ability to induce heat-shock and unfolded protein responses. Compounds 2 and 3 exhibited cytotoxicity to all five cancer cell lines tested and increased the level of the pro-apoptotic transcription factor CHOP, but only 3 induced the heat-shock response and caused a strong unfolded protein response.
authors.affiliation: Natural Products Center, School of Natural Resources and the Environment, College of Agriculture and Life Sciences, University of Arizona , 250 E. Valencia Road, Tucson, Arizona 85706, United States.
authors.forename: Bharat P
authors.initials: BP
authors.lastname: Bashyal
authors.affiliation: Natural Products Center, School of Natural Resources and the Environment, College of Agriculture and Life Sciences, University of Arizona , 250 E. Valencia Road, Tucson, Arizona 85706, United States.
authors.forename: E M Kithsiri
authors.initials: EM
authors.lastname: Wijeratne
authors.affiliation: Department of Pharmacology and Toxicology, College of Pharmacy, University of Arizona , Tucson, Arizona 85721, United States.
authors.forename: Joseph
authors.initials: J
authors.lastname: Tillotson
authors.affiliation: School of Plant Sciences, College of Agriculture and Life Sciences, University of Arizona , Tucson, Arizona 85721, United States.
authors.forename: A Elizabeth
authors.initials: AE
authors.lastname: Arnold
authors.affiliation: Department of Pharmacology and Toxicology, College of Pharmacy, University of Arizona , Tucson, Arizona 85721, United States.
authors.forename: Eli
authors.initials: E
authors.lastname: Chapman
authors.affiliation: Natural Products Center, School of Natural Resources and the Environment, College of Agriculture and Life Sciences, University of Arizona , 250 E. Valencia Road, Tucson, Arizona 85706, United States.
authors.forename: A A Leslie
authors.identifier: 0000-0001-9663-3600
authors.initials: AA
authors.lastname: Gunatilaka
mesh_terms: D000528:Alternaria / Q000737:chemistry*; D027883:Astragalus Plant / Q000382:microbiology*; D004354:Drug Screening Assays, Antitumor; D060026:Endophytes / Q000737:chemistry; D006801:Humans; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D015025:Zearalenone / Q000031:analogs & derivatives / Q000737:chemistry* / Q000302:isolation & purification*
chemical_list: C013914:dehydrocurvularin; D015025:Zearalenone