title: Anteaglonialides A-F and Palmarumycins CE(1)-CE(3) from Anteaglonium sp. FL0768, a Fungal Endophyte of the Spikemoss Selaginella arenicola.
abstract: Anteaglonialides A-F (1-6), bearing a spiro[6-(tetrahydro-7-furanyl)cyclohexane-1,2'-naphtho[1,8-de][1,3]-dioxin]-10-one skeleton, three new spirobisnaphthalenes, palmarumycins CE1-CE3 (7-9), nine known palmarumycin analogues, palmarumycins CP5 (10), CP4a (11), CP3 (12), CP17 (13), CP2 (14), and CP1 (15), CJ-12,371 (16), 4-O-methyl CJ-12,371 (17), and CP4 (18), together with a possible artifact, 4a(5)-anhydropalmarumycin CE2 (8a), and four known metabolites, O-methylherbarin (19), herbarin (20), herbaridine B (21), and hyalopyrone (22), were encountered in a cytotoxic extract of a potato dextrose agar culture of Anteaglonium sp. FL0768, an endophytic fungus of the sand spikemoss, Selaginella arenicola. The planar structures and relative configurations of the new metabolites 1-9 were elucidated by analysis of extensive spectroscopic data, and the absolute configuration of 1 was determined by the modified Mosher's ester method. Application of the modified Mosher's ester method combined with the NOESY data resulted in revision of the absolute configuration previously proposed for 10. Co-occurrence of 1-6 and 7-18 in this fungus led to the proposal that the anteagloniolides may be biogenetically derived from palmarumycins. Among the metabolites encountered, anteaglonialide F (6) and known palmarumycins CP3 (12) and CP1 (15) exhibited strong cytotoxic activity against the human Ewing's sarcoma cell line CHP-100, with IC50 values of 1.4, 0.5, and 1.6 μM, respectively.
authors.affiliation: Southwest Center for Natural Products Research and Commercialization, 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: Ya-ming
authors.initials: YM
authors.lastname: Xu
authors.affiliation: Southwest Center for Natural Products Research and Commercialization, 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.|Departamento de Química Orgânica e Inorgânica, Universidade Federal do Ceará , Campus do Pici, Caixa Postal 6044, Fortaleza-CE 60455-970, Brazil.
authors.forename: Jair
authors.initials: J
authors.lastname: Mafezoli
authors.affiliation: Southwest Center for Natural Products Research and Commercialization, 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.|Departamento de Química Orgânica e Inorgânica, Universidade Federal do Ceará , Campus do Pici, Caixa Postal 6044, Fortaleza-CE 60455-970, Brazil.
authors.forename: Maria C F
authors.initials: MC
authors.lastname: Oliveira
authors.forename: Jana M
authors.initials: JM
authors.lastname: U'Ren
authors.forename: A Elizabeth
authors.initials: AE
authors.lastname: Arnold
authors.affiliation: Southwest Center for Natural Products Research and Commercialization, 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.initials: AA
authors.lastname: Gunatilaka
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001203:Ascomycota / Q000737:chemistry; D004354:Drug Screening Assays, Antitumor; D060026:Endophytes / Q000737:chemistry; D005431:Florida; D006801:Humans; D020128:Inhibitory Concentration 50; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D009285:Naphthoquinones; D019906:Nuclear Magnetic Resonance, Biomolecular; D032503:Selaginellaceae / Q000737:chemistry*; D013141:Spiro Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
chemical_list: D000972:Antineoplastic Agents, Phytogenic; C092868:CJ 12371; D009281:Naphthalenes; D009285:Naphthoquinones; D013141:Spiro Compounds; C001334:herbarin