title: Delitschiapyrone A, a pyrone-naphthalenone adduct bearing a new pentacyclic ring system from the leaf-associated fungus Delitschia sp. FL1581.
abstract: Delitschiapyrone A (1), an α-pyrone-naphthalenone adduct with an unprecedented pentacyclic ring system, was isolated from a solid culture of the leaf-associated fungus Delitschia sp. FL1581. The structure of 1 was elucidated by spectroscopic analysis and X-ray crystallography, and its absolute configuration was defined by experimental and calculated ECD. Biosynthetically, the unique 6/6/5/7/6 pentacyclic core of 1 may be formed by an intermolecular Diels-Alder-type addition of the precursors derived from (1'R)-2',3'-dihydropyrenocine C (2) and 6-ethyl-2,7-dimethoxyjuglone (3) found to co-occur with 1 in this fungus.
authors.affiliation: State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University , 24 Tong Jia Xiang, Nanjing 210009, People's Republic of China.
authors.forename: Jian-Guang
authors.initials: JG
authors.lastname: Luo
authors.forename: Xiao-Bing
authors.initials: XB
authors.lastname: Wang
authors.forename: Ya-Ming
authors.initials: YM
authors.lastname: Xu
authors.forename: Jana M
authors.initials: JM
authors.lastname: U'Ren
authors.forename: A Elizabeth
authors.initials: AE
authors.lastname: Arnold
authors.forename: Ling-Yi
authors.initials: LY
authors.lastname: Kong
authors.forename: A A Leslie
authors.initials: AA
authors.lastname: Gunatilaka
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001203:Ascomycota / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D008968:Molecular Conformation; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D019906:Nuclear Magnetic Resonance, Biomolecular; D018515:Plant Leaves / Q000382:microbiology; D011753:Pyrones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
chemical_list: D000970:Antineoplastic Agents; D009281:Naphthalenes; D011753:Pyrones; C000599603:delitschiapyrone A