title: Chlorotheolides A and B, Spiroketals Generated via Diels-Alder Reactions in the Endophytic Fungus Pestalotiopsis theae.
abstract: Chlorotheolides A (1) and B (2), two new spiroketals possessing the unique [4,7]methanochromene and dispiro-trione skeletons, respectively, and their putative biosynthetic precursors, 1-undecen-2,3-dicarboxylic acid (3) and maldoxin (4), were isolated from the solid substrate fermentation of the plant endophytic fungus Pestalotiopsis theae (N635). Their structures were elucidated based on NMR spectroscopic data and electronic circular dichroism calculations. Biogenetically, compounds 1 and 2 could be generated from the co-isolated 3 and 4 via Diels-Alder reactions. Chlorotheolide (2) showed an antiproliferative effect against the human tumor cell line HeLa and induced an autophagic process in the cells.
authors.affiliation: State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences , Beijing 100101, People's Republic of China.
authors.forename: Ling
authors.initials: L
authors.lastname: Liu
authors.affiliation: State Key Laboratory of Toxicology & Medical Countermeasures, Beijing Institute of Pharmacology & Toxicology , Beijing 100850, People's Republic of China.|State Key Laboratory of Natural Medicines, China Pharmaceutical University , Nanjing 210009, People's Republic of China.
authors.forename: Yu
authors.initials: Y
authors.lastname: Han
authors.affiliation: State Key Laboratory of Toxicology & Medical Countermeasures, Beijing Institute of Pharmacology & Toxicology , Beijing 100850, People's Republic of China.
authors.forename: Junhai
authors.initials: J
authors.lastname: Xiao
authors.affiliation: Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College , Beijing 100050, People's Republic of China.
authors.forename: Li
authors.initials: L
authors.lastname: Li
authors.affiliation: State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences , Beijing 100101, People's Republic of China.
authors.forename: Liangdong
authors.initials: L
authors.lastname: Guo
authors.affiliation: State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences , Beijing 100101, People's Republic of China.
authors.forename: Xuejun
authors.initials: X
authors.lastname: Jiang
authors.affiliation: State Key Laboratory of Natural Medicines, China Pharmaceutical University , Nanjing 210009, People's Republic of China.
authors.forename: Lingyi
authors.initials: L
authors.lastname: Kong
authors.affiliation: State Key Laboratory of Toxicology & Medical Countermeasures, Beijing Institute of Pharmacology & Toxicology , Beijing 100850, People's Republic of China.
authors.forename: Yongsheng
authors.initials: Y
authors.lastname: Che
mesh_terms: D001203:Ascomycota / Q000737:chemistry*; D002681:China; D061565:Cycloaddition Reaction; D004354:Drug Screening Assays, Antitumor; D005663:Furans / Q000737:chemistry; D006367:HeLa Cells; D006801:Humans; D007783:Lactones / Q000378:metabolism; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010944:Plants; D013141:Spiro Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism; D013237:Stereoisomerism; D013098:Xylariales / Q000737:chemistry
chemical_list: D005663:Furans; D007783:Lactones; D013141:Spiro Compounds; C000620418:chlorotheolide A; C000620419:chlorotheolide B; C562279:maldoxin; C520774:spiroketal