title: Cytotoxic dihydrothiophene-condensed chromones from the marine-derived fungus Penicillium oxalicum.
abstract: Two new dihydrothiophene-condensed chromones and a new natural chromone, namely oxalicumones A-C (1-3), respectively, were isolated from a culture broth of a marine-derived fungus, Penicillium oxalicum. The structures of 1-3 and acetylated derivatives of 1 (4-7) were elucidated on the basis of spectroscopic methods and chemical reactions. The absolute configuration of 1 and 2 were established by using the modified Mosher ester method and circular dichroism data of an in situ formed [Rh2(OCOCF3)4] and [Mo2(OAc)4] complex. (R)-MTPA ester of 1 showed cytotoxicity against A375, SW-620, and HeLa carcinoma cell lines with IC50 values of 8.9, 7.8, and 18.4 µM, respectively. Compound 1 displayed cytotoxicity against A375 and SW-620 cell lines with IC50 values of 11.7 and 22.6 µM, respectively. The structure-biological activity relationship of 1 was discussed.
authors.affiliation: Key Laboratory of Marine Bio-resources Sustainable Utilization/Guangdong Key Laboratory of Marine Materia Medica/RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, The Chinese Academy of Sciences, Guangzhou, Guangdong, P. R. China.
authors.forename: Yu-Lin
authors.initials: YL
authors.lastname: Sun
authors.forename: Jie
authors.initials: J
authors.lastname: Bao
authors.forename: Kai-Sheng
authors.initials: KS
authors.lastname: Liu
authors.forename: Xiao-Yong
authors.initials: XY
authors.lastname: Zhang
authors.forename: Fei
authors.initials: F
authors.lastname: He
authors.forename: Yi-Fei
authors.initials: YF
authors.lastname: Wang
authors.forename: Xu-Hua
authors.initials: XH
authors.lastname: Nong
authors.forename: Shu-Hua
authors.initials: SH
authors.lastname: Qi
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology / Q000627:therapeutic use; D001688:Biological Products / Q000737:chemistry* / Q000494:pharmacology / Q000627:therapeutic use; D002867:Chromones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology / Q000627:therapeutic use; D005260:Female; D006367:HeLa Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D010407:Penicillium / Q000737:chemistry*; D013329:Structure-Activity Relationship; D013876:Thiophenes; D002583:Uterine Cervical Neoplasms / Q000188:drug therapy
chemical_list: D000970:Antineoplastic Agents; D001688:Biological Products; D002867:Chromones; D013876:Thiophenes