title: Rare Chromones from a Fungal Mutant of the Marine-Derived Penicillium purpurogenum G59.
abstract: Three new and rare chromones, named epiremisporine B (2), epiremisporine B1 (3) and isoconiochaetone C (4), along with three known remisporine B (1), coniochaetone A (5) and methyl 8-hydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate (6) were isolated from a mutant from the diethyl sulfate (DES) mutagenesis of a marine-derived Penicillium purpurogenum G59. The structures of 2-4 including the absolute configurations were determined by spectroscopic methods, especially by NMR analysis and electronic circular dichroism (ECD) experiments in conjunction with calculations. The absolute configuration of the known remisporine B (1) was determined for the first time. Compounds 2 and 3 have a rare feature that has only been reported in one example so far. The compounds 1-6 were evaluated for their cytotoxicity against several human cancer cell lines. The present work explored the great potential of our previous DES mutagenesis strategy for activating silent fungal pathways, which has accelerated the discovery of new bioactive compounds.
authors: State Key Laboratory of Toxicology and Medical Countermeasures, Beijing Institute of Pharmacology and Toxicology, Beijing 100850, China. xiamingwen@126.com.|Key Laboratory of Structure-Based Drug Design & Discovery of Ministry of Education, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, China. xiamingwen@126.com.
authors: Ming-Wen
authors: MW
authors: Xia
authors: State Key Laboratory of Toxicology and Medical Countermeasures, Beijing Institute of Pharmacology and Toxicology, Beijing 100850, China. cuicb@126.com.|Key Laboratory of Structure-Based Drug Design & Discovery of Ministry of Education, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, China. cuicb@126.com.
authors: Cheng-Bin
authors: CB
authors: Cui
authors: State Key Laboratory of Toxicology and Medical Countermeasures, Beijing Institute of Pharmacology and Toxicology, Beijing 100850, China. sdrlcw@126.com.
authors: Chang-Wei
authors: CW
authors: Li
authors: State Key Laboratory of Toxicology and Medical Countermeasures, Beijing Institute of Pharmacology and Toxicology, Beijing 100850, China. wucj2009@163.com.|Key Laboratory of Structure-Based Drug Design & Discovery of Ministry of Education, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, China. wucj2009@163.com.
authors: Chang-Jing
authors: CJ
authors: Wu
authors: Key Laboratory of Marine Drugs, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China. pengjixing1987@163.com.
authors: Ji-Xing
authors: JX
authors: Peng
authors: Key Laboratory of Marine Drugs, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China. dehaili@ouc.edu.cn.
authors: De-Hai
authors: DH
authors: Li
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry* / Q000494:pharmacology*; D059001:Aquatic Organisms / Q000737:chemistry / Q000187:drug effects / Q000378:metabolism*; D045744:Cell Line, Tumor; D002867:Chromones / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D002942:Circular Dichroism / Q000379:methods; D005658:Fungi / Q000737:chemistry / Q000187:drug effects / Q000378:metabolism*; D006801:Humans; D020014:K562 Cells; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D009154:Mutation / Q000187:drug effects; D010407:Penicillium / Q000737:chemistry / Q000187:drug effects / Q000378:metabolism*; D013463:Sulfuric Acid Esters / Q000494:pharmacology
chemical_list: D000970:Antineoplastic Agents; D002867:Chromones; D013463:Sulfuric Acid Esters; C011612:diethyl sulfate
keywords: DES mutagenesis; ECD; Penicillium purpurogenum G59; chromone derivatives; epiremisporine; isoconiochaetone; marine-derived fungus; remisporine