title: DNA Methyltransferase Inhibitor Induced Fungal Biosynthetic Products: Diethylene Glycol Phthalate Ester Oligomers from the Marine-Derived Fungus Cochliobolus lunatus.
abstract: Chemical epigenetic manipulation was applied to the marine-derived fungus Cochliobolus lunatus (TA26-46) with a DNA methyltransferase inhibitor resulting in the significant changes of the secondary metabolites. Cultivation of C. lunatus (TA26-46) with 5-azacytidine led to the isolation of seven new diethylene glycol phthalate esters, cochphthesters A-G (1-6, 10), along with four known analogues (7-9, 11). Their structures were determined by extensive NMR spectroscopic spectra as well as MS data. Compounds 2-6 and 8-11, characterized by the cross-polymerization of phthalate across diethylene glycol via ester bonds, represent the first example of naturally occurring phthalate ester oligomers. Graphical Abstract Chemical epigenetic manipulation was applied to a marine-derived fungus resulting in significant changes of secondary metabolites.
authors.affiliation: Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao, 266003, People's Republic of China.|Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao, 266071, People's Republic of China.
authors.forename: Min
authors.initials: M
authors.lastname: Chen
authors.affiliation: Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao, 266003, People's Republic of China.|Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao, 266071, People's Republic of China.
authors.forename: Wei
authors.initials: W
authors.lastname: Zhang
authors.affiliation: Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao, 266003, People's Republic of China. shaochanglun@163.com.|Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao, 266071, People's Republic of China. shaochanglun@163.com.
authors.forename: Chang-Lun
authors.initials: CL
authors.lastname: Shao
authors.affiliation: UNESCO Chinese Center of Marine Biotechnology and Key Laboratory of Marine Genetics and Gene Resource Exploitation (Ministry of Education), Ocean University of China, Qingdao, 266003, People's Republic of China.
authors.forename: Zhen-Ming
authors.initials: ZM
authors.lastname: Chi
authors.affiliation: Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao, 266003, People's Republic of China. changyun@ouc.edu.cn.|Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao, 266071, People's Republic of China. changyun@ouc.edu.cn.
authors.forename: Chang-Yun
authors.initials: CY
authors.lastname: Wang
mesh_terms: D059001:Aquatic Organisms; D001374:Azacitidine / Q000494:pharmacology*; D004248:DNA (Cytosine-5-)-Methyltransferases / Q000037:antagonists & inhibitors* / Q000235:genetics / Q000378:metabolism; D004791:Enzyme Inhibitors / Q000494:pharmacology*; D044127:Epigenesis, Genetic; D004952:Esters / Q000378:metabolism*; D005026:Ethylene Glycols / Q000378:metabolism; D005656:Fungal Proteins / Q000037:antagonists & inhibitors* / Q000235:genetics / Q000378:metabolism; D015394:Molecular Structure; D010795:Phthalic Acids / Q000378:metabolism; D004718:Saccharomycetales / Q000187:drug effects* / Q000235:genetics / Q000378:metabolism; D064210:Secondary Metabolism / Q000187:drug effects
chemical_list: D004791:Enzyme Inhibitors; D004952:Esters; D005026:Ethylene Glycols; D005656:Fungal Proteins; D010795:Phthalic Acids; C013484:diethylene glycol; D004248:DNA (Cytosine-5-)-Methyltransferases; D001374:Azacitidine
keywords: 5-Azacytidine; Chemical epigenetic manipulation; Cochliobolus lunatus (TA26–46); DNA methyltransferase inhibitor; Diethylene glycol phthalate ester oligomers; Marine fungus