title: Induced production of halogenated diphenyl ethers from the marine-derived fungus Penicillium chrysogenum.
abstract: Manipulation of the fermentation of the marine-derived fungus Penicillium chrysogenum by addition of CaBr(2) resulted in induced production of bromodiphenyl ether analogs. Two new free-radical-scavenging polybrominated diphenyl ethers, 1 and 2, and three known diphenyl ethers, 3,3'-dihydroxy-5,5'-dimethyldiphenyl ether (3), and an inseparable mixture of violacerol-I (4) and violacerol-II (5) were isolated. The structures of the two new polybromodiphenyl ethers 1 and 2 were assigned by combined spectroscopic-data analysis, including deuterium-induced isotope effect. Compounds 1-3, and a mixture of 4 and 5 exhibited radical-scavenging activities against 1,1-diphenyl-2-picrylhydrazyl with IC(50) values of 18, 15, 42, and 6 μM, respectively. With the exception of 3, the compounds were, therefore, more active than the positive control, ascorbic acid (IC(50) 20 μM).
authors.affiliation: Department of Chemistry, Pukyong National University, Busan, Korea.
authors.forename: Guohua
authors.initials: G
authors.lastname: Yang
authors.forename: Keumja
authors.initials: K
authors.lastname: Yun
authors.forename: Viviane N
authors.initials: VN
authors.lastname: Nenkep
authors.forename: Hong Dae
authors.initials: HD
authors.lastname: Choi
authors.forename: Jung Sook
authors.initials: JS
authors.lastname: Kang
authors.forename: Byeng Wha
authors.initials: BW
authors.lastname: Son
mesh_terms: D016166:Free Radical Scavengers / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D055768:Halogenated Diphenyl Ethers / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D006219:Halogens / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010408:Penicillium chrysogenum / Q000737:chemistry*; D010647:Phenyl Ethers / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology
chemical_list: D016166:Free Radical Scavengers; D055768:Halogenated Diphenyl Ethers; D006219:Halogens; D010647:Phenyl Ethers