title: Two benzaldehyde derivatives and their artefacts from a gorgonian-derived Eurotium sp. fungus.
abstract: Two new benzaldehyde derivatives, named 3'-OH-tetrahydroauroglaucin (1) and(3'S*,4'R*)-6-(3',5-epoxy-4'-hydroxy-1'-heptenyl)-2-hydroxy-3-(3''-methyl-2''-butenyl)benzaldehyde (2), were isolated from a gorgonian-derived Eurotium sp. fungus. Their structures were determined by extensive spectroscopic analysis including NMR and MS spectra. Dissolved 1 in CDCl3for several days could be detected its 2H-chromene skeleton derivatives (1a/1b), a pair of enantiomers with opposite configurations at C-3'. Compound 2 was also found to chemically convert to a pair of epimers non-enzymatically. The plausible mechanism to form the 2H-chromene artefacts with racemisation at C-3' undergoing nucleophilic substitution (SN1) was proposed.
authors.affiliation: a Marine Science & Technology Institute, College of Environmental Science & Engineering , Yangzhou University , Yangzhou , People's Republic of China.|b Key Laboratory of Marine Drugs, the Ministry of Education , School of Medicine and Pharmacy, Ocean University of China , Qingdao , People's Republic of China.
authors.forename: Min
authors.initials: M
authors.lastname: Chen
authors.affiliation: b Key Laboratory of Marine Drugs, the Ministry of Education , School of Medicine and Pharmacy, Ocean University of China , Qingdao , People's Republic of China.|c Laboratory for Marine Drugs and Bioproducts , Qingdao National Laboratory for Marine Science and Technology , Qingdao , People's Republic of China.
authors.forename: Qing
authors.initials: Q
authors.lastname: Zhao
authors.affiliation: b Key Laboratory of Marine Drugs, the Ministry of Education , School of Medicine and Pharmacy, Ocean University of China , Qingdao , People's Republic of China.|c Laboratory for Marine Drugs and Bioproducts , Qingdao National Laboratory for Marine Science and Technology , Qingdao , People's Republic of China.
authors.forename: Jun-Di
authors.initials: JD
authors.lastname: Hao
authors.affiliation: b Key Laboratory of Marine Drugs, the Ministry of Education , School of Medicine and Pharmacy, Ocean University of China , Qingdao , People's Republic of China.|c Laboratory for Marine Drugs and Bioproducts , Qingdao National Laboratory for Marine Science and Technology , Qingdao , People's Republic of China.
authors.forename: Chang-Yun
authors.initials: CY
authors.lastname: Wang
mesh_terms: D000818:Animals; D037421:Anthozoa / Q000382:microbiology; D016477:Artifacts; D001547:Benzaldehydes / Q000737:chemistry* / Q000302:isolation & purification; D001578:Benzopyrans / Q000737:chemistry; D055325:Eurotium / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: C412074:5,7-dimethoxy-2-methyl-2H-benzopyran; D001547:Benzaldehydes; D001578:Benzopyrans; C032175:benzaldehyde
keywords: 2H-chromene; Eurotium sp; Gorgonian-derived fungus; benzaldehyde derivative; racemisation