Title
Two benzaldehyde derivatives and their artefacts from a gorgonian-derived Eurotiumsp. fungus
Author
Min Chen, Qing Zhao, Jun-Di Hao, Chang-Yun Wang
Year
2016
Journal
Journal of Natural Product Research
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 CDCl3 for 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.
Instrument
J-810
Keywords
Circular dichroism, Stereochemistry, Natural products