A pair of new isocoumarin epimers from soil fungus Hypoxylon sp

In our research on novel secondary metabolites from micro-organisms, two new (1-2) and four known dihydroisocoumarins (3-6) were derived from soil fungus Hypoxylon sp. Their structures were determined with extensive NMR data analysis and ECD calculation comparing with those of experimental CD spectr...

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Bibliographic Details
Published in:Journal of asian natural products research 2017-10, Vol.19 (10), p.993-999
Main Authors: Zheng, Wei, Ji, Yu-Bin, Li, Wen-Lan, Dong, Jing, Chen, Ning, Yu, Xue-Fei, Wu, Jian, Zhao, Dan, Xiang, Zheng
Format: Article
Language:English
Subjects:
Cotton
Data analysis
Data processing
Drugs, Chinese Herbal - chemistry
Drugs, Chinese Herbal - isolation & purification
ECD investigation
Fungi
isocoumarin
Isocoumarins - chemistry
Isocoumarins - isolation & purification
Metabolites
Molecular Structure
NMR
Nuclear magnetic resonance
Nuclear Magnetic Resonance, Biomolecular
Secondary metabolites
Soil fungus
Soil Microbiology
Stereoisomerism
Xylariales - chemistry
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Summary:In our research on novel secondary metabolites from micro-organisms, two new (1-2) and four known dihydroisocoumarins (3-6) were derived from soil fungus Hypoxylon sp. Their structures were determined with extensive NMR data analysis and ECD calculation comparing with those of experimental CD spectra. Interestingly, compounds 1 and 2 possessed the same planar structure and very similar NMR data, suggesting 1 and 2 were a pair of epimers at either C-3 or at C-4, confirmed by the totally opposite cotton effect around 250 nm in the CD spectra of 1 and 2. Moreover, for the first time, we revealed that the CD absorption peak at 250 nm was dominated by C-3 orientation, rather than the orientation of C-3 substituents, by intensive ECD investigations.
ISSN:1028-6020
1477-2213
DOI:10.1080/10286020.2017.1347159