Structures and absolute configurations of phomalones from the coral-associated fungus sp. SCSIO 40430

Coral-associated microorganisms are likely to play an important role in host defense by the production of antimicrobials. Six new chromanones, namely, phomalichenones H-M ( 5 , 6 , and 8-11 ), and ten known analogues ( 1-4 , 7 , and 12-16 ) were isolated from the coral-associated fungus Parengyodont...

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Veröffentlicht in:Organic & biomolecular chemistry 2021-07, Vol.19 (27), p.63-637
Hauptverfasser: Wang, Lu, Huang, Yanbing, Zhang, Liping, Liu, Zhiwen, Liu, Wei, Xu, Huixin, Zhang, Qingbo, Zhang, Haibo, Yan, Yan, Liu, Zhiyong, Zhang, Tianyu, Zhang, Wenjun, Zhang, Changsheng
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Zusammenfassung:Coral-associated microorganisms are likely to play an important role in host defense by the production of antimicrobials. Six new chromanones, namely, phomalichenones H-M ( 5 , 6 , and 8-11 ), and ten known analogues ( 1-4 , 7 , and 12-16 ) were isolated from the coral-associated fungus Parengyodontium album sp. SCSIO 40430. Their structures were elucidated by comprehensive spectroscopic analyses. In addition, the structure of 8 was confirmed by X-ray crystallographic analysis. Resolution using a chiral column showed that each of the compounds 1-8 was an enantiomeric mixture with variable enantiomeric excess (ee) values. Their absolute configurations were determined by a comparison of the experimental and calculated ECD data and by a modified Mosher's method. A plausible biosynthetic scheme was proposed for the production of 1-16 . Compounds 2 , 3 , 13 , and 14 were found to be active against Mycobacterium tuberculosis H37Ra with MIC values of 16-64 μg mL −1 . Coral-associated microorganisms are likely to play an important role in host defense by the production of antimicrobials, such as enantiomeric mixture of phomalones.
ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob00869b