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 |
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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. |
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ISSN: | 1477-0520 1477-0539 |
DOI: | 10.1039/d1ob00869b |