Tetrahedron
Tetrahedron
5 years ago

Anti-inflammatory polyketides from the mangrove-derived fungus Ascomycota sp. SK2YWS-L

Anti-inflammatory polyketides from the mangrove-derived fungus Ascomycota sp. SK2YWS-L
A pair of novel 2,3-diaryl indone derivatives (+)- and (−)-ascomindone D [(+)-1 and (−)-1, respectively], as well as two new prenylated polyketides ascomfurans C (2) and ascomarugosin A (3) were obtained from the culture of a mangrove endophytic fungus Ascomycota sp. SK2YWS-L together with three known compounds (4–6). The enantiomers (+)-1 and (−)-1 were purified through chiral HPLC separation, which represented the first example of resolving 2,3-diaryl indone atropisomers in natural products. The structures of the new compounds were determined on the basis of interpretation of spectroscopic data including X-ray diffractions and the absolute configurations of (+)-1 and (−)-1 were elucidated by ECD calculations. The biosynthesis pathway was proposed. In the anti-inflammatory assay, (+)-1 and (−)-1 exhibited potential anti-inflammatory effects by inhibiting against the production of nitric oxide (NO) in lipopolysaccharide (LPS)-induced RAW 246.7 mouse macrophages with the IC50 values of 17.0 and 17.1 μM, respectively.

Publisher URL: www.sciencedirect.com/science

DOI: S0040402017313418

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