Cytotoxic and immunomodulatory phenol derivatives from a marine sponge-derived fungus Ascomycota sp. VK12

Chemical investigation of the marine-derived endophytic fungusAscomycotasp. VK12 resulted in isolation and identification of a new compound, (3R)-(3 ',5 '-dihydroxyphenyl)butan-2-one (1) and five known ones: AGI-7 (2), sescandelin (3), sescandelin-B (4), 4-hydroxybenzaldehyde (5), and hydroxysydonic acid (6). The absolute configuration of1was determined by time-dependent density functional theory electronic circular dichroism, specific optical rotation, and NMR calculations. Compounds1and2showed cytotoxicity towards HepG2, MCF-7, and SK-Mel2 carcinoma cells, with IC(50)values ranging from 48.6 to 96.5 mu M. Compounds1,2,4-6displayed NO inhibitory effects in LPS-stimulated BV2 cells, with IC(50)values in a range from 24.2 to 76.5 mu M. Compound2further inhibited PGE(2)overproduction, with an IC(50)value of 25.3 mu M. The inhibitory effects of2towards NO and PGE(2)overproduction were found to have a close relationship with its suppression of iNOS and COX-2 protein expression, respectively.

Automated summary

The chemical investigation of the marine-derived endophytic fungus led to the isolation of a new compound and five known compounds, with cytotoxic and anti-inflammatory effects on cancer cells observed.