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

Abstract

Chemical investigation of the marine-derived endophytic fungus Ascomycota sp. 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 of 1 was determined by time-dependent density functional theory electronic circular dichroism, specific optical rotation, and NMR calculations. Compounds 1 and 2 showed cytotoxicity towards HepG2, MCF-7, and SK-Mel2 carcinoma cells, with IC₅₀ values ranging from 48.6 to 96.5 µM. Compounds 1, 2, 4–6 displayed NO inhibitory effects in LPS-stimulated BV2 cells, with IC₅₀ values in a range from 24.2 to 76.5 µM. Compound 2 further inhibited PGE₂ overproduction, with an IC₅₀ value of 25.3 µM. The inhibitory effects of 2 towards NO and PGE₂ overproduction were found to have a close relationship with its suppression of iNOS and COX-2 protein expression, respectively.

Graphical Abstract

KEYWORDS:

• Marine-derived fungus
• Ascomycota
• phenylbutan-2-one
• cytotoxic
• anti-inflammatory

5. Supplementary material

Experimental; HR-IDA-TOF-MS, ECD, and NMR spectra for the new compound (1); ¹H and ¹³C NMR data of compounds 2-6; cytotoxic and anti-inflammatory activities of compounds 1–6.

Acknowledgements

The authors are thankful to the Institute of Chemistry, VAST for measurement of the NMR and HR-IDA-TOF-MS spectra; Prof. Do Thi Thao, Institute of Biotechnology, VAST for the cytotoxicity evaluation; and Dr. Bui Huu Tai, Institute of Marine Biochemistry, VAST for measurement of the ECD spectra.

Disclosure statement

No potential conflict of interest was reported by the authors.

Funding

This work was financially supported by Vietnam Academy of Science and Technology (VAST) under grant number VAST04.05/19-20.

Additional information

Funding

This work was financially supported by Vietnam Academy of Science and Technology (VAST) under grant number VAST04.05/19-20.