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

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...

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Bibliographic Details
Published in:Natural product research 2021-12, Vol.35 (23), p.5153-5159
Main Authors: Quang, Tran Hong, Phong, Nguyen Viet, Hanh, Tran Thi Hong, Cuong, Nguyen Xuan, Ngan, Nguyen Thi Thanh, Oh, Hyuncheol, Nam, Nguyen Hoai, Van Minh, Chau
Format: Article
Language:English
Subjects:
Absolute configuration
anti-inflammatory
Ascomycota
Circular dichroism
cytotoxic
Cytotoxicity
Density functional theory
Dichroism
Endophytes
Fungi
Hydroxybenzaldehydes
Immunomodulation
Lipopolysaccharides
Marine-derived fungus
Nitric-oxide synthase
NMR
Nuclear magnetic resonance
Optical properties
Optical rotation
Phenols
phenylbutan-2-one
Prostaglandin E2
Toxicity
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Summary: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 IC 50 values ranging from 48.6 to 96.5 µM. Compounds 1, 2, 4-6 displayed NO inhibitory effects in LPS-stimulated BV2 cells, with IC 50 values in a range from 24.2 to 76.5 µM. Compound 2 further inhibited PGE 2 overproduction, with an IC 50 value of 25.3 µM. The inhibitory effects of 2 towards NO and PGE 2 overproduction were found to have a close relationship with its suppression of iNOS and COX-2 protein expression, respectively.
ISSN:1478-6419
1478-6427
DOI:10.1080/14786419.2020.1786829