An Oxazole Alkaloid, Terpenoids, and Cyclodipeptides With Cytotoxic and Nitric Oxide Inhibitory Effects From a Mangrove‐Derived Fungus <i>Trichoderma</i> sp. GXT‐22.1

Chemical investigation of the mangrove-derived fungus Trichoderma sp. GXT-22.1 led to the isolation and identification of 10 secondary metabolites, including one new compound, 5'-(4-methoxyphenyl)-1',3'-oxazole (1), one new natural compound, (E)-6,10-dimethyl-5-undecene-2,9,10-triol (2), along with eight known compounds, tricholumin A (3), harzianol J (4), cyclonerodiol (5), 10,11-dihydro-11-hydroxycyclonerodiol (6), cyclonerodiol B (7), epicyclonerodiol oxide (8), cyclo(Val-Pro) (9), and cyclo-(4-hydroxyprolinyl-leucine) (10). The structural feature of oxazole in 1 was unusually found among the fungal metabolites. Compounds 1 and 4 exhibited weak cytotoxicity toward HepG2 and MCF-7 human carcinoma cell lines at the concentration of 100 µM, with induction of 41.5 ± 3.0% and 39.3 ± 2.3% cell death, respectively. Compounds 1-5, 8, and 10 showed their inhibitory effect against nitric oxide (NO) overproduction in lipopolysaccharide-stimulated RAW264.7 cells, with half inhibition concentration values ranging from 37.5 ± 2.6 to 86.5 ± 5.1 µM. Molecular docking simulation suggested that 1 inhibits NO overproduction via modulating the action of the inducible NO synthase protein.

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Publication Details

Journal
Chemistry & Biodiversity
Published
2024-12-13
DOI
https://doi.org/10.1002/cbdv.202402986
Citations
2
Primary Topic
Microbial Natural Products and Biosynthesis
Type
article
Field-Weighted Citation Impact
0.90
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article

An Oxazole Alkaloid, Terpenoids, and Cyclodipeptides With Cytotoxic and Nitric Oxide Inhibitory Effects From a Mangrove‐Derived Fungus Trichoderma sp. GXT‐22.1

Do Hoang Anh, Nguyễn Xuân Cường, Trần Hồng Quang, Le Thi Vien et al.
2 citations
Chemistry & Biodiversity
Microbial Natural Products and Biosynthesis
0.90
article

An Oxazole Alkaloid, Terpenoids, and Cyclodipeptides With Cytotoxic and Nitric Oxide Inhibitory Effects From a Mangrove‐Derived Fungus Trichoderma sp. GXT‐22.1

Do Hoang Anh, Nguyễn Xuân Cường, Trần Hồng Quang, Le Thi Vien, Tung Ngoc Nguyen, Phạm Thị Mai Hương, Dang Viet Anh, Nguyen Thi Thanh Ngan
article en
2 citations

Abstract

Chemical investigation of the mangrove-derived fungus Trichoderma sp. GXT-22.1 led to the isolation and identification of 10 secondary metabolites, including one new compound, 5'-(4-methoxyphenyl)-1',3'-oxazole (1), one new natural compound, (E)-6,10-dimethyl-5-undecene-2,9,10-triol (2), along with eight known compounds, tricholumin A (3), harzianol J (4), cyclonerodiol (5), 10,11-dihydro-11-hydroxycyclonerodiol (6), cyclonerodiol B (7), epicyclonerodiol oxide (8), cyclo(Val-Pro) (9), and cyclo-(4-hydroxyprolinyl-leucine) (10). The structural feature of oxazole in 1 was unusually found among the fungal metabolites. Compounds 1 and 4 exhibited weak cytotoxicity toward HepG2 and MCF-7 human carcinoma cell lines at the concentration of 100 µM, with induction of 41.5 ± 3.0% and 39.3 ± 2.3% cell death, respectively. Compounds 1-5, 8, and 10 showed their inhibitory effect against nitric oxide (NO) overproduction in lipopolysaccharide-stimulated RAW264.7 cells, with half inhibition concentration values ranging from 37.5 ± 2.6 to 86.5 ± 5.1 µM. Molecular docking simulation suggested that 1 inhibits NO overproduction via modulating the action of the inducible NO synthase protein.

Chemistry & BiodiversityVol. 22(5)
Vietnam Academy of Science and Technology (VN)
Life below water
Openalex Percentile: Top 22%
Microbial Natural Products and Biosynthesis
0.90
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An Oxazole Alkaloid, Terpenoids, and Cyclodipeptides With Cytotoxic and Nitric Oxide Inhibitory Effects From a Mangrove‐Derived Fungus <i>Trichoderma</i> sp. GXT‐22.1 — Do Hoang Anh, Nguyễn Xuân Cường, et al. · Chemistry & Biodiversity (2024) | TGRS Research Map | TGRS