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Author: search.filters.author.Boonyuen, NattawutSubject: search.filters.subject.Antibacterial activity

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    Eremophilane sesquiterpenoids from the endophytic fungus Curvularia lunata BCC76963
    (2023-03-21)
    Sadorn, Karoon
    ;
    Saepua, Siriporn
    ;
    Boonyuen, Nattawut
    ;
    Auncharoen, Patchanee
    ;
    Rachtawee, Pranee
    A chemical investigation on broth and mycelia extracts of the endophytic fungus Curvularia lunata BCC76963 led to the isolation of five new eremophilane sesquiterpenoids, curvuleremophilanes A−D (1–4) and septeremophilane I (5), one new conjugated unsaturated fatty acid, (6S,2E,4E)-8-hydroxy-4,6-dimethylocta-2,4-dienoic acid (6), and one new phenylacetic acid derivative, 4′-chlorocurvulin (8), along with ten known compounds. The chemical structures were elucidated based on the analyses of HRESIMS and NMR spectroscopic data. The absolute configurations of eremophilanes were assigned by the evidence from NOESY correlations, chemical conversion, optical rotation values, and ECD spectroscopic data in conjunction with biogenetic considerations. In addition, the absolute stereochemistry of compound 5 was confirmed by X-ray crystallography. Curvuleremophilane A (1), dendryphiellin I (10), chaetopenoid B (11), and bipolaroxin (12) displayed antimalarial activity against Plasmodium falciparum K1 with IC<inf>50</inf> values in a range of 3.64–7.77 μM and antibacterial activity against Bacillus cereus and Staphylococcus aureus with MIC values in a range of 3.13–12.50 and 1.56–25.00 μg/mL, respectively. These compounds, except for compound 11, also showed cytotoxicity against NCI-H187 and Vero cells with respective IC<inf>50</inf> values in a range of 2.76–3.97 and 2.34–4.67 μM.
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    Diphenyl ethers and depsidones from the endophytic fungus Aspergillus unguis BCC54176
    (2022-01-22)
    Sadorn, Karoon
    ;
    Saepua, Siriporn
    ;
    Bunbamrung, Nantiya
    ;
    Boonyuen, Nattawut
    ;
    Komwijit, Somjit
    Four new diphenyl ethers, aspergillusethers G−J (1–4), and one new depsidone, emeguisin D (7), together with eighteen known compounds have been isolated and characterized from the endophytic fungus Aspergillus unguis BCC54176. The chemical structures were established based on spectroscopic evidence in conjunction with a chemical transformation. Furthermore, the chemical structure of compound 7 was verified by single-crystal X-ray diffraction data. The isolated compounds were evaluated for biological activity. Compound 7, emeguisin C (10), and nidulin (14) showed antibacterial activity against Bacillus cereus with an equal MIC value of 1.56 μg/mL, while emeguisin A (8), nornidulin (13), 2-chlorounguinol (16), and aspergillusidone C (21) displayed anti-phytopathogenic activity against Colletotrichum acutatum with the equal MIC value of 3.13 μg/mL. Compound 7 was also active against Staphylococcus aureus with an MIC value of 1.56 μg/mL. However, none of the tested compounds had cytotoxicity against cancerous (MCF-7 and NCI–H187) and non-cancerous (Vero) cells.
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    Allahabadolactones A and B from the endophytic fungus, Aspergillus allahabadii BCC45335
    (2016-01-28)
    Sadorn, Karoon
    ;
    Saepua, Siriporn
    ;
    Boonyuen, Nattawut
    ;
    Laksanacharoen, Pattiyaa
    ;
    Rachtawee, Pranee
    Two new compounds, allahabadolactones A (1) and B (2), along with 10 known compounds including 16-amino-isopimar-7-en-19-oic acid (3), 16-α-d-glucopyranosyloxyisopimar-7-en-19-oic acid (4), 16-α-d-mannopyranosyloxyisopimar-7-en-19-oic acid (5), ergosterol, (22E)-5α,8α-epidioxyergosta-6,22-dien-3β-ol, cerevisterol, (R)-(-)-methoxycarbonylmellein, (-)-piliformic acid, 7-dechlorogriseofulvin, and cytochalasin D, were isolated from the endophytic fungus, Aspergillus allahabadii BCC45335. Their chemical structures were determined based on NMR spectroscopic and mass spectrometric analyses. The absolute stereochemistry of compound 1 was established by an X-ray crystallographic analysis and the reactions with Mosher's reagents. A plausible biosynthesis of allahabadolactones A (1) and B (2) was also proposed. Antibacterial activity against Bacillus cereus and cytotoxicity against MCF-7, KB, NCI-H187, and Vero cells of the isolated compounds were also evaluated.