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    Eremophilane sesquiterpenoids from the endophytic fungus Curvularia lunata BCC76963
    (2023-03-21) ;
    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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    Bioactive Dimeric Tetrahydroxanthones with 2,2′- And 4,4′-Axial Linkages from the Entomopathogenic FungusAschersonia confluens
    (2021-04-23) ;
    Saepua, Siriporn
    ;
    Boonyuen, Nattawut
    ;
    Choowong, Wilunda
    ;
    Rachtawee, Pranee
    Thirteen tetrahydroxanthone dimers,atrop-ascherxanthone A (1), ascherxanthones C-G (2-6), and confluxanthones A-G (7-13), were isolated from the entomopathogenic fungusAschersonia confluensBCC53152. The chemical structures were determined based on analysis of NMR spectroscopic and mass spectrometric data. The absolute configurations of compounds1and7were confirmed by single-crystal X-ray diffraction experiments, while the configurations of other compounds were assigned based upon evidence from NOESY and NOEDIFF experiments, modified Mosher’s method, and ECD spectroscopic data together with biogenetic considerations. Compounds1,3-5,7-11, and13showed antimalarial activity againstPlasmodium falciparum(K1, multidrug-resistant strain) (IC<inf>50</inf>0.6-6.1 μM), antitubercular activity againstMycobacterium tuberculosisH37Ra (MIC 6.3-25.0 μg/mL), and cytotoxicity against NCI-H187 (IC<inf>50</inf>0.5-3.5 μM) and Vero (IC<inf>50</inf>0.9-6.1 μM) cells. All tested compounds except for compound9exhibited cytotoxicity against KB cells (IC<inf>50</inf>1.3-9.7 μM).
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    Chromanones and aryl glucoside analogs from the entomopathogenic fungus Aschersonia confluens BCC53152
    (2020-07-01) ;
    Saepua, Siriporn
    ;
    Punyain, Wikorn
    ;
    Saortep, Wacharee
    ;
    Choowong, Wilunda
    Six new compounds [ascherlactones A (1) and B (2), ascherchromanone A (3), phenethyl 4′-O-methylglucoside (8), 4′-O-methylpleoside (10), and 4′-O-methyltorachrysone 8-O-glucoside (11)] and one naturally new compound [4′-O-methyl-β-D-benzylglucoside (9)] together with fourteen known compounds, including paecilodepsipeptides A (5), B (7), and D (4), conoideocrellide A (6), eugenin (12), 5-hydroxy-2,3-dimethyl-7-methoxychromone (13), (S)-1-phenyl-1,2-ethanediol (14), (2S)-L-3-phenyllactic acid (15), papuline [or (2S)-L-3-phenyllactic acid methyl ester, 16], 2′-epi terpendole A (17), terpendoles C (18) and D (19), cholic acid, and zeorin were isolated from the entomopathogenic fungus Aschersonia confluens BCC53152. Their chemical structures were elucidated on the basis of NMR spectroscopic and mass spectrometric analyses. The absolute configurations were determined by using the evidence from NOESY correlations, chemical means, optical rotation values together with comparison of ECD spectroscopic data with the calculated ECD spectra. The plausible biosynthetic pathway of compounds 1–3 was also proposed. Moreover, antimicrobial activity such as antimalarial, antitubercular, antifungal, and antibacterial activities and cytotoxicity against cancerous (MCF-7, KB, and NCI-H187) and non-cancerous (Vero) cells of the isolated compounds were evaluated.
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    Diphenyl ethers and depsidones from the endophytic fungus Aspergillus unguis BCC54176
    (2022-01-22) ;
    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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    Bioactive metabolites from cultures of the entomopathogenic fungus Pleurocordyceps ophiocordycipiticola TBRC-BCC 9612
    (2026-01-19)
    Saepua, Siriporn
    ;
    ;
    Kornsakulkarn, Jittra
    ;
    Auncharoen, Patchanee
    ;
    Mongkolsamrit, Suchada
    Pleurocordyceps ophiocordycipiticola TBRC-BCC 9612, an entomopathogenic fungus collected from Khao Yai National Park, Thailand, was investigated for its secondary metabolites. Large-scale fermentation, followed by multistep chromatographic separation, resulted in the isolation of seven new compounds, including an ergot-type alkaloid (dihydroergopleurine, 2), three tetramic acid derivatives (pleurocordines A–C, 4–6), two acyclic terpenoids (7 and 8), and a dihydroisobenzofuran derivative (9), along with twelve known compounds. The structures of the new compounds were elucidated based on spectroscopic analyses, including 1D and 2D NMR, HRMS, and ECD data. Selected compounds were evaluated for antimalarial activity against Plasmodium falciparum K1, antibacterial activity against Bacillus cereus, Staphylococcus aureus, and Acinetobacter baumannii, antifungal activity against phytopathogens (Alternaria brassicicola and Colletotrichum acutatum), as well as cytotoxicity toward cancerous (MCF-7, NCI-H187) and non-cancerous (Vero) cells. Among them, ergot alkaloids dihydroergosine (1) and dihydroergopleurine (2) showed antimalarial and cytotoxic activities, while pleurocordine C (6) demonstrated antibacterial and weak cytotoxic effects. 14-Nor-epicoccarine A (3) and pleurocordine A (4) exhibited moderate antifungal activity, and the known akanthomycin showed broad-spectrum bioactivity but lacked selectivity between cancerous and normal cells. These findings expand the chemical diversity known from P. ophiocordycipiticola and highlight several compounds with promising biological profiles for further pharmacological study.