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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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Antimalarial and antimicrobial substances isolated from the endophytic actinomycete, Streptomyces aculeolatus MS1-6
(2023-03-01)
Kuncharoen, Nattakorn
;
Bunbamrung, Nantiya
;
Intaraudom, Chakapong
;
Choowong, Wilunda
;
Thawai, Chitti
Seven undescribed compounds, including four naphthoquinone terpenoids (aculeolatins A – D), one rare 2-nitropyrrole terpenoid (nitropyrrolin F), and two hydroxamate siderophores (aculeolamides A and B) and one further undescribed compound (2,5,7-trihydroxy-3,6-dimethylnaphthalene-1,4-dione), together with eleven known compounds (arromycin, phenaziterpene A, nitropyrrolin A, heronapyrroles A and B, salaceyin A, 5,7-dihydroxy-2-isopropylchromone, 1-hydroxyphenazine, 1-methoxyphenazine, 1-acetyl-β-carboline, and N-(2-phenylethyl) acetamide), were isolated from the cultures of the endophytic Streptomyces aculeolatus MS1-6. The structures of the isolated compounds were determined using NMR spectroscopy and corroborated using chemical modification. These compounds exhibited a broad spectrum of biological activities, including antimalarial (IC<inf>50</inf> 6.03–9.84 μg/mL), antitubercular (MIC 3.13–6.25 μg/mL), anti-plant pathogenic fungal (MIC 25.0–50.0 μg/mL), and antibacterial (MIC 3.03–50 μg/mL) activities; however, they displayed unremarkable cytotoxicity against cancerous (MCF-7 and NCI–H187) and non-cancerous (Vero) cell lines.
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Abyssomicin derivatives from the rhizosphere soil actinomycete Microbispora rhizosphaerae sp. nov. TBRC6028
(2021-05-01)
Bunbamrung, Nantiya
;
Kittisrisopit, Suchada
;
Intaraudom, Chakapong
;
Dramae, Aibrohim
;
Thawai, Chitti
Three undescribed abyssomicin derivatives, including microbimisin, abyssomicins Z1, and Z2, were isolated from the soil actinomycete Microbispora rhizosphaerae sp. nov. TBRC6028. Chemical structures were determined by NMR spectroscopic data (<sup>1</sup>H, <sup>13</sup>C, COSY, HSQC, HMBC, and NOESY spectra) and the absolute configurations were verified by single-crystal X-ray diffraction analyses together with the ECD spectral data. Microbimisin and abyssomicin Z1 exhibited weak antibacterial activity against Bacillus cereus with MIC values of 25.0 and 50.0 μg/mL without cytotoxicity against MCF-7 and Vero cells at the concentration of 50 μg/mL.
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Antimicrobial activity and cytotoxicity of xanthoquinodin analogs from the fungus Cytospora eugeniae BCC42696
(2018-07-01)
Sadorn, Karoon
;
Saepua, Siriporn
;
Boonyuen, Nattawut
;
Boonruangprapa, Tanapong
;
Rachtawee, Pranee
Eleven previously undescribed compounds, including cytosporanthraxanthone, xanthoquinodins A7–A10, ketoxanthoquinodin A6, xanthoquinodins B6–B8, and spiroxanthoquinodins A and B, and one synthetically known compound, 2-methoxy pinselin, as well as ten known compounds, including xanthoquinodins A4−A6, B4, and B5, chrysophanol, physcion, (4S)-5-hydroxy-4-methoxy-α-tetralone, (4S)-4,8-dihydroxy-α-tetralone (or isosclerone), and gonytolide C were isolated from the fungus Cytospora eugeniae BCC42696. Their chemical structures were determined based on the analysis of NMR spectroscopic and mass spectrometric data. Moreover, the absolute configurations of the unknown compounds were established by using NOESY and NOEDIFF NMR experiments along with CD spectroscopic data. The isolated xanthoquinodins exhibited a broad range of antimalarial, antibacterial, and fungicidal activities as well as cytotoxicity. Xanthoquinodins A6, B4, and B5 showed strong activity to Plasmodium falciparum, K1 strain (IC<inf>50</inf> 0.52–0.92 μM) and displayed anti-Bacillus cereus (MIC 1.56 μg/mL). Xanthoquinodin A6 also showed anti-Curvularia lunata (MIC 3.13 μg/mL). In addition, xanthoquinodins A4, A6, B4, and B5 and ketoxanthoquinodin A6 showed cytotoxicity against both cancerous (MCF-7, KB, NCI-H187) and non-cancerous (Vero) cells.

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