Sadorn, Karoon

Preferred name

Sadorn, Karoon

Main Affiliation

School of Science

karoon.sa@kmitl.ac.th

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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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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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Bioactive Dimeric Tetrahydroxanthones with 2,2′- And 4,4′-Axial Linkages from the Entomopathogenic FungusAschersonia confluens
(2021-04-23)
Sadorn, Karoon
;
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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Phenolic glucosides and chromane analogs from the insect fungus Conoideocrella krungchingensis BCC53666
(2019-06-21)
Sadorn, Karoon
;
Saepua, Siriporn
;
Boonyuen, Nattawut
;
Komwijit, Somjit
;
Rachtawee, Pranee
Six new compounds, named conoideoglucosides A − C and conoideochromanes A − C, together with eight known compounds, including eutypinic acid, 2,2-dimethyl-2H-1-chromene-6-carboxylic acid, (−)-luteoskyrin, (−)-4a-oxyluteoskyrin, chrysophanol, islandicin, catenarin, and (22E)-5α,8α-epidioxyergosta-6,22-dien-3β-ol were isolated from the insect fungus Conoideocrella krungchingensis BCC53666. (−)-Luteoskyrin exhibited a broad range of antimicrobial activity such as antimalarial (IC<inf>50</inf> 0.51 μg/mL), antitubercular (MIC 6.25 μg/mL), antibacterial (both Gram positive; MIC 0.39–1.56 μg/mL and Gram negative; MIC 3.13–12.50 μg/mL), and antifungal (against various plant pathogens; MIC 3.13–50.00 μg/mL)activities, while (−)-4a-oxyluteoskyrin and catenarin showed weaker antibacterial activity. Moreover, eutypinic acid, (−)-luteoskyrin, (−)-4a-oxyluteoskyrin, and catenarin showed cytotoxicity against NCI-H187 cells with IC<inf>50</inf> in a range of 0.16–17.99 μg/mL, while eutypinic acid and catenarin had no cytotoxicity against non-cancerous (Vero)cells at maximum tested concentration (50 μg/mL). The complete NMR spectral data and biological activity of the known (−)-4a-oxyluteoskyrin was also reported for the first time.
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Antimicrobial activity and cytotoxicity of polyketides isolated from the mushroom: Xerula sp. BCC56836
(2016-01-01)
Sadorn, Karoon
;
Saepua, Siriporn
;
Boonyuen, Nattawut
;
Laksanacharoen, Pattiyaa
;
Rachtawee, Pranee
Twelve new compounds, including (-)-oudemansin A acid (1), (-)-oudemansin A ethyl ester (3) and (-)-oudemansin X ethyl ester (5), (+)-oudemansin A lactone (6) and (+)-oudemansin X lactone (7), (+)-dihydrooudemansinol (8), (-)-11-epidihydrooudemansinol (9), (+)-xeruhydrofuranol (10), (+)-9-epixeruhydrofuranol (11), xerucitrinic acids A (14) and B (15), and (2R,3R,8aR)-2-(E-hept-5-en-1-yl)-3-methyltetrahydro-2H-pyrrolo[2,1-b][1,3]oxazin-4(3H)-one (16) and one naturally new compound, strobilurin A acid (12), together with nine known compounds such as (-)-oudemansins A (2) and X (4), (3Z,5E)-3-methyl-6-phenylhexa-3,5-dien-1-ol (13), 2-(E-hept-5-en-1-yl)-3-methyl-6,7,8,8a-tetrahydro-4H-pyrrolo[2,1-b][1,3]oxazin-4-one (17), scalusamides A-C (18-20), phenol A acid (21), and dihydrocitrinone (22), were isolated from the mushroom Xerula sp. BCC56836. Their chemical structures were established based on the information from NMR spectroscopic and mass spectrometric analyses, specific rotation values, and chemical means. A plausible biosynthesis of xerucitrinic acids A (14) and B (15), the first citrinin dimers with spiro skeletons, was also proposed. In addition, the isolated compounds were evaluated for antimicrobial activity, including antimalarial, antifungal, and antibacterial activities, and their cytotoxicity against both cancerous (MCF-7, KB, NCI-H187) and non-cancerous (Vero) cells. Compounds 2, 4, and 5 possessed antimalarial activity against Plasmodium falciparum, K1 strain (IC<inf>50</inf> 1.19-13.70 μM) and compounds 3-5, 12-14, and 17 exhibited anti-Bacillus cereus activity (MIC 12.5-25.0 μg mL<sup>-1</sup>). Most isolated compounds showed low cytotoxicity against both cancerous and non-cancerous cells.
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Chromanones and aryl glucoside analogs from the entomopathogenic fungus Aschersonia confluens BCC53152
(2020-07-01)
Sadorn, Karoon
;
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)
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.
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Sadorn, Karoon

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