Sadorn, Karoon

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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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Phenolic glucosides and chromane analogs from the insect fungus Conoideocrella krungchingensis BCC53666
(2019-06-21)
Sadorn, Karoon
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Saepua, Siriporn
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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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Allahabadolactones A and B from the endophytic fungus, Aspergillus allahabadii BCC45335
(2016-01-28)
Sadorn, Karoon
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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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