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Author: search.filters.author.Prabpai, Samran

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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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    Triterpene lactones from cultures of Ganoderma sp. KM01
    (2014-07-25)
    Lakornwong, Waranya
    ;
    Kanokmedhakul, Kwanjai
    ;
    Kanokmedhakul, Somdej
    ;
    Kongsaeree, Palangpon
    ;
    Prabpai, Samran
    A revised structure of colossolactone G (1), seven new triterpene lactones, ganodermalactones A-G (2-8), and five known triterpene lactones, colossolactone I (9), schisanlactone B (10), colossolactone B (11), colossolactone E (12), and colossolactone IV (13), and ergosterol have been isolated from cultured biomass of the macrofungi Ganoderma sp. KM01. Their structures were identified by spectroscopic methods. Structures and relative configurations of 3, 7, and 8 were confirmed by X-ray crystallographic analysis. Compounds 7, 10, and 12 exhibited antimalarial activity against Plasmodium falciparum in the range 6.0-10.0 μM (IC<inf>50</inf>). © 2014 The American Chemical Society and American Society of Pharmacognosy.
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    Bioactive meroterpenoids and alkaloids from the fungus Eurotium chevalieri
    (2011-07-29)
    Kanokmedhakul, Kwanjai
    ;
    Kanokmedhakul, Somdej
    ;
    Suwannatrai, Ruchiruttikorn
    ;
    Soytong, Kasem
    ;
    Prabpai, Samran
    Five new meroterpenoids, chevalones A-D (1-4), aszonapyrone B (8), and a new sequiterpene alkaloid, eurochevalierine (5), together with four known compounds, sequiterpene (6), terpenoid pyrrolobenzoxazine named CJ-12662 (7), meroterpenoid, aszonapyrone A (9), and ergosterol were isolated from the fungus Eurotium chevalieri. The structures were established on the basis of spectroscopic evidence. The configurations of 1 and 5 were determined by X-ray analysis. The biosynthetic pathway of 1-3, 8, and 9 were proposed. Chemical transformation of aszonapyrone A (9) was also studied. Compounds 4, 5, and 7 exhibited antimalarial activity against Plasmodium falciparum, while 3, 5, and 7 showed antimycobacterial activity against Mycobacterium tuberculosis. In addition, compounds 2-7 showed cytotoxicity against cancer cell lines. © 2011 Elsevier Ltd. All rights reserved.
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    Cytotoxic pentacyclic and tetracyclic aromatic sesquiterpenes from phomopsis archeri
    (2011-04-25)
    Hemtasin, Chulida
    ;
    Kanokmedhakul, Somdej
    ;
    Kanokmedhakul, Kwanjai
    ;
    Hahnvajanawong, Chariya
    ;
    Soytong, Kasem
    Three new sesquiterpenes, named phomoarcherins A-C (1-3), and four known compounds, kampanol A (4), R-mevalonolactone, ergosterol, and ergosterol peroxide, were isolated from the endophytic fungus Phomopsis archeri. These structures were established on the basis of spectroscopic evidence. The structure and absolute configuration of 1 were confirmed by X-ray crystallographic analysis of its p-bromobenzoate derivative (1a). Compounds 1-4 showed cytotoxicity against five cholangiocarcinoma cell lines (0.1-19.6 μg/mL), while 1 and 2 exhibited weak cytotoxicity against the KB cell line with IC<inf>50</inf> values of 42.1 and 9.4 μg/mL, respectively. In addition, compound 2 showed antimalarial activity against Plasmodium falciparum with an IC<inf>50</inf> value of 0.79 μg/mL. © 2011 The American Chemical Society and American Society of Pharmacognosy.
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    Bis-spiro-azaphilones and azaphilones from the fungi Chaetomium cochliodes VTh01 and C. cochliodes CTh05
    (2008-09-29)
    Phonkerd, Nutchanat
    ;
    Kanokmedhakul, Somdej
    ;
    Kanokmedhakul, Kwanjai
    ;
    Soytong, Kasem
    ;
    Prabpai, Samran
    Four new dimeric spiro-azaplilones, cochliodones A-D (1-4), two new azaphliones, chaetoviridines E and F (5 and 6), a new epi-chaetoviridin A (7), together with five known compounds, chaetoviridin A (8), ergosterol (9), chaetochalasin A (10), 24(R)-5α,8α-epidioxyergosta-6-22-diene-3β-ol (11), and ergosterol-β-d-glucoside (12) were isolated from the fungi Chaetomium cochliodes VTh01 and C. cochliodes CTh05. Structures and stereochemistry of the atropisomers 1-3 were determined by single-crystal X-ray diffraction analysis. Compounds 5, 10, and 11 exhibited antimalarial activity against Plasmodium falciparum, while 3, 5, 6, 10, and 11 showed antimycobacterial activity against Mycobacterium tuberculosis. In addition, 5 and 6 also showed cytotoxicity against the KB, BC1, and NCI-H187 cell lines. © 2008 Elsevier Ltd. All rights reserved.
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    Antifungal azaphilones from the fungus Chaetomium cupreum CC3003
    (2006-06-01)
    Kanokmedhakul, Somdej
    ;
    Kanokmedhakul, Kwanjai
    ;
    Nasomjai, Pitak
    ;
    Louangsysouphanh, Sysavad
    ;
    Soytong, Kasem
    Three new azaphilones named rotiorinols A-C (1-3), two new stereoisomers, (-)-rotiorin (4) and epi-isochromophilone II (5), and a known compound, rubrorotiorin (6), were isolated from the fungus Chaetomium cupreum CC3003. Structures were established on the basis of spectroscopic evidence. The absolute configuration of 1 was determined by the modified Mosher's method along with an X-ray analysis of its acetate derivative, as well as by chemical transformation. Compounds 1, 3, 4, and 6 exhibited antifungal activity against Candida albicans with IC<inf>50</inf> values of 10.5, 16.7, 24.3, and 0.6 μg/mL, respectively. © 2006 American Chemical Society and American Society of Pharmacognosy.