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Cytotoxic and antibacterial depsidones from the endophytic fungus Chaetomium brasiliense isolated from Thai rice
(2022-01-01)
Promgool, Trinop
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Kanokmedhakul, Kwanjai
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Leewijit, Thianrat
;
Song, Jiaojiao
;
Soytong, Kasem
Four new depsidones, mollicellins V-Y (1-4), together with eight known depsidones (5-12) were isolated from the endophytic fungus, Chaetomium brasiliense, detached from stems of Thai rice. Their structures were determined by extensive spectroscopic methods. Mollicellins X, H, and F (3, 8 and 10) showed potent cytotoxicity against the human oral epidermoid carcinoma (KB) cell line, and mollicellin F (10) also showed a potent cytotoxicity against the human hepatocellular carcinoma (HepG2) cell line. Besides, mollicellin B (11) exhibited cytotoxicity against the colorectal adenocarcinoma (HT-29) cell line. Moreover, most of the isolated depsidones displayed potent antibacterial activity against Gram-positive bacteria, Bacillus cereus and Bacillus subtilis, and several of them showed moderate activity against Methicillin-resistant Staphylococcus aureus (MRSA) and clinical isolates of S. aureus. In addition, a few of them also showed moderate activity against a Gram-negative bacteria Pseudomonas aeruginosa.
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New Pyrrolobenzoxazine Sesquiterpenoid Derivatives from the Fungus Talaromyces trachyspermus
(2021-07-13)
Chaiyosang, Boonyanoot
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Kanokmedhakul, Kwanjai
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Soytong, Kasem
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Poeaim, Supattra
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Soytong, Mayamor
Three new pyrrolobenzoxazine sesquiterpenoids, talatrachyoxazines A-C (1-3), together with fourteen known compounds (4-17), were isolated from the fungus Talaromyces trachyspermus EU23. Their structures were identified by spectroscopic evidence and mass spectrometry. The absolute configurations of 1-3 were determined by NOESY data and comparison of their calculated and experimental electronic circular dichroism (ECD) spectra. Compound 1 showed cytotoxic activity against HelaS3, KB, HT-29, MCF-7, and HepG2 cell lines with IC50 values of 7, 11, 10, 12, and 10 μM, respectively. Compounds 1 and 14 showed weak antibacterial activity against the gram-positive bacteria Bacillus cereus and Bacillus subtilis, while 1-3 and 14 showed weak antibacterial activity against the gram-negative bacterium Pseudomonas aeruginosa. In addition, compound 1 showed weak antibacterial activity against Escherichia coli.
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Meroterpenoid pyrones, alkaloid and bicyclic brasiliamide from the fungus Neosartorya hiratsukae
(2020-04-01)
Paluka, Jakkapat
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Kanokmedhakul, Kwanjai
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Soytong, Mayamor
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Soytong, Kasem
;
Yahuafai, Jantana
Two new meroterpenoid pyrones, chevalone G (1) and aszonapyrone C (2), a new indole alkaloid, 7-chlorofischerindoline (3) and a new bicyclic brasiliamide, brasiliamide H (4), together with sixteen known compounds, 5–20 were isolated from the fungus Neosartorya hiratsukae. Their structures were established on the basis of spectroscopic evidence. The antibacterial activity and the cytotoxic activity of new compounds were evaluated.
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Bioactive xanthoquinodins and epipolythiodioxopiperazines from Chaetomium globosum 7s-1, an endophytic fungus isolated from Rhapis cochinchinensis (Lour.) Mart
(2020-02-16)
Tantapakul, Cholpisut
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Promgool, Trinop
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Kanokmedhakul, Kwanjai
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Soytong, Kasem
;
Song, Jiaojiao
A new xanthoquinodin B9 (1), together with two known xanthoquinodins, xanthoquinodin A1 (2) and xanthoquinodin A3 (3), three epipolythiodioxopiperazines, chetomin (4), chaetocochin C (5) and dethio-tetra(methylthio)chetomin (6), and four other compounds, chrysophanol (7), emodin (8), alatinone (9), and ergosterol (10) were isolated from the endophytic fungus Chaetomium globosum 7s-1, isolated from Rhapis cochinchinensis (Lour.) Mart. All isolated structures were established based on their spectroscopic data analyses. Compounds 1–6 showed antibacterial activity against Gram positive bacteria with MICs ranging from 0.02 pM to 10.81 µM. Compounds 1–6 also exhibited cytotoxicity against KB, MCF-7 and NCI-H187 cancer cell lines (IC<inf>50</inf> 0.04–18.40 µM). However, they were cytotoxic towards a normal cell line (Vero cell) with IC<inf>50</inf> values ranging from 0.04 to 3.86 µM.
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Antifungal activity of microbial nanoparticles derived from Chaetomium spp. against Magnaporthe oryzae causing rice blast
(2020-01-01)
Song, Jiao Jiao
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Soytong, Kasem
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Kanokmedhakul, Somdej
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Kanokmedhakul, Kwanjai
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Poeaim, Supattra
The Magnaporthe oryzae isolate PO2 was proven to cause rice blast var. PSL 2 in this study. Chaetomium elatum, Chaetomium lucknowense and Chaetomium brasiliense were antagonised to M. oryzae. The hexane extract of C. brasiliense gave the highest inhibition of the spore production with an ED<inf>50</inf> of 35 ppm, the EtOAC extract of C. lucknowense inhibited the spore production at 57 ppm and the EtOAC extracts of C. elatum inhibited the spore production at 106 ppm. The nano-CLM (C. lucknowense) inhibited the spore production at 5.24 ppm, the nano-CBH (C. brasiliense) inhibited the spore production at 6.86 ppm and the nano-CEE (C. elatum) inhibited the spore production at 7.89 ppm. The rice leaves treated with nano-CBH from C. brasiliense produced Sakuranertin and Oryzalexin B as seen on the thin layer chromatography where the Rf value was 0.08 assumed to be Sakuranertin, and the R<inf>f</inf> value of 0.28 supposed to be Oryzalexin B. It was found that the nanoparticles act as elicitors to induce immunity in rice plants through the production of phytoalexin.
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Meroditerpene pyrone, tryptoquivaline and brasiliamide derivatives from the fungus Neosartorya pseudofischeri
(2019-09-01)
Paluka, Jakkapat
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Kanokmedhakul, Kwanjai
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Soytong, Mayamor
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Soytong, Kasem
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Kanokmedhakul, Somdej
Two new meroditerpene pyrones, chevalone F (1) and 11-hydroxychevalone E (2), a new tryptoquivaline analog, tryptoquivaline V (3) and a new brasiliamide analog, brasiliamide G (4), together with thirteen known compounds, chevalones A-C (5–7), chevalone E (8), 11-hydroxychevalone C (9), pyripyropene A (10), isochaetominine C (11), pyrrolobenzoxazine terpenoids CJ-12662 (12) and CJ-12663 (13), fischerindoline (14), eurochevalierine (15), 1,4-diacetyl-2,5-dibenzylpiperazine-3,7′′-oxide (16) and lecanorin (17) were isolated from the fungus Neosartorya pseudofischeri. Their structures were established on the basis of spectroscopic evidence. Compound 2 showed weak antibacterial activity against Escherichia coli and Salmonella enterica serovar Typhimurium, whereas compounds 7, 12, 13 and 15 showed antibacterial activity against Bacillus cereus and Staphylococcus aureus. In addition, compounds 13 and 14 showed cytotoxicity against KB and MCF-7 cancer cell lines, as well as the Vero cell line.
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Types A and D Trichothecene Mycotoxins from the Fungus Myrothecium roridum
(2019-07-01)
Lakornwong, Waranya
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Kanokmedhakul, Kwanjai
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Soytong, Kasem
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Unartngam, Arm
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Tontapha, Sarawut
Chromatographic separation of extracts from the fungal biomass of a plant pathogenic fungus, Myrothecium roridum, yielded 8 trichothecene toxins including 6 type D trichothecenes (1 - 6) and 2 type A trichothecenes (7 - 8). 6′,12′-Epoxymyrotoxin A (1) and 7′-hydroxymytoxin B (2) were new macrocyclic trichothecenes, while the other trichothecenes were identified as myrotoxin B (3), myrotoxin D hydrate (4), 2′,3′-epoxymyrothecine A (5), miotoxin A (6), and 2 trichothecenes lacking the macrocyclic lactone system, roridin L-2 (7) and trichoverritone (8). The structures of these mycotoxins were characterized using spectroscopic methods. The absolute configurations of 1 and 2 were determined by NOESY and a comparison of their experimental and calculated ECD spectra. Most of these mycotoxins (1 - 4 and 6) exhibited highly potent antimalarial activity against Plasmodium falciparum. They also showed strong cytotoxicity towards KB and NCI-H187 cell lines (IC <inf>50</inf> 0.60-112.28 nM), as well as the Vero cell line (IC <inf>50</inf> 1.50-46.51 nM).
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Mycotoxins from the Fungus Botryotrichum piluliferum
(2017-02-22)
Rajachan, Oue Artorn
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Kanokmedhakul, Kwanjai
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Soytong, Kasem
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Kanokmedhakul, Somdej
Two new sterigmatocystin derivatives, oxisterigmatocystins E and F (1 and 2, respectively), along with nine known compounds, oxisterigmatocystins G and H (3 and 4, respectively), sterigmatocystin (5), N-0532B (6), O-methylsterigmatocystin (7), N-0532A (8), 6-O-methylversicolorin A (9), 6,8-O-dimethylversicolorin A (10), and 8-O-methylaverufin (11), were isolated from the fungus Botryotrichum piluliferum. The structures of these mycotoxins were elucidated by spectroscopic evidence. Among these, compounds 3, 4, and 9 were discovered as natural products for the first time. Compounds 1, 3, and 4 displayed antimalarial activity toward Plasmodium falciparum (IC<inf>50</inf> = 7.9-23.9 μM). In addition, compounds 1-6 and 8-11 exhibited cytotoxicity against KB, MCF-7, and NCI-H187 cell lines (IC<inf>50</inf> = 0.38-78.6 μM). However, compounds 1-9 showed cytotoxic effects against the Vero cell line (IC<inf>50</inf> = 0.65-12.3 μM). This finding should promote awareness of the contamination of B. piluliferum in the food chain and agricultural soil.
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A new xanthone from the fungus Apiospora montagnei
(2017-01-01)
Arthan, Supakorn
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Tantapakul, Cholpisut
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Kanokmedhakul, Kwanjai
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Soytong, Kasem
;
Kanokmedhakul, Somdej
A new xanthone derivative, methyl 8-hydroxy-3-hydroxymethylxanthone-1-carboxylate (1), and seven known compounds, 8-hydroxy-3-methylxanthone-1-carboxylate (2), methyl 8-hydroxy-6-methylxanthone-1-carboxylate (3), ergosterol (4), cyathisterone (5), ergosta-4,6,8(14),22-tetraen-3-one (6), calvasterone (7) and 2-hexyl-3-methylmaleic anhydride (8) were first isolated from the fungus Apiospora montagnei. Their structures were elucidated on the basis of spectroscopic analysis (UV, IR, MS, 1D, and 2D NMR). Compounds 5 and 6 showed weak to very weak cytotoxicity against cancer cell lines, NCI-H187 and KB.
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Bioactive azaphilones from the fungus Penicillium multicolor CM01
(2016-06-01)
Hemtasin, Chulida
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Kanokmedhakul, Somdej
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Moosophon, Panawan
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Soytong, Kasem
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Kanokmedhakul, Kwanjai
Two new azaphilones, dechloroisochromophilone II (1) and epi-isochromophilone III (2), a new natural product, 5-hydroxy-4-methoxy-5,6-dihydro-2H-pyran-2-one (3), together with eleven known compounds, 4-14 were isolated from the fungus, Penicillium multicolor CM01. Their structures were elucidated by spectroscopic methods. Compounds 2, 8, 10 and 11 exhibited antimalarial activity against Plasmodium falciparum (IC<inf>50</inf> 2.1-7.8 μg/mL), while compounds 9 and 10 showed antimycobacterial activity against Mycobacterium tuberculosis (MIC 6.2 and 50.0 μg/mL, respectively). Compounds 2, 4, and 7-11 showed cytotoxicity against three cancer cell lines, KB, MCF-7 and NCI-H187 (IC<inf>50</inf> 2.2-35.2 μg/mL). In addition, compounds 1, 5-8 and 11 showed a minimum inhibition requirement to acetylcholinesterase (AChE) assay in the range of 0.03-0.25 nM.

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