Publications by authors named "Nattawut Boonyuen"

17 Publications

  • Page 1 of 1

Bioactive Dimeric Tetrahydroxanthones with 2,2'- and 4,4'-Axial Linkages from the Entomopathogenic Fungus .

J Nat Prod 2021 Apr 14. Epub 2021 Apr 14.

National Center for Genetic Engineering and Biotechnology (BIOTEC), National Science and Technology Development Agency (NSTDA), Thailand Science Park, Phaholyothin Road, Khlong Luang, Pathum Thani 12120, Thailand.

Thirteen tetrahydroxanthone dimers, -ascherxanthone A (), ascherxanthones C-G (-), and confluxanthones A-G (-), were isolated from the entomopathogenic fungus BCC53152. The chemical structures were determined based on analysis of NMR spectroscopic and mass spectrometric data. The absolute configurations of compounds and were 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. Compounds , -, -, and showed antimalarial activity against (K1, multidrug-resistant strain) (IC 0.6-6.1 μM), antitubercular activity against H37Ra (MIC 6.3-25.0 μg/mL), and cytotoxicity against NCI-H187 (IC 0.5-3.5 μM) and Vero (IC 0.9-6.1 μM) cells. All tested compounds except for compound exhibited cytotoxicity against KB cells (IC 1.3-9.7 μM).
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http://dx.doi.org/10.1021/acs.jnatprod.0c01212DOI Listing
April 2021

Towards a Miniaturized Culture Screening for Cellulolytic Fungi and Their Agricultural Lignocellulosic Degradation.

J Microbiol Biotechnol 2020 Nov;30(11):1670-1679

National Center for Genetic Engineering and Biotechnology (BIOTEC), National Science and Technology Development Agency (NSTDA), 113 Thailand Science Park, Klong Luang, Pathumthani 12120, Thailand.

The substantial use of fungal enzymes to degrade lignocellulosic plant biomass has widely been attributed to the extensive requirement of powerful enzyme-producing fungal strains. In this study, a two-step screening procedure for finding cellulolytic fungi, involving a miniaturized culture method with shake-flask fermentation, was proposed and demonstrated. We isolated 297 fungal strains from several cellulose-containing samples found in two different locations in Thailand. By using this screening strategy, we then selected 9 fungal strains based on their potential for cellulase production. Through sequence-based identification of these fungal isolates, 4 species in 4 genera were identified: (3 strains: AG466, AG438 and AG499), (4 strains: AG452, AG496, AG498 and AG559), (1 strain: AG548) and (1 strain: AG500). After examining their lignocellulose degradation capacity, our data showed that AG452 exhibited the highest glucose yield after saccharification of pretreated sugarcane trash, cassava pulp and coffee silverskin. In addition, AG548 produced the highest glucose yield after hydrolysis of pretreated sugarcane bagasse. Our study demonstrated that the proposed two-step screening strategy can be further applied for discovering potential cellulolytic fungi isolated from various environmental samples. Meanwhile, the fungal strains isolated in this study will prove useful in the bioconversion of agricultural lignocellulosic residues into valuable biotechnological products.
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http://dx.doi.org/10.4014/jmb.2007.07005DOI Listing
November 2020

Antimalarial 9-Methoxystrobilurins, Oudemansins, and Related Polyketides from Cultures of Basidiomycete Species.

J Nat Prod 2020 04 20;83(4):905-917. Epub 2020 Mar 20.

National Center for Genetic Engineering and Biotechnology (BIOTEC), Thailand Science Park, 113 Phaholyothin Road, Klong Luang, Pathumthani 12120, Thailand.

Fourteen new compounds, oudemansins -, oudemansinols -, favolasins -, favolasinin (), polyketides -, and (,)-2,4-dimethyl-5-phenyl-4-pentene-2,3-diol (), together with nine known compounds were isolated from the basidiomycete fungus sp. BCC 18686. Two new compounds, favolasin E () and 9-oxostrobilurin E (), were isolated from the closely related organism BCC 36684 along with nine β-methoxyacrylate-type derivatives. Compounds in the class of oudemansins and strobilurins exhibited moderate to strong antimalarial activity with relatively low cytotoxicity against Vero cells (African green monkey kidney fibroblasts). Potent antimalarial activity was demonstrated for 9-methoxystrobilurins G, K, and E (IC values 0.061, 0.089, and 0.14 μM, respectively). The structure-activity relationships (SAR) for antimalarial activity is proposed on the basis of the activity of the new and several known β-methoxyacrylate derivatives in combination with the data from previously isolated compounds. Furthermore, several compounds showed specific cytotoxicity against NCI-187 cells (human small-cell lung cancer), although the SAR was different from that for antimalarial activity.
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http://dx.doi.org/10.1021/acs.jnatprod.9b00647DOI Listing
April 2020

Secondary metabolites from cultures of the ant pathogenic fungus BCC 2728.

Nat Prod Res 2020 Jan 14:1-6. Epub 2020 Jan 14.

National Center for Genetic Engineering and Biotechnology (BIOTEC), Pathumthani, Thailand.

Five new compounds, iranginins A-E (-), together with sixteen known compounds were isolated from the insect pathogenic fungus BCC 2728. The structures and the absolute configurations of the new compounds were established by spectroscopic analyses, the application of modified Mosher's method (for ), ECD calculation (for ), and X-ray crystallographic analysis (for ). LL-Z1640-5 and mucorisocoumarin C were active against (MIC 41.7 and 85.0 µM, respectively), while peyroisocoumarin D exhibited cytotoxic activity (IC 65.6 µM).
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http://dx.doi.org/10.1080/14786419.2020.1713119DOI Listing
January 2020

Chromone derivatives, - and - taeniolin, from the marine-derived fungus sp. BCC31839.

Nat Prod Res 2021 Feb 28;35(3):392-398. Epub 2019 Jun 28.

National Center for Genetic Engineering and Biotechnology (BIOTEC), Klong Luang, Pathum Thani, Thailand.

Two unknown enantiomeric compounds, named ()- and ()-taeniolin, along with six known compounds, were isolated from the marine-associated fungus sp. BCC31839. Chemical structures were determined by NMR spectroscopic techniques, and the absolute configurations were confirmed by Mosher application together with CD spectral analyses. Both were inactive for antimicrobial activity against multidrug-resistant malaria parasite () and bacteria ( and ) at maximum tested concentration.
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http://dx.doi.org/10.1080/14786419.2019.1634710DOI Listing
February 2021

Xanthones from a lignicolous freshwater fungus (BCC 28210).

Nat Prod Res 2020 May 19;34(9):1233-1237. Epub 2019 Jan 19.

National Center for Genetic Engineering and Biotechnology (BIOTEC), National Science and Technology Development Agency (NSTDA), Pathum Thani, Thailand.

Four xanthones (‒) and a known compound, mansonone D (), were isolated from the lignicolous freshwater fungus BCC 28210 (family, Chaetosphaeriaceae). The structures of these compounds were elucidated by extensive spectroscopic analysis. Among the isolated metabolites, compound and the known mansonone D () displayed antimalarial activity against K1 with IC values of 7.75 and 0.55 μg/mL, respectively. Compound displayed antibacterial activity against with an MIC value of 6.25 μg/mL.
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http://dx.doi.org/10.1080/14786419.2018.1556655DOI Listing
May 2020

Antimicrobial activity and cytotoxicity of xanthoquinodin analogs from the fungus Cytospora eugeniae BCC42696.

Phytochemistry 2018 Jul 24;151:99-109. Epub 2018 Apr 24.

National Center for Genetic Engineering and Biotechnology (BIOTEC), National Science and Technology Development Agency (NSTDA), Thailand Science Park, Phaholyothin Road, Klong Luang, Pathumthani 12120, Thailand.

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 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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http://dx.doi.org/10.1016/j.phytochem.2018.04.001DOI Listing
July 2018

Terphenyl derivatives and drimane - Phathalide/isoindolinones from Hypoxylon fendleri BCC32408.

Phytochemistry 2017 Jul 3;139:8-17. Epub 2017 Apr 3.

National Center for Genetic Engineering and Biotechnology (BIOTEC), National Science and Technology Development Agency (NSTDA), Thailand Science Park, Paholyothin Road, Klong Luang, Pathumthani, 12120, Thailand. Electronic address:

The genus Hypoxylon, a member of the family Xylariaceae, has been known to produce significant secondary metabolites in terms of chemical diversity. Moreover, the compounds isolated can also be used as chemotaxonomic characters for differentiation among the two sections, which are sect. Annulata and sect. Hypoxylon. In our continuing chemical screening programme for novel compounds, the crude extracts of H. fendleri BCC32408 gave significant chemical profiles in HPLC analyses. Thus, the chemical investigation of these crude extracts was then carried out. The investigation led to the isolation of ten previously undescribed compounds including three terphenylquinones (fendleryls A - C), one terphenyl (fendleryl D), and six novel drimane - phthalide-type lactone/isoindolinones derivatives (fendlerinines A - F) along with seven known compounds (2-O-methylatromentin, rickenyl E, atromentin, rickenyls C - D, (+)-ramulosin, and O-hydroxyphenyl acetic acid). The chemical structures were determined on the basis of spectroscopic analyses, including 1D, 2D NMR and high-resolution mass spectrometry, as well as chemical transformations. In addition, these isolated compounds were assessed for antimicrobial activity including antimalarial (against Plasmodium falciparum, K-1 strain), antifungal (against Candida albicans), antibacterial (against Bacillus cereus) activities. Cytotoxicity against both cancerous (KB, MCF-7, NCI-H187) and non-cancerous (Vero) cells of these compounds were also evaluated.
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http://dx.doi.org/10.1016/j.phytochem.2017.03.008DOI Listing
July 2017

Highly oxygenated chromones from mangrove-derived endophytic fungus Rhytidhysteron rufulum.

Phytochemistry 2016 Feb 19;122:172-177. Epub 2015 Dec 19.

Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand. Electronic address:

Five highly oxygenated chromones, rhytidchromones A-E, were isolated from the culture broth of a mangrove-derived endophytic fungus, Rhytidhysteron rufulum, isolated from Thai Bruguiera gymnorrhiza. Their structures were determined by analysis of 1D and 2D NMR spectroscopic data. The structure of rhytidchromone A was further confirmed by single-crystal X-ray diffraction analysis. These compounds were evaluated for cytotoxicity against four cancer cell lines (MCF-7, Hep-G2, Kato-3 and CaSki). All compounds, except for rhytidchromone D, displayed cytotoxicity against Kato-3 cell lines with IC50 values ranging from 16.0 to 23.3μM, while rhytidchromones A and C were active against MCF-7 cells with IC50 values of 19.3 and 17.7μM, respectively.
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http://dx.doi.org/10.1016/j.phytochem.2015.12.010DOI Listing
February 2016

Trichoderma matsushimae and T. aeroaquaticum: two aero-aquatic species with Pseudaegerita-like propagules.

Mycologia 2012 Sep-Oct;104(5):1109-20. Epub 2012 Apr 11.

National Institute of Technology and Evaluation, Kisarazu, Chiba, Japan.

Four isolates tentatively identified as Pseudaegerita matsushimae on the basis of the morphology of bulbil-like propagules were collected from substrates submerged in water in Thailand and Japan. In culture studies the two Thai isolates were found to produce phialoconidia on conidiogenous cells and phialoconidiophores whose morphology was similar to that of Trichoderma. Phylogenetic analysis based on D1/D2 regions of LSU rDNA sequences showed that the four isolates were nested in Hypocrea/Trichoderma (Hypocreales) while P. corticalis, the type species of Pseudaegerita, belongs to Hyaloscypha (Helotiales). Preliminary analysis by ISTH Web tools based on 5.8S-ITS rDNA and phylogenetic analysis based on rpb2 and tef1-int4 genes showed that the isolates have specific sequences of Trichoderma (anchors 1-5) and belong to the Hamatum clade but they grouped apart from any known species of Trichoderma. The sequences of the tef1-int4 gene, which were amplified from the authentic specimen of P. matsushimae (IMI 266915), also showed that it belongs to the Hamatum clade closely clustering with T. yunnanense but separate from our four isolates. The morphology of P. matsushimae (IMI 266915), especially the sizes of phialides and phialoconidia, were different from T. yunnanense. Thus, we conclude that IMI 266915 and our isolates are to be assigned to two different species in the Hamatum clade of Trichoderma, although both species have similar morphology of bulbils and phialoconidia. Morphology and molecular data revealed that P. matsushimae should be assigned to the genus Trichoderma as T. matsushimae and the Thai and Japanese isolates are placed in T. aeroaquaticum sp. nov. This finding supports the interpretation that aero-aquatic fungi have evolved from terrestrial fungi. We assume that these fungi probably were derived from typically soil-inhabiting species of Trichoderma; an adaptation to aquatic environments is shown by formation of bulbil-like propagules floating on water.
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http://dx.doi.org/10.3852/11-253DOI Listing
November 2012

Annulatascus aquatorba sp. nov., a lignicolous freshwater ascomycete from Sirindhorn Peat Swamp Forest, Narathiwat, Thailand.

Mycologia 2012 May-Jun;104(3):746-57. Epub 2012 Jan 5.

National Center for Genetic Engineering and Biotechnology, Pathumthani, Thailand.

As part of a long term study of fungi colonizing submerged wood in freshwater streams a new Annulatascus species, A. aquatorba, is described and illustrated from Erythrophleum teysmannii test blocks from Sirindhorn Peat Swamp Forest, southern Thailand. It differs from other species in the genus in ascospore measurements, thickness of the cell wall, 1-3-septate, fusoid to lunate shape, with central brown cells and subhyaline end cells and without a mucilaginous sheath. Asci are cylindrical, pedicellate, with a distinct, wedge-shaped and non-amyloid apical ring. Phylogenetic relationships of this species, based on the combined partial 18S and 28S rDNA, place it in the same clade as A. velatisporus (type species), A. hongkongensis and A. nilensis.
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http://dx.doi.org/10.3852/11-238DOI Listing
January 2013

Savoryellales (Hypocreomycetidae, Sordariomycetes): a novel lineage of aquatic ascomycetes inferred from multiple-gene phylogenies of the genera Ascotaiwania, Ascothailandia, and Savoryella.

Mycologia 2011 Nov-Dec;103(6):1351-71. Epub 2011 Jun 3.

Mycology Laboratory, Bioresources Technology Unit, National Center for Genetic Engineering and Biotechnology, 113 Thailand Science Park, Phaholyothin Road, Khlong 1, Khlong Luang, Pathumthani 12120, Thailand.

The taxonomic placement of freshwater and marine Savoryella species has been widely debated, and the genus has been tentatively assigned to various orders in the Sordariomycetes. The genus is characterized as possessing paraphyses that deliquesce early, elongate, clavate to cylindrical asci with a poorly developed apical ring and versicolored, three-septate ascospores. We performed two combined phylogenetic analyses of different genes: (i) partial small subunit rRNA (SSU), large subunit rRNA (LSU), DNA-dependent RNA polymerase II largest subunit (rpb2) dataset and (ii) SSU rDNA, LSU rDNA, DNA-dependent RNA polymerase II largest subunit (rpb1 and rpb2), translation elongation factor 1-alpha (tef1), the 5.8S ribosomal DNA (5.8S rDNA) dataset. Our results indicate that Savoryella species formed a monophyletic group within the Sordariomycetes but showed no affinity to the Hypocreales, Halosphaeriales (now Microascales), Sordariales and Xylariales, despite earlier assignments to these orders. Savoryella, Ascotaiwania and Ascothailandia (and its anamorph, Canalisporium) formed a new lineage that has invaded both marine and freshwater habitats, indicating that these genera share a common ancestor and are closely related. Because they show no clear relationship with any named order we erect a new order Savoryellales in the subclass Hypocreomycetidae, Sordariomycetes. The genera Savoryella and Ascothailandia are monophyletic, while the position of Ascotaiwania is unresolved. All three genera are phylogenetically related and form a distinct clade similar to the unclassified group of marine ascomycetes comprising the genera Swampomyces, Torpedospora and Juncigera (TBM clade: Torpedospora/Bertia/Melanospora) in the Hypocreomycetidae incertae sedis.
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http://dx.doi.org/10.3852/11-102DOI Listing
January 2012

Butyrolactones from the fungus Aspergillus terreus BCC 4651.

Chem Pharm Bull (Tokyo) 2010 Nov;58(11):1545-8

National Center for Genetic Engineering and Biotechnology, Thailand.

Two new butenolides, butyrolactones VI (1) and VII (2), were isolated together with six known compounds, butyrolactones I (3), II (4), IV (5), and V (6), aspernolide B (7), and bisdethiodi(methylthio)acetylaranotin (8) from the fungus Aspergillus terreus BCC 4651. Compound 8, exhibiting a minimum inhibitory concentration (MIC) value of 1.56 µg/ml against Mycobacterium tuberculosis H37Ra, proved to be the antimycobacterial principle from the culture of this fungus. On the other hand, butyrolactone V (6) showed antiplasmodial activity against Plasmodium falciparum K1 with an IC₅₀ of 7.9 µg/ml.
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http://dx.doi.org/10.1248/cpb.58.1545DOI Listing
November 2010

Butenolide and furandione from an endophytic Aspergillus terreus.

Chem Pharm Bull (Tokyo) 2010 Sep;58(9):1221-3

Program in Biotechnology, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand.

A new butenolide, aspernolide D (1), and furandione, asperterone (2), together with four known butenolides, butyrolactones I-IV and aspernolide B, were obtained from cultures of the endophytic fungus Aspergillus terreus, isolated from the flowering plant Mammea siamensis. The structures of these compounds were elucidated by analysis of NMR spectroscopic and mass spectrometric data.
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http://dx.doi.org/10.1248/cpb.58.1221DOI Listing
September 2010

Two new drimane sesquiterpenes, fudecadiones A and B, from the soil fungus Penicillium sp. BCC 17468.

Planta Med 2011 Jan 24;77(1):74-6. Epub 2010 Jun 24.

National Center for Genetic Engineering and Biotechnology, Thailand Science Park, Klong Luang, Pathumthani, Thailand.

Two new drimane sesquiterpenoids, fudecadione A and fudecadione B (1, 2), together with the known brefeldin A (3) and fulvic acid (4), were isolated from the soil fungus Penicillium sp. BCC 17468. Chemical structures were determined based on spectroscopic evidence including 1D and 2D NMR and mass spectral data. The proposed relative stereochemistry of fudecadiones A and B was based upon NOESY spectral data and chemical means. Compounds 1 and 4 exhibited anticancer activity against MCF-7, KB, and NCI-H187, with IC (50) values in the range of 5.05-45.43 µg/mL, while compound 2 was inactive against these tumor cells. Brefeldin (3) also displayed antimalarial activity against PLASMODIUM FALCIPARUM (K1, multidrug-resistant strain), with an IC (50) value of 1.12 µg/mL.
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http://dx.doi.org/10.1055/s-0030-1250057DOI Listing
January 2011

Gamma-lactones and ent-eudesmane sesquiterpenes from the endophytic fungus Eutypella sp. BCC 13199.

J Nat Prod 2009 Sep;72(9):1720-2

National Center for Genetic Engineering and Biotechnology, 113 Thailand Science Park, Phaholyothin Road, Klong Luang, Pathumthani 12120, Thailand.

Two new gamma-lactones, eutypellins A (1) and B (2), and two ent-eudesmane sesquiterpenes, ent-4(15)-eudesmen-11-ol-1-one (3) and ent-4(15)-eudesmen-1alpha,11-diol (4), together with three known pimarane diterpenes, diaporthein B, scopararane A, and libertellenone C, were isolated from the endophytic fungus Eutypella sp. BCC 13199. The structures of these compounds were elucidated by interpretation of spectroscopic data. The absolute configuration of 4 was confirmed by application of the modified Mosher's method. Eutypellin A (1) and sesquiterpene 3 exhibited weak cytotoxic activities.
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http://dx.doi.org/10.1021/np900316xDOI Listing
September 2009

Depsidones from the endophytic fungus BCC 8616.

J Nat Prod 2006 Sep;69(9):1361-3

National Center for Genetic Engineering and Biotechnology (BIOTEC), Thailand Science Park, Paholyothin Road, Klong Luang, Pathumthani 12120, Thailand.

Three new depsidones (1-3) have been isolated from the endophytic fungus BCC 8616 and their structures analyzed on the basis of spectroscopic data interpretation. Compound 1 exhibited weak cytotoxic activity against breast and epidermoid carcinoma cell lines.
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http://dx.doi.org/10.1021/np060190cDOI Listing
September 2006