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    Antimalarial and antimicrobial substances isolated from the endophytic actinomycete, Streptomyces aculeolatus MS1-6
    (2023-03-01)
    Kuncharoen, Nattakorn
    ;
    Bunbamrung, Nantiya
    ;
    Intaraudom, Chakapong
    ;
    Choowong, Wilunda
    ;
    Thawai, Chitti
    Seven undescribed compounds, including four naphthoquinone terpenoids (aculeolatins A – D), one rare 2-nitropyrrole terpenoid (nitropyrrolin F), and two hydroxamate siderophores (aculeolamides A and B) and one further undescribed compound (2,5,7-trihydroxy-3,6-dimethylnaphthalene-1,4-dione), together with eleven known compounds (arromycin, phenaziterpene A, nitropyrrolin A, heronapyrroles A and B, salaceyin A, 5,7-dihydroxy-2-isopropylchromone, 1-hydroxyphenazine, 1-methoxyphenazine, 1-acetyl-β-carboline, and N-(2-phenylethyl) acetamide), were isolated from the cultures of the endophytic Streptomyces aculeolatus MS1-6. The structures of the isolated compounds were determined using NMR spectroscopy and corroborated using chemical modification. These compounds exhibited a broad spectrum of biological activities, including antimalarial (IC<inf>50</inf> 6.03–9.84 μg/mL), antitubercular (MIC 3.13–6.25 μg/mL), anti-plant pathogenic fungal (MIC 25.0–50.0 μg/mL), and antibacterial (MIC 3.03–50 μg/mL) activities; however, they displayed unremarkable cytotoxicity against cancerous (MCF-7 and NCI–H187) and non-cancerous (Vero) cell lines.
      1
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    Bioactive azaphilones from the fungus Penicillium multicolor CM01
    (2016-06-01)
    Hemtasin, Chulida
    ;
    Kanokmedhakul, Somdej
    ;
    Moosophon, Panawan
    ;
    Soytong, Kasem
    ;
    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.
      1
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    Antimalarial and antitubercular C-glycosylated benz[α]anthraquinones from the marine-derived Streptomyces sp. BCC45596
    (2012-09-01)
    Supong, Khomsan
    ;
    Thawai, Chitti
    ;
    Suwanborirux, Khanit
    ;
    Choowong, Wilunda
    ;
    Supothina, Sumalee
    Three naturally new C-glycosylated benz[α]anthraquinone derivatives, urdamycinone E (1), urdamycinone G (2), dehydroxyaquayamycin (3) have been isolated from the marine Streptomycetes sp. BCC45596. Urdamycin E (4), the possible biosynthetic precursor of 1-3, has also been identified after a re-cultivation of the strain. These compounds (1-4) exhibited potent anti-Plasmodium palcifarum K1 strain with IC <inf>50</inf> values in a range of 0.0534-2.93 μg/mL and anti-Mycobacterium tuberculosis with minimum inhibition concentrations (MICs) in a range of 3.13-12.50 μg/mL. Cytotoxicity against KB, MCF-7, NCI-H187, and Vero cells was also evaluated. © 2012 Phytochemical Society of Europe.
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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.