Chromones from an ascomycete, Chaetomium aureus

Li, Li Mei; Zou, Qiang; Li, Guo You

doi:10.1016/j.cclet.2010.05.023

Cited by 22 publications

(12 citation statements)

References 9 publications

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“…The rich variation of structures is mirrored in a variety of biological activities especially including the cytotoxicity, antimalarial, antibacterial activity, phytotoxicity, inhibition of thioredoxin reductase [63], monoamine oxidase, metallo--lactamase [100,101], as well as of glyceraldehyde-3-phosphate dehydrogenase [139]. However, only the minority of the compounds discussed here have not yet been tested in biological assays.…”

Section: Resultsmentioning

confidence: 95%

“…Chaetoquadrin D (112), G(115), and H (116) have displayed appreciable monoamine oxidase inhibitory activity (IC 50 = 3.8 10 -5 , 4.5 10 -4 , and 2.3 10 -4 M, respectively). Another novel chromone chaetoaurin (120) and six known analogues eugenetin(121), eugenitol(122), chaetoquadrins A (109), B (110), G(115), and H (116), were isolated from a solid culture of C. aureus[100].…”

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confidence: 99%

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Chemical and Bioactive Diversities of the Genus Chaetomium Secondary Metabolites

Zhang

Li²,

Zong³

et al. 2012

MRMC

123

102

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The genus Chaetomium fungi are considered to be a rich source of novel and bioactive secondary metabolites of great importance. Up till now, a variety of more than 200 secondary metabolites belonging to diverse structural types of chaetoglobosins, epipolythiodioxopiperazines, azaphilones, xanthones, anthraquinones, chromones, depsidones, terpenoids, and steroids have been discovered. Most of these fungal metabolites exhibited antitumor, cytotoxic, antimalarial, enzyme inhibitory, antibiotic, and other activities. This review covers the extraction, structure elucidation, structural diversity, and biological activities of natural products isolated from about 30 fungi associated with marine- and terrestrial- origins, and highlights some bioactive compounds as well as their mechanisms of action and structure-activity relationships.

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Section: Resultsmentioning

confidence: 95%

mentioning

confidence: 99%

Chemical and Bioactive Diversities of the Genus Chaetomium Secondary Metabolites

Zhang

Li²,

Zong³

et al. 2012

MRMC

123

102

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show abstract

“…The UV spectrum showed maximal absorption bonds at 290, 258, 251, 238, and 232 nm, suggesting that 1 was a chromone derivative. 17 The 13 C NMR spectrum indicated the presence of 15 carbon signals, including two methyls, two methlenes, three methines, and eight quaternary carbons. The chemical shi of the phenolic hydroxy group (d H 12.81) suggested the presence of an intramolecular hydrogen bond between 5-OH and C-4 carbonyl groups.…”

Section: Resultsmentioning

confidence: 98%

Chaetosemins A–E, new chromones isolated from an Ascomycete Chaetomium seminudum and their biological activities

Tian

Tang

et al. 2015

RSC Adv.

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Fifteen aromatic polyketide metabolites, including four new chromones, chaetosemins B-E (2-5), with compound 4 bearing a new skeleton, and two new natural products, chaetosemin A (1) and (+)-(S)chaetoquadrin J (14), together with nine known ones (6-13, 15), were isolated from the organic extract of a solid fermented culture of an Ascomycete filamentous fungus, Chaetomium seminudum. The structures of 1-5 were determined by spectroscopic analysis, and the absolute configuration of chaetosemin A (1) was confirmed by X-ray crystallography, whereas the stereochemistry of 1-4 and 14 was assigned by comparison of their specific optical rotations with reported data for structurally related compounds. All compounds were isolated for the first time from Chaetomium seminudum. Compounds 1 and 2 consisted of L-cysteine and D-cysteine units, respectively. Most of them were evaluated for in vitro antifungal activities against some phytopathogenic fungi. Among them, chaetosemin B (2) was the most active against Magnaporthe oryzae and Gibberella saubinettii with MICs of 6.25 and 12.5 mM, respectively. In addition, chaetosemin C (3) showed antioxidant activity with 50.7% DPPH free radical scavenging activity at 50 mM, and chaetoquadrin J (14) displayed weak inhibition of soluble epoxide hydrolase (sEH).

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“…Chaetomium globosum , belonging to a well‐known member of the Chaetomiaceae family, was frequently found in plants, soil, animals, and dung . Previously phytochemical studies have afforded a wide range of bioactive secondary metabolites, exemplified as polysaccharides with anticancer and antibacterial activities from C. globosum CGMCC 6882, cytochathiazines A–C possessing a 2 H ‐1,4‐thiazine functionality from the coculture of C. globosum and Aspergillus flavipes , antibacterial cytochalasan alkaloids from the arthropod‐associated fungus C. globosum TW1‐1, aureochaeglobosins A–C as the novel [4+2] cycloaddition heterodimers of chaetoglobosin with significant cytotoxicity against human MDA‐MB‐231 cancer cells from C. globosum from the tuber of Pinellia ternata , antiproliferative cytoglobosins H and I from deep‐sea‐derived fungus C. globosum .…”

Section: Introductionmentioning

confidence: 99%

Aureonitols A and B, Two New C₁₃‐Polyketides from Chaetomium globosum, an Endophytic Fungus in Salvia miltiorrhiza

Shen

Zhao

Chen

et al. 2019

Chemistry & Biodiversity

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Two new C13‐polyketides, aureonitols A and B (1 and 2), along with five known compounds (3–7), were isolated from the solid fermentation culture of the plant endophytic fungus Chaetomium globosum from the aerial parts of Salvia miltiorrhiza. The structures and absolute configurations of 1 and 2 were determined by comprehensive spectroscopic data analysis and computed methods. Compound 5 was found to display the remarkable antimicrobial activities against four multidrug‐resistant bacteria (Enterococcus faecalis, Enterococcus faecium, Staphylococcus aureus, and Staphylococcus epidermidis) with MIC values of 3.13–6.25 μg/mL (ciprofloxacin: 0.78–1.56 μg/mL), and also against all tested fungal strains with MIC values of 3.13–25 μg/mL (ketoconazole: 0.78–12.50 μg/mL).

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Chromones from an ascomycete, Chaetomium aureus

Cited by 22 publications

References 9 publications

Chemical and Bioactive Diversities of the Genus Chaetomium Secondary Metabolites

Chemical and Bioactive Diversities of the Genus Chaetomium Secondary Metabolites

Chaetosemins A–E, new chromones isolated from an Ascomycete Chaetomium seminudum and their biological activities

Aureonitols A and B, Two New C₁₃‐Polyketides from Chaetomium globosum, an Endophytic Fungus in Salvia miltiorrhiza

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Chromones from an ascomycete, Chaetomium aureus

Cited by 22 publications

References 9 publications

Chemical and Bioactive Diversities of the Genus Chaetomium Secondary Metabolites

Chemical and Bioactive Diversities of the Genus Chaetomium Secondary Metabolites

Chaetosemins A–E, new chromones isolated from an Ascomycete Chaetomium seminudum and their biological activities

Aureonitols A and B, Two New C13‐Polyketides from Chaetomium globosum, an Endophytic Fungus in Salvia miltiorrhiza

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Aureonitols A and B, Two New C₁₃‐Polyketides from Chaetomium globosum, an Endophytic Fungus in Salvia miltiorrhiza