Structures of chaetoglobosins C, D, E, and F, cytotoxic indol-3-yl-[13]cytochalasans from Chaetomium globosum

Sekita, Setsuko; Yoshihira, Kunitoshi; Natori, Shinsaku; Kuwano, Harumitsu

doi:10.1016/s0040-4039(00)78062-2

Cited by 55 publications

(48 citation statements)

References 2 publications

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“…These data, coupled with 13 C NMR spectroscopic data, established the molecular formula of 10 as C 32 H 37 N 2 O 4 F (15 degrees of unsaturation), suggesting 2 amu more than the mass of chaetoglobosin F (7). The 1 H-decoupled 19 F NMR spectroscopic data also confirmed the existence of the fluorine atom (δ F −100) in 10 (see Figure S3 in the Supporting Figure 2). This gave rise to significant differences in the chemical shifts measured in C 5 D 5 N of C-17 to C-23 between 7 and 10 ( Table 1).…”

Section: ■ Results and Discussionmentioning

confidence: 59%

“…These data were identical to those recorded in the literature. 4,19,20 Chaetoglobosin Journal of Agricultural and Food Chemistry Semisynthesis of Chaetoglobosin F a (10). 22 To a solution of compound 7 (37 mg, 0.070 mmoL) in CH 2 Cl 2 (2 mL) was added DAST (28 μL, 0.21 mmoL), and the mixture was stirred at room temperature for 1.5 h. Water (2 mL) was added to the solution, and the mixture was diluted with CH 2 Cl 2 (30 mL).…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

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Chaetoglobosins from Chaetomium globosum, an Endophytic Fungus in Ginkgo biloba, and Their Phytotoxic and Cytotoxic Activities

Xiao

Gao

et al. 2014

J. Agric. Food Chem.

119

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In preceding studies, cultivation of Chaetomium globosum, an endophytic fungus in Ginkgo biloba, produced five cytochalasan mycotoxins, chaetoglobosins A, G, V, Vb, and C (1-5), in three media. In the present work, five known chaetoglobosins, C, E, F, Fex, and 20-dihydrochaetoglobosin A (5-9), together with the four known compounds (11-14), were isolated from the MeOH extracts of the solid culture of the same endophyte. The structures of these metabolites were elucidated on the basis of spectroscopic analysis. Treatment of chaetoglobosin F (7) with (diethylamino)sulfur trifluoride (DAST) in dichloromethane afforded an unexpected fluorinated chaetoglobosin, named chaetoglobosin Fa (10), containing an oxolane ring between C-20 and C-23. The phytotoxic effects of compounds 1, 3-8, and 10 were assayed on radish seedlings; some of these compounds (1, 3, and 6-8) significantly inhibited the growth of radish (Raphanus sativus) seedlings with inhibitory rates of >60% at a concentration of 50 ppm, which was comparable or superior to the positive control, glyphosate. In addition, the cytotoxic activities against HCT116 human colon cancer cells were also tested, and compounds 1 and 8-10 showed remarkable cytotoxicity with IC50 values ranging from 3.15 to 8.44 μM, in comparison to the positive drug etoposide (IC50 = 2.13 μM). The epoxide ring between C-6 and C-7 or the double bond at C-6(12) led to a drastically increased cytotoxicity, and chaetoglobosin Fa (10) displayed a markedly increased cytotoxicity but decreased phytotoxicity.

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Section: ■ Results and Discussionmentioning

confidence: 59%

Section: ■ Materials and Methodsmentioning

confidence: 99%

Chaetoglobosins from Chaetomium globosum, an Endophytic Fungus in Ginkgo biloba, and Their Phytotoxic and Cytotoxic Activities

Xiao

Gao

et al. 2014

J. Agric. Food Chem.

119

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“…Chaetoglobosin A is the most widely studied metabolite in the chaetoglobosin series. Meanwhile, six further metabolites, chaetoglobosins C-G (3-7) and J (8), were isolated and identified from the same fungus C. globosum [15][16][17][18][19][20][21].…”

Section: Chaetoglobosinsmentioning

confidence: 99%

Chemical and Bioactive Diversities of the Genus Chaetomium Secondary Metabolites

Zhang

Li²,

Zong³

et al. 2012

MRMC

116

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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“…The molecular formula of chaetocyclinone A (1) was determined by HR-ESI-MS to be C 17 (Figure 2). The connectivities between hydrogen and carbon atoms were confirmed by HSQC and HMBC experiments and two fragments (ring A and C) had been established (Figure 2).…”

Section: Structure Elucidationmentioning

confidence: 99%

Structure and Biosynthesis of Chaetocyclinones, New Polyketides Produced by an Endosymbiotic Fungus

et al. 2007

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Three new fungal polyketide metabolites, chaetocyclinone A to C, were produced by cultures of Chaetomium sp. (strain Gö 100/2), which was isolated from marine algae. The structures of the novel compounds were established by detailed spectroscopic analysis. Additionally, an X‐ray analysis of chaetocyclinone C (5) was performed. Chaetocyclinone A (1) exhibits inhibitory activity against selected phytopathogenic fungi. The biosynthesis of 1 and 5 was studied by feeding 13C‐labelled acetate. The results suggest the polyketide pathway for the isolated metabolites. In the case of chaetocyclinone C (5), we assume an unusual condensation of two highly reactive heptaketide intermediates. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Structures of chaetoglobosins C, D, E, and F, cytotoxic indol-3-yl-[13]cytochalasans from Chaetomium globosum

Cited by 55 publications

References 2 publications

Chaetoglobosins from Chaetomium globosum, an Endophytic Fungus in Ginkgo biloba, and Their Phytotoxic and Cytotoxic Activities

Chaetoglobosins from Chaetomium globosum, an Endophytic Fungus in Ginkgo biloba, and Their Phytotoxic and Cytotoxic Activities

Chemical and Bioactive Diversities of the Genus Chaetomium Secondary Metabolites

Structure and Biosynthesis of Chaetocyclinones, New Polyketides Produced by an Endosymbiotic Fungus

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