Chaetoglobosins, cytotoxic 10-(indol-3-yl)-(13)cytochalasans from Chaetomium spp. IV. 13C-Nuclear magnetic resonance spectra and their application to a biosynthetic study.

Sekita, Setsuko; Yoshihira, Kunitoshi; Natori, Shinsaku

doi:10.1248/cpb.31.490

Cited by 72 publications

(71 citation statements)

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“…Analysis of 1 H, 13 C and 2D NMR (COSY, HSQC, HMBC, tROESY) spectral data in DMSO- d 6 revealed that the structures of compounds 1 and 2 match those of the known chaetoglobosin A ( 1 ) and C ( 2 ) (Figure 1), respectively. A comparison of 13 C NMR values obtained in the present study for chaetoglobosin A ( 1 ) and chaetoglobosin C ( 2 ) with already-reported data is given in Table 3 (Sekita et al 1983). Chaetoglobosin A and C are members of the cytochalasan family of compounds, first isolated from the same fungus Chaetomium globosum from Japan in 1976 together with the chaetoglobosin D, E and F.…”

Section: Resultssupporting

confidence: 65%

“…A comparison of 13 C NMR values obtained in the present study for chaetoglobosin A ( 1 ) and chaetoglobosin C ( 2 ) with already-reported data is given in Table 3 (Sekita et al 1983). Chaetoglobosin A and C are members of the cytochalasan family of compounds, first isolated from the same fungus Chaetomium globosum from Japan in 1976 together with the chaetoglobosin D, E and F.…”

Section: Resultssupporting

confidence: 65%

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Antimicrobial activities of endophytic fungi of the Sri Lankan aquatic plantNymphaea nouchaliand chaetoglobosin A and C, produced by the endophytic fungusChaetomium globosum

et al. 2016

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Twenty distinct endophytic fungi were isolated from the surface-sterilized plant parts of Nymphaea nouchali and were identified using morphological and molecular techniques. At 300 µg/disc concentration, eight of the 20 fungal extracts exhibited antimicrobial activities against Staphylococcus aureus (ATCC 25923) and Bacillus cereus (ATCC 11778) while two within the eight showed activity against Pseudomonas aeruginosa (ATCC 9027) and Escherichia coli (ATCC 35218). Furthermore, investigation of the crude extract of Chaetomium globosum resulted in the isolation of two known cytochalasans, chaetoglobosin A and C, and their structures were elucidated and confirmed by mass and nuclear magnetic resonance (NMR) (1H, 13C, COSY, HSQC, HMBC and tROESY) spectral data. Chaetoglobosin A showed antibacterial activities against Bacillus subtilis (MIC 16 µg mL−1), Staphylococcus aureus (MIC 32 µg mL−1) and methicillin-resistant Staphylococcus aureus (MRSA, MIC 32 µg mL−1). This is the first study to report the isolation, identification and antimicrobial properties of endophytic fungi of N. nouchali in Sri Lanka.

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Section: Resultssupporting

confidence: 65%

Section: Resultssupporting

confidence: 65%

Antimicrobial activities of endophytic fungi of the Sri Lankan aquatic plantNymphaea nouchaliand chaetoglobosin A and C, produced by the endophytic fungusChaetomium globosum

et al. 2016

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“…A identificação destas substâncias foi realizada com base nos dados espectroscópicos obtidos (RMN 1 H e 13 C, DEPT, gCOSY 1 H-1 H, gHMQC, gHMBC e EM) e comparação com dados disponíveis na literatura. 13,23 As citocalasanas são micotoxinas que se caracterizam quimicamente pela presença de um anel peridroisoindol-1-ona altamente substituído e fundido a um anel macrocíclico (Figura 1). A natureza do substituinte em C-3 indica o aminoácido que originou a citocalasana, através da ligação com a cadeia policetídica precursora dos anéis peridroisoindol-1-ona e macrocíclico.…”

Section: Determinação Da Concentração Inibitória Mínima (Cim)unclassified

“…Mais de 30 chaetoglobosinas já foram isoladas e identificadas, e os dados de difração de raios-X permitiram o estabelecimento da estrutura cristalográfica das chaetoglobosinas. 22 Portanto, apesar da complexidade estrutural destas substâncias, é relativamente simples identificar a classe química com base na análise dos dados de RMN 1 H e 13 C, e, através da comparação com os dados da literatura, 13,23 estabelecer a estrutura da chaetoglobosina. A análise dos dados de RMN (ddd, J = 15,4; 10,1; 3,5 Hz, H-14) indicaram a presença de duas ligações duplas com geometria E no anel macrocíclico, geralmente encontradas nas chaetoglobosinas entre C-21 e C-22 e entre C-13 e C-14.…”

Section: Determinação Da Concentração Inibitória Mínima (Cim)unclassified

Chaetoglobosinas produzidas por Chaetomium globosum, fungo endofítico associado a Viguiera robusta Gardn. (Asteraceae)

Momesso¹,

Kawano²,

Ribeiro³

et al. 2008

Quím. Nova

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Chaetoglobosinas produzidas porRecebido em 1/10/07; aceito em 7/5/08; publicado na web em 19/9/08 CHAETOGLOBOSINS PRODUCED BY Chaetomium globosum, ENDOPHYTIC FUNGUS FOUND IN ASSOCIATION WITH Viguiera robusta Gardn (ASTERACEAE). Endophytes live in association with host plants during all or part of their life cycle without causing any apparent disease. They are considered outstanding and underexploited sources of novel bioactive compounds. Chaetomium globosum was isolated as an endophytic fungus from the healthy leaves of Viguiera robusta. C. globosum is a remarkable producer of chaetoglobosins, which are typically cytotoxic. In this work, chaetoglobosins B (1), D (2) and E (3) have been produced by the endophytic C. globosum strain. Chaetoglobosin B was evaluated against Jurkat (leukemia) and B16F10 (melanoma) tumoral cells and showed 89.55% and 57.10% of inhibition at 0.1 mg mL -1 , respectively. Chaetoglobosin B also showed weak antibacterial activity against Staphylococcus aureus (MIC 120 µg/mL) and Escherichia coli (MIC 189 µg/mL).

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“…Their structures were determined as chaetoglobosin A (1), C (2), D (3), E (4), G (5), R (6) (Fig. 2), ergosterol, allantoin and uracil on the basis of ESI-MS, 1 H and 13 C NMR together with 2D-NMR spectroscopic analysis, as well as comparison of chemical-physic properties with those of previously reported data in the literatures [17][18][19][20][21][22]. In the present paper, we report, for the first time, the potent antifungal activity of chaetoglobosins against these two agricultural important phytopathogenic fungi R. stolonifer and C. diplodiella, which can cause serious plant diseases, such as peach rhizopu rot and grape white rot, respectively.…”

Section: Isolation and Identification Of Antifungal Metabolitesmentioning

confidence: 89%

Antifungal Metabolites Produced by Chaetomium globosum No.04, an Endophytic Fungus Isolated from Ginkgo biloba

Zhang

Qin

et al. 2013

Indian J Microbiol

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The fungal endophyte Chaetomium globosum No.04 was isolated from the medicinal plant Ginkgo biloba. The crude extract of the fungus fermentation were active in the agar-diffusion tests against the phytopathogenic fungi Rhizopus stolonifer and Coniothyrium diplodiella. Further bioassay-guided chemical investigation led to the isolation and purification of six alkaloids and three non-targeted compounds from 50 L fermentation of this endophytic fungus and their structures were elucidated as chaetoglobosin A, C, D, E, G, R (1-6), ergosterol, allantoin and uracil, by means of spectroscopic analysis. Compounds 1-6 showed significant growth inhibitory activity against R. stolonifer and C. diplodiella at a concentration of 20 lg/disc. We present here, for the first time, the potent antifungal activity of chaetoglobosins from endophytic fungi against two important phytopathogenic fungi R. stolonifer and C. diplodiella.

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Chaetoglobosins, cytotoxic 10-(indol-3-yl)-(13)cytochalasans from Chaetomium spp. IV. 13C-Nuclear magnetic resonance spectra and their application to a biosynthetic study.

Cited by 72 publications

References 0 publications

Antimicrobial activities of endophytic fungi of the Sri Lankan aquatic plantNymphaea nouchaliand chaetoglobosin A and C, produced by the endophytic fungusChaetomium globosum

Antimicrobial activities of endophytic fungi of the Sri Lankan aquatic plantNymphaea nouchaliand chaetoglobosin A and C, produced by the endophytic fungusChaetomium globosum

Chaetoglobosinas produzidas por Chaetomium globosum, fungo endofítico associado a Viguiera robusta Gardn. (Asteraceae)

Antifungal Metabolites Produced by Chaetomium globosum No.04, an Endophytic Fungus Isolated from Ginkgo biloba

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