Chaetoviridin A
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| Category | Others |
| Catalog number | BBF-04679 |
| CAS | 128252-98-2 |
| Molecular Weight | 432.9 |
| Molecular Formula | C23H25ClO6 |
| Purity | >95% by HPLC |
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Description
Chaetoviridin A is a fungal metabolite isolated from Chaetomium globosum, which exhibits antifungal activity against plant pathogenic fungi.
Specification
| Storage | Store at -20°C |
| IUPAC Name | (6aS)-5-chloro-9-[(2S,3R)-3-hydroxy-2-methylbutanoyl]-6a-methyl-3-[(E,3S)-3-methylpent-1-enyl]furo[2,3-h]isochromene-6,8-dione |
| Canonical SMILES | CCC(C)C=CC1=CC2=C(C(=O)C3(C(=C(C(=O)O3)C(=O)C(C)C(C)O)C2=CO1)C)Cl |
| InChI | InChI=1S/C23H25ClO6/c1-6-11(2)7-8-14-9-15-16(10-29-14)18-17(20(26)12(3)13(4)25)22(28)30-23(18,5)21(27)19(15)24/h7-13,25H,6H2,1-5H3/b8-7+/t11-,12-,13+,23-/m0/s1 |
| InChI Key | HWSQVPGTQUYLEQ-CCBHEJLASA-N |
Properties
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 607.6°C at 760 mmHg |
| Melting Point | 157-158°C |
| Density | 1.31 g/cm3 |
| Solubility | Soluble in DMSO, methanol, chloroform, acetone |
Reference Reading
1. Azaphilones from the Endophyte Diaporthe sp. and Their Toxicity
Fangfang Huang, Xiao Lin, Quanyi Lu Chem Biodivers. 2022 Nov;19(11):e202200849. doi: 10.1002/cbdv.202200849. Epub 2022 Nov 4.
Chemotherapy and targeted therapies are increasingly used as conventional means to control tumor growth and prolong survival. Patient treated with anti-neoplastic agents experience severe side effects, especially those cytotoxic chemotherapies. Exploring chemo agents with less side effects is the hot spot of anticancer research. In this study, three azaphilone derivatives (chaetoviridin A (1), chaetoviridin E (2) and chaetomugilin D (3)) were isolated from the endophyte of the plant Anoectochilus roxburghii (Wall.) Lindl, their structures were elucidated by NMR. The toxicity of these compounds was evaluated by zebrafish model. The results show that these compounds had no toxicity against zebrafish. These compounds may act as safe anticancer drug leads according to this result. These three azaphilone derivatives were first time reported isolated from Diaporthe species which mainly used to isolate from Chaetomium species.
2. Detection of Chaetomium globosum, Ch. cochliodes and Ch. rectangulare during the Diversity Tracking of Mycotoxin-Producing Chaetomium-Like Isolates Obtained in Buildings in Finland
Johanna M Salo, Orsolya Kedves, Raimo Mikkola, László Kredics, Maria A Andersson, Jarek Kurnitski, Heidi Salonen Toxins (Basel). 2020 Jul 8;12(7):443. doi: 10.3390/toxins12070443.
The diversity of Chaetomium-like isolates in buildings in Finland is poorly documented. This paper describes a set of methods for rapid diversity tracking of 42 indoor Chaetomium-like isolates. These isolates were categorized based on their fluorescence emission, ascomatal hair morphology, responses in three bioassays and resistance/sensitivity to the wetting agent Genapol X-080. Thirty-nine toxigenic isolates were identified [Ch. globosum (n = 35), Ch. cochliodes (n = 2) and Ch. rectangulare (n = 2)]. These isolates were identified down to the species level by tef1α gene sequencing. The major toxic substances in the ethanol extracts of the Ch. globosum and Ch. cochliodes strains were chaetoglobosin, chaetoviridin A and C, chaetomugilin D and chaetomin, identified based on HPLC-UV and mass spectrometry data (MS and MS/MS). Ethanol extracts from pure Ch. globosum cultures exhibited a toxicological profile in the boar sperm motility inhibition assay (BSMI), sperm membrane integrity damage assay (SMID) and inhibition of cell proliferation (ICP) assay, similar to that exhibited by pure chaetoglobosin A. Overall, differences in fluorescence, morphology, toxicity profile, mycotoxin production and sensitivity to chemicals were consistent with those in tef1α sequencing results for species identification. The results indicate the presence of Ch. cochliodes and Ch. rectangulare in Finnish buildings, representing a new finding.
3. Antifungal Activity of Chaetoviridin A from Chaetomium globosum CEF-082 Metabolites Against Verticillium dahliae in Cotton
Yun Zhang, Heqin Zhu, Yonghao Ye, Canming Tang Mol Plant Microbe Interact. 2021 Jul;34(7):758-769. doi: 10.1094/MPMI-02-21-0032-R. Epub 2021 Aug 15.
Cotton Verticillium wilt (CVW) is a severe soilborne disease caused by the pathogen Verticillium dahliae, and it has a great impact on cotton production. Previous studies found that the biocontrol agent Chaetomium globosum CEF-082 and its metabolic filtrate could reduce the incidence of CVW; however, the underlying mechanism remains unclear. The metabolic crude extract of CEF-082 increased the sensitivity of V. dahliae to stress, degraded the cell wall of V. dahliae, and increased the emergence and plant height of cotton. Through separation and purification of the metabolic crude extract of CEF-082, chaetoviridin A was identified and found to be highly active against V. dahliae. The compound caused cell necrosis and mycelial deformation, increased the production of reactive oxygen species and nitrous oxide, and inhibited the germination of microsclerotia of V. dahliae, enhancing the cotton plant defense response. In addition, CEF-082 also colonized cotton plants.[Formula: see text] Copyright © 2021 The Author(s). This is an open access article distributed under the CC BY-NC-ND 4.0 International license.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
