Chaetoviridin A
目录号 : GC47075
A fungal metabolite
Cas No.:128252-98-2
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Chaetoviridin A is a fungal metabolite that has been found in Chaetomium.1 Plant pathogenic, antitumor, and cholesteryl ester transfer protein (CETP) inhibitory activity attributed to chaetoviridin A was determined prior to its structural reassignment by total synthesis, NMR, and circular dichroism analysis.1,2,3,4
1.Makrerougras, M., Coffinier, R., Oger, S., et al.Total synthesis and structural revision of chaetoviridins AOrg. Lett.19(15)4146-4149(2017) 2.Park, J.-H., Choi, G.J., Jang, K.S., et al.Antifungal activity against plant pathogenic fungi of chaetoviridins isolated from Chaetomium globosumFEMS Microbiol. Lett.252(2)309-313(2005) 3.Yasukawa, K., Takahashi, M., Natori, S., et al.Azaphilones inhibit tumor promotion by 12-O-tetradecanoylphorbol-13-acetate in two-stage carcinogenesis in miceOncology51(1)108-112(1994) 4.Tomoda, H., Matsushima, C., Tabata, N., et al.Structure-specific inhibition of cholesteryl ester transfer protein by azaphilonesJ. Antibiot. (Tokyo)52(2)160-170(1999)
| Cas No. | 128252-98-2 | SDF | |
| Canonical SMILES | O=C1O[C@]2(C)C(C(Cl)=C3C=C(/C=C/[C@@H](C)CC)OC=C3C2=C1C([C@H](C)[C@H](O)C)=O)=O | ||
| 分子式 | C23H25ClO6 | 分子量 | 432.9 |
| 溶解度 | Acetone: soluble,Chloroform: soluble,DMSO: soluble,Methanol: soluble | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 2.31 mL | 11.55 mL | 23.1 mL |
| 5 mM | 0.462 mL | 2.31 mL | 4.62 mL |
| 10 mM | 0.231 mL | 1.155 mL | 2.31 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Antifungal Activity of Chaetoviridin A from Chaetomium globosum CEF-082 Metabolites Against Verticillium dahliae in Cotton
Mol Plant Microbe Interact 2021 Jul;34(7):758-769.PMID:33646818DOI:10.1094/MPMI-02-21-0032-R.
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.
Azaphilones from the Endophyte Diaporthe sp. and Their Toxicity
Chem Biodivers 2022 Nov;19(11):e202200849.PMID:36193753DOI:10.1002/cbdv.202200849.
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.
Cytotoxic Nitrogenated Azaphilones from the Deep-Sea-Derived Fungus Chaetomium globosum MP4-S01-7
J Nat Prod 2020 Apr 24;83(4):1157-1166.PMID:32193933DOI:10.1021/acs.jnatprod.9b01165.
Eight new nitrogenated azaphilones (1-8) and two known compounds (Chaetoviridin A and chaetoviridin E, 9, 10) were isolated from the culture of the deep-sea-derived fungus Chaetomium globosum MP4-S01-7. The absolute configurations of new compounds were elucidated by HSQC-HECADE NMR data, J-based configuration analysis, and modified Mosher's method and finally verified by comparison of recorded and computed NMR chemical shifts from quantum chemical calculations coupled with a statistical procedure (DP4+). All of the compounds were evaluated for their in vitro cytotoxicities against the gastric cancer cell lines MGC803 and AGS, and most of them showed significant inhibition on cancer cell viability at 10 μM. Among them, compounds 1, 2, and 5 exerted the most potent cytotoxic activities, with IC50 values less than 1 μM. Further studies showed that compound 2 inhibited cell cycle progression, and both compounds 1 and 2 induced apoptosis of gastric cancer cells in a concentration-dependent manner.
Identification and characterization of the chaetoviridin and chaetomugilin gene cluster in Chaetomium globosum reveal dual functions of an iterative highly-reducing polyketide synthase
J Am Chem Soc 2012 Oct 31;134(43):17900-3.PMID:23072467DOI:10.1021/ja3090498.
We report the identification and characterization of the caz biosynthetic cluster from Chaetomium globosum and the characterization of a highly reducing polyketide synthase (PKS) that acts in both a sequential and convergent manner with a nonreducing PKS to form the chaetomugilin and chaetoviridin azaphilones. Genetic inactivation studies verified the involvement of individual caz genes in the biosynthesis of the azaphilones. Through in vitro reconstitution, we demonstrated the in vitro synthesis of Chaetoviridin A from the pyranoquinone intermediate cazisochromene using the highly reducing PKS and an acyltransferase.
Azaphilones inhibit tumor promotion by 12-O-tetradecanoylphorbol-13-acetate in two-stage carcinogenesis in mice
Oncology 1994 Jan-Feb;51(1):108-12.PMID:8265094DOI:10.1159/000227320.
Monascorubrin (an azaphilone derivative) was isolated from Monascus anka, 'Monascus pigment', a natural pigment of food additivies, was extracted from Monasucs spp., and Chaetoviridin A, one of the azaphilones, was isolated from Chaetomium globosum var. flavo-viridae. Application of 1 microgram of 12-O-tetradecanoylphorbol-13-acetate (TPA), a tumor promoting agent, to the mouse ear resulted in induction of inflammation. Among monascorubrin and related compounds assayed, monascorubrin, Chaetoviridin A and its related compounds inhibited the inflammatory activity of TPA in mice. The 50% inhibitory dose of these compounds for TPA-induced inflammation was 0.4-1.5 mumol. Furthermore, monascorubrin (2 mumol), Chaetoviridin A (2 mumol) and Monascus pigment (1 mg) markedly suppressed the promoting effect of TPA (1 microgram) on skin tumor formation in mice initiated with 7,12-dimethylbenz[a]anthracene (50 micrograms). It is assumed that the inhibition of tumor promotion by monascorubrin, Chaetoviridin A and Monascus pigment is due to anti-inflammatory activity.