Chaetoglobosin A
(Synonyms: 球毛壳菌素 A) 目录号 : GC43234
A mycotoxic cytochalasin
Cas No.:50335-03-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Chaetoglobosin A, the active principle within the extract of Penicillium aquamarinium, is a member of the cytochalasan family. Chaetoglobosin A preferentially induces apoptosis. Chaetoglobosin A targets filamentous actin in CLL cells and thereby induces cell-cycle arrest and inhibits membrane ruffling and cell migration[1].
References:
[1]. Knudsen PB, et al. Chaetoglobosin A preferentially induces apoptosis in chronic lymphocytic leukemia cells by targeting the cytoskeleton. Leukemia. 2014 Jun;28(6):1289-98.
| Cas No. | 50335-03-0 | SDF | |
| 别名 | 球毛壳菌素 A | ||
| Canonical SMILES | C/C([C@@H](O)C(/C=C/C1=O)=O)=C/[C@@H](C)C/C=C/[C@]2([H])[C@]1(C(N[C@H]3CC4=CNC5=C4C=CC=C5)=O)[C@@]3([H])[C@H](C)[C@]6(C)[C@H]2O6 | ||
| 分子式 | C32H36N2O5 | 分子量 | 528.6 |
| 溶解度 | 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 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 1.8918 mL | 9.4589 mL | 18.9179 mL |
| 5 mM | 0.3784 mL | 1.8918 mL | 3.7836 mL |
| 10 mM | 0.1892 mL | 0.9459 mL | 1.8918 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。
Functional analysis of a Chaetoglobosin A biosynthetic regulator in Chaetomium globosum
Fungal Biol 2021 Mar;125(3):201-210.PMID:33622536DOI:10.1016/j.funbio.2020.10.010.
Cytochalasins are a group of fungal secondary metabolites with diverse structures and bioactivities, including Chaetoglobosin A production. Chaetoglobosin A is produced by Chaetomium globosum and has potential antifungal activity. Bioinformatics analysis of the Chaetoglobosin A gene cluster (che) showed it that consists of nine open reading frames, including those encoding polyketide synthases (PKSs), PKS extender units, post-PKS modifications, and proposed regulators. Here, the role of the CgcheR regulator was investigated using gene disruption experiments. The CgcheR disruptant (ΔCgcheR) completely abolished the production of Chaetoglobosin A, which was restored by the introduction of a copy of the wild-type CgcheR gene, suggesting that CgcheR is involved in Chaetoglobosin A biosynthesis. A transcriptional analysis of the CgcheR disruptant indicated that CgCheR activates the transcription of chaetoglobosin biosynthetic genes in a pathway-specific manner. Furthermore, constitutive overexpression of CgcheR significantly improved the production of Chaetoglobosin A from 52 to 260 mg/L. Surprisingly, CgcheR also played a critical role in sporulation; the CgcheR disruptant lost the ability to produce spores, suggesting that the regulator modulates cellular development. Our results not only shed light on the regulation of Chaetoglobosin A biosynthesis, but also indicate a relationship between secondary metabolism and fungal morphogenesis.
New insight into the production improvement and resource generation of Chaetoglobosin A in Chaetomium globosum
Microb Biotechnol 2022 Oct;15(10):2562-2577.PMID:35930651DOI:10.1111/1751-7915.14111.
Chaetoglobosin A is a complex macrocyclic alkaloid with potent antimycotic, antiparasitic and antitumor properties. However, the low output and high cost of Chaetoglobosin A biosynthesis have hampered the application and commercialization of Chaetoglobosin A in agriculture and biomedicine. Here, the CgMfs1 gene, which encodes the major facilitator superfamily secondary transporter, was identified based on bioinformatics analysis, and an intensive study of its effects on Chaetoglobosin A biosynthesis and secretion was performed using CgMfs1-silencing and CgMfs1-overexpression strategies. Inactivation of CgMfs1 caused a notable decrease in Chaetoglobosin A yield from 58.66 mg/L to 19.95 mg/L (MFS1-3) and 17.13 mg/L (MFS1-4). The use of an efficient expression plasmid in Chaetomium globosum W7 to generate the overexpression mutant OEX13 resulted in the highest Chaetoglobosin A increase to 298.77 mg/L. Interestingly, the transcription level of the polyketide synthase gene significantly fluctuated with the change in CgMfs1, confirming that the predicted efflux gene CgMfs1 could play a crucial role in Chaetoglobosin A transportation. Effective efflux of Chaetoglobosin A could possibly alleviate feedback inhibition, resulting in notable increase in the expression of the polyketide synthase gene. Furthermore, we utilized cornstalk as the fermentation substrate to produce Chaetoglobosin A, and scanning electron microscopy and Fourier transform-infrared spectroscopy revealed that the strain OEX13 could well degrade cornstalk, presenting significant increases in the Chaetoglobosin A yield, when compared with that produced by the wild-type strain (from 40.32 to 191.90 mg/L). Thus, this research provides a novel analogous engineering strategy for the construction of high-yielding strain and offers new insight into large-scale Chaetoglobosin A production.
New production process of the antifungal Chaetoglobosin A using cornstalks
Braz J Microbiol 2017 Jul-Sep;48(3):410-418.PMID:28223029DOI:10.1016/j.bjm.2016.11.008.
Chaetoglobosin A is an antibacterial compound produced by Chaetomium globosum, with potential application as a biopesticide and cancer treatment drug. The aim of this study was to evaluate the feasibility of utilizing cornstalks to produce Chaetoglobosin A by C. globosum W7 in solid-batch fermentation and to determine an optimal method for purification of the products. The output of Chaetoglobosin A from the cornstalks was 0.34mg/g, and its content in the crude extract was 4.80%. Purification conditions were optimized to increase the content of Chaetoglobosin A in the crude extract, including the extract solvent, temperature, and pH value. The optimum process conditions were found to be acetone as the extractant, under room temperature, and at a pH value of 13. Under these conditions, a production process of the antifungal Chaetoglobosin A was established, and the content reached 19.17%. Through further verification, cornstalks could replace crops for the production of Chaetoglobosin A using this new production process. Moreover, the purified products showed great inhibition against Rhizoctonia solani, with Chaetoglobosin A confirmed as the main effective constituent (IC50=3.88μg/mL). Collectively, these results demonstrate the feasibility of using cornstalks to synthesize Chaetoglobosin A and that the production process established in this study was effective.
Deletion of a Rare Fungal PKS CgPKS11 Promotes Chaetoglobosin A Biosynthesis, Yet Defers the Growth and Development of Chaetomium globosum
J Fungi (Basel) 2021 Sep 13;7(9):750.PMID:34575788DOI:10.3390/jof7090750.
We previously reported that Chaetoglobosin A (ChA) exhibits a great potential in the biocontrol of nematodes and pathogenic fungi. To improve the production of ChA, a CRISPR-Cas9 system was created and applied for eliminating potential competitive polyketide products. One of the polyketide synthase encoding genes, Cgpks11, which is putatively involved in the biosynthesis of chaetoglocin A, was disrupted. Cgpks11 deletion led to the overexpression of the CgcheA gene cluster, which is responsible for ChA biosynthesis, and a 1.6-fold increase of ChA. Transcription of pks-1, a melanin PKS, was simultaneously upregulated. Conversely, the transcription of genes for chaetoglocin A biosynthesis, e.g., CHGG_10646 and CHGG_10649, were significantly downregulated. The deletion also led to growth retardation and seriously impaired ascospore development. This study found a novel regulatory means on the biosynthesis of ChA by CgPKS11. CgPKS11 affects Chaetoglobosin A biosynthesis, growth, and development in Chaetomium globosum.
Chaetoglobosin A contributes to the antagonistic action of Chaetomium globosum strain 61239 toward the apple Valsa canker pathogen Cytospora mali
Phytopathology 2023 Apr 17.PMID:37069143DOI:10.1094/PHYTO-01-23-0036-R.
Apple Valsa canker (AVC) weakens apple trees and significantly reduces apple production in China and other East Asian countries. Thus far, very few AVC-targeting biocontrol resources have been described. Here, we present a thorough description of a fungal isolate (Chaetomium globosum, 61239) that has strong antagonistic action toward the AVC causal agent Cytospora mali. Potato dextrose broth (PDB) culture filtrate of strain 61239 completely suppresses the mycelial growth of C. mali on PDA, and strongly constrained the development of AVC lesions in in vitro infection assays. UPLC and HPLC-MS/MS investigations supported that strain 61239 produces Chaetoglobosin A, an antimicrobial metabolite that inhibits C. mali. Using genome sequencing, we discovered a gene cluster in strain 61239 that may be responsible for Chaetoglobosin A production. Two of the cluster's genes - cheA, a PKS-NRPS hybrid enzyme, and cheB, an enoyl reductase - were individually silenced, which significantly decreased Chaetoglobosin A accumulation as well as the strain's antagonistic activity against C. mali. Together, the findings of our investigation illustrate the potential use of Ch. globosum for the management of AVC disease and emphasize the significant contribution of Chaetoglobosin A to the antagonistic action of strain 61239.