19,20-Epoxycytochalasin C
(Synonyms: 19,20-环氧细胞松弛素C) 目录号 : GC41982
A fungal metabolite
Cas No.:189351-79-9
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
19,20-Epoxycytochalasin C is a fungal metabolite originally isolated from Nemania sp. UM10M. It inhibits the growth of chloroquine-sensitive and -resistant strains of P. falciparum (IC50s = 0.07 and 0.05 ng/ml, respectively) without inducing cytotoxicity in Vero cells (IC50 = >4,760 ng/ml). 19,20-Epoxycytochalasin C is also phytotoxic, reducing growth of lettuce and bentgrass plants when used at a concentration of 1 mg/ml.
| Cas No. | 189351-79-9 | SDF | |
| 别名 | 19,20-环氧细胞松弛素C | ||
| Canonical SMILES | O=C1[C@@](O)(C)[C@H](O2)[C@@H]2[C@@H](OC(C)=O)[C@@]34[C@@]([C@H](CC5=CC=CC=C5)NC4=O)([H])C(C)=C(C)[C@@H](O)[C@]3([H])/C=C/C[C@@H]1C | ||
| 分子式 | C30H37NO7 | 分子量 | 523.6 |
| 溶解度 | DMF: soluble,DMSO: soluble,Ethanol: 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 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 1.9099 mL | 9.5493 mL | 19.0985 mL |
| 5 mM | 0.382 mL | 1.9099 mL | 3.8197 mL |
| 10 mM | 0.191 mL | 0.9549 mL | 1.9099 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。
Tandem MS-Based Metabolite Profiling of 19,20-Epoxycytochalasin C Reveals the Importance of a Hydroxy Group at the C7 Position for Biological Activity
ACS Omega 2021 Jan 25;6(5):3717-3726.PMID:33585752DOI:10.1021/acsomega.0c05307.
Seven cytochalasins, 19,20-epoxycytochalasin N, cytochalasin P1, deacetyl 19,20-Epoxycytochalasin C, 19,20-epoxycytochalasin D, 19,20-Epoxycytochalasin C, cytochalasin D, and cytochalasin C, were isolated from a fungal (Rosellinia sanctae-cruciana) crude extract. A cytotoxicity assay (sulforhodamine B) was performed on a series of cancer cell lines: HT-29, A-549, PC-3, HCT-116, SW-620, and MCF-7. Simultaneously, the liquid chromatography-mass spectrometry (LC-MS)/MS profile of 19,20-epoxycytochalasin C-treated cell lines revealed that 19,20-Epoxycytochalasin C (m/z 524.25) oxidized to a metabolite of m/z 522.25 Da (-2 Da (-2H) from 19,20-Epoxycytochalasin C). Further chemical oxidation of 19,20-Epoxycytochalasin C using the Dess-Martin reagent produced an identical metabolite. It has been noticed that the parent molecule (19,20-Epoxycytochalasin C) showed an IC50 of 650 nM (on HT-29), whereas for the oxidized metabolite (m/z 522.24) of 19,20-Epoxycytochalasin C, the IC50 was >10 μM. It is clear that the parent molecule had 16 times higher cytotoxic potential as compared to the oxidized metabolite. The spectroscopic investigation indicated that the oxidation of the hydroxyl (-OH) group occurred at the C7 position in 19,20-epoxycyctochalsin C and led to the inactivation of 19,20-Epoxycytochalasin C. Further, cell cycle analysis and histopathological evidence support the findings, and CDK2 could be a possible target of 19,20-epoxycyctochalasin C.
Six 19,20-epoxycytochalasans from endophytic Diaporthe sp. RJ-47
Nat Prod Res 2022 Jul;36(13):3375-3380.PMID:33325741DOI:10.1080/14786419.2020.1859504.
Two new cytochalasins, deacetyl-19-epi-cytochalasin P1 (1), deacetyl-19,20-epoxycytochalasin D (2) were isolated from the endophytic fungus Diaporthe sp. RJ-47, along with four known compounds deacetyl-5,6-dihydro-7-oxo-19,20-epoxycytochalasin C (3), 19,20-epoxycytochalasin Q (4), 19,20-Epoxycytochalasin C (5) and deacetyl-19,20-epoxy cytochalasin C (6). Their structures were unambiguously elucidated on the basis of the comprehensive analysis of extensive spectroscopic data. The antimicrobial effects of these compounds were evaluated.
Cytotoxic 19,20-epoxycytochalasans from endophytic fungus Xylaria cf. curta
Fitoterapia 2019 Sep;137:104253.PMID:31271786DOI:10.1016/j.fitote.2019.104253.
Nine new 19,20-epoxycytochalasans (1-9) were isolated from the rice fermentation extracts of endophytic fungus Xylaria cf. curta, along with four known compounds 19,20-Epoxycytochalasin C (10), 18-desoxy-19,20-epoxycytochalasin C (11), 19,20-epoxycytochalasin D (12) and 5,6-dihydro-7-oxo-19,20-epoxycytochalasin C (13). Their structures and absolute configurations were determined by 1D and 2D NMR, HRESIMS, X-ray diffraction and ECD calculation. The cytotoxicity of obtained compounds (1-13) was evaluated against human cancer cell lines HL-60, A549, SMMC-7721, MCF-7, and SW480. Remarkably, compound 10 showed significant specific cytotoxicity against HL-60 cell lines with IC50 value of 1.11 μM.
Antiplasmodial and Cytotoxic Cytochalasins from an Endophytic Fungus, Nemania sp. UM10M, Isolated from a Diseased Torreya taxifolia Leaf
Molecules 2019 Feb 21;24(4):777.PMID:30795572DOI:10.3390/molecules24040777.
Bioassay-guided fractionation of an EtOAc extract of the broth of the endophytic fungus Nemania sp. UM10M (Xylariaceae) isolated from a diseased Torreya taxifolia leaf afforded three known cytochalasins, 19,20-epoxycytochalasins C (1) and D (2), and 18-deoxy-19,20-epoxy-cytochalasin C (3). All three compounds showed potent in vitro antiplasmodial activity and phytotoxicity with no cytotoxicity to Vero cells. These compounds exhibited moderate to weak cytotoxicity to some of the cell lines of a panel of solid tumor (SK-MEL, KB, BT-549, and SK-OV-3) and kidney epithelial cells (LLC-PK11). Evaluation of in vivo antimalarial activity of 19,20-Epoxycytochalasin C (1) in a mouse model at 100 mg/kg dose showed that this compound had weak suppressive antiplasmodial activity and was toxic to animals.
[Secondary metabolites of mangrove endophytic fungus BL321 in the South China Sea]
Zhong Yao Cai 2010 Jun;33(6):901-3.PMID:21049610doi
Objective: To study the secondary metabolites of mangrove endophytic fungus BL321. Methods: The compounds were isolated by chromatographic technique. The structures were identified by comprehensive physico-chemical properties and spectral methods. Results: Five compounds were isolated and identified as 3,4a-dimethyl-2-oxo-2,4,4a,5,6,7-hexahydronaphtho[2,3-b]furan-5-carboxylic acid(1), cytochalasin C(2), cytochalasin D(3), 19,20-Epoxycytochalasin C(4), ergosterol(5). Conclusion: Compound 1 is isolated from nature for the first time. Further more, several kinds of strong bioactive compounds were islolate from this fungus indicate that it may develop to be medical source microorganism.