19,20-Epoxycytochalasin C
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04587 |
| CAS | 189351-79-9 |
| Molecular Weight | 523.62 |
| Molecular Formula | C30H37NO7 |
| Purity | >99% by HPLC |
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Description
It is a fungal metabolite originally isolated from Nemania sp. UM10M. It is a major component of the cytochalasin complex. It inhibits tumour cell growth in vitro and inhibits the growth of chloroquine-sensitive and -resistant strains of P. falciparum.
Specification
| Synonyms | (3S,3aR,4E,7S,9R,9aR,10aS,11S,11aR,14S,14aR)-11-(acetyloxy)-6,7,9,9a,10a,11,14,14a-octahydro-3,9-dihydroxy-1,2,7,9-tetramethyl-14-(phenylmethyl)-3H-oxireno[9,10]cycloundec[1,2-d]isoindole-8,12(3aH,13H)-dione |
| Storage | Store at -20°C |
| IUPAC Name | [(1R,2S,6R,8S,10E,12R,13S,16R,17S)-17-benzyl-6,13-dihydroxy-6,8,14,15-tetramethyl-7,19-dioxo-4-oxa-18-azatetracyclo[10.7.0.01,16.03,5]nonadeca-10,14-dien-2-yl] acetate |
| Canonical SMILES | CC1CC=CC2C(C(=C(C3C2(C(C4C(O4)C(C1=O)(C)O)OC(=O)C)C(=O)NC3CC5=CC=CC=C5)C)C)O |
| InChI | InChI=1S/C30H37NO7/c1-15-10-9-13-20-23(33)17(3)16(2)22-21(14-19-11-7-6-8-12-19)31-28(35)30(20,22)27(37-18(4)32)24-26(38-24)29(5,36)25(15)34/h6-9,11-13,15,20-24,26-27,33,36H,10,14H2,1-5H3,(H,31,35)/b13-9+/t15-,20-,21-,22-,23+,24?,26?,27+,29-,30-/m0/s1 |
| InChI Key | ZOSGFLUFAVFHCM-WSRKEQNVSA-N |
| Source | Geniculosporium sp. |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | Neoplastics (Tumor); Parasites |
| Boiling Point | 737.4±60.0°C at 760 mmHg |
| Density | 1.3±0.1 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water |
Reference Reading
1. [Secondary metabolites of mangrove endophytic fungus BL321 in the South China Sea]
Yong-Cheng Lin, Yong-Xiang Song, Jun Wang, Zhi-Gang She, Huan-Ge Ma, Lan Liu Zhong Yao Cai . 2010 Jun;33(6):901-3.
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.
2. Tandem MS-Based Metabolite Profiling of 19,20-Epoxycytochalasin C Reveals the Importance of a Hydroxy Group at the C7 Position for Biological Activity
Shubham Srivastava, Nisha Sharma, Arem Qayum, Shashank K Singh, Vidushi Abrol, Sundeep Jaglan, Shreyans K Jain, Ram A Vishwakarma, Jasvinder Singh, Manoj Kushwaha, Ruchi Malik, Amit Kumar Srivastava ACS Omega . 2021 Jan 25;6(5):3717-3726. doi: 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/z524.25) oxidized to a metabolite ofm/z522.25 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 IC50of 650 nM (on HT-29), whereas for the oxidized metabolite (m/z522.24) of 19,20-epoxycytochalasin C, the IC50was >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.
3. Antiplasmodial and Cytotoxic Cytochalasins from an Endophytic Fungus, Nemania sp. UM10M, Isolated from a Diseased Torreya taxifolia Leaf
Natascha Techen, Stephen O Duke, N P Dhammika Nanayakkara, Edward M Croom Jr, Babu L Tekwani, Daneel Ferreira, Rajnish Sahu, Mallika Kumarihamy, Shabana Khan Molecules . 2019 Feb 21;24(4):777. doi: 10.3390/molecules24040777.
Bioassay-guided fractionation of an EtOAc extract of the broth of the endophytic fungusNemaniasp. UM10M (Xylariaceae) isolated from a diseasedTorreya taxifolialeaf 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.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
