19,20-Epoxycytochalasin D
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04588 |
| CAS | 191349-10-7 |
| 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. It is active against the chloroquine-sensitive and -resistant strains of P. falciparum.
Specification
| Synonyms | (1S,3S,3aR,4E,7S,9R,9aR,10aS,11S,11aR,14S,14aR)-11-(Acetyloxy)-3,3a,6,7,9,9a,10a,11,14,14a-decahydro-3,9-dihydroxy-1,7,9-trimethyl-2-methylene-14-(phenylmethyl)-1H-oxireno[9,10]cycloundec[1,2-d]isoindole-8,12(2H,13H)-dione; [1aS-(1aR*,2R*,2aS*,5R*,5aS*,6R*,8R*,8aS*,9E,12R*,14S*,14aS*)]-2-(Acetyloxy)-5,5a,6,7,8,8a,11,12,14,14a-decahydro-8,14-dihydroxy-6,12,14-trimethyl-7-methylene-5-(phenylmethyl)-2H-oxireno[9,10]cycloundec[1,2-d]isoindole-3,13(1aH,4H)-dione |
| Storage | Store at -20°C |
| IUPAC Name | [(1R,2S,6R,8S,10E,12R,13S,15S,16R,17S)-17-benzyl-6,13-dihydroxy-6,8,15-trimethyl-14-methylidene-7,19-dioxo-4-oxa-18-azatetracyclo[10.7.0.01,16.03,5]nonadec-10-en-2-yl] acetate |
| Canonical SMILES | CC1CC=CC2C(C(=C)C(C3C2(C(C4C(O4)C(C1=O)(C)O)OC(=O)C)C(=O)NC3CC5=CC=CC=C5)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/h6-9,11-13,15-16,20-24,26-27,33,36H,3,10,14H2,1-2,4-5H3,(H,31,35)/b13-9+/t15-,16+,20-,21-,22-,23+,24?,26?,27+,29-,30-/m0/s1 |
| InChI Key | WHJRAYUHVRYTTH-SJPOVNCESA-N |
| Source | Geniculosporium sp. |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | Neoplastics (Tumor); Parasites |
| Boiling Point | 735.1±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. 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.
2. Kolokosides A-D: triterpenoid glycosides from a Hawaiian isolate of Xylaria sp
James B Gloer, Kerry O'Donnell, Donald T Wicklow, Stephen T Deyrup J Nat Prod . 2007 Mar;70(3):378-82. doi: 10.1021/np060546k.
Four new triterpenoid glycosides, kolokosides A-D (1-4), along with the known compound 19,20-epoxycytochalasin N, were isolated from cultures of a Hawaiian wood-decay fungus (Xylaria sp.). The structures and relative configurations of 1-4 were determined primarily by analysis of NMR data, and the absolute configuration of 1 was assigned by application of the exciton chirality method. Compound 1 exhibited activity against Gram-positive bacteria.
3. [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.
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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 ╳
