19,20-Epoxycytochalasin D
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Enzyme inhibitors |
| Catalog number | BBF-04588 |
| CAS | 191349-10-7 |
| Molecular Weight | 523.62 |
| Molecular Formula | C30H37NO7 |
| Purity | >99% by HPLC |
Online Inquiry
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.
Recommended Products
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
| BBF-02614 | Nystatin | Inquiry |
| BBF-01826 | Deoxymannojirimycin | Inquiry |
| BBF-01825 | Loganin | Inquiry |
| BBF-03753 | Baicalin | Inquiry |
| BBF-03755 | Actinomycin D | Inquiry |
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 ╳
