Cytochalasin H
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| Category | Mycotoxins |
| Catalog number | BBF-01760 |
| CAS | 53760-19-3 |
| Molecular Weight | 493.63 |
| Molecular Formula | C30H39NO5 |
| Purity | >95% by HPLC |
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Description
It is produced by the strain of Pestalotia sp. AB 1942R-114. It has many biological activities, such as inhibiting cytokinesis reversibly, inhibiting megasophil endocytosis and exocytosis. Cytosine H has immunosuppressive effects.
Specification
| Synonyms | (7S,13E,16S,18R,19E,21R)-21-(Acetyloxy)-7,18-dihydroxy-16,18-dimethyl-10-phenyl-[11]Cytochalasa-6(12),13,19-trien-1-one; (3S,3aR,4S,6S,6aR,7E,10S,12R,13E,15R,15aR)-15-(Acetyloxy)-2,3,3a,4,5,6,6a,9,10,11,12,15-dodecahydro-6,12-dihydroxy-4,10,12-trimethyl-5-methylene-3-(phenylmethyl)-1H-cycloundec[d]isoindol-1-one; Cytochalasin H; Kodocytochalasin 1; Paspalin P I; [3S-(3R*,3aS*,4R*,6R*,6aS*,7E,10R*,12S*,13E,15S*,15aS*)]-15-(Acetyloxy)-2,3,3a,4,5,6,6a,9,10,11,12,15-dodecahydro-6,12-dihydroxy-4,10,12-trimethyl-5-methylene-3-(phenylmethyl)-1H-cycloundec[d]isoindol-1-one; Paspalin; SC 305222; NSC305222; NSC-305222; (11)Cytochalasa-6(12),13,19-trien-1-one; phenyl-(11)cytochalasa-6(12),13,19-triene-1-one |
| Shelf Life | 2 years |
| Storage | -20 °C under inert atmosphere |
| IUPAC Name | [(1R,2R,3E,5R,7S,9E,11R,12S,14S,15R,16S)-16-benzyl-5,12-dihydroxy-5,7,14-trimethyl-13-methylidene-18-oxo-17-azatricyclo[9.7.0.01,15]octadeca-3,9-dien-2-yl] acetate |
| Canonical SMILES | CC1CC=CC2C(C(=C)C(C3C2(C(C=CC(C1)(C)O)OC(=O)C)C(=O)NC3CC4=CC=CC=C4)C)O |
| InChI | 1S/C30H39NO5/c1-18-10-9-13-23-27(33)20(3)19(2)26-24(16-22-11-7-6-8-12-22)31-28(34)30(23,26)25(36-21(4)32)14-15-29(5,35)17-18/h6-9,11-15,18-19,23-27,33,35H,3,10,16-17H2,1-2,4-5H3,(H,31,34)/b13-9+,15-14+/t18-,19+,23-,24-,25+,26-,27+,29-,30+/m0/s1 |
| InChI Key | NAEWXXDGBKTIMN-OWTACEMYSA-N |
| Source | Cytochalasin H is has been isolated from the fungus Phomopsis paspali. |
Properties
| Appearance | White to Off-White Solid |
| Boiling Point | 676.5 °C at 760 mmHg |
| Melting Point | 258-263 °C |
| Density | 1.19 g/cm3 |
| Solubility | Soluble in Ethanol, Chloroform; Slightly soluble in DMSO, Methanol |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Cytochalasins are known to bind to the barbed, fast growing plus ends of microfilaments, which then blocks both the assembly and disassembly of individual actin monomers from the bound end. Once bound, cytochalasin essentially caps the end of the new actin filament. One cytochalasin will bind to one actin filament. By blocking the polymerization and elongation of actin, cytochalasins can change cellular morphology, inhibit cellular processes such as cell division, and cause cells to undergo apoptosis. |
Reference Reading
1.Toxicity and plant growth regulator effects of cytochalasin H isolated from Phomopsis sp.
Wells JM, Cutler HG, Cole RJ. Can J Microbiol. 1976 Aug;22(8):1137-43.
A biologically active metabolite was found in crude extracts of an unidentified species of Phomopsis isolated from weevil-damaged pecans. Purified metabolite was toxic to day-old cockerels, with an LD50 of 12.5 mg/kg, and was markedly inhibitory to growth the floral development of tobacco plants at concentrations of 10(-2) to 10(-4) M. IR and 1H-nmr spectra indicated an alkylpheny moiety with a single nitrogen atom present as a secondary amide; and acetate ester, OH, CH3, and a trans-double bond function. Elemental and high-resolution mass-spectral analysis indicated a formula of C30H39NO5 and a molecular weight of 493.2886. The metabolite was identified as cytochalasin H.
2.A new cytochalasin from endophytic Phomopsis sp. IFB-E060.
Shen L1, Luo Q2, Shen ZP1, Li LY1, Zhang XJ1, Wei ZQ1, Fu Y1, Song YC3, Tan RX4. Chin J Nat Med. 2014 Jul;12(7):512-6. doi: 10.1016/S1875-5364(14)60080-7.
AIM: To study the chemical constituents of the solid culture of the endophyte Phomopsis sp. IFB-E060 in Vatica mangachapoi.
3.A novel phytotoxic nonenolide from Phomopsis sp. HCCB03520.
Yang Z1, Ge M, Yin Y, Chen Y, Luo M, Chen D. Chem Biodivers. 2012 Feb;9(2):403-8. doi: 10.1002/cbdv.201100080.
A novel phytotoxic nonenolide, (6S,7R,9R)-6,7-dihydroxy-9-propylnon-4-eno-9-lactone (1), was isolated from solid cultures of the endophytic fungus Phomopsis sp. HCCB03520, together with three known compounds, cytochalasin H (2), cytochalasin N (3), and epoxycytochalasin H (4). The structures of these compounds were elucidated through spectroscopic analysis, and the absolute configurations were determined by CD spectroscopy. Phytotoxic activities of compounds 1-4 were also investigated. Compound 1 showed phytotoxic activity on germination and radicle growth of Medicago sativa, Trifolium hybridum, and Buchloe dactyloides.
4.Bioactive secondary metabolites from Phomopsis sp., an endophytic fungus from Senna spectabilis.
Chapla VM1, Zeraik ML2, Ximenes VF3, Zanardi LM4, Lopes MN5, Cavalheiro AJ6, Silva DH7, Young MC8, Fonseca LM9, Bolzani VS10, Araújo AR11. Molecules. 2014 May 22;19(5):6597-608. doi: 10.3390/molecules19056597.
Chemical investigation of an acetonitrile fraction from the endophytic fungus Phomopsis sp. led to the isolation of the new natural product 2-hydroxy-alternariol (7) together with the known compounds cytochalasins J (1) and H (2), 5'-epialtenuene (3) and the mycotoxins alternariol monomethyl ether (AME, 4), alternariol (AOH, 5) and cytosporone C (6). The structure of the new compound was elucidated by using 1-D and 2-D NMR (nuclear magnetic resonance) and high resolution mass spectrometry. The cytochalasins J (1) and H (2) and AOH (5) exhibited potent inhibition of the total ROS (reactive oxygen species) produced by stimulated human neutrophils and acted as potent potential anti-inflammatory agents. Moreover, cytochalasin H (2) demonstrated antifungal and acetylcholinesterase enzyme (AChE) inhibition in vitro.
Spectrum
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C30H39NO5
Molecular Weight (Monoisotopic Mass): 493.2828 Da
Molecular Weight (Avergae Mass): 493.6344 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C30H39NO5
Molecular Weight (Monoisotopic Mass): 493.2828 Da
Molecular Weight (Avergae Mass): 493.6344 Da
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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 ╳
