Cerulenin
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| Category | Antibiotics |
| Catalog number | BBF-00766 |
| CAS | 17397-89-6 |
| Molecular Weight | 223.27 |
| Molecular Formula | C12H17NO3 |
| Purity | 98% |
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Description
It is produced by the strain of Cephctlosporium caerulene, Helicoceras oryzae, Acrooylindrium oryzae. It has weak antibacterial activity, but it has the effect of resisting yeast, ringworm epidermis, pear spore and mycoplasma. It can inhibit the biosynthesis of fatty acids and sterols, and also inhibit the biosynthesis of Polyketide. In recent years, it has been found to inhibit HIV.
Specification
| Synonyms | Cerulenin; Helicocerin; 2,3-Epoxy-4-oxo-7,10-dodecadienamide; 3-(1-Oxo-4,7-nonadienyl)oxiranecarboxamide |
| Storage | Store in a cool and dry place and at 0 - 4 °C for short term (days to weeks) or -20 °C for long term (months to years). |
| IUPAC Name | (2R,3S)-3-[(4E,7E)-nona-4,7-dienoyl]oxirane-2-carboxamide |
| Canonical SMILES | CC=CCC=CCCC(=O)C1C(O1)C(=O)N |
| InChI | InChI=1S/C12H17NO3/c1-2-3-4-5-6-7-8-9(14)10-11(16-10)12(13)15/h2-3,5-6,10-11H,4,7-8H2,1H3,(H2,13,15)/b3-2+,6-5+/t10-,11-/m1/s1 |
| InChI Key | GVEZIHKRYBHEFX-NQQPLRFYSA-N |
| Source | Cephalosporium caerulens |
Properties
| Appearance | White Acicular Crystal |
| Application | Antifungal Agents |
| Antibiotic Activity Spectrum | mycoplasma; yeast; fungi |
| Boiling Point | 456.1ºC at 760 mmHg |
| Melting Point | 93-94 °C |
| Density | 1.134 g/cm3 |
| Solubility | Soluble in Methanol, Ethanol, Acetone, Chloroform and other organic solvents; Slightly soluble in Water; Insoluble in Petroleum Ether |
| LogP | 1.2 |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Irreversibly binds to fatty acid synthase, specifically b-ketoacyl-acyl carrier protein synthase (FabH, FabB and FabF condensation enzymes). A number of tumor cells and cell lines have been observed to have highly upregulated expression and activity of fatty acid synthase (FAS). Inhibition of FAS by cerulenin leads to cytotoxicity and apoptosis in human cancer cell lines, an effect believed to be mediated by the accumulation of malonyl-coenzyme A in cells with an upregulated FAS pathway. |
| Toxicity | LD50: 547 mg/kg (Oral, Mouse). |
Reference Reading
1.De novo genome assembly and annotation of rice sheath rot fungus Sarocladium oryzae reveals genes involved in Helvolic acid and Cerulenin biosynthesis pathways.
Hittalmani S1, Mahesh HB2, Mahadevaiah C2, Prasannakumar MK3. BMC Genomics. 2016 Mar 31;17(1):271. doi: 10.1186/s12864-016-2599-0.
BACKGROUND: Sheath rot disease caused by Sarocladium oryzae is an emerging threat for rice cultivation at global level. However, limited information with respect to genomic resources and pathogenesis is a major setback to develop disease management strategies. Considering this fact, we sequenced the whole genome of highly virulent Sarocladium oryzae field isolate, Saro-13 with 82x sequence depth.
2.Effect of cerulenin on fatty acid composition and gene expression pattern of DHA-producing strain Colwellia psychrerythraea strain 34H.
Wan X1,2, Peng YF3, Zhou XR4,5, Gong YM6, Huang FH7,8, Moncalián G9. Microb Cell Fact. 2016 Feb 6;15:30. doi: 10.1186/s12934-016-0431-9.
BACKGROUND: Colwellia psychrerythraea 34H is a psychrophilic bacterium able to produce docosahexaenoic acid (DHA). Polyketide synthase pathway is assumed to be responsible for DHA production in marine bacteria.
3.Dephosphorylation and mitochondrial translocation of cofilin sensitizes human leukemia cells to cerulenin-induced apoptosis via the ROCK1/Akt/JNK signaling pathway.
Zhang Y1, Fu R1, Liu Y1, Li J1, Zhang H1, Hu X1, Chen Y1, Liu X1, Li Y1, Li P2, Liu E2, Gao N1. Oncotarget. 2016 Mar 8. doi: 10.18632/oncotarget.7994. [Epub ahead of print]
In this study, we determined that cerulenin, a natural product inhibitor of fatty acid synthase, induces mitochondrial injury and apoptosis in human leukemia cells through the mitochondrial translocation of cofilin. Only dephosphorylated cofilin could translocate to mitochondria during cerulenin-induced apoptosis. Disruption of the ROCK1/Akt/JNK signaling pathway plays a critical role in the cerulenin-mediated dephosphorylation and mitochondrial translocation of cofilin and apoptosis. In vivo studies demonstrated that cerulenin-mediated inhibition of tumor growth in a mouse xenograft model of leukemia was associated with mitochondrial translocation of cofilin and apoptosis. These data are consistent with a hierarchical model in which induction of apoptosis by cerulenin primarily results from activation of ROCK1, inactivation of Akt, and activation of JNK. This leads to the dephosphorylation and mitochondrial translocation of cofilin and culminates with cytochrome c release, caspase activation, and apoptosis.
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
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 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 ╳
