Myriocin
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| Category | Others |
| Catalog number | BBF-02568 |
| CAS | 35891-70-4 |
| Molecular Weight | 401.54 |
| Molecular Formula | C21H39NO6 |
| Purity | >97% by HPLC |
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Description
Myriocin is an unsaturated hydrocarbon and fatty acid derivative produced by Myriococcum albomyces NRRL 3858. It has antifungal activity.
Specification
| Synonyms | thermozymocidin |
| Storage | -20°C |
| IUPAC Name | (E,2S,3R,4R)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid |
| Canonical SMILES | CCCCCCC(=O)CCCCCCC=CCC(C(C(CO)(C(=O)O)N)O)O |
| InChI | InChI=1S/C21H39NO6/c1-2-3-4-10-13-17(24)14-11-8-6-5-7-9-12-15-18(25)19(26)21(22,16-23)20(27)28/h9,12,18-19,23,25-26H,2-8,10-11,13-16,22H2,1H3,(H,27,28)/b12-9+/t18-,19+,21+/m1/s1 |
| InChI Key | ZZIKIHCNFWXKDY-GNTQXERDSA-N |
| Source | Mycelia sterilia |
Properties
| Appearance | White Crystal |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 636.7°C at 760 mmHg |
| Melting Point | 183-184°C |
| Flash Point | 338.8±31.5 °C |
| Density | 1.123 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Limited water solubility. |
Reference Reading
1.Inhibition of ceramide de novo synthesis by myriocin produces the double effect of reducing pathological inflammation and exerting antifungal activity against A. fumigatus airways infection.
Caretti A1, Torelli R2, Perdoni F3, Falleni M4, Tosi D4, Zulueta A1, Casas J5, Sanguinetti M2, Ghidoni R1, Borghi E3, Signorelli P6. Biochim Biophys Acta. 2016 Jun;1860(6):1089-97. doi: 10.1016/j.bbagen.2016.02.014. Epub 2016 Feb 24.
BACKGROUND: Fungal infections develop in pulmonary chronic inflammatory diseases such as asthma, Chronic Obstructive Pulmonary Disease (COPD) and Cystic Fibrosis (CF). The available antifungal drugs may fail to eradicate fungal pathogens, that can invade the lungs and vessels and spread by systemic circulation taking advantage of defective lung immunity. An increased rate of sphingolipid de novo synthesis, leading to ceramide accumulation, was demonstrated in CF and COPD inflamed lungs. The inhibitor of sphingolipid synthesis myriocin reduces inflammation and ameliorates the response against bacterial airway infection in CF mice. Myriocin also inhibits sphingolipid synthesis in fungi and exerts a powerful fungistatic effect.
2.Myristic acid potentiates palmitic acid-induced lipotoxicity and steatohepatitis associated with lipodystrophy by sustaning de novo ceramide synthesis.
Martínez L1,2, Torres S1,2, Baulies A1,2, Alarcón-Vila C1,2, Elena M3, Fabriàs G4, Casas J4, Caballeria J2, Fernandez-Checa JC1,2,5, García-Ruiz C1,2,5. Oncotarget. 2015 Dec 8;6(39):41479-96. doi: 10.18632/oncotarget.6286.
Palmitic acid (PA) induces hepatocyte apoptosis and fuels de novo ceramide synthesis in the endoplasmic reticulum (ER). Myristic acid (MA), a free fatty acid highly abundant in copra/palmist oils, is a predictor of nonalcoholic steatohepatitis (NASH) and stimulates ceramide synthesis. Here we investigated the synergism between MA and PA in ceramide synthesis, ER stress, lipotoxicity and NASH. Unlike PA, MA is not lipotoxic but potentiated PA-mediated lipoapoptosis, ER stress, caspase-3 activation and cytochrome c release in primary mouse hepatocytes (PMH). Moreover, MA kinetically sustained PA-induced total ceramide content by stimulating dehydroceramide desaturase and switched the ceramide profile from decreased to increased ceramide 14:0/ceramide16:0, without changing medium and long-chain ceramide species. PMH were more sensitive to equimolar ceramide14:0/ceramide16:0 exposure, which mimics the outcome of PA plus MA treatment on ceramide homeostasis, than to either ceramide alone.
3.Sng1 associates with Nce102 to regulate the yeast Pkh-Ypk signalling module in response to sphingolipid status.
García-Marqués S1, Randez-Gil F1, Dupont S2, Garre E1, Prieto JA3. Biochim Biophys Acta. 2016 Mar 28;1863(6 Pt A):1319-1333. doi: 10.1016/j.bbamcr.2016.03.025. [Epub ahead of print]
All cells are delimited by biological membranes, which are consequently a primary target of stress-induced damage. Cold alters membrane functionality by decreasing lipid fluidity and the activity of membrane proteins. In Saccharomyces cerevisiae, evidence links sphingolipid homeostasis and membrane phospholipid asymmetry to the activity of the Ypk1/2 proteins, the yeast orthologous of the mammalian SGK1-3 kinases. Their regulation is mediated by different protein kinases, including the PDK1 orthologous Pkh1/2p, and requires the function of protein effectors, among them Nce102p, a component of the sphingolipid sensor machinery. Nevertheless, the mechanisms and the actors involved in Pkh/Ypk regulation remain poorly defined. Here, we demonstrate that Sng1, a transmembrane protein, is an effector of the Pkh/Ypk module and identify the phospholipid asymmetry as key for yeast cold adaptation. Overexpression of SNG1 impairs phospholipid flipping, reduces reactive oxygen species (ROS) and improves, in a Pkh-dependent manner, yeast growth in myriocin-treated cells, suggesting that excess Sng1p stimulates the Pkh/Ypk signalling.
4.Functions of Ceramide Synthase Paralogs YPR114w and YJR116w of Saccharomyces cerevisiae.
Mallela SK1, Almeida R2, Ejsing CS2, Conzelmann A1. PLoS One. 2016 Jan 11;11(1):e0145831. doi: 10.1371/journal.pone.0145831. eCollection 2016.
Ceramide is synthesized in yeast by two redundant acyl-CoA dependent synthases, Lag1 and Lac1. In lag1∆ lac1∆ cells, free fatty acids and sphingoid bases are elevated, and ceramides are produced through the redundant alkaline ceramidases Ypc1 and Ydc1, working backwards. Even with all four of these genes deleted, cells are surviving and continue to contain small amounts of complex sphingolipids. Here we show that these residual sphingolipids are not synthesized by YPR114w or YJR116w, proteins of unknown function showing a high degree of homology to Lag1 and Lac1. Indeed, the hextuple lag1∆ lac1∆ ypc1∆ ydc1∆ ypr114w∆ yjr116w∆ mutant still contains ceramides and complex sphingolipids. Yjr116w∆ exhibit an oxygen-dependent hypersensitivity to Cu2+ due to an increased mitochondrial production of reactive oxygen species (ROS) and a mitochondrially orchestrated programmed cell death in presence of copper, but also a general copper hypersensitivity that cannot be counteracted by the antioxidant N-acetyl-cysteine (NAC).
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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
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
