SML0104

Ascochlorin

≥98% (HPLC), from Verticillium hemipterigenum

• Synonym(e): 5-Chloro-2,4-dihydroxy-6-methyl-3-[(2E,4Z)-3-methyl-5-(1,2,6-trimethyl-3-oxocyclohexyl)penta-2,4-dienyl]benzaldehyde, Antibiotics LL-Z 1272g, Ilicicolin D, NSC 287492
• Empirische Formel (Hill-System): C₂₃H₂₉ClO₄
• CAS-Nummer: 26166-39-2
• Molekulargewicht: 404.93
• UNSPSC Code: 12352200
• NACRES: NA.77
• Assay: ≥98% (HPLC)

Eigenschaften

• biological source: Verticillium hemipterigenum
• assay: ≥98% (HPLC)
• solubility: DMSO: soluble, H₂O: insoluble, chloroform: soluble, ethyl acetate: soluble, methanol: soluble
• antibiotic activity spectrum: viruses
• mode of action: enzyme | inhibits
• storage temp.: −20°C
• InChI: 1S/C23H29ClO4/c1-13(10-11-23(5)14(2)7-9-19(26)16(23)4)6-8-17-21(27)18(12-25)15(3)20(24)22(17)28/h6,10-12,14,16,27-28H,7-9H2,1-5H3/b11-10+,13-6+
• InChI key: SETVRSKZJJWOPA-OGCXVWDESA-N

Beschreibung

Application

The effect of Ascochlorin on MMP-9 was compared with that of Silibinin in MCF-7 human breast carcinoma cells.[1]

Biochem/physiol Actions

Ascochlorin is a prenyl-phenol compound and a dihydroorotate dehydrogenase (DHODH) inhibitor. It has hypolipidemic functionality and suppresses hypertension as well as immune responses.[2] It is a glycoside, which also elicits inhibition of the respiratory chain cytochrome bc1.[3]

Ascochlorin is an isoprenoid antibiotic initially identified as an antiviral and antitumor agent.

Ascochlorin is an isoprenoid antibiotic produced by Verticillium hemipterigenum, initially identified as an antiviral and antitumor agent. Research also indicates that ascochlorin inhibits the Qi and Qo quinone binding sites of the mitochondria cytochrom bc1 complex. Moreover, ascochlorin activates p53, probably as a result of its inhibitory effect on mitochondrial respiration. In addition, ascochlorin has the ability to suppress the nuclear subscription enzyme protein-1, a nuclear transcription factor activator, which leads to suppression of the extra-cellular enzyme, matrix metalloproteinase-9 (MMP9). The regulation of MMP is implicated in renal development, macrophage differentiation, atherosclerosis, inflammation, rheumatoid arthritis, and tumor invasion. Ascochlorin was also found to be effective against Mx-1, an estrogen lacking breast cancer cell line.

Sicherheitshinweise

• Lagerklasse: 13 - Non Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable