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SML0104 Sigma-Aldrich

Ascochlorin

≥98% (HPLC), from Verticillium hemipterigenum

Synonym: 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

  • CAS Number 26166-39-2

  • Empirical Formula (Hill Notation) C23H29ClO4

  • Molecular Weight 404.93

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Properties

Related Categories AN-AZ, Antibiotics, Antibiotics A to Z, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules,
biological source   Verticillium hemipterigenum
assay   ≥98% (HPLC)
solubility   DMSO: soluble
  H2O: insoluble
  chloroform: soluble
  ethyl acetate: soluble
  methanol: soluble
Mode of action   enzyme | inhibits
antibiotic activity spectrum   viruses
storage temp.   −20°C

Description

Application

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

Biochem/physiol Actions

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.

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
3

Milli-Q® Water Purification Solutions
Protocols & Articles
Peer-Reviewed Papers
15

References

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