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SML0104

Sigma-Aldrich

Ascochlorin

≥98% (HPLC), from Verticillium hemipterigenum

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C23H29ClO4
CAS Number:
26166-39-2
Molecular Weight:
404.93
UNSPSC Code:
12352200
NACRES:
NA.77

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

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

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Wenbin Shen et al.
European journal of pharmacology, 791, 205-212 (2016-10-30)
Human dihydroorotate dehydrogenase (hDHODH) is an inner mitochondrial membrane enzyme that involves in the fourth step of the biosynthesis of pyrimidine base. Inhibitors of hDHODH have been proven efficacy for the treatments of inflammation, rheumatoid arthritis, multiple sclerosis and cancer.
Edward A Berry et al.
Biochimica et biophysica acta, 1797(3), 360-370 (2009-12-23)
Ascochlorin is an isoprenoid antibiotic that is produced by the phytopathogenic fungus Ascochyta viciae. Similar to ascofuranone, which specifically inhibits trypanosome alternative oxidase by acting at the ubiquinol binding domain, ascochlorin is also structurally related to ubiquinol. When added to
Syng-Ook Lee et al.
Biochemical and biophysical research communications, 354(1), 165-171 (2007-01-12)
Matrix metalloproteinase-9 (MMP-9) plays an important role in the invasion and metastasis of cancer cells. In this study, we examined the inhibitory effect of silibinin, a flavonoid antioxidant from milk thistle (Silybum marianum L.) on PMA-induced MMP-9 expression in MCF-7

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