SML0110

Ilicicolin F

≥98% (HPLC), from Verticillium hemipterigenum

• Synonym(s): 8′-Acetoxyascochlorin, Acetoxy-ascochlorin, Antibiotic LL-Z 1272 ζ, Benzaldehyde, 3-[(2E,4E)-5-[(1S,2S,3S,6R)-3-(acetyloxy)-1,2,6-trimethyl-5-oxocyclohexyl]-3-methyl-2,4-pentadien-1-yl]-5-chloro-2,4-dihydroxy-6-methyl
• Empirical Formula (Hill Notation): C₂₅H₃₁ClO₆
• CAS Number: 22738-98-3
• Molecular Weight: 462.96
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• biological source: Verticillium hemipterigenum
• assay: ≥98% (HPLC)
• form: solid
• solubility: DMSO: ≥10 mg/mL; H₂O: insoluble; chloroform: soluble; methanol: soluble
• storage temp.: −20°C

Description

Application

Ilicicolin F may be used in cell signaling and reactions mediated by acetycholinesterase and β-glucuronidase.

Biochem/physiol Actions

Ilicicolin F belongs to the ascochlorin family of molecules. Ascochlorin and its derivitaves have an inhibitory effect on the mitochondrial cytochrome bc1 complex. Ilicicolins have antiviral activity.

Ilicicolin F belongs to the ascochlorin family of molecules. Ascochlorin is an isoprenoid antibiotic produced by Verticillium hemipterigenum. Ascochlorin and its derivatives have an inhibitory effect on mitochondrial respiration by blocking the oxidation-reduction of cytochrome b through center N of the cytochrome bc1 complex. Ilicicolins have antiviral activity. They inhibit the growth of the tobacco mosaic virus, herpes simplex virus type-1(HSV-1) and newcastle disease virus.

Compounds of the ascochlorin family such as Ilicicolin F, C, D and H show a wide range of inhibitory effects on farnesyl protein transferase (FPTase) activity, and a significant inhibitory effect on the activity of testosterone-5α-reductase. Ilicicolin C and F have a moderate inhibitory activity toward the enzymes acetylcholinesterase (AChE) and β-glucuronidase and are active against Pseudomonas syringae with IC₅₀ values of 28.5 μg/mL.

All isolated ascochlorin analogs exhibit significant antitumor and cytotoxic activities. Ascochlorin and its homologues are usable in treating and/or preventing diseases that can be relieved by the retinoid X receptor ligand-dependent signal transcriptional regulation (i.e. hypertension, cerebrovascular diseases, rheumatoid arthritis, autoimmune diseases, complication of diabetes, arteriosclerosis etc.). Moreover, they can inhibit denaturation and/or necrosis of pancreatic Langerhans islet β-cells and therefore can sustain insulin productivity.

Safety Information

• Storage Class: 13 - Non Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable