ascochlorin
ascochlorin Basic information
- Product Name:
- ascochlorin
- Synonyms:
-
- 3-Chloro-4,6-dihydroxy-2-methyl-5-[(2E,4E)-3-methyl-5-[(1R)-1β,2β,6β-trimethyl-3-oxocyclohexyl]-2,4-pentadienyl]benzaldehyde
- Ilicicolin D
- 3-Chloro-4,6-dihydroxy-2-methyl-5-(3-methyl-5-(1,2,6-trimethyl-3-oxocyclohexyl)-2,4-pentadienyl)benzaldehyde (1R-(1alpha(2E,4E),2beta,6beta))-
- Antibiotic ll-Z1272 gamma
- ascochlorin
- Benzaldehyde, 3-chloro-4,6-dihydroxy-2-methyl-5-(3-methyl-5-(1,2,6-trimethyl-3-oxocyclohexyl)-2,4-pentadienyl)-, (1R-(1alpha(2E,4E),2beta,6beta))-
- beta-Resorcylaldehyde, 5-chloro-6-methyl-3-(3-methyl-5-(1,2,6-trimethyl-3-oxocyclohexyl)-2,4-pentadienyl)-, (E,E)-
- Ll-Z 1272 gamma
- CAS:
- 26166-39-2
- MF:
- C23H29ClO4
- MW:
- 404.931
- Mol File:
- 26166-39-2.mol
ascochlorin Chemical Properties
- Melting point:
- 172-174 °C
- Boiling point:
- 556.9±39.0 °C(Predicted)
- Density
- 1.199±0.06 g/cm3(Predicted)
- storage temp.
- -20°C
- solubility
- DMSO: soluble
- pka
- 6.26±0.50(Predicted)
- form
- A powder
ascochlorin Usage And Synthesis
Uses
Ascochlorin is an antitumor fungal metabolite which specifically inhibits matrix metalloproteinase-9 (MMP-9) activity through suppression of activator protein-1 (AP-1)-dependent induction of MMP-9 gene expression. Via AP-1 suppression, ascochlorin selectively kills MX-1 cells, a human breast cancer cell line lacking estrogen receptors. Ascochlorin also shows activity against Newcastle disease and herpes simplex viruses.
Uses
Ascochlorin is an isoprenoid antibiotic and antiviral that has diverse effects on mammalian cells. It suppresses PMA-induced invasion in renal carcinoma cells (IC50 = ~10 μM) by inhibiting the expression of matrix metalloproteinase-9. At 2 μM, ascochlorin profoundly increases the expression of p53 by increasing protein stability in cancer cells, and, at 50 μm, it inhibits signaling through STAT3. Ascochlorin also binds and inhibits the mitochondrial cytochrome bc1 complex, blocking reduction of cytochrome b by ubiquinone.[Cayman Chemical]
Definition
ChEBI: Ascochlorin is a dihydroxybenzaldehyde that is 2,4-dihydroxybenzaldehyde which is substituted by a (1E,3E)-3-methyl-1-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]penta-1,3-dien-5-yl group at position 3, chlorine at position 5, and a methyl group at position 6. A meroterpenoid produced by several fungi including Ascochyta viciae. It exhibits anticancer, antifungal and antiprotozoal activities. It has a role as an antineoplastic agent, a fungal metabolite, an antifungal agent, an antiprotozoal drug and an angiogenesis inhibitor. It is a dihydroxybenzaldehyde, a member of monochlorobenzenes, an olefinic compound, a member of resorcinols, a meroterpenoid, a sesquiterpenoid and a member of cyclohexanones. It is a conjugate acid of an ascochlorin(1-).
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