Ascochlorin
Names
Biological Activity
[Description]:
Ascochlorin (Ilicicolin D), an isoprenoid antibiotic, mediates its anti-tumor effects predominantly through the suppression of STAT3 signaling cascade. Ascochlorin induces apoptosis. Anti-inflammatory activity[1][2][3].
[Related Catalog]:
[Target]
STAT3
Apoptosis
[In Vitro]
Ascochlorin (Ilicicolin D) (10-50 μM; 24-72 hours) inhibits the viability of HepG2, HCCLM3 and Huh7 cells in a time and dose dependent manner[3]. Ascochlorin (50 μM; 48 hours) induces apoptosis in HCC cells[3]. Ascochlorin (1-50 μM) significantly suppresses the production of nitric oxide (NO) and prostaglandin E2 (PGE2) and decreases the gene expression of inducible NO synthase (iNOS) and cyclooxygenase-2 (COX-2) in a dose-dependent manner. Ascochlorin inhibits the mRNA expression and the protein secretion of interleukin (IL)-1β and IL-6 but not tumor necrosis factor (TNF)-α in LPS-stimulated RAW 264.7 macrophage cells. Ascochlorin suppresses nuclear translocation and DNA binding affinity of nuclear factor-κB (NF-κB). Ascochlorin down-regulates phospho-extracellular signal-regulated kinase 1/2 (p-ERK1/2) and p-p38[2]. Cell Viability Assay[3] Cell Line: HepG2, HCCLM3, Huh7 cells Concentration: 10, 25, 50 μM Incubation Time: 24, 48, 72 hours Result: Inhibit the viability of three different HCC cell lines tested (HepG2, HCCLM3 and Huh7) in a time and dose dependent manner. Western Blot Analysis[3] Cell Line: HepG2 cells Concentration: 50 μM Incubation Time: 48 hours Result: Inhibited expression of the cell cycle regulator protein cyclin D1, the anti-apoptotic proteins Bcl-2, Mcl-1, survivin and XIAP, and the invasive gene product MMP-9.
[In Vivo]
Ascochlorin (Ilicicolin D) (2.5-5 mg/kg; i.p.; day 0, 1, 2, 3, 13, 15, 17, 20, 22, 24, 27, 29 and 31) inhibits tumor growth in an orthotopic HCC mouse model[1]. Animal Model: Eight week-old athymic balb/c nude female mice (HCCLM3-Luc2 tumors)[3] Dosage: 2.5 mg/kg, 5 mg/kg Administration: I.p.; day 0, 1, 2, 3, 13, 15, 17, 20, 22, 24, 27, 29 and 31 Result: Induced significant inhibition of tumor growth.
[References]
Chemical & Physical Properties
[ Density]:
1.199g/cm3
[ Boiling Point ]:
556.9ºC at 760mmHg
[ Molecular Formula ]:
C23H29ClO4
[ Molecular Weight ]:
404.92700
[ Flash Point ]:
290.6ºC
[ Exact Mass ]:
404.17500
[ PSA ]:
74.60000
[ LogP ]:
5.55850
[ Vapour Pressure ]:
5.2E-13mmHg at 25°C
[ Index of Refraction ]:
1.603
MSDS
Toxicological Information
CHEMICAL IDENTIFICATION
- RTECS NUMBER :
- VH3707560
- CHEMICAL NAME :
- beta-Resorcylaldehyde, 5-chloro-6-methyl-3-(3-methyl-5-(1,2,6-trimethyl-3-ox ocyclohexyl)- 2,4-pentadienyl)-, (E,E)-
- CAS REGISTRY NUMBER :
- 26166-39-2
- LAST UPDATED :
- 199312
- DATA ITEMS CITED :
- 1
- MOLECULAR FORMULA :
- C23-H29-Cl-O4
- MOLECULAR WEIGHT :
- 404.97
- WISWESSER LINE NOTATION :
- L6VTJ B1 C1U1Y1&U2R BQ FQ CG D1 EVH& E1 F1
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 20 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 21,539,1968
Safety Information
[ RIDADR ]:
NONH for all modes of transport
Articles
Silibinin suppresses PMA-induced MMP-9 expression by blocking the AP-1 activation via MAPK signaling pathways in MCF-7 human breast carcinoma cells.
Biochem. Biophys. Res. Commun. 354(1) , 165-71, (2007)
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 m...