Ascochlorin

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.

Product information

CAS Number: 26166-39-2

Molecular Weight: 404.93

Formula: C23H29ClO4

Synonym:

Ilicicolin D

Chemical Name: 3-chloro-4, 6-dihydroxy-2-methyl-5-[(2E, 4E)-3-methyl-5-[(1R, 2R, 6R)-1, 2, 6-trimethyl-3-oxocyclohexyl]penta-2, 4-dien-1-yl]benzaldehyde

Smiles: C[C@@H]1CCC(=O)[C@H](C)[C@@]1(C)/C=C/C(/C)=C/CC1=C(O)C(Cl)=C(C)C(C=O)=C1O

InChiKey: SETVRSKZJJWOPA-FLDGXQSCSA-N

InChi: 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+/t14-,16+,23+/m1/s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

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. Ascochlorin (50 μM; 48 hours) induces apoptosis in HCC cells. 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.

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.

References:

1. Lee SH, et al. Anti-Inflammatory Effect of Ascochlorin in LPS-Stimulated RAW 264.7 Macrophage Cells Is Accompanied With the Down-Regulation of iNOS, COX-2 and Proinflammatory Cytokines Through NF-κB, ERK1/2, and p38 Signaling Pathway. J Cell Biochem. 2016 Apr;117(4):978-87.
2. Dai X, et al. Ascochlorin, an isoprenoid antibiotic inhibits growth and invasion of hepatocellular carcinoma by targeting STAT3 signaling cascade through the induction of PIAS3. Mol Oncol. 2015 Apr;9(4):818-33.

Products are for research use only. Not for human use.