Cardamonin

Cardamonin (Alpinetin chalcone), isolated from the fruits of Alpinia species, is a chalconoid with anti-inflammatory and anti-tumor activity. It has been shown to be a novel antagonist of hTRPA1 cation channel with IC50 of 454 nM while does not interact with TRPV1 nor TRPV4 channel.

Product information

CAS Number: 18956-16-6

Molecular Weight: 270.28

Formula: C16H14O4

Chemical Name: 1-(2,4-dihydroxy-6-methoxyphenyl)-3-phenylprop-2-en-1-one

Smiles: COC1=CC(O)=CC(O)=C1C(=O)C=CC1C=CC=CC=1

InChiKey: NYSZJNUIVUBQMM-BQYQJAHWSA-N

InChi: InChI=1S/C16H14O4/c1-20-15-10-12(17)9-14(19)16(15)13(18)8-7-11-5-3-2-4-6-11/h2-10,17,19H,1H3/b8-7+

Technical Data

Appearance: Solid Power

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

Solubility: DMSO : 125 mg/mL (462.48 mM; Need ultrasonic)

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:

Cardamonin selectively blocks TRPA1 activation while does not interact with TRPV1 nor TRPV4 channel. A concentration-dependent inhibitory effect is observed with IC50 of 454 nM. Cardamonin does not significantly reduce HEK293 cell viability, nor does it impair cardiomyocyte constriction. In vitro, cardamonin (25 and 50 μM) concentration dependently inhibits endothelium permeability and down-regulates phosphorylation of P38 in rat lung microvascular endothelial cells induced by lipopolysaccharide (LPS). In RAW 264.7 macrophage cells, cardamonin also shows selective inhibition of P38 phosphorylation induced by LPS. Cardamonin inhibits the growth of several cancer cell types including breast cancer, glioblastoma, ovarian, prostate, and lung. Treatment of cardamonin in CRC cell lines induces cell cycle arrest mostly in the S phase of cell cycle. It activates both apoptosis and induces cell cycle arrest to inhibit the cell proliferation. Cardamonin is known to inhibit various signaling pathways which play a major role in the process of inflammation and cancer. This natural product inhibits the phosphorylation and translocation of both STAT3 and NF-κB. Cardamonin also inhibits angiogenesis through downregulation of miR-21 expression.

In Vivo:

Cardamonin (30 and 100 mg/kg) significantly elevates the survival rate of septic mice, alleviates ALI and lung microvascular leak, and lowers the serum levels of proinflammatory cytokines TNF-α, IL-1β,and IL-6. Cardamonin inhibits Azoxymethane-induced colorectal cancer (CRC). Its treatment inhibits the tumor incidence, tumor multiplicity, Ki-67 and β-catenin positive cells. The preclinical pharmacokinetics and ADME characterization of cardamonin in mice reports that cardamonin is highly permeable with an effective permeability value in ileum is (Peff) 3 × 10−4 which is highly significant. Within 30 minutes of oral dosing, cardamonin is distributed to various tissues.

References:

1. Wang K, et al. Cardamonin, a natural flavone, alleviates inflammatory bowel disease by the inhibition of NLRP3 inflammasome activation via an AhR/Nrf2/NQO1 pathway. Biochem Pharmacol. 2018 Sep;155:494-509.

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