Isobavachalcone
Isobavachalcone is a prenylated chalcone flavonoid found in several species of Psoraleae; it exhibits neuroprotective, antithrombotic, antifungal, anticancer chemotherapeutic, and chemopreventive activities. In separate in vitro experiments, isobavachalcone inhibits platelet aggregation and displays activity against several fungi, including Candida albicans and Cryptococcus neoformans. Isobavachalcone also displays potential benefit as a treatment for Alzheimer’s disease, inhibiting oligomerization and fibrillization of amyloid-β (Aβ), decreasing neurotoxicity in cellular models. This compound inhibits skin tumor promotion induced by DMBA and TPA in animal models and increases caspase-3, caspase-9, and Bax levels, inducing both mitochondrial-mediated and caspase-mediated apoptosis in neuroblastoma cells. Additionally, isobavachalcone exhibits strand scission activity, relaxing supercoiled DNA to nicked DNA in cells. Isobavachalcone also non-competitively inhibits cholesterol acyltransferase, an enzyme that plays a significant role in intestinal absorption of cholesterol and hepatic production of lipoproteins.
References PubMed ID：:http://www.ncbi.nlm.nih.gov/pubmed/18931877
| Cas No. |
20784-50-3 |
|---|---|
| Purity |
≥97% |
| Formula |
C20H20O4 |
| Formula Wt. |
324.37 |
| Chemical Name |
(E)-1-[2,4-Dihydroxy-3-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)-2-propen-1-one |
| IUPAC Name |
(E)-1-[2,4-dihydroxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one |
| Appearance |
Yellow to light brown powder |
Chen X, Yang Y, Zhang Y. Isobavachalcone and bavachinin from Psoraleae Fructus modulate Aβ42 aggregation process through different mechanisms in vitro. FEBS Lett. 2013 Sep 17;587(18):2930-5. PMID: 23907009.
Jing H, Zhou X, Dong X, et al. Abrogation of Akt signaling by Isobavachalcone contributes to its anti-proliferative effects towards human cancer cells. Cancer Lett. 2010 Aug 28;294(2):167-77. PMID: 20167420.
Choi JH, Rho MC, Lee SW, et al. Bavachin and isobavachalcone, acyl-coenzyme A: cholesterol acyltransferase inhibitors from Psoralea corylifolia. Arch Pharm Res. 2008 Nov;31(11):1419-23. PMID: 19023538.
Nishimura R, Tabata K, Arakawa M, et al. Isobavachalcone, a chalcone constituent of Angelica keiskei, induces apoptosis in neuroblastoma. Biol Pharm Bull. 2007 Oct;30(10):1878-83. PMID: 17917255.
Chen YG, Song XP, Hai LN, et al. Compounds with DNA cleaving activity from Kadsura ananosma. Pharmazie. 2006 Oct;61(10):891-2. PMID: 17069433.
Akihisa T, Tokuda H, Hasegawa D, et al. Chalcones and other compounds from the exudates of Angelica keiskei and their cancer chemopreventive effects. J Nat Prod. 2006 Jan;69(1):38-42. PMID: 16441065.
ElSohly HN, Joshi AS, Nimrod AC, et al. Antifungal chalcones from Maclura tinctoria. Planta Med. 2001 Feb;67(1):87-9. PMID: 11270732.
Tsai WJ, Hsin WC, Chen CC. Antiplatelet flavonoids from seeds of Psoralea corylifolia. J Nat Prod. 1996 Jul;59(7):671-2. PMID: 8759164.
