Isoxanthohumol
Isoxanthohumol (IX) is a prenylflavinoid and derivative of xanthohumol found in Humulus lupulus. IX, similar to xanthohumol, exhibits anti-inflammatory, anti-angiogenic, and pro-apoptotic activities, although at a lesser potency than xanthohumol. IX modulates signaling between endothelial cells and vascular smooth muscle cells in a variety of cell lines, decreasing levels of TNF-α, NF-kB, VEGF-R2, and angiopoetins 1 and 2. In mature adipocytes, IX increases ROS and induces apoptosis; in preadipocytes, this compound inhibits differentiation and also induces apoptosis as exhibited by increases in cytochrome c and PARP and decreases in PPARy, adipocyte protein 2, and CEBP2 upon stimulation with IX. IX undergoes transformation in vitro and in the intestine to form 8-prenylnaringenin, a potent phytoestrogen.
References PubMed ID：:http://www.ncbi.nlm.nih.gov/pubmed/1893509
| Cas No. |
70872-29-6 |
|---|---|
| Purity |
≥98% |
| Formula |
C21H22O5 |
| Formula Wt. |
354.39 |
| Chemical Name |
7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one |
| IUPAC Name |
7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one |
| Appearance |
White to off white powder |
Negrão R, Duarte D, Costa R, et al. Isoxanthohumol modulates angiogenesis and inflammation via vascular endothelial growth factor receptor, tumor necrosis factor alpha and nuclear factor kappa B pathways. Biofactors. 2013 Aug 1. [Epub ahead of print] PMID: 23904052.
Negrão R, Costa R, Duarte D, et al. Angiogenesis and inflammation signaling are targets of beer polyphenols on vascular cells. J Cell Biochem. 2010 Dec 1;111(5):1270-9. PMID: 20803553.
Possemiers S, Rabot S, Espín JC, et al. Eubacterium limosum activates isoxanthohumol from hops (Humulus lupulus L.) into the potent phytoestrogen 8-prenylnaringenin in vitro and in rat intestine. J Nutr. 2008 Jul;138(7):1310-6. PMID: 18567753.
Yang JY, Della-Fera MA, Rayalam S, et al. Effect of xanthohumol and isoxanthohumol on 3T3-L1 cell apoptosis and adipogenesis. Apoptosis. 2007 Nov;12(11):1953-63. PMID: 17874298.
Possemiers S, Bolca S, Grootaert C, et al. The prenylflavonoid isoxanthohumol from hops (Humulus lupulus L.) is activated into the potent phytoestrogen 8-prenylnaringenin in vitro and in the human intestine. J Nutr. 2006 Jul;136(7):1862-7. PMID: 16772450.
