Rhapontigenin
 | |
| Names | |
|---|---|
| IUPAC name
5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]benzene-1,3-diol | |
| Other names
Protigenin 3,3',5-trihydroxy-4'-methoxystilbene piceatannol 4'-methyl ether | |
| Identifiers | |
| 500-65-2[1] | |
| 3D model (Jmol) | Interactive image |
| ChEMBL | ChEMBL113029 |
| ChemSpider | 4478875 |
| PubChem | 5320954 |
| |
| |
| Properties | |
| C15H14O4 | |
| Molar mass | 258.27 g/mol |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Rhapontigenin is a stilbenoid. It can be isolated from Vitis coignetiae or from Gnetum cleistostachyum.[2]
It shows an action on prostate cancer cells.[3] It has been shown to inhibit the human cytochrome P450 1A1,[4] an enzyme implicated in the biotransformation of a number of carcinogenic and immunotoxic compounds.
Injected in rats, rhapontigenin shows a rapid glucuronidation and a poor bioavailability.[5]
References
- ↑ http://www.caymanchem.com/app/template/Product.vm/catalog/13293
- ↑ Stilbenes from Gnetum cleistostachyum. Yao Chun-Suo, Lin Mao, LIiu Xin and Wang Ying-Hong, Huaxue xuebao, 2003, volume 61, no 8, pages 1331-1334, INIST:15332136
- ↑ Jung, D. B.; Lee, H. J.; Jeong, S. J.; Lee, H. J.; Lee, E. O.; Kim, Y. C.; Ahn, K. S.; Chen, C. Y.; Kim, S. H. (2011). "Rhapontigenin inhibited hypoxia inducible factor 1 alpha accumulation and angiogenesis in hypoxic PC-3 prostate cancer cells". Biological & Pharmaceutical Bulletin. 34 (6): 850–855. doi:10.1248/bpb.34.850. PMID 21628883.
- ↑ Chun, Y. J.; Ryu, S. Y.; Jeong, T. C.; Kim, M. Y. (2001). "Mechanism-based inhibition of human cytochrome P450 1A1 by rhapontigenin". Drug metabolism and disposition: the biological fate of chemicals. 29 (4 Pt 1): 389–393. PMID 11259321.
- ↑ Roupe, K. A.; Yáñez, J. A.; Teng, X. W.; Davies, N. M. (2006). "Pharmacokinetics of selected stilbenes: Rhapontigenin, piceatannol and pinosylvin in rats". Journal of Pharmacy and Pharmacology. 58 (11): 1443–1450. doi:10.1211/jpp.58.11.0004. PMID 17132206.
See also
- Rhaponticin, its glucoside, found in rhubarb.
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