Chemistry:Rhapontigenin
From HandWiki
| |
| Names | |
|---|---|
| Preferred IUPAC name
5-[(E)-2-(3-Hydroxy-4-methoxyphenyl)ethen-1-yl]benzene-1,3-diol | |
| Other names
Protigenin
3,3',5-trihydroxy-4'-methoxystilbene piceatannol 4'-methyl ether | |
| Identifiers | |
3D model (JSmol)
|
|
| ChEMBL | |
| ChemSpider | |
PubChem CID
|
|
| UNII | |
| |
| |
| 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 | |
Tracking categories (test):
Rhapontigenin is a stilbenoid. It can be isolated from Vitis coignetiae or from Gnetum cleistostachyum.[1]
It shows an action on prostate cancer cells.[2] It has been shown to inhibit the human cytochrome P450 1A1,[3] 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.[4]
See also
- Rhaponticin, its glucoside, found in rhubarb.
- Isorhapontigenin, a structural isomer.
References
- ↑ 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. et al. (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 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.
External links
 |  |
