Rhapontigenin

Rhapontigenin
Chemical structure of 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]
ChEMBL ChEMBL113029
ChemSpider 4478875
Jmol-3D images Image
PubChem 5320954
Properties
C15H14O4
Molar mass 258.27 g/mol
Except where noted otherwise, data is 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

  1. ↑ http://www.caymanchem.com/app/template/Product.vm/catalog/13293
  2. ↑ 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
  3. ↑ 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.
  4. ↑ 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.
  5. ↑ 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