Rhapontigenin
Chemical structure of rhapontigenin
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
UNII
  • InChI=1S/C15H14O4/c1-19-15-5-4-10(8-14(15)18)2-3-11-6-12(16)9-13(17)7-11/h2-9,16-18H,1H3/b3-2+
    Key: PHMHDRYYFAYWEG-NSCUHMNNSA-N
  • COc1ccc(cc1O)\C=C\c(cc2O)cc(O)c2
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).

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

References

  1. ^ 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
  2. ^ 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.
  3. ^ 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.
  4. ^ 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. S2CID 9538085.

External links


Hydroxystilbenes and their glycosides (monomeric forms)
Categories