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Rhapontigenin

From Wikipedia, the free encyclopedia
Rhapontigenin
Chemical structure of 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)
ChEBI
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 mass258.27 g/mol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Rhapontigenin is astilbenoid. It can be isolated fromVitis coignetiae or fromGnetum cleistostachyum.[1]

It shows an action onprostate cancer cells.[2] It has been shown to inhibit the humancytochrome P450 1A1,[3] an enzyme implicated in the biotransformation of a number of carcinogenic and immunotoxic compounds.

Injected in rats, rhapontigenin shows a rapidglucuronidation and a poorbioavailability.[4]

See also

[edit]

References

[edit]
  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

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Hydroxystilbenes and theirglycosides (monomeric forms)
Dihydroxylated
Trihydroxylated
Tetrahydroxylated
O-methylated
Combretastatins
carboxylated
other acylations
Glycosides
of resveratrol
of rhapontigenin
Oligomeric forms


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