Rhapontigenin

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
CAS Number	500-65-2 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:174376;
ChEMBL	ChEMBL113029;
ChemSpider	4478875;
PubChem CID	5320954;
UNII	22BG4NNH6W ;
CompTox Dashboard (EPA)	DTXSID501023634 ;
	InChI 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;
	SMILES COc1ccc(cc1O)\C=C\c(cc2O)cc(O)c2;
Properties
Chemical formula	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.^[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]

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.; 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. 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. S2CID 9538085.

External links

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[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.

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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
CAS Number	500-65-2^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:174376
ChEMBL	ChEMBL113029
ChemSpider	4478875
PubChem CID	5320954
UNII	22BG4NNH6W^Y
CompTox Dashboard (EPA)	DTXSID501023634
InChI 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
SMILES COc1ccc(cc1O)\C=C\c(cc2O)cc(O)c2
Properties
Chemical formula	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

See also

References

External links