Puerarin

Puerarin
Names
	IUPAC name 8-(β-D-Glucopyranosyl)-4′,7-dihydroxyisoflavone
	Systematic IUPAC name 7-Hydroxy-3-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-1-benzopyran-4-one
	Other names Daidzein-8-C-glucoside; 7,4'-Dihydroxy-8-C-glucosylisoflavone
Identifiers
CAS Number	3681-99-0 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:8633 ;
ChEMBL	ChEMBL486386 ;
ChemSpider	4445119 ;
ECHA InfoCard	100.130.674
KEGG	C10524 ;
PubChem CID	5486172;
UNII	Z9W8997416 ;
CompTox Dashboard (EPA)	DTXSID30958020 ;
	InChI InChI=1S/C21H20O9/c22-7-14-17(26)18(27)19(28)21(30-14)15-13(24)6-5-11-16(25)12(8-29-20(11)15)9-1-3-10(23)4-2-9/h1-6,8,14,17-19,21-24,26-28H,7H2/t14-,17-,18+,19-,21+/m1/s1 Key: HKEAFJYKMMKDOR-VPRICQMDSA-N ;
	SMILES C1=CC(=CC=C1C2=COC3=C(C2=O)C=CC(=C3C4C(C(C(C(O4)CO)O)O)O)O)O; O=C2c3c(O/C=C2/c1ccc(O)cc1)c(c(O)cc3)[C@@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O)CO;
Properties
Chemical formula	C21H20O9
Molar mass	416.382 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Puerarin, one of several known isoflavones, is found in a number of plants and herbs, such as the root of the kudzu plant.^[1]

Puerarin is the 8-C-glucoside of daidzein.^[2]

List of plants that contain the chemical

Pueraria lobata^[3]^[4]
Pueraria phaseoloides^[5]^[6]

Notes and references

^ Dennis K.Y. Yeunga; Susan W.S. Leung; Yan Chun Xua; Paul M. Vanhouttea; Ricky Y.K. Mana (2006). "Puerarin, an isoflavonoid derived from Radix puerariae, potentiates endothelium-independent relaxation via the cyclic AMP pathway in porcine coronary artery". European Journal of Pharmacology. 552 (1–3): 105–11. doi:10.1016/j.ejphar.2006.08.078. PMID 17027964.
^ Overstreet DH, Kralic JE, Morrow AL, Ma ZZ, Zhang YW, Lee DY (2003). "NPI-031G (puerarin) reduces anxiogenic effects of alcohol withdrawal or benzodiazepine inverse or 5-HT2C agonists". Pharmacology Biochemistry and Behavior. 75 (3): 619–625. doi:10.1016/S0091-3057(03)00114-X. PMID 12895679. S2CID 22252214.
^ Wang, Lingzhao; Yang, BAO; Du, Xiuqiao; et al. (2009). "Investigation of supercritical fluid extraction of puerarin from Pueraria Lobata". Journal of Food Process Engineering. 32 (5). John Wiley & Sons: 682–691. doi:10.1111/j.1745-4530.2007.00238.x.
^ Chen, Gang; Zhang, J; Ye, J; et al. (2001). "Determination of puerarin, daidzein and rutin in Pueraria lobata (Wild.) Ohwi by capillary electrophoresis with electrochemical detection". Journal of Chromatography A. 923 (1–2). Elsevier: 255–262. doi:10.1016/S0021-9673(01)00996-7. PMID 11510548.
^ Kintzios, Spiridon; Makri, Olga; Pistola, Eleni; Matakiadis, Theodoros; Ping Shi, He; Economou, Athanassios; et al. (2004). "Scale-up production of puerarin from hairy roots of Pueraria phaseoloides in an airlift bioreactor". Biotechnology Letters. 26 (13). Springer: 1057–1059. doi:10.1023/B:BILE.0000032963.41208.e8. ISSN 0141-5492. PMID 15218379. S2CID 23425268.
^ Shi, H. P; S. Kintzies (2003). "Genetic transformation of Pueraria phaseoloides with Agrobacterium rhizogenes and puerarin production in hairy roots". Plant Cell Reports. 21 (11). Springer: 1103–1107. doi:10.1007/s00299-003-0633-6. ISSN 0721-7714. PMID 12836005. S2CID 21825544.

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[1] Dennis K.Y. Yeunga; Susan W.S. Leung; Yan Chun Xua; Paul M. Vanhouttea; Ricky Y.K. Mana (2006). "Puerarin, an isoflavonoid derived from Radix puerariae, potentiates endothelium-independent relaxation via the cyclic AMP pathway in porcine coronary artery". European Journal of Pharmacology. 552 (1–3): 105–11. doi:10.1016/j.ejphar.2006.08.078. PMID 17027964.

[2] Overstreet DH, Kralic JE, Morrow AL, Ma ZZ, Zhang YW, Lee DY (2003). "NPI-031G (puerarin) reduces anxiogenic effects of alcohol withdrawal or benzodiazepine inverse or 5-HT2C agonists". Pharmacology Biochemistry and Behavior. 75 (3): 619–625. doi:10.1016/S0091-3057(03)00114-X. PMID 12895679. S2CID 22252214.

[isfe-3] Wang, Lingzhao; Yang, BAO; Du, Xiuqiao; et al. (2009). "Investigation of supercritical fluid extraction of puerarin from Pueraria Lobata". Journal of Food Process Engineering. 32 (5). John Wiley & Sons: 682–691. doi:10.1111/j.1745-4530.2007.00238.x.

[dpdr-4] Chen, Gang; Zhang, J; Ye, J; et al. (2001). "Determination of puerarin, daidzein and rutin in Pueraria lobata (Wild.) Ohwi by capillary electrophoresis with electrochemical detection". Journal of Chromatography A. 923 (1–2). Elsevier: 255–262. doi:10.1016/S0021-9673(01)00996-7. PMID 11510548.

[spph-5] Kintzios, Spiridon; Makri, Olga; Pistola, Eleni; Matakiadis, Theodoros; Ping Shi, He; Economou, Athanassios; et al. (2004). "Scale-up production of puerarin from hairy roots of Pueraria phaseoloides in an airlift bioreactor". Biotechnology Letters. 26 (13). Springer: 1057–1059. doi:10.1023/B:BILE.0000032963.41208.e8. ISSN 0141-5492. PMID 15218379. S2CID 23425268.

[gtpp-6] Shi, H. P; S. Kintzies (2003). "Genetic transformation of Pueraria phaseoloides with Agrobacterium rhizogenes and puerarin production in hairy roots". Plant Cell Reports. 21 (11). Springer: 1103–1107. doi:10.1007/s00299-003-0633-6. ISSN 0721-7714. PMID 12836005. S2CID 21825544.

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v t e Isoflavones and their glycosides
Isoflavones	Daidzein Genistein Orobol
O-methylated isoflavones	Biochanin A Calycosin Formononetin Glycitein Irigenin 5-O-methylgenistein Pratensein Prunetin Psi-tectorigenin Retusin Tectorigenin
Glycosides	Daidzin Genistin Iridin Mirificin Ononin Puerarin Sophoricoside Tectoridin
Prenylated isoflavones	Bidwillol A Derrubone Luteone 7-O-Methylluteone Wighteone
Pyranoisoflavones	Alpinumisoflavone Barbigerone Di-O-methylalpinumisoflavone 4'-methyl-alpinumisoflavone
Derivatives	Anagyroidisoflavone A and B Irilone Pseudobaptigenin Rotenoids
Synthetic	Ipriflavone
Category

Names

IUPAC name 8-(β-D-Glucopyranosyl)-4′,7-dihydroxyisoflavone
Systematic IUPAC name 7-Hydroxy-3-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-1-benzopyran-4-one
Other names Daidzein-8-C-glucoside 7,4'-Dihydroxy-8-C-glucosylisoflavone
Identifiers
CAS Number	3681-99-0^Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:8633^Y
ChEMBL	ChEMBL486386^Y
ChemSpider	4445119^Y
ECHA InfoCard	100.130.674
KEGG	C10524^Y
PubChem CID	5486172
UNII	Z9W8997416^Y
CompTox Dashboard (EPA)	DTXSID30958020
InChI InChI=1S/C21H20O9/c22-7-14-17(26)18(27)19(28)21(30-14)15-13(24)6-5-11-16(25)12(8-29-20(11)15)9-1-3-10(23)4-2-9/h1-6,8,14,17-19,21-24,26-28H,7H2/t14-,17-,18+,19-,21+/m1/s1^Y Key: HKEAFJYKMMKDOR-VPRICQMDSA-N^Y
SMILES C1=CC(=CC=C1C2=COC3=C(C2=O)C=CC(=C3C4C(C(C(C(O4)CO)O)O)O)O)O O=C2c3c(O/C=C2/c1ccc(O)cc1)c(c(O)cc3)[C@@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O)CO
Properties
Chemical formula	C₂₁H₂₀O₉
Molar mass	416.382 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references