Puerarin

Puerarin

IUPAC name 7-Hydroxy-3-(4-hydroxyphenyl)-8-[(3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
Other names Daidzein-8-C-glucoside 7,4'-Dihydroxy-8-C-glucosylisoflavone
Identifiers
CAS number	3681-99-0^Y
PubChem	5486172
ChemSpider	4445119^Y
ChEMBL	CHEMBL486386^Y
Jmol-3D images	Image 1
SMILES 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
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
Properties
Molecular formula	C₂₁H₂₀O₉
Molar mass	416.38 g mol⁻¹
Exact mass	416.110732
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Puerarin is one of several known isoflavones. Puerarin is found in a number of plants and herbs like the root of Pueraria (Radix puerariae)^[1] notably of the kudzu plant.

Puerarin is the 8-C-glucoside of daidzein.

Puerarin is a 5-HT_2C receptor and benzodiazepine site antagonist.^[2]

Puerarin is being investigated as a self-microemulsifying drug delivery system.

List of plants that contain the chemical

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

Notes & references

^ Puerarin, an isoflavonoid derived from Radix puerariae, potentiates endothelium-independent relaxation via the cyclic AMP pathway in porcine coronary artery, Dennis K.Y. Yeunga, Susan W.S. Leung, a, , Yan Chun Xua, Paul M. Vanhouttea and Ricky Y.K. Mana, 2006
^ 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.
^ Wang, Lingzhao et al.; Yang, BAO; Du, Xiuqiao (2009). "Investigation of supercritical fluid extraction of puerarin from Pueraria Lobata". Journal of Food Process Engineering (John Wiley & Sons) 32 (5): 682–691. doi:10.1111/j.1745-4530.2007.00238.x.
^ Chen, Gang et al.; Zhang, J; Ye, J (2001). "Determination of puerarin, daidzein and rutin in Pueraria lobata (Wild.) Ohwi by capillary electrophoresis with electrochemical detection". Journal of Chromatography A (Elsevier) 923 (1 – 2): 255–262. doi:10.1016/S0021-9673(01)00996-7. PMID 11510548.
^ Kintzios, Spiridon et al.; Makri, Olga; Pistola, Eleni; Matakiadis, Theodoros; Ping Shi, He; Economou, Athanassios (2004). "Scale-up production of puerarin from hairy roots of Pueraria phaseoloides in an airlift bioreactor". Biotechnology Letters (Springer) 26 (13): 1057–1059. doi:10.1023/B:BILE.0000032963.41208.e8. ISSN 0141-5492.
^ Shi, H. P; S. Kintzies (2003). "Genetic transformation of Pueraria phaseoloides with Agrobacterium rhizogenes and puerarin production in hairy roots". Plant Cell Reports (Springer) 21 (11): 1103–1107. doi:10.1007/s00299-003-0633-6. ISSN 0721-7714.

Isoflavones and their glycosides

Isoflavones	Daidzein \| Genistein \| Irilone \|Orobol \| Pseudobaptigenin \| Anagyroidisoflavone A and B

O-methylated isoflavones	Biochanin A \| Calycosin \| Formononetin \| Glycitein \| Irigenin \| 5-O-methylgenistein \| Pratensein \| Prunetin \| Psi-tectorigenin \| Retusin \| Tectorigenin

Glycosides	Daidzin \| Genistin \| Iridin \| Ononin \| Puerarin \| Tectoridin

Prenylated isoflavones	Bidwillol A \| Derrubone \| Luteone \| Wighteone

Pyranoisoflavones	Alpinumisoflavone \| Barbigerone \| Di-O-methylalpinumisoflavone \| 4'-methyl-alpinumisoflavone

Misc	Rotenoids

Synthetic	Ipriflavone