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 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
ChEBI
  • CHEBI:8633 checkY
ChEMBL
  • ChEMBL486386 checkY
ChemSpider
  • 4445119 checkY
ECHA InfoCard 100.130.674 Edit this at Wikidata
KEGG
  • C10524 checkY
PubChem CID
  • 5486172
UNII
  • Z9W8997416 checkY
CompTox Dashboard (EPA)
  • DTXSID30958020 Edit this at Wikidata
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 checkY
    Key: HKEAFJYKMMKDOR-VPRICQMDSA-N checkY
  • 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).
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Infobox references
Chemical compound

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

Notes and references

  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.
  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.
  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.
  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.
  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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Isoflavones and their glycosides
IsoflavonesO-methylated isoflavonesGlycosidesPrenylated isoflavones
Pyranoisoflavones
Derivatives
Synthetic
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Receptor
(ligands)
P0 (adenine)
P1
(adenosine)
P2
(nucleotide)
P2X
(ATPTooltip Adenosine triphosphate)
P2Y
Transporter
(blockers)
CNTsTooltip Concentrative nucleoside transporters
ENTsTooltip Equilibrative nucleoside transporters
PMATTooltip Plasma membrane monoamine transporter
Enzyme
(inhibitors)
XOTooltip Xanthine oxidase
Others
Others
See also: Receptor/signaling modulators


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