Phloretin

Source: Wikipedia, the free encyclopedia.
Phloretin
Names
Preferred IUPAC name
3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one
Other names
Dihydronaringenin
Phloretol
Identifiers
3D model (
JSmol
)
ChEBI
ChemSpider
ECHA InfoCard
 100.000.444 Edit this at Wikidata
IUPHAR/BPS
KEGG
UNII
  • InChI=1S/C15H14O5/c16-10-4-1-9(2-5-10)3-6-12(18)15-13(19)7-11(17)8-14(15)20/h1-2,4-5,7-8,16-17,19-20H,3,6H2 ☒N
    Key: VGEREEWJJVICBM-UHFFFAOYSA-N ☒N
  • InChI=1/C15H14O5/c16-10-4-1-9(2-5-10)3-6-12(18)15-13(19)7-11(17)8-14(15)20/h1-2,4-5,7-8,16-17,19-20H,3,6H2
    Key: VGEREEWJJVICBM-UHFFFAOYAB
  • C1=CC(=CC=C1CCC(=O)C2=C(C=C(C=C2O)O)O)O
Properties
C15H14O5
Molar mass 274.272 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Phloretin is a dihydrochalcone, a type of natural phenol. It can be found in apple tree leaves[1] and the Manchurian apricot.[2]

Metabolism

In rats, ingested phlorizin is converted into phloretin by hydrolytic enzymes in the small intestine.[3][4] Phloretin hydrolase hydrolyses phloretin into phloretic acid and phloroglucinol.

Pharmacological research

In an animal model, phloretin inhibited

aquaporin 9 (AQP9) on mouse hepatocytes.[9]

Nanoparticle Synthesis

Phloretin functionalized gold-nanoparticles (Pht-GNPs) were synthesized using a single-step synthesis method and tested for its anticancer activity. Pht-GNPs showed significant cancer cell toxicities compared to free phloretin.[10]

Glycosides

See also

  • Phloretin-glucosidase

References

  1. doi:10.1021/jf00056a057
    .
  2. ^ "Manchurian Apricot (Prunus armeniaca var. mandshurica)" (PDF). North Dakota State University. Retrieved January 30, 2014.
  3. ^
    PMID 19125776
    .
  4. ^
    PMID 11739871
    .
  5. PMID 14019989
    . Retrieved 2012-10-21.
  6. PMID 15123796
    .
  7. S2CID 22143248. Archived from the original
    on 2016-03-04. Retrieved 2012-10-21.
  8. S2CID 3638970
    .
  9. PMID 15123796
    .
  10. PMID 29636609
    .
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