title: Hesperidin
text: Hesperidin is a flavanone glycoside found in citrus fruits. Its aglycone is hesperetin. Its name is derived from the word "hesperidium", for fruit produced by citrus trees.
  
  Hesperidin was first isolated in 1828 by French chemist M. Lebreton from the white inner layer of citrus peels (mesocarp, albedo).
  
  Hesperidin is believed to play a role in plant defense.
  
  Sources
  
  Rutaceae
   700–2,500 ppm in fruit of Citrus aurantium (bitter orange, petitgrain)
   in orange juice (Citrus sinensis)
   in Zanthoxylum gilletii
   in lemon 
   in lime 
   in leaves of Agathosma serratifolia
  
  Lamiaceae
  Peppermint contains hesperidin.
  
  Content in foods
  
  Approximate hesperidin content per 100 ml
  
   481 mg peppermint, dried
   44 mg blood orange, pure juice
   26 mg orange, pure juice
   18 mg lemon, pure juice
   14 mg lime, pure juice
   1 mg grapefruit, pure juice
  
  Metabolism 
  Hesperidin 6-O-α--rhamnosyl-β--glucosidase, an enzyme that uses hesperidin and water to produce hesperetin and rutinose, is found in the Ascomycetes species.
  
  Research 
  As a flavanone found in the rinds of citrus fruits (such as oranges or lemons), hesperidin is under preliminary research for its possible biological properties in vivo. One review did not find evidence that hesperidin affected blood lipid levels or hypertension. Another review found that hesperidin may improve endothelial function in humans, but the overall results were inconclusive.
  
  Biosynthesis 
  
  The biosynthesis of hesperidin stems from the phenylpropanoid pathway, in which the natural amino acid -phenylalanine undergoes a deamination by phenylalanine ammonia lyase to afford (E)-cinnamate. The resulting monocarboxylate undergoes an oxidation by cinnamate 4-hydroxylase to afford (E)-4-coumarate, which is transformed into (E)-4-coumaroyl-CoA by 4-coumarate-CoA ligase. (E)-4-coumaroyl-CoA is then subjected to the type III polyketide synthase naringenin chalcone synthase, undergoing successive condensation reactions and ultimately a ring-closing Claisen condensation to afford naringenin chalcone. The corresponding chalcone undergoes an isomerization by chalcone isomerase to afford (2S)-naringenin, which is oxidized to (2S)-eriodictyol by flavonoid 3′-hydroxylase. After O-methylation by caffeoyl-CoA O-methyltransferase, the hesperitin product undergoes a glycosylation by flavanone 7-O-glucosyltransferase to afford hesperitin-7-O-β--glucoside. Finally, a rhamnosyl moiety is introduced to the monoglycosylated product by 1,2-rhamnosyltransferase, forming hesperidin.
  
  See also 
   Diosmin
   List of phytochemicals in food
   List of MeSH codes (D03)
   List of food additives
  
  References
  
  External links 
  
  Flavanone glycosides
  Flavonoid antioxidants
  Bitter compounds
  Flavonoids found in Rutaceae