Hesperidin

Hesperidin

Hesperidin

Chemical compound

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.

Not to be confused with hesperadin.
Quick Facts Names, Identifiers ...

Hesperidin was first isolated in 1828 by French chemist M. Lebreton from the white inner layer of citrus peels (mesocarp, albedo).[2][3]

Hesperidin is believed to play a role in plant defense.

Sources

Rutaceae

Lamiaceae

Peppermint contains hesperidin.[7]

Ultraviolet 280 nm chromatogram after UHPLC separation of commercial orange juice. Hesperidin is the peak at 16.44 min.

Content in foods

Approximate hesperidin content per 100 ml or 100 g[8]

Metabolism

Hesperidin 6-O-α-L-rhamnosyl-β-D-glucosidase, an enzyme that uses hesperidin and water to produce hesperetin and rutinose, is found in the Ascomycetes species.[9]

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.[10] Another review found that hesperidin may improve endothelial function in humans, but the overall results were inconclusive.[11]

Biosynthesis

The biosynthesis of hesperidin proceeds from L-phenylalanine in nine steps.

The biosynthesis of hesperidin stems from the phenylpropanoid pathway, in which the natural amino acid L-phenylalanine undergoes a deamination by phenylalanine ammonia lyase to afford (E)-cinnamate.[12] The resulting monocarboxylate undergoes an oxidation by cinnamate 4-hydroxylase to afford (E)-4-coumarate,[13] which is transformed into (E)-4-coumaroyl-CoA by 4-coumarate-CoA ligase.[14] (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.[15] The corresponding chalcone undergoes an isomerization by chalcone isomerase to afford (2S)-naringenin,[16] which is oxidized to (2S)-eriodictyol by flavonoid 3′-hydroxylase.[17] After O-methylation by caffeoyl-CoA O-methyltransferase,[18] the hesperitin product undergoes a glycosylation by flavanone 7-O-glucosyltransferase to afford hesperitin-7-O-β-D-glucoside.[19] Finally, a rhamnosyl moiety is introduced to the monoglycosylated product by 1,2-rhamnosyltransferase, forming hesperidin.[20]

See also

References

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    Dakshini KM (August 1991). "Hesperetin 7-rutinoside (hesperidin) and taxifolin 3-arabinoside as germination and growth inhibitors in soils associated with the weed, Pluchea lanceolata (DC) C.B. Clarke (Asteraceae)". Journal of Chemical Ecology. 17 (8): 1585–1591. Bibcode:1991JCEco..17.1585I. doi:10.1007/BF00984690. PMID 24257882. S2CID 35483504.
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    Lebreton, M (1828). "Sur la matière cristalline des orangettes, et analyse de ces fruits non encore developpés, famille des Hesperidées". Journal de Pharmacie et de Sciences Accessories. 14: 377. Archived from the original on 2020-10-20. Retrieved 2016-10-30.
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