Hesperidin

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Not to be confused with hesperadin.
Hesperidin
Hesperidin structure.svg
Names
IUPAC name
(2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one
Other names
Hesperetin 7-rutinoside[1]
Identifiers
520-26-3 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:28775 YesY
ChEMBL ChEMBL449317 YesY
ChemSpider 10176 YesY
ECHA InfoCard 100.007.536
PubChem 10621
UNII E750O06Y6O YesY
Properties
C28H34O15
Molar mass 610.57 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

Hesperidin is a flavan-on glycoside found in citrus fruits. Its aglycone form is called hesperetin. Its name is derived from the word "hesperidium", for fruit produced by citrus trees.

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

Hesperidin is believed to play a role in plant defense.

Sources[edit]

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

Peppermint also contains hesperidin.[7]

Metabolism[edit]

Hesperidin 6-O-alpha-L-rhamnosyl-beta-D-glucosidase, an enzyme that uses hesperidin and H2O to produce hesperetin and rutinose, is found in the Ascomycetes species.[8]

Research[edit]

As a flavanone found in citrus fruits (such as oranges, lemons or pummelo fruits), hesperidin is under laboratory research for possible biological properties.[9][10][11] One area of research is focused on the possible chemopreventive effects of hesperidin,[12] but there is no current proof that hesperidin has this role in human cancer mechanisms.

See also[edit]

References[edit]

  1. ^ Inderjit, Dakshini, K. M. (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)". J Chem Ecol. 17 (8): 1585–91. doi:10.1007/BF00984690. PMID 24257882. 
  2. ^ Lebreton, M (1828). "Sur la matiere cristalline des orangettes, et analyse de ces fruits non encore developpes, famille des Hesperidees". Journal de Pharmacie et de Sciences Accessories. 14: 377ff. 
  3. ^ "Metabocard for Hesperidin (HMDB03265)". Human Metabolome Database, The Metabolomics Innovation Centre, Genome Canada. 11 February 2016. Retrieved 30 October 2016. 
  4. ^ "Citrus aurantium L.". Dr. Duke's Phytochemical and Ethnobotanical Databases. 6 Oct 2014. 
  5. ^ Tringali, C.; Spatafora, C.; Calì, V.; Simmonds, M. S. (2001). "Antifeedant constituents from Fagara macrophylla". Fitoterapia. 72 (5): 538–43. doi:10.1016/S0367-326X(01)00265-9. PMID 11429249. 
  6. ^ a b Peterson, J. J.; Beecher, G. R.; Bhagwat, S. A.; Dwyer, J. T.; Gebhardt, S. E.; Haytowitz, D. B.; Holden, J. M. (2006). "Flavanones in grapefruit, lemons, and limes: A compilation and review of the data from the analytical literature" (PDF). Journal of Food Composition and Analysis. 19 (Supplement): S74–S80. doi:10.1016/j.jfca.2005.12.009. 
  7. ^ Dolzhenko, Y.; Bertea, C. M.; Occhipinti, A.; Bossi, S.; Maffei, M. E. (2010). "UV-B modulates the interplay between terpenoids and flavonoids in peppermint (Mentha × piperita L.)". Journal of Photochemistry and Photobiology B: Biology. 100 (2): 67–75. doi:10.1016/j.jphotobiol.2010.05.003. 
  8. ^ Mazzaferro, L; Piñuel, L; Minig, M; Breccia, J. D. (2010). "Extracellular monoenzyme deglycosylation system of 7-O-linked flavonoid beta-rutinosides and its disaccharide transglycosylation activity from Stilbella fimetaria". Archives of Microbiology. 192 (5): 383–93. doi:10.1007/s00203-010-0567-7. PMID 20358178. 
  9. ^ Benavente-García, O.; Castillo, J. (2008). "Update on Uses and Properties of Citrus Flavonoids: New Findings in Anticancer, Cardiovascular, and Anti-inflammatory Activity". Journal of Agricultural and Food Chemistry. 56 (15): 6185–205. doi:10.1021/jf8006568. PMID 18593176. 
  10. ^ Hwang, S. L.; Shih, P. H.; Yen, G. C. (2012). "Neuroprotective Effects of Citrus Flavonoids". Journal of Agricultural and Food Chemistry. 60 (4): 877–85. doi:10.1021/jf204452y. PMID 22224368. 
  11. ^ Roohbakhsh, A.; Parhiz, H.; Soltani, F.; Rezaee, R.; Iranshahi, M. (2014). "Neuropharmacological properties and pharmacokinetics of the citrus flavonoids hesperidin and hesperetin — A mini-review". Life Sciences. 113 (1–2): 1–6. doi:10.1016/j.lfs.2014.07.029. PMID 25109791. 
  12. ^ Tanaka, T.; Tanaka, T.; Tanaka, M.; Kuno, T. (2012). "Cancer Chemoprevention by Citrus Pulp and Juices Containing High Amounts of β-Cryptoxanthin and Hesperidin". Journal of Biomedicine and Biotechnology. 2012: 1–10. doi:10.1155/2012/516981. PMC 3228311Freely accessible. PMID 22174562.