Hesperidin

Not to be confused with hesperadin.
Hesperidin
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 Yes
ChEBI CHEBI:28775 Yes
ChEMBL ChEMBL449317 Yes
ChemSpider 10176 Yes
Jmol-3D images Image
PubChem 10621
UNII E750O06Y6O Yes
Properties
Molecular formula
 C28H34O15
Molar mass 610.56 g·mol−1
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 Yes verify (what is: Yes/?)
Infobox references

Hesperidin is a flavanone 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]

Hesperidin is believed to play a role in plant defense.

Sources

in Rutaceae
in Lamiaceae

Peppermint also contains hesperidin.[6]

Metabolism

Hesperidin 6-O-alpha-L-rhamnosyl-beta-D-glucosidase is an enzyme that uses hesperidin and H2O to produce hesperetin and rutinose. It is found in the hyphomycetes species Stilbella fimetaria.

Research

As a flavanone found in citrus fruits (such as oranges, lemons or pummelo fruits), hesperidin is under laboratory research for possible biological properties.[7][8][9] One area of research is focused on the possible chemopreventive effects of hesperidin,[10] but there is no current proof that hesperidin has this role in human cancer mechanisms.

See also

References

  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 (1828). Journal de Pharmacie et de sciences accessories 14: 377ff. Missing or empty |title= (help)
  3. ↑ "Citrus aurantium L.". Dr. Duke's Phytochemical and Ethnobotanical Databases. 6 Oct 2014.
  4. ↑ 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.
  5. ↑ 5.0 5.1 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.
  6. ↑ 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.
  7. ↑ 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.
  8. ↑ 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.
  9. ↑ 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.
  10. ↑ 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. doi:10.1155/2012/516981.