Hesperidin

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Not to be confused with hesperadin.
Hesperidin
Other names

Hesperetin 7-rutinoside[1]

Identifiers
CAS number 520-26-3 YesY
PubChem 10621
ChemSpider 10176 YesY
UNII E750O06Y6O YesY
ChEBI CHEBI:28775 YesY
ChEMBL CHEMBL449317 YesY
Jmol-3D images {{#if:O=C4c5c(O)cc(O[C@@H]2O[C@H](CO[C@@H]1O[C@H]([C@H](O)[C@@H](O)[C@H]1O)C)[C@@H](O)[C@H](O)[C@H]2O)cc5O[C@H](c3ccc(OC)c(O)c3)C4|Image 1
Properties
Molecular formula C28H34O15
Molar mass 610.56 g mol−1
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Hesperidin is a flavanone glycoside found abundantly in citrus fruits. Its aglycone form is called hesperetin. Its name is derived from the word "hesperidium", the kind of 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. It acts as an antioxidant according to in vitro studies.[3]

Pharmaceutical properties

Various preliminary studies reveal novel pharmaceutical properties, none of which has been confirmed as applicable to humans. Hesperidin reduced cholesterol[4] and blood pressure[5] in rats. In a mouse study, large doses of hesperidin decreased bone density loss.[6] Another animal study showed protective effects against sepsis.[7] In vitro and in laboratory research, hesperidin has anti-inflammatory effects.[8][9] Hesperidin is also a potential sedative, possibly acting through opioid or adenosine receptors.[10][11] Hesperidin exhibited pronounced anticancer activity against some selected human carcinoma cell lines.[12]

Some in vitro results applied only to the aglycone form. Hesperidin also showed potential to penetrate the blood–brain barrier in an in vitro model.[13]

Hesperidine and its synthetic derivative diosmin, components of the drug Daflon, can have a conservative role against the symptoms of varicose veins.

Sources

in Rutaceae
in Lamiaceae

Peppermint also contains hesperidin.[19]

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.

See also

References

  1. ↑ 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). Inderjit, Dakshini KM, J Chem Ecol. 1991, 17(8): 1585-91, doi:10.1007/BF00984690
  2. ↑ Lebreton (1828). Journal de Pharmacie et de sciences accessories. Vol 14, page 377ff
  3. ↑ Hirata A, Murakami Y, Shoji M, Kadoma Y, Fujisawa S (2005). "Kinetics of radical-scavenging activity of hesperetin and hesperidin and their inhibitory activity on COX-2 expression". Anticancer Res. 25 (5): 3367–74. PMID 16101151. 
  4. ↑ Monforte MT, Trovato A, Kirjavainen S, Forestieri AM, Galati EM, Lo Curto RB (September 1995). "Biological effects of hesperidin, a Citrus flavonoid. (note II): hypolipidemic activity on experimental hypercholesterolemia in rat". Farmaco 50 (9): 595–9. PMID 7495469. 
  5. ↑ Ohtsuki K, Abe A, Mitsuzumi H, et al. (December 2003). "Glucosyl hesperidin improves serum cholesterol composition and inhibits hypertrophy in vasculature". J. Nutr. Sci. Vitaminol. 49 (6): 447–50. PMID 14974738. 
  6. ↑ Chiba H, Uehara M, Wu J, et al. (June 2003). "Hesperidin, a citrus flavonoid, inhibits bone loss and decreases serum and hepatic lipids in ovariectomized mice". J. Nutr. 133 (6): 1892–7. PMID 12771335. 
  7. ↑ Kawaguchi K, Kikuchi S, Hasunuma R, Maruyama H, Yoshikawa T, Kumazawa Y (May 2004). "A citrus flavonoid hesperidin suppresses infection-induced endotoxin shock in mice". Biol. Pharm. Bull. 27 (5): 679–83. doi:10.1248/bpb.27.679. PMID 15133244. 
  8. ↑ Emim JA, Oliveira AB, Lapa AJ (February 1994). "Pharmacological evaluation of the anti-inflammatory activity of a citrus bioflavonoid, hesperidin, and the isoflavonoids, duartin and claussequinone, in rats and mice". J. Pharm. Pharmacol. 46 (2): 118–22. PMID 8021799. 
  9. ↑ Galati EM, Monforte MT, Kirjavainen S, Forestieri AM, Trovato A, Tripodo MM (November 1994). "Biological effects of hesperidin, a citrus flavonoid. (Note I): antiinflammatory and analgesic activity". Farmaco 40 (11): 709–12. PMID 7832973. 
  10. ↑ Loscalzo LM, Wasowski C, Paladini AC, Marder M (February 2008). "Opioid receptors are involved in the sedative and antinociceptive effects of hesperidin as well as in its potentiation with benzodiazepines". Eur. J. Pharmacol. 580 (3): 306–13. doi:10.1016/j.ejphar.2007.11.011. PMID 18048026. 
  11. ↑ Guzmán-Gutiérrez SL, Navarrete A (March 2009). "Pharmacological exploration of the sedative mechanism of hesperidin identified as the active principle of Citrus sinensis flowers". Planta Med. 75 (4): 295–301. doi:10.1055/s-0029-1185306. PMID 19219759. 
  12. ↑ Al-Ashaal HA, El-Sheltawy ST"Antioxidant capacity of hesperidin from citrus peel using electron spin resonance and cytotoxic activity against human carcinoma cell lines. Pharm Biol. 2011 Mar;49(3):276-82
  13. ↑ Youdim KA, Dobbie MS, Kuhnle G, Proteggente AR, Abbott NJ, Rice-Evans C (April 2003). "Interaction between flavonoids and the blood–brain barrier: in vitro studies". J. Neurochem. 85 (1): 180–92. doi:10.1046/j.1471-4159.2003.01652.x. PMID 12641740. 
  14. ↑ http://sun.ars-grin.gov:8080/npgspub/xsql/duke/plantdisp.xsql?taxon=276
  15. ↑ Antifeedant constituents from Fagara macrophylla. Corrado Tringali, Carmela Spatafora, Valeria Calı and Monique S.J Simmonds, Fitoterapia, June 2001, Volume 72, Issue 5, Pages 538–543, doi:10.1016/S0367-326X(01)00265-9
  16. ↑ Pearson, J. J.; Gary R. Beecher, Seema A. Bhagwat, Johanna T. Dwyer, Susan E. Gebhardt, David B. Haytowitz, Joanne M. Holden (2006). "Flavanones in grapefruit, lemons, and limes: A compilation and review of the data from the analytical literature". Journal of Food Composition and Analysis: S74–S80. Retrieved 25 January 2014. 
  17. ↑ Pearson, J. J.; Gary R. Beecher, Seema A. Bhagwat, Johanna T. Dwyer, Susan E. Gebhardt, David B. Haytowitz, Joanne M. Holden (2006). "Flavanones in grapefruit, lemons, and limes: A compilation and review of the data from the analytical literature". Journal of Food Composition and Analysis: S74–S80. Retrieved 25 January 2014. 
  18. ↑ Antifeedant constituents from Fagara macrophylla. Corrado Tringali, Carmela Spatafora, Valeria Calı and Monique S.J Simmonds, Fitoterapia, June 2001, Volume 72, Issue 5, Pages 538–543, doi:10.1016/S0367-326X(01)00265-9
  19. ↑ UV-B modulates the interplay between terpenoids and flavonoids in peppermint (Mentha × piperita L.). Yuliya Dolzhenko, Cinzia M. Bertea, Andrea Occhipinti, Simone Bossi and Massimo E. Maffei, Journal of Photochemistry and Photobiology B: Biology, Volume 100, Issue 2, 2 August 2010, Pages 67–75, doi:10.1016/j.jphotobiol.2010.05.003
Flavanones and their glycosides
Flavanones
O-methylated flavanones
C-methylated flavanones
Glycosides
Acetylated
Acetylated glycosides
  • Nirurin
Bond
  • O-glycosidic bond
  • N-glycosidic bond
  • S-glycosidic bond
  • C-glycosidic bond
Geometry
  • α-Glycoside
  • β-Glycoside
  • 1,4-Glycoside
  • 1,6-Glycoside
Glycone
Aglycone
  • Biochemical families: carbohydrates
    • alcohols
    • glycoproteins
    • glycosides
  • lipids
    • eicosanoids
    • fatty acids / intermediates
    • phospholipids
    • sphingolipids
    • steroids
  • nucleic acids
    • constituents / intermediates
  • proteins
    • Amino acids / intermediates
  • tetrapyrroles / intermediates
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