Hesperidin

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Not to be confused with hesperadin.
Hesperidin
Hesperidin structure.svg
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 Image 1
Properties
Molecular formula C28H34O15
Molar mass 610.56 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
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[edit]

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.

Possible cardioprotective effects[edit]

Hesperidin is a flavanone found in citrus fruits (such as oranges, lemons or pummelo fruits) that has antioxidant properties in laboratory studies.[14][15][16] In basic research, it has biological effects on rats and mice, such as cholesterol reduction, blood pressure reduction and anti-inflammatory abilities.[14][15][16]

In numerous studies, doxorubicin, a cancer chemotherapeutic, was not as damaging to cardiac tissues when hesperidin was applied.[14][15] Pre-treatment with hesperidin prior to doxorubicin also decreased serum nitric oxide levels due to inhibition of nitric oxide synthase.[14] Additionally, hesperidin protected cell integrity as shown in this one study by reduction in the number of cells undergoing apoptosis induced by doxorubicin.[15][16]

Sources[edit]

in Rutaceae
in Lamiaceae

Peppermint also contains hesperidin.[20]

Metabolism[edit]

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[edit]

References[edit]

  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. doi:10.3177/jnsv.49.447. 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. doi:10.1111/j.2042-7158.1994.tb03753.x. 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. ^ a b c d Abdel-Raheem IT, Abdel-Ghany AA (June 2009). "Hesperidin alleviates doxorubicin-induced cardiotoxicity in rats". Journal of the Egyptian Nat. Cancer Inst. 21(2): 175-184.
  15. ^ a b c d Trivedi PP, Kushwaha S, Tripathi DN, Jena GB (2011). "Cardioprotective effects of hesperetin against doxorubicin-induced oxidative stress and DNA damage in rats". Cardiovasc Toxicol. 11: 215-225.
  16. ^ a b c Chularojmontri I, Gerdprasert O, Wattanapitayakul SK (2013). "Pummelo protects doxorubicin-indiced cardiac cell death by reducing oxidative stress, modifying glutathione transferase expression, and preventing cellular senescence". Evidence-Based Complementary and Alternative Medicine 2013: 254835-254843
  17. ^ "Citrus aurantium L.". Dr. Duke's Phytochemical and Ethnobotanical Databases. 3 April 2014. Retrieved 3 April 2014. 
  18. ^ a b 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. ^ a b 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. 
  20. ^ 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