Hesperidin
| Hesperidin | |
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(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 |
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| Identifiers | |
| CAS number | 520-26-3  |
| PubChem | 10621 |
| ChemSpider | 10176 |
| UNII | E750O06Y6O |
| ChEBI | CHEBI:28775 |
| ChEMBL | CHEMBL449317 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C28H34O15 |
| Molar mass | 610.56 g mol−1 |
| Exact mass | 610.18977 |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Hesperidin is a flavanone glycoside found abundantly in citrus fruits. Its aglycone form is called hesperetin. Its name is derived from the Hesperides nymphs of Greek mythology. Hesperidin is believed to play a role in plant defense. It acts as an antioxidant according to in vitro studies.[1]
Various preliminary studies reveal novel pharmaceutical properties, none of which has been confirmed as applicable to humans. Hesperidin reduced cholesterol[2] and blood pressure[3] in rats. In a mouse study, large doses of hesperidin decreased bone density loss.[4] Another animal study showed protective effects against sepsis.[5] In vitro and in laboratory research, hesperidin has anti-inflammatory effects.[6][7] Hesperidin is also a potential sedative, possibly acting through opioid or adenosine receptors.[8][9]Hesperidin exhibited pronounced anticancer activity against some selected human carcinoma cell lines.[10]
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.[11]
[edit] References
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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
- ^ 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.
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