Hesperidin
Hesperidin is a phytoestrogen and flavonoid found in citrus plants that exhibits anti-hyperlipidemic, anti-osteoporotic, anti-inflammatory, analgesic, sedative, antinociceptive, and antioxidative activities. In vivo, hesperidin increases levels of HDL and decreases levels of LDL, triglycerides, and total lipids. In ovariectomized animals, hesperidin increases bone mineral density, preventing hormone-released changes in bone volume and thickness. Hesperidin also decreases carrageenan-induced edema and displays opioid-induced pain relief in various animal models. Additionally, hesperidin inhibits COX-2 activity and scavenges radicals.
References PubMed ID：:http://www.ncbi.nlm.nih.gov/pubmed/18930876
| Cas No. |
520-26-3 |
|---|---|
| Purity |
≥95% |
| Formula |
C28H34O15 |
| Formula Wt. |
610.56 |
| Chemical Name |
(2S)-7-[[6-O-(6-Deoxy-α-L-mannopyranosyl)-β-D- glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(3- hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one |
| IUPAC Name |
5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one |
| Synonym |
Hesperetin 7-rhamnoglucoside; Cirantin; Hesperetin-7- rutinoside |
| Melting Point |
258-262°C |
| Solubility |
Insoluble in water. Soluble in DMF and DMSO (30 mg/mL). Slightly soluble in ethanol and methanol (~1 mg/mL). |
| Appearance |
White to light brown powder |
Guzmán-Gutiérrez SL, Navarrete A. Pharmacological exploration of the sedative mechanism of hesperidin identified as the active principle of Citrus sinensis flowers. Planta Med. 2009 Mar;75(4):295-301. PMID: 19219759.
Loscalzo LM, Wasowski C, Paladini AC, et al. Opioid receptors are involved in the sedative and antinociceptive effects of hesperidin as well as in its potentiation with benzodiazepines. Eur J Pharmacol. 2008 Feb 12;580(3):306-13. PMID: 18048026.
Hirata A, Murakami Y, Shoji M, et al. Kinetics of radical-scavenging activity of hesperetin and hesperidin and their inhibitory activity on COX-2 expression. Anticancer Res. 2005 Sep-Oct;25(5):3367-74. PMID: 16101151.
Chiba H, Uehara M, Wu J, et al. Hesperidin, a citrus flavonoid, inhibits bone loss and decreases serum and hepatic lipids in ovariectomized mice. J Nutr. 2003 Jun;133(6):1892-7. PMID: 12771335.
Monforte MT, Trovato A, Kirjavainen S, et al. Biological effects of hesperidin, a Citrus flavonoid. (note II): hypolipidemic activity on experimental hypercholesterolemia in rat. Farmaco. 1995 Sep;50(9):595-9. PMID: 7495469.
Emim JA, Oliveira AB, Lapa AJ. 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. 1994 Feb;46(2):118-22. PMID: 8021799.
