Hesperidin

from Wikipedia, the free encyclopedia
Structural formula
Structure of hesperidin
General
Surname Hesperidin
other names
  • Cirantine
  • Hesperidoside
  • Hesperetin-7- O -rutinosid
  • Hesperetin-7-rhamnoglucoside
  • (2 S ) -7 - ((6- O - (6- Deoxy -α- L -mannopyranosyl) -β- D -glucopyranosyl) oxy) -2,3-dihydro-5-hydroxy-2- (3-hydroxy -4-methoxyphenyl) -4 H -1-benzopyran-4-one
  • HESPERIDIN ( INCI )
Molecular formula C 28 H 34 O 15
Brief description

fine dendritic needles, light brown

External identifiers / databases
CAS number 520-26-3
EC number 208-288-1
ECHA InfoCard 100.007.536
PubChem 10621
ChemSpider 10176
DrugBank DB04703
Wikidata Q385937
properties
Molar mass 610.56 g · mol -1
Physical state

firmly

Melting point

258–262 ° C ( softens at 250 ° C )

solubility
safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
Toxicological data

1000 mg kg −1 ( LD 50 ,  mouse ,  ip )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

As a glycoside from the flavanone hesperetin and the disaccharide rutinose, hesperidin belongs to the group of flavonoids , specifically to the bioflavonoids .

history

Hesperidin was first isolated in 1828 by the French pharmacist Lebreton from the white inner layer of the peel of citrus fruits ( mesocarp , albedo).

Occurrence

Whole and sliced ​​oranges

Hesperidin is the main flavonoid of the peels of oranges and lemons and occurs there alongside hesperetin . In some types of oranges, it makes up 4.1% of the dry matter of the peel. It's also common in other citrus fruits . It can be extracted from orange peel, taking care that a larger amount of the white inner layer is extracted with it. Sweet oranges ( Citrus sinensis ) and tangelos are considered the most important source of this bioflavonoid in the diet.

Orange juice with crushed pulp ( " pulp ") contains more of this flavonoid than those without.

properties

Hesperidin is chiral . The specific rotation value of natural hesperidin is -76 ° (c = 2.0 M in pyridine at 20 ° C).

Pharmacological effect

The hesperidin content in the plant protects against certain fungal infections.

Hesperidin is used medically in the form of a combination preparation with diosmin against venous leg problems such as varicose veins and, in addition to its effect as an antioxidant, also shows an increase in venous tone and lymphatic drainage , which has been proven in placebo-controlled studies in people with chronic venous insufficiency .

Clinical studies have also shown the good effect of tablets with diosmin and hesperidin for hemorrhoids .

According to results of animal experiments hesperidin also has anti-inflammatory and analgesic effect and lowers cholesterol and triglyceride levels in the blood.

Because of these effects, hesperidin is now widely advertised as a dietary supplement .

Web links

See also

Individual evidence

  1. ↑ Entry on HESPERIDIN in the CosIng database of the EU Commission, accessed on April 6, 2020.
  2. ↑ a b c d e f g h The Merck Index , 12th edition. Edition, Merck & Co. , Whitehouse Station, New Jersey, USA 1996.
  3. ↑ a b c Hesperidin data sheet from Sigma-Aldrich , accessed on February 7, 2019 ( PDF ).
  4. ↑ Sax, N. Irving; Lewis, RJ Dangerous Properties of Industrial Materials, 7th ed., Van Nostrand, New York: 1989.
  5. ^ Lebreton (1828). Journal de Pharmacie et de sciences accessories. Vol. 14, p. 377ff.
  6. ↑ a b Ortuño, A. et al. (2006): Citrus paradisi and Citrus sinensis flavonoids: Their influence in the defense mechanism against Penicillium digitatum. In: Food Chemistry . Vol. 98, No. 2, pp. 351-358. doi : 10.1016 / j.foodchem.2005.06.017
  7. ↑ infomed.ch: veins means , Section Diosmin, hesperidin , accessed on February 9, 2013.
  8. ↑ Cospite, M. (1994): Double-blind, placebo-controlled evaluation of clinical activity and safety of Daflon 500 mg in the treatment of acute haemorrhoids. In: Angiology. Vol. 45, pp. 566-573.
  9. ↑ Galati, EM et al. (1994): Biological effects of hesperidin, a citrus flavonoid. (Grade I): anti-inflammatory and analgesic activity. In: Farmaco. Vol. 40, pp. 709-712. PMID 7832973 .
  10. ↑ Monforte, MT et al. (1995): Biological effects of hesperidin, a Citrus flavonoid. (note II): hypolipidemic activity on experimental hypercholesterolemia in rat. In: Farmaco. Vol. 50, pp. 595-599. PMID 7495469 .