Aescin

Not to be confused with aesculin, an unrelated coumarin glycoside also found in horse chestnut.
β-Aescin (main component)
IUPAC name

(2S,3S,4S,5R,6R)-6-{[(3S,4S,4aR,6aR, 6bS,8R,8aR,9R,10R,12aS,14aR,14bR)
-9-acetoxy-8-hydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11, 14b-hexamethyl-10-[2-methyl-1-oxobut-2-enoxy]-1,2,3,4a,5,6,7,
8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-4-hydroxy-
3,5-bis{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-
2-tetrahydropyranyl]oxy}-2-tetrahydropyrancarboxylic acid
Other names

Escin
Identifiers
CAS number 6805-41-0 N
PubChem 6476031
ChemSpider 4977652 Y
UNII RUU8G67GQM Y
KEGG C08921 N
ChEMBL CHEMBL505939 Y
Jmol-3D images Image 1
Properties
Molecular formula C55H86O24
Molar mass 1131.26 g mol−1
 N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Aescin or escin is a mixture of saponins with anti-inflammatory, vasoconstrictor and vasoprotective effects found in Aesculus hippocastanum (the horse chestnut). Aescin is the main active compound in horse chestnut, and is responsible for most of its medicinal properties.

High-quality evidence suggests aescin is a safe and effective treatment for chronic venous insufficiency.[1][2] In one randomized controlled trial, horse chestnut extract was found to be as effective and well-tolerated as use of compression stockings.[3]

Mechanism of action

Aescin appears to produce effects through a wide range of mechanisms. It induces endothelial nitric oxide synthesis by making endothelial cells more permeable to calcium ions, and also induces release of prostaglandin F2α.[4][5][1] Other possible mechanisms include serotonin antagonism and histamine antagonism and reduced catabolism of tissue mucopolysaccharides.[1]

References

  1. ^ a b c Sirtori CR (September 2001). "Aescin: pharmacology, pharmacokinetics and therapeutic profile". Pharmacol. Res. 44 (3): 183–193. doi:10.1006/phrs.2001.0847. PMID 11529685. 
  2. ^ Pittler MH, Ernst E (2006). Pittler, Max H. ed. "Horse chestnut seed extract for chronic venous insufficiency". Cochrane Database Syst Rev (1): CD003230. doi:10.1002/14651858.CD003230.pub3. PMID 16437450. 
  3. ^ Diehm C, Trampisch HJ, Lange S, Schmidt C (February 1996). "Comparison of leg compression stocking and oral horse-chestnut seed extract therapy in patients with chronic venous insufficiency". Lancet 347 (8997): 292–294. doi:10.1016/S0140-6736(96)90467-5. PMID 8569363. 
  4. ^ Carrasco OF, Vidrio H (July 2007). "Endothelium protectant and contractile effects of the antivaricose principle escin in rat aorta". Vascul. Pharmacol. 47 (1): 68–73. doi:10.1016/j.vph.2007.04.003. PMID 17512261. 
  5. ^ Berti F, Omini C, Longiave D (August 1977). "The mode of action of aescin and the release of prostaglandins". Prostaglandins 14 (2): 241–249. doi:10.1016/0090-6980(77)90169-1. PMID 897216. 

External links