Aescin

β-Aescin (main component)
Names
	IUPAC names (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	11072-93-8 β-Aescin ; 6805-41-0 Aescin ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL505939 ;
ChemSpider	4977652 ;
ECHA InfoCard	100.027.164
KEGG	C08921 ;
PubChem CID	6476031;
UNII	RUU8G67GQM ;
	InChI InChI=1S/C55H86O24/c1-10-23(2)46(71)79-43-44(72-24(3)60)55(22-59)26(17-50(43,4)5)25-11-12-30-51(6)15-14-32(52(7,21-58)29(51)13-16-53(30,8)54(25,9)18-31(55)61)75-49-41(77-48-38(67)36(65)34(63)28(20-57)74-48)39(68)40(42(78-49)45(69)70)76-47-37(66)35(64)33(62)27(19-56)73-47/h10-11,26-44,47-49,56-59,61-68H,12-22H2,1-9H3,(H,69,70)/b23-10-/t26-,27+,28+,29+,30+,31+,32-,33+,34+,35-,36-,37+,38+,39-,40-,41+,42-,43-,44-,47-,48-,49+,51-,52+,53+,54+,55-/m0/s1 Key: AXNVHPCVMSNXNP-OXPBSUTMSA-N ; InChI=1/C55H86O24/c1-10-23(2)46(71)79-43-44(72-24(3)60)55(22-59)26(17-50(43,4)5)25-11-12-30-51(6)15-14-32(52(7,21-58)29(51)13-16-53(30,8)54(25,9)18-31(55)61)75-49-41(77-48-38(67)36(65)34(63)28(20-57)74-48)39(68)40(42(78-49)45(69)70)76-47-37(66)35(64)33(62)27(19-56)73-47/h10-11,26-44,47-49,56-59,61-68H,12-22H2,1-9H3,(H,69,70)/b23-10-/t26-,27+,28+,29+,30+,31+,32-,33+,34+,35-,36-,37+,38+,39-,40-,41+,42-,43-,44-,47-,48-,49+,51-,52+,53+,54+,55-/m0/s1 Key: AXNVHPCVMSNXNP-OXPBSUTMBO;
	SMILES CC=C(C)C(=O)OC1C(C2(C(CC1(C)C)C3=CCC4C5(CCC(C(C5CCC4(C3(CC2O)C)C)(C)CO)OC6C(C(C(C(O6)C(=O)O)OC7C(C(C(C(O7)CO)O)O)O)O)OC8C(C(C(C(O8)CO)O)O)O)C)CO)OC(=O)C;
Properties
Chemical formula	C55H86O24
Molar mass	1131.269 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Template:Distinguish2

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]^{[needs update]} 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 F_2α.^[1]^[4]^[5] Other possible mechanisms include serotonin antagonism and histamine antagonism and reduced catabolism of tissue mucopolysaccharides.^[1]

References

^ ^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.
^ Pittler MH, Ernst E (2006). Pittler MH (ed.). "Horse chestnut seed extract for chronic venous insufficiency". Cochrane Database Syst Rev (1): CD003230. doi:10.1002/14651858.CD003230.pub3. PMID 16437450.
^ 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.
^ 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.
^ 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

[Sirtori-1] 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 MH (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.

[1]

[2]

[3]

[4]

[5]