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Aescin

November 28, 2023

Not to be confused with aesculin, an unrelated coumarin glycoside also found in horse chestnut.

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 component in horse chestnut, and is responsible for most of its medicinal properties. The main active compound of aescin is β-aescin, although the mixture also contains various other components including α-aescin, protoescigenin, barringtogenol, cryptoescin and benzopyrones.[1]

β-Aescin (main component)
Names
IUPAC name
β-D-Glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-(22α-(acetyloxy)-16α,24,28-trihydroxy-21β-{[(2Z)-2-methylbut-2-enoyl]oxy}olean-12-en-3β-yl β-D-glucopyranosiduronic acid)
Systematic IUPAC name
(2S,3S,4S,5R,6R)-6-{[(3S,4S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-9-(Acetyloxy)-8-hydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-{[(2Z)-2-methylbut-2-enoyl]oxy}-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-4-hydroxy-3,5-bis{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid
Other names
Escin
Identifiers
  • 6805-41-0 Aescin Y
  • 11072-93-8 β-Aescin Y
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL505939 Y
ChemSpider
  • 4977652 Y
ECHA InfoCard 100.027.164
KEGG
  • C08921 N
  • 6476031
UNII
  • RUU8G67GQM Aescin Y
  • QYK0D6H79O β-Aescin Y
  • 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 Y
    Key: AXNVHPCVMSNXNP-OXPBSUTMSA-N Y
  • 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
  • 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
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).
N verify (what is YN ?)

Evidence suggests that aescin, especially pure β-aescin, is a safe and effective treatment for short-term treatment of chronic venous insufficiency;[2][3] however, more high quality randomized controlled trials are required to confirm the effectiveness.[3] Horse chestnut extract may be as effective and well tolerated as the use of compression stockings.[3]

Mechanism of action edit

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][6] Other possible mechanisms include serotonin antagonism and histamine antagonism and reduced catabolism of tissue mucopolysaccharides.[4]

References edit

  1. ^ Ramelet, Albert-Adrien. "Venoactive Drugs". Sclerotherapy: treatment of varicose and telangiectatic leg veins (6th ed.). Elsevier Science Health Science. pp. 426–434. ISBN 978-0-323-37726-3.
  2. ^ Goldman, Mitchel P. (2016). Sclerotherapy : treatment of varicose and telangiectatic leg veins. Weiss, Robert A.,, Guex, Jean-Jerome (6th ed.). Amsterdam: Elsevier Science Health Science. ISBN 978-0-323-37727-0. OCLC 959274899.
  3. ^ a b c Pittler, Max H.; Ernst, Edzard (2012-11-14). "Horse chestnut seed extract for chronic venous insufficiency". The Cochrane Database of Systematic Reviews. 11: CD003230. doi:10.1002/14651858.CD003230.pub4. ISSN 1469-493X. PMC 7144685. PMID 23152216.
  4. ^ a b Sirtori CR (September 2001). "Aescin: pharmacology, pharmacokinetics and therapeutic profile". Pharmacol. Res. 44 (3): 183–193. doi:10.1006/phrs.2001.0847. PMID 11529685.
  5. ^ 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.
  6. ^ 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 edit

November 28, 2023
aescin, confused, with, aesculin, unrelated, coumarin, glycoside, also, found, horse, chestnut, escin, mixture, saponins, with, anti, inflammatory, vasoconstrictor, vasoprotective, effects, found, aesculus, hippocastanum, horse, chestnut, main, active, compone. Not to be confused with aesculin an unrelated coumarin glycoside also found in horse chestnut 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 component in horse chestnut and is responsible for most of its medicinal properties The main active compound of aescin is b aescin although the mixture also contains various other components including a aescin protoescigenin barringtogenol cryptoescin and benzopyrones 1 b Aescin main component NamesIUPAC name b D Glucopyranosyl 1 2 b D glucopyranosyl 1 4 22a acetyloxy 16a 24 28 trihydroxy 21b 2Z 2 methylbut 2 enoyl oxy olean 12 en 3b yl b D glucopyranosiduronic acid Systematic IUPAC name 2S 3S 4S 5R 6R 6 3S 4S 4aR 6aR 6bS 8R 8aR 9R 10R 12aS 14aR 14bR 9 Acetyloxy 8 hydroxy 4 8a bis hydroxymethyl 4 6a 6b 11 11 14b hexamethyl 10 2Z 2 methylbut 2 enoyl oxy 1 2 3 4 4a 5 6 6a 6b 7 8 8a 9 10 11 12 12a 14 14a 14b icosahydropicen 3 yl oxy 4 hydroxy 3 5 bis 2S 3R 4S 5S 6R 3 4 5 trihydroxy 6 hydroxymethyl oxan 2 yl oxy oxane 2 carboxylic acidOther names EscinIdentifiersCAS Number 6805 41 0 Aescin Y11072 93 8 b Aescin Y3D model JSmol Interactive imageChEMBL ChEMBL505939 YChemSpider 4977652 YECHA InfoCard 100 027 164KEGG C08921 NPubChem CID 6476031UNII RUU8G67GQM Aescin YQYK0D6H79O b Aescin YInChI 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 YKey AXNVHPCVMSNXNP OXPBSUTMSA N YInChI 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 s1Key AXNVHPCVMSNXNP OXPBSUTMBOSMILES 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 CPropertiesChemical formula C 55H 86O 24Molar mass 1131 269 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Evidence suggests that aescin especially pure b aescin is a safe and effective treatment for short term treatment of chronic venous insufficiency 2 3 however more high quality randomized controlled trials are required to confirm the effectiveness 3 Horse chestnut extract may be as effective and well tolerated as the use of compression stockings 3 Mechanism of action editAescin 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 F2a 4 5 6 Other possible mechanisms include serotonin antagonism and histamine antagonism and reduced catabolism of tissue mucopolysaccharides 4 References edit Ramelet Albert Adrien Venoactive Drugs Sclerotherapy treatment of varicose and telangiectatic leg veins 6th ed Elsevier Science Health Science pp 426 434 ISBN 978 0 323 37726 3 Goldman Mitchel P 2016 Sclerotherapy treatment of varicose and telangiectatic leg veins Weiss Robert A Guex Jean Jerome 6th ed Amsterdam Elsevier Science Health Science ISBN 978 0 323 37727 0 OCLC 959274899 a b c Pittler Max H Ernst Edzard 2012 11 14 Horse chestnut seed extract for chronic venous insufficiency The Cochrane Database of Systematic Reviews 11 CD003230 doi 10 1002 14651858 CD003230 pub4 ISSN 1469 493X PMC 7144685 PMID 23152216 a b Sirtori CR September 2001 Aescin pharmacology pharmacokinetics and therapeutic profile Pharmacol Res 44 3 183 193 doi 10 1006 phrs 2001 0847 PMID 11529685 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 editInformation on horse chestnut extract from Memorial Sloan Kettering Cancer Center CID 76967409 from PubChem alpha Aescin Retrieved from https en wikipedia org w index php title Aescin amp oldid 1152172305, wikipedia, wiki, book, books, library,

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