Aescin

Last updated
β-Aescin (main component)
Beta-Aescin.svg
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
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.027.164 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • 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 Yes check.svgY
    Key: AXNVHPCVMSNXNP-OXPBSUTMSA-N Yes check.svgY
  • 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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

Contents

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

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. [4] [5] [6] Other possible mechanisms include serotonin antagonism and histamine antagonism and reduced catabolism of tissue mucopolysaccharides. [4]

Related Research Articles

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Varicose veins, also known as varicoses, are a medical condition in which superficial veins become enlarged and twisted. These veins typically develop in the legs, just under the skin. Varicose veins usually cause few symptoms. However, some individuals may experience fatigue or pain in the area. Complications can include bleeding or superficial thrombophlebitis. Varices in the scrotum are known as a varicocele, while those around the anus are known as hemorrhoids. Due to the various physical, social, and psychological effects of varicose veins, they can negatively affect one's quality of life.

<span class="mw-page-title-main">Vein</span> Blood vessels that carry blood towards the heart

Veins are blood vessels in the circulatory system of humans and most other animals that carry blood towards the heart. Most veins carry deoxygenated blood from the tissues back to the heart; exceptions are those of the pulmonary and fetal circulations which carry oxygenated blood to the heart. In the systemic circulation, arteries carry oxygenated blood away from the heart, and veins return deoxygenated blood to the heart, in the deep veins.

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The great saphenous vein(GSV), or long saphenous vein; ) is a large, subcutaneous, superficial vein of the leg. It is the longest vein in the body, running along the length of the lower limb, returning blood from the foot, leg and thigh to the deep femoral vein at the femoral triangle.

<span class="mw-page-title-main">Vascular surgery</span> Medical specialty, operative procedures for the treatment of vascular disorders

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<i>Aesculus hippocastanum</i> Species of tree in the lychee family Sapindaceae

Aesculus hippocastanum, the horse chestnut, is a species of flowering plant in the maple, soapberry and lychee family Sapindaceae. It is a large, deciduous, synoecious (hermaphroditic-flowered) tree. It is also called horse-chestnut, European horsechestnut, buckeye, and conker tree. It is not to be confused with the Spanish chestnut, Castanea sativa, which is a tree in another family, Fagaceae.

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<span class="mw-page-title-main">Diosmin</span> Chemical compound

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Vascular disease is a class of diseases of the vessels of the circulatory system in the body, including blood vessels – the arteries and veins, and the lymphatic vessels. Vascular disease is a subgroup of cardiovascular disease. Disorders in this vast network of blood and lymph vessels can cause a range of health problems that can sometimes become severe, and fatal. Coronary heart disease for example, is the leading cause of death for men and women in the United States.

<span class="mw-page-title-main">Chronic venous insufficiency</span> Medical condition

Chronic venous insufficiency (CVI) is a medical condition in which blood pools in the veins, straining the walls of the vein. The most common cause of CVI is superficial venous reflux which is a treatable condition. As functional venous valves are required to provide for efficient blood return from the lower extremities, this condition typically affects the legs. If the impaired vein function causes significant symptoms, such as swelling and ulcer formation, it is referred to as chronic venous disease. It is sometimes called chronic peripheral venous insufficiency and should not be confused with post-thrombotic syndrome in which the deep veins have been damaged by previous deep vein thrombosis.

Hydroxyethylrutosides are hydroxyethyl derivatives of rutosides. Examples include:

<span class="mw-page-title-main">Paolo Zamboni</span>

Paolo Zamboni is an Italian doctor and scientist. He is full Professor and Director of the School of Vascular Surgery at the University of Ferrara in Italy.

Daflon is an oral micronized purified phlebotonic flavonoid fraction containing 90% diosmin and 10% hesperidin. It is manufactured by Laboratoires Servier and often used to treat or manage disorders of the blood vessels. Flavonoids are a type of phytochemical that have been associated with various effects on human health and are a component of many different pharmaceutical, nutraceutical, and cosmetic preparations. Diosmin is a flavone glycoside that is derived from hesperidin. Hesperidin is a flavone that is extracted from citrus fruits.

<span class="mw-page-title-main">Pelvic congestion syndrome</span> Medical condition

Pelvic congestion syndrome, also known as pelvic vein incompetence, is a long-term condition believed to be due to enlarged veins in the lower abdomen. The condition may cause chronic pain, such as a constant dull ache, which can be worsened by standing or sex. Pain in the legs or lower back may also occur.

<span class="mw-page-title-main">Giacomini vein</span>

The Giacomini vein, or cranial extension of the small saphenous vein is a communicating vein between the great saphenous vein (GSV) and the small saphenous vein (SSV). It is named after the Italian anatomist Carlo Giacomini (1840–1898). The Giacomini vein courses the posterior thigh as either a trunk projection, or tributary of the SSV. In one study it was found in over two-thirds of limbs. Another study in India found the vein to be present in 92% of those examined. It is located under the superficial fascia and its insufficiency seemed of little importance in the majority of patients with varicose disease, but the use of ultrasonography has highlighted a new significance of this vein. It can be part of a draining variant of the SSV which continues on to reach the GSV at the proximal third of the thigh instead of draining into the popliteal vein. The direction of its flow is usually anterograde but it can be retrograde when this vein acts as a bypass from an insufficient GSV to SSV to call on this last one to collaborate in draining. Many discussions exist about this vein, some of them confusing to a non-expert reader. Insufficiency in the Giacomini vein can present in isolation but is mostly seen together with a GSV insufficiency. It has been shown to be effectively treated either with endovenous laser ablation or by ultrasound guided sclerotherapy.

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CHIVA method is a type of surgery used to treat varicose veins that occur as a result of long term venous insufficiency. The term is a French acronym for Conservatrice Hémodynamique de l'Insuffisance Veineuse en Ambulatoire.

References

  1. Ramelet A (24 November 2016). "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. 1 2 3 Pittler MH, Ernst E (2012-11-14). "Horse chestnut seed extract for chronic venous insufficiency". The Cochrane Database of Systematic Reviews. 11 (11): CD003230. doi:10.1002/14651858.CD003230.pub4. ISSN   1469-493X. PMC   7144685 . PMID   23152216.
  4. 1 2 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.