Escin

• CAT Number: R024765
• CAS Number: 6805-41-0
• Molecular Formula: C55H86O24
• Molecular Weight: 1131.26
• Purity: ≥95%
• Synonyms: 3-(4-O-β-D-glucopyranosyl-2-O-β-D-xylopyranosyl-β-D-glucopyranuronoside)escigenin 3-Hydroxy-2-methylbutyrate Acetate; 3,5-Epoxypicene, escin deriv.; Oleanane Escin deriv.; Aescin; Aescine; Aescusan; Ba 2672; Escusan; Eskuzan; Flebostasin Retard?Venoc
• Target: Apoptosis
• Storage: Store at -20°C
• IUPAC Name: (2S,3S,4S,5R,6R)-6-[[(4S,6bS,8R,9R)-9-acetyloxy-8-hydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(E)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
• 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?/m1/s1
• InChIKey: AXNVHPCVMSNXNP-YSYFQUGBSA-N
• 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

Escin (CAS 6805-41-0) a natural mixture of triterpenoid saponins isolated from horse chestnut (Aesculus hippocastanum) seeds, is used and studied as a vasoprotective anti-inflammatory, anti-edematous and anti-nociceptive agent. It may be used to study its pharmacokinetics, safety and efficacy as a chemosensitizer and modulator of NF-κ B cell signaling.

Reference

1.Wu, Xiu-Jun, et al. "Comparative pharmacokinetics and the bioavailability of escin Ib and isoescin Ib following the administration of escin, pure escin Ib and isoescin Ib in rats." Journal of ethnopharmacology 151.2 (2014): 839-845.
2.Int Arch Allergy Immunol. 2013;161(1):44-52. doi: 10.1159/000343289. Epub 2012 

Dec 14.Escin inhibits type I allergic dermatitis in a novel porcine model.Sipos W(1), Reutterer B, Frank M, Unger H, Grassauer A, Prieschl-Grassauer E, Doerfler P.

 

BACKGROUND: Current standard medications for the treatment of allergic inflammation consist primarily of glucocorticoids and anti-histamines, but adverse side effects or insufficient responsiveness by patient subpopulations illustrate the need for safe and novel alternatives. Thus, there is a demand to develop a porcine model that is able to mimic mast cell-mediated type I hypersensitivity. Previously, we found that escin, a pharmacologically active mix of triterpene saponins from horse chestnut extracts, exerts anti-allergic effects in murine models and merits further investigation as an anti-allergic therapeutic.

METHODS: We developed a new porcine model of allergic dermatitis based on a clinical pricktest protocol. Histamine clearly provoked erythema and swelling at the prick site, whereas the mast cell-degranulating compound 48/80 even more pronounced caused wheal and flare reactions known from the human prick response. This model was used to test the anti allergic efficacy of orally applied escin.

RESULTS: Oral pretreatment of animals with escin strongly inhibited the allergic skin response induced by compound 48/80 in a dose-dependent manner. Additional in vitro data from murine mast cells indicate an engagement of the glucocorticoid receptor pathway upon treatment with escin.

CONCLUSIONS: This model provides a valuable and easy-to-set-up tool for preclinical studies of mast cell-inhibiting compounds. The successful implementation of this model supports the development of oral escin applications as a novel anti-allergic therapy.