508-93-0

Basic information

• Product Name: EVOMONOSIDE
• Synonyms: a-hydroxy-;digitoxigenin3-rhamnoside;digitoxigeninrhamnoside;evomonosid;EVOMONOSIDE;DIGITOXIGENIN-3-O-ALPHA-L-RHAMNOPYRANOSIDE;DIGITOXIGENIN-3-O-A-L-RHAMNOPYRANOSIDE;DIGITOXIGENIN-3-O-RHAMNOSIDE
• CAS NO: 508-93-0
• Molecular Formula: C₂₉H₄₄O₈
• Molecular Weight: 520.65
• EINECS: 208-088-4
• Product Categories: Cardioglycosides & Glycosides;Carbohydrates & Derivatives;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
• Mol File: 508-93-0.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 694.6°Cat760mmHg
• Flash Point: 225.4°C
• Appearance: /
• Density: 1.31g/cm³
• CAS DataBase Reference: EVOMONOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: EVOMONOSIDE(508-93-0)
• EPA Substance Registry System: EVOMONOSIDE(508-93-0)

Safety Data

• Hazardous Substances Data: 508-93-0(Hazardous Substances Data)

Usage

Uses

Evomonoside, a Digitoxigenin analogue was isolated from seeds of L. apetalum, and showed antitumor activity.

Definition

ChEBI: A cardenolide glycoside consisting of digitoxigenin having an alpha-L-rhamnosyl moiety attached at the O3-position.

Upstream product

• 14917-55-6 methyl 6-deoxy-α-L-mannopyranoside 
• 161007-95-0 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyltrichloroacetimidate 
• 143-62-4 (+)-digitoxigenin 
• 71-63-6 digitoxin 
• 4208-64-4 (S)-1-(2-furanyl)ethanol 
• 247244-65-1 L-aculose 
• 33156-32-0 C₂₉H₄₂O₆ 
• 1256497-84-3 C₂₉H₄₀O₆ 
• 1192-62-7 1-(2-furyl)-1-ethanone 
• 865484-73-7 tert-butyl ((2S,6S)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl) carbonate 
• 103368-09-8 2,3,4-tri-O-benzyl-β-L-rhamnopyranose 1-O-trichloroacetimidate 
• 103383-31-9 3,5-dinitro-2-pyridyl-2,3,4-tri-O-benzyl-α-L-rhamnopyranose 
• 86795-38-2 2,3,4-tri-O-(phenylmethyl)-α-L-rhamnopyranoside 
• 83866-10-8 (2S,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yl 2,2,2-trichloroacetimidate 

Relevant articles and documents

Pregnanes That Bind to the Digitalis Receptor: Synthesis of 14-Hydroxy-5β,14β-pregnane Glycosides from Digitoxin and Digitoxigenin

The preparation of the mono-, bis-, and trisdigitoxosides of 14-hydroxy-5β,14β-pregnan-20-one and 14,20β-dihydroxy-5β,14β-pregnane by two routes, based on the conversion of the α,β-unsaturated γ-lactone in digitoxin to the 20-ketone and 20β-alcohol by ozonolysis and zinc-acetic acid treatment followed by lithium tri-tert-butoxyaluminum hydride reduction, are described.Synthesis of the α-L-rhamnoside derivatives is described also.Structures were confirmed by 1H and 13C NMR spectra.These derivatives show strong interaction with the cardiac glycoside receptor of heart muscle in an ouabain radioligand binding assay.Structure-activity relationships which are reported for glycosides and genins show that the α-L-rhamnoside derivatives are more potent than the β-D-digitoxoside or the β-D-glucoside and that the β-D-glucosides are more potent than the mono-, bis-, and trisdigitoxosides.Potency is not increased by the addition of the second and third digitoxose units.

Modular Total Synthesis and Cell-Based Anticancer Activity Evaluation of Ouabagenin and Other Cardiotonic Steroids with Varying Degrees of Oxygenation

A Cu(II)-catalyzed diastereoselective Michael/aldol cascade approach is used to accomplish concise total syntheses of cardiotonic steroids with varying degrees of oxygenation including cardenolides ouabagenin, sarmentologenin, 19-hydroxysarmentogenin, and 5-epi-panogenin. These syntheses enabled the subsequent structure activity relationship (SAR) studies on 37 synthetic and natural steroids to elucidate the effect of oxygenation, stereochemistry, C3-glycosylation, and C17-heterocyclic ring. Based on this parallel evaluation of synthetic and natural steroids and their derivatives, glycosylated steroids cannogenol-l-α-rhamnoside (79a), strophanthidol-l-α-rhamnoside (92), and digitoxigenin-l-α-rhamnoside (97) were identified as the most potent steroids demonstrating broad anticancer activity at 10-100 nM concentrations and selectivity (nontoxic at 3 μM against NIH-3T3, MEF, and developing fish embryos). Further analyses indicate that these molecules show a general mode of anticancer activity involving DNA-damage upregulation that subsequently induces apoptosis.

Synthesis and evaluation of the α- D -/α-l-rhamnosyl and amicetosyl digitoxigenin oligomers as antitumor agents

A highly regio- and stereoselective asymmetric synthesis of rhamnosyl- and amicetosyl-digitoxigenin analogues has been established via palladium-catalyzed glycosylation followed by bis-/tris-dihydroxylation or bis-/tris-diimide reduction. The α-l-rhamnose and α-l-amicetose digitoxin monosaccharide analogues displayed stronger apoptosis inducing activity and cytotoxicity against nonsmall cell human lung cancer cells (NCI-H460) than its d-diastereomeric isomers in a sugar-chain length dependent manner.

C5′-alkyl substitution effects on digitoxigenin α-l-glycoside cancer cytotoxicity

A highly regio- and stereoselective asymmetric synthesis of various C5′-alkyl side chains of rhamnosyl- and amicetosyl-digitoxigenin analogues has been established via palladium-catalyzed glycosylation with postglycosylated dihydroxylation or diimide reduction. The C5′-methyl group in both α-l-rhamnose and α-l-amicetose digitoxin analogues displayed a steric directed apoptosis induction and tumor growth inhibition against nonsmall cell human lung cancer cells (NCI-H460). The antitumor activity is significantly reduced when the steric hindrance is increased at the C5′-stereocenter.