Verbascoside
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Verbascoside
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CAS No:
61276-17-3
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Formula:
C29H36O15
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Chemical Name:
Verbascoside
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Synonyms:
β-D-Glucopyranoside,2-(3,4-dihydroxyphenyl)ethyl 3-O-(6-deoxy-α-L-mannopyranosyl)-,4-[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoate];β-D-Glucopyranoside,2-(3,4-dihydroxyphenyl)ethyl 3-O-(6-deoxy-α-L-mannopyranosyl)-,4-[3-(3,4-dihydroxyphenyl)-2-propenoate],(E)-;Verbascoside;Kusaginin;Acteoside;TJC 160;NSC 603831;Russetinol;Stereospermin;(3,4-Dihydroxyphenyl)ethyl O-α-rhamnopyranosyl(1→3)-4-O-caffeoyl-β-D glucopyranoside;O′′′-Desarabinosyllavandulifolioside A;Distinctive Phytostem Lilac;Distinctive Active Powder SL Special;trans-Verbascoside;trans-Acteoside;22323-52-0;27625-92-9
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CAS No:
Description
Verbascoside is isolated from Lantana camara, acts as an ATP-competitive inhibitor of PKC, with an IC50 of 25 µM, and has antitumor, anti-inflammatory and antineuropathic pain activity.
Characteristics
245
-1.01590
1.6±0.1 g/cm3
142-145 °C
908.8°C at 760 mmHg
294.7±27.8 °C
1.689
room temp
LD50 oral in rat: > 5gm/kg
Drug Information
Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)|Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)|Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging. (See all compounds classified as Immunosuppressive Agents.)|Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity. (See all compounds classified as Antineoplastic Agents, Phytogenic.)|Chemicals that bind to and remove ions from solutions. Many chelating agents function through the formation of COORDINATION COMPLEXES with METALS. (See all compounds classified as Chelating Agents.)
acteoside
Verbascoside Use and Manufacturing
To a solution of 1 (156 mg, 0.25 mmol) in 8 ml of dry CH2Cl2 and catalytic amount of DMAP, an amount of 108mg (1.0 mmol) of Ethyl Bromide was added and the reaction mixture was stirred at 40 C for 3 h until theappearance of product followed by TLC plates. The mixture was extracted with EtOAc (3 × 100 mL). Thecombined organic layer was dried over anhydrous sodium sulfate and evaporated to dryness. The residue waschromatographed over silica gel and eluted with n-hexane/EtOAc in increasing concentrations to obtain the O-alkylderivative 7 in 69% yield. Ethyl Bromide was prepared with 2 gr of KBr (11.2 mmol) in 8 ml of Ethanol. Then 3mL of H2SO4 cc were added and stirring was performed at 45 C for 2 h. Meanwhile, the mixture was distilled andthe organic layer was collected.A catalytic amount of H2SO4 20% v/v was added to a solution of 1 (156 mg, 0.25 mmol) in 10 ml of dry acetone and the reaction mixture was stirred at room temperature for 15 min until the appearance of product followed by TLC plates. The residue was diluted with brine solution (20 mL). The mixture was extracted with EtOAc (3 × 30mL). Then, this organic layer was diluted with cold water. The combined organic layer was dried over anhydrous sodium sulfate and evaporated to dryness. The residue was chromatographed over silica gel and eluted with n-hexane/EtOAc in increasing concentrations to obtain the cyclic ketal derivative 5 in 92% yield.General procedure: Compounds 1-8 (5 mg each) were treated in 5% HCl (0.5 mL) and heated at 90 C for 2 h, respectively (Chang & Case 2005). After cooling, each reaction mixture was extracted with EtOAc, and the aqueous layer was neutralised with 0.1 M NaOH. As a result, glucose and rhamnose were obtained from compound (1-4), which were detected by thin layer chromatography(TLC) with authentic sugars. Similarly, we obtained glucose from compounds (5-8). The type of glucose and rhamnose were identified by TLC method with authentic sugars (Ma et al. 2014).General procedure: In a typical experimental procedure for chemical transesterification, a solution of verbascoside(0.112 g, 1mmol) in dry DCM (10 mL) was taken, to which the anhydrides (acetic or butyricanhydride, 4mmol), DMAP (10 mg) were added and stirred for 24 h at ambient temperature.After the completion of reaction, solvent was evaporated in vacuo and the crude product wassubjected to column chromatography (silica gel, 100-200 mesh, elution; n-chloroform/MeOH(90:10) gradient) to obtain pure products. The pure products were characterised on the basis of1H NMR, 13C NMR and MS given in compound characterisation (supporting information).
Computed Properties
Molecular Weight:624.6
XLogP3:-0.5
Hydrogen Bond Donor Count:9
Hydrogen Bond Acceptor Count:15
Rotatable Bond Count:11
Exact Mass:624.20542044
Monoisotopic Mass:624.20542044
Topological Polar Surface Area:245
Heavy Atom Count:44
Complexity:936
Undefined Atom Stereocenter Count:10
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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