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Esculentoside A, EsA as well as preparation method and application thereof

A technology of pokeweed saponin A and derivatives, which is applied in the field of medicine and can solve problems such as restricting the use of injection drugs

Inactive Publication Date: 2011-07-20
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The acute toxicity test of pokeweed saponin A on mice shows that pokeweed saponin A has a strong hemolytic effect, which limits its use as an injection drug

Method used

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  • Esculentoside A, EsA as well as preparation method and application thereof
  • Esculentoside A, EsA as well as preparation method and application thereof
  • Esculentoside A, EsA as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1 3-O-[β-D-glucopyranose-(1,4)-β-D-xylopyranose]-2β, 3β, 23-trihydroxy-oleanane-12-ene- Synthesis of 28-(tyrosine methyl ester amide)-30-acid methyl ester

[0040] Dissolve pokeweed saponin A (EsA) (41.2 mg, 0.05 mmol) in dry DMF / THF (1:3, v / v), and put into N, N-dicyclohexylcarboimide (DCC, 20.7 mg , 0.1mmol) and N-hydroxybenzotriazole (HOBt, 13.5mg, 0.1mmol), stirred at room temperature for 1 hour, then added tyrosine methyl ester (39.0mg, 0.2mmol), under the protection of argon, heated to 60°C, stirred for 4 hours, filtered, separated by silica gel column chromatography (dichloromethane / methanol, 6:1), purified by HPLC (condition: C18, YMC 250×10mm, 5 μm; mobile phase: methanol / water, 75 %) to obtain 48.2 mg of white powder, the yield was 96%.

[0041] 1 H-NMR (600MHz, C 5 D. 5 N): δ6.89~6.86(m, 2H), 6.75~6.67(m, 2H), 6.58(brs, 1H), 5.39(t, 1H, J=3.6Hz), 5.01(d, 1H, J= 7.8Hz), 4.94(d, 1H, J=7.2Hz), 4.83(s, 1H), 4.79(m, 1H), 4.74(dd, 1H, J=2.4, 12.0Hz), ...

Embodiment 2

[0044] Example 2 3-O-[β-D-glucopyranose-(1,4)-β-D-xylopyranose]-2β, 3β, 23-trihydroxy-oleanane-12-ene- Synthesis of 28-(bisglycyl dipeptide methyl ester amide)-30-acid methyl ester

[0045] EsA (41.3mg, 0.05mmol) was dissolved in dry DMF / THF (1:3, v / v), and N, N-dicyclohexylcarboimide (DCC, 20.7mg, 0.1mmol) and N -Hydroxybenzotriazole (HOBt, 13.5mg, 0.1mmol), stirred at room temperature for 1 hour, then added diglycine dipeptide methyl ester (14.6mg, 0.1mmol), heated to 60°C under the protection of argon, Stir for 4 hours, filter, separate by silica gel column chromatography (dichloromethane / methanol, 7:1), and purify with HPLC (conditions: C18, YMC 250×10mm, 5 μm; mobile phase: methanol / water, 75%), to obtain White powder 42.7 mg, yield 91%.

[0046] 1 H-NMR (600MHz, C 5 D. 5 N): δ8.20(brs, 1H), 8.17(brs, 1H), 5.39(t, 1H, J=3.6Hz), 5.03(d, 1H, J=7.8Hz), 4.94(d, 1H, J =7.2Hz), 4.83(s, 1H), 4.79(m, 1H), 4.74(dd, 1H, J=2.4, 12.0Hz), 4.54~4.51(m, 1H), 4.33~4.28(m, 3H) , 4....

Embodiment 3

[0048] Example 3 3-O-[β-D-glucopyranose-(1,4)-β-D-xylopyranose]-2β,3β,23-trihydroxy-oleanane-12-ene- Synthesis of 28-[(3-amino)-1-propionamide]-30-acid methyl ester

[0049] EsA (1239 mg, 1.5 mmol) was dissolved in dry DMF / THF (1:3, v / v), and N, N-dicyclohexylcarboimide (DCC, 413 mg, 2 mmol) and N-hydroxybenzene And triazole (HOBt, 270mg, 2mmol), stirred at room temperature for 1 hour, then added 1,3-propanediamine (0.5ml, 6mmol), heated to 60°C under argon protection, stirred for 4 hours, filtered, Silica gel column chromatography (dichloromethane / methanol, 4:1), purified by HPLC (conditions: C18, YMC 250 × 10mm, 5 μm; mobile phase: methanol / water, 70%), to give white powder 1257mg, yield 95%.

[0050] 1 H-NMR (600MHz, C 5 D. 5N): δ6.50(brs, 1H), 5.39(t, 1H, J=3.6Hz), 5.01(d, 1H, J=7.8Hz), 4.96(d, 1H, J=7.2Hz), 4.79( d, 1H, J=1.2Hz), 4.67(dd, 1H, J=2.4, 12.0Hz), 4.33~4.28(m, 3H), 4.24~4.20(m, 2H), 4.18(d, 1H, J= 9Hz), 4.15(t, 1H, J=9Hz), 4.08(t, 1H, J=8.4Hz), 4.03(t, 1...

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Abstract

The invention discloses an Esculentoside A, EsA as well as a preparation method and application thereof. The general formula of the Esculentoside A, EsA is shown in the specification, wherein R is amino acid, polypeptide, piperazine base, substituted piperazine bases or substituted amido. An active ester intermediate formed by the Esculentoside A, EsA under the action of a condensation agent reacts with amine or piperazine or substituted piperazine or amino acid with the protected carboxyl or polypeptide; and the Esculentoside A, EsA is obtained by separation and purification. The Esculentoside A, EsA, as well as pharmaceutical salt and medical composite thereof can be used for preparing inflammatory medicaments.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a novel pokeweed saponin A derivative and its preparation method and application. Background technique [0002] Phytolacca esculenta (Phytolacca esculenta Van Houtte), a traditional Chinese medicine, is the tuber of Phytolacca esculenta Van Houtte, which is recorded in previous Chinese Pharmacopoeias. At present, it is used to treat a variety of tumors, breast hyperplasia, ovarian cysts, tracheitis, psoriasis, hemorrhagic diseases, allergic purpura, etc., and has obvious curative effects. [0003] The applicant has conducted systematic research on the traditional Chinese medicine Phytophthora chinensis since 1979. The research content includes resource distribution, separation and identification of chemical components, pharmacology, efficacy, toxicity of active components, and research on clinical treatment of related diseases. Successively isolated and identified 38 kinds of c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00C07K5/06C07K5/068C07K5/065A61K31/704A61K38/05A61P29/00
Inventor 易杨华张大志巩伟张文李玲孙鹏刘宝姝汤华
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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