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Method for preparing C20 position dehydroxylation dammarane type rare ginsenoside and aglycone thereof

A dehydration reaction and compound technology, applied in the field of natural medicine, can solve the problems of difficult separation, poor purity, low yield, etc., and achieve the effect of simple reaction steps and low preparation cost

Active Publication Date: 2013-02-06
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] At present, such rare saponins are mostly directly isolated and extracted from plants of the genus Panax (Liao PY et al., JAgric Food Chem, 2008, 56, 1751-1756). Complexity and other factors make total chemical synthesis difficult, so semi-synthetic preparation is a good choice
C in the current market 20 The commercial reference substances of dehydroxydammarane-type rare ginsenosides and their aglycones are rare, and at the same time, due to the similar polarity of the paired products, it is difficult to separate them by traditional chemical means, with low yield and poor purity

Method used

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  • Method for preparing C20 position dehydroxylation dammarane type rare ginsenoside and aglycone thereof
  • Method for preparing C20 position dehydroxylation dammarane type rare ginsenoside and aglycone thereof
  • Method for preparing C20 position dehydroxylation dammarane type rare ginsenoside and aglycone thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] 20mg ginsenoside Rh 1Respectively dissolve 40ml of 0.05% formic acid in methanol: water (V:V4:6) mixed solution, and heat at 120°C for 4 hours under the pressure of 0.12MPa. After the reaction liquid is cooled, select Agilent Zorbax SB-C18 semi-preparative column (250mm × 9.4mm I.D., 5 μ m), use mobile phase as the aqueous solution containing 50% acetonitrile for isocratic elution, and wait for the raw material Rh 1 After the peak, collect the two main chromatographic peaks (the former is ginsenoside Rk 3 , the latter being ginsenoside Rh 4 ), concentrated and freeze-dried to get a white powder, the weights are Rk 3 1.70mg (8.75% yield), Rh 4 3.97 mg (yield 20.44%), the purity determined by HPLC method was 98.9% and 92.7%, respectively. After MS, 13 C-NMR measurement (relevant data is attached), and verified with relevant literature data, confirmed that the white powder is ginsenoside Rk 3 and Rh 4 .

[0043] Ginsenoside Rk 3 Identification of:

[0044] White ...

Embodiment 2

[0050] 50mg ginsenoside Rg 3 Dissolve in 75ml of 0.02% formic acid ethanol: water (V:V5:5) mixed solution, and heat at 120°C for 6 hours under the pressure of 0.12MPa. After the reaction solution is cooled, select Agilent Zorbax SB-C18 semi-preparative column (250mm × 9.4mm I.D., 5 μm), use the mobile phase as the aqueous solution containing 65% acetonitrile for isocratic elution, and wait for the raw material Rg 3 After the peak, collect the two main chromatographic peaks (the former is ginsenoside Rk 1 , the latter being ginsenoside Rg 5 ), concentrated and freeze-dried to get a white powder, the weights are Rk 1 3.96mg (8.11% yield), Rg 5 8.01 mg (yield 16.40%), the purity determined by HPLC method was 94.7% and 98.5%, respectively. After MS, 13 C-NMR measurement (relevant data is attached), and verified with relevant literature data, confirmed that the white powder is ginsenoside Rk 1 and Rg 5 .

[0051] Ginsenoside Rk 1 Identification of:

[0052] White powder, ...

Embodiment 3

[0058] 100mg ginsenoside Rh 2Dissolve in 150ml of 0.01% formic acid methanol:water (V:V6:4) mixed solution, and heat at 120°C for 4 hours under 0.15MPa pressure. After the reaction liquid is cooled, select Agilent Zorbax SB-C18 semi-preparative column (250mm × 9.4mm I.D., 5 μ m), use mobile phase as the aqueous solution containing 80% acetonitrile for isocratic elution, and wait for the raw material Rh 2 After the peak, collect the two main chromatographic peaks (the former is ginsenoside Rk 2 , the latter being ginsenoside Rh 3 ), concentrated and freeze-dried to get a white powder, the weights are Rk 2 9.37mg (9.63% yield), Rh 3 14.01 mg (yield 14.39%), the purity determined by HPLC method was 96.8% and 98.7%, respectively. After MS, 13 C-NMR measurement (relevant data is attached), and verified with relevant literature data, confirmed that the white powder is ginsenoside Rk 2 and Rh 3 .

[0059] Ginsenoside Rk 2 Identification of:

[0060] White powder, easily sol...

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Abstract

The invention relates to the field of natural medicine, in particular to a method for preparing C20 position dehydroxylation dammarane type rare ginsenoside and aglycone thereof. The method for preparing the C20 position dehydroxylation dammarane type rare ginsenoside and the aglycone thereof is achieved by combining multiple means of semi-synthesis preparation, chromatogram separation and purification and the like. The method is characterized in that ginsenoside Rg2, Rh1, Rg3, Rs3 and Rh2, protopanoxadiol and protopanaxatriol are used as raw materials, one-step dehydration reaction is performed under the acidic condition, C20 position hydroxyl is removed to generate double bond isomerous series C20 position dehydroxylation dammarane type rare ginsenoside and the aglycone thereof, a liquid phase is prepared to enrich a target compound, and the target compound is concentrated and freeze-dried to obtain the C20 position dehydroxylation dammarane type rare ginsenoside and the aglycone thereof. According to the method, raw materials are easy to obtain, the reaction steps are simple, and the preparation cost is low.

Description

technical field [0001] The present invention relates to the field of natural medicines, in particular to a C 20 A method for preparing rare ginsenosides and aglycones of the dehydroxylated dammarane type, that is, combining semi-synthetic preparation, chromatographic separation and purification to obtain C 20 A method for the dehydroxylation of dammarane-type rare ginsenosides and their aglycones. Background technique [0002] Ginseng plants (ginseng, American ginseng, notoginseng, etc.) have a long history and definite curative effects, and have become one of the most popular and widely used Chinese herbal medicines in the world. Modern pharmacological studies have shown that its main active ingredient, ginsenoside, has multiple effects such as anti-inflammatory, anti-oxidant, neuroprotective, and improved cardiovascular blood supply (L.P.Christensen, AdvFoodNutrRes, 2008, 55, 1; W.D.Rausch et al., Acta Neurobiol Exp, 2006 , 66, 369; A.A. Pawar. et al., Phytother Res, 200...

Claims

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Application Information

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IPC IPC(8): C07J17/00C07J9/00C07J75/00
Inventor 李萍齐炼文万瑾毅
Owner CHINA PHARM UNIV
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