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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  • Abstract
  • Description
  • Claims
  • Application Information

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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 c

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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
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Example Embodiment

[0041] Example 1

[0042] 20mg ginsenoside Rh 1 Dissolved in 40ml of 0.05% formic acid in methanol: water (V:V4:6) mixed solution, heated at 120°C for 4 hours under a pressure of 0.12MPa. After the reaction solution is cooled, select Agilent Zorbax SB-C18 semi-preparative column (250mm×9.4mm I.D., 5μm), and elute isocratically with the mobile phase as an aqueous solution containing 50% acetonitrile. 1 After peaking, collect the two main chromatographic peaks (the former is ginsenoside Rk 3 , The latter is ginsenoside Rh 4 ), white powder after concentration and lyophilization, the weight is Rk 3 1.70mg (yield 8.75%), Rh 4 3.97mg (yield 20.44%), the purity determined by HPLC method was 98.9% and 92.7%, respectively. After MS, 13 C-NMR measurement (relevant data attached), and verify with relevant literature data, confirm that the white powder is ginsenoside Rk respectively 3 And Rh 4 .

[0043] Ginsenoside Rk 3 Identification of:

[0044] White powder, easily soluble in methanol. TO...

Example Embodiment

[0049] Example 2

[0050] Add 50mg ginsenoside Rg 3 Dissolved in 75ml of 0.02% formic acid in ethanol: water (V:V5:5) mixed solution, heated at 120°C for 6 hours under a pressure of 0.12MPa. After the reaction solution is cooled, select Agilent Zorbax SB-C18 semi-preparative column (250mm×9.4mm I.D., 5μm), and elute isocratically with the mobile phase as an aqueous solution containing 65% acetonitrile. 3 After peaking, collect the two main chromatographic peaks (the former is ginsenoside Rk 1 , The latter is ginsenoside Rg 5 ), white powder after concentration and lyophilization, the weight is Rk 1 3.96mg (8.11% yield), Rg 5 8.01mg (yield 16.40%), the purity determined by HPLC method was 94.7% and 98.5%. After MS, 13 C-NMR measurement (relevant data attached), and verify with relevant literature data, confirm that the white powder is ginsenoside Rk respectively 1 And Rg 5 .

[0051] Ginsenoside Rk 1 Identification of:

[0052] White powder, easily soluble in methanol. TOF-MS displa...

Example Embodiment

[0057] Example 3

[0058] 100mg ginsenoside Rh 2 Dissolved in 150ml 0.01% formic acid in methanol: water (V:V6:4) mixed solution, heated at 120°C for 4 hours under a pressure of 0.15MPa. After the reaction solution is cooled, select Agilent Zorbax SB-C18 semi-preparative column (250mm×9.4mm I.D., 5μm), and elute isocratically with 80% acetonitrile in the mobile phase. 2 After peaking, collect the two main chromatographic peaks (the former is ginsenoside Rk 2 , The latter is ginsenoside Rh 3 ), white powder after concentration and lyophilization, the weight is Rk 2 9.37mg (yield 9.63%), Rh 3 14.01mg (yield 14.39%), the purity was determined by HPLC method to be 96.8% and 98.7%, respectively. After MS, 13 C-NMR measurement (relevant data attached), and verify with relevant literature data, confirm that the white powder is ginsenoside Rk respectively 2 And Rh 3 .

[0059] Ginsenoside Rk 2 Identification of:

[0060] White powder, easily soluble in methanol. TOF-MS display [M+CH 3 COO]...

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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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