Application of amomum maximum roxb extract in preparation of alpha-glucosidase inhibitor drugs

A technology of glucosidase and cardamom, applied in the field of medicinal chemistry, to achieve the effects of reducing production and absorption, protecting pancreatic function, and slowing blood sugar rise

Active Publication Date: 2020-06-05
广东省科学院南繁种业研究所
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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However, there is no research report on the effect of some specif

Method used

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  • Application of amomum maximum roxb extract in preparation of alpha-glucosidase inhibitor drugs
  • Application of amomum maximum roxb extract in preparation of alpha-glucosidase inhibitor drugs
  • Application of amomum maximum roxb extract in preparation of alpha-glucosidase inhibitor drugs

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0032] Example 1 Preparation of compound of formula I

[0033] Take 2 kilograms of dried Nine-winged cardamom rhizome and crush it with 5L 95% ethanol for heating and refluxing for three times. Combine the three extracts and concentrate under reduced pressure until there is no alcohol. Add pure water to a total volume of 1L. Use an equal volume of ethyl acetate. The ester was extracted three times, the ethyl acetate extracts were combined, and concentrated to dryness under reduced pressure.

[0034] The ethyl acetate extract was subjected to silica gel column chromatography, eluting with a petroleum ether-acetone gradient. Collect the petroleum ether-acetone 9:1 elution fraction and recover it to dryness under reduced pressure. After silica gel column chromatography, dichloromethane-methanol gradient elution, the 98:2 elution fraction was collected, and the fraction was separated by preparative liquid chromatography, such as figure 1 Shown is the liquid chromatogram of this fract...

Example Embodiment

[0035] Example 2 Preparation of compound of formula I

[0036] Take 2 kilograms of dried Nine-winged cardamom rhizome and pulverize, extract with 20L 95% ethanol, combine the alcohol extracts, concentrate to about 2L under reduced pressure, add 500 grams of pretreated macroporous resin (resin model can be D101, AB -8, HPD-100 and HP20, etc.). After fully volatilizing and removing the ethanol, install the column, ethanol-water gradient elution (0, 30%, 60%, 80% and 95% ethanol), the 80% ethanol eluted fraction is divided into the target fraction, and concentrated to dryness under reduced pressure; pass through silica gel Column chromatography, dichloromethane-methanol gradient elution, collect 98:2 elution fraction, the fraction is separated by preparative liquid chromatography, the mobile phase is methanol-water 85:15, the flow rate is 6ml / min, the column is RP-C18 chromatographic column (10*250mm), the detection wavelength is set to 280nm, and the chromatographic peaks with ret...

Example Embodiment

[0037] Example 3 Structural identification of the compound of formula I

[0038] The structure of the compound of formula I was determined by nuclear magnetic resonance spectrum and mass spectrometry analysis.

[0039] The carbon spectrum and hydrogen spectrum data are as follows:

[0040] 1 H-NMR(600MHz,CDCl3)δ7.67(d,J=6.0Hz,1H), 7.56(s,1H), 6.33(d,J=6.0Hz,1H), 4.82(s,1H), 4.64( s, 1H), 2.69 (d, J = 16.2 Hz, 1H), 2.45 (dd, J = 11.4, 16.2 Hz, 1H), 2.40-2.36 (m, 1H), 2.04-1.95 (m, 2H), 1.89 -1.85(m,1H),1.78-1.73(m,1H),1.64-1.56(tq,J=3.0,13.8Hz,1H),1.55-1.48(m,1H),1.43-1.38(m,1H) ,1.37-1.32(dq,J=4.2,12.6Hz,1H),1.24-1.15(m,3H),0.88(s,3H),0.82(s,3H),0.78(s,3H).

[0041] 13 C-NMR(150MHz,CDCl3)δ178.70(-CO-,C-13), 154.61(=CH-,C-15),152.99(=CH-,C-16),147.70(C,C-8 ),129.85(C,C-12),116.36(=CH-,C-14),107.77(=CH-,C-17),55.54(CH,C-5),53.96(CH,C-9) ,42.06(CH2,C-3),39.98(C,C-10),39.01(CH2,C-1),38.07(CH2,C-7),33.63(CH3,C-18),33.63(C, C-4), 24.37 (CH2, C-6), 21.72 (CH3, C-19), 19.54 (CH2, C-11), ...

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Abstract

The invention relates to the field of medicinal chemistry, and in particular to application of amomum maximum roxb extract in the preparation of alpha-glucosidase inhibitor drugs. Specifically, the invention relates to application of a compound shown by a formula I or pharmaceutically acceptable salt of the compound in the preparation of the alpha-glucosidase inhibitor drugs. The compound of the formula I is extracted and isolated from the complex chemical components of amomum maximum roxb, and alpha-glucosidase activity can be significantly inhibited.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to the application of cardamom japonicus extract in the preparation of α-glucosidase inhibitor drugs. Background technique [0002] α-glucosidase (α-glucosidase) mainly includes enzymes such as maltase, sucrase, isomerized maltase, and lactase, which are widely distributed in the brush border of the small intestinal villous mucosa cells and participate in the digestion of food, glycoprotein It is a general term for a class of enzymes that can catalyze the hydrolysis of α-glucose groups from the non-reducing ends of substrates containing α-glucosidic bonds. [0003] α-glucosidase affects the formation of complex carbohydrates on the cell surface, and diseases such as diabetes, obesity, hyperlipidemia, inflammation, cancer, immune response, and viral infection are closely related to the formation of complex carbohydrates on the cell surface, so α-glucosidase inhibitors not only hav...

Claims

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Application Information

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IPC IPC(8): A61K31/351A23L33/105A61P3/10A61P3/04A61P3/06A61P29/00A61P35/00A61P37/02A61P31/12
CPCA23V2002/00A61K31/351A23L33/105A61P3/04A61P3/06A61P3/10A61P29/00A61P31/18A61P35/00A61P37/02A23V2200/30A23V2200/328A23V2200/3262A23V2200/332A23V2200/308A23V2200/324A23V2250/21
Inventor 卢传礼刘娟李亚军
Owner 广东省科学院南繁种业研究所
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