Alpha-glycosidase inhibitor compound in silkworm excrement total alkaloid and application thereof

A technology of glycosidase inhibition and total alkaloids, applied in the field of biomedicine, can solve problems such as heavy economic burden, lower quality of life, and great harm

Inactive Publication Date: 2010-03-17
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

These complications are extremely harmful, reduce people's q

Method used

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  • Alpha-glycosidase inhibitor compound in silkworm excrement total alkaloid and application thereof
  • Alpha-glycosidase inhibitor compound in silkworm excrement total alkaloid and application thereof
  • Alpha-glycosidase inhibitor compound in silkworm excrement total alkaloid and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1: Extraction of silkworm excrement total alkaloids

[0026] Preparation of silkworm excrement total alkaloid extract: take 1.2kg silkworm excrement, add 6L of deionized water, adjust pH to 3.0, keep warm at 40-50°C for 3 hours, and filter. The filter residue was extracted twice in the same way, and the three filtrates were combined, concentrated under reduced pressure to about 2.4 L, added with 3 L of absolute ethanol, mixed well, and left standing overnight. Centrifuge, take the supernatant and pass it through 001×7 type cation exchange resin, wash the non-adsorbed impurities with 50% (v / v) ethanol and deionized water successively, use 0.5-1.0mol / L ammonia solution to elute, collect α - For the positive part of the glycosidase inhibitory activity test, ammonia water was evaporated under reduced pressure, then decolorized by adsorption, eluted with absolute ethanol, and evaporated to dryness under reduced pressure to obtain 3.2 g of silkworm excrement total ...

Embodiment 2

[0027] Example 2: Separation and purification of active substances inhibiting α-glucosidase in silkworm excrement total alkaloid extract

[0028] The silkworm excrement total alkaloid extract obtained in Example 1 was separated and purified by HPLC, and the chromatographic conditions were: cation exchange detection column: Hypersil SCX (250mm × 4.0mm, 5 μm); mobile phase was acetonitrile: water (90: 10v / v-60:40v / v); flow rate is 0.6mL / min; -2.0mL / min; evaporative light scattering detection; column temperature 40°C; injection volume 50-100μL; The material corresponding to the chromatographic peak of 35.9 minutes is evaporated to dryness, and the separated and purified sample is 1-deoxynojirimycin (DNJ); the material corresponding to the chromatographic peak with a retention time of 35.9 minutes is collected for multiple experiments, and evaporated to dryness The mobile phase obtained from the separated and purified sample is (2R,4R)-dihydroxy-5(R)hydroxymethylpiperidine.

Embodiment 3

[0029] Embodiment 3: the structure of (2R, 4R)-dihydroxy-5 (R) hydroxymethyl piperidine, 1-deoxynojirimycin (DNJ)

[0030] (2R,4R)-dihydroxy-5(R)hydroxymethylpiperidine:

[0031] (c=6.02×10 -5 , H 2 O microtube assay); 1 H-NMR (D 2 O, 300MHz) δ: 1.53 (1H, ddt, J=14.0, 11.4, 4.5Hz, H-3ax), 2.02 (1H, dddd, J=14.0, 5.0, 2.4Hz, H-3eq), 2.91 (1H, m, H-1ax), 2.98(1H, m, H-2), 3.24(1H, ddd, J=13.1, 4.5, 2.4Hz, H-1eq), 3.28(1H, t, J=10.4Hz, H -5), 3.54 (1H, ddd, J=11.4, 9.1, 4.8Hz, H-4), 3.74 (2H, m, H-6). 13 C-NMR (D 2(2, 300 MHz) δ: 28.7 (C-3), 42.0 (C-1), 57.8 (C-6), 60.2 (C-2), 69.7 (C-5), 7.06 (C-4).

[0032] 1-Deoxynojirimycin (DNJ):

[0033] ESI-MS m / z: 164[M+H]+; 1H-NMR (D2O, 300MHz) δ: 3.86-3.63 (3H, m, 2H-6; H-3), 3.52-3.36 (3H, m, H-2; H-4; H-1e), 3.09 (1H, dd, H-1a), 2.86 (1H, t, H-5); 13C-NMR (D2O, 300MHz) δ: 76.2 (C-3 ), 67.7 (C-4), 66.9 (C-2), 59.9 (C-6), 57.7 (C-5), 45.8 (C-1). The above data are consistent with 1-deoxynojirimycin (DNJ) standard substance ...

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Abstract

The invention obtains (2R, 4R)-dihydroxy-5(R) hydroxymethyl piperidine (new compound) and 1-DNJ from silkworm excrement total alkaloid through separation. Enzymological measurement shows that the twoalkaloids have certain inhibitory activity to alpha-glycosidase. The alpha-glycosidase inhibitor compound can be applied in preparing machines for treating disasters such as diabetes, obesity and thelike.

Description

【Technical field】: [0001] The invention belongs to the technical field of biomedicine, and particularly relates to an alkaloid monomer having alpha-glucosidase inhibitory activity in total alkaloids of silkworm excrement, and its application in the preparation of medicines for treating diseases such as diabetes. 【Background technique】: [0002] Diabetes mellitus is a group of metabolic diseases characterized by hyperglycemia caused by insufficient insulin secretion and / or impaired insulin action. It is manifested by an abnormal increase in the concentration of glucose in the blood and urine. When the blood sugar and urine sugar are too high, the typical symptoms of "three more and one less" will appear, that is, polydipsia, polyuria, polyphagia and weight loss, accompanied by fatigue powerless. Diabetes is generally divided into several types such as type I diabetes, type II diabetes and gestational diabetes. Type II diabetes can not only cause microvascular complications,...

Claims

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Application Information

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IPC IPC(8): C07D211/46C07D211/42A61K31/445A61P3/10A61P3/04
Inventor 朱元元白钢亓晖
Owner NANKAI UNIV
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