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Composition for preventing or treating obesity-related diseases mediated by the activation of ampk and including 2,5-bis-aryl-3,4-dimethyltetrahydrofuran lignans as active ingredients

A technology of composition and lignans, applied in the direction of organic active ingredients, medical preparations containing active ingredients, active ingredients of heterocyclic compounds, etc., can solve the problem of increasing the number of fat cells and achieve good stability

Inactive Publication Date: 2012-05-30
IND ACADEMIC COOP FOUND YONSEI UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it is well known that the drug increases the number of adipocytes during treatment and has the side effect of inducing obesity

Method used

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  • Composition for preventing or treating obesity-related diseases mediated by the activation of ampk and including 2,5-bis-aryl-3,4-dimethyltetrahydrofuran lignans as active ingredients
  • Composition for preventing or treating obesity-related diseases mediated by the activation of ampk and including 2,5-bis-aryl-3,4-dimethyltetrahydrofuran lignans as active ingredients
  • Composition for preventing or treating obesity-related diseases mediated by the activation of ampk and including 2,5-bis-aryl-3,4-dimethyltetrahydrofuran lignans as active ingredients

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050]

[0051] Powdered nutmeg (100 g) was dissolved in each solution (500 mL, see Table 1), and then the active substance was extracted 3 times within 2 hours using an ultrasonic extractor. Use the same concentration of the active ingredient of the isolated extract. Myristicin was obtained using Sigma (Cat. No. M9237). Each solution was used to extract the nutmeg extract and passed through MeOH / H 2 O (0-32 min: 63% MeOH, 32-37 min: 63 → 100% MeOH) for analysis of myristyl ether. Table 1 shows the contents of myristicin and carmasin B in nutmeg extracts extracted using different solutions.

[0052] Table 1

[0053]

[0054]As shown in Table 1, the 30% ethanol extract contained an average of 0.45% myristicin, about one-third of the 1.27% of the 75% ethanol extract, and 1.85% of the 75% methanol extract under the same conditions . Also, using MeOH / H 2 O (0-35 minutes: 60% MeOH, 35-60 minutes: 60→100% MeOH) HPLC (Optima Pak C18 column 4.6x250mm, particle size 5μm, flo...

Embodiment 2

[0056]

[0057] Nutmeg (500 g) was extracted using 30% aqueous ethanol (1,000 mL) and passed through ion exchange resin Diaion HP-20 to adsorb onto the resin (500 g). Then, the extract was eluted with 1 liter of 50% ethanol, 60% ethanol, 70% ethanol, 80% ethanol, 90% ethanol, 100% ethanol and 100% acetone, respectively. Table 2 shows the degree of elution of calmasin B and myristicin adsorbed on Diaion HP-20 by ethanol solution and acetone.

[0058] Table 2

[0059]

[0060] As shown in Table 2, myristicin was hardly detected when the substances adsorbed on Diaion HP-20 were eluted with 80% or less ethanol.

[0061] The same solvent was used to monitor the elution of glabrinin B, one of the 2,5-diaryl-3,4-dimethyltetrahydrofuranolignans. As in Table 2, Figure 5 and Figure 6 As shown, when 80% ethanol was used as the eluent, the concentration of eluted calmaxinin B was the highest.

Embodiment 3

[0062]

[0063] In Example 1, using 1 H-and 13 C-NMR analysis of 2,5-diaryl-3,4-dimethyltetrahydrofuranolignans isolated from 30% ethanolic Myristica extract by HPLC. The physical and chemical properties of 2,5-diaryl-3,4-dimethyltetrahydrofuranolignans (compounds 1-6) extracted from nutmeg of the present invention are as follows.

[0064] 3-1. Tetrahydrofuran guaiacin (compound 1)

[0065] colorless powder; 1 H-NMR: ppm (500 MHz, CDCl 3 ): δ0.61 (6H, d, J = 6.0 Hz, 3- and 4-Me), 2.67 (2H, m, 3- and 4-H), 3.91 (6H, 3'- and 3"-OMe) , 5.12 (2H, d, J = 6.6 Hz, 2- and 5-H), 5.59 (2H, s, 4'- and 4"-OH), 6.90-6.99 (6H, m, 2'-, 5' -, 6'-, 2"-, 5"- and 6"-H); 13 C-NMR: ppm (125 MHz, CDCl 3 ): δ11.7 (3- and 4-Me), 41.5 (C-3 and C-4), 55.8 (2×OMe), 82.7 (C-2 and C-5), 109.0 (C-2' and C-2"), 113.9 (C-5' and C-5"), 119.3 (C-6' and C-6"), 132.5 (C-1' and C-1"), 144.3 (C-4 ' and C-4"), 146.2 (C-3' and C-3").

[0066] 3-2. Triasprosin (compound 2)

[0067] colorless oil; 1 H-NM...

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Abstract

The present invention relates to a 2,5-bis-aryl-3,4-dimethyltetrahydrofuran lignan compound which activates nutmeg-derived AMP-activated protein kinase (AMPK), and to a composition including same as active ingredients for preventing and treating metabolic syndromes such as obesity. More particularly, the present invention relates to an AMPK-activating compound comprising one of the 2,5-bis-aryl-3,4-dimethyltetrahydrofuran lignan-based compounds produced by extracting Myristica fragrans with a solution of 30% or less of ethanol and separating and purifying the extracts using chromatography, as expressed in chemical formula 1 below, and to a composition comprising same as an active ingredient for preventing and treating metabolic syndrome caused by AMPK enzyme activation, such as obesity, diabetes, high cholesterol and cardiopulmonary diseases.

Description

technical field [0001] The present invention relates to a lignan compound capable of activating AMP-activated protein kinase (AMPK) obtained from cardamom (Myristica meraceae), and to a composition comprising the lignan compound as an active ingredient . More specifically, the present invention relates to 2,5-diaryl-3,4-dimethyltetrahydrofuranolignans, which can be extracted from nutmeg by 10-30% aqueous ethanol, which can activate AMPK And can effectively prevent and treat metabolic syndrome such as obesity, diabetes, hyperlipidemia and cardiovascular disease, and the present invention relates to a composition for treating and preventing diseases mediated by the activation of AMPK, which contains as active Components of 2,5-diaryl-3,4-dimethyltetrahydrofuranolignans. Background technique [0002] Due to the development of economy and the improvement of living standards in recent years, dietary life has been improved, and the intake of calories is increasing rapidly. Howe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K36/185
CPCA61K2236/333A61K36/185A61K31/341A23C9/152A61K31/36A23L27/20A23L33/10A61K2300/00A61P3/00A61P3/04A61P3/10
Inventor 吴元根阮非红黎氏文秋姜厚远申宜锡崔镇圭徐大方李尚骏
Owner IND ACADEMIC COOP FOUND YONSEI UNIV
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