Application of arctigenin and its derivative in medicament preparation

A technology of arctigenin and its derivatives, which is applied in the fields of medicinal chemistry and pharmacotherapeutics to achieve the effects of easy preparation, abundant synthetic raw materials, and promotion of AMPK phosphorylation

Inactive Publication Date: 2012-02-08
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing literature has never mentioned that arctiin, arctigenin and their analogues can promote AMPK phosphorylation and improve the body's anti-fatigue function

Method used

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  • Application of arctigenin and its derivative in medicament preparation
  • Application of arctigenin and its derivative in medicament preparation
  • Application of arctigenin and its derivative in medicament preparation

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0046] Preparation of compound 1

[0047] Weigh 1 kg of dried burdock seeds, heat under reflux with 75% ethanol solution for 3 hours, filter, and extract the filter residue twice by the same method, combine the filtrates, and recover the ethanol solution under reduced pressure to obtain the extract. The extract was heated to reflux with 5% dilute sulfuric acid for 4-6 h, cooled to room temperature, extracted with dichloromethane for several times, concentrated in the dichloromethane solution, and the concentrated solution was passed through a silica gel column with petroleum ether:ethyl acetate=3:1 , the crude arctigenin was obtained, and the crude product was recrystallized from methanol to obtain 35 grams of pure arctigenin (1).

[0048] Compound 1, C 21 H 24 O 6 , MW: 372; white powdery solid, soluble in dichloromethane and acetone.

[0049] 1 H NMR (300MHz, CDCl 3 ,): δ6.76 (d, J=7.8Hz, 1H), 6.75 (d, J=7.8Hz, 1H), 6.63 (d, J=2Hz, 1H), 6.58 (d, J=7.8Hz, 1H) ), 6.55(d...

experiment Embodiment 1

[0116] Experimental Example 1: The effect of compound 1 and its derivatives on AMPK phosphorylation was tested at the cellular level

[0117] The present invention tests the effect of compound 1 and its derivatives on AMPK phosphorylation at the cellular level, and it is known that the phosphorylation level of AMPK directly reflects its activity level.

[0118] 1. Experimental principle

[0119] AMPK acts as an energy sensor that regulates the balance of energy metabolism in cells and the body, and its phosphorylation level directly reflects its activity level. During exercise, it can activate AMPK in skeletal muscle, adipose tissue, cardiac muscle and other tissues by increasing the ratio of AMP / ATP. Activated AMPK can increase the production of ATP through a series of biological processes such as increasing glucose uptake and promoting fatty acid oxidation. . It is known that activating AMPK can significantly increase the exercise endurance of mice, so we used the phosphor...

experiment Embodiment 2

[0133] Experimental Example 2: Effect of Compound 1 on Endurance (Anti-fatigue Ability) of C57BL6 Mice

[0134] The present invention detects the effect of compound 1 on the exhaustion time and distance of mice by measuring the time and distance of treadmill exhaustion in C57BL6 mice, and the results show that compound 1 can prolong the exhaustion time and distance of mice.

[0135] 1. Experimental principle

[0136] Determination of animal endurance levels can be indicated by time to exhaustion, distance, or final speed on a treadmill, runner, or swimming in rats and mice.

[0137] The present invention refers to the endurance, that is, the anti-fatigue ability of the mice, by the treadmill exhaustion time and distance of the C57BL6 mice. Each track of the flat treadmill consists of a belt at the front and an electrode at the tail. The belt rotates at a certain speed, and the electrode carries a current of 0.2 mA. Mice experience pain on the electrical level, but such curre...

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Abstract

The invention relates to application of arctigenin as shown in general formula (1) and its derivative in preparing medicaments for improving body tolerance (resisting fatigue), and application of pharmaceutical compositions containing arctigenin and its derivative for improving body tolerance (resisting fatigue). The arctigenin and its derivative play a promoting role in AMPK phosphorylation. Whole animal tests show that compounds of the invention can enhance fatigue tolerance and can be used for anti-fatigue treatment.

Description

technical field [0001] The present invention relates to the field of medicinal chemistry and pharmacotherapeutics, relates to the medicinal use of arctigenin and derivatives thereof, more particularly, relates to arctigenin and derivatives thereof that promote AMPK phosphorylation, as well as pharmaceutical compositions and medicinal use. Background technique [0002] Regular endurance training (regular endurance training) or aerobic exercise (aerobic exercise) can enhance the function of various organs and scavenge the level of oxidative free radicals, improve the tolerance of muscles and the body to fatigue; it is beneficial to physical health and prevents many metabolisms. The occurrence of sexually transmitted diseases; under certain conditions, it can also be used as a treatment for diseases. [0003] But the fact is that most people don't have the time or some people's heart conditions can't afford minimal endurance training, so can small molecule drugs that improve m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/365A61K31/7048A61K31/443A61P39/00
Inventor 胡立宏沈旭赵坤陈静沈思达
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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