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A kind of unsaturated ester derivative of oleanolic acid and its preparation method and application
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An oleanolic acid and unsaturated technology, applied in the field of oleanolic acid unsaturated ester derivatives, can solve the problems of low weight loss effect, liver function damage, large side effects and the like
Active Publication Date: 2017-08-08
SHANXI UNIV
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At present, Orlistat (Orlistat), as the only long-acting weight-loss drug, still has relatively large side effects, especially causing liver damage [Derosa G et al., Expert Opin Drug Saf., 2012, 11(3), 459 -471; Mary BC et al., Case Manager.,2004,15(6):47-49], and the compounds directly isolated from natural plants generally have low weight loss effect, so it is necessary to carry out structural modification to improve their activity
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Embodiment 1
[0026] Synthesis and characterization of embodiment 1 oleanolic acid unsaturated ester derivatives
[0027] Add 300mg of oleanolic acid and 45mg of potassiumcarbonate to DMF in sequence, and after stirring at room temperature for 20 minutes, add 163mg of ethyl 4-bromobutenoate dropwise, stir at 50°C, and detect the end point of the reaction by TLC. After 8 hours of reaction, Add 5ml of water, extract 3 times with ethyl acetate, combine the organic phases, dry over anhydrousmagnesiumsulfate, and concentrate under reduced pressure to obtain the crude product, which is purified by silica gelcolumn chromatography, and the eluent is petroleumether: ethyl acetate (24:7) , to obtain 159.16mg of colorless oily liquid, yield 68%. 1 H-NMR (600MHz, CDCl 3 ),δ0.70(s,3H,CH 3 ),0.77(s,3H,CH 3 ),0.89(s,3H,CH 3 ),0.91(s,3H,CH 3 ),0.94(s,3H,CH 3 )0.98(s,3H,CH 3 ),1.15(s,3H,CH 3 ),1.30(t,3H,CH 3 ),2.91(d,1H,J=12.2Hz,H-18),3.20(m,1H,H-3),4.22(d,J=8.4Hz,2H,CH 2 O), 4.70 (dd, 2H, J=...
Embodiment 2
[0029] Example 2 Experiment of Oleanane-28-α, β-Unsaturated Ester Inhibiting Pancreatic Lipase Activity
[0030] Enzyme activity was determined by the p-nitrophenol method. Add 780 μL Tris-HCl (pH=8) to the reaction system, then add 100 μL of 0.5 mg / mL PL and 20 μL of the substance to be tested, mix thoroughly, and incubate at 37°C for 15 minutes, then immediately add PNPB solution (12.5 mmol / L), mix evenly, put the solution in a 96-well microplate plate, set 4 duplicate holes for each concentration, and measure on a microplate reader with a detection wavelength of 400nm. Measure a point every 3 minutes, measure 15 minutes, and record all data. Calculate the absorbance change rate K with time, and calculate the inhibition rate according to the following formula:
[0031] Inhibition rate of PL (%)=(1-K 实验 / K 空白 )×100
[0032] The experiment was repeated 3 times, and the results were averaged.
[0033] When the inhibitor concentration was 10ug / mL, the inhibition rate was 4...
[0038] According to the enzyme activity test method, under different inhibitor concentration conditions, the residual enzyme activity is measured when the enzyme concentration is different (final concentration is 0.1, 0.2, 0.3, 0.4, 0.5mg / mL), and the corresponding reaction speed is obtained. Plot the amount of enzyme added. The result is as Figure 5 shown. Proved to be reversible inhibition.
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Abstract
The invention provides an oleanolic acid unsaturated ester derivative as well as a preparation method and an application thereof. The preparation method of the oleanolic acid unsaturated ester derivative such as oleanane-28-alpha,beta-unsaturated ester comprises the following steps: oleanolic acid and potassiumcarbonate are added to DMF (dimethyl formamide), ethyl 4-bromocrotonate is added dropwise, and the mixture is stirred; after reaction, water is added, ethyl acetate is used for extraction, an organic phase is dried with anhydrousmagnesiumsulfate, a crude product is obtained through decompressing concentration, and a final product is obtained after purification. Experiments prove that oleanolic acid unsaturated esters have a diet effect, the mechanism of action is that the diet effect is realized through pancreatic lipase inhibition, and the action type is a mixed inhibition type. The enzyme inhibition activity of the oleanane-28-alpha,beta-unsaturated ester is 4.74 times of that of oleanolic acid, and the oleanolic acid unsaturated ester derivative can be applied to preparation of novel pancreatic lipase inhibitor type diet pills and diet health care products..
Description
technical field [0001] The present invention relates to unsaturated ester derivatives of oleanolic acid, in particular to unsaturated ester derivatives of oleanolic acid and a preparation method thereof, and the use of unsaturated ester derivatives of oleanolic acid in the preparation of weight-loss drugs and weight-loss drugs. Application in health products. Background technique [0002] Obesity has become the largest chronic disease in the world [Haslam DW et al., Lancet, 2005, 366:1197-1209], which can cause type II diabetes, cardiovascular and cerebrovascular diseases, gallbladderdisease, osteoarthritis, obstructive sleep apnea, cancer, etc. At least 3.4 million adults die each year from being overweight or obese [Baretic M et al., Digest Dis Sci., 2012, 30(2): 168-172; Derosa G et al., Expert Opin Drug Saf., 2012, 11(3), 459- 471]. At present, Orlistat (Orlistat), as the only long-acting weight-loss drug, still has relatively large side effects, especially causing li...
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