Application of a kind of sterol derivative to inhibit lipase

A kind of use, the only technology, applied in the field of medicine and chemical industry, can solve problems such as adverse reactions

Active Publication Date: 2017-09-22
BEIJING WBL PEKING UNIV BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But these two drugs have obvious adverse reactions: the side effects of sibutramin mainly include thirst, constipation, dizziness and insomnia, and the adverse reactions of orlistat are mainly gastrointestinal symptoms, such as diarrhea, abdominal pain, oily spots, flatulence, etc. , and its long-term effect needs to be further evaluated

Method used

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  • Application of a kind of sterol derivative to inhibit lipase
  • Application of a kind of sterol derivative to inhibit lipase
  • Application of a kind of sterol derivative to inhibit lipase

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0121] Embodiment 1: the preparation of formula II compound (1)

[0122] Steps:

[0123] 1) Take Xuezhikang Capsules (manufactured by Peking University Weixin) about 1 kg dry powder content, use 2-6 times the volume of dichloromethane as solvent to ultrasonically extract 3 times, each time for 20-40 minutes, combine the extracts, concentrate under reduced pressure and The solvent was recovered to obtain 91 g of dichloromethane fine extract.

[0124] 2) 50 g of dichloromethane fine extract was taken, separated by silica gel column chromatography, and carried out gradient elution with petroleum ether and ethyl acetate. The volume ratio of petroleum ether-ethyl acetate is 75:25, 50:50, 25:75, 0:100 in sequence.

[0125] 3) Take 5.0 g of petroleum ether-ethyl acetate at a ratio of 25:75, separate by C18 reverse-phase column chromatography, and obtain 4 fractions (methanol-water 10 :90, 50:50, 75:25, 100:0), wherein 1.3 g of methanol-water (75:25) eluting fraction was purified...

Embodiment 2

[0126] Embodiment 2: the preparation of formula II compound (2)

[0127] Steps:

[0128] 1) Take 5 kg of red yeast rice, use 2-6 times the volume of dichloromethane as a solvent for ultrasonic extraction 3 times, each time for 20-40 minutes, combine the extracts, concentrate under reduced pressure and recover the solvent to obtain 78 g of dichloromethane fine extract .

[0129] 2) Take 30 g of dichloromethane fine extract, and separate it by silica gel column chromatography, and carry out gradient elution with petroleum ether and ethyl acetate. The volume ratio of petroleum ether-ethyl acetate is 75:25, 50:50, 25:75, 0:100 in sequence.

[0130]3) Take 3.0 g of petroleum ether-ethyl acetate at a ratio of 25:75, separate by C18 reverse phase column chromatography, and obtain 4 fractions (methanol-water 10 :90, 50:50, 75:25, 100:0), wherein 0.8 g of methanol-water (75:25) eluting fraction was purified by semi-preparative high-performance liquid chromatography and purified wi...

Embodiment 3

[0131] Embodiment 3: the structural identification of compound

[0132] The samples used were the compounds prepared in Examples 1 and 2.

[0133] 1. Physicochemical data of the compound

[0134] White powder, optical rotation: [α] 25 D -50.00 (c0.118, CH 2 Cl 2 :MeOH=1:1);

[0135] There are three maximum absorption peaks in the UV spectrum, which are λ max (CH 2 Cl 2 : MeOH) = 271.6 nm, 282.2 nm, 293.8 nm.

[0136] FT-IR (KBr, cm -1 ) Spectrum: 3392 (-OH), 2969, 2933 (saturated hydrocarbon), 1652, 1647 (C=C), 1456, 1378 (gem dimethyl).

[0137] 2. Determination of molecular formula

[0138] m / z 483.3104[M+Na] given by HR-ESI-MS + (calcd.483.3081, err2.3), it is deduced that the molecular weight of the compound is 460.32. exist 1 H-NMR and 13 C-NMR shows that there are 40 hydrogen signals and 28 carbon signals in total. From DEPT shows that there are 6 quaternary carbons, 10 CH, 6 CH 2 and 6 CH 3 . exist 13 In C-NMR, there are 4 olefinic carbon signals a...

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Abstract

The invention belongs to the field of medicine and chemical industry, and relates to the use of a sterol derivative for inhibiting lipase. Wherein, the sterol derivative is a compound shown in formula I, or a pharmaceutically acceptable salt thereof, wherein R1 is selected from -OH, =O, H, and C1-C3 alkyl; R2 is selected from -OH , H, and C1-C3 alkyl; R3 is selected from -OH, =O, H, and C1-C3 alkyl; R4 is selected from -OH, H, and C1-C3 alkyl; and R1, R2, R3, and any 2, 3 or 4 of R4 are ‑OH at the same time. The compound of the present invention can effectively inhibit lipase, and the inhibitory effect is in a concentration-effect relationship; thus, it has the potential of being a drug for preventing and / or treating and / or adjuvantly treating obesity or obesity-related diseases, or a weight-loss drug.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, and relates to the use of a sterol derivative for inhibiting lipase. Background technique [0002] Monascus-fermented rice is a purple-red rice koji made from rice as raw material and fermented by Monascus. Red koji was called Danqu in ancient times, and it was fermented by inoculating koji or distiller's yeast based on Monascus on rice. Its color is red, so it is also called red koji, red rice, red rice, and red rice. Fujian and other places. Therefore, it is also known as Fuqu, Fumi, etc. [0003] my country has a long history of using Monascus, and it has been used to make koji since the Han Dynasty. Red yeast rice is a traditional Chinese medicine that combines both diet and therapy. As early as in ancient times, it has been widely used in food coloring, wine making, fermentation, and traditional Chinese medicine. "Drinking Zheng Yao" has red yeast rice "sweet, flat, non-toxi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/58A61P3/06A61P9/10A61P3/10A61P3/04C07J71/00
Inventor 段震文郭树仁李雪梅
Owner BEIJING WBL PEKING UNIV BIOTECH
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