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Benzo macrolide compound (3R)- des-O-methyllasiodiplodin, its derivatives and preparation method and use

A technology of methylmadiprene and macrolides, which is applied in the field of benzomacrolides and can solve problems such as no biological activity research reports

Inactive Publication Date: 2012-10-03
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

After literature search, there is no research report on the biological activity of this type of compound in this respect

Method used

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  • Benzo macrolide compound (3R)- des-O-methyllasiodiplodin, its derivatives and preparation method and use
  • Benzo macrolide compound (3R)- des-O-methyllasiodiplodin, its derivatives and preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Preparation of benzomacrolide compound (3R)-des-O-methylmadiprelline

[0025] (1) Extraction: The dry weight of the mangrove plant Mango chinensis is 3.1kg, and it is extracted 4 times by percolation with 10L of methanol. The extracts are combined and then concentrated under reduced pressure. The obtained extract is suspended in 1000ml of 1N NaCl solution, and extracted repeatedly with 1000ml of petroleum ether. The suspension was collected three times, and the resulting extracts were combined and concentrated under reduced pressure to obtain 11 g of petroleum ether extract.

[0026] (2) Separation: 11g of petroleum ether extract was subjected to 100-200 mesh silica gel column chromatography, and petroleum ether / ethyl acetate 100:0→95:5→90:10→70:30→50:50→30:70 → 0:100 gradient elution, the amount of each gradient is 1000ml; among them, 1.2g of the eluted part with a volume ratio of petroleum ether / ethyl acetate of 60:40 is washed with a gradient of petroleum ether / ace...

Embodiment 2

[0029] (3R)-Methylate (R 1 and R 2 are all methyl) prepare

[0030] Weigh 5.0 mg of the (3R)-de-O-methylmaudeprene sample prepared in Example 1 in a 25 mL round bottom flask, add 2 mL of NaOH solution dissolved with 2.5 times the equivalent of methyl iodide, and add an appropriate amount of phase Transfer catalyst tetrabutylammonium bromide, heat and reflux in 10mL water / dichloromethane two-phase system for 4 hours to obtain the methylate (R 1 =R 2 =CH 3 ).

[0031] (3R)-De-O-methylmadipredine methylated spectral data are as follows: C 18 h 28 o 4 ; 1 HNMR (300MHz, CDCl 3) 6.24(d, J=2.6Hz, H-5′), 6.21(d, J=2.6Hz, H-3′), 5.18(m, H-3), 3.65, 3.61 (both s, 2×OCH 3 ), 3.26, 2.51 (m, H-10), 1.40~2.49 (H-4~9), 1.37 (d, J=7.0Hz, 3-Me).

Embodiment 3

[0033] (3R)-Acetylate (R 1 and R 2 are all acetyl) preparation

[0034] Weigh 5.0 mg of the (3R)-des-O-methylmaudeprene sample prepared in Example 1 and dissolve it in 4 mL of pyridine solution, add 2 mL of acetic anhydride solution, and react overnight at room temperature to obtain (3R)-des- The acetylated compound of O-methylmadipredrine (R 1 = R 2 =COCH 3 ).

[0035] (3R)-De-O-methylmadipredine acetylate spectral data are as follows: C 20 h 28 o 6 ; 1 HNMR (300MHz, CDCl 3 ) 6.24(d, J=2.6Hz, H-5'), 6.21(d, J=2.6Hz, H-3'), 5.18(m, H-3), 3.26, 2.51(m, H-10), 2.28, 2.26 (both s, 2×COCH 3 ) 1.40~2.49 (H-4~9), 1.37 (d, J=7.0Hz, 3-Me).

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Abstract

The invention relates to the technical field of medicine, in particular to a compound (3R)- des-O-methyllasiodiplodin obtained by extracting and separating from Cerbera in Chinese Mangrove, its derivatives and preparation method and use. The (3R)- des-O-methyllasiodiplodin and its derivatives has the following formula, if R1 and R2 are all hydrogen, the formula represents (3R)- des-O-methyllasiodiplodin. It is shown by the external detection that the compound and its derivatives have obvious steapsase inhibition activity, thus the compound and its derivatives can be used for preparing a medicament for preventing or treating the metabolic imbalance diseases such as obesity, diabetes, hyperlipidemia, fatty liver and the like. The invention also provides a lead compound for developing a new medicament for preventing or treating the metabolic imbalance diseases, thus the invention has important meaning for developing and using Chinese marine biological resources.

Description

technical field [0001] The present invention relates to the technical field of medicine, in particular to a class of benzomacrolide compound (3R)-des-O-methylmadiprolactone isolated from Chinese mangrove plant Cerbera manghas [ (3R)-des-O-methyllasiodiplodin], its derivatives and their preparation methods and uses. This type of compound has obvious inhibitory activity on pancreatic lipase, and can be used as a lead compound for the development of a new class of drugs for the prevention or treatment of obesity and related metabolic diseases, and can also be used as a treatment for common clinical obesity and related metabolic diseases application in medicine. Background technique [0002] In the past 20 years, the incidence of obesity has been increasing all over the world, especially in developed countries. There are many reasons for obesity, such as genetic factors, environmental factors, eating habits, etc. Among them, high-fat diet is an important cause of obesity. Due...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D313/00A61K31/365A61P3/04A61P3/10A61P3/06A61P1/16
Inventor 王贺瑶郭跃伟张小东李亮
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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