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Laurane type sesquiterpene compound or derivative thereof and preparation method and application thereof

A technology of sesquiterpenes and laurane, applied in the directions of digestive system, organic chemistry, drug combination, etc., can solve the problems of uncertain active ingredients and their amounts, difficult to control, insufficient effect, etc.

Inactive Publication Date: 2010-01-20
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

There are many reports on the extraction of lipase-inhibiting active ingredients from plants, but the effect is not sufficient. Even if the extract of a certain plant has an effect, the active ingredient and its amount are not sure
At present, Xenical is the best-selling lipase inhibitor in the market. Xenical has the characteristics of strong activity and good stability, but it has disadvantages such as uncontrollable intestinal symptoms, greasy stools, vomiting and abdominal distention.

Method used

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  • Laurane type sesquiterpene compound or derivative thereof and preparation method and application thereof
  • Laurane type sesquiterpene compound or derivative thereof and preparation method and application thereof
  • Laurane type sesquiterpene compound or derivative thereof and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Preparation of laurane-type sesquiterpenoids Lauzaol and Aplysia

[0028] (1) Extraction: 500g of the dry weight of Suatopina Okamura from East my country Sea, repeated ultrasonic extraction 3 times with 1000ml of acetone, the extracts were combined and concentrated under reduced pressure, the obtained crude extract was suspended in 500ml of aqueous solution, and extracted repeatedly with 500ml of ether. The suspension was collected three times, and the resulting extracts were combined and concentrated under reduced pressure to obtain 36.1 g of ether extract.

[0029] (2) Separation: 36.1g of ether extract was subjected to 200-300 mesh silica gel column chromatography, and petroleum ether / acetone 100:0→98:2→95:5→90:10→80:20→70:30→50 :50 gradient elution, the amount of each gradient is 1000ml; wherein, petroleum ether / acetone 98:2 eluent concentrate obtained 4.65g, through 200-300 mesh silica gel column chromatography, with petroleum ether / diethyl ether 100:0→98 : 2 → 95...

Embodiment 2

[0034] 8-Bromolauralol (R 1 is bromine, R 2 and R 3 at the same time as hydrogen)

[0035] Weigh 12.1 mg of Laualinol sample and dissolve it in 2.0 ml of ethyl acetate solution, add 1.5 times the equivalent of NaBrO 3 Aqueous solution, after mixing well, add 1.5 times equivalent of NaHSO dropwise under stirring 3 Aqueous solution, after reacting at room temperature for 18 hours, was extracted with ethyl acetate to terminate the reaction, and the solvent was recovered from the ethyl acetate extract under reduced pressure to obtain 11.7 mg of 8-bromolauralol.

[0036] The physical and chemical properties and spectral data of 8-bromolauralol are as follows: C 15 h 18 OBr 2 ; 1 H NMR (300MHz, CDCl 3 )δ: 7.70(s, H-11), 5.78(s, -OH), 2.53(s, H 3 -12), 2.23 (dd, J=12.6, 5.1Hz, H-5), 1.64 (dd, J=12.6, 7.2Hz, H-5), 1.94, 1.25 (all m, H 2 -4), 1.40(s, H 3 -13), 1.30 (s, H 3 -14), 1.10(m, H-3), 0.53(m, H 2 -15); EIMS m / z 374, 359, 306 [M] + .

Embodiment 3

[0038] 4,8,15-tribromolauralinol (R 1 , R 2 and R 3 while bromine)

[0039] Weigh 67.5 mg of Laualinol sample and dissolve it in 5.0 ml of chloroform solution, add 1.5 times the equivalent of NaBrO 3 Aqueous solution, after mixing well, add 1.5 times equivalent of NaHSO dropwise under stirring 3 Aqueous solution, after reacting at room temperature for 18 hours, was extracted with ethyl acetate to terminate the reaction, and the solvent was recovered from the ethyl acetate extract under reduced pressure to obtain 26.7 mg of 4,8,15-tribromolauralol.

[0040] The physical and chemical properties and spectral data of 4,8,15-tribromolauralol are as follows: C 15 h 16 OBr 4 ; 1 HNMR (300MHz, CDCl 3 )δ: 7.15(s, H-11), 5.58(s, -OH), 3.58(m, H-4), 3.43(m, H-15), 3.01(m, H-5), 2.69(m , H-5), 2.56(s, H 3 -12), 1.26(s, H 3 -13), 1.04 (s, H 3 -14), 2.54(m, H-3); EIMS m / z 532, 517, 357[M] + .

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Abstract

The invention relates to a laurane type sesquiterpene compound or a derivative thereof extracted and separated from a sea plant Laurencia okamurai in the East China Sea, and a preparation method and application thereof. The structural formula of the laurane type sesquiterpene compound or the derivative thereof is shown as above: when R1, R2 and R3 are hydrogen at the same time, the sesquiterpene compound or the derivative thereof is laurinferol, and when R4 is hydrogen, the sesquiterpene compound or the derivative thereof is aplysin. In vitro tests show that the sesquiterpene compound or the derivative thereof has obvious pancreatic lipase inhibition activity and is expected to be applied to preparing medicaments for preventing or treating decompensation diseases including adiposis, diabetes, hyperlipoidemia, fatty liver and the like. The sesquiterpene compound or the derivative thereof can also provide a lead compound for developing the new medicaments for preventing and treating the decompensation diseases, and is significant for developing and utilizing marine biological resources of China.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a class of laurane-type sesquiterpene compounds or derivatives thereof isolated from the marine plant Laurencia okamurai in the East my country Sea, and a preparation method and use thereof. 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 in the preparation and treatment of clinically common obesity and related metabolic diseases. application in disease 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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IPC IPC(8): C07C39/17C07D307/93A61K31/055A61K31/343A61P3/06A61P3/10A61P1/16
Inventor 郭跃伟王贺瑶毛水春张小东
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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