New Gelsmium elegans Benth. alkaloid compound as well as preparation method and application thereof

A technology of gynecine alkaloids and compounds, applied in the field of medicine, achieves the effect of therapeutic index 37, high yield and shortened separation cycle

Active Publication Date: 2012-01-18
FUJIAN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But, the compound that the present invention relates to has the following formula structure, up to now, have not yet found the compound disclosed by the present invention in patent or bibliography, a kind of new kelp alkaloid monomer and preparation method thereof, and above-mentioned compound in Application in preparation of medicine for treating pain

Method used

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  • New Gelsmium elegans Benth. alkaloid compound as well as preparation method and application thereof
  • New Gelsmium elegans Benth. alkaloid compound as well as preparation method and application thereof
  • New Gelsmium elegans Benth. alkaloid compound as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1: the preparation of formula (I) compound

[0036] 1. Sample: total alkaloids of Gelcyonium, refer to the classic extraction method of Gelkins alkaloids [Chen Zhongliang. Extraction and Separation of Gelkins Alkaloids, Bulletin of Traditional Chinese Medicine, 1987, 12 (5): 41; Xu Jian, Liang Chongzhen. Comparison of extraction methods of total alkaloids of Gelkins, Pharmaceutical Bulletin, 1988, 23 (6): 341-342; Chen Jingfeng, Yuan Hui. Extraction, separation, identification and general toxicity of total alkaloids of Gelkins, Journal of Hunan Agricultural University (Natural Science Edition), 2003, 29 (5): 422-425] obtained from the rhizome of Ficus chinensis, and the extract was vacuum-dried to obtain the crude extract of total alkaloids in brown-red powder form.

[0037] 2. Instrument: TBE-300A high-speed countercurrent chromatograph, Shanghai Tongtian Biotechnology Co., Ltd.

[0038] 3. Method:

[0039] 3.1 Prepare a solvent system, methyl tert-butyl...

Embodiment 2

[0043] Embodiment 2: identification of formula (I) compound

[0044] The target compound of above-mentioned light yellow crystal, in high-resolution mass spectrometry ESI-MS (see figure 1 ) gives the molecular ion peak [M+H] + m / z 343.1655, thus determining the molecular weight to be 342.1655. UV spectrum (see figure 2 ) The maximum absorption peak wavelength λmax (ethanol solvent) is located at 215 nm and 234 nm, showing the characteristic absorption of the indole ring. IR spectrum (see image 3 ) 1713.25cm -1 Shows carbonyl absorption, 1465.41cm -1 、1617.14cm -1 、756.41cm -1 Shows benzene ring absorption, 2850-2960cm -1 For methyl and methylene absorption, 1300-1000cm -1 It is absorbed by ether bond. 1 H-NMR (CDCl 3 and CD 3 OD) (see Figure 4 ) shows four groups of aromatic hydrogen signals δ7.62 (1H, d, 9-H, J =7.6 Hz), 7.20 (1H, td, 10-H, J =7.6, 1.0 Hz), 7.41 (1H, td, 11-H, J =7.8, 1.0 Hz), 7.06 (1H, d, 12-H, J =7.7 Hz); a methoxy signal δ3.99 (3H...

Embodiment 3

[0047] Embodiment 3: the acute toxicity test of formula (I) compound

[0048] 1. Drugs and reagents:

[0049] The compound of formula (I) was prepared by the above method with a purity of 98.3%. The compound of formula (I) was accurately weighed and diluted with normal saline to the required solution for each dosage group below.

[0050] 2. Animals

[0051] Kunming male mice, weighing 18-22 g, clean grade, provided by Shanghai Slack Experimental Animal Co., Ltd. The room temperature is 20-25°C, food and drink are free, and the light-dark cycle is 12 / 12 h. It is used for formal experiments after 3 days of adaptation to the laboratory.

[0052] 3. Method

[0053] The mice were randomly divided into 6 groups, 10 in each group, each group of mice were subcutaneously injected with 0.7 mg / kg, 0.49 mg / kg, 0.343 mg / kg, 0.24 mg / kg, 0.168 mg / kg, 0.118 mg / kg The compound of formula (I) was observed for 7 days and the death of mice was recorded, and the LD of the compound was calcul...

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Abstract

The invention discloses a new Gelsmium elegans Benth. alkaloid compound as well as a preparation method and application thereof. In the preparation method, a target compound is separated from Gelsmium elegans Benth. by using a pH-zone-refining countercurrent chromatography and taking a total Gelsmium elegans Benth. alkaloid crude extract as a raw material and a high-speed counter-current chromatographic instrument as separation equipment; and the method has the advantages of large preparation amount, less sample loss and strong controllability, and is convenient and fast and is suitable for industrial production. By the determination of high-resolution mass spectrometry, ultraviolet spectrum, infrared spectrum, <1>H, <13>C-NMR (nuclear magnetic resonance) spectrum, <1>H-<1>HCOSY (correlation spectrometry), HSQC (heteronuclear single quantum coherence) spectrum and HMBC (heteronuclear multiple-bond correlation) spectrum, the new Gelsmium elegans Benth. alkaloid compound has the structure of a formula (I). A pharmacological test shows that the compound in the invention has dose dependence, powerful analgesic effect, less tolerance, addiction and side effect and treatment index far higher than that of total Gelsmium elegans Benth. alkaloid, can be used for preparing a novel powerful low-toxicity medicament or lead compound used for treating pain, and has definite industrial prospect.

Description

technical field [0001] The invention relates to the technical field of medicines, in particular to a novel alkaloid compound isolated from a plant ginkgo. The present invention also relates to a process for the preparation of the compound. The present invention also relates to the application of the compound in the preparation of medicines, especially the application in the field of preparation of analgesics. Background technique [0002] Pain plagues tens of millions of patients. According to incomplete statistics, the current incidence of pain in the world is about 35% to 45%, and the incidence rate of the elderly is higher, about 75% to 90%. Pain seriously affects the work and life of patients. Drug analgesia is currently one of the main means of clinically treating pain in patients. Among them, opioid analgesics such as morphine and antipyretic, analgesic and anti-inflammatory drugs such as aspirin are the most commonly used, and the annual consumption is huge (the out...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/18A61K31/407A61P29/00
Inventor 俞昌喜苏燕评许盈杨渐
Owner FUJIAN MEDICAL UNIV
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