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WO2002022144A1 - The uses of chinese herb piper laetispicum c. dc and its extract for the preparation of pharmaceutical composition - Google Patents

The uses of chinese herb piper laetispicum c. dc and its extract for the preparation of pharmaceutical composition Download PDF

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WO2002022144A1
WO2002022144A1 PCT/CN2001/001172 CN0101172W WO0222144A1 WO 2002022144 A1 WO2002022144 A1 WO 2002022144A1 CN 0101172 W CN0101172 W CN 0101172W WO 0222144 A1 WO0222144 A1 WO 0222144A1
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chinese herbal
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loquat
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Shengli Pan
Fugang Qian
Ezhuo Wang
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Fudan University
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
    • A61K31/36—Compounds containing methylenedioxyphenyl groups, e.g. sesamin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/67—Piperaceae (Pepper family), e.g. Jamaican pepper or kava
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia

Definitions

  • the invention relates to extracting active ingredients from Chinese herbal medicine leaf medicine to make medicines, which are used for preventing and treating depression and mental disorders. Background technique
  • Kavacava is a new type of natural health medicine that has become popular in Europe, America and Japan in recent years. Used to relax tension, sedation and anti-depression. Its plant source is Piper methysticum Forst, which grows in the South Pacific island countries. 0
  • An object of the present invention is to provide a Chinese herbal medicine, a large leaf medicine Piper laetispicum C. DC, an extract thereof and a preparation method thereof.
  • Another object of the present invention is to use the above-mentioned extract as a raw material of a pharmaceutical preparation.
  • Still another object of the present invention is to provide the application of Chinese herbal medicine leaf medicine and its extract in the preparation of medicine for treating depression and mental disorders.
  • Large leaf Piper laetispicum C. DC is a Piper L. plant of the Piperaceae family, distributed in Guangdong, soiled Guangxi, and Hainan provinces. In the place of origin, it is used as an analgesic and blood swelling and analgesic agent for the treatment of bruises and bruises.
  • the research of the present invention finds that the extracts extracted from the ethanol and ethyl acetate of the large leaf have analgesic, sedative and antidepressant effects. Especially in terms of antidepressant effect, it is 2 to 3 times stronger than similar foreign products Kavakava.
  • An invention has been prepared by the following method.
  • the main ingredients are lactones, glycosides and alkaloids.
  • the lobular medicine and the extract thereof can be used as pharmaceutical raw materials to make preparations such as capsules, tablets, injections, oral liquids, and slow-release agents.
  • the large leaf extract (POS) of the present invention has obvious antidepressant effects, sedative and analgesic effects on mice.
  • the animal experiment method and results of the present invention are as follows-The kava kava used as a control in this experiment is a product of Nutratech. Rhizoma grandifolia extract is formulated with 2% Tween 80. Experimental animals: Kunming mice, male, 22-25g, 8 mice per group.
  • Antidepressant Forced swimming. Mice were randomly divided into groups and adapted to the environment for 1 day. The drug was administered orally on the second day. Half an hour after the administration, the mice were placed in a glass bottle with a diameter of 10 cm, a height of 30 cm, and a water depth of 15 cm at a water temperature of 2.4 ° C. Each mouse could only perform experiments once. The mice were separated from each other during the experiment. When the mouse was placed in a glass bottle, it began to swim exclusively, and when "despaired" it floated on the water. Use a stopwatch to record the continuous time within 6 minutes and the next 4 minutes.
  • mice were placed in a box with a diameter of 35cm and a height of 15cm, and a 5cm X 5cm box was drawn on the bottom. The mice were first allowed to acclimate to the environment for 3 minutes, and then the number of cells that the mice walked within 5 minutes was observed.
  • mice were injected intraperitoneally with 1% acetic acid 0.1ml 1 10g body weight. Observe the number of twists within 10 minutes after the first twist.
  • control group was administrated with an equal amount of 2% Tween 80 aqueous solution.
  • Compound 2 dihydropiperlonguminine dark white needle-like crystal, hardly soluble in water, easily soluble in organic solvents such as chloroform, acetone, ethyl acetate, etc. Melting point: m.p.90-95 "C, molecular formula CieHaiNOs, molecular weight 275, structural formula:

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  • Natural Medicines & Medicinal Plants (AREA)
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  • General Chemical & Material Sciences (AREA)
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  • Hospice & Palliative Care (AREA)
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Abstract

The invention provides one Chinese herb Piper laetispicum C. DC and its extract and a process for the preparation of the extract. Meanwhile, the invention also provides the uses of the Chinese herb and its extract as the raw material for the preparation of tablet, injection, sustained release dosage form, capsule and composition. In addition, the invention also provides the uses of the Chinese herb and its extract for the treatment of depression.

Description

说 书  Say book

中草药大叶銪及其提取物在制备药物组合物中的应用  Application of Chinese herbal medicine Loquat and its extract in preparing pharmaceutical composition

技术领域 Technical field

本发明是关于从中草药大叶葯中提取活性成分制成药物， 用于防治抑郁症 及精神障碍性疾病。 背景技术  The invention relates to extracting active ingredients from Chinese herbal medicine leaf medicine to make medicines, which are used for preventing and treating depression and mental disorders. Background technique

随着时代的进步， 工作的节律不断加快， 因工作压力造成的紧张情绪而引 起的抑郁症、 精神障碍及因此导致的早老性痴呆 (阿尔茨海默病）已成为当今世 界危害人类健康的 5大疾病之一。 世界卫生组织 (WHO)透露， 精神上的疾病已经 给人类社会带来沉重的负担。 中国卫生部也证实， 精神障碍在我国疾病总负担 的排名中居首位， 已超过了心脑血管、 呼吸系统及恶性肿瘤等疾患。  With the progress of the times, the rhythm of work is constantly accelerating. Depression, mental disorders, and premature dementia (Alzheimer's disease) caused by the stress caused by work stress have become the world's most harmful to human health. One of the big diseases. The World Health Organization (WHO) revealed that mental illness has placed a heavy burden on human society. The Chinese Ministry of Health has also confirmed that mental disorders rank first in the ranking of total disease burden in China and have surpassed diseases such as cardiovascular, cerebrovascular, respiratory and malignant tumors.

卡瓦卡瓦 (Kavakava)为近些年来风靡于欧美及日本等国的新型天然保健药 品。 用于放松紧张情绪、 镇静及抗抑郁等。 其植物来源为生长于南太平洋岛国 的卡瓦胡椒 (Piper methysticum Forst) 0 Kavacava is a new type of natural health medicine that has become popular in Europe, America and Japan in recent years. Used to relax tension, sedation and anti-depression. Its plant source is Piper methysticum Forst, which grows in the South Pacific island countries. 0

据透露卡瓦卡瓦在临床治疗中还有不尽人意之处， 在我国天然药物中发掘 抗抑郁和治疗精神障碍性疾病的药物已形成研究热点。 发明内容  According to reports, Kava Kava still has unsatisfactory results in clinical treatment. The discovery of antidepressants and treatment of mental disorders among natural medicines in China has become a research hot spot. Summary of the Invention

本发明的目的是提供中草药大叶药 Piper laetispicum C. DC和其提取 物及其制备方法。  An object of the present invention is to provide a Chinese herbal medicine, a large leaf medicine Piper laetispicum C. DC, an extract thereof and a preparation method thereof.

本发明的另一目的是将上述提取物作为药物制剂的原料。  Another object of the present invention is to use the above-mentioned extract as a raw material of a pharmaceutical preparation.

本发明还有一个目的是提供中草药大叶药及其提取物在制备治疗抑郁症及 精神障碍性疾病药物中的应用。  Still another object of the present invention is to provide the application of Chinese herbal medicine leaf medicine and its extract in the preparation of medicine for treating depression and mental disorders.

大叶 Piper laetispicum C. DC为胡椒科（Piperaceae)胡椒属（Piper L. ) 植物， 分布于我国广东及广西南部和海南省。 在产地用作活血消肿止痛药， 用 于治疗跌打损伤、 瘀血肿痛。 本发明研究发现大叶 其醇提取乙酸乙酯萃取之 抽提物具镇痛、 镇静和抗抑郁作用。 特别在抗抑郁作用方面， 比国外同类产品 卡瓦卡瓦（Kavakava)强 2— 3倍。  Large leaf Piper laetispicum C. DC is a Piper L. plant of the Piperaceae family, distributed in Guangdong, southwestern Guangxi, and Hainan provinces. In the place of origin, it is used as an analgesic and blood swelling and analgesic agent for the treatment of bruises and bruises. The research of the present invention finds that the extracts extracted from the ethanol and ethyl acetate of the large leaf have analgesic, sedative and antidepressant effects. Especially in terms of antidepressant effect, it is 2 to 3 times stronger than similar foreign products Kavakava.

有发明通过下述方法制备大 ^筠提取物。  An invention has been prepared by the following method.

取大叶葯根粗粉加 8倍量 95 %乙醇回流 2次， 每次 1小时， 过滤， 合并滤 液， 减压浓缩至干， 再加 3倍量乙酸乙酯萃取 3次， 合并萃取液， 减压浓缩至 干， 得淡黄褐色粘稠状固形物， 得率 3. 17% ,  Take the large powdered medicinal root powder and add 8 times the amount of 95% ethanol to reflux 2 times for 1 hour each time, filter, combine the filtrates, concentrate under reduced pressure to dryness, add 3 times the amount of ethyl acetate and extract 3 times, combine the extracts, 17%, Concentrated to dryness under reduced pressure to obtain a light yellow brown viscous solid, yield 3.17%,

主要成分为内酯类、 甙类和生物碱类。 The main ingredients are lactones, glycosides and alkaloids.

本发明大叶药及其提取物可作为药物原料制成胶囊、 片剂、 注射剂、 口服 液、 缓释剂等制剂。 经动物实验结果证明， 本发明大叶 提取物 (P0S)对小鼠有 明显的抗抑郁作用和镇静、 镇痛作用。  The lobular medicine and the extract thereof can be used as pharmaceutical raw materials to make preparations such as capsules, tablets, injections, oral liquids, and slow-release agents. According to the results of animal experiments, the large leaf extract (POS) of the present invention has obvious antidepressant effects, sedative and analgesic effects on mice.

本发明动物实验方法和结果如下 -- 本实验用作对照的卡瓦卡瓦为美国 Nutratech.公司产品。 大叶莼提取物以 2%吐温 80制剂。 实验动物： 昆明种小鼠， 雄性， 22— 25g， 每组 8只。 The animal experiment method and results of the present invention are as follows-The kava kava used as a control in this experiment is a product of Nutratech. Rhizoma grandifolia extract is formulated with 2% Tween 80. Experimental animals: Kunming mice, male, 22-25g, 8 mice per group.

实验方法：  experimental method:

抗抑郁： 强迫游泳法。 小鼠随机分组， 适应环境 1天。 于第 2天灌胃给药。 给药后半小时， 置直径 10cm、 高 30cm、 水深 15cm的玻璃瓶中， 水温 2.4 °C每只 小鼠只能实验 1 次。 实验时小鼠间互相隔开。 当小鼠置玻璃瓶中时， 开始拼命 游动， 当 "绝望"时就浮在水面不动。 以秒表记录 6分钟内， 后 4分钟连续不 动时间。  Antidepressant: Forced swimming. Mice were randomly divided into groups and adapted to the environment for 1 day. The drug was administered orally on the second day. Half an hour after the administration, the mice were placed in a glass bottle with a diameter of 10 cm, a height of 30 cm, and a water depth of 15 cm at a water temperature of 2.4 ° C. Each mouse could only perform experiments once. The mice were separated from each other during the experiment. When the mouse was placed in a glass bottle, it began to swim desperately, and when "despaired" it floated on the water. Use a stopwatch to record the continuous time within 6 minutes and the next 4 minutes.

镇静作用： 穿格行走法。 小鼠灌胃给药后半小时， 置直径 35cm， 高 15cm， 底部画有 5cm X 5cm方格的箱内。 先让小鼠在箱内适应环境 3分钟， 然后观察 小鼠在 5分钟内行走的格数。  Sedative effect: Cross lattice walking method. Half an hour after intragastric administration, mice were placed in a box with a diameter of 35cm and a height of 15cm, and a 5cm X 5cm box was drawn on the bottom. The mice were first allowed to acclimate to the environment for 3 minutes, and then the number of cells that the mice walked within 5 minutes was observed.

镇痛作用： 醋酸扭体法。 小鼠灌胃给药后半小时， 腹腔注射 1 %醋酸 0. 1ml 1 10g体重。 观察第 1次扭体发生后 10分钟内扭体的次数。  Analgesic effect: Acetic acid writhing method. Half an hour after intragastric administration, mice were injected intraperitoneally with 1% acetic acid 0.1ml 1 10g body weight. Observe the number of twists within 10 minutes after the first twist.

对照组以等量 2%吐温 80水溶液灌胃。  The control group was administrated with an equal amount of 2% Tween 80 aqueous solution.

实验结果采用 t检验法统计数据。 表 1抗抑郁作用（强迫游泳法) 组别 剂量 mg I kg 不动时间 min 对照组 2. 87±0· 17  The experimental results used t-test statistical data. Table 1 Antidepressant effect (forced swimming method) group dose mg I kg immobility time min control group 2. 87 ± 0 · 17

PDS 120 1. 41 ±0· 34**  PDS 120 1. 41 ± 0 · 34 **

PDS 60 1. 55±0. 41**  PDS 60 1. 55 ± 0. 41 **

PDS 30 2. 24±0. 33  PDS 30 2. 24 ± 0. 33

KaVakaVa 120 1. 30±0. 28**  KaVakaVa 120 1. 30 ± 0. 28 **

KaVakava 60 2. 71±0· 16  KaVakava 60 2. 71 ± 0 · 16

表 2镇静作用 (穿格行走法) 组别 剂量 mg/kg 穿格行走数 Table 2 Sedation effect (cross-frame walking method) Group dose mg / kg Number of cross-frame walking

170. 25 ±7. 53 170. 25 ± 7. 53

116. 88 ±5. 96**  116. 88 ± 5. 96 **

162. 13± 12. 86  162. 13 ± 12. 86

170. 13±15. 06  170. 13 ± 15. 06

138. 13± 12. 56*  138. 13 ± 12. 56 *

167. 38±8. 70 表 3镇痛作用 (醋酸扭体法） 组别 齐 U量 rag/kg 扭体数 对照组 29. 25±2. 61 167. 38 ± 8. 70 Table 3 Analgesic effect (acetic acid writhing method) Group U amount rag / kg writhing number control group 29. 25 ± 2. 61

PDS 120 10. 38± 1. 44*** PDS 120 10. 38 ± 1. 44 ***

PDS 60 19. 13 ±2. 82* PDS 60 19. 13 ± 2. 82 *

PDS 30 20. 34±2. 18*  PDS 30 20. 34 ± 2. 18 *

Kavakava 120 14. 25 ±2. 47**  Kavakava 120 14. 25 ± 2. 47 **

Kavakava 60 16. 25±0. 90**  Kavakava 60 16. 25 ± 0. 90 **

*P<0. 05 **P<0. 01 ***p<o. 001 在对大叶脔提取物进行分离鉴定， 发现提取物中存在的下述二种化合物有 抗抑郁作用， 化合物 1 : 5'-methoxy-3',4'-methylenedioxycinnamoylisobutylamide 白色针状晶体， 难溶于水， 易溶于氯仿、 丙酮、 乙酸乙酯等有机溶剂， 熔点为 : m.p.90-9rC, 分子式 Ci5Hi9NCk， 分子量为 227， 结构式： * P <0. 05 ** P <0. 01 *** p <o. 001 In the isolation and identification of the extract of P. macrophylla, the following two compounds present in the extract were found to have antidepressant effects, Compound 1 : 5'-methoxy-3 ', 4'-methylenedioxycinnamoylisobutylamide White needle-like crystal, hardly soluble in water, easily soluble in organic solvents such as chloroform, acetone, ethyl acetate, etc. Melting point : mp90-9rC, molecular formula Ci5Hi9NCk, molecular weight 227 , Structural formula:

Figure imgf000004_0001
Figure imgf000004_0001

0  0

化合物 2: dihydropiperlonguminine暗白色针状晶体， 难溶于水， 易溶于氯 仿、 丙酮、 乙酸乙酯等有机溶剂， 熔点为： m.p.90-95"C , 分子式 CieHaiNOs, 分 子量为 275， 结构式：  Compound 2: dihydropiperlonguminine dark white needle-like crystal, hardly soluble in water, easily soluble in organic solvents such as chloroform, acetone, ethyl acetate, etc. Melting point: m.p.90-95 "C, molecular formula CieHaiNOs, molecular weight 275, structural formula:

Figure imgf000004_0002
Figure imgf000004_0002

上述二种化合物的抗抑郁作用， 用强迫游泳法实验其结果见下表:  The antidepressant effects of the above two compounds are shown in the following table using the forced swimming test:

Figure imgf000004_0003
Figure imgf000004_0003

**Ρ<0.01 ***Ρ<0.001  ** P <0.01 *** P <0.001

Claims

中草药大叶菡及其裉取物:^制备药物组合物中的应用 权刺要求书 Chinese herbal medicine Loquat and its extracts 1. 一种中草药大叶筠及其提取物， 其在制备治疗抑郁症和精神障碍性疾病药 物组合物中的应用。 What is claimed is: 1. A Chinese herbal medicine, Rhizoma aurantium, and its extract, and its use in the preparation of a pharmaceutical composition for treating depression and mental disorders. 2. 按权利要求书 1所述的中草药大叶筠及其提取物， .  2. The Chinese herbal medicine Loquat and its extract according to claim 1,. 其特征在于 所述的提取物通过下述方法提取， 取大叶筠根粗粉加乙醇回流， 减压浓缩至干， 再加乙酸乙酯萃取， 减压浓缩至干， 得淡黄褐色粘稠状固形物。It is characterized in that the extract is extracted by the following method. The coarse powder of Rhizoma dahurica is added under reflux with ethanol, concentrated under reduced pressure to dryness, and then extracted with ethyl acetate, and concentrated to dryness under reduced pressure to obtain a light yellow brown viscous Like solids. 3. 按权利要求 1所述的中草药大叶筠及其提取物， 3. The Chinese herbal medicine Loquat and its extract according to claim 1, 其特征在于 用所述的大叶筠及其提取物作为原料制成胶囊、 片剂、 注射剂、 口服液、 缓释剂等制剂。 It is characterized in that the preparations such as capsules, tablets, injections, oral liquids, slow-release agents and the like are prepared by using the Rhizoma dahurica and its extract as raw materials. 4. 按权利要求 2所述的中草药大叶药及其提取物，  4. Chinese herbal medicine, large leaf medicine and extract thereof according to claim 2, 其特征在于 提取物中应包含下述化合物： 分子式 C15H19N04， 分子量为 227， 化 合物 5'-methoxy-3 ',4'-methylenedioxycinnamoylisobutylamide , 焰点为： m.p.90-9iIt is characterized in that the extract should contain the following compounds: molecular formula C 15 H 19 N0 4 , molecular weight 227, compound 5'-methoxy-3 ', 4'-methylenedioxycinnamoylisobutylamide, flame point: mp90-9i °C， 结构式： ° C, structural formula:
Figure imgf000005_0001
Figure imgf000005_0001
 5. 按权利要求 2所述的中草药大叶筠及其提取物，  5. The Chinese herbal medicine Loquat and its extract according to claim 2, 其特征在于 提取物中应包含下述化合物： 分子式 C16H21N03， 分子 It is characterized in that the extract should contain the following compounds: molecular formula C 16 H 21 N0 3 , molecular 合物 dihydropiperionguminine, 熔点为： m.p.90-95°C , 结构式： Compound dihydropiperionguminine, melting point: m.p.90-95 ° C, structural formula:
Figure imgf000005_0002
Figure imgf000005_0002
PCT/CN2001/001172 2000-07-14 2001-07-12 The uses of chinese herb piper laetispicum c. dc and its extract for the preparation of pharmaceutical composition Ceased WO2002022144A1 (en)

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CN100436407C (en) * 2003-03-20 2008-11-26 蒋毅 Preparation of piper laetispicum effective part and its use in medical therapy and health field
CN103063789A (en) * 2011-10-19 2013-04-24 天士力制药集团股份有限公司 Liquid phase analysis method for simultaneously detecting 12 amide alkaloids in Piper laetispicum

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CN100356940C (en) 2004-12-01 2007-12-26 蒋毅 Method for preparing piper laetispicum extract, extract and its use
CN102475746B (en) * 2010-11-23 2015-05-06 天士力制药集团股份有限公司 Preparation method of piper laetispicum active ingredient
CN113209165A (en) * 2017-11-01 2021-08-06 苏州颐华生物医药技术股份有限公司 Piper laetispicum extract and preparation method and application thereof

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100436407C (en) * 2003-03-20 2008-11-26 蒋毅 Preparation of piper laetispicum effective part and its use in medical therapy and health field
CN103063789A (en) * 2011-10-19 2013-04-24 天士力制药集团股份有限公司 Liquid phase analysis method for simultaneously detecting 12 amide alkaloids in Piper laetispicum

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