WO2006094456A1 - Extrait de styrax linn, preparation et utilisations correspondantes - Google Patents

Extrait de styrax linn, preparation et utilisations correspondantes Download PDF

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Publication number
WO2006094456A1
WO2006094456A1 PCT/CN2006/000341 CN2006000341W WO2006094456A1 WO 2006094456 A1 WO2006094456 A1 WO 2006094456A1 CN 2006000341 W CN2006000341 W CN 2006000341W WO 2006094456 A1 WO2006094456 A1 WO 2006094456A1
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WO
WIPO (PCT)
Prior art keywords
benzoin
extract
plant
benzofuran
jasmine
Prior art date
Application number
PCT/CN2006/000341
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English (en)
Chinese (zh)
Inventor
Qilin Li
Guolin Zhang
Jufang Yan
Xin Chen
Yu Huang
Bogang Li
Zhongrong Liu
Yuanqiao Ji
Original Assignee
Chengdu Di'ao Jiuhong Pharmaceutical Factory
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from CNB2005100204777A external-priority patent/CN100509803C/zh
Priority claimed from CN200510020478A external-priority patent/CN1830435B/zh
Priority claimed from CNB2005100204796A external-priority patent/CN100420690C/zh
Application filed by Chengdu Di'ao Jiuhong Pharmaceutical Factory filed Critical Chengdu Di'ao Jiuhong Pharmaceutical Factory
Publication of WO2006094456A1 publication Critical patent/WO2006094456A1/fr

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Classifications

    • 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)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
    • A61P5/30—Oestrogens
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/80—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings

Definitions

  • the present invention relates to a traditional Chinese medicine extract, a preparation method and use thereof, and more particularly to a succulent plant extract, a preparation method thereof and use thereof. Background technique
  • Estrogen (especially estrogen E 2 ) is one of the most important hormones in humans and other higher animals and has a wide range of physiological functions. 90% of women before menopause have sputum 2 , 50% from the ovary and adrenal gland, women after menopause, due to ovarian atrophy, ovarian function is significantly reduced, so estrogen secretion is greatly reduced, when the estrogen produced by fat cells becomes estrogen in the body The main source, if this source is insufficient, E 2 in the blood is only equivalent to the level of early follicular phase of women before menopause, which may cause bone density to decrease and lead to osteoporotic fracture.
  • the average life expectancy of a woman is 80 years old, then one third of a woman's life is after menopause, and about a quarter of people will get osteoporosis after age 65. As the population ages, the number of patients suffering from menopausal syndrome and osteoporosis will increase. In addition, some non-menopausal women may have premature ovarian failure or ovarian dysfunction, insufficient estrogen levels, and some diseases such as polyposis, infertility and other diseases are also associated with a relative reduction in estrogen levels. Therefore, drugs that seek to improve ovarian function and promote estrogen synthesis help prevent and treat these diseases.
  • Si racflcefle also known as wild jasmine, oleanaceae, about 11 genera, 180 species. China produces 9 genera, 50 species, 9 varieties, and is widely distributed.
  • Sty rax Linn also known as wild jasmine, has about 130 species. There are about 30 species and 7 varieties in China, which are mainly produced in the provinces and regions south of the Yangtze River basin. Most of the benzoin plants are available for viewing, and some are available for medicinal purposes. Its resin contains more scented acid, called “benzoin", which has the effect of clearing the spirit, promoting blood circulation and relieving pain. It is a valuable medicine in medicine; this resin can also be used to make high-grade aromatic oil.
  • the technical proposal of the present invention is to provide a benzoin plant extract and a preparation method thereof, and a pharmaceutical preparation processed from the extract for preventing or treating premature ovarian failure, climacteric syndrome, osteoporosis and ovarian dysfunction in adolescence, Use in multidrug ovarian syndrome, infertility, and pharmaceutical preparations for diseases caused by estrogen deficiency or relative deficiency.
  • the present invention provides a benzoin plant which contains a benzofuran total benzofuran in a weight percentage of 40 to 98%.
  • the benzofuran extract of the benzoin plant contains one or more benzofuran biomonomers having the following chemical structures: wherein 3, 6, 7, 8, 12 are novel compounds.
  • the extract also contains one or more benzofuran derivative monomers having the following chemical structure:
  • the benzofuran extract of the benzoin plant provided by the present invention is obtained by extracting plants of the genus [styrax]. More specifically, it is into the foot of Shishan Anxiang [Styrax perkinsiaej, Luchun benzoin 5. macranthus Pert], Chuxiong benzoin 5. limprichtii Lingelsh et BorzaJ, Vietnamese benzoin 5. tonkinensis (Pierre) Craib et Hartw.], Zhejiang benzoin 5 ⁇ Zhejiangensis SM Hwang et LL Yu], Fragrant benzoin 5.
  • the present invention also provides a method for preparing the above-mentioned benzofuran extract of benzoin, comprising the following steps:
  • extract with water, alcohol (methanol or ethanol), or aqueous alcohol, room temperature or heating (including reflux) for a certain period of time can be repeatedly extracted 1 ⁇ 3 times, and then filter the dregs , the extract liquid is concentrated under reduced pressure to obtain a total extract;
  • c, b step After the extracted aqueous layer is adsorbed by a macroporous resin column, it is eluted with a certain amount of water to remove the sugar component, and then the column is eluted with 30 to 95% ethanol, and the eluate is concentrated under reduced pressure. The extract is then vacuumed or freeze-dried into a dry powder of the benzofuran extract of benzofuran.
  • the extraction solvent is preferably a 50-90% ethanol solution.
  • the amount of the ethanol solution is 6-12 times the weight of the medicinal material, and 8 times is preferred.
  • Macroporous resin models are: D101, HPD100, HPD200, HPD300, LD140.
  • the latter step of the macroporous resin column is preferably 95% ethanol.
  • the dry powder prepared above is a light brown solid substance with a slight bitter taste.
  • the total benzofuran contained therein is 40% - 98% of the total weight.
  • the present invention also provides a method for preparing the above-mentioned benzofuran derivative monomer of the genus Benzoin, which is characterized by comprising the following steps:
  • extract with water, methanol or ethanol, or aqueous alcohol, room temperature or heating (including reflux) for a certain period of time can be repeatedly extracted 1 ⁇ 3 times, and then filter the dregs, the filtrate Concentration under reduced pressure gave a total extract.
  • the present invention also provides an extract of the genus Benzoin prepared by the above method.
  • the extract of the genus benzoin is Watzan benzoin "Sz ⁇ ra perkinsiaej, S. macranthus Perk., S. limprichtii Lingelsh et Borza", Vietnamese benzoin [S. tonkinensis (Pierre) Craib Et Hartw.], S. zhejiangensis SM Hwang et LL Yu, S. odoratissimus Champ., S. chinehsis H et SY Liang, S. benzoinoides Graib S. benzoin Dry and], S. argentifolius HL Li, ash 1 "S.
  • serrulatus Roxb sapphire scent [ An extract of any one or more of S. suberifolius Hook, et Am], S. wilsonii Rehd, S. ferrugineus, S. officinalis, S. obassia Sieb. et Zucc.
  • tile The extract of S. macranthus Perk. is an extract of the fruit of the sage of the scent of the scent of the scent of the scent of the scent of the scent of the scent of the scent of the scent of the scent of the scent of the scent of the sage Extract.
  • the present invention also provides the benzoin plant of the present invention or the total benzofuran extract thereof or the benzofuran derivative monomer of the benzoin plant for the prevention or treatment of premature ovarian failure, climacteric syndrome, osteoporosis and ovarian ovarian Uses in drugs with low function, multiple ovarian syndrome, infertility, and diseases caused by estrogen deficiency or relative deficiency.
  • the active ingredient of the medicament comprises the above-mentioned benzoin plant prodrug or its total benzofuran extract or benzoin benzofuran derivative monomer, or may contain a benzoin plant prodrug or its total benzofuran extract.
  • a compound of a monomer or a benzofuran derivative monomer that is, a western medicine or a traditional Chinese medicine active ingredient which is compatible with the synthesis of estrogen.
  • the preparation is an oral tablet, a capsule, an oral solution or an injection.
  • 1 tablet including ordinary tablets, film tablets, enteric tablets and the like.
  • dry powder of total benzofuran extract add appropriate amount of diluent such as starch, dextrin, nectar, microcrystalline fiber, etc., appropriate amount of binder such as water, ethanol, starch slurry, gelatin, cellulose, etc., moderate amount of disintegration
  • diluent such as starch, dextrin, nectar, microcrystalline fiber, etc.
  • binder such as water, ethanol, starch slurry, gelatin, cellulose, etc.
  • moderate amount of disintegration Such as dry starch, sodium methyl starch, sodium alginate, etc., and appropriate amount of lubricants such as magnesium stearate, talc, polyethylene glycol, etc., according to conventional wet granulation, drying, whole or dry granulation After pressing.
  • the film-coated tablets may be coated into a sealed bottle or an aluminum-plastic plate by conventional coating, such as cellulose, polyethylene glycol or the like
  • 2 capsules including ordinary capsules, intestinal sols and so on.
  • the above-mentioned total benzofuran extract dry powder is added with an appropriate amount of auxiliary materials such as starch, carbonic acid, mannitol, magnesium oxide, micro-silica gel, etc., and a suitable amount of lubricants such as talc, magnesium stearate, ethylene glycol ester, polysilicone, etc.
  • a suitable amount of adhesives such as mineral oil, edible oil, etc., mixed into a dry powder or granules, filled into a rubber sleeve, and packed in a closed aluminum plastic packaging.
  • a suitable amount of a sweetener such as D-xylose, xylitol, maltitol, stevioside, aspartame or the like may be added to each of the above dosage forms.
  • a medicinal additive such as a suspending agent (such as sorbitol syrup, cellulose derivative, glucose/sucrose syrup, gelatin, aluminum stearate) Or hydrogenated edible fat); emulsifiers (such as lecithin, acacia or sorbitan-oleate); non-aqueous carriers (such as almond oil, oily esters, ethanol or refined vegetable oils); and preservatives (for example, p-hydroxyl) Osteric acid decyl ester or propyl paraben or sorbic acid).
  • the liquid preparation may further contain a known buffering agent, a flavoring agent and an aroma component, a dye, and a sweetener, as needed.
  • injection using the above total benzofuran extract dry powder, adding pharmaceutical adjuvants, such as suspending agents, stabilizers and / or dispersing agents and / or reagents to adjust the osmotic pressure of the solution, can be formulated into injections, preferably muscles, veins Injection.
  • pharmaceutical adjuvants such as suspending agents, stabilizers and / or dispersing agents and / or reagents to adjust the osmotic pressure of the solution
  • the present invention also provides a pharmaceutical composition
  • a pharmaceutical composition comprising the benzoin plant or the benzoin plant extract according to any one of claims 1 to 14 or the compound according to any one of claims 2 to 12.
  • a preferred pharmaceutical composition wherein the active ingredient is a benzoin plant according to claims 1-14
  • the above-mentioned benzofuran extract of the benzoin plant can be combined with other traditional Chinese medicines and/or other chemical drugs to form a traditional Chinese medicine compound or a combination of Chinese and Western medicines, and the tablets are prepared according to a conventional method.
  • a variety of dosage forms such as oral liquid and injection.
  • the in vitro activity test showed that the benzofuran extract of benzoin plant has a good effect of promoting estrogen synthesis. It can be made into oral tablets, capsules and other dosage forms, suitable for premature ovarian failure, menopausal syndrome, Osteoporosis and ovarian dysfunction in adolescence, ovarian syndrome, infertility and treatment of diseases caused by estrogen deficiency or relative deficiency have the characteristics of remarkable curative effect, low price and convenient use.
  • the filtrate was combined twice and concentrated under reduced pressure to give 253 g of the total extract. Dissolve the total extract with 2L of hot water; take 2.5kg of D101 macroporous resin, and absorb the hot water dissolved extract with macroporous resin, elute with 20L of water, discard the eluate, then use 95%
  • the column was eluted with ethanol.
  • the eluate was concentrated under reduced pressure and then applied to a 1.5 kg polyamide column. The column was eluted with 95% ethanol.
  • the fruit of Washan benzoin is 2.2 kg (dry weight), and after pulverization, it is leached 3 times for 7 days at room temperature with 80-90% industrial alcohol 25 L.
  • the extract was concentrated in vacuo to obtain 550 g of total extract. It was suspended in 5 L of hot water, and extracted with petroleum ether, chloroform and n-butanol for 5 times, each time 5 L of solvent, and the extracts were separately concentrated.
  • Paste 16 g of petroleum ether, 200 g of chloroform, and 120 g of n-butanol. Sampling For in vitro activity screening, both chloroform and n-butanol fractions were shown to promote estrogen E2 production.
  • Infrared spectroscopy The main characteristic bands are located at 3456, 2946, 2919, 1600, 1504, 1482, 1459, 1236, 1042, 928 cm- 1 ;
  • Nuclear magnetic resonance carbon spectrum (150 MHz, DMSO-d6): ⁇ 32.2 (C-2"), 35.2 (Cl"), 60.6 (C-3") : 101.9 (-0-C3 ⁇ 4-0- ), 105.4 (C-2'), 111.0 (C-5'), 119.1 (C-6'), 124.8 (C-1'), 148.2 (C-4') , 148.4 (C-3'), 101.5 (C-3), 109.3 (C-6), 111.6 (C-4), 131.1 (C-9), 138.4 (C-5), 141.8 (C-8) 142.3 (C-7), 155.3 (C-2).
  • Color and shape pale yellow solid; melting point mp 76-79 ° C;
  • Infrared spectroscopy The main characteristic bands are located at 2959, 1729, 1599, 1504, 1477, 1449, 1236, 1186, 1042, 930 cm" 1 ;
  • the UV absorption of oleanol is similar, suggesting a benzofuran derivative.
  • Color and shape colorless needle crystals (acetone);
  • Infrared spectroscopy The main characteristic bands are located at 2923, 1673, 1620, 1474, 1234, 1129, 1038 cm" 1 ;
  • H-1 and C-4, C-6, and H- 4.
  • H-6 is related to Cl" with HMBC (as shown in the figure below), indicating that the 3-oxypropenyl group is located at C-5. Therefore, the structure of compound 7 is determined to be 5-(3-oxypropenyl)-7- Methoxy-2-(3,4-methylenedioxyphenyl)benzofuran.
  • Infrared spectroscopy The main characteristic bands are located at 3430, 2925, 2854, 1613, 1469, 1459, 1337, 1161, 1117, 1053, 963 cm" 1 ;
  • Compound 12 is characterized by:
  • Infrared spectroscopy The main characteristic i bands are located at 3427, 2924, 1620, 1503, 1474, 1363, 1256, 1232, 1074, 1038, 929, 810 cm" 1 ;
  • Magnesium stearate lg (total 1000 tablets) Benzoin total benzofuran extract, HPMC, lactose, mixed, wet granules with 75% ethanol as binder, dried through 22 mesh, 5CTC dried for 3 h, 22 mesh sieved whole, add 4 parts of stearic acid and mix well, each piece weighs O.lg, for patients with estrogen deficiency, oral, three times a week, one tablet each time, January is a course of treatment.
  • composition of the capsule The Luchun benzoin extract prepared in Example 3 0.5g
  • Magnesium stearate lg (total 1000 tablets) Benzoin total benzofuran extract, starch, magnesium stearate, mixed, rubber sleeve. 100mg per capsule, for estrogen deficiency patients, oral, three times a day, one tablet each time, one month for one course.
  • a benzoin extract 0.5 g, a soybean isoflavone extract 200 g, and a tanshinone extract 200 g were added to the corresponding excipients according to a conventional method to prepare tablets or capsules. 200mg per capsule, for estrogen deficiency patients, oral, three times a day, one tablet each time, one month for a course of treatment.
  • the mouse ovarian granulosa cells were collected, cultured in a 96-well culture plate, and E 2 was used to synthesize the desired substrate testosterone (0.5 mM), and the test drug at a concentration of 100 g/ml, and the drug was added without testosterone.
  • the drug control group was continuously cultured for 72 hours at 37 ° C and 5% C0 2 , and the culture solution was collected, centrifuged at 1000 rpm for 3 min, and the supernatant was taken.
  • the estradiol was detected by an enzyme-free kit (E 2 ). )content.
  • the differentiated mouse 3T3-L1 adipocytes were inoculated into 24-well culture medium at 2.4 ⁇ 105/well, 1 mL/well. After the cells were grown into a monolayer, E 2 was used to synthesize the desired substrate testosterone (0.5 mM). Concentration is ltX ⁇ g/ml of the drug to be tested, and a drug control group containing no drug and testosterone alone, and continuing to culture at 37 ° C, 5% C0 2 for 72 hours, collecting the culture solution, 1000 rpm After centrifugation for 3 min, the supernatant was taken, and the content of estradiol (E 2 ) therein was measured using an enzyme-free kit. The content of the synthetic E 2 in the control group in which only 0.5 mM of testosterone was added was regarded as 100%, and the synthesis ratio of the other sample groups E 2 was calculated based on this, and the results are shown in Table 2.
  • Compound 12 251.79 It is apparent from Table 3 that Compound 1-12 promotes estrogen production in rat ROS 17/2.8 osteosarcoma cells.
  • mice 50 adult female mice were divided into 5 groups, and 4 groups were surgically resected bilateral ovaries (castration). The remaining group underwent sham surgery (the same procedure was performed but the mouse ovaries were not removed). On the 4th day after surgery, vaginal smear was performed on each castration group until no vaginal epithelial keratinocytes were observed, which proved that oophorectomy was complete and met the "menopause" performance.
  • the model group was given normal saline by intragastric administration; the experimental group was intragastrically administered with compounds 10 and 11 (50 mg / kg / d); the positive control group was injected with estradiol benzoate (0.03113 ⁇ 4/13 ⁇ 4/(1), The sham operation group was used as a normal control group, and normal saline was administered by gavage. All the mice were subjected to blood sampling for 30 days after administration, and estrogen E 2 levels were determined by separating serum. The results are shown in the following table.
  • the present invention not only provides a novel plant extract of benzofuran benzofuran, and a novel benzofuran derivative monomer of the benzoin plant, but also provides a new drug for treating diseases associated with estrogen deficiency.
  • Composition due to the nature of the natural botanical itself, the present invention is for the treatment of premature ovarian failure, climacteric syndrome, osteoporosis and ovarian dysfunction in adolescence, polycystic ovary syndrome, infertility and estrogen deficiency or relative deficiency
  • the disease provides a safe, inexpensive, effective, and easy-to-use route of administration.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
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  • Biotechnology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Diabetes (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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Abstract

L’invention concerne un extrait de Styrax Linn qui comprend entre 40 et 98 % en poids total de benzofuranes de Styrax Linn. Elle concerne également la préparation et les utilisations dudit extrait. L’extrait, selon l’invention, a les caractéristiques d’une puissante efficacité thérapeutique, un prix avantageux, une utilisation commode et des avantages analogues.
PCT/CN2006/000341 2005-03-08 2006-03-07 Extrait de styrax linn, preparation et utilisations correspondantes WO2006094456A1 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
CN200510020479.6 2005-03-08
CN200510020477.7 2005-03-08
CNB2005100204777A CN100509803C (zh) 2005-03-08 2005-03-08 安息香属植物总苯并呋喃提取物及其制备方法和应用
CN200510020478.1 2005-03-08
CN200510020478A CN1830435B (zh) 2005-03-08 2005-03-08 齐墩果醇型苯并呋喃及其苷在制备抗雌激素缺乏药物中的应用
CNB2005100204796A CN100420690C (zh) 2005-03-08 2005-03-08 一种苯并呋喃化合物及其制备方法和应用

Publications (1)

Publication Number Publication Date
WO2006094456A1 true WO2006094456A1 (fr) 2006-09-14

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Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
ANIL H.: "Four benzofuran glycosides from Styrax officinalis", PHYTOCHEMISTRY, vol. 19, no. 12, 1980, pages 2784 - 2786 *
MENDONCA P.P. ET AL.: "Nor-lignans from the leaves of Styras ferrugineus (Styracaceae) with antibacterial and antifungal activity", PHYTOCHEMISTRY, vol. 55, no. 6, 2000, pages 597 - 601 *
TAKANASHI M. ET AL.: "New benzofurans related to egonol from immature seeds of Styrax obassia", PHYTOCHEMISTRY, vol. 27, no. 4, 1988, pages 1224 - 1226 *
YOSHIKAWA K. ET AL.: "A benzofuran glycoside and an acetylenic acid from the fungus Laetiporus sulphureus var. miniatus", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 49, no. 3, 2001, pages 327 - 329 *

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