CN115385883A - Preparation method of coumarin compound and application of coumarin compound in monoamine oxidase B inhibition resisting medicine - Google Patents
Preparation method of coumarin compound and application of coumarin compound in monoamine oxidase B inhibition resisting medicine Download PDFInfo
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- CN115385883A CN115385883A CN202210804707.2A CN202210804707A CN115385883A CN 115385883 A CN115385883 A CN 115385883A CN 202210804707 A CN202210804707 A CN 202210804707A CN 115385883 A CN115385883 A CN 115385883A
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- C—CHEMISTRY; METALLURGY
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- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61K31/00—Medicinal preparations containing organic active ingredients
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- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
- A61K31/366—Lactones having six-membered rings, e.g. delta-lactones
- A61K31/37—Coumarins, e.g. psoralen
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Abstract
The invention relates to a preparation method of coumarin compounds and application of the coumarin compounds in medicines for resisting monoamine oxidase B inhibition. Aiming at the problem of toxic and side effects of MAO-B inhibitor drugs in the prior art, the coumarin compound 5-demethoxy-10-ethoxytimarin F is extracted and separated from Murraya exotica L of Murraya koenigii, has inhibitory activity on MAO-B, and can be used for preparing a monoamine oxidase B inhibition drug composition.
Description
Technical Field
The invention relates to a preparation method of coumarin compounds and application of the coumarin compounds in medicines for resisting monoamine oxidase B inhibition, belonging to the technical field of medicines.
Background
Monoamine oxidase (MAO) is A type of flavin-dependent protein, and is divided into two subtypes, MAO-A and MAO-B, according to substrate selectivity and sensitivity to inhibitors. Monoamine oxidase plays an important role in maintaining normal levels of neurotransmitters and biogenic amines in brain and mammalian tissues. MAO-B is an important target for the treatment of Parkinson's disease and Alzheimer's disease. The first generation and the second generation of the MAO-B irreversible inhibitor have large toxic and side effects, and the clinical application is limited. As aging progresses. The search for new highly potent, reversible MAO-B selective inhibitors is imminent.
Coumarin is a natural organic compound widely distributed in plants of Rutaceae, umbelliferae, compositae, etc., and has parent nucleus structure of benzo alpha-pyrone. The coumarin compound has a plurality of pharmacological activities such as antibacterial activity, antiviral activity, antitumor activity, antioxidant activity, MAO-B resistance, neuroprotection and the like, has wide clinical application, and is favored by researchers in recent years due to the strong MAO-B inhibition activity and the characteristic of easy structural modification of the coumarin compound.
Murraya paniculata (Murraya exotica l.), also known as: QILIXIANG, DUOSHANXIANG, SHANHUANG, and YUEJU. Is evergreen shrub or small arbor of Murraya belonging to Murraya of Rutaceae, which is one of the main drugs of "Sanjiuweitai", and Murraya koenigii recorded for many times in pharmacopoeia of the people's republic of China has the effects of promoting qi circulation, relieving pain, promoting blood circulation and removing blood stasis. The murraya paniculata contains chemical components such as coumarins, flavonoids and alkaloids, wherein the coumarins are main active components and are the basis of medicinal substances of the plants, and the 8-isopentenyl coumarins are characteristic types of the murraya paniculata. The coumarin in the murraya jasminorage shows various physiological activities such as anti-inflammation, antioxidation, antibiosis and the like, and shows the pharmacological potential of the coumarin.
Therefore, the coumarin MAO-B inhibitor is found from natural products, the high-activity, high-selectivity, low-cytotoxicity and reversible larval-cephalic compound is searched, and the coumarin compound which aims at multiple signal paths or targets and is used for resisting neurodegenerative diseases is of great significance in research and development.
Disclosure of Invention
Toxicity against prior art MAO-B inhibitor drugsThe coumarin compound 5-demethoxy-10' -ethoxytimarine F is extracted and separated from Murraya exotica L of Murraya koenigii, has inhibitory activity to MAO-B, and has IC activity 50 (hMAO-B) values were: 153.25. + -. 1.58nM, IC 50 (hMAO-A) 26.3. + -. 1.03. Mu.M, selectivity index: 172, can be used for preparing the pharmaceutical composition for resisting monoamine oxidase B inhibition.
Coumarin compound has the following chemical structural formula
A pharmaceutical composition for inhibiting monoamine oxidase B comprises pharmaceutically acceptable carrier and/or excipient, and coumarin compounds. The monoamine oxidase B pharmaceutical composition is in the dosage form of injection, tablets, pills, capsules, solution, suspending agent or emulsion.
The extraction method of the coumarin compound comprises the following specific steps:
1. percolating Murraya exotica L. branch and leaf dry powder of Murraya paniculata with ethanol to obtain extractive solution, and concentrating under reduced pressure to obtain crude extract;
2. suspending the crude extract obtained in the step 1 in water to obtain a suspension, extracting the suspension with petroleum ether to obtain a petroleum ether extract and a petroleum ether extraction water phase, concentrating the petroleum ether extract to obtain a petroleum ether extract, extracting the petroleum ether extraction water phase with ethyl acetate to obtain an ethyl acetate extract, and concentrating the ethyl acetate extract to obtain an ethyl acetate extract;
3. performing silica gel column chromatography on the ethyl acetate extract obtained in the step 2, performing gradient elution by sequentially adopting a petroleum ether/ethyl acetate mixed liquor system and a dichloromethane/methanol mixed liquor system, and checking and merging similar fractions according to thin-layer chromatography to obtain 5 components, namely a, b, c, d and e;
4. subjecting the component c in the step 3 to gel column chromatography, eluting with dichloromethane, and combining similar fractions according to thin layer chromatography to obtain 5 components a, b, c, d and e;
5. and (4) performing silica gel column chromatography on the component b in the step (4), and eluting and purifying by adopting a dichloromethane/methanol mixed solution to obtain the coumarin compound 5-demethoxy-10' -ethyoxyxotimarin F.
6. The method for extracting coumarin compounds according to claim 4, wherein: step 3 the gradient elution is carried out by using a petroleum ether/ethyl acetate mixed solution, wherein the volume ratio of petroleum ether to ethyl acetate is 8, 2, 5, 6 and 0.
7. The method for extracting coumarin compounds according to claim 4, wherein: step 3 gradient elution with dichloromethane/methanol mixed solution the volume ratio of dichloromethane to methanol was 8, 7, 3, 6, 1 and 0.
8. The method for extracting coumarin compounds according to claim 4, wherein: in the dichloromethane/methanol mixed solution in the step 5, the volume ratio of dichloromethane to methanol is 50.
Further, the mass percentage content of the coumarin compound 5-demethoxy-10' -ethyoxyxotimarin F in the murraya jasminorage extract is 0.0144 per mill;
the pharmaceutically acceptable carrier and/or excipient is non-toxic to both humans and animals and is inert;
the medicinal carrier is one or more of solid diluent, semisolid diluent, liquid diluent, filler and pharmaceutical product adjuvant;
the pharmaceutical composition is administered in the form of an amount administered per unit body weight;
the medicine can be administered orally, by injection (intravenous injection, intramuscular injection), or transdermally.
The invention has the beneficial effects that:
(1) The coumarin compound 5-demethoxy-10' -ethoxytimarine F has the inhibitory activity on MAO-B, IC 50 (hMAO-B) values were: 153.25. + -. 1.58nM, IC 50 (hMAO-A) 26.3. + -. 1.03. Mu.M, selectivity index: 172; the coumarin compound 5-demethoxy-10-ethoxytimarine F can be mixed with medicinal carrier and/or excipient to make into preparationanti-MAO-B pharmaceutical compositions;
(2) The coumarin compound 5-demethoxy-10' -ethoxytimarin F is from edible natural plant components, and the prepared monoamine oxidase B inhibition resistant pharmaceutical composition is non-toxic or low-toxic.
Detailed Description
The present invention will be described in further detail with reference to specific embodiments, but the scope of the present invention is not limited to the description.
Example 1: the extraction method of the coumarin compound comprises the following specific steps:
1. percolating Murraya exotica L. branch and leaf dry powder of Murraya paniculata with ethanol to obtain extractive solution, and concentrating under reduced pressure to obtain crude extract;
2. suspending the crude extract obtained in the step 1 in water to obtain a suspension, extracting the suspension with petroleum ether to obtain a petroleum ether extract and a petroleum ether extraction aqueous phase, concentrating the petroleum ether extract to obtain a petroleum ether extraction extract, extracting the petroleum ether extraction aqueous phase with ethyl acetate to obtain an ethyl acetate extract, and concentrating the ethyl acetate extract to obtain an ethyl acetate extraction extract;
3. performing silica gel column chromatography on the ethyl acetate extract obtained in the step 2, performing gradient elution by sequentially adopting a petroleum ether/ethyl acetate mixed liquor system and a dichloromethane/methanol mixed liquor system, and checking and merging similar fractions according to thin-layer chromatography to obtain 5 components, namely a, b, c, d and e;
4. subjecting the component C in the step 3 to gel column chromatography, eluting with dichloromethane, and checking and combining similar fractions according to thin layer chromatography to obtain 5 components, namely a, b, C, d and e; wherein the diameter of the gel column is 3cm, the length is 160cm, and the dry weight of Sephadex LH-20 gel is 150g;
5. and (4) performing silica gel column chromatography on the component b in the step (4), and eluting and purifying by adopting a dichloromethane/methanol mixed solution to obtain the coumarin compound 5-demethoxy-10' -ethyoxyxotimarin F.
6. The method for extracting coumarin compounds according to claim 4, wherein: step 3 the gradient elution is carried out by using a petroleum ether/ethyl acetate mixed solution, wherein the volume ratio of petroleum ether to ethyl acetate is 8, 2, 5, 6 and 0.
7. The method for extracting coumarin compounds according to claim 4, characterized in that: step 3 gradient elution with dichloromethane/methanol mixture the volume ratio of dichloromethane to methanol was 8, 7, 3, 6, 1.
8. The method for extracting coumarin compounds according to claim 4, characterized in that: in the dichloromethane/methanol mixed solution in the step 5, the volume ratio of dichloromethane to methanol is 50.
The coumarin compound of the embodiment has the following chemical structural formula:
named 5-demethoxy-10' -ethyoxyxotimarin F.
Preparation of coumarin Compounds of the examples 1 H-NMR data (400 MHz) (delta in ppm, J in Hz) and 13 c NMR data (. Delta.in ppm, J in Hz) are shown in Table 1.
TABLE 1 preparation of coumarins 1 H-NMR data and 13 c NMR data (CDCl) 3 )
The coumarin compound 5-demethoxy-10' -ethoxytiminin F is white solid with molecular formula C 32 H 37 O 10 High resolution mass spectrum HRESIMS m/z 605.2359[ m + Na ]]+(calcd 605.2357)。
Example 2: in vitro MAO-B resistance assay of 5-demethoxy-10' -ethoxyxytimarin F, coumarin compound of example 1;
novel coumarin 5-demethoxy-10' -ethyoxyxotimarin F inhibition activity screening, compound activity screening is carried out by using MAO-B inhibitor screening kit, and specific operation is strictly carried out according to product instructionsAnd (4) performing the book. A sample solution, a blank solution, an enzyme solution and a substrate solution are prepared in advance by taking selegiline and isopropylhydrazine as reference medicaments and adopting an Amplex Red MAO detection kit according to a kit specification. The reaction system is sodium phosphate buffer Na 3 PO 4 (50mmol L -1 pH 7.4), na was used 3 PO 4 Buffer MAO-B diluted to 75mg L -1 MAO-A diluted to 12.5mg -1 (ii) a Diluting the compound to different final concentrations, adding the compound to be tested (20 μ L) and MAO (80 μ L) to 96-well blackboard, incubating at 37 deg.C for 15min, and adding 100 μ L working solution (containing 200 μmol L) -1 Amplex Red，2U mL -1 Horseradish peroxidase, 10mmol L -1 Benzylamine for MAO-B/2mmol L -1 Tyramine is used for MAO-A) incubation for 15min at 37 ℃, fluorescence values are recorded at the excitation wavelength of 545nm and the emission wavelength of 590nm by adopting an end-point method, the inhibition effect on MAO is investigated, datA are analyzed, and IC is calculated 50 Selectivity index equal to IC 50 (hMAO-A)/IC 50 (hMAO-B)。
The result of the inhibitory activity test is as follows: IC (integrated circuit) 50 (hMAO-B) values were: 153.25. + -. 1.58nM, IC 50 (hMAO-A) 26.3. + -. 1.03. Mu.M, selectivity index: 172;
through activity test experiments, the coumarin compound 5-demethoxy-10 '-ethoxyxotimarin F can show the anti-MAO-B activity, so that the coumarin compound 5-demethoxy-10' -ethoxyxotimarin F can be used for preparing an anti-MAO-B medicament and can be prepared into an anti-MAO-B medicinal composition with other medicaments;
the coumarin compound 5-demethoxy-10 '-ethoxytimarin F is taken as a raw material, and a medicinal carrier and/or an excipient are/is added to obtain the pharmaceutical composition containing the coumarin compound 5-demethoxy-10' -ethoxytimarin F;
the coumarin compound 5-demethoxy-10' -ethoxytimarin F is derived from edible natural plant components, and the prepared MAO-B resistant pharmaceutical composition is non-toxic or low-toxic;
the pharmaceutically acceptable carrier and/or excipient is non-toxic to humans and animals and is inert;
the pharmaceutically acceptable carrier and/or excipient is non-toxic to humans and animals and is inert;
the medicinal carrier is one or more of solid diluent, semisolid diluent, liquid diluent, filler and pharmaceutical product adjuvant;
the pharmaceutical composition is administered in the form of a unit weight dose;
the medicine can be administered by injection (intravenous injection, intramuscular injection), oral administration or skin administration.
The embodiments of the present invention have been described above. However, the present invention is not limited to the above embodiment. Any modification, equivalent replacement, or improvement made without departing from the spirit and principle of the present invention shall fall within the protection scope of the present invention.
Claims (7)
1. A coumarin compound is characterized in that: has the following structure: named 5-demethoxy-10' -ethyoxyxotimarin F.
2. A compound having monoamine oxidase B inhibitory activity, characterized by: comprises a pharmaceutically acceptable carrier and/or excipient, and the coumarin compound of claim 1.
3. The monoamine oxidase B pharmaceutical composition of claim 2 in the form of injection, tablet, pill, capsule, solution, suspension or emulsion.
4. The method for extracting coumarin compounds according to claim 1, comprising the following steps:
(1) Percolating Murraya exotica L branch and leaf dry powder with ethanol to obtain extractive solution, and concentrating under reduced pressure to obtain crude extract;
(2) Suspending the crude extract obtained in the step (1) in water to obtain a suspension, extracting the suspension with petroleum ether to obtain a petroleum ether extract and a petroleum ether extraction aqueous phase, concentrating the petroleum ether extract to obtain a petroleum ether extraction extract, extracting the petroleum ether extraction aqueous phase with ethyl acetate to obtain an ethyl acetate extract, and concentrating the ethyl acetate extract to obtain an ethyl acetate extraction extract;
(3) Performing silica gel column chromatography on the ethyl acetate extract obtained in the step (2), performing gradient elution by sequentially adopting a petroleum ether/ethyl acetate mixed solution system and a dichloromethane/methanol mixed solution system, and checking and merging similar fractions according to thin-layer chromatography to obtain 5 components, namely a, b, c, d and e;
(4) Subjecting the fraction c of step (3) to gel column chromatography, eluting with dichloromethane, and combining similar fractions according to thin layer chromatography to obtain 5 fractions a, b, c, d and e;
(5) And (4) performing silica gel column chromatography on the component b, and eluting and purifying by adopting a dichloromethane/methanol mixed solution to obtain the coumarin compound 5-demethoxy-10' -ethyoxyxotimarin F.
5. The method for extracting coumarin compounds according to claim 4, characterized in that: step (3) the gradient elution is carried out by using a petroleum ether/ethyl acetate mixed solution, wherein the volume ratio of petroleum ether to ethyl acetate is (8).
6. The method for extracting coumarin compounds according to claim 4, wherein: step (3) gradient elution with dichloromethane/methanol mixed solution the volume ratio of dichloromethane to methanol was 8, 7, 3, 6, 1 and 0.
7. The method for extracting coumarin compounds according to claim 4, wherein: in the step (5), the volume ratio of dichloromethane to methanol in the dichloromethane/methanol mixed solution is 50.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN118108727A (en) * | 2024-04-29 | 2024-05-31 | 昆明医科大学 | A carbazole alkaloid compound and its preparation method and application |
Citations (3)
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|---|---|---|---|---|
| US20090069313A1 (en) * | 2007-09-06 | 2009-03-12 | Orchid Research Laboratories Ltd. | Novel MAO-A inhibitors |
| CN106588847A (en) * | 2016-12-09 | 2017-04-26 | 上海中医药大学 | Dihydrocoumarin derivatives as well as preparation method and application thereof |
| CN110818613A (en) * | 2019-10-15 | 2020-02-21 | 云南大学 | Carbazole compound, preparation method thereof and application thereof in anti-HIV (human immunodeficiency virus) medicines |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090069313A1 (en) * | 2007-09-06 | 2009-03-12 | Orchid Research Laboratories Ltd. | Novel MAO-A inhibitors |
| CN106588847A (en) * | 2016-12-09 | 2017-04-26 | 上海中医药大学 | Dihydrocoumarin derivatives as well as preparation method and application thereof |
| CN110818613A (en) * | 2019-10-15 | 2020-02-21 | 云南大学 | Carbazole compound, preparation method thereof and application thereof in anti-HIV (human immunodeficiency virus) medicines |
Non-Patent Citations (2)
| Title |
|---|
| BING-YU LIU ET AL.: "Anti-Inflammatory Prenylated Phenylpropenols and Coumarin Derivatives from Murraya exotica" * |
| XIAOTING WANG ET AL.: "Panitins A-G: Coumarin derivatives from Murraya paniculata from Guangxi Province, China show variable NO inhibitory activity" * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN118108727A (en) * | 2024-04-29 | 2024-05-31 | 昆明医科大学 | A carbazole alkaloid compound and its preparation method and application |
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