CN111548380A - Preparation method of monotropein in morinda officinalis - Google Patents
Preparation method of monotropein in morinda officinalis Download PDFInfo
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- CN111548380A CN111548380A CN202010526847.9A CN202010526847A CN111548380A CN 111548380 A CN111548380 A CN 111548380A CN 202010526847 A CN202010526847 A CN 202010526847A CN 111548380 A CN111548380 A CN 111548380A
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- monotropein
- morinda officinalis
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- HPWWQPXTUDMRBI-UHFFFAOYSA-N (4aS)-1c-beta-D-Glucopyranosyloxy-7t-hydroxy-7c-hydroxymethyl-(4ar,7ac)-1,4a,7,7a-tetrahydro-cyclopenta[c]pyran-4-carbonsaeure Natural products OC1C(O)C(O)C(CO)OC1OC1C2C(O)(CO)C=CC2C(C(O)=O)=CO1 HPWWQPXTUDMRBI-UHFFFAOYSA-N 0.000 title claims abstract description 31
- HPWWQPXTUDMRBI-COZRGLNQSA-N Monotropein Natural products O=C(O)C=1[C@H]2[C@H]([C@H](O[C@H]3[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O3)OC=1)[C@](O)(CO)C=C2 HPWWQPXTUDMRBI-COZRGLNQSA-N 0.000 title claims abstract description 31
- HPWWQPXTUDMRBI-NJPMDSMTSA-N monotropein Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]1[C@@H]2[C@@](O)(CO)C=C[C@@H]2C(C(O)=O)=CO1 HPWWQPXTUDMRBI-NJPMDSMTSA-N 0.000 title claims abstract description 31
- 241000096284 Gynochthodes officinalis Species 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 238000001035 drying Methods 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 238000001914 filtration Methods 0.000 claims description 11
- 238000000605 extraction Methods 0.000 claims description 10
- 238000000746 purification Methods 0.000 claims description 8
- 239000000706 filtrate Substances 0.000 claims description 7
- 238000001514 detection method Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000012982 microporous membrane Substances 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 244000131360 Morinda citrifolia Species 0.000 claims 1
- 235000008898 Morinda citrifolia Nutrition 0.000 claims 1
- 238000004440 column chromatography Methods 0.000 claims 1
- 235000017524 noni Nutrition 0.000 claims 1
- 239000007791 liquid phase Substances 0.000 abstract description 7
- 230000008569 process Effects 0.000 abstract description 7
- 239000000178 monomer Substances 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 2
- 239000012071 phase Substances 0.000 description 12
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- ZUKLFFYDSALIQW-MSUKCBDUSA-N Iridoid glycoside Chemical compound [H][C@]12CC[C@H](C(O)=O)[C@@]1([H])[C@H](OC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)OC=C2 ZUKLFFYDSALIQW-MSUKCBDUSA-N 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229930182489 iridoid glycoside Natural products 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000000638 solvent extraction Methods 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 241001107098 Rubiaceae Species 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 241000233855 Orchidaceae Species 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- -1 anthraquinone compound Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 230000008468 bone growth Effects 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 210000000750 endocrine system Anatomy 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 230000004345 fruit ripening Effects 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 210000000777 hematopoietic system Anatomy 0.000 description 1
- 230000036737 immune function Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Extraction Or Liquid Replacement (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Abstract
The invention discloses a preparation method of monotropein in morinda officinalis, which comprises the steps of extracting, concentrating and drying morinda officinalis medicinal materials by ethanol, directly purifying by adopting a high-efficiency preparation liquid phase, collecting fractions, concentrating and drying to obtain a monomer with the monotropein content more than 96%. The invention has the advantages of simple process and convenient operation.
Description
Technical Field
The application relates to the technical field of extraction of plant active ingredients, and particularly relates to a preparation method of monotropein in morinda officinalis.
Background
Morinda Officinalis (scientific name: Morinda Officinalis Radix), is the dried root of Morinda Officinalis of Rubiaceae (Rubiaceae). The flowering period is 5-7 months, and the fruit ripening period is 10-11 months. Morinda officinalis is mainly distributed in Guangdong, Guangxi, Fujian, Hainan and Jiangxi provinces. Guangdong Deqing, Gaoyuan and Yunan are the most suitable areas for producing medicinal materials.
Morinda officinalis mainly contains anthraquinone compound, iridoid glycoside, organic acids, oligosaccharide, amino acids, trace elements and other components. Wherein iridoid, polysaccharide and monotropein have certain physiological activity. The traditional Chinese medicine theory considers that morinda officinalis has the effects of tonifying kidney yang, strengthening bones and muscles, dispelling wind-damp and the like, and modern researches prove that morinda officinalis has the effects of influencing bone growth, organism immune function, nervous system, endocrine system, aging resistance, fatigue resistance, hematopoietic system, cardiovascular system and tumor resistance, and the like, and is widely applied to traditional Chinese medicine formulas and Chinese patent medicines.
The monotropein is iridoid glycoside component, modern researches prove that iridoid glycoside component is closely related to pharmacological action of morinda officinalis, and the conventional monotropein extract is mainly treated by heating extraction, resin purification, organic solvent extraction and other methods, for example, CN101812098A discloses a method for extracting and separating monotropein monomer from morinda officinalis, which comprises the steps of ethanol solution extraction, ethyl acetate extraction, n-butanol extraction, filtration for further impurity removal, separation of monotropein monomer by preparative high performance liquid chromatography, macroporous resin enrichment, drying to obtain monotropein monomer product, and the like. Although the method can obtain the high-purity monotropein monomer, the method still cannot solve the defects of complex process, inconvenient operation, long period and the like.
Disclosure of Invention
The invention provides a preparation method of monotropein in morinda officinalis, which is convenient and direct, simple in process, low in production cost, easy to popularize and high in monotropein purity.
A method for preparing monotropein from radix Morindae officinalis comprises the following steps:
(1) extraction: crushing morinda officinalis, adding 10-15 times of ethanol, heating and refluxing at 70-80 ℃ for 2-3 times, each time for 1-2 hours, and coarsely filtering to obtain a crude morinda officinalis extract;
(2) concentrating and drying: vacuum concentrating the above filtered extractive solution at 55-65 deg.C;
(3) preparation and purification: adding 10-20 times of mobile phase into the dried extract, ultrasonic dissolving, and filtering with 0.22 μm microporous membrane to obtain liquid phase;
(4) and (3) fraction collection: collecting the fraction of the monotropein;
(5) concentrating and drying: vacuum concentrating the collected fraction at 55-65 deg.C.
As a preferred embodiment, the concentration of ethanol in step (1) is 65% to 75%.
As a preferred embodiment, the chromatographic column in step (3) is: c18 reversed phase chromatographic column, wherein the specific chromatographic conditions are as follows: the mobile phase is methanol: acetic acid as (3-7): (97-93) eluting at a flow rate of 30-40mL/min, a detection wavelength of 230-235nm and a column temperature of 25-35 ℃.
As a preferred embodiment, the concentration of acetic acid is 0.15% to 0.25%.
The invention has the beneficial effects that:
the method has the advantages of simple process and short production period: according to the conventional process of the monotropein, after extraction, macroporous resin is firstly carried out for adsorption impurity removal or organic solvent extraction is carried out, and then subsequent treatment is carried out. The method directly concentrates and dries the morinda officinalis extract, and then separates and purifies the morinda officinalis extract in a preparation liquid phase, so that high-purity monotropein is obtained, and the purposes of simplifying the process and shortening the period are achieved.
Secondly, high transfer rate: the conventional process of the monotropein needs to concentrate the extract of the morinda officinalis and then carry out operations such as macroporous resin purification, organic solvent extraction and the like, so that the monotropein loss is large.
Thirdly, the product purity is high: the morinda officinalis extract is subjected to high-efficiency preparation and liquid phase separation and purification to obtain high-purity monotropein monomers (the purity is more than 96%).
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present application clearer, the technical solutions of the embodiments of the present application will be clearly and completely described below. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
Example 1
A method for preparing monotropein in Morinda officinalis comprises the following steps:
(1) extraction: extracting 100g radix Morindae officinalis with 65% ethanol for 3 times (1000 mL each time), extracting at 70 deg.C for 2 hr, filtering with filter screen, collecting filtrate, and mixing filtrates.
(2) Concentrating and drying: concentrating the above extractive solution at 55 deg.C under reduced pressure, and drying to obtain extract 12.1 g.
(3) Preparation and purification: adding a proper amount of dried extract into 10 times of mobile phase for ultrasonic dissolution, filtering the extract by a microporous filter membrane, and then preparing a liquid phase on the extract by a chromatographic column: c18 reversed phase chromatographic column, wherein the specific chromatographic conditions are as follows: the mobile phase is methanol: 0.15% acetic acid as 3: 97 at a flow rate of 30mL/min, a detection wavelength of 230nm and a column temperature of 25 ℃.
(4) And (3) fraction collection: collecting the fraction of the monotropein;
(5) concentrating and drying: vacuum concentrating and drying the collected fractions at 55 deg.C, wherein the yield of monotropein is 0.47%, and the content is 96.98%.
Example 2
A method for preparing monotropein in Morinda officinalis comprises the following steps:
(1) extraction: extracting 100g radix Morindae officinalis with 70% ethanol for 2 times (1200 mL each time), extracting at 75 deg.C for 2 hr, filtering with filter screen, collecting filtrate, and mixing filtrates.
(2) Concentrating and drying: concentrating the above extractive solution at 55 deg.C under reduced pressure, and drying to obtain extract 11.9 g.
(3) Preparation and purification: taking a proper amount of dried extract, adding a mobile phase in an amount which is 15 times of the amount of the dried extract, performing ultrasonic dissolution, filtering the extract by a microporous filter membrane, and then preparing a liquid phase on the extract by a chromatographic column: c18 reversed phase chromatographic column, wherein the specific chromatographic conditions are as follows: the mobile phase is methanol: 0.20% acetic acid as 5: 95, the flow rate is 35mL/min, the detection wavelength is 233nm, and the column temperature is 30 ℃.
(4) And (3) fraction collection: collecting the fraction of the monotropein;
(5) concentrating and drying: vacuum concentrating and drying the collected fraction at 60 deg.C to obtain 0.47% crystal orchid glycoside with 97.71% content.
Example 3
A method for preparing monotropein in Morinda officinalis comprises the following steps:
(1) extraction: extracting 100g radix Morindae officinalis with 75% ethanol for 3 times (each time with 1500 mL) at 80 deg.C for 1 hr, filtering with filter screen, collecting filtrate, and mixing filtrates.
(2) Concentrating and drying: concentrating the above extractive solution at 55 deg.C under reduced pressure, and drying to obtain extract 12.5 g.
(3) Preparation and purification: adding a proper amount of dried extract into 20 times of mobile phase for ultrasonic dissolution, filtering the extract by a microporous filter membrane, and then preparing a liquid phase on the extract by a chromatographic column: c18 reversed phase chromatographic column, wherein the specific chromatographic conditions are as follows: the mobile phase is methanol: 0.25% acetic acid as 7: 93 at a flow rate of 40mL/min, a detection wavelength of 235nm and a column temperature of 35 ℃.
(3) And (3) fraction collection: collecting the fraction of the monotropein;
(4) concentrating and drying: vacuum concentrating and drying the collected fraction at 65 deg.C, wherein the yield of monotropein is 0.49%, and the content is 96.74%.
The above description is only an example of the present application and is not intended to limit the scope of the present application, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, improvement and the like made within the spirit and principle of the present application shall be included in the protection scope of the present application.
Claims (4)
1. A preparation method of monotropein in Morinda officinalis is characterized by comprising the following steps:
(1) extraction: crushing morinda officinalis, adding 10-15 times of ethanol, heating and refluxing at 70-80 ℃ for 2-3 times, each time for 1-2 hours, and coarsely filtering to obtain a crude morinda officinalis extract.
(2) Concentrating and drying: vacuum concentrating the above filtered extractive solution at 55-65 deg.C, and drying.
(3) Preparation and purification: adding 10-20 times of mobile phase into dried extract, ultrasonic dissolving, filtering with 0.22 μm microporous membrane, and collecting the filtrate.
(4) And (3) fraction collection: collecting the fraction of the monotropein.
(5) Concentrating and drying: vacuum concentrating the collected fraction at 55-65 deg.C.
2. The method of claim 1, wherein the concentration of ethanol in Morinda citrifolia of step (1) is 65% -75%.
3. The method of claim 1, wherein the column chromatography in step (3) comprises: c18 reversed phase chromatographic column, wherein the specific chromatographic conditions are as follows: the mobile phase is methanol: acetic acid as (3-7): (97-93) eluting at a flow rate of 30-40mL/min, a detection wavelength of 230-235nm and a column temperature of 25-35 ℃.
4. The method of claim 3, wherein the concentration of acetic acid is between about 0.15% and about 0.25%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN202010526847.9A CN111548380A (en) | 2020-06-10 | 2020-06-10 | Preparation method of monotropein in morinda officinalis |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202010526847.9A CN111548380A (en) | 2020-06-10 | 2020-06-10 | Preparation method of monotropein in morinda officinalis |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113189256A (en) * | 2021-05-12 | 2021-07-30 | 劲牌有限公司 | Method for extracting curculigoside from curculigo orchioides |
| CN113354539A (en) * | 2021-05-12 | 2021-09-07 | 广州中医药大学(广州中医药研究院) | Morinda officinalis iridoid compound with anti-inflammatory activity and preparation method and application thereof |
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| CN101812098A (en) * | 2009-12-13 | 2010-08-25 | 成都普思生物科技有限公司 | Method for extracting monotropein monomers from medicinal indianmulberry root |
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| WO2018106002A1 (en) * | 2016-12-08 | 2018-06-14 | 전북대학교 산학협력단 | Composition for preventing and treating male infertility, containing compound combination comprising flavonoid derivative and iridoid derivative as active ingredient, and use thereof |
| CN108721313A (en) * | 2018-05-17 | 2018-11-02 | 东莞广州中医药大学中医药数理工程研究院 | A kind of Vitamin D receptor agonist |
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| CN110711220A (en) * | 2019-10-14 | 2020-01-21 | 浙江海洋大学 | Application of morinda officinalis extract in preparation of anti-skeletal muscle fatigue agent |
-
2020
- 2020-06-10 CN CN202010526847.9A patent/CN111548380A/en active Pending
Patent Citations (6)
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Non-Patent Citations (2)
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113189256A (en) * | 2021-05-12 | 2021-07-30 | 劲牌有限公司 | Method for extracting curculigoside from curculigo orchioides |
| CN113354539A (en) * | 2021-05-12 | 2021-09-07 | 广州中医药大学(广州中医药研究院) | Morinda officinalis iridoid compound with anti-inflammatory activity and preparation method and application thereof |
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