CN109232298B - Octopamine dimer compound, preparation method and application - Google Patents
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Abstract
The invention provides an octopamine dimer compound, which is prepared by extracting rhizoma polygonati powder with ethanol, extracting the obtained extract with n-butanol, and concentrating the n-butanol layer to obtain an extract; subjecting the extract to gradient elution with macroporous adsorbent resin column with water-ethanol to obtain 7 different fractions A-G; and eluting the fraction E by using chloroform-methanol-water constant through column chromatography, further eluting the obtained elution component by using ethyl acetate-chloroform-methanol-water constant, and purifying the eluted liquid to obtain a novel octopamine dimer compound, wherein the compound is extracted from rhizoma polygonati for the first time, is a brand new compound in the nature, and can be used for preparing antibacterial drugs.
Description
Technical Field
The invention relates to the technical field of drug extraction, and particularly relates to an octopamine dimer compound, and a preparation method and application thereof.
Background
Polygonatum cyrtonema is derived from dried rhizome of Polygonatum cyrtonema of Polygonatum of Liliaceae, also known as rhizoma Polygonati. Mainly produced in southern areas of China, and the history of cultivating polygonatum cyrtonema in Hunan province is long, which is one of the real estate areas. The compendium of materia medica says that the extract of Kunjun soil is a superior product for nourishing the middle energizer, has the effects of tonifying kidney, benefiting essence, nourishing yin and moistening dryness, is used for treating the symptoms of deficiency of the kidney, weakness of the spleen and the stomach, lung deficiency, dry cough and fatigue for a long time, is also an important component of dozens of compound nourishing medicaments, has the shape of rhizoma polygonati rhizome like sweet potato, and is often used as a vegetable edible medicinal plant by people in mountainous regions, thereby having the effects of tonifying the spleen, moistening the lung and promoting the secretion of saliva or body fluid. In addition, because polygonatum contains various functional components, such as furostanol type saponin, spirostanol type saponin, polysaccharide and the like, the polygonatum is also generally used for resisting oxidation and fatigue.
At present, various active substances are extracted from rhizoma polygonati, for example, the patent application number CN104069348A discloses a rhizoma polygonati extract and a preparation method and application thereof, the invention extracts the rhizoma polygonati by using petroleum ether, ethyl acetate and n-butyl alcohol after the rhizoma polygonati is subjected to ethanol thermal extraction, and the obtained compound mainly contains 5-hydroxymethyl furfural, steroid saponin and phenolic acid (lignan and the like) components and is mainly used for resisting diabetes and complications thereof; patent application No. CN201510395570.X discloses a method for extracting and separating multiple active ingredients from rhizoma Polygonati, which is used for extracting and separating active ingredients such as rhizoma Polygonati polysaccharide, rhizoma Polygonati saponin and rhizoma Polygonati flavone by flash extraction technology. Aiming at the research of the chemical components of polygonatum, the active ingredients extracted from polygonatum are few at present, mainly comprising polygonatum polysaccharides, polygonatum saponins, polygonatum flavonoids and the like, but the active ingredients of polygonatum are very complex and are not enough, and the extraction process of polygonatum still needs to be deeply researched to extract more active ingredients. The extraction and separation of the octopamine dimer compound from the sealwort has not been reported so far, and no one can extract the octopamine dimer compound from other substances.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provides an octopamine dimer compound, a preparation method and application thereof.
The invention provides an octopamine dimer compound, which has the following structural formula:
the invention also provides a preparation method of the octopamine dimer compound, which comprises the following steps:
(1) extracting rhizoma Polygonati powder with ethanol, extracting the obtained extractive solution with n-butanol, and concentrating n-butanol layer to obtain extract;
(2) subjecting the extract to gradient elution with macroporous adsorbent resin column with water-ethanol to obtain 7 different fractions A-G;
(3) and eluting the fraction E by using chloroform-methanol-water for constant degree through column chromatography, further eluting the obtained elution component by using ethyl acetate-chloroform-methanol-water for constant degree, and drying the eluted liquid to obtain the octopamine dimer compound.
Preferably, the preparation method of the polygonatum sibiricum powder in the step (1) comprises the following steps: drying and crushing the roots of polygonatum cyrtonema and sieving to obtain polygonatum cyrtonema powder.
Preferably, the volume concentration of ethanol in the step (1) is 95%.
Preferably, the mass ratio of the sealwort powder to the ethanol in the step (1) is 1: 5-8.
Preferably, the volume ratio of the water to the ethanol in the step (2) is 1:20-19: 20.
Preferably, the volume ratio of chloroform-methanol-water in the step (3) is 8:2: 1.
Preferably, the volume ratio of the ethyl acetate-chloroform-methanol-water in the step (3) is 15:8:4: 1.
Preferably, the column chromatography in step (3) is silica gel column chromatography.
The invention also provides an application of the octopamine dimer compound in preparation of antibacterial drugs.
The method for extracting the polygonatum sibiricum powder by using the ethanol in the step (1) is divided into multiple times of extraction, so that the active ingredients in the raw materials are extracted to the maximum extent, and the extraction times are not less than 2 times.
The polarity of the eluent water-ethanol in the gradient elution in the step (2) of the invention is eluted from small to big, and 7 different fractions A-G are eluted in sequence, wherein the fraction A is eluted firstly, and the fraction G is eluted finally.
At present, researchers extract various active ingredients such as polygonatum polysaccharide, saponin, flavone and the like from polygonatum, and the active ingredients are obtained by mainly using an alcohol extraction method or a water extraction method, extracting an extracting solution for multiple times by using an organic solvent or water, and eluting and purifying an organic layer. However, the commonly used eluent is water, ethanol or petroleum ether-ethyl acetate, such as a new dihydrohomoisoflavone extracted from rhizoma Polygonati in patent application No. CN201710317110.4, and the used eluent is petroleum ether-ethyl acetate; the more used eluent for extracting other Chinese medicinal materials is water, ethanol or chloroform-methanol, such as Achillea Wilsoniana Hance extract with acetylcholinesterase inhibiting activity extracted from Achillea Wilsoniana Hance in patent application No. CN 201510058772.5, wherein the eluent is chloroform-methanol. Elution with a mixture of ethyl acetate-chloroform-methanol-water has not been shown at present,
but the elution is carried out by using single ethyl acetate, methanol or chloroform, and the person skilled in the art knows that the effect of the elution by using a mixture of a plurality of solvents is unpredictable compared with the elution by using a single organic solvent, so that the elution by using single ethyl acetate, methanol or chloroform in the prior art cannot be considered to be carried out by mixing the three as the eluent; in addition, in the extraction of other traditional Chinese medicine substances, elution is mostly carried out once, and the difference of the eluent is not great even if elution is carried out for multiple times. The invention firstly uses water-ethanol to carry out gradient elution on the extract obtained by n-butanol extraction, then uses chloroform-methanol-water and ethyl acetate-chloroform-methanol-water to carry out constant elution on the fraction E, and finally purifies the liquid obtained by elution to obtain the novel octopamine dimer compound. The eluent used in the method is greatly different from the existing eluent used for extracting the active ingredients of the traditional Chinese medicine substances, the types and polarities of the eluents are different, and finally the active ingredients extracted from the sealwort are different, so that on the basis of the prior art, the eluent in the prior art is replaced by the eluent in the application without any revelation, and the technical scheme of the application is difficult to obtain.
The method comprises the steps of extracting rhizoma polygonati powder with ethanol, extracting the obtained extracting solution with n-butyl alcohol, and concentrating to obtain an extract; the extract is subjected to gradient elution by using water-ethanol with the volume ratio of 1:20-19:20 to obtain 7 different fractions A-G, then the fraction E is subjected to constant elution by using chloroform-methanol-water with the volume ratio of 8:2:1 and ethyl acetate-chloroform-methanol-water with the volume ratio of 15:8:4:1 respectively, and the liquid obtained by elution is purified to obtain a novel octopamine dimer compound which is firstly extracted from rhizoma polygonati and is a brand new compound in the nature, and the preparation method is simple and is convenient to operate.
The preparation method provided by the invention is adopted to extract a brand new compound from rhizoma polygonati, namely a novel octopamine dimer compound.
The invention has the beneficial effects that:
1. the invention firstly uses water-ethanol to carry out gradient elution on the extract obtained by n-butanol extraction, then uses chloroform-methanol-water and ethyl acetate-chloroform-methanol-water to carry out constant elution on the fraction E, and finally purifies the liquid obtained by elution to obtain the novel octopamine dimer compound which is extracted from rhizoma polygonati for the first time and is a brand new compound in the nature, thereby fully utilizing the rhizoma polygonati resources, improving the use value of the raw materials and having important significance for promoting the research and application of the active ingredients of the rhizoma polygonati.
2. The preparation method of the invention is adopted to extract a brand new compound from the sealwort, namely a novel octopamine dimer compound, the compound has good antibacterial effect, can be used for preparing antibacterial drugs, has important clinical application value, and is beneficial to the development and quality control of sealwort medicinal materials and preparations thereof.
3. The organic solvent used in the method has low toxicity and is easy to recover; the method has the characteristics of few working procedures, simple equipment, convenient operation, good feasibility, low production cost and the like, and the finally obtained novel octopamine dimer compound has high purity which is more than 95%.
Drawings
FIG. 1 shows the preparation of octopamine dimer compounds of the present invention13C-NMR spectrum.
FIG. 2 shows the preparation of octopamine dimer compounds of the present invention1H-NMR spectrum.
FIG. 3 is a diagram of the heteronuclear single quantum relationship (HSQC) spectrum of the octopamine dimer compound of the present invention.
FIG. 4 is a multi-bond hydrocarbon relationship (HMBC) spectrum of the octopamine dimer compound of the present invention.
FIG. 5 shows homonuclear shift correlation of the octopamine dimers of the invention1H-1H COSY) spectrum.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to specific embodiments below.
Example 1
(1) Taking 500g of polygonatum cyrtonema root raw material, drying, crushing, sieving to obtain polygonatum cyrtonema powder, extracting with 2500ml of 95% ethanol by volume, repeatedly extracting for 2 times by using a DTQ-200 multifunctional extraction tank as an extraction instrument to obtain an extracting solution; extracting the extract with 2500ml of n-butanol, and concentrating the n-butanol layer to obtain an extract;
(2) loading the extract into AB-8 macroporous adsorbent resin column, and gradient eluting with 5000ml water-ethanol at volume ratio of 1:20-19:20 to obtain 7 different fractions A-G;
(3) loading fraction E on silica gel column chromatography, eluting with 3500ml of chloroform-methanol-water at a volume ratio of 8:2:1, further eluting the obtained eluate with 2000ml of ethyl acetate-chloroform-methanol-water at a volume ratio of 15:8:4:1, and drying the eluted liquid to obtain the novel octopamine dimer compound with a purity of more than 95%.
Example 2
(1) Taking 500g of polygonatum cyrtonema root raw material, drying, crushing, sieving to obtain polygonatum cyrtonema powder, extracting with 4000ml of 95% ethanol by volume, repeatedly extracting for 3 times by using a DTQ-200 multifunctional extraction tank as an extraction using instrument to obtain an extracting solution; extracting the extract with 2000ml n-butanol, and concentrating n-butanol layer to obtain extract;
(2) loading the extract into AB-8 macroporous adsorbent resin column, and gradient eluting with 5000ml water-ethanol at volume ratio of 1:20-19:20 to obtain 7 different fractions A-G;
(3) loading fraction E on silica gel column chromatography, eluting with 3500ml of chloroform-methanol-water at a volume ratio of 8:2:1, further eluting the obtained eluate with 2000ml of ethyl acetate-chloroform-methanol-water at a volume ratio of 15:8:4:1, and drying the eluted liquid to obtain the novel octopamine dimer compound with a purity of more than 95%.
1. And (3) identifying the structure of the compound:
the novel octopamine dimer compound obtained in example 1 is white powder, and the structure of the novel octopamine dimer compound is identified, wherein the data of the nuclear magnetic resonance spectrogram of the novel octopamine dimer compound is shown in table 1, the nuclear magnetic resonance carbon spectrum and the nuclear magnetic resonance hydrogen spectrum are shown in fig. 1 and 2, the HSQC spectrogram is shown in fig. 3, the HMBC spectrogram is shown in fig. 4, and the 1H-1H COSY spectrogram is shown in fig. 5.
TABLE 1 NMR spectra of novel octopamine dimers
As shown in fig. 1-5, in1In the H NMR spectrum, the 7.43(1H, d, J-15.7 Hz, H-7') and 6.47(1H, d, J-15.7 Hz, H-8') signals form a trans-substituted double bond, 7.16(2H, d, J-8.4 Hz, H-2and H-6),6.78(2H, d, J-8.4 Hz, H-3and H-5),129.2(d, C-2and C-6) and 116.3(d, C-3and C-5), in combination13CNMR spectra confirmed the presence of a para-substituted aromatic ring, and also 7.12(1H, d, J ═ 1.3Hz, H-2'),6.79(1H, d, J ═ 8.3Hz, H-5'),7.02(1H, dd, J ═ 8.3,1.3Hz, H-6'), and 111.5(d, C-2'),116.5(d, C-5'),123.3(d, C-6') confirmed 1,3, 4-trisubstituted aromatic rings. DeltaH3.88 and deltaC56.4 confirmation of the presence of a methoxy group, deltaH4.24,3.39,3.50 and δC83.2(d),47.1(t),169.2(s) confirmed the presence of the N-ethylformamide group.1H-1The H COSY spectrum shows that C7-C8 and C7'-C8' are connected. In addition, in the HMBC spectrum, 3.39(1H, dd, J ═ 13.8,8.5Hz, H-8a),3.50(1H, dd, J ═ 13.8,4.6Hz, H-8b),7.43(1H, d, J ═ 15.7Hz, H-7'), and C-9' (δ -7') were foundC169.2) signal correlation, 4.24(1H, dd, J ═ 8.5,4.6Hz, H-7) and C-2, C-6(δ)C129.2) signal correlation, 7.43(1H, d, J ═ 15.7Hz, H-7') and C-2' (δC111.5) and C-6' (delta)C123.3) signal correlation, 3.88(3H, s) and C-3' (delta)C149.3) signals are correlated, the above information indicates that the compound is possible to be trans-N-ferulamide, and further comparison of the change rule of chemical shift shows that the compound is a dimer compound further formed by ether bond (C-O-C) of the trans-N-ferulamide, and the novel octopamine dimer compound is identified to be trans-bis (N-feruloyl) octopamine.
2. Study of antibacterial Activity
The novel octopamine dimer compound is subjected to a Minimum Inhibitory Concentration (MIC) test experiment, and the specific experimental steps are as follows:
(1) inoculating a few bacteria from the plate into a conical flask filled with LB culture medium (Luria-Bertani culture medium), and performing shake culture at 37 ℃ for 12-14 h; wherein the test strains comprise gram-positive bacteria and gram-negative bacteria; the formulation of LB medium was as follows: 10g/L of Tryptone (Tryptophan), 5g/L of Yeast extract (Yeast extract) and 10g/L of sodium oxide (NaCl).
(2) And (3) sucking the bacterial liquid from the conical flask in the morning of 2 days, transferring the bacterial liquid into the conical flask filled with 20ml of LB culture medium in a volume ratio of 1%, continuously culturing the bacterial liquid in a shaking table at 37 ℃ for 6-7 h until OD600(OD600 represents the light absorption value of the bacterial liquid at the wavelength of 600 nm) is 0.6-0.8, and recording the specific OD (optical density) of the bacterial liquid.
(3) The cultured bacterial liquid was diluted 1000-fold with LB medium to a bacterial liquid concentration of 105CFU/ml, and the diluted bacterial liquid was aspirated and added to a 96-well plate at 150. mu.l per well.
(4) Preparing a novel octopamine dimer compound solution with the concentration of 128 mu g/ml, sucking 150 mu l of the novel octopamine dimer compound solution, adding the solution into the 1 st hole in a 96-hole plate, sucking 150 mu l of the solution into the 2 nd hole, and the like.
(5) After the dropwise addition, putting the 96-well plate into a shaking table, and culturing for 12-14 h at 37 ℃.
(6) After the dropwise addition, the mixture is put into a shaking table to be cultured for the optimal time of 12-14 h at 37 ℃.
The minimum concentration corresponding to the wells without turbidity is the minimum inhibitory concentration of the bacteria through visual observation, specifically referring to table 2, and table 2 is the Minimum Inhibitory Concentration (MIC) of the novel octopamine dimer compound to two bacteria.
TABLE 2 Minimum Inhibitory Concentration (MIC) of novel octopamine dimers
As shown in table 2, the novel octopamine dimer compound obtained in example 1 of the present invention can significantly inhibit the growth of gram-positive bacteria, and the minimum inhibitory concentration to staphylococcus aureus, bacillus, and the like is 1 to 2 μ g/ml, so that the novel octopamine dimer compound has a good antibacterial effect, and can be used for preparing antibacterial drugs.
Claims (10)
1. An octopamine dimer compound, which has the following structural formula:
2. a method for preparing the octopamine dimer compound of claim 1, comprising the steps of:
(1) extracting rhizoma Polygonati powder with ethanol, extracting the obtained extractive solution with n-butanol, and concentrating n-butanol layer to obtain extract;
(2) subjecting the extract to gradient elution with macroporous adsorbent resin column with water-ethanol to obtain 7 different fractions A-G;
(3) and eluting the fraction E by using chloroform-methanol-water for constant degree through column chromatography, further eluting the obtained elution component by using ethyl acetate-chloroform-methanol-water for constant degree, and drying the eluted liquid to obtain the octopamine dimer compound.
3. The method for preparing an octopamine dimer compound according to claim 2, wherein the method for preparing the polygonatum sibiricum powder in the step (1) comprises the following steps: drying and crushing the roots of polygonatum cyrtonema and sieving to obtain polygonatum cyrtonema powder.
4. The method for preparing an octopamine dimer compound according to claim 2, wherein the ethanol concentration in step (1) is 95% by volume.
5. The method for preparing octopamine dimer compounds according to claim 2 or 3, wherein the mass ratio of rhizoma Polygonati powder to ethanol in step (1) is 1: 5-8.
6. A method for preparing an octopamine dimer compound according to claim 2 or 3, wherein the volume ratio of water to ethanol in the step (2) is 1:20 to 19: 20.
7. A method for preparing octopamine dimers according to claim 2 or 3, wherein the volume ratio of chloroform-methanol-water in the step (3) is 8:2: 1.
8. A method for preparing octopamine dimers according to any one of claims 2 to 4, wherein the volume ratio of ethyl acetate-chloroform-methanol-water in the step (3) is 15:8:4: 1.
9. The process for producing an octopamine dimer compound according to any one of claims 2 to 4, wherein the column chromatography in the step (3) is silica gel column chromatography.
10. The use of the octopamine dimer compound of claim 1 in the preparation of an antibacterial agent.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104069348A (en) * | 2014-06-30 | 2014-10-01 | 天津中医药大学 | Sealwort extract as well as preparation method and use thereof |
| CN104940609A (en) * | 2015-07-08 | 2015-09-30 | 广州白云山汉方现代药业有限公司 | Method for extracting and separating multiple active constituents from polygonatum |
| CN105646439A (en) * | 2014-11-10 | 2016-06-08 | 中国人民解放军第二军医大学 | Synergist for antifungal drugs, and preparation and application thereof |
-
2018
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104069348A (en) * | 2014-06-30 | 2014-10-01 | 天津中医药大学 | Sealwort extract as well as preparation method and use thereof |
| CN105646439A (en) * | 2014-11-10 | 2016-06-08 | 中国人民解放军第二军医大学 | Synergist for antifungal drugs, and preparation and application thereof |
| CN104940609A (en) * | 2015-07-08 | 2015-09-30 | 广州白云山汉方现代药业有限公司 | Method for extracting and separating multiple active constituents from polygonatum |
Non-Patent Citations (5)
| Title |
|---|
| A New Antibacterial Tetrahydronaphthalene Lignanamide,Foveolatamide, from the Stems of Ficus foveolata;Wirod Meerungrueang等;《Natural Product Communications》;20161231;第11卷(第1期);第91-94页 * |
| Induced phenylamide accumulation in response to pathogen infection and hormone treatment in rice (Oryza sativa);Noriko Morimoto等;《Taylor & Francis》;20180209;第1-10页 * |
| NMR-based identification of the major bioactive molecules from an Italian cultivar of Lycium barbarum;Annalisa Lopatriello等;《Phytochemistry》;20170828;第144卷;第52-57页 * |
| NMR-based identification of the phenolic profile of fruits of Lycium barbarum (goji berries). Isolation and structural determination of a novel N-feruloyl tyramine dimer as the most abundant antioxidant polyphenol of goji berries;Martino Forino等;《Food Chemistry》;20150831;第194卷;第1254-1259页 * |
| Phytochemical Constituents from Salsola tetrandra;M. Habib Oueslati等;《J.Nat.Prod.》;20061231;第69卷;第1366-1369页 * |
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