CN109232298A - A kind of novel octopamine dimer class compound, preparation method and application - Google Patents
A kind of novel octopamine dimer class compound, preparation method and application Download PDFInfo
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- C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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Abstract
The present invention provides a kind of novel octopamine dimer class compound, and preparation method is that Solomonseal Rhizome, obtained extracting solution extracting n-butyl alcohol are extracted with ethyl alcohol, and n-butanol layer is concentrated to get medicinal extract；Medicinal extract carries out gradient elution with water-ethanol through large pore resin absorption column, obtains 7 different fraction A-G；Fraction E is eluted through column chromatography chloroform-methanol-water perseverance degree, by gained elution fraction, with ethyl acetate-chloroform-methanol-water, further perseverance degree is eluted, the liquid purifying eluted obtains novel octopamine dimer class compound, the compound is to be extracted in rhizoma polygonati for the first time, and it is compound completely new in nature, can be used for preparing antibacterials.
Description
Technical field
The present invention relates to medicine extractive technique fields, and in particular to a kind of novel octopamine dimer class compound, system
Preparation Method and application.
Background technique
Polygonatum cyrtonema, from the dry rhizome also known as RHIZOMA POLYGONATI ZINGIBERIFORME of Liliaceae Polygonatum polygonatum cyrtonema plant.Main product in
Southern region of China, it is one of its genuine place of production that Hunan Province cultivation polygonatum cyrtonema is with a long history.Compendium of Material Medica says that it " is obtained female
The essence of soil, for the victory product for taking a tonic or nourishing food to build up one's health Middle Palace " has the effect of tonifying kidney and benefiting sperm, nourishing Yin and moistening dryness, long-term for treating kidney deficiency loss, spleen
Stomach is weak, deficiency syndrome of the lung cough caused by dryness, the disease of fatigue and asthenia, while being also the important component of tens of kinds of compound nourishing medicaments, rhizoma polygonati rhizomes
Shape just like sweet potato, mountain area common people often it ought medicinal plant for vegetable consumption, there is tonifying spleen, the effect of moistening lung and producing body fluid.This
Outside, since rhizoma polygonati also contains multiple efficacies ingredient, such as furan steroid enol form saponin, spirostene alcohol type saponin and polysaccharide, usually also
For anti-oxidant, antifatigue aspect.
Various active substance is extracted from rhizoma polygonati at present, as number of patent application CN104069348A discloses one kind
Rhizoma Polygonati extract and the preparation method and application thereof, after which mentions rhizoma polygonati by ethyl alcohol heat, then with petroleum ether, ethyl acetate,
Extracting n-butyl alcohol mainly contains 5 hydroxymethyl furfural, steroid saponin and phenolic acid class (lignanoid etc.) ingredient in obtained compound, main
It is used for anti-diabetic and its complication；Number of patent application CN201510395570.X discloses various active in a kind of rhizoma polygonati
The extraction separation method of ingredient extracts separation Siberian solomonseal rhizome polysaccharide, sibiricoside and rhizoma polygonati flavones isoreactivity by homogenate extraction technology
Ingredient.For the research of rhizoma polygonati chemical component, the effective component extracted from rhizoma polygonati at present is also fewer, mainly rhizoma polygonati
Polysaccharide, sibiricoside and rhizoma polygonati flavones etc. are several, however rhizoma polygonati effective component is sufficiently complex, and only these types of ingredient is inadequate
, it is still necessary to rhizoma polygonati extraction process is furtherd investigate, to extract more effective components.It is extracted from rhizoma polygonati and isolates octopus
There is not been reported so far for amine dimer class compound, and also nobody extracts octopamine dimer class chemical combination from other substances
Object.
Summary of the invention
The purpose of the present invention is overcome the deficiencies of the prior art and provide a kind of novel octopamine dimer class compound, system
Preparation Method and application.
The present invention provides a kind of novel octopamine dimer class compound, the knots of the octopamine dimer class compound
Structure formula is as follows:
The present invention also provides a kind of preparation methods of novel octopamine dimer class compound, comprising the following steps:
(1) Solomonseal Rhizome, obtained extracting solution extracting n-butyl alcohol are extracted with ethyl alcohol, n-butanol layer is concentrated to get medicinal extract；
(2) medicinal extract carries out gradient elution with water-ethanol through large pore resin absorption column, obtains 7 different fraction A-G；
(3) fraction E is eluted through column chromatography chloroform-methanol-water perseverance degree, by gained elution fraction ethyl acetate-chloroform-
Further perseverance degree elutes methanol-water, and the liquid eluted is dried to obtain novel octopamine dimer class compound.
Preferably, the Solomonseal Rhizome in the step (1) the preparation method comprises the following steps: by polygonatum cyrtonema root by dry and powder
Broken processing obtains Solomonseal Rhizome after sieving.
Preferably, the volumetric concentration of ethyl alcohol is 95% in the step (1).
Preferably, the mass ratio of Solomonseal Rhizome and ethyl alcohol is 1:5-8 in the step (1).
Preferably, the volume ratio of water-ethanol is 1:20-19:20 in the step (2).
Preferably, chloroform-methanol-water volume ratio is 8:2:1 in the step (3).
Preferably, ethyl acetate-chloroform-methanol-water volume ratio is 15:8:4:1 in the step (3).
Preferably, column chromatography is silica gel column chromatography in the step (3).
The present invention also provides a kind of application of novel octopamine dimer class compound in preparation antibacterials.
Solomonseal Rhizome is extracted with ethyl alcohol described in step (1) of the present invention and is divided into multiple extraction, to extract to greatest extent
Active constituent in raw material out, extraction time are no less than 2 times.
The polarity of eluant, eluent water-ethanol is ascending elution in step (2) the of the present invention gradient elution, is successively washed
7 different fraction A-G, A fractions of abjection are eluted out at first, and G fraction is finally eluted out.
Currently, researcher is extracted a variety of active ingredients, such as Siberian solomonseal rhizome polysaccharide, saponin(e and flavones from rhizoma polygonati, mainly
With method be that alcohol extracting either water mentions, then extracting solution organic solvent or water are repeatedly extracted, organic layer using
Elution, purifying obtain active constituent.But common eluant, eluent is water, ethyl alcohol or petroleum ether-ethyl acetate, such as number of patent application
It is extracted from rhizoma polygonati in CN201710317110.4 and obtains a kind of new Homoisoflavonoids, eluant, eluent used is petroleum ether-
Ethyl acetate；The more eluant, eluent used when medicinal substances extract in other is also water, ethyl alcohol or chloroform-methanol, as specially
It is extracted from Herba Lycopodii in sharp application number CN 201510058772.5 and obtains a kind of Herba Lycopodii inhibiting activity of acetylcholinesterase and mention
Object is taken, eluant, eluent therein is chloroform-methanol.Do not occur being eluted with ethyl acetate-chloroform-methanol-water mixing at present,
But with the elution of single ethyl acetate, methanol or chloroform, those skilled in the art will know that mixed with multi-solvents
It closes elution to elute compared to single organic solvent, effect is uncertain, therefore is had in the prior art with single second
Acetoacetic ester, methanol or chloroform make eluant, eluent, do not make eluant, eluent it is contemplated that three is mixed；And medicinal substances in other
It is mostly once to elute, and just repeatedly elute its eluant, eluent at last and be also not much different in extraction.The present invention will pass through n-butanol
The medicinal extract being obtained by extraction first uses water-ethanol gradient elution, then fraction E is used to chloroform-methanol-water sum acetic acid second respectively again
Ester-chloroform-methanol-water perseverance degree elution, the liquid purifying finally afforded obtain novel octopamine dimer class compound.This
Invention eluant, eluent used has biggish difference with the eluant, eluent for being currently used for Chinese medicine species activity constituents extraction, and eluant, eluent
Type is different, and polarity is different, and the active constituent extracted in final rhizoma polygonati is also different, therefore, on the basis of the prior art
On, and any enlightenment is not present, eluant, eluent in the prior art is replaced with into the eluant, eluent in the application, it is also just difficult to obtain
The technical solution of the application.
The application extracts Solomonseal Rhizome with ethyl alcohol, and obtained extracting solution extracting n-butyl alcohol is concentrated to get medicinal extract；Medicinal extract is used
Volume ratio is the water-ethanol gradient elution of 1:20-19:20, obtains 7 different fraction A-G, fraction E is then used body respectively
The ethyl acetate-chloroform that the chloroform-methanol-water and volume ratio that product ratio is 8:2:1 are 15:8:4:1-methanol-water perseverance degree elution, is washed
De- obtained liquid purifying obtains novel octopamine dimer class compound, and this compound is to be extracted in rhizoma polygonati for the first time
Come, and be compound completely new in nature, preparation method is simple, easy to operate.
A kind of completely new compound, i.e., novel octopamine dimer are extracted from rhizoma polygonati using preparation method of the invention
Class compound, the inventor of the present application found through research that, which has good antibacterial effect, can be used for preparing antibacterial
Drug is conducive to exploitation and quality control to rhizoma polygonati medicinal material and its preparation.
The beneficial effects of the present invention are:
1, the medicinal extract obtained by extracting n-butyl alcohol is first used water-ethanol gradient elution by the present invention, then divides fraction E again
Not Yong the elution of chloroform-methanol-water sum ethyl acetate-chloroform-methanol-water perseverance degree, the liquid purifying finally afforded obtains
Novel octopamine dimer class compound, this compound are to be extracted in rhizoma polygonati for the first time, and are complete in nature
New compound takes full advantage of rhizoma polygonati resource, improves the use value of raw material, grinds to propulsion rhizoma polygonati active constituent
Study carefully, using significant.
2, a kind of completely new compound, i.e., novel octopamine dimerization are extracted from rhizoma polygonati using preparation method of the invention
Body class compound, the compound have good antibacterial effect, can be used for preparing antibacterials, have important clinical application valence
Value is conducive to exploitation and quality control to rhizoma polygonati medicinal material and its preparation.
3, organic solvent toxicity used in the method for the present invention is smaller, is easily recycled；And this method has that process is few, equipment
It is simple and convenient to operate, the features such as feasibility is good, low production cost, finally obtained novel octopamine dimer class compound
Purity is high reaches 95% or more.
Detailed description of the invention
Fig. 1 is the novel octopamine dimer class compound of the present invention13C-NMR spectrogram.
Fig. 2 is the novel octopamine dimer class compound of the present invention1H-NMR spectrum.
Fig. 3 is heteronuclear list quantum relation (HSQC) spectrogram of the novel octopamine dimer class compound of the present invention.
Fig. 4 is the hydrocarbon relationship of multikey (HMBC) spectrogram of the novel octopamine dimer class compound of the present invention.
Fig. 5 be the same core displacement of the novel octopamine dimer class compound of the present invention it is related (1H-1H COSY) spectrogram.
Specific embodiment
To make the objectives, technical solutions, and advantages of the present invention clearer, below in conjunction with specific embodiment, to this hair
Bright further description.
Embodiment 1
(1) 500g polygonatum cyrtonema root raw material is taken, through pulverization process after drying, sieving obtains Solomonseal Rhizome, uses 2500ml
The ethyl alcohol that volumetric concentration is 95% extracts, and extracting using instrument is DTQ-200 type multi-function extractor, repeats after extracting 2 times, obtains
To extracting solution；Extracting solution is extracted with the n-butanol of 2500ml, n-butanol layer is concentrated to get medicinal extract；
(2) medicinal extract is splined on AB-8 large pore resin absorption column, with the water-ethanol of 5000ml volume ratio 1:20-19:20 into
Row gradient elution obtains 7 different fraction A-G；
(3) fraction E is splined on silica gel column chromatography, is eluted with chloroform-methanol-water perseverance degree that 3500ml volume ratio is 8:2:1,
Further perseverance degree elutes the ethyl acetate-chloroform-methanol-water for being 15:8:4:1 with 2000ml volume ratio by gained elution fraction,
The liquid eluted is dried to obtain novel octopamine dimer class compound, and purity is greater than 95%.
Embodiment 2
(1) 500g polygonatum cyrtonema root raw material is taken, through pulverization process after drying, sieving obtains Solomonseal Rhizome, uses 4000ml
The ethyl alcohol that volumetric concentration is 95% extracts, and extracting using instrument is DTQ-200 type multi-function extractor, repeats after extracting 3 times, obtains
To extracting solution；Extracting solution is extracted with the n-butanol of 2000ml, n-butanol layer is concentrated to get medicinal extract；
(2) medicinal extract is splined on AB-8 large pore resin absorption column, with the water-ethanol of 5000ml volume ratio 1:20-19:20 into
Row gradient elution obtains 7 different fraction A-G；
(3) fraction E is splined on silica gel column chromatography, is eluted with chloroform-methanol-water perseverance degree that 3500ml volume ratio is 8:2:1,
Further perseverance degree elutes the ethyl acetate-chloroform-methanol-water for being 15:8:4:1 with 2000ml volume ratio by gained elution fraction,
The liquid eluted is dried to obtain novel octopamine dimer class compound, and purity is greater than 95%.
1, compound structure is identified:
The novel octopamine dimer class compound that embodiment 1 obtains is white powder, is identified its structure, this is new
The data of the nmr spectrum of type octopamine dimer class compound are as shown in table 1, carbon-13 nmr spectra and hydrogen nuclear magnetic resonance
Spectrum as illustrated in fig. 1 and 2, hsqc spectrum figure as shown in figure 3, HMBC spectrogram as shown in figure 4,1H-1H COSY spectrogram is as shown in Figure 5.
The nuclear magnetic spectrogram of the novel octopamine dimer class compound of table 1
As shown in Figs. 1-5, exist1In H NMR spectra, 7.43 (1H, d, J=15.7Hz, H-7') and 6.47 (1H, d, J=
15.7Hz, H-8') signal constitutes a trans- substituted double bond, 7.16 (2H, d, J=8.4Hz, H-2 and H-6), and 6.78
(2H, d, J=8.4Hz, H-3 and H-5), 129.2 (d, C-2 and C-6) and 116.3 (d, C-3 and C-5), knot
It closes13CNMR spectrogram, it can be verified that there are one to align the aromatic ring replaced, in addition, 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') confirm it for the trisubstituted aromatic ring of 1,3,4-.δH3.88 and δC56.4 confirm that there are a first
Oxygroup, δH4.24,3.39,3.50 and δC83.2 (d), 47.1 (t), 169.2 (s) confirm depositing for N- ethyl-formamide group
?.1H-1H COSY spectrogram shows that C7-C8 and C7'-C8' has connection.In addition, in HMBC spectrogram, 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'(δC169.2) signal is related, 4.24 (1H, dd, J=8.5,4.6Hz, H-7) and C-2, C-6 (δC129.2) signal is related,
7.43 (1H, d, J=15.7Hz, H-7') and C-2'(δCAnd C-6'(δ 111.5)C123.3) signal is related, 3.88 (3H, s) with
C-3'(δC149.3) signal is related, and information above illustrates that the compound is possible to as trans--N- asafoetide acid amide, further comparison
The changing rule of its chemical shift is it is found that find that the compound is by trans--N- asafoetide acid amide into ehter bond (C-O-C) further shape
At dimer compound, through reflecting
Fixed, which is trans--bis- (N- asafoetide acyl group) octopamine.
2, antibacterial activity is studied
Novel octopamine dimer class compound is subjected to minimum inhibitory concentration (Minimum Inhibition
Concentration, MIC) test experiments, steps are as follows for specific experiment:
(1) from be inoculated on plate a little bacterium in equipped with LB culture medium (Luria-Bertani culture medium) conical flask in, 37
DEG C 12~14h of shaking table culture；Wherein, test strain includes: gram-positive bacteria and Gram-negative bacteria；The formula of LB culture medium
It is as follows: tryptose old (Tryptone) 10g/L, yeast extract (Yeast extract) 5g/L, sodium oxide molybdena (NaCl) 10g/L.
(2) the 2nd day morning drew bacterium solution from conical flask with 1% volume ratio switching in the LB culture medium equipped with 20ml
In conical flask, culture 6h~7h in 37 DEG C of shaking tables is continued at, until (OD600 indicates suction of the bacterium solution at 600nm wavelength to OD600
Light value) it is 0.6~0.8, and record the specific OD value (optical density, optical density) of bacterium solution.
(3) bacterium solution after culture is diluted 1000 times with LB culture medium, makes bacterial concentration 105CFU/ml, draw dilution
Bacterium solution afterwards, and add in 96 orifice plates, every 150 μ l of hole.
(4) the novel octopamine dimer class compound solution that compound concentration is 128 μ g/ml respectively, drawing 150 μ l, this is new
Type octopamine dimer class compound solution adds in the 1st hole in 96 orifice plates, 150 μ l is then sucked out into the 2nd hole, with such
It pushes away.
(5) after being added dropwise, 96 orifice plates are put into shaking table through 37 DEG C of culture 12h~14h.
(6) after being added dropwise, being put into the Best Times cultivated in shaking table through 37 DEG C is 12h~14h.
It visually observes, the smallest concentration corresponding to the hole not become cloudy is the minimum inhibitory concentration of the bacterium, specifically
Referring to table 2, table 2 is minimum inhibitory concentration (MIC) of the novel octopamine dimer class compound to two kinds of bacteriums.
The minimum inhibitory concentration (MIC) of the novel octopamine dimer class compound of table 2
As shown in table 3, it is blue that the novel octopamine dimer class compound that the embodiment of the present invention 1 obtains can significantly inhibit leather
The growth of family name's positive bacteria, the minimum inhibitory concentration to staphylococcus aureus and bacillus etc. are 1~2 μ g/ml, it is seen that this is new
The antibacterial effect of type octopamine dimer class compound is good, can be used to prepare antibacterials.
Claims (10)
1. a kind of novel octopamine dimer class compound, which is characterized in that the structure of the octopamine dimer class compound
Formula is as follows:
2. it is a kind of as described in claim 1 novel octopamine dimer class compound preparation method, which is characterized in that including with
Lower step:
(1) Solomonseal Rhizome, obtained extracting solution extracting n-butyl alcohol are extracted with ethyl alcohol, n-butanol layer is concentrated to get medicinal extract；
(2) medicinal extract carries out gradient elution with water-ethanol through large pore resin absorption column, obtains 7 different fraction A-G；
(3) fraction E is eluted through column chromatography chloroform-methanol-water perseverance degree, by gained elution fraction ethyl acetate-chloroform-first
Further perseverance degree elutes alcohol-water, and the liquid eluted is dried to obtain novel octopamine dimer class compound.
3. the preparation method of novel octopamine dimer class compound as claimed in claim 2, which is characterized in that the step
(1) Solomonseal Rhizome in the preparation method comprises the following steps: by polygonatum cyrtonema root by dry and pulverization process, rhizoma polygonati powder is obtained after sieving
End.
4. the preparation method of novel octopamine dimer class compound as claimed in claim 2, which is characterized in that the step
(1) volumetric concentration of ethyl alcohol is 95% in.
5. the preparation method of novel octopamine dimer class compound as described in Claims 2 or 3, which is characterized in that the step
Suddenly the mass ratio of Solomonseal Rhizome and ethyl alcohol is 1:5-8 in (1).
6. the preparation method of novel octopamine dimer class compound as described in Claims 2 or 3, which is characterized in that the step
Suddenly the volume ratio of water-ethanol is 1:20-19:20 in (2).
7. the preparation method of novel octopamine dimer class compound as described in Claims 2 or 3, which is characterized in that the step
Suddenly chloroform-methanol-water volume ratio is 8:2:1 in (3).
8. the preparation method of novel octopamine dimer class compound as described in claim any one of 2-4, which is characterized in that institute
Stating ethyl acetate-chloroform-methanol-water volume ratio in step (3) is 15:8:4:1.
9. the preparation method of novel octopamine dimer class compound as described in claim any one of 2-4, which is characterized in that institute
Stating column chromatography in step (3) is silica gel column chromatography.
10. a kind of application of the novel octopamine dimer class compound described in claim 1 in preparation antibacterials.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114957181A (en) * | 2022-07-11 | 2022-08-30 | 山东省分析测试中心 | Method for separating and purifying high-isoflavone compounds in rhizoma polygonati by high-speed counter-current chromatography |
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| 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 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114957181A (en) * | 2022-07-11 | 2022-08-30 | 山东省分析测试中心 | Method for separating and purifying high-isoflavone compounds in rhizoma polygonati by high-speed counter-current chromatography |
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