CN108610258A - One new phenolic acid compound and preparation method thereof and medical usage - Google Patents
One new phenolic acid compound and preparation method thereof and medical usage Download PDFInfo
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- CN108610258A CN108610258A CN201810343914.6A CN201810343914A CN108610258A CN 108610258 A CN108610258 A CN 108610258A CN 201810343914 A CN201810343914 A CN 201810343914A CN 108610258 A CN108610258 A CN 108610258A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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Abstract
The present invention relates to the structure of a new phenolic acid compound, preparation method and applications in antibacterial field.The present invention has obtained a noval chemical compound, has been named as sedumol A, pharmacodynamic experiment shows that sedumol A show stronger inhibiting effect to escherichia coli and staphylococcus aureus etc. from dish aerial part extracting and developing, purifying is taken.
Description
Technical field
The invention belongs to pharmaceutical technology fields, and in particular to a new liposoluble ingredient preparation method of Fei Caizhong and doctor
Medicinal way.
Background technology
Take dish (Sedum aizoon L.) be Crassulaceae (Crassulaceae) sengreen, it is civil have it is long
Medicinal history is widely used in preventing and treating disease of cardiovascular system.Sedum belongs to entirely 470 kinds or so plants, main point
Cloth is on the Northern Hemisphere.China has 124 kinds, 1 subspecies, and 14 mutation and 1 modification are mainly distributed on southwest.Sengreen is at me
There is long medication history between its people, the category Medicinal plant kind is various, and effect is extensive, has clearing heat and detoxicating, hemostasis convergence, sore
Carbuncle serious case of furuncle and other effects.
Take dish also known as spend more aizoon stonecrop, Sedum uizoon, grass of returning to life from the nether world is invaluable, and pouring in June etc. is distributed mainly on the Yellow River the Changjiang river
Basin and the Northeast.Sweet, slightly sour, mild-natured, the thoughts of returning home Liver Channel of property, there is dissipate stasis of blood hemostasis, antitoxic heart-soothing and sedative and other effects.It is civil as
Vegetables and drug are used for prevention and cure of cardiovascular disease, are considered to have the function of blood pressure lowering and reducing blood lipid, because its is significant in efficacy, and quilt
Referred to as Study on Sedum aizoon L, life-saving grass.The chemical composition of funds dish plant has carried out Primary Study both at home and abroad at present, and research finds expense dish
Chemical composition include flavonoids, alkaloids and phenolic acid class etc., wherein phenolic acid class and flavone compound are in the platymiscium
Largely exist extensively, is the characteristic chemical constituent for taking dish.Studies have shown that taking dish has good antibacterial activity, however at present to it
Antibacterial substance basic research and report are simultaneously few.Phenolic acid compound is natural antiseptic, is not eaten such as gallic acid and
Sub- acid methyl esters etc..Fei Caizhong contains a large amount of gallic acid-derivate, therefore the present invention intends to find with antibacterial activity
Gallic acid-derivate.The present invention has obtained the phenolic acid compound of 1 new structure from Fei Caizhong.
Invention content
The purpose of the present invention is to provide new phenolic acid and preparation method thereof and medical usages.
The present invention provides a new phenolic acid to be named as sedumol A, and structure feature is by a molecule gallic acid
By carbonyl and a molecular polylol by dehydrating condensation, have the following structure.
The present invention also provides the preparation methods of the new phenolic acid sedumol A, and this method comprises the following steps：
(1) take dish (Sedum aizoon L.) to be extracted for 30%~90% ethyl alcohol with volume, recycling extracting solution, which obtains, slightly to be carried
Object；
(2) crude extract obtained by step (1) is detached through macroporous adsorbent resin chromatography method, with the alcohol-water of different volumes ratio
Or the mixed solvent of methanol-water carries out gradient elution, obtains the ethyl alcohol or methanol eluate at opposed polarity position；
(3) ethyl alcohol or methanol eluate obtained by above-mentioned steps (2) are detached through silica gel column chromatography, with ethyl acetate/methanol,
Methylene chloride/methanol mixed solvent gradient elution；
(4) gained flow point is detached through high performance liquid chromatography in above-mentioned steps (3), is flowing with Methanol+Water
Phase obtains sedumol A.
The preparation method of the new phenolic acid sedumol A provided by the invention, the plant is Crassulaceae
(Crassulaceae) take the drying herb of dish (Sedum aizoon L.).
The preparation method of the noval chemical compound sedumol A provided by the invention, the extracting method described in step (1) are
It is heated to reflux or heats ultrasonic extraction 1~3 time.Solvent for use is：30%~90% ethyl alcohol, it is preferable that solvent for use is that volume is
The ratio of the volume of 30%~90% ethyl alcohol, the quality for taking dish and solvent is 1:6~1:20.
The preparation method of the noval chemical compound sedumol A provided by the present invention, alcohol-water described in step (2) or
The volume ratio of the mixed solvent of methanol-water, mixed solvent is 0:100~95:5, the preferably first of water, 30%, 60% and 90%
The mixed solvent of alcohol-water or alcohol-water.
The preparation method of the noval chemical compound sedumol A provided by the present invention, ethyl acetate described in step (3)/
The volume ratio of methanol mixed solvent is 100:1~1:1, it is preferably in a proportion of 80:1~10:1, methylene chloride/methanol volume ratio
It is 100:1~2:1, preferably 40:1~4:1.
The preparation method of the noval chemical compound sedumol A provided by the present invention, flowing methanol described in step (4)/
The volume ratio of water mixed solvent is 15:85~90:10, preferably 40：60~70：30.
The present invention has carried out preliminary test and evaluation, selected bacterial strain packet to noval chemical compound sedumol A antibacterial activity in vitro
Include escherichia coli, staphylococcus aureus and bacillus subtilis.Therefore, the noval chemical compound sedumol prepared in the present invention
A can be applied in terms of developing antibacterials.
The present invention is provided for the first time to take dish herb as raw material, and a large amount of enrichments are prepared, identification noval chemical compound sedumol A
Method, and evaluate antibacterial activity, elaborate its application in developing antibacterials.
Description of the drawings
Fig. 1 sedumol A's of the present invention1H H NMR spectroscopies；
Fig. 2 sedumol A's of the present invention13C H NMR spectroscopies；
The hsqc spectrum of Fig. 3 sedumol A of the present invention；
The HMBC of Fig. 4 sedumol A of the present invention is composed；
The HRESIMS of Fig. 5 sedumol A of the present invention is composed
The structural formula of Fig. 6 sedumol A of the present invention.
Specific implementation mode
The following examples will be further described the present invention, but be not intended to limit the present invention.
Embodiment 1
(1) take the dry herb 1000g of dried vegetable, with 70% ethyl alcohol heating ultrasonic extraction 1 time (dosage 8L) after crushing, depressurize back
Receive the crude extract of extracting solution；
(2) 70% alcohol extracts obtained by step (1) are through macroporous resin adsorption, with mixing for the alcohol-water of water, 60% and 90%
Bonding solvent carries out gradient elution；
(3) 60% ethanol elution object of the middle gained of step (2), is detached through silica gel column chromatography, through ethyl acetate/methanol
100:1,100:2,100:5,100:8,100:10,4:1,2:1,1:1 mixed solvent gradient elution；
(4) step (3) ethyl acetate/methanol 100:3 flow points, carry out efficient liquid phase separation, 250nm detections, and flow velocity is
1mL/min, mobile phase are methanol：Water=60:40, obtain sedumol A (tR=7.9min).
Its structure (nuclear magnetic spectrogram and high resolution mass spectrum spectrum is identified according to the physicochemical property of sedumol A and spectral data
Figure is shown in attached drawing 1-5).
The Structural Identification data of sedumol A are as follows：
Colorless oil.HR-ESI-MS provides m/z：311.0723[M+Na]+, calc:311.0743[M+Na]+, in conjunction with1H、13C modal datas determine that molecular formula is：C12H16O8。1H NMR and13C NMR datas are shown in Table 1.
The NMR data ownership of sedumol A is shown in Table 1
The NMR data of 1 sedumol A of tablea
a 600MHz for 1H NMR and 150MHz for 13C NMR in DMSO-d6
Embodiment 2
(1) take the dry herb 2000g of dried vegetable, with 40% ethyl alcohol heating and refluxing extraction 2 times (dosage 20L), decompression after crushing
Recycle the crude extract of extracting solution；
(2) 40% alcohol extracts of gained are through macroporous resin adsorption in step (1), with the second of water, 10%, 50% and 90%
The mixed solvent of alcohol-water is eluted；
(3) 50% ethanol elution object in step (2), successively with methylene chloride/methanol mixed solvent 100:1,100:2,
100:3,100:8,100:10,4:1,2:1,1:1 gradient elution；
(4) methylene chloride/methanol 100 of the middle gained of step (3)：8 flow points are detached using efficient liquid phase, 250nm detections, stream
Speed is 1mL/min, and mobile phase is methanol：Water=60:40, obtain sedumol A (tR=7.9min).
Embodiment 3
(1) preparation method of bacteria suspension
Escherichia coli, staphylococcus aureus, bacillus subtilis are inoculated into meat soup culture, 18-24 is cultivated at 37 °C
Hour.10ml sterile distilled waters are added into sterile test tube respectively, are drawn in bacterium solution to test tube with liquid-transfering gun, shake well
Bacteria suspension is made in 30min.It is counted under the microscope with blood cell counting plate.Bacteria concentration is adjusted to l05CFU/ with fluid nutrient medium
ml。
(2) micro-amounts of liquids method minimal inhibitory concentration (MIC) detection method
The 100 μ L of fluid nutrient medium of corresponding detection are added to 96 hole polystyrene culture plates of sterilizing by sterile working
In each aperture, 100 μ L of sample to be tested are added in the 1st aperture, with liquid-transfering gun pressure-vaccum repeatedly, mixing.It is inhaled from the 1st aperture
It takes 100 μ L to be put into the 2nd aperture, mixes, carry out 2 times of dilution proportions, drawing 100 μ L from the 2nd aperture is added in the 3rd aperture
Mixing 2 is diluted to required concentration successively, then (removing the last one aperture H12 on each plate) adds in different apertures
Enter 100 μ L of corresponding test organisms bacteria suspension, liquid is not added in plate penultimate aperture (G12), as positive control.This
When, drug concentration, which is respectively the 1/2,1/4,1/8,1/16,1/32,1/64 of original liquid concentration, since the 2nd hole ... large intestine bar
Bacterium, staphylococcus aureus, bacillus subtilis culture plate cultivated 18-24 hours at 37 DEG C.(that often goes on 96 orifice plates is last
One hole (number 12) is not added with test organisms bacteria suspension, only culture medium and sample to be tested, as negative control).Every group of reality above
Repetition is tested to do 2 times.As a result judge：It observes by the naked eye, the lowest concentration of drug to completely inhibit bacterial growth in aperture is
MIC.When the apparent growth test of Positive control wells (i.e. not drug containing) interior bacterium is just significant (as the μ of MICs≤500 of test sample
When g/mL, it is believed that compound has bacteriostatic activity).
(3) preparation method of test sample：
Appropriate sample to be tested is weighed, is dissolved with fluid nutrient medium, appropriate DMSO hydrotropies are added in part turbid sample, are made clear
1000 μ L of clear solution.
(4) experimental result
MIC (μ g/mL) result of 2 compound sedumol 3 kinds of bacteriums of A couple of table
The foregoing is only a preferred embodiment of the present invention, but scope of protection of the present invention is not limited thereto,
Any one skilled in the art in the technical scope disclosed by the present invention, according to the technique and scheme of the present invention and its
Inventive concept is subject to equivalent substitution or change, should all cover in protection scope of the present invention.
Claims (8)
1. new phenolic acid compound sedumol A, it is characterised in that：It has the following structure：
2. the preparation method of sedumol A described in a kind of claim 1, it is characterised in that：This method comprises the following steps：
(1) take the ethyl alcohol that dish volume is 30%~90% to extract, recycling extracting solution obtains crude extract；
(2) crude extract obtained by above-mentioned steps (1) is detached through macroporous adsorbent resin chromatography, with the alcohol-water of different volumes ratio or
The mixed solvent of methanol-water carries out gradient elution, obtains the ethyl alcohol or methanol eluate at opposed polarity position；
(3) ethyl alcohol or methanol eluate obtained by above-mentioned steps (2) are detached through silica gel column chromatography, with ethyl acetate/methanol, dichloro
Methane/methanol mixed solvent gradient elution；
(4) gained flow point is detached through high performance liquid chromatography in above-mentioned steps (3), using Methanol+Water as mobile phase, is obtained
To sedumol A.
3. new phenolic acid compound sedumol A preparation methods according to claim 2, it is characterised in that：The plant
Object source is that the plant of Crassulaceae Sedum takes dish.
4. the preparation method of new phenolic acid compound sedumol A according to claim 2, it is characterised in that：Step
(1) extracting method described in is heating and refluxing extraction or heating ultrasonic extraction 1~3 time, solvent for use be volume be 30%~
The ratio of the volume of 90% ethyl alcohol, the quality for taking dish and solvent is 1:6~1:20.
5. according to the preparation method of the sedumol A described in right 2, it is characterised in that alcohol-water described in step (2) and
The volume ratio of the mixed solvent of methanol-water is 0:100~95:5.
6. according to the preparation method of the sedumol A described in right 2, it is characterised in that：Eluting solvent acetic acid described in step (3)
Ethyl ester/methanol, methylene chloride/methanol volume ratio are 100:0~2:1.
7. the preparation method of sedumol A according to claim 2, it is characterised in that：Methanol-water described in step (4)
The volume ratio of bonding solvent is 15:85~90:10.
8. applications of the sedumol A described in claim 1 in preparing antibacterials.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201810343914.6A CN108610258B (en) | 2018-04-17 | 2018-04-17 | Novel phenolic acid compound and preparation method and medical application thereof |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201810343914.6A CN108610258B (en) | 2018-04-17 | 2018-04-17 | Novel phenolic acid compound and preparation method and medical application thereof |
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| Publication Number | Publication Date |
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| CN108610258A true CN108610258A (en) | 2018-10-02 |
| CN108610258B CN108610258B (en) | 2021-03-19 |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110343045A (en) * | 2019-08-13 | 2019-10-18 | 中国科学院成都生物研究所 | Aryl-tetralin type Lignanoids compounds and preparation and application |
| CN110692702A (en) * | 2019-09-26 | 2020-01-17 | 宁波大学 | Antibacterial agent for inhibiting Shewanella putrefaciens, preparation method thereof and application of antibacterial agent in preparation of litopenaeus vannamei preservative |
| CN117122059A (en) * | 2023-08-29 | 2023-11-28 | 中国海洋大学 | Preparation method and application of antiallergic and anti-inflammatory seaweed polyphenol |
-
2018
- 2018-04-17 CN CN201810343914.6A patent/CN108610258B/en not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110343045A (en) * | 2019-08-13 | 2019-10-18 | 中国科学院成都生物研究所 | Aryl-tetralin type Lignanoids compounds and preparation and application |
| CN110343045B (en) * | 2019-08-13 | 2021-11-12 | 中国科学院成都生物研究所 | Aryltetrahydronaphthalene lignan compound and preparation and application thereof |
| CN110692702A (en) * | 2019-09-26 | 2020-01-17 | 宁波大学 | Antibacterial agent for inhibiting Shewanella putrefaciens, preparation method thereof and application of antibacterial agent in preparation of litopenaeus vannamei preservative |
| CN117122059A (en) * | 2023-08-29 | 2023-11-28 | 中国海洋大学 | Preparation method and application of antiallergic and anti-inflammatory seaweed polyphenol |
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Effective date of registration: 20210319 Address after: No. 27, Shan Dana Road, Ji'nan, Shandong Province, Shandong Patentee after: SHANDONG University Address before: 110000 2-2-2, no.105-3, Wenhua Road, Shenhe District, Shenyang City, Liaoning Province Patentee before: Lu Yilei |
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