CN106565451B - A kind of Chalcone Compounds with antibacterial activity, preparation method and application - Google Patents
A kind of Chalcone Compounds with antibacterial activity, preparation method and application Download PDFInfo
- Publication number
- CN106565451B CN106565451B CN201610898406.5A CN201610898406A CN106565451B CN 106565451 B CN106565451 B CN 106565451B CN 201610898406 A CN201610898406 A CN 201610898406A CN 106565451 B CN106565451 B CN 106565451B
- Authority
- CN
- China
- Prior art keywords
- chalcone
- silica gel
- preparation
- rose
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/36—Biocidal agents, e.g. fungicidal, bactericidal, insecticidal agents
Abstract
The invention discloses a kind of Chalcone Compounds, which is characterized in that has following structural formula:The name of the compound are as follows: dihydroxy -3 2 ', 4-, 4 '-dimethoxy -2- (2- ethoxy)-chalcone, molecular formula C19H20O6, the English name are as follows:-dimethoxy-2- of 2 ', 4-dihydroxyl-3,4 ' (2-hydroxyethyl)-chalcone.The application of bacteria breed and breeding in cigarette tipping paper is eliminated or reduced the invention also discloses the preparation method of the Chalcone Compounds and in cigarette antibiotic package paper.
Description
Technical field
The invention belongs to natural product chemistry technical fields, and in particular to it is a kind of from rose for the first time extract obtain look into
Ear ketone compounds.Meanwhile the invention further relates to the preparation methods of the compound and the application in cigarette antibiotic package paper.
Background technique
Rose (scientific name: Rosa rugosa Thunb.): source area China.The Chinese traditional rose product generally cultivated now
Kind have: bitter water rose (Gansu Province Yongdeng County misery town), Ping Yin Rose (Shandong Province's Pingying County), Damascus series rose and
More than ten kinds such as Rosa centifolia (French kind).The kind cultivated on a large scale in production only has 7-8 kind.Rose is as warp
Help crop when, flower is mainly used for food and refines essence attar of rose, and attar of rose is applied to tobacco, cosmetics, food, fine
The industry such as chemical industry.Contain 300 various chemical components in rose, such as alcohol of fragrance, aldehyde, fatty acid, phenol and oil containing essence and
Rouge, often eats the promoting blood circulation of having a respite with the awake stomach of soft liver in rose product, and beautifying face and moistering lotion makes us refreshing refreshing.Meanwhile rose just the flower opened and
Root can be used as medicine, and have qi-regulating, promoting blood circulation, Thyme Extract, cure mainly irregular menstruation, traumatic injury, irritability stomachache, the diseases such as too fat to move pain of cream.
Chalcone Compounds are a kind of chemical component of Chinese herbal medicine, are before synthesizing flavones and isoflavones in plant
Body, by the α of an open loop flavones in structure, β-insatiable hunger carbonyl system links two aromatic rings compositions.Since chalcone structure has
Biggish flexibility, can be in conjunction with different biological acceptors;Therefore finding from Chalcone Compounds improves cigarette smoking quality
Chemical component prospect it is boundless.The present invention a kind of isolated new Chalcone Compounds, the change from rose
It closes object and relevant report is not yet seen, it is worth mentioning at this point that the compound has significant antibacterial activity.The compound is used
In cigarette tipping paper, a possibility that capable of eliminating or reduce bacteria breed in cigarette tipping paper and breed.
Summary of the invention
The purpose of the present invention is to provide a kind of new Chalcone Compounds.
It is a further object to provide a kind of methods for preparing the Chalcone Compounds.
The object of the invention is also to provide application of the chalcone compounds in antibiotic package paper.
Unless otherwise indicated, percentage employed in the present invention is mass percent.
First aspect present invention is provided isolates a kind of new Chalcone Compounds from rose, and molecular formula is
C19H20O6, there is following structural formula:
The name of the compound are as follows: the name of the compound are as follows: 2 ', 4- dihydroxy -3,4 '-dimethoxy -2- (2- hydroxyl second
Base)-chalcone;English name are as follows: 2 ', 4-dihydroxyl-3,4 '-dimethoxy-2- (2-hydroxyethyl)-
Chalcone is light yellow gum object.
Second aspect of the present invention provides the preparation method of the Chalcone Compounds, method includes the following steps:
(1) medicinal extract extracts: by rose sample comminution, with high concentration methanol (wt%:80%~100%) or high concentration second
Alcohol (wt%:80%~100%) or high concentration acetone (wt%:60%~90%) are Extraction solvent, Extraction solvent: rose
(weight ratio)=2~4:1 impregnates for 24 hours~72h, extracts 3~5 times, combined extract, filtering and concentrating are at medicinal extract;
(2) silica gel column chromatography: the pure methanol or straight alcohol or pure acetone that medicinal extract is measured with 1.5~3 times of weight ratio are used after dissolving
0.8~1.2 times of weight ratio of 80~100 mesh silica gel mixed samples, 160~300 mesh silica gel dry column-packings measured with 2~4 times of weight ratio
Carry out silica gel column chromatography;It take volume proportion as the chloroform-acetone solution of (1:0,20:1,9:1,8:2,7:3,6:4,1:1 and 1:2)
Gradient elution is carried out, identical part is merged, collect each section eluent and is concentrated;
(3) high pressure liquid chromatography isolates and purifies: further using high pressure liquid in the part 7:3 that column chromatographic eluate volume proportion is
Phase chromatographic separation and purification is up to the Chalcone Compounds.
It is using 21.2mm × 250mm, 5 μm of C that high pressure liquid chromatography, which isolates and purifies,18Chromatographic column, flow velocity 20mL/min,
Mobile phase is the methanol of 52wt%, and UV detector Detection wavelength is 352nm, and each 200 μ L of sample introduction collects the color of 30.8min
Spectral peak, the compounds of this invention can be obtained by being evaporated after repeatedly adding up.
The structure for the Chalcone Compounds being in the above way prepared is measured by the following method.Of the present inventionization
Conjunction object is light yellow gum object;HRESI-MS shows that its quasi-molecular ion peak is 367.1164 [M+Na]+, in conjunction with1H and13C NMR
Molecular formula is set to C19H20O6.Its infrared spectroscopy, which is shown in compound, hydroxyl (3398cm-1), carbonyl (1686cm-1) and aromatic ring
(1608,1552 and 1447cm-1) signal, ultraviolet spectra has absorption maximum to also confirm that in compound and exists in 210,250 and 352nm
Aromatic ring structure.Including a quaternary phenyl ring of 1,2,3,4- (C-1~C-6, H-5 and H-6), the disubstituted benzene of 1,4-
Ring (C-1 '~C-6 ', H2- 2 ', 6 ' and H2- 3 ', 5 '), 2- ethoxy structure fragment (C-1 " and C-2 ", a H2- 1 " and H2-
2 ") a, carbonyl carbon (C- χ), one group of double bond (C- α and C- β, H- α and H- β), two methoxyl group (δC61.3q and 56.1q;δH
3.86s and 3.82s) and two phenolic hydroxyl group (δH13.11 10.91).Typical NMR signal (two phenyl ring, carbonyl
And α, β-unsaturated double-bond) and H- α and C-1, C-1', C- χ, C- β, H- β and C-1, C-2, C-6, C- χ, C- α, H2- 6 ' with
Related (figure -3) the susceptible of proof compound of the HMBC of C- χ, H-6 and C- β is Chalcone Compounds.The precursor structure of compound obtains
To after confirmation, remaining signal: 2- ethoxy, two methoxyl groups and two phenolic hydroxyl groups can be identified as the substituent group on parent nucleus.Change
Closing in object can be observed H-1 " (δHAnd C-1 (δ 2.65)C 125.1s)、C-2(δC 126.9s)、C-3(δC146.9s), H-2 "
(δHAnd C-2 (δ 3.60)CHMBC 126.9s) is related, this susceptible of proof 2- ethoxy is substituted in the position C-2 of parent nucleus.According to two
Methoxyl group hydrogen (δH3.83 and 3.80) with C-3 (δCAnd C-4 ' (δ 146.9)C145.5) HMBC is related, it can be verified that two first
Oxygroup is substituted in the position C-3 and C-4 ' of parent nucleus respectively.According to phenolic hydroxyl group hydrogen (δH13.11) with C-1 ' (δC 146.8)、C-2′(δC
And C-3 ' (δ 145.1)C113.4) HMBC correlation can determine that the phenolic hydroxyl group is substituted in C-2, another phenolic hydroxyl group is substituted in
C-4 can be by the phenolic hydroxyl group hydrogen (δH10.82) with C-3 (δC 146.9)、C-4(δCAnd C-5 (δ 145.5)C113.1)
HMBC correlation is confirmed.So far, the structure of the compounds of this invention can be determined, and be named as 2 ', dihydroxy -3 4-, 4 ' -
Dimethoxy -2- (2- ethoxy)-chalcone.
Infrared, the ultraviolet and mass spectrometric data of compound: UV (methanol), λmax(logε)210(3.87)、250(3.15)、352
(3.40), IR (pressing potassium bromide troche) νmax 3398、3115、3067、2960、2845、1686、1608、1552、1447、1351、
1169、1067、869、781cm-1;ESI-MS (positive ion mode) m/z 367 [M+Na]+;HR-ESI-MS (positive ion mode) m/
z[M+Na]+367.1164 (calculated value 367.1158, C19H20NaO6)。
- 1. compound of table1H NMR and13C NMR data (solvent C5D5N)
Antimicrobial Screening is carried out to the compound, to staphylococcus aureus, Escherichia coli, angstrom uncommon bacterium, withered grass
Bacillus, proteus etc. have significant activity.
The compound is applied in cigarette tipping paper to compare with control, and the tipping paper detection for adding this compound is thin
Bacterium sum, coliform, staphylococcus aureus, Pseudomonas aeruginosa, hemolytic streptococcus, total number of fungi substantially reduce;To large intestine
Bacillus (ATCC25922), staphylococcus aureus (ATCC6538) bacteriostasis rate entirely reach 90.8% or more, can reduce or
A possibility that eliminating cigarette tipping paper and during storage bacteria breed and breeding, in addition, in smoking property of cigarette, transmittance process
In, which also can play inhibiting effect to the contaminated microorganism of tipping paper on Cigarette.
Compared with prior art, the invention has the following outstanding advantages: (1) Chalcone Compounds of the invention are for the first time
It obtains;Raw material is easy to get, and extracting method is simple, can be easily separated to obtain;Molecular structure is also simple, easy to accomplish artificial synthesized.(2) it adopts
The preparation method combined with conventional column chromatography and high performance liquid chromatography, compound preparation manipulation process is simple, and obtained
Invention compound purity is high, and subsequent industrialized production is easy to accomplish.(3) the compounds of this invention is nontoxic to animal, and use is safe,
Good antibacterial activity is shown, 90.8% or more is entirely reached to the bacteriostasis rate of Escherichia coli, staphylococcus aureus etc.;It answers
For cigarette tipping paper, inhibiting effect can be played to the contaminated microorganism of cigarette tipping paper.Cigarette tipping paper directly and mouth
Chamber contact, use of the compound in cigarette tipping paper can avoid cigarette suck, microbial contamination in transmittance process,
Effectively increase the health and safety of cigarette.
Detailed description of the invention
Fig. 1 is the carbon-13 nmr spectra of Chalcone Compounds of the present invention;
Fig. 2 is the nuclear magnetic resonance spectroscopy of Chalcone Compounds of the present invention;
Fig. 3 is that the main HMBC of Chalcone Compounds of the present invention is related.
Specific embodiment
The present invention is described in further detail with reference to the accompanying drawings and examples, but not in any way to the present invention
It limits, based on present invention teach that made any transformation or improvement, each fall within protection scope of the present invention.
Embodiment 1
Prepare Chalcone Compounds C19H20O6, including medicinal extract extraction, silica gel column chromatography, high pressure liquid chromatography separation, tool
Body uses following steps:
1. medicinal extract extracts: take rose to crush, with high concentration methanol (wt%:95%) or high concentration ethanol (wt%:
95%) or high concentration acetone (wt%:70%) is Extraction solvent, and Extraction solvent: rose (weight ratio)=3:5 impregnates 54h,
It extracts 4 times, combined extract, filtering and concentrating are at medicinal extract.
2. silica gel column chromatography: the pure methanol or straight alcohol or pure acetone that medicinal extract is measured with 2.5 times of weight ratio use weight after dissolving
80~100 mesh silica gel mixed samples than 1.2 times, the 250 mesh silica gel dry column-packings measured with 3 times of weight ratio carry out silica gel column chromatography;With
Volume proportion is that the chloroform-acetone solution of (1:0,20:1,9:1,8:2,7:3,6:4,1:1 and 1:2) carries out gradient elution, is merged
Identical part is collected each section eluent and is concentrated.
3. high pressure liquid chromatography separates: the part 7:3 of column chromatographic eluate is further isolated and purified with high pressure liquid chromatography
Up to the Chalcone Compounds, it is using 21.2mm × 250mm, 5 μm of C that high pressure liquid chromatography, which isolates and purifies,18Chromatography
Column, flow velocity 20mL/min, mobile phase are the methanol of 52wt%, and UV detector Detection wavelength is 352nm, each 200 μ of sample introduction
L collects the chromatographic peak of 30.8min, is evaporated after repeatedly adding up.
High pressure lipuid chromatography (HPLC) isolate and purify after substance, a preferred post-processing scheme is that gained compound is again
It is dissolved with pure methanol, then using pure methanol as mobile phase, is separated with gel filtration chromatography, further to isolate and purify.
Rose used in the present invention is not limited by area and kind, and the present invention may be implemented, below to derive from Yunnan
The rose of different sources, the present invention will be further described:
Embodiment 2
Rose sample source is in Lijiang, yunnan.Rose sampling 2.0kg is crushed and is extracted 5 times with the methanol of 95wt%,
It extracts every time for 24 hours, extracting solution merges, and filtering is concentrated under reduced pressure into medicinal extract, obtains medicinal extract 105g.Medicinal extract is measured pure with 2.0 times of weight ratio
The thick silica gel mixed sample of 100 mesh of 120g is used after methanol dissolution, the 160 mesh silica gel dress column of 0.6kg carries out silica gel column chromatography, matched with volume
Than the chloroform for 1:0,20:1,9:1,8:2,7:3,6:4,1:1,1:2-acetone gradient elution, TLC monitoring merges identical portion
Point, 8 parts are obtained, chloroform-acetone elution fraction that wherein volume proportion is 7:3 pacifies prompt logical sequence 1,100 half and prepares efficient liquid phase
Chromatographic isolation, using the methanol of 52wt% as mobile phase, it is stationary phase that Zorbax SB-C18 (21.2 × 250mm, 5 μm), which prepares column,
Flow velocity is 20ml/min, and UV detector Detection wavelength is 352nm, and each 200 μ L of sample introduction collects the chromatographic peak of 30.8min, more
It is secondary it is cumulative after be evaporated;Products therefrom is dissolved with pure methanol again, then using pure methanol as mobile phase, with Sephadex LH-20 gel
Column chromatography for separation is to get the noval chemical compound.
Embodiment 3
Rose sample source is extracted rose sampling 3.5kg chopping with the ethyl alcohol of 95wt% in Shangri-La, Yunnan Province
4 times, 48h is extracted every time, and extracting solution merges, and filtering is concentrated under reduced pressure into medicinal extract, obtains medicinal extract 250g.Medicinal extract is measured with 2.0 times of weight ratio
Pure methanol dissolution after use 250g the thick silica gel mixed sample of 80 mesh, 1.2kg 200 mesh silica gel dress column carry out silica gel column chromatography, use body
Product proportion is chloroform-acetone gradient elution of 1:0,20:1,9:1,8:2,7:3,6:4,1:1,1:2, and TLC monitoring merges identical
Part obtains 8 parts, and chloroform-acetone elution fraction that wherein volume proportion is 7:3 pacifies prompt logical sequence 1,100 half and prepares efficient liquid
Phase chromatographic isolation, using the methanol of 52wt% as mobile phase, Zorbax SB-C18 (21.2 × 250mm, 5 μm) prepares column to fix
Phase, flow velocity 20ml/min, UV detector Detection wavelength are 352nm, and each 200 μ L of sample introduction collects the chromatography of 30.8min
Peak is evaporated after repeatedly adding up;Products therefrom is dissolved with pure methanol again, then using pure methanol as mobile phase, with Sephadex LH-
20 gel filtration chromatographies separate to get the noval chemical compound.
Embodiment 4
Rose sample source crushes rose sampling 5kg, in Yunnan Wei Xi with the acetone ultrasonic extraction of 75wt%
3 times, 72h is extracted every time, and extracting solution merges, and filtering is concentrated under reduced pressure into medicinal extract, obtains medicinal extract 380g.Medicinal extract is measured with 1.6 times of weight ratio
Pure methanol dissolution after use 400g the thick silica gel mixed sample of 90 mesh, 2.4kg 180 mesh silica gel dress column carry out silica gel column chromatography, use body
Product proportion is chloroform-acetone gradient elution of 1:0,20:1,9:1,8:2,7:3,6:4,1:1,1:2, and TLC monitoring merges identical
Part obtains 8 parts, and chloroform-acetone elution fraction that wherein volume proportion is 7:3 pacifies prompt logical sequence 1,100 half and prepares efficient liquid
Phase chromatographic isolation, using the methanol of 52wt% as mobile phase, Zorbax SB-C18 (21.2 × 250mm, 5 μm) prepares column to fix
Phase, flow velocity 20ml/min, UV detector Detection wavelength are 352nm, and each 200 μ L of sample introduction collects the chromatography of 30.8min
Peak is evaporated after repeatedly adding up;Products therefrom is dissolved with pure methanol again, then using pure methanol as mobile phase, with Sephadex LH-
20 gel filtration chromatographies separate to get the noval chemical compound.
Embodiment 5
The identification of --- --- compound structure
The compound of Example 1-4 preparation, the structure for the Chalcone Compounds being in the above way prepared pass through
Following methods are measured.The compounds of this invention is light yellow gum object;HRESI-MS shows that its quasi-molecular ion peak is
367.1164[M+Na]+, in conjunction with1H and13Molecular formula is set to C by C NMR19H20O6.Its infrared spectroscopy, which is shown in compound, hydroxyl
(3398cm-1), carbonyl (1686cm-1) and aromatic ring (1608,1552 and 1447cm-1) signal, ultraviolet spectra is in 210,250 and
352nm has absorption maximum to also confirm that there are aromatic ring structures in compound.Including a quaternary phenyl ring of 1,2,3,4- (C-1~
C-6, H-5 and H-6), the disubstituted phenyl ring of 1,4- (C-1 '~C-6 ', H2- 2 ', 6 ' and H2- 3 ', 5 '), a 2- hydroxyl second
Based structures segment (C-1 " and C-2 ", H2- 1 " and H2- 2 "), a carbonyl carbon (C- χ), one group of double bond (C- α and C- β, H- α and H-
β), two methoxyl group (δC61.3q and 56.1q;δH3.86s and 3.82s) and two phenolic hydroxyl group (δH13.11 10.91).
Typical NMR signal (two phenyl ring, carbonyl and α, β-unsaturated double-bond) and H- α and C-1, C-1', C- χ, C- β,
H- β and C-1, C-2, C-6, C- χ, C- α, H2- 6 ' with C- χ, H-6 (scheme -3) susceptible of proof related to the HMBC of the C- β compound is
Chalcone Compounds.After the precursor structure of compound is confirmed, remaining signal: 2- ethoxy, two methoxyl groups and two
A phenolic hydroxyl group can be identified as the substituent group on parent nucleus.H-1 " (δ can be observed in compoundHAnd C-1 (δ 2.65)C 125.1s)、
C-2(δC 126.9s)、C-3(δC146.9s), H-2 " (δHAnd C-2 (δ 3.60)CHMBC 126.9s) is related, this susceptible of proof
2- ethoxy is substituted in the position C-2 of parent nucleus.According to two methoxyl group hydrogen (δH3.83 and 3.80) with C-3 (δCAnd C-4 ' 146.9)
(δC145.5) HMBC is related, it can be verified that two methoxyl groups are substituted in the position C-3 and C-4 ' of parent nucleus respectively.According to phenolic hydroxyl group hydrogen
(δH13.11) with C-1 ' (δC 146.8)、C-2′(δCAnd C-3 ' (δ 145.1)C113.4) HMBC correlation can determine the phenol
Hydroxyl is substituted in C-2, another phenolic hydroxyl group is substituted in C-4 can be by the phenolic hydroxyl group hydrogen (δH10.82) with C-3 (δC
146.9)、C-4(δCAnd C-5 (δ 145.5)C113.1) HMBC correlation is confirmed.So far, the structure of the compounds of this invention
It can be determined, and be named as 2 ', dihydroxy -3 4-, 4 '-dimethoxy -2- (2- ethoxy)-chalcone.
Embodiment 6
Compound prepared by Example 3 is light yellow gum object.Measuring method is same as Example 5, confirms embodiment
The compound of 3 preparations is the Chalcone Compounds --- the name of the compound are as follows: 2 ', 4- dihydroxy -3,4 '-diformazan
Oxygroup -2- (2- ethoxy)-chalcone.
Embodiment 7
Compound prepared by Example 4 is yellow jelly.Measuring method is same as Example 5, confirms embodiment 4
The compound of preparation is the name of the compound are as follows: 2 ', 4- dihydroxy -3,4 '-dimethoxy -2- (2- ethoxy) -
Chalcone.
Embodiment 8
Any Chalcone Compounds of Example 1-4 preparation carry out antibacterial activity test, and test situation is as follows:
Antimicrobial test is carried out with agar diffusion method, and tested bacterium is equably coated in plain agar culture medium (ox first
Meat extract, peptone, sodium chloride, serum, agar) plate on, then by untested compound (benzofuran C prime compound 10mL
DMSO dissolution, is diluted with water into the solution of 50 μ g/mL) soaked tablet (diameter 5mm) is placed on the culture medium to carry disease germs, is put into
In insulating box, inhibition zone size is observed after 25 DEG C of incubation 24-72h.The result shows that: the compounds of this invention is to Staphylococcus aureus
Bacterium, Escherichia coli, angstrom uncommon bacterium, hay bacillus, proteus etc. have very strong activity;Inhibiting rate is more than 90.8%.
Embodiment 9
Safety evaluatio has been carried out to the compounds of this invention, has passed through Micronuclei In The Mouse Bone Marrow experiment, Ames experiment and TK gene
Mutating experiment, it was demonstrated that the compounds of this invention is nontoxic to animal, and use is safe.This compound is added to cigarette with the concentration of 50 μ g/mL
On tipping paper;By the detection method of the People's Republic of China (PRC) " Disposable Sanitary Accessory sanitary standard " GB15979-2002,
Take the volume cigarette tipping paper for adding the compounds of this invention, 2.0 × 3.0mm size, detection bacterium sum, coliform, golden yellow
Staphylococcus, Pseudomonas aeruginosa, hemolytic streptococcus, total number of fungi.The result shows that adding the tipping paper bacterium of the compounds of this invention
It falls sum to significantly reduce, this compound has obvious inhibiting effect to the bacterium of several tests, to Escherichia coli, golden yellow grape
The bacteriostasis rate of coccus etc. entirely reaches 90.8% or more.
Claims (4)
1. a kind of preparation method of Chalcone Compounds, which is characterized in that the Chalcone Compounds have following structures
Formula:
The name of the compound are as follows: dihydroxy -3 2 ', 4-, 4 '-dimethoxy -2- (2- ethoxy)-chalcone, molecular formula are
C19H20O6;English name are as follows: 2 ', 4-dihydroxyl-3,4 '-dimethoxy-2- (2-hydroxyethyl)-chalcone;
The preparation methods of the Chalcone Compounds the following steps are included:
(1) medicinal extract extracts: using Yunnan rose as raw material, rose being crushed, with the methanol of concentration expressed in percentage by weight 80%~100%
Or ethyl alcohol or the acetone of concentration expressed in percentage by weight 60%~90% are Extraction solvent, Extraction solvent: weight ratio=2~4 of rose:
1, for 24 hours~72h is impregnated, is extracted 3~5 times, combined extract, filtering and concentrating are at medicinal extract;
(2) silica gel column chromatography: 160~300 mesh silica gel dry column-packings that medicinal extract is measured with 2~4 times of weight ratio carry out silica gel column chromatography;
Gradient elution is carried out for 1:0,20:1,9:1,8:2,7:3,6:4,1:1 and 1:2 by volume with chloroform-acetone solution, merges phase
Same part is collected each section eluent and is simultaneously concentrated;
(3) high pressure liquid chromatography isolates and purifies: effluent volume ratio is that the part 7:3 is further isolated and purified with high pressure liquid chromatography
Up to required Chalcone Compounds.
2. preparation method according to claim 1, it is characterised in that: in step (3), after high pressure liquid chromatography isolates and purifies
Compound dissolved again with pure methanol, then using pure methanol as mobile phase, separated with gel filtration chromatography, it is pure further to separate
Change.
3. preparation method according to claim 1, it is characterised in that: in step (3), the high pressure liquid chromatography separation
Purifying is using 21.2mm × 250mm, 5 μm of C18Chromatographic column, flow velocity 20mL/min, the methanol that mobile phase is 52% are ultraviolet
Detector Detection wavelength is 352nm, and each 200 μ L of sample introduction collects the chromatographic peak of 30.8min, is evaporated after repeatedly adding up.
4. preparation method according to claim 1, it is characterised in that: in step (2), the medicinal extract is through silica gel column layer
Before analysing rough segmentation, after pure methanol or straight alcohol or the pure acetone dissolution measured with 1.5~3 times of weight ratio, with 0.8~1.2 times of weight ratio
80~100 mesh silica gel mixed samples.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610898406.5A CN106565451B (en) | 2016-10-14 | 2016-10-14 | A kind of Chalcone Compounds with antibacterial activity, preparation method and application |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610898406.5A CN106565451B (en) | 2016-10-14 | 2016-10-14 | A kind of Chalcone Compounds with antibacterial activity, preparation method and application |
Publications (2)
Publication Number | Publication Date |
---|---|
CN106565451A CN106565451A (en) | 2017-04-19 |
CN106565451B true CN106565451B (en) | 2019-02-19 |
Family
ID=58531952
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201610898406.5A Active CN106565451B (en) | 2016-10-14 | 2016-10-14 | A kind of Chalcone Compounds with antibacterial activity, preparation method and application |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN106565451B (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107366194B (en) * | 2017-08-31 | 2019-10-11 | 云南中烟工业有限责任公司 | It is a kind of to have effects that the cigarette paper additive of pharynx-clearing throat-benefiting and its application |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103483211A (en) * | 2013-08-26 | 2014-01-01 | 中南民族大学 | Compound with antibacterial synergism as well as preparation method and application thereof |
CN104337799A (en) * | 2013-07-25 | 2015-02-11 | 中国人民解放军军事医学科学院微生物流行病研究所 | Antibiosis use of licochalcone A |
-
2016
- 2016-10-14 CN CN201610898406.5A patent/CN106565451B/en active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104337799A (en) * | 2013-07-25 | 2015-02-11 | 中国人民解放军军事医学科学院微生物流行病研究所 | Antibiosis use of licochalcone A |
CN103483211A (en) * | 2013-08-26 | 2014-01-01 | 中南民族大学 | Compound with antibacterial synergism as well as preparation method and application thereof |
Non-Patent Citations (2)
Title |
---|
CHALCONES FROM Desmodium podocarpum AND THEIR CYTOTOXICITY;Ying Qin等;《Chemistry of Natural Compounds》;20151130;第51卷(第6期);1062-1065 |
Cytotoxic Chalcones from Desmodium oxyphyllum;Xue-Mei Gao等;《J. Braz. Chem. Soc.,》;20151231;第62卷(第4期);736-740 |
Also Published As
Publication number | Publication date |
---|---|
CN106565451A (en) | 2017-04-19 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN106117138B (en) | A kind of isoquinoline alkaloids bases compound, preparation method and application with antibacterial activity | |
Bannwart et al. | Detection and identification of the plant lignans lariciresinol, isolariciresinol and secoisolariciresinol in human urine | |
N’guessan et al. | In vitro assays for bioactivity-guided isolation of antisalmonella and antioxidant compounds in Thonningia sanguinea flowers | |
Kuiate et al. | Antidermatophytic triterpenoids from Syzygium jambos (L.) Alston (Myrtaceae) | |
CN107501065B (en) | Polysubstituted naphthalene compound with antibacterial activity in aloe and preparation method and application thereof | |
CN107098879A (en) | A kind of isoflavonoid with antibacterial activity and preparation method and application | |
Wang et al. | Isoflavones from green vegetable soya beans and their antimicrobial and antioxidant activities | |
Guvenalp et al. | Two antigenotoxic chalcone glycosides from Mentha longifolia subsp. longifolia | |
CN105924356B (en) | A kind of sesquiterpenoids and its preparation method and application | |
Lee et al. | Chemical constituents of Alnus firma and their inhibitory activity on lipopolysaccharide-induced nitric oxide production in BV2 microglia | |
CN106565654B (en) | A kind of novel flavone compound, Its Preparation Method And Use extracted from Bai Yun Shen | |
CN102267895B (en) | Phenylpropanoid compound as well as preparation method and application thereof | |
CN106565451B (en) | A kind of Chalcone Compounds with antibacterial activity, preparation method and application | |
CN107162891A (en) | A kind of naphthalene compounds extracted from lavender and its preparation method and application | |
Zahoor et al. | HPLC-UV analysis of antioxidants in Citrus sinensis stem and root extracts | |
CN107540532B (en) | Diphenyl ether compound with antibacterial activity in honeysuckle and preparation method and application thereof | |
Thanh Le et al. | Anti‐Inflammatory Lignans from the Roots of Asarum heterotropoides var. mandshuricum and Their Mechanism of Action | |
Milentyeva et al. | Biologically active compounds in Scutellaria baicalensis L. callus extract: Phytochemical analysis and isolation | |
CN107324983A (en) | A kind of multi-substituent naphthalene compounds and its preparation method and application | |
CN111018822B (en) | Compound with bacteriostatic action, preparation method thereof and application thereof in cigarettes | |
CN111777588B (en) | Pseudorufop-gracilis phenylpropanoids compound and application thereof | |
CN105906566B (en) | A kind of alkaloid compound, preparation method and use with antibacterial activity in tobacco | |
CN106187983B (en) | A kind of mouth xanthones compounds and its preparation method and application | |
CN108911958B (en) | Naphthalene formaldehyde compound with antibacterial activity, preparation method thereof and application of compound in cigarette paper | |
CN107721961B (en) | Flavonoid compound extracted from aloe, and preparation method and application thereof |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |