CN106565451A - Chalcones compound with antibacterial activity, preparation method and application thereof - Google Patents
Chalcones compound with antibacterial activity, preparation method and application thereof Download PDFInfo
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- CN106565451A CN106565451A CN201610898406.5A CN201610898406A CN106565451A CN 106565451 A CN106565451 A CN 106565451A CN 201610898406 A CN201610898406 A CN 201610898406A CN 106565451 A CN106565451 A CN 106565451A
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- compound
- silica gel
- chalcone
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- 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
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- 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 chalcones compound, which is characterized by having the following structural formula as shown in the specification; the compound is named as 2',4-dyhydroxyl-3,4'-dimethoxy-2-(2-hydroxyethyl)-chalcone; and the molecular formula of the compound is C19H20O6. The invention also discloses a preparation method of the chalcones compound and an application of the chalcones compound in cigarette antibacterial tipping paper for eliminating or reducing bacteria breeding and propagation in cigarette tipping paper.
Description
Technical field
The invention belongs to natural product chemistry technical field, and in particular to what a kind of extraction first from Flos Rosae Rugosae was obtained looks into
Ear ketone compounds.Meanwhile, the invention further relates to the preparation method of the compound and the application in Medicated cigarette antibiotic package paper.
Background technology
Flos Rosae Rugosae (scientific name：Rosa rugosa Thunb.)：Original producton location China.The Chinese traditional Flos Rosae Rugosae product generally cultivated now
Planting has：Rose grievances (Gansu Province Yongdeng County misery town), Ping Yin Rose (Shandong Province's Pingying County), Damascus series Flos Rosae Rugosae and
More than ten kinds such as Rosa centifolia (French kind).In production, the kind of extensive cultivation only has 7-8 kind.Flos Rosae Rugosae is used as Jing
During Ji crop, its flower is mainly used in food and refines essence Oleum Rosae Rugosae, and Oleum Rosae Rugosae is applied to Nicotiana tabacum L., cosmetics, food, fine
The industry such as chemical industry.Contain 300 various chemical components in Flos Rosae Rugosae, such as the alcohol of fragrance, aldehyde, fatty acid, phenol and the oil containing essence and
Fat, with the awake stomach of easing the affected liver, promoting blood circulation of having a respite, looks improving and the skin nourishing in often to eat Flos Rosae Rugosae product, makes us refreshing refreshing.Meanwhile, the flower opened at the beginning of Flos Rosae Rugosae and
Root can be used as medicine, and have qi-regulating, promoting blood circulation, Thyme Extract, cure mainly menoxenia, traumatic injury, irritability stomachache, the disease such as newborn too fat to move pain.
A class chemical composition of the Chalcone Compounds for Chinese herbal medicine, before synthesizing flavone and isoflavone in plant body
Body, in structure by an open loop flavone α, β-insatiable hunger carbonyl system links two aromatic rings compositions.As chalcone derivative structure has
Larger flexibility, can be combined from different biological acceptors；Therefore finding from Chalcone Compounds improves cigarette smoking quality
Chemical composition prospect it is boundless.The present invention a kind of isolated new Chalcone Compounds, the change from Flos Rosae Rugosae
Compound is not yet seen relevant report, it is worth mentioning at this point that the compound has significant antibacterial activity.The compound is used
In cigarette tipping paper, the probability of bacteria breed and breeding in cigarette tipping paper can be eliminated or reduce.
The content of the invention
It is an object of the invention to provide a kind of new Chalcone Compounds.
It is a further object to provide a kind of method for preparing the Chalcone Compounds.
The present invention also aims to provide application of the chalcone compounds in antibiotic package paper.
Unless otherwise stated, the percent employed in the present invention is mass percent.
First aspect present invention provides and a kind of new Chalcone Compounds is isolated from Flos Rosae Rugosae, and its molecular formula is
C19H20O6, with following structural formula：
The compound is named as：The compound is named as：2 ', 4- dihydroxy -3,4 '-dimethoxy -2- (2- hydroxyl second
Base)-chalcone derivative；English is entitled：2′,4-dihydroxyl-3,4′-dimethoxy-2-(2-hydroxyethyl)-
Chalcone, is light yellow gum thing.
Second aspect present invention provides the preparation method of the Chalcone Compounds, and the method is comprised the following steps：
(1) extractum is extracted：By Flos Rosae Rugosae sample comminution, with high concentration methanol (wt%：80%～100%) or high concentration second
Alcohol (wt%：80%～100%) or high concentration acetone (wt%：60%～90%) it is Extraction solvent, Extraction solvent：Flos Rosae Rugosae
(weight ratio)=2～4:1,24h～72h to be soaked, is extracted 3～5 times, united extraction liquid, filtering and concentrating are into extractum；
(2) silica gel column chromatography：Extractum weight than 1.5～3 times amount pure methanol straight alcohol or pure acetone dissolving after use
80～100 mesh silica gel mixed samples of the weight than 0.8～1.2 times, 160～300 mesh silica gel dry column-packings measured than 2～4 times with weight
Carry out silica gel column chromatography；With volume proportion as (1:0、20:1、9:1、8:2、7:3、6:4、1:1 and 1:2) chloroform-acetone solution
Gradient elution is carried out, merges identical part, collected each several part eluent and concentrate；
(3) high pressure liquid chromatography is isolated and purified：Column chromatography effluent volume proportioning be 7:High pressure liquid is used further in 3 parts
Phase chromatographic separation and purification obtains final product described Chalcone Compounds.
It is 5 μm of the C using 21.2mm × 250mm that high pressure liquid chromatography is isolated and purified18Chromatographic column, flow velocity are 20mL/min,
Methanol of the mobile phase for 52wt%, UV-detector Detection wavelength are 352nm, 200 μ L of each sample introduction, collect the color of 30.8min
Spectral peak, is evaporated after repeatedly adding up and can obtain the compounds of this invention.
The structure of the Chalcone Compounds that method described above is prepared is measured by the following method.The present inventionization
Compound is light yellow gum thing；HRESI-MS shows that its quasi-molecular ion peak is 367.1164 [M+Na]+, with reference to1H and13C NMR
Molecular formula is set to into C19H20O6.Its infrared spectrum has hydroxyl (3398cm in showing compound-1), carbonyl (1686cm-1) and aromatic ring
(1608,1552 and 1447cm-1) signal, ultraviolet spectra has absorption maximum to also confirm that in compound in 210,250 and 352nm and exists
Aromatic ring structure.Including the quaternary phenyl ring (C-1～C-6, H-5 and H-6) of 1,2,3,4-, the dibasic 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 ", 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 is obtained
To after confirmation, remaining signal：2- ethoxys, two methoxyl groups and two phenolic hydroxyl groups can be identified as the substituent group on parent nucleus.Change
H-1 " (δ can be observed in compoundH2.65) with C-1 (δC 125.1s)、C-2(δC 126.9s)、C-3(δC146.9s), H-2 "
(δH3.60) with C-2 (δCHMBC 126.9s) is related, and this susceptible of proof 2- ethoxys are substituted in the C-2 positions of parent nucleus.According to two
Methoxyl group hydrogen (δH3.83 and 3.80) with C-3 (δC146.9) with C-4 ' (δC145.5) HMBC is related, it can be verified that two first
Epoxide is substituted in the C-3 and C-4 ' position of parent nucleus respectively.According to phenolic hydroxyl group hydrogen (δH13.11) with C-1 ' (δC 146.8)、C-2′(δC
145.1) with C-3 ' (δC113.4) HMBC correlations can determine that the phenolic hydroxyl group is substituted in C-2 positions, and another phenolic hydroxyl group is substituted in
C-4 positions can be by phenolic hydroxyl group hydrogen (δH10.82) with C-3 (δC 146.9)、C-4(δC145.5) with C-5 (δC113.1)
HMBC correlations are confirmed.So far, the structure of the compounds of this invention can be determined, and be named as 2 ', 4- dihydroxy -3,4 ' -
Dimethoxy -2- (2- ethoxys)-chalcone derivative.
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 (value of calculation 367.1158, C19H20NaO6)。
- 1. compound of table1H NMR and13(solvent is C to C NMR datas5D5N)
Antimicrobial Screening is carried out to the compound, which is to staphylococcus aureuses, escherichia coli, angstrom uncommon bacterium, hay
Bacillus, Bacillus proteuss etc. have significant activity.
The compound is applied in cigarette tipping paper, is compared with control, and the tipping paper detection for adding this compound is thin
Bacterium sum, coliform, staphylococcus aureuses, bacillus pyocyaneus, Hemolytic streptococcuss, total number of fungi are substantially reduced；To large intestine
Bacillus (ATCC25922), the bacteriostasis rate of staphylococcus aureuses (ATCC6538) entirely reach more than 90.8%, can reduce or
Eliminate cigarette tipping paper and bacteria breed and the probability bred in storage process, in addition, in smoking property of cigarette, transmittance process
In, the antibacterial action also can play inhibitory action to the contaminated microorganism of tipping paper on Cigarette.
Compared with prior art, the present invention has advantage following prominent：(1) Chalcone Compounds of the invention are for first
Obtain；Raw material is easy to get, and extracting method is simple, can be easily separated and obtains；Molecular structure is also simple, easily realizes synthetic.(2) adopt
The preparation method combined with conventional column chromatography and high performance liquid chromatography, compound preparation manipulation flow process are simple, the sheet for being obtained
Invention compound purity is high, and follow-up industrialized production is easily realized.(3) the compounds of this invention is nontoxic to animal, using safety,
Good antibacterial activity is shown, more than 90.8% is entirely reached to the bacteriostasis rate of escherichia coli, staphylococcus aureuses etc.；Should
For cigarette tipping paper, inhibitory action can be played to the contaminated microorganism of cigarette tipping paper.Cigarette tipping paper is directly and mouth
Chamber contacts, use of the compound in cigarette tipping paper can avoid Medicated cigarette sucking, in transmittance process microbial contamination,
Effectively increase health and the safety of Medicated cigarette.
Description of the drawings
Fig. 1 is the carbon-13 nmr spectra of Chalcone Compounds of the present invention；
Fig. 2 is the proton nmr spectra 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 never in any form to the present invention
It is any limitation as, based on present invention teach that any conversion for being made or improvement, each fall within protection scope of the present invention.
Embodiment 1
Prepare Chalcone Compounds C19H20O6, separate including extractum extraction, silica gel column chromatography, high pressure liquid chromatography, tool
Body adopts following steps：
1. extractum is extracted：Flos Rosae Rugosae crushing is taken, with high concentration methanol (wt%：Or high concentration ethanol (wt% 95%)：
Or high concentration acetone (wt% 95%)：70%) it is Extraction solvent, Extraction solvent：Flos Rosae Rugosae (weight ratio)=3:5,54h is soaked,
Extract 4 times, united extraction liquid, filtering and concentrating are into extractum.
2. silica gel column chromatography：Extractum weight than 2.5 times amount pure methanol straight alcohol or pure acetone dissolving after use weight
80～100 mesh silica gel mixed samples than 1.2 times, carry out silica gel column chromatography with 250 mesh silica gel dry column-packings of the weight than 3 times of amounts；With
Volume proportion is (1:0、20:1、9:1、8:2、7:3、6:4、1:1 and 1:2) chloroform-acetone solution carries out gradient elution, merges
Identical part, collects each several part eluent and concentrates.
3. high pressure liquid chromatography is separated：The 7 of column chromatography eluent:3 parts are further isolated and purified with high pressure liquid chromatography
Described Chalcone Compounds are obtained final product, it is 5 μm of the C using 21.2mm × 250mm that high pressure liquid chromatography is isolated and purified18Chromatograph
Post, flow velocity are 20mL/min, and methanol of the mobile phase for 52wt%, UV-detector Detection wavelength are 352nm, 200 μ of each 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 material, a preferred post processing scheme is that gained compound is again
Dissolved with pure methanol, then with pure methanol as mobile phase, separated with gel filtration chromatography, further to isolate and purify.
Used by of the invention, Flos Rosae Rugosae is not limited by area and kind, can realize the present invention, below with from Yunnan
The Flos Rosae Rugosae of different sources, the present invention will be further described：
Embodiment 2
Flos Rosae Rugosae sample source is in Lijiang, yunnan.Flos Rosae Rugosae is sampled into 2.0kg and crushes methanol extraction 5 times with 95wt%,
24h is extracted every time, and extracting solution merges, and filters, and concentrating under reduced pressure obtains extractum 105g into extractum.Extractum weight is purer than 2.0 times of amounts
Use the 160 mesh silica gel dress post of the thick silica gel mixed sample of 100 mesh of 120g, 0.6kg to carry out silica gel column chromatography after methanol dissolving, matched somebody with somebody with volume
Than for 1:0、20:1、9:1、8:2、7:3、6:4、1:1、1:2 chloroform-acetone gradient elution, TLC monitorings merge identical portion
Point, 8 parts are obtained, wherein volume proportion is 7:3 chloroform-acetone elution fraction prepares efficient liquid phase with the prompt logical sequence 1,100 half of peace
Chromatographic isolation, as mobile phase, it is fixing phase that Zorbax SB-C18 (21.2 × 250mm, 5 μm) prepare post to the methanol with 52wt%,
Flow velocity is 20ml/min, and UV-detector Detection wavelength is 352nm, 200 μ L of each sample introduction, collects the chromatographic peak of 30.8min, many
It is secondary it is cumulative after be evaporated；Products therefrom is dissolved with pure methanol again, then with pure methanol as mobile phase, with Sephadex LH-20 gels
Column chromatography for separation, obtains final product the noval chemical compound.
Embodiment 3
Flos Rosae Rugosae sample source, is extracted Flos Rosae Rugosae sampling 3.5kg choppings with the ethanol of 95wt% in Shangri-La, Yunnan Province
4 times, 48h is extracted every time, extracting solution merges, and filters, and concentrating under reduced pressure obtains extractum 250g into extractum.Extractum is measured than 2.0 times with weight
The dissolving of pure methanol after carried out silica gel column chromatography, used body with the thick silica gel mixed sample of 80 mesh of 250g, the 200 mesh silica gel dress post of 1.2kg
Product proportioning is 1:0、20:1、9:1、8:2、7:3、6:4、1:1、1:2 chloroform-acetone gradient elution, TLC monitorings merge identical
Part, obtains 8 parts, and wherein volume proportion is 7:3 chloroform-acetone elution fraction prepares efficient liquid with the prompt logical sequence 1,100 half of peace
Phase chromatographic isolation, as mobile phase, Zorbax SB-C18 (21.2 × 250mm, 5 μm) prepare post to fix to the methanol with 52wt%
Phase, flow velocity are 20ml/min, and UV-detector Detection wavelength is 352nm, 200 μ L of each sample introduction, collects the chromatograph of 30.8min
Peak, is evaporated after repeatedly adding up；Products therefrom is dissolved with pure methanol again, then with pure methanol as mobile phase, uses Sephadex LH-
20 gel filtration chromatographies are separated, and obtain final product the noval chemical compound.
Embodiment 4
Flos Rosae Rugosae sampling 5kg is crushed, with the acetone supersound extraction of 75wt% by Flos Rosae Rugosae sample source in Yunnan Wei Xi
3 times, 72h is extracted every time, extracting solution merges, and filters, and concentrating under reduced pressure obtains extractum 380g into extractum.Extractum is measured than 1.6 times with weight
The dissolving of pure methanol after carried out silica gel column chromatography, used body with the thick silica gel mixed sample of 90 mesh of 400g, the 180 mesh silica gel dress post of 2.4kg
Product proportioning is 1:0、20:1、9:1、8:2、7:3、6:4、1:1、1:2 chloroform-acetone gradient elution, TLC monitorings merge identical
Part, obtains 8 parts, and wherein volume proportion is 7:3 chloroform-acetone elution fraction prepares efficient liquid with the prompt logical sequence 1,100 half of peace
Phase chromatographic isolation, as mobile phase, Zorbax SB-C18 (21.2 × 250mm, 5 μm) prepare post to fix to the methanol with 52wt%
Phase, flow velocity are 20ml/min, and UV-detector Detection wavelength is 352nm, 200 μ L of each sample introduction, collects the chromatograph of 30.8min
Peak, is evaporated after repeatedly adding up；Products therefrom is dissolved with pure methanol again, then with pure methanol as mobile phase, uses Sephadex LH-
20 gel filtration chromatographies are separated, and obtain final product the noval chemical compound.
Embodiment 5
The identification of --- --- compound structure
Compound prepared by Example 1-4, the structure of the Chalcone Compounds that method described above is prepared pass through
Following methods are measured.The compounds of this invention is light yellow gum thing；HRESI-MS shows that its quasi-molecular ion peak is
367.1164[M+Na]+, with reference to1H and13Molecular formula is set to C by C NMR19H20O6.Its infrared spectrum has hydroxyl in showing compound
(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 there is aromatic ring structure in also confirming that compound.Including the quaternary phenyl ring of 1,2,3,4- (C-1～
C-6, H-5 and H-6), 1,4- dibasic phenyl ring (C-1 '～C-6 ', H2- 2 ', 6 ' and H2- 3 ', 5 '), a 2- hydroxyl second
Based structures fragment (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 proofs related to the HMBC of the C- β compounds is
Chalcone Compounds.After the precursor structure of compound is confirmed, remaining signal：2- ethoxys, two methoxyl groups and two
Individual phenolic hydroxyl group can be identified as the substituent group on parent nucleus.H-1 " (δ can be observed in compoundH2.65) with C-1 (δC 125.1s)、
C-2(δC 126.9s)、C-3(δC146.9s), H-2 " (δH3.60) with C-2 (δCHMBC 126.9s) is related, this susceptible of proof
2- ethoxys are substituted in the C-2 positions of parent nucleus.According to two methoxyl group hydrogen (δH3.83 and 3.80) with C-3 (δC146.9) with C-4 '
(δC145.5) HMBC is related, it can be verified that two methoxyl groups are substituted in the C-3 and C-4 ' position of parent nucleus respectively.According to phenolic hydroxyl group hydrogen
(δH13.11) with C-1 ' (δC 146.8)、C-2′(δC145.1) with C-3 ' (δC113.4) HMBC correlations can determine that the phenol
Hydroxyl is substituted in C-2 positions, and another phenolic hydroxyl group is substituted in C-4 positions can be by phenolic hydroxyl group hydrogen (δH10.82) with C-3 (δC
146.9)、C-4(δC145.5) with C-5 (δC113.1) HMBC correlations are confirmed.So far, the structure of the compounds of this invention
Can be determined, and be named as 2 ', 4- dihydroxy -3,4 '-dimethoxy -2- (2- ethoxys)-chalcone derivative.
Embodiment 6
Compound prepared by Example 3, is light yellow gum thing.Assay method is same as Example 5, confirms embodiment
3 compounds for preparing are described Chalcone Compounds --- the compound is named as：- 3,4 '-diformazan of 2 ', 4- dihydroxy
Epoxide -2- (2- ethoxys)-chalcone derivative.
Embodiment 7
Compound prepared by Example 4, is yellow jelly.Assay method is same as Example 5, confirms embodiment 4
The compound of preparation is being named as the described compound：- 3,4 '-dimethoxy -2- of 2 ', 4- dihydroxy (2- ethoxys) -
Chalcone derivative.
Embodiment 8
Arbitrary Chalcone Compounds prepared by Example 1-4 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 (cattle first
Meat extract, peptone, Sodium Chloride, serum, agar) flat board on, then by testing compound (benzofuran C prime compound 10mL
DMSO dissolves, solution of the dilute into 50 μ g/mL) soaked tablet (diameter 5mm) is placed in the culture medium carried disease germs, is put into
In calorstat, observe inhibition zone size after 24-72h being incubated in 25 DEG C.As a result show：The compounds of this invention is to Staphylococcus aureus
Bacterium, escherichia coli, angstrom uncommon bacterium, bacillus subtilis, Bacillus proteuss etc. are with very strong activity；Suppression ratio is more than 90.8%.
Embodiment 9
Safety evaluatio is carried out to the compounds of this invention, by Micronuclei In The Mouse Bone Marrow experiment, Ames experiments and TK genes
Mutating experiment, it was demonstrated that the compounds of this invention is nontoxic to animal, using safety.This compound is added to Medicated cigarette with the concentration of 50 μ g/mL
On tipping paper；By the People's Republic of China (PRC)《Disposable Sanitary Accessory sanitary standard》The detection method of GB15979-2002,
Take the volume cigarette tipping paper for adding the compounds of this invention, 2.0 × 3.0mm sizes, detection bacterium sum, coliform, golden yellow
Staphylococcuses, bacillus pyocyaneus, Hemolytic streptococcuss, total number of fungi.As a result show, added the tipping paper bacterium of the compounds of this invention
The sum that falls is significantly reduced, and this compound has obvious inhibiting effect to the antibacterial of several tests, to escherichia coli, golden yellow Fructus Vitis viniferae
The bacteriostasis rate of coccus etc. entirely reaches more than 90.8%.
Claims (6)
1. a kind of Chalcone Compounds, it is characterised in that with following structural formula：
The compound is named as：2 ', 4- dihydroxy -3,4 '-dimethoxy -2- (2- ethoxys)-chalcone derivative, molecular formula is
C19H20O6；English is entitled：2′,4-dihydroxyl-3,4′-dimethoxy-2-(2-hydroxyethyl)-chalcone.
2. a kind of preparation method of Chalcone Compounds according to claim 1, comprises the following steps：
(1) extractum is extracted:With Yunnan Flos Rosae Rugosae as raw material, Flos Rosae Rugosae is crushed, with the methanol of concentration expressed in percentage by weight 80%～100%
Or ethanol, or the acetone of concentration expressed in percentage by weight 60%～90% be Extraction solvent, Extraction solvent：The weight ratio=2～4 of Flos Rosae Rugosae:
1,24h～72h to be soaked, is extracted 3～5 times, united extraction liquid, filtering and concentrating are into extractum；
(2) silica gel column chromatography：160～300 mesh silica gel dry column-packings of the extractum with weight than 2～4 times of amounts carry out silica gel column chromatography；
With chloroform-acetone solution by volume as 1:0、20:1、9:1、8:2、7:3、6:4、1:1 and 1:2 carry out gradient elution, merge phase
Same part, collects each several part eluent and simultaneously concentrates；
(3) high pressure liquid chromatography is isolated and purified：Effluent volume ratio is 7:3 parts are further isolated and purified with high pressure liquid chromatography
Chalcone Compounds needed for obtaining final product.
3. preparation method according to claim 2, it is characterised in that：In step (3), after high pressure liquid chromatography is isolated and purified
Compound dissolved with pure methanol again, then with pure methanol as mobile phase, separated with gel filtration chromatography, it is pure further to separate
Change.
4. preparation method according to claim 2, it is characterised in that：In step (3), described high pressure liquid chromatography is separated
Purification is 5 μm of the C using 21.2mm × 250mm18Chromatographic column, flow velocity are 20mL/min, and mobile phase is 52% methanol, ultraviolet
Detector Detection wavelength is 352nm, 200 μ L of each sample introduction, collects the chromatographic peak of 30.8min, is evaporated after repeatedly adding up.
5. preparation method according to claim 2, it is characterised in that：In step (2), described extractum is in Jing silica gel column layers
Before analysis rough segmentation, after the pure methanol measured than 1.5～3 times with weight or straight alcohol or pure acetone dissolving, with weight than 0.8～1.2 times
80～100 mesh silica gel mixed samples.
6. the Chalcone Compounds described in claim 1 eliminate or reduce thin in cigarette tipping paper in Medicated cigarette antibiotic package paper
The application that bacterium grows and breeds.
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| CN107366194A (en) * | 2017-08-31 | 2017-11-21 | 云南中烟工业有限责任公司 | A kind of cigarette paper additive and its application with pharynx-clearing throat-benefiting effect |
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