CN114736110B - Anthraquinone compound, preparation method and application thereof - Google Patents
Anthraquinone compound, preparation method and application thereof Download PDFInfo
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- CN114736110B CN114736110B CN202210504647.2A CN202210504647A CN114736110B CN 114736110 B CN114736110 B CN 114736110B CN 202210504647 A CN202210504647 A CN 202210504647A CN 114736110 B CN114736110 B CN 114736110B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/26—Quinones containing groups having oxygen atoms singly bound to carbon atoms
- C07C50/34—Quinones containing groups having oxygen atoms singly bound to carbon atoms the quinoid structure being part of a condensed ring system having three rings
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
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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
Abstract
The invention discloses an anthraquinone compound, a preparation method and application thereof, wherein the anthraquinone compound is separated from traditional Chinese medicinal material aloe, and is named as: 5-methoxy-3-hydroxy-2,6-dimethyl anthraquinone with molecular formula of C 17 H 14 O 4 . The preparation method of the anthraquinone compound takes aloe as a raw material and comprises the steps of extract extraction, silica gel column chromatography and high performance liquid chromatography separation. The anthraquinone compound has a good antibacterial effect, and can obviously reduce the possibility of bacterial breeding and reproduction in the cigarette tipping paper when being used on the cigarette tipping paper. The preparation method of the anthraquinone compound is simple, and the obtained anthraquinone compound has high purity and is very suitable for industrial production.
Description
Technical Field
The invention belongs to the technical field of phytochemistry, and particularly relates to an anthraquinone compound, a preparation method and application thereof.
Background
Aloe vera (Aloe vera) is a perennial evergreen succulent herb of the family Liliaceae. Aloe is native in Mediterranean sea and Africa, is an ornamental plant with both flowers and leaves, and is popular among the public. According to the examination, the wild aloe variety is more than 300, but the edible variety is only six, and the aloe variety with medicinal value mainly comprises: aloe vera, aloe ferox, aloe vera, etc. Aloe is a new plant star integrating edible, medicinal, beautifying and ornamental functions. The secretion (main active ingredient is anthraquinone substances such as aloin) has been widely used in medicine and daily chemicals. Aloe is used in china as a natural medicine for beauty, hair care and treatment of skin diseases. The aloe contains 160 or more components such as anthraquinone, polysaccharide, fatty acid, protein, amino acid, vitamin, mineral, etc., and has very outstanding nutritive value. The national food and agricultural organization of the united nations praise aloe as one of the best health care foods for people in the 21 st century, and the international food code lists aloe as vegetables. Particularly, in the 60 s of the 20 th century, aloe is widely used in various foods as research and development of aloe foods is continued, and is popular with consumers, and the main edible countries are united states, japan, korea and europe.
Anthraquinone compounds are the most abundant of various natural quinone compounds. Anthraquinone has long been used as a natural dye and has been found to have many medicinal values in the future and has been of great interest. Plants of Rubiaceae, rhamnaceae, leguminosae (mainly semen lablab album), lobeliae, zicanaceae, verbenaceae, scrophulariaceae, and Liliaceae all contain abundant anthraquinone compounds; in addition, anthraquinone compounds are also present in the metabolites of lower plant lichens and fungi. Modern phytochemistry and pharmacology research show that anthraquinone compounds have various effects of stopping bleeding, resisting bacteria, purging, resisting viruses, resisting cancers, protecting liver, promoting bile flow, improving eyesight, resisting aging and the like. In addition, due to the outstanding ultraviolet-proof effect of the anthraquinone compounds, the anthraquinone compounds can be added into skin care cosmetics, and the content and the properties of the anthraquinone compounds in the cosmetics can be detected to evaluate the content of effective components in the skin care cosmetics and the beauty and health care effects. The natural anthraquinone compounds have various structures, and more active compounds can be further researched and developed by researching the structure-activity relationship of the compounds, so that effective lead compounds and active groups can be searched. The invention separates new anthraquinone compound from aloe, the compound has not been reported so far, and the compound has remarkable antibacterial activity. The compound is used in cigarette tipping paper, and can prevent bacteria from breeding and reproducing in the cigarette tipping paper.
Disclosure of Invention
The invention separates a new anthraquinone compound from traditional Chinese medicinal material aloe, and the compound has not been reported so far.
The percentages used in the present invention are mass percentages unless otherwise indicated.
In a first aspect, the present invention provides an anthraquinone compound having the formula C 17 H 14 O 4 And has the following structure:
the compound was a red gum, named: 5-methoxy-3-hydroxy-2,6-dimethyl anthraquinone, the English name is: 5-methoxy-3-hydroxy-2,6-dimethyl-anthraquinone.
The second aspect of the present invention provides a method for preparing the anthraquinone compound according to the first aspect, which uses aloe as a raw material, and comprises the steps of extract extraction, silica gel column chromatography and high performance liquid chromatography separation preparation, and specifically comprises:
A. extracting extract: pulverizing aloe to 20-40 meshes, ultrasonically extracting with organic solvent for 2-5 times each for 30-60 min, mixing the extractive solutions, filtering, concentrating the extractive solution under reduced pressure, standing, filtering to remove precipitate, and concentrating to obtain extract;
B. silica gel column chromatography: loading the extract obtained in the step A into a column by using 160-200 mesh silica gel dry method, and performing silica gel column chromatography; the mass ratio of the silica gel to the extract is 6-10; gradient eluting with chloroform-acetone solution with volume ratio of 20:1,9:1,8:2,7:3,6:4, and 1:1, collecting eluate, concentrating, detecting by TLC, and mixing the same parts;
C. high performance liquid chromatography separation: and B, eluting the chloroform-acetone solution with the volume ratio of 7:3, and separating and purifying by high performance liquid chromatography, wherein the high performance liquid chromatography is carried out by taking a 52wt% methanol solution as a mobile phase, the flow rate is 20mL/min, adopting a 21.2X250 mm,5 mu m Zorbax PrepHT GF reversed phase preparation column as a stationary phase, detecting the wavelength by an ultraviolet detector to 398nm, injecting 150-300 mu L each time, collecting chromatographic peaks for 36.8min, accumulating for multiple times, and evaporating to dryness to obtain the anthraquinone compound.
Preferably, in the step C, the second eluent is 200. Mu.L per sample injection.
Preferably, the organic solvent in the step A is 70-100% of acetone, 90-100% of ethanol or 90-100% of methanol.
Preferably, the extract in the step B is dissolved by acetone or methanol which is 1.5 to 3 times of the weight of the extract before the silica gel column chromatography, and then 80 to 100 meshes of silica gel which is 0.8 to 1.2 times of the weight of the extract is used for mixing samples.
In a third aspect the present invention provides the use of an anthraquinone compound according to the first aspect as an antibacterial agent.
Preferably, the anthraquinone compound according to the third aspect of the present invention can be applied to cigarette tipping paper.
Specifically, the use of the third aspect of the present invention is achieved by screening the anthraquinone compounds for antibacterial activity, which have remarkable activities on escherichia coli, staphylococcus aureus, escherichia coli, pseudomonas aeruginosa, bacillus subtilis, proteus, streptococcus hemolyticus and the like. Compared with the cigarette tipping paper without the anthraquinone compound, the total number of coliform bacteria, staphylococcus aureus, escherichia, pseudomonas aeruginosa, bacillus subtilis, bacillus proteus and hemolytic streptococcus detected by the cigarette tipping paper with the anthraquinone compound is obviously reduced; the antibacterial rate to colibacillus, staphylococcus aureus and the like is over 93.5 percent, and the possibility of breeding and reproducing bacteria of the cigarette tipping paper can be obviously reduced. In addition, in the smoking and transferring process of the cigarettes, the microbial contamination of tipping paper on the cigarettes can be inhibited.
The aloe disclosed by the invention is not limited by regions and varieties, and can be realized.
The invention has the following beneficial effects:
compared with the prior art, the invention has the following outstanding advantages:
(1) The anthraquinone compound disclosed by the invention is nontoxic to animals, safe to use, and good in antibacterial activity, and the antibacterial rate of the anthraquinone compound on escherichia coli, staphylococcus aureus and the like is over 93.5%, so that the possibility of breeding and reproducing bacteria of cigarette tipping paper can be obviously reduced. The compound is applied to the tipping paper of cigarettes, and plays a role in inhibiting microbial contamination of the tipping paper on cigarettes. The compound can be used in the cigarette tipping paper to avoid microbial contamination during smoking and transferring of cigarettes because the cigarette tipping paper is in direct contact with the oral cavity.
(2) The anthraquinone compound is obtained by first extraction from the traditional Chinese medicinal material aloe, the raw materials of the compound are easy to obtain, the extraction method is simple, the anthraquinone compound is easy to separate and obtain, the molecular structure of the obtained anthraquinone compound is also simpler, and the artificial synthesis is easy to realize.
(3) The invention adopts the preparation method combining the conventional column chromatography and the high performance liquid chromatography, the preparation operation flow is simple, the purity of the obtained anthraquinone compounds is high, and the subsequent industrialized production is easy to realize.
Drawings
FIG. 1 shows nuclear magnetic resonance spectrum of anthraquinone compounds according to the invention 13 C NMR) map.
FIG. 2 shows the hydrogen nuclear magnetic resonance spectrum of anthraquinone compounds according to the invention 1 H NMR) map.
FIG. 3 is a diagram showing the correlation of critical HMBC based on anthraquinone compounds according to the present invention.
Detailed Description
The technical scheme of the invention is further described below.
Example 1
Taking 4.2kg of dried aloe, coarsely pulverizing to 30 meshes, ultrasonically extracting with 70% acetone solution for 4 times each for 60 minutes, mixing the extractive solutions, filtering, and concentrating under reduced pressure to 1/4 of the volume. Standing, filtering out precipitate, and concentrating to obtain 126g extract; adding 260g of acetone into the extract for dissolution, then adding 140g of 100-mesh silica gel for sample mixing, and filling 650g of 200-mesh silica gel into a column after sample mixing; gradient eluting with chloroform-acetone solution with volume ratio of 20:1,9:1,8:2,7:3,6:4 and 1:1 respectively, collecting gradient eluent, concentrating, detecting by TLC, combining the same parts to obtain 6 parts A-F, wherein the collected 22.5g D part sample (chloroform-acetone solution with volume ratio of 7:3) is separated and purified by high performance liquid chromatography with 52% methanol as mobile phase, zorbax PrepHT GF reversed phase preparation column with flow rate of 20ml/min, 21.2X105 mm and 5 μm is adopted as stationary phase, ultraviolet detector detection wavelength is 398nm, 200 μl of chromatographic peak is collected for 36.8min each time, and evaporating to dryness after multiple accumulation to obtain anthraquinone compound.
Example 2
Taking 4.8kg of dried aloe, coarsely pulverizing to 35 meshes, ultrasonically extracting with 70% acetone for 4 times each for 50 minutes, mixing the extractive solutions, filtering, and concentrating under reduced pressure to 1/4 of the volume. Standing, filtering out precipitate, and concentrating into 148g extract; adding 300g of acetone into the extract for dissolution, then adding 1150g of 100-mesh silica gel for sample mixing, and filling the mixture into a column by using 900g of 200-mesh silica gel after sample mixing; gradient eluting with ketone solutions with volume ratios of 20:1,9:1,8:2,7:3,6:4 and 1:1 respectively, collecting gradient eluent, concentrating, detecting by TLC, combining the same parts to obtain 6 parts A-F, wherein the collected 26.5g D part samples (volume ratio of chloroform-acetone solution is 7:3), separating and purifying with high performance liquid chromatography with 52% methanol as mobile phase, adopting Zorbax PrepHT GF reversed phase preparation column with flow rate of 20ml/min,21.2×250mm and 5 μm as stationary phase, detecting wavelength by ultraviolet detector to sample 200 μl each time, collecting chromatographic peaks of 36.8min, and evaporating after multiple accumulation to obtain anthraquinone compounds.
Example 3
The structure of the anthraquinone compound prepared by the method is determined by the following method:
the anthraquinone compound prepared by the invention is red jelly, and HRESI-MS shows that the excimer ion peak is 305.0783[ M+Na ]] + (calculated 305.0790), combined with 1 H NMR and DEPT spectra, molecular formula C is determined 17 H 14 O 4 The unsaturation was 11. The IR spectrum shows hydroxyl groups (3409 cm -1 ) Carbonyl (1666 cm) -1 ) And aromatic rings (1615, 1549 and 1442 cm) -1 ) Is a resonance absorption peak of (2). The maximum absorption of the ultraviolet spectrum at 215, 248, 276, 398nm also illustrates the possible presence of aromatic ring structures in the compounds.
Of compounds 1 H and 13 c NMR spectrum (Table-1) shows that it contains 17 carbons and 14 hydrogens, including two benzene rings (C1-C8, C-1a, C-4a, C-9a and C-10a; H-1, H-4, H-7 and H-8), two carbonyl groups (C-9 and C-10), two methyl groups (C-11H 3 -11；C-12，H 3 -12), a methoxy group (delta) C 61.2q；δ H 3.80 s), and a phenolic hydroxyl group (delta) H 11.28). According to the characteristic signals of two benzene rings and two carbonyl groups, and the correlation of H-1 and C-1a, C-4a, C-9,H-4 and C-1a, C-4a and C-10 and the correlation of H-8 and HMBC of C-9, C-9a and C-10a in the HMBC correlation spectrum, the compound can be fully determined to be an anthraquinone compound. Other NMR signals: methyl, methoxy and phenolic hydroxyl groups can be identified as substituents on the anthraquinone parent nucleus.
According to methyl hydrogen (H) 3 -11) the methyl substitution was determined at the C-2 position of the anthraquinone parent nucleus in connection with HMBC of C-1, C-2, C-3. According to another methyl hydrogen (H) 2 -12) in connection with HMBC of C-5, C-6, C-7, it can be determined that another methyl substitution is at the C-6 position of the anthraquinone parent nucleus. According to methoxy hydrogen (delta) H 3.80 s) and HMBC related to C-5 can determine that the methoxy group is substituted at C-5. Furthermore, according to the phenolic hydroxyl hydrogen (delta) H 11.28 s) can determine the phenolic hydroxyl group extraction in relation to HMBC of C-2, C-3, C-4Substituted at the C-3 position.
To this end, the structure of the compound was determined and named: 5-methoxy-3-hydroxy-2,6-dimethyl anthraquinone.
TABLE-1 Compounds of the invention 1 H NMR 13 C NMR data (CDCl 3)
Infrared, ultraviolet and mass spectral data for the compounds: UV (methanol), lambda max (log ε) 215 (4.14), 248 (3.78), 276 (3.62), 398 (3.08) nm; IR (potassium bromide tablet): v (v) max 3409、3050、2958、1666、1615、1549、1442、1327、1165、1042、828cm -1 ； 1 H and 13 c NMR data (500 and 125MHz, (C) 5 D 5 N) is shown in Table-1; positive ion mode ESIMS m/z 305[ M+Na ]] + The method comprises the steps of carrying out a first treatment on the surface of the Positive ion mode HRESIMS m/z 305.0783[ M+Na ]] + (calculated 305.0790, C) 17 H 14 NaO 4 )。
Example 4
Anthraquinone compound prepared in example 1 was taken as red gum. The measurement was carried out in the same manner as in example 3, and it was confirmed that the compound produced in example 1 was the anthraquinone compound-5-methoxy-3-hydroxy-2, 6-dimethyl anthraquinone.
Example 5
Anthraquinone compound prepared in example 2 was taken as red gum. The measurement was carried out in the same manner as in example 3, and it was confirmed that the compound produced in example 2 was the anthraquinone compound-5-methoxy-3-hydroxy-2, 6-dimethyl anthraquinone.
Example 6
An antibacterial activity test was performed on any anthraquinone compound prepared in examples 1 and 2, and the test conditions were as follows:
the in vitro antibacterial experiment is carried out by an agar diffusion method, firstly, the bacteria to be tested are uniformly coated on a flat plate of a common agar culture medium (beef extract, peptone, sodium chloride, serum and agar), then, the anthraquinone compound solution (the anthraquinone compound is dissolved by 10mL of DMSO and diluted into 50 mug/mL of solution by adding water) is soaked into a tablet (the diameter is 5 mm), the tablet is placed on the culture medium with bacteria, and the culture medium is placed in an incubator and incubated at 25 ℃ for 24-72 hours, and then the size of a bacteriostasis zone is observed. The results show that: the anthraquinone compound has strong activity on staphylococcus aureus, escherichia coli, bacillus subtilis, proteus, hemolytic streptococcus and the like, and the inhibition rate is more than 95.4 percent.
Example 7
The safety of the compound is evaluated, and the toxicity of the anthraquinone compound to animals and the safety of the anthraquinone compound are proved by a mouse bone marrow micronucleus experiment, an Ames experiment and a TK gene mutation experiment.
The anthraquinone compound is added to cigarette tipping paper at the concentration of 50 mug/mL, and the total number of staphylococcus aureus, escherichia coli, bacillus subtilis, proteus and hemolytic streptococcus is detected according to the detection of the disposable hygienic products hygienic Standard GB15979-2002 of the people's republic of China, and the tipping paper for cigarettes with the size of 2.0 multiplied by 3.0mm, to which the anthraquinone compound is added. Meanwhile, the total number of tipping paper staphylococcus aureus, escherichia coli, bacillus subtilis, bacillus proteus and hemolytic streptococcus for cigarettes with the size of 2.0 multiplied by 3.0mm without adding the anthraquinone compound is detected.
The detection result shows that compared with the cigarette tipping paper without the anthraquinone compound, the total number of coliform bacteria, staphylococcus aureus, escherichia coli, pseudomonas aeruginosa, bacillus subtilis, proteus and hemolytic streptococcus detected by the cigarette tipping paper with the anthraquinone compound has obviously reduced, and the antibacterial rate of the cigarette tipping paper with the anthraquinone compound reaches more than 93.5 percent on escherichia coli, staphylococcus aureus, escherichia coli, pseudomonas aeruginosa, bacillus subtilis, proteus, hemolytic streptococcus and the like. Therefore, the anthraquinone compound disclosed by the invention is added to the cigarette tipping paper, so that the possibility of bacterial breeding and reproduction of the cigarette tipping paper can be obviously reduced.
The foregoing is merely illustrative of the present invention, and the present invention is not limited thereto, and any changes or substitutions easily contemplated by those skilled in the art within the scope of the present invention should be included in the scope of the present invention.
Claims (7)
1. An anthraquinone compound, characterized in that the molecular formula of the compound is C 17 H 14 O 4 And has the following structure:
the compound was a red gum, named: 5-methoxy-3-hydroxy-2,6-dimethyl anthraquinone.
2. A method for producing the anthraquinone compound according to claim 1, comprising the steps of:
A. extracting extract: pulverizing aloe to 20-40 meshes, ultrasonically extracting with organic solvent for 2-5 times each for 30-60 min, mixing the extractive solutions, filtering, concentrating the extractive solution under reduced pressure, standing, filtering to remove precipitate, and concentrating to obtain extract;
B. silica gel column chromatography: loading the extract obtained in the step A into a column by using 160-200 mesh silica gel dry method, and performing silica gel column chromatography; the mass ratio of the silica gel to the extract is 6-10; gradient eluting with chloroform-acetone solution with volume ratio of 20:1,9:1,8:2,7:3,6:4, and 1:1, collecting eluate, concentrating, detecting by TLC, and mixing the same parts;
C. high performance liquid chromatography separation: and B, eluting the chloroform-acetone solution with the volume ratio of 7:3, and separating and purifying by high performance liquid chromatography, wherein the high performance liquid chromatography is carried out by taking a 52wt% methanol solution as a mobile phase, the flow rate is 20mL/min, adopting a 21.2X250 mm,5 mu m Zorbax PrepHT GF reversed phase preparation column as a stationary phase, detecting the wavelength by an ultraviolet detector to 398nm, injecting 150-300 mu L each time, collecting chromatographic peaks for 36.8min, accumulating for multiple times, and evaporating to dryness to obtain the anthraquinone compound.
3. The method for preparing anthraquinone compounds according to claim 2, wherein the organic solvent in the step a is 70-100% by mass of acetone, 90-100% by mass of ethanol or 90-100% by mass of methanol.
4. The method for preparing anthraquinone compounds according to claim 2, wherein the extract in the step B is dissolved in 1.5 to 3 times of acetone or methanol by weight of the extract before silica gel column chromatography, and then is stirred with 80 to 100 mesh silica gel by 0.8 to 1.2 times of the extract by weight.
5. The method for preparing anthraquinone compounds according to claim 2, wherein in the step C, the eluent is 200 μl per sample injection.
6. Use of the anthraquinone compound according to claim 1 as an antibacterial agent for the purpose of non-disease diagnosis and treatment.
7. Use of an anthraquinone compound according to claim 1 added to cigarette tipping paper for reducing bacterial growth and proliferation of the cigarette tipping paper.
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