CN111875651B - Monoterpene glycoside compound, preparation method thereof and application thereof in resisting pathogenic bacteria - Google Patents
Monoterpene glycoside compound, preparation method thereof and application thereof in resisting pathogenic bacteria Download PDFInfo
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- 229930003658 monoterpene Natural products 0.000 title claims abstract description 24
- 235000002577 monoterpenes Nutrition 0.000 title claims abstract description 24
- -1 Monoterpene glycoside compound Chemical class 0.000 title claims abstract description 22
- 229930182470 glycoside Natural products 0.000 title claims abstract description 21
- 244000052616 bacterial pathogen Species 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 241000366182 Melaleuca alternifolia Species 0.000 claims description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 239000000284 extract Substances 0.000 claims description 10
- 239000012046 mixed solvent Substances 0.000 claims description 10
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 7
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 claims description 6
- 239000003208 petroleum Substances 0.000 claims description 6
- 229920005654 Sephadex Polymers 0.000 claims description 5
- 239000012507 Sephadex™ Substances 0.000 claims description 5
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 claims description 5
- 238000004440 column chromatography Methods 0.000 claims description 5
- 238000007865 diluting Methods 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 5
- 244000063299 Bacillus subtilis Species 0.000 claims description 4
- 235000014469 Bacillus subtilis Nutrition 0.000 claims description 4
- 241000588724 Escherichia coli Species 0.000 claims description 4
- 241000193755 Bacillus cereus Species 0.000 claims description 3
- 241000191963 Staphylococcus epidermidis Species 0.000 claims description 3
- 239000003480 eluent Substances 0.000 claims description 3
- 239000002024 ethyl acetate extract Substances 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 3
- 238000010898 silica gel chromatography Methods 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 claims description 2
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 claims description 2
- 230000002829 reductive effect Effects 0.000 claims description 2
- 238000003745 diagnosis Methods 0.000 claims 1
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 abstract description 12
- 241000894006 Bacteria Species 0.000 abstract description 10
- 239000003814 drug Substances 0.000 abstract description 8
- 229940079593 drug Drugs 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 4
- 230000001775 anti-pathogenic effect Effects 0.000 abstract description 2
- 230000003115 biocidal effect Effects 0.000 abstract description 2
- 229940125904 compound 1 Drugs 0.000 description 13
- 229940125782 compound 2 Drugs 0.000 description 12
- 239000000243 solution Substances 0.000 description 8
- 230000000844 anti-bacterial effect Effects 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000008103 glucose Substances 0.000 description 5
- 239000001963 growth medium Substances 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 150000005179 3,4,5-trihydroxybenzoic acids Chemical class 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 150000002773 monoterpene derivatives Chemical class 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000001717 pathogenic effect Effects 0.000 description 2
- XILIYVSXLSWUAI-UHFFFAOYSA-N 2-(diethylamino)ethyl n'-phenylcarbamimidothioate;dihydrobromide Chemical class Br.Br.CCN(CC)CCSC(N)=NC1=CC=CC=C1 XILIYVSXLSWUAI-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000378467 Melaleuca Species 0.000 description 1
- 241000219926 Myrtaceae Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000005452 food preservative Substances 0.000 description 1
- 235000019249 food preservative Nutrition 0.000 description 1
- 238000003919 heteronuclear multiple bond coherence Methods 0.000 description 1
- 238000002114 high-resolution electrospray ionisation mass spectrometry Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010677 tea tree oil Substances 0.000 description 1
- 229940111630 tea tree oil Drugs 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
-
- 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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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Saccharide Compounds (AREA)
Abstract
The invention discloses a monoterpene glycoside compound, a preparation method and application thereof in resisting pathogenic bacteria, wherein the structural formula of the monoterpene glycoside compound is shown as the following, wherein R 1 、R 2 、R 3 、R 4 Independently selected from-H or 3,4, 5-trihydroxybenzoic acid. The invention discovers that the monoterpene glycoside compound has obvious and broad-spectrum anti-pathogenic bacteria activity for the first time, and can be used for preparing antibiotic medicines.
Description
Technical Field
The invention relates to the technical field of phytochemistry, in particular to a monoterpene glycoside compound extracted and separated from melaleuca alternifolia leaves, a preparation method thereof and application thereof in resisting pathogenic bacteria.
Background
Melaleuca alternifolia (academic name: melaleuca alternifolia (Maiden & Betche) Cheel) is a plant of the genus Melaleuca of the family Myrtaceae. Is native to the 23.5 DEG coastal region of the south latitude of Australia and the north part of the northern area. At present, there are cultivation in Hainan, guangdong, guangxi, chongqing and the like of China. Melaleuca alternifolia is an economic crop with higher economic value, and the fresh branches and leaves of melaleuca alternifolia can extract essential oil, namely tea tree oil. It can kill fungi and bacteria on the skin surface of human body with high efficiency, no toxicity and no irritation, and has inhibiting effect on certain viruses, so that it can be widely used in medicine, food preservative, cosmetics, skin care and health care products. Monoterpene glycoside compounds isolated from melaleuca alternifolia plants have been reported, but the novel compounds obtained are few and have no anti-pathogenic activity.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to extract novel monoterpene glycoside compounds from melaleuca alternifolia and further research the antibacterial efficacy of the monoterpene glycoside compounds.
The technical scheme adopted by the invention is as follows:
in one aspect, the invention provides a monoterpene glycoside compound with a structural general formula as follows:
wherein R is 1 、R 2 、R 3 、R 4 Independently selected from-H or 3,4, 5-trihydroxybenzoic acid.
Preferably, R 1 Is 3,4, 5-trihydroxybenzoic acid, R 2 Is 3,4, 5-trihydroxybenzoic acid, R 3 is-H, R 4 is-H; the structural formula is as follows:
preferably, R 1 Is 3,4, 5-trihydroxybenzoic acid, R 2 is-H, R 3 is-H, R 4 is-H; the structural formula is as follows:
on the other hand, the invention also provides the application of the monoterpene glycoside compound in resisting pathogenic bacteria, and the application does not aim at diagnosing and treating diseases. The pathogenic bacteria are preferably bacteria. The pathogenic bacteria are more preferably staphylococcus albus, escherichia coli, bacillus cereus, staphylococcus aureus or bacillus subtilis.
In addition, the invention also provides a preparation method of the monoterpene glycoside compound, which comprises the following steps:
(1) Extracting melaleuca alternifolia branch and leaf powder with ethanol water with the volume percentage of 30-95% to obtain an extracting solution, and concentrating the extracting solution under reduced pressure to form paste to obtain melaleuca alternifolia extract;
(2) Diluting the melaleuca alternifolia extract obtained in the step (1) with water to form a suspension, sequentially extracting with petroleum ether and ethyl acetate, concentrating the ethyl acetate extract to obtain an extract, performing silica gel column chromatography with a petroleum ether-ethyl acetate mixed solvent and an ethyl acetate-methanol mixed solvent according to increasing polarity, and collecting fractions; combining the similar streams into 8 components, fr.1-Fr.8; and (3) performing Sephadex column chromatography on Fr.5, preparing by using a high performance liquid phase, and eluting with acetonitrile water to obtain the compound 1 and the compound 2.
Preferably, in the step (1), the volume percentage of the ethanol water is 70 percent, and the ethanol water is leached for 3 to 4 times, each time for 6 to 7 days.
Preferably, in the step (2), the volume percentage of acetonitrile water is 30-35%.
Preferably, the eluent of the sephadex column chromatography is chloroform-methanol mixed solvent with the volume ratio of 50:50.
The invention has the beneficial effects that:
the invention obtains the novel monoterpene glycoside compound, discovers that the monoterpene glycoside compound has the activity of resisting pathogenic bacteria for the first time, and can be used for preparing antibiotics.
Drawings
Fig. 1: compound 1 structural formula
Fig. 2: compound 2 structural formula
Fig. 3: compound 1 hydrogen spectrum
Fig. 4: carbon spectrum of Compound 1
Fig. 5: carbon spectrum of Compound 2
Detailed Description
In order to better understand the technical content of the present invention, the following provides specific examples to further illustrate the present invention.
Example 1:
preparation of monoterpene glycoside compounds:
(1) 3Kg of melaleuca alternifolia branch and leaf powder is taken, ethanol with the concentration of 70% v/v is used for leaching for 3 times and 7 days each time to obtain an extracting solution, and the extracting solution is decompressed and concentrated into paste to obtain 320g of melaleuca alternifolia extract;
(2) Diluting the melaleuca alternifolia extract with water to obtain a suspension, sequentially extracting with petroleum ether and ethyl acetate, concentrating the ethyl acetate extract to obtain an extract, performing silica gel column chromatography (200-300 meshes) with mixed solvent of petroleum ether and ethyl acetate (100:0-0:100, V/V) and mixed solvent of ethyl acetate and methanol (100:0-0:100, V/V) according to increasing polarity, and collecting fractions about 500mL each time. The similar fractions were combined by TLC (10% chloroform-methanol mixed solvent as developing solvent) and separated into 8 components, fr.1-8. Fr.5 Sephadex column chromatography (Sephadex LH-20), eluting with chloroform-methanol (50:50, V/V); and then respectively preparing the materials by using a high performance liquid phase [ instrument is: agilent 1260 LC services; the column model is: agilent Eclipse XDB-C18 column (9.4X250 mm,5 μm) ], with 30% by volume of acetonitrile water as eluent, to give compound 1 (8 mg) and compound 2 (10 mg).
The structure of the 2 compounds was identified as follows:
compound 1: in the form of white powder, the optical rotation is [ alpha ]] 2 D 5 +15.6(c＝0.2,MeOH)，HR-ESI-MS m/z 635.1988[M-H] - Is combined with 1 H-NMR 13 The C NMR shows that the molecular formula is C 30 H 36 O 15 The calculated unsaturation was 13. According to 1 H, 13 The C-NMR and DEPT compounds are known to consist of one glucose, two 3,4, 5-trihydroxybenzoic acids and one monoterpene. From HMBC, it is known that: the hydrogens at positions 4 and 6 of glucose are respectively related to the carboxyl carbon of two 3,4, 5-trihydroxybenzoic acids, which indicates that the two 3,4, 5-trihydroxybenzoic acids are respectively connected at positions 4 and 6 of glucose through ester bonds; in addition, the hydrogen at position 1 of glucose is related to the carbon at position 2 of monoterpene, indicating that monoterpene is linked to position 1 of glucose via an ether linkage. The structure of compound 1 is shown in FIG. 1. Compound 1 1 H-NMR 13 The C-NMR data are shown in Table 1.
Table 1. Hydrogen and carbon spectra data for compound 1.
Compound 2: and is white powder. According to 1 H， 13 CNMR data is very similar to compound 1, except that one signal of 3,4, 5-trihydroxybenzoic acid is absent. From this, it was found that compound 2 was monoterpene glycoside compound. The structure of compound 2 is shown in figure 2.
Example 2
The main differences between this example and example 1 are:
in the step (1), the volume percentage of ethanol water is 30 percent, and ethanol water is leached for 4 times for 6 days each time.
In the step (2), the volume percentage of acetonitrile water is 35%.
The compound obtained was the same as in example 1.
Example 3
The main differences between this example and example 1 are:
in the step (1), the volume percentage of the ethanol water is 95%.
The compound obtained was the same as in example 1.
Experimental example 1: pharmacological Activity experiments
Bacteria are severely harmful to human health and are easily resistant to drugs. The invention discovers that the compound has better antibacterial activity through detecting that the compound 1 and the compound 2 have obvious inhibition effect on 5 pathogenic bacteria.
The test method comprises the following steps: the microdilution method is commonly used in assays for determining the inhibitory activity of pathogenic or new drugs on sensitive drugs or bacteria. The 96-well micro dilution plate is used, the bottom of each well is U-shaped, the capacity of each well is 0.20-0.30mL, the method is convenient to operate, the using amount of the culture medium is small, and the method can be used for mass drug sensitivity tests. The prepared liquid medicine is diluted in test tube twice in MH culture medium, and then is filled into 96 well plate or diluted in plate hole directly with micro liquid adding device, then diluted bacteria liquid is inoculated, in addition, a row of holes are needed to be reserved as liquid medicine contrast, only culture medium and bacteria liquid are added in the row of holes as bacteria contrast, after the test is completed, the micro stirrer is used for shaking and mixing uniformly, and then the 96 well plate is placed into a 28 or 37 ℃ incubator for incubation for 18-48h, and the absorbance at 630nm is measured by enzyme marker.
Preparation of pathogenic strains:
and respectively inoculating the activated pathogenic bacteria into the sterilized LB culture medium, and then placing the LB culture medium in a constant-temperature oscillator for shake culture at 28 ℃ for 24 hours.
Primary screening of the compound:
diluting the cultured pathogenic bacteria with a culture solution, wherein the dilution is 1:500-1:1000; quantitatively adding diluted bacteria-containing culture solution into each well of a 96-well plate respectively; samples were formulated at 1mg/mL and individually quantitated into each well. After the addition, the mixture is placed in a constant temperature incubator at 28 ℃ for culturing for 48 hours, and then the absorbance of each hole is measured at 630nm by an enzyme-labeled instrument. The test results show that the compound 1 and the compound 2 have remarkable inhibitory activity on 5 strains of pathogenic bacteria (staphylococcus albus, escherichia coli, bacillus cereus, staphylococcus aureus or bacillus subtilis).
Testing of minimum inhibitory concentration:
diluting the cultured pathogenic bacteria with a culture solution, wherein the dilution is 1:500-1:1000; respectively quantitatively adding diluted bacteria-containing culture solution into each hole of the first row of the 96-well plate, and carrying out downward multiple dilution for the next time; each sample was then added to each column of wells separately. After the addition, the mixture is placed in a constant temperature incubator at 28 ℃ for culturing for 48 hours, and then the absorbance of each hole is measured at 630nm by an enzyme-labeled instrument. The results are shown in Table 2.
TABLE 2 minimum inhibitory concentration of monoterpene glycosides in melaleuca alternifolia against 5 pathogenic bacteria
The test results show that the monoterpene glycoside compound has remarkable and broad-spectrum antibacterial activity. Both compound 1 and compound 2 show broad-spectrum antibacterial activity and most show activity comparable to that of positive control, and can be used for preparing antibiotic medicines. The results in Table 2 also show that the overall antibacterial effect of compound 1 is superior to compound 2, and that compound 1 exhibits the best antibacterial effect against Escherichia coli and that compound 2 has a relatively good antibacterial effect against Bacillus subtilis.
The foregoing description of the preferred embodiments of the invention is not intended to be limiting, but rather is intended to cover all modifications, equivalents, alternatives, and improvements that fall within the spirit and scope of the invention.
Claims (1)
1. Use of monoterpene glycosides for combating pathogenic bacteria, which use is not aimed at the diagnosis and treatment of diseases, characterized in that said compounds are:
the pathogenic bacteria are staphylococcus albus, escherichia coli, bacillus cereus and bacillus subtilis;
the preparation method of the monoterpene glycoside compound comprises the following steps:
(1) Extracting melaleuca alternifolia branch and leaf powder with ethanol water with the volume percentage of 30-95% to obtain an extracting solution, and concentrating the extracting solution under reduced pressure to form paste to obtain melaleuca alternifolia extract;
(2) Diluting the melaleuca alternifolia extract obtained in the step (1) with water to form a suspension, sequentially extracting with petroleum ether and ethyl acetate, concentrating the ethyl acetate extract to obtain an extract, performing silica gel column chromatography with a petroleum ether-ethyl acetate mixed solvent and an ethyl acetate-methanol mixed solvent according to increasing polarity, and collecting fractions; combining the similar streams into 8 components, fr.1-Fr.8; performing Sephadex column chromatography on Fr.5, and eluting with chloroform-methanol mixed solvent; preparing with high performance liquid phase, eluting with acetonitrile water to obtain monoterpene glycoside compound;
in the step (1), the volume percentage of ethanol water is 70 percent, ethanol water is leached for 3 to 4 times, and each time is 6 to 7 days;
in the step (2), the volume percentage of acetonitrile water is 30-35%;
the eluent of the sephadex column chromatography is chloroform-methanol mixed solvent with the volume ratio of 50:50.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101012255A (en) * | 2007-01-30 | 2007-08-08 | 温州医学院 | Monoterpene glycosides compound of ginger, antibiotic use thereof and pharmaceutical composition |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101012255A (en) * | 2007-01-30 | 2007-08-08 | 温州医学院 | Monoterpene glycosides compound of ginger, antibiotic use thereof and pharmaceutical composition |
Non-Patent Citations (2)
| Title |
|---|
| Bioactive monoterpene glycosides conjugated with gallic acid from the leaves of Eucalyptus globulus;Tatsuya Hasegawa，等;《Phytochemistry》;20071022;第69卷;第747–753页 * |
| Monoterpenoid glycoside derivatives from Melaleuca alternifolia;Jing-Yu Yang，等;《Biochemical Systematics and Ecology》;20200618;第92卷;104091 * |
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