CN108912200B - Jujube flower extract and antibacterial application thereof - Google Patents
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Abstract
The invention discloses a jujube flower extract and an antibacterial application thereof, wherein the jujube flower extract is prepared by crushing jujube flowers, soaking the crushed jujube flowers for 2 times by using 90% ethanol water solution according to the material-liquid ratio of 1: 2-1: 4, wherein the soaking time is 24-72 hours each time; concentrating the soak solution at 30-50 ℃ under reduced pressure to obtain an extract; and (3) carrying out water dispersion extraction on the extract by using ethyl acetate, and concentrating an ethyl acetate phase at 25-40 ℃ under reduced pressure to obtain the jujube flower extract. Through the activity screening of the jujube flower extract and the monomer compound on the selected seven kinds of bacteria (Grampositive staphylococcus aureus ATCC 43300, staphylococcus aureus ATCC33591, staphylococcus aureus ATCC 29213, staphylococcus aureus ATCC 25923, enterococcus faecalis ATCC 51299, enterococcus faecium ATCC 35667 and escherichia coli ATCC 25922), the jujube flower extract shows good antibacterial activity and can be used as an antibacterial agent.
Description
Technical Field
The invention relates to a chemical active component extracted from plant flowers and preparation and application thereof, in particular to a jujube flower extract and preparation and application thereof.
Background
The jujube tree is a jujube plant belonging to the Rhamnaceae family, is native to China, has a planting history of more than four thousand years in China, and is a traditional dominant tree species in China. Jujube plants are distributed in tropical and subtropical regions and temperate regions, about 170 plants are distributed all over the world, and about 14 plants are distributed in China. At present, the cultivation area of Chinese date trees is as high as 150 million hectares, the annual output is 300 million tons, and the total output of Chinese date trees accounts for more than 99 percent of the world. The jujube trees occupy very important positions in China due to the characteristics of high early fruit yield, rich jujube nutrition, drought resistance, barren resistance, remarkable ecological benefit and economic benefit and the like. Jujube trees grow on plains, hills or mountainous areas with an altitude of less than one thousand and seven hundred meters. Jujube trees have thorns, leaves are grown in April, and blossoming is conducted in May. The jujube fruit is long and round, has rich nutrition, has sweet taste and rich vitamin C, P, can be eaten fresh, can be made into candied fruits and preserved fruits such as candied jujubes, smoked jujubes, wine jujubes, dental jujubes and the like, can also be made into jujube paste, jujube flour, jujube wine, jujube vinegar and the like, and is a good raw material for food industry. The jujube is also used as a medicine, has the effects of strengthening the spleen, nourishing the stomach, nourishing, tonifying blood and strengthening the body, can be used as a medicine for jujube kernels and roots, and can soothe the nerves. The date tree has a long flowering phase from May to July, is fragrant and rich in honey, and is a good honey source plant.
Due to the wide physiological activity of the jujube plants, the research on the chemical components of the jujube plants draws attention. The research on the chemical components of the jujube plants mainly focuses on fruits, and the nutritional components in the red jujubes comprise organic nutritional components (such as crude protein, crude fiber, crude fat, total sugar and the like), vitamins (such as VC, VP1, VB2, VP, VA, VE and the like), mineral elements (P, K, Ca, Mg, Fe, Mn, Cu, Zn and the like), and bioactive components (such as organic acids, triterpenes, flavonoids, adenosine, saponins, alkaloids, sterols, red jujube polysaccharide and the like). The content of each component in red dates varies with varieties and production places.
Although the fruits and the red dates of the jujube trees are researched more, the jujube flowers of the jujube trees are only researched on the volatile chemical components, and other active chemical components in the jujube flowers are not researched and reported.
Disclosure of Invention
The invention aims to provide a jujube flower extract and provide a new application thereof.
The jujube flower extract comprises the following compounds 1-13:
it is extracted by the following method: crushing the jujube flower, soaking for 2 times by using 90% ethanol water solution according to the material-liquid ratio of 1: 2-1: 4, wherein the soaking time is 24-72 hours each time; concentrating the soak solution at 30-50 ℃ under reduced pressure to obtain an extract; and (3) carrying out water dispersion extraction on the extract by using ethyl acetate, and concentrating an ethyl acetate phase at 25-40 ℃ under reduced pressure to obtain the jujube flower extract.
In the extraction method, preferably, the jujube flower is crushed and then is cold-soaked for 2 times by using 90% ethanol aqueous solution according to the material-liquid ratio of 1:3, wherein the cold-soaking time is 48h each time; concentrating the cold extract at 35 deg.C under reduced pressure to obtain extract; and (3) performing water dispersion extraction on the extract by using ethyl acetate, and performing reduced pressure concentration on an ethyl acetate phase at 35 ℃ to obtain the jujube flower extract.
The separation method of the compounds 1-13 in the jujube flower extract comprises the following steps: mixing the jujube flower extract and silica gel according to a mass ratio of 1: 1-2, performing column chromatography, performing gradient elution by using chloroform/methanol as an eluent, wherein the elution gradient is respectively 100:1, 60:1, 30:1, 5:1, 1:1 and 0:1, and collecting two column volumes in each gradient; combining the eluates with the chloroform/methanol volume ratio of 30:1 and 3:1, named as component I, and combining the eluates with the chloroform/methanol volume ratio of 1:1 and 0:1, named as component II; performing middle-pressure chromatographic column chromatography, gel column chromatography and preparative liquid chromatographic separation on the component I through FlashODS C18 to respectively obtain compounds 1-6; and (3) sequentially carrying out flash ODS C18 medium-pressure chromatographic column chromatography, gel column chromatography and preparative liquid chromatographic separation on the component II to respectively obtain compounds 7-13.
The jujube flower extract is applied as a bacteriostatic material, and the bacteria are Grampositive staphylococcus aureus ATCC 43300, staphylococcus aureus ATCC33591, staphylococcus aureus ATCC 29213, staphylococcus aureus ATCC 25923, enterococcus faecalis ATCC 51299, enterococcus faecium ATCC 35667 and escherichia coli ATCC 25922.
The invention has the following beneficial effects: through the activity screening of the jujube flower extract and the monomer compound on the selected seven kinds of bacteria (Grampositive staphylococcus aureus ATCC 43300, staphylococcus aureus ATCC33591, staphylococcus aureus ATCC 29213, staphylococcus aureus ATCC 25923, enterococcus faecalis ATCC 51299, enterococcus faecium ATCC 35667 and escherichia coli ATCC 25922), the jujube flower extract shows good antibacterial activity and can be used as an antibacterial agent.
Detailed Description
The present invention will be described in further detail with reference to examples, but the scope of the present invention is not limited to these examples.
Example 1
Crushing 5kg of jujube flower, adding 15kg of ethanol aqueous solution with volume concentration of 90%, and cold-soaking for 2 times, wherein the cold-soaking time is 48h each time; concentrating the cold soaking solution at 35 deg.C under reduced pressure to obtain extract about 760 g; and (3) carrying out water dispersion extraction on the extract by using ethyl acetate, and concentrating an ethyl acetate phase at 35 ℃ under reduced pressure to obtain 200g of the jujube flower extract.
Mixing 200g of fructus Jujubae flower extract with 300g of silica gel, loading on column, and performing silica gel column chromatography with column volume of 1.5L. Performing gradient elution by using chloroform/methanol as an eluent, wherein the elution gradient is respectively 100:1, 60:1, 30:1, 5:1, 1:1 and 0:1, and two column volumes are collected in each gradient; analyzing and detecting each obtained effluent through a silica gel thin layer plate, combining the eluates with the chloroform/methanol volume ratio of 30:1 and 3:1, and naming the eluates as a component I, and combining the eluates with the chloroform/methanol volume ratio of 1:1 and 0:1, and naming the eluates as a component II; performing flash ODS C18 medium-pressure chromatography, gel column chromatography and preparative liquid chromatography separation on 25g of the component I in sequence to respectively obtain compounds 1-6; and (3) sequentially carrying out flash ODS C18 medium-pressure chromatographic column chromatography, gel column chromatography and preparative liquid chromatography on 13g of the component II to respectively obtain compounds 7-13.
The compound 1 is 3-keto-5, 11-dienoeostearyl alcohol, the compound 2 is mucic acid-3-O-cis-p-coumarate, the compound 3 is oleanolic acid, the compound 4 is mucic acid-3-O-trans-p-coumarate, the compound 5 is betulin, the compound 6 is betulinic acid, the compound 7 is crataegolic acid-3-O-trans-p-coumarate, the compound 8 is hederagenin, the compound 9 is 13-hydroxybetulinic acid, the compound 10 is p-methoxyphenylacrylic acid, the compound 11 is rapeseed, the compound 12 is rutin, the compound 13 is 3 β -D-glucoside-5, 11-dienoeostearyl alcohol, and the structural formula is shown as follows:
example 2
Antibacterial Activity of the jujube flower extract of example 1
Testing bacteria: grampositive Staphylococcus aureus ATCC 43300, Staphylococcus aureus ATCC33591, Staphylococcus aureus ATCC 29213, Staphylococcus aureus ATCC 25923, enterococcus faecalis ATCC 51299, enterococcus faecium ATCC 35667 and Escherichia coli ATCC 25922.
The antibacterial activity test is divided into primary screening and secondary screening. The concentration of the primary screen was 100. mu.g/mL. Samples active at a concentration of 100. mu.g/mL were re-screened. The secondary screening was carried out by microdilution (Nat Protoc,2008,3: 1494-1500). The microdilution method is simple and convenient to operate, the amount of the used culture medium is small, and the microdilution method can be used for large-scale tests. The specific operation method comprises the following steps: in a clean bench, the test bacteria solution was added to a 96-well plate using a pipette gun, 198. mu.L of the first well of each row and 100. mu.L of the remaining wells. And dissolving a sample to be detected by DMSO (dimethyl sulfoxide) to prepare a solution with a certain initial concentration. Taking 2 mu L of sample to be detected by a pipette, adding the sample into the first hole, sequentially diluting the sample to 8 th concentration gradient from the subsequent hole by twice, taking 100 mu L of sample out of the 8 th hole, throwing away the sample, and making 3 parallels for each concentration gradient. After the sample addition and dilution were completed, 100. mu.L of the test bacterial solution was added to each well to give a final volume of 200. mu.L per well, and the mixture was shaken and mixed by a micro-stirrer. Blank, negative (DMSO) and positive (vancomycin) controls were set. Each test plate was incubated at 37 ℃ for 20 h. The concentration corresponding to the last clear well, i.e., the Minimum Inhibitory Concentration (MIC), was observed and the results are shown in table 1.
TABLE 1 antibacterial Activity of jujube flower extract and compounds in jujube flower
Claims (1)
1. A separation method of compounds 1-13 in a jujube flower extract is characterized by comprising the following steps: mixing the jujube flower extract and silica gel according to a mass ratio of 1: 1-2, performing column chromatography, performing gradient elution by using chloroform/methanol as an eluent, wherein the elution gradient is respectively 100:1, 60:1, 30:1, 5:1, 1:1 and 0:1, and collecting two column volumes in each gradient; combining the eluates with the chloroform/methanol volume ratio of 30:1 and 3:1, named as component I, and combining the eluates with the chloroform/methanol volume ratio of 1:1 and 0:1, named as component II; performing middle-pressure chromatographic column chromatography, gel column chromatography and preparative liquid chromatographic separation on the component I through FlashODS C18 to respectively obtain compounds 1-6; performing middle-pressure chromatographic column chromatography, gel column chromatography and preparative liquid chromatographic separation on the component II through FlashODS C18 to respectively obtain compounds 7-13;
the jujube flower extract is extracted by the following method: crushing the jujube flower, and cold-soaking the crushed jujube flower for 2 times by using 90% ethanol aqueous solution according to the material-liquid ratio of 1:3, wherein the cold-soaking time is 48 hours each time; concentrating the cold extract at 35 deg.C under reduced pressure to obtain extract; extracting the extract with ethyl acetate and water, and concentrating ethyl acetate phase at 35 deg.C under reduced pressure to obtain flos Jujubae extract;
the structure of the compound 1-13 is as follows:
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| CN113336819B (en) * | 2021-05-13 | 2023-04-21 | 中国科学院西北高原生物研究所 | Method for separating and preparing three triterpenic acid compounds from sea buckthorn pomace |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104585651A (en) * | 2014-12-06 | 2015-05-06 | 西北大学 | Standardized red jujube extract and preparation method and analysis method thereof |
| CN105687367A (en) * | 2016-01-25 | 2016-06-22 | 西北大学 | Red jujube leaf standard extract, as well as preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104585651A (en) * | 2014-12-06 | 2015-05-06 | 西北大学 | Standardized red jujube extract and preparation method and analysis method thereof |
| CN105687367A (en) * | 2016-01-25 | 2016-06-22 | 西北大学 | Red jujube leaf standard extract, as well as preparation method and application thereof |
Non-Patent Citations (3)
| Title |
|---|
| Antimicrobial triterpenoids from Licania heteromorpha;Braca, Alessandra et al.;《Planta Medica》;20001231;第66卷(第8期);第768页摘要和右栏第2段 * |
| Chemical characterization of the main bioactive constituents from fruits of Ziziphus jujuba;Lu Bai et al.;《Food & Function》;20160519;第7卷;第2871页Fig1., 2872页 * |
| Lu Bai et al..Chemical characterization of the main bioactive constituents from fruits of Ziziphus jujuba.《Food & Function》.2016,第7卷第2870-2877页. * |
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