CN111848593A - Water-soluble isoorientin-zinc complex and preparation method and application thereof - Google Patents
Water-soluble isoorientin-zinc complex and preparation method and application thereof Download PDFInfo
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- CN111848593A CN111848593A CN202010675120.7A CN202010675120A CN111848593A CN 111848593 A CN111848593 A CN 111848593A CN 202010675120 A CN202010675120 A CN 202010675120A CN 111848593 A CN111848593 A CN 111848593A
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- 239000011701 zinc Substances 0.000 title claims abstract description 125
- 229910052725 zinc Inorganic materials 0.000 title claims abstract description 123
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 238000010668 complexation reaction Methods 0.000 title description 2
- ODBRNZZJSYPIDI-UHFFFAOYSA-N 3',4',5,7-tetrahydroxy-6-C-glucopyranosylflavone Natural products OC1C(O)C(O)C(CO)OC1C1=C(O)C=C(OC(=CC2=O)C=3C=C(O)C(O)=CC=3)C2=C1O ODBRNZZJSYPIDI-UHFFFAOYSA-N 0.000 claims abstract description 74
- ODBRNZZJSYPIDI-VJXVFPJBSA-N isoorientin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=C(O)C=C(OC(=CC2=O)C=3C=C(O)C(O)=CC=3)C2=C1O ODBRNZZJSYPIDI-VJXVFPJBSA-N 0.000 claims abstract description 74
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- 229930003944 flavone Natural products 0.000 description 3
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- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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Abstract
The invention belongs to the technical field of organic complex preparation, and relates to a water-soluble isoorientin-zinc complex, and a preparation method and application thereof, wherein the preparation method comprises the following steps: 1) adding absolute ethanol into isoorientin, dissolving, adding zinc acetate, and adjusting pH to 7.5-8.5 with NaOH-ethanol mixed solution; 2) water bath reflux magnetic stirring, cooling, aging, precipitating, and centrifuging to obtain precipitate and supernatant; 3) washing the precipitate with anhydrous ethanol, and vacuum freeze drying to obtain isoorientin-zinc complex; the water contact angle of the isoorientin-zinc complex is 17.4 degrees, and the isoorientin-zinc complex is applied to inhibiting escherichia coli and staphylococcus aureus. The isoorientin-zinc complex formed by the invention has good water solubility and bioactivity, good biological safety and strong oxidation resistance, has good inhibition effect on staphylococcus aureus and escherichia coli, and can be widely applied to the food and medicine industries.
Description
Technical Field
The invention belongs to the technical field of organic complex preparation, and relates to a water-soluble isoorientin-zinc complex, and a preparation method and application thereof.
Background
Isoorientin is a tetrahydroxyflavone compound, also called 3 ', 4', 5, 7-tetrahydroxyflavone-6-O-beta-D-glucopyranoside or luteolin 6-C-glucoside, has a molecular formula of C21H2OO11 and a molecular weight of 448.38, and has a chemical structural formula shown in figure 1 (a). The isoorientin solid is light yellow powder, the steam density is 15.48, the melting point/freezing point is 237-239 ℃, and the isoorientin solid is a natural flavonoid substance which is slightly soluble in water and soluble in solvents such as ethanol and methanol. It is widely used in food such as cucumber, buckwheat, passion flower, etc., and has antioxidant, antiinflammatory, antibacterial, hepatoprotective, and intestinal flora regulating effects. However, the poor water solubility and low bioavailability of isoorientin limit the application of isoorientin in the industries such as food, medicine and the like, and physiological effects cannot be fully exerted.
However, since flavonoids have a group containing a lone electron pair such as a hydroxyl group or a carbonyl group, they can undergo a chemical coordination reaction with a metal element to form a flavonoid metal complex. The research has proved that the flavone metal complex can not only improve the physicochemical property of flavone substance, improve the utilization rate of flavone by human body, but also enhance the biological activity.
Disclosure of Invention
Aiming at the technical problems of the existing isoorientin, the invention provides the water-soluble isoorientin-zinc complex and the preparation method thereof, the formed isoorientin-zinc complex can improve the water solubility and the bioactivity of the isoorientin, and meanwhile, the isoorientin-zinc complex has good biological safety and strong oxidation resistance, has good inhibition effect on staphylococcus aureus and escherichia coli, and can be widely applied to the food and medicine industries.
In order to achieve the purpose, the invention adopts the technical scheme that:
a preparation method of a water-soluble isoorientin-zinc complex comprises the following steps:
1) adding absolute ethanol into isoorientin, heating and dissolving in the dark, adding zinc acetate, and adjusting pH to 7.5-8.5 with NaOH-ethanol mixed solution to obtain mixed solution;
2) refluxing the mixed solution in a water bath, magnetically stirring, cooling, aging, precipitating, and centrifugally separating to obtain a precipitate and a supernatant;
3) washing the precipitate with anhydrous ethanol, and vacuum freeze drying to obtain yellow solid powder as isoorientin-zinc complex.
Further, the mass ratio of the isoorientin to the zinc acetate in the step 1) is 2: 3-4: 6, and the mass concentration of the NaOH-ethanol mixed solution is 2%.
Further, in the step 2), the temperature of the water bath is 50-65 ℃, and the stirring time is 6-10 hours.
An isoorientin-zinc complex prepared by the method for preparing isoorientin-zinc complex.
Further, the water contact angle of the isoorientin-zinc complex is 17.4 degrees.
An application of isoorientin-zinc complex in inhibiting bacteria is provided.
An application of isoorientin-zinc complex in inhibiting Escherichia coli is provided.
An application of isoorientin-zinc complex in inhibiting Staphylococcus is provided.
An application of isoorientin-zinc complex in inhibiting Staphylococcus aureus is provided.
The invention has the beneficial effects that:
1. according to the invention, isoorientin-zinc complex is formed through coordination reaction of isoorientin and zinc acetate, the binding sites are 4-carbonyl of ring C and hydroxyl on ring A and ring B, fat-soluble isoorientin is changed into water-soluble isoorientin-zinc complex, the water contact angle of the isoorientin-zinc complex is 17.4 degrees, and the water contact angle of the isoorientin is 37.8 degrees, which indicates that the hydrophilicity of the isoorientin-zinc complex is improved; and the preparation method is simple and easy to operate.
2. The isoorientin-zinc complex prepared by the invention does not generate toxicity to HL-7702 human liver cells, and has good biological safety; meanwhile, the scavenging rate of DPPH free radicals reaches 93.68%, and the antioxidant capacity is strong.
3. The isoorientin-zinc complex prepared by the invention is applied to bacteria, particularly has the bacteriostasis rate of 60.70% when being applied to escherichia coli, has good bacteriostasis effect on the escherichia coli, and can be widely applied to the food and medicine industries.
4. When the isoorientin-zinc complex prepared by the invention is applied to staphylococcus, especially staphylococcus aureus, the bacteriostasis rate is 63.41%, and the isoorientin-zinc complex has a strong bacteriostasis effect on the staphylococcus aureus and can be widely applied to the food and medicine industries.
Drawings
FIG. 1 shows chemical structural formulas of isoorientin and isoorientin-zinc complex;
FIG. 2 is a graph showing ultraviolet absorption spectra of isoorientin and isoorientin-zinc complex;
FIG. 3 is an infrared spectrum of isoorientin and isoorientin-zinc complex;
FIG. 4 is a thermogravimetric analysis chart of isoorientin-zinc complex;
FIG. 5 is a nuclear magnetic resonance spectrum analysis chart of isoorientin and isoorientin-zinc complex;
FIG. 6 is a water contact angle diagram of isoorientin and isoorientin-zinc complexes;
FIG. 7 shows the action of isoorientin-zinc complex on the activity of human hepatocytes;
figure 8 clearance of isoorientin and isoorientin-zinc complexes on DPPH radicals;
FIG. 9 is a photograph showing the inhibition zones of E.coli and Staphylococcus aureus by isoorientin and isoorientin-zinc complex.
Detailed Description
The invention will now be described in detail with reference to the drawings and specific embodiments.
A preparation method of a water-soluble isoorientin-zinc complex comprises the following steps:
1) adding absolute ethyl alcohol into isoorientin, heating and dissolving the isoorientin in the dark, adding zinc acetate, and adjusting the pH to 7.5-8.5 by using a NaOH-ethanol solution to obtain a mixed solution;
2) refluxing the mixed solution in a water bath, magnetically stirring, cooling, aging, precipitating, and centrifugally separating to obtain a precipitate and a supernatant;
3) washing the precipitate with anhydrous ethanol, and vacuum freeze drying to obtain yellow solid powder as isoorientin-zinc complex.
Further, the mass ratio of the isoorientin to the zinc acetate in the step 1) is 2: 3-4: 6 (preferably, a range is given), and the mass concentration of the NaOH-ethanol mixed solution is 2%.
Further, in the step 2), the temperature of the water bath is 50-65 ℃, and the stirring time is 6-10 hours.
An isoorientin-zinc complex prepared by the method for preparing isoorientin-zinc complex.
Further, the water contact angle of the isoorientin-zinc complex is 17.4 degrees.
An application of isoorientin-zinc complex in inhibiting bacteria is provided.
An application of isoorientin-zinc complex in inhibiting Escherichia coli is provided.
An application of isoorientin-zinc complex in inhibiting Staphylococcus is provided.
An application of isoorientin-zinc complex in inhibiting Staphylococcus aureus is provided.
Example 1
A preparation method of a water-soluble isoorientin-zinc complex comprises the following steps:
1) adding absolute ethanol into isoorientin, heating and dissolving in the dark, adding zinc acetate, and adjusting pH to 8 with NaOH-ethanol solution to obtain mixed solution;
2) refluxing the mixed solution in a water bath, magnetically stirring, cooling, aging, precipitating, and centrifugally separating to obtain a lower precipitate and a supernatant;
3) washing the lower precipitate with anhydrous ethanol, and vacuum freeze drying to obtain yellow solid powder as isoorientin-zinc complex.
In the embodiment, the mass ratio of the isoorientin to the zinc acetate in the step 1) is 2:3, and the mass concentration of the NaOH-ethanol mixed solution is 2%. The NaOH-ethanol mixed solution is prepared by dissolving 2g of sodium hydroxide in 98g of ethanol solution, and the mass concentration of the NaOH-ethanol mixed solution is 2%.
In the embodiment, in the step 2), the water bath temperature is 55 ℃ and the stirring time is 8 h.
In this example, the yield of the prepared isoorientin-zinc complex was 81.27% by weight calculation. The structural formula is shown in figure 1 (b).
Example 2
A preparation method of a water-soluble isoorientin-zinc complex comprises the following steps:
1) adding absolute ethanol into isoorientin, heating and dissolving in the dark, adding zinc acetate, and adjusting pH to 8.5 with NaOH-ethanol solution to obtain mixed solution;
2) refluxing the mixed solution in a water bath, magnetically stirring, cooling, aging, precipitating, and centrifugally separating to obtain a lower precipitate and a supernatant;
3) washing the lower precipitate with anhydrous ethanol, and vacuum freeze drying to obtain yellow solid powder as isoorientin-zinc complex.
In this embodiment, the mass ratio of isoorientin to zinc acetate in step 1) is 3:4, and the mass concentration of the NaOH-ethanol mixed solution is 2%. The NaOH-ethanol mixed solution is prepared by dissolving 2g of sodium hydroxide in 98g of ethanol solution, and the mass concentration of the NaOH-ethanol mixed solution is 2%.
In the embodiment, in the step 2), the water bath temperature is 65 ℃, and the stirring time is 6 hours.
In this example, the yield of the prepared isoorientin-zinc complex was 78.35% by weighing.
Example 3
A preparation method of a water-soluble isoorientin-zinc complex comprises the following steps:
1) Adding absolute ethanol into isoorientin, heating and dissolving in the dark, adding zinc acetate, and adjusting pH to 7.5 with NaOH-ethanol solution to obtain mixed solution;
2) refluxing the mixed solution in a water bath, magnetically stirring, cooling, aging, precipitating, and centrifugally separating to obtain a lower precipitate and a supernatant;
3) washing the lower precipitate with anhydrous ethanol, and vacuum freeze drying to obtain yellow solid powder as isoorientin-zinc complex.
In the embodiment, the mass ratio of the isoorientin to the zinc acetate in the step 1) is 4:6, and the mass concentration of the NaOH-ethanol mixed solution is 2%. The NaOH-ethanol mixed solution is prepared by dissolving 2g of sodium hydroxide in 98g of ethanol solution, and the mass concentration of the NaOH-ethanol mixed solution is 2%.
In the embodiment, in the step 2), the water bath temperature is 50 ℃, and the stirring time is 10 hours.
In this example, the yield of the prepared isoorientin-zinc complex is 80.14% by weighing calculation.
Further, in order to illustrate the structure, performance index and application of the isoorientin-zinc complex prepared by the invention in the aspect of bacteriostasis, the following comparative experiments are carried out.
Test groups: isoorientin-zinc complex prepared in example 1
Control group: isoorientin
The results of the ultraviolet spectroscopy, infrared spectroscopy, thermogravimetric analysis, nuclear magnetic resonance spectroscopy and elemental analysis of the experimental group and the control group are shown in fig. 2 to 5.
As can be seen from the ultraviolet absorption spectrum chart in FIG. 2, the maximum absorption wavelengths of isoorientin are mainly 250nm and 350nm, while the maximum absorption wavelengths of isoorientin-zinc complex are 270nm and 395nm, respectively, and the two peak bands shift, i.e., move in the long-wave direction, which indicates that the A ring and the B ring of isoorientin and Zn ring are both in the same direction2+A coordination reaction occurs to form a stable metal complex. Isoorientin and Zn2+The sites where the coordination reaction occurs may have hydroxyl groups of the A and B rings.
It is further determined from the infrared spectrum of fig. 3 and the wavelength positions of the infrared absorption peaks in table 1 that isoorientin and zinc acetate undergo a coordination reaction to form an isoorientin-zinc complex, and the binding sites are the 4-carbonyl of ring C and the hydroxyls on rings a and B.
TABLE 1 wavelength positions of major infrared absorption peaks of isoorientin and isoorientin-zinc complexes
As can be seen from the thermogravimetric analysis chart of fig. 4, the first weight loss stage of the isoorientin-zinc complex is about 120-160 ℃, the weight loss rate is 6.02%, and approximately the weight loss of 4 water molecules (the theoretical weight loss rate is 6.24%), which indicates that the isoorientin-zinc complex contains 4 molecules of crystal water; the second weight loss stage is about 250-550 ℃, which is the oxidative decomposition stage of the complex, and the weight loss rate is 75.31%, which is equivalent to the weight of 2 isoorientin ligands (the theoretical weight loss rate is 76.84%). The remainder obtained after the isoorientin-zinc complex is decomposed is the oxide of zinc.
Referring to fig. 5, fig. 5(a) is a nuclear magnetic resonance spectrum analysis chart of isoorientin; fig. 5(b) is a nuclear magnetic resonance spectrum analysis chart of isoorientin-zinc complex. From 1H NMR spectra of isoorientin and isoorientin-zinc complex, it can be seen that the signal peaks of hydroxyl protons of isoorientin at 13.558(C5-OH), 9.894(C3 '-OH) and 9.389 (C4' -OH) disappear in isoorientin-zinc complex, which indicates that the hydroxyl protons of isoorientin at positions 3 ', 4' and 5 and Zn all disappear in isoorientin-zinc complex2+A coordination reaction occurs.
TABLE 2 content of C, H, Zn elements in isoorientin-zinc complex
As can be seen from table 2, the content test values of isoorientin-zinc complex C, H, Zn are 44.67%, 4.02% and 18.56%, respectively. Combining the previous test results, isoorientin and Zn2+And (3) adding the following components in percentage by weight of 2: 3 to form the isoorientin-zinc complex.
Test groups: isoorientin-zinc complex prepared in example 1
Control group: isoorientin
The hydrophilicity of isoorientin-zinc complex was analyzed by water contact angle, and the results are shown in fig. 6. Fig. 6(a) is the water contact angle of isoorientin; fig. 6(b) shows water contact of isoorientin-zinc complex.
As can be seen from fig. 6, the water contact angle of isoorientin is 37.8 °, while the water contact angle of isoorientin-zinc complex is 17.4 °, which indicates that the hydrophilicity of isoorientin-zinc is better than that of isoorientin, i.e., isoorientin-zinc complex has high hydrophilicity; meanwhile, the method also shows that the originally fat-soluble isoorientin is converted into the water-soluble isoorientin-zinc complex after coordination.
Test groups: isoorientin-zinc complex prepared in example 1
The cell activity of the isoorientin-zinc complex with different concentrations on HL-7702 human liver cells is determined by adopting an MTT staining method. The results are shown in FIG. 7.
As can be seen from fig. 7, when the concentration of isoorientin-zinc complex is 4, 2, 1, 0.5ug/mL, the activity of HL-7702 human hepatocytes is 102.46%, 99.07%, 101.15% and 105.87%, respectively; when the addition amount of isoorientin-zinc complex is 0ug/mL, the activity of HL-7702 human liver cells is 100%. The results show that the isoorientin-zinc complex hardly affects the cell activity of HL-7702 human liver cells, that is to say that the isoorientin-zinc complex does not generate toxicity to HL-7702 human liver cells, and has good biological safety.
Test groups: isoorientin-zinc complex prepared in example 1
Control group: isoorientin
The experiment adopts isoorientin and isoorientin-zinc complex to remove DPPH free radicals, the concentrations of isoorientin and isoorientin-zinc complex are respectively 10, 20, 50 and 100ug/mL, the results are shown in figure 8, the (1) in figure 8 is the result of removing the DPPH free radicals by isoorientin, and the (2) in figure 8 is the result of removing the DPPH free radicals by isoorientin-zinc complex.
Since DPPH is an organic nitrogen free radical with a single electron, is dark purple in ethanol solution, has the strongest absorption peak at the wavelength of 517nm, and the absorbance and the concentration are linearly related, the free radical scavenger can be combined with DPPH free radical, so that the free radical is reduced, the color is lightened, and the absorbance is reduced.
As can be seen from fig. 8, the removal rate of isoorientin on DPPH radicals increases with the concentration of isoorientin, the removal rate of isoorientin-zinc complexes on DPPH radicals also increases with the concentration of isoorientin-zinc complexes, and under the same concentration, the removal rate of isoorientin-zinc complexes on DPPH radicals is higher than that of isoorientin, and the removal rate of isoorientin-zinc complexes on DPPH radicals is higher and higher.
When the concentration is 10 and 20 mu g/mL, the capability of the isoorientin-zinc complex for removing DPPH free radicals is obviously higher than that of isoorientin (p is less than 0.01). When the concentration reaches 100 mu g/mL, the clearance rate of the isoorientin and the isoorientin-zinc complex on DPPH free radicals reaches 91.48% and 93.68%.
Therefore, the isoorientin-zinc complex has stronger oxidation resistance to DPPH free radicals than isoorientin.
Test groups: isoorientin and the isoorientin-zinc complex prepared in example 1 were added
Control group: no isoorientin-zinc complex and isoorientin are added
The bacteriostatic action was analyzed by the zone of inhibition method. In a sterile operating platform, a sterilized steel pipe is used for punching a test flat plate, a small culture medium block is carefully picked off by using a sterile toothpick to form a round hole, and each small hole is baked for about 10 seconds under an alcohol lamp to carry out flame sealing. Absorbing isoorientin and isoorientin-zinc complex solutions with different concentrations by using a liquid transfer gun, and dripping into the round holes of the flat plate. 100 mul of activated escherichia coli and staphylococcus aureus bacteria liquid are respectively taken and coated on a flat plate. Placing the plate at 4 ℃ for pre-diffusion for 2h, then culturing at 37 ℃ for 24h at constant temperature, taking out after the culture time, measuring the diameter of each inhibition zone by using a vernier caliper, wherein the diameter comprises the diameter of a small hole, measuring each inhibition zone for 2 times by using a cross method, taking the average value of the inhibition zones, and recording data. The corn stigma chewable tablet suspension was replaced with sterile water as a blank and run in triplicate. The formula for calculating the bacteriostatic rate is as follows: the bacteriostatic rate (%) - (the diameter of the bacteriostatic zone of the treated sample-the diameter of the bacteriostatic zone of the blank sample)/the diameter of the bacteriostatic zone of the treated sample x 100%. The results are shown in fig. 9 and table 3.
TABLE 3 inhibition of growth of E.coli and S.aureus by isoorientin and isoorientin-zinc complex
Note:*representing the significant difference (p) between samples of different concentrations and the respective blank groups<0.05)；**Representing the very significant difference (p) between the samples of different concentrations and the respective blank<0.01)。#Representing significant differences (p) of samples of the same concentration<0.05)；##Represents a very significant difference (p) between samples of the same concentration<0.01)。
The photograph of the zone of inhibition in fig. 9 is specifically shown as:
(a0) is a photograph of the zone of inhibition when no substance is added to the Escherichia coli;
(a1) is a photograph of the inhibition zone when isoorientin is added into escherichia coli;
(a2) is a photograph of the inhibition zone when isoorientin-zinc complex is added into escherichia coli;
(b0) is a photograph of the zone of inhibition when no substance is added to staphylococcus aureus;
(b1) is a photograph of the inhibition zone when isoorientin is added into staphylococcus aureus;
(b2) respectively are photos of the inhibition zones when isoorientin-zinc complex is added into staphylococcus aureus.
Analysis of FIG. 9 and Table 3 reveals that:
1) as can be seen from fig. 9, when isoorientin and isoorientin-zinc complexes are added to the blank escherichia coli and staphylococcus aureus respectively, the diameter of the inhibition zone of isoorientin is larger than that of the blank group and smaller than that of the inhibition zone of isoorientin-zinc complexes, which indicates that the isoorientin-zinc complexes have good inhibition effect on escherichia coli and staphylococcus aureus;
2) From table 3, it can be seen that the isoorientin-zinc complex has a greater inhibition effect on escherichia coli than isoorientin at the same mass concentration, and particularly, when the concentration is 800 μ g/mL, the inhibition rate of isoorientin on escherichia coli is 54.62%, and the inhibition rate of isoorientin-zinc complex on escherichia coli is 60.70%, indicating that the isoorientin-zinc complex prepared by the invention has a greater inhibition effect on escherichia coli than isoorientin;
3) from table 3, the inhibition effect of the isoorientin-zinc complex on staphylococcus aureus is higher than that of isoorientin under the same mass concentration, particularly, when the concentration is 800 mug/mL, the inhibition rate of the isoorientin on staphylococcus aureus is 57.20%, and the inhibition rate of the isoorientin-zinc complex on staphylococcus aureus is 63.41%, which shows that the inhibition effect of the isoorientin-zinc complex on staphylococcus aureus is higher than that of the isoorientin;
4) from table 3, it can be seen that the isoorientin and the isoorientin-zinc complex have stronger inhibitory effect on staphylococcus aureus than escherichia coli at the same mass concentration.
In conclusion, the isoorientin-zinc complex prepared by the invention has good water solubility, high bioactivity, strong oxidation resistance and safety, particularly has better bacteriostatic effect on escherichia coli and staphylococcus aureus, can be widely applied to the food and medicine industries, and plays a role in inhibiting bacterial growth.
Claims (9)
1. A preparation method of the water-soluble isoorientin-zinc complex is characterized by comprising the following steps: the preparation method comprises the following steps:
1) adding absolute ethanol into isoorientin, heating and dissolving in the dark, adding zinc acetate, and adjusting pH to 7.5-8.5 with NaOH-ethanol mixed solution to obtain mixed solution;
2) refluxing the mixed solution in a water bath, magnetically stirring, cooling, aging, precipitating, and centrifugally separating to obtain a precipitate and a supernatant;
3) washing the precipitate with anhydrous ethanol, and vacuum freeze drying to obtain yellow solid powder as isoorientin-zinc complex.
2. The method for preparing the water-soluble isoorientin-zinc complex according to claim 1, wherein the water-soluble isoorientin-zinc complex comprises the following steps: the mass ratio of the isoorientin to the zinc acetate in the step 1) is 2: 3-4: 6, and the mass concentration of the NaOH-ethanol mixed solution is 2%.
3. The method for preparing the water-soluble isoorientin-zinc complex according to claim 1, wherein the water-soluble isoorientin-zinc complex comprises the following steps: in the step 2), the temperature of the water bath is 50-65 ℃, and the stirring time is 6-10 h.
4. An isoorientin-zinc complex prepared by the method of preparing isoorientin-zinc complex according to any one of claims 1-3.
5. The isoorientin-zinc complex of claim 4, wherein: the water contact angle of the isoorientin-zinc complex is 17.4 degrees.
6. Use of the isoorientin-zinc complex of claim 4 in inhibiting bacteria.
7. The use of the isoorientin-zinc complex of claim 4 in inhibiting escherichia coli.
8. The use of the isoorientin-zinc complex of claim 4 in inhibiting staphylococci.
9. The use of the isoorientin-zinc complex of claim 4 in inhibiting Staphylococcus aureus.
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| CN101843612A (en) * | 2010-05-21 | 2010-09-29 | 暨南大学 | Application of isoorientin in preparation of medicament for resisting respiratory syncytial virus |
| JP2017114860A (en) * | 2015-12-24 | 2017-06-29 | ロッテ コンフェクショナリー カンパニー リミテッド | Compositions for impotence improvement and increase in blood testosterone secretion |
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| JP2017114860A (en) * | 2015-12-24 | 2017-06-29 | ロッテ コンフェクショナリー カンパニー リミテッド | Compositions for impotence improvement and increase in blood testosterone secretion |
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