CN111518150B - Flavonoid glycoside compound, golden-edged rose active extract, preparation method and application - Google Patents
Flavonoid glycoside compound, golden-edged rose active extract, preparation method and application Download PDFInfo
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- CN111518150B CN111518150B CN202010466720.2A CN202010466720A CN111518150B CN 111518150 B CN111518150 B CN 111518150B CN 202010466720 A CN202010466720 A CN 202010466720A CN 111518150 B CN111518150 B CN 111518150B
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- methanol
- flavonoid glycoside
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- chloroform
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Abstract
The invention relates to a flavonoid glycoside compound, a rosa banksiae active extract, a preparation method and application thereof. The main technical scheme is as follows: a flavonoid glycoside compound has the following structure:
the flavonoid glycoside compounds belong to natural sources, and can be separated from Rosa canina. In addition, the invention also provides a rosa labrata active extract, wherein the rosa labrata active extract comprises the flavonoid glycoside compound with the structure. The flavonoid glycoside compound and the rose bengal active extract provided by the invention can be used as an antioxidant and/or an antibacterial agent and are applied to the fields of skin care products, foods, medicines and the like.
Description
Technical Field
The invention relates to the technical field of oxidation resistance and antibiosis, in particular to a flavonoid glycoside compound, a rosa laevigata active extract, a preparation method and application thereof.
Background
Skin aging is generally divided into intrinsic aging and extrinsic aging. Among them, endogenous aging is a natural aging process due to the change of hormones with age. Exogenous aging is mainly caused by excessive ultraviolet radiation, which causes excessive free radicals or Reactive Oxygen Species (ROS) in vivo, oxidative damage to the body and photoaging, and causes skin aging symptoms such as skin relaxation, wrinkles, dryness and the like. Therefore, the development of the antioxidant containing the free radical scavenging activity applied to the skin care product has an important effect on skin aging resistance. In addition, antioxidants have a wide range of applications in food products, for example, antioxidants can be used to prevent food from deteriorating due to oxidation.
Besides antioxidants, antibacterial agents also have a wide range of utility; for example, antibacterial agents are used as preservatives in cosmetics, foods and pharmaceuticals.
At present, antioxidants added in products such as skin care products, foods and the like are not natural sources, and chemically synthesized antioxidants may have the problems of safety, sensitization and the like; in addition, antimicrobial agents (preservatives) of non-natural origin used in products such as skin care products and foods also have safety risks. While the antioxidant and the antibacterial agent which are natural sources are safe and nontoxic. Plants contain active secondary metabolites, and the search for natural antioxidants and antibacterial agents from plants is an effective way.
Disclosure of Invention
In view of the above, the present invention provides a flavonoid glycoside compound, a rosa labra active extract, a preparation method and an application thereof, and mainly aims to provide or prepare a natural flavonoid glycoside compound and a rosa labra active extract containing the flavonoid glycoside compound; in addition, the flavonoid glycoside compound and the golden-edge rose active extract have double effects of antioxidation and antibacterial activity.
In order to achieve the purpose, the invention mainly provides the following technical scheme:
in one aspect, an embodiment of the present invention provides a flavonoid glycoside compound, where the structure of the flavonoid glycoside compound is as follows:
on the other hand, the application of the flavonoid glycoside compound in serving as or preparing an antioxidant and/or an antibacterial agent; preferably, the antioxidant is a DPPH radical scavenger; preferably, the antibacterial agent is an antibacterial agent for staphylococcus aureus.
On the other hand, in the above method for producing a flavonoid glycoside compound, the flavonoid glycoside compound is isolated from a first plant; wherein the first plant is a plant containing the flavonoid glycoside compound.
Preferably, the first plant is rose bengal.
Preferably, the method for separating the flavonoid glycoside compound from the rosa citrifolia comprises the following steps:
1) leaching, extracting and post-treating the rose flowers with golden edges to obtain a first solvent extract;
2) performing column chromatography separation on the first solvent extract to obtain an active extract of the rosa laevigata containing the flavonoid glycoside compounds;
3) performing silica gel column chromatography separation on the rose bengal active extract to prepare a target fraction containing the flavonoid glycoside compounds;
4) and purifying the target fraction by adopting reverse-phase high performance liquid chromatography to separate the flavonoid glycoside compound.
Preferably, the first solvent extract in step 1) is an ethanol extract; further preferably, the step 1) specifically comprises: leaching the golden-edge rose by adopting an ethanol-water solution with the volume fraction of 90-100%, and concentrating the leaching solution to obtain a first extract; leaching the residue with 60-70% ethanol-water solution, and concentrating the leaching solution to obtain a second extract; extracting the first extract with a second solvent; combining the extracted remainder and the second extract, and performing freeze drying treatment to obtain a first solvent extract; preferably, the second solvent is petroleum ether.
Preferably, in the step 2), the first solvent extract is subjected to column chromatography separation by using macroporous resin; preferably, a methanol-water solvent system is adopted for gradient elution; wherein the initial volume fraction of methanol is 0-5%, and the final volume fraction of methanol is 90-100%; preferably, the elution fractions with methanol volume fraction of 50-70% are combined and further concentrated to obtain the active extract of rosa rugosa containing the flavonoid glycoside compounds.
Preferably, the step 3) includes: performing silica gel column chromatography separation on the rose bengal active extract, and performing gradient elution by using a chloroform-methanol solvent system; wherein the initial volume ratio of chloroform to methanol is 8:1-10:1, preferably 9: 1; the final volume ratio of chloroform to methanol is 3:2 to 2:3, preferably 1: 1; during the gradient elution, the concentration of chloroform decreases progressively; wherein, the elution fractions with the volume ratio of chloroform to methanol of 2:1-5:1 are combined to obtain a first fraction; the first fraction is separated by silica gel column chromatography again, and gradient elution is carried out by a chloroform-methanol solvent system; wherein the initial volume ratio of chloroform to methanol is 4:1-6:1, preferably 5: 1; the final volume ratio of chloroform to methanol is 1:2 to 3:2, preferably 1: 1; during the gradient elution, the concentration of chloroform decreases progressively; and mixing elution fractions of chloroform and methanol in a volume ratio of 1:1-3:1 to obtain the target fraction.
Preferably, in the step 4): the target flow is subjected to semi-preparation by high performance liquid chromatography, and the detection wavelengths are 220nm and 254 nm; preferably, the type of column used is YMC-Pack ODS-AQ; preferably, the flow rate is 3 mL/min; preferably, the mobile phase adopts a methanol-water isocratic elution system, wherein the volume ratio of methanol to water is 44:55-45:56, preferably 45: 55; preferably, chromatographic peaks with retention time of 18-20.5min are collected and concentrated to obtain the flavonoid glycoside compounds.
On the other hand, the embodiment of the invention also provides the rose-bengal active extract, wherein the rose-bengal active extract comprises the flavonoid glycoside compounds.
Preferably, in the rosa forbescens active extract, the content of the flavonoid glycoside compound is 0.02-0.05%.
On the other hand, the preparation method of the rose bengal active extract comprises the following steps:
preparing a first solvent extract: leaching, extracting and post-treating the rose flowers with golden edges to obtain a first solvent extract;
and (3) column chromatography separation: performing column chromatography separation on the first solvent extract to obtain an active extract of the rosa laevigata containing the flavonoid glycoside compounds;
preferably, in the step of preparing the first solvent extract: the first solvent extract is an ethanol extract; further preferably, the step of preparing the first solvent extract specifically comprises: leaching the golden-edge rose by adopting an ethanol-water solution with the volume fraction of 90-100%, and concentrating the leaching solution to obtain a first extract; leaching the residue with 60-70% ethanol-water solution, and concentrating the leaching solution to obtain a second extract; extracting the first extract with a second solvent; combining the extracted remainder and the second extract, and performing freeze drying treatment to obtain a first solvent extract; preferably, the second solvent is petroleum ether;
preferably, in the column chromatography step: performing column chromatography separation on the first solvent extract by adopting macroporous resin; preferably, a methanol-water solvent system is adopted for gradient elution; wherein the initial volume fraction of methanol is 0-5%, and the final volume fraction of methanol is 90-100%; preferably, the active extract of Rosa canina containing flavonoid glycosides is obtained by mixing the eluates with methanol of 50-70 vol%, and concentrating.
On the other hand, the application of the rose mallow active extract in preparing or serving as an antioxidant and/or an antibacterial agent; preferably, the antioxidant is a DPPH radical scavenger; preferably, the antibacterial agent is an antibacterial agent against staphylococcus aureus.
In another aspect, the embodiments of the present invention further provide a composition, wherein the composition includes the flavonoid glycoside compound or the rosa citrifolia active extract;
preferably, the composition is any one of a pharmaceutical composition, a skin care composition and a food composition;
preferably, the flavonoid glycoside compound or the rosa forrestii active extract in the composition is used as an antioxidant and/or an antibacterial agent; further preferably, the antioxidant is a DPPH radical scavenger; further preferably, the antibacterial agent is an antibacterial agent for staphylococcus aureus.
Compared with the prior art, the flavonoid glycoside compound and the rose bengal active extract, and the preparation method and the application thereof have at least the following beneficial effects:
on one hand, the invention firstly provides a novel flavonoid glycoside compound which has double effects of oxidation resistance and antibiosis and can be used as an antioxidant and an antibacterial agent to be applied to skin care products, medicines and foods. The flavonoid glycoside compounds are natural and can be extracted from plants (such as Rosa canina), so that they have the advantages of safety and no toxicity when used as antioxidant and antibacterial agent (antiseptic).
Further, the flavonoid glycoside compounds provided by the invention can be extracted from the rosa laevigata, and specifically, the rosa laevigata is subjected to leaching, extraction and post-treatment by using an ethanol-water solution to obtain an ethanol extract, then the ethanol extract is subjected to column chromatography separation to obtain an active extract of the rosa laevigata, then the active extract of the rosa laevigata is subjected to silica gel column chromatography separation to obtain a target fraction, and finally the flavonoid glycoside compounds can be separated after the target fraction is purified. The flavone glycoside compounds can be extracted from the rosa forbescens through the synergistic cooperation of the steps.
On the other hand, the invention also provides a rosa forbescens active extract which comprises the flavonoid glycoside compound. Therefore, the rosa forbesii extract provided by the invention can be used as an antioxidant and an antibacterial agent to be applied to skin care products, medicines and foods, belongs to a natural source, and is safe and nontoxic.
In still another aspect, the present invention provides a composition comprising the above flavonoid glycoside compound or the above rose bengal active extract; the composition is any one of skin care composition, food composition and pharmaceutical composition; the flavone glycoside compound or the rose active extract is used as an additive to make the composition have antioxidant and antibacterial (antiseptic) effects.
The foregoing description is only an overview of the technical solutions of the present invention, and in order to make the technical solutions of the present invention more clearly understood and to implement them in accordance with the contents of the description, the following detailed description is given with reference to the preferred embodiments of the present invention and the accompanying drawings.
Drawings
FIG. 1 shows a flavonoid glycoside compound provided in the examples of the present invention1H-NMR spectrum;
FIG. 2 shows a flavonoid glycoside compound provided by the embodiment of the invention13C spectrum and dept spectrogram;
FIG. 3 shows a flavonoid glycoside compound provided by the embodiment of the present invention1H-1H COSY spectrogram;
FIG. 4 is an HSQC spectrum of a flavonoid glycoside compound provided by the embodiment of the present invention;
FIG. 5 is the HMBC chromatogram of a flavonoid glycoside compound provided by the embodiment of the present invention.
Detailed Description
To further illustrate the technical means and effects of the present invention adopted to achieve the predetermined objects, the following detailed description of the embodiments, structures, characteristics and effects according to the present invention will be made with reference to the accompanying drawings and preferred embodiments. In the following description, different "one embodiment" or "an embodiment" refers to not necessarily the same embodiment. Furthermore, the particular features, structures, or characteristics may be combined in any suitable manner in one or more embodiments.
Rosa canina (Rosa chinensis cv. 'JinBian') belongs to a cultivar under the China rose of Rosa of Rosaceae, is mainly developed into rose tea, and has wide planting area in Yunnan. At present, the chemical components and the biological activity of the rosa labrata thunb are rarely researched, and the invention researches the antioxidant and antibacterial active components in the rosa labrata thunb by means of natural medicinal chemistry research means.
The invention extracts a flavonoid glycoside compound from the rosa forbesii for the first time; wherein the structure of the flavonoid glycoside compound is shown as follows:
furthermore, the invention provides the application of the flavonoid glycoside compound in the antibacterial agent and/or the antioxidant for the first time (namely, the flavonoid glycoside compound can be directly used as the antibacterial agent and/or the antioxidant, or the flavonoid glycoside compound is used for preparing the antibacterial agent and/or the antioxidant).
In addition, the rose bengal active extract containing the flavonoid glycoside compounds also has antibacterial and antioxidant activities. Therefore, the rose bengal active extract can be directly used as an antibacterial agent and/or an antioxidant, or the rose bengal active extract is used for preparing the antibacterial agent and/or the antioxidant.
The flavonoid glycoside compounds and the active extract of Rosa canina can be used as antibacterial agent and antioxidant for skin care products, medicines and foods.
The term "skin care product" in the present invention means skin care water, skin care lotion, skin care mask, skin care cream, etc.; the skin care product of the embodiment of the invention can also be referred to as a cosmetic; and the skin care product of the embodiment of the invention can also refer to skin care medicines with antioxidant, anti-aging and antibacterial effects on the skin.
The invention is further illustrated in detail below by means of specific examples:
example 1
The present example prepares an active extract of rosa rugosa thunb, which includes the following steps:
selecting dry gold-edge rose flowers, crushing the dry gold-edge rose flowers, extracting the dry gold-edge rose flowers for three times by adopting an ethanol-water solution with the volume fraction of 95%, filtering, concentrating the filtrate, and recovering a solvent to obtain a first extract (namely 95% ethanol extract); extracting the residual plant residue (i.e. residue) with 65% ethanol-water solution for three times, filtering, concentrating the filtrate, and recovering solvent to obtain a second extract (i.e. 65% ethanol extract).
Adding water to the first extract for suspension, and extracting with petroleum ether for three times to remove small polar components; mixing the extraction residue and the second extract, and freeze drying to obtain ethanol extract.
Dissolving the ethanol extract in water, separating by macroporous resin (filler: HP-20) column chromatography, performing gradient elution with methanol-water solvent system (methanol volume fraction of 0-100%, during elution, methanol volume fraction of 0% and final volume fraction of 100%, and gradually increasing methanol concentration during gradient elution), and mixing the eluates with methanol volume fraction of 50-70%. Concentrating the combined elution fractions and recovering the solvent to obtain the active extract of the rosa forbesii.
Example 2
In the embodiment, the flavonoid glycoside compound is mainly separated from the rosa forrestii; the method specifically comprises the following steps:
1) preparing a rose mallotus active extract: the step is specifically referred to in example 1, and is not repeated herein.
2) Separating flavonoid glycoside compounds from the active extract of the rosa aurita: taking 15.68g of the active extract of the rosa rugosa thunb, and then carrying out silica gel column chromatography separation on the active extract of the rosa rugosa thunb; wherein, a chloroform-methanol solvent system is used for gradient elution (the volume ratio of chloroform to methanol is 1:1-9:1, wherein, during the gradient elution, the initial volume ratio of chloroform to methanol is 9:1, the final volume ratio is 1:1, and the concentration of chloroform is decreased progressively during the gradient elution process); after elution, the eluted fractions of chloroform and methanol in a volume ratio of 2:1 to 5:1 were combined to give a first fraction (subfraction B1). The first fraction (subfraction B1) was again separated by silica gel column; wherein a chloroform-methanol solvent system is adopted for gradient elution (the volume ratio of chloroform to methanol is 1:1-5:1, wherein, during the gradient elution, the initial volume ratio of chloroform to methanol is 5:1, the final volume ratio is 1:1, and the concentration of chloroform is decreased progressively during the elution process); after elution, the elution fractions with the chloroform-methanol volume ratio of 1:1-3:1 were combined to obtain the target fraction (fraction B1 a). The target fraction (fraction B1 a) was purified by reversed-phase high performance liquid chromatography (wherein the column type: YMC-Pack ODS-AQ,10 mm. times.250 mm, 5 μm; flow rate 3mL/min), the detection wavelengths were 220nm and 254nm, the mobile phase was an isocratic elution system of methanol-water at a volume ratio of 45:55, the chromatographic peak at a peak time of 19.47min was collected, and the solvent was concentrated and recovered to obtain 5mg of the target active compound A (i.e., the flavonoid glycoside compound).
3) Structural identification of the active compound a of interest:
the molecular formula of the target active compound A is determined by high resolution mass spectrum HR-ESI-MS [ M/z 897.1733[ M-H ]]-(calculated C41H38O23m/z897.1731[M-H]-)]Can be determined as C41H38O23。
According to one-dimensional nuclear magnetic resonance1H，13C and DEPT and two-dimensional nuclear magnetic resonance related signals, the structural formula of the target active compound A can be deduced to be shown as the following formula:
the two-dimensional correlation signals are shown below:
the nuclear magnetic resonance data and signal assignments of the target active compound a are shown in table 1.
TABLE 1 of the active compounds A of interest1H and13c NMR data attribution (CD)3OD)(δin ppm,J in Hz)
In addition, of the target active Compound A1H-NMR spectrum (600M, CD)3OD) is shown in figure 1; of the target active Compound A13C spectra and dept spectra (150M, CD)3OD) is shown in fig. 2; of the target active Compound A1H-1H COSY spectrogram (600MHz, CD)3OD) is shown in fig. 3; HSQC spectrum (600MHz, CD) of active Compound A of interest3OD) is shown in fig. 4; HMBC spectrum (600MHz, CD) of the active compound A of interest3OD) is shown in fig. 5.
In conclusion, the active compound a of interest isolated in this example was identified as a flavonoid glycoside compound represented by the above structure by the above test.
Example 3
In this example, an antioxidant activity assay experiment was performed on the flavonoid glycosides prepared in example 2 and the rosa laevigata active extract prepared in example 1, and the assay method is as follows:
the antioxidant activity was measured by DPPH free radical scavenging activity assay. Mixing a sample to be detected with a set concentration with DPPH (final concentration is 100mM) on a 96-well plate for reaction, setting 3 repeated wells, simultaneously setting a blank control without a medicament and a Trolox positive control, standing at 30 ℃ for 1h, and then determining an OD value by using an enzyme labeling instrument, wherein the detection wavelength is 515 nm.
Wherein the antioxidant rate is calculated according to the formula: oxidation resistance (%) (1-well experiment OD)515nmBlank well OD515 nm)×100％。
The results of the measurement of antioxidant activity are shown in table 2.
Table 2 shows the results of measuring the antioxidant activity of flavonoid glycoside compounds and the active extract of Rosa rugosa Thunb
As can be seen from table 2: the flavonoid glycoside compound and the rose active extract prepared by the embodiment of the invention have excellent antioxidant activity.
Example 4
In this embodiment, the flavonoid glycoside compound prepared in example 2 and the rosa labra active extract prepared in example 1 are mainly subjected to antibacterial activity determination, and the specific steps are as follows:
staphylococcus aureus (StaphyLococcus aureus) ATCC29213 was inoculated on LB medium and cultured in an incubator at 35 ℃. Picking a small amount of activated bacterial colonies by using an inoculating loop, transferring the bacterial colonies into a sterilized dry turbidimetric tube, diluting the bacterial colonies by using sterile physiological saline with the mass fraction of 0.9 percent, preparing a bacterial suspension with the concentration of 0.5 # Mach turbidimetric tube (1 × 108CFU/mL) according to the method standard of the 2017 CLSI related file, and diluting the prepared bacterial suspension by using sterile physiological saline with the mass fraction of 0.9 percent at a ratio of 1:100 to obtain the bacterial suspension with the concentration of 1 × 106 CFU/mL. Preparing a system mixed solution according to the quantity of the reaction coefficient plus 0.5, and then subpackaging 200ul into each reaction tube, wherein the final concentration of the sample is 128ug/mL, and the final concentration of the bacteria is 5 multiplied by 105 CFU/mL. Taking a 96-well culture plate, and respectively placing the mixed solution into each well (each sample is 3 in parallel); after culturing at 37 ℃ for 24h, determining the OD value under 625nm by using an enzyme-labeling instrument, setting penicillin G sodium as a positive control group, and calculating the inhibition rate and half bacteriostatic concentration. The results of the antimicrobial activity assay of the samples are shown in table 3.
Table 3 shows the results of the measurement of the antibacterial activity of the flavonoid glycoside compounds and the rose bengal extract against Staphylococcus aureus
As can be seen from table 3: the flavonoid glycoside compound prepared by the invention has obvious antibacterial activity, and the rose mallow active extract containing the flavonoid glycoside compound also has medium antibacterial activity.
In summary, the flavonoid glycoside compound and the rose bengal active extract provided by the embodiment of the invention have double effects of antioxidant activity and antibacterial activity, and can be used as an antioxidant and an antibacterial agent (preservative) to be applied to products such as skin care products, foods, medicines and the like.
While the invention has been described with reference to the preferred embodiments, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention as defined by the appended claims.
Claims (11)
1. The preparation method of the flavonoid glycoside compound is characterized in that the structure of the flavonoid glycoside compound is as follows:
the flavonoid glycoside compound is separated from a first plant, and the first plant is rose bengal;
wherein the step of separating the flavonoid glycoside compound from the rosa forrestii comprises the following steps:
1) leaching, extracting and post-treating the rose flowers with golden edges to obtain a first solvent extract;
wherein the first solvent extract is an ethanol extract; the step 1) is specifically as follows: leaching the golden-edge rose by adopting an ethanol-water solution with the volume fraction of 90-100%, and concentrating the leaching solution to obtain a first extract; leaching the residue with 60-70% ethanol-water solution, and concentrating the leaching solution to obtain a second extract; extracting the first extract with a second solvent; mixing the extracted remainder and the second extract, and performing freeze drying treatment to obtain a first solvent extract; the second solvent is petroleum ether;
2) performing column chromatography separation on the first solvent extract to prepare a rosa laevigata active extract containing the flavonoid glycoside compound; wherein, macroporous resin is adopted to carry out column chromatography separation on the first solvent extract; gradient elution is carried out by adopting a methanol-water solvent system; wherein the initial volume fraction of methanol is 0-5%, and the final volume fraction of methanol is 90-100%; mixing the eluted fractions with methanol volume fraction of 50-70%, and further concentrating to obtain flos Rosae Rugosae active extract containing flavonoid glycosides;
3) carrying out silica gel column chromatography separation on the rosa forbescens active extract to obtain a target fraction containing the flavonoid glycoside compound;
wherein the step 3) comprises: performing silica gel column chromatography separation on the active extract of the rosa forbescens, and performing gradient elution by using a chloroform-methanol solvent system; wherein the initial volume ratio of chloroform to methanol is 8:1-10: 1; the final volume ratio of chloroform to methanol is 3:2 to 2: 3; wherein, the elution fractions with the volume ratio of chloroform to methanol of 2:1-5:1 are combined to obtain a first fraction; the first fraction is separated again by silica gel column chromatography, and gradient elution is carried out by a chloroform-methanol solvent system; wherein the initial volume ratio of chloroform to methanol is 4:1-6: 1; the final volume ratio of chloroform to methanol is 1:2 to 3: 2; wherein, the elution fractions with the volume ratio of chloroform to methanol being 1:1-3:1 are combined to obtain the target fraction;
4) purifying the target fraction by adopting reverse-phase high performance liquid chromatography to separate the flavonoid glycoside compound; wherein the mobile phase adopts a methanol-water isocratic elution system, wherein the volume ratio of methanol to water is 44:55-45: 56; wherein, collecting chromatographic peak with retention time of 18-20.5min, and concentrating to obtain the flavonoid glycoside compound.
2. The method of claim 1, wherein the flavonoid glycoside is used as or in the preparation of an antioxidant and/or an antibacterial agent.
3. The method for producing flavonoid glycosides according to claim 2,
the antioxidant is a DPPH free radical scavenger.
4. The method for producing flavonoid glycosides according to claim 2,
the antibacterial agent is an antibacterial agent of staphylococcus aureus.
5. The method for producing a flavonoid glycoside compound according to claim 1, wherein in said step 3):
when the rosa forbescens active extract is subjected to silica gel column chromatography separation, the initial volume ratio of chloroform to methanol is 9: 1.
6. The method for producing a flavonoid glycoside compound according to claim 1, wherein in said step 3): when the rose mallotus philippinensis active extract is subjected to silica gel column chromatography separation, the final volume ratio of chloroform to methanol is 1: 1.
7. The method for producing a flavonoid glycoside compound according to claim 1, wherein in said step 3):
when the first fraction was separated again by silica gel column chromatography, the initial volume ratio of chloroform to methanol was 5: 1.
8. The method for producing a flavonoid glycoside compound according to claim 1, wherein in said step 3): when the first fraction was again separated by silica gel column chromatography, the final volume ratio of chloroform to methanol was 1: 1.
9. The method for producing a flavonoid glycoside compound according to claim 1, wherein in said step 4): the target flow is prepared by high performance liquid chromatography, and the detection wavelength is 220nm and 254 nm.
10. The method for producing flavonoid glycosides according to claim 9, wherein the type of the column used is YMC-Pack ODS-AQ; the flow rate was 3 mL/min.
11. The method according to claim 10, wherein the volume ratio of methanol to water is 45: 55.
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