CN113877237A - Method for extracting and identifying flavonoid metabolites in plum blossom petals - Google Patents

Method for extracting and identifying flavonoid metabolites in plum blossom petals Download PDF

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CN113877237A
CN113877237A CN202111095417.7A CN202111095417A CN113877237A CN 113877237 A CN113877237 A CN 113877237A CN 202111095417 A CN202111095417 A CN 202111095417A CN 113877237 A CN113877237 A CN 113877237A
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extraction
flavonoid
plum blossom
ultrasonic
extraction method
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张�杰
吴思惠
马召旭
高蓉蓉
熊涛
朱欢欢
张俊卫
包满珠
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Huazhong Agricultural University
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    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
    • G01N30/02—Column chromatography
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/02—Solvent extraction of solids
    • B01D11/0261—Solvent extraction of solids comprising vibrating mechanisms, e.g. mechanical, acoustical
    • B01D11/0265—Applying ultrasound
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D11/00—Solvent extraction
    • B01D11/02—Solvent extraction of solids
    • B01D11/0288—Applications, solvents

Abstract

The invention relates to the technical field of natural compound extraction and identification, in particular to a method for extracting and identifying flavonoid metabolites in plum blossom petals. The extraction method used by the invention is ultrasonic extraction, the ultrasonic temperature is not more than 25 ℃, and the ultrasonic time is 15-45 min; the ultrasonic power is 160-200W. The extract obtained by the extraction method can be directly used for flavonoid identification, and 31-50 flavonoid compounds can be effectively identified. The extraction and identification method provided by the invention has important significance for effectively evaluating and utilizing plum blossom germplasm resources.

Description

Method for extracting and identifying flavonoid metabolites in plum blossom petals
Technical Field
The invention relates to the technical field of natural compound extraction and identification, in particular to a method for extracting and identifying flavonoid metabolites in plum blossom petals.
Background
The flavonoid compound is widely present in various plants, and has various physiological activities and medicinal values of resisting oxidation and tumors, improving immune function, regulating blood fat and the like. The human body ingests flavonoids mainly by eating vegetables and fruits.
Plum blossom is a plant of Prunus of Rosaceae (Rosaceae), has been cultivated in the south of China for over three thousand years, and contains abundant flavonoid substances. Related researches are few at present on the extraction process of the flavonoids in the plum blossom, the plum blossom bioflavonoid mixture has no formal national standard, and no systematic and complete extraction method exists. The existing method for extracting and measuring the plum blossom petal flavonoid has the defects of complicated operation steps, much sample waste and the like.
In the prior art, after the plum blossom flavonoid is extracted, the extract cannot be subjected to accurate characteristic identification analysis due to low purity and high impurity content, and the characteristic of the plum blossom flavonoid component has no unified identification standard.
Disclosure of Invention
The invention aims to provide a method for extracting and identifying flavonoid metabolites in plum blossom petals.
When the organic solvent is used as an extracting agent for extracting flavonoid metabolites from the plum blossom petals, the extracting agent can not only extract the flavonoid, but also dissolve other metabolites from the plum blossom petals. In order to ensure that the purity of the extracted plum blossom flavonoid is higher, the plum blossom flavonoid can be directly tested on a machine. The invention optimizes the ultrasonic extraction process and the extracting agent.
The specific technical scheme provided by the invention is as follows:
the invention provides a method for extracting flavonoid, which uses ultrasonic treatment to assist extraction, wherein the temperature of ultrasonic treatment is not more than 25 ℃, and the time of ultrasonic treatment is 15-45 min; the ultrasonic power is 160-200W.
In the prior art, the extraction temperature is usually 60-80 ℃ because high temperature increases the extraction efficiency. The invention adopts low-temperature extraction, and overcomes the defect of low-temperature extraction efficiency and the defect of degradation of partial extract caused by high temperature by optimizing the ultrasonic time, the ultrasonic power and the extracting agent.
In the extraction method provided by the invention, the extracting agent is ethanol or methanoic acid.
In the extraction method provided by the invention, the ethanol is 55-65% ethanol; the methanoic acid is 1.5-2.5% methanoic acid.
In the extraction method provided by the invention, the material-liquid ratio of the used petals to the extracting agent is (0.015-0.025 g): 120-200 muL.
In the prior art, more raw materials and extracting agents are generally used, more flavonoids are expected to be extracted, after the extraction process is optimized, the high extraction rate can be obtained under the ultrasonic treatment of a small amount of raw materials and extracting agents, and the extract can be directly subjected to sample loading identification analysis.
Specifically, the extraction method provided by the invention comprises the steps of grinding petals, adding 55-65% of ethanol extracting agent, shaking uniformly, and treating for 30-45min at 4-25 ℃ by using 160-200W.
The extraction method provided by the invention also comprises the steps of placing the leaching liquor for 12-24 hours at the temperature of 4 ℃, centrifuging, collecting supernate, and carrying out quantitative analysis by using a spectrophotometer according to a rutin standard curve.
The use of the above extraction process in the production of flavonoid products is claimed in the present invention, as will be appreciated by those skilled in the art.
In a second aspect, the invention claims a plum blossom flavonoid product extracted by using the extraction method.
In a third aspect, the present invention provides a method for identifying flavonoids, wherein after the extract is obtained by the above extraction method, the flavonoid components are analyzed by high performance liquid chromatography-mass spectrometry.
The invention also requests to protect the application of the extraction method or the identification method in the screening of plum blossom germplasm resources.
The invention has the beneficial effects that:
(1) the extraction method provided by the invention ensures that the plum blossom flavonoid is stable and not degraded in the extraction process by optimizing the ultrasonic time, temperature, power and leaching agent, and ensures that the flavonoid extract with high extraction rate and capable of being directly subjected to sample loading detection is obtained by accurately controlling the material-liquid ratio;
(2) the flavonoid obtained by the extraction method has high purity and less impurities, and can be directly subjected to on-line detection on an LC-Q-TOF-MS (liquid chromatography-quadrupole-time of flight-mass spectrometry) instrument;
(3) the extract obtained by the method can accurately identify the characteristic components of 31-50 flavonoids in plum blossom petals, and provides good theoretical support for identifying plum blossom germplasm resources.
Drawings
Fig. 1 is a positive mode ion flow diagram in embodiment 1 of the present invention.
Fig. 2 is a negative mode ion flow diagram in example 1 of the present invention.
Fig. 3 is a positive mode ion flow diagram in embodiment 2 of the present invention.
Fig. 4 is a negative mode ion flow diagram in embodiment 2 of the present invention.
Detailed Description
The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
In the embodiment of the invention, the plum blossom is cinnabar with white whiskers, and the cinnabar with white whiskers is cultivated in various places in China.
The preparation method of the rutin standard curve in the embodiment of the invention comprises the following steps:
(1) accurately weighing 0.010g of rutin standard substance, adding 60% ethanol lixiviant for dissolving to constant volume to 5ml, and preparing into standard substance solution with mass concentration of 2 mg/ml.
(2) Respectively sucking 25 μ l, 50 μ l, 100 μ l, 150 μ l and 200 μ l of the standard solution into 5 test tubes, and adding 5% NaNO by mass2Shaking the solution 100 μ l, standing for 6min, adding 10% Al (NO)3)3Shaking the solution 100 μ l uniformly and standing for 6 min; then 1000 mul of NaOH solution with the mass fraction of 4 percent is added, water is added to 2.5ml, and the mixture is shaken up and placed for 15 min.
(3) Measuring absorbance of rutin standard solution with different mass concentrations at 510nm with UV-4802 double-beam scanning type ultraviolet-visible spectrophotometer with distilled water as blank reference, and drawing standard curve according to absorbance value and rutin standard solution concentration.
(4) Solving linear regression equation Abs 10.872c-0.1135 (R) by least square method20.9963, Abs is absorbance; and c is the mass concentration (mg/mL) of the total flavonoids.
Example 1 extraction and identification analysis of plum blossom petal flavonoid
The embodiment provides a method for extracting and quantitatively analyzing flavonoid in plum blossom petals, which comprises the following specific steps:
(1) taking petals of 'white-whisker cinnabar' in the full-bloom period as a test material, quickly freezing a fresh plum blossom sample in liquid nitrogen, weighing 0.015-0.025g of a plum blossom petal freeze-dried sample by an electronic balance, placing the plum blossom petal freeze-dried sample in a grinding tube of 2ml after quick freezing in liquid nitrogen, adding two steel balls into each tube, and automatically grinding by a grinding instrument.
(2) According to the material-liquid ratio of 1: 8000 (g/mul) of the extracting agent is added, the mixture is shaken by a vortex instrument and is stirred evenly, and an ultrasonic cleaner is used for ultrasonic treatment at the temperature of 25 ℃; in the embodiment, the extractant is 60% ethanol, the ultrasonic power of ultrasonic-assisted extraction is 200W, the ultrasonic time is 45min, and ice blocks are added during the ultrasonic period to ensure that the temperature does not exceed 25 ℃.
(3) The sample is placed at 4 ℃ for 24h and then centrifuged, with the centrifugation speed of 13000rmp for 10 min.
(4) Calculating the extraction amount of total flavonoids in plum blossom: according to a rutin standard curve, a UV-4802 double-beam scanning type ultraviolet visible spectrophotometer is used for quantitatively analyzing the total flavonoid content in the plum blossom petal sample, and the extraction rate of the 'white-whisker cinnabar' petal flavonoid in the full-bloom stage is 14.1731%.
(5) Obtaining mass spectrum information by using a Q-TOF-LC-MS (liquid chromatography-mass spectrometry) instrument, wherein the model of the Q-TOF instrument is 6520mass spectrometer; the chromatographic column is Thermo Hypersil Gold C18,100mm 2.1mm, 1.9 μm; the column temperature is 35 ℃; 28 min; the flow rate is 0.3 ml/min; the sample injection amount is 5 mu L; the scanning range is 30m/z-1200 m/z; full-scan Electrospray (ESI) is performed in positive and negative mode; drying gas (drying gas nitrogen) is 10L/min; gas temperature (gas temperature)350 ℃; atomization gas pressure (nebulizer pressure)40 psig; capillary voltage (capillary voltage)3.5 kv; rupture voltage (fragmentor)135 v; skimmer (skimmer)65 v; collision energy (The collision energy) is 10eV, 20eV, 30eV, respectively; the ultraviolet DVD has wavelength of 520nm, 350nm, and 320 nm. Mobile phase a (ultrapure water containing 0.1% V formic acid), mobile phase B (acetonitrile containing 0.1% V formic acid). Gradient elution conditions 0min 5% B; 20min 95% B; 22min 95% B; 22.1min 5% B; 28min 5% B, positive mode ion flow diagram see fig. 1, negative mode ion flow diagram see fig. 2. The peak types in fig. 1 and fig. 2 are clear, and the number of the peaks is large, which proves that the extract obtained by the extraction of the embodiment has high flavonoid content and abundant varieties.
And (3) comparing the m/z value and the ion fragment mode of the metabolite obtained according to the high performance liquid chromatography mass spectrum with the metabolites in a common mass spectrum database or published documents to identify the metabolite. Mass spectra libraries include METLIN (https:// METLIN. script. edu /), Mass Bank (http:// www.massbank.jp /), and HMDB (http:// www.hmdb.ca /). The metabolites obtained in this example are shown in Table 1. The retention time in Table 1 represents the time from the start of injection until a concentration maximum of a certain component appears after the column, the value of the molecular ion [ M + ] or [ M-H ] -represents the mass-to-charge ratio of the excimer ion peak, and the value of the fragment ion represents the mass-to-charge ratio of the product ion generated by the cleavage of the excimer ion.
Most of the former people only identify the anthocyanin compounds of the red plum blossom, and flavonoid substances except the anthocyanin are not comprehensively identified. When identifying yellowish green ' changed green calyx ' plum blossom, 13 identified flavonoid substances comprise perbenzoic acid, isorhamnetin, quercetin, kaempferol 3-O-beta-D-galactopyranoside, isorhamnetin-3-O-beta-D-glucopyranoside, isoquercitrin, hyperoside, rutin, isoquercitrin-6 ' -O-benzonate, pinoresinol, naringenin, ethyl-beta-D-glucopyranoside and astragalin.
This example first extracts and fully identifies purplish red 'white fibrous cinnabar' plum flavonoids.
This example identifies 50 important flavonoids in the petals of the 'white whisker cinnabar' plum blossom. The results are shown in Table 1. The invention firstly extracts and identifies cyanidin compounds, namely delphinidin and glycoside thereof, as well as chalcone, epicatechin and other substances except cyanidin and glycoside thereof, paeoniflorin and glycoside thereof from plum blossom.
TABLE 1 Flavonoids in the petals of Cinnabaris, Callicarpa obliqua, in the bloom stage
Figure BDA0003269030700000061
Figure BDA0003269030700000071
Figure BDA0003269030700000081
Figure BDA0003269030700000091
Figure BDA0003269030700000101
Example 2 extraction and quantitative analysis of plum blossom petal flavonoid
The method adopted in this example is the same as example 1, except that in step (2) of this example, the leaching agent is 2% formic acid methanol, the ultrasonic power for ultrasonic-assisted extraction is 200W, the ultrasonic time is 30min, and ice blocks are added during the ultrasonic period to make the temperature not exceed 25 ℃. The extraction rate of the obtained flavonoid was 12.9553%. And (3) obtaining mass spectrum information by using a Q-TOF-LC-MS (liquid chromatography-mass spectrometry) instrument, wherein a positive mode ion flow diagram is shown in figure 3, and a negative mode ion flow diagram is shown in figure 4. The peak patterns in fig. 3 and fig. 4 are clear, and the number of the peaks is large, which proves that the extract obtained by the extraction of the embodiment has high content and abundant varieties of flavonoids.
And (3) comparing the m/z value and the ion fragment mode of the metabolite obtained according to the high performance liquid chromatography mass spectrum with the metabolites in a common mass spectrum database or published documents to identify the metabolite. Mass spectra libraries include METLIN, Mass Bank and HMDB, and 31 flavonoid compounds were obtained in this example, as shown in Table 2. The retention time in Table 2 represents the time from the start of injection until a concentration maximum of a certain component appears after the column, the value of the molecular ion [ M + ] or [ M-H ] -represents the mass-to-charge ratio of the excimer ion peak, and the value of the fragment ion represents the mass-to-charge ratio of the product ion generated by the cleavage of the excimer ion.
This example identifies a total of 31 important flavonoids in plum blossom petals. The anthocyanin compounds, namely delphinidin and glycoside thereof, as well as chalcone, epicatechin and other substances except cyanidin and glycoside thereof, paeoniflorin and glycoside thereof are extracted and identified from the plum blossom for the first time.
TABLE 2 Flavonoids in the petals of Cinnabaris, Callicarpa obliqua, in the bloom stage
Figure BDA0003269030700000111
Figure BDA0003269030700000121
Figure BDA0003269030700000131
Figure BDA0003269030700000141
Comparative example 1 extraction Effect of different sonication times
The comparative example adopts the same extraction method as the example 1, and is different in that in the step (2), the ultrasonic time is 15min, 30min, 45min and 60 min; the flavonoid extraction rates in this comparative example are shown in table 3.
TABLE 3 extraction Effect for different sonication times
Figure BDA0003269030700000142
Wherein a, b and c represent the significant difference of the Duncan analysis of variance at the significance level of P0.05.
Comparative example 2 extraction Effect of different extractants
This comparative example was conducted in the same manner as in example 1 except for the difference in step (2). The extraction solvent is ethyl acetate-ethanol (1: 1, V/V). In this comparative example, ethyl acetate-ethanol was used as the extraction solvent, and the obtained flavonoid extraction yield is shown in table 4.
TABLE 4 ultrasonic extraction rate of ethyl acetate-ethanol as extraction solvent
Figure BDA0003269030700000143
As can be seen from table 4, when ethyl acetate-ethanol was used as the extraction solvent, the flavonoid extraction rate was significantly lower than that when 60% ethanol or 2% methanol formate was used as the extraction solvent.
Comparative example 3 extraction effect at different temperatures during sonication
The comparative example used the same extraction method as in example 1, except that the temperature during sonication was 60 ℃, the sonication power was 200W, sonication was 45min, and the flavonoid extraction rate was 13.225%, the results are shown in table 5.
TABLE 5 extraction Effect at different temperatures
Figure BDA0003269030700000151
Comparative example 4 Effect of optimizing ultrasonic Power, ultrasonic time, leaching agent
The comparative example, which was identical to example 1 in terms of ultrasound temperature and extraction procedure, provides results optimized for different ultrasound powers, ultrasound times, and extractants, as shown in table 6.
TABLE 6
Figure BDA0003269030700000152
Figure BDA0003269030700000161
As can be seen from the results of table 6, different ultrasonic powers, ultrasonic times and leaching agents produced different extraction effects, and either higher extraction rates were obtained with higher ultrasonic powers or higher extraction rates were obtained with longer ultrasonic times.
Further, as can be seen from the above data, the most influential factor in the extraction process on the extraction rate was the extractant (extractant), and the relationship of the flavonoid species to the extractant and the ultrasonic power and ultrasonic time was not clear. For example, when 2% methanol formate is used, the ultrasonic power for ultrasonic-assisted extraction is 200W, and the ultrasonic time is 30min, the obtained flavonoid extraction rate is 12.9553%, and 31 flavonoid species are identified; when 60% ethanol is used as an extracting agent, the ultrasonic power is 200W, and the ultrasonic time is 45min, the extraction rate is only improved to 14.1731%, and the identified flavonoid species reach 50.
Therefore, the ethanol is used as an extracting agent, the ultrasonic treatment temperature is not more than 25 ℃, and the ultrasonic treatment time is 15-45 min; the extract obtained by the extraction method with the ultrasonic power of 160-200W is most suitable for identifying the plum blossom flavonoid species.
Although the invention has been described in detail hereinabove with respect to a general description and specific embodiments thereof, it will be apparent to those skilled in the art that modifications or improvements may be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.

Claims (10)

1. The extraction method of flavonoid is characterized in that ultrasonic treatment is used for assisting extraction, the temperature of ultrasonic treatment is not more than 25 ℃, and the time of ultrasonic treatment is 15-45 min; the ultrasonic power is 160-200W.
2. The extraction process according to claim 1, wherein the leaching agent is ethanol or methanoic acid.
3. The extraction process according to claim 2, characterized in that the ethanol is 55-65% ethanol.
4. The extraction method according to any one of claims 1 to 3, wherein the petal to lixiviant ratio is (0.015g-0.025g) to (120 μ L-200 μ L).
5. The extraction method as claimed in any one of claims 1 to 4, wherein the petals are ground, added with 55-65% ethanol extractant, shaken and treated with 200W at 4-25 ℃ for 30-45 min.
6. The extraction method according to claim 5, wherein the extraction method further comprises standing the leach liquor for 12-24h, centrifuging, collecting the supernatant, and performing quantitative analysis using a spectrophotometer according to a rutin standard curve.
7. Use of the extraction process of any one of claims 1 to 5 in the manufacture of a flavonoid product.
8. A plum blossom flavonoid product obtained by extraction using the extraction method according to any one of claims 1 to 5.
9. A method for identifying flavonoids, characterized in that after the extract is obtained by the extraction method according to any one of claims 1 to 5, the flavonoid components are analyzed by high performance liquid chromatography-mass spectrometry.
10. Use of the identification method of claim 9 for screening quincunx germplasm resources.
CN202111095417.7A 2021-09-17 2021-09-17 Method for extracting and identifying flavonoid metabolites in plum blossom petals Pending CN113877237A (en)

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