CN113337141B - Preparation method of lycium ruthenicum murr yellow anthocyanin - Google Patents
Preparation method of lycium ruthenicum murr yellow anthocyanin Download PDFInfo
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- 241000169546 Lycium ruthenicum Species 0.000 title claims abstract description 41
- 238000002360 preparation method Methods 0.000 title description 6
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- 238000000034 method Methods 0.000 claims abstract description 23
- 239000003960 organic solvent Substances 0.000 claims abstract description 15
- 239000001060 yellow colorant Substances 0.000 claims abstract description 5
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- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 8
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- 238000007254 oxidation reaction Methods 0.000 description 3
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- 241000208292 Solanaceae Species 0.000 description 1
- 206010057040 Temperature intolerance Diseases 0.000 description 1
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
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- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
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- 150000008131 glucosides Chemical class 0.000 description 1
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- 230000008543 heat sensitivity Effects 0.000 description 1
- 230000009245 menopause Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 150000002982 petunidin derivatives Chemical class 0.000 description 1
- 150000007965 phenolic acids Chemical class 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
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- 150000008265 rhamnosides Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
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- 235000014101 wine Nutrition 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B61/00—Dyes of natural origin prepared from natural sources, e.g. vegetable sources
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0096—Purification; Precipitation; Filtration
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
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- Biotechnology (AREA)
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Abstract
The invention provides a method for extracting and preparing yellow anthocyanin from lycium ruthenicum murr, which mainly adopts inorganic salt, organic solvent and other modes for extraction. The obtained anthocyanin has similar color characteristics to bright yellow (CAS: 56279-27-7), and can be used as natural substitute for chemical synthetic yellow colorant.
Description
Technical Field
The invention relates to the technical field of plant extraction, and particularly relates to a preparation method of lycium ruthenicum murr yellow anthocyanin.
Background
Lycium ruthenicum (Lycium ruthenicum Murr.) belongs to Lycium of Solanaceae, is mainly distributed in middle Asia region, is distributed in Qinghai, ningxia, xinjiang, gansu, shaanxi and other places in China, and is a specific perennial shrub wild plant in arid region of China. According to the records of the four medical classics, the lycium ruthenicum murr is used for treating diseases such as heart heat disease, heart disease, irregular menstruation, menopause and the like in the Tibetan medicine; folk medicine is used as tonic, eyesight improving and blood pressure lowering medicine. Researches show that the lycium ruthenicum contains various active ingredients such as polysaccharide, flavone, proanthocyanidin, anthocyanin and phenolic acid, and has the effects of resisting fatigue, reducing blood sugar, resisting oxidation, inhibiting tumors, nourishing, protecting health and the like.
Anthocyanins (Anthocyanines) are water-soluble natural pigments widely existing in plants in nature, and belong to flavonoid compounds. Anthocyanins mainly exist in the forms of glucoside, rhamnoside, etc. in fruits, epidermis and flowers of plants. The content of anthocyanin in the lycium ruthenicum is extremely high, wherein more than 90% of anthocyanin is a petunidin derivative, has the functions of resisting oxidation, protecting eyesight, inhibiting tumors and the like, and has important biological activity and extraction value. However, the lycium ruthenicum anthocyanin has the characteristics of easiness in oxidation, heat sensitivity, extremely poor stability and the like, and a large number of sugar chains connected through glycosidic bonds can directly influence the purity of the anthocyanin, so that the extraction, separation and purification are difficult, and the effective extraction rate of the lycium ruthenicum anthocyanin in the prior art is low.
At present, it is reported at home and abroad that lycium ruthenicum anthocyanin is prepared by taking lycium ruthenicum fruits as raw materials, adopting a solvent extraction method and assisting modern technologies such as ultrasound, microwave, enzyme and the like for conventional preparation, the obtained lycium ruthenicum anthocyanin is all magenta, the aqueous solution of the anthocyanin is usually all magenta, and the anthocyanin shows color characteristics similar to bright blue (CAS: 3844-45-9) only under a specific pH value. Natural blue colorant containing anthocyanin is disclosed in patent publication No. CN105339437A, and anthocyanin is disclosed in patent publication No. CN109574979A as a blue colorant. However, no related yellow anthocyanin natural colorant is reported.
From the above, it is found that no natural yellow colorant containing anthocyanin has been reported. Therefore, the lycium ruthenicum anthocyanin which is simple and efficient to prepare and yellow has important significance and good market prospect.
Disclosure of Invention
In order to solve the problems, the invention relates to a simple and efficient method for providing lycium ruthenicum anthocyanin which is yellow.
Specifically, the invention provides a method for extracting and preparing yellow anthocyanin from lycium ruthenicum, which comprises the following steps:
(1) Adding lycium ruthenicum superfine powder into an inorganic salt A water solution and a hydrophilic low-molecular organic solvent, extracting, standing and phase splitting;
(2) Removing the upper phase solvent, adding anhydrous ethanol to precipitate inorganic salt, filtering, removing anhydrous ethanol from the liquid part to obtain solid, re-dissolving the solid in the inorganic salt B water solution, standing, and removing the solvent under reduced pressure to obtain yellow anthocyanin;
the inorganic salt A is selected from one or the combination of more than two of sodium chloride, ammonium sulfate, potassium dihydrogen phosphate and dipotassium hydrogen phosphate; the hydrophilic low molecular organic solvent is one or more of methanol, ethanol, acetone, isopropanol and n-butanol; the inorganic salt B is selected from magnesium chloride: calcium chloride: aluminum chloride is 0.2m.
Further, the inorganic salt a is selected from ammonium sulfate.
Further, the hydrophilic low-molecular organic solvent is selected from ethanol.
Wherein, in the step (2), the solid is re-dissolved in 0.1-3mg/mL of inorganic salt B aqueous solution with the concentration of 0-2 mol/L.
Wherein the hydrophilic low molecular organic solvent accounts for 20-40% of the total mass of the inorganic salt A aqueous solution and the hydrophilic low molecular organic solvent.
Wherein the inorganic salt A accounts for 15-25% of the total mass of the inorganic salt A aqueous solution and the hydrophilic low molecular weight organic solvent.
Wherein the total mass ratio of the lycium ruthenicum superfine powder to the inorganic salt A water solution and the hydrophilic low-molecular organic solvent is 1:5-1:20.
wherein, the extraction method of step (1) can adopt conventional extraction methods, such as ultrasound, dipping, reflux and the like. Ultrasonic extraction may be employed in the present invention.
The invention also provides the yellow anthocyanin prepared by the method.
The invention also provides a yellow colorant, which is characterized in that: it comprises the yellow anthocyanin of claim 9.
The invention provides lycium ruthenicum murr yellow anthocyanin: the aqueous solution has strong absorption peak at 500-780nm and hue angle h ab The value is 85 to 100; the powder is a yellow powder with metallic luster, and the powder has the highest reflection peak at 780 nm.
The method can effectively obtain the yellow anthocyanin of the lycium ruthenicum murr, and has the following advantages compared with the existing yellow coloring agent:
(1) The anthocyanin has similar color characteristics with bright yellow (CAS: 56279-27-7), and can be used as natural substitute of chemical synthetic yellow colorant;
(2) The process has simple steps, refined working procedures and high preparation efficiency.
Drawings
FIG. 1 Spectrophotometric spectra of products
FIG. 2 is a CIE1931 observer plot
FIG. 3 CIE1931 observer plots of different inorganic salt treatments
Detailed Description
In order that the present invention may be more readily understood, the present invention is further described without limiting in any way the invention by reference to the following specific examples which are intended only to illustrate the invention and are not intended to limit the scope of the invention, which are intended to be within the scope of the claims of the invention without departing from the technical solution of the invention.
Example 1 Lycium ruthenicum Murr yellow anthocyanin and preparation method thereof
(1) Crushing the dried lycium ruthenicum mill by using an ultrafine crusher, and sieving by using a 100-mesh sieve to obtain lycium ruthenicum submicron powder;
(2) Weighing 1.7g of ammonium sulfate, adding 5.9g of water to prepare an aqueous solution, then adding 2.4g of absolute ethyl alcohol to prepare an ethanol-ammonium sulfate two-aqueous-phase system, adding 1.0g of lycium ruthenicum super micropowder into the two-aqueous-phase system, carrying out ultrasonic assisted extraction for 30min, and standing for 1h at room temperature for layering;
(3) And (3) after the solvent is rotatably evaporated at the temperature of 50 ℃ on the upper phase in the step (2), dissolving the solvent with absolute ethyl alcohol, filtering and recovering inorganic salt, and rotatably evaporating at the temperature of 50 ℃ again to recover the absolute ethyl alcohol to obtain 50 mg of a crude anthocyanin product, wherein the content of the anthocyanin is 14% when the content of the anthocyanin is measured, the anthocyanin is redissolved in a mixed ion solution at the concentration of 0.2mg/mL, and each magnesium chloride in the ion solution is as follows: calcium chloride: the molar concentration ratio of aluminum chloride is 0.2M;
evaluation of analysis
Measuring the absorbance of the sample in the wavelength range of 380 to 780nm according to the specification of SN/T4675.25-2016 CIE1976 (L a b) color space law, pages 2 to 5, integrating the absorbance by a relative color stimulus function and a color matching function, comparing with a standard tristimulus value, and calculating the hue angle h of the sample ab A value; the reflectance spectrum of the sample is measured and the hue angle h of the sample is calculated according to the regulations on pages 2 to 4 of GB/T3979-2008 measuring method of body color ab A value; reference is made to AOAC Official Method 2005.02 Total monomer analysis antibiotic Content of Fruit J uises, beverages, natural colors and Wines pHDifferential Method First Action 2005 (J.AOAC int. 88,1269 (2005)), the anthocyanin content of the sample is determined.
Tests prove that the 0.2mg/mL aqueous solution of the lycium ruthenicum anthocyanin prepared by the method has an absorption peak h at 520-780 nm as shown in figure 1 ab A value of 99.32, as shown in FIG. 2 for the position of the aqueous solution in CIE1931 observer coordinates; the pH value is 7.0; the lycium ruthenicum anthocyanin is yellow powder with metallic luster, and has the highest reflection peak at 780 nm; the anthocyanin content of the lycium ruthenicum anthocyanin A is 14%.
Test examples
Using the method of example 1, the ratio of magnesium chloride: calcium chloride: relationship between aluminum chloride ratio and product color
The color determination method refers to GB/T3979-2008 method for measuring body color, and detects the anthocyanin concentration at 0.2 mg/mL;
group 1: lycium ruthenicum anthocyanin stock solution
Group 2:0.2:0.1:0.6
Group 3:0.1:0.6:0.1
Group 4:0.2:0.3:0.6
Group 5:0.2:0.6:0.3
The results are shown in FIG. 3.
As can be seen from fig. 3, by adjusting the ratio of chlorinated metal compounds to achieve different colors, the reason is that the metal and anthocyanin combine to produce complex, and different complexes and complex ratios produce different colors, which is one of the reasons why anthocyanidin presents different colors on different plant petals, we can select group 5 as the optimal color-changing formula in order to achieve yellow.
Example 2
The crude anthocyanin is prepared as follows, with additional steps as seen in example 1.
Crushing the dried lycium ruthenicum mill by using an ultrafine crusher, and sieving by using a 150-mesh sieve to obtain lycium ruthenicum submicron powder; weighing 300g of ammonium sulfate, adding 1300g of water to prepare an aqueous solution, then adding 400g of absolute ethyl alcohol to prepare an ethanol-ammonium sulfate two-aqueous-phase system, adding 100g of lycium ruthenicum super-fine powder into the two-aqueous-phase system, carrying out ultrasonic assisted extraction for 60min, and standing at room temperature for 3h for layering; and (3) after the solvent is subjected to rotary evaporation on the upper phase, dissolving the solvent by using absolute ethyl alcohol, filtering and recovering inorganic salt, and performing rotary evaporation again to recover the absolute ethyl alcohol to obtain a crude anthocyanin product.
Example 3
The crude anthocyanin is prepared as follows, with additional steps as seen in example 1.
Crushing the dried lycium ruthenicum murr by using an ultrafine crusher, and sieving by using a 80-mesh sieve to obtain lycium ruthenicum murr ultrafine powder; weighing 125g of ammonium sulfate, adding 200g of water to prepare an aqueous solution, then adding 200g of absolute ethyl alcohol to prepare an ethanol-ammonium sulfate two-aqueous-phase system, adding 100g of lycium ruthenicum superfine powder into the two-aqueous-phase system, carrying out ultrasonic assisted extraction for 20min, and standing at room temperature for 2h for layering; and (3) after the solvent is subjected to rotary evaporation on the upper phase, dissolving the solvent by using absolute ethyl alcohol, filtering and recovering inorganic salt, and performing rotary evaporation again to recover the absolute ethyl alcohol to obtain a crude anthocyanin product.
Example 4
The crude anthocyanin is prepared as follows, with additional steps as seen in example 1.
Crushing the dried lycium ruthenicum murr by using an ultrafine crusher, and sieving by using a 100-mesh sieve to obtain lycium ruthenicum murr ultrafine powder; weighing 200g of ammonium sulfate, adding 500g of water to prepare an aqueous solution, then adding 300g of absolute ethyl alcohol to prepare an ethanol-ammonium sulfate two-aqueous-phase system, adding 100g of lycium ruthenicum superfine powder into the two-aqueous-phase system, carrying out ultrasonic assisted extraction for 40min, and standing for 2h at room temperature for layering; and (3) after the solvent is subjected to rotary evaporation on the upper phase, dissolving the solvent by using absolute ethyl alcohol, filtering and recovering inorganic salt, and performing rotary evaporation again to recover the absolute ethyl alcohol to obtain a crude anthocyanin product.
Claims (9)
1. The method for extracting and preparing the yellow anthocyanin from the lycium ruthenicum is characterized by comprising the following steps of: it comprises the following contents: (1) Adding lycium ruthenicum superfine powder into an inorganic salt A water solution and a hydrophilic low-molecular organic solvent, extracting, standing and phase splitting;
(2) Removing the upper phase solvent, adding anhydrous ethanol to precipitate inorganic salt, filtering, removing anhydrous ethanol from the liquid part to obtain solid, re-dissolving the solid in the inorganic salt B water solution, standing, and removing the solvent under reduced pressure to obtain yellow anthocyanin;
the inorganic salt A is selected from ammonium sulfate; the hydrophilic low molecular organic solvent is one or the combination of more than two of methanol and ethanol; the inorganic salt B is selected from magnesium chloride: calcium chloride: aluminum chloride is 0.2m.
2. The method of claim 1, wherein: the hydrophilic low molecular organic solvent is selected from ethanol.
3. The method of claim 1, wherein: in the step (2), the solid is re-dissolved in 0 to 2mol/L inorganic salt B aqueous solution at 0.1 to 3 mg/mL.
4. The method of claim 1, wherein: the hydrophilic low molecular organic solvent accounts for 20-40% of the total mass of the inorganic salt A aqueous solution and the hydrophilic low molecular organic solvent.
5. The method of claim 1, wherein: the inorganic salt A accounts for 15-25% of the total mass of the inorganic salt A aqueous solution and the hydrophilic low-molecular organic solvent.
6. The method of claim 1, wherein: the total mass ratio of the lycium ruthenicum superfine powder to the inorganic salt A aqueous solution to the hydrophilic low-molecular organic solvent is 1:5-1:20.
7. the method of claim 1, wherein: ultrasonic extraction is adopted in the step (1).
8. A yellow anthocyanin produced by the process of any one of claims 1 to 7.
9. A yellow colorant characterized by: it comprises the yellow anthocyanin of claim 8.
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