CN111171597A - Method for separating and purifying rubropunctatin in red yeast glutinous rice - Google Patents
Method for separating and purifying rubropunctatin in red yeast glutinous rice Download PDFInfo
- Publication number
- CN111171597A CN111171597A CN202010041686.4A CN202010041686A CN111171597A CN 111171597 A CN111171597 A CN 111171597A CN 202010041686 A CN202010041686 A CN 202010041686A CN 111171597 A CN111171597 A CN 111171597A
- Authority
- CN
- China
- Prior art keywords
- silica gel
- column
- glutinous rice
- red yeast
- pigment
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Images
Classifications
-
- 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
- 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
- C09B67/006—Preparation of organic pigments
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
Abstract
The invention discloses a method for separating and purifying rubropunctatin in red yeast glutinous rice, which comprises the following steps: (1) extracting pigments; (2) preparing a sample solution; (3) silica gel column chromatography; (4) concentration: concentrating the collected monascus pigment with the darkest color; (5) thin layer chromatography; (6) scraping; (7) dissolving and concentrating; (8) and (5) drying. The method for separating and purifying the erythrosin simplifies the preparation of eluent and developing solvent of silica gel column chromatography and thin-layer chromatography, reduces the variety of reagents, simplifies the process flow of separating and purifying the monascus pigment to obtain the erythrosin, and improves the separation and purification efficiency.
Description
Technical Field
The invention belongs to the technical field of separation and purification of rubropunctatin, and particularly relates to a method for separating and purifying rubropunctatin in red yeast glutinous rice.
Background
The rubrum pigment is one of six classic pigments (yellow pigment, monascus pigment and ankaflavin, orange pigment, monascorubin and rubrum pigment, and red pigment, monascorubin and rubrum amine) in the monascus pigment. At present, Lian is mainly used for separating and purifying monascus pigment at home and abroad, Wang and Guo and the like firstly separate hypha from filtrate by using a filter membrane with 80 holes/square centimeter, then prepare the filtrate into freeze-dried powder by adopting a freeze-drying method to prepare a monascus pigment crude extract, and then directly wash and extract new haematochrome from the crude extract by using methanol, ethyl acetate and hexane in sequence. In 2014, Huang et al firstly extracted a monascus pigment crude extract (filtrate) from red yeast rice by an ultrasonic extraction method, and then the filtrate was filtered and concentrated; then loading the sample liquid into a silica gel column filled with 200-300 mesh silica gel, and carrying out silica gel column chromatography by using normal hexane and ethyl acetate (7/3, v/v) as eluents to obtain primarily separated monascus pigment; and finally, performing thin layer chromatography by using a thin layer plate (silica gel 60 meshes) by using normal hexane and ethyl acetate (7/3, v/v) as developing agents to obtain target pigments, namely two pigments with orange color band yellow fluorescence. The method for separating and purifying two orange and yellow fluorescent pigments by Huang et al has many steps, uses a plurality of reagents, and does not separate the two pigments separately. In 2010, Zheng grant et al used high-speed countercurrent chromatography to separate and purify monascus pigment components, mainly separating six classical pigments containing a diazotrophone host. Firstly, ultrasonically extracting monascus pigment from red yeast rice by adopting 70% ethanol, repeating the operation steps twice, combining the obtained extract liquor and concentrating; then, performing high-speed countercurrent chromatographic separation on the concentrated crude pigment extract, and analyzing and comparing, wherein a solvent system A used in the high-speed countercurrent chromatographic separation is n-hexane-ethyl acetate-methanol-water (10: 0: 7.5: 2.5, V/V), a solvent system B is n-hexane-ethyl acetate-methanol-water (2.5: 7.5: 5: 5, V/V), an upper layer liquid is taken as a stationary phase, a lower layer liquid is taken as a mobile phase, samples are collected according to different peak-off times of the pigment, and the erythema agent starts to peak in 60 minutes; and finally, precipitating by using an acetone solution to obtain the erythema pigment crystal. The separation and purification steps are complicated and time-consuming, the types of used reagents are more, and the monomer samples contain more impurities.
The separation and purification method of the erythrosin related by the invention is mainly based on a separation and purification method of Mukherjee and the like from red yeast rice, as shown in figure 1, a flow chart shows that the separation and purification process is complex, and the problems of multiple reagents are existed.
Disclosure of Invention
The invention aims to make up the defects of the prior art, simplify the preparation of eluent and developing agent of silica gel column chromatography and thin layer chromatography, reduce the types of used reagents and save the reagents, and provides a method for separating and purifying the erythrosin in the red yeast glutinous rice.
In order to achieve the above object, the present invention provides the following technical solutions:
a method for separating and purifying rubropunctatin in red yeast glutinous rice comprises the following steps:
(1) extraction of pigment
Beating the red yeast glutinous rice into powder, weighing the red yeast glutinous rice powder, mixing the red yeast glutinous rice powder with distilled water in an amount which is 200 times the mass of the red yeast glutinous rice powder, beating the red yeast glutinous rice powder by a beating machine for 5 minutes, putting the red yeast glutinous rice powder into an ultrasonic cleaning tank, carrying out ultrasonic treatment for 30 minutes, taking out the red yeast glutinous rice powder, beating the red yeast glutinous rice powder again for 5 minutes, carrying out;
(2) preparation of sample liquid
Centrifuging the filtrate in a centrifuge at 10000r/min for 30min, collecting supernatant, concentrating the supernatant into extract, and dissolving with 20ml of chromatographic grade methanol to obtain sample solution;
(3) silica gel column chromatography
①, treating silica gel, namely taking a proper amount of 100-200-mesh column chromatography silica gel, activating the column chromatography silica gel at 105 ℃ for 30min, taking out the column chromatography silica gel, cooling the column chromatography silica gel to room temperature, pouring the column chromatography silica gel into a dry beaker, adding a proper amount of chromatographic grade methanol to dissolve and soak the column chromatography silica gel for 20 min;
secondly, packing the column, namely washing a 30mm multiplied by 800mm silica gel column by using clear water, drying, vertically fixing the column on an iron stand, adding a proper amount of chromatographic grade methanol, exhausting air in the column, slightly and uniformly stirring the silica gel in a beaker by using a glass rod, introducing the silica gel into the column, opening a valve at the lower end of the chromatographic column, slowly flowing out a solvent, slowly adding silica gel suspension, slowly reducing the suspension at the upper end of the column to the height of about 75cm of the column, stopping filling, and finally balancing the column by using chromatographic grade methanol for 3-4 hours;
discharging redundant solvent at the upper end of a silica gel interface in the balanced chromatographic column, and draining the sample liquid to be separated to the surface of the silica gel phase when the meniscus of the balanced liquid is just level with the surface of the silica gel bed so as to avoid disturbing the surface of the stationary phase;
fourthly, collecting, namely opening the lower end of the silica gel column, keeping the flow rate of the eluent at 1 to 2 drops/second, and collecting test tubes to obtain 7 monascus pigments with different colors;
(4) concentration: concentrating the collected monascus pigment with the darkest color;
(5) thin layer chromatography:
activating silica gel plate G of 100mm × 200mm at 105 deg.C for 40 min;
sample application, wherein the concentrated pigment is densely applied with a glass capillary;
thirdly, preparing a developing agent, putting the spotted thin plate into a chromatographic cylinder, and developing for a distance to separate spots completely;
(6) scraping: r is to befThe ribbon at value 0.63 was scraped off and collected in a small beaker;
(7) dissolving and concentrating: dissolving out pigment in the color band powder by using chromatographic grade methanol, and concentrating in a round-bottom flask;
(8) drying: transferring the concentrated pigment solution into a culture dish, and drying in a 45 ℃ oven at constant temperature to obtain orange red monascus pigment crystals, namely the purpurin.
Furthermore, in the column filling process of the silica gel column chromatography, the silica gel is naturally settled to 1/4 to 1/3 of the height of the column after being introduced into the column.
Furthermore, the sample application base line of the thin layer chromatography is 2.0cm from the bottom edge in the sample application process, the sample application diameter is 2-4mm, the sample application amount is 0.5-5 muL each time, and the dot spacing is 1.5-2.0 cm.
Further, the developing agent used in the development process of the thin layer chromatography is a developing agent with v/v of 13: ethyl acetate of 7: methanol.
Furthermore, the depth of the developing agent dipped in the developing process of the thin layer chromatography is 0.5-1.0cm from the bottom edge of the thin plate to the liquid surface.
The invention has the advantages that:
the method for separating and purifying the erythrosin simplifies the preparation of eluent and developing solvent of silica gel column chromatography and thin-layer chromatography, reduces the variety of reagents, simplifies the process flow of separating and purifying the monascus pigment to obtain the erythrosin, and improves the separation and purification efficiency.
Drawings
FIG. 1 is a flow chart of the conventional process for separating and purifying haematochrome.
FIG. 2 is a flow chart of the process for separating and purifying the rubropunctatin in the red yeast glutinous rice of the invention.
FIG. 3 shows a thin layer chromatogram of the example.
FIG. 4 is a full wavelength scanning chart of the UV spectrophotometer for water extraction of monascus color in the examples.
FIG. 5 is a high performance liquid chromatogram of the target dye in the examples.
FIG. 6 is a UPLC-Q-TOF-MS spectrum of the target pigment in the example, wherein: (A) a first order mass spectrum (m/z) of the target pigment; (B) second-order mass spectrum (m/z) of the target pigment.
FIG. 7 shows a molecular structure diagram of erythematous pigment.
FIG. 8 is a nuclear magnetic resonance hydrogen spectrum of the target pigment in the example.
FIG. 9 shows the NMR carbon spectrum of the target dye in example.
FIG. 10 shows the NMR spectrum of erythematol.
Detailed Description
The technical scheme of the invention is further explained by combining the specific examples as follows:
examples
A method for separating and purifying rubropunctatin in red yeast glutinous rice comprises the following steps:
(1) extraction of pigment
Beating red yeast glutinous rice into powder, weighing 2g of red yeast glutinous rice powder, mixing with 400ml of distilled water, beating by a beating machine for 5 minutes, putting into an ultrasonic cleaning tank, ultrasonically treating for 30 minutes, taking out, beating again for 5 minutes, ultrasonically treating for 15 minutes, taking out, and performing suction filtration to obtain filtrate;
(2) preparation of sample liquid
Centrifuging the filtrate in a centrifuge at 10000r/min for 30 minutes, and taking supernatant; concentrating the supernatant to obtain extract, and dissolving with 20ml of chromatographic grade methanol to obtain sample solution;
(3) silica gel column chromatography:
①, treating silica gel, namely taking a proper amount of 100-200-mesh column chromatography silica gel, activating the column chromatography silica gel at 105 ℃ for 30min, taking out the column chromatography silica gel, cooling the column chromatography silica gel to room temperature, pouring the column chromatography silica gel into a dry beaker, adding a proper amount of chromatographic grade methanol to dissolve and soak the column chromatography silica gel for 20 min;
washing silica gel column (30mm × 800mm) with clear water, drying, vertically fixing the column on an iron stand, adding a proper amount of chromatographic grade methanol, removing air in the column, gently stirring silica gel in a beaker with a glass rod, introducing the silica gel into the column to naturally settle to 1/4 or 1/3 of the height of the column, opening a valve at the lower end of the chromatographic column to allow a solvent to slowly flow out, slowly adding silica gel suspension to slowly reduce the suspension at the upper end of the column to about 75cm of the height of the column, stopping filling, and finally balancing the column with chromatographic grade methanol for 3-4 hours;
discharging redundant solvent at the upper end of a silica gel interface in the balanced chromatographic column, and draining the sample liquid to be separated to the surface of the silica gel phase when the meniscus of the balanced liquid is just level with the surface of the silica gel bed so as to avoid disturbing the surface of the stationary phase;
fourthly, collecting, namely opening the lower end of the silica gel column, keeping the flow rate of the eluent at 1 to 2 drops/second, and collecting test tubes to obtain 7 monascus pigments with different colors;
(4) concentration: concentrating the collected monascus pigment with the darkest color;
(5) thin layer chromatography:
activating silica gel plate G (100mm × 200mm) at 105 deg.C for 40 min;
sample application, wherein the concentrated pigment is densely applied with a glass capillary, the distance between a sample application base line and the bottom edge is 2.0cm, the sample application diameter is 2-4mm, the sample application amount is 0.5-5 mu L each time, and the dot spacing is 1.5-2.0 cm;
thirdly, developing, namely preparing 13: 7(v/v) ethyl acetate and methanol as developing agents, putting the spotted thin plate into a chromatographic cylinder, and immersing the developing agents to a depth of 0.5-1.0cm from the bottom edge of the thin plate to the liquid level, so that spots are not immersed into the developing agents;
(6) scraping: as shown in FIG. 3, R isfThe ribbon at value 0.63 was scraped off and collected in a small beaker;
(7) dissolving and concentrating: dissolving out pigment in the color band powder by using chromatographic grade methanol, and concentrating in a round-bottom flask;
(8) drying: transferring the concentrated pigment solution into a culture dish, and drying in a 45 ℃ oven at constant temperature to obtain orange red monascus pigment crystals, namely the purpurin.
Index measurement:
and (4) carrying out full-wavelength scanning on the water-extracted monascus pigment by using an ultraviolet spectrophotometer. As shown in FIG. 4, the maximum absorption wavelengths (λ max) were 377nm and 492 nm. Since the number of peaks of the high performance liquid at 492nm was lower than that at 377nm, the target dye was not detected at 492 nm. Therefore, 377nm was chosen for HPLC and UPLC-Q-TOF-MS detection.
Target pigment (R)f0.63) was filtered through a 0.22 μm nylon needle filter and analyzed by hplc. As shown in fig. 5, the high performance liquid chromatogram showed a retention time of the target pigment peak of 8.301min in addition to the solvent peak and some impurity peaks.
And (3) carrying out qualitative analysis on the target pigment by adopting a liquid chromatography-quadrupole time-of-flight mass spectrometry combined technology. The mass spectrum peak of the target pigment appeared at 8.386min, and its primary mass spectrum showed that the [ M-H ] -ion of the target pigment was 353.2116M/z (see FIG. 6A). Thus, according to studies, the molecular weight of this pigment was reported to be 354, consistent with that of erythemin (see FIG. 7). In the secondary mass spectrum, the mass-to-charge ratio of the main daughter ion fragment was 248.9727m/z (see FIG. 6B).
The target dye (R)f0.63) of1H NMR and13the molecular structure of the pigment can be divided into two main parts, including a main structure of azone and two side chains, wherein the main structure of azone and the H on two connected unsaturated CH bonds are in the same structure as the main structure of azone, the acyl five-membered chain is combined with C3, and the two unsaturated CH. are connected on the carbon atom in the C6 inner ring1Shift homoenergetic shown on H NMR spectrum andthe shift in H of erythemin reported in previous studies corresponded to. FIG. 10 shows the NMR spectrum of erythrosin in CDCl as a solvent3Where the displacement of H is shown below: 0.90(t, 3H, J ═ 6.8Hz, CH)3CH2)；1.31(br，6H，CH2-18-20); 1.62(s, 3H, H-13); 1.94(d, 3H, J ═ 7.2Hz, H-1); 2.51(br dd, 1H, J ═ 7.2, 9.0Hz, Ha-17); 2.88(ddd, 1H, J ═ 5.2, 7.2, 7.2, Hb-17); 5.98(d, 1H, J ═ 16.8Hz, H-3); 6.14(s, 1H, H-7); 6.55(dq, 1H, J ═ 16.7, 7.2Hz, H-2); 6.87(s, 1H, H-5); 7.82(s, 1H, H-12). The data of the displacements of H of the target pigment counted in table 1 substantially match the data of the displacements of the erythema elements measured in zhaoxue et al. In these proton resonances the keto C ═ O and ester (lactone) groups on the C13 and C2 carbon atoms are signaled in13The peaks at 198.9ppm and 173.7ppm are shown on the C NMR spectrum, respectively. A carbonyl signal on a carbon atom of C9 ring was observed at 196.4 ppm. According to the relevant literature, in13In the C NMR spectrum, the proton resonance range of the methyl group is 8.0-30.0 ppm. According to detection, the proton resonance shifts of methyl groups (C9', C12 and C18) in the dye structure are respectively 30.3ppm, 15.6ppm and 14.7ppm (see FIGS. 8, 9 and Table 1), which is consistent with the conclusion of the literature. And resonance signals of other groups can be observed in the spectrum as well.
TABLE 1 Delta of target pigmentHAnd deltaC
The pigment obtained by the improved separation and purification process is the erythrosin according to the comprehensive measurement indexes.
The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (5)
1. A method for separating and purifying rubropunctatin in red yeast glutinous rice is characterized by comprising the following steps:
(1) extraction of pigment
Beating the red yeast glutinous rice into powder, weighing the red yeast glutinous rice powder, mixing the red yeast glutinous rice powder with distilled water in an amount which is 200 times the mass of the red yeast glutinous rice powder, beating the red yeast glutinous rice powder by a beating machine for 5 minutes, putting the red yeast glutinous rice powder into an ultrasonic cleaning tank, carrying out ultrasonic treatment for 30 minutes, taking out the red yeast glutinous rice powder, beating the red yeast glutinous rice powder again for 5 minutes, carrying out;
(2) preparation of sample liquid
Centrifuging the filtrate in a centrifuge at 10000r/min for 30min, collecting supernatant, concentrating the supernatant into extract, and dissolving with 20ml of chromatographic grade methanol to obtain sample solution;
(3) silica gel column chromatography
①, treating silica gel, namely taking a proper amount of 100-200-mesh column chromatography silica gel, activating the column chromatography silica gel at 105 ℃ for 30min, taking out the column chromatography silica gel, cooling the column chromatography silica gel to room temperature, pouring the column chromatography silica gel into a dry beaker, adding a proper amount of chromatographic grade methanol to dissolve and soak the column chromatography silica gel for 20 min;
secondly, packing the column, namely washing a 30mm multiplied by 800mm silica gel column by using clear water, drying, vertically fixing the column on an iron stand, adding a proper amount of chromatographic grade methanol, exhausting air in the column, slightly and uniformly stirring the silica gel in a beaker by using a glass rod, introducing the silica gel into the column, opening a valve at the lower end of the chromatographic column, slowly flowing out a solvent, slowly adding silica gel suspension, slowly reducing the suspension at the upper end of the column to the height of about 75cm of the column, stopping filling, and finally balancing the column by using chromatographic grade methanol for 3-4 hours;
discharging redundant solvent at the upper end of a silica gel interface in the balanced chromatographic column, and draining the sample liquid to be separated to the surface of the silica gel phase when the meniscus of the balanced liquid is just level with the surface of the silica gel bed so as to avoid disturbing the surface of the stationary phase;
fourthly, collecting, namely opening the lower end of the silica gel column, keeping the flow rate of the eluent at 1 to 2 drops/second, and collecting test tubes to obtain 7 monascus pigments with different colors;
(4) concentration: concentrating the collected monascus pigment with the darkest color;
(5) thin layer chromatography:
activating silica gel plate G of 100mm × 200mm at 105 deg.C for 40 min;
sample application, wherein the concentrated pigment is densely applied with a glass capillary;
thirdly, preparing a developing agent, putting the spotted thin plate into a chromatographic cylinder, and developing for a distance to separate spots completely;
(6) scraping: r is to befThe ribbon at value 0.63 was scraped off and collected in a small beaker;
(7) dissolving and concentrating: dissolving out pigment in the color band powder by using chromatographic grade methanol, and concentrating in a round-bottom flask;
(8) drying: transferring the concentrated pigment solution into a culture dish, and drying in a 45 ℃ oven at constant temperature to obtain orange red monascus pigment crystals, namely the purpurin.
2. The method for separating and purifying rubropunctatin in red yeast glutinous rice according to claim 1, wherein the silica gel is naturally settled to 1/4 to 1/3 of the height of the column after being introduced into the column during the column loading process of the silica gel column chromatography.
3. The method for separating and purifying the rubropunctatin in the red yeast glutinous rice according to claim 1, wherein the sample application base line of the thin layer chromatography is 2.0cm from the bottom edge, the sample application diameter is 2-4mm, the sample amount per time is 0.5-5 μ L, and the dot spacing is 1.5-2.0 cm.
4. The method for separating and purifying rubropunctatin in red yeast glutinous rice according to claim 1, wherein the developing agent used in the development process of the thin layer chromatography is a developing agent with v/v of 13: ethyl acetate of 7: methanol.
5. The method for separating and purifying rubropunctatin in red yeast glutinous rice according to claim 1, wherein the depth of the immersed developing agent in the development process of the thin layer chromatography is 0.5-1.0cm from the bottom edge of the thin plate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010041686.4A CN111171597A (en) | 2020-01-15 | 2020-01-15 | Method for separating and purifying rubropunctatin in red yeast glutinous rice |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010041686.4A CN111171597A (en) | 2020-01-15 | 2020-01-15 | Method for separating and purifying rubropunctatin in red yeast glutinous rice |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN111171597A true CN111171597A (en) | 2020-05-19 |
Family
ID=70654733
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010041686.4A Pending CN111171597A (en) | 2020-01-15 | 2020-01-15 | Method for separating and purifying rubropunctatin in red yeast glutinous rice |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111171597A (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101862324A (en) * | 2010-04-13 | 2010-10-20 | 福州大学 | Application of monascus color components and derivatives thereof in fighting cancers |
| CN104330375A (en) * | 2014-10-22 | 2015-02-04 | 西安莹朴生物科技股份有限公司 | Method for measuring light stability of monascus red pigment |
| CN105734091A (en) * | 2016-04-19 | 2016-07-06 | 天津科技大学 | Method for producing high-purity monascine and ankafaflavin through monascus liquid-state fermentation |
-
2020
- 2020-01-15 CN CN202010041686.4A patent/CN111171597A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101862324A (en) * | 2010-04-13 | 2010-10-20 | 福州大学 | Application of monascus color components and derivatives thereof in fighting cancers |
| CN104330375A (en) * | 2014-10-22 | 2015-02-04 | 西安莹朴生物科技股份有限公司 | Method for measuring light stability of monascus red pigment |
| CN105734091A (en) * | 2016-04-19 | 2016-07-06 | 天津科技大学 | Method for producing high-purity monascine and ankafaflavin through monascus liquid-state fermentation |
Non-Patent Citations (2)
| Title |
|---|
| 张皓雪: "天然红曲色素标准品的研制", 《浙江工业大学硕士学位论文》 * |
| 赵倩: "红曲色素热稳定性的研究", 《华中农业大学硕士学位论文》 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN111171597A (en) | Method for separating and purifying rubropunctatin in red yeast glutinous rice | |
| CN111398465B (en) | Method for measuring precursor FCPHA of PET imaging agent and cis-isomer thereof | |
| CN113061088A (en) | Asymmetric column [5] arene and preparation method and application thereof | |
| CN109499096B (en) | Method for separating and purifying 6-gingerol by vacuum column chromatography and production method of 6-gingerol | |
| CN109265494B (en) | Method for extracting kaempferol glucoside compounds from camellia reticulata | |
| CN109180622B (en) | Method for extracting guaiane type sesquiterpene compound from artichoke | |
| KR100562963B1 (en) | Process for manufacturing paclitaxel and 13-acetyl-9-dihydrobaccatin ? | |
| CN105906639A (en) | Method for separating and purifying metalloporphyrin compound in thick oil | |
| Musuku et al. | Isolation and structure determination of a new roquefortine-related mycotoxin from Penicillium verrucosum var. cyclopium isolated from cassava | |
| CN111116695B (en) | Preparation and purification method of four stereoisomers of benzopyrene DNA adduct | |
| CN111393501B (en) | Preparation method of taurine-3-dehydro-chenodeoxycholic acid | |
| CN108802246A (en) | A kind of nervonic acid process for separation and purification | |
| Bicchi et al. | Cyclodextrin derivatives in GC separation of racemates of different volatility Part XVIII: 2‐methyl‐3‐acetyl‐and 2‐acetyl‐3‐methyl‐6‐O‐t‐hexyldimethylsilyl‐γ‐cyclodextrin derivatives | |
| CN109369585B (en) | Method for extracting guaiane type sesquiterpene compound | |
| CN107064334A (en) | The method of quality control of anthracene shellfish element | |
| CN109265434B (en) | Method for extracting lignans from Nanshan tea by DAC (digital-to-analog converter) preparation method | |
| CN114276364A (en) | Sesquiterpenoids in artemisia mongolica and preparation method and application thereof | |
| CN113624893A (en) | Cis-trans monodiunsaturated fatty acid methyl ester on-line solid-phase extraction-high performance liquid chromatography combined detection method | |
| CN109265433B (en) | Method for extracting lignanoid compounds from Nanshan tea | |
| PHILLIPSON et al. | LANOMYCIN AND GLUCOLANOMYCIN, ANTIFUNGAL AGENTS PRODUCED BY Pycnidiophora dispersa II. STRUCTURE ELUCIDATION | |
| CN109369605B (en) | Method for extracting lignans from Nanshan tea | |
| CN109369750B (en) | Method for extracting kaempferol galactoside compounds from Nanshan tea | |
| CN115960029B (en) | Alkaloid in pseudo-tricholoma matsutake as well as extraction and separation method and application thereof | |
| SU765278A1 (en) | Method of chromatographic separation of methylglycopyranoside methyl ethers mixtures | |
| CN117820394A (en) | Method for preparing acylated flavonoid glycoside B from ginkgo leaf extract |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20200519 |