CN108586435B - Preparation method of Echinulin - Google Patents
Preparation method of Echinulin Download PDFInfo
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- CN108586435B CN108586435B CN201810718239.0A CN201810718239A CN108586435B CN 108586435 B CN108586435 B CN 108586435B CN 201810718239 A CN201810718239 A CN 201810718239A CN 108586435 B CN108586435 B CN 108586435B
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Abstract
The invention relates to a preparation method of Echinulin, and belongs to the technical field of chemical analysis. The invention aims to solve the problems that the raw materials are not easy to obtain and the preparation process is complex in the existing Echinulin preparation method, and the technical scheme for solving the problems is to provide the Echinulin preparation method which comprises the following steps: is separated from the yeast for making hard liquor, and the method comprises the following steps: a. crushing Daqu, extracting with an organic solvent, and concentrating to obtain Daqu extract; b. carrying out silica gel normal phase column chromatography on the Daqu extract, collecting an eluent containing Echinulin, and concentrating to obtain a crude product; c. and (3) performing sephadex column chromatography on the crude product, collecting an eluent containing the Echinulin, and concentrating to obtain the Echinulin. The method combines a plurality of chromatographic techniques, and the Echinulin is separated and prepared from the Daqu for the first time, and the product purity is high.
Description
Technical Field
The invention relates to a preparation method of Echinulin, and belongs to the technical field of chemical analysis.
Background
Echinulin, namely 3S,6S,3- [ [2- (1, 1-dimethyl-2-propene) -5, 7-bis (3, 3-dimethylpropenyl) -1H-indol-3-yl ] methyl ] -6-methyl-2, 5-piperazinedione, CAS NO: 1859-87-6, molecular weight: 461.64, is a cyclic dipeptide compound, and its chemical structure is as follows:
previous studies have shown that Echinulin has a wide range of physiological activities, such as antiviral, antitubercular, antioxidant, anti-inflammatory, immune enhancing, blood pressure lowering, etc. At present, the compound is mainly obtained by separating and extracting a single strain such as Aspergillus chevalieri, Eurotium cristatum, Aspergillus veriacolor and the like from a fermentation product through pure strain culture, and has the defects of harsh culture conditions of the single strain, multiple structural analogs in the fermentation product, multiple purification procedures, higher separation and purification difficulty and the like. Therefore, the development of the Echinulin preparation method with easily obtained raw materials and simple process is of great significance.
The Daqu is a raw material for brewing wine, and is prepared by using wheat and the like as raw materials, crushing, adding water, kneading, pressing into fermented grains and allowing various microorganisms in the nature to grow on the fermented grains, and complex operations such as single strain purification, culture and the like are not needed. In the process of preparing a koji, a complex microbial population metabolizes proteins, amino acids, and the like in raw materials by using various enzyme systems produced by the complex microbial population to produce small-molecule peptide compounds (compounds having amide bonds). When the white spirit is distilled, the small molecular peptide compounds from the Daqu can be brought into the spirit body under the actions of azeotropy, entrainment and the like, so that the white spirit product has a certain health-care effect. The separation of the small molecular peptide compounds with physiological activity in the Daqu can lay a foundation for further exploring health functional factors in the white spirit, provide a theoretical basis for explaining the view of 'proper drinking is beneficial to health', and have important significance for the market popularization of white spirit products.
Disclosure of Invention
The invention aims to provide a preparation method of Echinulin, and aims to solve the problems that raw materials are not easy to obtain, the preparation process is complex and the like in the existing preparation method of Echinulin.
The invention provides a preparation method of Echinulin, which comprises the following steps: is separated from the yeast for making hard liquor.
Further, the preparation method comprises the following steps:
a. crushing Daqu, extracting with an organic solvent, and concentrating to obtain Daqu extract;
b. carrying out silica gel normal phase column chromatography on the Daqu extract, collecting an eluent containing Echinulin, and concentrating to obtain a crude product;
c. and (3) performing sephadex column chromatography on the crude product, collecting an eluent containing the Echinulin, and concentrating to obtain the Echinulin.
The invention firstly selects an organic solvent to extract trace target substances in the yeast and simultaneously avoids the main components of the yeast such as starch, sugar, protein and the like from entering the extracting solution.
Then, silica gel normal phase column chromatography is adopted, and the principle is that the Echinulin is separated according to different polarities of the compounds, so that the aim of separating and purifying the Echinulin is fulfilled.
The column chromatography is carried out by adopting sephadex column, the principle is that the separation is carried out according to the difference of the molecular weight of the compounds, the compounds with large molecular weight flow out firstly, and the compounds with small molecular weight flow out later.
To separate high-purity Echinulin from a koji having a complex composition, the above separation means must be combined, and none of the three steps a, b and c is necessary.
Further, the organic solvent is an alcohol solvent or ethyl acetate.
Preferably, the alcohol solvent is methanol.
The method adopts an alcohol solvent or ethyl acetate as an extraction solvent, can fully extract Echinulin in the Daqu, and can prevent components such as starch, saccharides and protein from entering an extracting solution. In a preferred embodiment, the boiling points of the methanol and the ethyl acetate are low, and the temperature does not need to be set too high during the decompression concentration, so that the target compound can be prevented from being damaged by high temperature, the time can be saved, and the solvent can be conveniently recovered.
Further, when the organic solvent is methanol, at least one of the following is satisfied:
the using amount of the methanol is 2-4 times of the weight of the Daqu;
the extraction temperature is 15-40 ℃;
the extraction times are 2-4 times;
the extraction time is 5-15 days each time.
Preferably, the extraction temperature is 20 ℃.
Through investigation, the using amount of the methanol is 2-4 times of the weight of the yeast, so that Echinulin in the yeast can be fully extracted, and the waste of a solvent is avoided.
The extraction temperature is optimal at 15-40 ℃, Echinulin in the yeast can be fully extracted, and serious solvent volatilization and excessive loss can not be caused.
The extraction times are 2-4 times, the extraction time is 5-15 days at each time, Echinulin in the yeast for making hard liquor can be fully extracted, and the situation that impurities enter an extracting solution too much to bring difficulty to subsequent separation and purification can be avoided.
Further, when the organic solvent is methanol, the step a further comprises the following steps: adding water to the concentrated extract solution for uniform dispersion, adding petroleum ether for extraction, and concentrating the petroleum ether phase to obtain Daqu extract.
Preferably, the dispersion is homogeneous at 60 ℃.
When methanol is used as an extraction solvent, impurities with different polarities in the yeast can be dissolved in the methanol, so that the concentrated extracting solution is extracted by using petroleum ether with lower polarity, and compounds with lower polarity are extracted out, so that the subsequent separation difficulty is reduced.
When ethyl acetate is used as the extraction solvent, ethyl acetate is less polar than methanol and the amount of strongly polar compounds in the extract is much less, so that the petroleum ether extraction step is not required.
Further, when the organic solvent is ethyl acetate, at least one of the following is satisfied:
the using amount of the ethyl acetate is 2-4 times of the weight of the Daqu;
the extraction temperature is 15-40 ℃;
the extraction times are 2-4 times;
the extraction time is 5-15 days each time.
Preferably, the amount of ethyl acetate is 3 times the weight of the yeast.
Preferably, the extraction temperature is 30 ℃.
Preferably, the number of extractions is 3.
Further, step b satisfies at least one of the following:
the silica gel is 100-300 mesh normal phase silica gel;
uniformly stirring the Daqu extract and normal phase silica gel in a weight ratio of 1: 1;
petroleum ether-ethyl acetate or petroleum ether-acetone is used as an elution reagent;
gradient elution is carried out according to the ratio of petroleum ether to ethyl acetate, v/v, 20:1, 10:1, 5:1, 2:1 and 1:1, or the gradient elution is carried out according to the ratio of petroleum ether to acetone, v/v, 20:1, 10:1, 5:1, 2:1 and 1: 1.
The invention selects 100-300 mesh normal phase silica gel preferentially, which not only can achieve better purification effect, but also can ensure the separation speed.
Petroleum ether-ethyl acetate or petroleum ether-acetone is used as an elution reagent, and different compounds in the Daqu extract can be gradually eluted from weak polarity to strong polarity by adjusting the gradient of the eluent.
Further, step c satisfies at least one of the following:
the sephadex is sephadex LH-20;
chloroform-methanol and/or methanol are used as elution reagents.
Preferably, the chloroform-methanol elution reagent comprises chloroform: the volume ratio of methanol is 1: 1.
the sephadex LH-20 column is adopted for chromatography, and chloroform-methanol and/or methanol are/is used as an elution reagent for elution, so that sephadex LH-20 has gel filtration effect and reverse distribution effect, compounds with large molecular weight and large polarity are weakly retained and are eluted firstly, and compounds with small molecular weight and small polarity are strongly retained and are eluted later. Meanwhile, the solvent amount used by the scheme is small, the separation efficiency is high, and the cost is low.
Further, the preparation method also comprises a recrystallization step, and at least one of the following conditions is satisfied:
the recrystallization solvent is methanol or petroleum ether-ethyl acetate;
the number of recrystallization times is 2 to 4.
Further, the Daqu is medium-temperature wheat starter.
Preferably, the Daqu is a strong-flavor medium-temperature pure wheat starter.
The medium-temperature yeast for wheat is prepared from wheat-containing raw materials, and the temperature of a yeast blank is controlled to be 35-60 ℃.
The medium-temperature yeast for the strong-flavor pure wheat is prepared by completely taking wheat as a raw material, and the temperature of a yeast blank is controlled to be not more than 35-60 ℃.
The invention provides a preparation method of Echinulin, which combines various chromatographic techniques and separates and prepares the Echinulin from Daqu for the first time, and the preparation method mainly has the following advantages:
1. the raw materials are easy to obtain: the existing main method for preparing Echinulin comprises the following steps: firstly, inoculating special single strains such as Aspergillus chevalieri, Eurotium cristatum and the like into a specific culture medium which is sterilized at high temperature and high pressure, fermenting under a certain condition, and then separating Echinulin from a large amount of fermentation liquor, wherein raw materials for preparing the Echinulin are not easy to obtain; the method directly takes the yeast for brewing wine as a raw material to separate and prepare the Echinulin.
2. The preparation and separation method is simple and convenient, and the product purity is high: when the cyclo-dipeptide Echinulin is obtained by single strain fermentation, the cyclo-dipeptide Echinulin in fermentation liquor has a plurality of homologues, and the steps are complicated and the difficulty is particularly large when a target product with higher separation purity is required to be prepared; according to the method, the Echinulin is separated from the Daqu, the Daqu does not have homologues of a target object, the technical route is mature and clear, the method is efficient and accurate, and the prepared Echinulin is high in purity.
Drawings
FIG. 1 is an ESI mass spectrum of Echinulin obtained in example 1;
FIG. 2 is a one-dimensional NMR hydrogen spectrum of Echinulin obtained in example 1;
FIG. 3 is a one-dimensional NMR carbon spectrum of Echinulin obtained in example 1.
Detailed Description
The raw materials and equipment used in the embodiment of the present invention are known products and obtained by purchasing commercially available products.
The invention provides a novel method for preparing Echinulin, which comprises the following steps: is separated from the yeast for brewing wine.
In the process of exploring health functional factors in white spirit, the inventor discovers that Echinulin exists in the brewing raw material Daqu for the first time, provides possibility for separating and preparing Echinulin from Daqu, and also provides a new method for obtaining the compound in large quantity.
Furthermore, the invention creatively combines a plurality of separation technologies such as silica gel normal phase column chromatography, sephadex column chromatography and the like, and the yeast with complex components is firstly separated to obtain the yeast with the purity of more than 98 percent
Echinulin. And qualitatively analyzing the pure target compound by adopting detection means such as mass spectrum, nuclear magnetism and the like, and determining that the compound is Echinulin.
At present, no report related to Echinulin exists in the Daqu, and no report of Echinulin separated and prepared from the Daqu is found.
Example 1 Echinulin prepared by the Process of the present invention
(1) Taking 10kg of strong-flavor pure wheat medium-temperature yeast (prepared by completely taking wheat as a raw material and controlling the temperature of a yeast blank to be 35-60 ℃), crushing, adding 20kg of methanol, extracting for 2 times at 20 ℃ for 15 days each time, filtering an extracting solution, and concentrating under reduced pressure to obtain a yeast extract. Adding 10L of distilled water into the crude extract of the Daqu, uniformly dispersing at 60 ℃, adding 10L of petroleum ether into a separating funnel, extracting for 3 times, collecting petroleum ether phase, and concentrating under reduced pressure to obtain 120g of Daqu extract.
(2) Uniformly stirring the Daqu extract and 100-mesh normal phase silica gel according to the weight ratio of 1:1, performing normal phase column chromatography on the silica gel, performing gradient elution by using petroleum ether/ethyl acetate as an elution reagent and using the ratio of 20:1, 10:1, 5:1, 2:1, 1:1 (petroleum ether/ethyl acetate, v/v), and eluting 4 liters in each ratio; the 2:1 eluted fractions were collected in fractions, analyzed by thin layer chromatography (petroleum ether/acetone, 3:1, v/v), and the samples having an Rf value of 0.25 were combined and dried under reduced pressure to give a fraction Q-5.
(3) Subjecting the component Q-5 obtained in the step (2) to sephadex LH-20 column chromatography, eluting with chloroform/methanol as an eluting reagent at a ratio of 1:1 (chloroform/methanol, v/v), subjecting the eluate to thin layer chromatography (petroleum ether/acetone, 3:1, v/v), combining samples with Rf value of 0.25, and drying under reduced pressure to obtain Q-5-4; subjecting the fraction Q-5-4 to Sephadex LH-20 column chromatography, eluting with methanol as eluting reagent, subjecting the eluate to thin layer chromatography (petroleum ether/acetone, 3:1, v/v), mixing the samples with Rf value of 0.25, and drying under reduced pressure.
(4) And (4) dissolving the target compound obtained in the step (3) in methanol, recrystallizing for 2 times to obtain 85mg of a pure compound, and analyzing by HPLC to obtain the compound with the content of 98%.
Analyzing the pure compound obtained in the step (4) by adopting a mass spectrum (HR-ESI-MS), and determining the result: [ M + Na ]]+484.11, see FIG. 1; nuclear magnetic 1H-NMR (400MHz, CDCl) was used3) The pure product obtained in step (4) was analyzed, and the data were 8.05(1H, s),7.13(1H, s),6.80(1H, s),6.07(1H, dd, J ═ 17.2,10.8Hz),5.97(1H, s),5.66(1H, s),5.42(1H, t, J ═ 7.9Hz),5.34(1H, t, J ═ 7.9Hz),5.16(1H, d,7.2Hz),5.14(1H, s),4.40(1H, brd, J ═ 7.9Hz),4.10(1H, dd, J ═ 14.0,7.2Hz),3.64(1H, dd, J ═ 14.8,4.0Hz),3.52(2H, d, J ═ 2, 3.2, 3.8, 3.0 Hz),3.52(2H, d, J ═ 2, 3.2, 3.0, 3.6H, 3.2 Hz, 3.5H, 3.6H, 3.5.6H, 5(1H, s), 5.9 Hz, 3.6H, 6H, 3.6H, 3.9 Hz, 3.2 Hz, d, 3.2 Hz, 3.6H, 3.2 Hz, 3.2H, 3.2 Hz, d, 3; 13C-NMR (100MHz, CDCl)3):168.5,167.9,146.0,141.6,134.1,133.2,132.5,131.8,129.2,124.6,123.6,123.1,123.0,115.3,112.6,104.3,54.8,51.0,39.2,34.4,31.2,29.4,27.7,27.6,25.5,25.4,19.6,17.7,17.6, see fig. 3. The above spectroscopic data demonstrate that the compound is Echinulin, i.e.: 3S,6S,3- [ [2- (1, 1-dimethyl-2-propen) -5, 7-bis (3, 3-dimethylpropenyl) -1H-indol-3-yl]Methyl radical]-6-methyl-2, 5-piperazinedione.
Example 2 Echinulin preparation Using the Process of the invention
(1) Taking 10kg of Luzhou-flavor pure wheat medium-temperature yeast (prepared by completely taking wheat as a raw material and controlling the temperature of a yeast blank to be 35-60 ℃), crushing, adding 30kg of ethyl acetate, extracting for 3 times at 30 ℃ for 5 days each time, filtering the extracting solution, and concentrating under reduced pressure to obtain 220g of Daqu extract.
(2) Uniformly stirring the Daqu extract and 300-mesh normal phase silica gel according to the weight ratio of 1:1, performing normal phase column chromatography on the silica gel, performing gradient elution by using petroleum ether/acetone as an elution reagent and using the ratio of 20:1, 10:1, 5:1, 2:1, 1:1 (petroleum ether/acetone, v/v), and eluting 6 liters in each ratio; thin layer chromatography (petrol ether/acetone, 3:1, v/v) combined fractions of the sample with an Rf value of 0.25 and dried under reduced pressure to give fraction A4.
(3) Subjecting the fraction A4 obtained in the step (2) to Sephadex LH-20 column chromatography, eluting with chloroform/methanol as eluting reagent at a ratio of 1:1 (chloroform/methanol, v/v), performing thin layer chromatography (petroleum ether/acetone, 3:1, v/v), mixing the samples with Rf value of 0.25, and drying under reduced pressure.
(4) And (4) dissolving the target compound obtained in the step (3) in a petroleum ether/ethyl acetate mixed solution, recrystallizing for 4 times to obtain 120mg of a pure compound, and analyzing by HPLC (high performance liquid chromatography), wherein the content of the pure compound reaches more than 98%.
Analyzing the pure compound obtained in the step (4) by adopting a mass spectrum (HR-ESI-MS), and determining the result: [ M + Na ]]+484.11; nuclear magnetic 1H-NMR (400MHz, CDCl) was used3) The pure product obtained in step (4) was analyzed, and the data were 8.05(1H, s),7.13(1H, s),6.80(1H, s),6.07(1H, dd, J ═ 17.2,10.8Hz),5.97(1H, s),5.66(1H, s),5.42(1H, t, J ═ 7.9Hz),5.34(1H, t, J ═ 7.9Hz),5.16(1H, d,7.2Hz),5.14(1H, s),4.40(1H, brd, J ═ 7.9Hz),4.10(1H, dd, J ═ 14.0,7.2Hz),3.64(1H, dd, J ═ 14.8,4.0Hz),3.52(2H, d, J ═ 7.2Hz),3.38(2H,d,J＝7.2Hz),3.19(1H,dd,J＝14.4,12.0Hz),1.87(3H,s),1.80(3H,s),1.74(6H,s),1.52(3H,d,J＝6.8Hz),1.50(6H,s)；13C-NMR(100MHz,CDCl3) 168.5,167.9,146.0,141.6,134.1,133.2,132.5,131.8,129.2,124.6,123.6,123.1,123.0,115.3,112.6,104.3,54.8,51.0,39.2,34.4,31.2,29.4,27.7,27.6,25.5,25.4,19.6,17.7,17.6, the above spectroscopic data demonstrate that the compound is the cyclodipeptide Echinulin, i.e.: 3S,6S,3- [ [2- (1, 1-dimethyl-2-propen) -5, 7-bis (3, 3-dimethylpropenyl) -1H-indol-3-yl]Methyl radical]-6-methyl-2, 5-piperazinedione.
Claims (15)
- A preparation method of Echinulin is characterized by comprising the following steps: the method comprises the following steps:a. crushing Daqu, extracting with an organic solvent, and concentrating to obtain Daqu extract; wherein the organic solvent is an alcohol solvent or ethyl acetate;b. carrying out silica gel normal phase column chromatography on the Daqu extract, collecting an eluent containing Echinulin, and concentrating to obtain a crude product; wherein, petroleum ether-ethyl acetate or petroleum ether-acetone is used as an elution reagent;c. performing sephadex column chromatography on the crude product, collecting an eluent containing Echinulin, and concentrating to obtain Echinulin; wherein chloroform-methanol or methanol is used as an elution reagent.
- 2. The method of claim 1, wherein: the alcohol solvent is methanol.
- 3. The process according to claim 1 or 2, characterized in that: when the organic solvent is methanol, at least one of the following conditions is satisfied:the using amount of the methanol is 2-4 times of the weight of the Daqu;the extraction temperature is 15-40 ℃;the extraction times are 2-4 times;the extraction time is 5-15 days each time.
- 4. The method of claim 3, wherein: the extraction temperature was 20 ℃.
- 5. The process according to claim 1 or 2, characterized in that: when the organic solvent is methanol, the step a further comprises the following steps: adding water to the concentrated extract solution for uniform dispersion, adding petroleum ether for extraction, and concentrating the petroleum ether phase to obtain Daqu extract.
- 6. The method of claim 5, wherein: dispersing uniformly at 60 ℃.
- 7. The process according to claim 1 or 2, characterized in that: when the organic solvent is ethyl acetate, at least one of the following conditions is satisfied:the using amount of the ethyl acetate is 2-4 times of the weight of the Daqu;the extraction temperature is 15-40 ℃;the extraction times are 2-4 times;the extraction time is 5-15 days each time.
- 8. The method of claim 7, wherein: the amount of ethyl acetate is 3 times of the weight of the Daqu.
- 9. The method of claim 7, wherein: the extraction temperature was 30 ℃.
- 10. The method of claim 7, wherein: the extraction times are 3 times.
- 11. The method of claim 1, wherein: step b satisfies at least one of the following:the silica gel is 100-300 mesh normal phase silica gel;uniformly stirring the Daqu extract and normal phase silica gel in a weight ratio of 1: 1;gradient elution is carried out according to the ratio of petroleum ether to ethyl acetate, v/v, 20:1, 10:1, 5:1, 2:1 and 1:1, or the gradient elution is carried out according to the ratio of petroleum ether to acetone, v/v, 20:1, 10:1, 5:1, 2:1 and 1: 1.
- 12. The method of claim 1, wherein: step c satisfies at least one of the following:the sephadex is sephadex LH-20;chloroform in the chloroform-methanol elution reagent: the volume ratio of methanol is 1: 1.
- 13. the method of claim 1, wherein: further comprising a step of recrystallization, satisfying at least one of the following:the recrystallization solvent is methanol or petroleum ether-ethyl acetate;the number of recrystallization times is 2 to 4.
- 14. The method of claim 1, wherein: the Daqu is medium temperature wheat starter.
- 15. The method of claim 1, wherein: the Daqu is a strong-flavor medium-temperature yeast of pure wheat.
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Non-Patent Citations (3)
| Title |
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| Gregory J. SLACK,et al..Secondary metabolites from Eurotium species, Aspergillus calidoustus and A. insuetus common in Canadian homes with a review of their chemistry and biological activities.《MYCOLOGICAL RESEARCH》.2009,480-490. * |
| Xianwei Zou,et al..A New Prenylated Indole Diketopiperazine Alkaloid from Eurotium cristatum.《Molecules》.2014,17839-17847. * |
| 徐佳等.酱香型白酒酿造过程中霉菌的功能性研究.《酿酒》.2019,32-38. * |
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