CN113816886B - Method for extracting selenium-methyl selenocysteine from selenium-rich ganoderma lucidum mycelia - Google Patents
Method for extracting selenium-methyl selenocysteine from selenium-rich ganoderma lucidum mycelia Download PDFInfo
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Abstract
The invention discloses a method for extracting selenium-methyl selenocysteine from selenium-rich ganoderma lucidum mycelia. The method is characterized in that the ratio of nitrogen to oxygen is controlled, chitinase and ammonium dihydrogen phosphate solutions with different concentration gradients are used for fully releasing target seleno-amino acid in mycelia, and finally, preparative high performance liquid chromatography tandem inductively coupled plasma mass spectrometry is used for separation. The invention fills the technical gap of extracting selenium-methyl selenocysteine from selenium-rich fungi, the extraction rate of the selenium-methyl selenocysteine by adopting the method is up to 90 percent, and the method is simple and has stable effect.
Description
Technical Field
The invention relates to the field of food and chemistry, and provides a method for extracting selenium-methyl selenocysteine from selenium-rich ganoderma lucidum mycelia
Background
Selenium is a necessary trace element for human body, and selenium deficiency can cause keshan disease, Kaschin-Beck disease, heart disease, hypothyroidism, hypoimmunity and other diseases. Lowering the blood selenium level increases the risk of cancer, and selenium has a very definite help in tumor prevention and radiotherapy and chemotherapy. More than 40 countries and regions in the world are deficient in selenium, and 1 hundred million people in China are deficient in selenium or low in selenium, and diseases related to selenium deficiency are suffered from or are very easy to occur. Selenium is mainly ingested by the human body through the dietary route. The low selenium content in soil and the insufficient selenium content in diet are the common problems in China and even all over the world. Therefore, the search and development of selenium-enriched foods and selenium supplements to ensure the human body to take in sufficient selenium is the primary way to solve the problem. Because inorganic selenium such as sodium selenite and sodium selenate has high toxicity to cells, the current domestic selenium supplements mainly comprise organic selenium, such as seleno-carrageenan, selenium-enriched yeast and the like.
Selenium-methyl selenocysteine is a natural selenium-containing amino acid, is a methylated derivative of 21 kinds of essential amino acid-selenocysteine for human bodies, is an important precursor substance of methyl selenium, has the effects of preventing and treating cancers, resisting oxidation and aging, treating cardiovascular and cerebrovascular diseases, removing heavy metal toxicity and the like, and is approved as a third-generation selenium-source food nutrition enhancer by the Ministry of health in 2009. Modern pharmacological studies have shown that different forms of selenium have different anticancer effects, and selenium-methylselenocysteine has been shown to be one of the potent chemoanticancer agents. Compared with a second-generation selenium enhancer, namely selenoprotein, selenium-enriched yeast, seleno-carrageenan and selenium-enriched bacteria powder, the selenium-enriched microbial powder has the advantages of low toxicity, clear structure, stable content, clear metabolic mechanism in a human body and the like, and can be widely applied to the fields of foods and medicines. In industry, selenium-methylselenocysteine is mainly synthesized by a chemical method. However, the chemical synthesis method has the following disadvantages: the high price of raw materials leads to high production cost, the multiple reaction steps and the complex process route, and the used organic reagent and the generated intermediate product have great environmental pollution. Therefore, the development of a green, convenient and safe selenium-methyl selenocysteine obtaining method has important significance. In 1960, scientists first isolated selenium-methylselenocysteine from Astragalus membranaceus. Plants growing in selenium-rich areas have the ability to accumulate selenium-methylselenocysteine, such as garlic, onions, broccoli, leguminous plants, wild leeks, etc. However, natural plant-derived selenocysteine has a low content, and the yield is affected by a long plant growth cycle. The microbial conversion method can better overcome the defects. For example, the technology of converting inorganic selenium into selenium-methylselenocysteine by culturing yeast has been developed, the process cycle is short and the yield of selenium-methylselenocysteine is large. In addition to yeast, edible fungi can also be used to produce selenium-methylselenocysteine. The technology is mainly characterized in that inorganic selenium additives such as sodium selenite and the like are added into a culture base material of edible fungus mycelia, and the inorganic selenium is converted into organic selenium through a metabolic system of the mycelia under a specific culture condition. The selenium-enriched edible fungi not only is safe to eat and high in selenium bioavailability, but also can effectively improve the blood selenium level in animals or human bodies, and can be used as a selenium nutritional additive for developing and producing selenium-enriched health-care foods.
The ganoderma lucidum is a fungus with extremely strong selenium enrichment capability, the growth cycle of the mycelium is short, the yield is high, 13000 mu g/g or more organic selenium can be accumulated, wherein the proportion of selenium-methyl selenocysteine is as high as about 40 percent, and the ganoderma lucidum is an ideal food-grade raw material for obtaining the selenium-methyl selenocysteine. However, there is still a gap in the current technology for obtaining selenium-methylselenocysteine from selenium-enriched fungi, and "a method for extracting selenocysteine and selenocysteine from polyselenide plant cardamine hirsute" (granted application No. 201410361185.9) introduces a method for obtaining selenocysteine and selenocysteine from selenium-enriched plants. The chemical property of the selenium-methyl selenocysteine is very active, the selenium-methyl selenocysteine is quickly oxidized and volatilized by illumination, high temperature and oxygen, and the chemical form of the selenium-methyl selenocysteine is damaged by strong acid and strong alkali, so the method used in the invention is not suitable for extracting the selenium-methyl selenocysteine from fungal mycelia. In addition, the process of detecting the form of seleno-amino acid in a biological sample relates to a technology of releasing seleno-amino acid from protein, and the method for determining the form of selenium in high-selenium fungus (authorized application number: 201510656845.0) uses a weak alkaline solvent and ball milling to carry out wall breaking treatment on the high-selenium fungus, and then uses pepsin and trypsin to carry out stepwise continuous enzymolysis to release the seleno-amino acid. Similarly, there are patents which use proteinase K and proteinase XV to directly subject plant samples to enzymatic treatment to release seleno-amino acids for detection. However, unlike selenomethionine and selenocysteine, which are non-specific, by replacing methionine and cysteine, selenocysteine is not specifically incorporated into biological proteins, it is an intermediate product of selenium metabolism in plants and microorganisms, and therefore it is not involved in protein synthesis nor incorporated into proteins. It is reported to exist in tissues mainly in a free state. Therefore, physical grinding can cause oxidation when the selenium-methyl selenocysteine is exposed to air and light, and different types of protease are used for enzymolysis, so that the selenium-methyl selenocysteine can be mixed with selenomethionine and selenocysteine, and the extraction difficulty is increased, so that an efficient and targeted selenium-methyl selenocysteine extraction method needs to be developed.
Disclosure of Invention
The invention aims to develop a method for extracting selenium-methyl selenocysteine from selenium-enriched ganoderma lucidum mycelia on the premise of ensuring high extraction rate and not damaging the morphological structure of an extract.
In order to achieve the purpose, the technical scheme of the invention is as follows.
A method for extracting selenium-methyl selenocysteine from selenium-rich ganoderma lucidum mycelia comprises the following steps:
(1) weighing selenium-rich Ganoderma mycelia after vacuum freeze drying, placing in a pressure-resistant sealable container, adding water, and introducing nitrogen gas;
(2) adjusting the pH value of the mixed solution to 4.0-7.0, and then adding enzyme for enzymolysis;
(3) adding ammonium dihydrogen phosphate into the mixed solution to make the concentration of ammonium dihydrogen phosphate rise in a gradient manner, and maintaining the pH value at 5-6.5 all the time in the process;
(4) and (4) filtering the mixed solution obtained in the step (3) at low temperature and in a dark place, introducing the filtrate into a preparative high performance liquid chromatography-inductively coupled plasma mass spectrum for separation, collecting eluent, dialyzing to remove salt, and carrying out vacuum freeze drying on the dialysate to obtain the finished selenium-methyl selenocysteine.
Further, in the step (1), the volume ratio of the final nitrogen to the final oxygen in the container is 7: 1-9: 1.
Further, in the step (1), the pressure-resistant sealable container is an iron pressure-resistant sealable container.
Further, in the step (1), the addition amount of the water satisfies: the ratio of the feed to the liquid is 1:20 to 1:30 g/L.
Further, in the step (2), the selected enzyme is chitinase.
Further, the mass-to-volume ratio of the chitinase to the mycelium is 10-15 mg: 5-20 mL.
Further, in the step (2), the enzymolysis time is 15-24 hours, and the temperature is 8-10 ℃.
Further, in the step (3), the adding of ammonium dihydrogen phosphate to the mixed solution specifically includes: adding ammonium dihydrogen phosphate with the mass percent concentration of 0.5-1% into the mixed solution every 0.5-3 hours.
Furthermore, in the step (3), the concentration of ammonium dihydrogen phosphate is increased in a gradient manner from 0.1 to 3% by mass.
Further, in the step (4), the low-temperature condition is 15-20 ℃.
Compared with the prior art, the invention has the advantages that:
(1) by adjusting the nitrogen-oxygen ratio in the extraction device and maintaining the whole-course light-proof low-temperature condition, the selenium-methyl selenocysteine is ensured not to be oxidized or volatilized to the maximum extent in the extraction process.
(2) The chitinase can decompose the cell wall of the fungus in a targeted manner, so that the selenium-methyl selenocysteine is fully released from the tissue, and the protein is not subjected to enzymolysis, thereby avoiding the interference of selenomethionine and selenocysteine in the extraction process.
(3) Compared with strong acid and strong alkali extraction method, the ammonium dihydrogen phosphate solution with increased specific concentration gradient can extract the selenium-methyl selenocysteine from the tissue to the maximum extent without damaging the chemical form, the extraction rate of the selenium-methyl selenocysteine reaches more than 90%, and in contrast, the total extraction rate of the seleno-amino acid obtained from the plant by protease extraction method is less than 20%.
Detailed Description
The present invention is further described in detail below with reference to examples so that those skilled in the art can better understand the present invention and can practice it, but the method of practicing the present invention is not limited thereto.
Example 1
In the embodiment of extracting selenium-methyl selenocysteine from selenium-rich ganoderma lucidum mycelia, the total selenium content of the selected selenium-rich ganoderma lucidum mycelia (dry weight) is 8 mg/g.
(1) 100g of selenium-rich ganoderma lucidum mycelia subjected to vacuum freeze drying is weighed in an iron pressure-resistant sealable container (3L), 1.8L of water is added, and then nitrogen is filled in the container to ensure that the volume ratio of the nitrogen to the oxygen in the container is 7.6: 1.
(2) The pH of the mixture was adjusted to 5.5-6.0, and then 2g of chitinase was added and reacted at 10 ℃ for 20 hours.
(3) Adding ammonium dihydrogen phosphate into the mixed solution every 1.5 hours to ensure that the mass percent concentration of the ammonium dihydrogen phosphate is increased in a gradient manner within 1.0-3.0 percent, and the pH value is always maintained within the range of 5-6.5 in the process.
(4) And (4) filtering the mixed solution obtained in the step (3), feeding the filtrate into a preparative high performance liquid chromatography series inductance coupling plasma mass spectrum equipped with a Hamilton RPR-X100 type anion exchange column for separation, collecting eluent, dialyzing and desalting, and carrying out vacuum freeze drying on the dialysate to obtain the finished selenium-methyl selenocysteine.
The implementation effect is as follows: the extraction rate of the L-selenium-methyl selenocysteine reaches 90.8 percent.
Example 2
In the embodiment of extracting selenium-methyl selenocysteine from selenium-rich ganoderma lucidum mycelia, the total selenium content of the selected selenium-rich ganoderma lucidum mycelia (dry weight) is 8 mg/g.
(1) 100g of selenium-rich ganoderma lucidum mycelia subjected to vacuum freeze drying is weighed in an iron pressure-resistant sealable container (3L), 2.5L of water is added, and nitrogen is filled to ensure that the volume ratio of the nitrogen to the oxygen in the container is 8.5: 1.
(2) The pH of the mixture was adjusted to 5.5 to 6.0, and then 2g of chitinase was added thereto and reacted at 10 ℃ for 20 hours.
(3) Adding ammonium dihydrogen phosphate into the mixed solution every 1.5 hours to ensure that the mass percent concentration of the ammonium dihydrogen phosphate is increased in a gradient manner within 1.0-3.0 percent, and the pH value is always maintained within the range of 5-6.5 in the process.
(4) And (3) filtering the mixed solution in the step (3) at 15 ℃, feeding the filtrate into a preparative high performance liquid chromatography series inductance coupling plasma mass spectrum equipped with a Hamilton RPR-X100 type anion exchange column for separation, collecting eluent, dialyzing to remove salt, and carrying out vacuum freeze drying on dialysate to obtain the finished product of the selenium-methyl selenocysteine.
The implementation effect is as follows: the extraction rate of the L-selenium-methyl selenocysteine reaches 91.1 percent.
Example 3
In the embodiment of extracting selenium-methyl selenocysteine from selenium-rich Ganoderma sinensis mycelia, the total selenium content of the selenium-rich Ganoderma sinensis (dry weight) is 2 mg/g.
(1) 100g of selenium-rich ganoderma lucidum mycelia subjected to vacuum freeze drying is weighed in an iron pressure-resistant sealable container (3L), 2L of water is added, and then nitrogen is filled in the container to ensure that the volume ratio of the nitrogen to the oxygen in the container is 7.5: 1.
(2) The pH of the mixture was adjusted to 5.5 to 6.0, and then 3.0g of chitinase was added thereto and reacted at 10 ℃ for 24 hours.
(3) Adding ammonium dihydrogen phosphate into the mixed solution every 1.5 hours to ensure that the mass percent concentration of the ammonium dihydrogen phosphate is increased in a gradient manner within 0.1-1.5 percent, and the pH value is always maintained within the range of 5-6.5 in the process.
(4) And (4) filtering the mixed solution obtained in the step (3), feeding the filtrate into a preparative high performance liquid chromatography series inductance coupling plasma mass spectrum equipped with a Hamilton RPR-X100 type anion exchange column for separation, collecting eluent, dialyzing and desalting, and carrying out vacuum freeze drying on the dialysate to obtain the finished selenium-methyl selenocysteine.
The implementation effect is as follows: the extraction rate of the L-selenium-methyl selenocysteine reaches 86.4 percent.
Example 4
In the embodiment of extracting selenium-methyl selenocysteine from selenium-rich mixed ganoderma lucidum mycelia, the total selenium content (dry weight) of the selected mixed ganoderma lucidum mycelia is 13 mg/g.
(1) Weighing 50g of selenium-rich ganoderma lucidum mycelia subjected to vacuum freeze drying in a 3L iron pressure-resistant sealable container, adding 1.5L of water, and filling nitrogen to ensure that the volume ratio of nitrogen to oxygen in the container is 9: 1.
(2) The pH of the mixture was adjusted to 5.5 to 6.0, and then 3.5g of chitinase was added thereto and reacted at 10 ℃ for 24 hours.
(3) Adding ammonium dihydrogen phosphate into the mixed solution every 2 hours to ensure that the mass percent concentration of the ammonium dihydrogen phosphate is increased in a gradient manner within the range of 2.0-3.0 percent, and the pH value is always maintained within the range of 5-6.5 in the process.
(4) And (4) filtering the mixed solution obtained in the step (3), feeding the filtrate into a preparative high performance liquid chromatography series inductance coupling plasma mass spectrum equipped with a Hamilton RPR-X100 type anion exchange column for separation, collecting eluent, dialyzing and desalting, and carrying out vacuum freeze drying on the dialysate to obtain the finished selenium-methyl selenocysteine.
The implementation effect is as follows: the extraction rate of the L-selenium-methyl selenocysteine reaches 91.2 percent.
Example 5
In the embodiment of extracting selenium-methyl selenocysteine from selenium-rich mixed ganoderma lucidum mycelia, the total selenium content (dry weight) of the selected mixed ganoderma lucidum mycelia is 13 mg/g.
(1) Weighing 50g of selenium-rich Ganoderma mycelia after vacuum freeze drying in an iron pressure-resistant sealable container (3L), adding 1.0L of water, and introducing nitrogen to make the volume ratio of nitrogen to oxygen in the container at 8.0: 1.
(2) The pH of the mixture was adjusted to 5.5 to 6.0, and then 2.5g of chitinase was added thereto and reacted at 10 ℃ for 24 hours.
(3) Adding ammonium dihydrogen phosphate into the mixed solution every 2 hours to ensure that the mass percent concentration of the ammonium dihydrogen phosphate is increased in a gradient manner within the range of 2.5-3.0 percent, and the pH value is kept within the range of 5-6.5 all the time in the process.
(4) And (4) filtering the mixed solution obtained in the step (3), feeding the filtrate into a preparative high performance liquid chromatography series inductance coupling plasma mass spectrum equipped with a Hamilton RPR-X100 type anion exchange column for separation, collecting eluent, dialyzing and desalting, and carrying out vacuum freeze drying on the dialysate to obtain the finished selenium-methyl selenocysteine.
The implementation effect is as follows: the extraction rate of the L-selenium-methyl selenocysteine reaches 90.24 percent.
Example 6
In the embodiment of extracting selenium-methyl selenocysteine from selenium-rich ganoderma lucidum mycelia, the total selenium content of the selected selenium-rich ganoderma lucidum mycelia (dry weight) is 8 mg/g.
(1) 100g of selenium-rich ganoderma lucidum mycelia subjected to vacuum freeze drying is weighed in an iron pressure-resistant sealable container (3L), 2L of water is added, and then nitrogen is filled in the container to ensure that the volume ratio of the nitrogen to the oxygen in the container is 7.0: 1.
(2) The pH of the mixture was adjusted to 5.5-6.0, and then 3g of chitinase was added and reacted at 10 ℃ for 22 hours.
(3) Adding ammonium dihydrogen phosphate into the mixed solution every 3 hours to ensure that the mass percent concentration of the ammonium dihydrogen phosphate is increased in a gradient manner within 1.0-1.5 percent, and the pH value is always maintained within the range of 5-6.5 in the process.
(4) And (4) filtering the mixed solution obtained in the step (3), feeding the filtrate into a preparative high performance liquid chromatography series inductance coupling plasma mass spectrum equipped with a Hamilton RPR-X100 type anion exchange column for separation, collecting eluent, dialyzing and desalting, and carrying out vacuum freeze drying on the dialysate to obtain the finished selenium-methyl selenocysteine.
The implementation effect is as follows: the extraction rate of the L-selenium-methyl selenocysteine reaches 81.68 percent.
Example 7
In the embodiment of extracting selenium-methyl selenocysteine from selenium-rich ganoderma lucidum mycelia, the total selenium content of the selected selenium-rich ganoderma lucidum mycelia (dry weight) is 8 mg/g.
(1) 100g of selenium-rich ganoderma lucidum mycelia which are subjected to vacuum freeze drying are weighed in an iron pressure-resistant sealable container (3L), 1.8L of water is added, and then nitrogen is filled in the container to ensure that the volume ratio of the nitrogen to the oxygen in the container is 7.6:1 finally.
(2) The pH of the mixture was adjusted to 5.5 to 6.0, and then 2.5g of chitinase was added thereto and reacted at 10 ℃ for 24 hours.
(3) Adding ammonium dihydrogen phosphate into the mixed solution every 0.5 hours to ensure that the mass percent concentration of the ammonium dihydrogen phosphate is increased in a gradient manner within the range of 2.0-3.0 percent, and the process always maintains the pH value within the range of 5-6.5.
(4) And (4) filtering the mixed solution obtained in the step (3), feeding the filtrate into a preparative high performance liquid chromatography series inductance coupling plasma mass spectrum equipped with a Hamilton RPR-X100 type anion exchange column for separation, collecting eluent, dialyzing and desalting, and carrying out vacuum freeze drying on the dialysate to obtain the finished selenium-methyl selenocysteine.
The implementation effect is as follows: the extraction rate of the L-selenium-methyl selenocysteine reaches 93.8 percent.
Example 8
In the embodiment of extracting selenium-methyl selenocysteine from selenium-rich ganoderma lucidum mycelia, the total selenium content of the selected selenium-rich ganoderma lucidum mycelia (dry weight) is 8 mg/g.
(1) 100g of selenium-rich ganoderma lucidum mycelia subjected to vacuum freeze drying is weighed in an iron pressure-resistant sealable container (3L), 1.8L of water is added, and then nitrogen is filled in the container to ensure that the volume ratio of the nitrogen to the oxygen in the container is 7.6: 1.
(2) The pH of the mixture was adjusted to 5.5 to 6.0, and then 2g of chitinase was added thereto and reacted at 10 ℃ for 20 hours.
(3) Adding ammonium dihydrogen phosphate into the mixed solution every 1 hour to ensure that the mass percent concentration of the ammonium dihydrogen phosphate is increased in a gradient manner within the range of 2.5-3.0 percent, and the pH value is always maintained within the range of 5-6.5 in the process.
(4) And (4) filtering the mixed solution obtained in the step (3), feeding the filtrate into a preparative high performance liquid chromatography series inductance coupling plasma mass spectrum equipped with a Hamilton RPR-X100 type anion exchange column for separation, collecting eluent, dialyzing and desalting, and carrying out vacuum freeze drying on the dialysate to obtain the finished selenium-methyl selenocysteine.
The implementation effect is as follows: the extraction rate of the L-selenium-methyl selenocysteine reaches 92.4 percent.
Claims (9)
1. A method for extracting selenium-methyl selenocysteine from selenium-rich ganoderma lucidum mycelia is characterized by comprising the following steps:
(1) weighing selenium-rich Ganoderma mycelia after vacuum freeze drying, placing in a pressure-resistant sealable container, adding water, and introducing nitrogen gas;
(2) adjusting the pH value of the mixed solution to 4.0-7.0, and then adding enzyme for enzymolysis;
(3) adding ammonium dihydrogen phosphate into the mixed solution to make the concentration of ammonium dihydrogen phosphate rise in a gradient manner, and maintaining the pH value at 5-6.5 all the time in the process;
(4) filtering the mixed solution obtained in the step (3) under the condition of low temperature and light protection, introducing the filtrate into a preparative high performance liquid chromatography series inductively coupled plasma mass spectrum for separation, collecting eluent, dialyzing and desalting, and carrying out vacuum freeze drying on the dialysate to obtain a finished product of selenium-methyl selenocysteine;
in the step (2), the selected enzyme is chitinase.
2. The method for extracting selenium-methylselenocysteine from selenium-rich ganoderma lucidum mycelia according to claim 1, wherein in the step (1), the volume ratio of the final nitrogen to the final oxygen in the container is 7: 1-9: 1.
3. The method for extracting Se-methylselenocysteine from Se-enriched ganoderma lucidum mycelia as claimed in claim 1, wherein in the step (1), the pressure-resistant sealable container is an iron pressure-resistant sealable container.
4. The method for extracting selenium-methylselenocysteine from selenium-rich ganoderma lucidum mycelia according to claim 1, wherein in the step (1), the addition amount of the water meets the following requirements: the ratio of the feed to the liquid is 1:20 to 1:30 g/L.
5. The method for extracting Se-methylselenocysteine from Se-enriched ganoderma lucidum mycelia as claimed in claim 1, wherein the mass-volume ratio of chitinase to mycelia is 10-15 mg: 5-20 mL.
6. The method for extracting Se-methylselenocysteine from Se-enriched ganoderma lucidum mycelia as claimed in claim 1, wherein in the step (2), the enzymolysis time is 15-24 hours and the temperature is 8-10 ℃.
7. The method for extracting Se-methylselenocysteine from Se-enriched ganoderma lucidum mycelia as claimed in claim 1, wherein in the step (3), the step of adding ammonium dihydrogen phosphate into the mixed solution comprises the following specific steps: adding ammonium dihydrogen phosphate with the mass percent concentration of 0.5-1% into the mixed solution every 0.5-3 hours.
8. The method for extracting Se-methylselenocysteine from Se-enriched ganoderma lucidum mycelia as claimed in claim 1, wherein in step (3), the concentration of ammonium dihydrogen phosphate is increased in a gradient manner within the range of 0.1-3%.
9. The method for extracting Se-methylselenocysteine from Se-enriched ganoderma lucidum mycelia as claimed in claim 1, wherein in the step (4), the low temperature is 15-20 ℃.
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