WO2021163828A1 - 一种高效制备富含肌肽类化合物的工艺方法 - Google Patents

一种高效制备富含肌肽类化合物的工艺方法 Download PDF

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Publication number
WO2021163828A1
WO2021163828A1 PCT/CN2020/075490 CN2020075490W WO2021163828A1 WO 2021163828 A1 WO2021163828 A1 WO 2021163828A1 CN 2020075490 W CN2020075490 W CN 2020075490W WO 2021163828 A1 WO2021163828 A1 WO 2021163828A1
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WIPO (PCT)
Prior art keywords
carnosine
pure water
efficiently preparing
filtrate
compounds according
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PCT/CN2020/075490
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English (en)
French (fr)
Chinese (zh)
Inventor
骆峰
杨升平
董婷婷
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上海辉文生物技术股份有限公司
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Application filed by 上海辉文生物技术股份有限公司 filed Critical 上海辉文生物技术股份有限公司
Priority to PCT/CN2020/075490 priority Critical patent/WO2021163828A1/zh
Priority to JP2022549250A priority patent/JP7423803B2/ja
Publication of WO2021163828A1 publication Critical patent/WO2021163828A1/zh

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine

Definitions

  • the invention relates to the technical field of the preparation process of carnosine compounds, in particular to a process method for efficiently preparing high-quality carnosine compounds rich in low-content arsenic.
  • Carnosine (L-Carnosine), the scientific name ⁇ -alanyl-L-histidine, is a dipeptide composed of ⁇ -alanine and L-histidine, a crystalline solid.
  • Carnosine compounds exist in many forms, including carnosine, anserine, cetyl carnosine, etc., and their chemical structures all contain ⁇ -alanine and L-histidine units, but the histidine residues of anserine and cetyl carnosine are Different N atoms on the imidazole ring are substituted by methyl groups.
  • the muscles and brain tissues of animals contain very high concentrations of carnosine compounds, which have strong antioxidant capacity and are beneficial to the human body.
  • Carnosine has been proven to scavenge reactive oxygen free radicals (ROS) and ⁇ , ⁇ unsaturated aldehydes formed by excessive oxidation of fatty acids in cell membranes during oxidative stress.
  • ROS reactive oxygen free radicals
  • ⁇ , ⁇ unsaturated aldehydes formed by excessive oxidation of fatty acids in cell membranes during oxidative stress.
  • foods with carnosine compounds as functional substances have been on the market, mainly used for anti-aging, lowering uric acid, sports drinks, etc.
  • the purpose of the present invention is to overcome the above-mentioned problems in the prior art and provide a process method for efficiently preparing compounds rich in carnosine.
  • a process method for efficiently preparing carnosine-rich compounds includes the following steps:
  • Raw material processing the raw material is processed to obtain the filtrate, and the filter residue is ready for use;
  • step 2) Purification: The filtrate obtained in step 1) is adsorbed by ion exchange resin, and the mass ratio of ion exchange resin to filtrate is 1:0.5-3; after the adsorption is completed, the resin is washed with pure water and the waste liquid is discarded; after the water washing is completed Add 0.5-5% acetic acid solution for washing, the consumption of acetic acid solution is 1-10 times the amount of resin; start counting from the addition of acetic acid, and collect the acetic acid eluate;
  • step 3 Concentration: the liquid collected in step 2) is concentrated by rotating to dryness, then pure water is added and evaporated to dryness under reduced pressure, repeating several times;
  • step 3) The liquid obtained in step 3) is prepared by adding dextrin to form a preparation solution according to the requirements of the final product for the content of carnosine compounds, and the preparation solution is heated to 80-90°C, and sterilized by heat preservation for 30-50 minutes;
  • step 5) Spray drying: the sterilizing solution obtained in step 4) is spray dried to obtain a carnosine-rich sample.
  • a preferred solution of the present invention is that the raw material in step 1) is marine fish tissue, and the processing process is: take the marine fish tissue and pulverize it into fine solids; put the pre-pulverized solids into the extraction tank, add pure water and pure The mass ratio of water to solid matter is 0.5-2:1, heated to 50°C-100°C, hydrolyzed for 2-6 hours, and filtered to obtain the first extract; add pure water and pure water to the filter residue after the first extraction The mass ratio to the filter residue is 0.5-2:1, the temperature is raised to 50°C-100°C, hydrolyzed for 2-6 hours, and filtered to obtain the second extract. The first extract and the second extract are combined as the filtrate.
  • the marine fish tissue includes at least one of fish meat, fish bones, and fish skin.
  • the pulverization is coarse pulverization using a coarse crusher, and then pulverization for fine pulverization.
  • the ion exchange resin is an anion exchange resin.
  • step 2 the consumption of acetic acid solution in step 2) is 1-10 times the amount of resin
  • step 4 the temperature of the preparation solution is increased to 85°C, and the temperature is maintained and sterilized for 45 minutes.
  • the present invention can obtain hydrolyzed protein powder by-products during the process of extracting carnosine compounds.
  • the specific process is that pure water is added to the filter residue after the second extraction and the mass ratio of pure water to filter residue is 0.5-2:1, and the temperature is raised to 40-70. °C, add the alkaline protease with a mass fraction of 0.05%-10%, hydrolyze for 1-4 hours, filter and concentrate the filtrate to a viscous state, spray drying to obtain the by-product of hydrolyzed protein powder.
  • the mass ratio of pure water to filter residue is 1-1.8:1.
  • the raw material in step 1) is fish soup obtained during the processing of marine fish products.
  • the present invention obtains a functional substance applied to food through pre-crushing, extraction, purification, concentration, sterilization and spray drying of marine fish tissues, which has strong water solubility and significant It has anti-oxidation, anti-aging, and uric acid-lowering functions. It has been used in the food industry as natural antioxidants and uric acid-lowering dietary substances, namely carnosine compounds.
  • the present invention can avoid environmental pollution caused by traditional chemical synthesis and high cost problems caused by complicated synthesis steps, and at the same time solves the problem of excessive arsenic content in marine fish extracts, making the product safer.
  • the present invention can obtain by-products of hydrolyzed protein powder at the same time, improve resource utilization rate, and have higher economic and social value.
  • Figure 1 is a liquid chromatogram of Examples 1 to 4 and Comparative Examples 1-4 of the present invention
  • Fig. 2 is a diagram showing the detection results of arsenic spots of some examples and comparative examples of the present invention.
  • the first extract and the second extract are combined as the filtrate ,
  • the filter residue is ready for use; the filtrate is adsorbed with 717 anion exchange resin, and the mass ratio of ion exchange resin to filtrate is 1:2; after the adsorption is completed, the resin is washed with pure water and the waste liquid is discarded; after the water washing is completed, the mass fraction is 2.5% Wash with 2000ml of acetic acid solution, start counting from the addition of acetic acid, collect the acetic acid eluate; spin and concentrate the collected liquid to dryness, then add 100mL of pure water and evaporate to dryness, repeat once, then add 100mL of pure water to evaporate to dryness under reduced pressure; to get According to the requirements of the final product for the content of carnosine compounds, dextrin is added to prepare a preparation solution.
  • the preparation solution is heated to 85°C, and sterilized by insulation for 45 minutes; the obtained sterilization solution is spray-dried to obtain a carnosine-rich sample.
  • the sample is white or
  • the first extract and the second extract are combined as the filtrate ,
  • the filter residue is ready for use; the filtrate is adsorbed with 717 anion exchange resin, and the mass ratio of ion exchange resin to filtrate is 1:0.5; after the adsorption is completed, the resin is washed with pure water and the waste liquid is discarded; after the water washing is completed, the mass fraction is 0.5% Wash with 500ml of acetic acid solution, start counting from the addition of acetic acid, collect the acetic acid eluate; spin and concentrate the collected liquid to dryness, then add 100mL of pure water and evaporate to dryness, repeat once, then add 100mL of pure water to evaporate to dryness under reduced pressure; get According to the requirements of the final product for the content of carnosine compounds, dextrin is added to prepare a preparation solution.
  • the preparation solution is heated to 80°C, and sterilized for 50 minutes.
  • the obtained sterilization solution is spray-dried to obtain a carnosine-rich sample.
  • the sample is white
  • the first extract and the second extract are combined as the filtrate ,
  • the filter residue is ready for use; the filtrate is adsorbed with 717 anion exchange resin, and the mass ratio of ion exchange resin to filtrate is 1:3; after the adsorption is completed, the resin is washed with pure water and the waste liquid is discarded; after the water washing is completed, the mass fraction is added to 5% Wash with 1000ml of acetic acid solution, start counting from the addition of acetic acid, collect the acetic acid eluate; spin and concentrate the collected liquid to dryness, then add 100mL of pure water and evaporate to dryness, repeat once, then add 100mL of pure water to evaporate to dryness under reduced pressure; get According to the requirements of the final product for the content of carnosine compounds, dextrin is added to prepare a preparation solution, and the preparation solution is heated to 90°C, and sterilized by heat preservation for 30 minutes; the obtained sterilization solution is spray-dried to obtain a carnosine-rich sample.
  • the sample
  • the ammonia eluate was concentrated to dryness, and 100 mL of water was added and concentrated under reduced pressure until it became viscous. After sterilization, it was spray-dried to obtain a carnosine sample. The sample was white or light gray without ammonia smell.
  • the acetic acid eluate was concentrated to dryness, and 100 mL of water was added and evaporated to dryness under reduced pressure. The residual acetic acid was removed by this method. Repeatedly, 100 mL of water was added and spray-dried to obtain a carnosine sample. The sample was white or light gray without acetic acid smell.
  • Chromatographic column C18 reversed phase column (4.6x 150mm Shiseido Capcell Pak C18 ODS)
  • Mobile phase phase A: ammonium dihydrogen phosphate-sodium pentasulfonate; phase B: acetonitrile.
  • the process method for efficiently preparing carnosine-rich compounds provided by the present invention has the main product carnosine content as high as 40% or more, and the arsenic content is less than 2ppm, which meets the needs of the food industry.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Peptides Or Proteins (AREA)
  • Saccharide Compounds (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
PCT/CN2020/075490 2020-02-17 2020-02-17 一种高效制备富含肌肽类化合物的工艺方法 WO2021163828A1 (zh)

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PCT/CN2020/075490 WO2021163828A1 (zh) 2020-02-17 2020-02-17 一种高效制备富含肌肽类化合物的工艺方法
JP2022549250A JP7423803B2 (ja) 2020-02-17 2020-02-17 カルノシンに富む化合物を効率的に製造するためのプロセス方法

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114196640A (zh) * 2021-12-09 2022-03-18 中国科学院南海海洋研究所 一种源于新型贝类的l-肌肽合成酶atpgd及其应用

Citations (3)

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Publication number Priority date Publication date Assignee Title
CN1915980A (zh) * 2006-09-07 2007-02-21 重庆大学 肌肽类似物制备方法
CN108486185A (zh) * 2018-04-20 2018-09-04 江苏诚信药业有限公司 一种制备肌肽的新工艺方法
CN110343072A (zh) * 2019-07-12 2019-10-18 浙江海洋大学 一种从鲣鱼头中提取肌肽的方法

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JP5382633B2 (ja) 2006-05-25 2014-01-08 学校法人順正学園 脳血管性認知症の予防または治療薬
JP5142126B2 (ja) 2007-08-22 2013-02-13 東海物産株式会社 抗酸化性ジペプチドの製造方法

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CN1915980A (zh) * 2006-09-07 2007-02-21 重庆大学 肌肽类似物制备方法
CN108486185A (zh) * 2018-04-20 2018-09-04 江苏诚信药业有限公司 一种制备肌肽的新工艺方法
CN110343072A (zh) * 2019-07-12 2019-10-18 浙江海洋大学 一种从鲣鱼头中提取肌肽的方法

Non-Patent Citations (1)

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Title
ZHANG, SHUO: "Physiological Activities and Determination Methods of Carnosine", NATURAL PRODUCT RESEARCH AND DEVELOPMENT, 15 April 2008 (2008-04-15), pages 367 - 370, XP055839846, [retrieved on 20210910], DOI: 10.16333/j .1001 -6880.2008.02.002 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114196640A (zh) * 2021-12-09 2022-03-18 中国科学院南海海洋研究所 一种源于新型贝类的l-肌肽合成酶atpgd及其应用

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