WO2018028402A1 - Procédé de préparation de cristaux de bêta-carotène - Google Patents

Procédé de préparation de cristaux de bêta-carotène Download PDF

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Publication number
WO2018028402A1
WO2018028402A1 PCT/CN2017/093522 CN2017093522W WO2018028402A1 WO 2018028402 A1 WO2018028402 A1 WO 2018028402A1 CN 2017093522 W CN2017093522 W CN 2017093522W WO 2018028402 A1 WO2018028402 A1 WO 2018028402A1
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wet
carotene
crystals
cells
antioxidant
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PCT/CN2017/093522
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English (en)
Chinese (zh)
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李翔宇
汪志明
陆姝欢
田勇
周强
易德伟
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嘉必优生物技术（武汉）股份有限公司
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Publication of WO2018028402A1 publication Critical patent/WO2018028402A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/24—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by six-membered non-aromatic rings, e.g. beta-carotene
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
    • C12N1/12—Unicellular algae; Culture media therefor
    • C12N1/125—Unicellular algae isolates
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
    • C12N1/14—Fungi; Culture media therefor
    • C12N1/145—Fungal isolates
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P23/00—Preparation of compounds containing a cyclohexene ring having an unsaturated side chain containing at least ten carbon atoms bound by conjugated double bonds, e.g. carotenes
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
    • C12R2001/00—Microorganisms ; Processes using microorganisms
    • C12R2001/645—Fungi ; Processes using fungi
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
    • C12R2001/00—Microorganisms ; Processes using microorganisms
    • C12R2001/89—Algae ; Processes using algae

Definitions

  • the invention relates to a method for preparing ⁇ -carotene crystals, in particular to a method for preparing microbial-derived ⁇ -carotene crystals.
  • Carotenoids are nutrients that are widely found in plants, animals, and microorganisms and are closely related to human health. They mainly include ⁇ -carotene, lycopene, and lutein. Carotenoids not only have high medicinal value such as anti-cancer and anti-oxidation, but also an important source of vitamin A in the human body. As a food additive and a nutrient enhancer, carotenoids have been recognized by international organizations such as the FDA, the European Community, and the WHO. In recent years, carotenoids have been widely used in medicine, food, health care products, and cosmetics.
  • Natural carotenoids are mainly from plants.
  • plant raw materials have shortcomings such as insufficient supply and low content, and cannot be industrially utilized on a large scale.
  • Microorganisms have the advantages of fast growth, high content, and no seasonal influence. Therefore, it is an ideal method to produce carotenoids by microbial fermentation.
  • the main processes for extracting carotenoids from B. trispora include: high-quality homogenization of wet cells mixed with water, wet and dry cells and organic solvent extraction. After the crude extract is obtained, the steps of separation and purification are carried out to obtain a high content of crystals.
  • Chinese Patent No. 01804173.6 discloses the separation of a carotenoid crystal, which is mixed with water and then homogenized by a high pressure homogenizer to extract a mixture of carotenoids, and then the mixture is washed with ethanol and brine. The method has high temperature when extracting carotenoids, and is easy to cause oxidative degradation of carotenoids, and is difficult to separate and purify, and the yield is extremely low.
  • 201210180281.4 No. discloses a method for extracting ⁇ -carotene by using high pressure steam to break the wall.
  • this method uses higher temperatures and pressures, which tends to oxidize ⁇ -carotene, resulting in low product yield and affecting product quality.
  • the existing preparation of ⁇ -carotene crystals by microbial fermentation has the following disadvantages: high temperature treatment is required in the drying or extraction process, and it is easy to cause light and oxidative degradation of carotenoids, resulting in low yield and poor product quality. . Therefore, there is a need to consider an improved way to avoid loss of carotenoids during the preparation process.
  • a method for producing a ⁇ -carotene crystal of the present invention comprises the following steps:
  • an antioxidant is added.
  • the method for preparing ⁇ -carotene crystals as described above, and in the step (1), the microbial species is B. trispora, Dunaliella salina or yeast.
  • the antioxidant is dibutylhydroxytoluene, vitamin E, vitamin C palmitate, ethyl p-hydroxybenzoate or rosemary.
  • the antioxidant is preferably one of ethyl p-hydroxybenzoate, rosemary, vitamin E, dibutylhydroxytoluene, used in the above steps (3), (4), In at least one of the steps 6), it is further preferred to use dibutylhydroxytoluene, vitamin E and ethyl p-hydroxybenzoate for use in steps (3), (4) and (6), respectively, more preferably two.
  • Butylated hydroxytoluene is used in step (3)
  • vitamin E is used in step (4)
  • ethyl p-hydroxybenzoate is used in step (6).
  • the antioxidant is preferably dibutylhydroxytoluene or vitamin E, which is used in at least one of the above steps (3), (4), and (6).
  • the antioxidant is preferably vitamin E, vitamin C palmitate, dibutylhydroxytoluene or rosemary, which is used in at least one of the above steps (3), (4), (6) in.
  • the antioxidant is added in an amount of 0.1% to 5% by weight of the dry cells.
  • the mass ratio of the dry cells to the organic solvent is 1:3-1:30.
  • the organic solvent is hexane, dichloromethane, petroleum ether, ethyl acetate or acetone.
  • the method for preparing ⁇ -carotene of the invention has the following beneficial effects: due to the oxidative degradation of ⁇ -carotene, a series of volatile aroma substances are mainly produced, such as ⁇ -ionone, dihydro kiwi lactone, isophorone, oxidized Vorketone and so on.
  • a series of volatile aroma substances are mainly produced, such as ⁇ -ionone, dihydro kiwi lactone, isophorone, oxidized Vorketone and so on.
  • the large amount of these oxidative degradation products has a great influence on the purification of ⁇ -carotene, which affects the purity of ⁇ -carotene. Therefore, some or all of the antioxidants are added during the drying, solid-liquid separation and evaporative crystallization.
  • the agent not only reduces the loss of ⁇ -carotene during the extraction process, but also increases the yield of ⁇ -carotene.
  • the extraction rate of ⁇ -carotene crystals is increased to 64.1%, preferably to 66.1%, and further preferably to 69.1%. Further, it is further preferably increased to 73.3%, and more preferably to 80.1%, and a ⁇ -carotene crystal having higher purity and better quality can be obtained, wherein the purity of the obtained ⁇ -carotene is increased to 97.3%, preferably elevated. Up to 97.7%, further preferably increased to 98.1%, more preferably increased to 99.1%.
  • Detection method of ⁇ -carotene content of bacterial body weight accurately weigh 0.01 ⁇ 0.03g sample, accurate 0.0001g, after being broken by glass homogenizer, extract with ethyl acetate, and repeatedly extract until the sample is completely colorless. , set to 25ml. Then use a pipette to take 1ml and dilute to a certain multiple and then dilute to volume. Using ethyl acetate as a reference, the solution after constant volume was poured into a cuvette, the absorbance was measured at the maximum absorption wavelength in the range of 455 nm ⁇ 2 nm, and then ⁇ in the cells was calculated according to the ⁇ -carotene standard curve. - Carotene content.
  • m1 obtaining the crystal weight of ⁇ -carotene
  • M2 the weight of ⁇ -carotene dry cells
  • w content of ⁇ -carotene in ⁇ -carotene dry cells.
  • ⁇ -carotene crystal purity detection method refer to GB 28310-2012 national food safety standard food additive ⁇ -carotene (fermentation method).
  • the crystallization mother liquid is suction filtered to obtain coarse and wet crystals, and the coarse wet crystals are washed with 500 ml of petroleum ether, and then suction-filtered to obtain wet crystals.
  • the wet crystals are dried under vacuum at 80 ° C, -0.085 MPa for 2 hours to obtain finished carotenoid crystals. .
  • the extraction rate of the carotenoid crystal was calculated to be 73.3%, and the purity of the beta-carotene was determined to be 98.1%.
  • the yeast is inoculated and fermented, and the fermentation liquid is centrifuged to obtain a wet cell having a water content of 80.5%.
  • freeze-drying conditions vacuum 20 Pa, trap temperature is -40 ° C, and dried for 20 h.
  • the spray drying conditions are: hot air temperature 130°C, material temperature 65°C, fan frequency 45Hz, feed rate 5kg/ h.
  • the crystallization mother liquid was suction filtered to obtain coarse and wet crystals, and the crude wet crystals were further filtered with 5 L of ethanol to obtain wet crystals.
  • the wet crystals were dried under vacuum at 80 ° C, -0.085 MPa for 2 hours to obtain a finished carotenoid crystal.
  • the extraction rate of the carotenoid crystal was calculated to be 73.3%, and the purity of the beta-carotene was determined to be 98.1%.
  • freeze-drying conditions are: vacuum 20 Pa, trap temperature is -40 ° C, and dried for 20 h.
  • the spray drying conditions are: hot air temperature 130°C, material temperature 65°C, fan frequency 45Hz, feed rate 5kg/ h.
  • the crystallization mother liquid is suction filtered to obtain coarse and wet crystals, and the coarse wet crystals are washed with 500 ml of dichloromethane, and then suction-filtered to obtain wet crystals.
  • the wet crystals are dried under vacuum at 80 ° C, -0.085 MPa for 2 hours to obtain a finished carotenoid. Crystal.
  • the extraction rate of the carotenoid crystal was calculated to be 73.3%, and the purity of the beta-carotene was determined to be 98.1%.
  • the crystallization mother liquid is suction filtered to obtain coarse and wet crystals, and the coarse wet crystals are washed with 500 ml of dichloromethane, and then suction-filtered to obtain wet crystals.
  • the wet crystals are dried under vacuum at 80 ° C, -0.085 MPa for 2 hours to obtain a finished carotenoid. Crystal.
  • the extraction rate of the carotenoid crystal was calculated to be 80.1%, and the purity of the ⁇ -carotene was determined to be 99.1%.
  • the method for preparing ⁇ -carotene of the invention has the following beneficial effects: in the steps of drying, solid-liquid separation and evaporative crystallization, some or all of the antioxidants are added, the loss of ⁇ -carotene during the extraction process is reduced, and ⁇ - is improved.
  • the yield of carotene and the ⁇ -carotene crystal obtained at the same time are higher in purity and better in quality.
  • antioxidants mentioned in the present invention are not limited to the types exemplified in the examples, and other products having the same effects in use are within the scope of the present invention.
  • the invention provides a method for preparing ⁇ -carotene crystals, comprising the steps of: (1) inoculating a microbial strain to ferment, (2) performing solid-liquid separation of the fermentation liquid to obtain a wet bacterial body; and (3) wet bacteria After drying, the dried cells are obtained; (4) extracting the dried cells with an organic solvent; (5) obtaining an extract after solid-liquid separation; (6) evaporating and crystallizing the extract to obtain a crystallization mother liquid; (7) crystallization mother liquid is solidified The liquid is separated to obtain coarse wet crystals; (8) the crude wet crystals are washed with an organic solvent, and dried under vacuum to obtain ⁇ -carotene crystals; and in steps (3), (4) and (6), antioxidants are added.
  • the invention reduces the loss of ⁇ -carotene in the extraction process, improves the yield of ⁇ -carotene, and at the same time, the obtained ⁇ -carotene crystal has higher purity and better quality.
  • the method of the invention can be applied to the field of carotenoid extraction on a large scale, and has broad market prospects.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
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  • Biotechnology (AREA)
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  • Bioinformatics & Cheminformatics (AREA)
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  • General Health & Medical Sciences (AREA)
  • Microbiology (AREA)
  • General Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Botany (AREA)
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  • Tropical Medicine & Parasitology (AREA)
  • Medicinal Chemistry (AREA)
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  • General Chemical & Material Sciences (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé de préparation de cristaux de bêta-carotène, comprenant les étapes suivantes : (1) inoculation et fermentation d'une souche microbienne, et (2) réalisation d'une séparation solide-liquide du bouillon de fermentation pour obtenir des bactéries humides; (3) sécher les bactéries humides pour obtenir des bactéries sèches; (4) utiliser un solvant organique pour effectuer une extraction sur les bactéries sèches; (5) la réalisation d'une séparation solide-liquide pour obtenir une solution d'extrait; (6) l'évaporation et la cristallisation de la solution d'extrait pour obtenir une liqueur mère cristalline; (7) effectuer une séparation solide-liquide de la liqueur mère de cristal pour obtenir un cristal humide brut; (8) laver le cristal humide brut dans un solvant organique, et sécher sous vide pour obtenir les cristaux de bêta-carotène. Un antioxydant est ajouté aux étapes (3), (4) et (6). Un antioxydant est ajouté dans une partie ou la totalité des étapes de séchage, de séparation solide-liquide, d'évaporation et de cristallisation, la réduction de la perte de bêta-carotène dans le processus d'extraction et l'amélioration du rendement en bêta-carotène; la pureté et la qualité des cristaux de bêta-carotène obtenus sont élevées.
PCT/CN2017/093522 2016-08-09 2017-07-19 Procédé de préparation de cristaux de bêta-carotène WO2018028402A1 (fr)

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CN106278976A (zh) * 2016-08-09 2017-01-04 嘉必优生物技术（武汉）股份有限公司 制备β‑胡萝卜素晶体的方法
CN106278978A (zh) * 2016-08-09 2017-01-04 嘉必优生物技术（武汉）股份有限公司 制备β‑胡萝卜素晶体的方法
CN106278977A (zh) * 2016-08-09 2017-01-04 嘉必优生物技术（武汉）股份有限公司 制备β‑胡萝卜素晶体的方法
CN106278975A (zh) * 2016-08-09 2017-01-04 嘉必优生物技术（武汉）股份有限公司 制备β‑胡萝卜素晶体的方法
CN114133348A (zh) * 2021-11-09 2022-03-04 湖北广济药业股份有限公司 一种高纯度全反式β-胡萝卜素的提取方法

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