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WO2016076454A1 - Procédé de culture de microorganismes et procédé de séparation et de purification de 9-cis β-carotène à partir des microorganismes cultivés - Google Patents

Procédé de culture de microorganismes et procédé de séparation et de purification de 9-cis β-carotène à partir des microorganismes cultivés Download PDF

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Publication number
WO2016076454A1
WO2016076454A1 PCT/KR2014/010853 KR2014010853W WO2016076454A1 WO 2016076454 A1 WO2016076454 A1 WO 2016076454A1 KR 2014010853 W KR2014010853 W KR 2014010853W WO 2016076454 A1 WO2016076454 A1 WO 2016076454A1
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Prior art keywords
carotene
cis
microorganisms
cis beta
beta
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English (en)
Korean (ko)
Inventor
윤태성
신병철
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Arcaeir Inc
Korea Research Institute of Bioscience and Biotechnology KRIBB
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Arcaeir Inc
Korea Research Institute of Bioscience and Biotechnology KRIBB
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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
    • 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

Definitions

  • the present invention includes a method of culturing a microorganism using a photochemical gas generated by gas injection and light source control, and a method for separating and purifying 9-cis beta carotene (9-cis ⁇ -carotene) from the culture microorganism. , And a method for producing 9-cis beta-carotene from microorganisms.
  • Carotenoids are pigments that represent an orange-based (yellow to bright red) color that is primarily present in the peels of green and yellow vegetables such as carrots, old pumpkins, bell peppers, sesame leaves, lettuce, leeks, and spinach.
  • beta-carotene ⁇ -carotene
  • Beta-carotene is a precursor of almost all carotenoids, which are converted into vitamin A, an essential nutrient in the body. Beta-carotene is widely used as a food additive due to its antioxidant effect, high nutritional value, and unique color to prevent oxidation damage in animal tissues, and is also useful as an anticancer agent, vascular disease agent, and antioxidant related to skin aging. Is being used.
  • 9-cis beta-carotene (9-cis ⁇ -carotene) is known to have an excellent effect as a drug among the isomers of beta-carotene.
  • the amount of beta-carotene present in green yellow vegetables and fruits is not so high that its production does not meet the demand, and the purification of beta-carotene from natural products is a mixture of all-trans beta-carotene and 9-cis beta-carotene. Isomers do not separate the situation.
  • Dunaliella a natural microalgae, is a eukaryotes belonging to photosynthetic green algae, which can survive in salt concentrations ranging from about one tenth of seawater to 5M near salts. Exhibits high properties. Microalgae of the genus Dunaliella are found in places with low nitrogen content, strong sunlight and high salt concentrations, which can accumulate beta-carotene in the cells and become yellow-green to orange when exposed to such strong environmental stress conditions. Is found. These beta-carotenes have been reported to accumulate with oily granulocytes in the thylakoid interstitial spaces in the chloroplasts (Ben-Amotz et al., J. Phycol. 18: 529-537), and these accumulated beta-carotenes protect the photosynthetic system from strong light. We assume that it is for.
  • a series of processes in which microorganisms, animals, and plant cells are inoculated in proper breeding and propagated under appropriate conditions such as temperature and oxygen are called cultures, and the type of culture is classified into liquid culture and solid culture.
  • Important external conditions in culture include temperature, humidity, light gas phase composition (partial pressure of carbon dioxide and oxygen), and the most important direct influence on the cultured organisms is the medium.
  • the medium is also known as an incubator and is a direct environment for the organism, and is also a source of various nutrients necessary for survival and proliferation.
  • the liquid culture phase using the liquid medium cultures algae and microorganisms by controlling the temperature, roughness, gas and saturation amount of organic and inorganic matters contained in the medium, that is, nutrition culture method, and in general, the incubation time of algae and microorganisms
  • a method of adjusting the nutrient content of the medium is mainly used.
  • the aggregation of the culture cells occurs in proportion to the growth of the culture. This agglomeration phenomenon can be found in most algae and microorganisms and is a cause of inhibiting the speed of cell culture.
  • Patent Publication No. KR10-2014-0046132 discloses a method of preventing agglomeration of a culture through microspray of air on a liquid medium, and generating a photochemical gas by controlling light sources, thereby accelerating the growth rate of algae and microorganisms. It is adopted.
  • 9-cis beta-carotene is isolated and purified from the culture microorganisms. Research on how to produce is urgently needed.
  • the inventors of the present invention while searching for the production method of 9-cis beta-carotene (9-cis ⁇ -carotene), after culturing the microorganisms using the photochemical gas generated by gas injection and light source control, the culture When separating and purifying 9-cis beta-carotene from the microorganism, it is confirmed that the production of 9-cis beta-carotene is easy, and eco-friendly mass production, 9-cis beta-carotene shows excellent purity, the present invention was completed.
  • the present invention provides a method for improving the cultivation rate of microorganisms using photochemical gas generated by microspray of gas, and light source control, and a method for separating and purifying 9-cis beta-carotene from the culture microorganism. It is intended to provide a method for producing 9-cis beta-carotene.
  • the present invention comprises the steps of culturing the microorganisms using the photochemical gas generated by the gas injection and light source control; And separating and purifying 9-cis beta-carotene (9-cis ⁇ -carotene) from the cultured microorganisms, which provides a method for producing 9-cis beta-carotene from microorganisms.
  • the present invention comprises the steps of culturing the microorganisms using the photochemical gas generated by the gas injection and light source control; And separating and purifying 9-cis beta-carotene (9-cis ⁇ -carotene) from the cultured microorganisms, which provides a method for producing 9-cis beta-carotene from microorganisms.
  • the present invention can facilitate production of 9-cis beta-carotene by varying the composition and culture conditions of the medium, such as salt concentration, concentration of nitrogen source, or pressure, light source control, in order to maximize growth of the strain.
  • the micro-injection of the gas according to the present invention is controlled by a sensor unit for detecting the index of the aggregation point of the microbial mycelium, using a low pressure mist spray nozzle discharged in the incubator at the time of aggregation is formed as the culture of the microorganism in the medium is grown. By diffusing and spraying gas into the medium, the aggregated culture is pulverized.
  • the gas injected through the nozzle may be air, oxygen, nitrogen, nitrogen dioxide, carbon dioxide, or the like, and is preferably air.
  • the gas is microsprayed through a nozzle of 0.1 to 0.5 mm under low pressure to pulverize the agglomeration of the culture, resulting in a coagulation resolution index of 0 to 1%.
  • a certain amount of dissolved acid tank (DO), dissolved carbon dioxide (DCO 2 ), and ozone are required.
  • DO dissolved acid tank
  • DCO 2 dissolved carbon dioxide
  • ozone a method of generating a required gas by adjusting the light intensity and illuminance of a light source is adopted. Doing.
  • the light source adjustment may be performed at an illuminance range of 1000 to 7000 Lux, and a luminance range of 4000 to 12000K, and a required photochemical gas may be ozone or carbon dioxide. That is, by installing a sensor to detect the residual amount of dissolved oxygen, dissolved carbon dioxide and ozone in the incubator, when the ozone content is insufficient, nitrogen dioxide is introduced and in the oxidation process of nitrogen gas, the luminance range is 4000 to 5000K and the illuminance range is 6000 ⁇ 500Lux. Providing a light source produces ozone.
  • the infrared light source in the luminous intensity range of 10000 to 12000K and the illuminance range of 3000 ⁇ 500 Lux is irradiated to increase the dissolved carbon dioxide in the medium.
  • the microorganism is a microorganism of 0.1 mm or less including 9-cis beta-carotene, and is not particularly limited in the present invention, and includes microalgae, protozoa, filamentous fungi, yeasts, viruses, and the like.
  • the microalgae may be Dunaliella, Spirrolina, Chlamydomonas, Simbella, Chlorella, etc., which are cultured in a liquid medium, but Dunaliellane is preferable.
  • Dunaliella contains natural beta-carotene, and beta-carotene beneath the cell wall by synthesizing beta-carotene under the cell wall to protect chlorophyll a, a chlorophyll important for photosynthesis when the culture environment deteriorates, such as strong light irradiation. It is known to form a film.
  • the culture medium is a supply medium of nutrients necessary for the survival and proliferation of microorganisms, but may be a liquid medium or a solid medium, but is preferably a liquid medium.
  • it may include NaNO 3 , NaCl, NaH 2 PO 4 H 2 O, Na 2 SiO 3 9H 2 O, trace metals and vitamins.
  • the trace metals are FeCl 3 6H 2 O, Na 2 EDTA 4H 2 O, CuSO 4 5H 2 O, Na 2 MoO 4 2H 2 O, ZnSO 4 7H 2 O, MnCl 2 4H 2 O and Co (Cl) 2 ⁇ 6H 2 O and the like
  • the vitamin is cyanocobalamin (bioano), biotin (biotin), thiamine HCl, vitamin C, vitamin E, vitamin B12, calcium pantothenate (calcium pantothenate) , Folic acid, nicotinamide, and the like.
  • the cultured microorganisms can recover the cells by spontaneous precipitation of the culture or centrifugation.
  • Step (1) and (2) is a step of extracting beta carotene from the culture microorganism, according to an embodiment of the present invention, after washing the dry powder of the culture duraellia salina strain with ethanol, the carotenoid component Cyclo-nuxanon is added to separate and the hexane layer is evaporated, followed by addition of hexane and stirring and evaporation at -5 to 5 ° C. for 0.8 to 1.2 hours to obtain a dark brown semisolid. After adding the cyclo-nucleanone to the obtained semi-solid, it is maintained for 11 to 13 hours at -25 ⁇ -15 °C to obtain a beta carotene extract.
  • Step (3) is a step of purifying beta carotene, and may be performed using silica gel column chromatography, ODS column chromatography, or a combination thereof.
  • the beta carotene extract obtained above was purified by silica gel column chromatography using cyclohexane-ethyl and acetate (50: 1, v / v) as eluent to remove impurities and reddish brown foam.
  • a solid was obtained, which was ultrasonically pulverized to obtain an orange powder, which was then purified by ODS column chromatography using methanol and tetrahydrofuran (1: 0.2-1: 1, v / v) as eluent to give all trans beta.
  • An orange powder obtained by mixing carotene and 9-cis beta carotene was obtained. The powder thus obtained can be measured for absorbance at 450 nm or 475 nm using HPLC to determine the content of beta-carotene.
  • Step (4) is a step of separating and crystallizing 9-cis beta-carotene from the purified beta-carotene powder, an orange powder containing all-trans beta-carotene and 9-cis beta-carotene obtained according to an embodiment of the present invention.
  • methanol and tetrahydrofuran can be added at 1: 0.2 to 1: 1 (v / v) and rotovap to separate 9-cis beta-carotene from all trans beta-carotene.
  • the isolated 9-cis beta-carotene may be crystallized at -25 ⁇ -15 °C, preferably -20 °C.
  • the present invention also provides 9-cis beta-carotene produced by the above production method.
  • 9-cis beta-carotene produced according to the present invention has an average diameter of 0.1 ⁇ 0.4 ⁇ m, and has the advantage of showing excellent purity.
  • 9-cis beta-carotene according to the present invention is separated and purified from the cultured microorganisms by the micro-injection and light source control of the gas, it is easy to produce, eco-friendly mass production is possible, there is an effect showing excellent purity.
  • 1 is a diagram showing a 9-cis beta carotene according to the present invention.
  • Figure 2 (a, b, c, d, e, f) shows the UV-B measurements of HPLC for carotenoids and tocopherols of the Dunaliella salina strain according to the present invention It is a graph.
  • Figure 3a Figure 3b is a graph of the component analysis at 450 nm absorption band using a sample containing 9-cis beta-carotene purified according to Example 2-2 using HPLC.
  • Figure 4 is a graph of the component analysis at 470 nm absorption band using a sample containing 9-cis beta carotene purified according to Example 2-3.
  • 5A and 5B are graphs showing 1 H-NMR and 13 C-NMR spectra for 9-cis beta-carotene cultured, isolated and purified from Dunaliella salinaro strain according to the present invention.
  • Microalgae Dunaliella salina (KMMCC-1064) strains were cultured using an optical biocultivator (see KR10-2014-0046132).
  • the Dunaliella salina strain is inoculated in an f / 2 culture medium, pressure control and air injection of the optical bio-incubator is performed using a nozzle having a diameter in the range of 0.1 to 0.5mm under low pressure, the illumination range of the light source is 1000 To 7000Lux, the brightness range was performed by adjusting to 4000 to 12000K.
  • the strain had a size of 13.0 ⁇ 1.6 ⁇ m and was cultured for 15 days using the f / 2 culture medium of Tables 1 to 3 below.
  • Tables 1-3 Various media for culturing Dunaliella salina are shown in Tables 1-3 (Table 1: culture medium, Table 2: trace metal solution medium, Table 3: vitamin solution medium).
  • the cultured strain was filtered using a hollow fiber membrane of 0.05 ⁇ m size, and the carotenoid content of the strain was analyzed using HPLC (Tosoh, MCPD-3600).
  • Example 2-1 The extract according to Example 2-1 was subjected to silica gel column chromatography (silica gel: 900 ml, column: 5.5 cm ⁇ ⁇ 38 cm, eluent: cyclohexane and ethyl acetate (50: 1, v / v)). Purification removed impurities to obtain 16.6 g of a reddish brown foamy solid. 1660 mL of ethanol was added to the solid, which was then pulverized by ultrasonication. The solid was filtered, washed with ethanol and dried to obtain an orange powder (12 g,> 80%). The ultrasonic mill used (VCX750, Sonic & Materials Inc., USA) was operated for 6 minutes at a speed of 3000 rpm. The obtained powder was subjected to component analysis at 450 nm absorption band using HPLC, and the results are shown in FIGS. 3A and 3B.
  • the orange powder can be seen that isomers, such as all-trans beta carotene, 9-cis beta carotene are mixed.
  • the orange powder may be mixed with all-trans beta-carotene and 9-cis beta-carotene.
  • the orange powder containing all trans beta-carotene and 9-cis beta-carotene according to Example 2-3 was placed in a double jacketed reactor maintained at a temperature of 20 ° C. in a bath and 1 ° C. This was evaporated to a decrease of 1/5 to give an orange crystal. Methanol and tetrahydrofuran were added (5: 1-1: 1, v / v) to the crystals, and evaporated to give 75 mg of 9-cis beta-carotene per fraction, which was crystallized by maintaining at about -20 ° C. As a result, the total extraction rate of 7.5g of 9-cis beta-carotene was compared to 1kg of dry Dunalella salina dry powder, and it was confirmed that dark storage was possible at about -20 ° C for 2 weeks.
  • Example 2 Dunaliella salina strain cultured according to Example 1 was filtered using a 0.05 micron hollow fiber membrane (hollow fiber membrane), using high performance liquid chromatography (HPLC, Tosoh Co. MCPD-3600) The carotenoid content was analyzed.
  • HPLC comprises Nucleosil 5 ⁇ m C18 (250 ⁇ 4.6 mm id) (Macherey-Nagel) as the Guard column, Bondaclone 10 ⁇ m C18 (3.9 ⁇ 150 mm id) as the Analytical column, and Capillary column (15 mm ⁇ 0.53 mm id).
  • total carotenoid content was analyzed using ⁇ -carotene, zeaxanthin, lutein, astaxanthin and cryptoxanthin, tocopherol, ascorbic acid (Vitamin C), catalase, peroxidase, and superocide dismutase as a standard for comparison.
  • the list of standards includes ( ⁇ ) cis-trans abscisic acid, ( ⁇ ) cis-trans ABA, trans-ABA, all-trans-l3-carotene, ABA-Methyl ester, formaldehyde, polychlorinated f1occulant, 2,6-Di-terr -butyl-p-cresol, aqueous scintillant, and N-methyl-N'-nitro-nitrosoguanidine were used.
  • the membrane filter of ⁇ -carotene content of The United States Pharmacopeial Convention (USP) was 0.45 ⁇ m pore size, but the membrane tester was confirmed by passing the 0.4 ⁇ m pore size.
  • the membrane filter is made of PTFE and manufactured in the form of hollow fiber. Thereafter, 1 H-NMR and 13 C-NMR spectra were measured for 9-cis beta-carotene filtered through the membrane filter, and the results are shown in FIGS. 5A and 5B.

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Abstract

La présente invention concerne un procédé de production de 9-cis β-carotène à partir de microorganismes, comprenant un procédé destiné à améliorer la vitesse de culture des microorganismes à l'aide d'un gaz photochimique généré par la micro-pulvérisation de gaz et la commande d'une source de lumière et un procédé de séparation et de purification du 9-cis β-carotène à partir de la culture de microorganismes. Le 9-cis β-carotène selon la présente invention est séparé et purifié à partir des microorganismes mis en culture au moyen de la micro-pulvérisation de gaz et de la commande de la source de lumière, facilitant ainsi la production, permettant une production en masse respectueuse de l'environnement et présentant une excellente pureté.
PCT/KR2014/010853 2014-11-10 2014-11-12 Procédé de culture de microorganismes et procédé de séparation et de purification de 9-cis β-carotène à partir des microorganismes cultivés Ceased WO2016076454A1 (fr)

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CN116268424A (zh) * 2016-11-17 2023-06-23 德布勒森大学 提供维生素a5途径的维甲类的前体化合物及其用途
JP2025511655A (ja) * 2023-01-26 2025-04-16 バクサ テクノロジーズ リミテッド 対立しない活性ビタミンｂ１２の増強された含有量及び／又はバイオアベイラビリティを有する光合成的に制御されたスピルリナ生成物

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KR102289190B1 (ko) 2019-10-31 2021-08-12 (주)아크에이르 9-cis Beta-carotene의 합성방법
KR102107989B1 (ko) 2019-12-20 2020-05-07 한국해양바이오클러스터 주식회사 산업용 또는 상업용 공조기 악취 저감을 위한 탈취 미생물의 배지 최적화에 의한 대량생산방법
KR102311539B1 (ko) 2020-12-28 2021-10-12 (주)아크에이르 신규 화합물 Potassium all-trans retinoate 및 Potassium 9-cis retinoate를 포함하는 혈액응고 억제용 약학적 조성물
KR102271364B1 (ko) 2020-12-28 2021-06-30 (주)아크에이르 신규화합물 Potassium all-trans retinoate 및 Potassium 9-cis retinoate의 합성방법
KR102633825B1 (ko) * 2021-10-18 2024-02-02 연세대학교 산학협력단 박테리아를 이용한 가스 중 질소산화물의 저감 방법 및 시스템
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