CN108358772A - A kind of preparation method and applications of spirulina gamma-Linolenic acid extract - Google Patents

A kind of preparation method and applications of spirulina gamma-Linolenic acid extract Download PDF

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Publication number
CN108358772A
CN108358772A CN201711381573.3A CN201711381573A CN108358772A CN 108358772 A CN108358772 A CN 108358772A CN 201711381573 A CN201711381573 A CN 201711381573A CN 108358772 A CN108358772 A CN 108358772A
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spirulina
gamma
linolenic acid
gla
preparation
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熊婕
陈璇
汪明星
王家雄
陈进轩
李亚龙
邓中洋
卢凡
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Hubei University of Technology
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42Separation; Purification; Stabilisation; Use of additives
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42Separation; Purification; Stabilisation; Use of additives
    • C07C51/48Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/03Monocarboxylic acids
    • C07C57/12Straight chain carboxylic acids containing eighteen carbon atoms

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  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
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  • Bioinformatics & Cheminformatics (AREA)
  • Pain & Pain Management (AREA)
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  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

The invention discloses a kind of preparation methods of spirulina acid and gamma-linolenic extract, belong to microalgae Biochemical Engineering technical field.The present invention utilizes more violent undercritical conditions, to destroy the cell wall and subcellular wall of spirulina, make cell wall phosphatide be detached from and hydrolyze to generate GLA, it realizes in the wet frustule of slave spirulina rapidly and efficiently and extracts GLA, wherein, subcritical water is also used as hydrolysis agent, environmental friendliness high as solvent.The spirulina cells of High water cut can directly be utilized by extracting raw material, be not necessarily to the drying link of frustule, saved a large amount of energy consumption for drying.GLA recovery rates of the present invention are high, separation is simple, are easy to amplify.

Description

A kind of preparation method and applications of spirulina gamma-Linolenic acid extract
Technical field
The invention belongs to microalgae Biochemical Engineering technical fields, and in particular to a kind of to be carried from the wet algal gel of spirulina using subcritical water Take the method and its application of gamma-Linolenic acid.
Background technology
Gamma-Linolenic acid (gamma-linolenic acid, GLA) was sent out in 1919 from onagraceae plant oenothera biennis for the first time It is existing, it is GAMMA-Linolenic acid, molecular formula C18H30O2, belong to the serial polyunsaturated fatty acids of ω -6.Normal temperature condition It is in colourless or pale yellow oily liquid down, it is not soluble in water, it is soluble in the nonpolar solvents such as petroleum ether, ether, n-hexane.In air In it is unstable, oxidation reaction especially easily occurs under the high temperature conditions, position of double bond and configuration isomery easily occur under alkaline condition Change reaction, forms Conjugated polyenoic acids.GLA is the structural material that group adult body each group knits biomembrane, has antibacterial, antiviral, anti- Tumour, anti-inflammatory, reducing blood lipid resist athero- artery sclerosis, blood pressure lowering, improve the extensive pharmacological actions such as diabetic complication, weight-reducing, It is known as " leading role of 21 century functional food ".FAO (Food and Agriculture Organization of the United Nation)s in 1993 and the World Health Organization, which combine, delivers sound It is bright:Importance and the mankind in view of GLA general lack of present situation, determine worldwide special to promote GLA and its metabolin. The U.S., France, the equal law-making stipulation of Japan and other countries since the nineties must add GLA and metabolism object space in specified food It can be sold.
GLA is extremely limited in nature, and in main source evening primrose oil, GLA contents are only in 7%-10%, but oenothera biennis kind The yield and oil content of son are larger with the change fluctuation of the external conditions such as weather, far from meeting the needs of market.Spirulina is A kind of filamentous cyanobacteria of many cells, is mainly grown in salina, belongs to Cyanophyta, Oscillariaceae, Arthrospira, on earth Through there are 3,500,000,000 years, being earliest one of photosynthetic organism.Nutritious spirulina is abundant, removes and is given birth to containing a large amount of protein, a variety of dimensions Outside element and minerals, content of polyunsaturated fatty acid is also very high, and GLA contents account for the 8%-25% of its aliphatic acid, is very promising The sources GLA.
The extractive technique of existing spirulina GLA includes:Low temperature urea crystals method, supercritical CO2Method, organic solvent extraction Method etc..These extractive techniques rest on laboratory stage more, and there are complex process, equipment investment height, high energy consumption, organic substance residues The problems such as, it is so very big that limit its industrialized application.What use was most is the solvent extraction of dry algae powder at present, and spirulina Water content is up to 60% or more in cell, and the GLA added values that only energy consumption of drying process just produces spirulina are extremely low.Therefore, Need exploitation a kind of simple for process, energy consumption is relatively low, the practicable method for extracting GLA from spirulina.
Invention content
In view of the deficiencies of the prior art, the purpose of the present invention is to provide a kind of systems of spirulina gamma-Linolenic acid extract Preparation Method and its application, the present invention use water as spe medium and hydrolysis agent, avoid using and returning for organic solvent It receives, and the present invention directly utilizes the microalgae cell of High water cut, saves the highly energy-consumings link such as microalgae centrifugation, dry.
By a large number of experiments and unremitting effort, inventor is finally obtained the following technical solution:A kind of spirulina γ-Asia The preparation method of numb acid extract, the wet algal gel of microalgae is added into reaction kettle, and water is added and as Extraction medium and is passed through nitrogen Gas, setting reactor pressure are 15-25MPa, and temperature is 250-300 °C, reaction time 10-30min, and water is made to keep subcritical shape State, it is extract obtained that powdered spirulina gamma-Linolenic acid extract can be obtained through vacuum freeze drying, convenient for storage and again Processing;
The final volume ratio of the wet algal gel of microalgae and Extraction medium water is 1:1-20.
Preferably, a kind of preparation method of spirulina gamma-Linolenic acid extract as described above, the wet algal gel water content For 40-90%.
Preferably, a kind of preparation method of spirulina gamma-Linolenic acid extract as described above, the wet algal gel is to pass through Centrifugation in advance or filtering culture medium obtain.
A kind of application of spirulina gamma-Linolenic acid extract, can be used for alleviating and treat PM2.5Caused airway inflammation.
Compared with prior art, advantages of the present invention is:
1, spirulina GLA exists with cell wall phospholipid form, and the present invention utilizes more violent undercritical conditions, to destroy spiral shell The cell wall and subcellular wall for revolving algae make cell wall phosphatide be detached from and hydrolyze to generate GLA, realize that slave spirulina rapidly and efficiently is wet GLA is extracted in frustule.
2, subcritical water is also used as hydrolysis agent, environmental friendliness high as solvent.Extracting raw material can be directly sharp With the spirulina cells of High water cut, it is not necessarily to the drying link of frustule, saves a large amount of energy consumption for drying.GLA recovery rates of the present invention Height, separation is simple, is easy to amplify.
3, it is quantitative determined through gas-chromatography, obtained gamma-Linolenic acid yield is 9.0 g/kg (GLA/ dry weights).
Description of the drawings
Fig. 1 is mouse lung tissue rank scores
Fig. 2 is mouse bronchoalveolar lavage fluid inflammatory cell differential counting
Fig. 3 is mouse bronchoalveolar lavage fluid cytokine content, and wherein Fig. 3-a are mouse bronchoalveolar lavage fluid IL-4 contents, and Fig. 3-b are Mouse bronchoalveolar lavage fluid IL-5 contents, Fig. 3-c are mouse bronchoalveolar lavage fluid IFN-γ content, and Fig. 3-d are mouse bronchoalveolar lavage fluid IL-10 contents.
Fig. 4 is TNF-α and IL-6 contents in 264.7 cell culture fluids of mouse RAW.
Fig. 5 is 264.7 cell NF κ B access situations of mouse RAW.
Specific implementation mode
For that can understand the technical characterstic for illustrating the present invention program with reference to specific embodiments be illustrated to the present invention.But Protection scope of the present invention is not limited to these examples.It is every to include without departing substantially from the change of present inventive concept or equivalent substitute Within protection scope of the present invention.
Embodiment 1
Weigh wet 100 g of algal gel of spirulina(Water content 50%, initial total lipid content 7.7%, initial GLA contents 1.2%), microalgae with The ratio between water is 1:1, it is placed in reaction kettle and seals, N is passed through into reaction kettle2To 1.5 MPa, 260 DEG C are heated to, is pressurized to 15 MPa, 20 min of reaction time, separating still collect product, GLA yield 0.9%, conversion ratio 75%.
For the wet algal gel of spirulina as first passing through in advance obtained by centrifugal treating, centrifugal condition is 3000 rpm, 20 min.(Supplement)
Embodiment 2
Weigh the wet algal gel 100g of spirulina(Water content 60%, initial total lipid content 6.5%, initial GLA contents 1.1%,), add water 140 The volume ratio of mL, microalgae mud and water is 1:5, it is placed in reaction kettle and seals, N is passed through into reaction kettle2To 1.5MPa, it is heated to 300 °C, 20 MPa, 15 min of reaction time are pressurized to, separating still collects product, GLA yield 0.87%, conversion ratio 79%.
Wet algal gel is obtained by filtering culture medium, and filter method is that decompression filters.
Zoopery is carried out to sample prepared by embodiment 1, it was demonstrated that spirulina Subcritical water chromotagraphy object antagonism PM2.5It is caused The pharmacological action of airway inflammation, specific method and result are as follows:
Female Babl/c mouse are randomly divided into blank control group, PM2.5Control group, spirulina Subcritical water chromotagraphy object be small, in, Large dosage group and dexamethasone positive controls, continuous processing 12 weeks, observation spirulina Subcritical water chromotagraphy object is to PM2.5It is caused The inhibiting effect of airway inflammation.As a result as follows:
(1) spirulina Subcritical water chromotagraphy object inhibits PM2.5The airway inflammation of induction
As shown in Figure 1, according to " lung tissue inflammatory pathologies rank scores standard ", mouse lung tissue rank scores are observed.With sky White control group is compared, and model group mouse lung tissue inflammatory score significantly improves(P<0.01);Spirulina Subcritical water chromotagraphy object is small, Middle and high dosage group and dexamethasone in treatment group significantly reduce inflammatory score(P<0.01, P<0.05).
(2)Spirulina Subcritical water chromotagraphy object inhibits PM2.5The inflammatory cell infiltration of induction
As shown in Fig. 2, compared with blank control group, PM2.5Inflammatory cell content is significantly raised in model group mouse bronchoalveolar lavage fluid (P<0.01), with PM2.5Model group control group is compared, and spirulina Subcritical water chromotagraphy object can dose dependent reduction inflammatory cell Sum and eosinophil number(P<0.01), spirulina Subcritical water chromotagraphy object large dosage group can reduce neutrophil leucocyte, Macrophage(P<0.01, P<0.05).
(3) spirulina Subcritical water chromotagraphy object be adjusted in mouse asthmatic model bronchoalveolar lavage fluid Th1 and Th2 cells because Sub- content
As shown in figure 3, compared with blank control group, PM2.5In model group mouse bronchoalveolar lavage fluid IL-4, IL-5, IL-10 and IFN-γ content significantly increases(P < 0.01).With PM2.5Model group is compared, and each cytokine content of Dexamethasone group is notable It reduces(P < 0.01), spirulina Subcritical water chromotagraphy object dose-dependently reduce in mouse bronchoalveolar lavage fluid Th2 cells because Sub- IL-4, IL-5 content(P < 0.01, p < 0.05), increase Th1 cell factors IL-10, IFN-γ content(P < 0.01).
Test cell line is carried out to sample prepared by embodiment 1, it was demonstrated that spirulina Subcritical water chromotagraphy object can improve caused by LPS Cellular inflammatory reacts, and specific method and result are as follows:
Mouse monokaryon macrophage RAW 264.7 is divided for blank control group, LPS control groups, spirulina Subcritical water chromotagraphy object It is small, in, large dosage of group, under observation LPS stimulations, protective effect of the spirulina Subcritical water chromotagraphy object to cell.As a result as follows:
(1) spirulina Subcritical water chromotagraphy object reduces TNF-α and IL-6 contents in born of the same parents' culture solution
As shown in figure 4, compared with blank control group, TNF-α and IL-6 contents significantly increase in LPS model group cell culture fluids(p < 0.01);Compared with LPS model groups, the middle and high dosage group of spirulina Subcritical water chromotagraphy object reduces TNF-α in cell culture fluid (P < 0.01), microalgae fat extract high dose group reduce cell culture fluid in IL-6 contents(P < 0.01).
(2) spirulina Subcritical water chromotagraphy object inhibits cell NF κ B signal pathway activateds
As shown in figure 5, compared with blank control group, the p-IKK expression of LPS model groups significantly increases(P < 0.01), I κ B express aobvious Writing reduces(P < 0.01);Compared with LPS model groups, spirulina Subcritical water chromotagraphy object high dose group significantly reduces p-IKK expression (P < 0.01), spirulina Subcritical water chromotagraphy object high dose group significantly increases I κ B expression(P < 0.01).

Claims (4)

1. a kind of preparation method of spirulina gamma-Linolenic acid extract, it is characterised in that:The wet algal gel of microalgae is added to reaction In kettle, water is added and as Extraction medium and is passed through nitrogen, setting reactor pressure is 15-25MPa, and temperature is 250-300 °C, instead 10-30min between seasonable makes water keep subcritical state, extract obtained through vacuum freeze drying, and powdered spiral can be obtained Algae gamma-Linolenic acid extract;
The final volume ratio of the wet algal gel of microalgae and Extraction medium water is 1:1-20.
2. a kind of preparation method of spirulina gamma-Linolenic acid extract as described in claim 1, it is characterised in that:It is described wet Algal gel water content is 40-90%.
3. a kind of preparation method of spirulina gamma-Linolenic acid extract as described in claim 1, it is characterised in that:It is described wet Algal gel is obtained by centrifuging or filtering culture medium in advance.
4. a kind of preparation method of spirulina gamma-Linolenic acid extract, it is characterised in that:It can be used for alleviating and treat PM2.5It is caused Airway inflammation.
CN201711381573.3A 2017-12-20 2017-12-20 A kind of preparation method and applications of spirulina gamma-Linolenic acid extract Pending CN108358772A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109438222A (en) * 2018-11-21 2019-03-08 集美大学 A method of preparing 4- hydroxycinnamic acid from spirulina
CN109893520A (en) * 2019-03-21 2019-06-18 中国科学院水生生物研究所 The new application of spirulina gamma-Linolenic acid

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102630943A (en) * 2012-05-08 2012-08-15 北京林业大学 Spirulina gamma-linolenic acid extractive and preparation method thereof
CN103191579A (en) * 2013-04-27 2013-07-10 云南蓝钻生物科技有限公司 Method for extracting gamma-linolenic acid in spirulina through supercritical CO2
CN103222936A (en) * 2012-01-31 2013-07-31 株式会社爱茉莉太平洋 Skin external use composition comprising lotus seed extract
CN104611236A (en) * 2015-01-23 2015-05-13 孙敏 Cumminghamella echinulata(Thaxter) thaxter FAR3 and method for fermentation preparation of Gamma-linolenic acid grease with Cumminghamella echinulata(Thaxter) thaxter FAR3

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103222936A (en) * 2012-01-31 2013-07-31 株式会社爱茉莉太平洋 Skin external use composition comprising lotus seed extract
CN102630943A (en) * 2012-05-08 2012-08-15 北京林业大学 Spirulina gamma-linolenic acid extractive and preparation method thereof
CN103191579A (en) * 2013-04-27 2013-07-10 云南蓝钻生物科技有限公司 Method for extracting gamma-linolenic acid in spirulina through supercritical CO2
CN104611236A (en) * 2015-01-23 2015-05-13 孙敏 Cumminghamella echinulata(Thaxter) thaxter FAR3 and method for fermentation preparation of Gamma-linolenic acid grease with Cumminghamella echinulata(Thaxter) thaxter FAR3

Non-Patent Citations (10)

* Cited by examiner, † Cited by third party
Title
M.HERRERO等: "Sub- and supercritical fluid extraction of functional ingredients from different natural sources: Plants, food-by-products,algae and microalgae A review", 《FOOD CHEMISTRY》 *
SAQIB S. TOOR等: "Hydrothermal liquefaction of Spirulina and Nannochloropsis salinaunder subcritical and supercritical water conditions", 《BIORESOURCE TECHNOLOGY》 *
仇记红等: "松子油加工工艺及脂肪酸组成研究进展 ", 《粮食与油脂》 *
仇记红等: "松子油加工工艺及脂肪酸组成研究进展", 《粮食与油脂》 *
孔秀芹等: "γ-亚麻酸在RAW264.7细胞中的抗炎症作用机制", 《安徽农业科学》 *
孙培培等: "微藻脂类组成及脂肪酸分布的分析技术 ", 《食品安全质量检测学报》 *
孙培培等: "微藻脂类组成及脂肪酸分布的分析技术", 《食品安全质量检测学报》 *
王菲等: "螺旋藻γ-亚麻酸的提取优化及体外抗氧化活性的研究", 《食品工业科技》 *
邢立民: "CO_2超临界萃取技术在油脂生产中的应用 ", 《内蒙古科技与经济》 *
邢立民: "CO_2超临界萃取技术在油脂生产中的应用", 《内蒙古科技与经济》 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109438222A (en) * 2018-11-21 2019-03-08 集美大学 A method of preparing 4- hydroxycinnamic acid from spirulina
CN109438222B (en) * 2018-11-21 2021-08-31 集美大学 Method for preparing 4-hydroxycinnamic acid from spirulina
CN109893520A (en) * 2019-03-21 2019-06-18 中国科学院水生生物研究所 The new application of spirulina gamma-Linolenic acid

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