CN103755589A - Method for extracting mycosporine-like amino acid shinorine from microcystis - Google Patents
Method for extracting mycosporine-like amino acid shinorine from microcystis Download PDFInfo
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- CN103755589A CN103755589A CN201310702909.7A CN201310702909A CN103755589A CN 103755589 A CN103755589 A CN 103755589A CN 201310702909 A CN201310702909 A CN 201310702909A CN 103755589 A CN103755589 A CN 103755589A
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- 238000000034 method Methods 0.000 title claims abstract description 32
- 150000001413 amino acids Chemical class 0.000 title claims abstract description 19
- WXEQFJUHQIGKNG-MZNRBSSJSA-N shinorine Chemical compound COC1=C(C[C@@](O)(CO)C\C1=N/[C@@H](CO)C(O)=O)NCC(O)=O WXEQFJUHQIGKNG-MZNRBSSJSA-N 0.000 title claims abstract description 14
- WXEQFJUHQIGKNG-UHFFFAOYSA-N shinorine Natural products COC1=C(CC(O)(CO)C/C/1=NC(CO)C(=O)O)NCC(=O)O WXEQFJUHQIGKNG-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 241000192701 Microcystis Species 0.000 title abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 57
- 239000006228 supernatant Substances 0.000 claims abstract description 18
- 239000000706 filtrate Substances 0.000 claims abstract description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000000843 powder Substances 0.000 claims abstract description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- 238000002414 normal-phase solid-phase extraction Methods 0.000 claims abstract description 7
- 239000012153 distilled water Substances 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000001914 filtration Methods 0.000 claims abstract description 5
- 241000192710 Microcystis aeruginosa Species 0.000 claims description 29
- 238000012258 culturing Methods 0.000 claims description 10
- 241000195493 Cryptophyta Species 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 239000007789 gas Substances 0.000 claims description 9
- 238000011068 loading method Methods 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 230000004913 activation Effects 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 229910021642 ultra pure water Inorganic materials 0.000 claims description 6
- 239000012498 ultrapure water Substances 0.000 claims description 6
- 238000012545 processing Methods 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- 241000192700 Cyanobacteria Species 0.000 claims description 4
- 235000015097 nutrients Nutrition 0.000 claims description 3
- 239000012488 sample solution Substances 0.000 claims description 3
- 238000012360 testing method Methods 0.000 claims description 3
- 238000004506 ultrasonic cleaning Methods 0.000 claims description 3
- 230000001186 cumulative effect Effects 0.000 claims description 2
- 239000000523 sample Substances 0.000 claims description 2
- 239000000047 product Substances 0.000 abstract description 3
- 239000012467 final product Substances 0.000 abstract 2
- 238000002156 mixing Methods 0.000 abstract 2
- 238000007664 blowing Methods 0.000 abstract 1
- 238000004108 freeze drying Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000011002 quantification Methods 0.000 abstract 1
- 238000002604 ultrasonography Methods 0.000 abstract 1
- 239000007788 liquid Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 3
- 230000004087 circulation Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 239000003094 microcapsule Substances 0.000 description 2
- 238000002525 ultrasonication Methods 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- VVTDHOIRNPCGTH-NSHDSACASA-N Mycosporine Chemical compound COC1=C(NC(CO)CO)C[C@@](O)(CO)CC1=O VVTDHOIRNPCGTH-NSHDSACASA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000009545 invasion Effects 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 230000003711 photoprotective effect Effects 0.000 description 1
- 230000004224 protection Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
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- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Separation Of Suspended Particles By Flocculating Agents (AREA)
Abstract
The invention discloses a method for extracting mycosporine-like amino acid shinorine from microcystis. The method particularly comprises the following steps: (1) mixing microcystis powder with methanol, treating by ultrasounds and heating, centrifuging and collecting supernatant; (2) blowing the supernatant by using nitrogen to be dried and re-dissolving with distilled water; (3) adding chloroform and uniformly mixing; (4) centrifuging and collecting supernatant; (5) filtering by using a needle type filter; (6) treating by using a strata-x solid-phase extraction small column, and freeze-drying filtrate. The method for extracting the mycosporine-like amino acid shinorine is simple, convenient to operate and safe and reliable; the purity of a final product is up to 85%-95% and the final product can be used as a standard product and lays a firm foundation for follow-up large-scale quantification.
Description
Technical field
The present invention relates to biotechnology and the utilization of resources and Sustainable development field, more specifically relate to a kind of method of extracting class mycetocyte element amino acid Shinorine from Microcystis aeruginosa.
Background technology
At present, to the utilization of Microcystis aeruginosa, be almost blank, say nothing of and from Microcystis aeruginosa, extract class mycetocyte element amino acid and be used.
Class mycetocyte element amino acid (mycosporine and mycosporine-like) is that a large class is take cyclonene as basic framework, the water-soluble substances forming by condensation with dissimilar amino acid, can in fungi, marine bacteria, blue-green algae and Eukaryotic Algae cell, synthesize, and in sea the biological cylinder accumulation such as raw invertebrates and fish, its molecular size is generally less than 400Da, and this class material has very strong light absorpting ability within the scope of 310-360nm.A lot of Microcystis aeruginosas all contain class mycetocyte element amino acid, and they can help Microcystis aeruginosa to resist ultraviolet invasion and attack, for the growth of Microcystis aeruginosa creates conditions.This class of class mycetocyte element amino acid has the ability of extremely strong anti-ultraviolet radiation, can be used for light protection industry, particularly cosmetic industry.At present, the photoprotective substances that China is used is mainly chemosynthesis, and life-time service synthetics confrontation human body skin easily damages, thereby is unfavorable for human health.
And at present domestic to class mycetocyte element, amino acid whose extraction relates to seldom, and purity is not high.Particularly in current world wide, all there is no the class mycetocyte element amino acid standard substance of commodity.
Summary of the invention
The object of the present invention is to provide a kind of method of extracting class mycetocyte element amino acid Shinorine from Microcystis aeruginosa, the method is simple, easy to operate, safe and reliable.
Another object of the present invention has been to provide the application of a kind of method of extracting class mycetocyte element amino acid Shinorine from Microcystis aeruginosa in the class mycetocyte element amino acid Shinorine of preparation.By the method, the purity of the finished product that obtain reaches 85%-95%, and can be used as standard substance and use, or other commercialization purposes, for follow-up extensive Extraction and determination is taken a firm foundation.In order to achieve the above object, the present invention takes following technical measures:
A method of extracting class mycetocyte element amino acid Shinorine from Microcystis aeruginosa, concrete steps are as follows:
1. Microcystis aeruginosa powder is mixed with the ratio of 1g:10-40ml with anhydrous methanol, first be placed in ultrasonic cleaning instrument 100% supersound process 5-10min, then the water-bath that is placed in 40-50 ℃ is processed 2.5-4 hour, mix up and down during this time for several times, centrifugal under 9000-11000rpm/min condition, centrifugal 15-20min, gets supernatant; Filter residue rejoins anhydrous methanol extracting with the ratio of above-mentioned Microcystis aeruginosa powder and anhydrous methanol, repeats extracting 2～3 times, and the supernatant of collecting is merged;
2. the supernatant liquor of collection is placed in to Nitrogen evaporator, nitrogen dries up, and take distilled water and algae powder weight ratio, as 1:1～5:1 adds distilled water, redissolves;
3. after redissolution, in solution, add isopyknic chloroform, fully mix;
4. centrifugal 15-20min under the condition with 9000-11000rpm/min, collects supernatant liquor;
5. supernatant liquor is crossed 0.22 μ m needle type filtration device, collects filtrate;
6. filtrate is passed through the processing of strata-x solid phase extraction column again, and the filtrate of collection is weighed after lyophilize at-50～-60 ℃.
What agents useful for same of the present invention or material were commercially available all can use, and in step 6, with solid phase extraction column, processes during filtrate, can be according to usual manner processing, or select following processing mode, step is as follows:
A: activate, first use the anhydrous methanol of 10-40ml, then use 10-40ml ultrapure water activation pillar, flow velocity is 2-5ml/min;
B: loading: add the NaOH solution of 0.2m/L before loading in sample solution, make sample pH value value to 6.5-8.0;
C: drip washing: first use anhydrous methanol 20-60ml, re-use ultrapure water activation 20-60ml; Flow velocity is 2-5ml/min;
D: wash-out: elute soln is used 0.1%(v:v) HCl methyl alcohol 10-20ml(HCL concentration used is 1m/l), flow velocity 2-5ml/min;
E: the filtrate of collection is weighed after lyophilize at-50～-60 ℃.
Preferably, elute soln cumulative volume in steps d is constant, carry out the same terms wash-out twice.
Preferably, during loading, do not exert pressure, solution is flowed down naturally.
Described Microcystis aeruginosa can be cultivated by conventional methods, also can be undertaken by mode of the present invention, and concrete culturing step is as follows:
1. the preparation of nutrient solution: conventional blue-green algae substratum;
2. the cultivation of Microcystis aeruginosa:
(1) one-level is cultivated: by test tube original seed, be inoculated in the culturing bottle of 250ml, aerated culture, regulates gas to flow to 1-2L/min, and through syringe-driven filter, (0.22 μ m) aseptically process connects air-flow, and intensity control is at 40-60 μ Em
-2s
-1, temperature is controlled at 25-28 ℃, when cultivating after 5-8 days, proceeds to secondary and cultivates;
(2) secondary is cultivated: the culture of one-level being cultivated to gained is linked in 2L culturing bottle, and aerated culture is adjusted gas and flow to 3-4L/min, and through syringe-driven filter, (0.22 μ m) aseptically process connects air-flow, and intensity control is at 60-80 μ Em
-2s
-1, temperature is controlled at 25-28 ℃, when cultivating after 5-10 days, proceeds to three grades of cultivations;
(3) three grades of cultivations: the culture of secondary being cultivated to gained is transferred in the culturing bottle of 10L, aerated culture, adjusts gas and flows to 4-6L/min, and through syringe-driven filter, (0.22 μ m) aseptically process connects air-flow, and intensity control is at 80-100 μ Em
-2s
-1, temperature is controlled at 25-28 ℃, cultivates 8-10 days.
Described Microcystis aeruginosa powder can be prepared by conventional methods, or adopts preparation method of the present invention, specific as follows:
By 3 circulations of Microcystis aeruginosa liquid ultrasonication, each circulating ultrasonic is processed 3min, suspend 1min, it is centrifugal that algae liquid after ultrasonic is placed in whizzer, the centrifugal 15-20min of centrifugal speed 9000-11000rpm/min, obtains Microcystis aeruginosa algae mud ,-60--80 ℃ freezing after, be placed in freeze drier ,-50--60 ℃ obtain micro-capsule algae powder.
The present invention compared with prior art, has the following advantages and effect significantly:
Extract impurity is few, and Shinorine purity is high, easy to operate, and equipment is simple, safe and reliable, is applicable to preparation standard product.
Embodiment
Embodiment 1:
The cultivation of Microcystis aeruginosa:
1. the preparation of nutrient solution: conventional blue-green algae substratum;
2. the cultivation of Microcystis aeruginosa:
(1) one-level is cultivated: by test tube original seed (4ml), be inoculated in the culturing bottle of 250ml (inside having substratum 200ml), aerated culture, regulate gas to flow to 1-2L/min, through syringe-driven filter, (0.22 μ m) aseptically process connects air-flow, and intensity control is at 40-60 μ Em
-2s
-1, temperature is controlled at 25-28 ℃, when cultivating after 5-8 days, proceeds to secondary and cultivates;
(2) secondary is cultivated: the culture of one-level being cultivated to gained is all linked in 2L culturing bottle (inside having substratum 1L), aerated culture, adjust gas and flow to 3-4L/min, through syringe-driven filter, (0.22 μ m) aseptically process connects air-flow, and intensity control is at 60-80 μ Em
-2s
-1, temperature is controlled at 25-28 ℃, when cultivating after 5-10 days, proceeds to three grades of cultivations;
(3) three grades of cultivations: the culture of secondary being cultivated to gained is all transferred in the culturing bottle (inside having substratum 8L) of 10L, aerated culture, adjust gas and flow to 4-6L/min, through syringe-driven filter, (0.22 μ m) aseptically process connects air-flow, and intensity control is at 80-100 μ Em
-2s
-1, temperature is controlled at 25-28 ℃, cultivates 8-10 days, obtains Microcystis aeruginosa liquid.
By 3 circulations of Microcystis aeruginosa liquid ultrasonication, each circulating ultrasonic is processed 3min, suspends 1min, it is centrifugal that algae liquid after ultrasonic is placed in whizzer, the centrifugal 15-20min of 11000rpm/min ,-60--80 ℃ freezing after, be placed in freeze drier ,-50～-60 ℃ obtain micro-capsule algae powder.
Described Microcystis aeruginosa is PCC7806 microcystic aeruginosa.
Embodiment 2:
From Microcystis aeruginosa, extract a method of preparing class mycetocyte element amino acid Shinorine, its step is as follows:
1. take the Microcystis aeruginosa powder that 10g embodiment 1 makes and add 100ml anhydrous methanol, first be placed in ultrasonic cleaning instrument 100% supersound process 15min, then the water-bath that is placed in 45 ℃ is processed 3 hours, mix up and down during this time 10 times, under 11000rpm/min condition, centrifugal 15min, gets supernatant, rejoins the extracting of 100ml anhydrous methanol in filter residue, repeat extracting 3 times, the supernatant of collecting is merged;
2. the supernatant liquor of collection is placed in to Nitrogen evaporator, after nitrogen dries up, uses 10ml distilled water to redissolve;
3. the solution after redissolving is taken out, add isopyknic chloroform, fully mix;
4. centrifugal 15min under the condition with 11000rpm/min, collects supernatant liquor;
5. supernatant liquor is crossed 0.22 μ m needle type filtration device, collects filtrate;
6. filtrate is passed through solid phase extraction column processing again, and the filtrate of collection is weighed after lyophilize at-50～-60 ℃.The concrete steps of crossing post are as follows:
A: activate, first use the anhydrous methanol of 10ml, then use 10ml ultrapure water activation pillar, flow velocity 3ml/min;
B: loading: add the NaOH solution of 0.2m/l before loading in sample solution, making final pH value is 7.5;
C: drip washing: first use at the uniform velocity drip washing of anhydrous methanol 20ml, then use at the uniform velocity drip washing of ultrapure water 20ml; Flow velocity 3ml/min.
D: wash-out: use elute soln 0.1%(v/v) HCl methyl alcohol 5ml(HCL concentration used be 1m/l) carry out wash-out, flow velocity is 3ml/min, collects filtrate;
E: wash-out: use again elute soln 0.1%(v/v) HCl methyl alcohol 5ml carry out wash-out (HCL concentration used is 1m/l), collect filtrate, flow velocity is 3ml/min;
F: the filtrate of the collection that d, e two steps are collected is weighed after lyophilize at-50～-60 ℃.
The needle type filtration device that the present embodiment is used is nylon material; Solid-phase extraction column is that phenomenex produces strata-x model, and specification is 6ml200mg;
The algae powder of 10g obtains the Shinorine of 18.95mg, and purity is 95%.
Technical scheme described in the embodiment of the present invention if not otherwise specified, is this area routine techniques.
Claims (5)
1. a method of extracting class mycetocyte element amino acid Shinorine from Microcystis aeruginosa, concrete steps are as follows:
1) Microcystis aeruginosa powder is mixed with the ratio of 1g:10-40ml with anhydrous methanol, first be placed in ultrasonic cleaning instrument 100% supersound process 5-10min, then the water-bath that is placed in 40-50 ℃ is processed 2.5-4 hour, mix up and down during this time for several times, centrifugal under 9000-11000rpm/min condition, centrifugal 15-20min, gets supernatant; Filter residue rejoins anhydrous methanol extracting with the ratio of above-mentioned Microcystis aeruginosa powder and anhydrous methanol, repeats extracting 2 ~ 3 times, and the supernatant of collecting is merged;
2) supernatant liquor of collection is placed in to Nitrogen evaporator, nitrogen dries up, and take distilled water and algae powder weight ratio, as 1:1 ~ 5:1 adds distilled water, redissolves;
3) after redissolution, in solution, add isopyknic chloroform, fully mix;
4) centrifugal 15-20min under the condition with 9000-11000rpm/min, collects supernatant liquor;
5) supernatant liquor is crossed 0.22 μ m needle type filtration device, collects filtrate;
6) filtrate is passed through the processing of strata-x solid phase extraction column again, and the filtrate of collection is weighed after lyophilize at-50 ~-60 ℃.
2. method according to claim 1, the concrete steps of Solid-Phase Extraction are:
Activation: first use the anhydrous methanol of 10-40ml, then use 10-40ml ultrapure water activation pillar, flow velocity is 2-5ml/min;
Loading: add the NaOH solution of 0.2m/L before loading in sample solution, make sample pH value value to 6.5-8.0;
Drip washing: first use anhydrous methanol 20-60ml, re-use ultrapure water activation 20-60ml; Flow velocity is 2-5ml/min;
Wash-out: elute soln is used the HCl methyl alcohol 10-20ml of 0.1% volume ratio, flow velocity 2-5ml/min, the filtrate of collection is weighed after lyophilize at-50 ~-60 ℃, and described HCL concentration is 1m/l.
3. method according to claim 2, is characterized in that: in the situation that elute soln cumulative volume is constant, and twice of wash-out.
4. method according to claim 1 and 2, the cultural method of Microcystis aeruginosa is as follows:
A. the preparation of nutrient solution: conventional blue-green algae substratum;
B. the cultivation of Microcystis aeruginosa:
(1) one-level is cultivated: by test tube original seed, be inoculated in the culturing bottle of 250ml, aerated culture, regulates gas to flow to 1-2L/min, and air-flow connects through syringe-driven filter aseptically process, and intensity control is at 40-60 μ Em
-2s
-1, temperature is controlled at 25-28 ℃, when cultivating after 5-8 days, proceeds to secondary and cultivates;
(2) secondary is cultivated: the culture of one-level being cultivated to gained is linked in 2L culturing bottle, and aerated culture is adjusted gas and flow to 3-4L/min, and air-flow connects through syringe-driven filter aseptically process, and intensity control is at 60-80 μ Em
-2s
-1, temperature is controlled at 25-28 ℃, when cultivating after 5-10 days, proceeds to three grades of cultivations;
(3) three grades of cultivations: the culture of secondary being cultivated to gained is transferred in the culturing bottle of 10L, aerated culture, adjusts gas and flows to 4-6L/min, and air-flow connects through syringe-driven filter aseptically process, and intensity control is at 80-100 μ Em
-2s
-1, temperature is controlled at 25-28 ℃, cultivates 8-10 days.
5. the application of method in the class mycetocyte element amino acid Shinorine of preparation described in claim 1.
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| CN105817051A (en) * | 2016-03-30 | 2016-08-03 | 南通中国科学院海洋研究所海洋科学与技术研究发展中心 | Method for extracting micromolecular intracellular metabolite from nori |
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| CN114657222A (en) * | 2022-04-08 | 2022-06-24 | 湖北省水利水电科学研究院 | Method for extracting mycosporine-like amino acid from Aphanizomenon flos-aquae |
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| CN104887615A (en) * | 2015-06-15 | 2015-09-09 | 齐鲁工业大学 | Method for preparing crude products of mycosporine-like amino acids in nostoc commune cells |
| CN104887615B (en) * | 2015-06-15 | 2017-11-07 | 齐鲁工业大学 | A kind of method for preparing class mycetocyte element coarse amino acid in hair weeds cells |
| CN105037201A (en) * | 2015-06-26 | 2015-11-11 | 浙江海洋学院 | Method for extracting mycosporine-like amino acids from euphausua superba |
| CN105037201B (en) * | 2015-06-26 | 2017-01-04 | 浙江海洋学院 | A kind of extraction class mycetocyte amino acid whose method of element from Antarctic krill |
| CN107044928A (en) * | 2016-02-05 | 2017-08-15 | 中国科学院大连化学物理研究所 | A kind of microalgae intracellular metabolin sample extraction method |
| CN107044928B (en) * | 2016-02-05 | 2019-08-27 | 中国科学院大连化学物理研究所 | A kind of microalgae metabolin sample extraction method intracellular |
| CN105817051A (en) * | 2016-03-30 | 2016-08-03 | 南通中国科学院海洋研究所海洋科学与技术研究发展中心 | Method for extracting micromolecular intracellular metabolite from nori |
| CN105817051B (en) * | 2016-03-30 | 2018-03-06 | 南通中国科学院海洋研究所海洋科学与技术研究发展中心 | The method that small molecule intracellular metabolin is extracted from seaweed |
| CN114657222A (en) * | 2022-04-08 | 2022-06-24 | 湖北省水利水电科学研究院 | Method for extracting mycosporine-like amino acid from Aphanizomenon flos-aquae |
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