CN1651574A - Enzymatic synthesis of plant-type melanin - Google Patents

Enzymatic synthesis of plant-type melanin Download PDF

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Publication number
CN1651574A
CN1651574A CNA2004100041084A CN200410004108A CN1651574A CN 1651574 A CN1651574 A CN 1651574A CN A2004100041084 A CNA2004100041084 A CN A2004100041084A CN 200410004108 A CN200410004108 A CN 200410004108A CN 1651574 A CN1651574 A CN 1651574A
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melanin
enzyme
melanochrome
plant
enzymatic
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王敬文
张金萍
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Research Institute of Subtropical Forestry of Chinese Academy of Forestry
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Research Institute of Subtropical Forestry of Chinese Academy of Forestry
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    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
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    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

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Abstract

A process for synthesizing the vegetative melanin by enzyme method includes such steps as preparing polyphenol oxidase and phenol from plant, creating enzymatic reaction system in buffering phosphate solution, enzymatic reaction to synthesize malanin, separating and purifying.

Description

Plant type melanochrome enzyme process is synthetic
Technical field the invention belongs to biological chemistry goods field
Technical background melanochrome is biological protectiveness pigment, extensively is present in animal, plant and the microorganism, and black have and absorbs ultraviolet, anti-oxidant, as to eliminate free radical effect, and biological organism is played provide protection.Form by melanic structure, can be divided into three kinds of patterns, i.e. eumelanin (eumelanin), pheomelanins (phaeomelanin) and different melanochrome (allpmelanin).The eumelanin color is dark-brown or black, is transformed and generates via DOPA (Dopa) approach by tyrosine, and this melanochrome mainly is distributed in animal cuticle and the hair cell, and in internal organ film or the tissue, can be described as animal-type melanochrome.Pheomelanins is the cystine derivatives of eumelanin, and sulfur atom-containing, color are reddish brown or yellow, are common in the hair of animal.Different melanochrome mainly is distributed in the plant, platymiscium type melanochrome, and being similar to eumelanin is brown or black, it is mainly generated via poly hydroxyl naphthalene approach by dihydric phenols such as catechol, trihydric phenol.
Nicolaus et al proposes, and animal source melanochrome belongs to the indoles type more, and plant-sourced melanochrome belongs to the pyrocatechol type more.Porta is to be skeleton with indoles or benzothiazine according to its structural unit after further research, and animal source melanochrome is divided into eumelanin (eumelanin) and pheomelanins (pheomelanin).
Wang Yan etc. have studied the infrared spectrum characterization of several natural black pigment molecular structures, propose hair melanochrome and belong to eumelanin and pheomelanins mixed type melanochrome, Pericarpium Musae melanochrome, sunflower seeds melanochrome all belong to pyrocatechol type melanochrome, be that polyphenol substance is converted into hydroxyquinone under the effect of polyphenoloxidase and phenolic hydroxyl group enzyme, and then polymerization formation.They think that also Semen Sesami Nigrum melanochrome is the mixed type melanochrome of indoles type and pyrocatechol type simultaneously.Affirmations such as Yin Peiyu contain the phenols conjugated structure in the Semen Sesami Nigrum melanochrome, prove that tentatively Semen Sesami Nigrum melanochrome has the melanic constitutional features of catechol type, are made of catechol, Resorcinol and micro-catechuic acid, do not contain indoles type component.According to these research, show plant type melanochrome mainly be by monohydric phenol,
Phenols components such as dihydric phenol are synthetic under the effect of polyphenoloxidase and phenolic hydroxyl group enzyme.
Summary of the invention the present invention forms according to the plant type melanin structure, and with the synthetic plant type melanochrome of zymochemistry method, bare bones of the present invention is as follows:
1. the enzyme preparation of polyphenol oxidase enzyme system
From multiple polyphenol oxidase enzyme active high vegetable material and mushroom material, separate, produce the polyphenol oxidase enzyme comprising vegetable matters such as pears, apple, potato, sweet potato, bamboo shoots, alder, China fir, pine, mandarin jacket wood, mushroom, Lasiosphaera fenzliis, comprise the phenolic hydroxyl group enzyme.Vegetable matter is pulverized homogenate in phosphoric acid buffer PH7.0, centrifugal 15～20 minutes of 5000rpm removes slag and obtains supernatant liquor, adds to make the ammonium sulfate that reaches 40～50% saturation ratios, saltouts in 4 ℃ of refrigerators, centrifugal collection zymoprotein precipitation.Zymoprotein is dissolved in small volume phosphoric acid buffer (PH7.0), the desalination of last Sephadex G-25 post, and the phosphoric acid buffer wash-out is collected enzyme liquid.Add freezing acetone or alcohol in the enzyme liquid and be settled out zymoprotein, centrifugal collection zymoprotein, lyophilize gets the powder zymin, enzyme activity 11000～15000 units/g.
2. enzymatic is synthetic
Dissolve 0.1～2.0g Resorcinol, pyrocatechol, pyrogallol, gallic acid, tyrosine in the 1000ml phosphoric acid buffer (PH8.0) separately, or its different combination, transfer PH to 8.0 with 2MNaOH, 35～42 ℃ of insulations, add above-mentioned zymin 0.5～1.0g, continue insulation 3～5 hours, stirring that does not stop or ventilation.The blackening gradually of reaction solution color is up to thick black.
3. separation and purification
After the enzymatic building-up reactions finishes, add 6N HCL and transfer PH≤4, melanochrome is flocks separates out, left standstill 3～4 hours, and the supernatant liquor that inclines, centrifugal or filtration collecting precipitation, the deionized water thorough washing, lyophilize obtains the melanochrome crude product.
The melanochrome product often with protein or other compositions take place in conjunction with and separate out with precipitation, need carry out purification process.The melanochrome dried powder was joined among the 6N HCL backwash 16～24 hours, and backwash finishes the back standing over night, the supernatant liquor that inclines, and centrifugal collecting precipitation, the deionized water thorough washing, lyophilize obtains the pure product of melanochrome.Perhaps, with melanochrome powder suspension (0.5g/ liter) in trypsin solution, transfer PH7～8,40 ℃ insulation 2～3 hours, after the enzymic digestion reaction finishes, transfer PH≤4, leave standstill the back melanin deposition and get off the supernatant liquor that inclines, centrifugal collecting precipitation, the deionized water thorough washing obtains the pure product of melanochrome through lyophilize.
4. physico-chemical property detects
Though different (animal, plant, microorganism), the structure differences (indoles type, phenol quinoid) in melanochrome source, but the physico-chemical property that is shown is the same (Nicolaus R.A.et al, 1964), the common characteristic ultraviolet absorption is promptly arranged, water insoluble, be insoluble to acid, be insoluble to common organic solvents, dissolve in alkaline water, can be by KMnO 4Or H 2O 2Oxidation and fading etc. detects according to these physico-chemical properties, and detected result shows that obtained product all has these melanic physico-chemical properties, and successfully enzymatic has synthesized plant type melanochrome.
Embodiment
Example 1.
With cross-fertilize seed potato that 100g gathered in the crops 4 ℃ of precoolings 2 hours, remove the peel subsequently, shred, in ice bath, add an amount of 0.1mol/L phosphoric acid buffer (PH7.0) homogenate, centrifugal 15～20 minutes of 5000rpm, add ammonium sulfate in the supernatant liquor and reach 50% saturation ratio, in 4 ℃ of refrigerators, saltout centrifugal collection zymoprotein precipitation.Zymoprotein is dissolved in small volume 0.1mol/L phosphoric acid buffer (PH7.0), the desalination of last Sephadex G-25 post, the phosphoric acid buffer wash-out is collected enzyme liquid.Add 2.5 times of (V/V)-18 ℃ freezing acetone in the enzyme liquid, the centrifugal collection zymoprotein of 8000rpm obtains zymin 1.8g through lyophilize.Measure the required enzyme amount of L-Dopa generation 1mmol dopachrome with the MansonH.S. method and be defined as an enzyme activity unit, Dopachrome is 3600mol/L at the optical extinction coefficient of 475nm -1.cm -1, the zymin vitality test result that the present invention makes is 6744 units/g.
Example 2.
The new fresh mushroom of 100g 4 ℃ of precoolings 2 hours, is added an amount of 0.1mol/L phosphoric acid buffer (PH7.0) homogenate in ice bath, centrifugal 15～20 minutes of 5000rpm, ammonium sulfate reaches 50% saturation ratio in the supernatant liquor, saltouts centrifugal collecting precipitation in 4 ℃ of refrigerators.Obtain precipitation is dissolved in small volume phosphoric acid buffer (PH7.0), and elutriant is collected in the desalination of last Sephadex G-25 post, add 2.5 times of (V/V)-18 ℃ freezing acetone, separate out the zymoprotein precipitation, the centrifugal collection zymoprotein of 8000rpm obtains zymin 4.26g through lyophilize.The enzymic activity that records by example 1 method is 7546 units/g.
Example 3.
With pyrocatechol 1g and yellow soda ash 0.2g with a little hot water dissolving after, add in the 1000ml0.2mol/L phosphoric acid buffer (PH8.0), heat to 40～42 ℃, add example 1 zymin 1.0～1.5g, add CuSO 4.7H 2O 50mg, 40～42 ℃ are incubated 3～5 hours in water-bath, do not stop to stir.After reaction finishes, add 6N HCL and transfer PH≤4, the melanochrome flocks is separated out, left standstill 5 hours, and the supernatant liquor that inclines, centrifugal collection flocks, lyophilize obtains melanochrome phase product 1.24g.
Example 4.
With pyrocatechol 1g and yellow soda ash 0.2g with a little hot water dissolving after, add in the 1000ml 0.2mol/L phosphoric acid buffer (PH8.0), heat to 40～42 ℃, add example 2 zymins 1.0～1.2g, add CuSO 4.7H 2O 50mg, 40～42 ℃ are incubated 3～5 hours in water-bath, do not stop to stir.After reaction finishes, add 6N HCL and transfer PH≤4, the melanochrome flocks is separated out, left standstill 5 hours, and the supernatant liquor that inclines, centrifugal collecting precipitation, lyophilize obtains melanochrome crude product 0.98g.
Example 5.
With Resorcinol 1g and yellow soda ash 0.2g with a little hot water dissolving after, join in the 1000ml 0.2mol/L phosphoric acid buffer (PH8.0), heat to 40～42 ℃, add example 1 zymin 1.0～1.5g, add CuSO 4.7H 2O 50mg is incubated 3～5 hours in water-bath, do not stop to stir.After reaction finishes, add 6N HCL and transfer PH≤4, the melanochrome flocks is separated out, left standstill 5 hours, and the supernatant liquor that inclines, centrifugal collecting precipitation, lyophilize obtains melanochrome crude product 1.2g.
Example 6.
With pyrogallol 1g and 0.2g yellow soda ash with a little hot water dissolving after, join in the 1000ml 0.2mol/L phosphoric acid buffer (PH8.0), heat to 40～42 ℃, add example 1 zymin 1.0～1.5g, add CuSO 4.7H 2O 50mg, 40～42 ℃ are incubated 3～5 hours in water-bath, do not stop to stir.After reaction finishes, add 6N HCL and transfer PH≤4, the melanochrome flocks is separated out, left standstill 5 hours, and the supernatant liquor that inclines, centrifugal collecting precipitation, lyophilize obtains melanochrome crude product 1.05g.
Example 7.
With gallic acid 1g and 0.2g yellow soda ash with a little hot water dissolving after, join in the 1000ml 0.2mol/L phosphoric acid buffer (PH8.0), heat to 40～42 ℃, add example 1 zymin 1.0～1.5g, add CuSO 4.7H 2O 50mg, 40～42 ℃ are incubated 3～5 hours in water-bath, do not stop to stir.After reaction finishes, add 6N HCL and transfer PH≤4, the melanochrome flocks is separated out, left standstill 5 hours, and the supernatant liquor that inclines, centrifugal collecting precipitation, lyophilize obtains melanochrome crude product 0.92g.
Example 8.
With example 3,4,5,6, the 7 melanochrome crude products of being produced respectively take by weighing 1g, heat backwash 18～24 hours respectively in 50ml 6N HCL, cooled and filtered, the deionized water thorough washing, 105 ℃ of dryings, the purifying melanin that obtains is respectively 0.53g, 0.62g, 0.46g, 0.48g, 0.37g.
Example 9.
With example 3,4,5,6, the 7 melanochrome crude products of being produced respectively take by weighing 1g, join respectively in the 100ml phosphoric acid buffer (PH6.8), be heated to 40～42 ℃, add trypsinase 500mg more respectively, 40～42 ℃ are incubated 2～3 hours, add 6N HCL and transfer PH≤4, centrifugal collecting precipitation, and use the deionized water thorough washing, and 105 ℃ of dryings, the purifying melanin that obtains is respectively 0.43g, 0.63g, 0.41g, 0.46g, 0.40g.
Example 10.
Will be by example 3,4,5,6, the synthetic melanic physico-chemical property of producing of plant type of 7 enzyme process is measured, and the Dopa-melanine (Dopa melanochrome) that produces with Sigma company and the melanochrome of producing from vegetable material horse-chestnut (Aesculushippocastanicum), Sunflower Receptacle (Heliantus annus) by Kereatea et al method compare:
(1) ultraviolet and visible absorption are the strongest in the short-wave band absorption, increase to absorb with wavelength and weaken;
(2) the same with Sunflower Receptacle melanochrome, water insoluble with Dopa melanochrome, horse-chestnut, be insoluble to general common organic solvent;
(3) dissolving fully in 0.5mol/LNaOH or KOH solution;
(4) be insoluble to acid, some precipitation in PH＜5;
(5) FeCl 3Precipitate when existing;
(6) KMnO 4And H 2O 2Can oxidation and make and fade
(7) can make AgNO 3Regeneration NH 4Solution
These character all show example 3,4, and 5,6,7 enzymatic synthetic products are plant type melanochrome.
The present invention makes a living to produce and gets plant type melanochrome new way is provided, and technology is simple, produces conveniently, and is with low cost.
Nicolaus?R.A.，Piattellim.，Fattorusso?E.Tetrahedron，1964，20：1163?Porta?G.J.Invest.Dermatol，1980，75：122
Wang Yan etc., assay office, 1996, the 15 volumes, the 6th phase, 63-35.
Yin Peiyu etc., the gas chromatography/mass spectrometry method is identified melanic structure type in the Semen Sesami Nigrum, chromatogram, calendar year 2001 the 19th is rolled up the 3rd phase, 208-209.
Manson?H.S.Oxidase.Aun.Rev.Biochem.1965，34，595-634.
Kerestes?J.J.et?al.Biological?active?fraction?of?vegetable?melanin，process?for?itsproduction?and?its?use，United?States?Patent?Application，20020041905.April?11，2002.

Claims (8)

1.本发明提出了用酶促合成法生产制取植物型黑色素的新途径新方法。1. The present invention proposes a new approach and new method for producing plant-type melanin by enzymatic synthesis. 2.按权利要求1，酶促合成法生产制取植物型黑色素的新途径、新方法，包括酶制剂的分离制备、酶反应底物、酶促反应系统组成、酶促反应条件和酶促反应产物的分离和纯化。2. According to claim 1, a new approach and a new method for enzymatic synthesis to produce plant-type melanin, including the separation and preparation of enzyme preparations, enzyme reaction substrates, enzymatic reaction system composition, enzymatic reaction conditions and enzymatic reactions Product isolation and purification. 3.按权利要求2，所涉及的酶包括多酚氧化酶系统中的所有的参于合成黑色素的酶种类及其相应的辅酶、辅基和活化因子等，这种包括多酚氧化酶系统的酶制剂，既包括酶粗提物，也包括经部分纯化的酶制剂粉末和溶液。3. By claim 2, the enzymes involved include all enzymes involved in the synthesis of melanin in the polyphenol oxidase system and their corresponding coenzymes, prosthetic groups and activating factors. Enzyme preparations include both crude enzyme extracts and partially purified enzyme preparation powders and solutions. 4.按权利要求3，所涉及的多酚氧化酶系统的所有酶种类是从各种植物材料和微生物材料(包括真菌)按广为人知的方法制取的。4. According to claim 3, all enzyme species of the polyphenol oxidase system involved are obtained from various plant materials and microbial materials (including fungi) by widely known methods. 5.按权利要求2，酶反应底物包括一元酚及其衍生物(酪氨酸、酪胺、多巴、多巴胺等及其衍生物)、二元酚及其衍生物(对苯二酚、邻苯二酚、间本二酚、儿茶酸、异儿茶酸等及其衍生物)、三元酚及其衍生物(连苯三酚、没食子酸等及其衍生物)。5. by claim 2, enzyme reaction substrate comprises monohydric phenol and derivative thereof (tyrosine, tyramine, dopa, dopamine etc. and derivative thereof), dihydric phenol and derivative thereof (hydroquinone, Catechol, resorcinol, catechin, isocatechin, etc. and their derivatives), trihydric phenols and their derivatives (pyrogallol, gallic acid, etc. and their derivatives). 6.按权利要求2，酶促合成植物型黑色素反应系统组成包括磷酸缓冲液(PH6-9)、权利要求5中的底物0.1-3.0g/升、权利要求3中的酶系统5000-100000单位/升。6. According to claim 2, the enzymatic synthesis of plant-type melanin reaction system consists of phosphate buffer (PH6-9), substrate 0.1-3.0g/liter in claim 5, enzyme system 5000-100000 in claim 3 unit/liter. 7.按权利要求2，用酸调PH≤4沉淀析出黑色素，使黑色素从酶反应液中分离出来。7. According to claim 2, the melanin is separated out from the enzyme reaction solution by adjusting the pH to 4 with an acid to precipitate the melanin. 8.按权利要求2，用3-9N HCL洄流10-30小时或用胰酶水解消化法处理酶法合成制取的黑色素粗产物，使黑色素产品得以纯化。8. According to claim 2, use 3-9N HCL to flow back for 10-30 hours or treat the crude melanin produced by enzymatic synthesis with 3-9N HCL, so that the melanin product can be purified.
CNA2004100041084A 2004-02-06 2004-02-06 Enzymatic synthesis of plant-type melanin Pending CN1651574A (en)

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102090421A (en) * 2010-11-30 2011-06-15 中国农业科学院生物技术研究所 Biologically active substance and application thereof to prevention and control of soybean cyst nematode No.4 microspecies
CN102399824A (en) * 2010-09-13 2012-04-04 浙江医药股份有限公司新昌制药厂 Method for preparing plant carbon black substitute by using leaves of Vaccinium plants as raw materials
CN106146773A (en) * 2015-03-29 2016-11-23 西南林业大学 A kind of method of the natural melanin synthesized base resin of direct acid catalysis
CN106140107A (en) * 2015-03-27 2016-11-23 西南林业大学 A kind of method that natural black pigment base resin is prepared in ammonia catalytic thermal solidification
CN111778291A (en) * 2020-06-23 2020-10-16 南京师范大学 A kind of method that utilizes microorganism or enzyme to ferment or transform sunflower meal and sunflower shell to increase the production of melanin
CN111826406A (en) * 2020-07-20 2020-10-27 西安幸福未来化妆品有限公司 Preparation method and application of melanin precursor dopaquinone
CN113875990A (en) * 2021-10-11 2022-01-04 中北大学 Ferrous iron with antioxidant activity and preparation method thereof

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102399824A (en) * 2010-09-13 2012-04-04 浙江医药股份有限公司新昌制药厂 Method for preparing plant carbon black substitute by using leaves of Vaccinium plants as raw materials
CN102399824B (en) * 2010-09-13 2013-08-07 浙江医药股份有限公司新昌制药厂 Method for preparing plant carbon black substitute by using leaves of Vaccinium plants as raw material
CN102090421A (en) * 2010-11-30 2011-06-15 中国农业科学院生物技术研究所 Biologically active substance and application thereof to prevention and control of soybean cyst nematode No.4 microspecies
CN102090421B (en) * 2010-11-30 2013-06-26 中国农业科学院生物技术研究所 A biologically active substance and its application in the control of race 4 of soybean cyst nematode
CN106140107A (en) * 2015-03-27 2016-11-23 西南林业大学 A kind of method that natural black pigment base resin is prepared in ammonia catalytic thermal solidification
CN106140107B (en) * 2015-03-27 2019-06-21 西南林业大学 A kind of ammonia catalysis-thermal curing method for preparing natural melanin-based resin
CN106146773A (en) * 2015-03-29 2016-11-23 西南林业大学 A kind of method of the natural melanin synthesized base resin of direct acid catalysis
CN106146773B (en) * 2015-03-29 2018-05-04 西南林业大学 A kind of method of the directly natural melanin synthesized base resin of acid catalysis
CN111778291A (en) * 2020-06-23 2020-10-16 南京师范大学 A kind of method that utilizes microorganism or enzyme to ferment or transform sunflower meal and sunflower shell to increase the production of melanin
CN111826406A (en) * 2020-07-20 2020-10-27 西安幸福未来化妆品有限公司 Preparation method and application of melanin precursor dopaquinone
CN113875990A (en) * 2021-10-11 2022-01-04 中北大学 Ferrous iron with antioxidant activity and preparation method thereof
CN113875990B (en) * 2021-10-11 2024-06-11 中北大学 Ferrous melanin with antioxidant activity and preparation method thereof

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