CN105624247A - Preparation method for activator of Nrf2-ARE pathway in tuna high F ratio oligopeptide - Google Patents

Preparation method for activator of Nrf2-ARE pathway in tuna high F ratio oligopeptide Download PDF

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CN105624247A
CN105624247A CN201610110511.8A CN201610110511A CN105624247A CN 105624247 A CN105624247 A CN 105624247A CN 201610110511 A CN201610110511 A CN 201610110511A CN 105624247 A CN105624247 A CN 105624247A
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CN105624247B (en
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王斌
赵玉勤
孙坤来
罗红宇
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Zhejiang Ocean University ZJOU
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Abstract

The invention discloses a preparation method for an activator of an Nrf2-ARE pathway in a tuna high F ratio oligopeptide. The preparation method comprises the steps that an enzymatic hydrolysis solution is obtained by taking minced tuna meat as raw materials through bienzyme hydrolysis; the enzymatic hydrolysis solution is subjected to ultrafiltration, activated carbon adsorption and macroporous resin purification to obtain the tuna high F ratio oligopeptide; separation and purification are performed through gel column chromatography and reversed-phase high performance liquid chromatography to obtain an active peptide Ile-Glu-Leu-Val-Trp, and the molecular weight is determined to be 658.76 Da through ESI-MS. The prepared high-activity polypeptide has the good scavenging effect on hydroxyl free radicals and superoxide anion free radicals and also can promote accumulation of Nrf2 protein, activate the Nrf2-ARE pathway and be used as a drug and functional product for treating diseases such as liver injuries, skin photoaging and ageing which are closely related to the Nrf2-ARE pathway.

Description

A kind of preparation method of the Nrf2-ARE Pathway Activation agent in tuna high F value oligopeptide
Technical field
The preparation method that the present invention relates to a kind of Nrf2-ARE Pathway Activation agent, the preparation method of the Nrf2-ARE Pathway Activation agent being specifically related in a kind of tuna high F value oligopeptide.
Background technology
Oligo-peptide mixture be one by mixed small peptide (or the claim oligopeptide) system being made up of 3��7 residual amino acid residues of aminoacid. F value (Fischerratio) refers to the molal quantity ratio of branched-chain amino acid (BCAA:Val, Ile, Leu) and aromatic amino acid (AAA:Trp, Tyr, Phe) content. In the blood of normal person, F value is 3.0-3.5, and the F value suffering from hepatic disease patient only has 1.0 or lower, and the F value of high F value oligopeptide should be greater than 20, far above the ratio of this two amino acid in human body. Owing to it has aminoacid composition and the physiological function of uniqueness, have been subjected to showing great attention to of food and medicine circle.
Skipjack (Katsuwonuspelamis), belong to perch shape catalogue, tuna suborder, Thunnidae, frigate mackerel subfamily, oceanic bonito genus, have another name called positive oceanic bonito, bomb fish, hard fish, pine fish, flying tiger fish. Skipjack is ocean property Important Economic fish. Skipjack distribution is relatively wide, in the Indian Ocean, the Pacific Ocean and the Atlantic Ocean water temperature waters higher than more than 15 degrees Celsius, has the trace of Skipjack and rich reserves, exploitation prospect optimism.
Summary of the invention
The preparation method of the Nrf2-ARE Pathway Activation agent that the technical problem to be solved is to provide in a kind of tuna high F value oligopeptide.
The present invention solves that the technical scheme that above-mentioned technical problem is taked is: the preparation method of the Nrf2-ARE Pathway Activation agent in a kind of tuna high F value oligopeptide, it comprises the following steps:
1) enzymolysis of tuna minced meat:Depletion marlin minced meat homogenate, Gly-NaOH buffer (0.05mol/L is added by solid-to-liquid ratio 1g:10mL��15mL, pH9.5), pH to 9.0��10.0 is regulated with HCl or NaOH, solution temperature is modulated 55��65 DEG C, adds alkaline protease (enzyme activity >=1.95 �� 10 according to the 1.0%��1.5% of tuna minced meat quality5U/g), after enzymolysis time 3.5h��4.0h, enzymolysis solution is incubated 10��15min in 90��95 DEG C, and enzyme denaturing is lived; Enzymolysis solution temperature is adjusted to 45��55 DEG C, regulates pH to 6.0��7.0, add compound protease (enzyme activity >=1 �� 10 according to the 0.8%��1.0% of tuna minced meat quality3LAPU/g), enzymolysis time 2.5h��3.0h, enzymolysis solution is down to room temperature after being incubated 10��15min in 90��95 DEG C, in the centrifugal 15��20min of 8000��10000rpm, takes supernatant.
2) preparation of tuna minced meat high F value oligopeptide:Take above-mentioned supernatant, adopt 1kDa ultrafilter membrane to carry out hyperfiltration treatment, collect molecular weight less than 3kDa part, obtain ultrafiltration enzymolysis solution; Adjust pH value to 2.5 ~ 3.5 ultrafiltration enzymolysis solution, it is that ultrafiltration enzymolysis solution is slowly added in the glass column being mounted with activated carbon granule with 0.3��0.5mL/min flow velocity by 10��15:1 according to material with activated carbon granule ratio, after completion of the sample, adopt 1mol/L ammonia and the dehydrated alcohol mixed solution elution chromatography post of the 1:1 ratio of 2��3 times of column volumes, collect eluent, dry, obtain absorbent charcoal fine purification polypeptide; Absorbent charcoal fine purification polypeptide is made into the solution of 10��20mg/mL, adjust pH value to 6.5��7.5, be slowly added into material and D101 macroporous resin than be 10��15:1 the glass column loading D101 macroporous resin in, impurity is removed with the distilled water eluting of 2��3 times of column volumes, again with 95% ethanol elution of 2��3 times of column volumes, collect 95% ethanol elution thing, spray drying, be tuna minced meat high F value oligopeptide.
3) in tuna minced meat high F value oligopeptide prepared by Nrf2-ARE Pathway Activation agent:By tuna minced meat high F value oligopeptide successively through gel filtration chromatography and reversed-phase high-performance liquid chromatography purification, obtain Nrf2-ARE Pathway Activation agent.
As preferably, the tuna in described step 1) be Skipjack (Katsuwonuspelamis).
As preferably, the gel filtration chromatography of described step 3) and the detailed process of reversed-phase high-performance liquid chromatography purification be:
Gel filtration chromatography: refining for above-mentioned macroporous resin polypeptide is dissolved in distilled water and is made into the solution that concentration is 20��30mg/mL, through polydextran gel SephadexG-15 column chromatography for separation, eluting is carried out with distilled water, flow velocity is 0.5��0.8mL/min, the every 3min of wash solution collects a pipe and detects in 220nm, merges solution in test tube by peak, relatively each peak impact on Nrf2 protein level, select the highest component lyophilizing of Nrf2 protein level, be gel chromatography zymolyte;
Reversed-phase high-performance liquid chromatography purification: above-mentioned gel chromatography zymolyte distilled water is made into the solution of 90��100 �� g/mL, reversed-phase high-performance liquid chromatography is utilized to be purified, according to Nrf2 protein level is affected to obtain 1 active polypeptide Ile-Glu-Leu-Val-Trp (IELVW), it is 658.76Da that ESI-MS measures molecular weight.
Further preferably, described reversed-phase high-performance liquid chromatography condition is: sample size 10��15 �� L; Chromatographic column KromasilC18(250mm �� 4.6mm, 5 ��m); Mobile phase: water-acetonihile gradient elution (0��40min acetonitrile concentration is at the uniform velocity risen to 50% by 0); Elution speed 0.8 ~ 1.0mL/min; Ultraviolet detection wavelength 220nm.
Compared with present technology, hydroxyl radical free radical and ultra-oxygen anion free radical are had good scavenging action by Nrf2-ARE Pathway Activation agent Ile-Glu-Leu-Val-Trp (IELVW) in a kind of tuna high F value oligopeptide provided by the present invention; Nrf2 protein accumulation can be promoted, activate Nrf2-ARE path, raise antioxidase and II phase detoxication enzyme removes nuisance, the damage of the active oxygen that protection body produces from oxidative stress; Can be used as the medicine of preparation hepatic injury, skin photoage, aging and other and the closely-related disease of Nrf2-ARE path or health food.
Accompanying drawing explanation
Fig. 1 is the polydextran gel SephadexG-15 tomographic map of the present invention.
Fig. 2 polydextran gel SephadexG-15 prepares the reversed-phase high-performance liquid chromatography chromatogram of zymolyte.
Fig. 3 Ile-Glu-Leu-Val-Trp (IELVW) impact on Nrf2 protein expression level.
Detailed description of the invention
Below in conjunction with accompanying drawing embodiment, the present invention is described in further detail.
Embodiment:
The preparation method of the preparation method of the Nrf2-ARE Pathway Activation agent in a kind of tuna high F value oligopeptide, preparation technology flow process is as follows: tuna minced meat �� bis-enzyme enzymolysis �� zymolyte �� ultrafiltration �� activated carbon adsorption �� purification by macroporous resin �� tuna high F value oligopeptide �� gel permeation chromatography �� high performance liquid chromatography prepare �� Nrf2-ARE Pathway Activation agent.
1) enzymolysis of tuna minced meat:Take Skipjack minced meat homogenate, add Gly-NaOH buffer (0.05mol/L, pH9.5) by solid-to-liquid ratio 1g:12mL, regulate pH to 9.3 with HCl or NaOH, solution temperature is modulated 60 DEG C, adds alkaline protease (enzyme activity >=1.95 �� 10 according to the 1.2% of tuna minced meat quality5U/g), after enzymolysis time 3.5h, enzymolysis solution is incubated 12min in 95 DEG C, and enzyme denaturing is lived; Enzymolysis solution temperature is adjusted to 50 DEG C, regulates pH to 7.0, add compound protease (enzyme activity >=1 �� 10 according to the 0.9% of tuna minced meat quality3LAPU/g), enzymolysis time 3.0h, enzymolysis solution is down to room temperature after being incubated 15min in 95 DEG C, in the centrifugal 15min of 9000rpm, takes supernatant.
2) preparation of tuna minced meat high F value oligopeptide:Take above-mentioned supernatant, adopt 1kDa ultrafilter membrane to carry out hyperfiltration treatment, collect molecular weight less than 3kDa part, obtain ultrafiltration enzymolysis solution; Adjust pH value to 3.0 ultrafiltration enzymolysis solution, than for 12:1, ultrafiltration enzymolysis solution is slowly added into 0.3mL/min flow velocity in the glass column loading activated carbon granule with activated carbon granule according to material, after completion of the sample, adopt 1mol/L ammonia and the dehydrated alcohol mixed solution elution chromatography post of the 1:1 ratio of 3 times of column volumes, collect eluent, dry, obtain absorbent charcoal fine purification polypeptide; Absorbent charcoal fine purification polypeptide is made into the solution of 15mg/mL, adjust pH value to 7.0, it is slowly added into material with D101 macroporous resin ratio in the glass column loading D101 macroporous resin of 15:1, impurity is removed with the distilled water eluting of 3 times of column volumes, again with 95% ethanol elution of 3 column volumes, collect 95% ethanol elution thing, spray drying, be tuna minced meat high F value oligopeptide.
3) in tuna minced meat high F value oligopeptide prepared by Nrf2-ARE Pathway Activation agent:By tuna minced meat high F value oligopeptide successively through gel filtration chromatography and reversed-phase high-performance liquid chromatography purification, obtain Nrf2-ARE Pathway Activation agent.
As preferably, the gel filtration chromatography of described step 3) and the detailed process of reversed-phase high-performance liquid chromatography purification be:
1. gel filtration chromatography: refining for above-mentioned macroporous resin polypeptide is dissolved in distilled water and is made into the solution that concentration is 20mg/mL, through polydextran gel SephadexG-15 column chromatography for separation, eluting is carried out with distilled water, flow velocity is 0.6mL/min, the every 3min of wash solution collects a pipe and detects in 220nm, merges solution in test tube by peak, relatively each peak impact on Nrf2 protein level, select the highest component lyophilizing of Nrf2 protein level, be gel chromatography zymolyte Fr.3(Fig. 1).
2. reversed-phase high-performance liquid chromatography purification: above-mentioned gel chromatography zymolyte distilled water is made into the solution of 100 �� g/mL, (condition is: sample size 15 �� L to utilize reversed-phase high-performance liquid chromatography to be purified; Chromatographic column KromasilC18(250mm �� 4.6mm, 5 ��m); Mobile phase: water-acetonihile gradient elution (0��40min acetonitrile concentration is at the uniform velocity risen to 50% by 0); Elution speed 0.8mL/min; Ultraviolet detection wavelength 220nm. ), according to Nrf2 protein level affected to obtain 1 active polypeptide (Fig. 2).
3. structure detection: collect the polypeptide that the accumulative level of Nrf2 protein is the highest, the detection of inverted high performance liquid chromatography is simple spike, utilizing protein/polypeptide sequenator to measure aminoacid sequence is Ile-Glu-Leu-Val-Trp (IELVW), and it is 658.76Da that ESI-MS measures molecular weight.
Free radical scavenging is tested: prepared tuna minced meat polypeptide Ile-Glu-Leu-Val-Trp (IELVW) is carried out free radical scavenging experiment. Test result indicate that: Ile-Glu-Leu-Val-Trp (IELVW) is to hydroxyl radical free radical (EC500.12mg/mL) with ultra-oxygen anion free radical (EC500.06mg/mL) there is good scavenging action.
The anti-oxidation peptide effect to activating Nrf2/ARE path: after the human embryonic kidney cell line HEK293 cell of trophophase of taking the logarithm is inoculated in 60mm ware 24 hours, it is separately added into enzymolysis solution and the Ile-Glu-Leu-Val-Trp (IELVW) of 10 ��Ms, continues to cultivate 4 hours. Supernatant discarded, cell RIPA buffer (the green skies Bioisystech Co., Ltd in Shanghai) cracks, and BCA method measures protein concentration. Each sample takes 20 �� g albumen and separates through SDS-PAGE, and then western blotting method detects the protein level of Nrf2 routinely.
Compared with present technology, hydroxyl radical free radical and ultra-oxygen anion free radical are had good scavenging action by Nrf2-ARE Pathway Activation agent Ile-Glu-Leu-Val-Trp (IELVW) in a kind of tuna high F value oligopeptide provided by the present invention; Nrf2 protein accumulation can be promoted, activate Nrf2-ARE path, raise antioxidase and II phase detoxication enzyme removes nuisance, the damage of the active oxygen that protection body produces from oxidative stress; Can be used as the medicine of preparation hepatic injury, skin photoage, aging and other and the closely-related disease of Nrf2-ARE path or health food.
Finally, in addition it is also necessary to be only the specific embodiment of the present invention it is noted that listed above. It is clear that the invention is not restricted to above example, it is also possible to there are many deformation. All deformation that those of ordinary skill in the art can directly derive from present disclosure or associate, are all considered as protection scope of the present invention.
SEQUENCELISTING
<110>Oceanography Institute Of Zhejiang
<120>preparation method of the Nrf2-ARE Pathway Activation agent in a kind of tuna high F value oligopeptide
<130>zjou-wb-201602-103
<160>1
<170>PatentInversion3.5
<210>1
<211>5
<212>PRT
<213>synthetic
<400>1
IleGluLeuValTrp
15

Claims (5)

1. the preparation method of the Nrf2-ARE Pathway Activation agent in a tuna high F value oligopeptide, it is characterised in that comprise the following steps:
1) enzymolysis of tuna minced meat:Depletion marlin minced meat homogenate, Gly-NaOH buffer is added by solid-to-liquid ratio 1g:10mL��15mL, pH to 9.0��10.0 is regulated with HCl or NaOH, solution temperature is modulated 55��65 DEG C, alkaline protease is added according to the 1.0%��1.5% of tuna minced meat quality, after enzymolysis time 3.5h��4.0h, enzymolysis solution is incubated 10��15min in 90��95 DEG C, and enzyme denaturing is lived; Enzymolysis solution temperature is adjusted to 45��55 DEG C, regulate pH to 6.0��7.0, compound protease is added according to the 0.8%��1.0% of tuna minced meat quality, enzymolysis time 2.5h��3.0h, enzymolysis solution is down to room temperature after being incubated 10��15min in 90��95 DEG C, in the centrifugal 15��20min of 8000��10000rpm, take supernatant;
2) preparation of tuna minced meat high F value oligopeptide:Take above-mentioned supernatant, adopt 1kDa ultrafilter membrane to carry out hyperfiltration treatment, collect molecular weight less than 3kDa part, obtain ultrafiltration enzymolysis solution; Adjust pH value to 2.5 ~ 3.5 ultrafiltration enzymolysis solution, it is that ultrafiltration enzymolysis solution is slowly added in the glass column being mounted with activated carbon granule with 0.3��0.5mL/min flow velocity by 10��15:1 according to material with activated carbon granule ratio, after completion of the sample, adopt 1mol/L ammonia and the dehydrated alcohol mixed solution elution chromatography post of the 1:1 ratio of 2��3 times of column volumes, collect eluent, dry, obtain absorbent charcoal fine purification polypeptide; Absorbent charcoal fine purification polypeptide is made into the solution of 10��20mg/mL, adjust pH value to 6.5��7.5, be slowly added into material and D101 macroporous resin than be 10��15:1 the glass column loading D101 macroporous resin in, impurity is removed with the distilled water eluting of 2��3 times of column volumes, again with 95% ethanol elution of 2��3 times of column volumes, collect 95% ethanol elution thing, spray drying, be tuna minced meat high F value oligopeptide;
3) in tuna minced meat high F value oligopeptide prepared by Nrf2-ARE Pathway Activation agent:By tuna minced meat high F value oligopeptide successively through gel filtration chromatography and reversed-phase high-performance liquid chromatography purification, obtain Nrf2-ARE Pathway Activation agent;
Gly-NaOH buffer in wherein said step 1) is 0.05mol/L, and pH value is 9.5; Enzyme activity >=1.95 �� 10 of alkaline protease5U/g; Enzyme activity >=1 �� 10 of compound protease3LAPU/g��
2. preparation method according to claim 1, it is characterized in that the tuna in described step 1) is Skipjack and isKatsuwonuspelamis��
3. preparation method according to claim 1, it is characterised in that the gel filtration chromatography of described step 3) and the detailed process of reversed-phase high-performance liquid chromatography purification be:
Gel filtration chromatography: refining for above-mentioned macroporous resin polypeptide is dissolved in distilled water and is made into the solution that concentration is 20��30mg/mL, through polydextran gel SephadexG-15 column chromatography for separation, eluting is carried out with distilled water, flow velocity is 0.5��0.8mL/min, the every 3min of wash solution collects a pipe and detects in 220nm, merges solution in test tube by peak, relatively each peak impact on Nrf2 protein level, select the highest component lyophilizing of Nrf2 protein level, be gel chromatography zymolyte;
Reversed-phase high-performance liquid chromatography purification: above-mentioned gel chromatography zymolyte distilled water is made into the solution of 90��100 �� g/mL, reversed-phase high-performance liquid chromatography is utilized to be purified, according to affecting Nrf2 protein level 1 active polypeptide Ile-Glu-Leu-Val-Trp, ESI-MS to measure molecular weight be 658.76Da.
4. preparation method according to claim 1, it is characterised in that: described reversed-phase high-performance liquid chromatography condition is: sample size 10��15 �� L; Chromatographic column is specification is 250mm �� 4.6mm, and filler particles diameter is the KromasilC of 5 ��m18; Mobile phase is water-acetonihile gradient elution, and 0��40min acetonitrile concentration is at the uniform velocity risen to 50% by 0; Elution speed 0.8 ~ 1.0mL/min; Ultraviolet detection wavelength 220nm.
5. preparation method according to claim 1, it is characterised in that: prepared activator is pentapeptide compound, and aminoacid sequence is Ile-Glu-Leu-Val-Trp, ESI-MS mensuration molecular weight is 658.76Da.
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CN106632605A (en) * 2016-12-22 2017-05-10 浙江海洋大学 Liver injury and repair type active peptide prepared from tuna offal
CN107164440A (en) * 2017-05-11 2017-09-15 浙江海洋大学 High F value oligopeptide Coarse liquid separation purification process
CN108095125A (en) * 2017-12-12 2018-06-01 浙江海洋大学 A kind of brown croaker air bladder polypeptide health care food of liver protecting and preparation method thereof
CN113969301A (en) * 2021-10-25 2022-01-25 厦门大学 Method for preparing peptone from skipjack leftovers
CN115144508A (en) * 2022-09-02 2022-10-04 广州市乾相生物科技有限公司 HPLC separation method suitable for multiple water-soluble peptides
CN113801194B (en) * 2021-10-15 2023-06-20 浙江海洋大学 Hypolipidemic peptide of tuna roe and application thereof
CN117285595A (en) * 2023-11-27 2023-12-26 中国科学院烟台海岸带研究所 Pentapeptide LK5 with intestinal barrier protection function and application thereof

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CN103073621A (en) * 2012-12-20 2013-05-01 浙江海洋学院 Minced tuna protein antioxidative peptide and its preparation method and use
CN103275181A (en) * 2013-05-23 2013-09-04 浙江海洋学院 Tuna ground meat polypeptide angiogenesis inhibiting factor as well as preparation method and application thereof

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JP2009091306A (en) * 2007-10-10 2009-04-30 Yaizu Suisankagaku Industry Co Ltd Antioxidant
CN103073621A (en) * 2012-12-20 2013-05-01 浙江海洋学院 Minced tuna protein antioxidative peptide and its preparation method and use
CN103275181A (en) * 2013-05-23 2013-09-04 浙江海洋学院 Tuna ground meat polypeptide angiogenesis inhibiting factor as well as preparation method and application thereof

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106632605A (en) * 2016-12-22 2017-05-10 浙江海洋大学 Liver injury and repair type active peptide prepared from tuna offal
CN106632605B (en) * 2016-12-22 2020-06-16 浙江海洋大学 Active peptide prepared from tuna leftovers and having liver injury repair effect
CN107164440A (en) * 2017-05-11 2017-09-15 浙江海洋大学 High F value oligopeptide Coarse liquid separation purification process
CN108095125A (en) * 2017-12-12 2018-06-01 浙江海洋大学 A kind of brown croaker air bladder polypeptide health care food of liver protecting and preparation method thereof
CN108095125B (en) * 2017-12-12 2021-05-18 浙江海洋大学 Liver-protecting miichthys miiuy swim bladder polypeptide health food and preparation method thereof
CN113801194B (en) * 2021-10-15 2023-06-20 浙江海洋大学 Hypolipidemic peptide of tuna roe and application thereof
CN113969301A (en) * 2021-10-25 2022-01-25 厦门大学 Method for preparing peptone from skipjack leftovers
CN113969301B (en) * 2021-10-25 2024-01-02 厦门大学 Method for preparing peptone from bonito scraps
CN115144508A (en) * 2022-09-02 2022-10-04 广州市乾相生物科技有限公司 HPLC separation method suitable for multiple water-soluble peptides
CN115144508B (en) * 2022-09-02 2022-12-13 广州市乾相生物科技有限公司 HPLC separation method suitable for multiple water-soluble peptides
CN117285595A (en) * 2023-11-27 2023-12-26 中国科学院烟台海岸带研究所 Pentapeptide LK5 with intestinal barrier protection function and application thereof
CN117285595B (en) * 2023-11-27 2024-01-26 中国科学院烟台海岸带研究所 Pentapeptide LK5 with intestinal barrier protection function and application thereof

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