JPH0516836B2 - - Google Patents
Info
- Publication number
- JPH0516836B2 JPH0516836B2 JP63173393A JP17339388A JPH0516836B2 JP H0516836 B2 JPH0516836 B2 JP H0516836B2 JP 63173393 A JP63173393 A JP 63173393A JP 17339388 A JP17339388 A JP 17339388A JP H0516836 B2 JPH0516836 B2 JP H0516836B2
- Authority
- JP
- Japan
- Prior art keywords
- trypsin
- casein
- peptide
- activity
- cei
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 claims description 31
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 claims description 21
- 235000021240 caseins Nutrition 0.000 claims description 21
- 239000005018 casein Substances 0.000 claims description 20
- 238000010438 heat treatment Methods 0.000 claims description 13
- 238000000354 decomposition reaction Methods 0.000 claims description 6
- 239000002244 precipitate Substances 0.000 claims description 5
- 101710178392 Angiotensin-converting enzyme inhibitory peptide Proteins 0.000 claims description 3
- 108090000765 processed proteins & peptides Proteins 0.000 description 24
- 102000004142 Trypsin Human genes 0.000 description 22
- 108090000631 Trypsin Proteins 0.000 description 22
- 239000012588 trypsin Substances 0.000 description 22
- 102000011632 Caseins Human genes 0.000 description 21
- 108010076119 Caseins Proteins 0.000 description 21
- 230000000694 effects Effects 0.000 description 20
- 239000006228 supernatant Substances 0.000 description 14
- UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 description 9
- 101000984728 Chiropsoides quadrigatus Angiotensin-converting enzyme inhibitory peptide Proteins 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 9
- 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 9
- 230000002401 inhibitory effect Effects 0.000 description 8
- 102000004196 processed proteins & peptides Human genes 0.000 description 8
- 102000004190 Enzymes Human genes 0.000 description 7
- 108090000790 Enzymes Proteins 0.000 description 7
- 238000002835 absorbance Methods 0.000 description 7
- 229940088598 enzyme Drugs 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 6
- 229930014626 natural product Natural products 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 230000036772 blood pressure Effects 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 230000003276 anti-hypertensive effect Effects 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- -1 milk Chemical compound 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 102000015427 Angiotensins Human genes 0.000 description 3
- 108010064733 Angiotensins Proteins 0.000 description 3
- 206010020772 Hypertension Diseases 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 229940030600 antihypertensive agent Drugs 0.000 description 3
- 239000002220 antihypertensive agent Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000011033 desalting Methods 0.000 description 2
- 230000001079 digestive effect Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000001077 hypotensive effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000036454 renin-angiotensin system Effects 0.000 description 2
- 235000020183 skimmed milk Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- 239000005541 ACE inhibitor Substances 0.000 description 1
- GIQZFLZPSASIEJ-UHFFFAOYSA-N Ala-Val-Pro-Tyr-Pro-Gln-Arg Natural products CC(N)C(=O)NC(C(C)C)C(=O)N1CCCC1C(=O)NC(C(=O)N1C(CCC1)C(=O)NC(CCC(N)=O)C(=O)NC(CCCN=C(N)N)C(O)=O)CC1=CC=C(O)C=C1 GIQZFLZPSASIEJ-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 101000761020 Dinoponera quadriceps Poneritoxin Proteins 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 108010019160 Pancreatin Proteins 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- RKDYKIHMFYAPMZ-INIZCTEOSA-N ac1mbmqr Chemical compound N([C@@H](CCCN=C(N)N)C(=O)NC=1C=CC(=CC=1)[N+]([O-])=O)C(=O)C1=CC=CC=C1 RKDYKIHMFYAPMZ-INIZCTEOSA-N 0.000 description 1
- 235000013334 alcoholic beverage Nutrition 0.000 description 1
- 150000001413 amino acids Chemical group 0.000 description 1
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000004531 blood pressure lowering effect Effects 0.000 description 1
- 238000009530 blood pressure measurement Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229960005069 calcium Drugs 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229960000830 captopril Drugs 0.000 description 1
- 230000000963 caseinolytic effect Effects 0.000 description 1
- 229940021722 caseins Drugs 0.000 description 1
- 239000007910 chewable tablet Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000020247 cow milk Nutrition 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000007938 effervescent tablet Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 230000007071 enzymatic hydrolysis Effects 0.000 description 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007941 film coated tablet Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 235000021552 granulated sugar Nutrition 0.000 description 1
- 235000013402 health food Nutrition 0.000 description 1
- 238000003505 heat denaturation Methods 0.000 description 1
- 230000000415 inactivating effect Effects 0.000 description 1
- 238000001155 isoelectric focusing Methods 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 235000021056 liquid food Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 229940055695 pancreatin Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000016160 smooth muscle contraction Effects 0.000 description 1
- 239000003998 snake venom Substances 0.000 description 1
- 229940080237 sodium caseinate Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000021055 solid food Nutrition 0.000 description 1
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 1
- 235000011496 sports drink Nutrition 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 230000035488 systolic blood pressure Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 235000008939 whole milk Nutrition 0.000 description 1
- 235000013618 yogurt Nutrition 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63173393A JPH0223885A (ja) | 1988-07-12 | 1988-07-12 | ペプチドの取得方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63173393A JPH0223885A (ja) | 1988-07-12 | 1988-07-12 | ペプチドの取得方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0223885A JPH0223885A (ja) | 1990-01-26 |
| JPH0516836B2 true JPH0516836B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-03-05 |
Family
ID=15959572
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63173393A Granted JPH0223885A (ja) | 1988-07-12 | 1988-07-12 | ペプチドの取得方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0223885A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112662724B (zh) * | 2021-01-20 | 2023-04-28 | 重庆市药物种植研究所 | 一种鹿血多肽及其提取方法、应用 |
-
1988
- 1988-07-12 JP JP63173393A patent/JPH0223885A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0223885A (ja) | 1990-01-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4369985B2 (ja) | アンジオテンシン変換酵素阻害ペプチド | |
| JP3068656B2 (ja) | 新規なペプチド及びアンジオテンシン変換酵素阻害ペプチド並びにそれらを含有する経口摂食組成物 | |
| JP5417405B2 (ja) | アンジオテンシン変換酵素阻害性降圧ペプチド組成物の製造方法 | |
| WO2004002509A2 (fr) | Utilisation de peptides de la caseine pour traiter l’hypertension | |
| JP2010155788A (ja) | 新規トリペプチドおよびそれらトリペプチドの製造法、ならびにアンジオテンシン変換酵素阻害物質の製造方法 | |
| JPH04282400A (ja) | アンジオテンシン変換酵素阻害ペプチド組成物 | |
| WO2014002571A1 (ja) | アンジオテンシン変換酵素阻害ジペプチド | |
| JPWO2005061529A1 (ja) | アンジオテンシン変換酵素阻害ペプチド | |
| JPH02154693A (ja) | 機能性新規ペプチド及びその利用 | |
| JP2003026597A (ja) | 抗骨粗鬆症作用を発揮する骨量増進組成物 | |
| KR100653582B1 (ko) | 신규 펩티드 ｙ-2 | |
| JP5456100B2 (ja) | アンジオテンシン変換酵素阻害ジペプチド | |
| JPH0516836B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| JPH0521092B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| EA017609B1 (ru) | Применение гидролизата казеина молока животных и продукта ферментации исходного материала, содержащего молочный белок, включающих ile-pro-pro и/или val-pro-pro, в производстве профилактического средства от артериосклероза | |
| JPH0458947B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| KR101491902B1 (ko) | 콜라게나제의 활성 저해 효과를 갖는 신규 펩타이드 및 그의 용도 | |
| JP5456144B1 (ja) | アンジオテンシン変換酵素阻害ジペプチド | |
| JP2001106699A (ja) | 新規なヘクサペプチドおよびアンジオテンシン変換酵素阻害剤 | |
| JP3972104B2 (ja) | 新規なヘクサペプチド及びアンジオテンシン変換酵素阻害剤 | |
| JP2001106698A (ja) | 新規なテトラペプチドおよびアンジオテンシン変換酵素阻害剤 | |
| JP3031693B2 (ja) | アンギオテンシン変換酵素阻害剤含有組成物の製造方法 | |
| JP2990354B1 (ja) | 新規なペンタペプチドおよびアンジオテンシン変換酵素阻害剤 | |
| JP3108920B1 (ja) | 新規なテトラペプチドおよびアンジオテンシン変換酵素阻害剤 | |
| JP2920829B1 (ja) | 新規なペンタペプチドおよびアンジオテンシン変換酵素阻害剤 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313113 |
|
| R371 | Transfer withdrawn |
Free format text: JAPANESE INTERMEDIATE CODE: R371 |
|
| S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313113 |
|
| R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
| S202 | Request for registration of non-exclusive licence |
Free format text: JAPANESE INTERMEDIATE CODE: R315201 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20080305 Year of fee payment: 15 |
|
| R360 | Written notification for declining of transfer of rights |
Free format text: JAPANESE INTERMEDIATE CODE: R360 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20080305 Year of fee payment: 15 |
|
| S202 | Request for registration of non-exclusive licence |
Free format text: JAPANESE INTERMEDIATE CODE: R315201 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20080305 Year of fee payment: 15 |
|
| R370 | Written measure of declining of transfer procedure |
Free format text: JAPANESE INTERMEDIATE CODE: R370 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20080305 Year of fee payment: 15 |
|
| R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20090305 Year of fee payment: 16 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20090305 Year of fee payment: 16 |
|
| S533 | Written request for registration of change of name |
Free format text: JAPANESE INTERMEDIATE CODE: R313533 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20090305 Year of fee payment: 16 |
|
| R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
| EXPY | Cancellation because of completion of term | ||
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20090305 Year of fee payment: 16 |