| 编号: | 431660 |
| 中文名称: | β-Casomorphin(1-8), bovine |
| 英文名: | β-Casomorphin(1-8), bovine |
| 单字母: | H2N-YPFPGPIP-OH |
| 三字母: | H2N N端氨基：N-terminal amino group。在肽或多肽链中含有游离a-氨基的氨基酸一端。在表示氨基酸序列时，通常将N端放在肽链的左边。 -TyrL-酪氨酸：tyrosine。系统命名为(2S)-氨基-3-(4-羟基苯基)丙酸。是编码氨基酸。符号：Y，Tyr。 -ProL-脯氨酸：proline。系统命名为吡咯烷-(2S)-羧酸。为亚氨基酸。是编码氨基酸。在肽链中有特殊作用，如易形成顺式的肽键等。符号：P，Pro。 -PheL-苯丙氨酸：phenylalanine。系统命名为(2S)-氨基-3-苯基丙酸。是编码氨基酸。是哺乳动物的必需氨基酸。符号：F，Phe。 -ProL-脯氨酸：proline。系统命名为吡咯烷-(2S)-羧酸。为亚氨基酸。是编码氨基酸。在肽链中有特殊作用，如易形成顺式的肽键等。符号：P，Pro。 -Gly甘氨酸：glycine。系统命名为 2-氨基乙酸。是编码氨基酸中没有旋光性的最简单的氨基酸，因具有甜味而得名。符号：G，Gly。 -ProL-脯氨酸：proline。系统命名为吡咯烷-(2S)-羧酸。为亚氨基酸。是编码氨基酸。在肽链中有特殊作用，如易形成顺式的肽键等。符号：P，Pro。 -IleL-异亮氨酸：isoleucine。系统命名为(2S)-氨基-(3R)-甲基戊酸。是编码氨基酸。有两个手性碳原子，是哺乳动物的必需氨基酸。符号:I，Ile。 -ProL-脯氨酸：proline。系统命名为吡咯烷-(2S)-羧酸。为亚氨基酸。是编码氨基酸。在肽链中有特殊作用，如易形成顺式的肽键等。符号：P，Pro。 -OHC端羧基：C-terminal carboxyl group。在肽或多肽链中含有游离羧基的氨基酸一端。在表示氨基酸序列时，通常将C端放在肽链的右边。 |
| 氨基酸个数: | 8 |
| 分子式: | C46H62N8O10 |
| 平均分子量: | 887.03 |
| 精确分子量: | 886.46 |
| 等电点(PI): | - |
| pH=7.0时的净电荷数: | 1.97 |
| 平均亲水性: | -2.5666666666667 |
| 疏水性值: | -0.05 |
| 消光系数: | 1490 |
| 标签: | 酪啡肽(β-Casomorphin) |
酪啡肽(β-Casomorphin)的定义
β-酪啡肽是由β-酪蛋白消化产生的肽，长度为 4-11 个氨基酸。 它们表现出阿片类药物或吗啡样功能。
酪啡肽(β-Casomorphin)的发现
β-酪啡肽首先从豚鼠回肠的酪蛋白消化物中纯化，基于其显示阿片类活性的能力。
酪啡肽(β-Casomorphin)的分类
ß-酪啡肽是阿片肽。已鉴定出几种天然存在的β-酪啡肽 (BCM)：牛 BCM-4、牛 BCM-5、牛 BCM-6、牛 BCM-7、牛 BCM-8、牛 BCM-11、人 BCM-7、人 BCM-8 。 已经合成了几种类似物，它们是天然存在的 BCM 的结构修饰变体。
酪啡肽(β-Casomorphin)的结构特点
BCM 的长度为 4-11 个氨基酸。天然存在的 BCM 的序列如下1所示：
牛 BCM-4 Tyr-Pro-Phe-Pro
牛 BCM-5 Tyr-Pro-Phe-Pro-Gly
牛 BCM-6 Tyr-Pro-Phe-Pro-Gly-Pro
牛 BCM-7 Tyr-Pro-Phe-Pro-Gly-Pro-Ile
牛 BCM-8 Tyr-Pro-Phe-Pro-Gly-Pro-Ile-Pro
牛 BCM-11 Tyr-Pro-Phe-Pro-Gly-Pro-Ile-Pro-Asn-Ser-Leu
人 BCM-7 Tyr-Pro-Phe-Val-Glu-Pro-Ile
人 BCM-8 Tyr-Pro-Phe-Val-Glu-Pro-Ile-Pro
BCM类似物的一些序列如下所示：
H-Tyr-Pro-Phe-Pro-Gly-EtDA-Gly-II
H-Tyr-Pro-Phe-Pro-Gly-EtDA-Gly-Gly-II
H-Tyr-Pro-Phe-Pro-Gly-EtDA-Gly-Gly-CO-CH3
H-Tyr-Pro-Phe-Pro-Gly-EtDA-Gly-Gly-CO-CH2-CH2-COOH
酪啡肽(β-Casomorphin)的作用方式
关于 BCM 功能的确切机制目前还没有太多研究。众所周知，它们通过与细胞膜上的阿片受体结合来发挥阿片功能。 最近的研究表明，BCM-7 是大脑中血管紧张素受体的高亲和力配体。
酪啡肽(β-Casomorphin)的功能
BCM 对胃肠道产生影响。 例如，它们通过刺激胰岛素和生长抑素的分泌来影响餐后代谢，并调节肠道中氨基酸的转移5。 影响缺氧，因为已经表明，当给怀孕大鼠施用 BCM7 时，可以诱导其从缺氧状态中恢复。 BCM-5 和类似物参与大鼠旋转行为的产生。 BCM-8 参与哺乳期间母亲和孩子之间的相互作用。 最后，BCM 与多种疾病有关，包括 SIDS 和儿童自闭症。
酪啡肽(β-Casomorphin)的相关文献
1、Kamiñski S, Cieoeliñska A, Kostyra E (2007). Polymorphism of bovine beta-casein and its potential effect on human health. J Appl Genet, 48(3), 189–198.
2、Ramabadran K, Bansinath M (1989). Pharmacology of beta-casomorphins, opioid peptides derived from milk protein. Asia Pac J Pharmacol, 4, 45–58.
3、Sobirov MM, Khalikov ShKh, Saidov SS, Kodirov MZ, Zaitsev SV, Chichenkov ON, Varfolomeev SD (1994). Synthesis and biological activity of new analogs of beta-casomorphine-5. Bioorg Khim., 20(7), 740-50.
4、Book: Handbook of Biologically Active Peptides by Abba J. Kastin.
5、Zoghbi S, Trompette A, Claustre J, Homsi ME, Garzo´n J, Jourdan G, Scoazec JY and Plaisancie P (2006). Casomorphin-7 regulates the secretion and expression of gastrointestinal mucins through a opioid pathway. Am J Physiol Gastrointest Liver Physiol 290, G1105–G1113.
6、Marschitz HM, Terenius L, Grehn L, Ungerstedt U (1989). Rotational behaviour produced by intranigral injections of bovine and human beta-casomorphins in rats. Psychopharmacology (Berl), 99(3), 357-61.
7、Ivano DN, Richard JF, Hannu JTK, Yves LR, Chris TL, Inga T, Daniel T, Renger W, (2009). Review of the potential health impact of ß-casomorphins and related peptides. EFSA Scientific Report, 231, 1-107.
Definition
Casomorphins are peptides resulting from the digestion of beta-Casein and vary from 4-11 amino acids in length1. They exhibit opioid or morphine-like functions1.
Discovery
Casomorphins were first purified from casein digest of guinea pig ileum based on their ability to show opioid activity2.
Classification
Casomorphins are opioid peptides1. The most commonly studied peptides are ß-Casomorphins (BCM) which are several in number: Bovine BCM-4, Bovine BCM-5, Bovine BCM-6, Bovine BCM-7, Bovine BCM-8, Bovine BCM-11, Human BCM-7, Human BCM-81.
Structural Characteristics
BCMs are 4-11 amino acids in length. The sequences of naturally occurring BCMs are given below1:
Bovine BCM-4 Tyr-Pro-Phe-Pro,
Bovine BCM-5 Tyr-Pro-Phe-Pro-Gly
Bovine BCM-6 Tyr-Pro-Phe-Pro-Gly-Pro
Bovine BCM-7 Tyr-Pro-Phe-Pro-Gly-Pro-Ile
Bovine BCM-8 Tyr-Pro-Phe-Pro-Gly-Pro-Ile-Pro
Bovine BCM-11 Tyr-Pro-Phe-Pro-Gly-Pro-Ile-Pro-Asn-Ser-Leu
Human BCM-7 Tyr-Pro-Phe-Val-Glu-Pro-Ile
Human BCM-8 Tyr-Pro-Phe-Val-Glu-Pro-Ile-Pro
Mode of action
The exact mechanism of BCM function is not known. They exert their opioid functions by binding to opioid receptors on cell membranes4. Recent studies have shown that BCM-7 is an high affinity ligand for angiotensin receptor in the brain4.
Functions
BCMs produce effects in the gastrointestinal tract. For instance they influence post prandial metabolism by stimulating the secretion of insulin and somatostatin and modulate transfer of amino acids in the intestine5. The affect hypoxia as it has been shown that BCM7 when administered to pregnant rats induces their recovery from hypoxic condition4. BCM-5 and analogs are involved in producing rotational behavior in rats6. BCM-8 is involved in interplay between mother and child during lactation7. Finally, BCMs have been implicated in several diseases including SIDS and childhood autism1.
References
1. Kamiñski S, Cieoeliñska A, Kostyra E (2007). Polymorphism of bovine beta-casein and its potential effect on human health. J Appl Genet, 48(3),189–198.
2. Ramabadran K, Bansinath M (1989). Pharmacology of beta-casomorphins, opioid peptides derived from milk protein. Asia Pac J Pharmacol, 4, 45–58.
3. Sobirov MM, Khalikov ShKh, Saidov SS, Kodirov MZ, Zaitsev SV, Chichenkov ON, Varfolomeev SD (1994). Synthesis and biological activity of new analogs of beta-casomorphine-5. Bioorg Khim., 20(7), 740-50.
4. Book: Handbook of Biologically Active Peptides by Abba J. Kastin.
5. Zoghbi S, Trompette A, Claustre J, Homsi ME, Garzo´n J, Jourdan G, Scoazec JY and Plaisancie P (2006). Casomorphin-7 regulates the secretion and expression of gastrointestinal mucins through a opioid pathway. Am J Physiol Gastrointest Liver Physiol, 290, G1105–G1113.
6. Marschitz HM, Terenius L, Grehn L, Ungerstedt U (1989). Rotational behaviour produced by intranigral injections of bovine and human beta-casomorphins in rats. Psychopharmacology (Berl)., 99(3), 357-61.
7. Ivano DN, Richard JF, Hannu JTK, Yves LR, Chris TL, Inga T, Daniel T, Renger W, (2009). Review of the potential health impact of ß-casomorphins and related peptides. EFSA Scientific Report, 231, 1-107.
