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Opioid antagonist peptides derived from κ-casein

  • Hideo Chiba (a1), Fumito Tani (a1) and Masaaki Yoshikawa (a1)

Opioid antagonists were sought in the fragments of κ-casein which were obtained by chemical synthesis and enzymic digestion. A synthetic bovine κ-casein peptide (35–41), Tyr-Pro-Ser-Tyr-Gly-Leu-Asn (casoxin A) showed opioid antagonist activity at 200 μM in the guinea pig ileum assay. A synthetic peptide Tyr-Pro-Tyr-Tyr (casoxin B) which is found in bovine and human κ-casein, also showed opioid antagonist activity at 100 μM. Another opioid antagonist peptide (casoxin C) was isolated from tryptic digests of bovine κ-casein by reverse-phase HPLC. The structure of the peptide was Tyr-Ile-Pro-Ile-Gln-Tyr-Val-Leu-Ser-Arg, which corresponded to κ-casein (25–34). Casoxin C was active at 5 μM in the guinea pig ileum assay. Thus, bovine κ-casein contains three potential opioid antagonist sequences.

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Berthou, J., Migliore-Samour, D., Lifchitz, A., Delettré, J., Floc'H., F. & Jollés, P. 1987 Immunostimulating properties and three-dimensional structure of two tripeptides from human and cow caseins. FEBS Letters 218 5558
Brantl, V., Teschemacher, H., Henschen, A. & Lottspeich, F. 1979 Novel opioid peptides derived from casein (β-casomorphins), I. Isolation from bovine casein peptone. Hoppe-Seyler's Zeitschrift für Physiologische Chemie 360 12111216
Brignon, G., Chtourou, A. & Ribadeau-Dumas, B. 1985 Preparation and amino acid sequence of human κ-casein. FEBS Letters 188 4854
Chiba, H. & Yoshikawa, M. 1986 Biologically functional peptides from food proteins: New opioid peptides from milk proteins. In Protein Tailoring for Food and Medical Uses pp. 123153 (eds Feeney, R. E. and Whitaker, J. R.). New York: Marcel Dekker
Henschen, A., Lottspeich, F., Brantl, V. & Teschemacher, H. 1979 Novel Opioid peptide derived from casein β-casomorphins). II. Structure of active components from bovine casein peptone. Hoppe-Seyler's Zeitschrift für Physiologische Chemie 360 12171224.
Loukas, S., Varoucha, D., Zioudrou, G., Streaty, R. A. & Klee, W. A. 1983 Opioid activities and structures of α-casein-derived exorphins. Biochemistry 22 45674573
Maruyama, S., Nakagomi, K., Tomizuka, N. & Suzuki, H. 1985 Angiotensin I converting enzyme inhibitor derived from an enzymatic hydrolysate of casein. II. Isolation and bradykinin-potentiating activity on the uterus and the ileum of rats. Agricultural and Biological Chemistry 49 14051409
Maruyama, S. & Suzuki, H. 1982 A peptide inhibitor of angiotensin I converting enzyme inhibitor in the tryptic hydrolysate of casein. Agricultural and Biological Chemistry 46 13931394
Mercier, J.-C., Brignon, G. & Ribadeau-Dumas, B. 1973 Structure primaire de la caséine κB bovine, Sequence complete. European Journal of Biochemistry 35 222235
Parker, F., Migliore-Samour, D., Floc'H, F., Zerial, A., Werner, G. H., Jollès, J., Casaretto, M., Zahn, H. & Jollès, P. 1984 Immunostimulating hexapeptide from human casein: amino acid sequence, synthesis and biological properties. European Journal of Biochemistry 145 677682
Yoshikawa, M., Tani, F., Ashikaga, T., Yoshimara, T. & Chiba, H. 1986 b Purification and characterization of an opioid antagonist from peptic: digest of bovine κcasein. Agricultural and Biological Chemistry 50 29512954
Yoshikawa, M., Tani, F. & Chiba, H. 1988 Structure-activity relationship of opioid antagonist peptides derived from milk proteins. In Peptide Chemistry 1987 pp. 473476 (Ed. Shiba, T.). Osaka: Protein Research Foundation
Yoshikawa, M., Tani, F., Yoshimura, T. & Chiba, H. 1986 a Opioid peptides from milk proteins. Agricultural and Biological Chemistry 50 24192421
Yoshikawa, M., Yoshimura, T. & Chiba, H. 1984 Opioid peptides from human β-casein. Agricultural and Biological Chemistry 48 31853187
Zioudrou, C., Streaty, R. A. & Klee, W. A. 1979 Opioid peptides derived from food proteins, the exorphins. Journal of Biological Chemistry 254 24462449
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Journal of Dairy Research
  • ISSN: 0022-0299
  • EISSN: 1469-7629
  • URL: /core/journals/journal-of-dairy-research
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