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List of peptide properties
DFBP ID - DFBPOPIO0001(Opioid peptide)
DFBP ID DFBPOPIO0001
Peptide sequence RYLGYLE
Type Native peptide
Peptide/Function name Opioid peptide, αs1-Casein-exorphin [2]
Function-activity relationship
Main bioactivity Opioid activity
Otheir bioactivity N.D
Calculated physicochemical properties
Three-letter amino acid Arg-Tyr-Leu-Gly-Tyr-Leu-Glu
Single-letter amino acid RYLGYLE
Peptide length 7
Peptide mass
Experimental mass Theoretical mass
913.04 Da 913.03 Da c
Net charge

0.0

Isoelectric point (pI)

7.4

IC50 N.D
pIC50 N.D
GRAVY -0.4857 c
Hydrophilic residue ratio 42.86% c
Peptide calculator
To calculate the physicochemical properties of bioactive peptide.
Peptide source & Food-borne protein(s) search
Classification Animal
Organism/Source Bovine milk protien [2]
Precursor protein αs1-Casein
Residue position f(90-96)
Precursor protein(s) search
Link-research
There are no literature reports on the discovery of this sequence in other food-source proteins.
Biological/Functional activity & target protein
Opioid activity RYLGYLE showed potent opioid activity in all three bioassays and its potency was similar to that of the isolated α-casein exorphins. As shown in table 1.
Table 1 Opioid activity of peptide
Peptide
Opiate assay (IC50, uM)/Activity
References
Displacement of [3H]DALAMID from rat brain membranes
Displacement of [3H]DHM from rat brain membranes
Inhibition of adenylate cyclase in homogenates of NG108-15 cells
Inhibition of electrically stimulated mouse vas deferens
Isolated α-casein exorphin a
3.8
0.3
11.0
RYLGYLE0.7
1.2
0.8
30.0
This peptide showed potently active as opioid agonist (IC50 = 1.2 umol/l) and has been characterized as δ-selective type ligand[2]
a Opioid peptides from pepsin hydrolysates of α-casein.
Specific target protein(s) Specific Target Protein(s):
Delta-type opioid receptor
Taste properties & Structure
Bitterness
Literature report N.D
Bitter prediction tools Bitter taste prediction
SMILES N[C@@]([H])(CCCNC(=N)N)C(=O)N[C@@]([H])(Cc1ccc(O)cc1)C(=O)N[C@@]([H])(CC(C)C)C(=O)NCC(=O)N[C@@]([H])(Cc1ccc(O)cc1)C(=O)N[C@@]([H])(CC(C)C)C(=O)N[C@@]([H])(CCC(=O)O)C(=O)O
Preparation method
Mode of preparation Enzymatic hydrolysis
Enzyme(s)/starter culture

Hydrolysis with pepsin.

Stability & Cytotoxicity
Peptide stability
Literature report:

The peptide was resistant to hydrolysis by trypsin and homogenates of rat brain membranes, but was partially inactivated by chymotrypsin and subtilisin.

EHP-Tool: Enzymatic Hydrolysis Prediction Tool (EHP-Tool)
Peptide cytotoxicity
Literature report: N.D
Prediction: ToxinPred
Additional information
Additional information N.D
Database cross-references
BIOPEP-UWM [D1] 3473
APD [D2] -
BioPepDB [D3] -
MBPDB [D4] -
Reference(s)
Primary literature Loukas S, Varoucha D, Zioudrou C, Streaty RA, Klee WA. Opioid activities and structures of alpha-casein-derived exorphins. Biochemistry. 1983 Sep 13;22(19):4567-73.
PMID: 6313043
Other literature(s)

[1] Park Y W. Bioactive Components in Milk and Dairy Products[M]. 2009.
[2] Meisel H, Fitzgerald R J. Opioid peptides encrypted in intact milk protein sequences.[J]. British Journal of Nutrition, 2000, 84(S1):27-31.
[3]Teschemacher H. Opioid receptor ligands derived from food proteins.[J]. Current Pharmaceutical Design, 2003, 9(16):-.
[4] Xu, Ruo‐Jun. Bioactive Peptides in Milk and their Biological and Health Implications[J]. Food Reviews International, 1998, 14(1):1-16.
[5] Hatzoglou A, Bakogeorgou E, Hatzoglou C, et al. Antiproliferative and receptor binding properties of α- and β-casomorphins in the T47D human breast cancer cell line[J]. European Journal of Pharmacology, 1996, 310(2–3):217-223.
[6] Kostyra E, Sienkiewiczszłapka E, Jarmołowska B, et al. Opioid peptides derived from milk proteins.[J]. Polish Journal of Food & Nutrition Sciences, 2004.
[7] Meisel H. Overview on Milk Protein-derived Peptides[J]. International Dairy Journal, 1998, 8(5–6):363-373.
[8] Schlimme E, Meisel H. Bioactive peptides derived from milk proteins. Structural, physiological and analytical aspects.[J]. Nahrung, 1995, 39(1):1-20.

PubDate 1983
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