The DOI matches its Crossref record; 13 of the 13 references it cites were found in a registry or an index.
Opioid peptides derived from wheat gluten: their isolation and characterization.
Abstract
Four opioid peptides were isolated from the enzymatic digest of wheat gluten. Their structures were Gly‐Tyr‐Tyr‐Pro‐Thr, Gly‐Tyr‐Tyr‐Pro,Tyr‐Gly‐Gly‐Trp‐Leu and Tyr‐Gly‐Gly‐Trp, which were named gluten exorphins A5, A4, B5 and B4, respectively. The gluten exorphin A5 sequence was found at 15 sites in the primary structure of the high molecular weight glutenin and was highly specific for δ‐receptors. The structure—activity relationships of gluten exorphins A were unique in that the presence of Gly at their N‐termini increased their activities. Gluten exorphin B5, which corresponds to [Trp 4,Leu 5]enkephalin, showed the most potent activity among these peptides. Its IC 50 values were 0.05 μM and 0.017 μM, respectively, on the GPI and the MVD assays.
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In the citing paper
“opioid peptides (i.e., gluten exorphins A4, A5, B4, B5, and C), have been detected and characterized in wheat gluten since 1992 (Fukudome and Yoshikawa, 1992).”
From Bioactive Molecules Released in Food by Lactic Acid Bacteria: Encrypted Peptides and Biogenic Amines (2016) · cites this paper as Fukudome and Yoshikawa, 1992
In the citing paper
“It has long been established that wheat gluten is a good source of opioid peptides (Fukudome and Yoshikawa, 1992)”
From Bioactive Molecules Released in Food by Lactic Acid Bacteria: Encrypted Peptides and Biogenic Amines (2016) · cites this paper as Fukudome and Yoshikawa, 1992
Citations
Cites
Properties of Opiate-Receptor Binding in Rat Brain
Pert, C. B., & Snyder, S. H. (1973) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.70.8.2243 · Cited by 440
Opioid peptides derived from food proteins. The exorphins
Zioudrou, C., Streaty, R. A., & Klee, W. A. (1979) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(17)30243-0 · Cited by 379
A wheat HMW glutenin subunit gene reveals a highly repeated structure
Sugiyama, T., Rafalski, A. J., Peterson, D. M., et al. (1985) · Nucleic Acids Research · doi:10.1093/nar/13.24.8729 · Cited by 159
Structure of wheat gamma-gliadin genes
Rafalski, J. A. (1986) · Gene · doi:10.1016/0378-1119(86)90210-6 · Cited by 110
Developmentally regulated plant genes: the nucleotide sequence of a wheat gliadin genomic clone.
Rafalski, J. A., Scheets, K., Metzler, M., et al. (1984) · The EMBO Journal · doi:10.1002/j.1460-2075.1984.tb01985.x · Cited by 106
Effect of exorphins on gastrointestinal function, hormonal release, and appetite
Morley, J. E., Levine, A. S., Yamada, T., et al. (1983) · Gastroenterology · doi:10.1016/0016-5085(83)90374-8 · Cited by 94
Shewry, P. R., Autran, J., Nimmo, C. C., et al. (1980) · Nature · doi:10.1038/286520a0 · Cited by 85
β-Casomorphin immunoreactive materials in cows' milk incubated with various bacterial species
Hamel, U., Kielwein, G., & Teschemacher, H. (1985) · Journal of Dairy Research · doi:10.1017/s0022029900023967 · Cited by 65
Demonstration of high opioid-like activity in isolated peptides from wheat gluten hydrolysates
Huebner, F. R., Lieberman, K. W., Rubino, R. P., et al. (1984) · Peptides · doi:10.1016/0196-9781(84)90180-3 · Cited by 56
Identification of barley and wheat cDNA clones related to the high‐Mr polypeptides of wheat gluten
Forde, J., Forde, B., Fry, R. P., et al. (1983) · FEBS Letters · doi:10.1016/0014-5793(83)80788-1 · Cited by 40
Cited by
Bioactive Molecules Released in Food by Lactic Acid Bacteria: Encrypted Peptides and Biogenic Amines
Pessione, E., & Cirrincione, S. (2016) · Frontiers in Microbiology · doi:10.3389/fmicb.2016.00876 · Cited by 333
Rubiscolin, a δ selective opioid peptide derived from plant Rubisco.
Yang, S., Yunden, J., Sonoda, S., Doyama, N., Lipkowski, A. W., Kawamura, Y., & Yoshikawa, M. (2001) · FEBS Letters · doi:10.1016/s0014-5793(01)03042-3 · Cited by 102
Self-citationHirata, H., Sonoda, S., Agui, S., Yoshida, M., Ohinata, K., & Yoshikawa, M. (2007) · Peptides · doi:10.1016/j.peptides.2007.07.024 · Cited by 89
Self-citationArtemova, N. V., Bumagina, Z. M., Kasakov, A. S., Shubin, V. V., & Gurvits, B. Y. (2010) · Peptides · doi:10.1016/j.peptides.2009.11.025 · Cited by 20
Fanciulli, G., Dettori, A., Demontis, M. P., Tomasi, P. A., Anania, V., & Delitala, G. (2005) · Life Sciences · doi:10.1016/j.lfs.2004.09.023 · Cited by 17
Metadata
- Authors
- Fukudome, S.-I., & Yoshikawa, M.
- Affiliations
- Kyoto University (JP)
- Corresponding author
- Yoshikawa, Masaaki
- ORCID
- Yoshikawa, Masaaki
- Venue
- FEBS Letters
- Publisher
- Wiley
- Published
- 1992-01-13
- Volume
- 296
- Issue
- 1
- Pages
- 107-111
- ISSN
- 0014-5793 (ISSN-L)
- 1873-3468
- OpenAlex
- W2093645202
- Cited by
- 142
- References
- 13
- Citations by year
- 2026: 2 · 2025: 2 · 2024: 1 · 2023: 2 · 2022: 3 · 2021: 2 · 2020: 12 · 2019: 3 · 2018: 3 · 2017: 3 · 2016: 3 · 2015: 7 · 2014: 4 · 2013: 5 · 2012: 8
- FWCI
- 1.50
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- FEBS Letters (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Neuroscience › Cellular and Molecular Neuroscience › Neuropeptides and Animal Physiology
- Life Sciences › Agricultural and Biological Sciences › Food Science › Protein Hydrolysis and Bioactive Peptides
- Physical Sciences › Chemistry › Organic Chemistry › Chemical Synthesis and Analysis
- Keywords
- opioid peptides, wheat gluten, exorphins, glutenin, delta opioid receptor, structure-activity relationship, enkephalin, peptide isolation, enzymatic digestion
- MeSH terms
- Amino Acid Sequence, Chromatography, High Pressure Liquid, Chymotrypsin, Glutens, Molecular Sequence Data, Pepsin A, Peptides, Radioligand Assay, Receptors, Opioid, Sequence Homology, Nucleic Acid, Substrate Specificity, Thermolysin, Trypsin, Triticum, Receptors, Opioid, delta
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Bibliographic data: Semantic Scholar, OpenAlex, Crossref.
Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
