Quantitation and sensory properties of three newly identified pyroglutamyl oligopeptides in sake

References

• Iwaniak A, Minkiewicz P, Darewicz M, et al. Food protein-originating peptides as tastants - Physiological, technological, sensory, and bioinformatics approaches. Food Res Int. 2016;89:27–38.
   PubMed Web of Science ®Google Scholar
• Zhao CJ, Schieber A, Gänzle MG. Formation of taste-active amino acids, amino acid derivatives and peptides in food fermentation – A review. Food Res Int. 2016;89:39–47.
   PubMed Web of Science ®Google Scholar
• Zhang Y, Venkitasamy C, Pan Z, et al. Novel umami ingredients: umami peptides and their taste. J Food Sic. 2017;82:16–23.
   PubMed Web of Science ®Google Scholar
• Maehashi K, Huang L. Bitter peptides and bitter taste receptors. Cell Mol Life Sci. 2009;66:1661–1671.
   PubMed Web of Science ®Google Scholar
• Martínez-Maqueda D, Miralles B, Recio I, et al. Antihypertensive peptides from food proteins: a review. Food Funct. 2012;3:350–361.
   PubMed Web of Science ®Google Scholar
• Hashizume K, Okuda M, Numata M, et al. Bitter-tasting sake peptides derived from the N-terminus of the rice glutelin acidic subunit. Food Sci Technol Res. 2007;13:270–274.
   Web of Science ®Google Scholar
• Kaneko S, Kumazawa K, Nishimura O. Isolation and identification of the umami enhancing compounds in Japanese soy sauce. Biosci Biotechnol Biochem. 2011;75:1275–1282.
   PubMed Web of Science ®Google Scholar
• Hshizume K, Ito T, Shimohashi M, et al. Taste-guided fractionation and instrumental analysis of hydrophobic compounds in sake. Biosci Biotechnol Biochem. 2012;76:1291–1295.
   PubMed Web of Science ®Google Scholar
• Miyamura N, Iida Y, Kuroda M, et al. Determination and quantification of kokumi peptide,γ-glutamyl-valyl-glycine, in brewed alcoholic beverages. J Biosci Bioeng. 2015;120:311–314.
   PubMed Web of Science ®Google Scholar
• Hshizume K, Ito T, Igarashi S. Quantitation using a stable isotope dilution assay (SIDA) and thresholds of taste-active pyroglutamyl decapeptide ethyl esters (PGDPEs) in sake. Biosci Biotechnol Biochem. 2017;81:426–430.
   PubMed Web of Science ®Google Scholar
• Saito Y, Wanezaki(Nakamura) K, Kawato A, et al. Structure and activity of angiotensin I converting enzyme inhibitory peptides from sake and sake lees. Biosci Biotechnol Biochem. 1994;58:1767–1771.
   PubMed Web of Science ®Google Scholar
• Saito Y, Ohura S, Kawato A, et al. Prolyl endopeptidase inhibitors in sake and its byproducts. J Agric Food Chem. 1997;45:720–724.
   Web of Science ®Google Scholar
• Kiyono T, Hirooka K, Yamamoto Y, et al. Identification of pyroglutamyl peptides in Japanese rice wine (sake): presence of hepatoprotective pyroGlu-Leu. J Agric Food Chem. 2013;61:11660–11667.
   PubMed Web of Science ®Google Scholar
• Wada S, Sato K, Ohta R, et al. Ingestion of low dose pyroglutamyl leucine improves dextran sulfate sodium-induced colitis and intestinal microbiota in mice. J Agric Food Chem. 2013;61:8807–8813.
   PubMed Web of Science ®Google Scholar
• Kiyono T, Wada S, Ohta R, et al. Identification of pyroglutamyl peptides with anti-colitic activity in Japanese rice wine, sake, by oral administration in a mouse model. J Functional Foods. 2016;27:612–621.
   Web of Science ®Google Scholar
• Hirano H, Komatsu S, Nakamura A, et al. Structural homology between semidwarfism-related proteins and glutelin seed protein in rice (Oryza sativa L.). Theor Appl Genet. 1991;83:153–158.
   PubMed Web of Science ®Google Scholar
• Komatsu S, Kajiwara H, Hirano H. A rice protein library: a data-file of rice proteins separated by two-dimensional electrophoresis. Theor Appl Genet. 1993;86:935–942.
   PubMed Web of Science ®Google Scholar
• Hashizume K, Okuda M, Numata M, et al. Characterization of peptides generated in proteolytic digest of steamed rice grains by sake koji enzymes. J Biosci Bioeng. 2007;104:251–256.
   PubMed Web of Science ®Google Scholar
• Maeda Y, Okuda M, Hashizume K, et al. Analysis of peptides in sake mash: forming a profile of bitter-tasting peptides. J Biosci Bioeng. 2011;112:238–246.
   PubMed Web of Science ®Google Scholar
• Okuda M, Joyo M, Tamamoto Y, et al. Analysis of protein composition in rice cultivar used for sake brewing, and effects on nitrogen compounds in sake. Cereal Chem. 2018;95:320–329.
   Web of Science ®Google Scholar
• Kim TY, Brun YV, Reilly JP. Effects of tryptic peptide esterification in MALDI mass spectrometry. Anal Chem. 2005;77:4185–4193.
   PubMed Web of Science ®Google Scholar
• Suzuki N, Ito T, Hiroshima K, et al. Formation of ethyl ferulate from feruloylated oligosaccharide by transesterification of rice koji enzyme under sake mash conditions. J Biosci Bioeng. 2016;121:281–285.
   PubMed Web of Science ®Google Scholar
• Brewery Convention of Japan. BCOJ Kanno Hyoka Ho. Threshold of added substances. Tokyo: Nippon Jozo Kyokai; 2002.
   Google Scholar
• Isogai A, Kanda R, Sudo S, et al. Quantitation of the DMTS precursor, 1,2-dihydroxy-5-(methylsulfinyl) pentane-3-one (DMTS-P1) in alcoholic beverages and fermented solutions by a stable isotope dilution analysis. J Brew Soc Japan. 2013;108:605–614.
   Google Scholar
• Takahashi K, Tokuoka M, Kohno H, et al. Comprehensive analysis of dipeptides in alcoholic beverages by tag-based separation and determination using liquid chromatography/electrospray ionization tandem mass spectrometry and quadrupole-time-of-flight mass spectrometry. J Chromatogr. 2012;1242:17–25.
   PubMed Web of Science ®Google Scholar
• Mazur RH, Schlatter JM, Goldkamp AH. Structure-taste relationships of some dipeptides. J Am Chem Soc. 1969;91:2684–2691.
   PubMed Web of Science ®Google Scholar
• Matoba T, Hata T. Relationship between bitterness of peptides and their chemical structures. Agric Biol Chem. 1972;36:1423–1431.
   Web of Science ®Google Scholar
• Kim HO, Li-Chan ECY. Quantitative structure-activity relationship study of bitter peptides. J Agric Food Chem. 2006;54:10102–10111.
   PubMed Web of Science ®Google Scholar
• Otagiri K, Nosho Y, Shinoda I, et al. Studies on a model of bitter peptides including arginine, proline and phenylalanine residues. I. Bitter taste of di- and tripeptides, and bitterness increase of the model peptides by extension of the peptide chain. Agric Biol Chem. 1985;49:1019–1026.
   Web of Science ®Google Scholar
• Takahashi K, Tadenuma M, Kitamoto K, et al. L-Prolyl-L-leucine anhydride. A bitter compound formed in aged sake. Agric Biol Chem. 1974;38:927–932.
   Web of Science ®Google Scholar
• Takeuchi M, Ichishima E. Mode of action of a new Aspergillus oryzae carboxypeptidase O-1. Agric Biol Chem. 1981;45:1033–1035.
   Web of Science ®Google Scholar
• Takeuchi M, Ichishima EA. 155K acid carboxypeptidase O from Aspergillus oryzae. Agric Biol Chem. 1986;50:633–638.
   Web of Science ®Google Scholar