2,5-diketopiperazines in food and beverages: Taste and bioactivity

References

• Aninat, C., Hayashi, Y., Andre, F. and Delaforge, M. (2001). Molecular requirements for inhibition of cytochrome P450 activities by roquefortine. Chem. Res. Toxicol. 14:1259–1265.
   PubMed Web of Science ®Google Scholar
• Aninat, C., André, F. and Delaforge, M. (2005). Oxidative metabolism by P450 and function coupling to efflux systems: modulation of mycotoxin toxicity. Food Addit. Contam. 22:361–368.
   PubMed Web of Science ®Google Scholar
• Aniya, Y., Ohtani, I. I., Higa, T., Miyagi, C., Gibo, H., Shimabukuro, M., Nakanishi, H. and Taira. (2000). J. Free Rad. Biol. Med. 28:999–1004.
   Google Scholar
• Anonymous. (1980). Aspartame: availability of board inquiry decision. Fed. Reg. 45:69558.
   Google Scholar
• Anteunis, M. J. O. (1978). The cyclic dipeptides. Proper model compounds in peptide research. Bull. Soc. Chim. Belges. 87:627–650.
   Google Scholar
• Ben Ameur Mehdi, R., Shaaban, K. A., Rebai, I. K., Smaoui, S., Bejar, S. and Mellouli, L. (2009). Five naturally bioactive molecules including two rhamnopyranoside derivatives isolated from the Streptomyces sp. strain TN58. Nat. Prod. Res. 23:1095–1107.
   PubMed Web of Science ®Google Scholar
• Bertinetti, B. V., Peña, N. I. and Cabrera, G. M. (2009). An antifungal tetrapeptide from the culture of Penicillium canescens. Chem. Biodivers. 6:1178–1184.
   PubMed Web of Science ®Google Scholar
• Birkenshaw, J. H. and Mohammed, Y. S. (1962). Studies in the biochemistry of micro-organisms. III. The production of l-phenylalanine anhydride (cis-l-3,6-dibenzyl-2,5-dioxopiperazine) by penicillium nigricans (bainier) thom. Biochem. J. 85:523–528.
   PubMed Web of Science ®Google Scholar
• Bobylev, M. M., Bobyleva, L. I., Cutler, H. G., Cutler, S. J. and Strobel, G. A. (1999). Growth regulating activity of maculosin analogs in the etiolated wheat coleoptile bioassay (Triticum aestivum L. cv. Wakeland). PGRSA Q. 27:105–118.
   Google Scholar
• Borthwick, A. D. (2012). 2,5-Diketopiperazines: synthesis, reactions, medicinal chemistry, and bioactive natural products. Chem. Rev. 112:3641–3716.
   PubMed Web of Science ®Google Scholar
• Bull, S. D., Davies, S. G., Parkin, R. M. and Sánchez-Sancho, F. (1998). The biosynthetic origin of diketopiperazines derived from D-proline. J. Chem. Soc., Perkin Trans. 1, 14:2313–2320
   Google Scholar
• Caballero, E., Avendaño, C. and Menéndez, J. C. (2003). Brief total synthesis of the cell cycle inhibitor tryprostatin B and related preparation of its alanine analogue. J. Org. Chem. 68:6944–6951.
   PubMed Web of Science ®Google Scholar
• Cabrera, G. M., Butler, M., Rodriguez, M. A., Godeas, A., Haddad, R. and Eberlin, M. N. (2006). A sorbicillinoid urea from an intertidal Paecilomyces marquandii. J. Nat. Prod. 69:1806–1808.
   PubMed Web of Science ®Google Scholar
• Cavelier, F., Giraud, M., Bernard, N. and Martinez, J. (2001). Original and general strategy of dimerization of bioactive molecules. In: Peptides: The Wave of the Future, pp. 152–155. Lebl, M., and Houghten, R. A., Ed., American Peptide Society, San Diego.
   Google Scholar
• Chen, G., Zhu, Y., Wang, H. Z., Wang, S. J. and Zhang, R. Q. (2007). The metabolites of a mangrove endophytic fungus, Penicillium thomi. J. Asian Nat. Prod. Res. 9:159–164.
   PubMed Web of Science ®Google Scholar
• Chen, G., Lin, Y., Vrijmoed, L. L. and Fong, W. F. (2006). A new isoChroman from the marine endophytic fungus 1893#. Chem. of Nat. Comp. 42:138–141.
   Web of Science ®Google Scholar
• Chen, J. H., Lan, X. P., Liu, Y. and Jia, A. Q. (2012). The effects of diketopiperazines from Callyspongia sp. on release of cytokines and chemokines in cultured J774A. 1 macrophages. Bioorg. Med. Chem. Lett. 22:3177–3180.
   PubMed Web of Science ®Google Scholar
• Chen, M. Z., Dewis, M. L., Kraut, K., Merritt, D., Reiber, L., Trinnaman, L. and Da Costa, N.C. (2009), 2, 5-Diketopiperazines (Cyclic Dipeptides) in beef: Identification, synthesis, and sensory evaluation. J. Food Sci. 74: C100–C105.
   PubMed Web of Science ®Google Scholar
• Chen, Y. H., Liou, S. E. and Chen, C. C. (2004). Two-step mass spectrometric approach for the identification of diketopiperazines in chicken essence. Eur. Food Res. Tech. 218:589–597.
   Web of Science ®Google Scholar
• Cho, J. Y., Kang, J. Y., Hong, Y. K., Baek, H. H., Shin, H. W. and Kim, M. S. (2012). Isolation and structural determination of the antifouling diketopiperazines from marine-derived Streptomyces praecox, 291–11. Biosci. Biotech. Biochem. 76:1116–1121.
   PubMed Web of Science ®Google Scholar
• Cornacchia, C., Cacciatore, I., Baldassarre, L., Mollica, A., Feliciani, F. and Pinnen, F. (2012). 2,5-Diketopiperazines as neuroprotective agents. Mini-Rev. Med. Chem. 12:2–12.
   PubMed Web of Science ®Google Scholar
• Coursindel, T., Restouin, A., Dewynter, G., Martinez, J., Collette, Y. and Parrot, I. (2010). Stereoselective ring contraction of 2,5-diketopiperazines: an innovative approach to the synthesis of promising bioactive 5-membered scaffolds. Bioorg. Chem. 38:210–217.
   PubMed Web of Science ®Google Scholar
• Cryle, M. J., Bell, S. G. and Schlichting, I. (2010). Structural and biochemical characterization of the cytochrome P450 CypX (CYP134A1) from Bacillus Subtilis: a cyclo-L-leucyl-L-leucyl dipeptide oxidase. Biochem. 49:7282–7296.
   PubMed Web of Science ®Google Scholar
• Cui, H. B., Mei, W. L., Miao, C. D., Lin, H. P., Hong, K. and Dai, H. F. (2008). Antibacterial constituents from the endophytic fungus Penicillium sp. 0935030 of mangrove plant Acrostichum aureurm. Chin. J. Antibiot, 33: 407–410.
   Google Scholar
• Curtius, T. and Goebel, F. (1888). Uber glycollather. J. Prakt. Chem. 37:50–181.
   Google Scholar
• Da Costa, N. C., Chen, M. Z., Merritt, D. and Trinnaman, L. (2010). Methionine containing cyclic dipeptides: Occurrence in natural products, synthesis, and sensory evaluation. ACS Symposium Series, In Controlling Maillard Pathways to Generate Flavors. 1042:111–120.
   Google Scholar
• De Baere, S., Cherlet, M., Baert, K. and De Backer, P. (2002). Quantitative analysis of amoxicillin and its major metabolites in animal tissues by liquid chromatography combined with electrospray ionization tandem mass spectrometry. Anal. Chem. 74:1393–1401.
   PubMed Web of Science ®Google Scholar
• Ding, Y., de Wet, J. R., Cavalcoli, J., Li, S., Greshock, T. J., Miller, K. A., Finefield, J. M., Sunderhaus, J. D., McAfoos, T. J., Tsukamoto, S., Williams, R. M. and Sherman, D. H. (2010). Genome-based characterization of two prenylation steps in the assembly of the stephacidin and notoamide anticancer agents in a marine-derived aspergillus sp. J. Amer. Chem. Soc. 132:12733–12740.
   PubMed Web of Science ®Google Scholar
• Ding, Z. G., Zhao, J. Y., Yang, P. W., Li, M. G., Huang, R., Cui, X. L. and Wen, M. L. (2009). (1)H and (13)C NMR Assignments of eight nitrogen containing compounds from nocardia alba sp. nov (YIM 30243(T)). Magn. Reson. Chem. 47:366–370.
   PubMed Web of Science ®Google Scholar
• Dömling, A. (2006). Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chem. Rev. 106:17–89.
   PubMed Web of Science ®Google Scholar
• Eguchi, C. and Kakuta, A. (1974). Cyclic dipeptides. I. Thermodynamics of the cis-trans isomerization of the side chains in cyclic dipeptides. J. Amer. Chem. Soc. 96:3985–3989.
   PubMed Web of Science ®Google Scholar
• Emri, T., Tóth, V., Nagy, C. T., Nagy, G., Pócsi, I., Gyémánt, G., Antal, K., Balla, J., Balla, G., Román, G., Kovács, I. and Pócsi, I. (2013). Towards high-siderophore-content foods: Optimisation of coprogen production in submerged cultures of Penicillium nalgiovense. J. Sci. Food Agric. 93:2221–2228.
   PubMed Web of Science ®Google Scholar
• Faden, A. I., Movsesyan, V. A., Fang, X. and Wang, S. (2005). Identification of novel neuroprotective agents using pharmacophore modeling. Chem. Biodivers. 2:1564–1570.
   PubMed Web of Science ®Google Scholar
• Falorni, M., Giacomelli, G., Porcheddu, A. and Taddei, M. (2000). Solution-phase synthesis of mixed amide libraries by simultaneous addition of functionalities (SPSAF) to a diketopiperazine tetracarboxylic acid scaffold monitored by GC analysis of isobutyl alcohol. Eur. J. Org. Chem. 8:1669–1675.
   Google Scholar
• Friedrich, A., Jainta, M., Nieger, M. and Bräse, S. (2007). One-pot synthesis of symmetrical and unsymmetrical diketopiperazines from unprotected amino acids. Syn. Lett. 13:2127–2129.
   Google Scholar
• Furtadoa, N. A. J. C., Pupoa, M. T., Carvalhoa, I., Campoa, V. L., Duarteb, M. C. T. and Bastos, J. K. (2005). Diketopiperazines produced by an Aspergillus fumigatus brazilian strain. J. Braz. Chem. Soc. 16:1448–1453.
   Web of Science ®Google Scholar
• Furukawa, T., Akutagawa, T., Funatani, H., Uchida, T., Hotta, Y., Niwa, M. and Takaya, Y. (2012). Cyclic dipeptides exhibit potency for scavenging radicals. Bioorg. Med. Chem. 20:2002–2009.
   PubMed Web of Science ®Google Scholar
• Gautschi, M., Schmid, J. P., Peppard, T. L., Ryan, T. P., Tuorto, R. M. and Yang, X. (1997). Chemical characterization of diketopiperazines in beer. J. Agric. Food Chem. 45:3183–3189.
   Web of Science ®Google Scholar
• Geha, R., Buckley, C. E. and Greenberg, P. (1993). Aspartame is no more likely than placebo to cause Urticaria/Angioedema: Results of a multicenter, randomized, double-blind, placebo-controlled, crossover study. J. Allergy Clin. Immunol. 92:513–520.
   PubMed Web of Science ®Google Scholar
• Gillard, J., Frenkel, J., Devos, V., Sabbe, K., Paul, C., Rempt, M., Inzé, D., Pohnert, G., Vuylsteke, M. and Vyverman, W. (2013). Metabolomics enables the structure elucidation of a diatom sex pheromone. Angew. Chem. Int. Ed. Engl. 52:854–857.
   PubMed Web of Science ®Google Scholar
• Ginz, M. and Engelhardt, U. H. (2000). Identification of proline-based diketopiperazines in roasted coffee. J. Agric. Food Chem. 48:3528–3532.
   PubMed Web of Science ®Google Scholar
• Ginz, M. and Engelhardt, U. H. (2001). Identification of new diketopiperazines in roasted coffee. Eur. Food Res. Tech. 213:8–11.
   Web of Science ®Google Scholar
• Gondry, M., Sauguet, L., Belin, P., Thai, R., Amouroux, R., Tellier, C., Tuphile, K., Jacquet, M., Braud, S., Courçon, M., Masson, C., Dubois, S., Lautru, S., Lecoq, A., Hashimoto, S., Genet, R. and Pernodet, J. L. (2009). Cyclodipeptide synthases are a family of tRNA-dependent peptide bond-forming enzymes. Nat. Chem. Biol. 5:414–420.
   PubMed Web of Science ®Google Scholar
• Goodman, M. and Temussi, P. A. (1985). Structure-activity relationship of a bitter diketopiperazine revisited. Biopoly. 24:1629–1633.
   PubMed Web of Science ®Google Scholar
• Gozlan, I., Rotstein, A. and Avisar, D. (2013). Amoxicillin-degradation products formed under controlled environmental conditions: identification and determination in the aquatic environment. Chemosphere. 91:985–992.
   PubMed Web of Science ®Google Scholar
• Graz, M., Hunt, A., Jamie, H., Grant, G. and Milne, P. (1999). Antimicrobial activity of selected cyclic dipeptides. Pharmazie. 54:772–775.
   PubMed Web of Science ®Google Scholar
• Grove, J. F. and Pople, M. (1981). Nitrogen-containing minor metabolic products of Beauveria Bassiana. Phytochem. 20:815–816.
   Web of Science ®Google Scholar
• Guan, J., Mathai, S., Harris, P., Wen, J. Y., Zhang., R., Brimble, M. and Gluckman, P. (2007). Peripheral administration of a novel diketopiperazine, NNZ 2591, prevents brain injury and improves somatosensory-motor function following hypoxia-ischemia in adult rats. Neuropharm. 53:749–762.
   PubMed Web of Science ®Google Scholar
• Gudasheva, T. A., Boyko, S. S., Akparov, V. K., Ostrovskaya, R. U., Skoldinov, S. P., Rozantsev, G. G., Voronina, T. A., Zherdev, V. P. and Seredenin, S. B. (1996). Identification of a novel endogenous memory facilitating cyclic dipeptide cyclo-prolyl-glycine in rat brain. FEBS Lett. 391:149–152.
   PubMed Web of Science ®Google Scholar
• Guigoz, Y. and Solms, J. (1976). Bitter peptides, occurrence and structure. Chem. Senses Flav. 2:71–84.
   Web of Science ®Google Scholar
• Guo, X., Zheng, L., Zhou, W., Cui, Z., Han, P., Tian, L. and Wang, X. (2011). A case study on chemical defense based on quorum sensing: antibacterial activity of sponge-associated bacterium Pseudoalteromonas sp. NJ6-3-1 induced by quorum sensing mechanisms. Ann. Microbiol. 61:247–255.
   Web of Science ®Google Scholar
• Hider, R. C. and Kong, X. (2010). Chemistry and biology of siderophores. Nat. Prod. Rep. 27:637–657.
   PubMed Web of Science ®Google Scholar
• Hilton, C. W., Prasad, C., Vo, P. and Mouton, C. (1992). Food contains the bioactive peptide, cyclo(His-Pro), J. Clin. Endocrinol. Metab. 75:375–378.
   PubMed Web of Science ®Google Scholar
• Ho, C. T. (1996). Thermal generation of maillard aromas. In: The Maillard Reaction: Consequences for the Chemical and Life Sciences. pp. 27−53. Ikan, R., Ed., John Wiley & Sons Ltd., Chichester, UK.
   Google Scholar
• Ho, C. T., Lu, C. Y., Wang, Y., Raghavan, S. and Payne, R. (2007). Maillard flavor chemistry of cysteine and cysteine containing peptides. Chemistry of Flavors, 8th Wartburg Proceedings. 91–95.
   Google Scholar
• Houston, D. R., Synstad, B., Eijsink, V. G. H., Stark, M. J. R., Eggleston, I. M. and van Aalten, D. M. F. (2004). Structure-based exploration of cyclic dipeptide chitinase inhibitors. J. Med. Chem. 47:5713–5720.
   PubMed Web of Science ®Google Scholar
• Huang, G. H., Shen, Y. L. and Zhong, H. F. (2007). Analysis of flavor components of maillard reaction products using the hydrolysate of tilapia. China Condiment (Zhongguo Tiaoweipin). 8:68–70.
   Google Scholar
• Huberman, L., Gollop, N., Mumcuoglu, K. Y., Breuer, E., Bhusare, S. R., Shai, Y. and Galun, R. (2007). Antibacterial substances of low molecular weight isolated from the blowfly, Lucilia sericata. Med. Vet. Entomol. 21:127–131.
   PubMed Web of Science ®Google Scholar
• Isaka, M., Palasarn, S., Rachtawee, P., Vimuttipong, S. and Kongsaeree, P. (2005). Unique diketopiperazine dimers from the insect pathogenic fungus verticillium hemipterigenum BCC 1449. Org. Lett. 7:2257–2260.
   PubMed Web of Science ®Google Scholar
• Ishibashi, N., Sadamori, K., Yamamoto, O., Kanchisa, H., Kouge, K., Kikuchi, E., Okai, H. and Fukui, S. (1987). Bitterness of phenylalanine and tyrosine-containing peptides. Agric. Biol. Chem. 51:2389–2394.
   Web of Science ®Google Scholar
• Ishibashi, N., Kouge, K., Shinoda, I., Kanehisa, H. and Okai, H. (1988). A mechanism for bitter taste sensibility in peptides (Food & Nutrition). Agric. Biol. Chem. 52:819–827.
   Web of Science ®Google Scholar
• Ishibashi, N., Kubo, T., Chino, M., Fukui, H., Shinoda, I., Kikuchi, E., Okai, H. and Fukui, S. (1988). Taste of proline-containing peptides. Agric. Biol. Chem. 52:95–98.
   Web of Science ®Google Scholar
• Ishii, H. (1981a). Incidence of brain tumors in rats fed aspartame. Toxicol. Lett. 7:433–437.
   PubMed Web of Science ®Google Scholar
• Ishii, H., Koshimizu, T., Usami, S. and Fujimoto, T. (1981b). Toxicity of aspartame and its diketopiperazine for wistar rats by dietary administration for 104 weeks. Toxicology. 21:91–94.
   PubMed Web of Science ®Google Scholar
• Jainta, M., Nieger, M., Bräse, S. (2008). Microwave-assisted stereoselective one-pot synthesis of symmetrical and unsymmetrical 2,5-diketopiperazines from unprotected amino acids. Eur. J. Org. Chem. 32:5418–5424.
   Web of Science ®Google Scholar
• Jakas, A. and Horvat, Š. (2003). Study of degradation pathways of amadori compounds obtained by glycation of opioid pentapeptide and related smaller fragments: stability, reactions and spectroscopic properties. Biopolymers. 69:421–431.
   PubMed Web of Science ®Google Scholar
• Jamie, H., Kilian, G., Dyason, K and Milne, P. J. (2002a). The effect of the isomers of cyclo(Trp-Pro) on heart and ion-channel activity. J. Pharm. Pharmacol. 54:1659–1665.
   PubMed Web of Science ®Google Scholar
• Jamie, H., Kilian, G. and Milne, P. J. (2002b). Hepatotoxicity of the isomers of cyclo (Trp-Pro). Pharmazie, 57:638–642.
   PubMed Web of Science ®Google Scholar
• Jayatilake, G. S., Thornton, M. P., Leonard, A. C., Grimwade, J. E. and Baker, B. J. (1996). Metabolites from an antarctic sponge-associated bacterium, Pseudomonas aeruginosa. J. Nat. Prod. 59:293–296.
   PubMed Web of Science ®Google Scholar
• Jhaumeer-Laulloo, S., Khodabocus, A., Jugoo, A., Jheengut, D. and Sobha, S. (2003). Synthesis of diketopiperazines containing prolinyl unit-cyclo(L-Prolinyl-L-Leucine), Cyclo(L-Prolinyl-L-isoLeucine) and Cyclo(L-Tryptophyl-L-Proline). J. Ind. Chem. Soc. 80:765–768.
   Web of Science ®Google Scholar
• Jiang, Z., Boyd, K. G., Mearns-Spragg, A., Adams, D. R., Wright, P. C. and Burgess, J. G. (2000). Two diketopiperazines and one halogenated phenol from cultures of the marine bacterium, Pseudoalteromonas luteoviolacea. Nat. Prod. Lett. 14:435–440.
   Web of Science ®Google Scholar
• Julianti, E., Oh, H., Jang, K. H., Lee, J. K., Lee, S. K., Oh, D. C., Oh, K. B. and Shin, J. (2011). Acremostrictin, a highly oxygenated metabolite from the marine fungus Acremonium strictum. J. Nat. Prod. 74:2592–2594.
   PubMed Web of Science ®Google Scholar
• Kawai, T., Ishida, Y., Kakiuchi, H., Ikeda, N., Higshida, T. and Nakamura, S. (1991). Flavor components of dried squid. J. Agric. Food Chem. 39:770–777.
   Web of Science ®Google Scholar
• Kim, H.O., Li-Chan, E.C.Y. (2006). Quantitative structure-activity relationship study of bitter peptides. J. Agric. Food Chem. 54:10102–10111.
   PubMed Web of Science ®Google Scholar
• Kohl, S., Behrens, M., Dunkel, A., Hofmann, T. and Meyerhof, W. (2012). Amino acids and peptides activate at least five members of the human bitter taste receptor family. J. Agric. Food Chem. 61:53–60.
   PubMed Web of Science ®Google Scholar
• Kopp-Holtwiesche, B. and Rehm, H. J. J. (1990). Antimicrobial action of roquefortine. Environ. Pathol. Toxicol. 10:41–44.
   Google Scholar
• Kumar, N., Mohandas, C., Nambisan, B., Kumar, D. S. and Lankalapalli, R. S. (2013). Isolation of proline-based cyclic dipeptides from bacillus sp. n strain associated with rhabitid entomopathogenic nematode and its antimicrobial properties. World J. Microbio. Biotech. 29:355–364.
   PubMed Web of Science ®Google Scholar
• Lee, B. H. and Pan, T. M. (2013). Dimerumic acid, a novel antioxidant identified from monascus-fermented products exerts chemoprotective effects: mini review. J. Funct. Foods. 5:2–9.
   Web of Science ®Google Scholar
• Li, H., Liu, L., Zhang, S., Cui, W. and Lu, J. (2012). Identification of antifungal compounds produced by Lactobacillus casei AST18. Curr. Microbiol. 65:156–161.
   PubMed Web of Science ®Google Scholar
• Li, X. J., Tang, H. Y., Duan, J. L., Gao, J. M. and Xue, Q. H. (2013). Bioactive alkaloids produced by Pseudomonas brassicacearum subsp. Neoaurantiaca, an endophytic bacterium from Salvia miltiorrhiza. Nat. Prod. Res. 27:496–499.
   PubMed Web of Science ®Google Scholar
• Lin., L., Okada, S., York, D. A. and Bray, G. A. (1994). Structural requirements for the biological activity of enterostatin. Peptides. 15:849.
   PubMed Web of Science ®Google Scholar
• Lind, H., Sjögren, J., Gohil, S., Kenne, L., Schnürer, J. and Broberg, A. (2007). Antifungal compounds from cultures of dairy propionibacteria type strains. FEMS Microbiol. Lett. 271:310–315.
   PubMed Web of Science ®Google Scholar
• Liu, C. J., Liu, D. Y., Xiang, L., Zhou W. and Shao, N. N. (2009). Studies on the chemical constituents of Portulaca oleracea. Zhong Yao Cai. 32:1689–1691.
   PubMedGoogle Scholar
• Liu, C., Yang, X. Q., Ding, Z. T., Zhao, L. X., Cao, Y. R., Xu, L. H. and Yang, Y. B. (2011). Cyclodipeptides from the secondary metabolites of two novel actinomycetes. Chin. J. Nat. Med. 9:78–80.
   Google Scholar
• Long, C., Lu, X. L., Gao, Y., Jiao, B. H. and Liu, X.Y. (2011). Description of a sulfitobacter strain and its extracellular cyclodipeptides. Evid. Based Complement Alternat. Med. 393752:1–6.
   Google Scholar
• Lu, X., Shen, Y., Zhu, Y., Xu, Q., Liu, X., Ni, K. and Jiao, B. (2009). Diketopiperazine constituents of Marine Bacillus subtilis. Chem. of Nat. Comp. 45:290–292.
   Web of Science ®Google Scholar
• Machasashi, K. and Huang, L. (2009). Review: Bitter peptides and bitter taste receptors. Cellular and Molecular Life Sciences. 66:1661–1671.
   PubMed Web of Science ®Google Scholar
• Magnusson, J., Ström, K., Roos, S., Sjögren, J. and Schnürer, J. (2003). Broad and complex antifungal activity among environmental isolates of lactic acid bacteria. FEMS Microbiol. Lett. 219:129–135.
   PubMed Web of Science ®Google Scholar
• Mallikarjun, S. and Sieburth, R. M. (2013). Aspartame and risk of cancer: a meta-analytic review. Arch. Environ. Occup. Health. 70: 133–141.
   Web of Science ®Google Scholar
• Marcaccini, S., Pepino, R. and Pozo, M. C. (2001). A facile synthesis of 2,5-diketopiperazines based on isocyanide chemistry. Tet. Lett. 42:2727–2728.
   Web of Science ®Google Scholar
• Menna, M., Aiello, A., D'Aniello, F., Fattorusso, E., Imperatore, C., Luciano, P. and Vitalone, R. (2012). Further investigation of the mediterranean sponge Axinella polypoides: isolation of a new cyclonucleoside and a new betaine. Marine Drugs. 10:2509–2518.
   PubMed Web of Science ®Google Scholar
• Mercier, J. C., Grosclaude, F. and Ribadeau-Dumas, B. (1971). Structure primaire de la caséine αsl-bovine: séquence compléte. Eur. J. Biochem. 23:41–51.
   PubMedGoogle Scholar
• Minelli, A., Bellezza, I., Grottelli, S. and Galli, F. (2008) Focus on cyclo(His-Pro): history and perspectives as antioxidant peptide. Amino Acids. 35:283–289.
   PubMed Web of Science ®Google Scholar
• Mitova, M., Tommonaro, G., Hentschel, U., Muller, W. E. G. and De Rosa, S. (2004). Exocellular cyclic dipeptides from a Ruegeria strain associated with cell cultures of Suberites domuncula. Mar. Biotech. 6:95–103.
   PubMed Web of Science ®Google Scholar
• Mitova, M., Tutino, M. L., Infusini., G., Marino, G. and De Rosa, S. (2005). Exocellular peptides from antarctic psychrophile pseudoalteromonas haloplanktis. Mar. Biotechnol. 7:523–531.
   PubMed Web of Science ®Google Scholar
• Murray, T. K. and Baker, B. E. (1952). Studies on protein hydrolysis. Part I. Preliminary observations on the taste of enzymic protein hydrolysates. J. Sci. Food Agric. 3:470–475.
   Web of Science ®Google Scholar
• Musthafa, K. S., Balamurugan, K., Pandian, S. K. and Ravi, A. V. (2012). 2,5-Piperazinedione inhibits quorum sensing-dependent factor production in pseudomonas aeruginosa PAO1. J. Basic Microbiol. 52:679–686.
   PubMed Web of Science ®Google Scholar
• Ney, K. H. (1971). Predictions of bitterness of peptides from their amino acid composition. Z. Lebensm Unters Forsch. 147:64–71.
   Google Scholar
• Ney, K. H. (1986). Cocoa aroma: bitter compounds as important taste ingredients. Gordian. 5:84–88.
   Google Scholar
• Nierman, W., Pain, A., Anderson, M. J. and Wortman, J. (2005). Genomic sequence of the pathogenic and allergenic filamentous fungus Aspergillus fumigatus. Nature, 438:1151–1156.
   PubMed Web of Science ®Google Scholar
• Niku-Paavola, M. L., Laitila, A., Mattila-Sandholm, T. and Haikara, A. (1999). New types of antimicrobial compounds produced by Lactobacillus plantarum. J. Appl. Microbiol. 86:29–35.
   PubMed Web of Science ®Google Scholar
• Nishanth Kumar, S., Mohandas, C. and Nambisan, B. (2013). Purification of an antifungal compound, Cyclo(L-Pro-D-Leu) for cereals produced by Bacillus cereus subsp. thuringiensis associated with entomopathogenic nematode. Microbiol. Res. 168:278–288.
   PubMed Web of Science ®Google Scholar
• Ortiz-Castro, R., Díaz-Pérez, C., Martínez-Trujillo, M., Rosa, E., Campos-García, J. and López-Bucio, J. (2011). Transkingdom signaling based on bacterial cyclodipeptides with auxin activity in plants. Proc. Nat. Acad. Sci. 108:7253–7258.
   PubMed Web of Science ®Google Scholar
• Otagiri, K., Nosho, Y., Shinoda, I., Fukui, H. and Okai, H. (1985) Studies on a model of bitter peptides including arginine, proline and phenylalanine residues. Agric. Biol. Chem. 49:1019–1026.
   Web of Science ®Google Scholar
• Park, D. K., Lee, K. E., Baek, C. H., Kim, I. H., Kwon, J. H., Lee, W. K., Lee, K. H., Kim, B. S., Choi, S. H. and Kim, K. S. (2006). Cyclo (Phe-Pro) modulates the expression of ompU in Vibrio spp. J. Bacteriol. 188:2214–2221.
   PubMed Web of Science ®Google Scholar
• Park, Y. C., Gunasekera, S. P., Lopez, J. V., McCarthy, P. J. and Wright, A. E. (2006) Metabolites from the marine-derived fungus Chromocleista sp. isolated from a deep-water sediment sample collected in the Gulf of Mexico. J. Nat. Prod. 69:580–584.
   PubMed Web of Science ®Google Scholar
• Pedras, M. S. C., Yu, Y., Liu, J. and Tandron-Moya, Y. A. Z. (2005). Metabolites produced by the phytopathogenic fungus rhizoctonia solani: isolation, chemical structure determination, syntheses and bioactivity. Naturforsch. C. 60:717–722.
   PubMed Web of Science ®Google Scholar
• Peng, J. and Clive, D. L. J. (2008). Asymmetric synthesis of the ABC-ring system of the antitumor antibiotic MPC1001. J. Org. Chem. 74:513–519.
   Web of Science ®Google Scholar
• Pérez-Picaso, L., Escalante, J., Olivo, H. F. and Rios, M. Y. (2009). Efficient microwave assisted syntheses of 2,5-Diketopiperazines in aqueous media. Molecules. 14:2836–2849.
   PubMed Web of Science ®Google Scholar
• Pérez-Picaso, L., Olivo, H. F., Argotte-Ramos, R., Rodríguez-Gutiérrez, M. D. C. and Rios, M. Y. (2012). Linear and cyclic dipeptides with antimalarial activity. Bioorg. Med. Chem. Lett. 22:7048–7051.
   PubMed Web of Science ®Google Scholar
• Perry, T. I., Richardson, K. S. C., Hansen, S. and Friesen, A. J. D. (1965). Identification of the diketopiperazine of histidyl-proline in human urine. J. Biol. Chem. 240:4540–4542.
   PubMed Web of Science ®Google Scholar
• Pickenhagen, W. (1974). “Le Principe Amer du Cacao”, Thése, Université de Paris-Sud, Centre d'Orsay.
   Google Scholar
• Pitchen, R. (2002). The medicinal chemistry of the cyclic dipeptides Cyclo(Met-Met) and Cyclo(Met-Gly). Dissertation, Magister Scientiae, Faculty of Health Sciences, University of Port Elizabeth.
   Google Scholar
• Pócsi, I., Jeney, V., Kertai, P., Pócsi, I., Emri, T., Gyémánt, G., Fésüs, L., Balla, J. and Balla, G. (2008). Fungal siderophores function as protective agents of LDL oxidation and are promising anti-atherosclerotic metabolites in functional food. Mol. Nutr. Food Res. 52:1434–1447.
   PubMed Web of Science ®Google Scholar
• Prasad, C. (1995). Bioactive cyclic dipeptides. Peptides, 16:151–164.
   PubMed Web of Science ®Google Scholar
• Prasad, C. (2005). Food-derived neuroactive cyclic dipeptides. In: Nutritional Neuroscience, pp. 331–340. Lieberman, H. R., Kanarek, R. B., Prasad, C., Eds., CRC Press LLC, Boca Raton, Fla.
   Google Scholar
• Ramos, F., Boison, J., Friedlander, L. G. and Names, I. (2012). U.P.A.C. other information on identity and properties. Amoxicillin, Residues in Food and their Evaluation, ftp://ftp.fao.org/ag/agn/jecfa/vetdrug/12-2012-amoxicillin.pdf.
   Google Scholar
• Rhee, K. H., Choi, K. H., Kim, C. J. and Kim, C. H. (2001). Identification of streptomyces sp. AMLK-335 producing antibiotic substance inhibitory to vancomycin-resistant enterococci. J. Microbiol. Biotech. 11:469–474.
   Web of Science ®Google Scholar
• Rhee, K. H. (2002a). Inhibition of DNA topoisomerase I by Cyclo(L-Prolyl-L-Phenylalanyl) isolated from streptomyces sp. AMLK-335. J. Microbiol. Biotech. 12:1013–1016.
   Web of Science ®Google Scholar
• Rhee, K. H. (2002b). Isolation and characterization of Streptomyces sp. KH-614 producing anti-VRE (vancomycin-resistant enterococci) antibiotics. J. Gen. Appl. Microbiol. 48:321–327.
   PubMed Web of Science ®Google Scholar
• Rhee, K. H. (2003). Purification and identification of an antifungal agent from Streptomyces sp. KH-614 antagonistic to rice blast fungus, Pyricularia oryzae. J. Microbiol. Biotech. 13:984–988.
   Web of Science ®Google Scholar
• Rhee, K. H. (2004). Cyclic dipeptides exhibit synergistic, broad spectrum antimicrobial effects and have anti-mutagenic properties. Int. J. Antimicrob. Agents 24:423–427.
   PubMed Web of Science ®Google Scholar
• Rhee, K. H. (2006). In vitro activity of cyclic dipeptides against gram-positive and gram-negative anaerobic bacteria and radioprotective effect on lung cells. J. Microbiol. Biotech. 16:158–162.
   Web of Science ®Google Scholar
• Rhoden, C. R., Rivera, D. G., Kreye, O., Bauer, A. K., Westermann, B. and Wessjohann, L. A. (2009). Rapid access to N-substituted diketopiperazines by one-pot Ugi-4CR/deprotection+Activation/Cyclization (UDAC). J. Comb. Chem. 11:1078–1082.
   PubMed Web of Science ®Google Scholar
• Rizzi, G. P. (1989). Heat-induced flavor formation from peptides. Therm. Gener. Aromas ACS Symp. Ser. 409:172–181.
   Google Scholar
• Rose, G. D., Gierasch, L. M. and Smith, J. A. (1985). Turns in peptides and proteins. Adv. Protein Chem. 37:1–109.
   PubMedGoogle Scholar
• Roudot-Agaron, F., Le Barbs, D., Einhorn, J., Adda, J. and Gripon, J. C. (1993). Flavor constituents of aqueous fraction extracted from comte cheese by liquid carbon dioxide. J. Food Sci. 58:1005–1009.
   Web of Science ®Google Scholar
• Ryan, L. A., Dal Bello, F., Arendt, E. K. and Koehler, P. (2009). Detection and quantitation of 2,5-diketopiperazines in wheat sourdough and bread, J. Agric. Food Chem. 57:9563–9568.
   PubMed Web of Science ®Google Scholar
• Ryan, L. A., Zannini, E., Dal Bello, F., Pawlowska, A., Koehler, P. and Arendt, E. K. (2011). Lactobacillus amylovorus DSM 19280 as a novel food-grade antifungal agent for bakery products. Int. J. Food Microbiol. 146:276–283.
   PubMed Web of Science ®Google Scholar
• Samonina, G., Ashmarin, I. and Lyapina, L. (2002). Glyproline peptide family: review on bioactivity and possible origins. Pathophys. 8:229–234.
   PubMedGoogle Scholar
• Sansone, G., Rezza, I., Calvente, V., Benuzzi, D. and Tosetti, M. I. S. D. (2005). Control of Botrytis cinerea strains resistant to iprodione in apple with rhodotorulic acid and yeasts. Postharvest Biol. Technol. 35:245–251.
   Web of Science ®Google Scholar
• Santagada, V., Fiorino, F., Perissutti, E., Severino, B., Terracciano, S., Cirino, G. and Caliendo, G. (2003). A convenient strategy of dimerization by microwave heating and using 2,5-Diketopiperazine as scaffold. Tet. Lett. 44:1145–1148.
   Web of Science ®Google Scholar
• Schnürer, J. and Magnusson, J. (2005). Antifungal lactic acid bacteria as biopreservatives. Trends Food Sci. Technol. 16:70–78.
   Web of Science ®Google Scholar
• Shangguan, N., Hehre, W. J., Ohlinger, W. S., Beavers, M. P. and Joullié, M. M. (2008). The total synthesis of roquefortine C and a rationale for the thermodynamic stability of isoRoquefortine C over roquefortine C. J Amer. Chem. Soc. 130:6281–6287.
   PubMed Web of Science ®Google Scholar
• Shiba, T., Uratani, H., Kubota, I. and Sumi, Y. (1981). Some aspects of the relationship between the structure of a bitter diketopiperazine and its receptor. Biopoly. 20:1985–1987.
   PubMed Web of Science ®Google Scholar
• Shigemori, H., Tenma, M., Shimazaki, K. and Kobayashi, J. (1998). Three new metabolites from the marine yeast aureobasidium pullulans. J. Nat. Prod. 61:696–698.
   PubMed Web of Science ®Google Scholar
• Stark, T. and Hofmann T. (2005). Structures, sensory activity, and dose/response functions of 2,5-Diketopiperazines in roasted cocoa nibs (Theobroma Cacao). J. Agric. Food Chem. 53:7222–7231.
   PubMed Web of Science ®Google Scholar
• Steinberg, S. and Bada, J. L. (1981). Diketopiperazine formation during investigations of amino acid racemization in dipeptides. Science. 213:544–545.
   PubMed Web of Science ®Google Scholar
• Stierle, A. C., Cardellina, J. H. and Strobel, G. A. (1988). Maculosin, a host-specific phytotoxin for spotted knapweed from Alternaria alternata. Proc. Natl. Acad. Sci. U. S. A. 85:8008–8011.
   PubMed Web of Science ®Google Scholar
• Ström, K., Sjögren, J., Broberg, A. and Schnürer, J. (2002). Lactobacillus plantarum MiLAB 393 produces the antifungal cyclic dipeptides Cyclo(L-Phe-L-Pro) and Cyclo (L-Phe-trans-4-OH-L-Pro) and 3-Phenyllactic acid. J. Appl. Environ. Microbiol. 68:4322–4327.
   PubMed Web of Science ®Google Scholar
• Szafranek, J., Palacz, Z. and Grzonka, Z. (1976). A comparison of electron impact and field ionization spectra of some 2, 5-Diketopiperazines. Org. Mass. Spec. 11:920–930.
   Google Scholar
• Takaya, Y., Furukawa, T., Miura, S., Akutagawa, T., Hotta, Y., Ishikawa, N. and Niwa, M. (2007). Antioxidant constituents in distillation residue of awamori spirits. J. Agric. Food Chem. 55:75–79.
   PubMed Web of Science ®Google Scholar
• Takahashi, K., Tadenuma, M., Kitamoto, K. and Sato, S. (1974). L-Prolyl-L-Leucine anhydride a bitter compound formed in aged sake. Agr. Biol. Chem. 38:927–932.
   Web of Science ®Google Scholar
• Tamura, M., Miyoshi, T., Mori, N., Kinomura, K., Kawaguchi, M., Ishibashi, N. and Okai, H. (1990). Mechanism for the bitter tatsing potency of peptides using O-aminoacyl sugars as model compounds. Agric. & Biol. Chem. 54:1401–1409.
   PubMed Web of Science ®Google Scholar
• Thajudeen, H., Park, K., Moon, S. S. and Hong, I. S. (2010). An efficient green synthesis of proline-based cyclic dipeptides under water-mediated catalyst-free conditions. Tet. Lett. 51:1303–1305.
   Web of Science ®Google Scholar
• Tian, S. Z., Pu, X., Luo, G., Zhao, L. X., Xu, L. H., Li, W. J. and Luo, Y. (2013). Isolation and characterization of new p-Terphenyls with antifungal, antibacterial, and antioxidant activities from a halophilic actinomycete nocardiopsis gilva YIM 90087. J. Agric. Food Chem. 61:3006–3012.
   PubMed Web of Science ®Google Scholar
• Toelstede, S. and Hofmann, T. (2008). Sensomics mapping and identification of key bitter metabolites in Gouda cheese. J. Agric. Food Chem. 56:2795–2804.
   PubMed Web of Science ®Google Scholar
• Tsang, W. S., Clarke, M. A. and Parrish, F. W. (1985). Determination of aspartame and its breakdown products in soft drinks by reverse-phase chromatography with UV detection. J. Agric. Food Chem. 33:734–738.
   Web of Science ®Google Scholar
• Tsuruoka, N., Beppu, Y., Koda, H., Doe, N., Watanabe, H. and Abe, K., (2012). A DKP Cyclo(L-Phe-L-Phe) found in chicken essence is a dual inhibitor of the serotonin transporter and acetylcholinesterase. PloS One. 7: e50824.
   PubMed Web of Science ®Google Scholar
• Tullberg, M., Grotli, M. and Luthman, K. (2006). Efficient synthesis of 2,5-Diketopiperazines using microwave assisted heating. Tetrahedron. 62:7484–7491.
   Web of Science ®Google Scholar
• van der Helm, D and Winkelmann, G. (1994). Hydroxamates and polycarboxylates as ion transport agents (Siderophores). In: Fungi, 11, pp.39–98. Winkelmann, G. and Winge, D. R. Ed., Metal Ions in Fungi, Marcel Dekker, Inc., New York, N.Y.
   Google Scholar
• Vergne, C., Boury-Esnault, N., Perez, T., Martin, M., Adeline, M., Tran Huu Dau, E. and Al-Mourabit, A. (2006), Verpacamides A–D, A sequence of C11N5 Diketopiperazines relating Cyclo(Pro-Pro) to Cyclo(Pro-Arg), from the marine sponge Axinella vaceleti: Possible biogenetic precursors of Pyrrole-2-aminoimidazole alkaloids. Org. Lett. 8:2421–2424.
   PubMed Web of Science ®Google Scholar
• Walchshofer, N., Sarciron, M. E., Garnier, F., Delatour, P., Petavy, A. F. and Paris, (1997). Anthelmintic activity of 3,6-dibenzyl-2,5-dioxopiperazine, cyclo(L-Phe-L-Phe). Amino Acids 12:41–47.
   Web of Science ®Google Scholar
• Wang, R., Yang, C. and Song, H. (2012). Key meat flavour compounds formation mechanism in a glutathione-xylose maillard reaction. Food Chem. 131:280–285.
   Web of Science ®Google Scholar
• Yamashiro, J., Shiraishi, S., Fuwa, T. and Horie, T. (2008). Dimerumic acid protected oxidative stress-induced cytotoxicity in isolated rat hepatocytes. Cell Biol. Toxicol. 24:283–290.
   PubMed Web of Science ®Google Scholar
• Yan, P. S., Song, Y., Sakuno, E., Nakajima, H., Nakagawa, H. and Yabe, K. (2004). Cyclo(L-leucyl-L-prolyl) produced by Achromobacter xylosoxidans inhibits aflatoxin production by Aspergillus parasiticus. Appl. Environ. Microbiol. 70:7466–7473.
   PubMed Web of Science ®Google Scholar
• Yang, E. J. and Chang, H. C. (2010). Purification of a new antifungal compound produced by Lactobacillus plantarum AF1 isolated from kimchi. Int. J. Food Microbiol. 139:56–63.
   PubMed Web of Science ®Google Scholar
• Yang, Z., Yang, Y., Yang, X., Zhang, Y., Zhao, L., Xu, L. and Ding, Z. (2011). Sesquiterpenes from the secondary metabolites of Streptomyces sp. (YIM 56130). Chem. Pharm. Bull. 59:1430–1433.
   PubMed Web of Science ®Google Scholar
• Yaron, A. and Naider, F. (1993). Proline-dependent structural and biological properties of peptides and proteins. CRC Crit. Rev. Biochem. 28:31–81.
   Google Scholar
• Yin, J., Diao, Y., Wen, Z., Wang, Z. and Li, M. (2010). Studying peptides biological activities based on multidimensional descriptors (E) using support vector regression. Intern J. Peptide Res Therapeutics. 16:111–121.
   Web of Science ®Google Scholar
• Zhao, W. Y., Zhu, T. J., Fan, G.T., Liu, H. B., Fang, Y. C., Gu, Q. Q. and Zhu, W. M. (2010). Three new dioxopiperazine metabolites from a marine-derived fungus aspergillus fumigatus fres. Nat. Prod. Res. 24:953–957.
   PubMed Web of Science ®Google Scholar
• Zhu, F., Lin, Y. C., Zhou, S. N. and Vrijmoed, L. L. P. (2003). Metabolites of mangrove endophytic fungus no.2534 from the South China Sea. Acta Sci. Nat. Univ. Sunyatseni. 42:52–54.
   Google Scholar
• Zhuravleva, O. I., Leshchenko, E. V., Afiyatullov, S. S., Sobolevskaya, M. P., Denisenko, V. A. and Shevchenko, L. S. (2011). Metabolites from the Marine Actinobacterium Streptomyces sp. KMM 7210. Chem. of Nat. Comp. 47:494–495.
   Web of Science ®Google Scholar
• Zi, J. C., Lin, S., Zhu, C. G., Yang, Y. C. and Shi, J. G. (2012). Minor constituents from the tubers of Gymnadenia conopsea. J. Asian Nat. Prod. Res. 12:477–484.
   Web of Science ®Google Scholar