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Bitter taste of Brassica vegetables: The role of genetic factors, receptors, isothiocyanates, glucosinolates, and flavor context

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  • Alpizar, Y. A., Boonen, B., Gees, M., Sanchez, A., Nilius, B., Voets, T. and Talavera, K. (2014). Allyl isothiocyanate sensitizes TRPV1 to heat stimulation. Pflugers Arch. 466:507–515.
  • Avau, B. and Depoortere, I. (2016). The bitter truth about bitter taste receptors: Beyond sensing bitter in the oral cavity. Acta. Physiol. (Oxf). 216:407–420.
  • Baik, H. Y., Juvik, J. A., Jeffrey, E. H., Wallig, M. A., Kushad, M. and Klein, B. P. (2003). Relating glucosinolate content and flavor of broccoli cultivars. J. Food Sci. 68:1043–1050.
  • Bartoshuk, L. M., Duffy, V. B. and Miller, I. J. (1994). PTC/PROP tasting: Anatomy, psychophysics, and sex effects. Physiol. Behav. 56:1165–1171.
  • Beckett, E. L., Martin, C., Yates, Z., Veysey, M., Duesing, K. and Lucock, M. (2014). Bitter taste genetics – the relationship to tasting, liking, consumption and health. Food Funct. 5:3040–54.
  • Behrens, M., Gunn, H. C., Ramos, P. C., Meyerhof, W. and Wooding, S. P. (2013). Genetic, functional, and phenotypic diversity in TAS2R38-mediated bitter taste perception. Chem. Senses. 38:475–484.
  • Behrens, M. and Meyerhof, W. (2013). Seminars in Cell & Developmental Biology Bitter taste receptor research comes of age: From characterization to modulation of TAS2Rs. Semin. Cell Dev. Biol. 24:215–221.
  • Bones, A. M. and Rossiter, J. T. (1996). The myrosinase-glucosinolate system, its organisation and biochemistry. Physiologia Plantarum. 97:194–208.
  • Brewster, M. S. J. and Gaudet, R. (2016). How the TRPA1 receptor transmits painful stimuli: Inner workings revealed by electron cryomicroscopy Monique. Bio. Essays. 37:1184–1192.
  • Bufe, B., Breslin, P. A., Kuhn, C., Reed, D. R., Tharp, C. D., Slack, J. P., Kim, U. K., Drayna, D. and Meyerhof, W. (2005). The molecular basis of individual differences in phenylthiocarbamide and propylthiouracil bitterness perception. Curr. Biol. 15:322–327.
  • Buttery, R. G., Guadagni, D. G., Ling, L. C., Seifert, R. M. and Lipton, W. (1976). Additional volatile components of cabbage, broccoli, and cauliflower. J. Agric. Food Chem. 24:829–832.
  • Capuano, E., Dekker, M., Verkerk, R. and Oliviero, T. (2017). Food as pharma? The case of glucosinolates. Curr. Pharm. Des. 23:2697–2721.
  • Carlson, D. G., Daxenbichler, M. E. and Vanetten, C. H. (1987). Glucosinolates in crucifer vegetables: Broccoli, brussels sprouts, cauliflower, collards, kale, mustard greens and kohlrabi. J. Amer. Soc. Hort. Sci. 112:173–178.
  • Cavanaugh, E. J., Simkin, D. and Kim, D. (2008). Activation of transient receptor potential A1 channels by mustard oil, tetrahydrocannabinol and Ca2+ reveals different functional channel states. Neuroscience. 154:1467–1476.
  • Chang, W. I., Chung, J. W., Kim, Y. K., Chung, S. C. and Kho, H. S. (2006). The relationship between phenylthiocarbamide (PTC) and 6-n-propylthiouracil (PROP) taster status and taste thresholds for sucrose and quinine. Arch. Oral. Biol. 51:427–432.
  • Chin, H. W. and Lindsay, R. C. (1994). Mechanisms of formation of volatile sulfur compounds following the action of cysteine sulfoxide lyases. J. Agric. Food Chem. 42:1529–1536.
  • Cromer, B. A., McIntyre, P. (2008). Painful toxins acting at TRPV1. Toxicon. 51:163–73.
  • Dateo, G. P, Clapp, R. C., Mackay, D. A. M., Hewitt, E. J. and Hasselstorm, T. (1957). Identification of the volatile sulfur components of cooked cabbage and the nature of the precursors in the vegetable. J. Food Sci. 22:440–447.
  • Doerr, B., Wade, K. L., Stephenson, K. K., Reed, S. B. and Fahey, J. W. (2009). Cultivar effect on Moringaoleiferaglucosinolate content and taste: A pilot study. Ecol. Food Nutr. 48:199–211.
  • Drewnowski, A. and Gomez-Carneros, C. (2000). Bitter taste, phytonutrients and the consumer: A review. Am. J. Clin. Nutr. 72:1424–1435.
  • Engel, E., Baty, C., Le Corre, D., Souchon, I. and Martin, N. (2002). Flavor-active compounds potentially implicated in cooked cauliflower acceptance. J. Agric. Food Chem. 50:6459–6467.
  • Engel, E., Martin, N. and Issanchou, S. (2006). Sensitivity to allyl isothiocyanate, dimethyl trisulfide, sinigrin, and cooked cauliflower consumption. Apetite. 46:263–269.
  • Everaerts, W., Gees, M., Alpizar, Y. A., Farre, R., Leten, C., Apetrei, A., Dewachter, I., van Leuven, F., Vennekens, R., De Ridder, D., Nilius, B., Voets, T. and Talavera, K. (2011). The capsaicin receptor TRPV1 is a crucial mediator of the noxious effects of mustard oil. Curr. Biol. 21:316–321.
  • Fenwick, G. R., Curl, C. L., Griffiths, N. M., Heaney, R. K. and Price, K. R. (1990). Bitter principles in food plants. In: Bitterness in Foods and Beverages; Developments in Food Science 25, pp. 205–50. Rouseff, RL, ed., Amsterdam: Elsevier.
  • Fenwick, G. R., Griffiths, N. M. and Heaney, R. K. (1983a). Bitterness in Brussels sprouts (Brassica oleracea L vargemnifera): The role of glucosinolates and their breakdown products. J. Sci. Food Agric. 34:73–80.
  • Fenwick, G. R., Heaney, R. K. and Mullin, W. J. (1983b). Glucosinolates and their breakdown products in food and food plants. Crit. Rev. Food Sci. Nutr. 18:123–201.
  • Fischer, J. (1992). Sulphur- and nitrogen-containing volatile components of kohlrabi (Brassica oleracea var. gongylodes L.). Z Lebensm. Unters. Forsch. 194:259–262.
  • Gahbauer, S. and Böckmann, R. A. (2016). Membrane-mediated oligomerization of G protein coupled receptors and its implications for GPCR function. Front Physiol. 7:494–511.
  • Galindo, M. M., Schneider, N. Y., Stähler, F., Töle, J. and Meyerhof, W. (2012). Taste preferences. Prog. Mol. Biol. Transl. Sci. 108:383–426.
  • Gees, M., Alpizar, Y. A., Boonen, B., Sanchez, A., Everaerts, W., Segal, A., Xue, F., Janssens, A., Owsianik, G., Nilius, B., Voets, T., Talavera, K. (2013). Mechanisms of transient receptor potential vanilloid 1 activation and sensitization by allyl isothiocyanate. Mol. Pharmacol. 84:325–334.
  • Ghawi, S. K, Metheven, L., Rastal, R. A. and Niranjan, K. (2012). Thermal and high hydrostatic pressure inactivation of myrosinase from green cabbage: A kinetic study. Food Chem. 131:1240–1247
  • Ghawi, S. K., Shen, Y., Niranjan, K. and Methven, L. (2014). Consumer acceptability and sensory profile of cooked broccoli with mustard seeds added to improve chemoprotective properties. J Food Sci. 79:1756–1762.
  • Gilbert, J. and Nursten, H. E. (1972). Volatile compounds of horseradish roots. J. Sci. Food. Agric. 23:527–539.
  • Hamamoto, A. and Mazelis, M. (1986). The C-S lyases of higher plants: Isolation and properties of homogeneous cystinelyase from broccoli (Brassica oleraceavar botrytis) buds. Plant Physiol. 80:702–706.
  • Hanschen, F. S., Klopsch, R., Oliviero, T., Schreiner, M., Verkerk, R. and Dekker, M. (2017). Optimizing isothiocyanate formation during enzymatic glucosinolate breakdown by adjusting pH value, temperature and dilution in Brassica vegetables and Arabidopsis thaliana. Sci. Rep. 7:40807.
  • Hansen, M., Laustsen, A. M., Olsen, C. E., Poll, L. and Sorensen, H. (1997). Chemical and sensory quality of broccoli (Brassica oleracea L. var italica). J. Food Qual. 20:441–459.
  • Higdon, J. V., Delage, B., Williams, D. E. and Dashwood, R. H. (2007). Cruciferous vegetables and human cancer risk: Epidemiologic evidence and mechanistic basis. Pharmacol. Res. 55:224–36.
  • Hinman, A., Chuang, H. H., Bautista, D. M. and Julius, D. (2006). TRP channel activation by reversible covalent modification. Proc. Natl. Acad. Sci. U. S. A. 103:19564–8.
  • Inoue, H., Yamakawa-Kobayashi, K., Suzuki, Y., Nakano, T., Hayashi, H. and Kuwano, T. (2013). A case study on the association of variation of bitter-taste receptor gene TAS2R38 with the height, weight and energy intake in Japanese female college students. J. Nutr. Sci. Vitaminol. 59:16–21.
  • Ishida, M., Hara, M., Fukino, N., Kakizaki, T. and Morimitsu, Y. (2014). Glucosinolate metabolism, functionality and breeding for the improvement of Brassicaceae vegetables. Breed Sci. 64:48–59.
  • Jacobsson, A., Nielsen, T. and Sjoholm, I. (2004). Influence of temperature, modified atmosphere packaging, and heat treatment on aroma compounds in broccoli. J. Agric. Food Chem. 52:1607–1614.
  • Jara-Oseguera, A., Simon, S. and Rosenbaum, T. (2008). TRPV1: On the road to pain relief. Curr. Mol. Pharmacol. 1:255–269.
  • Keller, K. L., Reid, A., MacDougall, M. C., Cassano, H., Song, J. L., Deng, L., Lanzano, P., Chung, W. K. and Kissileff, H. R. (2010). Sex differences in the effects of inherited bitter thiourea sensitivity on body weight in 4–6-year-old children. Obesity. 18:1194–1200.
  • Khataan, N. H., Stewart, L., Brenner, D. M., Cornelis, M. C. and El-Sohemy, A. (2010). TAS2R38 genotypes and phenylthiocarbamide bitter taste perception in a population of young adults. J. Nutrigenet. Nutrigenomics. 2:251–256.
  • Kim, D. and Cavanaugh, E. J. (2007). Requirement of a soluble intracellular factor for activation of transient receptor potential A1 by pungent chemicals: Role of inorganic polyphosphates. J. Neurosci. 27:6500–6509.
  • Kim, U. K. and Drayna, D. (2005). Genetics of individual differences in bitter taste perception: Lessons from the PTC gene. Clin. Genet. 67:275–280.
  • Kim, U. K., Jorgenson, E., Coon, H., Leppert, M., Risch, N. and Drayna, D. (2003). Positional cloning of the human quantitative trait locus phenylthiocarbamide. Science. 299:1221–1226.
  • Kissen, R, Rossiter, J. T. and Bones, A. M. (2009). The “mustard oil bomb”: Not so easy to assemble?! Localization, expression and distribution of the components of the myrosinase enzyme system. Phytochem. Rev. 8:69–86.
  • Krul, C., Humblot, C., Philippe, C., Vermeulen, M., van Nuenen, M., Havenaar, R. and Rabot, S. (2002). Metabolism of sinigrin (2-propenyl glucosinolate) by the human colonic microflora in a dynamic in vitro large-intestinal model. Carcinogenesis. 23:1009–1016.
  • Kubec, R., Drhova, V. and Velı, J. (1998). Thermal degradation of S-methylcysteine and its sulfoxides important flavor precursors of brassica and allium vegetables. J. Agric. Food Chem. 46:4334–4340.
  • Kubec, R., Drhová, V. and Velíšek, J. (1998). Thermal degradation of S-methylcysteine and its sulfoxideimportant flavor precursors of brassica and allium vegetables. J. Agric. Food Chem. 46:4334–4340.
  • MacLeod, A. J. and MacLeod, G. (1970). Effects of variation in cooking methods on the flavor volatiles of cabbage. J. Food Sci. 35:744–750.
  • Macpherson, L. J., Dubin, A. E., Evans, M. J., Marr, F., Schultz, P. G., Cravatt, B. F. and Patapoutian, A. (2007). Noxious compounds activate TRPA1 ion channels through covalent modification of cysteines. Nature. 445:541–545.
  • Marks, H. S., Hilson, J. A., Leichtweis, H. C. and Stoewsand, G. S. (1992). S-Methylcysteine sulfoxide in Brassica vegetables and formation of methyl methanethiosulfinate from Brussels sprouts. J Agric Food Chem. 40:2098–2101.
  • Maryuama, F. T. (1970). Identification of dimethyl trisulfide as a major aroma component of cooked Brassicaceous vegetables. J. Food Sci. 35:540–543.
  • Martinez-Balesta, M. C. and Carvajal, M. (2015). Myrosinase in Brassicaceae: The most important issue for glucosinolate turnover and food quality. Phytochem. Rev. 14:1045–1051.
  • Matusheski, N. V., Juvik, J. A. and Jeffery, E. H. (2004). Heating decreases epithiospecifier protein activity and increases sulforaphane formation in broccoli. Phytochemistry. 65:1273–81.
  • Mazumder, A., Dwivedi, A. and du Plessis, J. (2016). Sinigrin and its therapeutic benefits. Molecules. 21:416.
  • McGorrin, R. J. (2011). The significance of volatile sulfur compounds in food flavors. In: Volatile Sulfur Compounds in Food, pp. 3–31. Qian, M (Ed.). ACS Symposium Series. Washington, DC.
  • Mennella, J. A., Pepino, M. Y. and Reed, D. R. (2005). Genetic and environmental determinants of bitter perception and sweet preferences. Pediatrics. 115:216–22.
  • Mickle, A. D, Shepherd, A. J. and Mohapatra, D. P. (2015). Sensory TRP channels: The key transducers of nociception and pain. Prog. Mol. Biol. Transl. Sci. 131:73–118.
  • Mihara, S. and Shibamoto, T. (2015). The role of flavor and fragrance chemicals in TRPA1 (transient receptor potential cation channel, member A1) activity associated with allergies. Allergy Asthma ClinImmunol. 11:11–23.
  • Montell, C., Birnbaumer, L. and Flockerzi, V. (2002). The TRP channels, a remarkably functional family. Cell, 108:595–598.
  • Nilius, B. and Owsianik, G. (2011). The transient receptor potential family of ion channels. Genome Biol. 12:218–229.
  • Patapoutian, A., Tate, S. and Woolf, C. J. (2009). Transient receptor potential channels: Targeting pain at the source. Nat. Rev. Drug. Discov. 8:55–68.
  • Paulsen, C. E., Armache, J. P., Gao, Y., Cheng, Y. and Julius, D. (2015). Structure of the TRPA1 ion channel suggests regulatory mechanisms. Nature. 520:511–517.
  • Persuy, M. A., Sanz, G., Tromelin, A., Thomas-Danguin, T., Gibrat, J. F. and Pajot-Augy, E. (2015). Mammalian olfactory receptors: Molecular mechanisms of odorant detection, 3D-modeling, and structure-activity relationships. Prog. Mol. Biol. Transl. Sci. 130:1–36.
  • Pino, A. (2014). Odor active compounds in papaya fruit cv. Red MAradol. Food Chem. 146:120–126.
  • Rask, L., Andréasson, E., Ekbom, B., Eriksson, S., Pontoppidan, B. and Meijer, J. (2000). Myrosinase: Gene family evolution and herbivore defense in Brassicaceae. Plant. Mol. Biol. 42:93–113.
  • Reinach, P. S., Chen, W. and Mergler, S. (2015). Polymodal roles of transient receptor potential channels in the control of ocular function. Eye Vis (Lond). 2:5–15.
  • Reineccius, G. (2005). An overview of flavor perception. In: Flavor Chemistry and Technology, 2nd ed., pp. 3–21. Reineccius, G., CRC Press, Taylor & Francis Group, Boca Raton, FL.
  • Risso, D. S., Mezzavilla, M., Pagani, L., Robino, A., Morini, G., Tofanelli, S., Carrai, M., Campa, D., Barale, R., Caradonna, F., Gasparini, P., Luiselli, D. and Wooding, D. (2016). Global diversity in the TAS2R38 bitter taste receptor: Revisiting a classic evolutionary PROPosal. Sci. Rep. 6:25506.
  • Roper, S. D. (2014). TRPs in taste and chemesthesis. Handb. Exp. Pharmacol. 223:827–71.
  • Roura, E., Aldayyani, A., Thavaraj, P., Prakash, S., Greenway, D., Thomas, W.G., Meyerhof, W., Roudnitzky, N. and Foster, S.R. (2015). Variability in human bitter taste sensitivity to chemically diverse compounds can be accounted for by differential TAS2R activation. Chem. Senses. 40:427–435.
  • Sarvan, I., Kramer, E., Bouwmeester, H., Dekker, M. and Verkerk, R. (2017). Sulforaphane formation and bioaccessibility are more affected by steaming time than meal composition during in vitro digestion of broccoli. Food Chemistry. 214:580–586.
  • Shankaranarayana, M. L., Raghavan, B., Abraham, K. O., Natarajan, C. P. and Brodnitz, H. H. (1974). Volatile sulfur compounds in food flavors. CRC Crit. Rev. Food Technol. 4:395–435.
  • Smutzer, G. and Devassy, R. K. (2016). Integrating TRPV1 Receptor Function with Capsaicin Psychophysics. Adv Pharmacol Sci. 2016:1512457.
  • Shapovalov, G., Ritaine, A., Skryma, R. and Prevarskaya, N. (2016). Role of TRP ion channels in cancer and tumorigenesis. Semin. Immunopathol. 38:357–369.
  • Spadone, J., Matthey-Doret, W. and Blank, I. (2006). Formation of methyl (methylthio) methyl disulfide in broccoli (Brassica oleracea (L.) var. italica). Dev. Food Sci. 43:309–314.
  • Springett, M. B. and Adams, J. B. (1989). Properties of Brussels sprouts thioglucosidase. Food Chem. 33:173–186.
  • Terada, Y., Masuda, H., Watanabe, T. (2015). Structure-Activity Relationship Study on Isothiocyanates: Comparison of TRPA1-Activating Ability between Allyl Isothiocyanate and Specific Flavor Components of Wasabi, Horseradish, and White Mustard. J. Nat. Prod. 78:1937–1941.
  • Ulrich, D., Krumbein, A., Schonhof, I. and Hoberg, E. (1998). Comparison of two sample preparation techniques for sniffing experiments with broccoli (Brassica oleracea var. italicaPlenck). Nahrung 42:392–4.
  • Valettea, L., Fernandeza, X., Poulaina, S., Loiseaua, A. M., Lizzani-Cuveliera, L., Levieilb, R. and Restier, L. (2003). Volatile constituents from Romanesco cauliflower. Food Chem. 80:353–358.
  • Van Doorn, H. E., Van der Kruk, G. C., Van Holst, G.-J., Raaijmakers-Ruijs, N. C., Postma, E., Groenweg, B. and Jongen, W. M. F. (1998). The glucosinolates sinigrin and progoitrin are important determinants for taste preference and bitterness from Brussels sprouts. J. Sci. Food Agric. 78:30–38.
  • Van Doorn, H. E. (1999). Development of vegetables with improved consumer quality: A case study in Brussels sprouts. PhD Thesis, Wageningen Universiteit, ISBN 90-5808-122-2
  • Van Eylen, D., Oey, I., Hendrickx, M. and Van Loey, A. (2007). Behavior of mustard seed (Sinapis alba L.) myrosinase during temperature/pressure treatments: A case study on enzyme activity and stability. Food Res Technol. 226:545–553.
  • Virtanen, A. I. (1965). Studies on organic sulphur compounds and other labile substances in plants. Phytochem. 4:207–228.
  • Wang, J. C., Hinrichs, A. L., Bertelsen, S., Stock, H., Budde, J. P., Dick, D. M., Bucholz, K. K., Rice, J., Saccone, N., Edenberg, H. J., Hesselbrock, V., Kuperman, S., Schuckit, M. A., Bierut, L. J. and Goate, A. M. (2007). Functional variants in TAS2R38 and TAS2R16 influence alcohol consumption in high-risk families of African-American origin. Alcohol Clin. Exp. Res. 31:209–215.
  • Yen, G. C. and Wei, Q. K. (1993). Myrosinase activity and total glucosinolate content of cruciferous vegetables, and some properties of cabbage myrosinase in Taiwan. J. Agric. Food Chem. 61:471–475.
  • Zabaras, D., Roohani, M., Krishnamurthy, R., Cochet, M. and Delahunty, C. (2013). Characterisation of taste-active extracts from raw Brassica oleracea vegetables. Food Funct. 4:592–601.
  • Zhang, Y. (2010). Allyl isothiocyanate as a cancer chemopreventive phytochemical. Mol. Nutr. Food Res. 54:127–135.

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