861
Views
3
CrossRef citations to date
0
Altmetric
Reviews

Biosynthesis, distribution, nutritional and organoleptic properties of bitter compounds in fruit and vegetables

, &

References

  • Akashi, T., T. Aoki, and S. Ayabe. 2005. Molecular and biochemical characterization of 2-hydroxyisoflavanone dehydratase. Involvement of carboxylesterase-like proteins in leguminous isoflavone biosynthesis. Plant Physiology 137 (3):882–91. doi: 10.1104/pp.104.056747.
  • Arora, S., P. Mohanpuria, G. S. Sidhu, I. S. Yadav, and V. Kumari. 2018. Cloning and characterization of limonoid glucosyltransferase from Kinnow Mandarin (Citrus reticulata Blanco). Food Technology and Biotechnology 56 (2):228–37. doi: 10.17113/ftb.56.02.18.5349.
  • Artigot, M.-P., M. Baes, J. Dayde, and M. Berger. 2013. Expression of flavonoid 6-hydroxylase candidate genes in normal and mutant soybean genotypes for glycitein content. Molecular Biology Reports 40 (7):4361–9. doi: 10.1007/s11033-013-2526-2.
  • Assefa, A. D., S. Choi, J.-E. Lee, J.-S. Sung, O.-S. Hur, N.-Y. Ro, H.-S. Lee, S.-W. Jang, and J.-H. Rhee. 2019. Identification and quantification of selected metabolites in differently pigmented leaves of lettuce (Lactuca sativa L.) cultivars harvested at mature and bolting stages. BMC Chemistry 13 (1):56. doi: 10.1186/s13065-019-0570-2.
  • Balkema-Boomstra, A. G., S. Zijlstra, F. W. A. Verstappen, H. Inggamer, P. E. Mercke, M. A. Jongsma, and H. J. Bouwmeester. 2003. Role of cucurbitacin C in resistance to spider mite (Tetranychus urticae) in cucumber (Cucumis sativus L.). Journal of Chemical Ecology 29 (1):225–35. doi: 10.1023/A:1021945101308.
  • Bischoff, T. A., C. J. Kelley, Y. Karchesy, M. Laurantos, P. Nguyen-Dinh, and A. G. Arefi. 2004. Antimalarial activity of Lactucin and Lactucopicrin: Sesquiterpene lactones isolated from Cichorium intybus L. Journal of Ethnopharmacology 95 (2-3):455–7. doi: 10.1016/j.jep.2004.06.031.
  • Bloxham, C. J., S. R. Foster, and W. G. Thomas. 2020. A Bitter Taste in Your Heart. Frontiers in Physiology 11:431. doi: 10.3389/fphys.2020.00431.
  • Bolarinwa, I. F., C. Orfila, and M. R. Morgan. 2014. Amygdalin content of seeds, kernels and food products commercially-available in the UK. Food Chemistry 152:133–9. doi: 10.1016/j.foodchem.2013.11.002.
  • Brockhoff, A., M. Behrens, A. Massarotti, G. Appendino, and W. Meyerhof. 2007. Broad tuning of the human bitter taste receptor hTAS2R46 to various sesquiterpene lactones, clerodane and labdane diterpenoids, strychnine, and denatonium. Journal of Agricultural and Food Chemistry 55 (15):6236–43. doi: 10.1021/jf070503p.
  • Busta, L., W. Yim, E. W. LaBrant, P. Wang, L. Grimes, K. Malyszka, J. C. Cushman, P. Santos, D. K. Kosma, and E. B. Cahoon. 2018. Identification of genes encoding enzymes catalyzing the early steps of carrot polyacetylene biosynthesis. Plant Physiology 178 (4):1507–21. doi: 10.1134/S0003683813030150.
  • Cárdenas, P. D., P. D. Sonawane, J. Pollier, R. Vanden Bossche, V. Dewangan, E. Weithorn, L. Tal, S. Meir, I. Rogachev, S. Malitsky, et al. 2016. GAME9 regulates the biosynthesis of steroidal alkaloids and upstream isoprenoids in the plant mevalonate pathway. Nature Communications 7:10654. doi: 10.1038/ncomms10654.
  • Chadwick, M., F. Gawthrop, R. W. Michelmore, C. Wagstaff, and L. Methven. 2016. Perception of bitterness, sweetness and liking of different genotypes of lettuce. Food Chemistry 197 (Pt A):66–74. doi: 10.1016/j.foodchem.2015.10.105.
  • Chan, K. T., F. Y. Meng, Q. Li, C. Y. Ho, T. S. Lam, Y. To, W. H. Lee, M. Li, K. H. Chu, and M. Toh. 2010. Cucurbitacin B induces apoptosis and S phase cell cycle arrest in BEL-7402 human hepatocellular carcinoma cells and is effective via oral administration. Cancer Letters 294 (1):118–24. doi: 10.1016/j.canlet.2010.01.029.
  • Chaudhary, P. R., X. Yu, G. K. Jayaprakasha, and B. S. Patil. 2017. Influence of storage temperature and low‐temperature conditioning on the levels of health‐promoting compounds in Rio Red grapefruit. Food Science & Nutrition 5 (3):545–53. doi: 10.1002/fsn3.429.
  • Chen, J., G. Li, H. Zhang, Z. Yuan, W. Li, Z. Peng, M. Shi, W. Ding, H. Zhang, Y. Cheng, et al. 2021. Primary bitter taste of citrus is linked to a functional allele of the 1, 2-rhamnosyltransferase gene originating from citrus grandis. Journal of Agricultural and Food Chemistry 69 (34):9869–82. doi: 10.1021/acs.jafc.1c01211.
  • Chen, J., S. Li, J. Xu, F. Ding, Z. Wang, Y. Cheng, and X. Deng. 2015. Concentration and distribution of main bitter compounds in fruittissues of ‘Oroblanco’ Citrus grandis L. × Citrus paradisi Macf). Scientia Horticulturae 193:84–9. doi: 10.1016/j.scienta.2015.05.034.
  • Chen, J., Z. Yuan, H. Zhang, W. Li, M. Shi, Z. Peng, M. Li, J. Tian, X. Deng, Y. Cheng, et al. 2019. Cit1,2RhaT and two novel CitdGlcTs participate in flavor-related flavonoid metabolism during citrus fruit development. Journal of Experimental Botany 70 (10):2759–71. doi: 10.1093/jxb/erz081.
  • D’Antuono, L. F., F. Ferioli, and M. A. Manco. 2016. The impact of sesquiterpene lactones and phenolics on sensory attributes: An investigation of a curly endive and escarole germplasm collection. Food Chemistry 199:238–45. doi: 10.1016/j.foodchem.2015.12.002.
  • Dagan-Wiener, A., A. Di Pizio, I. Nissim, M. S. Bahia, N. Dubovski, E. Margulis, and M. Y. Niv. 2019. BitterDB: Taste ligands and receptors database in 2019. Nucleic Acids Research 47 (D1):D1179–D1185. doi: 10.1093/nar/gky974.
  • Danciu, C., S. Avram, I. Z. Pavel, R. Ghiulai, C. A. Dehelean, A. Ersilia, D. Minda, C. Petrescu, E.-A. Moaca, and C. Soica. 2018. Main isoflavones found in dietary sources as natural anti-inflammatory agents. Current Drug Targets 19 (7):841–53. doi: 10.2174/1389450118666171109150731.
  • Dea, S., A. Plotto, J. A. Manthey, S. Raithore, M. Irey, and E. Baldwin. 2013. Interactions and thresholds of limonin and nomilin in bitterness perception in orange juice and other matrices. Journal of Sensory Studies 28 (4):311–23. doi: 10.1111/joss.12046.
  • Deshaware, S., S. Gupta, R. S. Singhal, M. Joshi, and P. S. Variyar. 2018. Debittering of bitter gourd juice using beta-cyclodextrin: Mechanism and effect on antidiabetic potential. Food Chemistry 262:78–85. doi: 10.1016/j.foodchem.2018.04.077.
  • Drewnowski, A, and C. Gomez-Carneros. 2000. Bitter taste, phytonutrients, and the consumer: A review. The American Journal of Clinical Nutrition 72 (6):1424–35. ISSN:0002-9165.
  • Duarte-Sierra, A., F. Nadeau, P. Angers, D. Michaud, and J. Arul. 2019. UV-C hormesis in broccoli florets: Preservation, phyto-compounds and gene expression. Postharvest Biology and Technology 157:110965. doi: 10.1016/j.postharvbio.2019.110965.
  • Fan, S., C. Zhang, T. Luo, J. Wang, Y. Tang, Z. Chen, and L. Yu. 2019. Limonin: A review of its pharmacology, toxicity, and pharmacokinetics. Molecules 24 (20):3679. doi: 10.3390/molecules24203679.
  • Ferioli, F., M. A. Manco, and L. F. D’Antuono. 2015. Variation of sesquiterpene lactones and phenolics in chicory and endive germplasm. Journal of Food Composition and Analysis 39:77–86. doi: 10.1016/j.jfca.2014.11.014.
  • Fernandez-Calvo, P., S. Inigo, G. Glauser, R. Vanden Bossche, M. Tang, B. Li, R. De Clercq, A. N. Durand, D. Eeckhout, K. Gevaert, et al. 2020. FRS7 and FRS12 recruit NINJA to regulate expression of glucosinolate biosynthesis genes. The New Phytologist 227 (4):1124–37. doi: 10.1111/nph.16586.
  • Friedman, M. 2013. Anticarcinogenic, Cardioprotective, and other health benefits of tomato compounds lycopene, alpha-tomatine, and tomatidine in pure form and in fresh and processed tomatoes. Journal of Agricultural and Food Chemistry 61 (40):9534–50. doi: 10.1021/jf402654e.
  • Gioia, F. D., P. Avato, F. Serio, and M. P. Argentieri. 2018. Glucosinolate profile of Eruca sativa, Diplotaxis tenuifolia and Diplotaxis erucoides grown in soil and soilless systems. Journal of Food Composition and Analysis 69:197–204. doi: 10.1016/j.jfca.2018.01.022.
  • Gugała, M., K. Zarzecka, H. Dołęga, M. Niewęgłowski, and A. Sikorska. 2016. The effect of biostimulants and herbicides on glycoalkaloid accumulation in potato. Plant, Soil and Environment 62 ( 6):256–60. doi: 10.17221/187/2016-PSE.
  • Hayashi, S., E. Nakamura, N. Takahashi, A. Yamaguchi, H. Matsui, S. J. Hagen, and K. Takeuchi. 2009. W1552 impairment by allyl isothiocyanate of gastric epithelial wound repair through inhibition of ion transporters. Gastroenterology 136 (5):A-690–690. ISSN:0016-5085. doi: 10.1016/S0016-5085(09)63177-2.
  • He, X.-Y., L.-J. Wu, W.-X. Wang, P.-J. Xie, Y.-H. Chen, and F. Wang. 2020. Amygdalin: A pharmacological and toxicological review. Journal of Ethnopharmacology 254:112717. doi: 10.1016/j.jep.2020.112717.
  • Hsu, W. J., M. Berhow, G. H. Robertson, and S. Hasegawa. 1998. Limonoids and flavonoids in juices of oroblanco and melogold grapefruit hybrids. Journal of Food Science 63 (1):57–60. ISSN:0018-5345. doi: 10.1111/j.1365-2621.1998.tb15675.x.
  • Hua, D., J. Fu, L. Liu, X. Yang, Q. Zhang, and M. Xie. 2019. Change in bitterness, accumulation of cucurbitacin B and expression patterns of CuB biosynthesis-related genes in melon during fruit development. The Horticulture Journal 88 (2):253–62. doi: 10.2503/hortj.UTD-004.
  • Itkin, M., U. Heinig, O. Tzfadia, A. J. Bhide, B. Shinde, P. D. Cárdenas, S. E. Bocobza, T. Unger, S. Malitsky, R. Finkers, et al. 2013. Biosynthesis of antinutritional alkaloids in solanaceous crops is mediated by clustered genes. Science (New York, N.Y.) 341 (6142):175–9. doi: 10.1126/science.1240230.
  • Jasper, J., C. Wagstaff, and L. Bell. 2020. Growth temperature influences postharvest glucosinolate concentrations and hydrolysis product formation in first and second cuts of rocket salad. Postharvest Biology and Technology 163:111157. doi: 10.1016/j.postharvbio.2020.111157.
  • Jorgensen, K., A. V. Morant, M. Morant, N. B. Jensen, C. E. Olsen, R. Kannangara, M. S. Motawia, B. L. Moller, and S. Bak. 2011. Biosynthesis of the cyanogenic glucosides linamarin and lotaustralin in cassava: Isolation, biochemical characterization, and expression pattern of CYP71E7, the oxime-metabolizing Cytochrome P450 enzyme. Plant Physiology 155 (1):282–92. doi: 10.1104/pp.110.164053.
  • Joshi, R. S., S. S. Jagdale, S. B. Bansode, S. S. Shankar, M. B. Tellis, V. K. Pandya, A. Chugh, A. P. Giri, and M. J. Kulkarni. 2021. Discovery of potential multi-target-directed ligands by targeting host-specific SARS-CoV-2 structurally conserved main protease. Journal of Biomolecular Structure & Dynamics 39 (9):3099–114. doi: 10.1080/07391102.2020.1760137.
  • Kazachkova, Y., I. Zemach, S. Panda, S. Bocobza, A. Vainer, I. Rogachev, Y. Dong, S. Ben-Dor, D. Veres, C. Kanstrup, et al. 2021. The GORKY glycoalkaloid transporter is indispensable for preventing tomato bitterness. Nature Plants 7 (4):468–80. doi: 10.1038/s41477-021-00865-6.
  • Kidmose, U., S. L. Hansen, L. P. Christensen, M. Edelenbos, E. Larsen, and R. Nørbaek. 2006. Effects of genotype, root size, storage, and processing on bioactive compounds in organically grown carrots (Daucus carota L.). Journal of Food Science 69 (9):S388–S94. doi: 10.1111/j.1365-2621.2004.tb09955.x.
  • Kim, H.-J., E.-J. Choi, H. S. Kim, C.-W. Choi, S.-W. Choi, S.-L. Kim, W.-D. Seo, and S. H. Do. 2019. Soyasaponin Ab alleviates postmenopausal obesity through browning of white adipose tissue. Journal of Functional Foods 57:453–64. doi: 10.1016/j.jff.2019.03.051.
  • Kim, S. J., K. Fujii, Z. I. S. Mohamed, H. W. Kim, and G. Ishii. 2008. Identification and quantitative determination of glucosinolates in Brassica napus cv. Hanakkori. Food Science & Biotechnology 17:1097–101.
  • Lee, H.-W., D.-K. Rhee, B.-O. Kim, and S. Pyo. 2018. Inhibitory effect of sinigrin on adipocyte differentiation in 3T3-L1 cells: Involvement of AMPK and MAPK pathways. Biomedicine & Pharmacotherapy = Biomedecine & Pharmacotherapie 102:670–80. doi: 10.1016/j.biopha.2018.03.124.
  • Li, X., C. Zhang, L. Liu, and M. Gu. 2020. Existing bitter medicines for fighting 2019-nCoV-associated infectious diseases. FASEB Journal 34 (5):6008–16. doi: 10.1096/fj.202000502.
  • Liang, J, and D. Chen. 2019. Advances in research on the anticancer mechanism of the natural compound cucurbitacin from Cucurbitaceae plants: A review. Traditional Medicine Research 4 (2):68–81–81. doi: 10.12032/TMR20190225102.
  • Lin, J., Y. Cheng, T. Wang, L. Tang, Y. Sun, X. Lu, and H. Yu. 2016. Soyasaponin Ab inhibits lipopolysaccharide-induced acute lung injury in mice. International Immunopharmacology 30:121–8. doi: 10.1016/j.intimp.2015.12.001.
  • Liu, Q., A. B. Kashkooli, D. Manzano, I. Pateraki, L. Richard, P. Kolkman, M. Fatima Lucas, V. Guallar, R. C. H. de Vos, M. C. R. Franssen, et al. 2018. Kauniolide synthase is a P450 with unusual hydroxylation and cyclization-elimination activity. Nature Communications 9 (1):4657. doi: 10.1038/s41467-018-06565-8.
  • Liu, Z., K. Ryota, M.-I. Tomomi, A. Alaa, K. Sun-Ju, and M.-N. Akiko. 2020. Sulfur deficiency-induced glucosinolate catabolism attributed to two β-glucosidases, BGLU28 and BGLU30, is required for plant growth maintenance under sulfur deficiency. Plant and Cell Physiology 61:803–13. doi: 10.1093/pcp/pcaa006.
  • Louarn, S., A. Nawrocki, M. Edelenbos, D. F. Jensen, O. N. Jensen, D. B. Collinge, and B. Jensen. 2012. The influence of the fungal pathogen Mycocentrospora acerina on the proteome and polyacetylenes and 6-methoxymellein in organic and conventionally cultivated carrots (Daucus carota) during post harvest storage. Journal of Proteomics 75 (3):962–77. doi: 10.1016/j.jprot.2011.10.014.
  • Lu, P., C. H. Zhang, L. M. Lifshitz, and R. Zhuge. 2017. Extraoral bitter taste receptors in health and disease. The Journal of General Physiology 149 (2):181–97. doi: 10.1085/jgp.201611637.
  • Lucini, L, and L. Bernardo. 2015. Comparison of proteome response to saline and zinc stress in lettuce. Frontiers in Plant Science 6:240. doi: 10.3389/fpls.2015.00240.
  • Mertens, J., J. Pollier, R. Vanden Bossche, I. Lopez-Vidriero, J. M. Franco-Zorrilla, and A. Goossens. 2016. The bHLH transcription factors TSAR1 and TSAR2 regulate triterpene saponin biosynthesis in Medicago truncatula. Plant Physiology 170 (1):194–210. doi: 10.1104/pp.15.01645.
  • Meyerhof, W., C. Batram, C. Kuhn, A. Brockhoff, E. Chudoba, B. Bufe, G. Appendino, and M. Behrens. 2010. The molecular receptive ranges of human TAS2R bitter taste receptors. Chemical Senses 35 (2):157–70. doi: 10.1093/chemse/bjp092.
  • Miller, V., A. Mente, M. Dehghan, S. Rangarajan, X. Zhang, S. Swaminathan, G. Dagenais, R. Gupta, V. Mohan, S. Lear, et al. 2017. Fruit, vegetable, and legume intake, and cardiovascular disease and deaths in 18 countries (PURE): A prospective cohort study. Lancet 390 (10107):2037–49. doi: 10.1016/S0140-6736(17)32253-5.
  • Olsson, M. E., K. E. Gustavsson, S. E. Svensson, and D. Hansson. 2018. Different types of organic pop-up fertilizers in carrot cultivation: Effects on the concentrations of polyacetylenes and sugars. Scientia Horticulturae 230:126–33. doi: 10.1016/j.scienta.2017.10.010.
  • Onishi, S., K. Nishi, S. Yasunaga, A. Muranaka, K. Maeyama, A. Kadota, and T. Sugahara. 2014. Nobiletin, a polymethoxy flavonoid, exerts anti-allergic effect by suppressing activation of phosphoinositide 3-kinase. Journal of Functional Foods 6:606–14. doi: 10.1016/j.jff.2013.12.005.
  • Ordonez-Vasquez, A., V. A. Arzola, M. A. De Garza-Ramo, V. H. Urrutia-Ba, and F. Suárez-Obando. 2019. Toxicity, teratogenicity and anti-cancer activity of alpha-solanine: A perspective on anti-cancer potential. International Journal of Pharmacology 15 (3):301–10. doi: 10.3923/ijp.2019.301.310.
  • Paradiso, R., C. Arena, Y. Rouphael, L. d’Aquino, K. Makris, P. Vitaglione, and S. De Pascale. 2019. Growth, photosynthetic activity and tuber quality of two potato cultivars in controlled environment as affected by light source. Plant Biosystems 153 (5):725–35. doi: 10.1080/11263504.2018.1549603.
  • Pena-Espinoza, M., A. H. Valente, L. Bornancin, H. T. Simonsen, S. M. Thamsborg, A. R. Williams, and R. Lopez-Munoz. 2020. Anthelmintic and metabolomic analyses of chicory (Cichorium intybus) identify an industrial by-product with potent in vitro antinematodal activity. Veterinary Parasitology 280:109088. doi: 10.1016/j.vetpar.2020.109088.
  • Qiao, N., Q. Liu, H. Meng, and D. Zhao. 2014. Haemolytic activity and adjuvant effect of soyasaponins and some of their derivatives on the immune responses to ovalbumin in mice. International Immunopharmacology 18 (2):333–9. doi: 10.1016/j.intimp.2013.12.017.
  • Ramezani, M., F. Rahmani, and A. Dehestani. 2017. Comparison between the effects of potassium phosphite and chitosan on changes in the concentration of Cucurbitacin E and on antibacterial property of Cucumis sativus. BMC Complementary and Alternative Medicine 17 (1):295. doi: 10.1186/s12906-017-1808-y.
  • Ramu, V., W.-S., Shim, E.-J ., Yeo, and S. Y. Kim. 2017. Lactucopicrin potentiates neuritogenesis and neurotrophic effects by regulating Ca2+/CaMKII/ATF1 signaling pathway. Journal of Ethnopharmacology 198:174–83. doi: 10.1016/j.jep.2016.12.035.
  • Ren, Y., Y. Zhou, X. Chen, and Y. Ye. 2005. Discovery, structural determination and anticancer activities of lactucinlike guaianolides. Letters in Drug Design & Discovery 2 (6):444–50. doi: 10.2174/1570180054771581.
  • Roland, W. S. U., L. van Buren, H. Gruppen, M. Driesse, R. J. Gouka, G. Smit, and J. P. Vincken. 2013. Bitter taste receptor activation by flavonoids and isoflavonoids: Modeled structural requirements for activation of hTAS2R14 and hTAS2R39. Journal of Agricultural and Food Chemistry 61 (44):10454–66. doi: 10.1021/jf403387p.
  • Sanchez-Perez, R., S. Pavan, R. Mazzeo, C. Moldovan, R. Aiese Cigliano, J. Del Cueto, F. Ricciardi, C. Lotti, L. Ricciardi, F. Dicenta, et al. 2019. Mutation of a bHLH transcription factor allowed almond domestication. Science (New York, N.Y.) 364 (6445):1095–8. doi: 10.1126/science.aav8197.
  • Sayama, T., E. Ono, K. Takagi, Y. Takada, M. Horikawa, Y. Nakamoto, A. Hirose, H. Sasama, M. Ohashi, H. Hasegawa, et al. 2012. The Sg-1 glycosyltransferase locus regulates structural diversity of triterpenoid saponins of soybean. The Plant Cell 24 (5):2123–38. doi: 10.1105/tpc.111.095174.
  • Sawai, S., K. Ohyama, S. Yasumoto, H. Seki, T. Sakuma, T. Yamamoto, Y. Takebayashi, M. Kojima, H. Sakakibara, T. Aoki, et al. 2014. Sterol side chain reductase 2 is a key enzyme in the biosynthesis of cholesterol, the common precursor of toxic steroidal glycoalkaloids in potato. The Plant Cell 26 (9):3763–74. doi: 10.1105/tpc.114.130096.
  • Seguin, P., P. Chennupati, G. Tremblay, and W. Liu. 2014. Crop management, genotypes, and environmental factors affect soyasaponin b concentration in soybean. Journal of Agricultural and Food Chemistry 62 (29):7160–5. doi: 10.1021/jf500966t.
  • Seljasen, R., H. L. Kristensen, C. Lauridsen, G. S. Wyss, U. Kretzschmar, I. Birlouez-Aragone, and J. Kahl. 2013. Quality of carrots as affected by pre- and postharvest factors and processing. Journal of the Science of Food and Agriculture 93 (11):2611–26. doi: 10.1002/jsfa.6189.
  • Senica, M., F. Stampar, R. Veberic, and M. Mikulic-Petkovsek. 2019. Cyanogenic glycosides and phenolics in apple seeds and their changes during long term storage. Scientia Horticulturae 255:30–6. doi: 10.1016/j.scienta.2019.05.022.
  • Seo, M. S., M. Jin, J. H. Chun, S. J. Kim, B. S. Park, S. H. Shon, and J. S. Kim. 2016. Functional analysis of three BrMYB28 transcription factors controlling the biosynthesis of glucosinolates in Brassica rapa. Plant Molecular Biology 90 (4-5):503–16. doi: 10.1007/s11103-016-0437-z.
  • Shang, Y., Y. Ma, Y. Zhou, H. Zhang, L. Duan, H. Chen, J. Zeng, Q. Zhou, S. Wang, W. Gu, et al. 2014. Biosynthesis, regulation, and domestication of bitterness in cucumber. Science (New York, N.Y.) 346 (6213):1084–8. doi: 10.1126/science.1259215.
  • Shen, K.-H., A. C.-H. Liao, J.-H. Hung, W.-J. Lee, K.-C. Hu, P.-T. Lin, R.-F. Liao, and P.-S. Chen. 2014. Alpha-solanine inhibits invasion of human prostate cancer cell by suppressing epithelial-mesenchymal transition and MMPs expression. Molecules (Basel, Switzerland) 19 (8):11896–914. doi: 10.3390/molecules190811896.
  • Shibuya, M., K. Nishimura, N. Yasuyama, and Y. Ebizuka. 2010. Identification and characterization of glycosyltransferases involved in the biosynthesis of soyasaponin I in Glycine max. FEBS Letters 584 (11):2258–64. doi: 10.1016/j.febslet.2010.03.037.
  • Singh, B., J. P. Singh, A. Kaur, and N. Singh. 2020. Phenolic composition, antioxidant potential and health benefits of citrus peel. Food Research International (Ottawa, Ont.) 132:109114– doi: 10.1016/j.foodres.2020.109114.
  • Singh, N., F. A. Shaik, Y. Myal, and P. Chelikani. 2020. Chemosensory bitter taste receptors T2R4 and T2R14 activation attenuates proliferation and migration of breast cancer cells. Molecular and Cellular Biochemistry 465 (1-2):199–214. doi: 10.1007/s11010-019-03679-5.
  • Sonawane, P. D., J. Pollier, S. Panda, J. Szymanski, H. Massalha, M. Yona, T. Unger, S. Malitsky, P. Arendt, L. Pauwels, et al. 2017. Plant cholesterol biosynthetic pathway overlaps with phytosterol metabolism. Nature Plants 3 (1):16205. doi: 10.1038/nplants.2016.205.
  • Sonderby, I. E., F. Geu-Flores, and B. A. Halkier. 2010. Biosynthesis of glucosinolates - gene discovery and beyond. Trends in Plant Science 15 (5):283–90. doi: 10.1016/j.tplants.2010.02.005.
  • Sugiyama, A., Y. Yamazaki, S. Hamamoto, H. Takase, and K. Yazaki. 2017. Synthesis and Secretion of Isoflavones by Field-Grown Soybean. Plant & Cell Physiology 58 (9):1594–600. doi: 10.1093/pcp/pcx084.
  • Takase, S., K. Kera, Y. Nagashima, K. Mannen, T. Hosouchi, S. Shinpo, M. Kawashima, Y. Kotake, H. Yamada, Y. Saga, et al. 2019. Allylic hydroxylation of triterpenoids by a plant cytochrome P450 triggers key chemical transformations that produce a variety of bitter compounds. Journal of Biological Chemistry 294 (49):18662–73. jbc.RA119.009944. doi: 10.1074/jbc.RA119.009944.
  • Tamura, Y., T. Mori, R. Nakabayashi, M. Kobayashi, K. Saito, S. Okazaki, N. Wang, and M. Kusano. 2018. Metabolomic evaluation of the quality of leaf lettuce grown in practical plant factory to capture metabolite signature. Frontiers in Plant Science 9:665. doi: 10.3389/fpls.2018.00665.
  • Testone, G., G. Mele, E. di Giacomo, G. C. Tenore, M. Gonnella, C. Nicolodi, G. Frugis, M. A. Iannelli, G. Arnesi, A. Schiappa, et al. 2019. Transcriptome driven characterization of curly- and smooth-leafed endives reveals molecular differences in the sesquiterpenoid pathway. Horticulture Research 6:1. doi: 10.1038/s41438-018-0066-6.
  • Thodberg, S., J. Del Cueto, R. Mazzeo, S. Pavan, C. Lotti, F. Dicenta, E. H. J. Neilson, B. L. Moller, and R. Sanchez-Perez. 2018. Elucidation of the amygdalin pathway reveals the metabolic basis of bitter and sweet almonds (Prunus dulcis). Plant Physiology 178 (3):1096–111. doi: 10.1104/pp.18.00922.
  • Usuki, T., M. Sato, S. Hara, Y. Yoshimoto, R. Kondo, S. Zimmermann, M. Kaiser, R. Brun, M. Hamburger, and M. Adams. 2014. Antitrypanosomal structure–activity-relationship study of synthetic cynaropicrin derivatives. Bioorganic & Medicinal Chemistry Letters 24 (3):794–8. doi: 10.1016/j.bmcl.2013.12.099.
  • Valcarcel, J., K. Reilly, M. Gaffney, and N. O’Brien. 2014. Effect of genotype and environment on the glycoalkaloid content of rare, heritage, and commercial potato varieties. Journal of Food Science 79 (5):T1039–T1048. doi: 10.1111/1750-3841.12443.
  • Vantoai, T. T., J. Lee, P. D. F. P. Goulart, J. G. Shannon, J. D. Alves, H. T. Nguyen, O. Yu, M. A. Rahman, R. Islam, and M. G. Brazil. 2012. Soybean (Glycine max L. Merr.) seed composition response to soil flooding stress. Journal of Food Agriculture & Environment 10:795–804. ISSN:1459-0255
  • Vranova, E., D. Coman, and W. Gruissem. 2013. Network analysis of the MVA and MEP pathways for isoprenoid synthesis. Annual Review of Plant Biology 64:665–700. doi: 10.1146/annurev-arplant-050312-120116.
  • Wulfkuehler, S., C. Gras, and R. Carle. 2013. Sesquiterpene lactone content and overall quality of fresh-cut witloof chicory (Cichorium intybus L. var. foliosum Hegi) as affected by different washing procedures. Journal of Agricultural and Food Chemistry 61 (32):7705–14. doi: 10.1021/jf402189v.
  • Wulfkuehler, S., C. Gras, and R. Carle. 2014. Influence of light exposure during storage on the content of sesquiterpene lactones and photosynthetic pigments in witloof chicory (Cichorium intybus L. var. foliosum Hegi). LWT - Food Science and Technology 58 (2):417–26. doi: 10.1016/j.lwt.2014.04.017.
  • Xi, W., B. Fang, Q. Zhao, B. Jiao, and Z. Zhou. 2014. Flavonoid composition and antioxidant activities of Chinese local pummelo (Citrus grandis Osbeck.) varieties. Food Chemistry 161:230–8. doi: 10.1016/j.foodchem.2014.04.001.
  • Xie, C., X. Wang, R. L. Young, M. Horowitz, C. K. Rayner, and T. Wu. 2018. Role of intestinal bitter sensing in enteroendocrine hormone secretion and metabolic control. Frontiers in Endocrinology 9:576. doi: 10.3389/fendo.2018.00576.
  • Yano, R., K. Takagi, Y. Takada, K. Mukaiyama, C. Tsukamoto, T. Sayama, A. Kaga, T. Anai, S. Sawai, K. Ohyama, et al. 2017. Metabolic switching of astringent and beneficial triterpenoid saponins in soybean is achieved by a loss-of-function mutation in cytochrome P450 72A69. The Plant Journal : For Cell and Molecular Biology 89 (3):527–39. doi: 10.1111/tpj.13403.
  • Yildirim, A. N., F. Akinci-Yildirim, M. Polat, B. Şan, and Y. Sesli. 2014. Amygdalin content in kernels of several almond cultivars grown in turkey. HortScience 49 (10):1268–70. doi: 10.21273/HORTSCI.49.10.1268.
  • Zhang, Y., F. Chen, J. Chen, S. Huang, J. Chen, J. Huang, N. Li, S. Sun, X. Chu, and L. Zha. 2016. Soyasaponin Bb inhibits the recruitment of toll-like receptor 4 (TLR4) into lipid rafts and its signaling pathway by suppressing the nicotinamide adenine dinucleotide phosphate (NADPH) oxidase-dependent generation of reactive oxygen species. Molecular Nutrition & Food Research 60 (7):1532–43. doi: 10.1002/mnfr.201600015.
  • Zhao, P., P. Liu, J. Shao, C. Li, B. Wang, X. Guo, B. Yan, Y. Xia, and M. Peng. 2015. Analysis of different strategies adapted by two cassava cultivars in response to drought stress: Ensuring survival or continuing growth. Journal of Experimental Botany 66 (5):1477–88. doi: 10.1093/jxb/eru507.
  • Zhao, X., X. Zeng, N. Lin, S. Yu, A. R. Fernie, and J. Zhao. 2021. CsbZIP1-CsMYB12 mediates the production of bitter-tasting flavonols in tea plants (Camellia sinensis) through a coordinated activator-repressor network. Horticulture Research 8 (1):18. doi: 10.1038/s41438-021-00545-8.
  • Zhou, C., J. G. Tokuhisa, D. R. Bevan, and A. Esen. 2012. Properties of β-thioglucoside hydrolases (TGG1 and TGG2) from leaves of Arabidopsis thaliana. Plant Science 191-192:82–92. doi: 10.1016/j.plantsci.2012.02.004.
  • Zhou, Y., Y. Ma, J. Zeng, L. Duan, X. Xue, H. Wang, T. Lin, Z. Liu, K. Zeng, Y. Zhong, et al. 2016. Convergence and divergence of bitterness biosynthesis and regulation in Cucurbitaceae. Nature Plants 2 (12):1–8. doi: 10.1038/nplants.2016.183.
  • Zou, C., G. Liu, S. Liu, S. Liu, Q. Song, J. Wang, Q. Feng, Y. Su, and S. Li. 2018. Cucurbitacin B acts a potential insect growth regulator by antagonizing 20-hydroxyecdysone activity. Pest Management Science 74 (6):1394–403. doi: 10.1002/ps.4817.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.