5-n-Alk(en)ylresorcinol accumulation across developmental stages of triticale through comparative metabolite profiling: implications of fresh and dry basis

References

• Arent, E., & Zannini, E. (2013). Cereal grains for the food and beverage industries (1st ed.). Woodhead publishing. https://doi.org/10.1533/9780857098924.201
   Google Scholar
• Athukorala, Y., Hosseinian, F. S., & Mazza, G. (2010). Extraction and fractionation of alkylresorcinols from triticale bran by two-step supercritical carbon dioxide. LWT - Food Science and Technology, 43(4), 660–11. https://doi.org/10.1016/j.lwt.2009.11.008
   Web of Science ®Google Scholar
• Baerson, S. R., Schröder, J., Cook, D., Rimando, A. M., Pan, Z., Dayan, F. E., Noonan, B. P., & Duke, S. O. (2010). Alkylresorcinol biosynthesis in plants. Plant Signaling & Behavior, 5(10), 1286–1289. https://doi.org/10.4161/psb.5.10.13062
   PubMedGoogle Scholar
• Barrero, A., Cabrera, E., Rodriguez, I., & Planelles, F. (1994). Alkylresorcinols and isocoumarins from ononis pubescens. Phytochemistry, 35(2), 493–498. https://doi.org/10.1016/S0031-9422(00)94789-7
   Web of Science ®Google Scholar
• Buitrago, D., Buitrago-Villanueva, I., Barbosa-Cornelio, R., & Coy-Barrera, E. (2019). Comparative examination of antioxidant capacity and fingerprinting of unfractionated extracts from different plant parts of quinoa (chenopodium quinoa) grown under greenhouse conditions. Antioxidants, 8(8), 238. https://doi.org/10.3390/antiox8080238
   Web of Science ®Google Scholar
• Chong, J., Wishart, D. S., & Xia, J. (2019). Using MetaboAnalyst 4.0 for comprehensive and integrative metabolomics data analysis. Current Protocols in Bioinformatics, 68(1), e86. https://doi.org/10.1002/cpbi.86
   PubMedGoogle Scholar
• Cooper, K. V., Mergoum, M., Singh, P. K., & Pen, R. J. (2009). Triticale: A ‘“new”’ crop with old challenges. In M. J. Carena (Ed.), Cereals. Springer US. https://doi.org/10.1007/978-0-387-72297-9
   Google Scholar
• Francisco, J. D. C., Danielsson, B., Kozubek, A., & Dey, E. S. (2005). Application of supercritical carbon dioxide for the extraction of alkylresorcinols from rye bran. The Journal of Supercritical Fluids, 35(3), 220–226. https://doi.org/10.1016/j.supflu.2005.01.010
   Web of Science ®Google Scholar
• Golovina, E. A., Hoekstra, F. A., & Hemminga, M. A. (1998). Drying increases intracellular partitioning of amphiphilic substances into the lipid Phase1: Impact on membrane permeability and significance for desiccation tolerance. Plant Physiology, 118(3), 975–986. https://doi.org/10.1104/pp.118.3.975
   PubMed Web of Science ®Google Scholar
• Grayer, R. J., & Kokubun, T. (2001). Plant-fungal interactions: The search for phytoalexins and other antifungal compounds from higher plants. Phytochemistry, 56(3), 253–263. https://doi.org/10.1016/S0031-9422(00)00450-7
   PubMed Web of Science ®Google Scholar
• Hess, M., Barralis, G., Bleiholder, H., Buhr, L., Eggers, T., Hack, H., & Stauss, R. (1997). Use of the extended BBCH scale—general for the descriptions of the growth stages of mono; and dicotyledonous weed species. Weed Research, 37(6), 433–441. https://doi.org/10.1046/j.1365-3180.1997.d01-70.x
   Web of Science ®Google Scholar
• Hussain, H. A., Hussain, S., Khaliq, A., Ashraf, U., Anjum, S. A., Men, S., & Wang, L. (2018). Chilling and drought stresses in crop plants: Implications, cross talk, and potential management opportunities. Frontiers in Plant Science, 9(April), 1–21. https://doi.org/10.3389/fpls.2018.00393
   PubMedGoogle Scholar
• Isah, T. (2019). Stress and defense responses in plant secondary metabolites production. Biological Research, 52(1), 39. https://doi.org/10.1186/s40659-019-0246-3
   PubMed Web of Science ®Google Scholar
• Jenks, M. A., Joly, R. J., Peters, P. J., Rich, P. J., Axtell, J. D., & Ashworth, E. N. (1994). Chemically induced cuticle mutation affecting epidermal conductance to water vapor and disease susceptibility in sorghum bicolor (L.) Moench. Plant Physiology, 105(4), 1239–1245. https://doi.org/10.1104/pp.105.4.1239
   PubMed Web of Science ®Google Scholar
• Ji, X., & Jetter, R. (2008). Very long chain alkylresorcinols accumulate in the intracuticular wax of rye (secale cereale L.) leaves near the tissue surface. Phytochemistry, 69(5), 1197–1207. https://doi.org/10.1016/j.phytochem.2007.12.008
   PubMed Web of Science ®Google Scholar
• Jones, W. P., & Kinghorn, A. D. (2012). Extraction of plant secondary metabolites. Natural Products Isolation, 3(12), 341–366. https://doi.org/10.1007/978-1-61779-624-1_13
   Google Scholar
• Kienzle, S., Carle, R., Sruamsiri, P., Tosta, C., & Neidhart, S. (2014). Occurrence of alk(en)ylresorcinols in the fruits of two mango (mangifera indica L.) cultivars during on-tree maturation and postharvest storage. Journal of Agricultural and Food Chemistry, 62(1), 28–40. https://doi.org/10.1021/jf4028552
   PubMed Web of Science ®Google Scholar
• Knödler, M., Kaiser, A., Carle, R., & Schieber, A. (2008). Profiling of Alk(en)ylresorcinols in cereals by HPLC-DAD-APcI-MS n. Analytical and Bioanalytical Chemistry, 391(1), 221–228. https://doi.org/10.1007/s00216-008-1937-8
   PubMed Web of Science ®Google Scholar
• Korycińska, M., Czelna, K., Jaromin, A., & Kozubek, A. (2009). Antioxidant activity of rye bran alkylresorcinols and extracts from whole-grain cereal products. Food Chemistry, 116(4), 1013–1018. https://doi.org/10.1016/j.foodchem.2009.03.056
   Web of Science ®Google Scholar
• Kozubek, A., & Tyman, J. H. P. (1999). Resorcinolic lipids, the natural non-isoprenoid phenolic amphiphiles and their biological activity. Chemical Reviews, 99(1), 1–31. https://doi.org/10.1021/cr970464o
   PubMed Web of Science ®Google Scholar
• Kozubek, A., Zarnowski, R., Stasiuk, M., & Gubernator, J. (2001). Natural amphiphilic phenols as bioactive compounds. Cellular and Molecular Biology Letters, 6(2A), 351–355.
   Web of Science ®Google Scholar
• Krakowska-Sieprawska, A., Kiełbasa, A., Rafińska, K., Ligor, M., & Buszewski, B. (2022). Modern methods of pre-treatment of plant material for the extraction of bioactive compounds. Molecules, 27(3), 730. https://doi.org/10.3390/molecules27030730
   PubMed Web of Science ®Google Scholar
• Lancashire, P. D., Bleiholder, H., Boom, T. V. D., Langelüddeke, P., Stauss, R., Weber, E., & Witzenberger, A. (1991). A uniform decimal code for growth stages of crops and weeds. Annals of Applied Biology, 119(3), 561–601. https://doi.org/10.1111/j.1744-7348.1991.tb04895.x
   Web of Science ®Google Scholar
• Landberg, R., Kamal-Eldin, A., Salmenkallio-Marttila, M., Rouau, X., & Åman, P. (2008). Localization of alkylresorcinols in wheat, rye and barley kernels. Journal of Cereal Science, 48(2), 401–406. https://doi.org/10.1016/j.jcs.2007.09.013
   Web of Science ®Google Scholar
• Magnucka, E. G., Pietr, S. J., & Zarnowski, R. (2015). Dynamics of alkylresorcinols during rye caryopsis germination and early seedling growth. Zeitschrift Fur Naturforschung - Section C Journal of Biosciences, 70(3–4), 71–73. https://doi.org/10.1515/znc-2014-4194
   PubMed Web of Science ®Google Scholar
• Marentes-Culma, R., & Coy-Barrera, E. (2022). Effect of soil type on the temporal and spatial 5-n-alk(en)ylresorcinol variation in triticale grown under greenhouse conditions. Journal of Soil Science and Plant Nutrition, 22(4), 4428–4437. https://doi.org/10.1007/s42729-022-01043-z
   Web of Science ®Google Scholar
• Marentes-Culma, R., Orduz-Díaz, L. L., & Coy-Barrera, E. (2019). Targeted metabolite profiling-based identification of antifungal 5-n-alkylresorcinols occurring in different cereals against Fusarium oxysporum. Molecules, 24(4), 770. https://doi.org/10.3390/molecules24040770
   PubMed Web of Science ®Google Scholar
• Mcgoverin, C. M., Snyders, F., Muller, N., Botes, W., Fox, G., & Manley, M. (2011). A review of triticale uses and the effect of growth environment on grain quality. Jornal Science Food Agriculture, 91(January), 1155–1165. https://doi.org/10.1002/jsfa.4338
   PubMedGoogle Scholar
• Melliou, E., Magiatis, P., & Skaltsounis, A. L. (2003). Alkylresorcinol derivatives and sesquiterpene lactones from cichorium spinosum. Journal of Agricultural and Food Chemistry, 51(5), 1289–1292. https://doi.org/10.1021/jf025848g
   PubMed Web of Science ®Google Scholar
• Miché, L., Belkin, S., Rozen, R., & Balandreau, J. (2003). Rice seedling whole exudates and extracted alkylresorcinols induce stress-response in Escherichia coli biosensors. Environmental Microbiology, 5(5), 403–411. https://doi.org/10.1046/j.1462-2920.2003.00432.x
   PubMed Web of Science ®Google Scholar
• Moldoveanu, S., & David, V. (2015). Solvent extraction. In Modern sample preparation for chromatography (pp. 131–189). Elsevier. https://doi.org/10.1016/B978-0-444-54319-6.00006-2
   Google Scholar
• Peña, R. J. (2004). Food uses of triticale. In M. Mergoum and H. Gómez-Macpherson (Eds.), Triticale improvement and production (pp. 119–122). Rome, Italy: Food and Agriculture Organization of the United Nations (FAO).
   Google Scholar
• Piasecka, A., Jedrzejczak-Rey, N., & Bednarek, P. (2015). Secondary metabolites in plant innate immunity: Conserved function of divergent chemicals. New Phytologist, 206(3), 948–964. https://doi.org/10.1111/nph.13325
   PubMed Web of Science ®Google Scholar
• Rebolleda, S., Beltrán, S., Sanz, M. T., González-Sanjosé, M. L., & Solaesa, Á. G. (2013). Extraction of alkylresorcinols from wheat bran with supercritical CO 2. Journal of Food Engineering, 119(4), 814–821. https://doi.org/10.1016/j.jfoodeng.2013.07.008
   Web of Science ®Google Scholar
• Ross, A. B. (2019). Alkylresorcinols. In J. Johnson and T. Wallace (Eds.), Whole grains and their bioactives: Composition and health (pp. 393–406). John Wiley & Sons Ltd. https://doi.org/10.1002/9781119129486
   Google Scholar
• Ross, A., Shepherd, M., Schüpphaus, M., Sinclair, V., Alfaro, B., Kamal-Eldin, A., & Åman, P. (2003). Alkylresorcinols in cereals and cereal products. Journal of Agricultural and Food Chemistry, 51(14), 4111–4118. https://doi.org/10.1021/jf0340456
   PubMed Web of Science ®Google Scholar
• Sampietro, D. A., Belizán, M. M. E., Apud, G. R., Juarez, J. H., Vattuone, M. A., & Catalán, C. A. N. (2013a). Alkylresorcinols: Chemical properties, methods of analysis and potential uses in food, industry and plant protection. Natural Antioxidants and Biocides from Wild Medicinal Plants June 2016, pp. 148–166. https://doi.org/10.1079/9781780642338.0148
   Google Scholar
• Sampietro, D. A., Jimenez, C. M., Belizán, M. M., Vattuone, M. A., & Catalán, C. A. N. (2013b). Development and validation of a micromethod for fast quantification of 5-n-alkylresorcinols in grains and whole grain products. Food Chemistry, 141(4), 3546–3551. https://doi.org/10.1016/j.foodchem.2013.06.069
   PubMed Web of Science ®Google Scholar
• Sapirstein, H. D. (2016). Bioactives in wheat bran. Encyclopedia of Food Grains, 1–9. https://doi.org/10.1016/B978-0-12-394437-5.00109-1
   Google Scholar
• Schirmer, M. A., Freo, J. D., Müller, M. M., Bueno, P. D. F., Prestes, D. H., & Elias, M. C. (2006). Effects of drying methods and storage period in the industrial quality of wheat. In I. Lorini, B. Bacaltchuk, H. Beckel, D. Deckers, E. Sundfeld. J. P. dos Santos, J. D. Biagi, J. C. Celaro, L. R. D’A. Faroni, L.de O. F. Bortolini, M. R. Sartori, M. C. Elias, R. N. C. Guedes, R. G. da Fonseca, & V. M. Scussel (Eds.), 9th International Working Conference on Stored-Product Protection, Campinas, São Paulo, Brazil, 15–18 October 2006 (pp. 1019–1025). Passo Fundo, RS, Brazil: Brazilian Post-harvest Association–ABRAPOS.
   Google Scholar
• Schultz, J. C., Appel, H. M., Ferrieri, A. P., & Arnold, T. M. (2013). Flexible resource allocation during plant defense responses. Frontiers in Plant Science, 4(AUG), 1–11. https://doi.org/10.3389/fpls.2013.00324
   PubMedGoogle Scholar
• Shah, I., Shah, M. A., Nawaz, M. A., Pervez, S., Noreen, N., Vargas de la Cruz, C., Khan, F., Blundell, R., Briffa, J., Azzopardi, J., & Niaz, K. (2020). Analysis of other phenolics (capsaicin, gingerol, and alkylresorcinols). In A. S. Silva; S. F. Nabavi; M. Saeedi, and S. M. Nabavi (Eds.), Recent advances in natural products analysis (1st ed. pp. 255–271). Elsevier Inc. https://doi.org/10.1016/b978-0-12-816455-6.00006-8
   Google Scholar
• Takeuchi, T., Pereira, G., Braga, M., Maróstica, M., Leal, P., & Meireles, A. (2009). Low-pressure solvent extraction (solid–liquid extraction, microwave assisted, and ultrasound assisted) from condimentary plants. In M. A. Meireles (Ed.), Extracting bioactive compounds for food products: Theory and applications (contemporary food engineering) (1st ed., pp. 137–218). Boca Raton, Fl, USA: CRC Press.
   Google Scholar
• Wang, J., Gao, X., & Wang, Z. (2019). Non-destructive determination of alkylresorcinol (ARs) content on wheat seed surfaces and prediction of ARs content in whole-grain flour. Molecules, 24(7), 21–23. https://doi.org/10.3390/molecules24071329
   Web of Science ®Google Scholar
• Witzenberger, A., Hack, H., & van den Boom, T. (1989). Erlâuterungen zum BBCH-Dezimal-Code fûr die Entwicklungsstadien des Getreides - mit Abbildungen. Gesunde Pflanzen, 41(11), 384–388.
   Google Scholar
• Żarnowski, R., Suzuki, Y., Yamaguchi, I., & Pietr, S. J. (2002). Alkylresorcinols in barley (hordeum vulgare L. distichon) grains. Zeitschrift Für Naturforschung C, 57(1–2), 57–62. https://doi.org/10.1515/znc-2002-1-210
   PubMed Web of Science ®Google Scholar
• Zaynab, M., Fatima, M., Abbas, S., Sharif, Y., Umair, M., Zafar, M. H., & Bahadar, K. (2018). Role of secondary metabolites in plant defense against pathogens. Microbial Pathogenesis, 124, 198–202. https://doi.org/10.1016/j.micpath.2018.08.034
   PubMed Web of Science ®Google Scholar
• Zhang, Q. W., Lin, L. G., & Ye, W. C. (2018). Techniques for extraction and isolation of natural products: A comprehensive review. Chinese Medicine (United Kingdom), 13(1), 1–26. https://doi.org/10.1186/s13020-018-0177-x
   PubMedGoogle Scholar
• Zhao, X., Huang, L., Kang, L., Jetter, R., Yao, L., Li, Y., Xiao, Y., Wang, D., Xiao, Q., Ni, Y., & Guo, Y. (2019). Comparative analyses of cuticular waxes on various organs of faba bean (vicia faba L.). Plant Physiology and Biochemistry, 139(March), 102–112. https://doi.org/10.1016/j.plaphy.2019.03.015
   PubMedGoogle Scholar
• Zhou, L., & Elias, R. J. (2013). Understanding antioxidant and prooxidant mechanisms of phenolics in food lipids. In Lipid oxidation: Challenges in food systems (pp. 297–321). AOCS Press. https://doi.org/10.1016/B978-0-9830791-6-3.50012-6
   Google Scholar