Published November 30, 2020
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Glucosinolate catabolism during postharvest drying determines the ratio of bioactive macamides to deaminated benzenoids in Lepidium meyenii (maca) root flour
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Esparza, Eliana, Yi, Winnie, Limonchi, Fabian, Cosio, Eric G. (2020): Glucosinolate catabolism during postharvest drying determines the ratio of bioactive macamides to deaminated benzenoids in Lepidium meyenii (maca) root flour. Phytochemistry (112502) 179: 1-10, DOI: 10.1016/j.phytochem.2020.112502, URL: http://dx.doi.org/10.1016/j.phytochem.2020.112502
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- urn:lsid:plazi.org:pub:B13EC93E5944141AC42C1F12E01B040B
References
- Agerbirk, N., Olsen, C.E., 2012. Glucosinolate structures in evolution. Phytochemistry 77, 16-45. https://doi.org/10.1016/j.phytochem.2012.02.005.
- Blaˇzevi´c, I., Montaut, S., Burˇcul, F., Olsen, C.E., Burow, M., Rollin, P., Agerbirk, N., 2020. Glucosinolate structural diversity, identification, chemical synthesis and metabolism in plants. Phytochemistry 169, 1. https://doi.org/10.1016/j. phytochem.2019.112100.
- Brown, P.D., Tokuhisa, J.G., Reichelt, M., Gershenzon, J., 2003. Variation of glucosinolate accumulation among different organs and developmental stages of Arabidopsis thaliana. Phytochemistry 62, 471-481. https://doi.org/10.1016/S0031- 9422(02)00549-6.
- Chen, J.J., Zhao, Q.S., Liu, Y.L., Gong, P.F., Cao, L., Wang, X.D., Zhao, B., 2017. Macamides present in the commercial maca (Lepidium meyenii) products and the macamide biosynthesis affected by postharvest conditions. Int. J. Food Prop. 20, 3112-3123. https://doi.org/10.1080/10942912.2016.1274905.
- Chrikishvili, D., Sadunishvili, T., Zaalishvili, G., 2006. Benzoic acid transformation via conjugation with peptides and final fate of conjugates in higher plants. Ecotoxicol. Environ. Saf. 64, 390-399. http://doi:10.1016/j.ecoenv.2005.04.009.
- De Nicola, G.R., Montaut, S., Rollin, P., Nyegue, M., Menut, C., Iori, R., Tatibou¨et, A., 2012. Stability of benzylic-type isothiocyanates in hydrodistillation-mimicking conditions. J. Agric. Food Chem. 61, 137-142. https://doi.org/10.1021/jf3041534.
- Esparza, E., Hadzich, A., Kofer, W., Mith¨ofer, A., Cosio, E.G., 2015. Bioactive Maca (Lepidium meyenii) alkamides are a result of traditional Andean postharvest drying practices. Phytochemistry 116, 138-148. https://doi.org/10.1016/j. phytochem.2015.02.030.
- Fechner, J., Kaufmann, M., Herz, C., Eisenschmidt, D., Lamy, E., Kroh, L.W., Hanschen, F. S., 2018. The major glucosinolate hydrolysis product in rocket (Eruca sativa L.), sativin, is 1,3-thiazepane-2-thione: elucidation of structure, bioactivity, and stability compared to other rocket isothiocyanates. Food Chem. 261, 57-65. https://doi.org/ 10.1016/j.foodchem.2018.04.023.
- Ganzera, M., Zhao, J., Muhammad, I., Khan, I.A., 2002. Chemical profiling and standardization of Lepidium meyenii (Maca) by reversed phase high performance liquid chromatography. Chem. Pharm. Bull. 50, 988-991. https://doi.org/10.1248/ cpb.50.988.
- Gimsing, A.L., Kirkegaard, J.A., 2009. Glucosinolates and biofumigation: fate of glucosinolates and their hydrolysis products in soil. Phytochemistry Rev. 8, 299-310. https://doi.org/10.1007/s11101-008-9105-5.
- G´omez-Alonso, S., Hermosin-Guti´errez, I., Garcia-Romero, E., 2007. Simultaneous HPLC analysis of biogenic amines, amino acids, and ammonium ion as aminoenone derivatives in wine and beer samples. J. Agric. Food Chem. 55, 608-613. https://doi. org/10.1021/jf062820m.
- Halkier, B.A., Gershenzon, J., 2006. Biology and biochemistry of glucosinolates. Annu. Rev. Plant Biol. 57, 303-333. https://doi.org/10.1146/annurev. arplant.57.032905.105228.
- Ibdah, M., Chen, Y.T., Wilkerson, C.G., Pichersky, E., 2009. An aldehyde oxidase in developing seeds of Arabidopsis converts benzaldehyde to benzoic acid. Plant Physiol. 150, 416-423. https://doi.org/10.1104/pp.109.135848.
- Jeschke, V., Gershenzon, J., Vassao, D.G., 2016. Insect detoxification of glucosinolates and their hydrolysis products. Adv. Bot. Res. 80, 199-245. https://doi.org/10.1016/ bs.abr.2016.06.003.
- McCollom, M.M., Villinski, J.R., McPhail, K.L., Craker, L.E., Gafner, S., 2005. Analysis of macamides in samples of Maca (Lepidium meyenii) by HPLC-UV-MS/MS. Phytochem. Anal. 16, 463-469. https://doi.org/10.1002/pca.871.
- Matile, P., 1990. The toxic compartment of plant cells. In: Progress in Plant Cellular and Molecular Biology Current Plant Science and Biotechnology in Agriculture, pp. 557-566. https://doi:10.1007/978-94-009-2103-0_84.
- Moldrup, M.E., Geu-Flores, F., Olsen, C.E., Halkier, B.A., 2011. Modulation of sulfur metabolism enables efficient glucosinolate engineering. BMC Biotechnol. 11, 12. https://doi.org/10.1186/1472-6750-11-12.
- Palani, K., Harbaum-Piayda, B., Meske, D., Keppler, J.K., Bockelmann, W., Heller, K.J., Schwarz, K., 2016. Influence of fermentation on glucosinolates and glucobrassicin degradation products in sauerkraut. Food Chem. 190, 755-762. https://doi.org/ 10.1016/j.foodchem.2015.06.012.
- Platz, S., Kuhn, C., Schiess, S., Schreiner, M., Kemper, M., Pivovarova, O., Pfeiffer, A.F. H., Rohn, S., 2015. Bioavailability and metabolism of benzyl glucosinolate in humans consuming Indian cress (Tropaeolum majus L.). Mol. Nutr. Food Res. 60, 652-660. https://doi.org/10.1002/mnfr.201500633.
- Rabie, M.A., Siliha, H., el-Saidy, S., el-Badawy, A.A., Malcata, F.X., 2011. Reduced biogenic amine contents in sauerkraut via addition of selected lactic acid bacteria. Food Chem. 129, 1778-1782. https://doi.org/10.1016/j.foodchem.2011.05.10600.
- Redruello, B., Ladero, V., Cuesta, I., Alvarez-Buylla ´, J.R., Martin, M.C., Fern´andez, M., Alvarez, M.A., 2013. A fast, reliable, ultra high performance liquid chromatography method for the simultaneous determination of amino acids, biogenic amines and ammonium ions in cheese, using diethyl ethoxymethylenemalonate as a derivatising agent. Food Chem. 139, 1029-1035. https://doi.org/10.1016/j. foodchem.2013.01.071.
- Senger, T., Wichard, T., Kunze, S., Gobel ¨, C., Lerchl, J., Pohnert, G., Feussner, I., 2005. A multifunctional lipoxygenase with fatty acid hydroperoxide cleaving activity from the moss Physcomitrella patens. J. Biol. Chem. 280, 7588-7596. https://doi.org/ 10.1074/jbc.M411738200.
- Simons, S.S., Johnson, D.F., 1978. Reaction of o -phthalaldehyde and thiols with primary amines: fluorescence properties of 1-alkyl(and aryl)thio-2-alkylisoindoles. Anal. Biochem. 90, 705-725. https://doi.org/10.1016/0003-2697(78)90163-X12100.
- Sorensen, J.C., Frandsen, H.B., Jensen, S.K., Kristensen, N.B., Sorensen, S., Sorensen, H., 2016. Bioavailability and in vivo metabolism of intact glucosinolates. Journal of Functional Foods 24, 450-460. https://doi.org/10.1016/j.jff.2016.04.023.
- Traka, M.H., 2016. Health benefits of glucosinolates. Adv. Bot. Res. 80, 247-279. https://doi.org/10.1016/bs.abr.2016.06.004.
- Tang, C.S., Bhothipaksa, K., Frank, H.A., 1972. Bacterial degradation of benzyl isothiocyanate. Appl. Microbiol. 23, 1145-1148.
- Vaughn, S., Berhow, M., 2005. Glucosinolate hydrolysis products from various plant sources: pH effects, isolation, and purification. Ind. Crop. Prod. 21, 193-202. https://doi.org/10.1016/j.indcrop.2004.03.004.
- Wittstock, U., Kurzbach, E., Steiner, A.M., Stauber, E.J., 2016. Glucosinolate breakdown. Adv. Bot. Res. 80, 125-169. https://doi.org/10.1016/bs.abr.2016.06.006.
- Wuensch, C., Lechner, H., Glueck, S.M., Zangger, K., Hall, M., Faber, K., 2013. Asymmetric biocatalytic Cannizzaro-type reaction. ChemCatChem 5, 1744-1748. https://doi.org/10.1002/cctc.201300028.
- Y´abar, E., Pedreschi, R., Chirinos, R., Campos, D., 2011. Glucosinolate content and myrosinase activity evolution in three maca (Lepidium meyenii Walp.) ecotypes during preharvest, harvest and postharvest drying. Food Chem. 127, 1576-1583. https://doi.org/10.1016/j.foodchem.2011.02.021.
- Zhang, S.Z., Yang, F., Shao, J.L., Pu, H.M., Ruan, Z.Y., Yang, W.L., Li, H., 2020. The metabolic formation profiles of macamides accompanied by the conversion of glucosinolates in maca (Lepidium meyenii) during natural air drying. Int. J. Food Sci. Technol. 55, 2428-2440. https://doi.org/10.1111/ijfs.14493.