Abstract
Plants have been the target of a growing interest by the scientific community in chemical and nutritional characterization studies, due to the presence of bioactive compounds and their potential industrial use, namely in food and pharmaceutical sectors. Different secondary metabolites found in plants ensure their survival and reproduction. Non-alkaloids compounds are an important group of secondary metabolites present in the plant kingdom, which have been widely studied and aimed at their industrial application, namely in the pharmaceutical area. This group of compounds has an important ecological function of protection; and in addiction an excellent bioactive performance has been highlighted and exploited for promising application in the pharmaceutical industry.
This chapter focuses on the characterization of different classes of non-alkaloid nitrogen compounds: non-protein amino acids, cyanogenic glycosides compounds, and glucosinolates. Its chemical and structural characteristics as well as its biosynthesis and presence in plants will be presented. The bioactivities presented by each of the classes will be equally focused as well as their applicability.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Similar content being viewed by others
References
Amaya-Salcedo JC, Cárdenas-González OE, Gómez-Castaño JA (2018) Solid-to-liquid extraction and HPLC/UV determination of amygdalin of seeds of apple (Malus pumila Mill): comparison between traditional-solvent and microwave methodologies. Acta Agron 67(3):381–388
Andréasson E, Jørgensen LB (2003) Localization of plant myrosinases and glucosinolates. In: Romeo JT (ed) Integrative phytochemistry: from ethnobotany to molecular ecology. Elsevier, New York, pp 79–99. https://doi.org/10.1016/S0079-9920(03)80019-9
Ares AM, Nozal MJ, Bernal J, Bernal JL (2014) Optimized extraction, separation and quantification of twelve intact glucosinolates in broccoli leaves. Food Chem 152:66–74. https://doi.org/10.1016/J.FOODCHEM.2013.11.125
Ares AM, Bernal J, Nozal MJ, Turner C, Plaza M (2015) Fast determination of intact glucosinolates in broccoli leaf by pressurized liquid extraction and ultra high performance liquid chromatography coupled to quadrupole time-of-flight mass spectrometry. Food Res Int 76(3):498–505. https://doi.org/10.1016/J.FOODRES.2015.06.037
Armstrong H, Bording-Jorgensen M, Dijk S, Wine E (2018) The complex interplay between chronic inflammation, the microbiome, and cancer: understanding disease progression and what we can do to prevent it. Cancers 10:83. https://doi.org/10.3390/CANCERS10030083
Ayon NJ (2020) Features, roles and chiral analyses of proteinogenic amino acids. AIMS Mol Sci 7:229–268
Baatouche S, Cheriet T, Sarri D, Mekkiou R, Boumaza O, Benayache S, Benayache F, Brouard I, León F, Seghiri R (2019) Centaurea microcarpa Coss. & Dur. (Asteraceae) extracts: new cyanogenic glucoside and other constituents. Nat Prod Res 33(21):3070–3076
Barba FJ, Nikmaram N, Roohinejad S, Khelfa A, Zhu Z, Koubaa M (2016) Bioavailability of glucosinolates and their breakdown products: impact of processing. Front Nutr 3:24. https://doi.org/10.3389/FNUT.2016.00024/BIBTEX
Barthet VJ, Bacala R (2010) Development of optimized extraction methodology for cyanogenic glycosides from flaxseed (Linum usitatissimum). J AOAC Int 93(2):478–484
Bell EA (2003) Nonprotein amino acids of plants: significance in medicine, nutrition, and agriculture. J Agric Food Chem 51:2854–2865
Bell EA, Watson AA, Nash RJ (2008) Non-protein amino acids: a review of the biosynthesis and taxonomic significance. Nat Prod Commun 9:93–110
Bence AK, Worthen DR, Adams VR, Crooks PA (2002) The antiproliferative and immunotoxic effects of L-canavanine and L-canaline. Anticancer Drugs 13(3):313–320
Bennett RN, Mellon FA, Kroon PA (2004) Screening crucifer seeds as sources of specific intact glucosinolates using ion-pair high-performance liquid chromatography negative ion electrospray mass spectrometry. J Agric Food Chem 52(3):428–438. https://doi.org/10.1021/JF030530P/SUPPL_FILE/JF030530P_S.PDF
Beran F, Köllner TG, Gershenzon J, Tholl D (2019) Chemical convergence between plants and insects: biosynthetic origins and functions of common secondary metabolites. New Phytol 223(1):52–67
Bernardi R, Negri A, Ronchi S, Palmieri S (2000) Isolation of the epithiospecifier protein from oil-rape (Brassica napus ssp. oleifera) seed and its characterization. FEBS Lett 467(2–3):296–298. https://doi.org/10.1016/S0014-5793(00)01179-0
Blažević I, Montaut S, Burčul F, Olsen CE, Burow M, Rollin P, Agerbirk N (2020) Glucosinolate structural diversity, identification, chemical synthesis and metabolism in plants. Phytochemistry 169:112100. https://doi.org/10.1016/J.PHYTOCHEM.2019.112100
Bolarinwa IF, Oke MO, Olaniyan SA, Ajala AS (2016a) A review of cyanogenic glycosides in edible plants. In: Toxicology - new aspects to this scientific conundrum. Springer, New York, pp 179–191
Bolarinwa IF, Olaniyan SA, Olatunde SJ, Ayandokun FT, Olaifa IA (2016b) Effect of processing on amygdalin and cyanide contents of some Nigerian foods. J Chem Pharm Res 8(2):106–113
Bones AM, Rossiter JT (2006) The enzymic and chemically induced decomposition of glucosinolates. Phytochemistry 67(11):1053–1067. https://doi.org/10.1016/J.PHYTOCHEM.2006.02.024
Brandi G, Amagliani G, Schiavano GF, De Santi M, Sisti M (2006) Activity of Brassica oleracea leaf juice on foodborne pathogenic bacteria. J Food Prot 69(9):2274–2279. https://doi.org/10.4315/0362-028X-69.9.2274
Buskov S, Hasselstrøm J, Olsen CE, Sørensen H, Sørensen JC, Sørensen S (2000) Supercritical fluid chromatography as a method of analysis for the determination of 4-hydroxybenzylglucosinolate degradation products. J Biochem Biophys Methods 43(1–3):157–174. https://doi.org/10.1016/S0165-022X(00)00081-6
Castada HZ, Liu J, Barringer SA, Huang X (2020) Cyanogenesis in macadamia and direct analysis of hydrogen cyanide in macadamia flowers, leaves, husks, and nuts using selected ion flow tube–mass spectrometry. Foods 9(2):174
Chen G, Fang Q, Zhang J, Zhou D, Wang Z (2011) Role of the Nrf2-ARE pathway in early brain injury after experimental subarachnoid hemorrhage. J Neurosci Res 89(4):515–523. https://doi.org/10.1002/JNR.22577
Cowan MF, Blomstedt CK, Møller BL, Henry RJ, Gleadow RM (2021) Variation in production of cyanogenic glucosides during early plant development: a comparison of wild and domesticated sorghum. Phytochemistry 184:112645
da Rodrigues-Corrêa KCS, Fett-Neto AG (2019) Abiotic stresses and non-protein amino acids in plants. Crit Rev Plant Sci 38:411–430
Davidson RK, Jupp O, De Ferrars R, Kay CD, Culley KL, Norton R, Driscoll C, Vincent TL, Donell ST, Bao Y, Clark IM (2013) Sulforaphane represses matrix-degrading proteases and protects cartilage from destruction in vitro and in vivo. Arthritis Rheum 65(12):3130–3140. https://doi.org/10.1002/ART.38133/ABSTRACT
de Castro RJS, Sato HH (2015) Biologically active peptides: processes for their generation, purification and identification and applications as natural additives in the food and pharmaceutical industries. Food Res Int 74:185–198
Deng Q, Zinoviadou KG, Galanakis CM, Orlien V, Grimi N, Vorobiev E, Lebovka N, Barba FJ (2015) The effects of conventional and non-conventional processing on glucosinolates and its derived forms, isothiocyanates: extraction, degradation, and applications. Food Eng Rev 7(3):357–381. https://doi.org/10.1007/S12393-014-9104-9
Ding Y, Ting JP, Liu J, Al-Azzam S, Pandya P, Afshar S (2020) Impact of non-proteinogenic amino acids in the discovery and development of peptide therapeutics. Amino Acids 52:1207–1226
Drobnica Ľ, Zemanová M, Nemec P, Antoš K, Kristián P, Štullerová A, Knoppová V, Nemec P (1967) Antifungal activity of isothiocyanates and related compounds. Appl Microbiol 15(4):701–709. https://doi.org/10.1128/AM.15.4.701-709.1967
Duan X, Ocen D, Wu F, Li M, Yang N, Xu J et al (2014) Purification and characterization of a natural antioxidant peptide from fertilized eggs. Food Res Int 56:18–24
Dunlop RA, Main BJ, Rodgers KJ (2015) The deleterious effects of non-protein amino acids from desert plants on human and animal health. J Arid Environ 112:152–158
Engel E, Baty C, Le Corre D, Souchon I, Martin N (2002) Flavor-active compounds potentially implicated in cooked cauliflower acceptance. J Agric Food Chem 50(22):6459–6467. https://doi.org/10.1021/JF025579U
Esfandiari A, Saei A, McKenzie MJ, Matich AJ, Babalar M, Hunter DA (2017) Preferentially enhancing anti-cancer isothiocyanates over glucosinolates in broccoli sprouts: how NaCl and salicylic acid affect their formation. Plant Physiol Biochem 115:343–353. https://doi.org/10.1016/J.PLAPHY.2017.04.003
Fahey J (2005) Method of extraction of isothiocyanates into oil from glucosinolate-containing plants and method of producing products with oil containing isothiocyanates extracted from glucosinolate-containing plants (Patent No. US11/302,118). United States Patent
Fahey J, Zalcmann AT, Talalay P (2001) The chemical diversity and distribution of glucosinolates and isothiocyanates among plants. Phytochemistry 56(1):5–51. https://doi.org/10.1016/S0031-9422(00)00316-2
Fahey J, Haristoy X, Dolan PM, Kensler TW, Scholtus I, Stephenson KK, Talalay P, Lozniewski A (2002) Sulforaphane inhibits extracellular, intracellular, and antibiotic-resistant strains of Helicobacter pylori and prevents benzo[a]pyrene-induced stomach tumors. Proc Natl Acad Sci 99(11):7610–7615. https://doi.org/10.1073/PNAS.112203099
Fomo G, Madzimbamuto TN, Ojumu TV (2020) Applications of nonconventional green extraction technologies in process industries: challenges, limitations and perspectives. Sustainability 12(13):5244. https://doi.org/10.3390/SU12135244
Gallaher CM, Gallaher DD, Peterson S (2012) Development and validation of a spectrophotometric method for quantification of total glucosinolates in cruciferous vegetables. J Agric Food Chem 60(6):1358–1362. https://doi.org/10.1021/JF2041142
Ganjewala D, Kumar S, Devi SA, Ambika K (2010) Advances in cyanogenic glycosides biosynthesis and analyses in plants: a review. Acta Biologica Szegediensis 54(1):1–14
Gleadow RM, Møller BL (2014) Cyanogenic glycosides: synthesis, physiology, and phenotypic plasticity. Annu Rev Plant Biol 65:155–185
Gupta AS (2019) Strategic approaches for the purification of glycosides from natural sources. Nat Bioact Compd 1:129–147
Guzmán-Pérez V, Bumke-Vogt C, Schreiner M, Mewis I, Borchert A, Pfeiffer AFH (2016) Benzylglucosinolate derived isothiocyanate from tropaeolum majus reduces gluconeogenic gene and protein expression in human cells. PLoS One 11(9):e0162397. https://doi.org/10.1371/JOURNAL.PONE.0162397
Halenár M, Medveďová M, Maruniaková N, Kolesárová A (2013) A review amygdalin and its effects on animal cells. J Microbiol 1(2):1414–1423
Halkier BA, 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
Hanschen FS, Lamy E, Schreiner M, Rohn S (2014) Reactivity and stability of glucosinolates and their breakdown products in foods. Angew Chem Int Ed 53(43):11430–11450. https://doi.org/10.1002/ANIE.201402639
Harenčár Ľ (2021) Cyanogenic glycosides - their role and potential in plant food resources. J Microbiol Biotechnol Food Sci 11(3):e4771–e4771
Haristoy X, Angioi-Duprez K, Duprez A, Lozniewski A (2003) Efficacy of sulforaphane in eradicating Helicobacter pylori in human gastric xenografts implanted in nude mice. Antimicrob Agents Chemother 47(12):3982–3984. https://doi.org/10.1128/AAC.47.12.3982-3984.2003
Hebert M, Mhemdi H, Vorobiev E (2020) Selective and eco-friendly recovery of glucosinolates from mustard seeds (Brassica juncea) using process optimization and innovative pretreatment (high voltage electrical discharges). Food Bioprod Process 124:11–23. https://doi.org/10.1016/J.FBP.2020.04.009
Huang T, Jander G, de Vos M (2011) Non-protein amino acids in plant defense against insect herbivores: representative cases and opportunities for further functional analysis. Phytochemistry 72:1531–1537
Hwang HJ, Kim P, Kim CJ, Lee HJ, Shim I, Yin CS, Yang Y, Hahm DH (2008) Antinociceptive effect of amygdalin isolated from Prunus armeniaca on formalin-induced pain in rats. Biol Pharm Bull 31(8):1559–1564
Ikeda K, Shoda T, Demizu Y, Tsuji G (2021) Discovery of non-proteinogenic amino acids inhibiting biofilm formation by S. aureus and methicillin-resistant S. aureus. Bioorg Med Chem Lett 48:128259
Ishida M, Hara M, Fukino N, Kakizaki T, Morimitsu Y (2014) Glucosinolate metabolism, functionality and breeding for the improvement of Brassicaceae vegetables. Breed Sci 64(1):48–59. https://doi.org/10.1270/JSBBS.64.48
Jaafaru MS, Abd Karim NA, Enas ME, Rollin P, Mazzon E, Razis AFA (2018) Protective effect of glucosinolates hydrolytic products in neurodegenerative diseases (NDDs). Nutrients 10(5):580. https://doi.org/10.3390/NU10050580
Jander G, Kolukisaoglu U, Stahl M, Yoon GM (2020) Physiological aspects of non-proteinogenic amino acids in plants. Front Plant Sci 11:519464
Jang YJ, Park B, Lee HW, Park HJ, Koo HJ, Kim BO, Sohn EH, Um SH, Pyo S (2017) Sinigrin attenuates the progression of atherosclerosis in ApoE−/− mice fed a high-cholesterol diet potentially by inhibiting VCAM-1 expression. Chem Biol Interact 272:28–36. https://doi.org/10.1016/J.CBI.2017.05.006
Jaszczak-Wilke E, Polkowska Ż, Koprowski M, Owsianik K, Mitchell AE, Bałczewski P (2021) Amygdalin: toxicity, anticancer activity and analytical procedures for its determination in plant seeds. Molecules 26(8)
Jezek J, Haggett BGD, Atkinson A, Rawson DM (1999) Determination of glucosinolates using their alkaline degradation and reaction with ferricyanide. J Agric Food Chem 47(11):4669–4674. https://doi.org/10.1021/JF9906026
Kasperkiewicz P, Gajda AD, Dra̧g, M. (2012) Current and prospective applications of non-proteinogenic amino acids in profiling of proteases substrate specificity. Biol Chem 393:843–851
Lafarga T, Bobo G, Viñas I, Collazo C, Aguiló-Aguayo I (2018) Effects of thermal and non-thermal processing of cruciferous vegetables on glucosinolates and its derived forms. J Food Sci Technol 55(6):1973–1981. https://doi.org/10.1007/S13197-018-3153-7/TABLES/3
Lai D, Pičmanová M, Abou Hachem M, Motawia MS, Olsen CE, Møller BL, Rook F, Takos AM (2015) Lotus japonicus flowers are defended by a cyanogenic β-glucosidase with highly restricted expression to essential reproductive organs. Plant Mol Biol 89(1–2):21–34
Lea PJ, Azevedo RA (2016) Amino acids encyclopedia of applied plant sciences, vol 2, 2nd edn. Elsevier, New York
Lee J, Zhang G, Wood E, Rogel Castillo C, Mitchell AE (2013) Quantification of amygdalin in nonbitter, semibitter, and bitter almonds (prunus dulcis) by UHPLC-(ESI)QqQ MS/MS. J Agric Food Chem 61(32):7754–7759
Lee S, Kim J, Seo SG, Choi BR, Han JS, Lee KW, Kim J (2014) Sulforaphane alleviates scopolamine-induced memory impairment in mice. Pharmacol Res 85:23–32. https://doi.org/10.1016/J.PHRS.2014.05.003
Lee SH, Oh A, Shin SH, Kim HN, Kang WW, Chung SK (2017a) Amygdalin contents in peaches at different fruit development stages. Prev Nutr Food Sci 22(3):237–240
Lee HW, Lee CG, Rhee DK, Um SH, Pyo S (2017b) Sinigrin inhibits production of inflammatory mediators by suppressing NF-κB/MAPK pathways or NLRP3 inflammasome activation in macrophages. Int Immunopharmacol 45:163–173. https://doi.org/10.1016/J.INTIMP.2017.01.032
Li X, Li J, Dong S, Li Y, Wei L, Zhao C, Li J, Liu X, Wang Y (2019) Effects of germination on tocopherol, secoisolariciresinol diglucoside, cyanogenic glycosides and antioxidant activities in flaxseed (Linum usitatissimum L.). Int J Food Sci Technol 54(7):2346–2354
Litwack G (2018) Proteins. In: Human biochemistry. Springer, New York, pp 63–94. https://doi.org/10.1016/B978-0-12-383864-3.00004-1
López-Chillón MT, Carazo-Díaz C, Prieto-Merino D, Zafrilla P, Moreno DA, Villaño D (2019) Effects of long-term consumption of broccoli sprouts on inflammatory markers in overweight subjects. Clin Nutr 38(2):745–752. https://doi.org/10.1016/J.CLNU.2018.03.006
Ma L, Liu G, Sampson L, Willett WC, Hu FB, Sun Q (2018) Dietary glucosinolates and risk of type 2 diabetes in 3 prospective cohort studies. Am J Clin Nutr 107(4):617–625. https://doi.org/10.1093/AJCN/NQY003
Mahn A, Comett R, Segura-Ponce LA, Díaz-Álvarez RE (2021) Effect of pulsed electric field-assisted extraction on recovery of sulforaphane from broccoli florets. J Food Process Eng e13837. https://doi.org/10.1111/JFPE.13837
Maloy S (2013) Amino acids. In: Brenner’s encyclopedia of genetics, 2nd edn. Elsevier, New York
Mamdouh AM, Khodeer DM, Tantawy MA, Moustafa YM (2021) In-vitro and in-vivo investigation of amygdalin, metformin, and combination of both against doxorubicin on hepatocellular carcinoma. Life Sci 285:119961
Manyes L, Luciano FB, Mañes J, Meca G (2015) In vitro antifungal activity of allyl isothiocyanate (AITC) against Aspergillus parasiticus and Penicillium expansum and evaluation of the AITC estimated daily intake. Food Chem Toxicol 83:293–299. https://doi.org/10.1016/J.FCT.2015.06.011
Marian E, Tita B, Tita IC, Jurca T, Vicas L (2018) Thermal behaviour and kinetic study of amygdalin. J Therm Anal Calorim 134(1):765–772
Martins T, Colaço B, Venâncio C, Pires MJ, Oliveira PA, Rosa E, Antunes LM (2018) Potential effects of sulforaphane to fight obesity. J Sci Food Agric 98(8):2837–2844. https://doi.org/10.1002/JSFA.8898
Mayton HS, Olivier C, Vaughn SF, Loria R (1996) Correlation of fungicidal activity of Brassica species with allyl isothiocyanate production in macerated leaf tissue. Phytopathology 86(3):267–271. https://doi.org/10.1094/PHYTO-86-267
Mi L, **ao Z, Hood BL, Dakshanamurthy S, Wang X, Govind S, Conrads TP, Veenstra TD, Chung FL (2008) Covalent binding to tubulin by isothiocyanates: a mechanism of cell growth arrest and apoptosis. J Biol Chem 283(32):22136–22146. https://doi.org/10.1074/JBC.M802330200/ATTACHMENT/4871425B-EAE4-4EC9-9531-5D6D79EA1F8E/MMC1.PDF
Mi L, **ao Z, Veenstra TD, Chung FL (2011) Proteomic identification of binding targets of isothiocyanates: a perspective on techniques. J Proteome 74(7):1036–1044. https://doi.org/10.1016/J.JPROT.2011.04.015
Mohn T, Cutting B, Ernst B, Hamburger M (2007) Extraction and analysis of intact glucosinolates—a validated pressurized liquid extraction/liquid chromatography–mass spectrometry protocol for Isatis tinctoria, and qualitative analysis of other cruciferous plants. J Chromatogr A 1166(1–2):142–151. https://doi.org/10.1016/J.CHROMA.2007.08.028
Moreno DA, Carvajal M, López-Berenguer C, García-Viguera C (2006) Chemical and biological characterisation of nutraceutical compounds of broccoli. J Pharm Biomed Anal 41(5):1508–1522. https://doi.org/10.1016/J.JPBA.2006.04.003
Mosayyebi B, Imani M, Mohammadi L, Akbarzadeh A, Zarghami N, Edalati M, Alizadeh E, Rahmati M (2020) An update on the toxicity of cyanogenic glycosides bioactive compounds: possible clinical application in targeted cancer therapy. Mater Chem Phys 246:122841
Munday R, Munday CM (2004) Induction of phase II detoxification enzymes in rats by plant-derived isothiocyanates: comparison of allyl isothiocyanate with sulforaphane and related compounds. J Agric Food Chem 52(7):1867–1871. https://doi.org/10.1021/JF030549S
Nadarajah D, Han JH, Holley RA (2005a) Inactivation of Escherichia coli O157:H7 in packaged ground beef by allyl isothiocyanate. Int J Food Microbiol 99(3):269–279. https://doi.org/10.1016/J.IJFOODMICRO.2004.08.019
Nadarajah D, Han JH, Holley RA (2005b) Use of mustard flour to inactivate Escherichia coli O157:H7 in ground beef under nitrogen flushed packaging. Int J Food Microbiol 99(3):257–267. https://doi.org/10.1016/J.IJFOODMICRO.2004.08.018
Nakagawa K, Umeda T, Higuchi O, Tsuzuki T, Suzuki T, Miyazawa T (2006) Evaporative light-scattering analysis of sulforaphane in broccoli samples: quality of broccoli products regarding sulforaphane contents. J Agric Food Chem 54(7):2479–2483. https://doi.org/10.1021/JF051823G
Narancic T, Almahboub SA, O’Connor KE (2019) Unnatural amino acids: production and biotechnological potential. World J Microbiol Biotechnol 35
Naveena K, Chinniah C, Shanthi M (2021) Cyanogenic glycosides and plant-herbivore interactions. J Entomol Zool Stud 9(1):1345–1350
Nepi M (2014) Beyond nectar sweetness: the hidden ecological role of non-protein amino acids in nectar. J Ecol 102:108–115
Nyirenda KK (2020, March 20). Toxicity potential of cyanogenic glycosides in edible plants. In: Erkekoglu P, Ogawa T (eds) Medical toxicology. IntechOpen. https://www.intechopen.com/chapters/71290
Olsen CE, Huang XC, Hansen CIC, Cipollini D, Ørgaard M, Matthes A, Geu-Flores F, Koch MA, Agerbirk N (2016) Glucosinolate diversity within a phylogenetic framework of the tribe Cardamineae (Brassicaceae) unraveled with HPLC-MS/MS and NMR-based analytical distinction of 70 desulfoglucosinolates. Phytochemistry 132:33–56. https://doi.org/10.1016/J.PHYTOCHEM.2016.09.013
Omirou M, Papastylianou I, Iori R, Papastephanou C, Papadopoulou KK, Ehaliotis C, Karpouzas DG (2009) Microwave-assisted extraction of glucosinolates from Eruca sativa seeds and soil: comparison with existing methods. Phytochem Anal 20(3):214–220. https://doi.org/10.1002/PCA.1117
Pandey A, Sauraj AA, Negi Y (2020) Synthesis of polygonal chitosan microcapsules for the delivery of amygdalin loaded silver nanoparticles in breast cancer therapy. Mater Tod Proc 43:3744–3748
Pane C, Rongai D, Zaccardelli M (2013) Foliar spray application of glucosinolates and essential oils on processing tomato in open field production system. Agric Sci 4(3):149–153. https://doi.org/10.4236/AS.2013.43022
Park D-S, Coats JR (2002) Cyanogenic glycosides: alternative insecticides? Kor J Pest Sci 6(2):1226–6183
Park CM, Taormina PJ, Beuchat LR (2000) Efficacy of allyl isothiocyanate in killing enterohemorrhagic Escherichia coli O157:H7 on alfalfa seeds. Int J Food Microbiol 56(1):13–20. https://doi.org/10.1016/S0168-1605(99)00202-0
Parthasarathy A, Borrego EJ, Savka MA, Dobson RCJ, Hudson AO (2021) Amino acid–derived defense metabolites from plants: a potential source to facilitate novel antimicrobial development. J Biol Chem 296:100438
Patel SS, Soni H, Mishra K, Singhai AK (2011) Recent updates on the genus Passiflora: a review. Int J Res Phytochem Pharmacol 1(1):1–16
Pongmalai P, Devahastin S, Chiewchan N, Soponronnarit S (2015) Enhancement of microwave-assisted extraction of bioactive compounds from cabbage outer leaves via the application of ultrasonic pretreatment. Sep Purif Technol 144:37–45. https://doi.org/10.1016/J.SEPPUR.2015.02.010
Puigserver P (2018) Signaling transduction and metabolomics. In: Hematology: basic principles and practice, 7th edn. Elsevier, New York, pp 68–78
Raiola A, Errico A, Petruk G, Monti DM, Barone A, Rigano MM (2017) Bioactive compounds in brassicaceae vegetables with a role in the prevention of chronic diseases. Molecules 23(1):15. https://doi.org/10.3390/MOLECULES23010015
Rodman JE, Karol KG, Price RA, Sytsma KJ (1996) Molecules, morphology, and Dahlgren’s expanded order capparales. Syst Bot 21(3):289–307. https://doi.org/10.2307/2419660
Rodríguez Madrera R, Suárez Valles B (2021) Analysis of cyanogenic compounds derived from mandelonitrile by ultrasound-assisted extraction and high-performance liquid chromatography in rosaceae and sambucus families. Molecules 26(24):7563
Román J, Castillo A, Mahn A (2018) Molecular docking of potential inhibitors of Broccoli Myrosinase. Molecules 23:1313. https://doi.org/10.3390/MOLECULES23061313
Roselló-Soto E, Parniakov O, Deng Q, Patras A, Koubaa M, Grimi N, Boussetta N, Tiwari BK, Vorobiev E, Lebovka N, Barba FJ (2016) Application of non-conventional extraction methods: toward a sustainable and green production of valuable compounds from mushrooms. Food Eng Rev 8(2):214–234. https://doi.org/10.1007/S12393-015-9131-1/FIGURES/5
Saladino F, Bordin K, Luciano FB, Franzón MF, Mañes J, Meca G (2017) Antimicrobial activity of the glucosinolates. In: Mérillon J-M, Gopal Ramawat K (eds) Glucosinolates, 1st edn. Springer, New York, pp 249–274. https://doi.org/10.1007/978-3-319-25462-3_18
Samanthi KAU, Welideniya DT, Acharige AD, Samarakoon SR, Rathnayaka RK, de Silva M, Perera SS, Pieris C, Wanninayake UK, Jayathilaka A, Karunaratne V, Amaratunga GAJ, Gunasekera DS (2021) An efficient and high-yielding method for extraction and purification of linamarin from Cassava; in vitro biological evaluation. Nat Prod Res 35(21):4169–4172
Sánchez-Pujante PJ, Borja-Martínez M, Pedreño MÁ, Almagro L (2017) Biosynthesis and bioactivity of glucosinolates and their production in plant in vitro cultures. Planta 246(1):19–32. https://doi.org/10.1007/S00425-017-2705-9/TABLES/2
Sarasa SB, Mahendran R, Muthusamy G, Thankappan B, Selta DRF, Angayarkanni J (2020) A brief review on the non-protein amino acid, gamma-amino butyric acid (GABA): its production and role in microbes. Curr Microbiol 77:534–544
Sarıkamış G (2011) Glucosinolates in crucifers and their potential effects against cancer: review. Can J Plant Sci 89(5):953–959. https://doi.org/10.4141/CJPS08125
Selmar D (2010) Biosynthesis of cyanogenic glycosides, glucosinolates and non-protein amino acids. Annu Plant Rev 40
Senica M, Stampar F, Veberic R, Mikulic-Petkovsek M (2016a) Transition of phenolics and cyanogenic glycosides from apricot and cherry fruit kernels into liqueur. Food Chem 203:483–490
Senica M, Stampar F, Veberic R, Mikulic-Petkovsek M (2016b) Processed elderberry (Sambucus nigra L.) products: a beneficial or harmful food alternative? LWT Food Sci Technol 72:182–188
Seo MS, Kim JS (2017) Understanding of MYB transcription factors involved in glucosinolate biosynthesis in brassicaceae. Molecules 22:1549. https://doi.org/10.3390/MOLECULES22091549
Shafaei A, Halim NHA, Zakaria N, Ismail Z (2017) Analysis of free amino acids in different extracts of Orthosiphon stamineus leaves by high-performance liquid chromatography combined with solid-phase extraction. Pharmacogn Mag 13:S385–S391
Shahwar D, Young LW, Shim YY, Reaney MJT (2019) Extractive silylation method for high throughput GC analysis of flaxseed cyanogenic glycosides. J Chromatogr B Anal Technol Biomed Life Sci 1132:121816
Shi J, Chen Q, Xu M, **a Q, Zheng T, Teng J, Li M, Fan L (2019) Recent updates and future perspectives about amygdalin as a potential anticancer agent: a review. Cancer Med 8(6):3004–3011
Sikorska-Zimny K, Beneduce L (2020) The glucosinolates and their bioactive derivatives in Brassica: a review on classification, biosynthesis and content in plant tissues, fate during and after processing, effect on the human organism and interaction with the gut microbiota. Crit Rev Food Sci Nutr 61(15):2544–2571. https://doi.org/10.1080/10408398.2020.1780193
Sivakumar G, Aliboni A, Bacchetta L (2007) HPLC screening of anti-cancer sulforaphane from important European Brassica species. Food Chem 104(4):1761–1764. https://doi.org/10.1016/J.FOODCHEM.2006.11.040
Śmiechowska A, Bartoszek A, Namieśnik J (2010) Determination of glucosinolates and their decomposition products—indoles and isothiocyanates in cruciferous vegetables. Crit Rev Anal Chem 40(3):202–216. https://doi.org/10.1080/10408347.2010.490489
Solana M, Boschiero I, Dall’Acqua S, Bertucco A (2014) Extraction of bioactive enriched fractions from Eruca sativa leaves by supercritical CO2 technology using different co-solvents. J Supercrit Fluids 94:245–251. https://doi.org/10.1016/J.SUPFLU.2014.08.022
Song Z, Xu X (2014) Advanced research on anti-tumor effects of amygdalin. J Cancer Res Ther 10(5):C3–C7
Stefanucci A, Zengin G, Llorent-Martinez EJ, Dimmito MP, Della Valle A, Pieretti S, Ak G, Sinan KI, Mollica A (2020) Chemical characterization, antioxidant properties and enzyme inhibition of Rutabaga root’s pulp and peel (Brassica napus L.). Arab J Chem 13(9):7078–7086. https://doi.org/10.1016/J.ARABJC.2020.07.013
Stevens JF, Reed RL (2011) Glucosinolate degradation products in fermented meadow foam seed meal and their herbicidal activities. In: Gang D (ed) The biological activity of phytochemicals, vol 41. Springer, New York, pp 141–157. https://doi.org/10.1007/978-1-4419-7299-6_10
Sturm C, Wagner AE (2017) Brassica-derived plant bioactives as modulators of chemopreventive and inflammatory signaling pathways. Int J Mol Sci 18:1890. https://doi.org/10.3390/IJMS18091890
Sun Z, Zhang K, Chen C, Wu Y, Tang Y, Georgiev MI, Zhang X, Lin M, Zhou M (2018) Biosynthesis and regulation of cyanogenic glycoside production in forage plants. Appl Microbiol Biotechnol 102(1):9–16
Szeja W, Grynkiewicz G, Rusin A (2016) Isoflavones, their glycosides and glycoconjugates. Synthesis and biological activity. Curr Org Chem 21(3):218–235
Talalay P, Fahey J, Talalay A (2011) Formulations for treatment with glucosinolates (Patent No. US13/577,181). United States Patent
Tang W, Zhang H, Wang L, Qian H, Qi X (2015) Targeted separation of antibacterial peptide from protein hydrolysate of anchovy cooking wastewater by equilibrium dialysis. Food Chem 168:115–123
Tang F, Fan K, Wang K, Bian C (2019) Amygdalin attenuates acute liver injury induced by D-galactosamine and lipopolysaccharide by regulating the NLRP3, NF-κB and Nrf2/NQO1 signalling pathways. Biomed Pharmacother 111:527–536
Thies W (1990) Photometric determination of indolyl glucosinolates in seeds of rapeseed. Eur J Lipid Sci Technol 92(4):161–164. https://doi.org/10.1002/LIPI.19900920409
Thinh Nguyen VP, Stewart J, Lopez M, Ioannou I, Allais F (2020) Glucosinolates: natural occurrence, biosynthesis, accessibility, isolation, structures, and biological activities. Molecules 25(19):4537. https://doi.org/10.3390/MOLECULES25194537
Tian Q, Rosselot RA, Schwartz SJ (2005) Quantitative determination of intact glucosinolates in broccoli, broccoli sprouts, Brussels sprouts, and cauliflower by high-performance liquid chromatography–electrospray ionization–tandem mass spectrometry. Anal Biochem 343(1):93–99. https://doi.org/10.1016/J.AB.2005.04.045
Verma S, Hussain ME (2017) Obesity and diabetes: an update. Diabetes Metab Syndr Clin Res Rev 11(1):73–79. https://doi.org/10.1016/J.DSX.2016.06.017
Vranova V, Rejsek K, Skene KR, Formanek P (2011) Non-protein amino acids: plant, soil and ecosystem interactions. Plant Soil 342:31–48
Vynnytska BO, Mayevska OM, Kurlishchuk YV, Bobak YP, Stasyk OV (2011) Canavanine augments proapoptotic effects of arginine deprivation in cultured human cancer cells. Anti-Cancer Drugs 22:148–157
Wagner AE, Will O, Sturm C, Lipinski S, Rosenstiel P, Rimbach G (2013) DSS-induced acute colitis in C57BL/6 mice is mitigated by sulforaphane pre-treatment. J Nutr Biochem 24(12):2085–2091. https://doi.org/10.1016/J.JNUTBIO.2013.07.009
Weng JR, Tsai CH, Kulp SK, Chen CS (2008) Indole-3-carbinol as a chemopreventive and anti-cancer agent. Cancer Lett 262(2):153–163. https://doi.org/10.1016/J.CANLET.2008.01.033
Wentzell AM, Kliebenstein DJ (2008) Genotype, age, tissue, and environment regulate the structural outcome of glucosinolate activation. Plant Physiol 147(1):415–428. https://doi.org/10.1104/PP.107.115279
Williams DJ, Critchley C, Pun S, Nottingham S, O’Hare TJ (2008) Epithiospecifier protein activity in broccoli: the link between terminal alkenyl glucosinolates and sulphoraphane nitrile. Phytochemistry 69(16):2765–2773. https://doi.org/10.1016/J.PHYTOCHEM.2008.09.018
Wittstock U, Meier K, Dörr F, Ravindran BM (2016) NSP-dependent simple nitrile formation dominates upon breakdown of major aliphatic glucosinolates in roots, seeds, and seedlings of Arabidopsis thaliana Columbia-0. Front Plant Sci 7(1821). https://doi.org/10.3389/FPLS.2016.01821/BIBTEX
Xue A, Liang W, Wen S, Gao Y, Huang X, Tong Y, Hao Y, Luo L (2021) Metabolomic analysis based on EESI-MS indicate blue LED light promotes aliphatic-glucosinolates biosynthesis in broccoli sprouts. J Food Compos Anal 97:103777. https://doi.org/10.1016/J.JFCA.2020.103777
Yamane H, Konno K, Sabelis M, Takabayashi J, Sassa T, Oikawa H (2010) Chemical defence and toxins of plants. In: Comprehensive natural products II: chemistry and biology, vol 4. Elsevier, New York, pp 339–385
Yang ZY, Zhong YY, Zheng J, Liu Y, Li T, Hu E, Zhu XF, Ding RQ, Wu Y, Zhang Y, Tang T, He F, Wang SS, Wang Y (2021) Fmoc-amino acid-based hydrogel vehicle for delivery of amygdalin to perform neuroprotection. Smart Mater Med 2:56–64
Yuan Y, Ran N, **ong L, Wang G, Guan X, Wang Z, Guo Y, Pang Z, Fang K, Lu J, Zhang C, Zheng R, Zheng J, Ma J, Wang F (2018) Obesity-related asthma: immune regulation and potential targeted therapies. J Immunol Res 1943497. https://doi.org/10.1155/2018/1943497
Yulvianti M, Zidorn C (2021) Chemical diversity of plant cyanogenic glycosides: an overview of reported natural products. Molecules 26(3):719
Zasada IA, Ferris H (2004) Nematode suppression with brassicaceous amendments: application based upon glucosinolate profiles. Soil Biol Biochem 36(7):1017–1024. https://doi.org/10.1016/J.SOILBIO.2003.12.014
Zhang Y, Cho CG, Posner GH, Talalay P (1992) Spectroscopic quantitation of organic isothiocyanates by cyclocondensation with vicinal dithiols. Anal Biochem 205(1):100–107. https://doi.org/10.1016/0003-2697(92)90585-U
Zhang Z, Ober JA, Kliebenstein DJ (2006) The gene controlling the quantitative trait locus EPITHIOSPECIFIER MODIFIER1 alters glucosinolate hydrolysis and insect resistance in arabidopsis. Plant Cell 18(6):1524–1536. https://doi.org/10.1105/TPC.105.039602
Zhao M, Bergaentzlé M, Flieller A, Marchioni E (2019) Development and validation of an ultra-high performance liquid chromatography-high resolution mass spectrometry method for simultaneous quantification of cyanogenic glycosides and secoisolariciresinol diglucoside in flaxseed (Linum usitatissimum L.). J Chromatogr A 1601:214–223
Zhong Y, Xu T, Chen Q, Li K, Zhang Z, Song H, Wang M, Wu X, Lu B (2020) Development and validation of eight cyanogenic glucosides via ultra-high-performance liquid chromatography-tandem mass spectrometry in agri-food. Food Chem 331:127305
Zhong Y, Xu T, Ji S, Wu X, Zhao T, Li S, Zhang P, Li K, Lu B (2021) Effect of ultrasonic pretreatment on eliminating cyanogenic glycosides and hydrogen cyanide in cassava. Ultrason Sonochem 78:105742
Zhou Y, Yang G, Tian H, Hu Y, Wu S, Geng Y, Lin K, Wu W (2018) Sulforaphane metabolites cause apoptosis via microtubule disruption in cancer. Endocr Relat Cancer 25(3):255–268. https://doi.org/10.1530/ERC-17-0483
Acknowledgments
The authors are grateful to the Foundation for Science and Technology (FCT, Portugal) for financial support by national funds FCT/MCTES to CIMO (UIDB/00690/2020). L. Barros thanks the national funding by FCT, P.I., through the institutional scientific employment program-contract, and F.A. Fernandes and F. Mandim Ph.D. grant (SFRH/BD/145467/2019 and SFRH/BD/146614/2019, respectively). C. Caleja thanks her contract through the project Healthy-PETFOOD (POCI-01-0247-FEDER-047073) and Manuel Ayuso is grateful to the LOCALNUTLEG project (PRIMA programme, Call 2020, Section 1 2021 Agrofood Value Chain topic 1.3.1.) for his postdoctoral research grant.
Author information
Authors and Affiliations
Corresponding authors
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2023 The Author(s), under exclusive license to Springer Nature Switzerland AG
About this chapter
Cite this chapter
Pereira, E. et al. (2023). Non-Alkaloid Nitrogen Containing Compounds. In: Carocho, M., Heleno, S.A., Barros, L. (eds) Natural Secondary Metabolites. Springer, Cham. https://doi.org/10.1007/978-3-031-18587-8_10
Download citation
DOI: https://doi.org/10.1007/978-3-031-18587-8_10
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-031-18586-1
Online ISBN: 978-3-031-18587-8
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)