Abstract
Glucosinolates are a group of sulfur- and nitrogen-containing glycosides found in the plant order Brassicales which includes several important vegetable crops of the Brassica genus such as broccoli, cabbage, radish and cauliflower among others. Their hydrolysis byproducts, namely isothiocyanataes, are responsible for the distinct aroma and pungent taste of cruciferous species, most of which contain species-specific glucosinolates, hence the high number of individual compounds. They are considered as beneficial to human compounds with several confirmed health effects, while a significant amount of research work has been carried out recently to identify those mechanisms and synergisms that are responsible for the activities of glucosinolates, as well to reveal physiological aspects in the plant × environment interactions. This chapter discusses the biochemistry and health properties of glucosinolates, their physiological significance as well as the hydrolysis process in the plant response to different abiotic stresses.
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
Abbaoui B, Telu KH, Lucas CR et al (2017) The impact of cruciferous vegetable isothiocyanates on histone acetylation and histone phosphorylation in bladder cancer. J Proteomics 156:94–103. https://doi.org/10.1016/j.jprot.2017.01.013
Abdull Razis AF, Bagatta M, De Nicola GR et al (2011) Up-regulation of cytochrome P450 and phase II enzyme systems in rat precision-cut rat lung slices by the intact glucosinolates, glucoraphanin and glucoerucin. Lung Cancer 71:298–305. https://doi.org/10.1016/j.lungcan.2010.06.015
Abdull Razis AF, De Nicola GR, Pagnotta E et al (2012) 4-Methylsulfanyl-3-butenyl isothiocyanate derived from glucoraphasatin is a potent inducer of rat hepatic phase II enzymes and a potential chemopreventive agent. Arch Toxicol 86:183–194. https://doi.org/10.1007/s00204-011-0750-x
Abe-Kanoh N, Kunisue N, Myojin T et al (2019) Yeast screening system reveals the inhibitory mechanism of cancer cell proliferation by benzyl isothiocyanate through down-regulation of Mis12. Sci Rep 9(1):8866. https://doi.org/10.1038/s41598-019-45248-2
Abuyusuf M, Robin A, Kim H-T et al (2018a) Altered glucosinolate profiles and expression of glucosinolate biosynthesis genes in ringspot-resistant and susceptible cabbage lines. Int J Mol Sci 19:2833. https://doi.org/10.3390/ijms19092833
Abuyusuf M, Robin A, Lee J-H et al (2018b) Glucosinolate profiling and expression analysis of glucosinolate biosynthesis genes differentiate white mold resistant and susceptible cabbage lines. Int J Mol Sci 19:4037. https://doi.org/10.3390/ijms19124037
Agerbirk N, Olsen CE (2012) Glucosinolate structures in evolution. Phytochemistry 77:16–45
Aggarwal M, Saxena R, Asif N et al (2019) P53 mutant-type in human prostate cancer cells determines the sensitivity to phenethyl isothiocyanate induced growth inhibition. J Exp Clin Cancer Res 38:1–17. https://doi.org/10.1186/s13046-019-1267-z
Aghajanzadeh T, Hawkesford MJ, De Kok LJ (2014) The significance of glucosinolates for sulfur storage in Brassicaceae seedlings. Front Plant Sci 5:1–10. https://doi.org/10.3389/fpls.2014.00704
Ahmad A, Dandawate P, Schruefer S et al (2019) Pentafluorophenyl substitution of natural Di(indol-3-yl)methane strongly enhances growth inhibition and apoptosis induction in various cancer cell lines. Chem Biodivers 16:e1900028. https://doi.org/10.1002/cbdv.201900028
Ahn J, Lee H, Im SW et al (2014) Allyl isothiocyanate ameliorates insulin resistance through the regulation of mitochondrial function. J Nutr Biochem 25:1026–1034. https://doi.org/10.1016/j.jnutbio.2014.05.006
Ahn M, Kim J, Bang H et al (2016) Hepatoprotective effects of allyl isothiocyanate against carbon tetrachloride-induced hepatotoxicity in rat. Chem Biol Interact 254:102–108. https://doi.org/10.1016/j.cbi.2016.05.037
Almuziny M, Decker C, Wang D et al (2017) Nutrient supply and simulated herbivory differentially alter the metabolite pools and the efficacy of the glucosinolate-based defense system in brassica species. J Chem Ecol 43:129–142. https://doi.org/10.1007/s10886-016-0811-y
Aronchik I, Kundu A, Quirit JG, Firestone GL (2014) The Anti-proliferative response of Indole-3-carbinol in human melanoma cells is triggered by an interaction with NEDD4-1 and disruption of wild-type PTEN degradation. Mol Cancer Res 12:1621–1624. https://doi.org/10.1038/jid.2014.371
Augustine R, Bisht NC (2015) Biofortification of oilseed Brassica juncea with the anti-cancer compound glucoraphanin by suppressing GSL-ALK gene family. Sci Rep 5:18005. https://doi.org/10.1038/srep18005
Bachiega P, Salgado JM, De Carvalho JE et al (2016) Antioxidant and antiproliferative activities in different maturation stages of broccoli (Brassica oleracea Italica) biofortified with selenium. Food Chem 190:771–776. https://doi.org/10.1016/j.foodchem.2015.06.024
Baenas N, Gómez-Jodar I, Moreno DA et al (2017) Broccoli and radish sprouts are safe and rich in bioactive phytochemicals. Postharvest Biol Technol 127:60–67. https://doi.org/10.1016/j.postharvbio.2017.01.010
Bai Y, Wang X, Zhao S et al (2015) Sulforaphane protects against cardiovascular disease via Nrf2 activation. Oxid Med Cell Longev 2015:407580. https://doi.org/10.1155/2015/407580
Bak S, Linde Nielsen H, Halkier BA (1998) The presence of CYP79 homologues in glucosinolate-producing plants shows evolutionary conservation of the enzymes in the conversion of amino acid to aldoxime in the biosynthesis of cyanogenic glucosides and glucosinolates. Plant Mol Biol 38(5):725–734
Bak S, Tax FE, Feldmann KA et al (2001) CYP83B1, a cytochrome P450 at the metabolic branch point in auxin and indole glucosinolate biosynthesis in Arabidopsis. Plant Cell 13:101–111. https://doi.org/10.1105/tpc.13.1.101
Banerjee S, Siemianowski O, Liu M et al (2019) Stress response to CO 2 deprivation by Arabidopsis thaliana in plant cultures. PLoS One 14:1–18. https://doi.org/10.1371/journal.pone.0212462
Bao C, Kim MC, Chen J et al (2016) Sulforaphene interferes with human breast cancer cell migration and invasion through inhibition of hedgehog signaling. J Agric Food Chem 64:5515–5524. https://doi.org/10.1021/acs.jafc.6b02195
Bell L, Oloyede OO, Lignou S et al (2018) Taste and flavor perceptions of glucosinolates, isothiocyanates, and related compounds. Mol Nutr Food Res 62(18):e1700990. https://doi.org/10.1002/mnfr.201700990
Bennett RN, Kiddle GUY, Wallsgrove RM (1997) Biosynthesis of benzylglucosinolate, cyanogenic glucosides and phenylpropanoids in Carica papaya. Phytochemistry 45:59–66
Bielecka M, Watanabe M, Morcuende R et al (2015) Transcriptome and Metabolome analysis of plant sulfate starvation and resupply provides novel information on transcriptional regulation of metabolism associated with sulfur, nitrogen and phosphorus nutritional responses in Arabidopsis. Front Plant Sci 5:1–18. https://doi.org/10.3389/fpls.2014.00805
Blažević I, Đulović A, Maravić A et al (2019) Antimicrobial and cytotoxic activities of Lepidium latifolium L. Hydrodistillate, extract and its major sulfur volatile allyl isothiocyanate. Chem Biodivers 16(4):e1800661. https://doi.org/10.1002/cbdv.201800661
Blažević I, Montaut S, Burčul F et al (2020) Glucosinolate structural diversity, identification, chemical synthesis and metabolism in plants. Phytochemistry 169:112100. https://doi.org/10.1016/j.phytochem.2019.112100
Bo P, Lien J-C, Chen Y-Y et al (2016) Allyl isothiocyanate induces cell toxicity by multiple pathways in human breast cancer cells. Am J Chin Med 44:415–437. https://doi.org/10.1142/S0192415X16500245
Bohinc T, Trdan S (2012) Environmental factors affecting the glucosinolate content in Brassicaceae. J Food Agric Environ 10:357–360
Bolarinwa IF, Oke MO, Olaniyan SA, Ajala AS (2016) A review of cyanogenic glycosides in edible plants. In: Toxicology - new aspects to this scientific conundrum. InTechOpen, New York
Bones AM, Rossiter JT (2006) The enzymic and chemically induced decomposition of glucosinolates. Phytochemistry 67:1053–1067. https://doi.org/10.1016/j.phytochem.2006.02.024
Bose C, Awasthi S, Sharma R et al (2018) Sulforaphane potentiates anticancer effects of doxorubicin and attenuates its cardiotoxicity in a breast cancer model. PLoS One 13:1–22. https://doi.org/10.1371/journal.pone.0193918
Brown AF, Yousef GG, Jeffery EH et al (2002) Glucosinolate profiles in broccoli: variation in levels and implications in breeding for cancer chemoprotection. J Am Soc Hortic Sci 127:807–813
Burčul F, Generalić Mekinić I, Radan M et al (2018) Isothiocyanates: cholinesterase inhibiting, antioxidant, and anti-inflammatory activity. J Enzyme Inhib Med Chem. 33(1):577–582. https://doi.org/10.1080/14756366.2018.1442832
Byun S, Shin SH, Park J et al (2016) Sulforaphene suppresses growth of colon cancer-derived tumors via induction of glutathione depletion and microtubule depolymerization. Mol Nutr Food Res 60:1068–1078. https://doi.org/10.1002/mnfr.201501011
Caglayan B, Kilic E, Dalay A et al (2019) Allyl isothiocyanate attenuates oxidative stress and inflammation by modulating Nrf2/HO-1 and NF-κB pathways in traumatic brain injury in mice. Mol Biol Rep 46:241–250. https://doi.org/10.1007/s11033-018-4465-4
Cavell BE, Syed Alwi SS, Donlevy A, Packham G (2011) Anti-angiogenic effects of dietary isothiocyanates: mechanisms of action and implications for human health. Biochem Pharmacol 81:327–336. https://doi.org/10.1016/j.bcp.2010.10.005
Chang W, Chen B, Inbaraj BS, Chien J (2019) Preparation of allyl isothiocyanate nanoparticles, their anti-inflammatory activity towards RAW 264.7 macrophage cells and anti-proliferative effect on HT1376 bladder cancer cells. J Sci Food Agric 99:3106–3116. https://doi.org/10.1002/jsfa.9524
Charron CS, Sams CE (2004) Glucosinolate content and myrosinase activity in rapid-cycling Brassica oleracea grown in a controlled environment. J Am Soc Hortic Sci 129:321–330. https://doi.org/10.21273/jashs.129.3.0321
Charron CS, Saxton AM, Sams CE (2005) Relationship of climate and genotype to seasonal variation in the glucosinolate-myrosinase system. I. Glucosinolate content in ten cultivars of Brassica oleracea grown in fall and spring seasons. J Sci Food Agric 85:671–681. https://doi.org/10.1002/jsfa.1880
Chatterjee S, Rhee Y-H, Ahn J-C (2016) Sulforaphene–carboplatin combination synergistically enhances apoptosis by disruption of mitochondrial membrane potential and cell cycle arrest in human non-small cell lung carcinoma. J Med Food 19:860–869. https://doi.org/10.1089/jmf.2016.3675
Chawalitpong S, Ichikawa S, Uchibori Y et al (2019) Long-term intake of glucoraphanin-enriched kale suppresses skin aging via activating Nrf2 and the TβRII/Smad pathway in SAMP1 mice. J Agric Food Chem 67:9782–9788. https://doi.org/10.1021/acs.jafc.9b02725
Chen J, Bao C, Kim JT et al (2018a) Sulforaphene inhibition of adipogenesis via hedgehog signaling in 3T3-L1 adipocytes. J Agric Food Chem 66:11926–11934. https://doi.org/10.1021/acs.jafc.8b04330
Chen Y, Li Y, Qian WX et al (2018b) Phenethyl isothiocyanate inhibits colorectal cancer stem cells by suppressing Wnt/β-catenin pathway. Phyther Res 32:2447–2455. https://doi.org/10.1002/ptr.6183
Cho HJ, Lee KW, Yoon Park JH (2013) Erucin exerts anti-inflammatory properties in murine macrophages and mouse skin: possible mediation through the inhibition of NFκB signaling. Int J Mol Sci 14:20564–20577. https://doi.org/10.3390/ijms141020564
Choi KM, Yoo HS (2018) 3,3′-Diindolylmethane enhances glucose uptake through activation of insulin signaling in 3T3-L1 adipocytes. Obesity 26:1153–1160. https://doi.org/10.1002/oby.22145
Choi K-M, Yoo H-S (2019) Amelioration of hyperglycemia-induced nephropathy by 3,3′-diindolylmethane in diabetic mice. Molecules 24:1–9
Choi KM, Lee YS, Sin DM et al (2012) Sulforaphane inhibits mitotic clonal expansion during adipogenesis through cell cycle arrest. Obesity 20:1365–1371. https://doi.org/10.1038/oby.2011.388
Choi E, Zhang P, Kwon H (2014a) Determination of goitrogenic metabolites in the serum of male Wistar rat fed structurally different glucosinolates. Toxicol Res 30:109–116
Choi KM, Lee YS, Kim W et al (2014b) Sulforaphane attenuates obesity by inhibiting adipogenesis and activating the AMPK pathway in obese mice. J Nutr Biochem 25:201–207. https://doi.org/10.1016/j.jnutbio.2013.10.007
Choi Y, Abdelmegeed MA, Song BJ (2018) Preventive effects of indole-3-carbinol against alcohol-induced liver injury in mice via antioxidant, anti-inflammatory, and anti-apoptotic mechanisms: role of gut-liver-adipose tissue axis. J Nutr Biochem 55:12–25. https://doi.org/10.1016/j.jnutbio.2017.11.011
Chuang W-Y, Kung P-H, Kuo C-Y, Wu C-C (2013) Sulforaphane prevents human platelet aggregation through inhibiting the phosphatidylinositol 3-kinase/Akt pathway. Thromb Haemost 109:1120–1130. https://doi.org/10.1160/TH12-09-0636
Chuang W-T, Liu Y-T, Huang C-S et al (2019) Benzyl isothiocyanate and phenethyl isothiocyanate inhibit adipogenesis and hepatosteatosis in mice with obesity induced by a high-fat diet. J Agric Food Chem 67:7136–7146. https://doi.org/10.1021/acs.jafc.9b02668
Chun JH, Kim S, Arasu MV et al (2017) Combined effect of nitrogen, phosphorus and potassium fertilizers on the contents of glucosinolates in rocket salad (Eruca sativa Mill.). Saudi J Biol Sci 24:436–443. https://doi.org/10.1016/j.sjbs.2015.08.012
Cipollini D, Gruner B (2007) Cyanide in the chemical arsenal of garlic mustard, Alliaria petiolata. J Chem Ecol 33:85–94. https://doi.org/10.1007/s10886-006-9205-x
Cirmi S, Ferlazzo N, Gugliandolo A et al (2019) Moringin from moringa oleifera seeds inhibits growth, arrests cell-cycle, and induces apoptosis of SH-SY5Y human neuroblastoma cells through the modulation of NF-kB and apoptotic related factors. Int J Mol Sci 20(8):1930. https://doi.org/10.3390/ijms20081930
Citi V, Martelli A, Testai L et al (2014) Hydrogen sulfide releasing capacity of natural isothiocyanates: is it a reliable explanation for the multiple biological effects of brassicaceae? Planta Med 80:610–613. https://doi.org/10.1055/s-0034-1368591
Citi V, Piragine E, Pagnotta E et al (2019) Anticancer properties of erucin, an H 2 S-releasing isothiocyanate, on human pancreatic adenocarcinoma cells (AsPC-1). Phyther Res 33:845–855. https://doi.org/10.1002/ptr.6278
Clarke DB (2010) Glucosinolates, structures and analysis in food. Anal Methods 2:310. https://doi.org/10.1039/b9ay00280d
Crowley E, Rowan NJ, Faller D, Friel AM (2019) Natural and synthetic isothiocyanates possess anticancer potential against liver and prostate cancer in vitro. Anticancer Res 39:3469–3485. https://doi.org/10.21873/anticanres.13493
Dall’Acqua S, Ertani A, Pilon-Smits EAH et al (2019) Selenium biofortification differentially affects sulfur metabolism and accumulation of phytochemicals in two rocket species (Eruca sativa Mill. and Diplotaxis tenuifolia) grown in hydroponics. Plants 8:1–19. https://doi.org/10.3390/plants8030068
De Souza CG, Da Motta LL, De Assis AM et al (2016) Sulforaphane ameliorates the insulin responsiveness and the lipid profile but does not alter the antioxidant response in diabetic rats. Food Funct 7:2060–2065. https://doi.org/10.1039/c5fo01620g
Del Carmen MBM, Moreno DA, Carvajal M (2013) The physiological importance of glucosinolates on plant response to abiotic stress in brassica. Int J Mol Sci 14:14. https://doi.org/10.3390/ijms140611607
Di Cesare ML, Lucarini E, Micheli L et al (2017) Effects of natural and synthetic isothiocyanate-based H2S-releasers against chemotherapy-induced neuropathic pain: role of Kv7 potassium channels. Neuropharmacology 121:49–59. https://doi.org/10.1016/j.neuropharm.2017.04.029
Di Gioia F, De Bellis P, Mininni C et al (2017a) Physicochemical, agronomical and microbiological evaluation of alternative growing media for the production of rapini (Brassica rapa L.) microgreens. J Sci Food Agric 97:1212–1219. https://doi.org/10.1002/jsfa.7852
Di Gioia F, Renna M, Santamaria P (2017b) Sprouts, microgreens and “baby leaf” vegetables. In: Food engineering series. Springer, Boston, pp 403–432
Di Gioia F, Avato P, Serio F, Argentieri MPMP (2018a) Glucosinolate profile of Eruca sativa, Diplotaxis tenuifolia and Diplotaxis erucoides grown in soil and soilless systems. J Food Compos Anal 69:197–204. https://doi.org/10.1016/j.jfca.2018.01.022
Di Gioia F, Rosskopf EN, Leonardi C, Giuffrida F (2018b) Effects of application timing of saline irrigation water on broccoli production and quality. Agric Water Manag 203:97–104. https://doi.org/10.1016/j.agwat.2018.01.004
Di Gioia F, Pinela J, de Haro Bailón A et al (2020) The dilemma of “good” and “bad” glucosinolates and the potential to regulate their content. In: Galanakis CM (ed) Glucosinolates: properties, recovery, and applications. Academic Press, London, pp 1–45
Dinkova-Kostova AT, Kostov RV (2012) Glucosinolates and isothiocyanates in health and disease. Trends Mol Med 18:337–347. https://doi.org/10.1016/j.molmed.2012.04.003
Drewnowski A, Gomez-Carneros C (2000) Bitter taste, phytonutrients, and the consumer: A review. Am J Clin Nutr 72:1424–1435. https://doi.org/10.1093/ajcn/72.6.1424
Eisenbrand G, Peter H (2016) Assessing the potential impact on the thyroid axis of environmentally relevant food constituents/contaminants in humans. Arch Toxicol 90:1841–1857. https://doi.org/10.1007/s00204-016-1735-6
Encinas-Basurto D, Ibarra J, Juarez J et al (2017) Poly(lactic-co-glycolic acid) nanoparticles for sustained release of allyl isothiocyanate: characterization, in vitro release and biological activity. J Microencapsul 34:231–242. https://doi.org/10.1080/02652048.2017.1323037
Encinas-Basurto D, Juarez J, Valdez MA et al (2018) Targeted drug delivery via human epidermal growth factor receptor for sustained release of allyl isothiocyanate. Curr Top Med Chem 18:1252–1260
Eschliman K, Bossmann SH (2019) Synthesis of isothiocyanates: an update. Synth 51:1746–1752. https://doi.org/10.1055/s-0037-1612303
Esfandiari A, Saei A, McKenzie MJ et al (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
Ettlinger MG, Lundeen AJ (1956) The structures of sinigrin and sinalbin; an enzymatic rearrangement. J Am Chem Soc 78:4172–4173. https://doi.org/10.1021/ja01597a090
Fahey JW, Zalcmann AT, Talalay P (2001) The chemical diversity and distribution of glucosinolates and isothiocyanates among plants. Phytochemistry 56(1):5–51
Fahey JW, Olson ME, Stephenson KK et al (2018) The diversity of chemoprotective glucosinolates in moringaceae (Moringa spp.). Sci Rep 8:1–14. https://doi.org/10.1038/s41598-018-26058-4
Farnham MW, Wilson PE, Stephenson KK, Fahey JW (2004) Genetic and environmental effects on glucosinolate content and chemoprotective potency of broccoli. Plant Breed 123(1):60–65. https://doi.org/10.1046/j.0179-9541.2003.00912.x
Felker P, Bunch R, Leung AM (2016) Concentrations of thiocyanate and goitrin in human plasma, their precursor concentrations in brassica vegetables, and associated potential risk for hypothyroidism. Nutr Rev 74:248–258. https://doi.org/10.1093/nutrit/nuv110
Fimognari C, Turrini E, Ferruzzi L et al (2012) Natural isothiocyanates: genotoxic potential versus chemoprevention. Mutat Res- Rev Mutat Res 750:107–131. https://doi.org/10.1016/j.mrrev.2011.12.001
Gaitan E (1990) Goitrogens in food and water. Annu Rev Nutr 10:21–39
Galuppo M, De Nicola GR, Iori R et al (2013) Antibacterial activity of glucomoringin bioactivated with myrosinase against two important pathogens affecting the health of long-term patients in hospitals. Molecules 18:14340–14348. https://doi.org/10.3390/molecules181114340
Gao M, Li G, Potter D et al (2006) Comparative analysis of methylthioalkylmalate synthase (MAM) gene family and flanking DNA sequences in Brassica oleracea and Arabidopsis thaliana. Plant Cell Rep 25:592–598. https://doi.org/10.1007/s00299-005-0078-1
Giacoppo S, Galuppo M, Montaut S et al (2015) An overview on neuroprotective effects of isothiocyanates for the treatment of neurodegenerative diseases. Fitoterapia 106:12–21
Grubb CD, Abel S (2006) Glucosinolate metabolism and its control. Trends Plant Sci 11:89–100. https://doi.org/10.1016/j.tplants.2005.12.006
Grubb CD, Zipp BJ, Ludwig-Müller J et al (2004) Arabidopsis glucosyltransferase UGT74B1 functions in glucosinolate biosynthesis and auxin homeostasis. Plant J 40:893–908. https://doi.org/10.1111/j.1365-313X.2004.02261.x
Gründemann C, Huber R (2018) Chemoprevention with isothiocyanates – From bench to bedside. Cancer Lett 414:26–33. https://doi.org/10.1016/J.CANLET.2017.10.033
Gupta R, Bhatt LK, Momin M (2019) Potent antitumor activity of Laccaic acid and Phenethyl isothiocyanate combination in colorectal cancer via dual inhibition of DNA methyltransferase-1 and Histone deacetylase-1. Toxicol Appl Pharmacol 377:114631. https://doi.org/10.1016/j.taap.2019.114631
Halkier BA (2016) General introduction to glucosinolates. In: Advances in botanical research. Elsevier, Amsterdam
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
Han KWW, Po WW, Sohn UD, Kim HJ (2019a) Benzyl isothiocyanate induces apoptosis via reactive oxygen species-initiated mitochondrial dysfunction and DR4 and DR5 death receptor activation in gastric adenocarcinoma cells. Biomolecules 9(12):839. https://doi.org/10.3390/biom9120839
Han N, Ku KM, Kim J (2019b) Postharvest variation of major glucosinolate and their hydrolytic products in Brassicoraphanus ‘BB1’. Postharvest Biol Technol 154:70–78. https://doi.org/10.1016/j.postharvbio.2019.04.011
Hanlon PR, Robbins MG, Hammon LD, Barnes DM (2009) Aqueous extract from the vegetative portion of Spanish black radish (Raphanus sativus L. var. niger) induces detoxification enzyme expression in HepG2 cells. J Funct Foods 1:356–365. https://doi.org/10.1016/j.jff.2009.08.001
Hanschen FS, Herz C, Schlotz N, Kupke F (2015) The Brassica epithionitrile 1-cyano-2, 3-epithiopropane triggers cell death in human liver cancer cells in vitro. Mol Nutr Food Res 59:2178–2189. https://doi.org/10.1002/mnfr.201500296
Hansen CH, Du L, Naur P et al (2001) CYP83B1 is the oxime-metabolizing enzyme in the glucosinolate pathway in arabidopsis. J Biol Chem 276:24790–24796. https://doi.org/10.1074/jbc.M102637200
Hasan H, Ismail H, El-Orfali Y, Khawaja G (2018) Therapeutic benefits of Indole-3-Carbinol in adjuvant-induced arthritis and its protective effect against methotrexate induced-hepatic toxicity. BMC Complement Altern Med 18:1–12. https://doi.org/10.1186/s12906-018-2408-1
Hassini I, Rios JJ, Garcia-Ibañez P et al (2019) Comparative effect of elicitors on the physiology and secondary metabolites in broccoli plants. J Plant Physiol 239:1–9. https://doi.org/10.1016/j.jplph.2019.05.008
He Y, Mawhinney TP, Preuss ML et al (2009) A redox-active isopropylmalate dehydrogenase functions in the biosynthesis of glucosinolates and leucine in Arabidopsis. Plant J 60:679–690. https://doi.org/10.1111/j.1365-313X.2009.03990.x
He Y, Chen B, Pang Q et al (2010) Functional specification of Arabidopsis isopropylmalate isomerases in glucosinolate and leucine biosynthesis. Plant Cell Physiol 51:1480–1487. https://doi.org/10.1093/pcp/pcq113
Hirai MY, Klein M, Fujikawa Y et al (2005) Elucidation of gene-to-gene and metabolite-to-gene networks in arabidopsis by integration of metabolomics and transcriptomics. J Biol Chem 280:25590–25595. https://doi.org/10.1074/jbc.M502332200
Holst B, Fenwick GR (2003) Glucosinolates. In: Caballero B, Finglas P, Toldra F (eds) Encyclopedia of food sciences and nutrition, 2nd edn. Academic Press, Oxford, pp 2922–2930
Huang CS, Lin AH, Liu CT et al (2013) Isothiocyanates protect against oxidized LDL-induced endothelial dysfunction by upregulating Nrf2-dependent antioxidation and suppressing NFκB activation. Mol Nutr Food Res 57:1918–1930. https://doi.org/10.1002/mnfr.201300063
Humphrey PT, Gloss AD, Alexandre NM et al (2016) Aversion and attraction to harmful plant secondary compounds jointly shape the foraging ecology of a specialist herbivore. Ecol Evol 6(10):3256–3268. https://doi.org/10.1002/ece3.2082
Hung C-N, Huang H-P, Wang C-J et al (2014) Sulforaphane inhibits TNF-α-induced adhesion molecule expression through the Rho A/ROCK/NF-κB signaling pathway. J Med Food 17:1095–1102. https://doi.org/10.1089/jmf.2013.2901
Ibrahim MD, Kntayya SB, Mohd Ain N et al (2018) Induction of apoptosis and cytotoxicity by raphasatin in human breast adenocarcinoma MCF-7 cells. Molecules 23(12):3092. https://doi.org/10.3390/molecules23123092
Ishida M, Hara M, Fukino N et al (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 et al (2018a) Protective effect of glucosinolates hydrolytic products in neurodegenerative diseases (NDDs). Nutrients 10:1–15. https://doi.org/10.3390/nu10050580
Jaafaru MS, Karim NAA, Eliaser EM et al (2018b) Nontoxic glucomoringin-isothiocyanate (GMG-ITC) rich soluble extract induces apoptosis and inhibits proliferation of human prostate adenocarcinoma cells (PC-3). Nutrients 10(9):1174. https://doi.org/10.3390/nu10091174
Jaafaru MS, Nordin N, Rosli R et al (2019) Neuroprotective effects of glucomoringin-isothiocyanate against H2O2-induced cytotoxicity in neuroblastoma (SH-SY5Y) cells. Neurotoxicology 75:89–104. https://doi.org/10.1016/j.neuro.2019.09.008
Jadhav U, Ezhilarasan R, Vaughn SF et al (2007) Iberin induces cell cycle arrest and apoptosis in human neuroblastoma cells. Int J Mol Med 19:353–361. https://doi.org/10.3892/ijmm.2012.1167
Jakobsen TH, Bragason SK, Phipps RK et al (2012) Food as a source for quorum sensing inhibitors: iberin from horseradish revealed as a quorum sensing inhibitor of Pseudomonas aeruginosa. Appl Environ Microbiol 78:2410–2421. https://doi.org/10.1128/AEM.05992-11
Jakubikova J, Bao Y, Sedlak J (2005) Isothiocyanates induce cell cycle arrest, apoptosis and mitochondrial potential depolarization in HL-60 and multidrug-resistant cell lines. Anticancer Res 25:3375–3386
Jakubikova J, Bao Y, Bodo J, Sedlak J (2006) Isothiocyanate iberin modulates phase II enzymes, posttranslational modification of histones and inhibits growth of Caco-2 cells by inducing apoptosis. Neoplasma 53:463–470
Jang M, Hong E, Kim GH (2010) Evaluation of antibacterial activity of 3-butenyl, 4-pentenyl, 2-phenylethyl, and benzyl isothiocyanate in Brassica vegetables. J Food Sci 75:412–416. https://doi.org/10.1111/j.1750-3841.2010.01725.x
Jayakumar T, Chen WF, Lu WJ et al (2013) A novel antithrombotic effect of sulforaphane via activation of platelet adenylate cyclase: ex vivo and in vivo studies. J Nutr Biochem 24:1086–1095. https://doi.org/10.1016/j.jnutbio.2012.08.007
Jeong WS, Kim IW, Hu R, Kong ANT (2004) Modulatory properties of various natural chemopreventive agents on the activation of NF-κB signaling pathway. Pharm Res 21:661–670. https://doi.org/10.1023/B:PHAM.0000022413.43212.cf
Jiang Z, Liu X, Chang K et al (2016) Allyl isothiocyanate inhibits the proliferation of renal carcinoma cell line GRC-1 by inducing an imbalance between Bcl2 and Bax. Med Sci Monit 22:4283–4288. https://doi.org/10.12659/MSM.897315
Jiang Y, Fang Y, Ye Y et al (2019) Anti-cancer effects of 3, 3′-diindolylmethane on human hepatocellular carcinoma cells is enhanced by calcium ionophore: the role of cytosolic Ca2+ and P38 mapk. Front Pharmacol 10:1–23. https://doi.org/10.3389/fphar.2019.01167
Jirovetz L, Smith D, Buchbauer G (2002) Aroma compound analysis of Eruca sativa (Brassicaceae) SPME headspace leaf samples using GC, GC-MS, and olfactometry. J Agric Food Chem 50:4643–4646. https://doi.org/10.1021/jf020129n
Justen VL, Science A, Falls R, Fritz VA (2013) Temperature-induced glucosinolate accumulation is associated with expression of BrMYB transcription factors. HortScience 48:47–52
Kaiser SJ, Mutters NT, Blessing B, Günther F (2017) Natural isothiocyanates express antimicrobial activity against developing and mature biofilms of Pseudomonas aeruginosa. Fitoterapia 119:57–63. https://doi.org/10.1016/j.fitote.2017.04.006
Kassie F, Knasmüller S (2004) 21 - Glucosinolates and the prevention of cancer. In: Remacle C, Reusens B (eds) Functional food, ageing and degenerative disease, Woodhead publishing series in food science, technology and nutrition. Woodhead Publishing, Sawston, pp 615–627
Kim S-H, Singh SV (2019) Role of Krüppel-like factor 4-p21 CIP1 axis in breast cancer stem-like cell inhibition by benzyl isothiocyanate. Cancer Prev Res 12:125 LP–125134. https://doi.org/10.1158/1940-6207.CAPR-18-0393
Kim Y-J, Lee D-H, Ahn J et al (2015) Pharmacokinetics, Tissue distribution, and anti-lipogenic/adipogenic effects of allyl-isothiocyanate metabolites. PLoS One 10:e0132151. https://doi.org/10.1371/journal.pone.0132151
Kim J, Bang H, Ahn M et al (2018a) Allyl isothiocyanate reduces liver fibrosis by regulating Kupffer cell activation in rats. J Vet Med Sci 80:893–897. https://doi.org/10.1292/jvms.17-0637
Kim MW, Choi S, Kim SY et al (2018b) Allyl isothiocyanate ameliorates dextran sodium sulfate-induced colitis in mouse by enhancing tight junction and mucin expression. Int J Mol Sci:19. https://doi.org/10.3390/ijms19072025
Kissen R, Rossiter JT, Bones AM (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
Kntayya SB, Ibrahim MD, Ain NM et al (2018) Induction of apoptosis and cytotoxicity by isothiocyanate sulforaphene in human hepatocarcinoma HepG2 cells. Nutrients 10:1–15. https://doi.org/10.3390/nu10060718
Ko MO, Kim MB, Bin LS (2016) Relationship between chemical structure and antimicrobial activities of isothiocyanates from cruciferous vegetables against oral pathogens. J Microbiol Biotechnol 26:2036–2042. https://doi.org/10.4014/jmb.1606.06008
Kopriva S, Gigolashvili T (2016) Glucosinolate synthesis in the context of plant metabolism. Elsevier, Amsterdam
Kopsell DA, Sams CE (2013) Increases in shoot tissue pigments, glucosinolates, and mineral elements in sprouting broccoli after exposure to short-duration blue light from light emitting diodes. J Am Soc Hortic Sci 138:31–37
Koroleva OA, Gibson TM, Cramer R, Stain C (2010) Glucosinolate-accumulating S-cells in Arabidopsis leaves and flower stalks undergo programmed cell death at early stages of differentiation. Plant J 64:456–469. https://doi.org/10.1111/j.1365-313X.2010.04339.x
Kuchernig JC, Backenköhler A, Lübbecke M et al (2011) A thiocyanate-forming protein generates multiple products upon allylglucosinolate breakdown in Thlaspi arvense. Phytochemistry 72(14-15):1699–1709. https://doi.org/10.1016/j.phytochem.2011.06.013
Kumar G, Tuli HS, Mittal S et al (2015) Isothiocyanates: a class of bioactive metabolites with chemopreventive potential. Tumor Biol 36:4005–4016
Kupke F, Herz C, Hanschen FS et al (2016) Cytotoxic and genotoxic potential of food-borne nitriles in a liver in vitro model. Sci Rep 6:37631. https://doi.org/10.1038/srep37631
Kwapong AA, Stapleton P, Gibbons S (2019) Inhibiting plasmid mobility: the effect of isothiocyanates on bacterial conjugation. Int J Antimicrob Agents 53:629–636. https://doi.org/10.1016/j.ijantimicag.2019.01.011
Kyriacou MC, Rouphael Y, Di Gioia F et al (2016) Micro-scale vegetable production and the rise of microgreens. Trends Food Sci Technol 57:103–115
La Marca M, Beffy P, Della Croce C et al (2012) Structural influence of isothiocyanates on expression of cytochrome P450, phase II enzymes, and activation of Nrf2 in primary rat hepatocytes. Food Chem Toxicol 50:2822–2830. https://doi.org/10.1016/j.fct.2012.05.044
Lachance JC, Radhakrishnan S, Madiwale G et al (2020) Targeting hallmarks of cancer with a food-system–based approach. Nutrition 69:110563. https://doi.org/10.1016/j.nut.2019.110563
Lamy E, Mersch-Sundermann V (2009) MTBITC mediates cell cycle arrest and apoptosis induction in human hepg2 cells despite its rapid degradation kinetics in the in vitro model. Environ Mol Mutagen 50:190–200. https://doi.org/10.1002/em.20448
Latté KP, Appel K, Lampen A (2011) Health benefits and possible risks of broccoli – an overview. Food Chem Toxicol 49:3287–3309. https://doi.org/10.1016/j.fct.2011.08.019
Lee CM, Park S-H, Nam MJ (2018) Anticarcinogenic effect of indole-3-carbinol (I3C) on human hepatocellular carcinoma SNU449 cells. Hum Exp Toxicol 38:136–147. https://doi.org/10.1177/0960327118785235
Lee BD, Yoo J-M, Baek SY et al (2020) 3,3′-Diindolylmethane Promotes BDNF and Antioxidant Enzyme Formation via TrkB/Akt Pathway Activation for Neuroprotection against Oxidative Stress-Induced Apoptosis in Hippocampal Neuronal. Antioxidants 9:1–14
Li G, Quiros CF (2002) Genetic analysis, expression and molecular characterization of BoGSL-ELONG, a major gene involved in the aliphatic glucosinolate pathway of Brassica species. Genetics 162:1937–1943
Li W, Guo Y, Zhang C et al (2016) Dietary phytochemicals and cancer chemoprevention: a perspective on oxidative stress, inflammation, and epigenetics. Chem Res Toxicol 29:2071–2095. https://doi.org/10.1021/acs.chemrestox.6b00413
Li C-X, Gao J-G, Wan X-Y et al (2019) Allyl isothiocyanate ameliorates lipid accumulation and inflammation in nonalcoholic fatty liver disease via the Sirt1/AMPK and NF-κB signaling pathways. World J Gastroenterol 25:5120–5133. https://doi.org/10.3748/wjg.v25.i34.5120
Liang K, Qian WH, Zong J (2017) 3,3′-Diindolylmethane attenuates cardiomyocyte hypoxia by modulating autophagy in H9c2 cells. Mol Med Rep 16:9553–9560. https://doi.org/10.3892/mmr.2017.7788
Lim S, Han SW, Kim J (2016) Sulforaphene identified from radish (Raphanus sativus L.) seeds possesses antimicrobial properties against multidrug-resistant bacteria and methicillin-resistant Staphylococcus aureus. J Funct Foods 24:131–141. https://doi.org/10.1016/j.jff.2016.04.005
Liu P, Behray M, Wang Q et al (2018) Anti-cancer activities of allyl isothiocyanate and its conjugated silicon quantum dots. Sci Rep 8:1–11. https://doi.org/10.1038/s41598-018-19353-7
Lo C-W, Chen C-S, Chen Y-C et al (2018) Allyl isothiocyanate ameliorates obesity by inhibiting Galectin-12. Mol Nutr Food Res 62:1700616. https://doi.org/10.1002/mnfr.201700616
Lu Z, Dockery CR, Crosby M et al (2016) Antibacterial activities of wasabi against Escherichia coli O157: H7 and Staphylococcus aureus. Front Microbiol 7:1–9. https://doi.org/10.3389/fmicb.2016.01403
Ma YS, Hsiao YT, Lin JJ et al (2017) Phenethyl isothiocyanate (PEITC) and benzyl isothiocyanate (BITC) inhibit human melanoma A375.S2 cell migration and invasion by affecting MAPK signaling pathway in vitro. Anticancer Res 37:6223–6234. https://doi.org/10.21873/anticanres.12073
Ma L, Liu G, Sampson L et al (2018a) Dietary glucosinolates and risk of type 2 diabetes in 3 prospective cohort studies. Am J Clin Nutr 107:617–625. https://doi.org/10.1093/ajcn/nqy003
Ma YS, Lin JJ, Lin CC et al (2018b) Benzyl isothiocyanate inhibits human brain glioblastoma multiforme GBM 8401 cell xenograft tumor in nude mice in vivo. Environ Toxicol 33:1097–1104. https://doi.org/10.1002/tox.22581
Macleod G, MacLeod AJ (1990) The glucosinolates and aroma volatiles of green kohlrabi. Phytochemistry 29:1183–1187. https://doi.org/10.1016/0031-9422(90)85425-F
Marino D, Ariz I, Lasa B et al (2016) Quantitative proteomics reveals the importance of nitrogen source to control glucosinolate metabolism in Arabidopsis thaliana and Brassica oleracea. J Exp Bot 67:3313–3323. https://doi.org/10.1093/jxb/erw147
Martelli A, Testai L, Citi V et al (2014) Pharmacological characterization of the vascular effects of aryl isothiocyanates: Is hydrogen sulfide the real player? Vascul Pharmacol 60:32–41. https://doi.org/10.1016/j.vph.2013.11.003
Martelli A, Piragine E, Citi V et al (2019) Erucin exhibits vasorelaxing effects and antihypertensive activity by H 2 S-releasing properties. Br J Pharmacol 4:1–12. https://doi.org/10.1111/bph.14645
Martins T, Colaço B, Venâncio C et al (2018) Potential effects of sulforaphane to fight obesity. J Sci Food Agric 98:2837–2844. https://doi.org/10.1002/jsfa.8898
Melchini A, Traka MH, Catania S et al (2013) Antiproliferative activity of the dietary isothiocyanate erucin, a bioactive compound from cruciferous vegetables, on human prostate cancer cells. Nutr Cancer 65:132–138. https://doi.org/10.1080/01635581.2013.741747
Meng Q, Goldberg ID, Rosen EM, Fan S (2000) Inhibitory effects of indole-3-carbinol on invasion and migration in human breast cancer cells. Breast Cancer Res Treat 63:147–152. https://doi.org/10.1023/A:1006495824158
Mikkelsen MD, Naur P, Halkier BA (2004) Arabidopsis mutants in the C-S lyase of glucosinolate biosynthesis establish a critical role for indole-3-acetaldoxime in auxin homeostasis. Plant J 37:770–777. https://doi.org/10.1111/j.1365-313X.2004.02002.x
Mithen R (2001) Glucosinolates - biochemistry, genetics and biological activity. Plant Growth Regul 34:91–103. https://doi.org/10.1023/A:1013330819778
Mithen R, Faulkner K, Magrath R et al (2003) Development of isothiocyanate-enriched broccoli, and its enhanced ability to induce phase 2 detoxification enzymes in mammalian cells. Theor Appl Genet 106:727–734. https://doi.org/10.1007/s00122-002-1123-x
Mithen R, Bennett R, Marquez J (2010) Glucosinolate biochemical diversity and innovation in the Brassicales. Phytochemistry 71:2074–2086. https://doi.org/10.1016/j.phytochem.2010.09.017
Mitsiogianni M, Amery T, Franco R et al (2018) From chemo-prevention to epigenetic regulation: the role of isothiocyanates in skin cancer prevention. Pharmacol Ther 190:187–201. https://doi.org/10.1016/J.PHARMTHERA.2018.06.001
Mitsiogianni M, Mantso T, Trafalis DT et al (2019) Allyl isothiocyanate regulates lysine acetylation and methylation marks in an experimental model of malignant melanoma. Eur J Nutr 59(2):557–569. https://doi.org/10.1007/s00394-019-01925-6
Mokbel K, Mokbel K (2019) Chemoprevention of breast cancer with vitamins and micronutrients: a concise review. In Vivo (Brooklyn) 33:983–997. https://doi.org/10.21873/invivo.11568
Møller BL (2010) Functional diversifications of cyanogenic glucosides. Curr Opin Plant Biol 13:337–346
Mondal A, Biswas R, Rhee Y-H et al (2016) Sulforaphene promotes Bax/Bcl2, MAPK-dependent human gastric cancer AGS cells apoptosis and inhibits migration via EGFR, p-ERK1/2 down-regulation. Gen Physiol Biophys 35:25–34. https://doi.org/10.4149/gpb
Moosavi MA, Haghi A, Rahmati M et al (2018) Phytochemicals as potent modulators of autophagy for cancer therapy. Cancer Lett 424:46–69. https://doi.org/10.1016/j.canlet.2018.02.030
Mori N, Kurata M, Yamazaki H et al (2018) Allyl isothiocyanate increases carbohydrate oxidation through enhancing insulin secretion by TRPV1. Biosci Biotechnol Biochem 82:698–708. https://doi.org/10.1080/09168451.2017.1407234
Morroni F, Sita G, Djemil A et al (2018) Comparison of adaptive neuroprotective mechanisms of sulforaphane and its interconversion product erucin in in Vitro and in Vivo models of Parkinson’s disease. J Agric Food Chem 66:856–865. https://doi.org/10.1021/acs.jafc.7b04641
Nadeem A, Ahmad SF, Al-Ayadhi LY et al (2020) Differential regulation of Nrf2 is linked to elevated inflammation and nitrative stress in monocytes of children with autism. Psychoneuroendocrinology 113:104554. https://doi.org/10.1016/j.psyneuen.2019.104554
Newton EL, Bullock JM, Hodgson DJ (2009) Glucosinolate polymorphism in wild cabbage (Brassica oleracea) influences the structure of herbivore communities. Oecologia 160:63–76. https://doi.org/10.1007/s00442-009-1281-5
Nowicki D, Rodzik O, Herman-Antosiewicz A, Szalewska-Pałasz A (2016) Isothiocyanates as effective agents against enterohemorrhagic Escherichia coli: insight to the mode of action. Sci Rep 6:1–12. https://doi.org/10.1038/srep22263
Nowicki D, Maciąg-Dorszyńska M, Bogucka K et al (2019) Various modes of action of dietary phytochemicals, sulforaphane and phenethyl isothiocyanate, on pathogenic bacteria. Sci Rep 9:1–12. https://doi.org/10.1038/s41598-019-50216-x
Núñez-Iglesias MJ, Novío S, García C et al (2019) Glucosinolate-degradation products as co-adjuvant therapy on prostate cancer in vitro. Int J Mol Sci 20:4977. https://doi.org/10.3390/ijms20204977
Okamura T, Umemura T, Inoue T et al (2013) Chemopreventive effects of 4-methylthio-3-butenyl isothiocyanate (raphasatin) but not curcumin against pancreatic carcinogenesis in hamsters. J Agric Food Chem 61:2103–2108. https://doi.org/10.1021/jf3003174
Okulicz M (2010) Multidirectional time-dependent effect of sinigrin and allyl isothiocyanate on metabolic parameters in rats. Plant Foods Hum Nutr 65:217–224. https://doi.org/10.1007/s11130-010-0183-3
Olafsdottir ES, Bolt L, Jaroszewski JW (2002) Cyanogenesis in glucosinolate-producing plants: Carica papaya. Phytochemistry 60:269–273
Palliyaguru DL, Yuan JM, Kensler TW, Fahey JW (2018) Isothiocyanates: translating the power of plants to people. Mol Nutr Food Res 62:1–10. https://doi.org/10.1002/mnfr.201700965
Pant BD, Pant P, Erban A et al (2015) Identification of primary and secondary metabolites with phosphorus status-dependent abundance in Arabidopsis, and of the transcription factor PHR1 as a major regulator of metabolic changes during phosphorus limitation. Plant Cell Environ 38:172–187. https://doi.org/10.1111/pce.12378
Papi A, Farabegoli F, Iori R et al (2013) Vitexin-2-O-xyloside, raphasatin and (-)-epigallocatechin-3-gallate synergistically affect cell growth and apoptosis of colon cancer cells. Food Chem 138:1521–1530. https://doi.org/10.1016/j.foodchem.2012.11.112
Pastorczyk M, Bednarek P (2016) The function of glucosinolates and related metabolites in plant innate immunity. Elsevier, Amsterdam
Patel B, Mann GE, Chapple SJ (2018) Concerted redox modulation by sulforaphane alleviates diabetes and cardiometabolic syndrome. Free Radic Biol Med 122:150–160. https://doi.org/10.1016/j.freeradbiomed.2018.02.004
Patel J, Yin HB, Bauchan G, Mowery J (2020) Inhibition of Escherichia coli O157:H7 and Salmonella enterica virulence factors by benzyl isothiocyanate. Food Microbiol 86:103303. https://doi.org/10.1016/j.fm.2019.103303
Pawlik A, Wała M, Hać A et al (2017) Sulforaphene, an isothiocyanate present in radish plants, inhibits proliferation of human breast cancer cells. Phytomedicine 29:1–10. https://doi.org/10.1016/j.phymed.2017.03.007
Petretto GL, Urgeghe PP, Massa D, Melito S (2019) Effect of salinity (NaCl)on plant growth, nutrient content, and glucosinolate hydrolysis products trends in rocket genotypes. Plant Physiol Biochem 141:30–39. https://doi.org/10.1016/j.plaphy.2019.05.012
Petropoulos S, Di Gioia F, Ntatsi G (2017) Vegetable organosulfur compounds and their health promoting effects. Curr Pharm Des 23(19):2850–2875. https://doi.org/10.2174/1381612823666170111100531
Piotrowski M, Schemenewitz A, Lopukhina A et al (2004) Desulfoglucosinolate sulfotransferases from Arabidopsis thaliana catalyze the final step in the biosynthesis of the glucosinolate core structure. J Biol Chem 279:50717–50725. https://doi.org/10.1074/jbc.M407681200
Pocasap P, Weerapreeyakul N (2016) Sulforaphene and sulforaphane in commonly consumed cruciferous plants contributed to antiproliferation in HCT116 colon cancer cells. Asian Pac J Trop Biomed 6:119–124. https://doi.org/10.1016/j.apjtb.2015.11.003
Pocasap P, Weerapreeyakul N, Thumanu K (2018) Structures of isothiocyanates attributed to reactive oxygen species generation and microtubule depolymerization in HepG2 cells. Biomed Pharmacother 101:698–709. https://doi.org/10.1016/j.biopha.2018.02.132
Pocasap P, Weerapreeyakul N, Thumanu K (2019) Alyssin and iberin in cruciferous vegetables exert anticancer activity in HepG2 by increasing intracellular reactive oxygen species and tubulin depolymerization. Biomol Ther 27:540–552. https://doi.org/10.4062/biomolther.2019.027
Prełowska M, Kaczyńska A, Herman-Antosiewicz A (2017) 4-(Methylthio)butyl isothiocyanate inhibits the proliferation of breast cancer cells with different receptor status. Pharmacol Rep 69:1059–1066. https://doi.org/10.1016/j.pharep.2017.04.014
Psurski M, Filip-Psurska B, Cuprych M et al (2019) 3,4-dimethoxybenzyl isothiocyanate enhances doxorubicin efficacy in LoVoDX doxorubicin-resistant colon cancer and attenuates its toxicity <i>in vivo. Life Sci 231:116530. https://doi.org/10.1016/j.lfs.2019.06.005
Qi M, Anderson AE, Chen DZ et al (2005) Indole-3-carbinol prevents PTEN loss in cervical cancer in vivo. Mol Med 11:59–63. https://doi.org/10.2119/2006-00007.Auborn
Qin G, Li P, Xue Z (2018) Effect of allyl isothiocyanate on the viability and apoptosis of the human cervical cancer heLa cell line in vitro. Oncol Lett 15:8756–8760. https://doi.org/10.3892/ol.2018.8428
Radovich TJK, Kleinhenz MD, Streeter JG (2005) Irrigation timing relative to head development infl uences yield components, sugar levels, and glucosinolate concentrations in cabbage. J Am Soc Hortic Sci 130(6):943–949
Raiola A, Errico A, Petruk G et al (2018) Bioactive compounds in Brassicaceae vegetables with a role in the prevention of chronic diseases. Molecules 23:1–10. https://doi.org/10.3390/molecules23010015
Rajakumar T, Pugalendhi P, Jayaganesh R et al (2018a) Effect of allyl isothiocyanate on NF-κB signaling in 7,12-dimethylbenz(a)anthracene and N-methyl-N-nitrosourea-induced mammary carcinogenesis. Breast Cancer 25:50–59. https://doi.org/10.1007/s12282-017-0783-y
Rajakumar T, Pugalendhi P, Thilagavathi S et al (2018b) Allyl isothiocyanate, a potent chemopreventive agent targets AhR/Nrf2 signaling pathway in chemically induced mammary carcinogenesis. Mol Cell Biochem 437(1–2):1–12. https://doi.org/10.1007/s11010-017-3091-0
Rajan TS, De Nicola GR, Iori R et al (2016) Anticancer activity of glucomoringin isothiocyanate in human malignant astrocytoma cells. Fitoterapia 110:1–7. https://doi.org/10.1016/j.fitote.2016.02.007
Rakariyatham K, Yang X, Gao Z et al (2019) Synergistic chemopreventive effect of allyl isothiocyanate and sulforaphane on non-small cell lung carcinoma cells. Food Funct 10:893–902. https://doi.org/10.1039/c8fo01914b
Rampal G, Thind TS, Arora R et al (2017) Synergistic antimutagenic effect of isothiocyanates against varied mutagens. Food Chem Toxicol 109:879–887. https://doi.org/10.1016/j.fct.2017.05.017
Raut JS, Bansode BS, Jadhav AK, Karuppayil SM (2017) Activity of allyl isothiocyanate and its synergy with fluconazole against candida albicans biofilms. J Microbiol Biotechnol 27:685–693. https://doi.org/10.4014/jmb.1607.07072
Rhee YH, Mondal A, Chung PS, Ahn JC (2017) Dietary isothiocyanate sulforaphene induces reactive oxygen species, caspase -9, -8, -3-dependent apoptosis and modulates PTEN/PI3Kinase in human cervical cancer cells. Trop J Pharm Res 16:2811–2821. https://doi.org/10.4314/tjpr.v16i12.4
Robbins R, Keck A, Banuelos G, Finley J (2005) Cultivation conditions and selenium fertilization alter the phenolic profile, glucosinolate, and sulforaphane content of broccoli. J Med Food 8:204–214
Romeo L, Iori R, Rollin P et al (2018) Isothiocyanates: an overview of their antimicrobial activity against human infections. Molecules 23(3):624
Rosen CJ, Fritz VA, Gardner GM et al (2005) Cabbage yield and glucosinolate concentrations as affected by nitrogen and sulfur fertility. HortScience 40:1493–1498. https://doi.org/10.3390/molecules200915827
Roy R, Hahm ER, White AG et al (2019) AKT-dependent sugar addiction by benzyl isothiocyanate in breast cancer cells. Mol Carcinog 58:996–1007. https://doi.org/10.1002/mc.22988
Sahin N, Orhan C, Erten F et al (2019) Effects of allyl isothiocyanate on insulin resistance, oxidative stress status, and transcription factors in high-fat diet/streptozotocin-induced type 2 diabetes mellitus in rats. J Biochem Mol Toxicol 33(7):e22328. https://doi.org/10.1002/jbt.22328
Saleh NM, Mabrouk MI, Salem-Bekhit MM, Hafez EH (2017) Challenge of Moringa peregrina Forssk as an antimicrobial agent against multi-drug-resistant Salmonella sp. Biotechnol Biotechnol Equip 31:380–386. https://doi.org/10.1080/13102818.2016.1262750
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 246:19–32
Sarikamiş G (2009) Glucosinolates in crucifers and their potential effects against cancer: review. Can J Plant Sci 89:953–959. https://doi.org/10.4141/CJPS08125
Sawada Y, Kuwahara A, Nagano M et al (2009) Omics-based approaches to methionine side chain elongation in arabidopsis: characterization of the genes encoding Methylthioalkylmalate Isomerase and Methylthioalkylmalate Dehydrogenase. Plant Cell Physiol 50:1181–1190. https://doi.org/10.1093/pcp/pcp079
Schiavon M, Berto C, Malagoli M et al (2016) Selenium biofortification in radish enhances nutritional quality via accumulation of methyl-selenocysteine and promotion of transcripts and metabolites related to glucosinolates, phenolics amino acids. Front Plant Sci 7:1371. https://doi.org/10.3389/fpls.2016.01371
Scholl C, Eshelman BD, Barnes DM, Hanlon PR (2011) Raphasatin is a more potent inducer of the detoxification enzymes than its degradation products. J Food Sci 76:504–511. https://doi.org/10.1111/j.1750-3841.2011.02078.x
Schreiner M, Beyene B, Krumbein A, Stützel H (2009) Ontogenetic changes of 2-propenyl and 3-Lndolylmethyl glucosinolates in Brassica carinata leaves as affected by water supply. J Agric Food Chem 57:7259–7263. https://doi.org/10.1021/jf901076h
Schuster J, Knill T, Reichelt M et al (2006) Branched-chain Aminotransferase4 is part of the chain elongation pathway in the biosynthesis of methionine-derived glucosinolates in Arabidopsis. Plant Cell 18:2664–2679. https://doi.org/10.1105/tpc.105.039339
Sestito S, Pruccoli L, Runfola M et al (2019) Design and synthesis of H2S-donor hybrids: a new treatment for Alzheimer’s disease? Eur J Med Chem 184:111745. https://doi.org/10.1016/j.ejmech.2019.111745
Si W, Liu X, Wei R et al (2019) MTA2-mediated inhibition of PTEN leads to pancreatic ductal adenocarcinoma carcinogenicity. Cell Death Dis 10(3):206. https://doi.org/10.1038/s41419-019-1424-5
Singh K, Connors SL, Macklin EA et al (2014) Sulforaphane treatment of autism spectrum disorder (ASD). Proc Natl Acad Sci U S A 111:15550–15555. https://doi.org/10.1073/pnas.1416940111
Sønderby IE, Geu-flores F, Halkier BA (2010) Biosynthesis of glucosinolates – gene discovery and beyond. Trends Plant Sci 15(5):283–290. https://doi.org/10.1016/j.tplants.2010.02.005
Spcijers GJA (1995) Toxicological data needed for safety evaluation and regulation on inherent plant toxins. Nat Toxins 3(4):222–226. https://doi.org/10.1002/nt.2620030410
Stasiłojć G, Nagel A, Koszałka P, Bigda JJ (2019) Defective apoptosis of U937 cells induced by benzyl isothiocyanate (BITC). Acta Biochim Pol 66:401–407. https://doi.org/10.18388/abp.2019_2769
Subedi L, Venkatesan R, Kim SY (2017) Neuroprotective and anti-inflammatory activities of allyl isothiocyanate through attenuation of JNK/NF-κB/TNF-α signaling. Int J Mol Sci 18:1–16. https://doi.org/10.3390/ijms18071423
Suzuki I, Cho Y-M, Hirata T et al (2016) 4-Methylthio-3-butenyl isothiocyanate (Raphasatin) exerts chemopreventive effects against esophageal carcinogenesis in rats. J Toxicol Pathol 29:237–246
Suzuki I, Cho YM, Hirata T et al (2017) Toxic effects of 4-methylthio-3-butenyl isothiocyanate (Raphasatin) in the rat urinary bladder without genotoxicity. J Appl Toxicol 37:485–494. https://doi.org/10.1002/jat.3384
Tan SYY, Liu Y, Chua SL et al (2014) Comparative systems biology analysis to study the mode of action of the isothiocyanate compound iberin on Pseudomonas aeruginosa. Antimicrob Agents Chemother 58:6648–6659. https://doi.org/10.1128/AAC.02620-13
Testai L, Marino A, Piano I et al (2016) The novel H2S-donor 4-carboxyphenyl isothiocyanate promotes cardioprotective effects against ischemia/reperfusion injury through activation of mitoKATP channels and reduction of oxidative stress. Pharmacol Res 113:290–299. https://doi.org/10.1016/j.phrs.2016.09.006
Textor S, Gershenzon J (2009) Herbivore induction of the glucosinolate-myrosinase defense system: Major trends, biochemical bases and ecological significance. Phytochem Rev 8:149–170. https://doi.org/10.1007/s11101-008-9117-1
Thangarasu R, Pachaiappan P, Subbaiyan T (2019) Anti-estrogenic and anti-cell proliferative effect of allyl isothiocyanate in chemoprevention of chemically induced mammary carcinogenesis in rats. Pathol Oncol Res 26(2):913–925. https://doi.org/10.1007/s12253-019-00638-9
Tian X, Liu KD, Zu X et al (2019) 3,3′-Diindolylmethane inhibits patient-derived xenograft colon tumor growth by targeting COX1/2 and ERK1/2. Cancer Lett 448:20–30. https://doi.org/10.1016/j.canlet.2019.01.031
Trolove SN, Tan Y, Morrison SC et al (2018) Development of a method for producing selenium-enriched radish sprouts. LWT 95:187–192. https://doi.org/10.1016/j.lwt.2018.04.048
Troufflard S, Mullen W, Larson TR et al (2010) Potassium deficiency induces the biosynthesis of oxylipins and glucosinolates in Arabidopsis thaliana. BMC Plant Biol 10:172. https://doi.org/10.1186/1471-2229-10-172
Tsai T-F, Chen P-C, Lin Y-C et al (2020) Benzyl isothiocyanate promotes miR-99a expression through ERK/AP-1-dependent pathway in bladder cancer cells. Environ Toxicol 35:47–54. https://doi.org/10.1002/tox.22841
Tumer TB, Rojas-Silva P, Poulev A et al (2015) Direct and indirect antioxidant activity of polyphenol- and isothiocyanate-enriched fractions from Moringa oleifera. J Agric Food Chem 63:1505–1513. https://doi.org/10.1021/jf505014n
Vale J, Ribeiro M, Abreu AC et al (2019) The use of selected phytochemicals with EDTA against Escherichia coli and Staphylococcus epidermidis single- and dual-species biofilms. Lett Appl Microbiol 68:313–320. https://doi.org/10.1111/lam.13137
Van Die MD, Bone KM, Emery J et al (2016) Phytotherapeutic interventions in the management of biochemically recurrent prostate cancer: A systematic review of randomised trials. BJU Int 117:17–34. https://doi.org/10.1111/bju.13361
Velasco P, Rodríguez VM, Francisco M et al (2016) Genetics and breeding of brassica crops. In: Glucosinolates. Springer, Cham, pp 1–26
Vig AP, Rampal G, Thind TS, Arora S (2009) Bio-protective effects of glucosinolates – a review. LWT - Food Sci Technol 42:1561–1572. https://doi.org/10.1016/j.lwt.2009.05.023
Vo QV, Van Bay M, Nam PC, Mechler A (2019) Hydroxyl radical scavenging of indole-3-carbinol: a mechanistic and kinetic study. ACS Omega 4:19375–19381. https://doi.org/10.1021/acsomega.9b02782
Wagner AE, Boesch-Saadatmandi C, Dose J et al (2012) Anti-inflammatory potential of allyl-isothiocyanate - role of Nrf2, NF-κB and microRNA-155. J Cell Mol Med 16:836–843. https://doi.org/10.1111/j.1582-4934.2011.01367.x
Wang W, Wang S, Howie AF et al (2005) Sulforaphane, erucin, and iberin up-regulate thioredoxin reductase 1 expression in human MCF-7 cells. J Agric Food Chem 53:1417–1421. https://doi.org/10.1021/jf048153j
Wang X, He H, Lu Y et al (2015) Indole-3-carbinol inhibits tumorigenicity of hepatocellular carcinoma cells via suppression of microRNA-21 and upregulation of phosphatase and tensin homolog. Biochim Biophys Acta - Mol Cell Res 1853:244–253. https://doi.org/10.1016/j.bbamcr.2014.10.017
Wang N, Wang W, Liu C et al (2016) Inhibition of growth and induction of apoptosis in A549 cells by compounds from oxheart cabbage extract. J Sci Food Agric 96:3813–3820. https://doi.org/10.1002/jsfa.7575
Wiesner M, Schreiner M, Glatt H (2014) High mutagenic activity of juice from pak choi (Brassica rapa ssp. chinensis) sprouts due to its content of 1-methoxy-3-indolylmethyl glucosinolate, and its enhancement by elicitation with methyl jasmonate. Food Chem Toxicol 67:10–16. https://doi.org/10.1016/j.fct.2014.02.008
Wiesner-Reinhold M, Schreiner M, Baldermann S et al (2017) Mechanisms of selenium enrichment and measurement in brassicaceous vegetables, and their application to human health. Front Plant Sci 8:1365. https://doi.org/10.3389/fpls.2017.01365
Williams DJ, Pun S, Chaliha M et al (2013) An unusual combination in papaya (Carica papaya): The good (glucosinolates) and the bad (cyanogenic glycosides). J Food Compos Anal 29:82–86. https://doi.org/10.1016/j.jfca.2012.06.007
Wilson AE, Bergaentzlé M, Bindler F et al (2013) In vitro efficacies of various isothiocyanates from cruciferous vegetables as antimicrobial agents against foodborne pathogens and spoilage bacteria. Food Control 30:318–324. https://doi.org/10.1016/j.foodcont.2012.07.031
Winde I, Wittstock U (2011) Insect herbivore counteradaptations to the plant glucosinolate – myrosinase system. Phytochemistry 72:1566–1575. https://doi.org/10.1016/j.phytochem.2011.01.016
Wisniak J (2013) Pierre-Jean Robiquet. Educ Quim 24:139–149. https://doi.org/10.1016/S0187-893X(13)72507-2
Wittstock U, Halkier BA (2002) Glucosinolate research in the Arabidopsis era. Trends Plant Sci 7(6):263–270
Wu Y, Li RW, Huang H et al (2019) Inhibition of tumor growth by dietary indole-3-carbinol in a prostate cancer xenograft model may be associated with disrupted gut microbial interactions. Nutrients 11. https://doi.org/10.3390/nu11020467
Xiao D (2003) Allyl isothiocyanate, a constituent of cruciferous vegetables, inhibits proliferation of human prostate cancer cells by causing G2/M arrest and inducing apoptosis. Carcinogenesis 24:891–897. https://doi.org/10.1093/carcin/bgg023
Xiao D, Srivastava SK, Lew KL et al (2003) Allyl isothiocyanate, a constituent of cruciferous vegetables, inhibits proliferation of human prostate cancer cells by causing G2/M arrest and inducing apoptosis. Carcinogenesis 24:891–897
Xie B, Zhao L, Guo L et al (2019) Benzyl isothiocyanate suppresses development and metastasis of murine mammary carcinoma by regulating the Wnt/β-catenin pathway. Mol Med Rep 20:1808–1818. https://doi.org/10.3892/mmr.2019.10390
Yang R, Guo L, Jin X et al (2015) Enhancement of glucosinolate and sulforaphane formation of broccoli sprouts by zinc sulphate via its stress effect. J Funct Foods 13:345–349. https://doi.org/10.1016/j.jff.2015.01.007
Yang M, Ren M, Qu Y et al (2016a) Sulforaphene inhibits hepatocellular carcinoma through repressing keratin 8 and activating anoikis. RSC Adv 6:70326–70334. https://doi.org/10.1039/C6RA11176A
Yang M, Teng W, Qu Y et al (2016b) Sulforaphene inhibits triple negative breast cancer through activating tumor suppressor Egr1. Breast Cancer Res Treat 158:277–286. https://doi.org/10.1007/s10549-016-3888-7
Yang M, Wang H, Zhou M et al (2016c) The natural compound sulforaphene, as a novel anticancer reagent, targeting PI3K-AKT signaling pathway in lung cancer. Oncotarget 7:76656–76666. https://doi.org/10.18632/oncotarget.12307
Yang R, Hui Q, Gu Z, Zhou Y (2016d) Effects of CaCl 2 on the metabolism of glucosinolates and the formation of isothiocyanates as well as the antioxidant. J Funct Foods 24:156–163. https://doi.org/10.1016/j.jff.2016.04.007
Yang H, Seo SG, Shin SH et al (2017) 3,3’-Diindolylmethane suppresses high-fat diet-induced obesity through inhibiting adipogenesis of pre-adipocytes by targeting USP2 activity. Mol Nutr Food Res 61:1–12. https://doi.org/10.1002/mnfr.201700119
Yang CX, Wu HT, Li XX et al (2020) Comparison of the inhibitory potential of benzyl isothiocyanate and phenethyl isothiocyanate on Shiga toxin-producing and enterotoxigenic Escherichia coli. LWT - Food Sci Technol 118:108806. https://doi.org/10.1016/j.lwt.2019.108806
Yuan G, Wang X, Guo R, Wang Q (2010) Effect of salt stress on phenolic compounds, glucosinolates, myrosinase and antioxidant activity in radish sprouts. Food Chem 121(4):1014–1019. https://doi.org/10.1016/j.foodchem.2010.01.040
Zanichelli F, Capasso S, Di Bernardo G et al (2012) Low concentrations of isothiocyanates protect mesenchymal stem cells from oxidative injuries, while high concentrations exacerbate DNA damage. Apoptosis 17:964–974. https://doi.org/10.1007/s10495-012-0740-3
Zhang Y (2010) Allyl isothiocyanate as a cancer chemopreventive phytochemical. Mol Nutr Food Res 54:127–135. https://doi.org/10.1002/mnfr.200900323
Zhang Y, Talalay P, Cho CG, Posner GH (1992) A major inducer of anticarcinogenic protective enzymes from broccoli: isolation and elucidation of structure. Proc Natl Acad Sci U S A 89:2399–2403. https://doi.org/10.1073/pnas.89.6.2399
Zhang Y, Kensler TW, Cho CG et al (1994) Anticarcinogenic activities of sulforaphane and structurally related synthetic norbornyl isothiocyanates. Proc Natl Acad Sci U S A 91:3147–3150. https://doi.org/10.1073/pnas.91.8.3147
Zhang J, Zhou X, Fu M (2016) Integrated utilization of red radish seeds for the efficient production of seed oil and sulforaphene. Food Chem 192:541–547. https://doi.org/10.1016/j.foodchem.2015.07.051
Zhang QC, Pan ZH, Liu BN et al (2017) Benzyl isothiocyanate induces protective autophagy in human lung cancer cells through an endoplasmic reticulum stress-mediated mechanism. Acta Pharmacol Sin 38:539–550. https://doi.org/10.1038/aps.2016.146
Zhang C, Zhang J, Wu Q et al (2019a) Sulforaphene induces apoptosis and inhibits the invasion of esophageal cancer cells through MSK2/CREB/Bcl-2 and cadherin pathway in vivo and in vitro. Cancer Cell Int 19:4–13. https://doi.org/10.1186/s12935-019-1061-1
Zhang M, Xu Y, Qiu Z, Jiang L (2019b) Sulforaphane attenuates angiotensin ii-induced vascular smooth muscle cell migration via suppression of NOX4/ROS/Nrf2 signaling. Int J Biol Sci 15:148–157. https://doi.org/10.7150/ijbs.28874
Zhao F, Evans EJ, Bilsborrow PE, Syers JK (1994) Influence of nitrogen and sulphur on the glucosinolate profile of rapeseed (brassica napus l). J Sci Food Agric 64:295–304. https://doi.org/10.1002/jsfa.2740640309
Acknowledgement
This work was supported by the USDA National Institute of Food and Agriculture and Hatch Appropriations under Project #PEN04723 and Accession #1020664.
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2021 Springer Nature Switzerland AG
About this chapter
Cite this chapter
Di Gioia, F., Petropoulos, S.A. (2021). Glucosinolates. In: Galanakis, C.M. (eds) Food Bioactives and Health. Springer, Cham. https://doi.org/10.1007/978-3-030-57469-7_2
Download citation
DOI: https://doi.org/10.1007/978-3-030-57469-7_2
Publisher Name: Springer, Cham
Print ISBN: 978-3-030-57468-0
Online ISBN: 978-3-030-57469-7
eBook Packages: Biomedical and Life SciencesBiomedical and Life Sciences (R0)