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The chemical diversity and distribution of glucosinolates and isothiocyanates among plants
Abstract
Glucosinolates (beta-thioglucoside-N-hydroxysulfates), the precursors of isothiocyanates, are present in sixteen families of dicotyledonous angiosperms including a large number of edible species. At least 120 different glucosinolates have been identified in these plants, although closely related taxonomic groups typically contain only a small number of such compounds. Glucosinolates and/or their breakdown products have long been known for their fungicidal, bacteriocidal, nematocidal and allelopathic properties and have recently attracted intense research interest because of their cancer chemoprotective attributes. Numerous reviews have addressed the occurrence of glucosinolates in vegetables, primarily the family Brassicaceae (syn. Cruciferae; including Brassica spp and Raphanus spp). The major focus of much previous research has been on the negative aspects of these compounds because of the prevalence of certain "antinutritional" or goitrogenic glucosinolates in the protein-rich defatted meal from widely grown oilseed crops and in some domesticated vegetable crops. There is, however, an opposite and positive side of this picture represented by the therapeutic and prophylactic properties of other "nutritional" or "functional" glucosinolates. This review addresses the complex array of these biologically active and chemically diverse compounds many of which have been identified during the past three decades in other families. In addition to the Brassica vegetables, these glucosinolates have been found in hundreds of species, many of which are edible or could provide substantial quantities of glucosinolates for isolation, for biological evaluation, and potential application as chemoprotective or other dietary or pharmacological agents.
... However, when the plant is damaged by insect feeding or pathogen infection, the glucosinolates are hydrolyzed by myrosinase enzymes to bioactive isothiocyanates 55,61 . Isothiocyanates are volatile compounds known to have a broad-spectrum antimicrobial and insecticidal activity that vary substantially in structure, biological activity, and content among Brassicaceae species 42,59,62,63 . ...
... Isothiocyanates are produced from www.nature.com/scientificreports/ hydrolysis of glucosinolates by the enzyme myrosinase when the seed meal is hydrated 38,55,70 and are known to have fungicidal, bactericidal, nematocidal, and insecticidal effects as well as other attributes including allelopathic and chemotherapeutic properties 61,62,70 . Several studies reported that mustard plants and seed meals effectively acted as fumigants to suppress soil and stored product insect pests 57,59,71,72 . ...
... Only Ls seed meal contained substantial amount of glucotropaeolin while PG and DFP had sinigrin and IG had sinalbin as the predominant glucosinolates (Table 1). Glucotropaeolin is hydrolyzed into BITC and sinalbin is hydrolyzed into 4-HBITC 61,62 . The results of our bioassays demonstrated consistent high toxicity of both the Ls seed meal and the synthetic BITC against mosquito larvae. ...
Strategic, sustainable, and ecofriendly alternatives to chemical pesticides are needed to effectively control mosquitoes and reduce the incidence of their vectored diseases. We evaluated several Brassicaceae (mustard family) seed meals as sources of plant derived isothiocyanates produced from the enzymatic hydrolysis of biologically inactive glucosinolates for the control of Aedesaegypti (L., 1762). Five defatted seed meals (Brassicajuncea (L) Czern., 1859, Lepidiumsativum L., 1753, Sinapisalba L., 1753, Thlaspiarvense L., 1753, and Thlaspiarvense—heat inactivated and three major chemical products of enzymatic degradation (allyl isothiocyanate, benzyl isothiocyanate and 4-hydroxybenzyl isothiocyanate) were assayed to determine toxicity (LC50) to Ae.aegypti larvae. All seed meals except the heat inactivated T.arvense were toxic to mosquito larvae. L.sativum seed meal was the most toxic treatment to larvae (LC50 = 0.04 g/120 mL dH2O) at the 24-h exposure. At the 72-h evaluation, the LC50 values for B.juncea,S.alba and T.arvense seed meals were 0.05, 0.08 and 0.1 g/120 mL dH2O, respectively. Synthetic benzyl isothiocyanate was more toxic to larvae 24-h post treatment (LC50 = 5.29 ppm) compared with allyl isothiocyanate (LC50 = 19.35 ppm) and 4-hydroxybenzyl isothiocyanate (LC50 = 55.41 ppm). These results were consistent with the higher performance of the benzyl isothiocyanate producing L.sativum seed meal. Isothiocyanates produced from seed meals were more effective than the pure chemical compounds, based on calculated LC50 rates. Using seed meal may provide an effective method of delivery for mosquito control. This is the first report evaluating the efficacy of five Brassicaceae seed meals and their major chemical constituent against mosquito larvae and demonstrates how natural compounds from Brassicaceae seed meals can serve as a promising ecofriendly larvicides to control mosquitoes.
... Isothiocyanates on the other hand appear in masked form as glucosinolates, which occur in 17 orders of Brassicales, especially in the family Brassicaceae but also in Capparaceae, Moringaceae, Resedaceae and Tropaeolaceae species 50 . BITC and PITC come from the arylaliphatic glucosinolates, glucotropaeolin and gluconasturtiin, respectively 50,51 . ...
... Isothiocyanates on the other hand appear in masked form as glucosinolates, which occur in 17 orders of Brassicales, especially in the family Brassicaceae but also in Capparaceae, Moringaceae, Resedaceae and Tropaeolaceae species 50 . BITC and PITC come from the arylaliphatic glucosinolates, glucotropaeolin and gluconasturtiin, respectively 50,51 . AITC are aliphatic-like ITC commonly found in Wasabia japonica 50,51 . ...
... BITC and PITC come from the arylaliphatic glucosinolates, glucotropaeolin and gluconasturtiin, respectively 50,51 . AITC are aliphatic-like ITC commonly found in Wasabia japonica 50,51 . ...
Aims
This study evaluated the antimicrobial effect of coriander oil (CO) and isothiocyanates (ITC; Allyl, Benzyl and Phenyl-A-, B-, P-ITC) on clinical oral isolate Streptococcus mutans. We evaluated inhibition of biofilm, metabolic activity and exopolysaccharide formation.
Methods
The composition of CO was determined by gas chromatography- mass spectrometry (GC-MS). CO and ITC were dissolved in 0.1% Tween 80. Different concentrations (0.0039-1%) of CO, ITC and CO-ITC were made in Tryptic soy broth (TSB) and with sucrose (TSBS). Broth dilution method was used to determine the minimum inhibitory concentration (MIC). Minimum biofilm inhibitory concentrations (MBIC) were established by staining biofilm with crystal violet. Checkerboard assay was used to evaluate combination effects. An XTT assay was used to determine the metabolic activity and a sulphuric acid-phenol assay for inhibition of S. mutans exopolysaccharide production.
Results
CO was dominated by Linalool (65.5%) followed by 2-bornanone (6.16%) and Gamma-terpinene (4.31%). The least was Terpinen-4-ol (0.13%). The MIC of CO was 0.00195% and < 0.00195% for ITCs. MBIC for B-ITC was at < 0.0039%, while with CO-ITC at 0.00195% (p < 0.05). The MBC of CO was 0.125% and for CO-B-ITC MBIC was < 0.00195%. The B-ITC MBC was > 0.25%. Strong S. mutans exopolysaccharide inhibition was observed with ITC and CO at 0.0039%. CO reduced S. mutans metabolic activity at 0.125% and ITC at 0.0078%.
Conclusion and clinical relevance
CO and ITC are promising agents in prevention of both periodontal disease and dental caries. Further data is required to warrant development of products to help mitigate dental caries and periodontal disease.
... Many species of Reseda are restricted to the Mediterranean Basin, while four species, R. alba, R. lutea, R. luteola, and R. phyteuma, are distributed worldwide [3]. There are five spp. of Reseda genus (mignonettes) known to be wild-growing in Croatia, i.e., Reseda alba L. (white mignonette), R. lutea L. (yellow or wild or [24,25] [24,26-28] [24] [24] [14,24,25,29] [ 6,24,25,27,[30][31][32][33] [24,34] [6,24,25,27,30] [ 24,30,35] [ 24,30] [30] [24,35] [ 36] * No.-Numbering system is related to the GSL numbers given in a review paper by Blažević et al. Qualitative analyses of GSLs in Resedaceae published up to 2001 were reviewed by Fahey et al. [24]. ...
... Many species of Reseda are restricted to the Mediterranean Basin, while four species, R. alba, R. lutea, R. luteola, and R. phyteuma, are distributed worldwide [3]. There are five spp. of Reseda genus (mignonettes) known to be wild-growing in Croatia, i.e., Reseda alba L. (white mignonette), R. lutea L. (yellow or wild or [24,25] [24,26-28] [24] [24] [14,24,25,29] [ 6,24,25,27,[30][31][32][33] [24,34] [6,24,25,27,30] [ 24,30,35] [ 24,30] [30] [24,35] [ 36] * No.-Numbering system is related to the GSL numbers given in a review paper by Blažević et al. Qualitative analyses of GSLs in Resedaceae published up to 2001 were reviewed by Fahey et al. [24]. ...
... Many species of Reseda are restricted to the Mediterranean Basin, while four species, R. alba, R. lutea, R. luteola, and R. phyteuma, are distributed worldwide [3]. There are five spp. of Reseda genus (mignonettes) known to be wild-growing in Croatia, i.e., Reseda alba L. (white mignonette), R. lutea L. (yellow or wild or [24,25] [24,26-28] [24] [24] [14,24,25,29] [ 6,24,25,27,[30][31][32][33] [24,34] [6,24,25,27,30] [ 24,30,35] [ 24,30] [30] [24,35] [ 36] * No.-Numbering system is related to the GSL numbers given in a review paper by Blažević et al. Qualitative analyses of GSLs in Resedaceae published up to 2001 were reviewed by Fahey et al. [24]. ...
Glucosinolates (GSLs) are a unique class of thioglucosides that evolved as defense mechanisms in the 16 families of the Brassicales order and present molecular tags which can be placed in a robust phylogenetic framework through investigations into their evolution and diversity. The GSL profiles of three Resedaceae species, Reseda alba, R. lutea, and R. phyteuma, were examined qualitatively and quantitatively with respect to their desulfo-counterparts utilizing UHPLC-DAD-MS/MS. In addition, NMR analysis of isolated 2-hydroxy-2-methylpropyl desulfoGSL (d31) was performed. Three Phe-derived GSLs were found in R. lutea, including glucotropaeolin (11) (0.6–106.69 mol g−1 DW), 2-(α-L-ramnopyranosyloxy)benzyl GSL (109) (8.10–57.89 μmol g−1 DW), glucolepigramin (22) (8.66 μmol g−1 DW in flower), and Trp-derived glucobrassicin (43) (0.76–5.92 μmol g−1 DW). The Phe-derived GSLs 109 (50.79–164.37 μmol g−1 DW), gluconasturtiin (105) (1.97 μmol g−1 DW), and 11 (tr), as well as the Trp-derived GSL glucobrassicin (43) (3.13–11.26 μmol g−1 DW), were all present in R. phyteuma. R. alba also contained Phe-derived 105 (0.10–107.77 μmol g−1 DW), followed by Trp-derived 43 (0.85–3.50 μmol g−1 DW) and neoglucobrassicin (47) (0.23–2.74 μmol g−1 DW). However, regarding the GSLs in R. alba, which originated from Leu biosynthesis, 31 was the major GSL (6.48 to 52.72 μmol g−1 DW) and isobutyl GSL (62) was the minor GSL (0.13 to 1.13 μmol g−1 DW). The discovered Reseda profiles, along with new evidence provided by GSL characterizations, were studied in the context of the current knowledge on GLSs in the Resedaceae family. With the exception of R. alba, the aliphatic GSLs of which were outliers among the Resedaceae species studied, this family typically contains GSLs derived primarily from Trp and Phe biosynthesis, which modifications resulted in GSLs unique to this family, implying presence of the specific genes. responsible for this diversification.
... isothiocyanates, thiocyanates, nitriles). These thioglucosidases, known as myrosinases, co-occur with glucosinolates but are stored separately from glucosinolates in intact plants (Fahey et al. 2001). Upon tissue damage, for example by herbivores, myrosinases come into contact with the glucosinolates and catalyze the formation of the corresponding aglycones, transient species that usually rearrange spontaneously into isothiocyanates. ...
... The hydrolysis of glucosinolates impacts the taste, flavor, and nutritional value of spices and vegetables derived from plants belonging to the Brassicaceae family, such as mustard, horseradish, cabbage, cauliflower, and broccoli. From a plant perspective, this process is crucial for the function of glucosinolates as chemical plant defenses (Fahey et al., 2001). The glucosinolate hydrolysis products have many different biological activities and are of importance to humans, as well (Halkier and Gershenzon, 2006). ...
... The most common glucosinolate autolysis products are isothiocyanates which exhibit marked biological activities in a number of models and are toxic to a variety of organisms, including microorganisms, nematodes, and insects (Chew, 1988;Louda and Mole, 1991;Rask et al. 2000). In addition to isothiocyanates, other hydrolysis products are formed upon tissue damage, including simple nitriles, epithionitriles, and organic thiocyanates (Fahey et al., 2001). The formation of these alternative products depends on the side-chain structure of the parent glucosinolate and it is established that for some of them the presence of specific plant proteins diverts glucosinolate hydrolysis away from isothiocyanates. ...
Glucosinolates are abundant in plants of the order Brassicales, and they are degraded by myrosinases into various organic breakdown products: isothiocyanates, thiocyanates, nitriles, etc., depending on their structure, conditions of hydrolysis, the presence of certain protein cofactors. Their most common hydrolysis products are isothiocyanates, while simple nitriles, epithionitriles, and thiocyanates are produced occasionally. Organic thiocyanates are described from a very limited number of Brassicales taxa. Up to now benzyl, (4-hydroxyphenyl)methyl, (4-methoxyphenyl)methyl, 4- methylthiobutyl, and allyl thiocyanates were reported as products of glucosinolates autolysis. The present review summarizes the knowledge on the mechanism of organic thiocyanate formation from the corresponding thioglucosides. The enzymatic formation of organic thiocyanates is believed to be enabled by thiocyanate-forming protein (TFP), but they could be formed via metabolic routes that do not involve TFP. All of the reported thiocyanates are produced from stable (carbo)cationic species that allow an isomerization of an isothiocyanate to thiocyanate, and vice versa. Although the possibility that thiocyanates can be biosynthesized in plats under certain conditions cannot be dismissed, allyl thiocyanate can be a thermal isomerization artefact of the original isothiocyanate that is formed in the heated zones of the gas chromatograph, while other thiocyanates could form in an aqueous medium via heterolytic dissociation to ambident nucleophilic SCN- and its recapture. One should always be aware of this analytical shortcoming when concluding on the presence and quantity of these specific (iso)thiocyanantes in the analyzed sample.
... The neighboring receptor plants may be positively or negatively affected [5]. Flavonoids, terpenoids, alkaloids, phenolic acids, glucosinolates and amino acids are the common known allelochemicals in allelopathic plants [6,7]. Allelochemicals in brassica plants have been recorded to have inhibitory allelopathic effect on weeds. ...
... By disrupting brassica tissue myrosinase enzyme is released to hydrolyze glucosinolates other simple products such as nitriles, isothiocyanates, thiocyanates, oxazoliolines and epithionitriles [11]. Isothiocyanates are the main phytotoxic pesticidal product [6][7][8][9]. Many scientists ensured that brassica seeds glucosinolates contents is higher than other plant parts [6,7]. ...
... Isothiocyanates are the main phytotoxic pesticidal product [6][7][8][9]. Many scientists ensured that brassica seeds glucosinolates contents is higher than other plant parts [6,7]. ...
... It is important to point out that most studies are still in preclinical stages, and in order to have nanotechnological options for cancer treatment, large-scale production and in vivo effects must be better understood. Fig. 15.1 Sulforaphane biological synthesis reaction myrosinase, but hydrolysis in the intestinal tract manages to convert only between 14 and 20% of glucoraphanin in sulforaphane (Fahey et al. 2001;Rungapamestry et al. 2007;Van Eylen et al. 2007). ...
... In this chapter, a discussion associating SFN molecular mechanisms of action with its potential pharmacological applications and the main nanocarriers for SFN delivery are provided, highlighting the relationships between biological synthesis, pharmacological aspects, and the new nanotechnological strategies for developing effective and safe pharmacotherapeutic alternatives. (Fahey et al. 2001(Fahey et al. , 2015. Among them, broccoli and, in particular, its sprouts, have the greatest potential for extracting SFN (Totušek et al. 2011). ...
Although heart diseases continue to be the leading cause of death worldwide, advances performed in recent decades have facilitated a decrease in the mortality rate related to severe heart diseases. This is due to the recognition that has been acquiring the role of the immune system and its contribution to the progression of heart disease. Recent studies have shown that there is a close relationship between cardiac disturbances and inflammatory mediators produced by immune system cells since there is a close interaction between the innate and adaptive immune response in the pathophysiology of heart diseases. Regarding innate immune response, macrophages are the leading cells, which play a fundamental role in a wide variety of cardiac disorders. These cells produce a variety of cytokines that open up a wide range of therapeutic possibilities in the treatment of heart diseases. However, under certain circumstances, it is known that immune system cells can cause irreparable damage that contributes to heart failure. Therefore, it is essential to study the crosstalk between innate and adaptive response in order to better understand the mechanism of action of the different cardiac disturbances. In this sense, biotechnology emerges as a pioneering tool that allows on the one hand to effectively detect the various cardiovascular and inflammatory diseases, and on the other, to develop innovative therapies that result in effective treatments.
... Biosynthetic pathways for 1 and 2 are proposed in Scheme 1. The typical isothiocyanate derived from phenylalanine was considered to be the starting unit [24]. The initial head-to-tail cyclization of isothiocyanate (A) with methyl alanine would produce B with the removal of a methoxy moiety [25]. ...
... Biosynthetic pathways for 1 and 2 are proposed in Scheme 1. The typical isothiocyanate derived from phenylalanine was considered to be the starting unit [24]. The initial headto-tail cyclization of isothiocyanate (A) with methyl alanine would produce B with the removal of a methoxy moiety [25]. ...
Spiroleiferthione A (1), with a 2-thiohydantoin a heterocyclic spiro skeleton, and oleiferthione A (2), an imidazole-2-thione derivative, were isolated from the aqueous extract of Moringa oleifera Lam. seeds. The unprecedented structures of 1 and 2 were elucidated by extensive spectroscopic data, X-ray diffraction, and gauge-independent atomic orbital (GIAO) NMR calculation, as well as electronic circular dichroism (ECD) calculation. The structures of 1 and 2 were determined to be (5R,7R,8S)-8-hydroxy-3-(4′-hydroxybenzyl)-7-methyl-2-thioxo-6-oxa-1, 3-diazaspiro [4.4] nonan-4-one, and 1-(4′-hydroxybenzyl)-4,5-dimethyl-1,3-dihydro-2H-imidazole-2-thione, respectively. Biosynthetic pathways for 1 and 2 have been proposed. Compounds 1 and 2 are considered to have originated from isothiocyanate and then undergone a series of oxidation and cyclization reactions to form 1 and 2. Compounds 1 and 2 demonstrated weak inhibition rates of NO production, 42.81 ± 1.56% and 33.53 ± 2.34%, respectively, at a concentration of 50 μM. Additionally, Spiroleiferthione A demonstrated moderate inhibitory activity against high glucose-induced human renal mesangial cell proliferation in a dosage-dependent manner. A wider range of biological activities, and the diabetic nephropathy protective activity of Compound 1 in vivo and its mechanism of action, need further investigation after the sufficient enrichment of Compound 1 or total synthesis.
... Glucosinolates (GSs), a class of secondary metabolites, are nitrogen-and sulfur-containing thioglucosides derived from glucose and amino acids. They are mainly found in the Capparales order and almost exclusively in the Brassicaceae family, which include Brassica crops of economic and nutritional importance as well as the model plant Arabidopsis thaliana (Fahey et al., 2001;Halkier and Gershenzon, 2006). ...
... Additionally, isothiocyanates prevent carcinogenesis via inhibition of phase I enzymes, such as cytochrome P450 enzymes, which have the ability to transform and activate procarcinogens that may later induce mutations (Wu et al., 2009). It has been stated that SFN inhibits cytochrome P450, which serves as a mechanism of action for the reduction of carcinogen-DNA adduct formation (Fahey et al., 2001). ...
... In particular, cruciferous vegetables contain glucosinolates and isothiocyanates, which are highly volatile and spicy with a unique aroma, thereby preventing stomach cancer, liver cancer, and lung cancer [6,7]. Cruciferous vegetables contain approximately 100 types of glucosinolates, mainly glucobrassicanapin, glucoraphanin, gluconapin, and sinigrin [8]. The total glucosinolate content of cruciferous vegetables is affected by the type and variety of vegetables, growing conditions, harvest time, and climate [9,10]. ...
... On the other hand, cruciferous vegetables contain about 120 kinds of glucosinolates with various physiological activities. These glucosinolates are hydrolyzed by myrosinase when the tissue of the plant is injured by pests or during harvesting or cooking, and are decomposed into isothiocyanate, nitrile, thiocyanate, and glucose [8]. Sulforaphane (S-methylsulfinylbutyl isothiocyanate) is produced together with sulforaphane nitrile upon decomposing glucoraphanin, a precursor, by myrosinase when plant tissues are damaged [32]. ...
... When we fed P. brassicae larvae on 11 different, ecologically relevant Brassicaceae host plant species, NSP and MA showed different expression patterns, which were commonly complementary ( Fig. 2A). NSP was primarily up-regulated in response to plants with high concentrations of aliphatic GSL, such as sinigrin-rich Thlaspi arvense (35,36). MA was up-regulated in response to plants with high benzylic GSL concentrations, such as Nasturtium officinale, which is rich in gluconasturtiin (36,37). ...
... NSP was primarily up-regulated in response to plants with high concentrations of aliphatic GSL, such as sinigrin-rich Thlaspi arvense (35,36). MA was up-regulated in response to plants with high benzylic GSL concentrations, such as Nasturtium officinale, which is rich in gluconasturtiin (36,37). Our observations in P. brassicae are consistent with those for P. melete in finding statistical support for the differential regulation of NSP and MA in response to diverse host plants, lending further support to other preliminary observations of differential NSP and MA regulation in response pnas.org to hostplant differences in four species of Pieris butterflies (29). ...
Coevolutionary interactions are responsible for much of the Earth's biodiversity, with key innovations driving speciation bursts on both sides of the interaction. One persistent question is whether macroevolutionary traits identified as key innovations accurately predict functional performance and selection dynamics within species, as this necessitates characterizing their function, investigating their fitness consequences, and exploring the selection dynamics acting upon them. Here, we used CRISPR-Cas9 mediating nonhomologous end joining (NHEJ) in the butterfly species Pieris brassicae to knock out and directly assess the function and fitness impacts of nitrile specifier protein (NSP) and major allergen (MA). These are two closely related genes that facilitate glucosinolate (GSL) detoxification capacity, which is a key innovation in mustard feeding Pierinae butterflies. We find NSP and MA are both required for survival on plants containing GSLs, with expression differences arising in response to variable GSL profiles, concordant with detoxification performance. Importantly, this concordance was only observed when using natural host plants, likely reflecting the complexity of how these enzymes interact with natural plant variation in GSLs and myrosinases. Finally, signatures of positive selection for NSP and MA were detected across Pieris species, consistent with these genes' importance in recent coevolutionary interactions. Thus, the war between these butterflies and their host plants involves more than the mere presence of chemical defenses and detoxification mechanisms, as their regulation and activation represent key components of complex interactions. We find that inclusion of these dynamics, in ecologically relevant assays, is necessary for coevolutionary insights in this system and likely others.
... These volatile compounds are the main breakdown products of glucosinolate hydrolysis. They are nitrogen-and sulphur-containing secondary metabolites found almost exclusively in the Brassicaceae plant family (Fahey et al. 2001;Wittstock et al. 2016). ...
... Ratios are expressed as the number of germinated seeds exhibiting prehaustoria (swollen radicles with papillae) on total germinated seeds, relatively to the average ratio obtained with the positive control (TDZ 10 − 8 M, a cytokinin-like molecule). Different lowercase letters indicate significant differences of treatments (p-value < 0.05), determined by an ANOVA on a logistic model host pre-existing germination signal by the hydrolysis of the host-exuded glucosinolates thanks to soil microbial myrosinase activities (Fahey et al. 2001;Rumberger and Marschner 2003;Bressan et al. 2009;Auger et al. 2012). This hypothesis is further supported by in vitro germination assays which showed that soil microorganisms stimulated broomrape seed germination, only when supplied with the main glucosinolate of rapeseed roots GNT . ...
Purpose
The root holoparasitic plant Phelipanche ramosa has become a major constraint for rapeseed cultivation in western France for the last decades and its control remains challenging. To date, few studies have considered soil microbiota as a third partner of the parasitic plant-plant interaction. Therefore, we here addressed the question of how soil microbiota interferes with host-derived signal metabolites required for host plant recognition by the parasitic plant.
Methods
Using a branched broomrape infested soil (genetic group 1) from a rapeseed field, we first provided soil physicochemical and microbiological descriptions by metabarcoding, followed by P. ramosa seed germination and prehaustorium formation bioassays, and by in vitro co-cultivation with Brassica napus.
Results
Co-cultivation in presence of soil microorganisms promoted parasitic plant seed germination and attachments to host’s roots. Seed germination assays showed that only the combination of gluconasturtiin (main rapeseed glucosinolate) with soil extracts stimulated broomrape germination. This suggests a microbial conversion of gluconasturtiin into germination stimulants via soil microbial myrosinase enzymes. Furthermore, soil bacteria Arthrobacter, Ralstonia, Actinobacterium, Proteobacterium spp. and fungus Penicillium spp. were isolated and screened for myrosinase activity. Pre-germinated seeds treated with soil extracts or differentially filtrated soil extracts also promoted the formation of P. ramosa prehaustorium and led to more parasitic attachments on rapeseed roots in co-cultivation assays. This thus suggests that this enhancement of parasitic attachments could also be partly attributed to soil microbial production of haustorium inducing factors.
Conclusion
Soil microbiota influences B. napus - P. ramosa interaction by altering direct and indirect recognition signals.
... Relatively few studies have assessed the influence of garlic mustard-derived secondary compounds upon saprotrophic fungi or decomposition rates. It is wellestablished that many saprotrophs are capable of metabolizing glucosinolates (Fahey et al., 2001), though the resulting isothiocyanates are considered more toxic, less susceptible to degradation, and capable of inhibiting the growth of saprotrophic fungi in culture (Drobnica et al., 1967). This antagonism towards fungal saprotrophs may be responsible for observations of reduced soil respiration associated with decomposing garlic mustard litter . ...
Differences between fungal and bacterial decomposition trajectories can be related to differences in sensitivity to nutrient input and to plant secondary metabolites. The invasive plant Alliaria petiolata (Beib. Cavara and Grande; garlic mustard) produces unique secondary metabolites (glucosinolates) capable of altering the functioning of root-associated communities. However, few studies explore whether these compounds can alter litter decomposition a route for ecosystem-level impacts of garlic mustard invasion. This preliminary study investigated the potential for aqueous garlic mustard leachate to alter mass loss from tea litterbags in artificially fungal-dominant compared to intact soils (fungal and bacterial components) in laboratory microcosm incubations. Garlic mustard and native Acer saccharum (Marsh.; sugar maple) leachates stimulated fungal decomposition indistinguishably. In intact soils, garlic mustard suppressed mass loss relative to a water control and native leachate, though this later effect was only marginally significant. These results suggest the energetic benefit of labile carbon in garlic mustard leachate may exceed any negative effect of glucosinolates for fungal decomposers, but that bacteria were more sensitive to leachate toxicity and the inhibitory effects of high nutrient input. Overall, our results imply the direction of garlic mustard's effect on decomposition may depend on saprotrophic community composition and therefore the consequences for litter decay in garlic mustard invaded soils may be context-dependent.
... Many previous studies suggest that these proteins are responsible for the coagulation and flocculation processes [191,206]. Further, these proteins have the ability to flocculate gram-positive and gram-negative bacterial cells [168]. Furthermore, other studies suggest that the properties of the coagulant in mature, dry Moringa Oleifera seeds emerge from the availability of cationic and water-soluble proteins, while other authors suggest that the properties of the coagulant may be improved by adding cations [47,48]. ...
In this review, collected information related to Moringa Oleifera seeds was evaluated, such as their properties and the main active components involved in their processes, as well as their dual efficiency as both antimicrobials and natural coagulants for treating contaminated effluents. Furthermore, discussions were completed about perspectives on progress related to this field of research to understand the bioactive properties of these seed compounds, including their antibacterial, antifungal, and antiviral activity. In addition to the coagulant properties that have been quantitatively assessed, studies have examined the underlying coagulating mechanism, and seed processing techniques. In addition, the challenges associated with the use of conventional coagulants (metals or polymers) have led to numerous research efforts towards the development of natural plant-based coagulants that are eco-friendly to treat wastewater and offer a large variety of other advantages, such as their wide availability, the reduction of by-product generation, the reduction of costs, and greater biodegradability. Based on the results of different researchers, and regarding the appraisals using Moringa Oleifera seeds for wastewater treatment processes, many studies encourage their use for those operations. Due to their extensive and potent properties as an antibacterial and a coagulant, Moringa Oleifera seeds are still used today as a promising wastewater treatment method. Finally, this paper provides suggestions and comments, as well as identifies the knowledge gaps, and makes recommendations for future research development strategies, such as studying the contents of Moringa Oleifera seeds, their interactions with colloids present in wastewater, understanding their stability and behavior, assessing the performance of seed-derived flocculants according to pH values, isolating and characterizing the active compounds to determine the toxicity and optimum dose to be used as effective antimicrobials, and removing heavy metals.
... This is the case of glucosinolates, S-containing glucosidic compounds, which constitute a natural class of organic compounds and are derived from glucose and an amino acid present in Brassicaceae, Euphorbiaceae, etc. The interest in glucosinolates has increased due to the biocidal [43] and cancer chemopreventive activity [44] of their hydrolysis products (isothiocyanates, nitriles, thiocyanates, epithionitriles, and oxazolidines). ...
Light is an important environmental factor for plants. The quality of light and the wavelength stimulate enzyme activation, regulate enzyme synthesis pathways and promote bioactive compound accumulation. In this respect, the utilization of LED light under controlled conditions in agriculture and horticulture could be the most suitable choice for increasing the nutritional values of various crops. In recent decades, LED lighting has been increasingly used in horticulture and agriculture for commercial-scale breeding of many species of economic interest. Most studies on the influence of LED lighting on the accumulation of bioactive compounds in any type of plants (horticultural, agricultural species or sprouts) and also biomass production, were carried out in growth chambers under controlled conditions, without natural light. Illumination with LED could be a solution for obtaining an important crop with maximum efficiency, with a high nutritional value and minimum effort. To demonstrate the importance of LED lighting in agriculture and horticulture, we carried out a review based on a large number of results cited in the literature. The results were collected from 95 articles and were obtained using the keyword LED combined with plant growth; flavonoids; phenols; carotenoids; terpenes; glucosinolates; food preservation. We found the subject regarding the LED effect on plant growth and development in 11 of the articles analyzed. The treatment of LED on phenol content was registered in 19 articles, while information regarding flavonoid concentrations was revealed by 11 articles. Two articles we reviewed debate the accumulation of glucosinolates and four articles analyzed the synthesis of terpenes under LED illumination and 14 papers analyzed the variation in content of carotenoids. The effect of LED on food preservation was reported in 18 of the works analyzed. Some of the 95 papers contained references which included more keywords.
... Various crop plants synthesize S-containing organic compounds, and especially plants belonging to Brassicaceae family synthesize sulfated metabolites including glucosinolates (Fahey et al., 2001). These glucosinolates provide protection against insects, fungi, microorganisms, and herbivores (Holst and Fenwick, 2003). ...
Reduction in soil fertility and depletion of natural resources due to current intensive agricultural practices along with climate changes are the major constraints for crop productivity and global food security. Diverse microbial populations’ inhabiting the soil and rhizosphere participate in biogeochemical cycling of nutrients and thereby, improve soil fertility and plant health, and reduce the adverse impact of synthetic fertilizers on the environment.
Sulphur is 4th most common crucial macronutrient required by all organisms including plants, animals, humans and microorganisms. Effective strategies are required to enhance sulphur content in crops for minimizing adverse effects of sulphur deficiency on plants and humans. Various microorganisms are involved in sulphur cycling in soil through oxidation, reduction, mineralization, and immobilization, and volatalization processes of diverse sulphur compounds. Some microorganisms possess the unique ability to oxidize sulphur compounds into plant utilizable sulphate (SO4
2-) form. Considering the importance of sulphur as a nutrient for crops, many bacteria and fungi involved in sulphur cycling have been characterized from soil and rhizosphere. Some of these microbes have been found to positively affect plant growth and crop yield through multiple mechanisms including the enhanced mobilization of nutrients in soils (i.e., sulphate, phosphorus and nitrogen), production of growthpromoting hormones, inhibition of phytopathogens, protection against oxidative damage and mitigation of abiotic stresses. Application of these beneficial microbes as biofertilizers may reduce the conventional fertilizer
application in soils. However, large-scale, well-designed, and long-term field trials are necessary to recommend the use of these microbes for increasing nutrient availability for growth and yield of crop plants. This review discusses the current knowledge regarding sulphur deficiency symptoms in plants, biogeochemical cycling of
sulphur and inoculation effects of sulphur oxidizing microbes in improving plant biomass and crop yield in different crops.
... Increasing the beneficial GSL content has been a major breeding goal for Brassica species in recent years (Ishida et al., 2014;Barba et al., 2016). The hydrolysis products of GRA such as isothiocyanates have anticancer effects in humans (Fahey et al., 2001;Fahey et al., 2002). Furthermore, enzymatic degradation of GRA to PRO inhibits iodine uptake in mammals, leading to thyroid dysfunction. ...
The major enzyme encoded by the glucosinolate biosynthetic gene AOP2 is involved in catalyzing the conversion of glucoiberin (GIB) into sinigrin (SIN) in Brassicaceae crops. The AOP2 proteins have previously been identified in several Brassicaceae species, but not in Tumorous stem mustard. As per this research, the five identified members of the AOP2 family from the whole genome of Brassica juncea named BjuAOP2.1-BjuAOP2.5 were found to be evenly distributed on five chromosomes. The subcellular localization results implied that BjuAOP2 proteins were mainly concentrated in the cytoplasm. Phylogenetic analysis of the AOP2 proteins from the sequenced Brassicaceae species in BRAD showed that BjuAOP2 genes were more closely linked to Brassica carinata and Brassica rapa than Arabidopsis. In comparison with other Brassicaceae plants, the BjuAOP2 members were conserved in terms of gene structures, protein sequences, and motifs. The light response and hormone response elements were included in the BjuAOP2 genes’ cis-regulatory elements. The expression pattern of BjuAOP2 genes was influenced by the different stages of development and the type of tissue being examined. The BjuAOP2 proteins were used to perform the heterologous expression experiment. The results showed that all the five BjuAOP2 proteins can catalyze the conversion of GIB to SIN with different catalytic activity. These results provide the basis for further investigation of the functional study of BjuAOP2 in Tumorous stem mustard glucosinolate biosynthesis.
... Brassica vegetables, such as kale, cabbage, broccoli, and cauliflower, constitute a popular food crop of nutritional and economic significance worldwide. 3 Kale (Brassica oleracea var. acephala) contains a high level of dietary fiber, vitamins, carotenoids, phenolic compounds, and glucosinolates. ...
... Simple sugar, rhamnose, also known as glucosinolates, and isothiocyanates are among the substances found in Moringa oleifera [34,35] . Two alkaloids, Moringinine and Moringine, are present in the bark and stem of the Moringa plant [36] . ...
... Glucosinolates (GSLs) are an important class of plant secondary metabolites. Currently, about 200 GSLs are known, which are distributed in 16 families of dicotyledonous plants, especially in Brassicaceae [1][2][3]. The GSL hydrolysis products display diverse bioactivities, function both in defence and as an attractant in plants, play a role in cancer prevention in humans, and act as flavour compounds. ...
Cabbage (Brassica oleracea var. capitata) is a vegetable rich in glucosinolates (GSLs) that have proven health benefits. To gain insights into the synthesis of GSLs in cabbage, we systematically analyzed GSLs biosynthetic genes (GBGs) in the entire cabbage genome. In total, 193 cabbage GBGs were identified, which were homologous to 106 GBGs in Arabidopsis thaliana. Most GBGs in cabbage have undergone negative selection. Many homologous GBGs in cabbage and Chinese cabbage differed in expression patterns indicating the unique functions of these homologous GBGs. Spraying five exogenous hormones significantly altered expression levels of GBGs in cabbage. For example, MeJA significantly upregulated side chain extension genes BoIPMILSU1-1 and BoBCAT-3-1, and the expression of core structure construction genes BoCYP83A1 and BoST5C-1, while ETH significantly repressed the expression of side chain extension genes such as BoIPMILSU1-1, BoCYP79B2-1, and BoMAMI-1, and some transcription factors, namely BoMYB28-1, BoMYB34-1, BoMYB76-1, BoCYP79B2-1, and BoMAMI-1. Phylogenetically, the CYP83 family and CYP79B and CYP79F subfamilies may only be involved in GSL synthesis in cruciferous plants. Our unprecedented identification and analysis of GBGs in cabbage at the genome-wide level lays a foundation for the regulation of GSLs synthesis through gene editing and overexpression.
... Moringa (Division: Angiospermae/Magnoliophyta) is a flowering plant, The flowers are fragrant, bisexual, and pentapetalous, it includes five Petals that are unequal, distinct, thinly veiled, yellowish-white, the flower is syncarpous (Subclass: Dilleniidae) and has united carpels, they grow on slender, hairy stalks in spreading or drooping later flower clusters, the leaves of these plants are feathery, pale green, compound, and tripinnate, they are about 30-60 cm long and contain many small leaflets (12,13). Moringa oleifera has been more utilized in the remediation of different types of illness because of its antibacterial activity, it is rich in compounds containing simple sugar, rhamnose, and a unique group of compounds called glucosinolates and isothiocyanate (14,15). Other medicinal properties include antipyretic, anti-epileptic, anti-inflammatory, antiulcerative, anti-hypertensive, anti-cholesterol, anti-oxidant, anti-bacterial and anti-fungal, anti-diabetic, antihepatoprotective (16)(17)(18)(19)(20). ...
Moringa oleifera is a well-known medicinal herb because it has antibacterial and antifungal activity, M.oleifera is A strong source of several phytochemicals that are a drug that's widely used to cure a number of illnesses, such as Anti-Pyretic, Epileptic, Inflammatory disorders Ulcerative, anti-Hypertensive, Cholesterol-lowering, antioxidant, and other medicinal effects. M.oleifera leaf extracts were utilized in the plant component examination and the assessment of the antifungal activity. For experimental purposes, the strain Candida albicans was utilized. To test the anti-Fungal effect of the extracts on fungal cultures, the Well diffusion method was used. The phytochemical screening indicated the presence of ( Alkaloids, Flavonoids, Saponins, Steroids, Tannins, Cardiac glycoside, Terpenoids, and the absence of Reducing sugar, Anthraquinones, Phlobatannins) in both extracts. Anti-Fungal activity against Candida albicans was strongly active in Aqueous & Alcoholic Leaf Extracts of Moringa oleifera. Due to the Moringa leaf aqueous extract, an area of inhibition was found from ( 0.23cm, 0.27, 0.3, 0.39, to 0.58 cm ) As there is an increase in concentration from (100 to 500 µg/ml ), respectively. While an area It was found that the inhibition induced by ethanolic extract for Moringa leaf increased from (1.29cm,1.40,1.44,1.53,to1.87cm) As there is an increase in concentration from (100 to 500 µg/ml), against Candida albicans, respectively. Nystatin is an antibiotic made of polyene, A section of polyene antifungal compounds, Used for treating fungal infections most commonly. Nystatin has been used against Candida albicans as a positive control, While the region of inhibition appeared (0.5cm) of anti-Nystatin against Candida albicans. This study evaluated various concentrations of extracts Moringa oleifera leaves and anti-Nystatin against Candida albicans. The ethanolic alcoholic extract of Moringa oleifera leaf showed a higher inhibition zone than the aqueous extract and anti-Nystatin.
... We targeted the aliphatic GSL biosynthesis pathway since the aliphatic profile comprises up to 92% of all GSLs reported from rapeseed 9 . Moreover, major GSLs such as progoitrin that have adverse metabolic effects in animals belong to the aliphatic profile 6,16,48 . We reasoned that functional mutations in genes involved in the Aliphatic and other GSL types measured from homozygous BnMYB28 (genotype A 1 A 1 B 1 B 1 , seed code 200527) and BnCYP79F1 (genotype C 1 C 1 D 1 D 1 , seed code 200529) originating from M 3 xM 3 crosses. ...
The presence of anti-nutritive compounds like glucosinolates (GSLs) in the rapeseed meal severely restricts its utilization as animal feed. Therefore, reducing the GSL content to < 18 µmol/g dry weight in the seeds is a major breeding target. While candidate genes involved in the biosynthesis of GSLs have been described in rapeseed, comprehensive functional analyses are missing. By knocking out the aliphatic GSL biosynthesis genes BnMYB28 and BnCYP79F1 encoding an R2R3 MYB transcription factor and a cytochrome P450 enzyme, respectively, we aimed to reduce the seed GSL content in rapeseed. After expression analyses on single paralogs, we used an ethyl methanesulfonate (EMS) treated population of the inbred winter rapeseed ‘Express617’ to detect functional mutations in the two gene families. Our results provide the first functional analysis by knock-out for the two GSL biosynthesis genes in winter rapeseed. We demonstrate that independent knock-out mutants of the two genes possessed significantly reduced seed aliphatic GSLs, primarily progoitrin. Compared to the wildtype Express617 control plants (36.3 µmol/g DW), progoitrin levels were decreased by 55.3% and 32.4% in functional mutants of BnMYB28 (16.20 µmol/g DW) and BnCYP79F1 (24.5 µmol/g DW), respectively. Our study provides a strong basis for breeding rapeseed with improved meal quality in the future.
... Correspondingly, GSLs can be divided into three types based on the source of precursor amino acids, for example, aliphatic GSLs derived from alanine (Ala), leucine (Leu), isoleucine (Ile), methionine (Met) and valine (Val); indole GSLs derived from tryptophan (Trp); and aromatic GSLs derived from phenylalanine (Phe) and tyrosine (Tyr) [12][13][14]. To date, over 200 GSLs have been discovered [15,16], which were usually synthesized through three steps. The first step is the lengthening of the progenitor amino acid side chain. ...
Glucosinolates (GSLs) are secondary plant metabolites that are enriched in rapeseed and related Brassica species, and they play important roles in defense due to their anti-nutritive and toxic properties. Here, we conducted a genome-wide association study of six glucosinolate metabolites (mGWAS) in rapeseed, including three aliphatic glucosinolates (m145 gluconapin, m150 glucobrassicanapin and m151 progoitrin), one aromatic glucosinolate (m157 gluconasturtiin) and two indole glucosinolates (m165 indolylmethyl glucosinolate and m172 4-hydroxyglucobrassicin), respectively. We identified 113 candidate intervals significantly associated with these six glucosinolate metabolites. In the genomic regions linked to the mGWAS peaks, 187 candidate genes involved in glucosinolate biosynthesis (e.g., BnaMAM1, BnaGGP1, BnaSUR1 and BnaMYB51) and novel genes (e.g., BnaMYB44, BnaERF025, BnaE2FC, BnaNAC102 and BnaDREB1D) were predicted based on the mGWAS, combined with analysis of differentially expressed genes. Our results provide insight into the genetic basis of glucosinolate biosynthesis in rapeseed and should facilitate marker-based breeding for improved seed quality in Brassica species.
... Glucosinolates (GSL) (β-thioglucoside-N-hydroxy sulfates) are rich-sulfur secondary metabolites raising potential biofumigation interest due to their biological properties. These molecules are inactive in their native form but they are precursors of various highly reactive products presenting fungicidal, bactericidal and insecticidal properties [1][2][3][4][5][6]. These properties raise the interest of GSL as natural biopesticides and suitable biofumigant agents for crop protection instead of chemical products [7,8]. ...
Glucosinolates (GSL) (β-thioglucoside-N-hydroxy sulfates) are rich-sulfur secondary metabolites raising potential biofumigation interest due to their biological properties. Sinigrin and gluconapin are the main glucosinolates present in brown mustard seeds (Brassica juncea). These glucosinolates are very suitable for the development of phytosanitary products due to their fungicidal, bactericidal and insecticidal effects. In this work, the purification of sinigrin and gluconapin extracted from defatted mustard seeds was studied using macroporous anion exchange resins. A strongly and a weakly anionic resin were first tested according to the nature of their functional group and through their selectivity towards glucosinolates. Anion-exchange resin purification was first studied in static (batch) mode in order to determine the optimal operating conditions; it was then tested in a dynamic (continuous) mode (column) to validate the process. In static mode, the adsorption behavior and characteristics of both resins were compared. The results showed that the strongly basic resin PA312LOH ensures better adsorption of glucosinolates and that the experimental data fit well with the Freundlich isotherm. Moreover, analysis showed that PA312LOH resin was selective for glucosinolates purification towards the proteins. The desorption of glucosinolates was then investigated. Firstly, the operating conditions were optimized by studying the effects of salt concentration and the eluate-resin ratio. This preliminary optimization allowed recovering 72.9% of intact sinigrin and the juice purity was increased from 43.05% to 79.63%. Secondly, dynamic (continuous mode) experiments allowed the recovery of 64.5% of sinigrin and 28% of gluconapin by varying the eluent ionic strength and the flow rate. Resin was finally successfully regenerated using NaOH.
... Glucosinolates are sulphur containing plant secondary metabolites, which are predominately found in the Brassicaceae family. The isothiocyanates and other hydrolytic breakdown products of glucosinolates are well known to have beneficial effects, such as reducing the incidence of cancer in humans and other mammals and the risk of degenerative diseases (Li et al. 2001a;Fahey and Talalay 1995;Fahey et al. 2001;Lin et al. 1998). Dietary groups of sulforaphane, isothiocyanates and indoles derived from Brassica vegetables are also known to stimulate apoptosis and confer protection against DNA damage in human colon cells (Bonnesen et al. 2001;Chiao et al. 2002). ...
... Broccoli is rich in vitamins C and E, quercetin and kaempferol glycosides [2]. Broccoli is also rich in glucosinolates, a group of about 120 molecules derived from amino acids that have a β-D-glucopyranose residue linked through a sulphur atom to a (Z)-N-hydroximinosulfate ester, plus a variable R group [3]. These molecules confer the characteristic pungent flavor of broccoli. ...
Broccoli (Brassica oleracea L. var. Italica Plenck) is a cruciferous crop that is considered to be a good source of micronutrients. Better taste is a main objective for breeding, as consumers are demanding novel cultivars suited for a healthy diet, but ones that are more palatable. This study aimed to identify primary metabolites related to cultivars with better taste according to a consumer panel. For this purpose, we performed a complete primary metabolomic profile of 20 different broccoli cultivars grown in the field and contrasted the obtained data with the results of a consumer panel which evaluated the taste of the same raw buds. A statistical analysis was conducted to find primary metabolites correlating with better score in the taste panels. According to our results, sugar content is not a distinctive factor for taste in broccoli. The accumulation of the amino acids leucine, lysine and alanine, together with Myo-inositol, negatively affected taste, while a high content of γ-aminobutyric acid (GABA) is a distinctive trait for cultivars scoring high in the consumer panels. A Principal Component Analysis (PCA) allowed us to define three different groups according to the metabolomic profile of the 20 broccoli cultivars studied. Our results suggest molecular traits that could be useful as distinctive markers to predict better taste in broccoli or to design novel biotechnological or classical breeding strategies for improving broccoli taste.
... Broccoli sprouts and Brussels sprouts were in vitro digested using an oral, gastric, and intestinal phase as previously published [22,[55][56][57][58][59][60][61][62][63]. Briefly, salivary amylase was added to simulate the oral phase of digestion, which was followed by a gastric phase where samples were acidified to a pH of 2.5 with hydrochloric acid, and pepsin was added. ...
Brassica vegetables contain a multitude of bioactive compounds that prevent and suppress cancer and promote health. Evidence suggests that the gut microbiome may be essential in the production of these compounds; however, the relationship between specific microbes and the abundance of metabolites produced during cruciferous vegetable digestion are still unclear. We utilized an ex vivo human fecal incubation model with in vitro digested broccoli sprouts (Broc), Brussels sprouts (Brus), a combination of the two vegetables (Combo), or a negative control (NC) to investigate microbial metabolites of cruciferous vegetables. We conducted untargeted metabolomics on the fecal cultures by LC-MS/MS and completed 16S rRNA gene sequencing. We identified 72 microbial genera in our samples, 29 of which were significantly differentially abundant between treatment groups. A total of 4499 metabolomic features were found to be significantly different between treatment groups (q ≤ 0.05, fold change > 2). Chemical enrichment analysis revealed 45 classes of compounds to be significantly enriched by brassicas, including long-chain fatty acids, coumaric acids, and peptides. Multi-block PLS-DA and a filtering method were used to identify microbe–metabolite interactions. We identified 373 metabolites from brassica, which had strong relationships with microbes, such as members of the family Clostridiaceae and genus Intestinibacter, that may be microbially derived.
... La biosynthèse de ces métabolites se fait à partir des acides aminés aromatiques et aliphatiques. 42 44 Plus communément on retrouve des glucosinolates dans tous les végétaux de notre alimentation quotidienne appartenant à la famille des choux, des brocolis, des radis, des câpres, le wasabi, la moutarde, le raifort etc. ...
Depuis longtemps les réactifs isothiocyanates (ITCs) sont largement utilisés dans le domaine de la bioconjugaison. Ces électrophiles forts réagissent avec les cystéines et les lysines des protéines pour former une liaison stable. Cette réactivité click permet de réaliser des marquages sélectifs ainsi que des fonctionnalisations de protéines. Cependant, les ITCs ne sont pas faciles à synthétiser et à isoler et leur stabilité ne permet pas une conservation optimale.Le but de ce projet est de développer le système enzymatique myrosinase-glucosinolate (MG) comme outil de conjugaison capable de former un ITC in situ. Le tandem MG est un mécanisme de défense des plantes de l’ordre des Brassicales bien connu. Dans ce système biochimique, la myrosinase opère comme thioglucosidase, en hydrolysant les glucosinolates (GLs), pour générer des ITCs. L’avantage de ce tandem enzymatique est de produire les ITCs à partir de précurseurs solubles dans l’eau, non toxiques, sous conditions douces.Afin d’explorer cet outil enzymatique, deux types de GLs non naturels ont été conçus. En raison de l’importance de l’interaction lectine-mannose dans les mécanismes d’adhésion bactérienne, nous avons conçu une petite librairie de GLs intégrant un mannoside. De cette façon il est possible d’étudier des lectines bactérienne (FimH). Le second type de glucosinolate est caractérisé par une deuxième fonction chimique, permettant de réaliser des réactions orthogonales.Le système MG a été évalué dans plusieurs approches de bioconjugaison telles que le marquage sélectif d’une lectine, la synthèse de néoglycoprotéines et la fonctionnalisation de nanoparticules.
... 242 This phytochemical group in its intact form is relatively biologically inactive. 243 However, products resulting from glucosinolate hydrolysis, such as isothiocyanates, have anticarcinogenic, antioxidant, and antimicrobial activities. 244 Furthermore, some studies demonstrate that isothiocyanates could inhibit biolm formation through interaction with the QS system. ...
Covering: 2009 to 2021Antimicrobial resistance is now rising to dangerously high levels in all parts of the world, threatening the treatment of an ever-increasing range of infectious diseases. This has becoming a serious public health problem, especially due to the emergence of multidrug-resistance among clinically important bacterial species and their ability to form biofilms. In addition, current anti-infective therapies have low efficacy in the treatment of biofilm-related infections, leading to recurrence, chronicity, and increased morbidity and mortality. Therefore, it is necessary to search for innovative strategies/antibacterial agents capable of overcoming the limitations of conventional antibiotics. Natural compounds, in particular those obtained from plants, have been exhibiting promising properties in this field. Plant secondary metabolites (phytochemicals) can act as antibiofilm agents through different mechanisms of action from the available antibiotics (inhibition of quorum-sensing, motility, adhesion, and reactive oxygen species production, among others). The combination of different phytochemicals and antibiotics have revealed synergistic or additive effects in biofilm control. This review aims to bring together the most relevant reports on the antibiofilm properties of phytochemicals, as well as insights into their structure and mechanistic action against bacterial pathogens, spanning December 2008 to December 2021.
... Glucosinolates are secondary metabolites in Brassicaceae plants and share a general structure of glucose covalently bonded to a sulfur and a sulfated dioxamine with an R moiety of different linkages. The R groups are classified as aliphatic, aromatic, ωmethylthioalkyl, and heterocyclic (indole) [9]. Tissue compartmentalization has evolutionarily separated the chemically and thermally stable glucosinolates and their hydrolytic enzyme myrosinase, a beta thioglucosidase [10]. ...
Camelina sativa (camelina) seed, oil, and defatted meal are widely used for food, animal feed, and other purposes. The accurate quantification of camelina glucosinolates is critical as their functionalities are highly dose-dependent. The classic quantification of glucosinolates in camelina products involves tedious desulfation steps, toxic reagents, and a lengthy instrument time because glucosinolates are easy to degrade and subject to interference in the liquid chromatography. Thus, we developed and validated an eco-efficient UPLC-DAD method for determining glucoarabin (GS9), glucocamelinin (GS10), and homoglucocamelinin (GS11) in camelina seed, oil, and defatted meal. Glucosinolates were extracted using 80% cold methanol to denature myrosinase, and were separated by an HSS T3 column without desulfation. Glucotropaeolin was used as an internal standard to track analyte degradation and loss during sample preparation. The method has shown high precision (relative standard deviations ranging from 4.12% to 6.54%) and accuracy (>94.4% spike recovery) for GS9-11, and all validation parameters passed the industry-consensus AOAC Appendix F criteria. To our best knowledge, this is the first eco-efficient and low-cost analytical method that is validated against strict AOAC criteria for the quantification of intact camelina glucosinolates. The method is suitable to be adopted as a new industrial testing standard to assist in the quality control of camelina products.
... These authors also provided a list of about sixty Brassicaceae sharing the potential to form isothiocyanates. Hence, rapeseed may be only one among many Brassicaceae sharing the potential to form COS during the late stages of growth. COS is also produced from wheat [8] although it lacks the capacity to produce glucosinolates and myrosinase [30]. ...
Carbonyl sulfide (COS) fluxes simulated by vegetation and soil component models, both implemented in the ORCHIDEE land surface model, were evaluated against field observations at two agroecosystems in central France. The dynamics of a biogenic process not yet accounted for by this model, i.e., COS emissions from croplands, was examined in the context of three independent and complementary approaches. First, during the growing seasons of 2019 and 2020, monthly variations in the nighttime ratio of vertical mole fraction gradients of COS and carbon dioxide measured between 5 and 180 m height (GradCOS/GradCO2), a proxy of the ratio of their respective nocturnal net fluxes, were monitored at a rural tall tower site near Orléans (i.e., a "profile vs. model" approach). Second, field observations of COS nocturnal fluxes, obtained by the Radon Tracer Method (RTM) at a sub-urban site near Paris, were used for that same purpose (i.e., a "RTM vs. model" approach of unaccounted biogenic emissions). This site has observations going back to 2014. Third, during the growing seasons of 2019, 2020 and 2021, horizontal mole fraction gradients of COS were calculated from downwind-upwind surveys of wheat and rapeseed crops as a proxy of their respective exchange rates at the plot scale (i.e., a "crop based" comparative approach). The "profile vs. model" approach suggests that the nocturnal net COS uptake gradually weakens during the peak growing season and recovers from August on. The "RTM vs. model" approach suggests that there exists a biogenic source of COS, the intensity of which culminates in late June early July. Our "crop based" comparative approach demonstrates that rapeseed crops shift from COS uptake to emission in early summer during the late stages of growth (ripening and senescence) while wheat crops uptake capacities lower markedly. Hence, rapeseed appears to be a much larger source of COS than wheat at the plot scale. Nevertheless, compared to current estimates of the largest COS sources (i.e., marine and anthropogenic emissions), agricultural emissions during the late stages of growth are of secondary importance.
... L-Sulforaphane (SFN) is an isothiocyanate in cruciferous vegetables of the brassica class such as; broccoli, cauliflower, and cabbage [16,45]. Several studies have revealed that SFNe has antitumor [53], immune-enhancing [50], and antioxidative effects [10,15]. ...
In the last decade, most of the evidence on the clinical benefits of including cruciferous foods in the diet has been focused on the content of glucosinolates (GSL) and their corresponding isothiocyanates (ITC), and mercapturic acid pathway metabolites, based on their capacity to modulate clinical, biochemical, and molecular parameters. The present systematic review summarizes findings of human studies regarding the metabolism and bioavailability of GSL and ITC, providing a comprehensive analysis that will help guide future research studies and facilitate the consultation of the latest advances in this booming and less profusely researched area of GSL for food and health. The literature search was carried out in Scopus, PubMed and the Web of Science, under the criteria of including publications centered on human subjects and the use of Brassicaceae foods in different formulations (including extracts, beverages, and tablets), as significant sources of bioactive compounds, in different types of subjects, and against certain diseases. Twenty-eight human intervention studies met inclusion criteria, which were classified into three groups depending on the dietary source. This review summarizes recent studies that provided interesting contributions, but also uncovered the many potential venues for future research on the benefits of consuming cruciferous foods in our health and well-being. The research will continue to support the inclusion of GSL-rich foods and products for multiple preventive and active programs in nutrition and well-being.
Brassicaceae are known to contain compounds that are biofumigants. This study aimed to determine the effect of Brassicaceae waste application on soil nematode community. Broccoli leaves and stems (Brassica oleracea var. italic), cabbage leaves and stems (B. oleracea var. capitate), kailan stems (B. oleracea var. alboglabra), radish leaves (Raphanus sativus), and leaves of kamanilan weed (Rorippa indica) were tested in this study. The total glucosinolate content of Brassicaceae waste was estimated using the palladium method with a modified spectrophotometer. The experiment was carried out in polybags containing 500 grams of soil-infested nematodes. Brassicaceae waste (15 grams/polybag) was chopped and mixed into the soil, watered, and polybags were tightly closed for 14 days. The experiment was arranged in a completely randomized design with nine treatments and five replications. The results of the total glucosinolate analysis showed that broccoli, radish, and kamanilan leaves fall into the high category (144.7-185.2 µmol/g); cabbage leaves, cabbage stems, and kailan stems fall into the medium category (52.0-56.0 µmol/g); and broccoli stems fall into the low category (35.4 µmol/g). There was no correlation between total glucosinolate contents and their effect on suppressing soil nematode communities at the applied effluent dose. The population of bacterivorous nematodes increased in each waste treatment, especially in kamanilan leaf treatment (R. indica) which reached 13,008 individuals. These results indicate that kamanilan weed has good potential to improve soil health. The treatment of Brassicaceae waste against soil nematode communities showed a low diversity index, an uneven evenness index, and a high dominance index.
Sulforaphane (SFN), a natural isothiocyanate derivative, has been extensively studied as therapeutic compound. Different cellular pathways were described for explaining its promising pharmacological effects such as anti-inflammatory, antitumoral, and antioxidant. In this sense, several studies have investigated SFN as single or in association with conventional drugs, specially as anti-inflammatory and antitumoral. In this sense, new strategies for delivering SFN have been discussed for overcoming physicochemical and/or biopharmaceutics limitations by using a variety of nanocarriers types such as micelles, polymeric/lipid/inorganic nanoparticles, nanocomposites, and gels. In this chapter, a discussion associating SFN molecular mechanisms of action with its potential pharmacological applications and the main nanocarriers for SFN delivery are provided, highlighting the relationships between biological synthesis, pharmacological aspects, and the new nanotechnological strategies for developing effective and safe pharmacotherapeutic alternatives.KeywordsSulforaphaneNanomedicinesInflammationCancer
The study of primary plant metabolism has been the main focus of scientists for several years, seconding research related to the secondary metabolism. Nowadays, with the better understanding of the processes and products involved in primary metabolism, the focus has switched to the expansion of knowledge involving secondary metabolism. Initially, plants were the focus of secondary metabolite studies due to their ease of acquisition and availability, reasons for being a term coined by plant physiologists. Only in the twentieth century has the secondary metabolites from microorganisms began to be recognized and investigated due to the value that these metabolites could bring to science. Not by chance, it was in the twentieth century that the era of antibiotics began. In this chapter, a voyage through the centuries is proposed, focused on secondary metabolism and metabolites, highlighting how they shifted from disregarded molecules to the powerhouses of bioactivity for modern science.
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.
Isothiocyanates are ubiquitous building blocks used across the fields. Nevertheless, their classical syntheses very often rely on the use of toxic and expensive reagents. Herein, we report a new practical, mild, high-yielding, and supporting-electrolyte-free electrochemical method for the preparation of aliphatic and aromatic isothiocyanates from amine and carbon disulfide.
The NLRP3 inflammasome plays an important role in the pathogenesis of numerous inflammation-related diseases. Benzyl isothiocyanate (BITC) is rich in cruciferous vegetables and possesses potent antioxidant, anti-inflammatory, anti-cancer, and anti-obesogenic properties. In this study, we investigated the role of the NLRP3 inflammasome in the protection by BITC against steatohepatitis and insulin resistance. A mouse model of high-fat/cholesterol/cholic acid diet (HFCCD)-induced steatohepatitis, LPS/nigericin-stimulated primary Kupffer cells, and IL-1β treated primary hepatocytes were used. BITC attenuated LPS/nigericin-induced activation of the NLRP3 inflammasome by enhancing protein kinase A-dependent NLRP3 ubiquitination, which increased the degradation of NLRP3 and reduced IL-1β secretion in Kupffer cells. In hepatocytes, BITC pretreatment reversed the IL-1β-induced decrease in the phosphorylation of IR, AKT, and GSK3β in response to insulin. After 12 weeks of HFCCD feeding, increases in blood alanine aminotransferase (ALT) and glucose levels were ameliorated by BITC. Hepatic IL-1β production, macrophage infiltration, and collagen expression induced by HFCCD were also mitigated by BITC. BITC suppresses activation of the NLRP3 inflammasome in Kupffer cells by enhancing the PKA-dependent ubiquitination of NLRP3, which leads to suppression of IL-1β production and subsequently ameliorates hepatic inflammation and insulin resistance.
In this study, endophytic and rhizospheric bacteria were isolated from Moringa olifera and M. perigreina from Oman, and their in vitro antagonistic activity against Pythium aphanidermatum was tested using a dual culture assay. The promising strains were tested further for their compatibility and potential for plant growth promotion, biofilm formation, antifungal volatile organic compound (VOC) production, and the biological control of P. aphanidermatum damping-off of cabbage (Brassica oleracea L.) under greenhouse conditions. A total of 12 endophytic and 27 rhizospheric bacteria were isolated from Moringa spp. Among them, Bacillus pumilus MPE1 showed the maximum antagonistic activity against P. aphanidermatum in the dual culture assay, followed by Paenibacillus glucanolyticus MPE3 and Pseudomonas indica MOR3 and MOR8. These bacterial isolates induced abundant morphological abnormalities in the hyphae of P. aphanidermatum, as observed via scanning electron microscopy. The in vitro cross-streak assay showed that these bacterial isolates were compatible among themselves, except for P. indica MOR8 × P. glucanolyticus MPE3. These antagonists released VOCs that restricted the growth of P. aphanidermatum in an in vitro assay. These antagonistic bacteria released 2,4-dimethylheptane and 4-methyloctane as the predominant volatile compounds. Of the four antagonistic bacterial strains, P. indica MOR8 was capable of forming biofilm, which is considered a trait that improves the efficacy of rhizosphere inoculants. The results of the greenhouse experiments showed that the soil treatment with B. pumilus MPE1 showed the highest reduction (59%) in the incidence of P. aphanidermatum damping-off in cabbage, evidencing its potential as a biological control agent for the management of this disease. Further research is needed to characterize the antifungal traits and activities of B. pumilus MPE1 and to assert its potential use against other soil-borne plant pathogens.
Mass spectrometry has developed into a platform for the assessment of health, sensory, quality and safety aspects of food. Current nutrition research focuses on unravelling the link between acute or chronic dietary and nutrient intake and the physiological effects at cellular, tissue and whole body level. The bioavailability and bioefficacy of food constituents and dose-effect correlations are key to understanding the impact of food on defined health outcomes. To generate this information, appropriate analytical tools are required to identify and quantify minute amounts of individual compounds in highly complex matrices (such as food or biological fluids) and to monitor molecular changes in the body in a highly specific and sensitive manner. Mass spectrometry has become the method of choice for such work and now has broad applications throughout all areas of nutrition research. This book focuses the contribution of mass spectrometry to the advancement of nutrition research. Aimed at students, teachers and researchers, it provides a link between nutrition and analytical biochemistry. It guides nutritionists to the appropriate techniques for their work and introduces analytical biochemists to new fields of application in nutrition and health. The first part of the book is dedicated to the assessment of macro- and micro-nutrient status with a view to making dietary recommendations for the treatment of diet-related diseases. The second part shows how mass spectrometry has changed nutrition research in fields like energy metabolism, body composition, protein turnover, immune modulation and cardiovascular health.
Kimchi cabbage is the main ingredient in kimchi, and improvements in yield and quality are therefore meaningful for the health of the consumer and the kimchi industry. In light of this, the present study investigated whether the gluconasturtiin (GNT) content of kimchi cabbage can be increased by applying the endophytic fungus Heteroconium chaetospira (HC). We observed that the composition of amino acids in kimchi cabbage leaves differed depending on the type of fertilizer applied during cultivation. Kimchi cabbage seedlings grew well in glutamine medium supplied with nitrate nitrogen regardless of HC inoculation. However, unfertilized kimchi cabbage seedlings that were not inoculated with HC grew poorly while those inoculated with HC grew well, suggesting HC has a beneficial effect on phenylalanine absorption by the root. When kimchi cabbage was grown with endophytic fungi inoculation and oil cake application, phenylaniline content in the leaves increased. Furthermore, when the 'Suho' cultivar inoculated with HC was grown in oil cake-supplemented soil, the gluconapin and glucobrassicanapin contents were slightly lowered and the GNT content was 8.36 μmole/g, or 74% of the total glucosinolate (GSL) content (11.3 μmole/g). When the 'Asiaipssam' cultivar was grown under the same conditions, its GNT content increased to 6.7 μmole/g, or 81% of the total GSL content (8.3 μmole/g). This cultivar difference was due an increase in GNT content without any change in the content of other GSLs. In conclusion, we propose the use of endophytic root fungi is an effective means to increase kimchi cabbage growth by improving the absorption of amino acids, making it an appropriate strategy for increasing specific glucosinolates.
Background
Beauveria are entomopathogenic fungi of a broad range of arthropod pests. Many strains of Beauveria have been developed and marketed as biopesticides. Beauveria species are well-suited as the active ingredient within biopesticides because of their ease of mass production, ability to kill a wide range of pest species, consistency in different conditions, and safety with respect to human health. However, the efficacy of these biopesticides can be variable under field conditions. Two under-researched areas, which may limit the deployment of Beauveria -based biopesticides, are the type and amount of insecticidal compounds produced by these fungi and the influence of diet on the susceptibility of specific insect pests to these entomopathogens.
Methods
To understand and remedy this weakness, we investigated the effect of insect diet and Beauveria -derived toxins on the susceptibility of diamondback moth larvae to Beauveria infection. Two New Zealand-derived fungal isolates, B. pseudobassiana I12 Damo and B. bassiana CTL20, previously identified with high virulence towards diamondback moth larvae, were selected for this study. Larvae of diamondback moth were fed on four different plant diets, based on different types of Brassicaceae, namely broccoli, cabbage, cauliflower, and radish, before their susceptibility to the two isolates of Beauveria was assessed. A second experiment assessed secondary metabolites produced from three genetically diverse isolates of Beauveria for their virulence towards diamondback moth larvae.
Results
Diamondback moth larvae fed on broccoli were more susceptible to infection by B. pseudobassiana while larvae fed on radish were more susceptible to infection by B. bassiana . Furthermore, the supernatant from an isolate of B. pseudobassiana resulted in 55% and 65% mortality for half and full-strength culture filtrates, respectively, while the filtrates from two other Beauveria isolates, including a B. bassiana isolate, killed less than 50% of larvae. This study demonstrated different levels of susceptibility of the insects raised on different plant diets and the potential use of metabolites produced by Beauveria isolates in addition to their conidia.
Two wild-growing Brassicaceae plants of Croatian origin, Aurinia leucadea (Guss.) K. Koch and Lepidium draba L., were investigated to uncover glucosinolates via GC/MS analysis of their degradation products. The main constituents of Aurinia leucadea (Guss.) K.Koch distillate were hex-5-enenitrile (28.8%) and but-3-enyl isothiocyanate (18.8%), while 4,5-epithiopentanenitrile (50%) and 5,6-epithiohexanenitrile (18.5%) were the main volatile compounds in autolysate. 4-(Methylsulfanyl)butyl isothiocyanate (96.4%) constituted almost the entire Lepidium draba L. distillate, while the autolysate was characterized by 4-(methylsulfinyl)butyl isothiocyanate (57.3%). So, regarding the glucosinolate degradation products, the main glucosinolates of A. leucadea were glucobrassicanapin and gluconapin, and of L. draba glucoerucin and glucoraphanin.
Plasmodiophora brassicae causes a serious threat to cruciferous plants including radish (Raphanus sativus L.). Knowledge on the pathogenic regularity and molecular mechanism of P. brassicae and radish is limited, especially on the metabolism level. In the present study, clubroot-susceptible and clubroot-resistant cultivars were inoculated with P. brassicae Race 4, root hairs initial infection of resting spores (107 CFU/mL) at 24 h post-inoculation and root galls symptom arising at cortex splitting stage were identified on both cultivars. Root samples of cortex splitting stage of two cultivars were collected and used for untargeted metabonomic analysis. We demonstrated changes in metabolite regulation and pathways during the cortex splitting stage of diseased roots between clubroot-susceptible and clubroot-resistant cultivars using untargeted metabonomic analysis. We identified a larger number of differentially regulated metabolites and heavier metabolite profile changes in the susceptible cultivar than in the resistant counterpart. The metabolites that were differentially regulated in both cultivars were mostly lipids and lipid-like molecules. Significantly regulated metabolites and pathways according to the P value and variable important in projection score were identified. Moreover, four compounds, including ethyl α-D-thioglucopyranoside, imipenem, ginsenoside Rg1, and 6-gingerol, were selected, and their anti-P. brassicae ability and effects on seedling growth were verified on the susceptible cultivar. Except for ethyl α-D-thioglucopyranoside, the remaining could inhibit clubroot development of varing degree. The use of 5 mg/L ginsenoside Rg1 + 5 mg/L 6-gingerol resulted in the lowest disease incidence and disease index among all treatments and enhanced seedling growth. The regulation of pathways or metabolites of carbapenem and ginsenoside was further explored. The results provide a preliminary understanding of the interaction between radish and P. brassicae at the metabolism level, as well as the development of measures for preventing clubroot.
The existence of ' ‘N-acetyl-3-indolylmethylglucosinolate in young seedlings of Tovaria pendula Ruiz et Pav. has been proven by HPLC and mass-spectrometric methods. This compound is accompanied by 4-hydroxy-glucobrassicin, glucobrassicin, 4-methoxy-glucobrassicin and neo-glucobrassicin (' ‘N-methoxy-glucobrassicin).
The myrosinase-glucosinolate system is involved in a range of biological activities affecting herbivorous insects, plants and fungi. The system characteristic of the order Capparales includes sulphur-containing substrates, the degradative enzymes myrosinases, and cofactors. The enzyme-catalyzed hydrolysis of glucosinolates initially involves cleavage of the thioglucoside linkage, yielding D-glucose and an unstable thiohydroximate-Ο-sulphonate that spontaneously rearranges, resulting in the production of sulphate and one of a wide range of possible reaction products. The products are generally a thiocyanate, isothiocyanate or nitrile, depending on factors such as substrate, pH or availability of ferrous ions. Glucosinolates in crucifers exemplify components that are often present in food and feed plants and are a major problem in the utilization of products from the plants. Toxic degradation products restrict the use of cultivated plants, e.g. those belonging to the Brassicaceae. The myrosinase-glucosinolate system may, however, have several functions in the plant. The glucosinolate degradation products are involved in defence against insects and phytopathogens, and potentially in sulphur and nitrogen metabolism and growth regulation. The compartmentalization of the components of the myrosinase-glucosinolate system and the cell-specific expression of the myrosinase represents a unique plant defence system. In this review, we summarize earlier results and discuss the organisation and biochemistry of the myrosinase-glucosinolate system.
The U.S. Clean Air Act bans the use of methyl bromide after 2005. Consequently, the development of alternative methods for control of soilborne pathogens is imperative. One alternative is to exploit the pesticidal properties of Brassica L. species. Macerated leaves (10 g) from 'Premium Crop' broccoli [B. oleracea L. (Botrytis Group)], 'Charmant' cabbage [B. oleracea L. (Capitata Group)], 'Michihili Jade Pagoda' Chinese cabbage [B. rapa L. (Pekinensis Group)], 'Blue Scotch Curled' kale [B. oleracea L. (Acephala Group)], Indian mustard [B. juncea (L.) Czerniak, unknown cultivar] or 'Florida Broadleaf' mustard [B. juncea (L.) Czerniak] were placed in 500-mL glass jars. Petri dishes with either Pythium ultimum Trow or Rhizoctonia solani Kuhn plugs on potato-dextrose agar were placed over the jar mouths. Radial growth of both fungi was suppressed most by Indian mustard. Volatiles were collected by solid-phase microextraction (SPME) and analyzed by gas chromatography-mass spectrometry. Allyl isothiocyanate (AITC) comprised >90% of the volatiles measured from 'Florida Broadleaf' mustard and Indian mustard whereas (Z)-3-hexenyl acetate was the predominant compound emitted by the other species. Isothiocyanates were not detected by SPME from 'Premium Crop' broccoli and 'Blue Scotch Curled' kale although glucosinolates were found in freeze-dried leaves of all species. When exposed to AITC standard, P. ultimum growth was partially suppressed by 1.1 μmol · L-1 (μmol AITC/headspace volume) and completely suppressed by 2.2 μmol · L-1 R. solani was partially suppressed by 1.1, 2.2, and 3.3 μmol · L-1 AITC. Use of Brassica species for control of fungal pathogens is promising; the presence of AITC in both lines of B. juncea suppressed P. ultimum and R. solani but some Brassicas were inhibitory even when isothiocyanates were not detected.
The glucosinolates are a large group of sulphur-containing compounds which occur in all the economically important varieties of Brassica vegetable. Their common structure comprises a beta-D-thioglucose group, a sulphonated oxime moiety and a variable side-chain derived from methionine, tryptophan or phenylalanine. When the plant tissue is damaged the glucosinolates are hydrolysed by the endogenous enzyme 'myrosinase' (thioglucoside glycohydrolase EC 3:2:3:1), to release a range of breakdown products including the bitter, biologically active isothiocyanates. Although these compounds exert antinutritional effects in animals there is also substantial evidence that they are the principal source of anticarcinogenic activity in Brassica vegetables, and this provides a strong motive for the manipulation of glucosinolate levels in vegetables for human consumption. This review provides an overview of the evidence for a beneficial role for glucosinolates in human health, and describes the current state of knowledge regarding the genetics and biosynthesis of glucosinolates, their chemical analysis, their behaviour during cooking and processing, and their bioavailability to humans. As the genetic basis of glucosinolate biosynthesis becomes more apparent, and tools for marker-assisted plant breeding become more available, the selective breeding of horticultural brassicas with different levels and types of glucosinolates, whether by conventional means or genetic manipulation, is becoming a practical possibility. However before this strategy becomes commercially viable, the health benefits of glucosinolates for human beings must be unequivocally established. (C) 2000 Society of Chemical Industry.
Specialist Periodical Reports provide systematic and detailed review coverage of progress in the major areas of chemical research. Written by experts in their specialist fields the series creates a unique service for the active research chemist, supplying regular critical in-depth accounts of progress in particular areas of chemistry. For over 80 years the Royal Society of Chemistry and its predecessor, the Chemical Society, have been publishing reports charting developments in chemistry, which originally took the form of Annual Reports. However, by 1967 the whole spectrum of chemistry could no longer be contained within one volume and the series Specialist Periodical Reports was born. The Annual Reports themselves still existed but were divided into two, and subsequently three, volumes covering Inorganic, Organic and Physical Chemistry. For more general coverage of the highlights in chemistry they remain a 'must'. Since that time the SPR series has altered according to the fluctuating degree of activity in various fields of chemistry. Some titles have remained unchanged, while others have altered their emphasis along with their titles; some have been combined under a new name whereas others have had to be discontinued.
The occurrence and distribution of myrosinases in different plant organs in several species of Brassicaceae (Brassica chinensis, B. napus L., B. oleracea L., Iberis amara L., Iberis amara var. coronaria, Lepidium sativum L., Raphanus sativus L. and Sinapis alba L.) was studied. Myrosinase solutions were prepared from roots, stems, leaves, callus cultures and protoplasts and after dialysis the enzymatic activity was detected after hydrolytic cleavage of sinigrin. Specific activity was calculated in relation to protein, and it was found to vary within the range of 0.490 to 0.010 ,µmol · min-1 · mg-1 in 1 to 2 day old seedlings. The activity was found to decrease throughout the development of the plant but even at the flowering stage myrosinase activity could be detected.
The Brassicaceae (syn. Cruciferae) is an economically important botanical family providing a diverse range of foliar, root and seed crops for both human and domesticated animal consumption. However, in common with other plant species the Brassicacae have been endowed with the capacity to synthesize a range of antinutritional compounds, the most important of which are the glucosinolates, S-methylcysteine sulfoxide, tannins and erucic acid. In this review the adverse and possible beneficial effects of the inclusion of these compounds in human and animal diets are reviewed together with their chemistry, biosynthesis and methods for their analysis.
A method was developed for the quantitative determination of rapeseed glucosinolates as the desulfo derivatives, using liquid chromatography. Glucosinolates were desulfated at 37°C with the enzyme aryl sulfatase in Tris buffer, pH 8.0. All glucosinolates present in rapeseed were separated in 30 min on a Waters C18 Z-module using an acetonitrile gradient at 4 mL/min. Recoveries of benzyl, 4-hydroxybenzyl, and allylglucosinolates added to plant extracts were quantitative.
The following chapter presents an up-to-date account of the rapidly expanding knowledge of a group of naturally occurring glycosides undergoing enzymic hydrolysis to isothiocyanates (mustard oils), glucose and sulfate ions.
Enzymatic hydrolysis of glucosinolates, a class of compounds found in Brassica species, results in a number of products with potential to inhibit seed germination. To investigate the impact of both volatile and water soluble allelochemicals, germination bioassays were conducted with Lactuca sativa seeds in the presence of defatted seed meal of Brassica napus. Seed meal in which glucosinolates were hydrolyzed to remove volatile glucosinolate degradation products was compared with intact seed meal and water controls. Only tissues containing glucosinolates produced volatiles that inhibited germination. Biologically active volatiles were identified by GC-MS as isothiocyanates and nitriles, products of glucosinolate hydrolysis. Water-soluble components also inhibited germination, with analysis confirming the presence of nonvolatile products of glucosinolate hydrolysis. The results suggest that allelochemical control of germination with glucosinolate-containing plants may contribute to reductions in synthetic pesticide usage if weed seeds are targeted.
The glucosinolate-thioglucosidase system potentially generates hundreds of compounds, but knowledge of autolysis conditions permits prediction of the products. How these products are generated, how their precursors are distributed and compartmentalized, and how these products affect herbivorous insects, pathogens, other plants, and potential symbionts are examined.
Emergence of snap beans (Phaseolus vulgaris L.) in field soil in 1995 to 1997 was reduced by the addition of dried, ground canola [Brassica napus L. ssp. oleifera (Metzg.) Sinsk. f. biennis] leaves and petioles to the furrow at planting. Soil amendment with the tissue increased the number of nodules on bean roots in all years. In plots with reduced stand, leaf area was increased and yield on a per-plant basis was larger than in plots with a better stand. Total yield was increased in plots with fewer plants only in 1995. Frequency of isolation of fungi that cause damping-off was not affected by the addition of canola at planting. When used as a seed treatment and incorporated at planting, canola residues were detrimental to emergence of snap bean.
A number of studies suggest a protective role of cruciferous vegetables in colon cancer risk. We conducted meta-analyses on the twenty published epidemiological studies which we could identify that contained information on the relationship of consumption of the cabbage or vegetables of the Brassica genus to the incidence of colon or rectal cancer or their precursors. Most of these studies were conducted to examine relationships between fiber and colon cancer, which reduces the risk of publication bias. Differences in the design and exposure assessment among the studies was accounted for in a deductive analysis of alternative hypothesis with general variance-based, homogeneity testing and meta-regression methods. A general protective effect of cruciferous vegetables on colorectal cancer was found. The odds ratio of the meta-analysis equaled 0.94 (95% CI = 0.92, 0.96) for every 4.3 grams/day intake of cruciferae (weighted mean intake of studies). Meta-regression models based on linear regression were used to estimate the effect across reported cruciferae consumption levels and studies. The crude model suggested highly protective effect of cruciferous vegetable and total vegetable on colorectal cancer with OR of 0.91 (CI = 0.90, 0.94) and 0.90 (CI = 0.86, 0.93), respectively, for each 10 gram of consumption per day. The effect was OR=0.91 per 10 gram of cruciferae consumed for colon cancer and 0.95 for rectal cancer (both were significant at α=0.05). To discriminate a cruciferous vegetable effect from the effect of greater consumption of vegetables in general, we modeled the residual cruciferae intake along with the frequency of total vegetable intake. A marginally significant protective effect (p=0.053) remained for the association to colorectal cancer with OR equal to 0.95 (CI=0.91, 1.00) for each 10 grams/day of cruciferae consumed. These findings suggest that even infrequent consumption of cruciferous vegetables provides protection against colon cancer in man.
Glucosinolates were detected as their aglycones in cell suspension cultures of two of seven plant species known to contain glucosinolates. 2-Phenylethyl-glucosinolate and 2-hydroxy-2-phenylethylglucosinolate were present in cell cultures of Reseda luteola and benzylglucosinolate was found in Tropaeolum majus cultures. The glucosinolate-hydrolyzing enzyme, myrosinase (E.C. 3.2.3.1), was detected in all seven cultures. Although no glucosinolates were detected in cultures of Sinapis alba, retention, in part, of biosynthetic capability was demonstrated by the occurrence of a glucosyltransferase associated with glucosinolate biosynthesis. It is suggested that plant tissue cultures may be of potential value for further study of glucosinolate biosynthesis.
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Broccoli (Brassica oleracea L., Italica Group) has been recognized as a source of glucosinolates and their isothiocyanate metabolites that may be chemoprotective against human cancer. A predominant glucosinolate of broccoli is glucoraphanin and its cognate isothiocyanate is sulforaphane. Sulforaphane has been shown to be a potent inducer of mammalian detoxication (Phase 2) enzyme activity and to inhibit chemical-induced tumorigenesis in animal models. Little is known about phenotypic variation in broccoli germplasm for Phase 2 enzyme (e.g., quinone reductase) induction potential. Thus, this study was undertaken to evaluate: 1) quinone reductase induction potential (QRIP) diversity among a population of broccoli inbreds; 2) QRIP levels in selected lines; 3) correlation of QRIP with other horticultural characteristics; and 4) QRIP expression in a sample of synthesized hybrids. In 1996, 71 inbreds and five hybrid checks (all field-grown), ranged from a QRIP of nearly zero to 150,000 units/g fresh weight (FW) (mean of 34,020 units/g FW). These values were highly correlated with methylsulphinylalkyl glucosinolate (MSAG; primarily glucoraphanin) concentrations that ranged from 0.04 to 2.94 μmol·g-1 FW. A select subset of lines evaluated in 1996 were reevaluated in 1997. QRIP and MSAG values in this second year were similar to and correlated with those observed in 1996 (r = 0.73, P < 0.0001 and r = 0.79, P < 0.0001, respectively). In addition, both QRIP and MSAG concentration were highly correlated with days from transplant to harvest. Average F1 hybrid values for QRIP and MSAG in 1997 fell typically between their parental means, but were often closer to the mean of the low parent. Results of this study indicate that divergent QRIP expression can effectively be used to select enhanced inbred lines to use in development of value-added hybrids. Evidence is also provided that there is a significant genetic component to both QRIP and MSAG concentration, and that selection for either one may provide an effective means for developing broccoli hybrids with enhanced chemoprotective attributes. Chemical names used: 4-methylsulphinylbutyl glucosinolate (glucoraphanin) and 4-methylsulphinylbutyl isothiocyanate (sulforaphane).
Isolation of intact glucosinolates requires knowledge of their occurrence, structures and properties.Of equal importance is knowledge of instrumentation, structures and properties of column materials required as well as knowledge of occurrence, structures and properties of co-occurring natural products, including the myrosinases (Thioglucoside glucohydrolase, EC 3.2. 3.1). The purposes of glucosinolate isolation can be quite different. This can be isolation of small amounts on mini-columns for quantitative methods of analysis, isolation of pure reference compounds, isolation and identification of new compounds, and finally, isolation of appreciable amounts for feeding trials or other special purposes. Thereby, differences between recommendable techniques exist and need to be considered. It is important to realize that it is nearly impossible to obtain 100% pure glucosinolates. For several reasons, including possibilities for performance of reliable quantitative methods of analysis, the exact and actual purity of the glucosinolates must be determined. Therefore, we need to consider the limitations and possibilities of different methods suitable for determination of purity of isolated glucosinolates. The data obtained in our laboratory show that it is recommendable to use several, of each other independent, methods. This paper comprises a brief discussion and presentation of recent advances within the above mentioned points of interest in relation to glucosinolate isolation and methods required for determinations of their purity.
Myrosinase in cell-free extract of Enterobacter cloacae, no. 506, was purified about 1, 000 fold by precipitation with ammonium sulfate, chromatography on CM-Sephadex and gelfiltration on Sephadex G-200 and Sephadex G-100. The enzyme was shown to be homogeneous by chromatography and by ultracentrifuge. Molecular weight obtained by gelfiltration was 61, 000 and the sedimentation coefficient was 4.5S. Maximum activity occurred at pH 6.8. The enzyme was stable in a pH range of 5.0 to 7.0 at temperature below 40°C and for 24 hr. Copper(I) and (II), mercury (II) and ferrous(II) ions strongly inhibited the activity. Sulfhydryl reagents had little effect but EDTA was a strong inhibitor. In contrast to plant myrosinase, this enzyme was inhibited by L-ascorbic acid. Many glucosides and sugars inhibited the enzyme. The relation between bacterial myrosinase and β-glucosidase is discussed in comparison to plant and fungous myrosinases. Some comparative properties of bacterial, fungous and plant myrosinases are discussed.
Stability of 4-methylthio-3-butenyl isothiocyanate (MTBI) was studied in an aqueous medium. Most of (E)-MTBI was degraded within 3h by shaking or sonicating and within 6h on an agar plate. (Z)MTBI was more stable. Antimicrobial activity of MTBI on 8 bacteria, 3 yeasts, and 5 fungi was estimated in a gaseous phase. The growth of fungi were strongly inhibited by MTBI in the dose range 2.5-7.5 μmol/ plate. The fact that the maximum amount of MTBI in head space was only 0.2% of the dose suggested that the antimicrobial activity of MTBI was very high.
Four proteins (F-IA, B, F-IIA & F-IIB), having myrosinase activity, were separated and purified from mustard powder. Each enzyme was shown to be homogeneous chromatographically, ultracentrifugally and Disc electrophoretically. Molecular weights obtained by gel-filtration and sedimentation equilibrium were 153, 000 (F-IA, F-I B & F-IIA) and 125, 000 (F-IIB). Sedimentation coefficients were 6.8S (F-IA, B & F-IIA) and 5.8S (F-11B). Stokes radius (Å), diffusion coefficient (cm2/sec) and frictional ratio (f/fo) were 47, 4.28×10-7 and 1.33 (F-IA, B & F-III), and 43, 4.67×10-7 and 1.29 (FIIB), respectively. Isoelectric points were pH 4.6 (F-IA, B & F-IIA) and pH 4.8 (F-IIA). The enzymes were glycoprotein with 9_??_22% carbohydrate. Amino acid composition of F-IA, Band F-IIA were very similar, but in case of F-IIB, glutamic acid, arginine and methionine contents were higher and aspartic acid and histidine contents were lower than others. The molecular weights estimated from SDS-polyacrylamide gel electrophoresis were 40, 000 (F-IA, B & F-IIA) and 30, 000 (F-IIB), respectively, and hence the enzymes are considered to have at least 4 subunits. From these results, it may be confirmed that F-IA, B & F-IIA have striking resemblances and only F-IIB is rather different.