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At least 19 recordsLinked to original sources
PubMed2002

Benzoic acid glucosinolate esters and other glucosinolates from Arabidopsis thaliana.

The spectacular recent progress in Arabidopsis thaliana molecular genetics furnishes outstanding tools for studying the formation and function of all metabolites in this cruciferous species. One of the major groups of secondary metabolites in A. thaliana is the glucosinolates. These hydrophilic, sulfur-rich glycosides appear to serve as defenses against some generalist herbivores and pathogens, and as feeding and oviposition stimulants to specialist herbivores. To help study their biosynthesis and role in plant-insect interactions, we wanted to determine the complete glucosinolate content of A. thaliana. In previous studies, 24 glucosinolates had been identified from ecotype Columbia. We reinvestigated Columbia as well as additional ecotypes and mutant lines, and identified 12 further glucosinolates, including five novel compounds. Structures were elucidated by MS and NMR spectroscopy of their desulfated derivatives, and by enzymatic cleavage of the attached ester moieties. Four of the novel glucosinolates are benzoate esters isolated from the seeds. In all but one of these compounds, esterification is on the glucose moiety rather than the side chain, a very unusual feature for glucosinolates. Among additional glucosinolates identified were the first non-chain elongated, methionine-derived glucosinolate from A. thaliana and the first compounds that appear to be derived from leucine.

Arabidopsis↗
PubMed1995

Dietary glucosinolates as blocking agents against carcinogenesis: glucosinolate breakdown products assessed by induction of quinone reductase activity in murine hepa1c1c7 cells.

We have tested the ability of a representative range of dietary glucosinolates and their breakdown products, found in high concentrations in cruciferous vegetables, to act as blocking agents against carcinogenesis by inducing the activity of the anticarcinogenic phase II marker enzyme quinone reductase in murine hepa1c1c7 cells. Breakdown of glucosinolates was catalysed by the endogenous plant enzyme thioglucoside glucohydrolase at neutral and acid pH. Only two unmodified glucosinolates, p-hydroxybenzyl and 2-hydroxybut-3-enyl, significantly induced quinone reductase activity. However, after enzymic hydrolysis at near-neutral pH, some of the glucosinolates yielded breakdown products that significantly induced quinone reductase in the order: 3-methylsulphinylpropyl-->prop-2-enyl-->pent-4-enyl approximately 2-phenylethyl approximately benzyl-->all others tested. Incubation with myrosinase at acidic pH resulted in induction of quinone reductase activity by the hydrolysis products of only three of the tested glucosinolates:3-methylsulphinyl-propyl approximately 2-phenylethyl-->benzyl-->all others, activity due to the two alkenyl compounds being lost. The results show that the potential cancer-blocking action of both intact and thioglucoside glucohydrolase-treated glucosinolates, as assessed by induction of phase II enzyme activity, is dependent on the nature of the side chain of the parent glucosinolate.

Animals↗
PubMed2002

Effects of intact glucosinolates and products produced from glucosinolates in myrosinase-catalyzed hydrolysis on the potato cyst nematode (Globodera rostochiensis Cv. Woll).

The potato cyst nematode (Globodera rostochiensis cv. Woll) is responsible for large yield losses in the potato crop, and opportunities for reducing the attack of these plant nematode species are, therefore, important. This study has been devoted to the testing of the in vitro effects on the potato cyst nematode of eight glucosinolates [prop-2-enyl-, but-3-enyl-, (R)-4-methylsulfinylbut-3-enyl-, benzyl-, phenethyl-, 4-hydroxybenzyl-, (2S)-2-hydroxybut-3-enyl-, and (2R)-2-hydroxy-2-phenylethylglucosinolate] as well as the effects of the products of this myrosinase-catalyzed hydrolysis. The glucosinolates were used at three concentrations, 0.05, 0.3, and 1.0 mg/mL, in the presence or absence of the enzyme myrosinase. The effects of the compounds on the mortality were monitored every 8 h for a 72 h period. No effects were found for any of the intact glucosinolates. However, when active myrosinase was included with 1 mg/mL phenethylglucosinolate at pH 6.5, 100% mortality was observed within just 16 h. A similar effect was achieved at the same concentration of benzyl- and prop-2-enylglucosinolates in the myrosinase-containing solutions, although longer exposures were required (24 and 40 h, respectively). The main aglucone products released from the glucosinolates with pronounced effects on the nematodes were shown to be the corresponding isothiocyanates. The results suggest that mixtures of these specific glucosinolates and active myrosinase or autolysis of plant materials containing these enzymes and glucosinolates might be used to control the potato cyst nematode in the soil.

Animals↗
PubMed1998

The presence of CYP79 homologues in glucosinolate-producing plants shows evolutionary conservation of the enzymes in the conversion of amino acid to aldoxime in the biosynthesis of cyanogenic glucosides and glucosinolates.

A cDNA encoding CYP79B1 has been isolated from Sinapis alba. CYP79B1 from S. alba shows 54% sequence identity and 73% similarity to sorghum CYP79A1 and 95% sequence identity to the Arabidopsis T42902, assigned CYP79B2. The high identity and similarity to sorghum CYP79A1, which catalyses the conversion of tyrosine to p-hydroxyphenylacetaldoxime in the biosynthesis of the cyanogenic glucoside dhurrin, suggests that CYP79B1 similarly catalyses the conversion of amino acid(s) to aldoxime(s) in the biosynthesis of glucosinolates. Within the highly conserved 'PERF' and the heme-binding region of A-type cytochromes, the CYP79 family has unique substitutions that define the family-specific consensus sequences of FXP(E/D)RH and SFSTG(K/R)RGC(A/I)A, respectively. Sequence analysis of PCR products generated with CYP79B subfamily-specific primers identified CYP79B homologues in Tropaeolum majus, Carica papaya, Arabidopsis, Brassica napus and S. alba. The five glucosinolate-producing plants identified a CYP79B amino acid consensus sequence KPERHLNECSEVTLTENDLRFISFSTGKRGC. The unique substitutions in the 'PERF' and the heme-binding domain and the high sequence identity and similarity of CYP79B1, CYP79B2 and CYP79A1, together with the isolation of CYP79B homologues in the distantly related Tropaeolaceae, Caricaceae and Brassicaceae within the Capparales order, show that the initial part of the biosynthetic pathway of glucosinolates and cyanogenic glucosides is catalysed by evolutionarily conserved cytochromes P450. This confirms that the appearance of glucosinolates in Capparales is based on a cyanogen 'predisposition'. Identification of CYP79 homologues in glucosinolate-producing plants provides an important tool for tissue-specific regulation of the level of glucosinolates to improve nutritional value and pest resistance.

Amino Acid Sequence↗
PubMed1999

Indole glucosinolate and auxin biosynthesis in Arabidopsis thaliana (L.) Heynh. glucosinolate mutants and the development of clubroot disease.

Mutants and wild type plants of Arabidopsis thaliana were analysed for differences in glucosinolate accumulation patterns, indole-3-acetic acid (IAA) biosynthesis and phenotype. A previously identified series of mutants, termed TU, with altered glucosinolate patterns was used in this study. Only the line TU8 was affected in shoot phenotype (shorter stems, altered branching pattern). Synthesis of IAA and metabolism were not much affected in the TU8 mutant during seedling development, although the content of free IAA peaked earlier in TU8 during plant development than in the wild type. Indole glucosinolates and IAA may, however, be involved in the development of clubroot disease caused by the obligate biotrophic fungus Plasmodiophora brassicae since the TU3 line had a lower infection rate than the wild type, and lines TU3 and TU8 showed decreased symptom development. The decline in clubroot formation was accompanied by a reduced number of fungal structures within the root cortex and slower development of the fungus. Indole glucosinolates were lower in infected roots of TU3 and TU8 than in control roots of these lines, whereas in wild-type plants the differences were not as prominent. Free IAA and indole-3-acetonitrile (IAN) were increased in infected roots of the wild type and mutants with normal clubroot symptoms, whereas they were reduced in infected roots of mutants TU3 and TU8. These results indicate a role for indole glucosinolates and IAN/IAA in relation to symptom development in clubroot disease.

Arabidopsis↗
PubMed1977

Glucosinolates and derived products in cruciferous vegetables: total glucosinolates by retention on anion exchange resin and enzymatic hydrolysis to measure released glucose.

Details are given for determining total glucosinolates in Cruciferae plants by a procedure measuring released glucose. The glucosinolates are separated from about 90% of other material in the plant extract by adsorption on an anion exchange resin. Then, by a selective thioglucosidase hydrolysis of the glucosinolates retained on the exchange resin, the glucose and aglucons are separated from other substances retained by the resin. Glucose is released into an aqueous medium and is equivalent to the total glucosinolates. The aglucons formed by the hydrolysis are extracted into methylene chloride and determined by gas-liquid chromatography. Based on 29 determinations of the glucose from sinigrin, analyzed under different conditions, accuracy of the total glucosinolate determination was 94.8 +/- 7.3%. The coefficient of variation, determined by duplicate analyses on extracts from 58 cabbage samples, was 4.6%.

Anion Exchange Resins↗
PubMed1987

Differential induction of mixed-function oxidase (MFO) activity in rat liver and intestine by diets containing processed cabbage: correlation with cabbage levels of glucosinolates and glucosinolate hydrolysis products.

Both white and Savoy-type cabbage added to a semi-purified diet at 25% dry weight and fed to rats ad lib. for 5 days significantly induced ethoxyresorufin (ERR) deethylation in the small and large intestine. Savoy cabbage also induced hepatic activity and, in general, exhibited a greater inducing effect than white cabbage. These enzyme-inducing effects were altered when the cabbage had been processed. The content of intact glucosinolate was greater in Savoy than in white cabbage. The indole glucosinolate (glucobrassicin) content of both types of cabbage was approximately halved by cooking but was unaffected by fermentation, whilst homogenization of Savoy cabbage led to the total disappearance of intact glucosinolates. Levels of the indole glucosinolate breakdown products ascorbigen and indole-3-carbinol were highest in homogenized cabbage, and ascorbigen levels were also higher in cooked than in fresh cabbage of either type. When added to the semi-purified diet and fed ad lib. to rats for 5 days, indole-3-carbinol was a potent inducer of hepatic ERR deethylation and cytochrome P-450 activity, but had much less effect in the intestine. Other glucobrassicin metabolites, diindolylmethane and indole-3-acetonitrile, also had some inducing effect in the liver but no effect in the intestine, while ascorbigen significantly induced ERR deethylation in the small and large intestine but had no effect on hepatic MFO activity.

Animals↗
PubMed2006

Changes in glucosinolate concentrations, myrosinase activity, and production of metabolites of glucosinolates in cabbage (Brassica oleracea Var. capitata) cooked for different durations.

In cabbage, glucosinolates such as sinigrin are hydrolyzed by plant myrosinase to allyl isothiocyanate (AITC), allyl cyanide, and, in the presence of an epithiospecifier protein, 1-cyano-2,3-epithiopropane (CEP). Isothiocyanates have been implicated in the cancer-protective effects of Brassica vegetables. The effect of processing on the hydrolysis of glucosinolates was investigated in cabbage. Cabbage was steamed or microwaved for six time durations over 7 min. Glucosinolate concentrations were slightly reduced after microwave cooking (P < 0.001) but were not influenced after steaming (P < 0.05). Myrosinase activity was effectively lost after 2 min of microwave cooking and after 7 min of steaming. Hydrolysis of residual glucosinolates following cooking yielded predominantly CEP at short cooking durations and AITC at longer durations until myrosinase activity was lost. Lightly cooked cabbage produced the highest yield of AITC on hydrolysis in vitro, suggesting that cooking Brassica vegetables for a relatively short duration may be desirable from a health perspective.

Brassica↗
PubMed1994

Isolation of glucosinolate degrading microorganisms and their potential for reducing the glucosinolate content of rapemeal.

A range of microorganisms were assessed for their ability to degrade glucosinolates, using sinigrin (2-propenyl glucosinolate) as a model compound. Eight different species capable of growing on sinigrin as a sole carbon source were isolated. These were predominantly Gram-positive bacteria which also degraded the natural glucosinolates within rapemeal. Growth of the majority of these organisms in a sinigrin/glucose liquid medium wass biphasic; glucose was utilised during the initial rapid phase of growth. The ability to degrade sinigrin was found to be unstable and was rapidly and irreversibly lost when organisms were cultured on sinigrin-free media.

Animal Feed↗
PubMed1993

Rapeseed meal-glucosinolates and their antinutritional effects. Part 1. Rapeseed production and chemistry of glucosinolates.

This review, which will be presented in seven parts is concerned with the use of rapeseed meal as an animal feeding stuff. The presence of glucosinolates in the meal limits its use due to a number of antinutritional and physiological effects. Whilst not in itself exhaustive, this review updates earlier reviews by reference to recent papers on the above topics. In this first paper the history of the crop and the current production situation are presented and the nature of glucosinolates and methods for their analysis are reviewed in order to facilitate a better appreciation of the problems referred in later sections.

Animal Feed↗
PubMedDate not supplied

A new approach to the study of glucosinolates by isocratic liquid chromatography. Part I. Rapid determination of desulfated derivatives of rapeseed glucosinolates.

Liquid chromatographic (LC) analysis of desulfated derivatives of rapeseed glucosinolates has been carried out under isocratic elution conditions with different CN-bonded stationary phases. The effects of the eluant composition (water, acetonitrile, and methanol) with the stationary phase (Zorbax CN, Lichrospher CN, and Ultrasphere CN) and temperature (20 and 50 degrees C) are described. An isocratic LC method performed at room temperature using a Lichrospher CN column and water as mobile phase is proposed. The chromatographic analysis can be done in less than 12 min, and it is easier and less expensive than the traditional gradient mode. Four commercial samples of rapeseed containing various quantities of other cruciferous seeds (wild mustard and stinkweed) as an admixture have been analyzed to determine the total glucosinolate content. Relative standard deviations of repeatability of the isocratic and gradient LC methods ranged from 0.4 to 1.7% and from 2.7 to 4.7%, respectively. Comparison of the results showed good agreement between the 2 methods (beter than 98%).

Acetonitriles↗
PubMed2002

Identification of the major glucosinolate (4-mercaptobutyl glucosinolate) in leaves of Eruca sativa L. (salad rocket).

The major and structurally unique glucosinolate (GLS) in leaves of Eruca sativa L. (salad rocket) was identified as 4-mercaptobutyl GLS. Both 4-methylthiobutyl GLS and 4-methylsulfinylbutyl GLS were also present, but at lower concentrations. The 4-mercaptobutyl GLS was observed to oxidise under common GLS extraction conditions, generating a disulfide GLS that may be reduced efficiently by tris(2-carboxyethyl) phosphine hydrochloride (TCEP) to reform the parent molecule. The identities of 4-mercaptobutyl GLS and of the corresponding dimeric GLS were confirmed by LC/MS, MS/MS and NMR. Myrosinase treatment of an enriched GLS fraction or of the purified dimer GLS generated a mixture of unique bi-functional disulfides, including bis-(4-isothiocyanatobutyl) disulfide (previously identified elsewhere). TCEP reduction of the purified dimer, followed by myrosinase treatment, yielded only 4-mercaptobutyl ITC. GLS-derived volatiles generated by autolysis of fresh seedlings and true leaves were 4-mercaptobutyl ITC (from the newly identified GLS), 4-methylthiobutyl ITC (from 4-methylthiobutyl GLS) and 4-methylsulfinylbutyl ITC (from 4-methylsulfinyl-butyl GLS); no unusual bi-functional disulfides were found in fresh leaf autolysate. These results led to the conclusion that, in planta, the new GLS must be present as 4-mercaptobutyl GLS and not as the disulfide found after extraction and sample concentration. This new GLS and its isothiocyanate are likely to contribute to the unique odour and flavour of E. sativa.

Brassicaceae↗
PubMed2006

Variation of glucosinolates in vegetable crops of Brassica rapa.

Glucosinolate levels in leaves were determined in a collection of 113 varieties of turnip greens (Brassica rapa L.) from northwestern Spain grown at two sites. Sensorial attributes were also assessed by a consumer panel. The objectives were to determine the diversity among varieties in total glucosinolate content and glucosinolate profile and to evaluate their sensory attributes in relation to glucosinolate content for breeding purposes. Sixteen glucosinolates were identified, being the aliphatic glucosinolates, gluconapin and glucobrassicanapin the most abundant. Other aliphatic glucosinolates, such as progoitrin, glucoalyssin, and gluconapoleiferin were relatively abundant in varieties with a different glucosinolate profile. Indolic and aromatic glucosinolate concentrations were low and showed few differences among varieties. Differences in total glucosinolate content, glucosinolate profile and bitterness were found among varieties, with a total glucosinolate content ranging from 11.8 to 74.0micromolg(-1) dw at one site and from 7.5 to 56.9micromolg(-1) dw at the other site. Sensory analysis comparing bitterness with variation in glucosinolate, gluconapin and glucobrassicanapin concentrations suggested that these compounds and their breakdown products are not the only determinants of the characteristic flavour of this vegetable. Other phytochemicals are probably involved on the characteristic bitter flavour. The varieties MBG-BRS0132, MBG-BRS0082, MBG-BRS0173, and MBG-BRS0184 could be good candidates for future breeding programs since they had high total glucosinolate content and good agronomic performance. The presence of glucoraphanin in some varieties should be studied more extensively, because this aliphatic glucosinolate is the precursor of sulforaphane, a potent anti-cancer isothiocyanate.

Brassica napus↗
PubMed2006

Gene expression and glucosinolate accumulation in Arabidopsis thaliana in response to generalist and specialist herbivores of different feeding guilds and the role of defense signaling pathways.

Glucosinolate accumulation and expression of glucosinolate biosynthetic genes were studied in response to four herbivores in Arabidopsis thaliana (L.) wild-type (Columbia) and mutant lines affected in defense signaling. Herbivory on wild-type plants led to increased aliphatic glucosinolate content for three of four herbivores tested, the aphid generalist Myzus persicae (Sulzer), the aphid specialist Brevicoryne brassicae (L.), and the lepidopteran generalist Spodoptera exigua Hübner. The lepidopteran specialist Pieris rapae L. did not alter aliphatic glucosinolate content in the wild-type, but indole glucosinolates increased slightly. Gene expression associated with aliphatic glucosinolate biosynthesis increased after feeding by all species, indicating that glucosinolate accumulation is not always regulated at the level of these gene transcripts. A. thaliana lines with mutations in jasmonate (coi1), salicylate (npr1), and ethylene signaling (etr1) diverged in gene expression, glucosinolate content, and insect performance compared to wild-type suggesting the involvement of all three modes of signaling in responses to herbivores. The coi1 mutant had much lower constitutive levels of aliphatic glucosinolates than wild-type but content increased in response to herbivory. In contrast, npr1 had higher constitutive levels of aliphatic glucosinolates and levels did not increase after feeding. Glucosinolate content of the etr1 mutant was comparable to wild-type and did not change with herbivory, except for P. rapae feeding which elicited elevated indolyl glucosinolate levels. Unlike the wild-type response, gene transcripts of aliphatic glucosinolate biosynthesis did not generally increase in the mutants. Both glucosinolate content and gene expression data indicate that salicylate and ethylene signaling repress some jasmonate-mediated responses to herbivory.

Animals↗
PubMed2004

Screening crucifer seeds as sources of specific intact glucosinolates using ion-pair high-performance liquid chromatography negative ion electrospray mass spectrometry.

Seeds, of either commercial crucifer crops or some wild and weed relatives, were screened for intact glucosinolates using a previously developed ion-pair LC-MS method. This method, in contrast to GC-MS techniques, ensures the accurate measurement of all classes of glucosinolates. Many crucifer seeds contained very high concentrations of glucosinolates with low concentrations of additional pigments and secondary metabolites. The other common seed metabolites were cinnamoylcholine esters, for example, sinapine. Glucosinolates derived from homologues of l-methionine were characteristic of Brassica and related crucifer species. In addition, significant concentrations of 4-hydroxy-3-indolylmethylglucosinolate were found in the majority of Brassica species. Wild and weed species often had relatively simple glucosinolate profiles: either a single glucosinolate or a predominant glucosinolate together with trace amounts of others. Species identified with seed glucosinolate profiles suitable for purification included various Alyssum, Erysimum, and Iberis species for 3-methythiopropyl-glucosinolate and 3-methylsulfinylpropyl-glucosinolate and various Alyssum, Erysimum, and Lepidium species with very high concentrations of C4-C6 aliphatic glucosinolates. Seeds of Arabis, Barbarea, Lepidium, Moringa, and Sinapis species were good sources of aromatic glucosinolates, and Azima tetracantha was a good source for N-methoxy-3-indolylmethyl-glucosinolate. MS data are reported for all of the intact glucosinolates detected from the screening process.

Brassicaceae↗
PubMed2004

Correlation of glucosinolate content to myrosinase activity in horseradish (Armoracia rusticana).

Fully developed horseradish (Armoracia rusticana Gaertn., Mey., & Scherb.) roots from 27 accessions and leaves from a subset of 9 accessions were evaluated for glucosinolates and myrosinase enzyme activity. Eight different glucosinolates were detected (based on HPLC retention times as desulfoglucosinolates) in both root and leaf tissues. The sum of these glucosinolates, referred to as total, ranged from 2 to 296 micromol g(-1) of dry weight (DW) in both tissues. Four glucosinolates (sinigrin, glucobrassicin, neoglucobrassicin, and gluconasturtiin) were detected in major quantities. In fully developed roots, sinigrin concentration represented approximately 83%, gluconasturtiin approximately 11%, and glucobrassicin approximately 1% of the total glucosinolates. Approximately the same proportions of individual glucosinolates appeared in fully developed leaves, except that glucobrassicin was substituted by neoglucobrassicin and gluconasturtiin concentration was significantly lower (<1%). At least four other glucosinolates were detected in very small quantities (<1%) in both roots and leaves. Myrosinase (beta-thioglucoside glucohydrolase, EC 3.2.3.1) is the enzyme responsible for the hydrolysis of the parent glucosinolates into biologically active products. Very little is known about myrosinase activity and the correlation of its activity to total and individual glucosinolates in plant tissues. Significant differences in myrosinase activity were detected between the roots and leaves, ranging from 1.2 to 57.1 units g(-1) of DW. Data showed no correlation between myrosinase activity and total and/or individual glucosinolates in the roots. However, in the leaves, significant correlations were found between myrosinase activity and total glucosinolates (0.78 at P = 0.01) and between myrosinase activity and sinigrin (0.80 at P = 0.01). Glucosinolates content and myrosinase activity were also correlated in young and fully developed roots and leaves and during tissue crushing. Glucobrassicin concentration in the roots and neoglucobrassicin concentration in the leaves were significantly higher in young than in fully developed tissue. Crushing of the tissue resulted in rapid hydrolysis of sinigrin and glucobrassicin, as expected, from the presence of myrosinase. Likewise, myrosinase activity declined rapidly after crushing, perhaps due to inactivation by the reaction products and/or the depletion of its substrates.

Armoracia↗