The glucosinolates sinigrin and progoitrin are important determinants for taste preference and bitterness of Brussels sprouts

Doorn, Hans E van; Kruk, G.C. van der; Holst, G J van; Raaijmakers-Ruijs, NC; Postma, Erik; Groeneweg, B.; Jongen, W.

doi:10.1002/(sici)1097-0010(199809)78:1<30::aid-jsfa79>3.0.co;2-n

Cited by 115 publications

(70 citation statements)

References 4 publications

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“…While some enzyme reactions lead to a racemic mixture of products, it is unusual to find a reaction that yields a mixture of two enantiomers in a fixed, nonequivalent ratio. In con-trast, Brassica napus and Arabis alpina make only the 2R enantiomer of 2-hydroxybut-3-enyl glucosinolate, while Crambe abyssinica makes only the 2S enantiomer (Daubos et al, 1998;van Doorn et al, 1998). The lack of stereospecificity in Arabidopsis could result from the fact that the enzyme has evolutionarily lost the ability to form a single enantiomer.…”

Section: Stereoselectivity Of the 2-hydroxylasementioning

confidence: 99%

“…This glucosinolate arises by oxidation of 3-butenyl glucosinolate to produce either the 2R-or 2S-hydroxylated derivative (Rossiter et al, 1990;Daubos et al, 1998). Arabidopsis contains both the 2R and 2S enantiomers of 2-hydroxybut-3-enyl glucosinolate, whereas Brassica napus makes only the 2R enantiomer and Crambe abyssinica makes only the 2S enantiomer (Daubos et al, 1998;van Doorn et al, 1998). This suggests that there may be enzymatic differences in the production of 2-hydroxybut-3-enyl glucosinolate among different plant species.…”

mentioning

confidence: 99%

“…It is toxic to insects, bacteria, and nematodes, inhibits the germination of various plant species, and is a major source of bitter flavor in Brassica vegetables (Donkin et al, 1995;Angelini et al, 1998;van Doorn et al, 1998;Manici et al, 2000;Peterson et al, 2000). In addition, upon tissue disruption, 2-hydroxybut-3-enyl glucosinolate can be hydrolyzed to form an oxazolidine-2-thione derivative (goitrin), a compound that causes goiter disease in mammals and is a major impediment to the use of Brassica crops as cattle feed (Greer, 1956;Greer and Deeney, 1959;Pearson et al, 1983).…”

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confidence: 99%

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A Novel 2-Oxoacid-Dependent Dioxygenase Involved in the Formation of the Goiterogenic 2-Hydroxybut-3-enyl Glucosinolate and Generalist Insect Resistance in Arabidopsis

et al. 2008

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Glucosinolates are secondary metabolites found almost exclusively in the order Brassicales. They are synthesized from a variety of amino acids and can have numerous side chain modifications that control biological function. We investigated the biosynthesis of 2-hydroxybut-3-enyl glucosinolate, which has biological activities including toxicity to Caenorhabditis elegans, inhibition of seed germination, induction of goiter disease in mammals, and production of bitter flavors in Brassica vegetable crops. Arabidopsis (Arabidopsis thaliana) accessions contain three different patterns of 2-hydroxybut-3-enyl glucosinolate accumulation (present in leaves and seeds, seeds only, or absent) corresponding to three different alleles at a single locus, GSL-OH. Fine-scale mapping of the GSL-OH locus identified a 2-oxoacid-dependent dioxygenase encoded by At2g25450 required for the formation of both 2R-and 2S-2-hydroxybut-3-enyl glucosinolate from the precursor 3-butenyl glucosinolate precursor. Naturally occurring null mutations and T-DNA insertional mutations in At2g25450 exhibit a complete absence of 2-hydroxybut-3-enyl glucosinolate accumulation. Analysis of herbivory by the generalist lepidopteran Trichoplusia ni showed that production of 2-hydroxybut-3-enyl glucosinolate provides increased resistance. These results show that At2g25450 is necessary for the hydroxylation of but-3-enyl glucosinolate to 2-hydroxybut-3-enyl glucosinolate in planta and that this metabolite increases resistance to generalist herbivory.

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Section: Stereoselectivity Of the 2-hydroxylasementioning

confidence: 99%

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confidence: 99%

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confidence: 99%

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A Novel 2-Oxoacid-Dependent Dioxygenase Involved in the Formation of the Goiterogenic 2-Hydroxybut-3-enyl Glucosinolate and Generalist Insect Resistance in Arabidopsis

et al. 2008

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“…In addition, the breakdown products of GSLs contribute to the unique flavor and fragrance of Brassicaceae vegetables (Van Doorn et al, 1998;Macleod, 1976), and also act in plant defense mechanisms due to their significant physiological activities (Grubb and Abel, 2006 Table 3). In general, Chinese cabbage is distributed after storage at 4-8°C, and its nutrient content (including its GSL content)…”

Section: Changes In Gsl Levels In Chinese Cabbagementioning

confidence: 99%

Physicochemical Quality Changes in Chinese Cabbage with Storage Period and Temperature: A Review

Shim¹,

Kim²,

Park³

et al. 2016

Journal of Biosystems Engineering

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Background: Recent inquiries into high-quality foods have discussed the importance of the functional aspects of foods, in addition to traditional quality indicators such as color, firmness, weight, trimming loss, respiration rate, texture, and soluble solid content. Recently, functional Chinese cabbage, which makes up a large portion of the vegetables consumed in Korea, has been identified as an anticancer treatment. However, the investigation of practical issues, such as the effects of storage conditions on quality indicators (including functional compounds), is still limited. Purpose: We reviewed various studies on variations in the quality indicators and functional compounds of Chinese cabbage in response to different storage environments, focusing on storage temperature and storage period. In particular, we emphasized the effect of storage temperature and storage period on glucosinolate (GSL) levels, in order to provide guidelines for optimizing storage environments to maximize GSLs. Additionally, we used response surface methodology to propose experimental designs for future studies exploring the optimal storage conditions for enhancing GSL contents. Review: Large variations in quality indicators were observed depending on the cultivar, the type of storage, the storage conditions, and the harvest time. In particular, GSL content varied with storage conditions, indicating that either low temperatures or adequate air composition by controlled atmospheric storage may preserve GSL levels, as well as prolonging shelf life. Even though genetic and biochemical approaches are preferred for developing functional Chinese cabbage, it is important to establish a practical method for preserving quality for marketability; a prospective study into optimal storage conditions for preserving functional compounds (which can be applied in farms), is required. This may be achievable with the comprehensive meta-analysis of currently published data introduced in this review, or by conducting newly designed experiments investigating the relationship between storage conditions and the levels of functional compounds.

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“…Glucosinolates are associated with the bitter taste of Brassicaceae (van Doorn et al, 1998). A previous study revealed that cytochrome P450 is important in the glucosinolate biosynthetic pathway (Du et al, 1995).…”

Section: Storage Protein and Glucosinolate-related Genesmentioning

confidence: 99%

Effect of exogenous gibberellin on reserve accumulation during the seed filling stage of oilseed rape

Huang¹,

He²,

Liao³

et al. 2014

Genet. Mol. Res.

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ABSTRACT. Exogenous gibberellins (GAs) are widely applied to increase crop yields, with knowledge about the physiological functioning and biochemistry mechanisms of these phytohormones improving; however, information remains limited about the effect of GAs on seed filling. In this study, the siliques (containing the seeds) of oilseed rape (Brassica napus L.) were treated with GA 3 at 3 stages of seed filling. We confirmed that GA 3 regulates the deposition of storage reserves in developing seeds. The percentage of crude fat in the seeds increased during the early stage, but remained stable during the middle and late stages. In comparison, the percentage of total protein decreased during the early and middle stages, but significantly increased during the late stage. In addition, Q-PCR was employed to analyze the expression level of related genes in 2828 X.Q. Huang et al.©FUNPEC-RP www.funpecrp.com.br Genetics and Molecular Research 13 (2): 2827-2839 (2014) response to GA 3 . It was found that the expression of WRI and ABI3 transcription factors corresponded to crude fat content and total protein content, respectively. The expression of storage reserve related genes DGAT, MCAT, SUC2, and GPT was consistent with crude fat content, whereas the expression of Napin corresponded to total protein content. The results of this study indicate that exogenous GA 3 has a different effect on storage reserve deposition in seed during different stages of seed filling, and the effect might be achieved via changing the expression of related genes.

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The glucosinolates sinigrin and progoitrin are important determinants for taste preference and bitterness of Brussels sprouts

Cited by 115 publications

References 4 publications

A Novel 2-Oxoacid-Dependent Dioxygenase Involved in the Formation of the Goiterogenic 2-Hydroxybut-3-enyl Glucosinolate and Generalist Insect Resistance in Arabidopsis

A Novel 2-Oxoacid-Dependent Dioxygenase Involved in the Formation of the Goiterogenic 2-Hydroxybut-3-enyl Glucosinolate and Generalist Insect Resistance in Arabidopsis

Physicochemical Quality Changes in Chinese Cabbage with Storage Period and Temperature: A Review

Effect of exogenous gibberellin on reserve accumulation during the seed filling stage of oilseed rape

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