Inactivation of Thioglucosidase from Sinapis alba (White Mustard) Seed by Metal Salts

Marcinkowska, Monika; Jeleń, Henryk H.

doi:10.3390/molecules25194363

Cited by 9 publications

(12 citation statements)

References 29 publications

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“…To investigate this further, additional controls such as protein standard solutions and gut content extracts of other insect species should be included in future experiments. In general, plant myrosinase activity can be influenced by various factors including the levels of ascorbic acid (cofactor of myrosinases), sulfate, sodium chloride and silver ions ( Shikita et al, 1999 ; Andersson et al, 2009 ; Bhat and Vyas, 2019 ; Marcinkowska and Jelen, 2020 ). In addition, the gut pH can have a strong influence on the activity of ingested plant enzymes ( Pentzold et al, 2014b ).…”

Section: Discussionmentioning

confidence: 99%

Hijacking the Mustard-Oil Bomb: How a Glucosinolate-Sequestering Flea Beetle Copes With Plant Myrosinases

et al. 2021

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Myrosinase enzymes play a key role in the chemical defense of plants of the order Brassicales. Upon herbivory, myrosinases hydrolyze the β-S-linked glucose moiety of glucosinolates, the characteristic secondary metabolites of brassicaceous plants, which leads to the formation of different toxic hydrolysis products. The specialist flea beetle, Phyllotreta armoraciae, is capable of accumulating high levels of glucosinolates in the body and can thus at least partially avoid plant myrosinase activity. In feeding experiments with the myrosinase-deficient Arabidopsis thaliana tgg1 × tgg2 (tgg) mutant and the corresponding Arabidopsis Col-0 wild type, we investigated the influence of plant myrosinase activity on the metabolic fate of ingested glucosinolates in adult P. armoraciae beetles. Arabidopsis myrosinases hydrolyzed a fraction of ingested glucosinolates and thereby reduced the glucosinolate sequestration rate by up to 50% in adult beetles. These results show that P. armoraciae cannot fully prevent glucosinolate hydrolysis; however, the exposure of adult beetles to glucosinolate hydrolysis products had no impact on the beetle’s energy budget under our experimental conditions. To understand how P. armoraciae can partially prevent glucosinolate hydrolysis, we analyzed the short-term fate of ingested glucosinolates and found them to be rapidly absorbed from the gut. In addition, we determined the fate of ingested Arabidopsis myrosinase enzymes in P. armoraciae. Although we detected Arabidopsis myrosinase protein in the feces, we found only traces of myrosinase activity, suggesting that P. armoraciae can inactivate plant myrosinases in the gut. Based on our findings, we propose that the ability to tolerate plant myrosinase activity and a fast glucosinolate uptake mechanism represent key adaptations of P. armoraciae to their brassicaceous host plants.

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Section: Discussionmentioning

confidence: 99%

Hijacking the Mustard-Oil Bomb: How a Glucosinolate-Sequestering Flea Beetle Copes With Plant Myrosinases

et al. 2021

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“…Therefore, their potential formation/release during cooking is an open question. An opposite situation (in terms of FD) could be observed for some nitriles (33,41), benzyl thiocyanate (44), and 2-pentylfuran (6).…”

Section: ■ Results and Discussionmentioning

confidence: 91%

“…They consist of an oxime sulfate group, the carbon atom of which is bound via a sulfur atom to a β- d -glucopyranosyl group and on the other side carries an aliphatic or aromatic side chain derived from an amino acid. , Tissue disruption brings glucosinolates in direct contact with the endogenous enzyme myrosinase, which cleaves the glycosidic bond. The aglycone spontaneously reacts to yield compounds such as isothiocyanates, nitriles, thiocyanates, epithionitriles, indoles, and 1,3-oxazolidine-2-thiones. , …”

Section: Introductionmentioning

confidence: 99%

“…The aglycone spontaneously reacts to yield compounds such as isothiocyanates, nitriles, thiocyanates, epithionitriles, indoles, and 1,3oxazolidine-2-thiones. 5,6 Glucosinolate breakdown products can greatly affect the flavor of Brassica vegetables. Favored by hydrolysis at neutral pH, isothiocyanates 5 include volatile compounds with a strong garlic and sulfur odor, frequently found at a low odor threshold concentration (OTC) in the range of μg/L in water.…”

Section: ■ Introductionmentioning

confidence: 99%

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Key Odorants of Raw and Cooked Green Kohlrabi (Brassica oleracea var. gongylodes L.)

Marcinkowska

Frank

Steinhaus

et al. 2021

J. Agric. Food Chem.

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Volatile compounds of raw and cooked green kohlrabi were investigated using a sensomics approach. A total of 55 odor-active compounds were detected and identified in raw and cooked green kohlrabi using GC-O. Twenty-eight odor-active compounds with high flavor dilution (FD) factors ranging from 64 to 1024 were quantitated, and odor activity values (OAVs) were determined. Eight compounds showed high OAVs in raw and cooked kohlrabi: five sulfur compounds (dimethyl trisulfide, methyl 2-methyl-3-furyl disulfide, and three isothiocyanates (1-isothiocyanato-3-(methylsulfanyl)propane, benzyl isothiocyanate, and 1-isothiocyanato-4-(methylsulfanyl)butane)), two lipid oxidation products (1-octen-3-one and trans-4,5-epoxy-(2E)-dec-2-enal), and 2-isopropyl-3-methoxypyrazine. Among these, the sulfur compounds contributed most to the overall smell of the raw and cooked vegetables. The quantitation analysis indicates that the eight odorants are the backbone compounds for raw and cooked kohlrabi. The OAVs for the backbone compounds and also for minor odorants are clearly higher in raw kohlrabi than in the cooked one. Differences can be explained by the influence of the cooking process.

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“…These results provide direct evidence for suppression of myrosinase activity in the gut of P. armoraciae and indicate that several factors contribute to myrosinase inhibition, of which some are sensitive to heat. Candidate agents that can modify plant myrosinase activity include ascorbic acid (cofactor of myrosinases), sulfate, sodium chloride and silver ions (Shikita et al, 1999; Andersson et al, 2009; Bhat and Vyas, 2019; Marcinkowska and Jelen, 2020). In addition, the gut pH can have a strong influence on the activity of ingested plant enzymes (Pentzold et al, 2014b).…”

Section: Discussionmentioning

confidence: 99%

A specialist flea beetle manipulates and tolerates the activated chemical defense in its host plant

Sporer

Körnig

Wielsch

et al. 2021

Preprint

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Glucosinolates, the characteristic secondary metabolites of Brassicales, are hydrolyzed upon herbivory by myrosinases to toxic and deterrent defense metabolites. The specialist flea beetle, Phyllotreta armoraciae, sequesters glucosinolates in the body despite myrosinase activity, but it is unknown whether plant myrosinase activity influences sequestration and how beetles prevent the hydrolysis of ingested glucosinolates. In feeding experiments performed with the myrosinase-deficient Arabidopsis thaliana tgg1tgg2 (tgg) mutant and the corresponding wild type, we found that plant myrosinases reduced the glucosinolate sequestration rate by up to 50% and hydrolyzed a fraction of ingested glucosinolates in adult beetles. Although these results show that P. armoraciae cannot fully prevent glucosinolate hydrolysis, we observed no negative influence on beetle performance. To understand how P. armoraciae can avoid the hydrolysis of some ingested glucosinolates, we analyzed their fate directly after ingestion. P. armoraciae rapidly absorbed glucosinolates across the gut epithelium, a strategy that has been proposed to prevent hydrolysis in the gut lumen of sequestering insects. Moreover, beetle gut content suppressed in vitro myrosinase activity, and almost no myrosinase activity was detectable in the feces, which indicates that ingested myrosinases are inactivated in the beetle gut. In summary, we show that P. armoraciae uses several strategies to prevent the hydrolysis of ingested glucosinolates but can also tolerate the formation of glucosinolate hydrolysis products.

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Inactivation of Thioglucosidase from Sinapis alba (White Mustard) Seed by Metal Salts

Cited by 9 publications

References 29 publications

Hijacking the Mustard-Oil Bomb: How a Glucosinolate-Sequestering Flea Beetle Copes With Plant Myrosinases

Hijacking the Mustard-Oil Bomb: How a Glucosinolate-Sequestering Flea Beetle Copes With Plant Myrosinases

Key Odorants of Raw and Cooked Green Kohlrabi (Brassica oleracea var. gongylodes L.)

A specialist flea beetle manipulates and tolerates the activated chemical defense in its host plant

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