Glucosinolate structural diversity, identification, chemical synthesis and metabolism in plants

Blažević, Ivica; Montaut, Sabine; Burčul, Franko; Olsen, Carl Erik; Burow, Meike; Rollin, Patrick; Agerbirk, Niels

doi:10.1016/j.phytochem.2019.112100

Cited by 376 publications

(352 citation statements)

References 483 publications

Supporting

Mentioning

337

Contrasting

Unclassified

Order By: Relevance

“…By incorporating Brassicaceae plants into the soil, isothiocyanates and other compounds are released by enzymatic hydrolysis from glucosinolates, secondary plant metabolites occurring in Brassicales plants [46]. So far, around 137 glucosinolates have been identified and according to their variable side chain they can be classified into aliphatic, aryl(aliphatic), and indole glucosinolates [47]. In Brassicaceae plants, glucosinolates are present in all plants parts but their profile and levels differ enormously within plant organs, ontogenetic stages, species, and varieties [48][49][50].…”

Section: Biofumigationmentioning

confidence: 99%

Biofumigation for Fighting Replant Disease- A Review

Hanschen

Winkelmann

2020

Agronomy

View full text Add to dashboard Cite

Replant disease is a soil (micro-) biome-based, harmfully-disturbed physiological and morphological reaction of plants to replanting similar cultures on the same sites by demonstrating growth retardation and leading to economic losses especially in Rosaceae plant production. Commonly, replant disease is overcome by soil fumigation with toxic chemicals. With chemical soil fumigation being restricted in many countries, other strategies are needed. Biofumigation, which is characterized by the incorporation of Brassicaceae plant materials into soil, is a promising method. We review the potential of biofumigation in the fight against replant disease. Biofumigation using optimized Brassicaceae seed meal compositions in combination with replant disease tolerant plant genotypes shows promising results, but the efficacy is still soil and site-dependent. Therefore, future studies should address the optimal timing as well as amount and type of incorporated plant material and environmental conditions during incubation in dependence of the soil physical and chemical characteristics.

show abstract

Section: Biofumigationmentioning

confidence: 99%

Biofumigation for Fighting Replant Disease- A Review

Hanschen

Winkelmann

2020

Agronomy

View full text Add to dashboard Cite

show abstract

“…Glucosinolates are a group of about 130 structurally different amino acid-derived thioglucosides produced by Brassicales plants (Agerbirk & Olsen, 2012;Blažević et al, 2020). Plant GLS levels and compositions vary within and between species and are also influenced by biotic and abiotic factors (Burow, 2016).…”

Section: Most Species Of the Genus Phyllotreta Are Closely Associatedmentioning

confidence: 99%

Ontogenetic differences in the chemical defence of flea beetles influence their predation risk

2020

View full text Add to dashboard Cite

käfern mindestens so hoch ist wie in den Blättern der Futterpflanze, fragten sich die Wissenschaftler, ob sich den Käferlarven damit eine neue Option der Abwehr von Feinden eröffnet, zu denen auch die räuberischen Larven des asiatischen Marienkäfers (Harmonia axyridis, Abbildung 2) gehören. Wurden diesen im Experiment Larven des Meerretticherdflohs angeboten, die Senfölglykoside mit ihrer Nahrung zu sich genommen hatten, hörten die Marienkäferlarven schon nach wenigen Sekunden auf zu fressen, und jede dritte von ihnen erbrach die aufgenommene Mahlzeit. Da die Räuber nach dem Kontakt mit Gift enthaltenden Erdflohkäferlarven schnell lernten, die Artgenossen zu meiden, konnten mehr als zwei Drittel von ihnen überleben. Dagegen wurden Larven, die ernährungsbedingt wenig Senfölglykoside enthielten, von den Marienkäfern bereitwillig gefressen, und 90 Prozent dieser Erdflohkäferlarven überlebten den Angriff nicht. Solche Fütterungsexperimente bestätigten auch die toxische Wirkung der Senfölglykoside auf die Marienkäferlarven. Demnach setzen die Larven der Erdflohkäfer das Gift ihrer Futterpflanze als chemische Waffe für die Abwehr der eigenen Feinde ein. Allerdings wird dadurch nicht jede einzelne Larve geschützt, denn nur wenn einige von ihnen dem Angriff der Räuber zum Opfer fallen, kann die gesamte Population von dem so ausgelösten Lernprozess profitieren. Überraschend war, dass die Marienkäferlarven Eier, Puppen oder ausgewachsene Erdflohkäfer unbeschadet fressen konnten, obwohl diese deutlich mehr Senfölglykoside enthielten als die Erdflohkäferlarven. Und wenn die Räuber die Wahl hatten, bevorzugten sie stets die Puppen vor den Larven. Dieses Paradox erklärten die Wissenschaftler damit, dass vor allem die Larven des Erdflohkäfers in der Lage sind, die Glykoside zu spalten und Senföle freizusetzen, denn sie besitzen etwa 43fach mehr von der dafür benötigten Myrosinase. Deren Aktivität war unabhängig von der aufgenommenen Nahrung und selbst dann nachweisbar, wenn die Larven auf einer Mutante als Futterpflanze gezüchtet wurden, die das pflanzeneigene Enzym nicht bilden konnte. Die Erdflöhe beziehen also nur die Senf-öle von der Futterpflanze. Die zweite Komponente ihrer Abwehrstrategie produzieren die Larven selbst, um die Waffe zu schärfen. Dass dies nur die Larven tun, nicht aber die ausgewachsenen, zum Sprung bereiten Käfer, ist eine bemerkenswerte Anpassung an den durch räuberische Feinde ausgeübten Selektionsdruck. Eine spannende Frage bleibt noch zu lösen: Auch beim Erdflohkäfer werden wie bei den Pflanzen die toxischen Senföle nur nach Verletzungen freigesetzt. Demnach speichert auch der Erdfloh die Senfölglykoside räumlich getrennt von der körpereigenen Myrosinase. Im Experiment lassen sich die beiden Komponenten in Kontakt bringen, indem die Hämolymphe eingefroren und wieder aufgetaut wird, um die darin enthaltenen Zellen zum Platzen zu bringen. Wie der entsprechende Vorgang im Darm des räuberischen Insekts innerhalb kürzester Zeit abläuft, ist bislang noch unklar. Literatur [1] T. Sporer et al., Functional ...

show abstract

“…Between them vitamin C, polyphenols, and minerals can be found. However, one of the most relevant biomolecules are glucosinolates (GSLs), mainly found in plant species and varieties of the order Brassicales, mainly Brassicaceae as the most well-known representatives of this horticultural, botanical, and socioeconomically relevant botanical family [8]. They consist of a basic structure of a thiohydroximate-O-sulfate group with a glycosylation and, depending on which amino acid they are derived from, a different side chain [8].…”

Section: Introductionmentioning

confidence: 99%

“…However, one of the most relevant biomolecules are glucosinolates (GSLs), mainly found in plant species and varieties of the order Brassicales, mainly Brassicaceae as the most well-known representatives of this horticultural, botanical, and socioeconomically relevant botanical family [8]. They consist of a basic structure of a thiohydroximate-O-sulfate group with a glycosylation and, depending on which amino acid they are derived from, a different side chain [8]. GSLs are stable secondary metabolites, but after tissue disruption, they are hydrolyzed by the enzyme myrosinase (EC 3.2.1.147), generating different GSL hydrolysis products ( Figure 1) including bioactive isothiocyanates (ITCs) if the pH is 5-8, in the range of neutrality.…”

Section: Introductionmentioning

confidence: 99%

“…GSLs are stable secondary metabolites, but after tissue disruption, they are hydrolyzed by the enzyme myrosinase (EC 3.2.1.147), generating different GSL hydrolysis products ( Figure 1) including bioactive isothiocyanates (ITCs) if the pH is 5-8, in the range of neutrality. In some plants, epithiospecifier proteins exist and can modify the outcome of the hydrolysis process, typically to promote other products than ITCs, as it is the case of nitrile specifier protein originating simple nitriles and elemental sulfur [8][9][10]. On the other hand, the epithiospecifier proteins (ESP) with similar function may also carry out a different reaction for the few aliphatic GSLs with a terminal double bond by adding the sulfur to this bond, forming an epitionitrile.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

The Role of Brassica Bioactives on Human Health: Are We Studying It the Right Way?

Quirante-Moya¹,

García-Ibáñez

Quirante-Moya

et al. 2020

Molecules

View full text Add to dashboard Cite

Brassica vegetables and their components, the glucosinolates, have been suggested as good candidates as dietary coadjutants to improve health in non-communicable diseases (NCDs). Different preclinical and clinical studies have been performed in the last decade; however, some concerns have been posed on the lack of established and standardized protocols. The different concentration of bioactive compounds used, time of intervention or sample size, and the lack of blinding are some factors that may influence the studies’ outcomes. This review aims to analyze the critical points of the studies performed with Brassica-related biomolecules and propose some bases for future trials in order to avoid biases.

show abstract

Glucosinolate structural diversity, identification, chemical synthesis and metabolism in plants

Cited by 376 publications

References 483 publications

Biofumigation for Fighting Replant Disease- A Review

Biofumigation for Fighting Replant Disease- A Review

Ontogenetic differences in the chemical defence of flea beetles influence their predation risk

The Role of Brassica Bioactives on Human Health: Are We Studying It the Right Way?

Contact Info

Product

Resources

About