Molecular interactions of the phytotoxins destruxin B and sirodesmin PL with crucifers and cereals: Metabolism and elicitation of plant defenses

Pedras, M. Soledade C.; Khallaf, Iman

doi:10.1016/j.phytochem.2012.02.010

Cited by 10 publications

(15 citation statements)

References 21 publications

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Section: Hydroxylationmentioning

confidence: 99%

“…Destruxin B (17) can be detoxified into hydroxydestruxin B (18) by the hydroxylase from cruciferous plants such as Brassica napus ( Figure S5). It was considered as an important detoxification step made by the host plant [24,25].Fusaric acid (FA, 19), also called 5-butylpicolinic acid, is a host non-specific phytotoxin produced by the fungi from the genus Fusarium [26]. FA (19) was converted to 8-hydroxyfusaric acid (20) with hydroxylation by the fungus Mucor rouxii ( Figure S6) [27].Ochratoxin A (OTA, 21) consists of a chlorinated dihydroisocoumarin linked through a 7-carboxyl group to L-phenylalanine by an amide bond.OTA (21) was hydroxylated into 7-carboxy-(2 -hydroxy-1-phenylalanine-amide)-5-chloro-8-hydroxy-3,4-dihydro-3R-methylisocoumarin (22) and a dihydrodiol derivative (23) by a Gram-negative bacterium Phenylobacterium immobile ( Figure S7) [28].Toxins 2020, 12, 121 3 of 37 (4R)-4-Hydroxyochratoxin A (24), or 4-hydroxyochratoxin A, was isolated from the urine of rats after injection with OTA (21), which indicated that OTA (21) was converted to (4R)-4-hydroxyochratoxin A (24) ( Figure S8) [29].OTA (21) was hydroxylated into (4R)-4-hydroxyochratoxin A (24) and (4S)-4-hydroxyochratoxin A (25) as well as 10-hydroxyochratoxin A (26) by rabbit liver microsomes ( Figure S9) [30,31].When ochratoxin B (OTB, 27) was incubated with horse radish peroxidase (HPR), the high level of the hydroquinone metabolite of ochratoxin (OTHQ, 28) was produced ( Figure S10).…”

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confidence: 99%

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Detoxification of Mycotoxins through Biotransformation

Yin

et al. 2020

Toxins

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Mycotoxins are toxic fungal secondary metabolites that pose a major threat to the safety of food and feed. Mycotoxins are usually converted into less toxic or non-toxic metabolites through biotransformation that are often made by living organisms as well as the isolated enzymes. The conversions mainly include hydroxylation, oxidation, hydrogenation, de-epoxidation, methylation, glycosylation and glucuronidation, esterification, hydrolysis, sulfation, demethylation and deamination. Biotransformations of some notorious mycotoxins such as alfatoxins, alternariol, citrinin, fomannoxin, ochratoxins, patulin, trichothecenes and zearalenone analogues are reviewed in detail. The recent development and applications of mycotoxins detoxification through biotransformation are also discussed.

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Section: Hydroxylationmentioning

confidence: 99%

mentioning

confidence: 99%

Detoxification of Mycotoxins through Biotransformation

Yin

et al. 2020

Toxins

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“…Until now, dtxs have only been extracted with organic solvents [16][17][18][19][20]. Using that procedure, Liu et al quantified dtx B in plants [16].…”

Section: Optimization Of Quechers-based Sample Treatmentmentioning

confidence: 99%

“…In the bibliography, most of the articles have reported the extraction of these secondary metabolites in insects or plants with organic solvents [16][17][18][19][20]. In case of insects, the investigations have paid attention to dtxs A, B and E found after the inoculation of different strains [17,19,20].…”

Section: Introductionmentioning

confidence: 99%

“…In case of insects, the investigations have paid attention to dtxs A, B and E found after the inoculation of different strains [17,19,20]. On the other hand, for instance, dtx B has been detected in plants and cereals in order to understand its metabolic degradation route [18]. Moreover, one study has been found [16], in which a dtx was quantified in cabbage plants, however there is a lack of full validated methodologies to determine dtxs present in different types of samples.…”

Section: Introductionmentioning

confidence: 99%

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Development of a QuEChERS-based extraction method for the determination of destruxins in potato plants by UHPLC–MS/MS

Carpio

Arroyo‐Manzanares

Ríos-Moreno

et al. 2016

Talanta

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Interactions of Bunias orientalis plant chemotypes and fungal pathogens with different host specificity in vivo and in vitro

Tewes

Müller

2020

Sci Rep

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Within several plant species, a high variation in the composition of particular defence metabolites can be found, forming distinct chemotypes. Such chemotypes show different effects on specialist and generalist plant enemies, whereby studies examining interactions with pathogens are underrepresented. We aimed to determine factors mediating the interaction of two chemotypes of Bunias orientalis (Brassicaceae) with two plant pathogenic fungal species of different host range, Alternaria brassicae (narrow host range = specialist) and Botrytis cinerea (broad hostrange = generalist) using a combination of controlled bioassays. We found that the specialist, but not the generalist, was sensitive to differences between plant chemotypes in vivo and in vitro. The specialist fungus was more virulent (measured as leaf water loss) on one chemotype in vivo without differing in biomass produced during infection, while extracts from the same chemotype caused strong growth inhibition in that species in vitro. Furthermore, fractions of extracts from B. orientalis had divergent in vitro effects on the specialist versus the generalist, supporting presumed adaptations to certain compound classes. This study underlines the necessity to combine various experimental approaches to elucidate the complex interplay between plants and different pathogens. Plants produce a multitude of defensive compounds that mediate interactions with attacking organisms from different taxa 1. Generalists may be fended-off by (sets of) defence compounds effectively, while specialists instead use such compounds as host selection cues 2,3. These distinct roles of individual compounds in interactions with different natural enemies, including herbivores and pathogens, is discussed to be one of the major drivers of the evolution of diverse plant defences 4-6. A high variation in chemical defence profiles can be particularly found within plant species, in which so-called chemotypes are formed, that differ in the composition of a certain metabolite class 7-10. Several studies address the responses of insect herbivores to distinct chemical defence profiles in plant families or species 8,11,12. In contrast, only little is known about the role of phytochemical variation in interactions with pathogens (but see, e.g. 7). Various plant species of the Brassicaceae family show different chemotypes and are well-studied for interactions of certain chemotypes with plant enemies. For example, distinct chemotypes have been found in Arabidopsis thaliana 13,14 , Barbarea vulgaris 10,15 and Brassica oleracea 16,17. Interestingly, in B. vulgaris one chemotype is resistant to two herbivore species, while another is instead resistant to an oomycete pathogen 18 , underlining the importance to consider enemies from different taxa in chemo-ecological studies. Chemotypes in the Brassicaceae are typically characterised by variations in profiles of glucosinolates, a structurally highly diverse group of defence compounds 19. Glucosinolates are assumed to be largely involved in resistance of ...

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Molecular interactions of the phytotoxins destruxin B and sirodesmin PL with crucifers and cereals: Metabolism and elicitation of plant defenses

Cited by 10 publications

References 21 publications

Detoxification of Mycotoxins through Biotransformation

Detoxification of Mycotoxins through Biotransformation

Development of a QuEChERS-based extraction method for the determination of destruxins in potato plants by UHPLC–MS/MS

Interactions of Bunias orientalis plant chemotypes and fungal pathogens with different host specificity in vivo and in vitro

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