Phytoalexins from crucifers: synthesis, biosynthesis, and biotransformation

Pedras, M. Soledade C.; Okanga, Francis I.; Zaharia, Irina L.; Khan, Adnan

doi:10.1016/s0031-9422(99)00494-x

Cited by 169 publications

(130 citation statements)

References 65 publications

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“…Brassinin and 1-methoxybrassinin, which contain a dithiocarbamate group, were the first phytoalexins to be reported. Dithiocarbamates have been recognised as important pesticides and herbicides and until now crucifers are the only plants known to produce such compounds (Pedras et al, 2000).…”

Section: Phytoalexins and Phytoanticipinsmentioning

confidence: 99%

Defence mechanisms of Brassicaceae: implications for plant-insect interactions and potential for integrated pest management. A review

Ahuja

Rohloff

Bones

2010

Agron. Sustain. Dev.

212

165

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-Brassica crops are grown worldwide for oil, food and feed purposes, and constitute a significant economic value due to their nutritional, medicinal, bioindustrial, biocontrol and crop rotation properties. Insect pests cause enormous yield and economic losses in Brassica crop production every year, and are a threat to global agriculture. In order to overcome these insect pests, Brassica species themselves use multiple defence mechanisms, which can be constitutive, inducible, induced, direct or indirect depending upon the insect or the degree of insect attack. Firstly, we give an overview of different Brassica species with the main focus on cultivated brassicas. Secondly, we describe insect pests that attack brassicas. Thirdly, we address multiple defence mechanisms, with the main focus on phytoalexins, sulphur, glucosinolates, the glucosinolate-myrosinase system and their breakdown products. In order to develop pest control strategies, it is important to study the chemical ecology, and insect behaviour. We review studies on oviposition regulation, multitrophic interactions involving feeding and host selection behaviour of parasitoids and predators of herbivores on brassicas. Regarding oviposition and trophic interactions, we outline insect oviposition behaviour, the importance of chemical stimulation, oviposition-deterring pheromones, glucosinolates, isothiocyanates, nitriles, and phytoalexins and their importance towards pest management. Finally, we review brassicas as cover and trap crops, and as biocontrol, biofumigant and biocidal agents against insects and pathogens. Again, we emphasise glucosinolates, their breakdown products, and plant volatile compounds as key components in these processes, which have been considered beneficial in the past and hold great prospects for the future with respect to an integrated pest management.Brassicas / insect pests / chemical ecology / trophic levels / glucosinolates / isothiocyanates / defence mechanisms / biocontrol / trap crops / integrated pest management

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Section: Phytoalexins and Phytoanticipinsmentioning

confidence: 99%

Defence mechanisms of Brassicaceae: implications for plant-insect interactions and potential for integrated pest management. A review

Ahuja

Rohloff

Bones

2010

Agron. Sustain. Dev.

212

165

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“…C haracteristic for cruciferous plants is the synthesis of a wide range of species-specific phytoalexins that structurally are sulfur-containing indole alkaloids (1) and the synthesis of glucosinolates (reviewed in ref. 2).…”

mentioning

confidence: 99%

Camalexin is synthesized from indole-3-acetaldoxime, a key branching point between primary and secondary metabolism in Arabidopsis

Glawischnig¹,

Hansen²,

Olsen³

et al. 2004

Proc. Natl. Acad. Sci. U.S.A.

284

287

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Characteristic for cruciferous plants is their production of N-and S-containing indole phytoalexins with disease resistance and cancer-preventive properties, previously proposed to be synthesized from indole independently of tryptophan. We show that camalexin, the indole phytoalexin of Arabidopsis thaliana, is synthesized from tryptophan via indole-3-acetaldoxime (IAOx) in a reaction catalyzed by CYP79B2 and CYP79B3. Cyp79B2͞cyp79B3 double knockout mutant is devoid of camalexin, as it is also devoid of indole glucosinolates [Zhao, Y., Hull, A. K., Gupta, N. R., Goss, K. A., Alonso, J., Ecker, J. R., Normanly, J., Chory, J. & Celenza, J. L. (2002) Genes Dev. 16, 3100 -3112], and isotope-labeled IAOx is incorporated into camalexin. These results demonstrate that only CYP79B2 and CYP79B3 contribute significantly to the IAOx pool from which camalexin and indole glucosinolates are synthesized. Furthermore, production of camalexin in the sur1 mutant devoid of glucosinolates excludes the possibility that camalexin is derived from indole glucosinolates. CYP79B2 plays an important role in camalexin biosynthesis in that the transcript level of CYP79B2, but not CYP79B3, is increased upon induction of camalexin by silver nitrate as evidenced by microarray analysis and promoter-␤-glucuronidase data. The structural similarity between cruciferous indole phytoalexins suggests that these compounds are biogenetically related and synthesized from tryptophan via IAOx by CYP79B homologues. The data show that IAOx is a key branching point between several secondary metabolic pathways as well as primary metabolism, where IAOx has been shown to play a critical role in IAA homeostasis.C haracteristic for cruciferous plants is the synthesis of a wide range of species-specific phytoalexins that structurally are sulfur-containing indole alkaloids (1) and the synthesis of glucosinolates (reviewed in ref.2). Both groups of natural products are involved in plant defense and have cancer-preventive properties (3, 4). Very little is known about the biosynthetic pathway of the S-containing indole phytoalexins. Their similar structure with N-and S-containing side chains at C-3 of the indole ring suggests a biogenetic relationship (5). Camalexin (3-thiazol-2Ј-yl-indole) is produced in the model plant Arabidopsis thaliana (6). It is induced by a variety of microorganisms, e.g., Pseudomonas syringae (6) and Alternaria brassisicola (7), and by abiotic factors, such as AgNO 3 (8). These findings make camalexin a good model compound for studying biosynthesis and regulation of cruciferous indole phytoalexins. In vivo feeding experiments where radiolabeled anthranilate and tryptophan were applied on leaves treated with AgNO 3 led to the suggestion that tryptophan was not a precursor in camalexin biosynthesis because tryptophan was much less efficiently incorporated into camalexin compared with anthranilate (8, 9). The data were further supported by labeling studies performed in three tryptophan mutants (8), where reduced levels of camalexin accumulated in ...

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“…Brassinin and 1-methoxybrassinin, which contain a dithiocarbamate group, were the first phytoalexins to be reported. Dithiocarbamates have been recognized as important pesticides and herbicides and until know crucifers are the only plants known to produce such compounds (Pedras et al, 2000). Glucosinolates: Glucosinolates are the most studied defense related secondary compounds in Brassicaceae.…”

Section: Different Chemical Defenses In Brassica Plantsmentioning

confidence: 99%

Plant secondary metabolites (PSMs) of Brassicaceae and their role in plant defense against insect herbivores – A review

Kumar

2017

JANS

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Abstract:The genus Brassica includes economically important oilseed and vegetable plants. A number of insect pests are known to infest these crops and cause significant losses in yield. The plants in the family Brassicaceae have multiple defense mechanisms to overcome or reduce the damage by these pests including defensive biochemicals. These Plant Secondary Metabolites (PSMs) involve myrosinase-glucosinolate system, different volatile compounds, lectins, phytoalexins and phytoanticipins. While some of the compounds are always present in the plant system, the others are synthesized after herbivore attack. These compounds can either directly protect the plant by having effect(s) on insects' biology/behaviour or indirectly by attracting the natural enemies of the pests. Because of these secondary compounds, Brassicas have the potential to be used in pest management such as biofumigation against soil pests, as trap crops and cover crops and hence, can be a part of push-pull strategy. An attempt has been made to review these compounds in Brassicas, their role in defense against insects and potential in pest management.

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Phytoalexins from crucifers: synthesis, biosynthesis, and biotransformation

Cited by 169 publications

References 65 publications

Defence mechanisms of Brassicaceae: implications for plant-insect interactions and potential for integrated pest management. A review

Defence mechanisms of Brassicaceae: implications for plant-insect interactions and potential for integrated pest management. A review

Camalexin is synthesized from indole-3-acetaldoxime, a key branching point between primary and secondary metabolism in Arabidopsis

Plant secondary metabolites (PSMs) of Brassicaceae and their role in plant defense against insect herbivores – A review

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