Metabolic Modifications of Birch Leaf Phenolics by an Herbivorous Insect: Detoxification of Flavonoid Aglycones via Glycosylation

Salminen, Juha‐Pekka; Lahtinen, Maria; Lempa, Kyösti; Kapari, Lauri; Haukioja, Erkki; Pihlaja, Kalevi

doi:10.1515/znc-2004-5-627

Cited by 42 publications

(46 citation statements)

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“…Glycosylation of xenobiotics in plants is often paired with sequestration of the glycoside that is formed in the vacuole. Insect larvae can also detoxify plant flavonoids by glycosylation (38). While detoxification via glycosylation is not unusual in plant systems, it has not been frequently reported in microbes.…”

Section: Biotransformation Of T-2 Toxinmentioning

confidence: 99%

Glucosylation and Other Biotransformations of T-2 Toxin by Yeasts of the Trichomonascus Clade

McCormick

Price

Kurtzman

2012

Appl Environ Microbiol

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bTrichothecenes are sesquiterpenoid toxins produced by Fusarium species. Since these mycotoxins are very stable, there is interest in microbial transformations that can remove toxins from contaminated grain or cereal products. Twenty-three yeast species assigned to the Trichomonascus clade (Saccharomycotina, Ascomycota), including four Trichomonascus species and 19 anamorphic species presently classified in Blastobotrys, were tested for their ability to convert the trichothecene T-2 toxin to less-toxic products. These species gave three types of biotransformations: acetylation to 3-acetyl T-2 toxin, glycosylation to T-2 toxin 3-glucoside, and removal of the isovaleryl group to form neosolaniol. Some species gave more than one type of biotransformation. Three Blastobotrys species converted T-2 toxin into T-2 toxin 3-glucoside, a compound that has been identified as a masked mycotoxin in Fusarium-infected grain. This is the first report of a microbial whole-cell method for producing trichothecene glycosides, and the potential large-scale availability of T-2 toxin 3-glucoside will facilitate toxicity testing and development of methods for detection of this compound in agricultural and other products.T he fungal T-2 toxin (see Fig. 1) is a sesquiterpenoid trichothecene produced by Fusarium sporotrichioides and related species. Trichothecenes inhibit protein synthesis in eukaryotes and can cause both acute and chronic health problems for humans and animals that ingest contaminated food or feed. T-2 toxin in overwintered wheat was the cause of outbreaks of alimentary toxic aleukia in the 1930s in the former Soviet Union and has been associated with other gastrointestinal problems (42).Trichothecenes are very stable mycotoxins. Consequently, there is interest in identifying chemical treatments or microbial transformations that effectively remove the compounds from contaminated grain or cereal products. For example, treatment of contaminated grain with the preservative sodium bisulfite converts the trichothecene deoxynivalenol (DON) into nontoxic DON sulfonates (13). Several types of microbial bioconversions of trichothecenes have also been reported (49), including oxygenation (3), acetylation (1, 24), deacetylation (5, 47), oxidation (41), deepoxidation (16, 20, 25, 43, 44, 48), and epimerization (19, 22). Some of these transformations lead to a complete loss of toxicity of the trichothecenes (e.g., deepoxidation) or reduce their toxicity (e.g., acetylation, oxidation) and thereby protect organisms from the deleterious effects of the toxins. Changes to the C-3 position and the epoxide have the greatest impact on toxicity (49). Indeed, microbes or enzymes that degrade or detoxify mycotoxins have possible practical applications as additives in animal feeds. These microbes can also be a source of genes that can be used to engineer disease-resistant crop plants. For example, the trichothecene acetyltransferase gene has been used to confer resistance to DON (33), which is a major virulence factor in Fusarium graminearum whe...

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Section: Biotransformation Of T-2 Toxinmentioning

confidence: 99%

Glucosylation and Other Biotransformations of T-2 Toxin by Yeasts of the Trichomonascus Clade

McCormick

Price

Kurtzman

2012

Appl Environ Microbiol

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“…If that were the case, the abundance of these metabolites would have been considerably higher in the caterpillar extracts than in those of the plants (Müller et al 2001). Caterpillars of the species Epirrita autumnata, which is unrelated to P. rapae, isomerise p-CoQAs and chlorogenic acids (Salminen et al 2004). However, because we did not measure any ions with m/z 337.092 in the caterpillar extracts that were absent in the plant extracts it is unlikely that P. rapae has similar capacities.…”

Section: A 'Metabolic Interface' Emerges Between Plants and Caterpillarsmentioning

confidence: 99%

Metabolomic analysis of the interaction between plants and herbivores

et al. 2008

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Insect herbivores by necessity have to deal with a large arsenal of plant defence metabolites. The levels of defence compounds may be increased by insect damage. These induced plant responses may also affect the metabolism and performance of successive insect herbivores. As the chemical nature of induced responses is largely unknown, global metabolomic analyses are a valuable tool to gain more insight into the metabolites possibly involved in such interactions. This study analyzed the interaction between feral cabbage (Brassica oleracea) and small cabbage white caterpillars (Pieris rapae) and how previous attacks to the plant affect the caterpillar metabolism. Because plants may be induced by shoot and root herbivory, we compared shoot and root induction by treating the plants on either plant part with jasmonic acid. Extracts of the plants and the caterpillars were chemically analysed using Ultra Performance Liquid Chromatography/Time of Flight Mass Spectrometry (UPLCT/MS). The study revealed that the levels of three structurally related coumaroylquinic acids were elevated in plants treated on the shoot. The levels of these compounds in plants and caterpillars were highly correlated: these compounds were defined as the 'metabolic interface'. The role of these metabolites could only be discovered using simultaneous analysis of the plant and caterpillar metabolomes. We conclude that a metabolomics approach is useful in discovering unexpected bioactive compounds involved in ecological interactions between plants and their herbivores and higher trophic levels.

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“…Haukioja 2003). Salminen et al (2004) proposed that understanding the true effects of particular phenolic compounds on insect performance requires knowledge of how phenolics are metabolized in the digestive tract of insects. Recently, we have reported fates of individual birch (Betula pubescens) leaf phenolics in larvae of the geometrid moth Epirrita autumnata, the main defoliator of birch (Salminen & Lempa 2002;Salminen et al 2004).…”

Section: Introductionmentioning

confidence: 99%

“…Salminen et al (2004) proposed that understanding the true effects of particular phenolic compounds on insect performance requires knowledge of how phenolics are metabolized in the digestive tract of insects. Recently, we have reported fates of individual birch (Betula pubescens) leaf phenolics in larvae of the geometrid moth Epirrita autumnata, the main defoliator of birch (Salminen & Lempa 2002;Salminen et al 2004). However, so far we have not studied the fate of birch leaf phenolics in any other insect species, although we know that birch is also attacked, for example, by numerous species of sawflies; mountain birch alone accommodates close to 40 sawfly species, most of which are birch specialists (Hanhimäki et al 1995).…”

Section: Introductionmentioning

confidence: 99%

“…In our earlier studies with birch and flush-feeding E. autumnata we have reported particular reactions of foliar phenolics in larvae, such as partial hydrolysis of hydrolysable tannins, isomerisation of chlorogenic acid and glycosylation of flavonoid aglycones (Salminen & Lempa 2002;Salminen et al 2004). Because of drastic changes in the composition of foliar phenolics during the growing season (e.g.…”

Section: Introductionmentioning

confidence: 99%

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Biochemical transformation of birch leaf phenolics in larvae of six species of sawflies

et al. 2005

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We investigated the biochemical transformation of individual phenolic compounds of mountain birch leaves in larvae of six birch-feeding sawfly species: Amauronematus amplus, Pristiphora alpestris, Nematus brevivalvis, Priophorus pallipes, Arge sp. and Nematus viridis by comparing the phenolic residues in larval faeces to those of their leaf diet. Partial hydrolysis of hydrolysable tannins, isomerisation of chlorogenic acid and glycosylation of flavonoid aglycones were observed in all studied species. Moreover, we found considerable among-species variation in the composition of phenolic compounds in larval faeces. In addition to foliar phenolics, seventeen non-foliar phenolic metabolites, including eight phenolic acids and nine flavonoid glycosides were detected from the faeces. Of the non-foliar phenolic acids, four were egested speciesspecifically and only two by all six sawfly species. We also detected differences in the ratios of chlorogenic acid isomers in the faeces of different species, which can indicate different physiological conditions in the guts of studied larvae. In addition to the qualitative differences, quantitative differences were detected in the egestion of chlorogenic acids, possible o-quinone precursors in the larvae. Detected differences, either qualitative or quantitative, could not be explained by seasonal changes in the content of compounds in the leaf diet.

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Metabolic Modifications of Birch Leaf Phenolics by an Herbivorous Insect: Detoxification of Flavonoid Aglycones via Glycosylation

Cited by 42 publications

References 3 publications

Glucosylation and Other Biotransformations of T-2 Toxin by Yeasts of the Trichomonascus Clade

Glucosylation and Other Biotransformations of T-2 Toxin by Yeasts of the Trichomonascus Clade

Metabolomic analysis of the interaction between plants and herbivores

Biochemical transformation of birch leaf phenolics in larvae of six species of sawflies

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