Evolutionary recruitment of a flavin-dependent monooxygenase for stabilization of sequestered pyrrolizidine alkaloids in arctiids

Langel, Dorothee; Ober, Dietrich

doi:10.1016/j.phytochem.2010.12.014

Cited by 23 publications

(20 citation statements)

References 85 publications

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“…In L. japonicus, it appears likely that only two more enzymes are necessary to produce all the non-cyanogenic HNGs, and they could very well be closely related to the two cytochromes P450 already known to be involved in the pathway Takos et al, 2011;Saito et al, 2012). As previously mentioned, biosynthesis of sarmentosin presumably only requires an additional hydroxylation of rhodiocyanoside A, a reaction frequently used by insects to handle sequestered toxins (Langel and Ober, 2011;Pinto et al, 2011) and possibly present in P. clodius if it does not feed on S. lanceolatum. Given the similar structure of the CNglc biosynthetic pathway in insects and plants, it is likely that some insects could also possess the few additional enzymes needed to produce the remaining compounds as suspected for the Abraxas species (Nishida, 1994;Nishida et al, 1994).…”

Section: Discussionmentioning

confidence: 95%

Occurrence of Sarmentosin and Other Hydroxynitrile Glucosides in Parnassius (Papilionidae) Butterflies and Their Food Plants

et al. 2012

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Sequestration of plant secondary metabolites is a widespread phenomenon among aposematic insects. Sarmentosin is an unsaturated γ-hydroxynitrile glucoside known from plants and some Lepidoptera. It is structurally and biosynthetically closely related to cyanogenic glucosides, which are commonly sequestered from food plants and/or de novo synthesized by lepidopteran species. Sarmentosin was found previously in Parnassius (Papilionidae) butterflies, but it was not known how the occurrence was related to food plants or whether Parnassius species could biosynthesize the compound. Here, we report on the occurrence of sarmentosin and related compounds in four different Parnassius species belonging to two different clades, as well as their known and suspected food plants. There were dramatic differences between the two clades, with P. apollo and P. smintheus from the Apollo group containing high amounts of sarmentosin, and P. clodius and P. mnemosyne from the Mnemosyne group containing low or no detectable amounts. This was reflected in the larval food plants; P. apollo and P. smintheus larvae feed on Sedum species (Crassulaceae), which all contained considerable amounts of sarmentosin, while the known food plants of the two other species, Dicentra and Corydalis (Fumariaceae), had no detectable levels of sarmentosin. All insects and plants containing sarmentosin also contained other biosynthetically related hydroxynitrile glucosides in patterns previously reported for plants, but not for insects. Not all findings could be explained by sequestration alone and we therefore hypothesize that Parnassius species are able to de novo synthesize sarmentosin.

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Section: Discussionmentioning

confidence: 95%

Occurrence of Sarmentosin and Other Hydroxynitrile Glucosides in Parnassius (Papilionidae) Butterflies and Their Food Plants

et al. 2012

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“…Three FMO genes were identified from S. exigua , the same number as in B. mori and H. armigera , according to the prediction using genomic data (Langel & Ober, ; Wang et al ., ). Phylogenetic analysis showed that there was no orthologous relationship between insect and mammalian FMOs (Naumann et al ., ), and the branching pattern of the tree displayed two obvious clusters of insect FMOs far separated from human FMOs.…”

Section: Discussionmentioning

confidence: 97%

“…In insects, P450s were regarded as the important detoxifying enzymes and thus the role of FMOs was overlooked for a long time until 2002, when the first insect FMO gene ( senecionine N‐oxygenase ) was identified in Tyria jacobaeae (Naumann et al ., ). The enzyme encoded by TjFMO was found to have high N‐oxidation activity on pyrrolizidine alkaloids (PAs), and to transform toxic PAs from host plants to their nontoxic N‐oxides leading to relatively safe accumulation (Langel & Ober, ). Since then, FMOs from moths and grasshoppers have been characterized as a result of research on PA detoxification (Sehlmeyer et al ., ; Wang et al ., ).…”

Section: Introductionmentioning

confidence: 99%

Molecular characterization, expression pattern and metabolic activity of flavin‐dependent monooxygenases inSpodoptera exigua

Tian

Zhao²,

Guo

et al. 2018

Insect Molecular Biology

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Enhanced detoxification is one of the important mechanisms for insecticide resistance. Most research in this field to date has focused on the role of cytochrome P450s. Our previous work revealed that flavin-dependent monooxygenases (FMOs) were involved in metabolic resistance of Spodoptera exigua. In the present study we investigated the molecular characteristics, expression patterns and oxidative activities of SeFMO on insecticides. Three FMO genes, which encode proteins with the typical FMO motifs, were cloned from S. exigua. The oxidative activities of eukaryotically expressed SeFMO enzymes were verified with the model substrate of FMO. Importantly, the SeFMOs had significantly higher oxidative activities on metaflumizone and lambda-cyhalothrin than on model substrates and other insecticides tested. The three SeFMOs were mainly expressed in the midgut, fat body and Malpighian tubules. The tissues responsible for xenobiotic metabolism and their expression characteristics were similar to those of P450s acting as detoxification genes. The study also revealed that the expression of SeFMOs could be induced by insecticide exposure, and that SeFMOs were over-expressed in a metaflumizone-resistant strain of S. exigua. These results suggest that SeFMOs are important insecticide detoxifying enzymes, and that over-expression of FMO genes may be one of the mechanisms for metabolic resistance in S. exigua.

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“…The lack of such overproduction in strains isolated from insects found on the non-toxic boxelder and maple trees may be explained by the hypothesis that overproduction of riboflavin allows the insects to live on alkaloid-producing toxic plants using a mechanism of detoxification of alkaloids using flavin cofactor (Miranda et al 1991; Cashman et al 1996; Sehlmeyer et al 2010; Langel and Ober 2011). …”

Section: Discussionmentioning

confidence: 99%

Genomes of Ashbya Fungi Isolated from Insects Reveal Four Mating-Type Loci, Numerous Translocations, Lack of Transposons, and Distinct Gene Duplications

Dietrich

Voegeli

Kuo

et al. 2013

G3 Genes|Genomes|Genetics

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The filamentous fungus Ashbya gossypii is a cotton pathogen transmitted by insects. It is readily grown and manipulated in the laboratory and is commercially exploited as a natural overproducer of vitamin B2. Our previous genome analysis of A. gossypii isolate ATCC10895, collected in Trinidad nearly 100 years ago, revealed extensive synteny with the Saccharomyces cerevisiae genome, leading us to use it as a model organism to understand the evolution of filamentous growth. To further develop Ashbya as a model system, we have investigated the ecological niche of A. gossypii and isolated additional strains and a sibling species, both useful in comparative analysis. We isolated fungi morphologically similar to A. gossypii from different plant-feeding insects of the suborder Heteroptera, generated a phylogenetic tree based on rDNA-ITS sequences, and performed high coverage short read sequencing with one A. gossypii isolate from Florida, a new species, Ashbya aceri, isolated in North Carolina, and a genetically marked derivative of ATCC10895 intensively used for functional studies. In contrast to S. cerevisiae, all strains carry four not three mating type loci, adding a new puzzle in the evolution of Ashbya species. Another surprise was the genome identity of 99.9% between the Florida strain and ATCC10895, isolated in Trinidad. The A. aceri and A. gossypii genomes show conserved gene orders rearranged by eight translocations, 90% overall sequence identity, and fewer tandem duplications in the A. aceri genome. Both species lack transposable elements. Finally, our work identifies plant-feeding insects of the suborder Heteroptera as the most likely natural reservoir of Ashbya, and that infection of cotton and other plants may be incidental to the growth of the fungus in its insect host.

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Evolutionary recruitment of a flavin-dependent monooxygenase for stabilization of sequestered pyrrolizidine alkaloids in arctiids

Cited by 23 publications

References 85 publications

Occurrence of Sarmentosin and Other Hydroxynitrile Glucosides in Parnassius (Papilionidae) Butterflies and Their Food Plants

Occurrence of Sarmentosin and Other Hydroxynitrile Glucosides in Parnassius (Papilionidae) Butterflies and Their Food Plants

Molecular characterization, expression pattern and metabolic activity of flavin‐dependent monooxygenases inSpodoptera exigua

Genomes of Ashbya Fungi Isolated from Insects Reveal Four Mating-Type Loci, Numerous Translocations, Lack of Transposons, and Distinct Gene Duplications

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