Survey of volatile oxylipins and their biosynthetic precursors in bryophytes

Croisier, Emmanuel; Rempt, Martin; Pohnert, Georg

doi:10.1016/j.phytochem.2009.12.004

Cited by 38 publications

(52 citation statements)

References 25 publications

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“…Volatile oxylipins derived from arachidonic acid were also detected after wounding P. patens tissues [48]. Novel acetylenic oxylipins have been identified in other mosses [49], and it remains an open question if some of these metabolites play a role in defense against fungal and oomycete pathogens. P. patens is for these reasons a very suitable system allowing the identification of new defense-related compounds that could have been changed or lost during the evolution of plants.…”

Section: Defense Responses Activated In P Patens After Fungal Andmentioning

confidence: 99%

The MossPhyscomitrella patensas a Model System to Study Interactions between Plants and Phytopathogenic Fungi and Oomycetes

León

2011

Journal of Pathogens

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The moss Physcomitrella patens has a great potential as a model system to perform functional studies of plant interacting with microbial pathogens. P. patens is susceptible to fungal and oomycete infection, which colonize and multiply in plant tissues generating disease symptoms. In response to infection, P. patens activates defense mechanisms similar to those induced in flowering plants, including the accumulation of reactive oxygen species, cell death with hallmarks of programmed cell death, cell wall fortification, and induction of defense-related genes like PAL, LOX, CHS, and PR-1. Functional analysis of genes with possible roles in defense can be performed due to the high rate of homologous recombination present in this plant that enables targeted gene disruption. This paper reviews the current knowledge of defense responses activated in P. patens after pathogen assault and analyzes the advantages of using this plant to gain further insight into plant defense strategies.

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Section: Defense Responses Activated In P Patens After Fungal Andmentioning

confidence: 99%

The MossPhyscomitrella patensas a Model System to Study Interactions between Plants and Phytopathogenic Fungi and Oomycetes

León

2011

Journal of Pathogens

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“…Since the profiling of volatiles indicated that other mosses are also rich in oxylipins, [4] it can be speculated that in general oxylipins might significantly contribute to the effective chemical defense of mosses.…”

Section: Angewandte Chemiementioning

confidence: 99%

“…In a recent survey of the volatile oxylipins (products of the oxidative transformation of polyunsaturated fatty acids) from mosses, we identified D. scoparium as a prolific producer of such metabolites. [4] In addition, this moss produces unusual acetylenic cyclopentenones from the dominant acetylenic fatty acid dicranin presumably also by means of oxylipin pathways. [5] Motivated by the observation that oxylipins often serve as defense metabolites or regulators of defense reactions in higher plants, [6,7] we explored the chemistry and chemical ecology of oxylipins of D. scoparium.…”

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confidence: 98%

Novel Acetylenic Oxylipins from the Moss Dicranum scoparium with Antifeeding Activity against Herbivorous Slugs

Rempt

Pohnert

2010

Angew Chem Int Ed

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Dedicated to Professor Wilhelm Boland on the occasion of his 60th birthdayMosses are seldom fed upon even in areas where intense herbivore pressure is observed on other plants. But even more than 100 years after the first investigations of Ernst Stahl on the chemical defense of plants and mosses against slugs and snails [1] we know very little about the nature and biosynthesis of metabolites responsible for moss chemical defense. [2,3] Dicranum scoparium is an example of a well-defended moss; it is globally distributed in temperate and arctic forests and often occurs in dense patches that show no sign of herbivory. In a recent survey of the volatile oxylipins (products of the oxidative transformation of polyunsaturated fatty acids) from mosses, we identified D. scoparium as a prolific producer of such metabolites.[4] In addition, this moss produces unusual acetylenic cyclopentenones from the dominant acetylenic fatty acid dicranin presumably also by means of oxylipin pathways. [5] Motivated by the observation that oxylipins often serve as defense metabolites or regulators of defense reactions in higher plants, [6,7] we explored the chemistry and chemical ecology of oxylipins of D. scoparium. As observed in higher plants and diatoms, the production of volatile oxylipins is triggered by mechanical wounding in mosses as well. [6,8] Comparing the ultraperformance liquid chromatography/ mass spectrometry (UPLC/MS) profiles of methanolic extracts obtained from D. scoparium before and after tissue disruption revealed that a complex mixture of metabolites is produced within seconds after wounding (Figure 1). Owing to the complexity of the chromatograms, we aimed to address the metabolic pathways guided by biosynthetic precursors labeled with stable isotopes. Therefore we prepared monoand dideuterated fatty acids and administered them to the moss (Scheme 1).The acetylenic fatty acid dicranin proved to be of special interest as a precursor of unusual novel oxylipins. After a 10 min administration of mono-or dideuterated dicranin suspended in water to frozen powdered moss, a complex mix of deuterated metabolites formed. Since not all oxylipins were chromatographically separated a manual evaluation of UPLC/MS data ran the risk of overlooking relevant signals. We therefore used an automated peak extraction routine that delivers mass/retention time pairs for every compound. These data from nontreated controls and mixtures obtained after treatment with mono-or dideuterated dicranin were then evaluated using a canonical analysis of principal coordinates [9] that enabled the rapid identification of dicranin-derived peaks (Figure 1; see the Supporting Information for experimental details). In contrast to the established manual evaluation of UPLC/MS runs this analysis allows an automated quick and comprehensive survey of metabolites derived from labeled precursors. This method covers the entire range of polarities and molecular weights recorded in LC/MS runs and picks up even minor or chromatographically not separated metabolites.T...

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“…Dies ist in guter Übereinstimmung mit der berichteten Freisetzung von 1-Penten-3-on, (E)-2-Pentenal, Hexenol und Hexenal nach mechanischer Verwundung von D. scoparium. [4] Die aufgereinigten Verbindungen dienten als Standard für die Quantifizierung der Oxylipinproduktion mit UPLC/MS. Oxylipine wurden nur in den grünen, blattartigen Phylloiden des Mooses gebildet, nicht aber in den verholzten Stämmen.…”

Section: Nach Demselben Experimentellen Schema Konnten Nach Applikatiunclassified

“…Unlängst zeigte ein Screening, dass D. scoparium durch die Oxidation von ungesättigten Fettsäuren zahlreiche flüchtige Oxylipine produziert. [4] Aus diesem Moos wurden außerdem ungewöhnliche acetylenische Cyclopentenone isoliert, die wahrscheinlich auch über Oxylipin-Stoffwechselwege aus der im Moos dominanten acetylenischen Fettsäure Dicranin biosynthetisiert werden. [5] Motiviert durch die Beobachtung, dass in anderen Organismen Oxylipine oft direkt als Verteidigungsmetabolite fungieren oder an der Regulation von Verteidigungsreaktionen beteiligt sind, [6,7] untersuchen wir die chemische Ökologie dieser Verbindungen aus D. scoparium.…”

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Neue acetylenische Oxylipine mit fraßhemmenden Eigenschaften gegen herbivore Schnecken aus dem Moos Dicranum scoparium

Rempt

Pohnert

2010

Angewandte Chemie

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Survey of volatile oxylipins and their biosynthetic precursors in bryophytes

Cited by 38 publications

References 25 publications

The MossPhyscomitrella patensas a Model System to Study Interactions between Plants and Phytopathogenic Fungi and Oomycetes

The MossPhyscomitrella patensas a Model System to Study Interactions between Plants and Phytopathogenic Fungi and Oomycetes

Novel Acetylenic Oxylipins from the Moss Dicranum scoparium with Antifeeding Activity against Herbivorous Slugs

Neue acetylenische Oxylipine mit fraßhemmenden Eigenschaften gegen herbivore Schnecken aus dem Moos Dicranum scoparium

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