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Patrick Rollin - One of the best experts on this subject based on the ideXlab platform.
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Glucosinolates of the only three Brassicales indigenous to French Polynesia.
Natural product research, 2019Co-Authors: Sabine Montaut, Phila Raharivelomanana, Jean-françois Butaud, Tamatoa Lehartel, Patrick RollinAbstract:The glucosinolate (GL) profiles in leaf and stem of Rorippa sarmentosa (G.Forst. ex DC.) J.F.Macbr., Lepidium bidentatum Montin var. bidentatum, and Capparis spinosa subsp. cordifolia (Lam.) Fici indigenous to French Polynesia were investigated for the first time using LC-MS analysis. In the present study, we have established the presence of 8 known GLs in R. sarmentosa: 4-(methylsulfinyl)butyl- (1), but-3-enyl- (2), 5-(methylsulfinyl)pentyl- (3), 6-(methylsulfinyl)hexyl- (4), indol-3-ylmethyl- (6), 2-phenylethyl- (7), 8-(methylsulfinyl)octyl- (8), and 9-(methylsulfinyl)nonyl- (9) GLs. We have also tentatively identified for the first time the presence in R. sarmentosa of 7-(methylsulfinyl)heptyl GL (5). In addition, we have identified two known GLs in L. bidentatum var. bidentatum: benzyl- (10) and 4-methoxybenzyl- (11) GLs. Finally, the known methyl GL (12) was shown to be largely predominant in C. spinosa subsp. cordifolia.
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Glucosinolate turnover in Brassicales species to an oxazolidin-2-one, formed via the 2-thione and without formation of thioamide
Phytochemistry, 2018Co-Authors: Niels Agerbirk, Annemarie Matthes, Pernille Ø. Erthmann, Luisa Ugolini, Susanna Cinti, Eleni Lazaridi, Jean-marc Nuzillard, Caroline Muller, Søren Bak, Patrick RollinAbstract:Glucosinolates are found in plants of the order Brassicales and hydrolyzed to different breakdown products, particularly after tissue damage. In Barbarea vulgaris R.Br. (Brassicaceae), the dominant glucosinolate in the investigated “G-type” is glucobarbarin, (S)-2-hydroxy-2-phenylethylglucosinolate. Formation of the nitrile from glucobarbarin was observed in vitro, while a previously suggested thioamide (synonym thionamide) was not confirmed. Resedine (5-phenyl-1,3-oxazolidin-2-one) was detected after glucobarbarin hydrolysis in crushed B. vulgaris leaves and siliques, but not in intact parts. The abundance increased for several hours after completion of hydrolysis. The corresponding 1,3-oxazolidine-2-thione (OAT), with the common name barbarin, was also formed, and appeared to be the precursor of resedine. Addition of each of two non-endogenous OATs, (S)-5-ethyl-5-methylOAT and (R)-5-vinylOAT (R-goitrin), to a leaf homogenate resulted in formation of the corresponding 1,3-oxazolidin-2-ones (OAOs), confirming the metabolic connection of OAT to OAO. Formation of OAOs was inhibited by prior brief heating of the homogenate, suggesting enzyme involvement. We suggest the conversion of OATs to OAOs to be catalyzed by an enzyme (“oxazolidinethionase”) responsible for turnover of OAT formed in intact plants. Resedine had been reported as an alkaloid from another species - Reseda luteola L. (Resedaceae) - naturally containing the glucosinolate glucobarbarin. However, resedine was not detected in intact R. luteola plants, but formed after tissue damage. The formation of resedine in two families suggests a broad distribution of putative OATases in the Brassicales; potentially involved in glucosinolate turnover that needs myrosinase activity as the committed step. In agreement with the proposed function of OATase, several candidate genes for myrosinases in glucosinolate turnover in intact plants were discovered in the B. vulgaris genome. We also suggest that biotechnological conversion of OATs to OAOs might improve the nutritional value of Brassicales protein. HPLC-MS/MS methods for detection of these glucobarbarin products are described.
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Glucosinolates: Novel Sources and Biological Potential
Glucosinolates, 2017Co-Authors: Ivica Blaževic, Franko Burčul, Sabine Montaut, Patrick RollinAbstract:In this chapter, some of the most recent information on glucosinolate-containing plant families is presented. Glucosinolates (GLs) are structurally homogenous secondary metabolites present in the Brassicaceae, Capparidaceae, Moringaceae, and Resedaceae families, as well as in other less-studied families of the order Brassicales. Based on the GL contents, new subdivisions of GL-containing plants are suggested. It was shown that only a limited number of the reported ca 130 GLs are available in fair quantities, acceptable for further investigation of the biological potential. In recent years, degradation products of a limited number of GLs (e.g., gluconasturtiin, glucoraphanin, glucomoringin), mostly isothiocyanates, have been found to possess real pharmacological activity. Some of the biological aspects of GLs and isothiocyanates which have been in recent focus are presented.
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Unexpected matrix interactions in liquid secondary ion mass spectrometry of two pyranosyl mercaptans
Rapid Communications in Mass Spectrometry, 2011Co-Authors: Christian Gardrat, Benoît Joseph, Christiane Vitry, Alain Castellan, Patrick RollinAbstract:An unexpected interaction with a thioglycerol matrix appeared in the liquid secondary ion mass spectrometry (LSIMS) spectra of two pyranosyl mercaptans [2,3,4,6-tetra-O-acetyl-1-thio-beta-D-glucopyranose (1a) and 2,3,4,6-tetra-O-acetyl-1,5-dithio-beta-D-glucopyranose (1b)] often used to prepare glucosinolates, important thiosaccharidic metabolites found in all plants of the order Brassicales. The reactions, probably occurring in the solvent cage, seem to involve radical mechanisms.
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Unexpected matrix interactions in liquid secondary ion mass spectrometry of two pyranosyl mercaptans.
Rapid Communications in Mass Spectrometry, 2011Co-Authors: Christian Gardrat, Benoît Joseph, Christiane Vitry, Alain Castellan, Patrick RollinAbstract:An unexpected interaction with a thioglycerol matrix appeared in the liquid secondary ion mass spectrometry (LSIMS) spectra of two pyranosyl mercaptans [2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranose (1a) and 2,3,4,6-tetra-O-acetyl-1,5-dithio-β-D-glucopyranose (1b)] often used to prepare glucosinolates, important thiosaccharidic metabolites found in all plants of the order Brassicales. The reactions, probably occurring in the solvent cage, seem to involve radical mechanisms.
Danièle Werck-reichhart - One of the best experts on this subject based on the ideXlab platform.
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Evolutionary interplay between sister cytochrome P450 genes shapes plasticity in plant metabolism
Nature Communications, 2016Co-Authors: Raquel Tavares, Evan S. Forsythe, Gabriella Jonasson, Stéphanie Boutet-mercey, Mark A. Beilstein, Takayuki Tohge, Raphaël Lugan, Francois Andre, Danièle Werck-reichhartAbstract:Genes in the cytochrome P450 family have evolved a wide range of functions. Here, Liu et al. reconstruct the evolution of the P450 genes CYP98A8 and CYP98A9 in the Brassicales, revealing a complex history of retrotransposition, tandem duplication and neofunctionalization, followed by subfunctionalization or gene loss in specific lineages.
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Evolutionary interplay between sister cytochrome P450 genes shapes plasticity in plant metabolism
Nature Communications, 2016Co-Authors: Zhenhua Liu, Evan S. Forsythe, Gabriella Jonasson, Stéphanie Boutet-mercey, Mark A. Beilstein, Takayuki Tohge, Raquel Tavares, Raphaël Lugan, Francois Andre, Danièle Werck-reichhartAbstract:Genes in the cytochrome P450 family have evolved a wide range of functions. Here, Liu et al. reconstruct the evolution of the P450 genes CYP98A8 and CYP98A9 in the Brassicales, revealing a complex history of retrotransposition, tandem duplication and neofunctionalization, followed by subfunctionalization or gene loss in specific lineages. Expansion of the cytochrome P450 gene family is often proposed to have a critical role in the evolution of metabolic complexity, in particular in microorganisms, insects and plants. However, the molecular mechanisms underlying the evolution of this complexity are poorly understood. Here we describe the evolutionary history of a plant P450 retrogene, which emerged and underwent fixation in the common ancestor of Brassicales, before undergoing tandem duplication in the ancestor of Brassicaceae. Duplication leads first to gain of dual functions in one of the copies. Both sister genes are retained through subsequent speciation but eventually return to a single copy in two of three diverging lineages. In the lineage in which both copies are maintained, the ancestral functions are split between paralogs and a novel function arises in the copy under relaxed selection. Our work illustrates how retrotransposition and gene duplication can favour the emergence of novel metabolic functions.
Christian Gardrat - One of the best experts on this subject based on the ideXlab platform.
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Unexpected matrix interactions in liquid secondary ion mass spectrometry of two pyranosyl mercaptans
Rapid Communications in Mass Spectrometry, 2011Co-Authors: Christian Gardrat, Benoît Joseph, Christiane Vitry, Alain Castellan, Patrick RollinAbstract:An unexpected interaction with a thioglycerol matrix appeared in the liquid secondary ion mass spectrometry (LSIMS) spectra of two pyranosyl mercaptans [2,3,4,6-tetra-O-acetyl-1-thio-beta-D-glucopyranose (1a) and 2,3,4,6-tetra-O-acetyl-1,5-dithio-beta-D-glucopyranose (1b)] often used to prepare glucosinolates, important thiosaccharidic metabolites found in all plants of the order Brassicales. The reactions, probably occurring in the solvent cage, seem to involve radical mechanisms.
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Unexpected matrix interactions in liquid secondary ion mass spectrometry of two pyranosyl mercaptans.
Rapid Communications in Mass Spectrometry, 2011Co-Authors: Christian Gardrat, Benoît Joseph, Christiane Vitry, Alain Castellan, Patrick RollinAbstract:An unexpected interaction with a thioglycerol matrix appeared in the liquid secondary ion mass spectrometry (LSIMS) spectra of two pyranosyl mercaptans [2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranose (1a) and 2,3,4,6-tetra-O-acetyl-1,5-dithio-β-D-glucopyranose (1b)] often used to prepare glucosinolates, important thiosaccharidic metabolites found in all plants of the order Brassicales. The reactions, probably occurring in the solvent cage, seem to involve radical mechanisms.
Benoît Joseph - One of the best experts on this subject based on the ideXlab platform.
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Unexpected matrix interactions in liquid secondary ion mass spectrometry of two pyranosyl mercaptans
Rapid Communications in Mass Spectrometry, 2011Co-Authors: Christian Gardrat, Benoît Joseph, Christiane Vitry, Alain Castellan, Patrick RollinAbstract:An unexpected interaction with a thioglycerol matrix appeared in the liquid secondary ion mass spectrometry (LSIMS) spectra of two pyranosyl mercaptans [2,3,4,6-tetra-O-acetyl-1-thio-beta-D-glucopyranose (1a) and 2,3,4,6-tetra-O-acetyl-1,5-dithio-beta-D-glucopyranose (1b)] often used to prepare glucosinolates, important thiosaccharidic metabolites found in all plants of the order Brassicales. The reactions, probably occurring in the solvent cage, seem to involve radical mechanisms.
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Unexpected matrix interactions in liquid secondary ion mass spectrometry of two pyranosyl mercaptans.
Rapid Communications in Mass Spectrometry, 2011Co-Authors: Christian Gardrat, Benoît Joseph, Christiane Vitry, Alain Castellan, Patrick RollinAbstract:An unexpected interaction with a thioglycerol matrix appeared in the liquid secondary ion mass spectrometry (LSIMS) spectra of two pyranosyl mercaptans [2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranose (1a) and 2,3,4,6-tetra-O-acetyl-1,5-dithio-β-D-glucopyranose (1b)] often used to prepare glucosinolates, important thiosaccharidic metabolites found in all plants of the order Brassicales. The reactions, probably occurring in the solvent cage, seem to involve radical mechanisms.
Alain Castellan - One of the best experts on this subject based on the ideXlab platform.
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Unexpected matrix interactions in liquid secondary ion mass spectrometry of two pyranosyl mercaptans
Rapid Communications in Mass Spectrometry, 2011Co-Authors: Christian Gardrat, Benoît Joseph, Christiane Vitry, Alain Castellan, Patrick RollinAbstract:An unexpected interaction with a thioglycerol matrix appeared in the liquid secondary ion mass spectrometry (LSIMS) spectra of two pyranosyl mercaptans [2,3,4,6-tetra-O-acetyl-1-thio-beta-D-glucopyranose (1a) and 2,3,4,6-tetra-O-acetyl-1,5-dithio-beta-D-glucopyranose (1b)] often used to prepare glucosinolates, important thiosaccharidic metabolites found in all plants of the order Brassicales. The reactions, probably occurring in the solvent cage, seem to involve radical mechanisms.
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Unexpected matrix interactions in liquid secondary ion mass spectrometry of two pyranosyl mercaptans.
Rapid Communications in Mass Spectrometry, 2011Co-Authors: Christian Gardrat, Benoît Joseph, Christiane Vitry, Alain Castellan, Patrick RollinAbstract:An unexpected interaction with a thioglycerol matrix appeared in the liquid secondary ion mass spectrometry (LSIMS) spectra of two pyranosyl mercaptans [2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranose (1a) and 2,3,4,6-tetra-O-acetyl-1,5-dithio-β-D-glucopyranose (1b)] often used to prepare glucosinolates, important thiosaccharidic metabolites found in all plants of the order Brassicales. The reactions, probably occurring in the solvent cage, seem to involve radical mechanisms.