Metabolomics-oriented isolation and structure elucidation of 37 compounds including two anthocyanins from Arabidopsis thaliana

Nakabayashi, Ryo; Kusano, Miyako; Kobayashi, Makoto; Tohge, Takayuki; Yonekura‐Sakakibara, Keiko; Kogure, Noriyuki; Yamazaki, Mami; Kitajima, Mariko; Saito, Kazuki; Takayama, Hiromitsu

doi:10.1016/j.phytochem.2009.03.021

Cited by 110 publications

(76 citation statements)

References 68 publications

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“…LC-MS analyses of individual flavonoids was performed as previously described (Routaboul et al, 2006(Routaboul et al, , 2012 using a Quattro LC with an ESI Z-Spray interface (MicroMass), an Alliance 2695 RP-HPLC system, and a Waters 2487 UV detector set at 280 nm. Anthocyanins and flavonols were identified based on mass fragmentation in comparison with reported data (Tohge et al, 2005;Nakabayashi et al, 2009). Flavonol contents were expressed relative to quercetin-3-O-rhamnoside, rutin, and epicatechin (Extrasynthese) external standards, or monoglycosylated and diglycosylated flavonols and flavan-3-ols (PAs), respectively.…”

Section: Flavonoid Analysis Using Lc-msmentioning

confidence: 99%

Stitching together the Multiple Dimensions of Autophagy Using Metabolomics and Transcriptomics Reveals Impacts on Metabolism, Development, and Plant Responses to the Environment inArabidopsis

et al. 2014

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Autophagy is a fundamental process in the plant life story, playing a key role in immunity, senescence, nutrient recycling, and adaptation to the environment. Transcriptomics and metabolomics of the rosette leaves of Arabidopsis thaliana autophagy mutants (atg) show that autophagy is essential for cell homeostasis and stress responses and that several metabolic pathways are affected. Depletion of hexoses, quercetins, and anthocyanins parallel the overaccumulation of several amino acids and related compounds, such as glutamate, methionine, glutathione, pipecolate, and 2-aminoadipate. Transcriptomic data show that the pathways for glutathione, methionine, raffinose, galacturonate, and anthocyanin are perturbed. Anthocyanin depletion in atg mutants, which was previously reported as a possible defect in flavonoid trafficking to the vacuole, appears due to the downregulation of the master genes encoding the enzymes and regulatory proteins involved in flavonoid biosynthesis. Overexpression of the PRODUCTION OF ANTHOCYANIN PIGMENT1 transcription factor restores anthocyanin accumulation in vacuoles of atg mutants. Transcriptome analyses reveal connections between autophagy and (1) salicylic acid biosynthesis and response, (2) cytokinin perception, (3) oxidative stress and plant defense, and possible interactions between autophagy and the COP9 signalosome machinery. The metabolic and transcriptomic signatures identified for the autophagy mutants are discussed and show consistencies with the observed phenotypes.

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Section: Flavonoid Analysis Using Lc-msmentioning

confidence: 99%

Stitching together the Multiple Dimensions of Autophagy Using Metabolomics and Transcriptomics Reveals Impacts on Metabolism, Development, and Plant Responses to the Environment inArabidopsis

et al. 2014

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“…Finally, analytes, which can be measured but are not yet annotated, can readily be included in the STATIS analysis. In combination with enrichment analysis, such comparative analyses may hint at the putative roles of nonannotated metabolites in preserved metabolic functions and may help in prioritizing which nonannotated metabolites would be most valuable to place into highly labor-intensive structural identification pipelines (Nakabayashi et al, 2009). …”

Section: Discussionmentioning

confidence: 99%

Conserved Changes in the Dynamics of Metabolic Processes during Fruit Development and Ripening across Species

et al. 2013

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Computational analyses of molecular phenotypes traditionally aim at identifying biochemical components that exhibit differential expression under various scenarios (e.g. environmental and internal perturbations) in a single species. High-throughput metabolomics technologies allow the quantification of (relative) metabolite levels across developmental stages in different tissues, organs, and species. Novel methods for analyzing the resulting multiple data tables could reveal preserved dynamics of metabolic processes across species. The problem we address in this study is 2-fold. (1) We derive a single data table, referred to as a compromise, which captures information common to the investigated set of multiple tables containing data on different fruit development and ripening stages in three climacteric (i.e. peach [Prunus persica] and two tomato [Solanum lycopersicum] cultivars, Ailsa Craig and M82) and two nonclimacteric (i.e. strawberry [Fragaria 3 ananassa] and pepper [Capsicum chilense]) fruits; in addition, we demonstrate the power of the method to discern similarities and differences between multiple tables by analyzing publicly available metabolomics data from three tomato ripening mutants together with two tomato cultivars. (2) We identify the conserved dynamics of metabolic processes, reflected in the data profiles of the corresponding metabolites that contribute most to the determined compromise. Our analysis is based on an extension to principal component analysis, called STATIS, in combination with pathway overenrichment analysis. Based on publicly available metabolic profiles for the investigated species, we demonstrate that STATIS can be used to identify the metabolic processes whose behavior is similarly affected during fruit development and ripening. These findings ultimately provide insights into the pathways that are essential during fruit development and ripening across species.

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“…× cultorum 'Royal Violet' and 'Royal Red' were shown to comprise acylated cyanidin 3-sambubioside-5-glucosides as the main anthocyanins, and these anthocyanins (1-3) were classified into the group of 3-sambubioside-5-glucoside pattern as the glycosylation of anthocyanidins. To the best of our knowledge, plants containing this group of anthocyanins are Arabidopsis (Bloor and Abrahams, 2002;Nakabayashi et al, 2009), Cheiranthus (Tatsuzawa et al, 2006), Heliophila (Saito et al, 2011b), Lobularia (Tatsuzawa et al, 2006(Tatsuzawa et al, , 2007(Tatsuzawa et al, , 2010c, Lunaria (Tatsuzawa et al, 2006), Matthiola (Saito et al, 1995(Saito et al, , 1996Tatsuzawa et al, 2012), Orychophragmus (Honda et al, 2005), and Sinapis (Takeda et al, 1988) in the family Brassicaceae. The acylation pattern of the three anthocyanins (1-3) was rather simple, with 1 and 3 being acylated with one molecule each of hydroxycinnamic acid and malonic acid, and 2 being acylated with one molecule of hydroxycinnamic acid.…”

Section: Discussionmentioning

confidence: 99%

Copigmentation with Acylated Anthocyanin and Kaempferol Glycosides in Violet and Purple Flower Cultivars of Aubrieta ^|^times; cultorum (Brassicaceae)

Tatsuzawa

Aiba

Morino

et al. 2012

J. Japan. Soc. Hort. Sci.

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Flavonoid pigments and flower colors of the violet and purple flower cultivars 'Royal Violet' and 'Royal Red', respectively, of Aubrieta × cultorum in the family Brassicaceae were investigated. Three acylated cyanidin 3-sambubioside-5-glucosides (1-3) were isolated as the main anthocyanins from violet and purple flowers of both cultivars. In particular, 1 was the dominant anthocyanin in both cultivars. Furthermore, an acylated flavonol glycoside (4) and another acylated flavonol glycoside (5) were isolated as the main flavonol pigments from flowers of 'Royal Violet' and 'Royal Red', respectively. The structures of 1-5 were elucidated by chemical and spectroscopic methods. Pigments 1, 2, 4, and 5 were found to be new flavonoid pigments. The structures of 1 and 2 were determined to be cyanidin On the visible absorption spectral curve, fresh petals and pressed petal juices of 'Royal Violet' in pH 5.0 buffer solution showed two characteristic absorption maxima at 560 and 604 nm and those of 'Royal Red' showed a single broad absorption maximum near 546 nm. In the reproducible experiments of their flower colors in pH 5.0 buffer solution, the violet solution was produced by the mixture of 1 and 4 (1 : 2) and exhibited characteristic absorption maxima at 560 and 604 nm, similar to those of the flower of 'Royal Violet'. In contrast, a mixture of 1 and 5 or that of 1 and other common copigments produced a purple solution with only one absorption maximum near 547 nm. From these results, it was revealed that 4 was more appropriate for the bluing effect of A. × cultorum cultivars by intermolecular copigmentation with 1 than 5.

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Metabolomics-oriented isolation and structure elucidation of 37 compounds including two anthocyanins from Arabidopsis thaliana

Cited by 110 publications

References 68 publications

Stitching together the Multiple Dimensions of Autophagy Using Metabolomics and Transcriptomics Reveals Impacts on Metabolism, Development, and Plant Responses to the Environment inArabidopsis

Stitching together the Multiple Dimensions of Autophagy Using Metabolomics and Transcriptomics Reveals Impacts on Metabolism, Development, and Plant Responses to the Environment inArabidopsis

Conserved Changes in the Dynamics of Metabolic Processes during Fruit Development and Ripening across Species

Copigmentation with Acylated Anthocyanin and Kaempferol Glycosides in Violet and Purple Flower Cultivars of Aubrieta ^|^times; cultorum (Brassicaceae)

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