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Flavonoid diversity and biosynthesis in seed of Arabidopsis thaliana

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Abstract

Functional characterization of genes involved in the flavonoid metabolism and its regulation requires in-depth analysis of flavonoid structure and composition of seed from the model plant Arabidopsis thaliana. Here, we report an analysis of the diverse and specific flavonoids that accumulate during seed development and maturation in wild types and mutants. Wild type seed contained more than 26 different flavonoids belonging to flavonols (mono and diglycosylated quercetin, kaempferol and isorhamnetin derivatives) and flavan-3-ols (epicatechin monomers and soluble procyanidin polymers with degrees of polymerization up to 9). Most of them are described for the first time in Arabidopsis. Interestingly, a novel group of four biflavonols that are dimers of quercetin-rhamnoside was also detected. Quercetin-3-O-rhamnoside (the major flavonoid), biflavonols, epicatechin and procyanidins accumulated in the seed coat in contrast to diglycosylated flavonols that were essentially observed in the embryo. Epicatechin, procyanidins and an additional quercetin-rhamnoside-hexoside derivative were synthesized in large quantities during seed development, whereas quercetin-3-O-rhamnoside displayed two peaks of accumulation. Finally, 11 mutants affected in known structural or regulatory functions of the pathway and their three corresponding wild types were also studied. Flavonoid profiles of the mutants were consistent with previous predictions based on genetic and molecular data. In addition, they also revealed the presence of new products in seed and underlined the plasticity of this metabolic pathway in the mutants.

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Abbreviations

ANR:

Anthocyanidin reductase

C:

Catechin

CE:

Condensing enzyme

CHI:

Chalcone isomerase

CHS:

Chalcone synthase

DAF:

Days after flowering

DFR:

Dihydroflavonol-4-reductase

EC :

Epicatechin

F3H:

Flavonol 3-hydroxylase

F3′H:

Flavonol 3′-hydroxylase

FLS:

Flavonol synthase

GST:

Gluthatione S-transferase

GT:

Glycosyltransferase

LC:

Liquid chromatography

LDOX:

Leucoanthocyanidin dioxygenase

mDP:

Mean degree of polymerization

MS:

Mass spectrometry

OMT:

Methyltransferase

PA:

Proanthocyanidin

PC:

Procyanidin

tt :

Transparent testa

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Acknowledgements

We wish to thank B. Weisshaar (Universität Bielefeld, Germany) for the gift of the fls1 mutant seed and N. Nesi (INRA Le Rheu, France) for her contribution to the initial characterization of the Versailles transparent testa mutants. Finally, we acknowledge V. Cheynier (INRA Montpellier, France), A. Baudry and H. North (INRA Versailles) for comments on the manuscript. This work was supported by GENOPLANTE (NO2001 00045) and the European Commission (FOOD-CT-2004-513960 FLAVO).

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Authors and Affiliations

  1. Laboratoire de Biologie des Semences, UMR 204 INRA-INAPG, Institut Jean-Pierre Bourgin, 78026, Versailles Cedex, France

    Jean-Marc Routaboul, Isabelle Debeaujon, Lucille Pourcel, Michel Caboche & Loïc Lepiniec

  2. Laboratoire de Phytopharmacie et Médiateurs Chimiques, INRA, 78026, Versailles Cedex, France

    Lucien Kerhoas & Jacques Einhorn

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  1. Jean-Marc Routaboul
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  2. Lucien Kerhoas
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  3. Isabelle Debeaujon
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  4. Lucille Pourcel
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  5. Michel Caboche
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  6. Jacques Einhorn
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  7. Loïc Lepiniec
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Correspondence to Jean-Marc Routaboul.

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Routaboul, JM., Kerhoas, L., Debeaujon, I. et al. Flavonoid diversity and biosynthesis in seed of Arabidopsis thaliana . Planta 224, 96–107 (2006). https://doi.org/10.1007/s00425-005-0197-5

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