2-Hydroxyisoflavanone Dehydratase is a Critical Determinant of Isoflavone Productivity in Hairy Root Cultures of Lotus japonicus

Shimamura, Mie; Akashi, Tomoyoshi; Sakurai, Nozomu; Suzuki, Hideyuki; Saito, Kazuki; Shibata, Daisuke; Ayabe, Shin Ichi; Aoki, Takeshi

doi:10.1093/pcp/pcm125

Cited by 58 publications

(38 citation statements)

References 21 publications

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“…3b). Recently, it was reported that overexpression of soybean HID in hairy roots of Lotus japonicus led to accumulation of daidzein and genistein at comparable levels to those found in transgenic Arabidopsis or alfalfa over-expressing IFS (Liu et al 2002;Deavours and Dixon 2005), but that over-expression of licorice IFS did not lead to accumulation of isoflavones (Shimamura et al 2007). The authors concluded that HID was a critical determinant for isoflavone biosynthesis in L. japonicus hairy root cultures.…”

Section: Genes Of Isoflavone Biosynthesis In Kudzu Rootsmentioning

confidence: 97%

A genomic approach to isoflavone biosynthesis in kudzu (Pueraria lobata)

Blount

Shu-jun

et al. 2011

Planta

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Roots of kudzu (Pueraria lobata) are a rich source of isoflavone O- and C-glycosides. Although O-glycosylation of (iso)flavonoids has been well characterized at the molecular level, no plant isoflavonoid C-glycosyltransferase genes have yet been isolated. To address the biosynthesis of kudzu isoflavonoids, we generated 6,365 high-quality expressed sequence tags (ESTs) from a subtraction cDNA library constructed using RNA from roots that differentially accumulate puerarin. The ESTs were clustered into 722 TCs and 3,913 singletons, from which 15 family I glycosyltransferases (UGTs) were identified. Hierarchical clustering analysis of the expression patterns of these UGTs with isoflavone synthase (IFS) in a range of tissues identified UGTs with potential functions in isoflavone glycosylation. The open reading frames of these UGTs were expressed in E. coli for functional analysis, and one was shown to preferentially glycosylate isoflavones at the 7-O-position. In addition, ESTs corresponding to chalcone synthase, chalcone reductase, chalcone isomerase (CHI) and 2-hydroxyisoflavanone dehydratase were identified. Recombinant CHI proteins had high activities with both 6'-deoxy- and 6'-hydroxy chalcones, typical of Type II CHIs. Establishment of this EST database and identification of genes associated with kudzu isoflavone biosynthesis and glycosylation provide a new resource for metabolic engineering of bioactive kudzu isoflavones.

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Section: Genes Of Isoflavone Biosynthesis In Kudzu Rootsmentioning

confidence: 97%

A genomic approach to isoflavone biosynthesis in kudzu (Pueraria lobata)

Blount

Shu-jun

et al. 2011

Planta

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“…Both of them are found in numerous edible plant species primarily belonging to the Fabaceae 1–3 or Amaryllidaceae families, 4 but are also found in the Asparagaceae 5 and Bignonaceae 6 families. Despite their wide distribution, these two polyphenols have been mainly studied as bio-active constituents of Glycyrrhiza species (licorice, Fabaceae).…”

Section: Introductionmentioning

confidence: 99%

Dynamic Residual Complexity of the Isoliquiritigenin–Liquiritigenin Interconversion During Bioassay

Simmler

Hajirahimkhan

Lankin

et al. 2013

J. Agric. Food Chem.

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Bioactive components in food plants can undergo dynamic processes that involve multiple chemical species. For example, 2′-hydroxychalcones can readily isomerize into flavanones. Although chemically well documented, this reaction has barely been explored in the context of cell-based assays. The present time-resolved study fills this gap by investigating the isomerization of isoliquiritigenin (a 2′-hydroxychalcone) and liquiritigenin (a flavanone) in two culture media (DMEM and RPMI) with and without MCF-7 cells, using HPLC-DAD-ESI/APCI-MS for analysis. Both compounds isomerized and epimerized under all investigated biological conditions, leading to mixtures of isoliquiritigenin and R/S-liquiritigenin, with 19.6% R enantiomeric excess. Consequently, all three species can potentially modulate the biological responses. This exemplifies dynamic residual complexity and demonstrates how both non-chiral reactions and enantiomeric discrimination can occur in bioassay media, with or without cells. The findings highlight the importance of controlling in situ chemical reactivity, influenced by biological systems when evaluating the mode of action of bioactives.

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“…Most of the genes involved in the biosynthesis of the isoflavonoid phytoalexin vestitol in Lotus japonicus have been identified (2,3,(40)(41)(42)(43)(44), however there have seen few studies on the interaction between leguminous plant defenses and symbioses with compatible and incompatible fungi through isoflavonoids. Here is, to analyze the fungal colonization of legume roots, the plant response during establishment of an associative symbiotic or incompatible interaction was investigated.…”

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confidence: 99%

Plant Growth-Promoting Fungus, Trichoderma koningi Suppresses Isoflavonoid Phytoalexin Vestitol Production for Colonization on/in the Roots of Lotus japonicus

2011

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The relationship between the colonization of Lotus japonicus by plant growth-promoting fungi (PGPF) and biosynthesis of the isoflavonoid phytoalexin vestitol, a major defensive response of leguminous plants, was analyzed. When PGPF including Trichoderma koningi, Fusarium equiseti, and Penicillium simplicissimum were inoculated onto L. japonicus roots, only T. koningi colonized the roots long-term and increased plant dry weight (126%). Microscopic observations of transverse sections of roots colonized by T. koningi demonstrated intercellular hyphal growth and the formation of yeast-like cells. The induction of plant defenses by fungal infections was examined by Northern analysis of genes involved in vestitol biosynthesis and HPLC of vestitol production in L. japonicus. Inoculation with symbiotic Mesorhizobium loti did not induce any accumulation of the transcripts. T. koningi immediately suppressed transcript levels to those induced by M. loti. The vestitol transuded from roots by T. koningi was detected at a level equivalent to that transuded by M. loti. Other PGPF and Calonectoria ilicola pathogenic to soybean but not to L. japonicus, stimulated continuous expression of genes and exudation of vestitol. These PGPF resembled mycorrhizal fungi in the establishment of symbiotic associations rather than fungal parasites.

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2-Hydroxyisoflavanone Dehydratase is a Critical Determinant of Isoflavone Productivity in Hairy Root Cultures of Lotus japonicus

Cited by 58 publications

References 21 publications

A genomic approach to isoflavone biosynthesis in kudzu (Pueraria lobata)

A genomic approach to isoflavone biosynthesis in kudzu (Pueraria lobata)

Dynamic Residual Complexity of the Isoliquiritigenin–Liquiritigenin Interconversion During Bioassay

Plant Growth-Promoting Fungus, Trichoderma koningi Suppresses Isoflavonoid Phytoalexin Vestitol Production for Colonization on/in the Roots of Lotus japonicus

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