ArticlePlant physiology2005
Molecular and biochemical characterization of 2-hydroxyisoflavanone dehydratase. Involvement of carboxylesterase-like proteins in leguminous isoflavone biosynthesis.
Article in Plant physiology, 2005. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 71 papers.
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71 citing papers in PubMed, 164 citations in OpenAlex.
- Functional identification of key enzymes in calycosin biosynthesis inPharmaceutical science advances · 2026Article
- The Biosynthesis of a Fungal Flavonoid, Chlorflavonin, Precisely Controlled by Two Types of Equilibrium States.Journal of the American Chemical Society · 2026Article
- Integrated Multi-Omics Analysis Revealed the Synergistic Regulatory Mechanisms of Salt Tolerance in Soybean (Kefeng 1).Plants (Basel, Switzerland) · 2026Article
- Glyceollin biosynthesis in a plant chassis engineered for isoflavone production.Nature chemical biology · 2025Article
- Key genes in a "Galloylation-Degalloylation cycle" controlling the synthesis of hydrolyzable tannins in strawberry plants.Horticulture research · 2025Article
- Integrative analysis of metabolite and transcriptome reveals the biosynthetic pathway and candidate genes for iridoid glycoside biosynthesis inFrontiers in plant science · 2025Article
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- Elucidating the metabolic roles of isoflavone synthase-mediated protein-protein interactions in yeast.bioRxiv : the preprint server for biology · 2024Article
- Whole-genome sequencing analysis of soybean diversity across different countries and selection signature of Korean soybean accession.G3 (Bethesda, Md.) · 2024Article
- Differentially Expressed Genes Related to Isoflavone Biosynthesis in a Soybean Mutant Revealed by a Comparative Transcriptomic Analysis.Plants (Basel, Switzerland) · 2024Article
- Evolution and diversification of carboxylesterase-like [4+2] cyclases in aspidosperma and iboga alkaloid biosynthesis.Proceedings of the National Academy of Sciences of the United States of America · 2024Article
- Identification of Genes Responsible for the Synthesis of Glycitein Isoflavones in Soybean Seeds.Plants (Basel, Switzerland) · 2024Article
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- Biosynthesis and metabolic engineering of isoflavonoids in model plants and crops: a review.Frontiers in plant science · 2024Review
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- Discovery of isoflavone phytoalexins in wheat reveals an alternative route to isoflavonoid biosynthesis.Nature communications · 2023Article
- New dual functionalSynthetic and systems biotechnology · 2023Article
- Redesigning plant specialized metabolism with supervised machine learning using publicly available reactome data.Computational and structural biotechnology journal · 2023Review
- The protein conformational basis of isoflavone biosynthesis.Communications biology · 2022Article
11 more citing papers are in PubMed but not listed here.
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3 authors at 1 institution in 1 country.
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No grant is acknowledged in the PubMed record.
Abstract
Isoflavonoids are ecophysiologically active secondary metabolites of the Leguminosae and known for health-promoting phytoestrogenic functions. Isoflavones are synthesized by 1,2-elimination of water from 2-hydroxyisoflavanones, the first intermediate with the isoflavonoid skeleton, but details of this dehydration have been unclear. We screened the extracts of repeatedly fractionated Escherichia coli expressing a Glycyrrhiza echinata cDNA library for the activity to convert a radiolabeled precursor into formononetin (7-hydroxy-4'-methoxyisoflavone), and a clone of 2-hydroxyisoflavanone dehydratase (HID) was isolated. Another HID cDNA was cloned from soybean (Glycine max), based on the sequence information in its expressed sequence tag library. Kinetic studies revealed that G. echinata HID is specific to 2,7-dihydroxy-4'-methoxyisoflavanone, while soybean HID has broader specificity to both 4'-hydroxylated and 4'-methoxylated 2-hydroxyisoflavanones, reflecting the structures of isoflavones contained in each plant species. Strikingly, HID proteins were members of a large carboxylesterase family, of which plant proteins form a monophyletic group and some are assigned defensive functions with no intrinsic catalytic activities identified. Site-directed mutagenesis with soybean HID protein suggested that the characteristic oxyanion hole and catalytic triad are essential for the dehydratase as well as the faint esterase activities. The findings, to our knowledge, represent a new example of recruitment of enzymes of primary metabolism during the molecular evolution of plant secondary metabolism.
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