ArticlePlant physiology2012
A structural basis for the biosynthesis of the major chlorogenic acids found in coffee.
Article in Plant physiology, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 67 papers, 1 of them a synthesis that pooled it.
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Who cites it
67 citing papers in PubMed, 1 synthesis or guideline pooled it.
- Genome-Wide Datasets of Chicories (International journal of molecular sciences · 2023Pooled it
- Biostimulatory Effect of 3-Acetonyl-3-Hydroxyoxindole on the Growth and Secondary Metabolites ofInternational journal of molecular sciences · 2026Article
- Completing the acylation landscape in plants: GDSL enzymes join the BAHD and SCPL acyltransferase families.Journal of experimental botany · 2026Review
- Advances in the Function Roles of Hydroxycinnamoyl-CoA Shikimate/Quinate Hydroxycinnamoyl Transferases: A Key Enzyme Linking Phenylpropanoid Metabolism to Plant Terrestrial Adaptation.Plants (Basel, Switzerland) · 2026Review
- Cloning and Characterization ofGenes · 2026Article
- Research Advances in the Synthesis, Metabolism, and Function of Chlorogenic Acid.Foods (Basel, Switzerland) · 2025Review
- Biosynthetic Mechanisms of Plant Chlorogenic Acid from a Microbiological Perspective.Microorganisms · 2025Review
- Hydroxycinnamoyl-coenzyme A: tetrahydroxyhexanedioate hydroxycinnamoyl transferase (HHHT) fromPeerJ · 2025Article
- Identification of the first plant caffeoyl-quinate esterases inFrontiers in plant science · 2025Article
- Identification of genetic factors influencing flavonoid biosynthesis through pooled transcriptome analysis in mungbean sprouts.Frontiers in plant science · 2025Article
- Biosynthesis of Feruloyl Glycerol from Ferulic Acid and Glycerol Through a Two-Enzyme Cascade Reaction.Applied biochemistry and biotechnology · 2024Article
- Mechanistic basis for the emergence of EPS1 as a catalyst in salicylic acid biosynthesis of Brassicaceae.Nature communications · 2024Article
- Seqrutinator: scrutiny of large protein superfamily sequence datasets for the identification and elimination of non-functional homologues.Genome biology · 2024Article
- Analysing a Group of Homologous BAHD Enzymes Provides Insights into the Evolutionary Transition of Rosmarinic Acid Synthases from Hydroxycinnamoyl-CoA:Shikimate/Quinate Hydroxycinnamoyl Transferases.Plants (Basel, Switzerland) · 2024Article
- Risk Assessment of Chlorogenic and Isochlorogenic Acids in Coffee By-Products.Molecules (Basel, Switzerland) · 2023Review
- Identification ofPhysiology and molecular biology of plants : an international journal of functional plant biology · 2023Article
- New cup out of old coffee: contribution of parental gene expression legacy to phenotypic novelty in coffee beans of the allopolyploid Coffea arabica L.Annals of botany · 2023Article
- Family characteristics, phylogenetic reconstruction, and potential applications of the plant BAHD acyltransferase family.Frontiers in plant science · 2023Review
- Structural identification of catalytic His158 of PtMAC2p fromFrontiers in bioengineering and biotechnology · 2023Article
- Exploring the metabolic and physiological roles ofFrontiers in plant science · 2023Article
7 more citing papers are in PubMed but not listed here.
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Authors and funding
10 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Chlorogenic acids (CGAs) are a group of phenolic secondary metabolites produced by certain plant species and an important component of coffee (Coffea spp.). The CGAs have been implicated in biotic and abiotic stress responses, while the related shikimate esters are key intermediates for lignin biosynthesis. Here, two hydroxycinnamoyl-coenzyme A shikimate/quinate hydroxycinnamoyl transferases (HCT/HQT) from coffee were biochemically characterized. We show, to our knowledge for the first time, that in vitro, HCT is capable of synthesizing the 3,5-O-dicaffeoylquinic acid diester, a major constituent of the immature coffee grain. In order to further understand the substrate specificity and catalytic mechanism of the HCT/HQT, we performed structural and mutagenesis studies of HCT. The three-dimensional structure of a native HCT and a proteolytically stable lysine mutant enabled the identification of important residues involved in substrate specificity and catalysis. Site-directed mutagenesis confirmed the role of residues leucine-400 and phenylalanine-402 in substrate specificity and of histidine-153 and the valine-31 to proline-37 loop in catalysis. In addition, the histidine-154-asparagine mutant was observed to produce 4-fold more dichlorogenic acids compared with the native protein. These data provide, to our knowledge, the first structural characterization of a HCT and, in conjunction with the biochemical and mutagenesis studies presented here, delineate the underlying molecular-level determinants for substrate specificity and catalysis. This work has potential applications in fine-tuning the levels of shikimate and quinate esters (CGAs including dichlorogenic acids) in different plant species in order to generate reduced or elevated levels of the desired target compounds.
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