Phenylpropanoid Metabolism

Abstract

Phenylpropanoid compounds encompass a wide range of structural classes with diverse biological functions in defence, survival and structural support associated with normal plant development (belying the term 'secondary metabolite'). The biosynthesis of phenylpropanoids is regulated by diverse environmental stimuli. Phenylpropanoid metabolism (other than flavonoids, not covered here) occupies a central place in the general aromatic metabolism of plants from shikimate to phenylalanine to lignin polymers and also to coumarins, phenolic volatiles and hydrolysable tannins. In recent years, genetics and biochemistry, along with methodology‐driven, computational, transgenic and comparative transcriptomic approaches, have led to significant advances in the identification of the families of genes encoding enzymes, transporters, regulatory factors involved in phenylpropanoid metabolism and a clearer picture of their functions in biotic and abiotic stress responses, plant development and enzyme/pathway evolution driven by interactions of species with their environment.

Key Concepts

  • Having one phenyl aromatic ring with one or more hydroxyl groups attached gives phenylpropanoids amphiphilic and reducing properties, underlying their ability to physically interact with other biomolecules.
  • Plants invest a large percentage of their fixed carbon into synthesising phenylpropanoids, from simple volatile phenolic acids such as the defence hormone salicylic acid to complex polyphenolic flavonoids encompassing thousands of compounds with myriad physiological and adaptive functions.
  • The shikimate pathway is the starting point for phenylpropanoid biosynthesis from shikimate product phenylalanine (l‐Phe), via the intermediate chorismate, which also serves as substrate for the synthesis of quinones and tocopherols important as electron acceptors in photosynthesis and aerobic respiration.
  • Phenylpropanoid biosynthesis proceeds from deamination of Phe to cinnamate by the rate‐limiting and environmentally regulated enzyme PAL, followed by oxidation of the ring to p‐coumarate, its activation with coenzymeA and a series of hydroxylation, methylation and reduction reactions to give cinnamic acids, ‐aldehydes and ‐alcohols that serve as substrates to generate a wide range of complex structures, notably polymers of coumaroyl, conferyl and sinapyl alcohols comprising lignin.
  • Recent studies have established the major pathway in plants which proceeds from p‐coumaroyl‐CoA → p‐coumaryl‐shikimate → caffeoyl‐shikimate → caffeoyl‐CoA → feruloyl CoA → coniferaldehyde → 5‐OH coniferaldehyde → sinapaldehyde → sinapate/sinapyl alcohol (oxidation versus reduction, respectively), instead of the original model of a grid/matrix of parallel ring oxidation and side‐chain redox pathways from hydroxycinnamic acids to alcohols.
  • Synthesis involves three subcellular compartments: chloroplast for Phe, cytosol for sinapoyl‐esters and the vacuole for trans‐esterifications. The identity of specific transporters, temporal‐ or organ‐specific regulatory factors for phenylpropanoid flux to (in)soluble polymers in the apoplast in response to biotic and abiotic stressors and whether lignin formation proceeds via precise channeling of individual precursors through metabolons (temporary structural–functional complexes formed between sequential enzymes) are key questions of practical significance that remain to be answered.

Keywords: shikimate pathway; hydroxycinnamic acids; coumarins; lignins; lignans

Figure 1. The shikimate pathway enzymes: (1) 3‐deoxy‐d‐arabino‐heptulosonate 7‐phosphate (DAHP); (2) 3‐dehydroquinate (DHQ) synthase; (3) 3‐dehydroquinate dehydratase; (4) shikimate oxidoreductase; (5) shikimate kinase; (6) 5‐enol‐puruvylshikimate 3‐phosphate synthase; (7) chorismate synthase; (8) chorismate mutase; (9) prephenate aminotransferase; (10) arogenate/prephenate dehydratase; (11) arogenate dehydrogenase; (12) anthranilate synthase; (13) anthranilate P‐ribosyltransferase; (14) P‐ribosylanthranilate isomerase; (15) indole 3‐glycerol‐P synthase; (16) tryptophan synthase; (17) aromatic amino acid aminotransferase; Pi, H2PO3 and KG, α‐keto‐glutarate. The major arogenate pathway steps (9, 10) to Phe are underlined.
Figure 2. Phenylpropanoid metabolic pathway enzymes from Phe leading to lignin et al. Horizontal and diagonal reactions correspond to ring modifications, vertical reactions correspond to side‐chain modifications. (18) Phenylalanine ammonia‐lyase; (19) cinnamate 4‐hydroxylase; (20) 4‐coumarate:CoA ligase; (21) hydroxycinnamoyl‐coenzyme A shikimate:quinate hydroxycinnamoyl‐transferase; (22) p‐coumaroyl shikimate 3′‐hydroxylase; (23) caffeoyl CoA 3‐O‐methyltransferase; (24) cinnamoyl‐CoA reductase; (25) ferulate 5‐hydroxylase; (26) caffeic/5‐hydroxyferulic bispecific O‐methyltransferase; (27) cinnamyl alcohol dehydrogenase; (28) hydroxycinnamaldehyde dehydrogenase; (29) sinapic acid:UDP‐glucose glucosyl transferase; (30) sinapoyl glucose:malate sinapoyl transferase; (31) sinapoyl glucose:choline sinapoyl transferase; (32) sinapoyl glucose:anthocyanin sinapoyltransferase; (33) sinapoyl glucose:sinapoylglucose sinapoyltransferase; (34) spermidine disinapoyl transferase; (35) spermidine dicoumaroyl transferase; (36) p‐coumaroyl‐CoA 2′ hydroxylase; (37) feruloyl CoA 6′ hydroxylase; (38) bergaptol O‐methyltransferase; (39) caffeoyl shikimate esterase; (40) laccase; (41) peroxidase, H2O2‐dependent and (42) Dirigent proteins.
Figure 3. An example of systems biology of Arabidopsis root xylem secondary cell wall biosynthesis in response to the environment. (a) Gene regulatory network for root xylem. Nodes represent transcription factors or wall gene promoters and edges (lines) represent protein–DNA interactions. Edges in feed‐forward loops are red. (b) A sample feed‐forward loop in red. (c) ‘Power edges’ between node sets represent suites of transcription factors that bind to the same set of promoters. (d) The secondary wall network from subfragments of cell‐wall promoters. (e) Proposed regulation of xylem‐specific network responsive to high salinity and iron deprivation. Reproduced with permission from Taylor‐Teeples et al. 2015 © Nature Publishing Group.
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Further Reading

Cheynier V, Comte G, Davies KM, Lattanzio V and Martens S (2013) Plant phenolics: Recent advances on their biosynthesis, genetics, and ecophysiology. Plant Physiology and Biochemistry 72: 1–20.

Dewick PM (2009) Medicinal Natural Products: A Biosynthetic Approach. Chichester, UK: John Wiley and Sons.

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Le Roy J, Huss B, Creach A, et al. (2016) Glycosylation is a major regulator of phenylpropanoid availability and biological activity in plants. Frontiers in Plant Science. DOI: doi.org/10.3389/fpls.2016.00735.

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Rock, Christopher D(Apr 2017) Phenylpropanoid Metabolism. In: eLS. John Wiley & Sons Ltd, Chichester. http://www.els.net [doi: 10.1002/9780470015902.a0001912.pub2]