Hydroxycinnamoyltransferases in plant metabolism

Abstract

Hydroxycinnamoyltransferases are enzymes transferring hydroxycinnamoyl units like cinnamoyl, 4-coumaroyl, caffeoyl, feruloyl and sinapoyl moieties from an activating residue such as coenzyme A or glucose or activated as hydroxycinnamoyl ester (e.g. chlorogenate) to an acceptor molecule, most commonly to an OH or NH 2 group as ester or amide. The hydroxycinnamoyl groups play either a ''decorating'' role or are building blocks of more complex structures. Proteins catalysing hydroxycinnamoyl transfer have been known for many decades and are nowadays investigated on molecular and structural levels. At least four different protein families give rise to enzymes with hydroxycinnamoyltransferase activity: serine carboxypeptidase-like proteins, tyramine hydroxycinnamoyltransferase-like enzymes, BAHD acyltransferases and GDSL-lipase/esterase-like enzymes. Interestingly, the same or very similar products can be formed by enzymes from different enzyme classes and using differently activated hydroxycinnamoyl units. This review will summarise the current literature data on the features of hydroxycinnamoyltransferases from the four different enzyme groups. Keywords BAHD acyltransferase Á GDSL lipase/esterase-like acyltransferase Á Phenolic metabolism Á Serine carboxypeptidase-like acyltransferase Á THT-like hydroxycinnamoyltransferase Abbreviations HCT Hydroxycinnamoyltransferase HQT Hydroxycinnamoyl-CoA:quinate hydroxycinnamoyltransferase HST Hydroxycinnamoyl-CoA:shikimate hydroxycinnamoyltransferase SCPL Serine caryboxypeptidase-like THT Tyramine hydroxycinnamoyltransferase Hydroxycinnamic acid moieties in plant secondary products (Hydroxy)cinnamoyl units such as cinnamic, 4-coumaric, caffeic, ferulic and sinapic acids and their reduced derivatives (aldehydes, alcohols) are ubiquitous building blocks in plant secondary metabolites. In many cases, the (hydroxy)cinnamoyl unit is an essential structural feature, in other cases it is a ''decorating'' part of the molecule (Petersen et al. 2010 and literature cited therein). Substituted hydroxycinnamyl alcohols (4-coumaryl, coniferyl = guajacyl, sinapyl = syringyl units) are the basis for the M. Petersen (&)

Proteomic Profiles of Cotton Fiber Developmental Transition from Cell Elongation to Secondary Wall Deposition

“…Phenylpropanoids are a group of plant secondary metabolites derived from phenylalanine which have a wide variety of functions both as structural and signaling molecules[36]. Plant HCTL enzyme participates in phenylpropanoid biosynthesis[37]. The marked downregulation in HCTL expression, consistent with prior reports that cotton fiber thickening is negatively related to phenylpropanoid content, suggest that the HTCL associated with phenylalanine metabolic pathways might play a key role in the fiber developmental transition process.…”

De novo assembly of Phlomis purpurea after challenging with Phytophthora cinnamomi

“…Play various roles including response to biotic and environmental stress. 17.7 0.0009 3.1 0.01 [ 72 , 73 ] 2245 53577 GDSL (esterases/lipases) Involved in defence from pathogens and stress, plant development, morphogenesis 30.9 4.18 e-22 9.92 4.2 e-08 [ 74 , 77 ] 51706 - lipase 6.2 0.007 - - [ 76 , 77 ] 766 9217 phospholipase 11.0 1.13 e-09 2.4 0.009 [ 76 , 92 ] - 24143 esterase - - 8.9 0.0004 [ 76 , 77 ] 15968 - cc-nbs-lrr resistance-genes in plant response to pathogens 7.7 0.0006 - - [ 82 , 83 ] 64844 - glycosyltransferase catalyzes transfer of sugars from nucleotide DP to a nucleophilic glycosyl acceptor 7.7 0.0006 - - [ 78 ] 12279 69649 udp-glycosyltransferase catalyzes conversion of cycloartenol to steroidal saponins 11.1 1.01 e-14 3.5 0.0016 [ ...…”

“…The involvement of gdsl genes in plants is still poorly understood. Recently it has been subject of much attention in studies regarding for example, gene family diversity or structural and functional studies [ 75 – 77 ].…”

An essential role of caffeoyl shikimate esterase in monolignol biosynthesis in Medicago truncatula

“…Incubation of caffeoyl shikimate with buffer alone, or with enzyme extracts with low CSE activity, resulted in the appearance of a new compound with lower retention time but identical UV spectrum to the initial substrate. Initially, we thought that this compound might be an additional ester of shikimate, formed either by trans‐esterification (Petersen, ) or possibly through additional activity of HCT; this latter type of reaction has recently been reported for formation of dicaffeoyl quinate (Vanholme et al ., 2013a; Moglia et al ., ). However, MS analysis indicated that the compound could not be a dicaffeoyl ester, and, because it is formed in the absence of enzyme, it is probably an adduct formed by reaction with a component in the buffer.…”