Phenolic metabolism in the hornwort Anthoceros agrestis: 4-coumarate CoA ligase and 4-hydroxybenzoate CoA ligase

Abstract

Key message 4-Coumarate coenzyme A ligase and 4-hydroxybenzoate coenzyme A ligase from the hornwort Anthoceros agrestis expressed in E. coli were characterized on biochemical and molecular levels and showed interesting substrate specificities. Abstract Acyl-activating enzymes are associated with the biosynthesis or degradation of various metabolic products such as lipids, amino acids, sugars, and natural compounds. In this work, cDNA sequences encoding 4-coumarate coenzyme A ligase (4CL) and 4-hydroxybenzoate coenzyme A ligase (4HBCL) were amplified from the hornwort Anthoceros agrestis. The coding sequences were expressed in E. coli and purified by Ni-chelate chromatography. The CoA ligases exhibited different substrate specificities. 4CL catalyzed the activation of 4-coumaric acid, 3-coumaric acid, 2-coumaric acid, caffeic acid, isoferulic acid, ferulic acid, and cinnamic acid but lacked activities towards sinapic acid and benzoic acids. In contrast, 4HBCL preferred 4-hydroxybenzoic acid and benzoic acid, but also accepted other benzoic acid derivatives except salicylic acid and 3-aminosalicylic acid. Furthermore, 4HBCL also activated isoferulic acid, cinnamic acid, 2-coumaric acid, 3-coumaric acid, 4-coumaric acid and caffeic acid, but lacked affinity for ferulic acid and sinapic acid. These substrate specificities could be related to the phenolic compounds identified in Anthoceros agrestis.

Natural Products from Bryophytes: From Basic Biology to Biotechnological Applications

“…Either because the divergence of hornworts occurred before flavonoid pathway evolved or the hornwort ancestor acquired mutations that caused loss of the flavonoid biosynthetic ability and subsequently caused flavonoid loss in this lineage (Davies et al, 2020). The derivatives of the cinnamic acid, which is the central intermediate in the biosynthesis of flavonoids and other phenylpropanoids, are reported in the hornwort Anthoceros agrestis (Soriano et al, 2018;Wohl and Petersen, 2020).…”

Genome-Wide Identification of Genes Related to Biosynthesis of Phenolic Acid Derivatives in Bletilla striata at Different Suspension Culture Stages

“…Phenylalanine was deaminated and transformed into trans-cinnamic acid by phenylalanine ammonia-lyase (PAL) (Trivedi et al, 2022). Subsequently, phenolic acids such as trans-cinnamic acid, pcoumarate, and ferulic acid are formed under the action of cinnamate 4-hydroxylase (C4H), 4-coumaratecoa-ligase (4CL), O-methyltransferase (OMT), and other enzymes catalyzed further into caffeic acid and chlorogenic acid (Wohl and Petersen, 2020). HBA was one of the main components of phenolic compounds and the main precursor of aromatic compounds (Zhang Z. L. et al, 2020).…”

Physiological and Proteomic Responses of Contrasting Alfalfa (Medicago sativa L.) Varieties to High Temperature Stress

“…It is worth noting that 4-coumarate: CoA ligase-like protein (TRINITY_DN17517_c0_g1_Gene_20937) in MS30 has been down-regulated under HT stress. 4-coumarate: coenzyme A ligase (4CL) converts 4-coumaric acid and its hydroxylated derivatives into the CoA thiol esters, directing carbon flux into various end-products of phenylpropanoid metabolism, such as flavonoids and lignins ( Wohl and Petersen, 2020 ). Studies have shown that inhibiting the activity of COMT and 4CL could lead to a decrease in lignin content ( Awasthi et al, 2019 ; Wohl and Petersen, 2020 ).…”

“…4-coumarate: coenzyme A ligase (4CL) converts 4-coumaric acid and its hydroxylated derivatives into the CoA thiol esters, directing carbon flux into various end-products of phenylpropanoid metabolism, such as flavonoids and lignins ( Wohl and Petersen, 2020 ). Studies have shown that inhibiting the activity of COMT and 4CL could lead to a decrease in lignin content ( Awasthi et al, 2019 ; Wohl and Petersen, 2020 ). Therefore, we speculate that HT stress could also affect the heat tolerance of alfalfa by affecting the metabolic pathway of lignin.…”