Amino acids L-phenylalanine and L-lysine involvement in trans and cis piperamides biosynthesis in two Piper species
Year: 2022
Type: article
Abstract: Several Piper species accumulate piperamides as secondary metabolites, and although they have relevant biological importance, many details of their biosynthetic pathways have not yet been described experimentally. Experiments involving enzymatic reactions and labeled precursor feeding were performed using the species Piper tuberculatum and Piper arboreum. The activities of the phenylalanine ammonia lyase (PAL) enzymes, which are involved in the general phenylpropanoid pathway, were monitored by the conversion of the amino acid L-phenylalanine to cinnamic acid. The activity of the 4-hydroxylase (C4H) enzyme was also observed in P. tuberculatum by converting cinnamic acid to p-coumaric acid. L-[UL-14C]-phenylalanine was fed into the leaves of P. tuberculatum and incorporated into piperine (1), 4,5-dihydropiperine (2), fagaramide (4), trans-piplartine (7), and dihydropiplartine (9). In P. arboreum, it was only incorporated into the piperamide 4,5-dihydropiperiline (3). L-[UL-14C]-lysine was successfully incorporated into the 4,5-dihydropiperine piperidine group (2), dihydropyridinone, and trans- (7) and cis-piplartine (8). These data corroborate the proposal of mixed biosynthetic origin of piperamides with the aromatic moiety originating from cinnamic acid (shikimic acid pathway) and key amide construction with amino acids as precursors.
Source: Brazilian Journal of Biology
Language: English
Subfield: Pharmacology
Domain: Life Sciences
Open Access status: gold
Estimated APC paid: $680
Funders: Fundação de Amparo à Pesquisa do Estado de São Paulo, Coordenação de Aperfeiçoamento de Pessoal de Nível Superior, Conselho Nacional de Desenvolvimento Científico e Tecnológico, Fundação Carlos Chagas Filho de Amparo à Pesquisa do Estado do Rio de Janeiro, Agencia Nacional de Promoción Científica y Tecnológica
Awards: G1242077719, G1395192598, G1840770272, G1938623563, G1979085988, CIBFar - Center for Innovation in Biodiversity and Drug Discovery, G29316538, G3325778992, G350075096, G3572101131, G4058094409, G407438531, G4517143547, G5279469395, G6423199046, G6822879463, Cloning and functional characterization of oxidoesqualene cyclases of Maytenus ilicifolia, INCT 2014: biodiversity and natural products, G8778821334, G974782458
OpenAlex ID: W4317359883