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(Reference retrieved automatically from SciELO through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Amino acids L-phenylalanine and L-lysine involvement in trans and cis piperamides biosynthesis in two Piper species

Full text
Author(s):
F. Cotinguiba ; H. M. Debonsi ; R. V. Silva [3] ; R. M. Pioli ; R. A. Pinto [5] ; L. G. Felippe [6] ; S. N. López ; M. J. Kato [8] ; M. Furlan [9]
Total Authors: 9
Document type: Journal article
Source: Brazilian Journal of Biology; v. 82, 2023-01-13.
Abstract

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. (AU)

FAPESP's process: 14/25705-0 - Metabolic engineering of the ergosterol pathway of Saccharomyces cerevisiae to improve production of the triterpene friedelin
Grantee:Tatiana Maria de Souza Moreira
Support Opportunities: Scholarships abroad - Research Internship - Post-doctor
FAPESP's process: 06/50086-5 - Characterization of prenyltransferase of Piper crassinervium and gaudichaudianum (Piperaceae)
Grantee:Silvia Noelí López
Support Opportunities: Scholarships in Brazil - Post-Doctoral
FAPESP's process: 11/10379-1 - CLONING AND CHARACTERIZATION OF OXIDOSQUALENE CYCLASES FROM Maytenus ilicifolia Mart. ex Reissek
Grantee:Tatiana Maria de Souza Moreira
Support Opportunities: Scholarships in Brazil - Post-Doctoral
FAPESP's process: 14/03819-3 - Cloning and functional characterization of oxidoesqualene cyclases of Maytenus ilicifolia
Grantee:Cleslei Fernando Zanelli
Support Opportunities: Regular Research Grants