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

Friedelin Synthase from Maytenus ilicifolia: Leucine 482 Plays an Essential Role in the Production of the Most Rearranged Pentacyclic Triterpene

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Souza-Moreira, Tatiana M. ; Alves, Thas B. ; Pinheiro, Karina A. ; Felippe, Lidiane G. ; De Lima, Gustavo M. A. ; Watanabe, Tatiana F. ; Barbosa, Cristina C. ; Santos, Vania A. F. F. M. ; Lopes, Norberto P. ; Valentini, Sandro R. ; Guido, Rafael V. C. ; Furlan, Maysa ; Zanelli, Cleslei F.
Total Authors: 13
Document type: Journal article
Source: SCIENTIFIC REPORTS; v. 6, NOV 22 2016.
Web of Science Citations: 9
Abstract

Among the biologically active triterpenes, friedelin has the most-rearranged structure produced by the oxidosqualene cyclases and is the only one containing a cetonic group. In this study, we cloned and functionally characterized friedelin synthase and one cycloartenol synthase from Maytenus ilicifolia (Celastraceae). The complete coding sequences of these 2 genes were cloned from leaf mRNA, and their functions were characterized by heterologous expression in yeast. The cycloartenol synthase sequence is very similar to other known OSCs of this type (approximately 80% identity), although the M. ilicifolia friedelin synthase amino acid sequence is more related to beta-amyrin synthases (65-74% identity), which is similar to the friedelin synthase cloned from Kalanchoe daigremontiana. Multiple sequence alignments demonstrated the presence of a leucine residue two positions upstream of the friedelin synthase Asp-Cys-Thr-Ala-Glu (DCTAE) active site motif, while the vast majority of OSCs identified so far have a valine or isoleucine residue at the same position. The substitution of the leucine residue with valine, threonine or isoleucine in M. ilicifolia friedelin synthase interfered with substrate recognition and lead to the production of different pentacyclic triterpenes. Hence, our data indicate a key role for the leucine residue in the structure and function of this oxidosqualene cyclase. (AU)

FAPESP's process: 12/21005-8 - Study of the friedelin production from the gene mutations of friedelin synthase of Maytenus ilicifolia
Grantee:Karina Alves Pinheiro
Support type: Scholarships in Brazil - Master
FAPESP's process: 14/03819-3 - Cloning and functional characterization of oxidoesqualene cyclases of Maytenus ilicifolia
Grantee:Cleslei Fernando Zanelli
Support type: Regular Research Grants
FAPESP's process: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
Grantee:Glaucius Oliva
Support type: Research Grants - Research, Innovation and Dissemination Centers - RIDC
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 type: Scholarships in Brazil - Post-Doctorate
FAPESP's process: 12/09584-2 - Cloning of oxidosqualene cyclase genes from Maytenus ilicifolia Mart. ex Reissek
Grantee:Cristina Carvalho Barbosa
Support type: Scholarships in Brazil - Scientific Initiation
FAPESP's process: 13/15306-8 - Studies concerning the biosynthesis of quinonemethides triterpenes by metabolic engineering: evaluation of the micro- and macromolecular metabolic flow of heterologous system by proteomics and metabolomics techniques
Grantee:Lidiane Gaspareto Felippe
Support type: Scholarships in Brazil - Post-Doctorate