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

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dc.contributor.authorSouza-Moreira, Tatiana M. [UNESP]
dc.contributor.authorAlves, Thaís B. [UNESP]
dc.contributor.authorPinheiro, Karina A. [UNESP]
dc.contributor.authorFelippe, Lidiane G. [UNESP]
dc.contributor.authorDe Lima, Gustavo M. A.
dc.contributor.authorWatanabe, Tatiana F. [UNESP]
dc.contributor.authorBarbosa, Cristina C. [UNESP]
dc.contributor.authorSantos, Vânia A.F.F.M. [UNESP]
dc.contributor.authorLopes, Norberto P.
dc.contributor.authorValentini, Sandro R. [UNESP]
dc.contributor.authorGuido, Rafael V. C.
dc.contributor.authorFurlan, Maysa [UNESP]
dc.contributor.authorZanelli, Cleslei F. [UNESP]
dc.contributor.institutionUniversidade Estadual Paulista (Unesp)
dc.contributor.institutionUniversidade de Saõ Paulo
dc.date.accessioned2018-12-11T17:23:17Z
dc.date.available2018-12-11T17:23:17Z
dc.date.issued2016-11-22
dc.description.abstractAmong 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 β-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.en
dc.description.affiliationInstituto de Química Univ. Estadual Paulista UNESP, Rua Prof. Francisco Degni 55
dc.description.affiliationCentro de Pesquisa e Inovaçaõ em Biodiversidade e Fármacos Instituto de Física de Saõ Carlos Universidade de Saõ Paulo
dc.description.affiliationFaculdade de Ciências Farmaceûticas Univ. Estadual Paulista-UNESP, Rod. Araraquara-Jaú km 1
dc.description.affiliationFaculdade de Ciências Farmaceûticas Universidade de Saõ Paulo, Avenida do Café s/n
dc.description.affiliationUnespInstituto de Química Univ. Estadual Paulista UNESP, Rua Prof. Francisco Degni 55
dc.description.affiliationUnespFaculdade de Ciências Farmaceûticas Univ. Estadual Paulista-UNESP, Rod. Araraquara-Jaú km 1
dc.identifierhttp://dx.doi.org/10.1038/srep36858
dc.identifier.citationScientific Reports, v. 6.
dc.identifier.doi10.1038/srep36858
dc.identifier.file2-s2.0-84996940074.pdf
dc.identifier.issn2045-2322
dc.identifier.lattes1308042794786872
dc.identifier.lattes1525665408900195
dc.identifier.orcid0000-0001-7831-1149
dc.identifier.scopus2-s2.0-84996940074
dc.identifier.urihttp://hdl.handle.net/11449/176962
dc.language.isoeng
dc.relation.ispartofScientific Reports
dc.relation.ispartofsjr1,533
dc.rights.accessRightsAcesso aberto
dc.sourceScopus
dc.titleFriedelin Synthase from Maytenus ilicifolia: Leucine 482 Plays an Essential Role in the Production of the Most Rearranged Pentacyclic Triterpeneen
dc.typeArtigo
unesp.author.lattes1308042794786872
unesp.author.lattes1525665408900195[13]
unesp.author.orcid0000-0001-7831-1149[13]
unesp.departmentFármacos e Medicamentos - FCFpt

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