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

Unnatural spirocyclic oxindole alkaloids biosynthesis in Uncaria guianensis

Full text
Author(s):
Lopes, Adriana A. [1] ; Chioca, Bianca [1] ; Musquiari, Bruno [1] ; Crevelin, Eduardo J. [2] ; Franca, Suzelei de C. [1] ; Fernandes da Silva, Maria Fatima das G. [3] ; Pereira, Ana Maria S. [1]
Total Authors: 7
Affiliation:
[1] Univ Ribeirao Preto UNAERP, Unidade Biotecnol, Av Costabile Romano 2201, BR-14096900 Ribeirao Preto, SP - Brazil
[2] Univ Sao Paulo, Fac Filosofia Ciencias & Letras Ribeirao Preto, Av Cafe S-N, BR-14040900 Ribeirao Preto, SP - Brazil
[3] Univ Fed Sao Carlos UFSCar, Dept Quim, Ctr Ciencias Exatas & Tecnol, Rod Washington Luis S-N, BR-13565905 Sao Carlos, SP - Brazil
Total Affiliations: 3
Document type: Journal article
Source: SCIENTIFIC REPORTS; v. 9, AUG 5 2019.
Web of Science Citations: 0
Abstract

Spiro-oxindole scaffolds have been studied due to their promising therapeutic potential. In the Amazon rainforest there are two important Uncaria species known as ``cat's claw{''}, which biosynthesize spirocyclic oxindole alkaloids; Uncaria tomentosa (Willd. ex Schult.) DC. and Uncaria guianensis (Aublet) Gmell. We carried out a precursor-directed biosynthesis approach with U. guianensis and successfully obtained oxindole alkaloid analogues with molecular mass corresponding to the addition of a methyl or fluorine group on the oxindole ring using tryptamine analogue precursors. Two of these novel oxindole alkaloid analogues (3b-7-methyl-isomitraphylline and 3c-6-fluoro-isomitraphylline) were isolated and characterized by NMR spectroscopy and ESI-QTOF-MS/MS. Having established a substrate feeding protocol for these plantlets, the biosynthetic route for mitraphylline (1), rhynchophylline (2), isomitraphylline (3) and isorhynchophylline (4) was also investigated using C-13-precursors (1-C-13-D-glucose, 2-C-13-tryptophan, 1-C-13-DL-glyceraldehyde, and methyl-C-13-D-methionine). (AU)

FAPESP's process: 13/22609-7 - Oxindole alkaloids from Uncaria tomentosa: biosynthetic studies and alkaloids analogues obtained by precursor-directed biosynthesis
Grantee:Adriana Aparecida Lopes
Support type: Scholarships in Brazil - Young Researchers
FAPESP's process: 15/18978-2 - Production of methylated oxindole alkaloid analogues by precursor-directed biosynthesis using in vitro Uncaria guianensis
Grantee:Bianca Chioca
Support type: Scholarships in Brazil - Scientific Initiation
FAPESP's process: 13/07349-9 - Oxindole alkaloids from Uncaria tomentosa: biosynthetic studies and alkaloids analogues obtained by precursor-directed biosynthesis
Grantee:Adriana Aparecida Lopes
Support type: Research Grants - Young Investigators Grants