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

Biosynthetic Insights into p-Hydroxybenzoic Acid-Derived Benzopyrans in Piper gaudichaudianum

Full text
Author(s):
Batista, Andrea N. L. [1] ; Batista, Jr., Joao M. [2] ; Souza-Moreira, Tatiana M. [3] ; Valentini, Sandro R. [3] ; Kato, Massuo J. [4] ; Zanelli, Cleslei F. [3] ; Furlan, Maysa [1]
Total Authors: 7
Affiliation:
[1] Univ Estadual Paulista UNESP, Inst Quim, BR-14800060 Araraquara, SP - Brazil
[2] Univ Fed Sao Carlos UFSCar, Dept Quim, BR-13565905 Sao Carlos, SP - Brazil
[3] Univ Estadual Paulista UNESP, Fac Ciencias Farmaceut, BR-14801902 Araraquara, SP - Brazil
[4] Univ Sao Paulo, Inst Quim, BR-05508000 Sao Paulo, SP - Brazil
Total Affiliations: 4
Document type: Journal article
Source: Journal of the Brazilian Chemical Society; v. 29, n. 5, p. 1105-1114, MAY 2018.
Web of Science Citations: 0
Abstract

Piper gaudichaudianum Kunth (Piperaceae) accumulates gaudichaudianic acid, a prenylated benzopyran, as its major component. Interestingly, this trypanocidal compound occurs as a racemic mixture. Herein, transcriptomic investigations of Piper gaudichaudianum using the RNA-seq approach are reported, and from the analysis of the transcripts expressed it was possible to propose a complete biosynthetic pathway for the production of gaudichaudianic acid, including the steps that originate its precursor, p-hydroxybenzoic acid. Peperomia obtusifolia (L.) A. Dietr. (Piperaceae) also accumulates racemic benzopyrans, however, its chromanes originate from the polyketide pathway, while the chromenes from Piper derives from the shikimate pathway. Recent transcriptomic and proteomic studies of the former species did not identify polyketide synthases involved in the production of the benzopyran moiety, but revealed the expression of tocopherol cyclase, which may be responsible for the cyclization of the 3,4-dihydro-2H-pyran ring. The analysis of the enzymes involved in the secondary metabolism of Piper gaudichaudianum and the comparison with the data previously obtained from Peperomia obtusifolia can provide valuable information on how these compounds are biosynthesized. (AU)

FAPESP's process: 14/50316-7 - Dimensions US-Biota São Paulo: Chemically mediated multi-trophic interaction diversity across tropical gradients
Grantee:Massuo Jorge Kato
Support Opportunities: BIOTA-FAPESP Program - Thematic Grants
FAPESP's process: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
Grantee:Glaucius Oliva
Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC
FAPESP's process: 15/07089-2 - Vibrational chiroptical spectroscopy for stereochemical characterization of small molecules and macromolecules
Grantee:João Marcos Batista Junior
Support Opportunities: Scholarships in Brazil - Young Researchers
FAPESP's process: 11/01003-8 - Proteomic studies in Peperomia obtusifolia (Piperaceae)
Grantee:Andrea Nastri de Luca Batista
Support Opportunities: Scholarships in Brazil - Post-Doctoral
FAPESP's process: 14/25222-9 - Vibrational chiroptical spectroscopy for stereochemical characterization of small molecules and macromolecules
Grantee:João Marcos Batista Junior
Support Opportunities: Research Grants - Young Investigators Grants