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

Authors:            

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


Astract:

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 RNAseq 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.


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

 Univ Sao Paulo, Inst Quim, BR-05508000 Sao Paulo, SP – Brazil


Link to full article:  http://jbcs.sbq.org.br/imagebank/pdf/2017-0476AR_IUPAC.pdf