Study on the structural and biosynthetic Piper Fuligineum Kunth (Piperaceae)

• Grant number: 11/16752-6
• Support Opportunities: Scholarships in Brazil - Master
• Start date: March 01, 2012
• End date: February 28, 2014
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Maysa Furlan
• Grantee: Bruna Fonseca Mazzeu
• Host Institution: Instituto de Química (IQ). Universidade Estadual Paulista (UNESP). Campus de Araraquara. Araraquara , SP, Brazil

Abstract

Piper fuligineum Kunth hasn´t been studied from the chemical point of view. A preliminary chemical study conducted during the student's scientific initiation demonstrated that this species acumulates a very rare class of metabolites: the piperolides, concomitant with chromanones and benzoic acid prenylated derivatives. Furthermore, initial tests with crude extracts of this species have shown promising activities in clinical trials against Trypanosoma cruzi and human fungal pathogens as Candida tropicallis and C. albicans and the yeast Saccharomyces cerevisiae. The piperolides are phenolic compounds identified only in three Piper species , thus becoming an interesting target for biosynthetic studies. These compounds have cyclic and acyclic aliphatic chain and the stereogenic centers are not yet determined. The proposed initial biogenesis in this study would be a coupling between a C6-C3 derivative (phenylpropanoid pathway) with one unit of acetoacetyl-CoA (acetate pathway). The piperolides are formed after successive oxidations and enzymatic ciclizations. Based on the results achieved in the previous stage, the chemical studies will be continued, beyond experiments to determine the absolute configuration of stereogenic centers using technique circular dichroism and NMR, and if necessary, by vibrational dichroism. Whereas piperolides are rare compounds, and isolated a few species of Piper, and with few reports of biological tests performed, the extracts and isolated compounds will undergo testing are also evaluated against fungals, Trypanosoma cruzi, tumors cells and virus (HIV). A biosynthetic approach will also be focus of this project, verifying the participation of the phenylpropanoid pathway (phenylalanine by incubation with extracts enriched with the enzyme PAL) and the route of acetate (by incorporation of isotopically labeled precursors such as acetate, glucose and malonyl) in the piperolides biosynthesis

Scientific publications

(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)

BRUNA F. MAZZEU; LIDIANE G. FELIPPE; FERNANDO COTINGUIBA; MASSUO J. KATO; MAYSA FURLAN. Kavalactones and Benzoic Acid Derivatives from Leaves of Piper fuligineum Kunth (Piperaceae). Journal of the Brazilian Chemical Society, v. 29, n. 6, p. 1286-1290, 2018-06-00. (13/15306-8, 14/50316-7, 11/16752-6)

MAZZEU, BRUNA F.; FELIPPE, LIDIANE G.; COTINGUIBA, FERNANDO; KATO, MASSUO J.; FURLAN, MAYSA. Kavalactones and Benzoic Acid Derivatives from Leaves of & IT;Piper & IT; & IT;fuligineum & IT; Kunth (Piperaceae). Journal of the Brazilian Chemical Society, v. 29, n. 6, p. 1286-1290, JUN 2018. (13/07600-3, 14/50316-7, 11/16752-6, 13/15306-8)

Academic Publications

(References retrieved automatically from State of São Paulo Research Institutions)

MAZZEU, Bruna Fonseca. Estudo de aspectos químicos, biológicos e biossintéticos em Piper fuligineum Kunth(Piperaceae). 2014. Master's Dissertation - Universidade Estadual Paulista (Unesp). Instituto de Química. Araraquara Araraquara.