An unprecedented chlorine-containing piperamide from Piper pseudoarboreum as potential leishmanicidal agent

Ninoska Flores, Juan C. Ticona, Pablo Bilbao-Ramos, M. Auxiliadora Dea-Ayuela, Juan C. Ruiz Macedo, Isabel L. Bazzocchi, Francisco Bolás-Fernández, Ignacio A. Jiménez

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

A phytochemical investigation of the ethanolic extract of leaves from Piper pseudoarboreum led to the isolation of 3-chlorosintenpyridone 1, an unprecedented chlorinated piperamide, together with the known compounds 2–12. Their structures were established based on 1D and 2D (COSY, ROESY, HMQC, and HMBC) NMR spectroscopy, in addition to high resolution mass spectrometry. The proposed biosynthetic pathway of compound 1 is discussed. Compounds 1–12 were tested in vitro for their leishmanicidal potential against promastigote stages of Leishmania amazonensis, L braziliensis, L. guyanensis and L. infantum. Two compounds from this series, the alkamide 1 (IC 50 3.4–5.2 μM) and the fatty acid 9 (IC 50 18.7–29.6 μM) displayed higher or similar potency to Miltefosine, used as the reference drug.

Original languageEnglish
Pages (from-to)340-345
Number of pages6
JournalFitoterapia
Volume134
DOIs
StatePublished - Apr 2019

Bibliographical note

Funding Information:
This study was supported by the SAF2015-65113-C2-1-R Spanish MINECO, co-funded by the European Regional Development Fund (FEDER), and PCI-Iberoamerica A/030160/10 and AP/039767/11 projects. J.C.T. and P·B-R. are grateful to MAEC-AECID for their fellowships.

Funding Information:
This study was supported by the SAF2015-65113-C2-1-R Spanish MINECO , co-funded by the European Regional Development Fund (FEDER) , and PCI-Iberoamerica A/030160/10 and AP/039767/11 projects. J.C.T. and P·B-R. are grateful to MAEC-AECID for their fellowships.

Publisher Copyright:
© 2019 Elsevier B.V.

Keywords

  • Biosynthetic pathway
  • Chlorinated-piperamide
  • Leishmanicidal
  • Piper pseudoarboreum

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