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

doi:10.1016/j.fitote.2019.03.004

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 journal › Article › peer-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 language	English
Pages (from-to)	340-345
Number of pages	6
Journal	Fitoterapia
Volume	134
DOIs	https://doi.org/10.1016/j.fitote.2019.03.004
State	Published - 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

Access to Document

10.1016/j.fitote.2019.03.004

Cite this

@article{2b92a64c74384cb8a7ecf1a23d9be851,

title = "An unprecedented chlorine-containing piperamide from Piper pseudoarboreum as potential leishmanicidal agent",

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.",

keywords = "Biosynthetic pathway, Chlorinated-piperamide, Leishmanicidal, Piper pseudoarboreum",

author = "Ninoska Flores and Ticona, {Juan C.} and Pablo Bilbao-Ramos and Dea-Ayuela, {M. Auxiliadora} and {Ruiz Macedo}, {Juan C.} and Bazzocchi, {Isabel L.} and Francisco Bol{\'a}s-Fern{\'a}ndez and Jim{\'e}nez, {Ignacio A.}",

note = "Publisher Copyright: {\textcopyright} 2019 Elsevier B.V.",

year = "2019",

month = apr,

doi = "10.1016/j.fitote.2019.03.004",

language = "Ingl{\'e}s",

volume = "134",

pages = "340--345",

journal = "Fitoterapia",

issn = "0367-326X",

publisher = "Elsevier",

}

TY - JOUR

T1 - An unprecedented chlorine-containing piperamide from Piper pseudoarboreum as potential leishmanicidal agent

AU - Flores, Ninoska

AU - Ticona, Juan C.

AU - Bilbao-Ramos, Pablo

AU - Dea-Ayuela, M. Auxiliadora

AU - Ruiz Macedo, Juan C.

AU - Bazzocchi, Isabel L.

AU - Bolás-Fernández, Francisco

AU - Jiménez, Ignacio A.

PY - 2019/4

Y1 - 2019/4

N2 - 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.

AB - 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.

KW - Biosynthetic pathway

KW - Chlorinated-piperamide

KW - Leishmanicidal

KW - Piper pseudoarboreum

UR - http://www.scopus.com/inward/record.url?scp=85062702740&partnerID=8YFLogxK

U2 - 10.1016/j.fitote.2019.03.004

DO - 10.1016/j.fitote.2019.03.004

M3 - Artículo

C2 - 30840916

AN - SCOPUS:85062702740

VL - 134

SP - 340

EP - 345

JO - Fitoterapia

JF - Fitoterapia

SN - 0367-326X

ER -

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

Abstract

Bibliographical note

Keywords

Access to Document

Fingerprint

Cite this