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

Acetylenic fatty acids from Porcelia macrocarpa (Annonaceae) against trypomastigotes of Trypanosoma cruzi: Effect of octadec-9-ynoic acid in plasma membrane electric potential

Full text
Author(s):
Londero, Vinicius S. [1] ; da Costa-Silva, Thais A. [2] ; Gomes, Kaio S. [2] ; Ferreira, Daiane D. [3] ; Mesquita, Juliana T. [3] ; Tempone, Andre G. [3] ; Young, Maria Claudia M. [4] ; Jerz, Gerold [5] ; Lago, Joao Henrique G. [2]
Total Authors: 9
Affiliation:
[1] Univ Fed Sao Paulo, Inst Environm Chem & Pharmaceut Sci, BR-09972270 Sao Paulo - Brazil
[2] Fed Univ ABC, Ctr Nat & Human Sci, BR-09210580 Santo Andre - Brazil
[3] Adolfo Lutz Inst, Ctr Parasitol & Mycol, BR-01246000 Sao Paulo - Brazil
[4] Inst Bot Sao Paulo, Nucleus Res Physiol & Biochem, BR-04301902 Sao Paulo - Brazil
[5] Tech Univ Carolo Wilhelmina Braunschweig, Inst Food Chem, D-38106 Braunschweig - Germany
Total Affiliations: 5
Document type: Journal article
Source: BIOORGANIC CHEMISTRY; v. 78, p. 307-311, AUG 2018.
Web of Science Citations: 3
Abstract

Porcelia macrocarpa (Warm.) R. E. Fries (Annonaceae) is an endemic plant in Brazil where its tasty pulp has been eaten fresh. The hexane extract from its flowers was subjected to chromatographic procedures to afford four acetylene derivatives identified as octadec-9-ynoic (stearolic acid - 1), (11E)-octadec-11en- 9-ynoic (santalbic acid - 2), 8-hydroxyoctadec-9,11-diynoic (3) and 8-hydroxyoctadec-17-en-9,11-d iynoic (isanolic acid - 4) acids by NMR and HRESIMS. Among tested compounds against trypomastigote forms of T. cruzi, octadec-9-ynoic acid (1) displayed higher potential with IC50 = 27.6 mu M and a selectivity index (SI) higher than 7. Compounds 2 and 3 showed IC50 of approximately 60 mM while compound 4 was inactive. The lethal action of the compound 1 was investigated using spectrofluorometric techniques to detect ROS content, plasma membrane permeability and plasma membrane potential by flow cytometry. Compound 1 showed no alteration in the production of ROS of treated trypomastigotes and no alteration of the plasma membrane permeability was observed as detected by the fluorescent probe SYTOX-green after 120 min of incubation. However, by using the potential-sensitive fluorescent probe DiSBAC(2)(3), compound 1 caused depolarization of the plasma membrane potential when compared to untreated parasites. Our results demonstrated the anti-T. cruzi effects of compounds 1-3 isolated from flowers of P. macrocarpa and indicated that the lethal effect of compound 1 in T. cruzi could be associated to the plasma membrane disturbance of the parasite. (C) 2018 Elsevier Inc. All rights reserved. (AU)

FAPESP's process: 15/23403-9 - Rational pre-clinical study of new drug candidates against neglected protozoan diseases using pharmacokinetic approaches
Grantee:André Gustavo Tempone Cardoso
Support type: Regular Research Grants