New antimalarials with a triterpenic scaffold from Momordica balsamina

C, Ramalhete , Dinora Ferreira, S, Mulhovo , J, Molnár , Virgilio Estólio do Rosário, MJ. Ferreira

Research output: Contribution to journalArticlepeer-review

40 Citations (Scopus)

Abstract

Bioassay-guided fractionation of the methanol extract of Momordica balsamina led to the isolation of three new cucurbitane-type triterpenoids, balsaminols C-E (1-3). Their structures were elucidated on the basis of spectroscopic methods including 2D NMR experiments (COSY, HMQC, HMBC and NOESY). Balsaminols C-E, together with ten cucurbitacins isolated from the same plant (4-13), were evaluated for their antimalarial activity against the Plasmodium falciparum chloroquine-sensitive strain 3D7 and the chloroquine-resistant clone Dd2. Most of the compounds displayed antimalarial activity. Compounds 9 and 12 revealed the highest antiplasmodial effects against both strains (IC50 values: 4.6, and 7.4 mu M, 3D7, respectively; 4.0, and 8.2 mu M, Dd2, respectively). Structure-activity relationships are discussed. Furthermore, the preliminary toxicity toward human cells of compounds 1-5 and 9 was investigated in breast cancer cell line (MCF-7). Compounds were inactive or showed weak toxicity (IC50 values > 19.0). (C) 2010 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)5254-5260
Number of pages7
JournalBioorganic & Medicinal Chemistry
VolumeVol. 18
Issue numbern.º 14
DOIs
Publication statusPublished - 15 Jul 2010

Keywords

  • Momordica balsamina
  • Cucurbitane-type triterpenes
  • Malaria
  • lasmodium falciparum
  • Antimalarial activity

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