New antimalarials with a triterpenic scaffold from Momordica balsamina

Cátia Ramalhete, Dinora Lopes, Silva Mulhovo, Joseph Molnár, Virgílio E. Rosário, Maria José U. Ferreira

Research output: Contribution to journalArticle

39 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 (IC 50 values: 4.6, and 7.4 μM, 3D7, respectively; 4.0, and 8.2 μM, 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 (IC 50 values >19.0).

Original languageEnglish
Pages (from-to)5254-5260
Number of pages7
JournalBioorganic and Medicinal Chemistry
Volume18
Issue number14
DOIs
Publication statusPublished - Jul 15 2010

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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  • Cite this

    Ramalhete, C., Lopes, D., Mulhovo, S., Molnár, J., Rosário, V. E., & Ferreira, M. J. U. (2010). New antimalarials with a triterpenic scaffold from Momordica balsamina. Bioorganic and Medicinal Chemistry, 18(14), 5254-5260. https://doi.org/10.1016/j.bmc.2010.05.054