New antimalarial and cytotoxic 4-nerolidylcatechol derivatives.

4-Nerolidylcatechol (1) was isolated from cultivated Pothomorphe peltata root on a multigram scale using straight-forward solvent extraction-column chromatography. New semi-synthetic derivatives of 1 were prepared and tested in vitro against multidrug-resistant Plasmodium falciparum K1 strain. Mono-O-methyl, mono-O-benzyl, O,O-dibenzyl and O,O-dibenzoyl derivatives 2-8 exhibited IC(50) in the 0.67-22.52 microM range. Mono-O-methyl ethers 6 and 7 inhibited the in vitro growth of human tumor cell lines HCT-8 (colon carcinoma), SF-295 (central nervous system), LH-60 (human myeloblastic leukemia) and MDA/MB-435 (melanoma). In general, derivatives 2-8 are more stable to light, air and pH at ambient temperatures than their labile, natural precursor 1. These derivatives provide leads for the development of a novel class of antimalarial drugs with enhanced chemical and pharmacological properties.
AuthorsAna Cristina da Silva Pinto, Luis Francisco Rocha Silva, Bruno Coelho Cavalcanti, Márcia Rúbia Silva Melo, Francisco Célio Maia Chaves, Letícia Vera Costa Lotufo, Manoel Odorico de Moraes, Valter Ferreira de Andrade-Neto, Wanderli Pedro Tadei, Claudia O Pessoa, Pedro Paulo Ribeiro Vieira, Adrian Martin Pohlit
JournalEuropean journal of medicinal chemistry (Eur J Med Chem) Vol. 44 Issue 6 Pg. 2731-5 (Jun 2009) ISSN: 1768-3254 [Electronic] France
PMID19084293 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Chemical References
  • 4-nerolidylcatechol
  • Antimalarials
  • Antineoplastic Agents, Phytogenic
  • Catechols
  • Plant Extracts
  • Animals
  • Antimalarials (chemical synthesis, chemistry, pharmacology, toxicity)
  • Antineoplastic Agents, Phytogenic (chemical synthesis, chemistry, pharmacology, toxicity)
  • Catechols (chemical synthesis, chemistry, pharmacology, toxicity)
  • Cell Line, Tumor
  • Cell Proliferation (drug effects)
  • Dose-Response Relationship, Drug
  • Drug Resistance
  • Drug Screening Assays, Antitumor
  • HL-60 Cells
  • Humans
  • Molecular Structure
  • Parasitic Sensitivity Tests
  • Piperaceae (chemistry)
  • Plant Extracts (chemical synthesis, chemistry, pharmacology, toxicity)
  • Plant Roots (chemistry)
  • Plasmodium falciparum (drug effects)
  • Stereoisomerism

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