Hydroxyalkenylresorcinols from Stylogyne turbacensis

J Nat Prod. 2007 Aug;70(8):1249-52. doi: 10.1021/np070081d. Epub 2007 Jul 13.

Abstract

Two new compounds, 5-(11'(S)-hydroxy-8'-heptadecenyl)resorcinol (3) and 5-(12'(S)-hydroxy-8',14'-heptadecadienyl)resorcinol (4), were isolated from the leaves of Stylogyne turbacensis together with the known analogue metabolites 1 and 2. Compounds 3 and 4 showed the strongest activity in the leishmania assay, 7 and 3 microM, respectively, while compounds 1, 2, and 4 showed moderate activity against a drug-resistant strain of Trypanosoma cruzi with IC(50) values of 30, 25, and 22 microM, respectively. Additional testing in MCF-7 and NCI-H460 was performed for compounds 3 and 4. The structures of compounds 1-4 were elucidated using NMR, MS, and other spectroscopic data. The absolute stereochemistry of compounds 3 and 4 was also investigated using the Mosher ester approach. Peracetylated derivatives of these four metabolites were produced and their activities determined in the Trypanosoma cruzi assay.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Animals
  • Antiprotozoal Agents / chemistry
  • Antiprotozoal Agents / isolation & purification*
  • Antiprotozoal Agents / pharmacology
  • Chlorocebus aethiops
  • Female
  • Humans
  • Leishmania / drug effects*
  • Nuclear Magnetic Resonance, Biomolecular
  • Panama
  • Plants, Medicinal / chemistry*
  • Primulaceae / chemistry*
  • Resorcinols / chemistry
  • Resorcinols / isolation & purification*
  • Resorcinols / pharmacology
  • Trypanosoma cruzi / drug effects*
  • Vero Cells

Substances

  • 5-(11'(S)-hydroxy-8'-heptadecenyl)resorcinol
  • 5-(12'(S)-hydroxy-8',14'-heptadecadienyl)resorcinol
  • Antiprotozoal Agents
  • Resorcinols