Antifeedant and cytotoxic activity of longipinane derivatives

Carlos M. Cerda-García-Rojas, Eleuterio Burgueño-Tapia, Luisa U. Román-Marín, Juan D. Hernández-Hernández, Teresa Agulló-Ortuño, Azucena González-Coloma, Pedro Joseph-Nathan

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19 Scopus citations

Abstract

The polyoxygenated longipinane derivatives 18 were tested as antifeedant compounds against the herbivorous insects Spodoptera littoralis, Rhopalosiphum padi, and Myzus persicae. Compounds 13 and 8 exhibited significant antifeedant activity against S. littoralis and M.persicae. The antifeedant activity against S. littoralis increased moderately after the C-8 hydroxy group in 3 was removed to afford 1 and increased strongly after the remaining two hydroxy groups were acetylated to afford 2. Compound 1 was active on M.persicae. Compounds 1, 3, and 4, with an unsaturated six-membered ring, exhibited an increase in post-ingestive effects on S. littoralis ranging from antifeedant in the case of 1 to toxic for compounds 3 and 4. These compounds did not have any phytotoxic effect on Lactuca sativa. When tested on a panel of tumoral cells, compounds 2 and 6 exhibited moderate selective cytotoxic effects on the p53 null lung carcinoma cells H1299, which were not affected by the drug paclitaxel. In addition, vibrational circular dichroism (VCD) was applied to the representative longipinene derivative 2 to verify its absolute configuration, and the sensitivity of the VCD methodology was evaluated by comparing spectra of the three diastereoisomers (4R,5S,7R,9R,10R,11R)-7,9-diacetyloxylongipin-2-en-1-one (2), (4R,5S,7S,9R,10R,11R)-7,9-diacetyloxylongipin-2-en-1-one, and (4R,5S,7R,9S,10R,11R)-7,9-diacetyloxylongipin-2-en-1-one.

Original languageEnglish
Pages (from-to)297-302
Number of pages6
JournalPlanta Medica
Volume76
Issue number3
DOIs
StatePublished - 2010

Keywords

  • Antifeedant
  • Asteraceae
  • Cytotoxic
  • Longipinane derivatives
  • Stevia
  • Vibrational circular dichroism

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