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Antifeedant and Cytotoxic Activity of Longipinane Derivatives

AuthorsCerda-García Rojas, Carlos M.; Burgueño-Tapia, Eleuterio; Román-Marín, Luisa U.; Hernández-Hernández, Juan D.; Agulló-Ortuño, María Teresa ; González-Coloma, Azucena ; Joseph-Nathan, Pedro
Longipinane derivatives
Vibrational circular dichroism
Issue Date2010
PublisherVerlagsgruppe Handelsblatt
CitationPlanta medica 76:297-302 (2010)
AbstractThe polyoxygenated longipinane derivatives 1–8 were tested as antifeedant compounds against the herbivorous insects Spodop- tera littoralis, Rhopalosiphum padi, and Myzus persicae. Compounds 1–3 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.
Description6 pages, figures, and tables statistics.
Appears in Collections:(ICA) Artículos
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