Abstract
The polyoxygenated longipinane derivatives 1 –8 were tested as antifeedant compounds against the herbivorous insects Spodoptera 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.
Key words
Stevia
- Asteraceae - longipinane derivatives - antifeedant - cytotoxic - vibrational circular
dichroism
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pjoseph@nathan.cinvestav.mx
