TY - JOUR
T1 - Antifeedant and cytotoxic activity of longipinane derivatives
AU - Cerda-García-Rojas, Carlos M.
AU - Burgueño-Tapia, Eleuterio
AU - Román-Marín, Luisa U.
AU - Hernández-Hernández, Juan D.
AU - Agulló-Ortuño, Teresa
AU - González-Coloma, Azucena
AU - Joseph-Nathan, Pedro
PY - 2010
Y1 - 2010
N2 - 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.
AB - 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.
KW - Antifeedant
KW - Asteraceae
KW - Cytotoxic
KW - Longipinane derivatives
KW - Stevia
KW - Vibrational circular dichroism
UR - http://www.scopus.com/inward/record.url?scp=77049096925&partnerID=8YFLogxK
U2 - 10.1055/s-0029-1186080
DO - 10.1055/s-0029-1186080
M3 - Artículo
SN - 0032-0943
VL - 76
SP - 297
EP - 302
JO - Planta Medica
JF - Planta Medica
IS - 3
ER -