Structure and Conformation of a New Longipinene Diester from <i>Stevia nepetifolia</i>

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 (4 R,5 S,7 R,9 R,10 R,11 R)-7,9-diacetyloxylongipin-2-en-1-one (2), (4 R,5 S,7 S,9 R,10 R,11 R)-7,9-diacetyloxylongipin-2-en-1-one, and (4 R,5 S,7 R,9 S,10 R,11 R)-7,9-diacetyloxylongipin-2-en-1-one.

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Antifeedant and Cytotoxic Activity of Longipinane Derivatives

Cerda-Garcı́a-Rojas

Burgueño‐Tapia

Román-Marín

et al. 2009

Planta Med

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A New Longipinene Diester from Stevia Monardifolia Kunth

Rojas-Pérez

Cedillo-Portugal

Joseph‐Nathan

et al. 2009

Natural Product Communications

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Nonpolar and medium polarity fractions from whole plant methanolic extracts of Stevia monardifolia afforded the new 7β-angeloyloxy-8α-isovaleroyloxylongipin-2-en-1-one 1 along with known 7β,8α-diangeloyloxylongipin-2-en-1-one 2 and 7β,8α-diangeloyloxylongipinan-1-one 3. Alkaline hydrolysis of a mixture of 1 and 2 gave 7β,8α-dihydroxylongipin-2-en-1one 4 which was subjected to a single crystal X-ray diffraction study. The new compound 1, which is the third 7β,8α-dihydroxylongipin-2-en-1-one diester natural product isolated from a Stevia especies, was fully characterized by oneand two-dimensional NMR spectroscopy and its absolute configuration was confirmed as the 4R,5S,7S,8S,10R,11R enantiomer by vibrational circular dichroism (VCD) measurements in comparison to calculation at the B3LYP/DGDZVP level of theory.

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Structure and Conformation of a New Longipinene Diester from Stevia nepetifolia

Cited by 2 publications

References 15 publications

Antifeedant and Cytotoxic Activity of Longipinane Derivatives

Antifeedant and Cytotoxic Activity of Longipinane Derivatives

A New Longipinene Diester from Stevia Monardifolia Kunth

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