New Pregnane Glycosides from Brucea javanica and Their Antifeedant Activity

Chemistry & Biodiversity
2011.0

Abstract

<jats:title>Abstract</jats:title><jats:p>Three new pregnane glycosides, 3‐<jats:italic>O</jats:italic>‐<jats:italic>β</jats:italic>‐<jats:sc>D</jats:sc>‐glucopyranosyl‐(1→2)‐<jats:italic>α</jats:italic>‐<jats:sc>L</jats:sc>‐arabinopyranosyl‐(20<jats:italic>R</jats:italic>)‐pregn‐5‐ene‐3<jats:italic>β</jats:italic>,20‐diol (<jats:bold>1</jats:bold>), 3‐<jats:italic>O</jats:italic>‐<jats:italic>α</jats:italic>‐<jats:sc>L</jats:sc>‐arabinopyranosyl‐(20<jats:italic>R</jats:italic>)‐pregn‐5‐ene‐3<jats:italic>β</jats:italic>,20‐diol‐20‐<jats:italic>O</jats:italic>‐<jats:italic>β</jats:italic>‐<jats:sc>D</jats:sc>‐glucopyranoside (<jats:bold>2</jats:bold>), 3‐<jats:italic>O</jats:italic>‐<jats:italic>α</jats:italic>‐<jats:sc>L</jats:sc>‐arabinopyranosyl‐(20<jats:italic>R</jats:italic>)‐pregn‐5‐ene‐3<jats:italic>β</jats:italic>,20‐diol‐20‐<jats:italic>O‐β</jats:italic>‐<jats:sc>D</jats:sc>‐glucopyranosyl‐(1→2)‐<jats:italic>β</jats:italic>‐<jats:sc>D</jats:sc>‐glucopyranoside (<jats:bold>3</jats:bold>) were isolated along with four known compounds, <jats:bold>4</jats:bold>–<jats:bold>7</jats:bold>, from the leaves and stems of <jats:italic>Brucea javanica.</jats:italic> Their structures were determined by detailed analyses of 1D‐ and 2D‐NMR spectroscopic data. All of the compounds isolated from <jats:italic>Brucea javanica</jats:italic> were tested for the antifeedant activities against the larva of <jats:italic>Pieris rapae.</jats:italic> Compounds <jats:bold>1, 3</jats:bold>, and <jats:bold>5</jats:bold> showed significant antifeedant activities after 72 h incubation.

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