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Methyl angolensate changes in Khaya ivorensis after fungal infection

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Reche, K. V. G., de Souza, G. D., Trapp, M. A., Rodrigues-Filho, E., Silva, S. C., Fernandes, J. B., et al. (2009). Methyl angolensate changes in Khaya ivorensis after fungal infection. Phytochemistry, 70(17-18), 2027-2033. doi:10.1016/j.phytochem.2009.08.013.

Khaya ivorensis with and without symptoms of stem and branch cankers, caused by Botryosphaeria rhodina were examined in order to determine whether the secondary metabolites in this plant were associated with a chemical defense response. This study provides evidence that the limonoid methyl angolensate (MA) is present at higher concentrations in K. ivorensis with symptoms of stem cankers rather than in the plants without symptoms. A rapid, sensitive and selective HPLC–ESI-MS/MS method (using selected reaction monitoring – SRM – mode) was developed for quantification of MA in all aerials parts of such plants, with a good linearity over a range of 0.1–20.0 g/kg, with r2 > 0.996 ± 6.1%. The limits of detection (LOD) and quantification (LOQ) were less than 0.03 g/kg and 0.08 g/kg, respectively. Relative Standard Deviations (RSDs) ranged from 1.7% to 19.2% for all matrices. While the MA concentration did not change in the stem bark, its amounts increased nearly fourfold in stems and by 20% in leaves, when plants with symptoms were compared with those without symptoms. These data suggest that MA plays a role in plant–pathogen interactions, probably as a phytoanticipin.