PMID- 19765786 OWN - NLM STAT- MEDLINE DCOM- 20100427 LR - 20091201 IS - 1873-3700 (Electronic) IS - 0031-9422 (Linking) VI - 70 IP - 17-18 DP - 2009 Dec TI - Methyl angolensate changes in Khaya ivorensis after fungal infection. PG - 2027-33 LID - 10.1016/j.phytochem.2009.08.013 [doi] AB - 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 r(2)>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. FAU - Reche, Karine V G AU - Reche KV AD - Laboratorio de Produtos Naturais, Departamento de Quimica, UFSCar. Rodovia Washington Luiz, Km 235, Postcode 676, CEP 13565-905, Sao Carlos, Sao Paulo, Brazil. FAU - de Souza, Gezimar D AU - de Souza GD FAU - Trapp, Marilia A AU - Trapp MA FAU - Rodrigues-Filho, Edson AU - Rodrigues-Filho E FAU - Silva, Sebastiao C AU - Silva SC FAU - Fernandes, Joao B AU - Fernandes JB FAU - Vieira, Paulo C AU - Vieira PC FAU - Muller, Manfred W AU - Muller MW FAU - da Silva, M Fatima das G F AU - da Silva MF LA - eng PT - Journal Article PT - Research Support, Non-U.S. Gov't DEP - 20090916 PL - England TA - Phytochemistry JT - Phytochemistry JID - 0151434 RN - 0 (Triterpenes) RN - 2629-14-3 (methyl angolensate) SB - IM MH - Fungi/*pathogenicity MH - *Host-Pathogen Interactions MH - Meliaceae/*metabolism/microbiology MH - *Plant Diseases MH - Plant Structures MH - Triterpenes/*metabolism EDAT- 2009/09/22 06:00 MHDA- 2010/04/28 06:00 CRDT- 2009/09/22 06:00 PHST- 2008/10/07 00:00 [received] PHST- 2009/07/28 00:00 [revised] PHST- 2009/08/18 00:00 [accepted] PHST- 2009/09/22 06:00 [entrez] PHST- 2009/09/22 06:00 [pubmed] PHST- 2010/04/28 06:00 [medline] AID - S0031-9422(09)00365-3 [pii] AID - 10.1016/j.phytochem.2009.08.013 [doi] PST - ppublish SO - Phytochemistry. 2009 Dec;70(17-18):2027-33. doi: 10.1016/j.phytochem.2009.08.013. Epub 2009 Sep 16.