Methyl angolensate changes in Khaya ivorensis after fungal infection

HPLC–ESI-MS/MS using Selected Reaction Monitoring (SRM) mode was employed to develop a rapid, selective and sensitive method for detecting methyl angolensate (MA) in all aerial parts of Khaya ivorensis with and without symptoms of stem and branch cankers, caused by Botryosphaeria rhodina. Outcomes s...

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Bibliographic Details
Published in:Phytochemistry (Oxford) 2009-12, Vol.70 (17), p.2027-2033
Main Authors: Reche, Karine V.G., de Souza, Gezimar D., Trapp, Marília A., Rodrigues-Filho, Edson, Silva, Sebastião C., Fernandes, João B., Vieira, Paulo C., Muller, Manfred W., da Silva, M. Fátima das G.F.
Format: Article
Language:English
Subjects:
Biological and medical sciences
Botryosphaeria
Botryosphaeria rhodina
Chemical constitution
disease resistance
Fundamental and applied biological sciences. Psychology
Fungi - pathogenicity
Host-Pathogen Interactions
host-pathogen relationships
HPLC
Khaya
Khaya ivorensis
limonoids
Mahogany
Meliaceae
Meliaceae - metabolism
Meliaceae - microbiology
Methyl angolensate
Phytoanticipins
Plant Diseases
plant pathogenic fungi
Plant physiology and development
Plant Structures
resistance mechanisms
secondary metabolites
SRM
Triterpenes - metabolism
Validation
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Summary:HPLC–ESI-MS/MS using Selected Reaction Monitoring (SRM) mode was employed to develop a rapid, selective and sensitive method for detecting methyl angolensate (MA) in all aerial parts of Khaya ivorensis with and without symptoms of stem and branch cankers, caused by Botryosphaeria rhodina. Outcomes strongly suggested that MA plays a role in plant–pathogen interactions probably as a phytoanticipin. 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.
ISSN:0031-9422
1873-3700
DOI:10.1016/j.phytochem.2009.08.013