In vivo localization and identification of the antiplasmodial alkaloid dioncophylline A in the tropical liana Triphyophyllum peltatum by a combination of fluorescence, near infrared Fourier transform Raman microscopy, and density functional theory calculations.
Near infrared Fourier transform (NIR FT) micro Raman spectroscopy in combination with density functional theory (DFT) calculations has been applied for an in vivo localization of the antiplasmodial naphthylisoquinoline alkaloid dioncophylline A (1) in the tropical liana Triphyophyllum peltatum. Fluorescence microscopy images suggest finding this active agent in 10 mum big inclusions located in the cortex of the stem or the beginning of the leaves. By means of spatially resolved FT Raman micro spectroscopy, we could detect dioncophylline A (1) in these inclusions. FT Raman spectroscopy is an extremely selective tool capable of differentiating between various structurally similar naphthylisoquinoline alkaloids. With the help of DFT calculations, we succeeded in assigning the differences found in the FT Raman spectra of the various naphthylisoquinolines to nuC=C vibrations of the naphthyl ring. The presented results are of relevance for the investigation and extraction of new antimalarial active agents.
Frosch
Torsten
T
Institut für Physikalische Chemie, Friedrich-Schiller-Universität Jena, Helmholtzweg 4, D-07743 Jena, Germany.
Schmitt
Michael
M
Schenzel
Karla
K
Faber
Johan H
JH
Bringmann
Gerhard
G
Kiefer
Wolfgang
W
Popp
Jürgen
J
D000465:Algorithms; D000470:Alkaloids / Q000032:analysis / Q000737:chemistry; D000962:Antimalarials / Q000032:analysis / Q000737:chemistry; D045603:Dioncophyllaceae / Q000737:chemistry*; D007546:Isoquinolines / Q000032:analysis* / Q000737:chemistry; D008856:Microscopy, Fluorescence / Q000379:methods*; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D017550:Spectroscopy, Fourier Transform Infrared / Q000379:methods*; D019265:Spectroscopy, Near-Infrared / Q000379:methods; D013059:Spectrum Analysis, Raman / Q000379:methods; D014732:Vibration
D000470:Alkaloids; D000962:Antimalarials; D007546:Isoquinolines; D009281:Naphthalenes; C031721:naphthalene; C104320:dioncophylline A