Detection of polyhydroxyalkaloids in Lonchocarpus extracts by GC-MS of acetylated derivatives.
The methanol extracts of the roots of Lonchocarpus cultratus, L. latifolius and L. subglaucescens, species native to Brazil, were all active in the brine shrimp lethality test. Fractions rich in polyhydroxylated alkaloids were obtained from these extracts and, following acetylation, were analysed by GC-MS leading to the identification of acetylated derivatives of 2,5-trans-dihydroxymethyl-3,4-trans-dihydroxypyrrolidine (1), 1-deoxymannojirimycin, 1-deoxynojirimycin, fagomine and homonojirimycin. Only from L. subglaucescens could a compound with the constitution and relative configuration expected for the penta-acetate of 1 be isolated, and its molecular structure was determined for the first time through extensive spectral data analysis.
Departamento de Química Orgânica, Instituto de Química-Unicamp, PO Box 6154, CEP 13087-930, Campinas-SP, Brazil. aderbal@iqm.unicamp.br
Aderbal F
AF
Magalhães
Celira C
CC
Santos
Eva G
EG
Magalhães
Marisa A
MA
Nogueira
D000107:Acetylation; D000470:Alkaloids / Q000032:analysis*; D000818:Animals; D003445:Crustacea / Q000187:drug effects; D029866:Derris / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods*; D010936:Plant Extracts / Q000737:chemistry* / Q000494:pharmacology; D013057:Spectrum Analysis
D000470:Alkaloids; D010936:Plant Extracts