Quinolizidine Alkaloids from Plants and their Cell Suspension Cultures.

Abstract

The alkaloid composition of cell suspension cultures and differentiated plants of Lupinus polyphyllus was evaluated using quartz capillary gas-liquid chromatography, GLC-MS and FD-MS. Lupanine (97% of total alkaloids), sparteine, 13-angeloyloxylupanine and 13-tigloyloxylupanine were detected in alkaloid extracts of L. polyphyllus cell suspension cultures. Lupanine, 13-cis and 13-trans-cinnamoyloxylupanine were found in the spent cell culture medium. No significant difference was found in the alkaloid composition of photomixotrophic and heterotrophic cell strains although the alkaloid content was 5 to 10 times higher in photomixotrophic cell strains. In the respective plants we could identify 18 alkaloids which include the following esters of 13-hydroxylupanine: 13-tigloyloxylupanine, 13-angeloyloxylupanine, 13-cis-cinnamoyloxylupanine, 13-trans-cinnamoyloxylupanine, 13-benzoyloxylupanine, 13-(2-methylbutyryl)-oxylupanine; and 13-vanilloyloxylupanine.

Attraction, deterrence or intoxication of bees (Apis mellifera) by plant allelochemicals

“…Alkaloids were separated by eapillary GLC and analysed by a nitrogen-specific detector (Figs 4-10) and mass spectrometry (GLC-MS). For most compounds reference spectra had been recorded in our laboratories before, so that most alkaloids could be unequivocally identified (Tables 4-6) (Wink et al 1982(Wink et al , 1983Witte et al 1986;Christen et al 1990;Wink & Witte 1991). Table 4 Pollen and nectar of both Lupinus polyphyllus and Brugmansia aurea show a much simpler pattern of alkaloids than other aerial plant parts, although the main alkaloids are identical.…”

Alkaloids

“…PND was shown to be 10 to 50 times more sensitive than FID (Wink et al 1982). The other detection method commonly used to obtain further information on the chemical structures was EI-MS.…”

“…Wink et al (1980) analyzed by capillary GC the quinolizidine alkaloids from plants and cell suspension cultures of Lupinus polyphyllus. Using the same method, the analysis of quinolizidine alkaloids from several other genera have been reported by the same group (Wink et al 1981b(Wink et al , 1982Wink and Hartmann 1980;Hatzold et al 1983;Strack et al 1991). Tables with the retention indices of a large number of quinolizidine alkaloids and th~ir characteristic ion fragments (EI-MS) have been given by Wink et al (1981aWink et al ( , 1983 and Muehlbauer et al (1988).…”

“…The other detection method commonly used to obtain further information on the chemical structures was EI-MS. From some esters of hydroxylupanine it was not possible to detect the molecular ion (Wink et al 1982). From some esters of hydroxylupanine it was not possible to detect the molecular ion (Wink et al 1982).…”

Alkaloid variation in New Zealand kōwhai, Sophora species

“…The alkane standards produced a linear correlation with respect to retention time, from which RIs for alkaloids were determined (Kovats, 1958). Additional validation of alkaloid identity was obtained by review (Ausloos et al, 1999) of the NIST08 library (NIST, 2008) and comparison of previously reported fragmentation patterns for lupin alkaloids (Wink et al, 1982(Wink et al, , 1995Kite and Pennington, 2003;Lee et al, 2013). Analyses were performed on an Agilent 7890A gas chromatograph with a CTC Analytics PAL system autosampler and an Agilent 5975C inert XL MSD with triple axis detector, under the control of Enhanced ChemStation software.…”