Comparative qualitative and quantitative determination of alkaloids in narcotic and condiment Papaver somniferum cultivars.
In the present study morphinan, tetrahydrobenzylisoquinoline, benzo[c]phenanthridine, and phthalideisoquinoline alkaloids were determined qualitatively and quantitatively by HPLC and LC-MS analysis in tissues of the Tasmanian Papaver somniferum L. elite cultivar C048-6-14-64. The data were compared with the results from the low-morphine cultivar "Marianne". In the elite cultivar, 91.2% of the latex alkaloids consist of the three pharmaceutically most valuable alkaloids: morphine, codeine, and thebaine. In the root system, the major alkaloids are sanguinarine/10-hydroxysanguinarine and dihydrosanguinarine/10-hydroxydihydrosanguinarine. In the stems and leaves of C048-6-14-64, the same alkaloids were measured as in the latex. In the stems, a gradient in relative total alkaloid content from the top downward toward the roots was observed. The concentration of morphine was decreasing toward the roots, whereas an increasing gradient from the upper to the lower stem parts was detected for codeine. The relative total alkaloid concentration in leaves remained constant; no gradient was observed. The cultivar "Marianne" displayed a shifted pattern of alkaloid accumulation and reduced levels of total alkaloid. In the condiment cultivar, 80.5% of the alkaloids of the latex consisted of the two phthalideisoquinoline alkaloids narcotoline and noscapine. Only 18.8% of the relative total alkaloid content were morphinan alkaloids. In contrast to the narcotic cultivar, in which the benzo[c]phenanthridines in roots dominated over the morphinan and tetrahydrobenzylisoquinoline alkaloids, the concentration of benzo[c]phenanthridines in "Marianne" was similar to that of morphinan and tetrahydrobenzylisoquinoline alkaloids. These data suggest a differential alkaloid regulation in each cultivar of P. somniferum.
Frick
Susanne
S
Leibniz Institute of Plant Biochemistry, Weinberg 3, D-06120 Halle (Saale), Germany. sfrick@ipb-halle.de
Kramell
Robert
R
Schmidt
Jürgen
J
Fist
Anthony J
AJ
Kutchan
Toni M
TM
D000470:Alkaloids / Q000032:analysis* / Q000737:chemistry*; D001315:Australia; D003061:Codeine / Q000032:analysis; D015394:Molecular Structure; D009019:Morphinans / Q000032:analysis; D009294:Narcotics / Q000737:chemistry; D010207:Papaver / Q000737:chemistry*; D010946:Plants, Medicinal / Q000737:chemistry*
D000470:Alkaloids; D009019:Morphinans; D009294:Narcotics; D003061:Codeine