title: 13,14-dihydrocoptisine--the genuine alkaloid from Chelidonium majus.
abstract: The genuine major benzylisoquinoline alkaloid occurring in the traditional medicinal plant greater celandine (Chelidonium majus L.) is 13,14-dihydrocoptisine and not - as described previously - coptisine. Structure of 13,14-dihydrocoptisine was elucidated. The discrepancy between the alkaloid pattern of the living plants and that of detached and dried leaves is due to the rapid and prompt conversion of 13,14-dihydrocoptisine to coptisine in the course of tissue injuries. Indeed, apart from the major alkaloid, some minor alkaloids might also be converted; this however is not in the centre of focus of this paper. This conversion is initiated by the change of pH. In vivo 13,14-dihydrocoptisine is localized in the acidic vacuoles, where it is stable. In contrast, in the neutral milieu, which results when vacuoles are destroyed in the course of tissue injuries, the genuine alkaloid is oxidized to yield coptisine. Accordingly, when alkaloids from C.majus should be analyzed, any postmortal conversion of 13,14-dihydrocoptisine has to be prevented.
authors: Institute for Plant Biology, TU Braunschweig, Mendelssohnstr. 4, 38106 Braunschweig, Germany.
authors: Jana
authors: J
authors: Paulsen
authors: Institute for Plant Biology, TU Braunschweig, Mendelssohnstr. 4, 38106 Braunschweig, Germany; Yasouj University, Yasouj, Kohgiluyeh Va Boyer Ahmad, Iran.
authors: Mahdi
authors: M
authors: Yahyazadeh
authors: Institute for Plant Biology, TU Braunschweig, Mendelssohnstr. 4, 38106 Braunschweig, Germany.
authors: Sophie
authors: S
authors: Hänsel
authors: Institute for Plant Biology, TU Braunschweig, Mendelssohnstr. 4, 38106 Braunschweig, Germany.
authors: Maik
authors: M
authors: Kleinwächter
authors: Chemistry Department, Central NMR Laboratory, TU Braunschweig, Hagenring 30, 38106 Braunschweig, Germany.
authors: Kerstin
authors: K
authors: Ibrom
authors: Institute for Plant Biology, TU Braunschweig, Mendelssohnstr. 4, 38106 Braunschweig, Germany. Electronic address: d.selmar@tu-bs.de.
authors: Dirk
authors: D
authors: Selmar
mesh_terms: D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification*; D001599:Berberine / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism; D001600:Berberine Alkaloids / Q000737:chemistry / Q000302:isolation & purification*; D028281:Chelidonium / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*
chemical_list: C000598000:13,14-dihydrocoptisine; D000470:Alkaloids; D001600:Berberine Alkaloids; C034384:coptisine; D001599:Berberine
keywords: Benzylisoquinoline alkaloids; Chelidonium majus; Coptisine; Dihydrocoptisine; Greater celandine