title: Structural analyses of metabolites of phenolic 1-benzyltetrahydroisoquinolines in plant cell cultures by LC/NMR, LC/MS, and LC/CD.
abstract: The metabolism of the phenolic 1-benzyltetrahydroisoquinoline alkaloids was studied in cell cultures of Macleaya and Corydalis species. The crude alkaloid fraction obtained from feeding experiments was investigated by application of the combined LC/NMR and LC/APCI-MS (/MS) techniques. Several metabolites were detected, and their structures (6 and 8-14) were identified. Bioconversion of the phenolic 1-benzyltetrahydroisoquinoline (2) into the pseudoprotoberberine (8) was demonstrated for the first time. LC/APCI-MS and LC/CD experiments carried out on a chiral column permitted the deduction of the major enantiomeric form of the chiral metabolites. Thus, the combination of NMR, MS, and CD data permitted the structural elucidation and stereochemical analysis of the metabolites in the extract matrix solution, without isolation and sample purification prior to the coupling experiments.
authors.affiliation: Kobe Pharmaceutical University, 4-19-1 Motoyamakita, Higashinada-ku, Kobe-shi 658-8558, Japan. k-iwasa@kobepharma-u.ac.jp
authors.forename: Kinuko
authors.initials: K
authors.lastname: Iwasa
authors.forename: Wenhua
authors.initials: W
authors.lastname: Cui
authors.forename: Makiko
authors.initials: M
authors.lastname: Sugiura
authors.forename: Atsuko
authors.initials: A
authors.lastname: Takeuchi
authors.forename: Masataka
authors.initials: M
authors.lastname: Moriyasu
authors.forename: Kazuyoshi
authors.initials: K
authors.lastname: Takeda
mesh_terms: D002478:Cells, Cultured; D031311:Corydalis / Q000737:chemistry*; D007564:Japan; D013058:Mass Spectrometry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D028101:Papaveraceae / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry / Q000378:metabolism*; D013237:Stereoisomerism; D044005:Tetrahydroisoquinolines / Q000737:chemistry / Q000378:metabolism*
chemical_list: D010636:Phenols; D044005:Tetrahydroisoquinolines