title: Biotransformation of phenolic 1-benzyl-N-methyltetrahydroisoquinolines in plant cell cultures followed by LC/NMR, LC/MS, and LC/CD.
abstract: (+/-)-1-Benzyl- N-methyltetrahydroisoquinolines 7-10 and 11-14 with one and two hydroxy groups on the aromatic rings, respectively, were fed individually to cultured cells of Corydalis and Macleaya species, respectively. The structures of the metabolites were determined by using combinatorial techniques, including LC/NMR, LC/MS-MS, and LC/CD. The enantiomeric excesses of the metabolites were derived from LC/CD and LC/MS-MS analyses. In cell cultures of Corydalis and Macleaya species, laudanine (7), with a hydroxy group at C-3', can form the berberine bridge at C-2' and C-6' to produce S- and R-enantiomers of 2,3,9,10- and 2,3,10,11-oxygenated protoberberines (20 and 21), respectively, whereas reticuline (11) and protosinomenine (12), incoporating a hydroxy group at C-3', form the berberine bridge at C-2' to furnish the S-enantiomer of 2,3,9,10-oxygenated protoberberines (23 and 21), respectively.
authors.affiliation: Kobe Pharmaceutical University, 4-19-1 Motoyamakita, Kobe-shi 658-8558, Japan.
authors.forename: Wenhua
authors.initials: W
authors.lastname: Cui
authors.forename: Kinuko
authors.initials: K
authors.lastname: Iwasa
authors.forename: Makiko
authors.initials: M
authors.lastname: Sugiura
authors.forename: Atsuko
authors.initials: A
authors.lastname: Takeuchi
authors.forename: Chisato
authors.initials: C
authors.lastname: Tode
authors.forename: Yumi
authors.initials: Y
authors.lastname: Nishiyama
authors.forename: Masataka
authors.initials: M
authors.lastname: Moriyasu
authors.forename: Harukuni
authors.initials: H
authors.lastname: Tokuda
authors.forename: Kazuyoshi
authors.initials: K
authors.lastname: Takeda
mesh_terms: D001711:Biotransformation; D002478:Cells, Cultured; D031311:Corydalis / Q000737:chemistry*; D007564:Japan; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry / Q000378:metabolism*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D044005:Tetrahydroisoquinolines / Q000737:chemistry / Q000378:metabolism*
chemical_list: D010636:Phenols; D044005:Tetrahydroisoquinolines