Biotransformation of phenolic 1-benzyl-N-methyltetrahydroisoquinolines in plant cell cultures followed by LC/NMR, LC/MS, and LC/CD.
(+/-)-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.
Cui
Wenhua
W
Kobe Pharmaceutical University, 4-19-1 Motoyamakita, Kobe-shi 658-8558, Japan.
Iwasa
Kinuko
K
Sugiura
Makiko
M
Takeuchi
Atsuko
A
Tode
Chisato
C
Nishiyama
Yumi
Y
Moriyasu
Masataka
M
Tokuda
Harukuni
H
Takeda
Kazuyoshi
K
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*
D010636:Phenols; D044005:Tetrahydroisoquinolines