Enantiomeric separation of racemic 1-benzyl-N-methyltetrahydroisoquinolines on chiral columns and chiral purity determinations of the O-methylated metabolites in plant cell cultures by HPLC-CD on-line coupling in combination with HPLC-MS.
Effective enantiomeric separations of 1-benzyl-N-methyltetrahydroisoquinolines were achieved using commercially available Chiralcel OD-H and OJ-H columns. Online LC-CD analysis allowed for the establishment of a correlation between the absolute configuration of the separated enantiomers and their characteristic CD transitions. LC-MS combined with LC-CD analysis permitted chiral purity determinations of O-methylated metabolites of nine phenolic 1-benzyl-N-methyltetrahydroisoquinolines in cell cultures of Corydalis, Macleaya, and Nandina species.
Iwasa
Kinuko
K
Kobe Pharmaceutical University, Natural Medicinal Chemistry, 4-19-1 Motoyamakita-machi, Higashinada-ku, Kobe 658-8558, Japan. K-iwasa@kobepharma-u.ac.jp
Doi
Yasuhiro
Y
Takahashi
Teturo
T
Cui
Wenhua
W
Nishiyama
Yumi
Y
Tode
Chisato
C
Moriyasu
Masataka
M
Takeda
Kazuyoshi
K
Minami
Hiromichi
H
Ikezawa
Nobuhiro
N
Sato
Fumihiko
F
D002478:Cells, Cultured; D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D006859:Hydrogen / Q000737:chemistry*; D013058:Mass Spectrometry; D008745:Methylation; D015394:Molecular Structure; D009862:Online Systems; D010936:Plant Extracts / Q000737:chemistry; D011804:Quinolines / Q000737:chemistry* / Q000378:metabolism*; D013237:Stereoisomerism
D010936:Plant Extracts; D011804:Quinolines; D006859:Hydrogen