• Journal of Crop Science and Biotechnology
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• v.11 no.1
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• pp.45-50
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• 2008

Lignans and neolignans are optically active plant secondary metabolites. Research on biosynthesis of lignans has already been advanced especially for the formation of (+) pinoresinol but information on the biosynthesis of 8-O-4'- neolignans is still limited. Moreover, the chemical structure(position of substituents on aromatic rings) and stereochemistry of 8-O-4' neolignans is not clear. Katayama and Kado discovered that incubation of cell-free extracts from E. ulmoides with coniferyl alcohol in the presence of hydrogen peroxide gave (+)-erythro- and (-)-threo- guaiacylglycerol 8-O-4'-(coniferyl alcohol) ether (GGCE)(diastereomeric ratio, 3:2) which is the first report on enzymatic formation of optically active -8-O-4' neolignans from an achiral monolignol. In this aspect, enzymatic formation of guaiacyl 8-O-4' neolignan is noteworthy to clarify its stereochemistry from incubation of coniferyl alcohol with enzyme prepared from Eucommia ulmoides. In this experiment, soluble and insoluble enzymes prepared from E. ulmoides were incubated with 30 mM coniferyl alcohol(CA) for 60 min. The enzyme catalyzed GGCE, dehydrodiconiferyl alcohol(DHCA), and pinoresinol identified by reversed phase HPLC. Consequently, diastereomeric compositions of GGCE were determined as erythro and threo isomer. Enantiomeric composition was determined by the chiral column HPLC. Both enzyme preparations enantioselectively formed (-)-erythro, (+)-erythro and (+)-threo, (-)-threo-GGCEs respectively.

• YAKHAK HOEJI
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• v.42 no.6
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• pp.576-582
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• 1998

Fenfluramine, an anorectic agent, is widely abused as a diet pill in Korea because it is freely marketed in China without any regulation. The optical isomers of fenfluramine hav e different phamacological actions: d-form is used as an anorectic agent, while l-form as a neuroleptic agent. To investigate the metabolism when racemic fenfluramine was administered orally, the urinary excretion of fenfluramine was studied in rats. The enantiomeric separation of fenfluramine was performed on achiral column by gas chromatography using (S)-N-(trifluoroacetyl)-l-prolyl chloride (TFP) as a derivatizing agent. After administration of 15mg/kg of racemic fenfluramine to rats, d-, l-fenfluramine and its metabolites d- and l norfenfluramine in urine were determined by chromatographic separation of TFP derivatives on DB-1 at retention time of 11.2, 11.8, 8.4 and 8.6 min respectively. Urinary recoveries of d and l-fenfluramine in rat were 0.42-5.9O% and 0.18-1.20% respectively in urine specimens collected during first 24hr. The comparison in the levels of isomers showed that d- fenfluramine were higher than l-form, while d-norfenfluramine were lower than l-form. The ratios between parent compound and metabolite revealed that d-norfenfluramine to d-fenfluramine ranged from 1.0 to 4.4, while the ratio of l-norfenfluramine to l-fenfluramine was 8.2-21.1 indicating that l-fenfluramine is metabolized faster than the d-isomer.