Biosynthesis of podophyllotoxin in Linum album cell cultures
| Autor: | Jorg Windhövel, Graham Eaton, Jack G. Woolley, A. Wilhelm Alfermann, Veronique Seidel, Maike Petersen, Manuel Medarde, Randolph R.J. Arroo |
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| Rok vydání: | 2001 |
| Předmět: |
Coumaric Acids
Stereochemistry Cinnamyl-alcohol dehydrogenase Phenylalanine Plant Science Phenylalanine ammonia-lyase Cinnamic acid Lignans Mass Spectrometry Ferulic acid Hydroxylation chemistry.chemical_compound Flax Coenzyme A Ligases Genetics medicine Cells Cultured Chromatography High Pressure Liquid Phenylalanine Ammonia-Lyase Podophyllotoxin Lignan Carbon Isotopes Molecular Structure Hydrogen-Ion Concentration Aldehyde Oxidoreductases Alcohol Oxidoreductases chemistry Biochemistry Cinnamates Cell Division medicine.drug Drugs Chinese Herbal |
| Zdroj: | Planta. 215(6) |
| ISSN: | 0032-0935 |
| Popis: | Cell cultures of Linum album Kotschy ex Boiss. (Linaceae) showing high accumulation of the lignan podophyllotoxin (PTOX) were established. Enzymological studies revealed highest activities of phenylalanine ammonia-lyase, cinnamyl alcohol dehydrogenase, 4-hydroxycinnamate:CoA ligase and cinnamoyl-CoA:NADP oxidoreductase immediately prior to PTOX accumulation. To investigate PTOX biosynthesis, feeding experiments were performed with [2-(13)C]3',4'-dimethoxycinnamic acid, [2-(13)C]3',4'-methylenedioxycinnamic acid (MDCA), [2-(13)C]3',4',5'-trimethoxycinnamic acid, [2-(13)C]sinapic acid, [2-(13)C]- and [2,3-(13)C(2)]ferulic acid. Analysis of the metabolites by HPLC coupled to tandem mass spectrometry revealed incorporation of label from ferulic acid into PTOX and deoxypodophyllotoxin (DOP). In addition, MDCA was also unambiguously incorporated intact into PTOX. These observations suggest that in L. album both ferulic acid and methylenedioxy-substituted cinnamic acid can be incorporated into lignans. Furthermore, it appears that, in this species, the hydroxylation of DOP is a rate-limiting point in the pathway leading to PTOX. Electronic supplementary material to this paper can be obtained by using the Springer LINK server located at http://dx.doi.org/wo.1007/s00425-002-0834-1. |
| Databáze: | OpenAIRE |
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