Kinetic study of littorine rearrangement in Datura innoxia hairy roots by 13C NMR spectroscopy
| Autor: | Lanoue, A., Boitel-Conti, M., Portais, J.C., Laberche, J.C., Barbotin, J.N., Christen, P., Sangwaan-Norreel, B. |
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| Přispěvatelé: | Génie Enzymatique et Cellulaire (GEC), Université de Technologie de Compiègne (UTC)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS) |
| Jazyk: | angličtina |
| Rok vydání: | 2002 |
| Zdroj: | Journal of Natural Products Journal of Natural Products, American Chemical Society, 2002, 65, pp.1131-1135 |
| ISSN: | 0163-3864 1520-6025 |
| Popis: | The kinetics of tropane alkaloid biosynthesis, particularly the isomerization of littorine into hyoscyamine, were studied by analyzing the kinetics of carbon-13 (13C) in metabolites of Datura innoxia hairy root cultures fed with labeled tropoyl moiety precursors. Both littorine and hyoscyamine were the major alkaloids accumulated, while scopolamine was never detected. Feeding root cultures with (RS)-phenyl[1,3-13C2]lactic acid led to 13C spin-spin coupling detected on C-1' and C-2' of the hyoscyamine skeleton, which validated the intramolecular rearrangement of littorine into hyoscyamine. Label from phenyl[1-13C]alanine or (RS)-phenyl[1,3-13C2]lactic acid was incorporated at higher levels in littorine than in hyoscyamine. Initially, the apparent hyoscyamine biosynthesized rate (vapphyo = 0.9 mol 13C·flask-1·d-1) was lower than littorine formation (vapplitto = 1.8 mol 13C·flask-1·d-1), suggesting that the isomerization reaction could be rate limiting. The results obtained for the kinetics of littorine biosynthesis were in agreement with the role of this compound as a direct precursor of hyoscyamine biosynthesis. |
| Databáze: | OpenAIRE |
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