title: Selective amination of secoiridoid glycosides to give monomeric pyridine, dimeric pyridine, and naphthyridine alkaloids.
abstract: Treatment of the secoiridoids oleuropein (4), ligstroside (5) and methyloleoside (6) by beta-D-glucosidase in the presence of ammonium chloride led exclusively to monomeric pyridine alkaloids 7, 1, and 8. Dimeric 3,4,5-trisubstituted pyridines were obtained from methyloleoside (6) when ammonium chloride was generated in the reaction mixture by successive additions of ammonia and hydrochloric acid. The use of ammonium acetate permitted conversion of secoiridoids 4 and 5 into the naphthyridine alkaloid jasminine (3).
authors.affiliation: Laboratoire de Pharmacognosie de l'Université René Descartes, UMR/CNRS no. 8638, Faculté des Sciences Pharmaceutiques et Biologiques, 4 avenue de l'Observatoire, F-75006 Paris, France.
authors.forename: Y
authors.initials: Y
authors.lastname: Ranarivelo
authors.forename: P
authors.initials: P
authors.lastname: Magiatis
authors.forename: A L
authors.initials: AL
authors.lastname: Skaltsounis
authors.forename: F
authors.initials: F
authors.lastname: Tillequin
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification; D000586:Amination; D000641:Ammonia / Q000737:chemistry; D002384:Catalysis; D002845:Chromatography; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification*; D006851:Hydrochloric Acid / Q000737:chemistry; D057888:Iridoid Glucosides; D039823:Iridoids; D015394:Molecular Structure; D009287:Naphthyridines / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification; D009525:Niacin / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification; D019906:Nuclear Magnetic Resonance, Biomolecular; D029592:Oleaceae / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry / Q000302:isolation & purification*; D011725:Pyridines / Q000737:chemistry / Q000302:isolation & purification*; D001617:beta-Glucosidase / Q000378:metabolism
chemical_list: C445383:4,4'-bis-methyl-5,5'-((1-methyltrimethylene)di)methylnicotinate; C445382:4-hydroxyphenylethyl-5-ethyl-3-methoxycarbonyl-4-pyridineacetate; D000470:Alkaloids; D005960:Glucosides; D057888:Iridoid Glucosides; D039823:Iridoids; D009287:Naphthyridines; D011714:Pyrans; D011725:Pyridines; C445384:jasminine; C445381:methyloleoside; D009525:Niacin; C002769:oleuropein; D000641:Ammonia; C445380:ligstroside; D001617:beta-Glucosidase; D006851:Hydrochloric Acid