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).
MeSH terms
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Alkaloids / chemical synthesis
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Alkaloids / chemistry
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Alkaloids / isolation & purification
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Amination
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Ammonia / chemistry
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Catalysis
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Chromatography
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Glucosides / chemistry
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Glucosides / isolation & purification*
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Hydrochloric Acid / chemistry
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Iridoid Glucosides
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Iridoids
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Molecular Structure
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Naphthyridines / chemical synthesis
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Naphthyridines / chemistry
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Naphthyridines / isolation & purification
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Niacin / analogs & derivatives
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Niacin / chemistry
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Niacin / isolation & purification
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Nuclear Magnetic Resonance, Biomolecular
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Oleaceae / chemistry*
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Pyrans / chemistry
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Pyrans / isolation & purification*
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Pyridines / chemistry
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Pyridines / isolation & purification*
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beta-Glucosidase / metabolism
Substances
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4,4'-bis-methyl-5,5'-((1-methyltrimethylene)di)methylnicotinate
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4-hydroxyphenylethyl-5-ethyl-3-methoxycarbonyl-4-pyridineacetate
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Alkaloids
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Glucosides
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Iridoid Glucosides
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Iridoids
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Naphthyridines
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Pyrans
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Pyridines
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jasminine
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methyloleoside
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Niacin
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oleuropein
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Ammonia
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ligstroside
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beta-Glucosidase
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Hydrochloric Acid