84272-48-0Relevant articles and documents
PEROXIDASE, MIXED-FUNCTION OXIDASE- AND METAL-CATALYSED OXIDATION OF PHENYLPROPENOIDIC COMPOUNDS
Bassoli, Angela,Gregorio, Giuseppina Di,Rindone, Bruno,Tollari, Stefano,Chioccara, Francesco,Salmona, Mario
, p. 763 - 768 (2007/10/02)
The system HRP-H2O2 transforms the phenolic phenylpropenoidic compounds methyl ferulate, 4, isoeugenol, 6, eugenol, 8, and 3-O-methyldopamine, 12, into oxidative dimerisation products or compounds therefrom.Resinification occurs when an ortho-diphenol structure, as in caffeic acid, 3, dopa, 10, and dopamine, 11, is present.This behaviour could derive from the formation of phenoxy radicals arising from an oxidation effected by the horseradish peroxidase compound I, 20.Rat-liver microsomes and prostaglandine endo-peroxidase synthetase give O-demethylation of ferulic acid, 2, via a similar co-enzymatic system.The dimer 5 is obtained from methyl ferulate, 4, when treated with the biomimetic catalyst manganese(III)tetraphenylporphyrinate acetate (MnTPPOAc), 30, with iodosylbenzene as the oxidant.The bis(salicylaldehyde)ethylenediiminocobalt(II)-catalysed oxidation of ferulic acid, 2, with dioxygen in methanol gives some demolition products such as vanillic aldehyde, 33, methyl vanillate, 34, a methyl ketone, 42, and a β-keto acid, 44, which retains the original carbon atom skeleton.
Biosynthesis of Phenanthroindolizidine Alkaloids: Incorporation of 2-Pyrrolidin-2-ylacetophenone and Benzoylacetic Acid and Derivatives
Herbert, Richard B.,Jackson, Frederick B.,Nicolson, Ian T.
, p. 825 - 831 (2007/10/02)
2-Pyrrolidin-2-ylacetophenone (12) and its oxygenated derivatives, (13) and (14), bearing 14C and 3H labels are synthesized and are shown to be intact precursors for the phenanthroindolizidine alkaloid, tylophorinine (16), in Tylophora asthmatica; the three amines, singly labelled with tritium, are shown to be precursors for tylophorine (3) and tylophorinidine (17).Benzoylacetic acid (9) and p-hydroxybenzoylacetic acid (10), but not 4-hydroxy-3-methoxybenzoylacetic acid, are also precursors for tylophorinine (16).The results allow partial description of the biosynthetic pathways tophenanthroindolizidine alkaloids.A degradation is described which allowed the location of label in 2-pyrrolidin-2-ylacetophenone, derived from ornithine, to be established.
