Identification of alkaloids; the condensation products of biogenic amines with formaldehyde, enzymatically formed from 5-methyltetrahydrofolic acid.
The use of thin-layer chromatography has demonstrated that incubations of indoleamines with 5-methyl[14-C]tetrahydrofolic acid and an enzyme previously described as an N-methyltransferase, do not yield Nw, N1, or O-methylated products. Further elucidation by thin-layer chromatography, gas chromatography, mass spectrometry and selected ion monitoring enabled us to identify the reaction products as tetrahydroisoquinolines and tetrahydro-beta-carbolines in mixtures incubated respectively with catecholamines and indoleamines in the presence of 5-methyl[14-C]tetrahydrofolic acid and enzyme. The alkaloids have been shown to originate from a spontaneous condensation of the corresponding amines with formaldehyde, this latter being formed in the first stage of the reaction by enzymatic conversion from 5-methyltetrahydrofolic acid.
D000470:Alkaloids / Q000138:chemical synthesis*; D000818:Animals; D001679:Biogenic Amines; D001921:Brain / Q000201:enzymology; D002243:Carbolines / Q000138:chemical synthesis; D055598:Chemical Phenomena; D002621:Chemistry; D002849:Chromatography, Gas; D002855:Chromatography, Thin Layer; D005492:Folic Acid / Q000031:analogs & derivatives*; D005557:Formaldehyde; D007546:Isoquinolines / Q000138:chemical synthesis; D007668:Kidney / Q000201:enzymology; D013058:Mass Spectrometry; D008780:Methyltransferases; D051381:Rats; D013552:Swine
D000470:Alkaloids; D001679:Biogenic Amines; D002243:Carbolines; D007546:Isoquinolines; D005557:Formaldehyde; D005492:Folic Acid; D008780:Methyltransferases