Peganol — A new alkaloid from Peganum harmala

Chemistry of Natural Compounds
1971.0

Abstract

Continuing the separation of the mixture of bases isolated from Peganum harmala at the flowering and incipient fruit-bearing stage, we obtained a new base called peganol, which has mp 178-180°C (decomp°), is optically inactive, has the composition C₁₁H₁₂N₂O and mol. wt. 188 (mass spectrometry), and is isomeric with peganine. The UV spectrum of peganol has only one maximum at 275 nm (log a 3.96), indicating the absence of a quinazolone structure, confirmed by the IR spectrum with no carbonyl group absorption. We assumed peganine and peganol have the same heterocyclic skeleton and are isomers with respect to the hydroxy group position. The mass spectrum of peganol shows the main peak of the ion with m/e 171 (M-17), suggesting the hydroxy group is at C-4 or C-11. The NMR spectrum lacks a sharp two-proton singlet in the 4.5-4.6 ppm region, so the substituent is at C-4, and the structure is expressed by formula (I). Peganol oxidized by potassium permanganate in acetone solution yielded a substance with properties coinciding with deoxyvasicinone (no melting point depression in mixture), confirming the proposed structure.

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