Leptorhabine — A new alkaloid from Leptorhabdos parviflora

Chemistry of Natural Compounds
1974.0

Abstract

We have investigated the epigeal part of the plant L. parviflora collected in the valley of the R. Talas (close to the town of Dzhambul) in the flowering period. When the combined ether-soluble alkaloids were separated on a column of alumina, from ether-chloroform (10 : 2) eluates we isolated a liquid base with the composition C9H11NO, [α]D +10° (c 1.015; chloroform); M+ 149; Rf 0.56 [TLC on silica gel in the benzene-methanol (4:1) system]. The UV spectrum of the base has two maxima at λmax 263,269 nm (log ε 3.36, 3.33) which are characteristic for alkaloids of the pyridine type. In the IR spectrum of the base, absorption bands appear at 3400-3200 cm-1 (OH), 2980-2940 cm-1 (C-CH3), and 1605 and 1580 cm-1 (pyridine ring). The base is a new one and we have called it leptorhabine. NMR spectrum analysis (showing aromatic protons, hydroxy group, methyl, methylene, and methine protons), oxidation with KMnO4 in an alkaline medium (producing pyridine-3,4-dicarboxylic acid), NMR of O-acetylleptorhabine, and mass spectrum data enabled us to suggest two possible structures: 1-hydroxy-3-methylcyclopenta [d]pyridine and 1-methyl-3-hydroxycyclopenta [d]pyridine. From a comparison of the NMR spectrum of leptorhabine with literature data, a consideration of Dreiding models, and biogenetic considerations, we determined the probable structure of leptorhabine.

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