Piperidone derivative from Dalbergia sympathetica

Abstract

An alcoholic extract of Dalbergia sympathetica, on column chromatography, yielded a compound which analyzed for C(6)H(11)NO(3) (M(+) 145). The IR spectrum of the compound showed the presence of carbonyl and hydroxyl groups. PMR, (13)C and DEPT NMR spectral studies of the compound showed the presence of one N-methyl, two methine and two methylene groups. A quaternary carbon signal at delta 172.88 ppm was assigned to C-2 carbonyl of the compound. From all the above observations and also from the HMQC 2D NMR spectrum, the compound was identified as 3, 6-dihydroxy-N-methyl-2-piperidone. This is the first report of the natural occurrence of this compound from plant sources.

Comments on ‘Piperidone derivative from Dalbergia sympathetica’

“…E-mail: tammo.winkler@syngenta.com authentic 4 3 is rather good. Finally, the EI MS spectra 1,4 are very similar. In particular, the base peak at m/z 100 is easily explained 4 by the loss of COOH to form the stable pyrrolinium ion.…”

“…This interpretation implies that the additional triplet splitting of ca 5 Hz in the complex 4,5 signal of H-4 has been missed by the authors. 1 On the other hand, the typical 5b,6 long-range coupling between Ha-3 and Ha-5 was observed. 1 The 1 H chemical shift data 4,5 differ slightly from each other due to the strong pH dependence 7 of the chemical shifts of amino acids in D 2 O solution.…”

“…1 On the other hand, the typical 5b,6 long-range coupling between Ha-3 and Ha-5 was observed. 1 The 1 H chemical shift data 4,5 differ slightly from each other due to the strong pH dependence 7 of the chemical shifts of amino acids in D 2 O solution. Table 1 shows furthermore, that the agreement of the 13 C chemical shifts reported 1 for the isolated compound with those of Ł Correspondence to: Tammo Winkler, Syngenta Crop Protection AG, CH 4002 Basel, Switzerland.…”