Piperamides from Piper ottonoides by NMR and GC-MS Based Mixture Analysis
| Autor: | Wolff,Thiago, Santos,Priscila F. P., Valente,Ligia M. M., Magalhães,Alvicler, Tinoco,Luzineide W., Pereira,Rita C. A., Guimarães,Elsie F. |
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| Jazyk: | angličtina |
| Rok vydání: | 2015 |
| Předmět: | |
| Zdroj: | Journal of the Brazilian Chemical Society, Volume: 26, Issue: 11, Pages: 2321-2330, Published: NOV 2015 Journal of the Brazilian Chemical Society v.26 n.11 2015 Journal of the Brazilian Chemical Society Sociedade Brasileira de Química (SBQ) instacron:SBQ |
| Popis: | The species Piper ottonoides Yuncker (Piperaceae), known as “joão-brandim”, is a shrub that occurs in the Brazilian Amazon rainforest. Its roots and leaves are used in traditional medicine as local anesthetic to treat toothache and sore throat. In this study, the structural characterization in mixture of isobutyl amides present in semi-purified fractions from fruits, leaves, stems and roots of P. ottonoides was achieved by employing gas chromatography-mass spectrometry (GC-MS) and a combination of nuclear magnetic resonance (NMR) techniques (1H, 1H-1H COSY, 1H-13C HSQC, 1H-13C HMBC, TOCSY and 1H-1H J-RES). The MS fragmentation patterns and the NMR chemical shifts, multiplicities, coupling constants and the signal correlations in the two-dimensional spectra were carefully analyzed also taking into account some key elements of differentiation among the compounds. The data set allowed identifying unequivocally the new amide N-isobutyl-7-(4’- methoxyphenyl)-2E,4E-heptadienamide, which we named ottonoidenamide as well as piperovatine and chingchengenamide A in all parts of the plant, the additional presence of pipercallosine and pipercallosidine in roots and of dihydropiperlonguminine in fruits and leaves. The presence of piperovatine and pipercallosine in P. ottonoides should be associated to its traditional use. |
| Databáze: | OpenAIRE |
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