Gas chromatographic techniques and spectroscopic approaches for a deep characterization of Piper gaudichaudianum Kunth essential oil from Brazil

• Published in: Journal of Chromatography A Vol. 1732; p. 465208
• Main Authors: Cucinotta, Lorenzo, Rotondo, Archimede, Coppolino, Carmelo, Irrera, Elisa, Duarte, Laura A., Cipriano, Roger R., Amaral, Wanderlei do, Loureiro, Wilson, Deschamps, Cicero, Bizzo, Humberto Ribeiro, Donato, Paola, Sciarrone, Danilo, Mondello, Luigi, Salerno, Tania Maria Grazia
• Format: Journal Article
• Language: English
• Published: Netherlands Elsevier B.V 13.09.2024
• Subjects: Enantiomeric separation; GC-FTIR; GC-MS; NMR; Preparative gas chromatography; GC-MS; Enantiomeric separation; GC-FTIR; NMR; Preparative gas chromatography
• ISSN: 0021-9673; 1873-3778
• DOI: 10.1016/j.chroma.2024.465208

•Characterization of the essential oil through GC–MS analysis.•Fast isolation of a high-purity amount of an unknown molecule through preparative gas chromatography.•GC-FTIR, GC–MS, and NMR analyses for the structural elucidation of the unknown molecule.•Investigation of the enantiomeric ratios of eight chiral terpenes by means of multidimensional gas chromatography. Piper gaudichaudianum Kunth essential oil (EO) is a natural source of bioactive components, having multiple therapeutic applications. Its chemical composition is highly variable, and strictly depends on abiotic factors, resulting in various biological activities. The present study details the utilization of multiple gas chromatographic techniques alongside nuclear magnetic resonance (NMR) spectroscopy to characterize the essential oil of Piper gaudichaudianum Kunth from Brazil. Seventy-six components were identified using GC–MS analysis, while enantio‑selective multidimensional gas chromatography elucidated the enantiomeric distribution of eight chiral components, for the first time in the literature. Following GC–MS analysis, an unidentified component, constituting approximately 27 % of the total oil, prompted an isolation step through preparative gas chromatography. Through the combined use of nuclear magnetic resonance, GC-Fourier transform infrared spectroscopy (FTIR), and mass spectrometry (MS), the unknown molecule was structurally identified as 4-[(3E)‑dec-3-en-1-yl]phenol. Remarkably, it was identified as a known molecule, gibbilimbol B, and not previously listed in any MS database. Subsequently, the spectrum was included in a commercial library, specifically the FFNSC 4.0 MS database, for the first time.