Piper nigrum Oil – Determination of Selected Terpenes for Quality Evaluation

Mei Wang; Amar G. Chittiboyina; Jon F. Parcher; Zulfiqar Ali; Paul Ford; Jianping Zhao; Bharathi Avula; Yan-Hong Wang; Ikhlas A. Khan

doi:10.1055/a-0782-0548

Planta Medica, Inhaltsverzeichnis

Planta Med 2019; 85(03): 185-194
DOI: 10.1055/a-0782-0548

Natural Product Chemistry and Analytical Studies

Original Papers

Georg Thieme Verlag KG Stuttgart · New York

Piper nigrum Oil – Determination of Selected Terpenes for Quality Evaluation

Mei Wang

¹National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS, USA

,

Amar G. Chittiboyina

¹National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS, USA

,

Jon F. Parcher

¹National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS, USA

,

Zulfiqar Ali

¹National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS, USA

,

Paul Ford

²Technical Innovation Center, McCormick and Company, Inc., Hunt Valley, MD, USA

,

Jianping Zhao

¹National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS, USA

,

Bharathi Avula

¹National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS, USA

,

Yan-Hong Wang

¹National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS, USA

,

Ikhlas A. Khan

¹National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS, USA

³Division of Pharmacognosy, Department of BioMolecular Sciences, School of Pharmacy, University of Mississippi, University, MS, USA

› Institutsangaben

Abstract

The growing demand and commercial value of black pepper (Piper nigrum) has resulted in considerable interest in developing suitable and cost-effective methods for chemical characterization and quality evaluation purposes. In the current study, an extensive set of oil samples (n = 23) that were extracted by steam distillation from black pepper seeds was investigated to compare the chemical profiles of samples originating from nine major producing countries, as well as to identify potential chemical markers for quality evaluation. The twenty-two most abundant volatile compounds, mainly terpenes, in these oils were determined by conventional GC/MS analysis. Principal component analysis with this set of data revealed distinct clusters for samples that originated from China and Malaysia. Relatively low concentrations of sabinene (< 0.2%) and high concentrations of 3-carene (10.9 – 21.1%) were observed in these samples, respectively, compared to oil samples from other countries. The enantiomeric distributions of key terpene markers, viz., β-pinene, sabinene, limonene, and terpinen-4-ol, were determined by chiral GC/MS analysis. Interestingly, for these four monoterpenes, levo-isomers were found to be predominant, emphasizing the highly conserved enzymatic processes occurring in P. nigrum. Moreover, consistent enantiomeric ratios ((−) isomer/(+) isomer) of 92.2 ± 3.0% for β-pinene, 94.8 ± 2.8% for sabinene, 60.7 ± 1.1% for limonene, and 78.3 ± 1.3% for terpinen-4-ol were observed, independent of geographical location. These results demonstrate the potential of using stereospecific compositions as chiral signatures for establishing the authenticity and quality of black pepper oil.

Key words

Piper nigrum - Piperaceae - conventional GC/MS - chiral GC/MS - enantiomeric distribution - authenticity - quality evaluation

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Referenzen

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