Piper nigrum Oil – Determination of Selected Terpenes for Quality Evaluation

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.

Comparison of Chemical Compositions of the Pepper EOs From Different Cultivars and Their AChE Inhibitory Activity

“…However, it is important to collect more pepper samples to establish the authenticity and quality of white and black pepper from different cultivar by Q-markers. 16…”

“…Currently, the quality of black pepper oil is regulated under the International Standard Organization (ISO) "ISO 3061:2008 Oil of black pepper (P. nigrum L.)", in which the content of some major chemical constituents from 4 countries, including India, Sri Lanka, Indonesia, and Madagascar, was limited. 16 For example, it suggested that the content of β-pinene of the black pepper EOs produced in India should be 5%-12%. The content of β-selinene was 3%-6% in the EOs of black pepper produced in Indonesia.…”

An unprecedented chlorine-containing piperamide from Piper pseudoarboreum as potential leishmanicidal agent

“…Compound 2 is biogenetically derived from L-lysine, which is converted to piperidine, precursor of piperidone, and further catalysis by chloroperoxidase (CPO) in the last step of its biosynthesis yield 2. Moreover, compound 12 could be derived from L-phenylalanine by the typical of shikimic acid pathway through cinnamic acid (10), which is the precursor of ferulic acid (11). Precursors 10 and 11 were also isolated from the plant (Scheme 1).…”

“…terpenoids [11], phenylpropanoids [12], phenolic acids [13] and lignans [14]. These constituents have been reported to possess antioxidant [10], anti-inflammatory [15], antitumor [16] and antiparasitic properties [13,14,17].…”

“…As part of an intensive investigation into potential leishmanicidal agents from Piper species, we report herein on the isolation and structure elucidation of a new piperamide (1), along with eleven known compounds (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)…”