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Cannabinoid Profiling of Hemp Seed Oil by Liquid Chromatography Coupled to High-Resolution Mass Spectrometry

Hemp seed oil is well known for its nutraceutical, cosmetic and pharmaceutical properties due to a perfectly balanced content of omega 3 and omega 6 polyunsaturated fatty acids. Its importance for human health is reflected by the success on the market of organic goods in recent years. However, it is of utmost importance to consider that its healthy properties are strictly related to its chemical composition, which varies depending not only on the manufacturing method, but also on the hemp…

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. 2019 Feb 13;10:120.

doi: 10.3389/fpls.2019.00120. eCollection 2019.

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Cinzia Citti et al. Front Plant Sci. .

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Abstract

Hemp seed oil is well known for its nutraceutical, cosmetic and pharmaceutical properties due to a perfectly balanced content of omega 3 and omega 6 polyunsaturated fatty acids. Its importance for human health is reflected by the success on the market of organic goods in recent years. However, it is of utmost importance to consider that its healthy properties are strictly related to its chemical composition, which varies depending not only on the manufacturing method, but also on the hemp variety employed. In the present work, we analyzed the chemical profile of ten commercially available organic hemp seed oils. Their cannabinoid profile was evaluated by a liquid chromatography method coupled to high-resolution mass spectrometry. Besides tetrahydrocannabinol and cannabidiol, other 30 cannabinoids were identified for the first time in hemp seed oil. The results obtained were processed according to an untargeted metabolomics approach. The multivariate statistical analysis showed highly significant differences in the chemical composition and, in particular, in the cannabinoid content of the hemp oils under investigation.

Keywords: cannabinoids; cannabinoids mass spectra; hemp; hemp seed oil; high-resolution mass spectrometry.

Figures

FIGURE 1

FIGURE 1

Extracted Ion Chromatograms (EICs) in positive (A) and negative (B) ionization mode of a mix solution of cannabinoid standards (1 μg/mL). From the top: CBD, Δ9-THC and Δ8-THC ([M+H]+ 315.2319, [M–H] 313.2173), CBG ([M+H]+ 317.2475, [M–H] 315.2330), CBDA and THCA ([M+H]+ 359.2217, [M–H] 357.2071), CBDV ([M+H]+ 287.2006, [M–H] 285.1860), CBGA ([M+H]+ 361.2373, [M–H] 359.2228), internal standards (IS) (2 μg/mL) CBD-d3 and THC-d3 ([M+H]+ 318.2517, [M–H] 313.2361), and CBN ([M+H]+ 311.2006, [M–H] 309.1860).

FIGURE 2

FIGURE 2

HRMS fragmentation spectrum of cannabidiol (CBD) in positive (A) and negative (B) ionization mode.

FIGURE 3

FIGURE 3

HRMS fragmentation spectrum of Δ9-tetrahydrocannabinol (Δ9-THC or THC) in positive (A) and negative (B) ionization mode.

FIGURE 4

FIGURE 4

HRMS fragmentation spectrum of cannabinol (CBN) in positive (A) and negative (B) ionization mode.

FIGURE 5

FIGURE 5

HRMS fragmentation spectrum of cannabigerol (CBG) in positive (A) and negative (B) ionization mode.

FIGURE 6

FIGURE 6

HRMS fragmentation spectrum of cannabichromene (CBC) in positive (A) and negative (B) ionization mode.

FIGURE 7

FIGURE 7

Total ion Chromatograms (TICs) of a hemp seed oil sample (oil_1) in positive (A) and negative (B) ionization mode.

FIGURE 8

FIGURE 8

Principal Component Analysis (PCA) in positive (A) and negative (B) ionization mode of LC-HRMS data of hemp seed oils. Samples are named as “oil_number” (e.g., oil_1); the colored ellipsoids represent the 95% confidence region. Partial Least Squares Discriminant Analysis (PLS-DA) in positive (C) and negative (D) ionization mode of the LC-HRMS data of hemp seed oils. PLS-DA is performed by rotating the PCA components in order to obtain the maximum separation among the groups. Validation parameters: R2 = 0.915; Q2 = 0.755.

FIGURE 9

FIGURE 9

One-way ANOVA test of the ten hemp seed oil samples. Red points indicate statistically significant features, green points indicate features that do not contribute to the statistical difference (adjusted p-value cut-off: 0.01, post hoc test: Tukey’s Honest Significant Difference test).

FIGURE 10

FIGURE 10

One-way ANOVA test of the ten hemp seed oil samples limited to the selected cannabinoids. Red points indicate statistically significant features, green points indicate features that do not contribute to the statistical difference (adjusted p-value cut-off: 0.01, post hoc test: Tukey’s Honest Significant Difference test).

FIGURE 11

FIGURE 11

Heatmap built with the identified cannabinoids. Color-coding consists of shades of red and blue, where higher intensity of red stands for very high concentration and higher intensity of blue stands for very low concentration. The samples are shown in colors at the top of the heatmap, while cannabinoids are reported on each row.

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References

    1. Berman P., Futoran K., Lewitus G. M., Mukha D., Benami M., Shlomi T., et al. (2018). A new ESI-LC/MS approach for comprehensive metabolic profiling of phytocannabinoids in Cannabis. Sci. Rep. 8:14280. 10.1038/s41598-018-32651-4 – DOI PMC PubMed
    1. Bolognini D., Rock E., Cluny N., Cascio M., Limebeer C., Duncan M., et al. (2013). Cannabidiolic acid prevents vomiting in Suncus murinus and nausea-induced behaviour in rats by enhancing 5-HT1A receptor activation. Br. J. Pharmacol. 168 1456–1470. 10.1111/bph.12043 – DOI PMC PubMed
    1. Bosy T. Z., Cole K. A. (2000). Consumption and quantitation of Δ9-tetrahydrocannabinol in commercially available hemp seed oil products. J. Anal. Toxicol. 24 562–566. 10.1093/jat/24.7.562 – DOI PubMed
    1. Callaway J. C. (2004). Hempseed as a nutritional resource: an overview. Euphytica 140 65–72. 10.1007/s10681-004-4811-6 – DOI PubMed
    1. Callaway J. C., Weeks R. A., Raymon L. P., Walls H. C., Hearn W. L. (1997). A positive thc urinalysis from hemp (Cannabis) seed oil. J. Anal. Toxicol. 21 319–320. 10.1093/jat/21.4.319 – DOI PubMed

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