Elucidation of the Lipid Composition of Hemp (Cannabis sativa L.) Products by Means of Gas Chromatography and Ultra-High Performance Liquid Chromatography Coupled to Mass Spectrometry Detection
Abstract
:1. Introduction
2. Results and Discussion
2.1. Fatty Acid Methly Ester Analysis
2.1.1. Choice of the Chromatographic Method and Qualitative Results
2.1.2. Quantitative Results
2.2. Triacylglycerol Analysis
2.2.1. Choice of the Chromatographic Method
2.2.2. Qualitative Analysis: Application of a Novel LRI-Based Identification Strategy
2.2.3. Quantitative Results
3. Materials and Methods
3.1. Reagents and Materials
3.2. Samples
3.3. Sample Preparation
3.4. Instruments and Analytical Conditions
3.4.1. GC-MS/FID
+ (Ʃn3-PUFA/Ʃn6-PUFA)],
3.4.2. LC-MS
3.4.3. LC-MS Data Processing
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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n. | Compound | LRIexp | LRIlib | MS % Similarity | Oil I | Oil II | Oil III | Oil IV | Flour II | Flour IV | Residue IV |
---|---|---|---|---|---|---|---|---|---|---|---|
1 | Me. C14:0 | 1401 | 1400 | 96 | 0.03 ± 0.00 | 0.04 ± 0.01 | 0.04 ± 0.00 | 0.04 ± 0.00 | 0.05 ± 0.00 | 0.05 ± 0.01 | 0.05 ± 0.00 |
2 | Me. C15:0 | 1503 | 1500 | 95 | 0.02 ± 0.00 | 0.02 ± 0.01 | 0.03 ± 0.00 | 0.03 ± 0.00 | 0.03 ± 0.01 | 0.04 ± 0.00 | 0.04 ± 0.01 |
3 | Me. C16:0 | 1603 | 1600 | 97 | 6.76 ± 0.01 | 6.36 ± 0.03 | 7.01 ± 0.01 | 7.31 ± 0.00 | 6.94 ± 0.01 | 6.87 ± 0.00 | 7.46 ± 0.01 |
4 | Me. C16:1n7 | 1618 | 1609 | 97 | 0.11 ± 0.00 | 0.03 ± 0.00 | 0.11 ± 0.00 | 0.12 ± 0.00 | 0.11 ± 0.00 | 0.11 ± 0.00 | 0.12 ± 0.00 |
5 | Me. C16:2n4 (9Z.12Z) | 1665 | 1663 | 90 | 0.02 ± 0.00 | 0.09 ± 0.00 | 0.02 ± 0.00 | 0.02 ± 0.00 | 0.01 ± 0.00 | 0.02 ± 0.01 | 0.02 ± 0.00 |
6 | Me. C17:0 | 1703 | 1700 | 95 | 0.04 ± 0.00 | 0.05 ± 0.01 | 0.04 ± 0.00 | 0.04 ± 0.00 | 0.04 ± 0.00 | 0.05 ± 0.00 | 0.05 ± 0.00 |
7 | Me. C17:1n7 | 1716 | 1713 | 94 | 0.02± 0.00 | 0.03 ± 0.00 | 0.03 ± 0.00 | 0.02 ± 0.00 | 0.03 ± 0.01 | 0.03 ± 0.00 | 0.03 ± 0.00 |
8 | Me. C17:2n6 (9Z.12Z) a | 1757 | - | - | 0.03± 0.00 | 0.02 ± 0.00 | 0.04 ± 0.00 | 0.02 ± 0.00 | 0.02 ± 0.00 | 0.02 ± 0.00 | 0.03 ± 0.00 |
9 | Me. C18:0 | 1806 | 1800 | 97 | 2.77 ± 0.01 | 2.78 ± 0.01 | 2.83 ± 0.01 | 2.97 ± 0.00 | 2.96 ± 0.01 | 2.97 ± 0.01 | 3.04 ± 0.01 |
10 | Me. C18:1n9 | 1817 | 1810 | 94 | 13.86 ± 0.00 | 17.01 ± 0.04 | 14.75 ± 0.05 | 18.31 ± 0.02 | 17.01 ± 0.01 | 17.09 ± 0.01 | 18.40 ± 0.00 |
11 | Me. C18:1n7 | 1824 | 1826 | 96 | 0.98 ± 0.01 | 0.69 ± 0.01 | 0.98 ± 0.00 | 1.01 ± 0.01 | 0.94 ± 0.02 | 0.96 ± 0.01 | 1.01 ± 0.00 |
12 | Me. C18:2n6 (9Z.12Z) | 1860 | 1851 | 98 | 56.11 ± 0.07 | 56.52 ± 0.28 | 55.66 ± 0.17 | 53.56 ± 0.17 | 54.28 ± 0.42 | 54.48 ± 0.24 | 53.30 ± 0.32 |
13 | Me. C18:3n6 (6Z.9Z.12Z) | 1865 | 1858 | 96 | 2.58 ± 0.03 | 1.49 ± 0.00 | 1.98 ± 0.17 | 1.78 ± 0.18 | 2.28 ± 0.35 | 2.21 ± 0.15 | 2.08 ± 0.17 |
14 | Me. C18:3n3 (9Z.12E.15E) | 1873 | 1875 | 92 | 0.03 ± 0.00 | 0.02 ± 0.00 | 0.02 ± 0.00 | 0.02 ± 0.00 | 0.02 ± 0.00 | 0.03 ± 0.01 | 0.01 ± 0.00 |
15 | Me. C18:3n3 (9Z.12E.15Z) | 1883 | 1880 | 96 | 0.05 ± 0.00 | 0.04 ± 0.00 | 0.05 ± 0.00 | 0.05 ± 0.00 | 0.04 ± 0.00 | 0.03 ± 0.02 | 0.04 ± 0.00 |
16 | Me. C18:3n3 (9Z.12Z.15Z) | 1906 | 1902 | 98 | 13.85 ± 0.00 | 12.78 ± 0.06 | 13.77 ± 0.04 | 12.13 ± 0.01 | 12.52 ± 0.15 | 12.38 ± 0.07 | 11.56 ± 0.09 |
17 | Me. C18:4n3 (6Z.9Z.12Z.15Z) | 1913 | 1909 | 97 | 0.75 ± 0.00 | 0.40 ± 0.03 | 0.61 ± 0.01 | 0.44 ± 0.00 | 0.61 ± 0.08 | 0.58 ± 0.06 | 0.52 ± 0.08 |
18 | Me. C20:0 | 2002 | 2000 | 96 | 0.89 ± 0.00 | 0.72 ± 0.00 | 0.90 ± 0.01 | 0.90± 0.00 | 0.85 ± 0.01 | 0.87 ± 0.01 | 0.89 ± 0.01 |
19 | Me. C20:1n9 | 2009 | 2008 | 92 | 0.02 ± 0.00 | 0.02 ± 0.00 | 0.01 ± 0.00 | 0.02 ± 0.00 | 0.04 ± 0.00 | 0.03 ± 0.01 | 0.03 ± 0.00 |
20 | Me. C20:1n7 | 2016 | 2015 | 98 | 0.40 ± 0.00 | 0.33 ± 0.01 | 0.43 ± 0.00 | 0.44 ± 0.00 | 0.44 ± 0.00 | 0.44 ± 0.00 | 0.47 ± 0.00 |
21 | Me. C20:2n6 (11Z.14Z) | 2057 | 2055 | 96 | 0.06 ± 0.00 | 0.04 ± 0.00 | 0.06 ± 0.00 | 0.06 ± 0.00 | 0.05 ± 0.00 | 0.05 ± 0.00 | 0.06 ± 0.00 |
22 | Me. C21:0 | 2103 | 2102 | 90 | 0.02 ± 0.00 | 0.03 ± 0.02 | 0.02 ± 0.00 | 0.02 ± 0.00 | 0.03 ± 0.01 | 0.02 ± 0.01 | 0.02 ± 0.00 |
23 | Me. C20:3n3 (11Z.14Z.17Z) | 2110 | 2109 | 89 | 0.01 ± 0.00 | 0.01 ± 0.00 | 0.01 ± 0.00 | 0.01 ± 0.00 | 0.02 ± 0.00 | 0.01 ± 0.00 | 0.01 ± 0.00 |
24 | Me. C22:0 | 2201 | 2200 | 91 | 0.37 ± 0.00 | 0.31 ± 0.00 | 0.40 ± 0.00 | 0.42 ± 0.00 | 0.40 ± 0.00 | 0.41 ± 0.00 | 0.45 ± 0.01 |
25 | Me. C22:1n9 | 2219 | 2217 | 91 | 0.03 ± 0.00 | 0.02 ± 0.00 | 0.02 ± 0.00 | 0.03 ± 0.00 | 0.04 ± 0.00 | 0.04 ± 0.00 | 0.07 ± 0.00 |
26 | Me. C23:0 | 2303 | 2301 | 95 | 0.04 ± 0.00 | 0.03 ± 0.01 | 0.04 ± 0.00 | 0.05 ± 0.00 | 0.04 ± 0.00 | 0.04 ± 0.00 | 0.05 ± 0.00 |
27 | Me. C24:0 | 2401 | 2400 | 93 | 0.16 ± 0.00 | 0.13 ± 0.01 | 0.18 ± 0.00 | 0.19 ± 0.00 | 0.18 ± 0.00 | 0.19 ± 0.00 | 0.22 ± 0.00 |
28 | Me. C24:1n9 | 2421 | 2420 | 90 | 0.02 ± 0.00 | 0.02 ± 0.00 | 0.02 ± 0.00 | 0.03 ± 0.00 | 0.04 ± 0.01 | 0.03 ± 0.00 | 0.03 ± 0.00 |
29 | Me. C25:0 | 2496 | 2494 | 89 | 0.01 ± 0.00 | 0.02 ± 0.01 | 0.02 ± 0.00 | 0.02 ± 0.00 | 0.02 ± 0.01 | 0.02 ± 0.00 | 0.02 ± 0.00 |
30 | Me. C26:0 | 2598 | 2600 | 91 | 0.03 ± 0.00 | 0.02 ± 0.01 | 0.03 ± 0.01 | 0.03 ± 0.00 | 0.03 ± 0.01 | 0.03 ± 0.00 | 0.02 ± 0.00 |
SFA | 11.15 ± 0.04 | 10.51 ± 0.18 | 11.53 ± 0.05 | 12.02 ± 0.04 | 11.59 ± 0.08 | 11.54 ± 0.05 | 12.30 ± 0.06 | ||||
MUFA | 15.43 ± 0.02 | 18.13 ± 0.06 | 16.33 ± 0.06 | 19.96 ± 0.03 | 18.61 ± 0.04 | 18.70 ± 0.04 | 20.13 ± 0.02 | ||||
PUFA | 73.49 ± 0.11 | 71.41 ± 0.38 | 72.21 ± 0.40 | 68.07 ± 0.37 | 69.85 ± 1.00 | 69.81 ± 0.56 | 67.63 ± 0.87 | ||||
ω6 | 58.78 ± 0.10 | 58.07 ± 0.28 | 57.74 ± 0.34 | 55.42 ± 0.35 | 56.63 ± 0.78 | 56.76 ± 0.39 | 55.46 ± 0.71 | ||||
ω3 | 14.69 ± 0.01 | 13.25 ± 0.09 | 14.45 ± 0.05 | 12.64 ± 0.01 | 13.21 ± 0.22 | 13.04 ± 0.16 | 12.14 ± 0.17 | ||||
ω6/ω3 | 4.00 ± 0.01 | 4.38 ± 0.05 | 4.00 ± 0.04 | 4.39 ± 0.03 | 4.29 ± 0.13 | 4.35 ± 0.09 | 4.57 ± 0.12 | ||||
SFA/MUFA | 0.72 ± 0.01 | 0.58 ± 0.01 | 0.71 ± 0.01 | 0.60 ± 0.01 | 0.62 ± 0.01 | 0.62 ± 0.01 | 0.61 ± 0.01 | ||||
PUFA/SFA | 6.59 ± 0.04 | 6.79 ± 0.16 | 6.26 ± 0.06 | 5.66 ± 0.05 | 6.03 ± 0.13 | 6.05 ± 0.08 | 5.49 ± 0.10 | ||||
AI | 0.08 ± 0.00 | 0.07 ± 0.00 | 0.08 ± 0.00 | 0.08 ± 0.00 | 0.08 ± 0.00 | 0.08 ± 0.00 | 0.08 ± 0.00 | ||||
TI | 0.12 ± 0.00 | 0.11 ± 0.01 | 0.12 ± 0.00 | 0.13 ± 0.02 | 0.13 ± 0.00 | 0.13 ± 0.00 | 0.14 ± 0.00 | ||||
h/H | 12.86 ± 0.03 | 13.81 ± 0.16 | 12.33 ± 0.09 | 11.73 ± 0.08 | 12.42 ± 0.16 | 12.61 ± 0.19 | 11.45 ± 0.14 |
PN | Compound | CN | DB | LRIexp | LRItab a | Δ | Oil I | Oil II | Oil III | Oil IV | Flour II | Flour IV | Residue IV |
---|---|---|---|---|---|---|---|---|---|---|---|---|---|
24 | LnLn | 36 | 6 | 2608 # | - | - | 0.67 ± 0.04 | 0.27 ± 0.01 | 0.88 ± 0.01 | 0.68 ± 0.04 | 1.16 ± 0.04 | 1.37 ± 0.09 | 0.54 ± 0.01 |
26 | LLn | 36 | 5 | 2764 | - | - | 1.00 ± 0.06 | 1.04 ± 0.04 | 1.6 ± 0.02 | 0.57 ± 0.03 | 2.83 ± 0.08 | 3.59 ± 0.23 | 1.71 ± 0.00 |
26 | OSt | 36 | 5 | 2781 | - | - | 0.15 ± 0.01 | 0.18 ± 0.02 | 0.26 ± 0.01 | 0.14 ± 0 | 0.66 ± 0.02 | 0.97 ± 0.11 | 0.46 ± 0.04 |
28 | LL | 36 | 4 | 2895 | - | - | 1.53 ± 0.15 | 1.92 ± 0.05 | 2.02 ± 0.13 | 0.79 ± 0.02 | 4.23 ± 0.1 | 5.29 ± 0.07 | 2.79 ± 0.04 |
28 | OLn + LnP | 36/34 | 4/3 | 2917 | - | - | 0.3 ± 0.02 | 0.35 ± 0.01 | 0.46 ± 0.05 | 0.37 ± 0.01 | 0.91 ± 0.09 | 1.11 ± 0.1 | 0.82 ± 0.02 |
30 | LO + LP | 36/34 | 3/2 | 3100 | - | - | 0.54 ± 0.10 | 0.34 ± 0.06 | 0.51 ± 0.02 | 0.32 ± 0.01 | 1.13 ± 0.08 | 1.29 ± 0.15 | 0.94 ± 0.12 |
36 | LnLnLn | 54 | 9 | 3675 * | 3668 | 7 | 0.87 ± 0.02 | 1.14 ± 0.05 | 1.08 ± 0.04 | 0.89 ± 0.01 | 0.86 ± 0.06 | 1.37 ± 0.16 | 0.83 ± 0.04 |
36 | LLnSt + γLnLnLn | 54 | 9 | 3703 | - | - | 1.14 ± 0.05 | 1.08 ± 0.03 | 1.14 ± 0.05 | 0.66 ± 0.08 | 0.82 ± 0.07 | 0.82 ± 0.06 | 0.55 ± 0.01 |
36 | γLnγLnLn | 54 | 9 | 3720 | - | - | 0.13 ± 0.01 | 0.26 ± 0.02 | 0.22 ± 0.01 | 0.34 ± 0.04 | - | - | - |
38 | LnLLn + γLnLLn | 54 | 8 | 3845 * | 3830/- | 15/- | 6.95 ± 0.27 | 6.94 ± 0.20 | 7.42 ± 0.16 | 5.84 ± 0.22 | 6.27 ± 0.26 | 5.97 ± 0.28 | 6.29 ± 0.00 |
38 | γLnγLnL + LLSt | 54 | 8 | 3876 * | 3867/3890 b | 9/14 | 3.89 ± 0.03 | 2.61 ± 0.00 | 3.42 ± 0.05 | 2.29 ± 0.01 | 2.62 ± 0.05 | 2.69 ± 0.25 | 2.54 ± 0.04 |
40 | LLLn + LLγLn + LnOLn | 54 | 7 | 4008 | 3993/3999/4011 | 15/9/3 | 17.53 ± 0.49 | 15.66 ± 0.49 | 16.96 ± 0.53 | 16.60 ± 0.33 | 14.57 ± 0.76 | 15.65 ± 1.06 | 14.90 ± 0.11 |
40 | OLSt + LnLnP + LnOγLn | 54/52/54 | 7/6/7 | 4036 * | -/4023/- | -/13/- | 4.38 ± 0.13 | 2.98 ± 0.05 | 4.21 ± 0.3 | 2.93 ± 0.05 | 2.62 ± 0.32 | 2.97 ± 0.04 | 2.67 ± 0.01 |
40 | γLnLnP + StLP | 52 | 6 | 4048 * | -/4049 b | - | 0.46 ± 0.06 | 0.50 ± 0.05 | 0.68 ± 0.14 | 0.42 ± 0.07 | 0.34 ± 0.02 | 0.42 ± 0.03 | 0.36 ± 0.07 |
42 | LLL | 54 | 6 | 4165 * | 4160 | 5 | 20.31 ± 0.3 | 19.35 ± 0.21 | 19.86 ± 0.5 | 20.11 ± 0.13 | 18.31 ± 0.22 | 17.12 ± 0.37 | 19.18 ± 0.01 |
42 | OLLn | 54 | 6 | 4191 | 4192 | −1 | 5.56 ± 0.14 | 5.97 ± 0.04 | 5.04 ± 0.04 | 5.98 ± 0.35 | 5.56 ± 0.19 | 5.74 ± 0.20 | 5.79 ± 0.09 |
42 | OLγLn+ LnLP | 54/52 | 6/5 | 4209 | 4196/4217 | 13/−8 | 4.95 ± 0.15 | 4.54 ± 0.38 | 4.41 ± 0.34 | 4.88 ± 0.21 | 4.37 ± 0.18 | 3.90 ± 0.08 | 4.63 ± 0.13 |
42 | SLnLn + γLnLP | 54/52 | 6/5 | 4235 | 4216/-/4221/4221 | 19/-/14/14 | 1.19 ± 0.03 | 0.82 ± 0.01 | 0.94 ± 0.18 | 0.96 ± 0.14 | 0.91 ± 0.06 | 0.93 ± 0.08 | 1.02 ± 0.02 |
44 | OLL | 54 | 5 | 4348 | 4342 | 6 | 8.57 ± 0.16 | 9.76 ± 0.08 | 8.52 ± 0.43 | 11.13 ± 0.32 | 9.72 ± 0.42 | 9.55 ± 0.20 | 10.18 ± 0.14 |
44 | LLP + OOLn | 52/54 | 4/5 | 4369 | 4358/4360 | 11/9 | 6.84 ± 0.18 | 7.15 ± 0.03 | 6.41 ± 0.60 | 7.97 ± 0.12 | 6.86 ± 0.05 | 6.18 ± 0.21 | 7.69 ± 0.12 |
44 | SLLn + LnOP | 54/52 | 5/4 | 4396 | 4378/4383 | 18/13 | 2.15 ± 0.12 | 2.34 ± 0.07 | 1.99 ± 0.29 | 2.36 ± 0.13 | 2.36 ± 0.08 | 2.04 ± 0.08 | 2.05 ± 0.07 |
44 | SLγLn + γLnOP | 54/52 | 5/4 | 4420 | -/4403 | -/17 | 0.48 ± 0.07 | 0.40 ± 0.01 | 0.42 ± 0.07 | 0.38 ± 0.05 | 0.57 ± 0.12 | 0.40 ± 0.02 | 0.31 ± 0.02 |
46 | C20:1LL | 56 | 5 | 4502 | 4512 | −10 | 2.93 ± 0.23 | 4.24 ± 0.07 | 3.16 ± 0.19 | 4.14 ± 0.23 | 3.71 ± 0.28 | 3.66 ± 0.19 | 4.1 ± 0.05 |
46 | OOL | 54 | 4 | 4537 | 4522 | 15 | |||||||
46 | OLP + SLL | 52/54 | 3/4 | 4562 | 4548/4548 | 14/14 | 3.63 ± 0.07 | 4.64 ± 0.1 | 3.7 ± 0.04 | 4.26 ± 0.44 | 4.09 ± 0.37 | 3.8 ± 0.23 | 4.19 ± 0.03 |
46 | ALLn + SOLn + PLP | 56/54/50 | 5/4/2 | 4586 | -/4575/4571 | /11/15 | 0.69 ± 0.09 | 0.84 ± 0.02 | 0.61 ± 0.04 | 0.72 ± 0.08 | 0.78 ± 0.03 | 0.73 ± 0.06 | 0.74 ± 0.07 |
48 | C20:1LO | 56 | 4 | 4728 | 4708 | 20 | 0.11 ± 0.01 | 0.16 ± 0 | 0.22 ± 0.03 | 0.13 ± 0 | 0.18 ± 0.02 | 0.12 ± 0.01 | 0.24 ± 0.02 |
48 | OOO | 54 | 3 | 4740 | 4729 | 11 | 0.24 ± 0.05 | 0.49 ± 0.04 | 0.39 ± 0 | 0.51 ± 0.02 | 0.4 ± 0.03 | 0.35 ± 0.07 | 0.56 ± 0.04 |
48 | ALL + SOL + OOP | 56/54/52 | 4/3/2 | 4761 | -/4746/4756 | -/15/5 | 1.41 ± 0.29 | 2.03 ± 0.13 | 1.63 ± 0.07 | 1.95 ± 0.07 | 1.81 ± 0.07 | 1.66 ± 0.36 | 2.26 ± 0.28 |
48 | BLLn + AOLn | 58/56 | 5/4 | 4777 | - | - | 0.19 ± 0.01 | 0.23 ± 0.02 | 0.25 ± 0 | ||||
48 | SLP + POP | 52/50 | 2/1 | 4789 | -/4776 | -/13 | 0.04 ± 0.01 | 0.06 ± 0 | 0.06 ± 0.01 | ||||
50 | BLL+ ALO +LgLLn+ SOO | 58/56/60/54 | 4/3/5/2 | 4948 | -/-/-/4948 | -/-/-/0 | 0.91 ± 0.03 | 1.24 ± 0.05 | 1.09 ± 0.02 | 1.23 ± 0.03 | 1 ± 0.16 | 1.08 ± 0.1 | 1.23 ± 0.01 |
52 | LgLL + BLO + AOO | 60/58/56 | 4/3/2 | 5126 | -/-/5138 c | -/-/-12 | 0.24 ± 0 | 0.38 ± 0 | 0.36 ± 0.02 | 0.43 ± 0.05 | 0.35 ± 0.06 | 0.34 ± 0.03 | 0.44 ± 0 |
54 | LgLO + BOO | 60/58 | 3/2 | 5336 | - | - | 0.05 ± 0.00 | 0.08 ± 0.01 | 0.08 ± 0.01 |
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Arena, P.; Rigano, F.; Guarnaccia, P.; Dugo, P.; Mondello, L.; Trovato, E. Elucidation of the Lipid Composition of Hemp (Cannabis sativa L.) Products by Means of Gas Chromatography and Ultra-High Performance Liquid Chromatography Coupled to Mass Spectrometry Detection. Molecules 2022, 27, 3358. https://doi.org/10.3390/molecules27103358
Arena P, Rigano F, Guarnaccia P, Dugo P, Mondello L, Trovato E. Elucidation of the Lipid Composition of Hemp (Cannabis sativa L.) Products by Means of Gas Chromatography and Ultra-High Performance Liquid Chromatography Coupled to Mass Spectrometry Detection. Molecules. 2022; 27(10):3358. https://doi.org/10.3390/molecules27103358
Chicago/Turabian StyleArena, Paola, Francesca Rigano, Paolo Guarnaccia, Paola Dugo, Luigi Mondello, and Emanuela Trovato. 2022. "Elucidation of the Lipid Composition of Hemp (Cannabis sativa L.) Products by Means of Gas Chromatography and Ultra-High Performance Liquid Chromatography Coupled to Mass Spectrometry Detection" Molecules 27, no. 10: 3358. https://doi.org/10.3390/molecules27103358