Simultaneous Determination of Five Cannabinoids in Hempseed Oil by HPLC

SUN Dongmei; LAN Tao; YUN Zhenyu; YU Congcong; CHU Qiao; ZHANG Weibing

doi:10.13386/j.issn1002-0306.2021020160

Volume 42 Issue 22

Nov. 2021

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Science and Technology of Food Industry > 2021 > 42(22): 261-267. > DOI: 10.13386/j.issn1002-0306.2021020160

SUN Dongmei, LAN Tao, YUN Zhenyu, et al. Simultaneous Determination of Five Cannabinoids in Hempseed Oil by HPLC[J]. Science and Technology of Food Industry, 2021, 42(22): 261−267. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2021020160.

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Simultaneous Determination of Five Cannabinoids in Hempseed Oil by HPLC

1.
East China University of Science and Technology, Shanghai 200237, China
2.
China National Institute of Standardization, Beijing 100191, China

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Received Date: February 22, 2021
Available Online: September 12, 2021

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Abstract

Abstract

Hemp oil contains cannabidiol acid(CBDA), cannabidiol(CBD), cannabinol(CBN), Δ9-tetrahydrocannabi-nol(THC), tetrahydrocannabinol acid(THCA) and other cannabidiol substances. The properties of the matrix were fully considered, and a simple and rapid sample preparation method for extracting five cannabinoids from hemp oil was developed. A HPLC method for simultaneous detection of five cannabinoids in hemp oil was established by optimizing the chromatographic conditions. The five cannabinoids and other substances in the matrix were successfully separated based on this method. The method was verified by precision experiments, repeatability experiments, and recovery experiments. The results showed that the five cannabinoids had a good linear relationship in the range of 0.5~50 μg/mL, and the limits of quantification(LOQ, S/N=10) were between 0.33~0.80 mg/kg, the recovery rate was 77.1%~103.3% with RSD≤4.7%. A few cannabinoids were found in actual hemp oil samples from 4 domestic production areas in China. THC contents in these four samples were less than 0.3%, but the THC content of some products was higher than the upper limit in EU countries, and might cause some kinds of safety risk. The method developed in this article would lay a methodological foundation for the establishment of relevant determination method standards.
- hempseed oil,
- cannabidiol(CBD),
- Δ9-tetrahydrocannabinol(THC),
- high performance liquid chromato-graphy(HPLC)

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References (35)

References

[1]	DA PORTO C, DECORTI D, TUBARO F. Fatty acid composition and oxidation stability of hemp (Cannabis sativa L.) seed oil extracted by supercritical carbon dioxide[J]. Industrial Crops and Products,2012,36:401−404. doi: 10.1016/j.indcrop.2011.09.015
[2]	EFSA. Scientific opinion of the panel on dietetic products, nutrition and allergies on a request from European Commission related to labelling reference intake values for n-3 and n-6 polyunsaturated fatty acids[J]. The EFSA Journal,2009,1176:1−11.
[3]	宁康, 董林林, 李孟芝, 等. 非精神活性药用大麻的应用及开发[J]. 中国实验方剂学杂志,2020,26(8):236−248. [NING K, DONG L L, LI M Z, et al. Application and development of non-psychoactive medicinal cannabis[J]. Chinese Journal of Experimental Formulas,2020,26(8):236−248.
[4]	田兆飞, 刘诗涵, 李立佳, 等. 火麻仁及其制品研究进展[J]. 农业科技与装备,2017(12):53−54. [TIAN Z F, LIU S H, LI L J, et al. Research progress of hemp seed and its products[J]. Agricultural Science and Technology and Equipment,2017(12):53−54.
[5]	王超, 杨宏丽, 李清, 等. RP-HPLC法同时测定火麻仁油中3种大麻酚类成分的含量[J]. 药物分析杂志,2010,30(9):1742−1745. [WANG C, YANG H L, LI Q, et al. Simultaneous determination of three cannabinols in hemp seed oil by RP-HPLC method[J]. Chinese Journal of Pharmaceutical Analysis,2010,30(9):1742−1745.
[6]	ORRIN D, MARIA R C, HELEN C, et al. Cannabidiol: Pharmacology and potential therapeutic role in epilepsy and other neuropsychiatric disorders[J]. Epilepsia,2014,55(6):791−802. doi: 10.1111/epi.12631
[7]	DEVINSKY O, MARSH E, FRIEDMAN D, et al. Cannabidiol in patients with treatment-resistant epilepsy: An open-label interventional trial[J]. Lancet Neurology,2016,15:270−278. doi: 10.1016/S1474-4422(15)00379-8
[8]	RAHIMI A, FAIZI M, TALEBI F, et al. Interaction between the protective effects of cannabidiol and palmitoylethanolamide in experimental model of multiple sclerosis in C57BL/6 mice[J]. Neuroence,2015,290(2):279−287.
[9]	CITTI C, PACCHETTI B, VAN DE LLI M A, et al. Analysis of cannabinoids in commercial hemp seed oil and decarboxylation kinetics studies of cannabidiolic acid (CBDA)[J]. Journal of Pharmaceutical and Biomedical Analysis,2017,149:532−540.
[10]	PETROVIC M, DEBELJAK Z, KEZIC N, et al. Relationship between cannabinoids content and composition of fatty acids in hempseed oils[J]. Food Chemistry,2015,170:218−225. doi: 10.1016/j.foodchem.2014.08.039
[11]	杨建远, 陈芳, 宋沥文, 等. 油茶籽油提取技术研究进展[J]. 食品与机械,2016,2:183−187. [YANG J Y, CHEN F, SONG L W, et al. Research progress in extraction technology of Camellia seed oil[J]. Food and Machinery,2016,2:183−187.
[12]	周莹, 陈念念, 韩丽, 等. 国内外工业大麻食品法律法规及大麻素检测方法研究进展[J]. 食品安全质量检测学报,2019(23):7959−7966. [ZHOU Y, CHEN N N, HAN L, et al. Research progress on domestic and foreign industrial hemp food laws and regulations and cannabinoid detection methods[J]. Journal of Food Safety and Quality Inspection,2019(23):7959−7966.
[13]	ATOLANI O, OGUNTOYE H, AREH E T, et al. Chemical composition, anti-toxoplasma, cytotoxicity, antioxidant, and anti-inflammatory potentials of Cola gigantea seed oil[J]. Pharmaceutical Biology,2019,57(1):154−160. doi: 10.1080/13880209.2019.1577468
[14]	MANDRIOLI M, TURA M, SCOTTI S, et al. Fast detection of 10 cannabinoids by RP-HPLC-UV method in Cannabis sativa L[J]. Molecules,2019,24(11):2113. doi: 10.3390/molecules24112113
[15]	BURNIER C, ESSEIVA P, ROUSSEL C. Quantification of THC in cannabis plants by fast-HPLC-DAD: A promising method for routine analyses[J]. Talanta,2019,192:135−141. doi: 10.1016/j.talanta.2018.09.012
[16]	翟晚枫, 吴俊陶, 张春水. 近年来国内外气相色谱及气质联用检测大麻方法综述[J]. 化学工程与装备,2012(5):143−145. [ZHAI W F, WU J T, ZHANG C S. In recent years, domestic and foreign gas chromatography and GC/MS detection methods for cannabis are reviewed[J]. Chemical Engineering and Equipment,2012(5):143−145.
[17]	NAHAR L, GUO M, SARKER S D. Gas chromatographic analysis of naturally occurring cannabinoids: A review of literature published during the past decade[J]. Phytochemical Analysis,2020,31(2):135−146. doi: 10.1002/pca.2886
[18]	张岗, 郭江宁, 徐占美. 高效液相色谱法测定火麻仁油中大麻酚的含量[J]. 中国药学杂志,2003,38(3):214−215. [ZHANG G, GUO J N, XU Z M. Determination of cannabidiol in hemp seed oil by high performance liquid chromatography[J]. Chinese Pharmaceutical Journal,2003,38(3):214−215. doi: 10.3321/j.issn:1001-2494.2003.03.020
[19]	傅强, 舒智, 邓轲, 等. 反相HPLC法同时测定大麻植物中的三种有效成分[J]. 法医学杂志,2016,32(4):261−263. [FU Q, SHU Z, DENG K, et al. Simultaneous determination of three active ingredients in cannabis plants by reversed-phase HPLC[J]. Journal of Forensic Medicine,2016,32(4):261−263. doi: 10.3969/j.issn.1004-5619.2016.04.006
[20]	CIOLINO L A, RANIERI T L, TAYLOR A M. Commercial cannabis consumer products part 1: GC-MS qualitative analysis of cannabis cannabinoids[J]. Forensic Science International,2018,289:429−437. doi: 10.1016/j.forsciint.2018.05.032
[21]	PACIFICI R, MARCHEI E, SALVATORE F, et al. Evaluation of cannabinoids concentration and stability in standardized preparations of cannabis tea and cannabis oil by ultra-high performance liquid chromatography tandem mass spectrometry[J]. Clinical Chemistry & Laboratory Medicine,2017,55(10):1555−1563.
[22]	张爱芝, 王全林, 莫世杰. 超高效液相色谱-串联质谱法同时测定食用油中痕量的Δ9-四氢大麻酚、大麻酚和大麻二酚[J]. 色谱,2010,28(11):1015−1019. [ZHANG A Z, WANG Q L, MO S J, et al. Simultaneous determination of trace Δ9-tetrahydrocannabinol, cannabidiol and cannabidiol in edible oil by ultra-performance liquid chromatography-tandem mass spectrometry[J]. Chinese Journal of Chromatography,2010,28(11):1015−1019.
[23]	Aizpurua-Olaizola O, Zarandona I, Ortiz L, et al. Simultaneous quantification of major cannabinoids and metabolites in human urine and plasma by HPLC-MS/MS and enzyme-alkaline hydrolysis[J]. Drug Testing and Analysis,2017,9(4):626−633. doi: 10.1002/dta.1998
[24]	王全林, 张爱芝. 超高效液相色谱-串联质谱法测定火麻食品中特征大麻酚[J]. 理化检验(化学分册),2013,49(6):720−724. [WANG Q L, ZHANG A Z. Determination of characteristic cannabidiol in hemp food by ultra-performance liquid chromatography-tandem mass spectrometry[J]. Physical Testing and Chemical Analysis Part B: Chemistry,2013,49(6):720−724.
[25]	CAS M D, CASAGNI E, SACCARDO A, et al. The Italian panorama of cannabis light preparation: Determination of cannabinoids by LC-UV[J]. Forensic Science International,2020,307:110113. doi: 10.1016/j.forsciint.2019.110113
[26]	KITAMURA M, KIBA Y, SUZUKI R, et al. Cannabidiol content and in vitro biological activities of commercial cannabidiol oils and hemp seed oils[J]. Medicines,2020,7(9):57. doi: 10.3390/medicines7090057
[27]	HÄDENER M, KÖNIG S, WEINMANN W. Quantitative determination of CBD and THC and their acid precursors in confiscated cannabis samples by HPLC-DAD[J]. Forensic Science International,2019,299:142−150. doi: 10.1016/j.forsciint.2019.03.046
[28]	CIOLINO L A, RANIERI T L, TAYLOR A M. Commercial cannabis consumer products part 2: HPLC-DAD quantitative analysis of cannabis cannabinoids[J]. Forensic Science International,2018,289:438−447. doi: 10.1016/j.forsciint.2018.05.033
[29]	ELKINS A C, DESEO M A, ROCHFORT S. et al. Development of a validated method for the qualitative and quantitative analysis of cannabinoids in plant biomass and medicinal cannabis resin extracts obtained by super-critical fluid extraction[J]. Journal of Chromatography B,2019,1109:76−83. doi: 10.1016/j.jchromb.2019.01.027
[30]	JANG E, KIM H, JANG S, et al. Concentrations of THC,CBD,and CBN in commercial hemp seeds and hempseed oil sold in Korea[J]. Forensic Science International,2020,306, 110064:0379−0738.
[31]	司法鉴定科学研究院. SF/Z JD0107022-2018 毛发中Δ9-四氢大麻酚、大麻二酚和大麻酚的液相色谱-串联质谱检验方法[S]. 北京: 中国标准出版社, 2018. Academy of Forensic Science. SF/Z JD0107022-2018 determination of Δ9 tetrahydro-cannabinol, cannabidiol, cannabinolin hair by liquid chromatography-tandem mass spectrometry[S]. Beijing: Standards Press of China.
[32]	The Board of Food Standards Australia New Zealand. Food standards (Proposal P1042-low THC hemp seeds as food) variation[EB/OL]. The Board of Food Standards Australia New Zealand.[2021-05-17].https://www.legislation.gov.au/Details/F2017L00499.
[33]	广西工业职业技术学院. DBS 45/001-2014 广西食品安全地方标准-火麻油[S]. 广西: 广西壮族自治区卫生计生委, 2014. Guangxi Institute of Industry and Technology. DBS 45/001-2014 Guangxi food safety local standard-Hemp oil[S]. Guangxi: Health and Family Planning Commission of Guangxi Zhuang Autonomous Region, 2014.
[34]	广西壮族自治区分析测试研究中心. DBS 45/015-2015 广西食品安全地方标准-火麻仁[S]. 广西: 广西壮族自治区卫生计生委, 2015. Guangxi Zhuang Autonomous Region Analysis and Testing Research Center. DBS 45/015-2015 Guangxi food safety local standard-Hema ren[S]. Guangxi: Health and Family Planning Commission of Guangxi Zhuang Autonomous Region, 2015.
[35]	广西壮族自治区轻工产品质量检验站. DBS 45/048-2018 广西食品安全地方标准-火麻糊[S]. 广西: 广西壮族自治区卫生计生委, 2018. Guangxi Zhuang Autonomous Region Light Indus-trial Product Quality Inspection Station. DBS 45/048-2018 Guangxi food safety local standard-Hemp paste[S]. Guangxi: Health and Family Planning Commission of Guangxi Zhuang Autonomous Region, 2018.

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Simultaneous Determination of Five Cannabinoids in Hempseed Oil by HPLC