Process Optimization of the Method of Ionic Liquid Assisted Ultrasonic Extraction of Cannabidiol from Industrial Hemp Leaves

WANG Kunlun; GUAN Lijun; GAO Yang; YAN Song; LI Jialei; LI Bo; ZHOU Ye

doi:10.13386/j.issn1002-0306.2022050272

Volume 44 Issue 3

Jan. 2023

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Science and Technology of Food Industry > 2023 > 44(3): 203-212. > DOI: 10.13386/j.issn1002-0306.2022050272

WANG Kunlun, GUAN Lijun, GAO Yang, et al. Process Optimization of the Method of Ionic Liquid Assisted Ultrasonic Extraction of Cannabidiol from Industrial Hemp Leaves[J]. Science and Technology of Food Industry, 2023, 44(3): 203−212. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2022050272.

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Process Optimization of the Method of Ionic Liquid Assisted Ultrasonic Extraction of Cannabidiol from Industrial Hemp Leaves

WANG Kunlun^{1, 2,},
GUAN Lijun^{1, 2, ,},
GAO Yang^{1, 2},
YAN Song^{1, 2},
LI Jialei^{1, 2},
LI Bo^{1, 2},
ZHOU Ye^{1, 2}

1.
Heilongjiang Province Academy of Agricultural Sciences Institute of Food Processing, Harbin 150086, China
2.
Heilongjiang Province Key Laboratory of Food Processing, Harbin 150086, China

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Received Date: May 24, 2022
Available Online: December 01, 2022

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Abstract

Abstract

In order to improve the economic value of industrial hemp, an active ingredient cannabinoid (CBD) with medicinal value from industrial hemp leaves was extracted by ionic liquid assisted ultrasonic method and the extraction process was optimized. In this study, [C₈mim]NTF₂ was selected as the best extraction solvent from 16 kinds of imidazole ionic liquids based on the yield of CBD. Then single factor experiment was conducted on six factors affecting the yield of CBD extraction by ionic liquid assisted ultrasonic method. The six factors included: Ultrasonic power, ultrasonic temperature, ultrasonic time, ethanol concentration, molar concentration of ionic liquid and liquid material ratio. And the ethanol concentration was 65%. The ionic liquid molar concentration was 0.3 mol/L (65% ethanol solution preparation). On the basis of these results, four significant factors (ultrasonic power, ultrasonic temperature, ultrasonic time and liquid material ratio) were screened out by Plackett-Burman experimental design. The extraction process was further optimized by response surface Box-Behnken experimental design. The optimum extraction process conditions of CBD significant factors were as follows: Ultrasonic power 280 W, ultrasonic temperature 50 ℃, ultrasonic time 62.5 min, liquid material ratio 25 mL/g. Under the above conditions, the yield of CBD extracted by ionic liquid [C₈mim]NTF₂ was 7.66%±0.2%, the yield of CBD extracted by methanol was 6.42%±0.3%, and the yield of CBD extracted by 65% ethanol solution was 5.81%±0.2%. The extraction ability of CBD was ionic liquid [C₈mim]NTF₂>methanol>65% ethanol solution. The CBD degradation experiment showed that the CBD degradation rate of ionic liquid [C₈mim]NTF₂ was 16.40%±0.3%, which was smaller than that of methanol (24.65%±0.6%) and 65% ethanol solution (32.88%±0.5%). The results showed that adding 65% ethanol solution into ionic liquid [C₈mim]NTF₂ could not only reduce the degradation rate of CBD, but also increase the yield of CBD. This study proved that ionic liquid was not only a protective agent for CBD, but also an excellent solvent for CBD extraction. The technology of extracting CBD by ionic liquid assisted ultrasonic method was developed, which provided data support for the development and utilization of industrial hemp CBD.
- industrial hemp leafs,
- cannabidiol (CBD),
- ionic liquid,
- ultrasonic extraction,
- Plackett-Burman design,
- response surface

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References

[1]	DAS L, LI W, DODGE L A, et al. Comparative evaluation of industrial hemp cultivars: Agronomical practices, feedstock characterization and potential for biofuels and bioproducts[J]. ACS Sustainable Chemistry & Engineering,2020,8(16):6200−6210.
[2]	GUNNARSSON I B, KUGLARZ M, KARAKASHEV D, et al. Thermochemical pretreatments for enhancing succinic acid production from industrial hemp (Cannabis sativa L.)[J]. Bioresource Technology,2015,182:58−66. doi: 10.1016/j.biortech.2015.01.126
[3]	HARTSEL J A, EADES J, HICKORY B, et al. Cannabis sativa and hemp[J]. Nutraceuticals,2016:735−754.
[4]	BURKHARD H, ROBERT R. Anti-tumour actions of cannabinoids[J]. British Journal of Pharmacology,2019,176(10):1384−1394. doi: 10.1111/bph.14426
[5]	MARCUS S D. Tetrahydrocannabinol levels in hemp (Cannabis sativa) germplasm resources[J]. Economic Botany,2003,57(4):545−558. doi: 10.1663/0013-0001(2003)057[0545:TLIHCS]2.0.CO;2
[6]	GRASSA C J, WEIBLEN G D, WENGER J P, et al. A new Cannabis genome assembly associates elevated cannabidiol (CBD) with hemp introgressed into marijuana[J]. New Phytologist,2021,230(4):1665−1679. doi: 10.1111/nph.17243
[7]	WANG Y, MUKHOPADHYAY P, CAO Z, et al. 201-Cannabidiol protects against chronic plus binge alcohol induced liver injury by modulating neutrophil infiltration, E selectin, inflammation and oxidative/nitrative stress[J]. Free Radical Biology and Medicine,2014,76:S88.
[8]	WIRTH P W, WATSON E S, ELSOHLY M, et al. Anti-inflammatory properties of cannabichromene[J]. Life Sciences,1980,26(23):1991−1995.
[9]	HUBER S, HARDER M, FUNCK K, et al. Novel room temperature ionic liquid for liquid-phase microextraction of cannabidiol from natural cosmetics[J]. Separations,2020,7(3):45. doi: 10.3390/separations7030045
[10]	李焰梅, 郝丹, 蒋献. 大麻二酚在皮肤科的研究进展[J]. 中国皮肤性病学杂志,2019,33(10):1202−1205. [LI Yanmei, HAO Dan, JIANG Xian. Research progress of cannabidiol in dermatology[J]. Chin J Derm Venereol,2019,33(10):1202−1205. doi: 10.13735/j.cjdv.1001-7089.201901008
[11]	刘凯, 张静, 何媛, 等. 大麻二酚临床疗效及递送系统研究进展[J]. 沈阳医科大学学报,2021,38(12):1361−1372. [LIU Kai, ZHANG Jing, HE Yuan, et al. Research progress on clinical efficacy and delivery system of cannabidiol[J]. Journal of Shenyang Pharmaceutical University,2021,38(12):1361−1372.
[12]	BOEHNKE K F, GAGNIER J J, MATALLANA L, et al. Substituting cannabidiol for opioids and pain medications among individuals with fibromyalgia: A large online survey[J]. The Journal of Pain,2021,22(11):1418−1428. doi: 10.1016/j.jpain.2021.04.011
[13]	MOLTKE J, HINDOCHA C. Reasons for cannabidiol use: A cross-sectional study of CBD users, focusing on self-perceived stress, anxiety, and sleep problems[J]. Journal of Cannabis Research,2021,3(1):5. doi: 10.1186/s42238-021-00061-5
[14]	高哲, 张志军, 李晓君, 等. 火麻叶中大麻二酚的热回流法提取工艺研究[J]. 中国油脂,2019,44(3):107−111. [GAO Zhe, ZHANG Zhijun, LI Xiaojun, et al. Hot reflux extraction of cannabidiol from hemp leaves[J]. China Oils and Fats,2019,44(3):107−111. doi: 10.3969/j.issn.1003-7969.2019.03.023
[15]	LEIMAN K, COLOMO L, ARMENTA S, et al. Fast extraction of cannabinoids in marijuana samples by using hard-cap espresso machines[J]. Talanta,2018,190:321−326. doi: 10.1016/j.talanta.2018.08.009
[16]	DRINI Z, VLADI J, KOREN A, et al. Microwave-assisted extraction of cannabinoids and antioxidants from Cannabis sativa aerial parts and process modeling[J]. Journal of Chemical Technology & Biotechnology,2020,95(3):831−839.
[17]	GRIJO D R, VIEITEZ O I A, CARDOZO F L. Supercritical extraction strategies using CO₂ and ethanol to obtain cannabinoid compounds from Cannabis hybrid flowers[J]. Journal of CO₂ Utilization,2018,28:174−180. doi: 10.1016/j.jcou.2018.09.022
[18]	HAN G, ZHANG D, KONG C, et al. Flexible, thermostable and flame-resistant epoxy-based thermally conductive layered films with aligned ionic liquid-wrapped boron nitride nanosheets via cyclic layer-by-layer blade-casting[J]. Chemical Engineering Journal,2022,437:135482. doi: 10.1016/j.cej.2022.135482
[19]	ALAYOUBI R, MEHMOOD N, HUSSON E, et al. Low temperature ionic liquid pretreatment of lignocellulosic biomass to enhance bioethanol yield[J]. Renewable Energy,2020,145:1808−1816. doi: 10.1016/j.renene.2019.07.091
[20]	PENG L Q, YU W Y, XU J J, et al. Pyridinium ionic liquid-based liquid-solid extraction of inorganic and organic iodine from Laminaria[J]. Food Chemistry,2018,239:1075−1084. doi: 10.1016/j.foodchem.2017.07.031
[21]	FAN C, LI N, CAO X, et al. Ionic liquid-modified countercurrent chromatographic isolation of high-purity delphinidin-3-rutinoside from eggplant peel[J]. Journal of Food Science,2020,85(4):1132−1139. doi: 10.1111/1750-3841.15089
[22]	曾理. 化学溶剂离子液体研究进展[J]. 广州化工,2016,44(1):56−58. [ZENG Li. Research progress on application of ionic liquids[J]. Guangzhou Chemical Industry,2016,44(1):56−58. doi: 10.3969/j.issn.1001-9677.2016.01.023
[23]	XU H, HAN Z, ZHANG D, et al. Theoretical elucidation of the dual role of [HMIM]BF₄ ionic liquid as catalyst and extractant in the oxidative desulfurization of dibenzothiophene[J]. Journal of Molecular Catalysis A Chemical,2015,398:297−303. doi: 10.1016/j.molcata.2014.12.018
[24]	MAZID R R, DIVISEKERA U, YANG W, et al. Biological stability and activity of siRNA in ionic liquids[J]. Chemical Communications,2014,50(88):13457−13460. doi: 10.1039/C4CC05086J
[25]	STOLTE S, ABDULKARIM S, ARNING J, et al. Primary biodegradation of ionic liquid cations, identification of degradation products of 1-methyl-3-octylimidazolium chloride and electrochemical wastewater treatment of poorly biodegradable compounds[J]. Green Chemistry,2008,10(2):214−224. doi: 10.1039/B713095C
[26]	次仁曲宗, 罗禹, 屈晓宇, 等. 黑龙江汉麻叶中化学成分研究与大麻二酚(CBD)含量测定[J]. 四川大学学报(自然科学版),2019,56(5):957−962. [CIREN Quzong, LUO Yu, QU Xiaoyu, et al. Study on chemical constituents and determination of cannabidiol (CBD) in hemp leaves of Heilongjiang Province[J]. Journal of Sichuan University (Natural Science Edition),2019,56(5):957−962.
[27]	廖钦洪, 李会合, 刘奕清, 等. 碳酸钾活化剂法制备稻壳活性炭的工艺优化[J]. 农业工程学报,2015,31(11):256−261. [LIAO Qinhong, LI Huihe, LIU Yiqing, et al. Optimizing preparation of activated carbons from rice husk by K₂CO₃ chemical activation[J]. Transactions of the Chinese Society of Agricultural Engineering (Transactions of the CSAE),2015,31(11):256−261. doi: 10.11975/j.issn.1002-6819.2015.11.037
[28]	WU X, ZHANG L, SUI A, et al. Optimization of fermentation process parameters for ginsenoside Re bioconversion by Plackett-Burman and Box-Benhnken design[J]. Matec Web of Conferences,2018,238(4):04001.
[29]	CAI C, YU W, WANG C, et al. Green extraction of cannabidiol from industrial hemp (Cannabis sativa L.) using deep eutectic solvents coupled with further enrichment and recovery by macroporous resin[J]. Journal of Molecular Liquids,2019,287:110957. doi: 10.1016/j.molliq.2019.110957
[30]	TOMA K, BURSOVA M, HORSLEY R, et al. Menthol-based hydrophobic deep eutectic solvents: Towards greener and efficient extraction of phytocannabinoids[J]. Journal of Cleaner Production,2018,278:391−396.
[31]	AHMED F E. Analysis of polychlorinated biphenyls in food products[J]. TrAC Trends in Analytical Chemistry,2003,22(3):170−185. doi: 10.1016/S0165-9936(03)00305-4
[32]	邓永, 刘东红. 超声处理对石榴皮多酚提取效果的影响[J]. 食品科学技术学报,2021,39(1):65−69,77. [DENG Yong, LIU Donghong. Effects of ultrasound treatment on extraction of pomegrante peel polyphenols[J]. Journal of Food Science and Technology,2021,39(1):65−69,77. doi: 10.12301/j.issn.2095-6002.2021.01.007
[33]	SEOUD O, SILVA V, POSSIDONIO S, et al. Microwave-assisted derivatization of cellulose, 2-the surprising effect of the structure of ionic liquids on the dissolution and acylation of the biopolymer[J]. Macromolecular Chemistry & Physics,2011,212(23):2541−2550.
[34]	王崑仑, 李家磊, 谢学军, 等. 纤维素酶辅助超声法提取葛根多糖及其DPPH自由基清除能力[J]. 食品工业科技,2019,40(20):174−179, 187. [WANG Kunlun, LI Jialei, XIE Xuejun, et al. The research of cellulase assisted ultrasound extraction of pueraria polysaccharides and DPPH antioxidant capacity[J]. Science and Technology of Food Industry,2019,40(20):174−179, 187. doi: 10.13386/j.issn1002-0306.2019.20.028
[35]	于殿宇, 王彤, 唐洪琳, 等. 挤压法制备富钙强化重组大米的工艺优化及其结构表征[J]. 农业工程学报,2018,34(22):291−298. [YU Dianyu, WANG Tong, TANG Honglin, et al. Process optimization and structure characterization of calcium-fortified recombinant rice prepared by extrusion[J]. Transactions of the Chinese Society of Agricultural Engineering (Transactions of the CSAE),2018,34(22):291−298. doi: 10.11975/j.issn.1002-6819.2018.22.036
[36]	SHA Ruyi, WU Dongyang, WANG Wenxing, et al. Application of Plackett-Burman design in screening the significant parameters in extraction of phytic acid from defatted rice bran by acetic acid[J]. Waste & Biomass Valorization,2019,10(4):1003−1011.
[37]	CHEN Fengli, ZHANG Qiang, FEI Shimin, et al. Optimization of ultrasonic circulating extraction of samara oil from Acer saccharum using combination of Plackett-Burman design and Box-Behnken design[J]. Ultrasonics Sonochemistry, 2017, 35(Pt A): 161−175.
[38]	FAN Yunchang, CHEN Meilan, CHAO Shentu, et al. Ionic liquids extraction of Para Red and Sudan dyes from chilli powder, chilli oil and food additive combined with high performance liquid chromatography[J]. Analytica Chimica Acta,2009,650(1):65−69. doi: 10.1016/j.aca.2009.03.025
[39]	刘师师. 喜树碱和盐酸小檗碱在离子液体中的溶解性能及应用研究[D]. 南宁: 广西大学, 2015 LIU Shishi. Reasearch on the solubility and application of camptothecin and berberine chloride in several ionic liquids[D]. Nanning: Guangxi University, 2015.
[40]	CAI Changyong, WANG Yani, YI Yongjian, et al. Ionic liquids simultaneously used as accelerants, stabilizers and extractants for improving the cannabidiol extraction from industrial hemp[J]. Industrial Crops & Products,2020,155:112796.

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