Journal of Shandong University (Health Sciences) ›› 2018, Vol. 56 ›› Issue (9): 17-22.doi: 10.6040/j.issn.1671-7554.0.2018.588

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Chemical constituents from hemp seeds and hemp flowers

ZHANG Li1, ZHOU Yuefang2, WANG Shanshan2, WU Xuyi2, LIANG Xiaomin2, YAN Xiaoli2, FAN Peihong2   

  1. 1. Department of Pharmacy, Jinan 2nd Peoples Hospital, Jinan 250001, Shandong, China;
    2. Department of Natural Product Chemistry, School of Pharmaceutical Sciences, Shandong University, Jinan 250012, Shandong, China
  • Published:2022-09-27

Abstract: Objective To isolate and identify the chemical constituents from hemp seeds and hemp flowers, and study their bioactivities. Methods The chemical constituents were isolated and purified by macroporous adsorption resin, silica gel, octadecylsilyl, sephadex LH-20 column chromatography and HPLC. The structures of compounds were identified by 1HNMR, 13CNMR, HSQC, and HMBC spectral data. The anti-neuroinlammatory activity of the compounds were screened using lipopolysaccharide(LPS)stimulated BV2 microglia cell model, and the inflammatory factors in BV2 cells were measured using ELISA test. Results Five compounds isolated from the hemp seeds, and were identified as 1-monolinolein(1), 1-monopalmitin(2), 4-methoxy-3H-benzofuran-2-one(3),(E)-3-(4-hydroxyphenyl)acrylic acid ethyl ester(4)and polybotrin(5). Furthermore, five compounds were isolated from hemp flowers and identified as β-sitosterol(6), acacetin(7), cannflavin A(8), apigenin-7-O-β-D-glucuronide(9), and kaempferol-3-O-sophoroside(10). In addition, compounds 8-10 exhibited inhibitory effects on tumor necrosis factor α(TNF-α)released from lipopolysaccharide(LPS)-induced BV2 microglia cells. Conclusion Compounds 3 and 4 are obtained from hemp seed for the first time, and compounds 7, 9, and 10 are obtained from hemp flowers for the first time; compounds 8, 9, and 10 have potential anti-neuroinflammation effects.

Key words: Hemp seed, Hemp flower, Anti-neuroinflammation, Chemical constituents

CLC Number: 

  • R932
[1] Russo EB. History of cannabis and its preparations in saga, science, and sobriquet [J]. Chem Biodivers, 2007, 4(8): 1614-1648.
[2] Holler JM, Bosy TZ, Dunkley CS, et al. Δ9-Tetrahydrocannabinol content of commercially available hemp products [J]. J Anal Toxicol, 2008, 32(6): 428-432.
[3] Radwan MM, ElSohly MA, El-Alfy AT, et al. Isolation and pharmacological evaluation of minor cannabinoids from high-potency cannabis sativa[J]. J Nat Prod, 2015, 78(6): 1271-1276.
[4] 祝庆明,周胜建,张德鸿,等.《神农本草经》药物解读—麻子 [J]. 中国中医药现代远程教育, 2017, 15(23): 75-77. ZHU Qingming, ZHOU Shengjian, ZHANG Dehong, et al. The interpretation of materia medica of Shennongs Classic of Materia Medica—Cannabis sativa[J]. Chinese Medicine Modern Distance Education of China, 2017, 15(23): 75-77.
[5] Luo J, Yin JH, Wu HZ, et al. Extract from Fructus cannabis activating calcineurin improved learning and memory in mice with chemical drug-induced dysmnesia [J]. Acta Pharmacol Sin, 2003, 24(11): 1137-1142.
[6] 吴娜,沈谦,蔡光明,等.巴马火麻仁木脂素酰胺类提取物的鉴定及清除自由基活性的研究 [J].化学学报, 2009, 67(7): 700-704. WU Na, SHEN Qian, CAI Guangming, et al. Identification and free radical scavenging activity of lignanamide extract from Fructus Cannabis of Bama[J]. Acta Chimica Sinica, 2009, 67(7): 700-704.
[7] 蔡霈,付珣,邓安刚,等.巴马火麻仁油、蛋白粉和木脂素酰胺提取物对老年小鼠的抗衰老作用研究[J].中南药学, 2010, 8(3): 165-170. CAI Pei, FU Xun, DENG Angang, et al. Anti-aging effect of hemp seed oil, protein and lignanamide of bama on old mice [J]. Central South Pharmacy, 2010, 8(3): 165-170.
[8] 林珍梅,陈林妹,梁梓敏,等.火麻仁不同提取物对实验性Alzheimers症小鼠的治疗作用 [J].中药药理与临床, 2016, 32(6): 130-134. LIN Zhenmei, CHEN Linmei, LIANG Zimin, et al. The effect of different extractants from Hemp seed in mice with experimental Alzheimers disease[J]. Pharmacology and Clinics of Chinese Materia Medica, 2016, 32(6):130-134.
[9] Chen NY, Liu CW, Lin W, et al. Extract of Fructus Cannabis ameliorates learning and memory impairment induced by D-galactose in an aging rats model [J]. Evid Based Complement Alternat Med, 2017, 2017:4757520. doi: 10.1155/2017/4757520.
[10] 李根林,曹亚蕊,吴宿慧,等.火麻仁油对衰老模型小鼠血脂水平及炎症、抗氧化相关指标的影响[J].中药药理与临床, 2015, 31(1): 109-111. LI Genlin, CAO Yarui, WU Suhui, et al. Influence of semen cannabis oil on lipid levels, inflammatory cytokines and anti-oxidant of aging model mice [J]. Pharmacology and Clinics of Chinese Materia Medica, 2015, 31(1): 109-111.
[11] Girgih AT, Alashi AM, He R, et al. A novel hemp seed meal protein hydrolysate reduces oxidative stress factors in spontaneously hypertensive rats[J]. Nutrients, 2014, 6(12): 5652-5666.
[12] 赵翾,李红良,陈素金.火麻仁黄酮的超声提取工艺及其抗氧化活性研究[J].中国食品添加剂, 2014(6): 112-118. doi:10.3969/j.issn.1006-2513.2014.06.015 ZHAO Xuan, LI Hongliang, CHEN Sujin. Extraction of flavonoids from fructus cannabis under ultrasonic wave and its scavenging activity of DPPH radical[J]. China Food Additives, 2014(6): 112-118.
[13] 扈学俸,李永进,王军波,等.火麻仁油安全性评价及血清抗氧化功能初步研究[J].中国食品卫生杂志, 2008, 20(5): 388-392. HU Xuefeng, LI Yongjin, WANG Junbo, et al. Study on safety assessment and antioxidant function in serum of hemp seed oil [J]. Chinese Journal of Food Hygiene, 2008, 20(5): 388-392.
[14] Formukong EA, Evans FJ. The medical uses of cannabis and its constituents [J]. Phytother Res, 1989, 3(6): 219-231.
[15] Lversen L, Chapman V. Cannabinoids: a real prospect for pain relief? [J]. Curr Opin Pharmacol, 2002, 2(1): 50-55.
[16] Choi YH, Hazekamp A, Peltenburglooman AM, et al. NMR assignments of the major cannabinoids and cannabiflavonoids isolated from flowers of Cannabis sativa[J]. Phytochem Anal, 2004, 15(6), 345-354.
[17] Yan XL,Tang JJ, Passos CD, et al. Characterization of lignanamides from hemp(Cannabis sativa L.)seed and their antioxidant and acetylcholinesterase inhibitory activities [J]. J Agric Food Chem, 2015, 63(49): 10611-10619.
[18] Zhou YF, Wang SS, Lou HX, et al. Chemical constituents of hemp(Cannabis sativa L.)seed with potential anti-neuroinflammatory activity[J]. Phytochem Lett, 2018, 23: 57-61.
[19] Luo Q, Yan XL, Bobrovskaya L, et al. Anti-neuroinflammatory effects of grossamide from hemp seed via suppression of TLR-4-mediated NF-κB signaling pathways in lipopolysaccharide-stimulated BV2 microglia cells [J]. Mol Cell Biochem, 2017, 428(1-2): 129-137.
[20] Prinsen P, Gutiérrez A, Faulds CB, et al. Comprehensive study of valuable lipophilic phytochemicals in wheat bran [J]. J Agric Food Chem, 2014, 62(7): 1664-1673.
[21] 李涛,白虹,仲浩,等.毛果一枝黄花化学成分研究[J].中国实验方剂学杂志, 2013, 19(7): 140-143. LI Tao, BAI Hong, ZHONG Hao, et al. Studies on chemical constituents of Solidago virgaurea[J]. Chinese Journal of Experimental Traditional Medical Formulae, 2013, 19(7): 140-143.
[22] 余群英,张德武,戴胜军.半枝莲化学成分的分离与鉴定[J].中国现代中药, 2011, 13(2): 25-28. YU Qunying, ZHANG Dewu, DAI Shengjun. Isolation and identification of chemical constituents from the whole herb of Scutellaria Barbata[J]. Modern Chinese Medicine, 2011, 13(2): 25-28.
[23] Zou K, Komatsu K, Zhu S. A novel compound from Hedysarum polybotrys[J]. J Asian Nat Prod Res, 2007, 9(6-8): 699-703.
[24] Zhang BB, Dai Y, Liao ZX. Chemical constituents of Saussurea eopygmaea[J]. Chin J Nat Med, 2011, 9(1): 33-37.
[25] Vanhoenacker G, Van Rompaey P, de Keukeleire D, et al. Chemotaxonomic features associated with flavonoids of cannabinoid-free Cannabis(Cannabis sativa subsp.sativa L.)in relation to hops(Humulus lupulus L.)[J]. Nat Prod Lett, 2002, 16(1): 57-63.
[26] Ross SA, Elsohly MA, Sultana GNN, et al. Flavonoid glycosides and cannabinoids from the pollen of Cannabis sativa L. [J]. Phytochem Anal, 2005, 16(1): 45-48.
[27] Gong QH, Wang Q, Pan LL, et al. S-Propargyl-cysteine, a novel hydrogen sulfide-modulated agent, attenuates lipopolysaccharide-induced spatial learning and memory impairment: Involvement of TNF signaling and NF-κB pathway in rats[J]. Brain Behav Immun, 2011, 25(1): 110-119.
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