Page 162 - 《精细化工》2022年第3期

第 39 卷第 3 期 精 细 化 工 Vol.39, No.3
2022 年 3 月 FINE CHEMICALS Mar. 2022

医药与日化原料
大麻二酚类似物的合成及其抗氧化性和抑菌性

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吴 淇 1,2 ，邹亮华 ，胡学一 ，夏咏梅
（1. 江南大学 食品科学与技术国家重点实验室，江苏 无锡 214122；2. 江南大学 化学与材料工程学院，
江苏 无锡 214122；3. 江南大学 药学院，江苏 无锡 214122）

摘要：以 α-水芹烯为烷基化试剂，烷基酚为受体，在三氯化铁催化下，通过傅克烷基化反应合成了 4 种大麻二
酚（CBD）的类似物（Ⅰ~Ⅳ）；并以 8,9-二氢大麻二酚（H2CBD）和 2,2,8,9-四氢大麻酚（2,2,8,9-THC）为原料，
通过与有机溴化物的 O-烷基化反应合成了另外 8 种 CBD 类似物（Ⅴ~Ⅻ）。对 CBD 及其类似物的抗氧化活性及
抑菌活性进行了测试。结果表明，所合成化合物中，仅 2′-异丙基-5′-甲基-1′,2′-二氢-3′,4′-四氢-[1,1′-联苯]-2,4,6-三
醇（类似物Ⅰ）有抑菌性和抗氧化性。类似物Ⅰ具有三羟基结构，表现出比 CBD 更好的抗氧化能力，其 1,1-
二苯基-2-三硝基苯肼（DPPH）和 2,2′-联氮-双-3-乙基苯并噻唑啉-6-磺酸（ABTS）自由基清除的半最大效应浓
度（EC 50 ）分别是 CBD 的 23.8%和 25.1%，略低于 V C 。类似物Ⅰ对 4 种细菌均表现出较好的抑菌活性，最小抑
菌浓度均<100 μg/mL，表明酚羟基的存在可能是 CBD 类似物具有抗氧化性和抑菌性的必要条件。
关键词：大麻二酚；α-水芹烯；傅克烷基化；抑菌性；抗氧化性；医药原料
中图分类号：TQ28 文献标识码：A 文章编号：1003-5214 (2022) 03-0584-08

Synthesis and antioxidant and bacteriostatic properties of cannabidiol analogs

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WU Qi , ZOU Lianghua , HU Xueyi , XIA Yongmei
（1. State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi 214122, Jiangsu, China; 2. School
of Chemical and Material Engineering, Jiangnan University, Wuxi 214122, Jiangsu, China; 3. School of Pharmaceutical
Science, Jiangnan University, Wuxi 214122, Jiangsu, China）
Abstract: Four analogues of cannabidiol (CBD) were synthesized by Friedel-Crafts alkylation using α-
phellandrene as alkylation reagent, alkylphenols as nucleophilic receptor in the catalytic amount of ferric
chloride. Other eight cannabinol analogues were synthesized from 8,9-dihydrocannabidiol and 2,2,8,9-
tetrahydrocannabinol by O-alkylation with organic bromide compounds. The antioxidant and antibacterial
activities of CBD and its analogues were tested. The results showed that among the synthesized compounds,
only 2′-isopropyl-5′-methyl-1′,2′-dihydro-3′,4′-tetrahydro-[1,1′-biphenyl]-2,4,6-triol (analogue Ⅰ ) had
antibacterial and antioxidant activities. AnalogueⅠexhibited better antioxidative activity than CBD due to
its trihydroxyl structure in the molecular. The concentration for 50% of maximum effect (EC 50) of
1,1-diphenyl-2-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS)
free radical scavenging were 23.8% and 25.1% of that of CBD, respectively, even slightly lower than that of
V C. AnalogueⅠpresented better antibacterial activity against four kinds of assayed bacteria and the
minimum antibacterial concentrations were all lower than 100 μg/mL, indicating that the presence of
phenolic hydroxyl might be a necessary condition for the antioxidant and bacteriostatic properties of CBD
analogues.
Key words: cannabinol; α-phellandrene; Friedel-Crafts alkylation; antibacterial activity; antioxidant activity;
drug materials

收稿日期：2021-10-30; 定用日期：2021-12-27; DOI: 10.13550/j.jxhg.20211112
基金项目：江南大学食品科学与技术国家重点实验室开放项目（SKLF-KF-202005）
作者简介：吴 淇（1997—），男，硕士生，E-mail：wuqi0518@163.com。联系人：夏咏梅（1965—），女，教授，E-mail：ymxia@
jiangnan.edu.cn。