大麻二酚类似物的合成及其抗氧化性和抑菌性  

Synthesis and antioxidant and bacteriostatic properties of cannabidiol analogs

作　　者：吴淇 邹亮华 胡学一 夏咏梅[1] WU Qi;ZOU Lianghua;HU Xueyi;XIA Yongmei(State Key Laboratory of Food Science and Technology,Jiangnan University,Wuxi 214122,Jiangsu,China;School of Chemical and Material Engineering,Jiangnan University,Wuxi 214122,Jiangsu,China;School of Pharmaceutical Science,Jiangnan University,Wuxi 214122,Jiangsu,China)

机构地区：[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

出　　处：《精细化工》2022年第3期584-591,共8页Fine Chemicals

基　　金：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)。

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<100μg/m L,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。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(analogueⅠ)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).Analogue Ⅰ presented better antibacterial activity against four kinds of assayed bacteria and the minimum antibacterial concentrations were all lower than 100μg/m L,indicating that the presence of phenolic hydroxyl might be a necessary condition for the antioxidant and bacteriostatic properties of CBD analogues.

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 

分 类 号：TQ28[化学工程—有机化工]