蒎烯基生物活性化合物研究进展  

Recent advances of biological activated compounds based on pinene

作　　者：张明光 李明新 王忠龙 王石发[2] ZHANG Mingguang;LI Mingxin;WANG Zhonglong;WANG Shifa(Jiangsu Vocational College of Medicine,Yancheng 224005,China;Co-Innovation Center of Efficient Processing and Utilization of Forest Resources,College of Chemical Engineering,Nanjing Forestry University,Nanjing 210037,China)

机构地区：[1]江苏医药职业学院,盐城224005 [2]南京林业大学化学工程学院,林业资源高效加工利用协同创新中心,南京210037

出　　处：《林业工程学报》2022年第5期23-34,共12页Journal of Forestry Engineering

基　　金：国家自然科学基金(32071707)。

摘　　要：α-和β-蒎烯是天然松节油的主要成分,具有良好的抑菌、杀虫、抗炎等生物活性,广泛应用于香精、香料、化妆品和医药等领域。蒎烯属于双环单萜类化合物,具有独特的双环结构和碳碳双键,因而化学性质特别活泼。通过烯烃双键加成或环外甲基氧化等反应引入新的官能团,得到双环结构蒎烷基衍生物;通过对烯烃双键的开环氧化或异构化等反应,可以打开桥环分子,形成四元或六元环衍生物,从而制备结构丰富的功能性化合物。目前,以天然、可再生的蒎烯为原料合成具有生物活性高、应用性强的新型蒎烷基衍生物已成为蒎烯深加工研究热点。总结了蒎烯生物活性及化学性质,综述了近年来基于蒎烯结构的蒎烯基嘧啶类衍生物、蒎烯基硫脲类衍生物、蒎烯基噻唑类衍生物、蒎烯基吡唑酰胺衍生物、蒎烯基磺酸衍生物、蒎烯基取代烷衍生物、桃金娘烯醛衍生物、马鞭草烯酮衍生物等双环结构蒎烷基衍生物,以及蒎酸衍生物、二氢枯铭酸衍生物、蒎酮酸衍生物、对孟烷胺衍生物和松油烯马来酸酐衍生物等开环蒎烷基衍生物的合成及其在抑菌、杀虫、抗肿瘤、除草、消炎和降糖等活性研究进展,探讨了化合物结构与活性关系,提出了当前存在问题并展望了未来的发展方向。As the dominant constituents of natural turpentine,α-andβ-pinene show good antibacterial,insecticidal,anti-inflammatory and other biological activities.They are widely used in the fields of flavors,fragrances,cosmetics and medicine.With the unique bicyclic structure and the alkene C C bond for the bicyclic monoterpene compounds,pinene is chemically active.By the addition of C C bond or the oxidation reaction of exocyclic methyl,new functional groups are introduced and the novel bicyclic pinanyl derivatives are obtained,such as pinenyl pyrimidine derivatives,pinenyl thiourea derivatives,pinenyl thiazole derivatives,pinenyl pyrazole amide derivatives,pinenyl sulfonic acid derivatives,pinenyl alkane derivatives,myrtenal derivatives,verbenone derivatives et al.By the epoxidation of C C bond or isomerization of the pinene structures,the ring bridge could be opened and the new compounds with four or six membered rings are generated,such as pinic acid derivatives,dihydrocuminic acid derivatives,pinonic acid derivatives,p-mentanamine derivatives and terpinene maleic anhydride derivatives et al.Based on the above reactions,generous functional pinenyl compounds with rich structures are prepared.Pinenyl pyrimidine derivatives,pinenyl pyrazole amide derivatives and pinenyl thiazole derivatives mainly inhibit bacteria growth,especially for Bacillus subtilis.Pinenyl alkane derivatives,myrtenal derivatives,verbenone derivatives,pinic acid derivatives,p-mentanamine derivatives and terpinene maleic anhydride derivatives obviously inhibit fungi growth including Physalospora piricola and sp.Cucumerinum,while pinenyl thiourea derivatives,pinenyl sulfonic acid derivatives and dihydrocuminic acid derivatives show moderate anticancer activities for SMMC-7721,Hela and MCF-7 cell lines.Pinonic acid derivatives exhibit insecticidal activity for Ostrinia furnacalis.New pinanyl derivatives with high biological activity or high practical values have been designed and synthesized using natural and renewable pinene as a raw material,which ha

关 键 词：蒎烯 蒎烷基衍生物 双环单萜 抑菌 生物活性 

分 类 号：TQ455.4[化学工程—农药化工]