柏木醇及其乙酸酯的制备和抗植物病原菌活性研究  

Preparation of cedrol and cedryl acetate and their antifungal activities

作　　者：王思禹 刘飞[2] 周倩 徐曙[2] 黄申林 罗金岳[1] WANG Siyu;LIU Fei;ZHOU Qian;XU Shu;HUANG Shenlin;LUO Jinyue(College of Chemical Engineering,Nanjing Forestry University,Nanjing 210037,China;Institute of Botany,Jiangsu Province and Chinese Academy of Sciences,Nanjing 210014,China)

机构地区：[1]南京林业大学化学工程学院,南京210037 [2]江苏省中国科学院植物研究所,南京210014

出　　处：《林业工程学报》2021年第3期74-80,共7页Journal of Forestry Engineering

基　　金：国家重点研发计划(2018YFD0600405);江苏省自然科学基金青年基金(BK20180311)。

摘　　要：为了探究柏木醇以及乙酸柏木酯作为植物源农药的潜力,以柏木油为原料,采用分馏以及重结晶的方法,分离得到柏木醇,通过液相色谱-高分辨质谱联用、核磁共振波谱及红外光谱对其进行结构确证。再以柏木醇为原料研究乙酸柏木酯的合成,发现使用脲基偶联剂可以在比较温和的条件下以较高的产率得到乙酸柏木酯。进一步通过菌丝速率生长法,研究柏木醇以及乙酸柏木酯对7种植物病原真菌(黄瓜灰霉病菌、油菜菌核病菌、小麦赤霉病菌、香蕉枯萎病菌、水稻纹枯病菌、稻瘟病菌以及枸杞炭疽病菌)的抗菌活性。发现柏木醇具有更优的活性,对黄瓜灰霉病菌及小麦赤霉病菌抑制效果明显,而乙酸柏木酯的活性相对较低。同时研究发现,柏木醇及乙酸柏木酯对正常人体细胞没有毒性(对人肺成纤维细胞HFL1的IC 50值大于80μmol/L)。实验结果证实柏木醇及其衍生物有一定的抗植物病原菌活性,具有开发成为植物源农药的潜力。Along with the extensive attention of people to the problems related with chemical pesticides,such as high toxicity,high residual,insect resistance,detrimental effect on natural enemies,environmental pollution as well as the threaten to the health of human being,it is an urgent need for the research and development of environment friendly botanical pesticides.The advantages of the botanical pesticides include their specificity,safety to non-target organisms.Cedrol is a sesquiterpene alcohol widely found in cedarwood oil and cedryl acetate is an important derivative of the cedrol series.The purpose of this paper is to explore the potential of cedrol and cedryl acetate as botanical pesticides.In this paper,HPLC-ESI-HRMS was used to analyze the chemical composition of cedarwood oil.Cedrol was separated from cedarwood oil by fractionation and recrystallization,and its structure was confirmed by the HPLC-ESI-HRMS,NMR and IR spectroscopic methods.The cedryl acetate was synthesized with cedrol as a raw material.As cedrol is a tricyclic macrosterically hindered tertiary alcohol and has a large steric hindrance,the acylation reaction of cedrol is more difficult.It was found that the high yield of cedryl acetate(approximately 93%)could be prepared under mild conditions by the coupling agent.The antifungal activities of cedrol and cedryl acetate against seven plant pathogens(Rhizoctonia solani,Sclerotinia sclerotiorum,Gibberella zeae,Fusarium oxysporum f.sp.cubense,Botrytis cinerea,Colletotrichum gloeosporioides Penz and Magnaporthe grisea)were further studied using the mycelial growth rate method.The results showed that the antifungal activity of cedrol was better than that of cedryl acetate,and cedrol had obvious inhibitory effect on Botrytis cinerea and Gibberella zeae.The highest inhibitory rate of cedrol to Botrytis cinerea was 70.39%.This study showed that hydroxyl was a necessary active group of cedrol.At the same time,it was found that cedrol and cedryl acetate had no toxicity to normal human cells(IC 50 is more tha

关 键 词：柏木油 柏木醇 乙酸柏木酯 抗植物病原真菌 植物源农药 

分 类 号：TQ351.0[化学工程]