摘要
倍半萜类化合物是橐吾属植物中主要的化感活性成分,常常表现出植物毒活性。为寻找更多潜在化感物质,用于筛选生态友好型天然除草剂的先导化合物,对舟叶橐吾根95%甲醇部位中具有植物毒活性的佛术烷类倍半萜进行研究。利用多种色谱分离方法从舟叶橐吾根部分离纯化到13个佛术烷类倍半萜,根据理化性质和波谱技术鉴定这些化合物分别为ligulacymlactam A(1)、3β-angeloyloxy-8β-hydroxyeremophil-7(11)-ene-12,8α(14β,6α)-diolide(2)、8β-hydroxyeremophil-7(11)-en-12,8α-olide(3)、10β-hydroxy-8β-methoxyeremophilenolide(4)、6β,8β-dihydroxyeremophil-7(11)-en-12,8α-olide(5)、8β-H-eremophil-3,7(11)-dien-12,8α;15,6α-diolide(6)、8β-hydroxyeremophil-3,7(11)-diene-8α,12(6α,15)-diolide(7)、8β-methoxyeremophil-3,7(11)-diene-8α,12(6α,15)-diolide(8)、eremophil-7(11)-ene-12,8α,14β,6α-diolide(9)、8β-hydroeremophil-7(11)-en-12β,8α(14β,6α)-diolide(10)、3-(methacryloyloxy)furanoeremophilan-15,6α-olide(11)、furanoeremophilan-14,6α-olide(12)、10β-hydroxy-6β-isobutyrylfuranoeremophilane(13),其中化合物1为新化合物。采用琼脂萌发法测试化合物1~13对拟南芥(Arabidopsis thaliana)的植物毒活性,所有化合物均未表现出对种子萌发的抑制活性,但能使种子全部萌发的时间较空白对照组提前大约1~2天;同时所有化合物均表现出一定的根生长抑制活性,其中化合物13的抑制作用最强(EC;=44.15±5.21μg/mL)。构效关系分析提示,含有10位羟基和6位侧链取代的furanermophilane型佛术烷类倍半萜具有作为生态友好型天然除草剂先导化合物的潜力。
Sesquiterpenes were the main allelopathic active ingredients in Ligularia plants and often exhibit phytotoxic activity.In order to find the major compounds from allelochemicals for developing the eco-friendly natural herbicides,the phytotoxic eremophilane sesquiterpenes in Ligularia cymbulifera were studied.Thirteen eremophilane sesquiterpenes were isolated and purified by several chromatographic techniques from the root of L.cymbulifera.Their structures were identified by physicochemical property and analysis of spectroscopic data,including a new eremophilane sesquiterpenes,ligulacymlactam A(1),together with twelve known ones,3β-angeloyloxy-8β-hydroxyeremophil-7(11)-ene-12,8α(14β,6α)-diolide(2),8β-hydroxyeremophil-7(11)-en-12,8α-olide(3),10β-hydroxy-8β-methoxyeremophilenolide(4),6β,8β-dihydroxyeremophil-7(11)-en-12,8α-olide(5),8β-H-eremophil-3,7(11)-dien-12,8α;15,6α-diolide(6),8β-hydroxyeremophil-3,7(11)-diene-8α,12(6α,15)-diolide(7),8β-methoxyeremophil-3,7(11)-diene-8α,12(6α,15)-diolide(8),eremophil-7(11)-ene-12,8α,14β,6α-diolide(9),8β-hydroeremophil-7(11)-en-12β,8α(14β,6α)-diolide(10),3-(methacryloyloxy)furanoeremophilan-15,6α-olide(11),furanoeremophilan-14,6α-olide(12),10β-hydroxy-6β-isobutyrylfuranoeremophilane(13).The phytotoxic activities against A.thaliana of compounds 1-13 were measured by agar germination method.None of them showed inhibitory activities on seed germination,but some of them could promote the germinate time earlier than blank about 1-2 days.As well as,all compounds showed weak root growth inhibitory activity,and compound 13 was the most active compound(EC_(50 )=44.15±5.21 μg/mL).Further structure-activity relationship analysis suggests that the furanermophilane sesquiterpenes which containing the 10-position hydroxyl group and the 6-position side chain substitution have potential to be the lead compound for eco-friendly natural herbicides.
作者
陈佳
李明明
邢海晶
郑国伟
浦仕彪
CHEN Jia;LI Ming-ming;XIN Hai-jing;ZHENG Guo-wei;PU Shi-biao(Yunnan Key Laboratory of Dai and Yi Medicines,Yunnan University of Chinese Medicine;Yunnan University of Chinese Medicine,Kunming 650500,China)
出处
《天然产物研究与开发》
CAS
CSCD
2022年第4期570-578,638,共10页
Natural Product Research and Development
基金
国家自然科学基金地区科学基金(82060785)
云南省教育厅科学研究基金教师类项目(2019J1064)
云南中医药大学高层次人才项目(2019YZG07)。
关键词
舟叶橐吾
佛术烷类倍半萜
植物毒活性
构效关系
Ligularia cymbulifera
eremophilane sesquiterpenes
phytotoxic activity
structure-activity relationship
作者简介
通信作者:郑国伟,E-mail:gwzheng@ynutcm.edu.cn;通信作者:浦仕彪,E-mail:pushi511@126.com。
