白花夹竹桃内生真菌NR3次生代谢产物的分离鉴定及抗菌活性研究
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摘要
为了探究白花夹竹桃内生真菌NR3次生代谢产物的结构和抗菌活性,本研究对NR3的发酵产物进行了分离纯化,得到9个单体化合物.采用核磁共振光谱1 HNMR、13 CNMR及HSQC、HMBC结合理化性质进行结构表征,最终确定了7个化合物,分别为圆弧菌醇(1)、赤藓醇(2)、胡萝卜苷(3)、十六烷酸(4)、β-谷甾醇(5)、甘露醇(6)、交链孢酚(7),化合物1~7在白花夹竹桃内生真菌中均为首次分离得到.通过二倍稀释法对七种化合物进行抗菌活性测试,结果显示化合物7对供试的四种细菌都具有很强的抑制作用,MIC均为7.82μg/mL.对供试植物病原菌具有很强的抑制作用,尤其是对芍药炭疽病菌和辣椒疫霉菌的抑制效果优于阳性对照,MIC分别为1.96μg/mL和3.91μg/mL,本研究为发现新的抗菌活性物质提供了一定的理论依据.
To explore the structure and antibacterial activity of secondary metabolites of NR3 from endophytic fungi of NeriumindicumMill.Cv Paihua,9 secondary metabolites were isolated.Their structures were identified by 1 HNMR,13 CNMR,HSQC,HMBC and physicochemical properties.Seven compounds were identified as eyelopenol(1),erythritol(2),daucosterol(3),palmitic acid(4),β-sitosterol(5),mannitol(6),alternariol(7).Compounds 1~7 was isolated from endophytic fungi of NeriumindicumMill.Cv Paihua.And MIC method was used in antibacterial acitivity test.The results showed that Compound 7 had a strong inhibitory effect on the four bacteria tested,and the MIC was 7.82μg/mL.It has a strong inhibitory effect on the tested phytopathogenic fungi,especially the inhibitory effect on the Peony longipes and Phytophthora capsici is better than the positive control.The MIC was 1.96μg/mL and 3.91μg/mL respectively.This study provides a theoretical basis for the discovery of new antibacterial active substances.
To explore the structure and antibacterial activity of secondary metabolites of NR3 from endophytic fungi of NeriumindicumMill.Cv Paihua,9 secondary metabolites were isolated.Their structures were identified by 1 HNMR,13 CNMR,HSQC,HMBC and physicochemical properties.Seven compounds were identified as eyelopenol(1),erythritol(2),daucosterol(3),palmitic acid(4),β-sitosterol(5),mannitol(6),alternariol(7).Compounds 1~7 was isolated from endophytic fungi of NeriumindicumMill.Cv Paihua.And MIC method was used in antibacterial acitivity test.The results showed that Compound 7 had a strong inhibitory effect on the four bacteria tested,and the MIC was 7.82μg/mL.It has a strong inhibitory effect on the tested phytopathogenic fungi,especially the inhibitory effect on the Peony longipes and Phytophthora capsici is better than the positive control.The MIC was 1.96μg/mL and 3.91μg/mL respectively.This study provides a theoretical basis for the discovery of new antibacterial active substances.
引文
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[3]田建平,胡远艳,杨卫丽,等.夹竹桃科植物叶表皮特征及其系统学研究[J].西北植物学报,2013,33(6):1 151-1 158.
[4]马养民,冯成亮.植物内生真菌抗肿瘤活性成分研究进展[J].有机化学,2008,28(10):1 697-1 706.
[5]华永丽,欧阳少林,陈美兰,等.药用植物内生真菌研究进展[J].世界科学技术-中医药现代化,2008,10(4):104-111.
[6]Derwich E,Benziane Z,Boukir A.Chemical composition of leaf essential oil of juniperus phoenicea and evaluation of its antibacterial activity[J].International Journal of Agriculture and Biology,2010,12(2):199-204.
[7]刘少华,陆金萍,朱瑞良,等.一种快速简便的植物病原真菌基因组DNA提取方法[J].植物病理学报2005,35(4):362-365.
[8]曹永军,程萍,喻国辉,等.利用ITS1和ITS4通用引物扩增香蕉枯萎病菌核酸片段鉴定其生理小种[J].热带作物学报,2010,31(7):1 098-1 102.
[9]Bharate S B,Khan S I,Yunus N A M,et al.Antiprotozoal and antimicrobial activities of o-alkylated and formylated acylphloroglucinols[J].Bioorganic&Medicinal Chemistry,2007,15(1):87-96.
[10]李爱华,岳思君,马海滨.真菌孢子三种计数方法相关性的探讨[J].微生物学杂志,2006,26(2):107-110.
[11]刘军亮,楼盈凯,胡志钰,等.圆弧菌醇和圆弧菌素的分离纯化及结构解析[J].厦门大学学报(自然科学版),2012,51(3):386-390.
[12]李明月,常敏,张庆华,等.木榄内生真菌菌株ZD6及其代谢产物的抑菌活性[J].菌物学报,2010,29(5):739-745.
[13]韵小娟,舒火明,纪明慧,等.厚皮树树皮的化学成分研究[J].化学研究与应用,2012,24(4):610-613.
[14]Ge H M,Shen Y,Zhu C H,et al.Penicidones A-C three cytotoxic alkaloidal metabolites of an endophytic Penicillium sp.[J].Phytochemistry,2008,69:571-576.
[15]Zhang Y,Zhang T T.Studies on the chemical constituents from the stem and leaves of tagetes erecta[J].Journal of Chinese Medicinal Materials,2010,33(9):1 412-
[16]杨秀芳,龙园园,许倩,等.猫儿屎内生真菌DL06次生代谢产物及抑菌活性的研究[J].陕西科技大学学报,2017,35(4):138-141.
[17]Ma Y M,Qiao K,Kong Y,et al.A new isoquinolone alkaloid from an endophytic fungus R22of Nerium indicum[J].Natural Product Research,2017,31(8):951-958.