摘要
目的分离鉴定冈村凹顶藻(Laurencia okamurai Yamada)中的倍半萜类成分,供抗菌活性筛选。方法综合利用各种柱层析方法分离纯化化合物并利用光谱学方法解析化合物结构;选择4株真菌为实验菌株,对6个倍半萜进行体外抗真菌活性测定;选择2株细菌为实验菌株,对所有倍半萜进行体外抗细菌活性测定。结果分离得到17个倍半萜,分别鉴定为海兔阿普里醇(1)、劳藻过氧素(2)、海兔阿普里醛(3)、α-异溴花侧伯烯(4)、α-异花侧伯烯醇(5)、花侧伯烯醚(6)、月桂烷-11-烯-10-醇(7)、劳藻酚(8)、劳藻酚乙酰化物(9)、去溴劳藻酚(10)、异劳藻酚(11)、异劳藻酚乙酰化物(12)、约翰斯顿醇(13)、帕西菲醇(14)、10-溴-α-花柏烯(15)、10-溴-β-花柏烯(16)、9-羟基-3-氯-4,10-二溴-α-花柏烯(17),并对所获得的倍半萜进行抗菌活性筛选。结论化合物5和7为首次从冈村凹顶藻中分离得到;应用1D和2D NMR首次对化合物6的~1 H和^(13) C NMR数据进行了全归属;化合物5和13对光滑假丝酵母菌显示了明显的抑制作用,其MIC_(80)值分别为1和4μg·mL^(-1),与两性霉素B(2μg/mL)和氟康唑(1μg/mL)相当,而化合物2、8和9对新生隐球菌均具有一定的抑制作用;另外,化合物2、8~10、15和17对金黄色葡萄球菌均显示了不同程度的抑制作用,其中化合物8和9具有良好的杀菌活性,其MIC_(80)值分别为2.3和10.5μg/mL。
Objective To isolate and identify sesquiterpenes of the red algaLaurencia okamurai Yamada and to evaluate their antimicrobial activities.Methods Compounds were isolated and purified by means of various chromatographic techniques including silica gel and Sephadex LH-20 column chromatography and reverse phase HPLC,while their structures were elucidated on the basis of spectroscopic analysis.The in vitro antifungal activity of six sesquiterpenes against four fungi（Cryptococcus neoformans,Candida glabrata,Trichophyton rubrum,and Aspergillus fumigatus）and antibacterial activity of all the isolates against two bacteria（Staphylococcus aureus and Pseudomonas aeruginosa）were evaluated using broth micro-dilution method.Results Seventeen known sesquiterpenes were isolated and identified as aplysinol（1）,laureperoxide（2）,aplysinal（3）,α-isobromocuparene（4）,α-isocuparenol（5）,cuparene-type ether（6）,laur-11-en-10-ol（7）,laurinterol（8）,laurinterol acetate（9）,debromolaurinterol（10）,isolaurinterol（11）,isolaurinterol acetate（12）,johnstonol（13）,pacifenol（14）,10-bromo-α-chamigrene（15）,10-bromo-β-chamigrene（16）,and 4,10-dibromo-3-chloro-9-hydroxy-α-chamigrene（17）,respectively.All of the isolated sesquiterpenes were evaluated for antimicrobial activities.Conclusion Compounds 5 and 7 were isolated for the first time fromLaurencia okamurai.The full ~1 H and ^（13） C NMR data were unambiguously assigned by 1Dand 2DNMR（~1 H^1 H COSY,HMQC,HMBC,and ROESY）experiments.Inin vitro antifungal bioassays,compounds 5 and13 exhibited potent inhibitory activity against the fungus Candida glabrata with MIC_（80） values of 1and 4μg/mL,respectively,when compared to the positive controls,amphotericin B（MIC_（80）= 2μg/mL）and fluconazole（MIC_（80）= 1μg/mL）,while compounds 2,8,and 9 showed moderate inhibitory activity against the fungus Cryptococcus neoformans.In addition,compounds 2,8-10,15,and 17 displayed different levels of antibacterial activity against the bacteriumStaphylococcus aureus.Among them,compounds 8and 9exhibited potent antibacterial activity with MIC_（80） values of 2.3and 10.5μg/mL,respectively.
出处
《中国海洋药物》
CAS
CSCD
2015年第6期12-22,共11页
Chinese Journal of Marine Drugs
基金
国家自然科学基金项目(21362024
21162016
81001397
20862013)
江西省青年科学家培养对象计划(20133BCB23004)
江西省自然科学基金(2010GQY0217
20114BAB205034)
江西省教育厅课题(GJJ12028)
教育部留学回国人员科研启动基金资助
关键词
冈村凹顶藻
化学成分
倍半萜
抗真菌活性
抗细菌活性
Laurencia okamurai
chemical constituents
sesquiterpenes
antifungal activity
antibacterial activity
