维药多伞阿魏的化学成分研究

金鹏飞; 李敏; 李韶勇; 尹宏权; 唐生安

doi:10.15918/j.tbit1001-0645.2021.241

摘要: 为明确维药多伞阿魏(Ferula ferulaeoides)的主要化学成分及其抗肿瘤活性，采用硅胶柱色谱、Sephadex LH-20 凝胶柱色谱及半制备高效液相色谱法等技术进行分离纯化，运用NMR和HRMS等波谱学方法鉴定各化合物的结构，采用计算电子圆二色谱法（ECD）判定新化合物的绝对构型. 同时运用MTT法对分离得到的单体化合物在人源乳腺癌（MCF-7）细胞系上进行细胞毒活性测试. 结果从多伞阿魏的乙酸乙酯萃取物中分离得到15个化合物，分别鉴定为1- (2- hydroxyl- 4- methoxybenzoyl)- 2S*- hydroxy- 5,9,13- trimethyl- 4(E),8(E),12- tetradecatrien- 1- one ( 1 )，愈创木醇 ( 2 )，1- (2,4- dihydroxyphenyl)- 3,7,11- trimethyl- 3- vinyl- 6(E),10- dodecadiene- 1- one ( 3 )，dshamirone ( 4 )，2,3- dihydro-7- hydroxy- 2S^*,3R^*- dimethyl- 2- 4,8-dimethyl- 3(E),7- nonadienyl- furo3,2-ccoumarin ( 5 )，3- (2-hydroxyl-4-methoxybenzoyl)- 4S^*,5R^*- dimethyl- 5- 4,8- dimethyl- 3(E),7(E)- nonadien- 1- yltetrahydro- 2- furanone ( 6 )，fukanedone A ( 7 )，2,3- dihydro- 7- methoxy- 2S^*,3R^*- dimethyl- 2- 4- methyl- 5- (4-methyl-2-furyl)- 3(E)- pentenyl- furo3,2-ccoumarin ( 8 )，伞形花素 ( 9 )，2,3- dihydro- 7- methoxy- 2S^*,3S^*- dimethyl- 3- 4,8- dimethyl- 3(E),7- nonadienyl- furo3,2-ccoumarin ( 10 )，2,3- dihydro- 7- methoxy- 2S^*,3R^*- dimethyl- 3- 4,8-dimethyl-3(E),7-nonadienyl- furo3,2-ccoumarin ( 11 )，2,3- dihydro- 7- hydroxy- 2S^*,3R^*- dimethyl- 3- 4,8- dimethyl- 3(E),7- nonadienyl- furo3,2-ccoumarin ( 12 )，2,3- dihydro- 7- methoxy- 2S^*,3R^*- dimethyl- 2- 4,8- dimethyl- 3(E),7- nonadienyl- furo3,2-ccoumarin ( 13 )，2,3- dihydro- 7- methoxy- 2R^*,3R^*- dimethyl- 2- 4,8- dimethyl- 3(E),7- nonadienyl- furo3,2-ccoumarin ( 14 )，ferulaeone C ( 15 ). 其中，化合物 1 为新杂萜类化合物，化合物 9 是从该植物中首次分离得到. 化合物 3 、 4 、 5 和 15 表现出潜在的抗肿瘤活性，半数抑制浓度（IC₅₀）分别为15.11，12.98，18.01和12.87 μmol/L.

Abstract: To study the chemical constituents of Ferula. ferulaeoides (Steud.) Korov. and their antitumor activities, it's chemical constituents were separated and purified by sephadex LH-20, silica gel, semi-preparative high performance liquid chromatography (HPLC) methods, and their structures were identified by physicochemical property and NMR, HRMS spectroscopic methods. The absolute configuration of new compound was determined by ECD. The cytotoxic activity of isolated compounds on human breast cancer (MCF-7) cell line was determined by MTT assay. Fifteen compounds ( 1 - 15 ) were isolated, and were identified as 1- (2- hydroxyl- 4- methoxybenzoyl)- 2S*- hydroxy- 5,9,13- trimethyl- 4(E),8(E),12- tetradecatrien- 1- one ( 1 ), guaiol ( 2 ), 1- (2,4- dihydroxyphenyl)- 3,7,11- trimethyl- 3- vinyl- 6(E),10- dodecadiene- 1- one ( 3 )，dshamirone ( 4 ), 2,3- dihydro-7- hydroxy- 2S^*,3R^*- dimethyl- 2- 4,8-dimethyl- 3(E),7- nonadienyl- furo3,2-ccoumarin ( 5 ),3- (2-hydroxyl-4-methoxybenzoyl)- 4S^*,5R^*- dimethyl- 5- 4,8- dimethyl- 3(E),7(E)- nonadien- 1- yltetrahydro- 2- furanone ( 6 )，fukanedone A ( 7 ), 2,3- dihydro- 7- methoxy- 2S^*,3R^*- dimethyl- 2- 4- methyl- 5- (4-methyl-2-furyl)- 3(E)- pentenyl- furo3,2-ccoumarin ( 8 ), umbelliprenin ( 9 ), 2,3- dihydro- 7- methoxy- 2S^*,3S^*- dimethyl- 3- 4,8- dimethyl- 3(E),7- nonadienyl- furo3,2-ccoumarin ( 10 ), 2,3- dihydro- 7- methoxy- 2S^*,3R^*- dimethyl- 3- 4,8-dimethyl-3(E),7-nonadienyl- furo3,2-ccoumarin ( 11 ), 2,3- dihydro- 7- hydroxy- 2S^*,3R^*- dimethyl- 3- 4,8- dimethyl- 3(E),7- nonadienyl- furo3,2-ccoumarin ( 12 ), 2,3- dihydro- 7- methoxy- 2S^*,3R^*- dimethyl- 2- 4,8- dimethyl- 3(E),7- nonadienyl- furo3,2-ccoumarin ( 13 ),2,3- dihydro- 7- methoxy- 2R^*,3R^*- dimethyl- 2- 4,8- dimethyl- 3(E),7- nonadienyl- furo3,2-ccoumarin ( 14 ), ferulaeone C ( 15 ). Compound 1 is a new compound, compound 9 is isolated from this plant for the first time. Compounds 3 、 4 、 5 and 15 show potential antitumor activity with 50% inhibitory concentration ( IC₅₀) values of 15.11, 12.98, 18.01 and 12.87 μmol/L, respectively.

维药多伞阿魏的化学成分研究

Study on Chemical Constituents in Ferula feruloides