[关键词]
[摘要]
目的 研究蓬莪术Curcuma phaeocaulis根茎中吉玛烷型倍半萜化学成分及其抗血小板聚集活性。方法 采用硅胶柱色谱、葡聚糖凝胶Sephadex LH-20柱色谱、反相中压液相色谱、制备薄层色谱及半制备高效液相色谱等技术进行分离纯化,运用现代波谱学手段鉴定各化合物的结构,采用计算电子圆二色谱(ECD)方法确定新化合物的绝对构型;对分离得到的相应化合物分别进行了体外腺苷-5'-二磷酸钠盐(ADP)及花生四烯酸(AA)诱导的抗血小板聚集活性筛选。结果 从蓬莪术茎95%乙醇提取物的中醋酸乙酯及正丁醇萃取部位共分离得到8个吉玛烷型倍半萜,分别鉴定为新蓬莪术环氧酮(1)、curdionolide B(2)、curdionolide A(3)、(-)-phaeocaulin A(4a)、(+)-phaeocaulin A(4b)、heyneanone C(5)、(4S,5S)-13-hydroxygermacrone 4,5-epoxide(6)、phagermadiol(7),测试了分离所得化合物1~3、6对ADP及AA诱导的抗血小板聚集活性。结论 共从蓬莪术中分离得到8个吉玛烷型倍半萜,其中化合物1为新化合物,并通过计算ECD确定了绝对构型,其对ADP及AA诱导的血小板聚集具有一定的抑制作用;化合物4a和4b为一对对映异构体;化合物2、3、5、6均为首次从蓬莪术中分离得到。
[Key word]
[Abstract]
Objective To study the chemical constituents and anti-platelet aggregative activities of germacrane-type sesquiterpenoids from the rhizome of Curcuma phaeocaulis. Methods Ethyl acetate and n-butanol fractions were separated and purificated by silica gel column, sephadex LH-20 column, reversed-phase medium pressure chromatography, preparative thin-layer chromatography, and semi-preparative high performance liquid chromatography. The structures of isolates were determined by modern spectroscopy techniques, and the absolute configuration of new compound was identified by calculating ECD. The isolates were tested for their effects on ADP- and AA-induced platelet aggregation. Results Eight germacrane-type sesquiterpenoids were isolated from the rhizome of C. phaeocaulis, and identified as neozederone epoxide (1), curdionolide B (2), curdionolide A (3), (−)-phaeocaulin A (4a), (+)-phaeocaulin A (4b), heyneanone C (5), (4S,5S)-13-hydroxygermacrone 4,5-epoxide (6), phagermadiol (7). The anti-platelet aggregation effects of compounds 1—3 and 6 were tested by suppressing ADP- and AA-induced platelet aggregation. Conclusion Eight germacrane-type sesquiterpenoids were isolated from C. phaeocaulis. Compound 1 is a new compound, and the absolute configuration of 1 is determined by calculating ECD, and compound 1 has a certain inhibitory effect on ADP- and AA-induced platelet aggregation. Compounds 4a and 4b are a pair of enantiomers. Furthermore, compounds 2, 3, 5 and 6 are isolated from the rhizome of C. phaeocaulis for the first time.
[中图分类号]
R284.1
[基金项目]
国家自然科学基金项目(81903777);国家自然科学基金项目(82022072);中国博士后科学基金资助项目(2019M653362);成都中医药大学“杏林学者”学科人才科研提升计划(BSH2018009);四川省青年科技创新研究团队专项计划项目(2017TD0001,2016TD0006)