八角莲中两对新的双黄酮对应异构体  

Two pairs of new biflavonoid enantiomers from Dysosma versipellis

作　　者：王慧杰[1,2,3] 韩瑞杰 孙彦君[1,3] 弓建红 白红云[1,3] 王浩杰[1,3] 冯卫生 WANG Hui-jie;HAN Rui-jie;SUN Yan-jun;GONG Jian-hong;BAI Hong-yun;WANG Hao-jie;FENG Wei-sheng(Co-construction Collaborative Innovation Center for Chinese Medicine and Respiratory Diseases by Henan&Education Ministry of P.R.China,Henan University of Chinese Medicine,Zhengzhou 450046,China;Zhoukou Vocational and Technical College,Zhoukou 466000,China;School of Pharmacy,Henan University of Chinese Medicine,Zhengzhou 450046,China)

机构地区：[1]河南中医药大学呼吸疾病中医药防治省部共建协同创新中心,郑州450046 [2]周口职业技术学院,周口466000 [3]河南中医药大学药学院,郑州450046

出　　处：《天然产物研究与开发》2024年第5期787-792,824,共7页Natural Product Research and Development

基　　金：河南中医药大学省属高校基本科研业务专项(2014KYY WF-QN26);河南中医药大学科技创新人才项目(2016XCXRC01);河南省中医药科学研究专项(20-21ZY1039);河南省高校科技创新团队支持计划(24IRTSTHN039)。

摘　　要：采用硅胶柱色谱、Sephadex LH-20柱色谱和制备型高效液相色谱法,从八角莲乙醇提取物中分离得到5个双黄酮类化合物。通过波谱数据分析(MS、UV、IR、NMR)与电子圆二色谱(ECD)技术,分别鉴定为(+)-八角莲双黄酮H(1a)、(-)-八角莲双黄酮H(1b)、(+)-八角莲双黄酮I(2a)、(-)-八角莲双黄酮I(2b)、podoverine F(3),其中,1a与1b、2a与2b为2对新的双黄酮对应异构体。DPPH自由基清除实验结果显示,化合物2、2a、2b对DPPH自由基具有较强的清除能力,IC 50值分别为8.87、10.18、11.35μmol/L,且强于阳性药trolox(14.95μmol/L)。化合物2、2a、2b对DPPH自由基的清除能力分别强于化合物1、1a、1b,进一步的构效关系研究表明,B环上邻二酚羟基是黄酮类化合物具有DPPH自由基清除活性的必需结构基团。Five biflavonoids were isolated and purified from the ethanol extract of Dysosma versipellis by silica gel column chromatography,Sephadex LH-20 column chromatography,and preparative HPLC.Their structures were identified as(+)-dysosmabiflavonoid H(1a),(-)-dysosmabiflavonoid H(1b),(+)-dysosmabiflavonoid I(2a),(-)-dysosmabiflavonoid I(2b),podoverine F(3)by extensive spectroscopic analysis(MS,UV,IR,NMR)and electronic circular dichroism(ECD)calculations.Compounds 1a and 1b,2a and 2b are two pairs of new biflavonoid enantiomers.Compounds 2,2a,and 2b showed significant DPPH scavenging capacity with IC 50 values of 8.87,10.18,11.35μmol/L,respectively,in comparison with trolox(IC 50,14.95μmol/L).Compounds 2,2a,and 2b displayed more potent DPPH radical scavenging activity than compounds 1,1a,1b,and trolox,respectively.The preliminary structure-activity relationship exhibited that the catechol hydroxyl group in B ring of flavonoids is essential for DPPH radical scavenging activity.

关 键 词：八角莲 双黄酮 DPPP自由基清除 抗氧化 

分 类 号：R284.2[医药卫生—中药学] R285.5[医药卫生—中医学]