板蓝根乙醇提取物化学成分及其抑制一氧化氮释放活性研究  

Chemical constitutes from alcohol extract of Isatidis Radix and their nitric oxide inhibitory activities

作　　者：张东东[1,2] 孙玉 李婧伊 阮德清 陈凯先 李医明[2] 王瑞[2] ZHANG Dong-dong;SUN Yu;LI Jing-yi;RUAN De-qing;CHEN Kai-xian;LI Yi-ming;WANG Rui(School of Pharmacy,Shaanxi University of Chinese Medicine,Xianyang 712046,China;School of Pharmacy,Shanghai University of Traditional Chinese Medicine,Shanghai 201203,China;Shanghai Institute of Materia Medica,Chinese Academy of Science,Shanghai 201203,China)

机构地区：[1]陕西中医药大学药学院,陕西咸阳712046 [2]上海中医药大学中药学院,上海201203 [3]中国科学院上海药物研究所,上海201203

出　　处：《中草药》2022年第7期1943-1948,共6页Chinese Traditional and Herbal Drugs

基　　金：国家自然科学基金项目(81573571);国家自然科学基金项目(81673570);上海市进一步加快中医药传承创新发展三年行动计划项目[ZY(2021-2023)-0215];陕西中医药大学学科创新团队项目(2019-YL12)。

摘　　要：目的研究板蓝根Isatidis Radix的化学成分及其抑制一氧化氮(NO)释放活性。方法采用硅胶、反相ODS C18、葡聚糖凝胶、半制备液相等色谱技术分离纯化,结合理化性质,NMR、MS等波谱数据解析结构,CCK-8法测定化合物抑制NO释放活性。结果从板蓝根中共分离鉴定了17个化合物,分别为(7S,8R,7′S,8′R)-3,4,3′,4′-tetramethoxy-9,7-dihydroxy-8.8′,7.O.9′-lignan(1)、(-)-(7R,7′R,8S,8′S)-4-β-D-吡喃葡萄糖基-4′-羟基-3,3′,5′-三甲氧基-7,9′:7′,9-双环氧木脂烷(2)、liballinol(3)、2-amino-1-(4-hydroxy-3-methoxyphenyl)propane-1,3-diol(4)、对羟基苯丙醇(5)、3-甲氧基-4-羟基苯丙醇(6)、3-羟基-1-(3-甲氧基-4-羟基-苯基)-丙基-1-酮(7)、3,4,5-三甲氧基肉桂酸(8)、(E)-4-(3R,4S)-3,4-(dihydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one(9)、对羟基苯甲醛(10)、香草酸(11)、3,4-二羟基苯乙酸(12)、苯甲酰胺(13)、苯乙酰胺(14)、L-焦谷氨酸(15)、L-焦谷氨酸甲酯(16)和(4R,5S)-5-hydroxyhexan-4-olide(17)。化合物7和8具有抑制NO释放活性,半数抑制浓度(median inhibition concentration,IC50)值分别为98.5、58.3μmol/L。结论化合物9为新天然产物,化合物1~4、9、12~17为首次从板蓝根中分离鉴定,化合物7和8表现出抑制NO释放活性。Objective To study the chemical constitutes from the alcohol extract of Isatis indigotica roots and their nitric oxide inhibitory activities.Methods The chemical components were isolated and purified by silica gel,ODS C18 gel,sephadex LH-20and semi preparative-HPLC chromatographic techniques while the structures were deduced by NMR and MS spectral data analysis,the NO inhibitory activities were tested by CCK-8 methods.Results Seventeen compounds were obtained and elucidated as(7S,8R,7′S,8′R)-3,4,3′,4′-tetramethoxy-9,7-dihydroxy-8.8′,7.O.9′-lignan(1),(-)-(7S,7′S,8R,8′R)-4-β-D-glucopyranosyloxy-3,3′,5′-trimethoxy-7,9′:7′,9-diepoxy-lignane(2),liballinol(3),2-amino-1-(4-hydroxy-3-methoxyphenyl)propane-1,3-diol(4),p-hydroxyl benzyl propanol(5),3-methoxy-4-hydroxyphenylpropanol(6),4-β-hydroxypropiovanillone(7),3,4,5-trimethoxy-cinnammic acid(8),(E)-4-(3R,4S)-3,4-dihydroxy-2,6,6-(trimethylcyclohex-1-en-1-yl)but-3-en-2-one(9),p-hydroxybenzaldehyde(10),vanillic acid(11),3,4-dihydroxyphenylacetic acid(12),benzamide(13),phenylacetamide(14),L-pyroglutamate(15),methyl-L-pyroglutamate(16),and(4R,5S)-5-hydroxyhexan-4-olide(17).Compounds 7 and 8 exhibited NO inhibitory activities with IC50 values of 98.5 and 58.3μmol/L,respectively.Conclusion Compound 9 was a new natural product,compounds 1-4,9 and 12-17 were isolated from Isatis indigotica root for the first time,compounds 7 and 8 showed NO inhibitory activities.

关 键 词：板蓝根 菘蓝 一氧化氮抑制活性 苯丙素 苯甲酸衍生物 3 4 5-三甲氧基肉桂酸 

分 类 号：R284.1[医药卫生—中药学]