紫玉兰叶中木脂素类成分及抗炎活性研究  

Lignans from leaves of Magnolia liliflora and their anti-inflammatory activities

作　　者：丁林芬 刘佳 宋京风 雷铁 聂伟 宋流东 吴兴德 DING Lin-fen;LIU Jia;SONG Jing-feng;LEI Tie;NIE Wei;SONG Liu-dong;WU Xing-de(Yunnan Key Laboratory of Pharmacology for Natural Products,School of Pharmaceutical Science,Kunming Medical University,Kunming 650500,China;Key Laboratory of Ethnic Medicine Resource Chemistry,State Ethnic Affairs Commission&Ministry of Education,Yunnan Minzu University,Kunming,650500,China;Haiyuan College,Kunming Medical University,Kunming 650101,China;State Key Laboratroy of Phytochemistry and Plant Resources in Western China,Kunming Institute of Botany,Chinese Academy of Sciences,Kunming 650201,China)

机构地区：[1]昆明医科大学药学院暨云南省天然药物药理重点实验室,云南昆明650500 [2]云南民族大学,民族药资源化学国家民族事务委员会-教育部重点实验室,云南昆明650500 [3]昆明医科大学海源学院,云南昆明650101 [4]中国科学院昆明植物研究所,植物化学与西部植物资源持续利用国家重点实验室,云南昆明650201

出　　处：《中草药》2022年第13期3912-3919,共8页Chinese Traditional and Herbal Drugs

基　　金：云南省科技厅-昆明医科大学应用基础研究联合专项基金资助项目(2019FE001-028);云南省教育厅科学研究基金项目(2021J0876);云南省万人计划“教学名师”(宋流东)资助项目;云南省创新团队(202005AE160004)。

摘　　要：目的研究紫玉兰Magnolialiliflora叶中木脂素类化学成分及其抗炎活性。方法采用硅胶、MCIgel、Sephadex LH-20、半制备HPLC等色谱方法进行分离纯化,根据波谱数据鉴定化合物的结构;通过测定化合物对脂多糖(lipopolysaccharide,LPS)诱导小鼠RAW 264.7巨噬细胞释放炎症介质NO的抑制能力,评价化合物的抗炎活性。结果从紫玉兰95%乙醇提取物中分离得到16个木脂素,分别鉴定为burcellin(1)、(7S*,8S*,1′S*)-3,4,1′-三甲氧基-1′,6′-二氢-7,4′-环氧-8,3′-新木脂烷-8′-烯-6′-酮(2)、(7S*,8S*,1′R*)-3,4,5,1′-四甲氧基-1′,6′-二氢-7,4′-环氧-8,3′-新木脂烷-8′-烯-6′-酮(3)、(7S*,8S*,1′S*)-3,4,5,5′-四甲氧基-1′,4′-二氢-7,2′-环氧-8,1′-新木脂烷-8′-烯-4′-酮(4)、(7S*,8S*,1′R*)-3,4,5,5′-四甲氧基-1′,4′-二氢-7,2′-环氧-8,1′-新木脂烷-8′-烯-4′-酮(5)、(7S*,8S*,1′R*)-3,4,5′-三甲氧基-1′,4′-二氢-7,2′-环氧-8,1′-新木脂烷-8′-烯-4′-酮(6)、(7R*,8S*,1′S*)-3,4-亚甲二氧基-5′-甲氧基-1′,4′-二氢-7,2′-环氧-8,1′-新木脂烷-8′-烯-4′-酮(7)、simulanol(8)、落叶松树脂醇(9)、5′-甲氧基落叶松树脂醇(10)、5,5′-二甲氧基落叶松树脂醇(11)、nectandrin A(12)、nectandrin B(13)、杜仲树脂酚(14)、丁香脂素(15)和松脂醇(16)。化合物8、10、11、13和16对LPS诱导RAW 264.7细胞释放NO具有显著抑制作用,其半数抑制浓度(median inhibition concentration,IC_(50))分别为(8.38±0.07)、(16.24±0.35)、(229.71±1.30)、(21.68±0.72)、(19.74±0.39)μmol/L。结论化合物2、4~6、8、10、11和13为首次从木兰属植物中分离得到;所有化合物均为首次从该植物中分离得到,首次报道化合物1的H-和C-NMR数据,并且首次报道化合物2和4的C-NMR数据。化合物8、10、11、13和16具有潜在的抗炎作用。Objective To study the lignans from Magnolia liliflora and their anti-inflammatory activities.Methods Chemical constituents were separated and purified by column chromatography on silica gel,MCI gel,Sephadex LH-20,and semepreparative HPLC.The structures were characterized via spectroscopic data analysis.All isolated compounds were evaluated their inhibitory activity on lipopolysaccharide(LPS)induced nitric oxide(NO)production in RAW 264.7 macrophages.Results Sixteen compounds were isolated from 95%ethanol extract of M.liliflora.Their structures were identified as burcellin(1),(7S*,8S*,1′S*)-3,4,1′-trimethoxy-1′,6′-dihydro-7,4′-epoxy-8,3′-neoligna-8′-en-6′-one(2),(7S*,8S*,1′R*)-3,4,5,1′-tetramethoxy-1′,6′-dihydro-7,4′-epoxy-8,3′-neoligna-8′-en-6′-one(3),(7S*,8S*,1′S*)-3,4,5,5′-tetramethoxy-1′,4′-dihydro-7,2′-epoxy-8,1′-neoligna-8′-en-4′-one(4),(7S*,8S*,1′R*)-3,4,5,5′-tetramethoxy-1′,4′-dihydro-7,2′-epoxy-8,1′-neoligna-8′-en-4′-one(5),(7R*,8S*,1′S*)-3,4,5′-trimethoxy-1′,4′-dihydro-7,2′-epoxy-8,1′-neoligna-8′-en-4′-one(6),(7S*,8S*,1′R*)-3,4-methylenedioxy-5′-methoxy-1′,4′-dihydro-7,2′-epoxy-8,1′-neoligna-8′-en-4′-one(7),simulanol(8),lariciresinol(9),5′-methoxylariciresinol(10),5,5′-dimethoxylariciresinol(11),nectandrin A(12),nectandrin B(13),medioresinol(14),syringaresinol(15),pinoresinol(16).Compounds 8,10,11,13,and 16displayed potent NO inhibitory activities,with IC_(50) values of(8.38±0.07),(16.24±0.35),(22.71±1.30),(21.68±0.72),and(19.74±0.39)μmol/L,respectively.Conclusion Compounds 2,4—6,8,10,11,and 13 are isolated from the genus of Magnolia for the first time.All compounds were obtained from M.liliflora for the first time.The~1H-andC-NMR spectroscopic data of 1 was reported for the first time.In addition,theC-NMR spectroscopic data of 2 and 4 were also reported for the first time.Compounds 8,10,11,13,and 16 indicate their potential anti-inflammatory effects.

关 键 词：木兰属 紫玉兰 木脂素 抗炎活性 burcellin (7S* 8S* 1′S*)-3 4 1′-三甲氧基-1′ 6′-二氢-7 4′-环氧-8 3′-新木脂烷-8′-烯-6′-酮 5′-甲氧基落叶松树脂醇 

分 类 号：R284.1[医药卫生—中药学]