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红大戟中的非蒽醌类化学成分
引用本文:赵峰,王素娟,吴秀丽,于洋,岳正刚,刘波,林生,朱承根,杨永春,石建功. 红大戟中的非蒽醌类化学成分[J]. 中国中药杂志, 2012, 37(14): 2092-2099
作者姓名:赵峰  王素娟  吴秀丽  于洋  岳正刚  刘波  林生  朱承根  杨永春  石建功
作者单位:天然药物活性物质与功能国家重点实验室,中国医学科学院北京协和医学院药物研究所,北京100050
基金项目:国家自然科学基金项目(30825044,20932007);国家"重大新药创制"科技重大专项(2009ZX09311-004)
摘    要:运用硅胶、Sephadex LH-20柱色谱和HPLC制备色谱等方法进行分离和纯化,从茜草科红芽大戟属植物红大戟根的乙醇提取物中首次分离得到21个非蒽醌类成分;通过NMR和MS等波谱数据鉴定了化合物的结构,包括10个三萜:乌苏酸(1),齐墩果酸(2),3β,19α-二羟基-2-氧-乌苏-12-烯-28-酸(3),坡模酸(4),马斯里酸(5),3β,19α,24-三羟基-乌苏-12-烯-28-酸(6),委陵菜酸(7),救必应酸-3,23-缩丙酮(8),2α,3β,19α,23-四羟基-齐墩果-12-烯-28-酸(9),2α,3β,19α,23-四羟基-乌苏-12-烯-28-酸(10);4个豆甾酮:(24R)-24-豆甾-4,22-二烯-3-酮(11),(24R)-24-豆甾-4-烯-3-酮(12),(24R)-24-豆甾-3β-羟基-5,22-二烯-7-酮(13),(24R)-24-豆甾-3β-羟基-5-烯-7-酮(14);2个木脂素:桉脂素(15),刺五加酮(16);1个香豆素:8-甲氧基异欧前胡素(17);4个简单芳香类化合物:5-羟甲基呋喃醛(18),3-羟基-4-甲氧基苯甲酸(19),苯甲酸(20),2-羟基-5-甲氧基-苯丙烯醛(21)。在肿瘤细胞毒(MTT法,HCT-8,Bel7402,BGC-823,A549和A2780),神经细胞保护(去血清和谷氨酸损伤模型),抗氧化(Fe2+-Cys诱导大鼠肝微粒体丙二醛生成模型),抗炎(小鼠腹腔巨噬细胞分泌NO模型),抗HIV(VS-VG/HIV-luc模型)和抗糖尿病(PTP1B酶抑制模型)药理模型上筛选结果显示,在1.0×10-5mol.L-1浓度下,这些化合物均未表现出活性。

关 键 词:茜草科  红芽大戟属  红大戟  三萜  化学成分
收稿时间:2011-12-13

Non-anthraquinones constituents from the roots of Knoxia valerianoides
ZHAO Feng,WANG Sujuan,WU Xiuli,YU Yang,YUE Zhenggang,LIU Bo,LIN Sheng,ZHU Chenggen,YANG Yongchun and SHI Jiangong. Non-anthraquinones constituents from the roots of Knoxia valerianoides[J]. China Journal of Chinese Materia Medica, 2012, 37(14): 2092-2099
Authors:ZHAO Feng  WANG Sujuan  WU Xiuli  YU Yang  YUE Zhenggang  LIU Bo  LIN Sheng  ZHU Chenggen  YANG Yongchun  SHI Jiangong
Affiliation:State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China;State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China;State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China;State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China;State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China;State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China;State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China;State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China;State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China;State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China
Abstract:Twenty-one non-anthraquinones constituents were isolated for the first time from an ethanol extract of the roots of Knoxia valerianoides by using a combination of various chromatographic techniques including column chromatography over silica gel,Sephadex LH-20,and reversed-phase HPLC.Their structures were identified by their physical-chemical properties and spectroscopic analysis including NMR and MS.The compounds include ten triterpenoids: ursolic acid(1),oleanolic acid(2),2-oxo pomolic acid(3),pomolic acid(4),maslinic acid(5),rotungenic acid(6),tormentic accid(7),rotundic acid 3,23-acetonide(8),arjungenin(9),and 2α,3β,19α,23-tetrahydroxy-urs-12-en-28-oic acid(10),four sitosterones:(24R)-24-ethylcholesta-4,22-dien-3-one(11),3-oxo-4-en-sitosterone(12),7-oxostigmasterol(13),and 7-oxo-β-sitosterol(14),two lignans: eudesmin(15) and ciwujiatone(16),one coumarin: cnidilin(17),and four simple aromatic analogues: 5-hydroxymethylenefural(18),3-hydroxy-4-methoxybenzoic acid(19),benzoic acid(20),and 2-hydroxy-5-methxoycinnamaldehydes(21).In the in vitro assays against human cancer cell lines(HCT-8,Bel7402,BGC-823,A549,and A2780),against deserum and glutamate induced PC12-syn cell damage,and against HIV-1 replication,and inhibiting protein tyrosine phosphatase 1B(PTP1B),LPS induced NO production in macrophage,and Fe2+-cystine induced rat liver microsomal lipid peroxidation,at a concentration of 1×10-5 mol·L-1,no compound showed activity.
Keywords:Rubiaceae  Knoxia  Knoxia valerianoides  triterpenoids  chemical constituent
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