牡荆子的化学成分与生物活性研究  

Chemical constituents from the fruits of Vitex negundo var. cannabifolia and their biological activities in vitro

作　　者：李月婷[1,2] 庞道然 朱枝祥[1] 霍会霞 任易[1,2] 彭治添 郑姣[1] 赵云芳[1] 屠鹏飞[1] 李军 

机构地区：[1]北京中医药大学中药现代研究中心,北京100029 [2]北京中医药大学中药学院,北京100102

出　　处：《中国中药杂志》2016年第22期4197-4203,共7页China Journal of Chinese Materia Medica

基　　金：教育部新世纪优秀人才支持计划资助项目(NCET-13-0693);国家"重大新药创制"科技重大专项(2013ZX09402201001)

摘　　要：研究牡荆Vitex negundo var.cannabifolia果实的化学成分及其生物活性。利用硅胶、Sephadex LH-20柱色谱和半制备HPLC等色谱方法分离纯化,结合其理化性质和MS、NMR等波谱学数据鉴定化合物的结构。从牡荆子70%丙酮提取物的二氯甲烷萃取部位分离鉴定了19个化合物,包括13个木脂素和6个酚类化合物,分别鉴定为6-羟基-4-(4-羟基-3-甲氧基苯基)-3-羟甲基-7-甲氧基-3,4-二氢-2-萘醛(1),6-羟基-4-(4-羟基-3-甲氧基苯基)-3-羟甲基-5-甲氧基-3,4-二氢-2-萘醛(2),vitexdoin F(3),去四氢铁杉脂素(4),vitexdoin E(5),4-氧代芝麻素(6),L-芝麻素(7),(+)-beechenol(8),ligballinol(9),2-(4-hydroxyphenyl)-6-(3-methoxy-4-hydroxyphenyl)-3,7-dioxabicyclo[3.3.0]octane(10),松脂素(11),balanophonin(12),thero-guaiacylglycerol-β-coniferyl aldehyde ether(13),对羟基肉桂醛(14),松柏醛(15),5,7-二羟基色原酮(16),反-3,5-二甲氧基-4-羟基-肉桂醛(17),覆盆子酮(18)和alternariol 4-methyl ether(19)。化合物8~10,14,18,19为首次从马鞭草科植物中分离得到,化合物13为首次从牡荆属植物中分离得到,化合物6,7,12,15~17为首次从该植物中分离得到。对分离得到的化合物进行了体外抗炎和细胞毒活性评价,8个化合物(3,5,7,10,11,14,15,17)能够明显抑制LPS诱导的RAW 264.7细胞释放一氧化氮(NO),其IC_(50)在7.8~81.1μmol·L-1;4个化合物(1~4)对Hep G-2细胞具有明显的细胞毒作用,IC_(50)在5.2~24.2μmol·L^(-1)。Chemical constituents from the fruits of Vitex negundo var. cannabifolia and their nitric oxide （NO） inhibitory and cytotoxic activities were investigated. The compounds were isolated and purified by various column chromatography, and their structures were identified by physiochemical properties and spectroscopic data. Thirteen lignans and six phenolic compounds were isolated from the CH2 C12 extract of the fruits of V. negundo var. cannabifolia, respectively. Their structures were elucidated as 6-hydroxy-4-（4-hydroxy-3-methoxyphenyl） -3-hydroxymethyl-7-methoxy-3,4-dihydro-2-naphthaldehyde （ 1 ）, vitedoin A （ 2 ）, vitexdoin F （ 3 ）, detetrahydroconidendrin （4）, vitexdoin E （5）, 4-oxosesamin （6）, L-sesamin （7）, （ ＋ ）-beechenol （8）, ligballinol （9）, 2-（4-hydroxyphenyl） -6- （3-methoxy-4-hydroxyphenyl） -3,7-dioxabicyclo [ 3.3.01 octane （10） , （ - ） -pinoresinol （ 11 ） , balanophonin （12） , theroguaiacylglycerol-β-coniferyl aldehyde ether （13） , trans-p-coumaryl aldehyde （14）, coniferyl aldehyde （15） , 5,7-dihydroxychromone （ 16）, trans-3,5-dimethoxy-4-hydroxy-cinnamic aldehyde （ 17 ）, frambinone （18） , and alternariol 4-methyl ether （ 19 ）. Compounds 8-10,14,18,19 were firstly isolated from Verbenaceae family, compound 13 was obtained from Vitex species, and 6,7,12,15-17 from V. negundo var. cannabifolia for the first time, respectively. The isolated compounds were evaluated for their anti-inflammatory and cytotoxic effects in vitro. Eight compounds （3,5,7,10,11,14,15,17） showed inhibition against NO production in LPS-stimulated RAW 267.4 cells （IC50 in the range of 7. 8-81.1 μmol · L^-1） and four compounds （1-4） showed eytotoxicity on HepG-2 cells （IC5o in the range of 5.2-24. 2 μmol · L^-1 ）.

关 键 词：牡荆子 木脂素 酚类化合物 抗炎 细胞毒 

分 类 号：R284.1[医药卫生—中药学]