马尾伸筋草化学成分及抗骨质疏松活性研究

Chemical constituents from Lycopodium fargesii and their anti-osteoporotic activity

为研究马尾伸筋草(Lycopodium fargesii Hert.)的化学成分及其抗骨质疏松活性,采用硅胶、MCI、RP-18、Sephadex LH-20柱色谱及半制备高效液相色谱对马尾伸筋草的乙醇提取物进行系统分离,从乙酸乙酯部位中得到18个化合物,综合利用NMR、HR-ESI-MS等技术,分析鉴定化合物的结构,分别鉴定为α-芒柄蜡素(1)、26-去甲-8-氧化-α-芒柄蜡素(2)、serrat-14-en-3β,21α,24-triol(3)、serrat-14-en-3β,21β,24-triol(4)、1,20-eicosanediol(5)、二十三烷(6)、glycerolmonolinoleate(7)、glyceryl linolentate(8)、3-(4′-formylphenoxy)-4-methoxybenzaldehyde(9)、芹菜素(10)、对羟基苯甲醛(11)、香草酸(12)、3-羟基-4-甲氧基苯甲酸(13)、2-羟基-1-(4-羟基-3-甲氧基-苯基)-丙基-1-酮(14)、3-甲氧基-4-羟基桂皮醛(15)、8-acetoxy-5-hydroxyumbelliprenin(16)、trans-4-hydroxy-2-nonenoic acid(17)和正十烷硫醇(18)。化合物1~18均为首次从马尾伸筋草中分离得到,其中化合物16对破骨细胞活性具有显著的抑制作用,其IC_(50)为1.98μM。

To investigate anti-osteoporosis active constituents of Lycopodium fargesii Hert.,the ethanol extracts of L.fargesii were isolated by silica gel, MCI,RP-18,Sephadex LH-20 column chromatography and semi-preparative HPLC methods.Eighteen compounds were obtained from the ethyl acetate fraction.Their structures were elucidated as α-onocerin(1),26-nor-8-oxo-α-onocerin(2),serrat-14-en-3β,21α,24-triol(3),serrat-14-en-3β,21β,24-triol(4),1,20-eicosanediol(5),tricosane(6),glycerolmonolinoleate(7),glyceryl linolentate(8),3-(4′-formylphenoxy)-4-methoxybenzaldehyde(9),apigenin(10),4-hydroxybenzaldehyde(11),vanillic acid(12),3-hydroxy-4-methoxybenzoic acid(13),2-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-propan-1-one(14),3-hydroxy-4-methoxyzimtaldehyde(15),8-acetoxy-5-hydroxyumbelliprenin(16),trans-4-hydroxy-2-nonenoic acid(17) and decane-1-thiol(18) by analysis of their NMR and HR-ESI-MS data as well as by comparison with the literature reported data.Compounds 1-18 were isolated from L.fargesii for the first time.Compound 16 displayed significant anti-osteoclasts activity with IC_(50) value of 1.98 μM.