Neolignans from Selaginella moellendorffii

Two new neolignans selaginellol(1)and selaginellol 4'-O-β-D-glucopyranoside(2),together with seven known compounds(3–9),were isolated from the whole plant of Selaginella moellendorffii.The structures of the new isolates were determined through spectroscopic data analysis.Compounds 1–9,as well as compounds 10–18 previously isolated from the species,were measured for the activity against platelet aggregation induced by ADP or collagen.Three neoligans(8,11,and 12),one flavanone(14),and one alkaloid(16)showed inhibitory activity against ADP-or collagen-induced platelet aggregation as compared with tirofiban.The dihydrobenzofuran neolignans(8,11,and 12)are more potent than the benzofuran neolignan(13)and other types of neolignans(1–7).Glucosidation of the dihydrobenzofuran neolignans(11 and 12)is helpful for the activity.Graphical Abstract Two new neolignans selaginellol(1)and selaginellol 40-O-b-D-glucopyranoside(2)were isolated from the whole plant of Selaginella moellendorffii.Several compounds from this plant showed the activity against platelet aggregation induced by ADP or collagen.

深绿卷柏中木脂素成分及10个木脂素结构的修订

从传统中药深绿卷柏(Selaginella doederleinii)中分离得到5个已知的木脂素,并利用高分辨质谱及1D和2D NMR数据确定了其结构分别为3个8,4′−氧新木脂素类[(−)−赤式−(7′E)−4,9−二羟基−3,3′,5′−三甲氧基−8,4′−氧新木脂素−7′−烯−9′−醛(1)、(−)−赤式−愈创木基甘油−β−O−4′−丁香树脂酚醚(2)和(7′E)−3,5,3′,5′−四甲氧基−8,4′−氧新木脂素−7′−烯−4,9,9′−三醇(3)],1个苯骈呋喃类[(+)−(7R,8S)−5−甲氧二氢去氢二松柏醇(4)]和1个双四氢呋喃类[丁香脂素(5)]。硫氧还蛋白氧化还原酶抑制活性评价显示3个化合物具有中等强度活性,其IC50值为10.1~20.2μmol/L。化合物1~4是首次分离自该植物。另外,发现10个已知木脂素[2,6,2′,6′−四甲氧基−4,4′−二(1−羟基−2,3−环氧丙基)联苯(I)、2,2′−二甲氧基−4,4′−二(1−羟基−2,3−环氧丙基)联苯(Ⅱ)、2−羟基−3,2′,6′−三甲氧基−4′−(1−羟基−2,3−环氧丙基)−5−(3−羟基丙烯基)联苯(Ⅲ)、2−羟基−3,2′−二甲氧基−4′−(1−羟基−2,3−环氧丙基)−5−(3−羟基丙烯基)联苯(Ⅳ)、2,2′−二甲氧基−4−(3−羟基丙烯基)−4′−(1,2,3−三羟丙基)二苯醚(Ⅴ和Ⅵ)、(7′R,8′R)−2,2′−二甲氧基−4−(3−羟丙烯基)−4′−(1,2,3−三羟丙基)二苯醚(Ⅶ)、野花椒乙素(Ⅷ)、地黄新木甲素(Ⅸ)和地黄新木乙素(Ⅹ)]的结构因解析不正确而误定为联苯新木脂素类和4,4′−氧新木脂素类。经过与模型化合物如一些报道的合成物及分离到的化合物(1~5)进行NMR数据对比分析后将化合物Ⅰ~Ⅹ的结构分别修订为(+)−丁香脂素(5)、(+)−松脂素(6)、(−)−simulanol(7)、(−)−去氢二松柏醇(8)、(−)−苏式−愈创木基甘油−β−O−4′−松柏醇醚(9)、(+)−赤式−愈创木基甘油−β−O−4′−松柏醇醚(10a)、(−)−赤式−愈创木基甘油−β−O−4′−松柏醇醚(10b)、(+)−苏式−愈创木基甘油−β−O−4′−丁香树脂酚醚(11)、(−)−苏式−4−O−[1−羟甲基−2−羟基−2−(3−甲氧基−4−羟苯基)乙基]阿魏酸甲酯(12)和(+)−赤式−4−O−[1−羟甲基−2−羟基−2−(3−甲氧基−4−羟苯基)乙基]阿魏酸甲酯(13)。因此,尚无证据表明自然界中存在这10种木脂素,实际上其修正后的结构分别属于双四氢呋喃类,苯骈呋喃类及8,4′−氧新木脂素类等类型。