中华青牛胆中2个新的木脂素葡萄糖苷

Two new lignan glucosides from caulis of Tinospora sinensis

目的研究中华青牛胆Tinospora sinensis的化学成分及其体外抗神经炎症活性。方法采用硅胶、Sephadex LH-20、ODS和制备型HPLC等色谱分离技术对化学成分进行分离纯化,并运用理化性质结合现代谱学(ESI-MS、1H-NMR、13C-NMR、ECD)解析技术进行结构鉴定。利用脂多糖(LPS)诱导的BV-2小胶质细胞模型进行抗神经炎症活性筛选。结果从中华青牛胆藤茎的95%乙醇水提取物中分离得到13个化合物,分别鉴定为中华青牛胆木脂苷C(1)、中华青牛胆木脂苷D(2)、裂环异落叶松脂醇-9-O-β-吡喃葡萄糖苷(3)、(+)-松脂醇-4-O-β-D-吡喃葡萄糖苷(4)、(+)-丁香脂素(5)、tanegoside A(6)、(E)-3-[(2,3-trans)-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-2,3-dihydrobenzo[b][1,4]dioxin-6-yl]-N-(4-hydroxy-phenethyl)acrylamide(7)、银钩花胺酰B(8)、反式-N-p-香豆酰基酪胺(9)、N-反式-阿魏酰酪胺(10)、N-反式-咖啡酰酪胺(11)、克罗酰胺K(12)、顺式-克罗酰胺K(13)。发现7个化合物具有抗神经炎症活性。结论所分离鉴定的化合物包括木脂素和生物碱,其中化合物1和2为新化合物,3、5、7、8、10~13为首次从该植物中分离得到。化合物9和10的活性强于阳性对照米诺环素。

Objective To study the chemical constituents and anti-neuroinflammatory activity of the caulis of Tinospora sinensis as a ＂Yao＂ medicine. Methods The chemical constituents were isolated and purified by silica gel, Sephadex LH-20, ODS column chromatographies, and semi-preparative HPLC. The structures of these compounds were elucidated by extensive spectroscopic analyses and chemical methods. All compounds were evaluated for their anti-neuroinflammatory effect by inhibiting the nitric oxide（NO） production in lipopolysaccharide（LPS）-activated murine BV-2 microglial cells except for compounds 7 and 8. Results Thirteen compounds were isolated from the caulis of T. sinensis. They were identified as tinosposide C（1）, tinosposide D（2）, seco-isolariciresinol 9-O-β-glucopyranoside（3）,（＋）-pinoresinol 4-O-β-D-glucopyranoside（4）,（＋）-syringaresinol（5）, tanegoside A（6）,（E）-3-[（2,3-trans）-2-（4-hydroxy-3-methoxyphenyl）-3-hydroxymethyl-2,3-dihydrobenzo [b] [1,4]dioxin-6-yl]-N-（4-hydroxyphenethyl） acrylamide（7）, thoreliamide B（8）, trans-N-p-coumaroyltyramine（9）, N-trans-feruloyltyramine（10）, N-trans-caffeoyltyramine（11）, grossamide K（12）, and cis-grossamide K（13）, seven of which exhibited significant anti-neuroinflammatory activity with IC50 values ranging from 1.46 to 51.25 μmol/L. Conclusion Compounds 1 and 2 are new compounds and their absolute configurations are confirmed by ECD experiments, compounds 3, 5, 7, 8, and 10—13 are isolated from the plants for the first time. The activity of compounds 9 and 10 is better than positive control minocycline.