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目的研究石松Lycopodium japonicum全草的生物碱成分。方法采用正、反相硅胶柱色谱及半制备型HPLC等技术进行分离纯化,根据理化性质及波谱数据鉴定化合物的结构,并以脂多糖(LPS)诱导RAW264.7细胞建立细胞炎症模型,采用Griess法检测一氧化氮(NO)量以评价化合物的抗炎活性。结果从石松全草甲醇提取物中分离得到19个化合物,分别鉴定为lycoposerramine-M N-oxide(1)、acetyllycoposerramine-M(2)、石松碱(3)、lycoposerramine-M(4)、miyoshianine-C(5)、12-epilycodoline N-oxide(6)、gnidioidine(7)、lycoposerramine-K(8)、光泽石松灵碱(9)、4a-hydroxyanhydrolycodoline(10)、flabelline(11)、hydroxypropyllycodine(12)、石松定碱(13)、去-N-甲基-α-玉柏碱(14)、α-玉柏碱(15)、去-N-甲基-β-玉柏碱(16)、石松佛利星碱(17)、lycoflexine N-oxide(18)和法氏石松定碱(19)。化合物5和18可以抑制LPS诱导的RAW264.7细胞的NO释放,其IC_(50)分别为31.82、40.69μmol/L。结论化合物1为新化合物,命名为N-氧化石松碱M,化合物2、6、11、12、16、18、19为首次从该植物中分离得到;化合物5和18表现出潜在的抗炎活性。
Objective To study the alkaloid composition of Lycopodium japonicum. Methods The compounds were isolated and purified by normal and reverse phase silica gel column chromatography and semi-preparative HPLC. The structures of compounds were identified by physico-chemical properties and spectral data. The cell inflammatory model was induced by lipopolysaccharide (LPS) in RAW264.7 cells. Griess Method to measure the amount of nitric oxide (NO) to evaluate the anti-inflammatory activity of the compounds. Results Nineteen compounds were isolated from the methanolic extract of Isatis obscurus and identified as lycoposerramine-M N-oxide (1), acetyllycoposerramine-M (2), lycopene (3), lycoposerramine-M (9), 4a-hydroxyanhydrolycodoline (10), flabelline (11), hydroxypropyllycodine (12), 12- epilycodoline N-oxide (6), gnidioidine (7), lycoposerramine-K (13), N-methyl-α-cumulus base (14), α-cumin base (15), N-methyl- Alkaloids (17), lycoflexine N-oxide (18) and famotidine (19). Compounds 5 and 18 inhibited LPS-induced NO release in RAW264.7 cells with IC 50 values of 31.82 and 40.69 μmol / L, respectively. Conclusion Compound 1 is a new compound, named as N-oxide, and compounds 2, 6, 11, 12, 16, 18 and 19 were isolated from this plant for the first time. Compounds 5 and 18 showed potential anti-inflammatory activity .