西红花柱头化学成分及其抗炎活性

Chemical constituents from the stigma of Crocus sativus and their anti-inflammatory activities

目的研究西红花Crocus sativus L.柱头的化学成分及其抗炎活性。方法西红花95%乙醇提取物采用D101型大孔树脂、硅胶、Sephadex LH-20和HPLC等进行分离纯化,根据理化性质及波谱数据鉴定所得化合物的结构。用LPS诱导的小鼠RAW 246.7细胞炎症模型评价化合物抗炎活性。结果从中分离得到14个化合物,分别鉴定为(2E,4E)-2-甲基-6-羰基-2,4-庚二烯酸-1-O-β-D-吡喃葡萄糖酯(1)、(2E,4E)-2-甲基-6-羰基-2,4-庚二烯酸甲酯(2)、山柰酚(3)、单侧西红花酸龙胆二糖酯(4)、(2E,4E)-2-甲基-6-羰基-2,4-庚二烯酸龙胆二糖酯(5)、(2E,4E)-2-甲基-6-羰基-2,4-庚二烯酸(6)、crocusatin M(7)、crocusatin K(8)、3,4-二羟基丁酸(9)、对羟基苯甲酸(10)、山柰酚-7-O-β-D-葡萄糖苷(11)、山柰酚-3-O-β-D-葡萄糖苷(12)、柚皮素-7-O-β-D-葡萄糖苷(13)、柚皮素-4′-O-β-D-葡萄糖苷(14)。化合物3、11可降低LPS诱导RAW 264.7细胞NO的释放量。结论化合物1是新化合物,化合物2是新天然产物,化合物6、8、13~14为首次从该属植物中分离得到,化合物3、11具有一定抗炎活性。

AIM To investigate the chemical from the stigma of Crocus sativus L.and their anti-inflammatory activities.METHODS The 95% ethanol extract from the stigma of C.sativus was isolated and purified by D101,silica,Sephadex LH-20 and semi-preparative HPLC,then the structures of obtained compounds were identified by physicochemical properties and spectral data.The anti-inflammatory activities were evaluated by LPS induced RAW 264.7 inflammatory cell model.RESULTS Fourteen compounds were isolated and identified as(2E,4E)-2-menthyl-6-oxohepta-2,4-dienoicacid-β-D-glucosyl ester(1),(2E,4E)-2-menthyl-6-oxohepta-2,4-dienoicacid-methyl ester(2),kaempferol(3),crocetin-β-D-gentiobiosyl ester(4),(2E,4E)-2-methyl-6-oxohepta-2,4-dienoicacid-β-D-gentiobiosyl ester(5),(2E,4E)-2-methyl-6-oxohepta-2,4-dienoic acid(6),crocusatin M(7),crocusatin K(8),3,4-dihydroxybutyric acid(9),p-hydroxybenzoic acid(10),kaempferol-7-O-glucoside.(11),kaempferol-3-O-glucoside(12),naringenin-7-O-glucoside(13) and naringenin-4′-O-glucoside(14).Compounds 3 and 11 could inhibit the production of NO by LPS-induced RAW 264.7 cells.CONCLUSION Compound 1 is a new compound.Compound 2 is a new natural product.Compounds 6,8,13-14 are isolated from genus Croucus for the first time.Compounds 3 and 11 have anti-inflammatory activities.