[关键词]
[摘要]
目的 研究洋金花Datura metel叶黄酮类和生物碱类化学成分和生物活性。方法 综合运用大孔吸附树脂、硅胶、ODS、HPLC等液相色谱法和MS、NMR等波谱法以及理化性质对化合物进行分离、纯化和鉴定,采用MTT法和Griess法研究其抗炎活性。结果 从洋金花叶70%乙醇提取物中分离得到39个化合物,分别鉴定为紫杉叶素(1)、(+)-儿茶素(2)、kaempferol-3-O-α-L-rhamnopyranoside(3)、紫云英苷(4)、异槲皮苷(5)、紫杉叶素-3-O-α-L-呋喃阿拉伯糖苷(6)、(2R,3R)-(+)-glucodistylin(7)、(2S,3S)-(-)-glucodistylin(8)、quercetin-3-O-β-xylopyranosyl-(1→2)-β-glucopyranoside(9)、异鼠李素-3-O-β-D-吡喃葡萄糖-7-O-α-L-吡喃鼠李糖苷(10)、芹菜素-7-O-β-D-吡喃葡萄糖苷(11)、香叶木素-7-O-β-D-葡萄糖苷(12)、木犀草素-7-O-β-D-(6''-乙酰基)-吡喃葡萄糖苷(13)、plantaginin(14)、木犀草素-7-O-β-D-龙胆二糖苷(15)、7-O-primverosylformononetin(16)、isoetin-7-O-β-D-glucopyranosyl-2'-O-α-D-glucopyranoside(17)、银锻苷(18)、2,3,6,7-tetrahydroxyxanthone(19)、1,2,6,7-tetrahydroxyxanthone(20)、N-反式-对-香豆酰基酪胺(21)、N-反式-对-香豆酰基章鱼胺(22)、eleutherazine B(23)、1,2,3,4-tetrahydro-1-methyl-β-carboline-3-carboxylic acid(24)、naphthisoxazol A(25)、1-甲氧甲酰-β-咔巴啉(26)、1-benzyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid(27)、(±)-1-phenyl-2-imido-1-propanol(28)、(1S,2R)-N-acetylephedrine(29)、(1R,2S)-N-acetylephedrine(30)、(1S,2R)-N-formylephedrine(31)、(1R,2S)-N-formylephedrine(32)、胸腺嘧啶(33)、脱氧胸腺嘧啶核苷(34)、2-氨基腺苷(35)、3-吲哚甲醛(36)、L-苯丙氨酸(37)、bacilsubteramide A(38)、金色酰胺醇酯(39)。生物活性测定结果表明,化合物3、5、8~11、13~15、17~18、21~27、35~36、39对脂多糖诱导的RAW264.7细胞的一氧化氮释放展现出了不同程度的抑制作用。结论 化合物6~10、13~17、19、20、23、24、27~32、35~36、38首次从茄科植物中分离得到,化合物1~3、5、11~12、18、26、33、37首次从曼陀罗属植物中分离得到。其中化合物3、5、8~11、13~15、17、18、21~27、35、36、39具有一定程度的抗炎活性。
[Key word]
[Abstract]
Objective To investigate the chemical structure and bioactivity of the flavonoids and alkaloids from leaves of Datura metel. Methods The compounds were isolated, purified and identified by various liquid chromatography methods (macroporous resin, silica gel, ODS, HPLC) and spectroscopic analysis (MS, NMR) as well as physicochemical properties. The anti-inflammatory activity of the compounds was investigated by MTT method and Griess method. Results Thirty-nine compounds were isolated from the 70% EtOH extract of the leaves of D. metel and identified as taxifolin (1), (+)-catechin (2), kaempferol-3-O-α-L-rhamnopyranoside (3), astragalin (4), isoquercitrin (5), taxifolin-3-O-α-L-arabinofuranoside (6), (2R,3R)-(+)-glucodistylin (7), (2S,3S)-(-)-glucodistylin (8), quercetin-3-O-β-xylopyranosyl-(1→2)-β-glucopyranoside (9), isorhamnetin-3-O-β-D-glucopyranosyl-7-O-α-L-rhamnopyranoside (10), apigenin-7-O-β-D-glucopyranoside (11), diosmetin-7-O-β-D-glucoside (12), luteolin-7-O-β-D-(6''-acetyl)-glucopyranoside (13), plantaginin (14), luteolin-7-O-β-D-gentiobioside (15) 7-O-primverosylformononetin (16), isoetin-7-O-β-D-glucopyranosyl-2'-O-α-D-glucopyranoside (17), tiliroside (18), 2,3,6,7-tetrahydroxyxanthone (19), 1,2,6,7-tetrahydroxyxanthone (20), N-trans-p-coumaroyltyramine (21), N-trans-p-coumaroyloctopamine (22), eleutherazine B (23), 1,2,3,4-tetrahydro-1-methyl-β-carboline-3-carboxylic acid (24), naphthisoxazol A (25), 1-carbomethoxy-β-carboline (26), 1-benzyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid (27), (±)-1-phenyl-2-imido-1-propanol (28), (1S,2R)-N-acetylephedrine (29), (1R,2S)-N-acetylephedrine (30), (1S,2R)-N-formylephedrine (31), (1R,2S)-N-formylephedrine (32), thymine (33), thymidine (34), 2-amino adenosine (35), 1H-indole-3-carboxaldehyde (36), L-phenylalanine (37), bacilsubteramide A (38), aurantiamide acetate (39). And the results of bioassay showed that compounds 3, 5, 8—11, 13—15, 17, 18, 21—27, 35, 36, 39 exhibited different degrees of inhibitory effect against NO production in lipopolysaccharide-stimulated RAW264.7 cells. Conclusion Compounds 6—10, 13—17, 19, 20, 23, 24, 27—32, 35, 36, 38 are isolated from the Solanaceae for the first time, and compounds 1—3, 5, 11, 12, 18, 26, 33, 37 are isolated from the genus Datura for the first time. Compounds 3, 5, 8—11, 13—15, 17, 18, 21—27, 35, 36, 39 displayed some anti-inflammatory activity.
[中图分类号]
R284.1
[基金项目]
国家自然科学基金资助项目(81773883,81903781);博士后科学基金资助项目(2018M631978);国家重点研发计划项目(2018YFC1707100);黑龙江省自然科学基金优秀青年项目(YQ2019H029);黑龙江中医药大学校基金资助项目(2018pt01,2018bs03)