苦碟子和苍耳化学成分及生物活性研究
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摘要
本文分别将干燥苦碟子Ixeris sonchifolia (Bge.) Hance的根部、地上部分和蒙古苍耳Xanthium mongolicum Kitag.的茎叶、苍耳子用乙醇浸泡提取,提取液浓缩后分别依次用石油醚、乙酸乙酯和正丁醇萃取,制得各种不同极性萃取物。利用柱色谱和高效液相色谱等方法对各种萃取物进行分离纯化,通过1H NMR,13C NMR, HMQC, HMBC, NOESY, IR, UV, MS等现代波谱技术进行结构鉴定。结果从苦碟子中分离鉴定了35个化合物,主要为倍半萜内酯类化合物,其中14个为新化合物,14个首次从苦碟子中分离得到；从蒙古苍耳中分离鉴定了30个化合物,其中3个化合物与苦碟子中分离得到的化合物相同,21个化合物首次从蒙古苍耳中分离得到。新化合物的结构分别为10αH-3,11(13)-愈创木二烯-12,6-内酯-2-酮-9β-O-β-D-葡萄糖苷(1)、10αH-3,11(13)-愈创木二烯-12,6-内酯-2-酮-9β-O-对羟基苯乙酸酯(2)、10αH-3,11(13)-愈创木二烯-12,6-内酯-2-酮-9β-O-β-D-(对羟基苯乙酸-6-葡萄糖酯)苷(3)、9β-羟基-10αH-3,11(13)-愈创木二烯-12,6-内酯-2-酮(4)、9β-羟基-10α,11βH-3-愈创木烯-12,6-内酯-2-酮(5)、15-羟基-10αH-3,11(13)-愈创木二烯-12,6-内酯-2-酮(6)、15-羟基-10β,11αH-3-愈创木烯-12,6-内酯-2-酮(7)、9β-羟基-10α,11α,11αH-3-愈创木烯-12,6-内酯-2-酮(8)、9α-羟基-100α,11αH-3-愈创木烯-12,6-内酯-2-酮(9)、10α,11βH-3-愈创木烯-12,6-内酯-2-酮-9β-O-β-D-葡萄糖苷(10)、10αH-3,5,11(13)-愈创木三烯-12-酸-2-酮-9β-O-β-D-葡萄糖苷(11)、10α,11βH-3,5-愈创木二烯-12-酸-2-酮-9β-O-β-D-葡萄糖苷(12)、3α-羟基-4(15)-桉烯-12,6-内酯(13)、3-羟基-11αH-1(10),3-愈创木二烯-12,6-内酯-2-酮(14),并将其分别命名为：苦碟子苦素A～M和11-epi-8-desoxyartelin。
通过对苦碟子苦素A在盐酸、硫酸、醋酸以及葡聚糖酶等条件下水解脱糖反应的研究,探讨了以苦碟子苦素A为原料制备苦碟子苦素D及其它衍生物的途径。
对部分倍半萜类化合物进行了活性测试,结果表明,苦碟子苦素A、C、J和苦碟子内酯A、B以及Ixerin Z对P-388小鼠白血病细胞显示一定的抑制活性；苦碟子苦素A、B、C、D、M和苦碟子内酯A、B对HepG2肝癌细胞的生长都有较好的抑制作用；苦碟子苦素A和苦碟子的正丁醇提取物对叶霉病病原菌抑制效果较好；苍耳亭、苍耳皂素、11α,13-二氢苍耳亭对细胞粘附分子ICAM-1的诱导产生具有一定阻碍活性。
The air-dried roots and aerial parts ofⅠ. sonchifolia and the air-dried fruits and aerial parts of X. mongolicum were investagated in this research. The ethanol extracts of the different parts of these plants were gradient extracted with petroleum ether, EtOAc and n-BuOH, respectively. As the results, fourteen new sesquiterpene lactone type compounds together with twenty-one known ones were isolated fromⅠ. sonchifolia and thirty known compounds were isolated fromⅩ. mongolicum by the methods of silica gel column chromatography, thin layer chromatography and high performance liquid chromatography. Also, three common known compounds were isolated from these two type plants and fourteen known compounds isolated fromⅠ. sonchifolia and twenty-one known ones isolated from X. mongolicum were first purified from this plants. The structures of these compounds were elucidated on the basis of spectroscopic analysis of IR, UV, EI-MS, HREIMS, and NMR. Fourteen new compounds are 2-oxoguaia-3,11(13)-dieno-12,6-lactone-9β-O-β-D-glucopyra-noside (1),9β-(p-hydroxypheny lacetyloxy)-2-oxoguaia-3,11(13)-dieno-12,6-lactone (2),9β-(6'-phydroxyl-phenylacetyloxy)-β-D-glucopyranosyloxy-2-oxoguania-3,11(13)-dieno-12,6-lactone (3),9β-hydroxy-2-oxoguaia-3,11(13)-dieno-12,6-lactone (4),11βH-9β-hydroxy-2-oxoguaia-3-eno-12,6-lactone (5),15-hydroxy-2-oxoguaia-3,11(13)-dieno-12,6-lactone (6), 10β,11αH-15-hydroxy-2-oxoguaia-3-eno-12,6-lactone (7),11 aH-9β-hydroxy-2-oxoguaia-3-eno-12,6-lactone (8),11αH-9α-hydroxy-2-oxoguaia-3-eno-12,6-lactone (9),1 1βH-2-oxogu-aia-3-eno-12,6-lactone-9β-O-β-D-glucopyranoside (10),2-oxoguaia-3,5,1 1(13)-trieno-12-car-boxylicacid-2-ketone-9β-O-β-D-glucopyranoside (11),1 1βH-2-oxoguaia-3,5-dieno-12-carb-oxylicacid-2-ketone-9β-O-β-D-glucopyranoside (12),3α-hydroxy-4(15)-eucalyptus-diene-12,6-lactone (13), 11αH-3-hydroxy-2-oxoguaia-1(10),3-dieno-12,6-lactone (14), namely, sonchifoliasolide A to M and 11-epi-8-desoxyartelin.
The reaction route of preparing sonchifoliasolide D and other derivatives from sonchifoliasolide A was discussed by the hydrolysis reaction of sonchifoliasolide A at the conditions of HCl, H2SO4, HNO3, and glucose enzyme.
The bioactivities of some sesquiterpene compounds were tested and sonchifoliasolides A, C, and J, sonchifolactons A and B, and Ixerin Z showed inhibited activity to P-388 mouse leukaemia cells. Sonchifoliasolides A, B, C, D, and M, sonchifolactons A and B exhibited excellent growth inhibit effect on HepG2 cells. Sonchifoliasolide A and n-BuOH extract ofⅠ. sonchifolia indicated inhibiting growth activity to pathogen of leaf mold and verticillium. Compounds xanthatin, xanthinosin, and 11α,13-dihydroxanthatin showed the induction hindrance activity to ICAM-1 cells.
通过对苦碟子苦素A在盐酸、硫酸、醋酸以及葡聚糖酶等条件下水解脱糖反应的研究,探讨了以苦碟子苦素A为原料制备苦碟子苦素D及其它衍生物的途径。
对部分倍半萜类化合物进行了活性测试,结果表明,苦碟子苦素A、C、J和苦碟子内酯A、B以及Ixerin Z对P-388小鼠白血病细胞显示一定的抑制活性；苦碟子苦素A、B、C、D、M和苦碟子内酯A、B对HepG2肝癌细胞的生长都有较好的抑制作用；苦碟子苦素A和苦碟子的正丁醇提取物对叶霉病病原菌抑制效果较好；苍耳亭、苍耳皂素、11α,13-二氢苍耳亭对细胞粘附分子ICAM-1的诱导产生具有一定阻碍活性。
The air-dried roots and aerial parts ofⅠ. sonchifolia and the air-dried fruits and aerial parts of X. mongolicum were investagated in this research. The ethanol extracts of the different parts of these plants were gradient extracted with petroleum ether, EtOAc and n-BuOH, respectively. As the results, fourteen new sesquiterpene lactone type compounds together with twenty-one known ones were isolated fromⅠ. sonchifolia and thirty known compounds were isolated fromⅩ. mongolicum by the methods of silica gel column chromatography, thin layer chromatography and high performance liquid chromatography. Also, three common known compounds were isolated from these two type plants and fourteen known compounds isolated fromⅠ. sonchifolia and twenty-one known ones isolated from X. mongolicum were first purified from this plants. The structures of these compounds were elucidated on the basis of spectroscopic analysis of IR, UV, EI-MS, HREIMS, and NMR. Fourteen new compounds are 2-oxoguaia-3,11(13)-dieno-12,6-lactone-9β-O-β-D-glucopyra-noside (1),9β-(p-hydroxypheny lacetyloxy)-2-oxoguaia-3,11(13)-dieno-12,6-lactone (2),9β-(6'-phydroxyl-phenylacetyloxy)-β-D-glucopyranosyloxy-2-oxoguania-3,11(13)-dieno-12,6-lactone (3),9β-hydroxy-2-oxoguaia-3,11(13)-dieno-12,6-lactone (4),11βH-9β-hydroxy-2-oxoguaia-3-eno-12,6-lactone (5),15-hydroxy-2-oxoguaia-3,11(13)-dieno-12,6-lactone (6), 10β,11αH-15-hydroxy-2-oxoguaia-3-eno-12,6-lactone (7),11 aH-9β-hydroxy-2-oxoguaia-3-eno-12,6-lactone (8),11αH-9α-hydroxy-2-oxoguaia-3-eno-12,6-lactone (9),1 1βH-2-oxogu-aia-3-eno-12,6-lactone-9β-O-β-D-glucopyranoside (10),2-oxoguaia-3,5,1 1(13)-trieno-12-car-boxylicacid-2-ketone-9β-O-β-D-glucopyranoside (11),1 1βH-2-oxoguaia-3,5-dieno-12-carb-oxylicacid-2-ketone-9β-O-β-D-glucopyranoside (12),3α-hydroxy-4(15)-eucalyptus-diene-12,6-lactone (13), 11αH-3-hydroxy-2-oxoguaia-1(10),3-dieno-12,6-lactone (14), namely, sonchifoliasolide A to M and 11-epi-8-desoxyartelin.
The reaction route of preparing sonchifoliasolide D and other derivatives from sonchifoliasolide A was discussed by the hydrolysis reaction of sonchifoliasolide A at the conditions of HCl, H2SO4, HNO3, and glucose enzyme.
The bioactivities of some sesquiterpene compounds were tested and sonchifoliasolides A, C, and J, sonchifolactons A and B, and Ixerin Z showed inhibited activity to P-388 mouse leukaemia cells. Sonchifoliasolides A, B, C, D, and M, sonchifolactons A and B exhibited excellent growth inhibit effect on HepG2 cells. Sonchifoliasolide A and n-BuOH extract ofⅠ. sonchifolia indicated inhibiting growth activity to pathogen of leaf mold and verticillium. Compounds xanthatin, xanthinosin, and 11α,13-dihydroxanthatin showed the induction hindrance activity to ICAM-1 cells.
引文
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