松节藻和盾叶木的化学成分和生物活性研究
摘要
该学位论文工作主要包括两个方面的内容，其一，对松节藻科Rhodomelaceae海藻松节藻Rhodomela confervoides乙醇提取物的较大极性部位的化学成分进行了系统的分离纯化、结构鉴定和活性筛选；在此基础上，以松节藻中含量较高的化合物为合成前体，探索了松节藻中分离鉴定的其他两类新型天然产物的半合成方法：其二，对大戟科Euphorbiaceae铁苋菜亚科Acalyphoideae血桐属Macaranga植物，盾叶木Macaranga adenantha乙醇提取物中的化学成分进行了较系统的分离、结构鉴定和活性筛选。主要结果如下：
(1)运用硅胶、凝胶Sephadex LH-20、闪式快速分离系统、中压液相色潜、高效液相色谱，从松节藻乙醇提取物的大极性部位，共分离得到23个化合物，用UV、IR、1D NMR、2D NMR、MS等波谱方法鉴定了其中22个化合物的结构，包括：2-氨基-3-(3-溴-5-羟基-4-甲氧基苯基)丙酸(1)、8-溴-6-羟基-7-甲氧基-1，2，3，4-四氢异喹啉-3-羧酸(2)、8．溴-6-羟基-7甲氧基-1，2，3，4-四氢异喹啉-3-羧酸甲酯(3)、6-溴-8-羟基-7-甲氧基-1，2，3，4-四氢异喹啉-3-羧酸甲酯(4)、2，3-二溴-4，5-二羟基苯乙醇(5)、2，3-二溴-4，5-二羟基苯乙醇磺酸酯钠盐(6)、3-溴-4，5-二羟基苯乙醇磺酸酯钠盐(7)、3-溴-2-(2，3-二溴-4，5-二羟基苄基)-4，5-二羟基苯乙醇磺酸酯钠盐(8)、9-[3-溴-2-(2，3-二溴-4，5-二羟基苄基)-4，5-二羟基苄基1腺嘌呤(9)、2，3-二溴-4，5-二羟基苯甲醇-4，7-二磺酸酯钾盐(10)、2，3-二溴-4，5-二羟基苯甲醇(11)、2，3-二溴-4，5-二羟基苯甲基甲醚(12)、3-溴-5-羟基-4-甲氧基苯乙酸(13)、3-溴-5-羟基-4-甲氧基苯乙酸甲酯(14)、3-溴-5-羟基-4-甲氧基苯甲酸(15)、3，5-二溴-4-羟基苯甲基甲醚(16)、2，2’，3-三溴-4，4’，5，5’-四羟基-6’-甲氧甲基二苯甲烷(17)、2-(3-溴-5-羟基-4-甲氧基苯基)-3-(2，3-二溴-4，5-二羟基苯基)丙酸(18)、丁二酸(19)、甘露醇(20)、十六酸甲酯(21)、尿嘧啶核苷(22)。其中化合物2-9为新化合物，化合物1为新天然产物，化合物10、16、19、20、21和22为首次从松节藻中得到。
细胞毒活性筛选结果显示化合物5-7、11和12对BGC-823(人胃癌细胞)，A2780(人卵巢癌细胞)，A549(人肺腺癌细胞)，HCT-8(人结肠癌细胞)，Bel7402(人肝癌细胞)细胞株有抑制作用，化合物8和17分别对BGC-823、A549、
This thesis includes two main works. Firstly, the chemical constituents of polar portions of the ethanolic extract of Rhodomela confervoides, a red alga belonging to the Rhodomelaceae family, was investigated. Meanwhile, synthesis of two types of new compounds obtained from the alga was explored by using the co-occuring products as the starting materials. Secondly, the chemical constituents of the ethanolic extract of Macaranga adenantha, a plant belonging to the Euphorbiaceae family, was investigated. The results were listed below:
1. By using middle pressure and high pressure liquid chromatographic technigues, and column chromatography over silica gel and Sephadex LH-20, 23 compounds were isolated from the polar portions of the ethanolic extract of R. confervoides. Of which structures of 22 compounds were identified, by spectroscopic methods including UV, IR, 1D NMR, 2D NMR, and MS, as 2-amino-3-(3-bromo-5-hydroxy-4-methoxyphenyl) propionic acid (1). 8-bromo-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (2), 8-bromo-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid methyl ester (3), 6-bromo-8-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carb-oxylic acid methyl ester (4), 2,3-dibromo-4,5-dihydroxyphenylethanol (5), 2,3-dibr-omo-4,5-dihydroxyphenylethanol sulfate sodium salt (6), 3-dibromo-4,5-dihydroxyp-henylethanol sulfate sodium salt (7), 3-bromo-2-(2,3-dibromo-4,5-hydroxybenzyl)-4,5 -dihydroxyphenylethanol sulfate sodium salt (8), 9-[3-bromo-2-(2,3-dibromo-4,5-hyd-roxybenzyl)-4,5-dihydroxybenzyl]adenine(9), 2,3-dibromo-4,5-hydroxyphenylmetha-nol-4,7-disulfate potassium salt (10), 2,3-dibromo-4,5-hydroxyphenylmethanol (11), 2,3-dibromo-4,5-hydroxybenzyl methyl ether (12), 3-bromo-5-hydroxy-4-methoxyp-henyl-acetic acid (13), 3-bromo-5-hydroxy-4-methoxyphenyl-acetic acid methyl ester (14), 3-bromo-5-hydroxy-4-methoxybenzoic acid (15), 3,5-dibromo-4-hydroxybenzyl methyl ether (16), 2,2',3-tribromo-4,4',5,5'-tetrahydroxy-6'-methoxylmethyldiphenyl
(1)运用硅胶、凝胶Sephadex LH-20、闪式快速分离系统、中压液相色潜、高效液相色谱，从松节藻乙醇提取物的大极性部位，共分离得到23个化合物，用UV、IR、1D NMR、2D NMR、MS等波谱方法鉴定了其中22个化合物的结构，包括：2-氨基-3-(3-溴-5-羟基-4-甲氧基苯基)丙酸(1)、8-溴-6-羟基-7-甲氧基-1，2，3，4-四氢异喹啉-3-羧酸(2)、8．溴-6-羟基-7甲氧基-1，2，3，4-四氢异喹啉-3-羧酸甲酯(3)、6-溴-8-羟基-7-甲氧基-1，2，3，4-四氢异喹啉-3-羧酸甲酯(4)、2，3-二溴-4，5-二羟基苯乙醇(5)、2，3-二溴-4，5-二羟基苯乙醇磺酸酯钠盐(6)、3-溴-4，5-二羟基苯乙醇磺酸酯钠盐(7)、3-溴-2-(2，3-二溴-4，5-二羟基苄基)-4，5-二羟基苯乙醇磺酸酯钠盐(8)、9-[3-溴-2-(2，3-二溴-4，5-二羟基苄基)-4，5-二羟基苄基1腺嘌呤(9)、2，3-二溴-4，5-二羟基苯甲醇-4，7-二磺酸酯钾盐(10)、2，3-二溴-4，5-二羟基苯甲醇(11)、2，3-二溴-4，5-二羟基苯甲基甲醚(12)、3-溴-5-羟基-4-甲氧基苯乙酸(13)、3-溴-5-羟基-4-甲氧基苯乙酸甲酯(14)、3-溴-5-羟基-4-甲氧基苯甲酸(15)、3，5-二溴-4-羟基苯甲基甲醚(16)、2，2’，3-三溴-4，4’，5，5’-四羟基-6’-甲氧甲基二苯甲烷(17)、2-(3-溴-5-羟基-4-甲氧基苯基)-3-(2，3-二溴-4，5-二羟基苯基)丙酸(18)、丁二酸(19)、甘露醇(20)、十六酸甲酯(21)、尿嘧啶核苷(22)。其中化合物2-9为新化合物，化合物1为新天然产物，化合物10、16、19、20、21和22为首次从松节藻中得到。
细胞毒活性筛选结果显示化合物5-7、11和12对BGC-823(人胃癌细胞)，A2780(人卵巢癌细胞)，A549(人肺腺癌细胞)，HCT-8(人结肠癌细胞)，Bel7402(人肝癌细胞)细胞株有抑制作用，化合物8和17分别对BGC-823、A549、
This thesis includes two main works. Firstly, the chemical constituents of polar portions of the ethanolic extract of Rhodomela confervoides, a red alga belonging to the Rhodomelaceae family, was investigated. Meanwhile, synthesis of two types of new compounds obtained from the alga was explored by using the co-occuring products as the starting materials. Secondly, the chemical constituents of the ethanolic extract of Macaranga adenantha, a plant belonging to the Euphorbiaceae family, was investigated. The results were listed below:
1. By using middle pressure and high pressure liquid chromatographic technigues, and column chromatography over silica gel and Sephadex LH-20, 23 compounds were isolated from the polar portions of the ethanolic extract of R. confervoides. Of which structures of 22 compounds were identified, by spectroscopic methods including UV, IR, 1D NMR, 2D NMR, and MS, as 2-amino-3-(3-bromo-5-hydroxy-4-methoxyphenyl) propionic acid (1). 8-bromo-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (2), 8-bromo-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid methyl ester (3), 6-bromo-8-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carb-oxylic acid methyl ester (4), 2,3-dibromo-4,5-dihydroxyphenylethanol (5), 2,3-dibr-omo-4,5-dihydroxyphenylethanol sulfate sodium salt (6), 3-dibromo-4,5-dihydroxyp-henylethanol sulfate sodium salt (7), 3-bromo-2-(2,3-dibromo-4,5-hydroxybenzyl)-4,5 -dihydroxyphenylethanol sulfate sodium salt (8), 9-[3-bromo-2-(2,3-dibromo-4,5-hyd-roxybenzyl)-4,5-dihydroxybenzyl]adenine(9), 2,3-dibromo-4,5-hydroxyphenylmetha-nol-4,7-disulfate potassium salt (10), 2,3-dibromo-4,5-hydroxyphenylmethanol (11), 2,3-dibromo-4,5-hydroxybenzyl methyl ether (12), 3-bromo-5-hydroxy-4-methoxyp-henyl-acetic acid (13), 3-bromo-5-hydroxy-4-methoxyphenyl-acetic acid methyl ester (14), 3-bromo-5-hydroxy-4-methoxybenzoic acid (15), 3,5-dibromo-4-hydroxybenzyl methyl ether (16), 2,2',3-tribromo-4,4',5,5'-tetrahydroxy-6'-methoxylmethyldiphenyl
引文
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