小粘膜藻和苔海绵活性先导化合物研究
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摘要
为了从海洋生物中寻找新的药用活性先导化合物，开发利用我国的海洋生物资源，在已有研究基础之上，对13种海藻的乙醇提取物以及乙酸乙酯相、正丁醇相和水相萃取物，进行了10种肿瘤细胞株的抗肿瘤活性筛选，确定对小粘膜藻的乙酸乙酯相进行进一步的研究；继续对小粘膜藻乙酸乙酯相进行正相硅胶柱层析，所得到的24个极性部位进行了6种肿瘤细胞株的抗肿瘤活性筛选，确定了抗肿瘤活性较好的极性部位。综合考虑生物活性和样品生物量，对小粘膜藻进行了活性跟踪的化学成分研究。
应用重结晶、正相硅胶柱色谱、生物胶柱色谱、凝胶柱色谱、反相中压液相色谱和高压液相色谱等分离纯化手段，从小粘膜藻乙醇提取物的乙酸乙酯相中，分离得到溴酚、生物碱、甘油酯和甾醇等25个化合物，其结构通过红外光谱、质谱、高分辨质谱、核磁共振波谱和X-射线单晶衍射技术等现代光谱手段以及与文献数据对比进行鉴定，其中8个为新结构化合物，分别命名为：(E)-2-甲基-3-(2,3-二溴-4,5-二羟基苯)丙烯醛 (1)，(+)-2-甲基-3-(2,3-二溴-4,5-二羟基苯)-1-丙醇 (2)，5,6(-二乙氧甲基-3,4,2(-三溴-2,3(,4(-三羟基二苯醚 (3)，2-(2,3-二溴-4,5-二羟基苯甲基)-3,5-二羟基-4-甲氧基苯甲醇 (4)，6-(2,3-二溴-4,5-二羟基苯甲基)-2,3-二溴-4,5-二羟基苯甲基甲醚 (5)，9,10-二氢-9,10-二甲氧基-3,4,7,8-四溴-1,2,5,6-四羟基蒽 (6)，(+)-3-(2,3-二溴-4,5-二羟基苯)-4-溴-5,6-二羟基-1,3-二氢异苯并呋喃 (7) 和rel-(4aS*,10aR*)-(()-6,7-二溴-4a-羟基-3,8-二羟甲基-10a-甲氧基-1,4,4a,10a-四氢二苯并[b,e][1,4]二氧六环-1-酮 (8)；17个为已知结构化合物，分别为：3-溴-4-羟基苯甲酸 (9)，2-溴-4,5-二羟基苯甲醛 (10)，3-溴-4,5-二羟基苯甲醛 (11)，2,3-二溴-4,5-二羟基苯甲醛 (12)，2,3-二溴-4,5-二羟基苯甲醇 (13)，2,3-二溴-4,5-二羟基苯甲基甲醚 (14)，2,3-二溴-4,5-二羟基苯甲基乙醚 (15)，双-(2,3-二溴-4,5-二羟基苯甲基)醚 (16)，2,2(,3,3(-四溴-4,4(,5,5(-四羟基双苯基甲烷 (17)，2-(2,3-二溴-4,5-二
羟基苯甲基)-3-溴-4,5-二羟基苯甲基甲醚 (18)，2-(2,3-二溴-4,5-二羟基苯甲基)-3-溴-4,5-二羟基苯甲基乙醚 (19)，吲哚-3-甲酸 (20)，3-羟基乙酰基吲哚 (21)，3,5-二羟基-4-甲氧基苯甲醇 (22)，4-羟基苯甲酸 (23)，1-O-十六烷酰基甘油酯 (24) 和岩藻甾醇 (25)。以上得到的纯化合物分别对HCT-8、Bel7402、BGC823、A549、A2780和MCF-7肿瘤细胞株进行了抗肿瘤活性筛选；对乙酰胆碱酯酶AChE、环氧化酶COX-2和蛋白质酪氨酸磷酸酯酶PTP1B进行了酶抑制活性筛选；对T、B淋巴细胞进行了免疫调节活性筛选以及对白色假丝酵母菌、金黄色葡萄球菌和大肠杆菌进行了抗菌活性筛选。实验表明：新化合物5，已知化合物16~19和24具有较好的抗肿瘤活性，其中新化合物5对Bel7402、BGC823、A549和A2780四种肿瘤细胞的IC50值分别为2.83、5.21、1.49和1.58 μg/mL；化合物16、17和19对蛋白质酪氨酸磷酸酯酶PTP1B具有极强的抑制活性，对应的IC50值分别为1.5、2.4和0.84 μmol/L；化合物16~19对T、B淋巴细胞具有非常好的免疫抑制活性，但具有细胞毒性；以上化合物均未表现明显的抗菌活性。
海绵是海洋天然产物研究报道最多的海洋生物之一，它富含结构新颖，活性显著的次级代谢产物。对采自青岛海域罕见的苔海绵乙醇提取物以及乙酸乙酯相、正丁醇相和水相萃取物，进行了10种肿瘤细胞株的抗肿瘤活性筛选，并对其乙酸乙酯相进行了化学成分研究。应用重结晶、正相硅胶柱色谱、凝胶柱色谱和反相中压液相色谱等分离纯化手段，从苔海绵乙醇提取物的乙酸乙酯相分离得到6个化合物，其结构通过红外光谱、质谱和核磁共振等现代光谱手段以及与文献数据对比进行鉴定，确定结构分别为：胸腺嘧啶 (26)，胸腺嘧啶脱氧核苷 (27)，尿嘧啶脱氧核苷 (28)，4-羟基苯甲酸 (29)，苯乙酰胺 (30) 和正十六碳酸 (31)。并采用MTT方法，在HCT-8、Bel7402、BGC823、A549、A2780和MCF-7肿瘤细胞株模型上对化合物26~31进行了抗肿瘤活性筛选。实验表明，以上6个化合物均未表现明显的抗肿瘤活性。
In order to search for new active lead compounds from marine organisms and make good use of marine resources, the ethanolic extract, EtOAc portion, n-BuOH portion and water portion of thirteen marine algae were screened for antitumor activity against ten human cancer cell lines. The EtOAc portion of the brown alga Leathesia nana S. et G. was further studied. Fractions L1~L24 obtained by normal phase silica gel chromatography of the EtOAc soluble extract were screened for antitumor activity against six human cancer cell lines to search for active portions. On the basis of bioactivity and sample quantity, the brown alga Leathesia nana was subjected to bioassay-guided purification and identification.
Twenty-five compounds, including bromophenol, alkaloid, glyceride and steroid, were isolated from the EtOAc portion of the ethanolic extract of the brown alga Leathesia nana by means of recrystallization, normal phase silica gel chromatography, Bio-Beads SX3 chromatography, Sephadex LH-20 chromatography, reverse phase MPLC and HPLC. Their structures were elucidated by spectroscopic methods, including IR, MS, HRMS, NMR and X-ray single crystal diffraction experiments, and comparison of their physical and spectral data with those in literatures. Among these twenty-five compounds, eight new were named as (E)-2-methyl-3-(2,3-dibromo- 4,5-dihydroxyphenyl)-propenal (1), (+)-2-methyl-3-(2,3-dibromo-4,5-dihydroxyphenyl)
-1-propanol (2), 5,6(-diethyloxymethyl-3,4,2(-tribromo-2,3(,4(-trihydroxydiphenyl ether (3), 2-(2,3-dibromo-4,5-dihydroxybenzyl)-3,5-dihydroxy-4-methoxybenzyl alcohol (4), 6-(2,3-dibromo-4,5-dihydroxybenzyl)-2,3-dibromo-4,5-dihydroxybenzyl methyl ether (5), 9,10-dihydro-9,10-dimethoxy-3,4,7,8-tetrabromo-1,2,5,6- tetrahydroxyanthracene (6), (+)-3-(2,3-dibromo-4,5-dihydroxy-phenyl)-4-bromo-5,6- dihydroxy-1,3-dihydroiso -benzofuran (7) and rel-(4aS*,10aR*)-(()-6,7- dibromo-4a-hydroxy-3,8-dihydroxy-methyl-10a-methoxy-1,4,4a,10a-tetrahydrodibenzo[b,e][1,4]dioxin-1-one (8); and seventeen known were named as 3-bromo- 4-hydroxybenzoic acid (9), 2-bromo-4,5-dihydroxybenzaldehyde (10), 3-bromo- 4,5-dihydroxybenzaldehyde (11), 2,3-dibromo-4,5-dihydroxybenzaldehyde (12), 2,3-dibromo-4,5-dihydroxybenzyl alcohol (13), 2,3-dibromo-4,5-dihydroxybenzyl methyl ether (14), 2,3-dibromo-4,5-dihydroxybenzyl ethyl ether (15), bis(2,3- dibromo-4,5-dihydroxybenzyl) ether (16), 2,2(,3,3(-tetra-bromo-4,4(,5,5(- tetrahydroxydiphenyl methane (17), 2-(2,3-dibromo-4,5-dihydroxy-benzyl)- 3-bromo-4,5-dihydroxybenzyl methyl ether (18), 2-(2,3-dibromo-4,5-di- hydroxybenzyl)-3-bromo-4,5-dihydroxybenzyl ethyl ether (19), 1H-indole-3- carboxylic acid (20), 3-hydroxyacetyl-1H-indole (21), 3,5-dihydroxy- 4-methoxyl benzyl alcohol (22), 4-hydroxybenzoic acid (23), 1-O-hexanoyl-glycerol ester (24) and fucosterol (25). Compounds 1~25 were screened for antitumor activity against six human tumor cell lines HCT-8, Bel7402, BGC823, A549, A2780 and MCF-7, enzymatic inhibitory activity against three enzymes AChE, COX-2 and PTP1B, immune modulatory activity toward T and B lymphocyte, antifungal activity against Canidia albicans and antibacterial activity against Staphylococcus aurens and Escherichia coli. In the in vitro activity test, new compound 5 and known compounds 16~19 and 24 exhibited strong antitumor activity. Especially, IC50 value of compound 5 was found to be 2.83, 5.21, 1.49 and 1.58 μg/mL against four human tumor cell lines Bel7402, BGC823, A549 and A2780, respectively. Compounds 16, 17 and 19 showed significant enzymatic inhibitory activity against protein tyrosine phosphatase PTP1B
with an IC50 value of 1.5, 2.4 and 0.84 μmol/L, respectively. Compounds 16~19 exhibited powerful immune modulatory activity toward T and B lymphocyte while they displayed toxicity against normal cells. All compounds do not show significant antifungal and antibacterial activity.
It has been reported marine sponge is one of the marine organisms that are studied most for marine natural products. They have proven to be a rich source for novel organic com
应用重结晶、正相硅胶柱色谱、生物胶柱色谱、凝胶柱色谱、反相中压液相色谱和高压液相色谱等分离纯化手段，从小粘膜藻乙醇提取物的乙酸乙酯相中，分离得到溴酚、生物碱、甘油酯和甾醇等25个化合物，其结构通过红外光谱、质谱、高分辨质谱、核磁共振波谱和X-射线单晶衍射技术等现代光谱手段以及与文献数据对比进行鉴定，其中8个为新结构化合物，分别命名为：(E)-2-甲基-3-(2,3-二溴-4,5-二羟基苯)丙烯醛 (1)，(+)-2-甲基-3-(2,3-二溴-4,5-二羟基苯)-1-丙醇 (2)，5,6(-二乙氧甲基-3,4,2(-三溴-2,3(,4(-三羟基二苯醚 (3)，2-(2,3-二溴-4,5-二羟基苯甲基)-3,5-二羟基-4-甲氧基苯甲醇 (4)，6-(2,3-二溴-4,5-二羟基苯甲基)-2,3-二溴-4,5-二羟基苯甲基甲醚 (5)，9,10-二氢-9,10-二甲氧基-3,4,7,8-四溴-1,2,5,6-四羟基蒽 (6)，(+)-3-(2,3-二溴-4,5-二羟基苯)-4-溴-5,6-二羟基-1,3-二氢异苯并呋喃 (7) 和rel-(4aS*,10aR*)-(()-6,7-二溴-4a-羟基-3,8-二羟甲基-10a-甲氧基-1,4,4a,10a-四氢二苯并[b,e][1,4]二氧六环-1-酮 (8)；17个为已知结构化合物，分别为：3-溴-4-羟基苯甲酸 (9)，2-溴-4,5-二羟基苯甲醛 (10)，3-溴-4,5-二羟基苯甲醛 (11)，2,3-二溴-4,5-二羟基苯甲醛 (12)，2,3-二溴-4,5-二羟基苯甲醇 (13)，2,3-二溴-4,5-二羟基苯甲基甲醚 (14)，2,3-二溴-4,5-二羟基苯甲基乙醚 (15)，双-(2,3-二溴-4,5-二羟基苯甲基)醚 (16)，2,2(,3,3(-四溴-4,4(,5,5(-四羟基双苯基甲烷 (17)，2-(2,3-二溴-4,5-二
羟基苯甲基)-3-溴-4,5-二羟基苯甲基甲醚 (18)，2-(2,3-二溴-4,5-二羟基苯甲基)-3-溴-4,5-二羟基苯甲基乙醚 (19)，吲哚-3-甲酸 (20)，3-羟基乙酰基吲哚 (21)，3,5-二羟基-4-甲氧基苯甲醇 (22)，4-羟基苯甲酸 (23)，1-O-十六烷酰基甘油酯 (24) 和岩藻甾醇 (25)。以上得到的纯化合物分别对HCT-8、Bel7402、BGC823、A549、A2780和MCF-7肿瘤细胞株进行了抗肿瘤活性筛选；对乙酰胆碱酯酶AChE、环氧化酶COX-2和蛋白质酪氨酸磷酸酯酶PTP1B进行了酶抑制活性筛选；对T、B淋巴细胞进行了免疫调节活性筛选以及对白色假丝酵母菌、金黄色葡萄球菌和大肠杆菌进行了抗菌活性筛选。实验表明：新化合物5，已知化合物16~19和24具有较好的抗肿瘤活性，其中新化合物5对Bel7402、BGC823、A549和A2780四种肿瘤细胞的IC50值分别为2.83、5.21、1.49和1.58 μg/mL；化合物16、17和19对蛋白质酪氨酸磷酸酯酶PTP1B具有极强的抑制活性，对应的IC50值分别为1.5、2.4和0.84 μmol/L；化合物16~19对T、B淋巴细胞具有非常好的免疫抑制活性，但具有细胞毒性；以上化合物均未表现明显的抗菌活性。
海绵是海洋天然产物研究报道最多的海洋生物之一，它富含结构新颖，活性显著的次级代谢产物。对采自青岛海域罕见的苔海绵乙醇提取物以及乙酸乙酯相、正丁醇相和水相萃取物，进行了10种肿瘤细胞株的抗肿瘤活性筛选，并对其乙酸乙酯相进行了化学成分研究。应用重结晶、正相硅胶柱色谱、凝胶柱色谱和反相中压液相色谱等分离纯化手段，从苔海绵乙醇提取物的乙酸乙酯相分离得到6个化合物，其结构通过红外光谱、质谱和核磁共振等现代光谱手段以及与文献数据对比进行鉴定，确定结构分别为：胸腺嘧啶 (26)，胸腺嘧啶脱氧核苷 (27)，尿嘧啶脱氧核苷 (28)，4-羟基苯甲酸 (29)，苯乙酰胺 (30) 和正十六碳酸 (31)。并采用MTT方法，在HCT-8、Bel7402、BGC823、A549、A2780和MCF-7肿瘤细胞株模型上对化合物26~31进行了抗肿瘤活性筛选。实验表明，以上6个化合物均未表现明显的抗肿瘤活性。
In order to search for new active lead compounds from marine organisms and make good use of marine resources, the ethanolic extract, EtOAc portion, n-BuOH portion and water portion of thirteen marine algae were screened for antitumor activity against ten human cancer cell lines. The EtOAc portion of the brown alga Leathesia nana S. et G. was further studied. Fractions L1~L24 obtained by normal phase silica gel chromatography of the EtOAc soluble extract were screened for antitumor activity against six human cancer cell lines to search for active portions. On the basis of bioactivity and sample quantity, the brown alga Leathesia nana was subjected to bioassay-guided purification and identification.
Twenty-five compounds, including bromophenol, alkaloid, glyceride and steroid, were isolated from the EtOAc portion of the ethanolic extract of the brown alga Leathesia nana by means of recrystallization, normal phase silica gel chromatography, Bio-Beads SX3 chromatography, Sephadex LH-20 chromatography, reverse phase MPLC and HPLC. Their structures were elucidated by spectroscopic methods, including IR, MS, HRMS, NMR and X-ray single crystal diffraction experiments, and comparison of their physical and spectral data with those in literatures. Among these twenty-five compounds, eight new were named as (E)-2-methyl-3-(2,3-dibromo- 4,5-dihydroxyphenyl)-propenal (1), (+)-2-methyl-3-(2,3-dibromo-4,5-dihydroxyphenyl)
-1-propanol (2), 5,6(-diethyloxymethyl-3,4,2(-tribromo-2,3(,4(-trihydroxydiphenyl ether (3), 2-(2,3-dibromo-4,5-dihydroxybenzyl)-3,5-dihydroxy-4-methoxybenzyl alcohol (4), 6-(2,3-dibromo-4,5-dihydroxybenzyl)-2,3-dibromo-4,5-dihydroxybenzyl methyl ether (5), 9,10-dihydro-9,10-dimethoxy-3,4,7,8-tetrabromo-1,2,5,6- tetrahydroxyanthracene (6), (+)-3-(2,3-dibromo-4,5-dihydroxy-phenyl)-4-bromo-5,6- dihydroxy-1,3-dihydroiso -benzofuran (7) and rel-(4aS*,10aR*)-(()-6,7- dibromo-4a-hydroxy-3,8-dihydroxy-methyl-10a-methoxy-1,4,4a,10a-tetrahydrodibenzo[b,e][1,4]dioxin-1-one (8); and seventeen known were named as 3-bromo- 4-hydroxybenzoic acid (9), 2-bromo-4,5-dihydroxybenzaldehyde (10), 3-bromo- 4,5-dihydroxybenzaldehyde (11), 2,3-dibromo-4,5-dihydroxybenzaldehyde (12), 2,3-dibromo-4,5-dihydroxybenzyl alcohol (13), 2,3-dibromo-4,5-dihydroxybenzyl methyl ether (14), 2,3-dibromo-4,5-dihydroxybenzyl ethyl ether (15), bis(2,3- dibromo-4,5-dihydroxybenzyl) ether (16), 2,2(,3,3(-tetra-bromo-4,4(,5,5(- tetrahydroxydiphenyl methane (17), 2-(2,3-dibromo-4,5-dihydroxy-benzyl)- 3-bromo-4,5-dihydroxybenzyl methyl ether (18), 2-(2,3-dibromo-4,5-di- hydroxybenzyl)-3-bromo-4,5-dihydroxybenzyl ethyl ether (19), 1H-indole-3- carboxylic acid (20), 3-hydroxyacetyl-1H-indole (21), 3,5-dihydroxy- 4-methoxyl benzyl alcohol (22), 4-hydroxybenzoic acid (23), 1-O-hexanoyl-glycerol ester (24) and fucosterol (25). Compounds 1~25 were screened for antitumor activity against six human tumor cell lines HCT-8, Bel7402, BGC823, A549, A2780 and MCF-7, enzymatic inhibitory activity against three enzymes AChE, COX-2 and PTP1B, immune modulatory activity toward T and B lymphocyte, antifungal activity against Canidia albicans and antibacterial activity against Staphylococcus aurens and Escherichia coli. In the in vitro activity test, new compound 5 and known compounds 16~19 and 24 exhibited strong antitumor activity. Especially, IC50 value of compound 5 was found to be 2.83, 5.21, 1.49 and 1.58 μg/mL against four human tumor cell lines Bel7402, BGC823, A549 and A2780, respectively. Compounds 16, 17 and 19 showed significant enzymatic inhibitory activity against protein tyrosine phosphatase PTP1B
with an IC50 value of 1.5, 2.4 and 0.84 μmol/L, respectively. Compounds 16~19 exhibited powerful immune modulatory activity toward T and B lymphocyte while they displayed toxicity against normal cells. All compounds do not show significant antifungal and antibacterial activity.
It has been reported marine sponge is one of the marine organisms that are studied most for marine natural products. They have proven to be a rich source for novel organic com
引文
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Fan Xiao, Xu Nianjun, Shi Jiangong. Bromophenols from the red alga Rhodomela confervoides. Journal of Natural Products, 2003a, 66 (3): 455-458
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Handayani Dian, Edrada Ru Angelie, Proksch Peter, Wray Victor, Witte Ludger, Van Soest Rob W. M., Kunzmann Andreas, Soedarsono. Four new bioactive polybrominated diphenyl ethers of the sponge Dysidea herbacea from West Sumatra, Indonesia. Journal of Natural Products, 1997, 60 (12): 1313-1316
Hardt Ingo H., Jensen Paul R., Fenical William. Neomarinone, and new cytotoxic marinone derivatives, produced by a marine filamentous bacterium (Actinomycetales). Tetrahedron Letters, 2000, 41 (13): 2073-2076
Hattori Tadamasa, Konno Aya, Adachi Kyoko, Shizuri Yoshikazu. Four new bioactive bromophenols from the palauan sponge Phyllospongia dendyi. Fisheries Science, 2001, 67 (5): 899-903
Hideyuki Kurihara, Takeshi Mitani, Jun Kawabata, Koretaro Takahashi. Two new bromophenols from the red alga Odonthalia corymbifera. Journal of Natural Products, 1999, 62 (6): 882-884
Higa Tatsuo, Scheuer Paul J.. Constituents of the hemichordate Ptychodera flava laysanica. NATO Conference Series, [Series] (Marine Natural Product Chemistry),
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