三种海洋红藻和两株放线菌次级代谢产物研究
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摘要
海洋是一个巨大的天然产物宝库,约占地球表面积70%的海洋蕴藏着80%的生物资源。由于海洋生态环境的特殊性,导致海洋生物能够产生大量结构独特多变和活性特殊多样的代谢产物。我国海域辽阔,海洋资源丰富,为寻找结构新颖、生理活性独特的先导化合物,加强对海洋资源的开发利用,本论文对中国沿海的三种海洋红藻和两株放线菌次生代谢产物以及生物活性进行研究,为新药研究与开发提供模式结构和药物前体。
对红藻似瘤凹顶藻Laurencia similis乙酸乙酯萃取物进行分离纯化,从中得到单体化合物35个,通过波谱学方法(IR、MS、NMR等)鉴定了他们的结构。分别为:2, 2′, 5, 5′, 6, 6′-sixibromo-3, 3′-bi-1H-indole (1),3,5-dibromo- 1-methyl-indole (2),3',5',6,6'-tetrabromo-2,4-dimmethyldiphenyl ether (3),1,2,5- tribromo-3-bromoamino-7-bromomethylnaphthalene (4),2,5,8-tribromo-3-bromo- amino-7-bromomethylnaphthalene (5) , 2,5,6-tribromo-3-bromoamino-7-bromo- methylnaphthalene (6), 2,5,6,5',6'-pentabromo-3,4,3',4'-tetramethoxybenzophenone (7), (4E)-1-bromo-5-[(1'S*,3'R*)-3'-bromo-2',2'-dimethyl-6'-methylenecyclohexyl] -3-methylpent-4-ene-2,3-diol (8),4-hydroxy-Palisadin C (9),Isopalisol (10),Luzonensol (11),Palisadin B (12),Aplysistatin (13),Palisadin A (14),5-Acetoxypalisadin B (15),Aristolan-1(10)- en-9-ol (16),Aristol-8-en-1-one (17),Aristolan-9-en-1-one (18),Aristolan-1(10)-en- 9-one (19),Aristofone (20),Aristolan-1(10)-8-diene (21),Aristolan-1,9-diene (22),10-Hydroxyaristolan-9-one (23),7,11,15-trimethyl-3-methylene-hexadecan-1,2-diol (24),3β-Hydroxyergosta- 5,24(28)-dien-7-one (25),Isofucosterol (26),β-sitosterol (27),豆甾-4-烯-3α,6β-二醇(28),Cholesta-5-en-3β-ol (29),Stigmasterol (30),2,3,5,6-四溴-吲哚(31),2,3,6-tribromo-1H-indole (32),3,5,6-tribromo-1-methylindole (33),3,5,6-tribromo -1H-indole (34),2,3,5-tribromo-1-methylindole (35),其中化合物1-9为新化合物,化合物10-15、20和化合物24-30均为首次从该种海藻中得到。对新化合物1-9进行PTP1B酶抑制剂活性筛选,新化合物1、3、7显示强的PTP1B酶抑制活性。
对红藻齐藤凹顶藻Laurencia saitoi乙酸乙酯萃取物进行分离纯化,从中得到单体化合物11个,通过波谱学方法(IR、MS、NMR等)鉴定了他们的结构,分别为:2-hydroxyl-Luzofuranone (1),2-hydroxyl-Luzofuranone B (2),4-hydroxyl-Palisudin C (3) , 2-bromo-γ-ionone (4) , Aplysistatin (5) ,5-Acetoxypalisadin B (6),Palisadin B (7),Palisadin A (8),Pacifigorgiol (9),豆甾-4-烯-3α,6β-二醇(10),2, 3, 5, 6-四溴-吲哚(11),其中化合物1-4为新化合物,所有化合物均为首次从该种海藻中得到。通过MTT法对分离得到的新化合物1-4进行肿瘤细胞毒活性筛选,结果显示4个新化合物对所测肿瘤细胞株均无明显的活性。
对红藻瘤状软骨凹顶藻Chondrophycus papillous乙酸乙酯萃取物进行分离纯化,从中得到单体化合物5个,通过波谱学方法(MS、NMR等)鉴定了他们的结构,分别为邻苯二甲酸二丁酯(1),邻苯二甲酸二异辛酯(2),胆甾醇(3),3,7,11,15-tetramethyl-hexadec-2-en-1-ol (4),4-羟基苯甲醛(5),所有化合物均为首次从该种海藻中得到。
对海洋放线菌M159乙酸乙酯萃取物进行分离纯化,从中得到单体化合物13个,通过波谱学方法(MS、NMR等)鉴定了他们的结构,分别为:5-(4',6'-dihydroxy-6-methyloctyl)furan-2(5H)-one (A),phenethyl alcohol (1),4-羟基苯甲醛(2),anthranilic acid (3),4-Hydroxy-3-methoxy- phenyl-propionic acid (4),5-(6,7-dihydroxy-6-methyloctyl)furan-2(5H)-one (5),p-Hydroxyphenylethyl alcohol (6),3-Indoleacrylic acid (7),Indol-3-carboxylic acid (8),Adenine cordyceposide (9),腺嘌呤核苷(10),尿嘧啶核苷(11),Thymidine (12),其中化合物A为新化合物。所有化合物均为首次从该株放线菌中得到。
对海洋放线菌L211乙酸乙酯萃取物进行分离纯化,从中得到单体化合物15个,通过波谱学方法(MS、NMR等)鉴定了7个结构,分别为:spatozoate (1) , anthranilic acid (2) , 3-Indolylethanol (3) , 1-Acetyl-β-carbolin (4) ,p-Hydroxyphen- ylethyl alcohol (5),Indole-3-acetic acid (6),Indol-3-carboxylic acid (7),所有化合物均为首次从该株放线菌中得到。
The sea, covering nearly 70% of the world's surface, contain 80% resources. Because of the particular ecological environment, marine organism are rich of secondary metabolites owning novel structure and unique bioactive. In order to search for new bioactive compounds from marine organism, three red algae and two actinomycetes were investigated.
35 compounds were isolated from EtOAc-soluble portion of red alga Laurencia similis by chromatography including normal phase silica gel, Sephadex LH-20 gel, as well as recrystallization. Structures were elucidated by spectroscopic methods including IR, MS and NMR. They were 2, 2′, 5, 5′, 6, 6′-sixibromo-3, 3′-bi-1H-indole (1), 3,5-dibromo-1-methyl-indole (2), 3',5',6,6'-tetrabromo-2,4- dimmethyldiphenyl ether (3), 1,2,5-tribromo-3-bromoamino-7-bromomethyl- naphthalene (4), 2,5,8-tribromo-3-bromoamino-7-bromomethylnaphthalene (5), 2,5,6-tribromo-3-bromoamino-7-bromomethylnaphthalene (6), 2,5,6,5',6'-penta- bromo-3,4,3',4'-tetramethoxybenzophenone (7), (4E)-1-bromo-5-[(1'S*,3'R*)-3'- bromo-2',2'-dimethyl-6'-methylenecyclohexyl]-3-methylpent-4-ene-2,3-diol (8), 4-hydroxypalisadin C (9), Isopalisol (10), Luzonensol (11), Palisadin B (12), Aplysistatin (13), Palisadin A (14), 5-Acetoxypalisadin B (15), Aristolan-1(10)-en- 9-ol (16), Aristol-8-en-1-one (17), Aristolan-9-en-1-one (18), Aristolan-1(10)-en-9- one (19), Aristofone (20), Aristolan- 1(10)-8-diene (21), Aristolan-1,9-diene (22), 10-Hydroxyaristolan-9-one (23), 7,11,15-trimethyl-3-methylene-hexadecan-1,2- diol (24), 3β-Hydroxyergosta-5,24(28)-dien-7-one (25), Isofucosterol (26),β-sitosterol (27), Stigmast-4-en-3α,6β-diol (28), Cholesta-5-en-3β-ol (29), Stigmasterol (30), 2,3,5,6-tetrabromo-1H-indole (31), 2,3,6-tribromo-1H-indole (32), 3,5,6-tribromo-1-methylindole (33), 3,5,6-tribromo-1H-indole (34), 2,3,5- tribromo-1-methylindole (35). Compounds of 10-15、20、24-30 were obtained from this species for the first time including nine new compounds 1-9. The inhibitory effects on protein tyrosine phosphatase 1B (PTP1B) activity of nine new compounds were evaluated, compound 1, 3, 7 showed strong inhibitory PTP1B activity at the concentration of 5μg/ml.
11 compounds were isolated from EtOAc-soluble portion of red alga Laurencia saitoi by chromatography including normal phase silica gel , Sephadex LH-20 gel, as well as recrystallization. Structures were elucidated by spectroscopic methods including IR, MS and NMR. They were 2-hydroxyl-Luzofuranone (1), 2-hydroxyl-Luzofuranone B (2), 4-hydroxyl- Palisudin C (3), 2-bromo-γ-ionone (4), Aplysistatin (5), 5-Acetoxypalisadin B (6), Palisadin B (7), Palisadin A (8), Pacifigorgiol (9), Stigmast-4-en-3α,6β-diol (10), 2, 3, 5, 6-tetrabromo-1H-indole (11). All of the compounds were obtained from this species for the first time including four new compounds, 1-4. Cytotoxicity of new compounds was screened by MTT method on human cancer cell lines including HCT-8, BEl-7402, BGC-823 and A549. All the compounds showed no significantly activity.
From the red alga Chondrophycus papillous, 5 compounds were isolated and identified. They were Dibutyl orthophthalates (1), 1,2-benzenedicar boxylic acid (2), cholesterol (3), Phytol (4), p-hydroxy phenyl aldehyde (5). These compounds were all obtained from this species for the first time.
From actinomycetes M159, 13 compounds were isolated and identified, including a new compound 5-(4',6'-dihydroxy-6-methyloctyl)furan-2(5H)-one (A) and other known compounds phenethyl alcohol (1), 4-hydroxybenzal- dehyde (2), anthranilic acid (3), 4-Hydroxy-3-methoxy-phenylpropionic acid (4), 5-(6,7- dihydroxy-6-methyl-octyl)-furan-2(5H)-one (5), p-Hydroxyphenylethyl alcohol (6), 3-Indoleacrylic acid (7), Indol-3-carboxylic acid (8), Adenine cordyceposide (9), adenosine (10), uridine (11), Thymidine (12). All of the compounds were obtained from this marine strain for the first time.
From actinomycetes L211, 15 compounds were isolated and 7 compounds were identified, including spatozoate (1), anthranilic acid (2), 3-indolylethanol (3), 1-acetyl-β-carbolin (4), p-hydroxyphenylethyl alcohol (5), indole-3-acetic acid (6), indole-3-carboxylic acid (7). All of the compounds were obtained from this marine strain for the first time.
对红藻似瘤凹顶藻Laurencia similis乙酸乙酯萃取物进行分离纯化,从中得到单体化合物35个,通过波谱学方法(IR、MS、NMR等)鉴定了他们的结构。分别为:2, 2′, 5, 5′, 6, 6′-sixibromo-3, 3′-bi-1H-indole (1),3,5-dibromo- 1-methyl-indole (2),3',5',6,6'-tetrabromo-2,4-dimmethyldiphenyl ether (3),1,2,5- tribromo-3-bromoamino-7-bromomethylnaphthalene (4),2,5,8-tribromo-3-bromo- amino-7-bromomethylnaphthalene (5) , 2,5,6-tribromo-3-bromoamino-7-bromo- methylnaphthalene (6), 2,5,6,5',6'-pentabromo-3,4,3',4'-tetramethoxybenzophenone (7), (4E)-1-bromo-5-[(1'S*,3'R*)-3'-bromo-2',2'-dimethyl-6'-methylenecyclohexyl] -3-methylpent-4-ene-2,3-diol (8),4-hydroxy-Palisadin C (9),Isopalisol (10),Luzonensol (11),Palisadin B (12),Aplysistatin (13),Palisadin A (14),5-Acetoxypalisadin B (15),Aristolan-1(10)- en-9-ol (16),Aristol-8-en-1-one (17),Aristolan-9-en-1-one (18),Aristolan-1(10)-en- 9-one (19),Aristofone (20),Aristolan-1(10)-8-diene (21),Aristolan-1,9-diene (22),10-Hydroxyaristolan-9-one (23),7,11,15-trimethyl-3-methylene-hexadecan-1,2-diol (24),3β-Hydroxyergosta- 5,24(28)-dien-7-one (25),Isofucosterol (26),β-sitosterol (27),豆甾-4-烯-3α,6β-二醇(28),Cholesta-5-en-3β-ol (29),Stigmasterol (30),2,3,5,6-四溴-吲哚(31),2,3,6-tribromo-1H-indole (32),3,5,6-tribromo-1-methylindole (33),3,5,6-tribromo -1H-indole (34),2,3,5-tribromo-1-methylindole (35),其中化合物1-9为新化合物,化合物10-15、20和化合物24-30均为首次从该种海藻中得到。对新化合物1-9进行PTP1B酶抑制剂活性筛选,新化合物1、3、7显示强的PTP1B酶抑制活性。
对红藻齐藤凹顶藻Laurencia saitoi乙酸乙酯萃取物进行分离纯化,从中得到单体化合物11个,通过波谱学方法(IR、MS、NMR等)鉴定了他们的结构,分别为:2-hydroxyl-Luzofuranone (1),2-hydroxyl-Luzofuranone B (2),4-hydroxyl-Palisudin C (3) , 2-bromo-γ-ionone (4) , Aplysistatin (5) ,5-Acetoxypalisadin B (6),Palisadin B (7),Palisadin A (8),Pacifigorgiol (9),豆甾-4-烯-3α,6β-二醇(10),2, 3, 5, 6-四溴-吲哚(11),其中化合物1-4为新化合物,所有化合物均为首次从该种海藻中得到。通过MTT法对分离得到的新化合物1-4进行肿瘤细胞毒活性筛选,结果显示4个新化合物对所测肿瘤细胞株均无明显的活性。
对红藻瘤状软骨凹顶藻Chondrophycus papillous乙酸乙酯萃取物进行分离纯化,从中得到单体化合物5个,通过波谱学方法(MS、NMR等)鉴定了他们的结构,分别为邻苯二甲酸二丁酯(1),邻苯二甲酸二异辛酯(2),胆甾醇(3),3,7,11,15-tetramethyl-hexadec-2-en-1-ol (4),4-羟基苯甲醛(5),所有化合物均为首次从该种海藻中得到。
对海洋放线菌M159乙酸乙酯萃取物进行分离纯化,从中得到单体化合物13个,通过波谱学方法(MS、NMR等)鉴定了他们的结构,分别为:5-(4',6'-dihydroxy-6-methyloctyl)furan-2(5H)-one (A),phenethyl alcohol (1),4-羟基苯甲醛(2),anthranilic acid (3),4-Hydroxy-3-methoxy- phenyl-propionic acid (4),5-(6,7-dihydroxy-6-methyloctyl)furan-2(5H)-one (5),p-Hydroxyphenylethyl alcohol (6),3-Indoleacrylic acid (7),Indol-3-carboxylic acid (8),Adenine cordyceposide (9),腺嘌呤核苷(10),尿嘧啶核苷(11),Thymidine (12),其中化合物A为新化合物。所有化合物均为首次从该株放线菌中得到。
对海洋放线菌L211乙酸乙酯萃取物进行分离纯化,从中得到单体化合物15个,通过波谱学方法(MS、NMR等)鉴定了7个结构,分别为:spatozoate (1) , anthranilic acid (2) , 3-Indolylethanol (3) , 1-Acetyl-β-carbolin (4) ,p-Hydroxyphen- ylethyl alcohol (5),Indole-3-acetic acid (6),Indol-3-carboxylic acid (7),所有化合物均为首次从该株放线菌中得到。
The sea, covering nearly 70% of the world's surface, contain 80% resources. Because of the particular ecological environment, marine organism are rich of secondary metabolites owning novel structure and unique bioactive. In order to search for new bioactive compounds from marine organism, three red algae and two actinomycetes were investigated.
35 compounds were isolated from EtOAc-soluble portion of red alga Laurencia similis by chromatography including normal phase silica gel, Sephadex LH-20 gel, as well as recrystallization. Structures were elucidated by spectroscopic methods including IR, MS and NMR. They were 2, 2′, 5, 5′, 6, 6′-sixibromo-3, 3′-bi-1H-indole (1), 3,5-dibromo-1-methyl-indole (2), 3',5',6,6'-tetrabromo-2,4- dimmethyldiphenyl ether (3), 1,2,5-tribromo-3-bromoamino-7-bromomethyl- naphthalene (4), 2,5,8-tribromo-3-bromoamino-7-bromomethylnaphthalene (5), 2,5,6-tribromo-3-bromoamino-7-bromomethylnaphthalene (6), 2,5,6,5',6'-penta- bromo-3,4,3',4'-tetramethoxybenzophenone (7), (4E)-1-bromo-5-[(1'S*,3'R*)-3'- bromo-2',2'-dimethyl-6'-methylenecyclohexyl]-3-methylpent-4-ene-2,3-diol (8), 4-hydroxypalisadin C (9), Isopalisol (10), Luzonensol (11), Palisadin B (12), Aplysistatin (13), Palisadin A (14), 5-Acetoxypalisadin B (15), Aristolan-1(10)-en- 9-ol (16), Aristol-8-en-1-one (17), Aristolan-9-en-1-one (18), Aristolan-1(10)-en-9- one (19), Aristofone (20), Aristolan- 1(10)-8-diene (21), Aristolan-1,9-diene (22), 10-Hydroxyaristolan-9-one (23), 7,11,15-trimethyl-3-methylene-hexadecan-1,2- diol (24), 3β-Hydroxyergosta-5,24(28)-dien-7-one (25), Isofucosterol (26),β-sitosterol (27), Stigmast-4-en-3α,6β-diol (28), Cholesta-5-en-3β-ol (29), Stigmasterol (30), 2,3,5,6-tetrabromo-1H-indole (31), 2,3,6-tribromo-1H-indole (32), 3,5,6-tribromo-1-methylindole (33), 3,5,6-tribromo-1H-indole (34), 2,3,5- tribromo-1-methylindole (35). Compounds of 10-15、20、24-30 were obtained from this species for the first time including nine new compounds 1-9. The inhibitory effects on protein tyrosine phosphatase 1B (PTP1B) activity of nine new compounds were evaluated, compound 1, 3, 7 showed strong inhibitory PTP1B activity at the concentration of 5μg/ml.
11 compounds were isolated from EtOAc-soluble portion of red alga Laurencia saitoi by chromatography including normal phase silica gel , Sephadex LH-20 gel, as well as recrystallization. Structures were elucidated by spectroscopic methods including IR, MS and NMR. They were 2-hydroxyl-Luzofuranone (1), 2-hydroxyl-Luzofuranone B (2), 4-hydroxyl- Palisudin C (3), 2-bromo-γ-ionone (4), Aplysistatin (5), 5-Acetoxypalisadin B (6), Palisadin B (7), Palisadin A (8), Pacifigorgiol (9), Stigmast-4-en-3α,6β-diol (10), 2, 3, 5, 6-tetrabromo-1H-indole (11). All of the compounds were obtained from this species for the first time including four new compounds, 1-4. Cytotoxicity of new compounds was screened by MTT method on human cancer cell lines including HCT-8, BEl-7402, BGC-823 and A549. All the compounds showed no significantly activity.
From the red alga Chondrophycus papillous, 5 compounds were isolated and identified. They were Dibutyl orthophthalates (1), 1,2-benzenedicar boxylic acid (2), cholesterol (3), Phytol (4), p-hydroxy phenyl aldehyde (5). These compounds were all obtained from this species for the first time.
From actinomycetes M159, 13 compounds were isolated and identified, including a new compound 5-(4',6'-dihydroxy-6-methyloctyl)furan-2(5H)-one (A) and other known compounds phenethyl alcohol (1), 4-hydroxybenzal- dehyde (2), anthranilic acid (3), 4-Hydroxy-3-methoxy-phenylpropionic acid (4), 5-(6,7- dihydroxy-6-methyl-octyl)-furan-2(5H)-one (5), p-Hydroxyphenylethyl alcohol (6), 3-Indoleacrylic acid (7), Indol-3-carboxylic acid (8), Adenine cordyceposide (9), adenosine (10), uridine (11), Thymidine (12). All of the compounds were obtained from this marine strain for the first time.
From actinomycetes L211, 15 compounds were isolated and 7 compounds were identified, including spatozoate (1), anthranilic acid (2), 3-indolylethanol (3), 1-acetyl-β-carbolin (4), p-hydroxyphenylethyl alcohol (5), indole-3-acetic acid (6), indole-3-carboxylic acid (7). All of the compounds were obtained from this marine strain for the first time.
引文
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