Study On The Secondary Metabolites From Three Red Algae And Two Marine Actinomycetes

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.