Studies on the chemical constituents from marine sponge Agelas sp.
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摘要: 目的 研究海绵Agelas sp.的化学成分。 方法 运用乙醇提取、硅胶、Sephadex-LH20色谱柱、HPLC等多种方法进行分离和纯化，根据理化性质和波谱数据进行结构鉴定。 结果 分离得到9个化合物，经结构鉴定分别为4，5-二溴吡咯-2-甲酰胺（ 1 ）、4，5-二溴吡咯-2-甲酸（ 2 ）、4，5-二溴吡咯-2-甲酸甲酯（ 3 ）、N-（4，5-二溴-2-吡咯甲酰基）甘氨酸甲酯（ 4 ）、1-（4，5-二溴-2-吡咯甲酰胺基）丙酸甲酯（ 5 ）、1-（4，5-二溴-2-吡咯甲酰胺基）丙酸乙酯（ 6 ）、异吲哚-1，3-二酮（ 7 ）、2（3H）-苯并噻唑酮（ 8 ）和manzacidin C（ 9 ）。 结论 化合物 4 ~ 9 为首次从该属海绵中分离得到，其中化合物 4 ~ 6 为新天然产物。Abstract: Objective To investigate the chemical constituents from marine sponge Agelas sp. Methods Multi-chromatographic methods including silica gel column chromatography, Sephadex-LH20 gel permeation and HPLC were employed for the isolation and purification. The structures were identified on the basis of chemical evidence and NMR spectra data. Results Nine compounds were isolated and identified as: 4,5-dibromo-1H-pyrrole-2-carboxylic acid amide ( 1 ), 4,5-dibromo-1H-pyrrole-2-carboxylic acid ( 2 ), 4,5-dibromo-1H-pyrrole-2-carboxylic acid methyl ester ( 3 ), N-(4,5-dibromopyrrole-2-carbonyl) glycine methyl ester ( 4 ), 3-{[1-(4,5-dibromopyrrole-2-yl)-methanoyl]-amino}-propionic acid methyl ester ( 5 ), 3-{[1-(4,5-dibromopyrrole-2-yl)-methanoyl]-amino}-propionic acid ethyl ester ( 6 ),isoindole-1,3-dione ( 7 ), 2 (3H)-benzothiazolone ( 8 ), and manzacidin C ( 9 ). Conclusion Compounds 4 ~ 9 were isolated from the sponge of Agelas sp. for the first time,and compounds 4 ~ 6 were new natural products.
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Key words:
- Agelas sp. /
- chemical constituents /
- structure identification /
- bromopyrrole /
- alkaloids
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[1] Forenza S, Minale L, Riccio R, et al. New bromopyrrole derivatives from the sponge Agelas oroides［J］. J Chem Soc Chem Commun, 1971, (18):1129-1130. [2] 朱 彦,洪丽莉,甘建红,等. 群海绵属化学成分及生物活性研究进展［J］. 中国海洋药物,2013,32(6):97-110. [3] Lindel T, Hoffmann H, Hochgurtel M, et al. Structure-activity relationship of inhibition of fish feeding by sponge-derived and synthetic pyrrole-imidazole alkaloids［J］.J Chem Ecol,2000, 26(6):1477-1496. [4] Reddy NS, Venkateswarlu Y. S-(+)-methyl ester of hanishin from the marine sponge Agelas ceylonica［J］. Biochem Syst Ecol, 2000, 28(10): 1035-1037. [5] 徐石海,李毅群,曾向潮,等. N-(溴代-2-吡咯甲酰基)氨基酸甲酯的合成［J］. 有机化学,2005,25(11):1420-1426. [6] Sawant DN, Wagh YS, Bhatte KD, et al. Carbon monoxide-free one-step synthesis of isoindole-1,3-dionesby cycloaminocarbonylation of o-haloarenes using formamides［J］. Eur J Org Chem, 2011(33), 6719-6724. [7] 高 昊,陈国栋,唐金山,等,海洋细菌Bacillus sp.次生代谢产物的分离与鉴定［J］.沈阳药科大学学报,2010,27(1):69-75. [8] Kobayashi J, Kanda F, Ishibashi M, et al. Manzacidins A-C, novel tetrahydropyrimidine alkaloids from the Okinawan marine sponge Hymeniacidon sp.［J］.J Org Chem, 1991,56(14):4574-4576. -
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