Abstract: Eudistomin Y class compounds are a series of β-carbolines which was originally isolated from a marine turnicate or ascidian near the South Korea Sea. These compounds contain bromo-substituted groups, which is one of the typical characters of marine natural products. We report herein the chemical synthesis and biological evaluation of seven new β-carboline-based metabolites, Eudistomins Y1–Y7, and their hydroxyl-methylated phenyl derivatives. Using bromo-substituted tryptamines and bromo-substituted phenylglyoxals as the key intermediates, Eudistomins Y1–Y7 and their derivatives were synthesized via the acid-catalyzed Pictet-Spengler reaction and fully characterized by 1H- and 13C-NMR and mass spectroscopy. Biological studies revealed that all of the compounds showed moderate growth inhibitory activity against breast carcinoma cell line MDA-231 with IC50 of 15–63 μM and the inhibitory activities of hydroxyl-methylated phenyl products were higher than that of the corresponding natural products Eudistomins Y1–Y7.
Keywords: marine alkaloid; Eudistomins Y1–Y7; β-carboline; Pictet-Spengler reaction
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Jin, H.; Zhang, P.; Bijian, K.; Ren, S.; Wan, S.; Alaoui-Jamali, M.A.; Jiang, T. Total Synthesis and Biological Activity of Marine Alkaloid Eudistomins Y1–Y7 and Their Analogues. Mar. Drugs 2013, 11, 1427-1439.
Jin H, Zhang P, Bijian K, Ren S, Wan S, Alaoui-Jamali MA, Jiang T. Total Synthesis and Biological Activity of Marine Alkaloid Eudistomins Y1–Y7 and Their Analogues. Marine Drugs. 2013; 11(5):1427-1439.
Jin, Huijuan; Zhang, Puyong; Bijian, Krikor; Ren, Sumei; Wan, Shengbiao; Alaoui-Jamali, Moulay A.; Jiang, Tao. 2013. "Total Synthesis and Biological Activity of Marine Alkaloid Eudistomins Y1–Y7 and Their Analogues." Mar. Drugs 11, no. 5: 1427-1439.