Total Synthesis and Biological Activity of Marine Alkaloid Eudistomins Y1–Y7 and Their Analogues

Marine Drugs

Huijuan Jin²  Puyong Zhang²  Krikor Bijian¹  Sumei Ren²  Shengbiao Wan²  Moulay A. Alaoui-Jamali¹ 

[1] Departments of Medicine, Oncology, and Pharmacology and Therapeutics, Lady Davis Institute for Medical Research, Segal Cancer Center of the Sir Mortimer B. Davis Jewish General Hospital, McGill University, Montreal, QC H3T 1E2, Canada; E-Mail:;Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China; E-Mails:

关键词: marine alkaloid;    Eudistomins Y₁–Y₇;    β-carboline;    Pictet-Spengler reaction;   

DOI  :  10.3390/md11051427

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2013 by the authors; licensee MDPI, Basel, Switzerland.