Mar. Drugs 2013, 11(5), 1427-1439; doi:10.3390/md11051427
Article

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

1 Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China 2 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 These authors contributed equally to this work.
* Author to whom correspondence should be addressed.
Received: 25 February 2013; in revised form: 25 March 2013 / Accepted: 7 April 2013 / Published: 29 April 2013
PDF Full-text Download PDF Full-Text [658 KB, Updated Version, uploaded 30 April 2013 09:13 CEST]
The original version is still available [11 KB, uploaded 29 April 2013 16:05 CEST]
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

Article Statistics

Load and display the download statistics.

Citations to this Article

Cite This Article

MDPI and ACS Style

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.

AMA Style

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.

Chicago/Turabian Style

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.

Mar. Drugs EISSN 1660-3397 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert