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.
Highlights
The diversity of marine compounds offers a great advantage for being developed into new drugs because of their unique and complex structures, developed through old and underexplored species evolution
We report the total chemical syntheses of the marine alkaloid Eudistomins Y1–Y7 23–29 and their hydroxyl-methylated phenyl derivatives (16–22) with modified one-pot oxidation via the acid-catalyzed Pictet-Spengler reaction, as well as their biological activities against breast carcinoma cell line MDA-231
The particularity of the marine environment leads to the rich bromine in the marine natural products, so the syntheses of bromo-substituted indole compounds are the key step in the preparations of marine alkaloid Eudistomins Y1–Y7 23–29
Summary
The diversity of marine compounds offers a great advantage for being developed into new drugs because of their unique and complex structures, developed through old and underexplored species evolution. Β-carbolines are a large group of natural and synthetic indole alkaloids with different substitutions at the C-1, C-6 and C-7 position, some of which are widely distributed in many plants and mammals and exhibit a wide spectrum of biological activities [2,3,4]. Eudistomin Y class β-carboline compounds are different from previously isolated marine metabolites due to the presence of a benzoyl group attached to the β-carboline nucleus at C-1. These compounds contain bromo-substituted groups, which is one of the typical characters of the marine natural products. The spectra data of synthetic compounds 23–29 were consistent with those of natural β-carboline alkaloids Eudistomins Y1–Y7 in the literature [5]
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