Pyrrole-imidazole alkaloids (PIAs) constitute a highly diverse and densely functionalized subclass of marine natural products. Among them, the uncommon dimeric PIAs with ornate molecular architectures, attractive biological properties and interesting biosynthetic origin have spurred a considerable interest of chemists and biologists. The present review comprehensively summarized 84 dimeric PIAs discovered during the period from 1981 to September 2022, covering their source organisms, chemical structures, biological activities as well as biosynthesis. For a better understanding, these structurally intricate PIA dimers are firstly classified and presented according to their carbon skeleton features as well as biosynthesis pathways. Furthermore, relevant summaries focusing on the source organisms and the associated bioactivities of these compounds belonging to different chemical classes are also provided, which will help elucidate the fascinating chemistry and biology of these unusual PIA dimers.
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http://dx.doi.org/10.1016/j.bioorg.2022.106332 | DOI Listing |
Mar Drugs
October 2024
Department of Natural Medicinal Chemistry and Pharmacognosy, School of Pharmacy, Qingdao University, Qingdao 266021, China.
Pyrrole-imidazole alkaloids (PIAs) are a class of marine sponge derived natural products which have complex carbon frameworks and broad bioactivities. In this study, four new alkaloids, stylimassalins A-B (-), , and , together with two known compounds ( and ), were isolated from . Compounds , , and are the C-2 brominated analogues of , , and , respectively.
View Article and Find Full Text PDFOrg Lett
July 2024
School of Pharmacy, Qingdao University, Qingdao, Shandong 266021, China.
Pyrrole alkaloids (PAs) are a diverse class of natural products with complex carbon frameworks and broad bioactivities that are usually derived from marine sponges. and are two independent sponges collected from the South China Sea in 2013 and 2018, respectively. We discovered PAs are common constituents in both two sponges; more specifically, produces pyrrole-imidazole alkaloids, and contains pyrrolidone alkaloids.
View Article and Find Full Text PDFMolecules
September 2023
Laboratory of Bioorganic Chemistry, Department of Physics, Università degli Studi di Trento, Via Sommarive 14, 38123 Trento, Italy.
Agelastatin A is a marine alkaloid with potent biological activity. To date, at least 17 different strategies have achieved its total synthesis, along with many analogues. The present study focuses on the acidity stability of some -methyl derivatives of agelastatin A.
View Article and Find Full Text PDFJ Org Chem
July 2023
Department of Chemistry, Michigan State University, East Lansing, Michigan 48823, United States.
Herein, we report the total synthesis of nagelamide W (), a pyrrole imidazole alkaloid of the nagelamide family isolated in 2013. The key approach in this work involves the construction of the 2-aminoimidazoline core of nagelamide W from alkene 6 through a cyanamide bromide intermediate. The synthesis of nagelamide W was accomplished with an overall yield of 6.
View Article and Find Full Text PDFBioorg Chem
April 2023
College of Veterinary Medicine, Qingdao Agricultural University, Qingdao 266109, China. Electronic address:
Pyrrole-imidazole alkaloids (PIAs) constitute a highly diverse and densely functionalized subclass of marine natural products. Among them, the uncommon dimeric PIAs with ornate molecular architectures, attractive biological properties and interesting biosynthetic origin have spurred a considerable interest of chemists and biologists. The present review comprehensively summarized 84 dimeric PIAs discovered during the period from 1981 to September 2022, covering their source organisms, chemical structures, biological activities as well as biosynthesis.
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