Laboratório de Química Orgânica e Farmacêutica, Departamento de Ciências Químicas, Faculdade de Farmácia, Universidade do Porto, Rua de Jorge Viterbo Ferreira 228, 4050-313 Porto, Portugal.
Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), Edifício do Terminal de Cruzeiros do Porto de Leixões, Avenida General Norton de Matos s/n, 4050-208 Matosinhos, Portugal.
Molecules. 2023 Jan 7;28(2):615. doi: 10.3390/molecules28020615.
Cyclopeptides are considered as one of the most important classes of compounds derived from marine sources, due to their structural diversity and a myriad of their biological and pharmacological activities. Since marine-derived cyclopeptides consist of different amino acids, many of which are non-proteinogenic, they possess various stereogenic centers. In this respect, the structure elucidation of new molecular scaffolds obtained from natural sources, including marine-derived cyclopeptides, can become a very challenging task. The determination of the absolute configurations of the amino acid residues is accomplished, in most cases, by performing acidic hydrolysis, followed by analyses by liquid chromatography (LC). In a continuation with the authors' previous publication, and to analyze the current trends, the present review covers recently published works (from January 2018 to November 2022) regarding new cyclopeptides from marine organisms, with a special focus on their biological/pharmacological activities and the absolute stereochemical assignment of the amino acid residues. Ninety-one unreported marine-derived cyclopeptides were identified during this period, most of which displayed anticancer or antimicrobial activities. Marfey's method, which involves LC, was found to be the most frequently used for this purpose.
环肽被认为是一类非常重要的化合物,源于海洋,具有结构多样性和多种生物和药理学活性。由于海洋来源的环肽由不同的氨基酸组成,其中许多是非蛋白源的,因此它们具有各种立体中心。在这方面,从天然来源(包括海洋来源的环肽)获得的新分子支架的结构阐明可能成为一项非常具有挑战性的任务。在大多数情况下,通过进行酸性水解,并通过液相色谱(LC)进行分析,来确定氨基酸残基的绝对构型。作为作者之前出版物的延续,并为了分析当前的趋势,本综述涵盖了最近发表的(从 2018 年 1 月至 2022 年 11 月)关于海洋生物中环肽的新研究工作,特别关注其生物/药理学活性和氨基酸残基的绝对立体化学分配。在此期间,共鉴定出 91 种未报告的海洋来源的环肽,其中大多数具有抗癌或抗菌活性。Marfey 法,涉及 LC,被发现是最常用于此目的的方法。