Discovery of Anti-Inflammatory Alkaloids from Sponge Stylissa massa Suggests New Biosynthetic Pathways for Pyrrole-Imidazole Alkaloids.

IF 4.9 2区 医学 Q1 CHEMISTRY, MEDICINAL Marine Drugs Pub Date : 2024-10-18 DOI:10.3390/md22100477
Xiaojing Liu, Qi Wang, Yun Zhang, Hanting Zhang
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Abstract

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 (1-2), 3, and 5, together with two known compounds (4 and 6), were isolated from Stylissa massa. Compounds 2, 4, and 6 are the C-2 brominated analogues of 1, 3, and 5, respectively. Their structures display three different scaffolds, of which scaffold 1 (compounds 1,2) is new. A new biosynthetic pathway from oroidin, through spongiacidin, to latonduine and scaffold 1 was proposed by our group, in which the C12-N13-cleavaged compounds of spongiacidin (scaffold 2), dubbed seco-spongiacidins (3 and 4), are recognized as a key bridged scaffold, to afford PIA analogues (1,2 and 5,6). An anti-inflammatory evaluation in a zebrafish inflammation model induced by copper sulphate (CuSO4) demonstrated that stylimassalins A and B (1 and 2) could serve as a promising lead scaffold for treating inflammation.

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从海绵 Stylissa massa 中发现抗炎生物碱,为吡咯-咪唑生物碱提供了新的生物合成途径。
吡咯-咪唑生物碱(PIAs)是一类从海洋海绵中提取的天然产物,具有复杂的碳框架和广泛的生物活性。本研究从 Stylissa massa 中分离出了四种新生物碱:stylimassalins A-B (1-2)、3 和 5,以及两种已知化合物(4 和 6)。化合物 2、4 和 6 分别是 1、3 和 5 的 C-2 溴化类似物。它们的结构显示出三种不同的支架,其中支架 1(化合物 1、2)是新的。我们的研究小组提出了一条新的生物合成途径,从鹅膏蕈素到海绵苷,再到拉通杜因和支架 1,其中海绵苷的 C12-N13 裂解化合物(支架 2),被称为仲海绵苷(3 和 4),被认为是一个关键的桥接支架,从而产生了 PIA 类似物(1,2 和 5,6)。在硫酸铜(CuSO4)诱导的斑马鱼炎症模型中进行的抗炎评估表明,木犀草苷 A 和 B(1 和 2)可作为治疗炎症的先导支架。
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来源期刊
Marine Drugs
Marine Drugs 医学-医药化学
CiteScore
9.60
自引率
14.80%
发文量
671
审稿时长
1 months
期刊介绍: Marine Drugs (ISSN 1660-3397) publishes reviews, regular research papers and short notes on the research, development and production of drugs from the sea. Our aim is to encourage scientists to publish their experimental and theoretical research in as much detail as possible, particularly synthetic procedures and characterization information for bioactive compounds. There is no restriction on the length of the experimental section.
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