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从[来源未明确]中提取的新型代谢产物马代酮和新海葵酮作为海洋抗生物膜和防污剂。

Novel metabolite madeirone and neomarinone extracted from as marine antibiofilm and antifouling agents.

作者信息

Wissner Julian L, Almeida Joana R, Grilo Inês R, Oliveira Jhenifer F, Brízida Carolina, Escobedo-Hinojosa Wendy, Pissaridou Panayiota, Vasquez Marlen I, Cunha Isabel, Sobral Rita G, Vasconcelos Vítor, Gaudêncio Susana P

机构信息

Associate Laboratory i4HB, Institute for Health and Bioeconomy, NOVA Faculty of Sciences and Technology, NOVA University of Lisbon, Lisbon, Portugal.

UCIBIO, Applied Molecular Biosciences Unit, Chemistry and Life Sciences Departments, NOVA Faculty of Sciences and Technology, NOVA University of Lisbon, Lisbon, Portugal.

出版信息

Front Chem. 2024 Jul 25;12:1425953. doi: 10.3389/fchem.2024.1425953. eCollection 2024.

Abstract

Biofouling poses a significant economic threat to various marine industries, leading to financial losses that can reach billions of euros annually. This study highlights the urgent need for effective alternatives to traditional antifouling agents, particularly following the global ban on organotin compounds. PTM-346 was isolated from sediment samples on the shores of the Madeira Archipelago, Portugal. The crude extract was fractionated using silica flash chromatography and preparative HPLC, resulting in two isolated marinone compounds: madeirone (), a novel marinone derivative discovered in this study, and neomarinone (). The antifouling activities of these compounds were tested against five marine bacterial species and the larvae of the mussel . Additionally, and environmental toxicity evaluations of madeirone () and neomarinone () were conducted. Madeirone () demonstrated significant antibiofilm efficacy, inhibiting by up to 66%, by up to 60%, and by up to 40%. Neomarinone (2) also exhibited substantial antibiofilm activity, with inhibition rates of up to 41% against , 40% against , 56% against , 46% against C. marina, and 40% against . The growth inhibition activity at the same concentrations of these compounds remained below 20% for the respective bacteria, highlighting their effectiveness as potent antibiofilm agents without significantly affecting bacterial viability. Additionally, both compounds showed potent effects against the settlement of larvae, with EC values of 1.76 µg/mL and 0.12 µg/mL for compounds () and (), respectively, without impairing the viability of the targeted macrofouling species. toxicity predictions and toxicity assays both support their potential for further development as antifouling agents. The newly discovered metabolite madeirone () and neomarinone () effectively inhibit both micro- and macrofouling. This distinct capability sets them apart from existing commercial antifouling agents and positions them as promising candidates for biofouling prevention. Consequently, these compounds represent a viable and environmentally friendly alternative for incorporation into paints, primers, varnishes, and sealants, offering significant advantages over traditional copper-based compounds.

摘要

生物污损对各种海洋产业构成了重大的经济威胁,每年导致的经济损失可达数十亿欧元。本研究强调了迫切需要有效的传统防污剂替代品,特别是在全球禁止使用有机锡化合物之后。PTM - 346是从葡萄牙马德拉群岛海岸的沉积物样本中分离出来的。粗提物通过硅胶快速柱色谱和制备型高效液相色谱进行分离,得到两种分离的海葵酮类化合物:马德拉酮(),本研究中发现的一种新型海葵酮衍生物,以及新海葵酮()。测试了这些化合物对五种海洋细菌物种和贻贝幼虫的防污活性。此外,还对马德拉酮()和新海葵酮()进行了环境毒性评估。马德拉酮()表现出显著的抗生物膜功效,对 抑制率高达66%,对 抑制率高达60%,对 抑制率高达40%。新海葵酮(2)也表现出显著的抗生物膜活性,对 的抑制率高达41%,对 的抑制率高达40%,对 的抑制率高达56%,对滨海隐杆藻的抑制率高达46%,对 的抑制率高达40%。在相同浓度下,这些化合物对相应细菌的生长抑制活性保持在20%以下,突出了它们作为强效抗生物膜剂的有效性,且不会显著影响细菌活力。此外,两种化合物对贻贝幼虫的附着均显示出强效作用,化合物()和()的半数有效浓度(EC)值分别为1.76 μg/mL和0.12 μg/mL,且不会损害目标大型污损物种的活力。毒性预测和毒性测定均支持它们作为防污剂进一步开发的潜力。新发现的代谢产物马德拉酮()和新海葵酮()有效抑制了微观和宏观污损。这种独特的能力使它们有别于现有的商业防污剂,并使它们成为生物污损预防的有前途的候选物。因此,这些化合物是一种可行且环保的替代品,可用于涂料、底漆、清漆和密封剂中,比传统的铜基化合物具有显著优势。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8527/11306024/87f6b698e4f9/fchem-12-1425953-g001.jpg

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