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含酰胺基团的辣椒素衍生物的合成及抗污染性能。

Synthesis and fouling resistance of capsaicin derivatives containing amide groups.

机构信息

Key Laboratory of Marine Chemistry Theory and Technology, Ministry of Education, Ocean University of China, Qingdao 266100, China.

Key Laboratory of Marine Chemistry Theory and Technology, Ministry of Education, Ocean University of China, Qingdao 266100, China; Open Studio for Marine Corrosion and Protection, Pilot National Laboratory for Marine Science and Technology, Qingdao 266100, China.

出版信息

Sci Total Environ. 2020 Mar 25;710:136361. doi: 10.1016/j.scitotenv.2019.136361. Epub 2019 Dec 28.

DOI:10.1016/j.scitotenv.2019.136361
PMID:31926417
Abstract

Capsaicin, which inhibits the attachment and growth of fouling organisms, is a bioactive substance that is generally recognized as a highly active environmental algaecide agent. Its derivatives are simple in structure and have been proven to have low toxicity and be environmentally friendly. Six capsaicin derivatives were synthesized via Friedel-Crafts alkylation and characterized using melting point (MP) analysis, infrared (IR) spectroscopy, nuclear magnetic resonance (H NMR) spectroscopy and high-resolution mass spectrometry (HRMS). The inhibition effect and toxicity of these compounds towards Phaeodactylum tricornutum (P. tricornutum), Skeletonema costatum (S. costatum) and Chaetoceros curvisetus (C. curvisetus) were tested. The capsaicin derivatives all showed inhibitory effects. In particular, compound E with over 95% (3 mg·L) inhibition and intermediate toxicity was superior to the other compounds, reflecting an environmentally friendly effect. This finding indicates that capsaicin derivatives possess the potential to become environmentally friendly algaecide agents. The fouling resistance of capsaicin derivatives incorporated into the coatings as antifouling agents was measured in the marine environment. The results showed that capsaicin derivatives possess excellent fouling resistance, with only a small amount of algae and muck attached to the tested panel at 90 days. The above results provide a scientific basis for the application of capsaicin derivatives as environmentally friendly antifouling agents.

摘要

辣椒素是一种生物活性物质,可抑制污损生物的附着和生长,通常被认为是一种高效的环境杀藻剂。其衍生物结构简单,已被证明具有低毒性和环境友好性。通过傅克烷基化反应合成了 6 种辣椒素衍生物,并通过熔点(MP)分析、红外(IR)光谱、核磁共振(H NMR)光谱和高分辨率质谱(HRMS)对其进行了表征。测试了这些化合物对三角褐指藻(P. tricornutum)、中肋骨条藻(S. costatum)和旋链角毛藻(C. curvisetus)的抑制作用和毒性。这些辣椒素衍生物均表现出抑制作用。特别是化合物 E 具有超过 95%(3mg·L)的抑制率和中等毒性,优于其他化合物,反映出环境友好的效果。这一发现表明,辣椒素衍生物具有成为环境友好型杀藻剂的潜力。在海洋环境中,将辣椒素衍生物作为防污剂加入涂料中,测量其抗污性能。结果表明,辣椒素衍生物具有优异的抗污性能,在 90 天内仅少量藻类和污垢附着在测试板上。上述结果为将辣椒素衍生物作为环境友好型防污剂的应用提供了科学依据。

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