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用杂环化合物修饰羧甲基菊粉:合成、表征、抗氧化和抗真菌活性。

Modification of carboxymethyl inulin with heterocyclic compounds: Synthesis, characterization, antioxidant and antifungal activities.

机构信息

Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China; Center for Ocean Mega-Science, Chinese Academy of Sciences, 7 Nanhai Road, Qingdao 266071, China; University of Chinese Academy of Sciences, Beijing 100049, China.

Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China; Center for Ocean Mega-Science, Chinese Academy of Sciences, 7 Nanhai Road, Qingdao 266071, China.

出版信息

Int J Biol Macromol. 2021 Jun 30;181:572-581. doi: 10.1016/j.ijbiomac.2021.03.109. Epub 2021 Mar 22.

Abstract

A series of novel inulin derivatives were designed and synthesized by the introduction of amino heterocyclic moieties onto carboxymethyl inulin with the aid of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride and N-hydroxysuccinimide. The target products were prepared via three - step chemical synthesis, and structures were identified by FTIR and H NMR spectroscopy. Antioxidant activities of inulin derivatives including DPPH - radical scavenging assay, superoxide - radical scavenging assay, hydroxyl - radical scavenging assay, and reducing power were estimated. Meanwhile, their antifungal activities, including Colletotrichum lagenarium and Botrytis cinerea, were also explored by hyphal measurement. In particular, inulin derivatives bearing heterocyclic moieties exhibited a remarkable improvement over inulin on antioxidant and antifungal activities, and their bioactivities decreased roughly in the order of 2ATCMI > 4APCMI > 3APCMI > 2APCMI > 3ATCMI > CMI > inulin. Furthermore, the cytotoxicities of inulin derivatives against L929 cells were evaluated by CCK-8 in vitro, and all samples showed weak cytotoxicities. In a nutshell, the paper provides a practical approach to synthesize novel inulin derivatives with dramatically enhanced bioactivity and good biocompatibility. The product described in paper might serve as a new leading structure for further design of antioxidants or antifungal agents in biomedicine, cosmetics, and other fields.

摘要

一系列新型的菊粉衍生物通过在羧甲基菊粉上引入氨基杂环结构,利用 1-乙基-3-(3-二甲基氨基丙基)碳二亚胺盐酸盐和 N-羟基琥珀酰亚胺合成。目标产物通过三步化学合成制备,并通过傅里叶变换红外光谱(FTIR)和核磁共振氢谱(1H NMR)进行了结构鉴定。评估了菊粉衍生物的抗氧化活性,包括 DPPH 自由基清除能力、超氧自由基清除能力、羟自由基清除能力和还原能力。同时,还通过菌丝测量法研究了它们对胶孢炭疽菌和灰葡萄孢的抗真菌活性。特别是,含有杂环结构的菊粉衍生物在抗氧化和抗真菌活性方面比菊粉有显著提高,其生物活性大致按以下顺序降低:2ATCMI>4APCMI>3APCMI>2APCMI>3ATCMI>CMI>菊粉。此外,通过 CCK-8 体外法评估了菊粉衍生物对 L929 细胞的细胞毒性,所有样品均表现出较弱的细胞毒性。总之,本文提供了一种实用的方法来合成具有显著增强的生物活性和良好的生物相容性的新型菊粉衍生物。本文所述的产品可能成为进一步设计生物医学、化妆品和其他领域的抗氧化剂或抗真菌剂的新先导结构。

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