摘要
单端孢霉烯族毒素类是由真菌和菊科酒神菊属的植物产生的倍半萜类代谢产物 。它们包含一个在C-12和C-13处为环氧化物的三环核心,由此可以划分为非大环和大环化合物。尽管此类化合物中许多与农业有关,大环代谢产物被认为抗病毒、抗癌、抗疟和抗真菌化合物。一些真核细胞的细胞毒性反应,包括抑制蛋白质,核酸和核糖核酸的合成,干扰线粒体功能,对细胞分裂和膜的影响作用已被发现。然而,这些靶点已阐明其根本上利用非大环单端孢并且只有一个或两个密切相关的大环化合物。一些大环单端孢菌素对真菌的种类和对癌细胞株的高选择性的报道表明大环及其立体化学结构对生物活性和选择性至关重要。这篇综述将大环类化合物作为重点,其环状酯或三酯环结合在C-4的单端孢霉烯部分和属于沙曲毒素,木霉菌素,真菌毒素和酒神菊素C - 15先导的天然产品。其生物活性、毒性机理和构效关系(SAR)已进行了讨论。从所报告的数据可明显得出,即使是小的分子的变化也可能会导致明显的生物活性或选择性对癌细胞株的影响。了解潜在的机制可能有助于用于癌症治疗的高度特异性药物的设计。
关键词: 倍半萜,大环单端孢霉素,细胞毒性,抗肿瘤活性,杆孢菌素,作用方式,构效关系。
Current Medicinal Chemistry
Title:Macrocyclic trichothecenes as antifungal and anticancer compounds
Volume: 23 Issue: 1
Author(s): Maira Peres de Carvalho, Herbert Weich and Wolf-Rainer Abraham
Affiliation:
关键词: 倍半萜,大环单端孢霉素,细胞毒性,抗肿瘤活性,杆孢菌素,作用方式,构效关系。
摘要: Trichothecenes are sesquiterpenoid metabolites produced by fungi and species of the plant genus Baccharis, family Asteraceae. They comprise a tricyclic core with an epoxide at C-12 and C-13 and can be grouped into non-macrocyclic and macrocyclic compounds. While many of these compounds are of concern in agriculture, the macrocyclic metabolites have been evaluated as antiviral, anti-cancer, antimalarial and antifungal compounds. Some known cytotoxic responses on eukaryotic cells include inhibition of protein, DNA and RNA syntheses, interference with mitochondrial function, effects on cell division and membranes. These targets however have been elucidated essentially employing non-macrocyclic trichothecenes and only one or two closely related macrocyclic compounds. For several macrocyclic trichothecenes high selectivity against fungal species and against cancer cell lines have been reported suggesting that the macrocycle and its stereochemistry are of crucial importance regarding biological activity and selectivity. This review is focused on compounds belonging to the macrocyclic type, where a cyclic diester or triester ring binds to the trichothecane moiety at C-4 and C- 15 leading to natural products belonging to the groups of satratoxins, verrucarins, roridins, myrotoxins and baccharinoids. Their biological activities, cytotoxic mechanisms and structure-activity relationships (SAR) are discussed. From the reported data it becomes evident that even small changes in the molecules can lead to pronounced effects on biological activity or selectivity against cancer cells lines. Understanding the underlying mechanisms may help to design highly specific drugs for cancer therapy.
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Cite this article as:
Maira Peres de Carvalho, Herbert Weich and Wolf-Rainer Abraham , Macrocyclic trichothecenes as antifungal and anticancer compounds, Current Medicinal Chemistry 2016; 23 (1) . https://dx.doi.org/10.2174/0929867323666151117121521
DOI https://dx.doi.org/10.2174/0929867323666151117121521 |
Print ISSN 0929-8673 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-533X |
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