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寄生藤叶的绿原酸成分的多样化学修饰:抵御过度阳光照射的准备状态的一个前提。

Diverse chemical modifications of the chlorogenic acid composition of Viscum combreticola Engl.: A premise for the state of readiness against excessive sunlight exposure.

作者信息

Moyo Babra, Tavengwa Nikita Tawanda, Madala Ntakadzeni Edwin

机构信息

Department of Biochemistry and Microbiology, Faculty of Science, Engineering and Agriculture, University of Venda, Private Bag X5050, Thohoyandou 0950, South Africa; Department of Food Science and Technology, Faculty of Science, Engineering and Agriculture, University of Venda, Private Bag X5050, Thohoyandou 0950, South Africa.

Department of Chemistry, Faculty of Science, Engineering and Agriculture, University of Venda, Private Bag X5050, Thohoyandou 0950, South Africa.

出版信息

J Photochem Photobiol B. 2022 Aug;233:112501. doi: 10.1016/j.jphotobiol.2022.112501. Epub 2022 Jun 17.

Abstract

Mistletoe plants that are positioned on the canopy of their hosts are more susceptible to UV radiation exposure. These aerial plants are resistant to damage by UV radiation due the presence of epidermal constituents such as the cuticle, cork layer, trichomes and antioxidant secondary metabolites. In response to the photo-oxidative stress associated with UV exposure, plants generally deploy photo-protective responsive mechanisms that involve the biosynthesis of UV absorbing phenolic compounds such as chlorogenic acids (CGAs). The hydroxycinnamic acid moieties of these CGAs are predominantly in the trans configuration, naturally. However, excessive sunlight exposure of plants containing these compounds can result in geometrical isomerisation, characterized by the formation of cis isomers. Therefore, in this study, the effect of UV light radiation on the CGA composition of Viscum combreticola Engl. (Santalacaeae) plants using an in vitro model was unravelled through UHPLC-q-TOF-MS-based metabolic profiling. Interestingly, the findings of this study revealed that this plant has a diverse chemical composition of CGAs that is characterized by epimerization, monoacylation, homodiacylation and heterodiacylation of the quinic acid (QA), thereby, contributing to the state of readiness in these plants against sunlight or UV exposure. In addition to the commonly reported cinnamoyl containing heterodiacylated CGAs, hydroxybenzoyl containing heterodiacylated CGAs were also reported in this study. Moreover, cis isomers (24 in total) of some CGAs were identified in the non-irradiated samples and the formation of these compounds has been reported to help plants in the mitigation of photo-oxidative stress. An additional 28 cis isomers of CGAs and HCA derivatives were observed in the UV-irradiated samples, hence, further increasing the complexity of the metabolome of this plant, with a total of 108 compounds identified in this study. The presence of epimers, positional and geometrical isomers of these compounds could be a biochemical strategy to maximize the chemical arsenal of this plant to withstand the photo-oxidative stress posed by UV radiation from the sunlight. Due to purported pharmacological properties associated with the identified compounds these parasitic plants can be a rich source of prospective therapeutic compounds that can be employed as drug discovery leads. Moreover, UV radiation might be essential in future to produce potent drugs since plants naturally produce these compounds in low quantities.

摘要

寄生于宿主树冠层的槲寄生植物更容易受到紫外线辐射。这些气生植物由于存在表皮成分,如角质层、木栓层、毛状体和抗氧化次生代谢产物,因而对紫外线辐射造成的损害具有抗性。为应对与紫外线照射相关的光氧化应激,植物通常会启动光保护反应机制,其中包括生物合成吸收紫外线的酚类化合物,如绿原酸(CGAs)。这些绿原酸的羟基肉桂酸部分通常天然地以反式构型存在。然而,含有这些化合物的植物过度暴露于阳光下会导致几何异构化,其特征是顺式异构体的形成。因此,在本研究中,通过基于超高效液相色谱-四极杆飞行时间质谱的代谢谱分析,揭示了紫外线辐射对体外培养的粘叶槲寄生(桑寄生科)植物绿原酸组成的影响。有趣的是,本研究结果表明,这种植物的绿原酸具有多样的化学组成,其特征在于奎尼酸(QA)的差向异构化、单酰化、同二酰化和异二酰化,从而有助于这些植物抵御阳光或紫外线照射。除了常见报道的含肉桂酰基的异二酰化绿原酸外,本研究还报道了含羟基苯甲酰基的异二酰化绿原酸。此外,在未辐照样品中鉴定出了一些绿原酸的顺式异构体(总共24种),据报道这些化合物的形成有助于植物减轻光氧化应激。在紫外线辐照样品中还观察到另外28种绿原酸和顺式异构体以及羟基肉桂酸衍生物,因此进一步增加了这种植物代谢组的复杂性,本研究共鉴定出108种化合物。这些化合物的差向异构体、位置异构体和几何异构体的存在可能是一种生化策略,以最大化这种植物的化学武器库,从而抵御阳光紫外线辐射造成的光氧化应激。由于所鉴定化合物具有据称的药理特性,这些寄生植物可能是潜在治疗化合物的丰富来源,可作为药物发现的先导。此外,由于植物天然产生这些化合物的量很少,紫外线辐射未来可能对生产强效药物至关重要。

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