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Synthesis, Anti-TMV Activities, and Action Mechanisms of a Novel Cytidine Peptide Compound
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2024-09-12 , DOI: 10.1021/acs.jafc.4c02767 Miao Yu 1 , He Liu 1, 2 , Yan Wang 1 , Shidong Zhou 1 , Xiaojie Ding 1 , Zihao Xia 1 , Mengnan An 1 , Yuanhua Wu 1
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2024-09-12 , DOI: 10.1021/acs.jafc.4c02767 Miao Yu 1 , He Liu 1, 2 , Yan Wang 1 , Shidong Zhou 1 , Xiaojie Ding 1 , Zihao Xia 1 , Mengnan An 1 , Yuanhua Wu 1
Affiliation
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Cytidine has a broad range of applications in the pharmaceutical field as an intermediate of antitumor or antiviral agent. Here, a series of new cytidine peptide compounds were synthesized using cytidine and Boc group-protected amino acids and analyzed for their antiviral activities against tobacco mosaic virus (TMV). Among these compounds, the structure of an effective antiviral cytidine peptide SN11 was characterized by 1H NMR, 13C NMR, and high-resolution mass spectrometer. The compound SN11 has a molecular formula of C15H22N6O8 and is named 2-amino-N-(2- ((1- (3,4-dihydroxy-5-(hydroxymethyl) tetrahydrofuran-2-yl) -2-oxo-1,2-dihydropyrimidin-4-yl) amino) -2-oxyethyl) amino). The protection, inactivation, and curation activities of SN11 at a concentration of 500 μg/mL against TMV in Nicotiana glutinosa were 82.6%, 84.2%, and 72.8%, respectively. SN11 also effectively suppressed the systemic transportation of a recombinant TMV carrying GFP reporter gene (p35S-30B:GFP) in Nicotiana benthamiana by reducing viral accumulation to 71.3% in the upper uninoculated leaves and inhibited the systemic infection of TMV in Nicotiana tabacum plants. Furthermore, the results of RNA-seq showed that compound SN11 induced differential expression of genes involved in the biogenesis and function of ribosome, plant hormone signal transduction, plant pathogen interaction, and chromatin. These results validate the antiviral mechanisms of the cytidine peptide compound and provide a theoretical basis for their potential application in the management of plant virus diseases.
中文翻译：
新型胞苷肽化合物的合成、抗TMV活性及作用机制
胞苷作为抗肿瘤或抗病毒剂的中间体在医药领域具有广泛的应用。在这里，使用胞苷和 Boc 基团保护的氨基酸合成了一系列新的胞苷肽化合物，并分析了它们对烟草花叶病毒 (TMV) 的抗病毒活性。其中，一种有效的抗病毒胞苷肽SN11的结构通过1 H NMR、 13 C NMR和高分辨率质谱仪进行了表征。化合物SN11的分子式为C 15 H 22 N 6 O 8 ，命名为2-氨基-N- (2-((1-(3,4-二羟基-5-(羟甲基)四氢呋喃-2-基)) -2-氧代-1,2-二氢嘧啶-4-基)氨基)-2-氧基乙基)氨基)。浓度为500 μg/mL的SN11对烟草TMV的保护活性、灭活活性和清除活性分别为82.6%、84.2%和72.8%。 SN11还通过将未接种上部叶片中的病毒积累减少至71.3％，有效抑制了携带GFP报告基因（p35S-30B：GFP）的重组TMV在烟草中的系统运输，并抑制了TMV在烟草植物中的系统感染。此外，RNA-seq结果表明，化合物SN11诱导涉及核糖体生物发生和功能、植物激素信号转导、植物病原体相互作用和染色质的基因的差异表达。这些结果验证了胞苷肽化合物的抗病毒机制，并为其在植物病毒病防治中的潜在应用提供了理论基础。
更新日期：2024-09-12
中文翻译：
新型胞苷肽化合物的合成、抗TMV活性及作用机制
胞苷作为抗肿瘤或抗病毒剂的中间体在医药领域具有广泛的应用。在这里，使用胞苷和 Boc 基团保护的氨基酸合成了一系列新的胞苷肽化合物，并分析了它们对烟草花叶病毒 (TMV) 的抗病毒活性。其中，一种有效的抗病毒胞苷肽SN11的结构通过1 H NMR、 13 C NMR和高分辨率质谱仪进行了表征。化合物SN11的分子式为C 15 H 22 N 6 O 8 ，命名为2-氨基-N- (2-((1-(3,4-二羟基-5-(羟甲基)四氢呋喃-2-基)) -2-氧代-1,2-二氢嘧啶-4-基)氨基)-2-氧基乙基)氨基)。浓度为500 μg/mL的SN11对烟草TMV的保护活性、灭活活性和清除活性分别为82.6%、84.2%和72.8%。 SN11还通过将未接种上部叶片中的病毒积累减少至71.3％，有效抑制了携带GFP报告基因（p35S-30B：GFP）的重组TMV在烟草中的系统运输，并抑制了TMV在烟草植物中的系统感染。此外，RNA-seq结果表明，化合物SN11诱导涉及核糖体生物发生和功能、植物激素信号转导、植物病原体相互作用和染色质的基因的差异表达。这些结果验证了胞苷肽化合物的抗病毒机制，并为其在植物病毒病防治中的潜在应用提供了理论基础。
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