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Nitidumpeptins A and B, Cyclohexapeptides Isolated from Zanthoxylum nitidum var. tomentosum: Structural Elucidation, Total Synthesis, and Antiproliferative Activity in Cancer Cells
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2021-01-07 , DOI: 10.1021/acs.joc.0c02057 Feng Qin 1 , Cai Yi Wang 2 , Donghwa Kim 2 , Heng-Shan Wang 1 , Yan-Kui Zhu 1 , Sang Kook Lee 2 , Gui-Yang Yao 1, 3 , Dong Liang 1
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2021-01-07 , DOI: 10.1021/acs.joc.0c02057 Feng Qin 1 , Cai Yi Wang 2 , Donghwa Kim 2 , Heng-Shan Wang 1 , Yan-Kui Zhu 1 , Sang Kook Lee 2 , Gui-Yang Yao 1, 3 , Dong Liang 1
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Nitidumpeptins A and B (1 and 2), two novel cyclic hexapeptides, were isolated from the herb Zanthoxylum nitidum var. tomentosum. Their planar structures were elucidated based on NMR and MS spectrometric analysis, and the absolute configurations were determined by the Marfey’s method. Structurally, 1 is a unique peptide with a backbone bearing a pyrrolidine-2,5-dione unit, which is the first occurrence moiety specifically in a naturally occurring cyclohexapeptide. The total synthesis of 1 and 2 was achieved by solution-phase in parallel with solid-phase peptide synthesis, and their absolute configurations were further confirmed. The combination of 2 with gefitinib exhibited synergistic antiproliferative activity in acquired gefitinib-resistant non-small cell lung cancer cells (HCC827-gef). The underlying mechanism for the antiproliferative activity of 2 was in part associated with the suppression of YAP expression in HCC827-gef cells.
中文翻译：
Nitdumpeptins A和B，分离自花椒花椒的环六肽。绒毛：癌细胞中的结构阐明，总合成和抗增殖活性
Nitdumpeptins A和B（1和2），两个新的环状六肽，是从药草花椒中分离得到的。绒毛。根据NMR和MS光谱分析阐明了它们的平面结构，并通过Marfey方法确定了绝对构型。在结构上，1是独特的肽，其骨架带有带有吡咯烷-2,5-二酮单元的主链，吡咯烷-2,5-二酮单元是天然存在的环六肽中首先出现的部分。1和2的总合成是通过固相肽合成与溶液相平行实现的，并且进一步证实了它们的绝对构型。的结合2与吉非替尼在获得的耐吉非替尼的非小细胞肺癌细胞（HCC827-gef）中表现出协同的抗增殖活性。2的抗增殖活性的潜在机制部分与抑制HCC827-gef细胞中的YAP表达有关。
更新日期：2021-01-16
中文翻译：
Nitdumpeptins A和B，分离自花椒花椒的环六肽。绒毛：癌细胞中的结构阐明，总合成和抗增殖活性
Nitdumpeptins A和B（1和2），两个新的环状六肽，是从药草花椒中分离得到的。绒毛。根据NMR和MS光谱分析阐明了它们的平面结构，并通过Marfey方法确定了绝对构型。在结构上，1是独特的肽，其骨架带有带有吡咯烷-2,5-二酮单元的主链，吡咯烷-2,5-二酮单元是天然存在的环六肽中首先出现的部分。1和2的总合成是通过固相肽合成与溶液相平行实现的，并且进一步证实了它们的绝对构型。的结合2与吉非替尼在获得的耐吉非替尼的非小细胞肺癌细胞（HCC827-gef）中表现出协同的抗增殖活性。2的抗增殖活性的潜在机制部分与抑制HCC827-gef细胞中的YAP表达有关。
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