Nitidumpeptins A and B, Cyclohexapeptides Isolated from Zanthoxylum nitidum var. tomentosum : Structural Elucidation, Total Synthesis, and Antiproliferative Activity in Cancer Cells

Nitidumpeptins A and B ( and ), two novel cyclic hexapeptides, were isolated from the herb var. . Their planar structures were elucidated based on NMR and MS spectrometric analysis, and the absolute configurations were determined by the Marfey's method. Structurally, is a unique peptide with a...

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Bibliographic Details
Published in:Journal of organic chemistry 2021-01, Vol.86 (2), p.1462-1470
Main Authors: Qin, Feng, Wang, Cai Yi, Kim, Donghwa, Wang, Heng-Shan, Zhu, Yan-Kui, Lee, Sang Kook, Yao, Gui-Yang, Liang, Dong
Format: Article
Language:English
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Summary:Nitidumpeptins A and B ( and ), two novel cyclic hexapeptides, were isolated from the herb var. . Their planar structures were elucidated based on NMR and MS spectrometric analysis, and the absolute configurations were determined by the Marfey's method. Structurally, 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 and was achieved by solution-phase in parallel with solid-phase peptide synthesis, and their absolute configurations were further confirmed. The combination of 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 was in part associated with the suppression of YAP expression in HCC827-gef cells.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c02057