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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
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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Published in: | Journal of organic chemistry 2021-01, Vol.86 (2), p.1462-1470 |
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Main Authors: | , , , , , , , |
Format: | Article |
Language: | English |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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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. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.0c02057 |