Structures of neo-RA-VII and cyclorubipeptide A, new cyclic hexapeptides from Rubia cordifolia

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-05-29 DOI:10.1016/j.tet.2025.134747

Asami Mikura, Koki Tani, Erina Sasahira, Shunsuke Nakano, Jun-ichi Kusano, Hiroto Sato, Tomoyo Hasuda, Koichi Takeya, Yukio Hitotsuyanagi

引用次数: 0

Abstract

A new bicyclic hexapeptide, neo-RA-VII (3), incorporating a 12-membered cyclodityrosine structure, and a new cyclic hexapeptide, cyclorubipeptide A (4), were isolated from the roots of Rubia cordifolia L. Their structures were elucidated through the interpretation of spectroscopic data. The structure of 3 was confirmed through total synthesis and that of 4 through chemical correlation with O-seco-RA-V (14). The cyclodityrosine unit in compound 3 was synthesized via an intramolecular Suzuki–Miyaura cross-coupling reaction of a dipeptide bearing an iodine atom and a boronic acid group on each aryl ring. Peptides 3 and 4 exhibited cytotoxic activity, with IC₅₀ values of 5.1 and 4.3 μM against HL-60 cells and 17 and 15 μM against HCT-116 cells, respectively.

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芦花新环六肽新ra - vii和环二肽A的结构

从鲁bia cordifolia L.的根中分离到一个新的具有12元环二酪氨酸结构的双环六肽neo-RA-VII(3)和一个新的环六肽cycloruubipeptide A(4)，并通过光谱分析对其结构进行了鉴定。通过全合成确定了3的结构，通过与O-seco-RA-V的化学关联确定了4的结构（14）。化合物3中的环二酪氨酸单元是由每个芳基环上带有一个碘原子和一个硼酸基团的二肽通过分子内Suzuki-Miyaura交叉偶联反应合成的。肽3和肽4对HL-60细胞的IC50分别为5.1和4.3 μM，对HCT-116细胞的IC50分别为17和15 μM。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.