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

被引：0

作者：

Mikura, Asami ^{[1
]}

Tani, Koki ^{[1
]}

Sasahira, Erina ^{[1
]}

Nakano, Shunsuke ^{[1
]}

Kusano, Jun-ichi ^{[1
]}

Sato, Hiroto ^{[1
]}

Hasuda, Tomoyo ^{[1
]}

Takeya, Koichi ^{[1
]}

Hitotsuyanagi, Yukio ^{[1
]}

机构：

[1] Tokyo Univ Pharm & Life Sci, Sch Pharm, 1432-1 Horinouchi, Hachioji, Tokyo 1920392, Japan

来源：

TETRAHEDRON | 2025年 / 184卷

关键词：

Neo-RA-VII; Cyclorubipeptide A; Rubia cordifolia; Cyclodityrosine; CYTOTOXIC BICYCLIC HEXAPEPTIDES; PROTEIN-SYNTHESIS; INHIBITION; BOUVARDIN;

D O I：

10.1016/j.tet.2025.134747

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 mu M against HL-60 cells and 17 and 15 mu M against HCT-116 cells, respectively.

引用

页数：9

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