RA-dimer B, a New Dimeric RA-series Cyclopeptide Incorporating Two Different Types of Cycloisodityrosine Units, from Rubia cordifolia L.
RA-dimer B, a New Dimeric RA-series Cyclopeptide Incorporating Two Different Types of Cycloisodityrosine Units, from Rubia cordifolia L.
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DOI：
10.1002/asia.201601138
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发表时间：
2016-12-06
影响因子：
4.1
通讯作者：
Kawahara, Nobuo
中科院分区：
文献类型：
--
作者：
Hitotsuyanagi, Yukio;Tsuchiya, Takayuki;Kawahara, Nobuo
RA二聚体B是从茜草根中分离得到的一种新的具有细胞毒性的RA系列肽。其结构经光谱分析确定为脱氧Bouvardin和allo-RA-V的二聚体环肽。脱氧Bouvardin的酚氧原子和allo-RA-V的Tyr-6的ea碳原子之间通过醚键连接。RA-二聚体B由脱氧Bouvardin与allo-RA-V的硼酸衍生物偶联反应合成。和随后的脱保护，确认相对立体化学并建立该肽的绝对构型。RA-二聚体B显示对人早幼粒细胞白血病HL-60、人结肠癌HCT-116和人肾细胞癌ACHN细胞的细胞毒活性，IC 50值分别为0.59、0.54和0.74 μ m。
RA-dimer B, a new cytotoxic RA-series peptide, was isolated from the roots of Rubia cordifolia L. Its structure was elucidated on the basis of spectroscopic analysis to be a dimeric cyclopeptide composed of deoxybouvardin and allo-RA-V. Those two cyclopeptide units are connected by an ether linkage between the phenolic oxygen atom of deoxybouvardin and the ea carbon atom of Tyr-6 of allo-RA-V. RA-dimer B was synthesized by the coupling reaction of deoxy-bouvardin with the boronic acid derivative of allo-RA-V, and subsequent deprotection, confirming the relative stereochemistry and establishing the absolute configuration of this peptide. RA-dimerB showed cytotoxic activity against human promyelocytic leukaemia HL-60, human colonic carcinoma HCT-116, and human renal cell carcinoma ACHN cells with IC50 values of 0.59, 0.54, and 0.74 mu m, respectively.