RA‐dimer B, a New Dimeric RA‐series Cyclopeptide Incorporating Two Different Types of Cycloisodityrosine Units, from Rubia cordifolia L. Issue 23 (8th November 2016)

• Record Type: Journal Article
• Authors: Hitotsuyanagi, Yukio; Tsuchiya, Takayuki; Ohata, Masako; Yoshida, Ayaka; Fukaya, Haruhiko; Park, Hyun Sun; Takeya, Koichi; Kawahara, Nobuo
• Is Part Of: Chemistry, an Asian journal. Volume 11:Issue 23(2016)
• Page Start: 3389
• Page End: 3397
• Publication Date: 2016-11-08
• Subjects: configuration determination -- cytotoxicity -- peptides -- structure elucidation -- synthesis; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.201601138
• Languages: English
• ISSNs: 1861-4728

Abstract

Abstract: 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 ϵa carbon atom of Tyr‐6 of allo‐RA‐V. RA‐dimer B was synthesized by the coupling reaction of deoxybouvardin 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‐dimer B 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 μm, respectively. Abstract : Rooted in Asia : RA‐dimer B, a new cytotoxic RA‐series peptide, was isolated from the roots of Rubia cordifolia L. Its structure was elucidated to be a dimeric cyclopeptide composed of deoxybouvardin and allo‐RA‐V on the basis of spectroscopic analysis, and was confirmed by synthesis.