O-Seco-RA-XXIV, a possible precursor of an antitumor peptide RA-XXIV, from Rubia cordifolia L.

Genus Rubia fell into about 70 species distributed widely around the world, a total of 36 species and 2 varieties were reported from China. The extracts and phytochemicals of Rubia plants had drawn considerable attention due to their potent bioactivities. As the two major ingredients from these plants, pentacyclic triterpenes and cyclopeptides were becoming a hot topic over the past twenty years for their remarkable anticancer, antioxidant and other effects. This paper compiled all 65 terpenes and 44 cyclopeptides with their distributions, physiological activities and melting points (or optical rotations) as reported in 85 references; besides, structure-activity relationships of these derivatives were briefly discussed. The information involved in this paper was expected to be meaningful for the further studies of the Genus Rubia.

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“…Just in last year, Y. Hitotsuyanagi etc . got a series of special cyclopeptides from the Genus Rubia [62,63]. …”

Section: Reviewmentioning

confidence: 99%

“…The newly identified compounds 106–108, and RA-V, VII were evaluated for their cytotoxic activities against HL-60 and HCT-116 while only the latter had potent cytotoxicities [62]. Moreover, compound 109 exhibited cytotoxic effects on HL-60 cells, but which was much weaker than those of RA-XXIV and RA-VII [63]. …”

Section: Reviewmentioning

confidence: 99%

Structural and bioactive studies of terpenes and cyclopeptides from the Genus Rubia

Wang

Yuan

et al. 2013

Chemistry Central Journal

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“…[15,16] O-Seco-deoxybouvardin (16)h as been isolated from this plant as ap ossible biosynthetic precursor of deoxybouvardin (4)a nd allo-RA-V (5). [9,17] RA-dimer B( 3)m ay be biosynthesized by oxidative couplingo f16 with 4 to produce dimeric inter-mediate 17 and the subsequento xidative formation of the diphenyle ther ring of the allo-RA-V unit of 3 (Scheme 3). Alternatively, the biosynthesis of peptide 3 may occur by the direct oxidative coupling of deoxybouvardin (4)w ith allo-RA-V (5).…”

Section: Ra-dimer B( 3)h As Unusuals Tructural Featuresmentioning

confidence: 99%

RA‐dimer B, a New Dimeric RA‐series Cyclopeptide Incorporating Two Different Types of Cycloisodityrosine Units, from Rubia cordifolia L.

Hitotsuyanagi

Tsuchiya

Ohata

et al. 2016

Chemistry An Asian Journal

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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 IC values of 0.59, 0.54, and 0.74 μm, respectively.

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“…yunnanensis and R . akane , and more than 200 analogues have been synthesized [ 1 , 4 – 8 ]. Studies on antitumor mechanisms of RAs have indicated that RA-VII suppresses protein synthesis through interaction with eukaryotic 80S ribosomes [ 9 ].…”

Section: Introductionmentioning

confidence: 99%

Rubipodanin A, the First Natural N-Desmonomethyl Rubiaceae-Type Cyclopeptide from Rubia podantha, Indicating an Important Role of the N9-Methyl Group in the Conformation and Bioactivity

Wang

Zhao

et al. 2015

PLoS ONE

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One new cyclic hexapeptide named rubipodanin A (1), which is the first identified natural N-desmonomethyl Rubiaceae-type cyclopeptide, together with six known Rubiaceae-type cyclopeptides (2–7) were obtained using the TLC cyclopeptide protosite detection method with ninhydrin from the roots and rhizomes of Rubia podantha. The cyclopeptide structures were elucidated by extensive spectroscopic analysis, including 1D-NMR, 2D-NMR, IR, UV and MS. The solution conformation and biological activities of 1 and RA-V (4) were evaluated, and the results demonstrated that the N 9-methyl group plays a vital role in the maintenance of the conformation and bioactivity.

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O-Seco-RA-XXIV, a possible precursor of an antitumor peptide RA-XXIV, from Rubia cordifolia L.

Cited by 14 publications

References 10 publications

Structural and bioactive studies of terpenes and cyclopeptides from the Genus Rubia

Structural and bioactive studies of terpenes and cyclopeptides from the Genus Rubia

RA‐dimer B, a New Dimeric RA‐series Cyclopeptide Incorporating Two Different Types of Cycloisodityrosine Units, from Rubia cordifolia L.

Rubipodanin A, the First Natural N-Desmonomethyl Rubiaceae-Type Cyclopeptide from Rubia podantha, Indicating an Important Role of the N9-Methyl Group in the Conformation and Bioactivity

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