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. 2015 Dec 22;10(12):e0144950.
doi: 10.1371/journal.pone.0144950. eCollection 2015.

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

Zhe Wang  1   2 , Si-Meng Zhao  1 , Li-Mei Zhao  1 , Xiao-Qiang Chen  1 , Guang-Zhi Zeng  1 , Ning-Hua Tan  1   3
Affiliations

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

Zhe Wang et al. PLoS One. .

Abstract

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 N9-methyl group plays a vital role in the maintenance of the conformation and bioactivity.

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Conflict of interest statement

Competing Interests: The authors have declared that no competing interests exist.

Figures

Fig 1
Fig 1. Chemical structures of 1–7.
Fig 2
Fig 2. Key HMBC, 1H-1H COSY, and ROESY correlations of 1.
Fig 3
Fig 3. 1H NMR spectra comparison of rubipodanin A (1, top) and RA-V (4, bottom).
Fig 4
Fig 4. The cytotoxicity and inhibitory activity of rubipodanin A (1) and RA-V (4) against the NF-κB signaling pathway.
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