2. Academic Validation
  3. Rubipodanones A-D, naphthohydroquinone dimers from the roots and rhizomes of Rubia podantha

Rubipodanones A-D, naphthohydroquinone dimers from the roots and rhizomes of Rubia podantha

  • Phytochemistry. 2018 Jan;145:153-160. doi: 10.1016/j.phytochem.2017.11.002.
Zhe Wang 1,  Si-Meng Zhao 2,  Yan-Yun Hu 3,  Li Feng 3,  Li-Mei Zhao 2,  Ying-Tong Di 2,  Ning-Hua Tan 4
Affiliations

Affiliations

  • 1 School of Traditional Chinese Pharmacy and State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing 211198, People's Republic of China; State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China.
  • 2 State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China.
  • 3 School of Traditional Chinese Pharmacy and State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing 211198, People's Republic of China.
  • 4 School of Traditional Chinese Pharmacy and State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing 211198, People's Republic of China; State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China. Electronic address: [email protected].
PMID: 29132078 DOI: 10.1016/j.phytochem.2017.11.002
Abstract

Four previously undescribed naphthohydroquinone dimers named rubipodanones A-D, together with 19 known Quinones containing three known napthohydroquinone dimers named rubioncolin C, methyl 5-hydroxy-dinaphtho[1,2-2',3']furan-7,12-dione-6-carboxylate and rubialatin B, were isolated from the roots and rhizomes of Rubia podantha. Their structures and absolute configurations were determined mainly by NMR, X-ray diffraction, and computational methods. Rubipodanones C and D, the glycosides of rubipodanone A and a pair of C-3 epimer, are the first identified dimeric napthohydroquinone glycosides from the Rubia Plants. All naphthohydroquinone dimers were evaluated for their cytotoxicities against ten tumor cell lines and effects on the tumor-associated NF-κB signaling pathway, and rubioncolin C showed the best cytotoxicity with IC50 value of 1.53 μM and NF-κB inhibitory activity with IC50 value of 2.97 μM. These results also demonstrated that the key roles of C-3 configuration and sugar group for biological activities of rubipodanone C.

Keywords

Cytotoxicity; NF-κB signaling pathway; Naphthohydroquinone dimers; Rubia podantha; Rubiaceae; Rubipodanones A-D.

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