Recurvataside, a new saponin from aerial parts of Mussaenda recurvata

Nat Prod Res. 2023 Jul;37(14):2303-2310. doi: 10.1080/14786419.2022.2039137. Epub 2022 Feb 17.

Abstract

A new glycoside, recurvataside (1) and six known compounds, quinovic acid (2), quinovic acid 28-O-β-D-glucopyranosyl ester (3), 3-O-β-D-glucopyranosylquinovic acid (4), 3-O-β-D-glucopyranosylquinovic acid 28-O-β-D-glucopyranosyl ester (5), pomolic acid (6), and ursolic acid (7) were isolated from aerial parts of Mussaenda recurvata. The structure of compound 1 was identified from its spectroscopic data and by comparison with the literature. Recurvataside represents the first occurrence of δ-oleanolic acid saponin bearing two D-glucose units at C-3 and C-28 in nature. This is the first time δ-oleanane-type saponin reported in the genus Mussaenda. Compounds 1-7 were evaluated the cytotoxicity against two cancer cell lines MCF-7 and HepG2. Among them, only compound 7 exhibited moderate activity against MCF-7 and HepG2 cell lines with IC50 value of 16.97 ± 1.55 and 20.28 ± 1.00 μM, respectively. Compounds 1-7 were also tested for their inhibitory NO production in LPS-stimulated RAW264.7 cells. Compounds 3, 5, and 7 showed significant reduction of nitrite accumulation in LPS-stimulated RAW 264.7 cells with the IC50 values of 8.81 ± 0.48, 13.42 ± 0.84, and 18.37 ± 0.67 μM, respectively.

Keywords: Mussaenda recurvata; Rubiaceae; glycoside; recurvataside; saponin.

MeSH terms

  • Lipopolysaccharides
  • Molecular Structure
  • Plant Components, Aerial
  • Rubiaceae* / chemistry
  • Saponins* / chemistry
  • Saponins* / pharmacology
  • Triterpenes* / chemistry
  • Triterpenes* / pharmacology

Substances

  • Saponins
  • quinovic acid
  • Lipopolysaccharides
  • Triterpenes