New flavonoid glycosides from Sedum aizoon L

Fitoterapia. 2015 Mar:101:125-32. doi: 10.1016/j.fitote.2014.12.014. Epub 2015 Jan 3.

Abstract

Five new flavonoid glucosides (3-4, 10-12) and a new phenolic derivative (5), together with eight known compounds including three flavonoid glucosides (6-8), three phenolic compounds (1-2, 9) and two megastigmane glucosides (13, 14), were isolated from the ethanol extract of the aerial part of Sedum aizoon L. Among them, compounds 9, 13 and 14 were isolated and identified from this genus for the first time. The structures of compounds were elucidated on the basis of 1D and 2D NMR (HSQC, HMBC and COSY) spectra and the HR-ESI-MS data. These compounds were tested for their antibacterial efficacies against both Gram-positive and Gram-negative bacteria. Compounds 1, 2, 3, 7 and 10 showed certain antibacterial activity; it showed more potency against Gram-positive than against Gram-negative bacteria. Compound 2 showed the most pronounced antibacterial effectiveness against Staphylococcus aureus Rosenbach with MIC value of 7.8μg·mL(-1). The in vitro anti-proliferative activities against HepG2, MCF-7 and A549 tumor cell lines were also evaluated. The result suggested compound 7 exhibited moderate cytotoxic activities with IC50 values of 46.30, 75.27 and 49.76μmol/L, respectively.

Keywords: (3S,5R,6R,7E,9S)-megastigman-7-ene-3,5,6,9-tetrol 3-O-β-d-glucopyranoside (PubChem CID: 23757168); (3S,5R,6R,7E,9S)-megastigman-7-ene-3,5,6,9-tetrol 9-O-β-d-glucopyranoside (PubChem CID: 71694406); 1-O-sinpoyl glucopyranoside (PubChem CID: 77338752); Antibacterial activity; Cytotoxicity; Flavonoid glucoside; Gallic acid (PubChem CID: 370); Herbacetin-8-O-β-d-glucopyranoside (PubChem CID: 44259936); Methyl gallate (PubChem CID: 7428); Myricetin-3-O-β-d-glucopyranoside (PubChem CID: 44259426); Phenolic compounds; Quercetin-3-O-α-l-rhamnopyranoside (PubChem CID: 40486293); Sedum aizoon L.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification
  • Cell Line, Tumor
  • Cyclohexanones / chemistry*
  • Cyclohexanones / isolation & purification
  • Flavonoids / chemistry*
  • Flavonoids / isolation & purification
  • Glucosides / chemistry*
  • Glucosides / isolation & purification
  • Humans
  • Inhibitory Concentration 50
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Norisoprenoids / chemistry*
  • Norisoprenoids / isolation & purification
  • Phenols / chemistry*
  • Phenols / isolation & purification
  • Sedum / chemistry*
  • Staphylococcus aureus / drug effects

Substances

  • Anti-Bacterial Agents
  • Cyclohexanones
  • Flavonoids
  • Glucosides
  • Norisoprenoids
  • Phenols
  • megastigmane