Spiroketones and a Biphenyl Analog from Stems and Leaves of Larrea nitida and Their Inhibitory Activity against IL-6 Production

Molecules. 2018 Jan 31;23(2):302. doi: 10.3390/molecules23020302.

Abstract

Bioactivity-guided fractionation for the stems of leaves of Larrea nitida Cav., using interleukin-6 (IL-6) inhibitory assay in human mast cells (HMC-1), led to the isolation of three new compounds with an unprecedented skeleton in nature (1-3) and three known compounds (4-6). Their structures were elucidated through extensive spectroscopic analysis. The three new compounds were elucidated as two new spiroketones, nitidaones A (1), and B (2) and one new biphenyl analog, nitidaol (3). The known compounds were identified as nordihydroguaiaretic acid (4), 7,3',4'-tri-O-methylquercetin (5) and ayanin (6). All the isolates were tested for their inhibitory activity against IL-6 production in HMC-1 cells. Of them, compounds 1, 3-6 showed potent anti-inflammatory activity, with IC50 values of 12.8, 17.5, 14.9, 22.9, and 17.8 µM, respectively.

Keywords: HMC-1; IL-6; Larrea nitida; biphenyl analog; spiroketones.

MeSH terms

  • Anti-Inflammatory Agents* / chemistry
  • Anti-Inflammatory Agents* / pharmacology
  • Biphenyl Compounds* / chemistry
  • Biphenyl Compounds* / pharmacology
  • Cell Line
  • Humans
  • Interleukin-6 / biosynthesis*
  • Larrea / chemistry*
  • Mast Cells / cytology
  • Mast Cells / metabolism*
  • Plant Leaves / chemistry*
  • Plant Stems / chemistry*
  • Spironolactone* / chemistry
  • Spironolactone* / pharmacology

Substances

  • Anti-Inflammatory Agents
  • Biphenyl Compounds
  • IL6 protein, human
  • Interleukin-6
  • Spironolactone
  • diphenyl