Isolation of Terpenoids from the Stem of Ficus aurantiaca Griff and their Effects on Reactive Oxygen Species Production and Chemotactic Activity of Neutrophils

Molecules. 2016 Jan 5;21(1):9. doi: 10.3390/molecules21010009.

Abstract

Three new triterpenoids; namely 28,28,30-trihydroxylupeol (1); 3,21,21,26-tetrahydroxy-lanostanoic acid (2) and dehydroxybetulinic acid (3) and seven known compounds; i.e., taraxerone (4); taraxerol (5); ethyl palmitate (6); herniarin (7); stigmasterol (8); ursolic acid (9) and acetyl ursolic acid (10) were isolated from the stem of Ficus aurantiaca Griff. The structures of the compounds were established by spectroscopic techniques. The compounds were evaluated for their inhibitory effects on polymorphonuclear leukocyte (PMN) chemotaxis by using the Boyden chamber technique and on human whole blood and neutrophil reactive oxygen species (ROS) production by using a luminol-based chemiluminescence assay. Among the compounds tested, compounds 1-4, 6 and 9 exhibited strong inhibition of PMN migration towards the chemoattractant N-formyl-methionyl-leucyl-phenylalanine (fMLP) with IC50 values of 6.8; 2.8; 2.5; 4.1; 3.7 and 3.6 μM, respectively, comparable to that of the positive control ibuprofen (6.7 μM). Compounds 2-4, 6, 7 and 9 exhibited strong inhibition of ROS production of PMNs with IC50 values of 0.9; 0.9; 1.3; 1.1; 0.5 and 0.8 μM, respectively, which were lower than that of aspirin (9.4 μM). The bioactive compounds might be potential lead molecules for the development of new immunomodulatory agents to modulate the innate immune response of phagocytes.

Keywords: Ficus aurantiaca Griff; chemotaxis; immunomodulatory; neutrophils; reactive oxygen species; terpenoids.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aspirin / pharmacology
  • Chemotaxis / drug effects
  • Ficus / chemistry*
  • Humans
  • Ibuprofen / pharmacology
  • Immunologic Factors / chemistry
  • Immunologic Factors / isolation & purification*
  • Immunologic Factors / pharmacology
  • Inhibitory Concentration 50
  • Luminescent Measurements
  • N-Formylmethionine Leucyl-Phenylalanine / antagonists & inhibitors
  • N-Formylmethionine Leucyl-Phenylalanine / pharmacology
  • Neutrophils / cytology
  • Neutrophils / drug effects*
  • Neutrophils / immunology
  • Plant Extracts / chemistry
  • Plant Stems / chemistry
  • Reactive Oxygen Species / antagonists & inhibitors*
  • Reactive Oxygen Species / metabolism
  • Respiratory Burst / drug effects
  • Respiratory Burst / immunology
  • Terpenes / chemistry
  • Terpenes / isolation & purification*
  • Terpenes / pharmacology

Substances

  • Immunologic Factors
  • Plant Extracts
  • Reactive Oxygen Species
  • Terpenes
  • N-Formylmethionine Leucyl-Phenylalanine
  • Aspirin
  • Ibuprofen