Immunomodulatory effects of 1-(6-hydroxy-2-isopropenyl-1-benzofuran-5-yl)- 1-ethanone from Petasites hybridus and its synthesized benzoxazepine derivatives

Fatemeh Khaleghi, Ibrahim Jantan, Laily Bin Din, Wan Yaacob Wan Ahmad, Mohammad A. Khalilzadeh, Bukhari Syed Nasir Abbas

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

1-(6-Hydroxy-2-isopropenyl-1-benzofuran-5-yl)-1-ethanone (1), isolated from the roots of Petasites hybridus L., and a series of synthetic benzoxazepine derivatives of compound 1 (2-6) were evaluated for their immunomodulatory effects. The compounds were evaluated for their effects on the respiratory burst of human whole blood and isolated human polymorphonuclear leukocytes (PMNs) using luminol- and lucigenin-based chemiluminescence (CL) assays, and their effect on chemotactic migration of PMNs was assessed using the Boyden chamber technique. Compound 1 exhibited stronger inhibition than acetylsalicylic acid (ASA) on luminol-enhanced CL of PMNs. It also inhibited PMN chemotaxis with an IC50 value comparable to that of ibuprofen. Of the compounds tested, 5 was the most effective in inhibiting luminol-enhanced CL and also strongly inhibited lucigenin-enhanced CL with IC50 values lower than that of ASA. Compound 2 was the most active in inhibiting migration of PMNs and was five times stronger than ibuprofen. The results suggest that compound 1 and its synthesized benzoxazepine derivatives, especially compounds 2 and 5, were able to modulate the innate immune response of phagocytes at different steps, emphasizing their potential as leads for the development of new immunomodulatory agents.

Original languageEnglish
Pages (from-to)351-357
Number of pages7
JournalJournal of Natural Medicines
Volume68
Issue number2
DOIs
Publication statusPublished - 2014

Fingerprint

Petasites
Chemiluminescence
Luminescence
Luminol
Derivatives
Ibuprofen
Aspirin
Inhibitory Concentration 50
Respiratory Burst
Chemotaxis
Phagocytes
Innate Immunity
Assays
Neutrophils
Blood
1-(6-hydroxy-2-isopropenyl-1-benzofuran-5-yl)-1-ethanone

Keywords

  • Benzofuran derivative
  • Benzoxazepines
  • Chemiluminescence
  • Chemotactic activity
  • Immunomodulatory effects
  • Petasites hybridus L.

ASJC Scopus subject areas

  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science
  • Complementary and alternative medicine

Cite this

Immunomodulatory effects of 1-(6-hydroxy-2-isopropenyl-1-benzofuran-5-yl)- 1-ethanone from Petasites hybridus and its synthesized benzoxazepine derivatives. / Khaleghi, Fatemeh; Jantan, Ibrahim; Din, Laily Bin; Wan Ahmad, Wan Yaacob; Khalilzadeh, Mohammad A.; Syed Nasir Abbas, Bukhari.

In: Journal of Natural Medicines, Vol. 68, No. 2, 2014, p. 351-357.

Research output: Contribution to journalArticle

Khaleghi, Fatemeh ; Jantan, Ibrahim ; Din, Laily Bin ; Wan Ahmad, Wan Yaacob ; Khalilzadeh, Mohammad A. ; Syed Nasir Abbas, Bukhari. / Immunomodulatory effects of 1-(6-hydroxy-2-isopropenyl-1-benzofuran-5-yl)- 1-ethanone from Petasites hybridus and its synthesized benzoxazepine derivatives. In: Journal of Natural Medicines. 2014 ; Vol. 68, No. 2. pp. 351-357.
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