Anti-inflammatory, analgesic and antioxidant activities of 3,4-oxo-isopropylidene-shikimic acid

Pharm Biol. 2016 Oct;54(10):2282-7. doi: 10.3109/13880209.2016.1153663. Epub 2016 Mar 24.

Abstract

Context 3,4-Oxo-isopropylidene-shikimic acid (ISA) is an analog of shikimic acid (SA). SA is extracted from the dry fruit of Illicium verum Hook. f. (Magnoliaceae), which has been used for treating stomachaches, skin inflammation and rheumatic pain. Objective To investigate the anti-inflammatory, analgesic and antioxidant activities of ISA. Materials and methods Analgesic and anti-inflammatory activities of ISA were evaluated using writhing, hot plate, xylene-induced ear oedema, carrageenan-induced paw oedema and cotton pellets-induced granuloma test, meanwhile the prostaglandin E2 (PGE2) and malondialdehyde (MDA) levels were assessed in the oedema paw tissue. ISA (60, 120 and 240 mg/kg in mice model and 50, 120 and 200 mg/kg in rat model) was administered orally, 30 min before induction of inflammation/pain. Additionally, ISA was administered for 12 d in rats from the day of cotton pellet implantation. The active oxygen species scavenging potencies of ISA (10(-3)-10(-5) M) were evaluated by the electron spin resonance spin-trapping technique. Results ISA caused a reduction of inflammation induced by xylene (18.1-31.4%), carrageenan (7.8-51.0%) and cotton pellets (11.4-24.0%). Furthermore, ISA decreased the production of PGE2 and MDA in the rat paw tissue by 1.0-15.6% and 6.3-27.6%, respectively. ISA also reduced pain induced by acetic acid (15.6-48.9%) and hot plate (10.5-28.5%). Finally, ISA exhibited moderate antioxidant activity by scavenging the superoxide radical and hydroxyl radical with IC50 values of 0.214 and 0.450 μg/mL, respectively. Discussion and conclusion Our findings confirmed the anti-inflammatory, analgesic and antioxidant activities of ISA.

Keywords: Carrageenan; Illicium verum Hook.f.; malondialdehyde; prostaglandin E2; xylene.

Publication types

  • Comparative Study

MeSH terms

  • Acetic Acid
  • Analgesics / pharmacology*
  • Animals
  • Anti-Inflammatory Agents / pharmacology*
  • Antioxidants / pharmacology*
  • Carrageenan
  • Cotton Fiber
  • Dinoprostone / metabolism
  • Disease Models, Animal
  • Dose-Response Relationship, Drug
  • Edema / chemically induced
  • Edema / metabolism
  • Edema / prevention & control*
  • Female
  • Granuloma, Foreign-Body / chemically induced
  • Granuloma, Foreign-Body / prevention & control*
  • Hot Temperature
  • Hydroxyl Radical / chemistry
  • Indomethacin / pharmacology
  • Male
  • Malondialdehyde / metabolism
  • Mice, Inbred ICR
  • Pain / etiology
  • Pain / prevention & control*
  • Rats, Sprague-Dawley
  • Shikimic Acid / analogs & derivatives*
  • Shikimic Acid / pharmacology
  • Superoxides / chemistry
  • Time Factors
  • Xylenes

Substances

  • 3,4-oxoisopropylideneshikimic acid
  • Analgesics
  • Anti-Inflammatory Agents
  • Antioxidants
  • Xylenes
  • Superoxides
  • Shikimic Acid
  • Hydroxyl Radical
  • Malondialdehyde
  • Carrageenan
  • Dinoprostone
  • Acetic Acid
  • Indomethacin