3,4-Dihydroxyphenethyl nitrate with nitric oxide releasing, antioxidant, hypoglycemic and hypolipidemic effects

Bioorg Med Chem Lett. 2020 Aug 1;30(15):127277. doi: 10.1016/j.bmcl.2020.127277. Epub 2020 May 20.

Abstract

Nitric oxide (NO) dysfunction, oxidative stress, and dyslipidemia are main risk factors associated with the pathophysiology of diabetic complications. In this study, 3,4-dihydroxyphenethyl nitrate (HT-ONO2) was designed, synthesized and evaluated, which incorporated hydroxytyrosol (HT) and nitrate. HT-ONO2 significantly exhibited hypoglycemic activity after oral administration to diabetic mice induced by streptozocin (STZ). HT-ONO2 also potently decreased plasma triglyceride (TG), total cholesterol (TC) in hyperlipidemia mice induced by Triton WR 1339. Meanwhile, HT-ONO2 displayed NO-releasing and antioxidant activity both in diabetic and hyperlipidemia mice and in vitro. Moreover, HT-ONO2 shown definite vasodilation and α-glucosidase inhibition activity in vitro. The results suggested that the hybrid hydroxytyrosol-based nitrate with NO supplement, antioxidant, hypoglycemia and hypolipidemia provided a potential multi-target agent to ameliorate the diabetes mellitus and its complications.

Keywords: 3,4-Dihydroxyphenethyl nitrate; Antioxidant; Hypoglycemia; Hypolipidemia; NO releasing; Vasodilatation.

MeSH terms

  • Administration, Oral
  • Animals
  • Antioxidants / administration & dosage
  • Antioxidants / pharmacology*
  • Diabetes Mellitus, Experimental / chemically induced
  • Diabetes Mellitus, Experimental / drug therapy
  • Diabetes Mellitus, Experimental / metabolism
  • Hypoglycemic Agents / administration & dosage
  • Hypoglycemic Agents / pharmacology*
  • Hypolipidemic Agents / administration & dosage
  • Hypolipidemic Agents / pharmacology*
  • Mice
  • Molecular Structure
  • Nitrates / administration & dosage
  • Nitrates / pharmacology*
  • Nitric Oxide / metabolism*
  • Phenylethyl Alcohol / administration & dosage
  • Phenylethyl Alcohol / analogs & derivatives*
  • Phenylethyl Alcohol / pharmacology
  • Streptozocin

Substances

  • Antioxidants
  • Hypoglycemic Agents
  • Hypolipidemic Agents
  • Nitrates
  • 3,4-dihydroxyphenylethanol
  • Nitric Oxide
  • Streptozocin
  • Phenylethyl Alcohol