HPLC-UV and LC-MS Analyses of Acylquinic Acids in Geigeria alata (DC) Oliv. & Hiern. and their Contribution to Antioxidant and Antimicrobial Capacity

Phytochem Anal. 2017 May;28(3):176-184. doi: 10.1002/pca.2658. Epub 2016 Dec 1.

Abstract

Introduction: Geigeria alata is a traditional plant used in Sudanese folk medicine for treatment of diabetes, cough, epilepsy and intestinal complaints.

Objective: To analyze phenolic acids in Geigeria alata roots and leaves and to evaluate their antioxidant and antimicrobial activities.

Methodology: Phenolic acids in the aqueous-methanol extracts were identified by LC-MS. Major compounds were isolated using low-pressure liquid chromatography. The quantitative analysis of phenolic acids was performed by a validated HPLC-UV method with limits of detection ranging from 0.04 to 0.57 μg/mL. 2,2-Diphenyl-1-picrylhydrazyl (DPPH), 2,2'-azinobis-(3-ethylbenzothiazine-6-sulphonic acid) (ABTS) and ferric reducing antioxidant power (FRAP) methods were used for antioxidant activity evaluation. In addition, the minimal inhibitory concentration and the minimal bactericidal concentration against a panel of pathogenic bacteria and fungi were determined by the broth microdilution test.

Results: For the first time protocatechuic, caffeic, p-coumaroylquinic, caffeoylsinapoylquinic, caffeoylferuloylquinic, three feruloylquinic, six caffeoylquinic acids, and a caffeic acid hexoside were detected in Geigeria alata roots by LC-MS. HPLC-UV analyses showed that 3,5-dicaffeoylquinic acid (25.96 ± 2.08 mg/g dry weight (DW)) was the most abundant phenolic acid in roots, while 4,5-dicaffeoylquinic acid (8.99 ± 0.56 mg/g DW) was the main compound present in leaves. 3,5-Dicaffeoylquinic acid demonstrated stronger radical scavenging activity and reducing power compared with the crude extracts and the positive control 5-caffeoylquinic acid. 3,4,5-Tricaffeoylquinic acid revealed the highest antibacterial potential against the penicillin sensitive and resistant Staphylococcus aureus strains, as well as methicillin-resistant S. aureus.

Conclusion: The caffeoylquinic acids content of up to 6.22% in Geigeria alata roots establishes this species as a new source rich in these bioactive molecules. Copyright © 2016 John Wiley & Sons, Ltd.

Keywords: Caffeoylquinic acids; Geigeria alata; HPLC-UV; LC-MS.

MeSH terms

  • Anti-Infective Agents / analysis
  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / pharmacology*
  • Antioxidants / analysis
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Caffeic Acids / analysis
  • Chlorogenic Acid / analogs & derivatives
  • Chlorogenic Acid / analysis
  • Chromatography, High Pressure Liquid / methods*
  • Chromatography, Liquid
  • Flavonoids / analysis
  • Geigeria / chemistry*
  • Mass Spectrometry / methods
  • Methicillin-Resistant Staphylococcus aureus / drug effects
  • Microbial Sensitivity Tests
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology
  • Plant Leaves / chemistry
  • Plant Roots / chemistry
  • Plants, Medicinal / chemistry
  • Polyphenols / analysis
  • Quinic Acid / analogs & derivatives
  • Quinic Acid / analysis

Substances

  • Anti-Infective Agents
  • Antioxidants
  • Caffeic Acids
  • Flavonoids
  • Plant Extracts
  • Polyphenols
  • caffeoylquinic acid
  • Quinic Acid
  • Chlorogenic Acid
  • 3,5-dicaffeoylquinic acid
  • caffeic acid