Metabolite Profiling by Hyphenated Liquid Chromatographic Mass Spectrometric Technique (HPLC-DAD-ESI-Q-TOF-MS/MS) and Neurobiological Potential of Haplophyllum sahinii and H. vulcanicum Extracts

Karahisar E., TUGAY O., ERDOĞAN ORHAN İ., ŞENOL DENİZ F. S., Luca S. V., Skalicka-Wozniak K., ...More

CHEMISTRY & BIODIVERSITY, vol.16, no.9, 2019 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 16 Issue: 9
  • Publication Date: 2019
  • Doi Number: 10.1002/cbdv.201900333
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Keywords: Haplophyllum sahinii, Haplophyllum vulcanicum, cholinesterase, tyrosinase, metabolite profiling, biological activity, TYROSINASE INHIBITORS, CHOLINESTERASE-INHIBITORS, ANTIOXIDANT ACTIVITIES, ALKALOIDS, COUMARINS, LIGNANS, ANTICHOLINESTERASE, DERIVATIVES, DISCOVERY, ALZHEIMER
  • Gazi University Affiliated: Yes


In the current study, the ethanol extracts of flower, stem, and root parts of two endemic Turkish species, e. g., Haplophyllum sahinii O. Tugay & D. Ulukus and H. vulcanicum Boiss. & Heldr., were screened against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) associated with Alzheimer's disease as well as tyrosinase (TYR) linked to Parkinson's disease using ELISA microplate assay at 200 mu g/mL. Among the extracts, the highest inhibition was caused by the stem extract of H. sahinii against BChE (IC50=64.93 +/- 1.38 mu g/mL). Consistently, all of the extracts were found to exert a selective inhibition towards BChE to some extent. It was only the root extract of H. vulcanicum that could inhibit AChE at low level (IC50=203.18 +/- 5.33 mu g/mL). None of the extracts displayed an inhibition over 50 % against TYR. Metabolite profiling of the extracts was achieved by a highly hyphenated liquid chromatographic mass spectrometric technique (HPLC-DAD-ESI-Q-TOF-MS/MS), which revealed the presence of furoquinoline (beta-fagarine, gamma-fagarine) and amide (tubasenicine, tubacetine) alkaloids; furano- (rutamarin), pyrano- (xanthyletine), and geranyloxy coumarins; phenylpropanoid (secoisolariciresinol), arylnaphthalene (mono-O-acetyldiphyllin apioside), and dibenzylbutyrolactone (kusunokinin, haplomyrfolin) lignans. Several important differences were observed between the extracts analyzed. beta-Fagarine was the major alkaloid in H. vulcanicum, whereas gamma-fagarine was present only in the roots of both Haplophyllum species; moreover, secoisolariciresinol and secoisolariciresinol dimethyl ether were the main lignans in the stems and flowers. This is the first study identifying ChE and TYR inhibitory effect and metabolic profiles of H. vulcanicum and H. sahinii.