Preparation and Evaluation of 6-Gingerol Derivatives as Novel Antioxidants and Antiplatelet Agents

Author:

Ahmed Sara H. H.1ORCID,Gonda Tímea1,Agbadua Orinamhe G.1,Girst Gábor1,Berkecz Róbert2ORCID,Kúsz Norbert1,Tsai Meng-Chun3,Wu Chin-Chung3,Balogh György T.45,Hunyadi Attila16ORCID

Affiliation:

1. Institute of Pharmacognosy, University of Szeged, H-6720 Szeged, Hungary

2. Institute of Pharmaceutical Analysis, University of Szeged, H-6720 Szeged, Hungary

3. Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, Taiwan

4. Institute of Pharmacodynamics and Biopharmacy, University of Szeged, H-6720 Szeged, Hungary

5. Department of Chemical and Environmental Process Engineering, Budapest University of Technology and Economics, H-1111 Budapest, Hungary

6. Interdisciplinary Centre of Natural Products, University of Szeged, H-6720 Szeged, Hungary

Abstract

Ginger (Zingiber officinale) is widely used as a spice and a traditional medicine. Many bioactivities have been reported for its extracts and the isolated compounds, including cardiovascular protective effects. Different pathways were suggested to contribute to these effects, like the inhibition of platelet aggregation. In this study, we synthesised fourteen 6-gingerol derivatives, including eight new compounds, and studied their antiplatelet, COX-1 inhibitor, and antioxidant activities. In silico docking of selected compounds to h-COX-1 enzyme revealed favourable interactions. The investigated 6-gingerol derivatives were also characterised by in silico and experimental physicochemical and blood–brain barrier-related parameters for lead and preclinical candidate selection. 6-Shogaol (2) was identified as the best overall antiplatelet lead, along with compounds 3 and 11 and the new compound 17, which require formulation to optimize their water solubility. Compound 5 was identified as the most potent antioxidant that is also promising for use in the central nervous system (CNS).

Funder

National Research, Development and Innovation Office

Ministry of Innovation and Technology

Publisher

MDPI AG

Subject

Cell Biology,Clinical Biochemistry,Molecular Biology,Biochemistry,Physiology

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