2. Academic Validation
  3. Unsaturation-Driven Modulation of Antioxidant and Acetylcholinesterase Inhibitory Activities of Cardanol Derivatives

Unsaturation-Driven Modulation of Antioxidant and Acetylcholinesterase Inhibitory Activities of Cardanol Derivatives

  • Bioengineering (Basel). 2025 Dec 1;12(12):1316. doi: 10.3390/bioengineering12121316.
Roberta Bussons Rodrigues Valério 1 2 3,  Halisson de Souza 2,  Vitor Martins 2,  Katherine Silva 2,  Jane Eire de Manezes 1,  Anderson Chaves 3,  Leonardo F Serafim 4,  Antônio Vieira-Neto 5,  José Cleiton S Dos Santos 1 6,  Selene de Morais 1 2
Affiliations

Affiliations

  • 1 Postgraduate Program in Natural Sciences, State University of Ceará-UECE, Itaperi Campus, Fortaleza 60714-903, CE, Brazil.
  • 2 Laboratory of Natural Products Chemistry, State University of Ceará-UECE, Itaperi Campus, Fortaleza 60714-903, CE, Brazil.
  • 3 Advanced Materials Chemistry Group (GQMAT), Department of Analytical and Physical Chemistry, Federal University of Ceará-UFC, Pici Campus, CP 12100, Fortaleza 60451-970, CE, Brazil.
  • 4 Department of Chemistry, Georgia State University, Atlanta, GA 30302, USA.
  • 5 Center for Experimental Biology, University of Fortaleza, Av. Washington Soares, 1321, Fortaleza 60811-905, CE, Brazil.
  • 6 Institute of Engineering and Sustainable Development (IEDS), University of International Integration of Afro-Brazilian Lusophony-UNILAB, Campus das Auroras, Rua José Franco de Oliveira, s/n, Redenção 62790-970, CE, Brazil.
PMID: 41463613 DOI: 10.3390/bioengineering12121316
Abstract

Background: Cardanol, a bioactive alkylphenol obtained from technical cashew nutshell liquid (CNSL), consists of mono-, di-, and tri unsaturated side chain derivatives. These compounds are of increasing interest for their diverse industrial applications. Methods: In this study, three major cardanol components-3-[(8E)-8-pentadecen-1-yl] phenol (C1), 3-[(8E,11E)-8,11-pentadecadien-1-yl] phenol (C2), and 3-[(8E,11E,14E)-8,11,14-pentadecatrien-1-yl] phenol (C3)-were isolated from CNSL via chromatographic separation. Their structures were confirmed by FTIR and detailed 1H and 13C NMR spectroscopy, with complete carbon and proton assignments reported. Results: Among the three, C3 exhibited the highest antioxidant potential, with a DPPH IC50 value of 0.179 ± 0.005 mg/mL, approximately five times more potent than C1 (IC50 = 1.000 ± 0.200 mg/mL). C3 also showed the highest lethality against Artemia salina (LC50 = 4.118 ± 0.328 mg/mL) and the most pronounced inhibition of acetylcholinesterase (AChE), with a 0.8 cm inhibition zone. Computational studies using molecular docking and molecular dynamics simulations further supported the interaction of these compounds with both the catalytic active site (CAS) and the peripheral anionic site (PAS) of AChE. Conclusions: These results expand our understanding of the chemical composition and potential applications of CNSL. The identified unsaturated alkylphenols, particularly the triene compound, demonstrate promise as sustainable candidates for the development of new Materials and pharmaceuticals that combat oxidative stress and neurodegenerative diseases.

Keywords

acetylcholinesterase; antioxidant; cardanol; docking; molecular dynamics; spectroscopy.

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