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Investigating the potential of prenylated and geranylated acylphloroglucinol-based xanthenones as potent soybean 15-lipoxygenase inhibitors: a combined in vitro and in silico approach

  • Raaginie Tamil Segaran ORCID logo , Mohd Fadhlizil Fasihi Mohd Aluwi ORCID logo , Kok Wai Lam ORCID logo , Khozirah Shaari ORCID logo , Mazura Md Pisar ORCID logo , Siti Nur Aisyah Mohd Hashim ORCID logo , Syahrul Imran ORCID logo and Chean Hui Ng ORCID logo EMAIL logo
Published/Copyright: February 24, 2025
Pure and Applied Chemistry
From the journal Pure and Applied Chemistry Volume 97 Issue 6

Abstract

The 15-lipoxygenase (15-LOX) plays a key role in various diseases associated with inflammation. A geranylated acylphloroglucinol, namely 2,4,6-trihydroxy-3-geranylacetophenone or tHGA, 1 is a natural lead compound which exhibited significant LOXs inhibition. To further improve its 15-LOX inhibitory activity, xanthone moiety was incorporated into its scaffold using molecular hybridization (MH). In vitro soybean 15-LOX inhibition showed that all synthesized hybrids, 8a-c, 9a-c showed 4.5 to 590 times higher activity than tHGA, 1 with IC50 values ranging from 0.04 to 5.27 µM. Structure activity relationships (SARs) identified that aromatic substitutions (–Cl, –N(C2H5)2) on ring C of xanthenone improved activity. The most potent hybrid, 9b exhibited the highest docking score (−10.67 kcal/mol), with molecular dynamics (MD) simulations (100 ns) validating its strong soybean 15-LOX inhibitory potential. The results suggest the therapeutic potential of these LOX inhibitors in inflammation and provide valuable insight and understanding for further structural optimization around the tHGA 1 scaffold.

Keywords: docking simulations; hybrids; ICYC 2024; lipoxygenase inhibitor
Corresponding author: Chean Hui Ng, Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Malaya, 50603, Kuala Lumpur, Malaysia; and School of Pharmacy, Management and Science University, University Drive, Off Persiaran Olahraga, 40100 Shah Alam, Selangor, Malaysia, e-mail:
Article note: A collection of invited papers based on presentations at the 9th International Conference for Young Chemists (ICYC 2024) held on 9–11 Oct 2024 in Penang, Malaysia. All authors contributed equally to this work.

Funding source: Ministry of Higher Education

Award Identifier / Grant number: FRGS/1/2021/STG04/MSU/02/1

Acknowledgments

The authors acknowledge Forest Research Institute Malaysia (FRIM) for soybean 15-LOX inhibition assay service, and Atta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA (UiTM) for the MD simulation services.

  1. Research ethics: Not applicable.

  2. Informed consent: Not applicable.

  3. Author contributions: Conception: Ng, C. H., Shaari, K., Lam, K. W., Mohd Aluwi, M. F. F.; Design: Ng, C. H., Mohd Aluwi, M. F. F.; Execution: Tamil Segaran, R., Mohd Hashim, S. N. A., Md Pisar, M., Imran, S.; Interpretation: Ng, C. H., Tamil Segaran, R., Mohd Aluwi, M. F. F., Md Pisar, M., Imran, S.

  4. Use of Large Language Models, AI and Machine Learning Tools: None declared.

  5. Conflict of interest: The authors state no conflict of interest.

  6. Research funding: The work was funded by the Ministry of Higher Education, Fundamental Research Grant Scheme, FRGS/1/2021/STG04/MSU/02/1.

  7. Data availability: Authors confirm that the data supporting the findings of this study are available within the article and its Supplementary materials.

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Supplementary Material

This article contains supplementary material (https://doi.org/10.1515/pac-2024-0356).

Published Online: 2025-02-24
Published in Print: 2025-06-26

© 2025 IUPAC & De Gruyter

Articles in the same Issue

  1. Frontmatter
  2. In this issue
  3. Preface
  4. Preface: 9th International Conference for Young Chemists (ICYC) 2024
  5. Research Articles
  6. Doping TiO2 with Cu from electroplating wastewater for remarkable improvement of its activity under visible light for E. coli bacterial disinfection in water
  7. Investigating the potential of prenylated and geranylated acylphloroglucinol-based xanthenones as potent soybean 15-lipoxygenase inhibitors: a combined in vitro and in silico approach
  8. Intelligent food packaging from Ganyong starch (Canna Edulis Kerr.) modified with nanocellulose from corn husk (Zea mays) and curcumin as bioindicator
  9. Evaluation of 2-(1H-1,2,3-triazol-1-yl) acetic acid derivatives as potential human hypoxia-inducible factor (HIF) prolyl hydroxylase domain-2 (PHD2) inhibitors
  10. Microparticles zerumbone from Zingiber zerumbet rhizome in chitosan modified oleic acid
  11. Enhanced visible photocatalytic degradation of diclofenac by ultrasound-assisted prepared C and N co-doping TiO2
  12. Enhanced stability and permeability of graphene oxide nanocomposite membranes via glycine and diglycine cross-linking
  13. Furanyl-Chalcones as antimalarial agent: synthesis, in vitro study, DFT, and docking analysis of PfDHFR inhibition
https://doi.org/10.1515/pac-2024-0356
Keywords for this article
docking simulations; hybrids; ICYC 2024; lipoxygenase inhibitor

Articles in the same Issue

  1. Frontmatter
  2. In this issue
  3. Preface
  4. Preface: 9th International Conference for Young Chemists (ICYC) 2024
  5. Research Articles
  6. Doping TiO2 with Cu from electroplating wastewater for remarkable improvement of its activity under visible light for E. coli bacterial disinfection in water
  7. Investigating the potential of prenylated and geranylated acylphloroglucinol-based xanthenones as potent soybean 15-lipoxygenase inhibitors: a combined in vitro and in silico approach
  8. Intelligent food packaging from Ganyong starch (Canna Edulis Kerr.) modified with nanocellulose from corn husk (Zea mays) and curcumin as bioindicator
  9. Evaluation of 2-(1H-1,2,3-triazol-1-yl) acetic acid derivatives as potential human hypoxia-inducible factor (HIF) prolyl hydroxylase domain-2 (PHD2) inhibitors
  10. Microparticles zerumbone from Zingiber zerumbet rhizome in chitosan modified oleic acid
  11. Enhanced visible photocatalytic degradation of diclofenac by ultrasound-assisted prepared C and N co-doping TiO2
  12. Enhanced stability and permeability of graphene oxide nanocomposite membranes via glycine and diglycine cross-linking
  13. Furanyl-Chalcones as antimalarial agent: synthesis, in vitro study, DFT, and docking analysis of PfDHFR inhibition
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