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Free Radical Scavenging and Cytotoxic Properties of Acylated and Non-Acylated Kaempferol Glycosides from Stenochlaena Palustris: a Perspective on Their Structure – Activity Relationships

  • Nelson Jeng-Yeou Chear
  • Agustine Nengsih Fauzi
  • Kooi-Yeong Khaw
  • Sy-Bing Choi
  • Nik Soriani Yaacob
  • Choon-Sheen LaiEmail author
Article
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Flavonoid glycosides that are present in acylated form have good prospect to be developed into therapeutic agents due to their improved biological properties, stability and physico-chemical properties compared to their maternal compounds. The present study aimed to compare the free radical scavenging and cytotoxic activities of a series of acylated and non-acylated kaempferol glycosides isolated from Stenochlaena palustris. The in silico binding interactions of the most cytotoxic glycoside with epidermal growth factor receptor was also evaluated. Results indicated that the free radical scavenging capability and cytotoxicity of kaempferol 3-O-β-D-glucopyranoside were enhanced through acylation with selected hydroxycinnamoyl groups, whereas mono-acylation did not improve both activities. Molecular docking study revealed that di-acylation was essential for the compound to bind to five major active sites of the receptor. Kaempferol 3-O-β-D-glucopyranosides that are di-acylated may be further explored for their chemopreventive and anticancer properties due to their significant antioxidant and cytotoxic properties.

Keywords

free radical scavenging cytotoxicity acylated kaempferol glycosides structure-activity relationships Stenochlaena palustris molecular docking 

Notes

Acknowledgments

This study was funded by the Short Term Grant (304/CDADAH/6311104) and Research University Grant of Universiti Sains Malaysia (USM) (1001/CDADAH/815096). NJYC was supported by MyBrain15 scholarship from the Ministry of Higher Education of Malaysia. ANF was supported by the USM Academic Staff Training Scheme and the Ministry of Higher Education of Malaysia.

Disclosure Statement

The authors declare that there is no conflict of interest regarding the publication of this paper.

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Nelson Jeng-Yeou Chear
    • 1
  • Agustine Nengsih Fauzi
    • 2
  • Kooi-Yeong Khaw
    • 3
  • Sy-Bing Choi
    • 4
  • Nik Soriani Yaacob
    • 2
  • Choon-Sheen Lai
    • 1
    Email author
  1. 1.Centre for Drug ResearchUniversiti Sains MalaysiaPenangMalaysia
  2. 2.Department of Chemical Pathology, School of Medical SciencesUniversiti Sains Malaysia Health CampusKubang KerianMalaysia
  3. 3.Discipline of Pharmacology, School of Pharmaceutical SciencesUniversiti Sains MalaysiaPenangMalaysia
  4. 4.Malaysian Institute of Pharmaceuticals and Nutraceuticals, National Institutes of Biotechnology Malaysia, Ministry of Science, Technology and InnovationPenangMalaysia

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