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Polymerized Luteolin Nanoparticles: Synthesis, Structure Elucidation, and Anti-Inflammatory Activity

[Image: see text] Luteolin is an anti-inflammatory flavonoid commonly found in many edible plants. The compound is popularly consumed as a supplement regardless of its poor water solubility (27.8 μg/mL at 25 °C) and low bioavailability. Here, mild one-pot polymerization of luteolin into water-disper...

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Autores principales: Tawornchat, Parichat, Pattarakankul, Thitiporn, Palaga, Tanapat, Intasanta, Varol, Wanichwecharungruang, Supason
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7860061/
https://www.ncbi.nlm.nih.gov/pubmed/33553902
http://dx.doi.org/10.1021/acsomega.0c05142
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author Tawornchat, Parichat
Pattarakankul, Thitiporn
Palaga, Tanapat
Intasanta, Varol
Wanichwecharungruang, Supason
author_facet Tawornchat, Parichat
Pattarakankul, Thitiporn
Palaga, Tanapat
Intasanta, Varol
Wanichwecharungruang, Supason
author_sort Tawornchat, Parichat
collection PubMed
description [Image: see text] Luteolin is an anti-inflammatory flavonoid commonly found in many edible plants. The compound is popularly consumed as a supplement regardless of its poor water solubility (27.8 μg/mL at 25 °C) and low bioavailability. Here, mild one-pot polymerization of luteolin into water-dispersible nanospheres, with an average dry size of 234.8 ± 101.6 nm, an aqueous size distribution of 379.1 ± 220.5 nm (PDI = 0.338), an average ζ-potential of −36.2 ± 0.2 mV, and an 89.3 ± 4.8% yield, is described. The nanospheres consist of polymerized luteolin (polyluteolin) with a weight-average molecular mass of around 410000 Da. The chemical structure of polyluteolin is identified through (1)H–(1)H correlated spectroscopy (COSY), (1)H–(13)C heteronuclear single-quantum coherence (HSQC), and (1)H–(13)C heteronuclear multiple-bond correlation (HMBC) NMR spectroscopic analyses of the oligomers, and a polymerization mechanism is proposed. Unlike luteolin that showed both dose-dependent anti-inflammatory activity and cytotoxicity when tested in lipopolysaccharide-stimulated macrophages, the polyluteolin nanoparticles possess dose-dependent anti-inflammatory activity without causing cell death even at high concentrations.
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spelling pubmed-78600612021-02-05 Polymerized Luteolin Nanoparticles: Synthesis, Structure Elucidation, and Anti-Inflammatory Activity Tawornchat, Parichat Pattarakankul, Thitiporn Palaga, Tanapat Intasanta, Varol Wanichwecharungruang, Supason ACS Omega [Image: see text] Luteolin is an anti-inflammatory flavonoid commonly found in many edible plants. The compound is popularly consumed as a supplement regardless of its poor water solubility (27.8 μg/mL at 25 °C) and low bioavailability. Here, mild one-pot polymerization of luteolin into water-dispersible nanospheres, with an average dry size of 234.8 ± 101.6 nm, an aqueous size distribution of 379.1 ± 220.5 nm (PDI = 0.338), an average ζ-potential of −36.2 ± 0.2 mV, and an 89.3 ± 4.8% yield, is described. The nanospheres consist of polymerized luteolin (polyluteolin) with a weight-average molecular mass of around 410000 Da. The chemical structure of polyluteolin is identified through (1)H–(1)H correlated spectroscopy (COSY), (1)H–(13)C heteronuclear single-quantum coherence (HSQC), and (1)H–(13)C heteronuclear multiple-bond correlation (HMBC) NMR spectroscopic analyses of the oligomers, and a polymerization mechanism is proposed. Unlike luteolin that showed both dose-dependent anti-inflammatory activity and cytotoxicity when tested in lipopolysaccharide-stimulated macrophages, the polyluteolin nanoparticles possess dose-dependent anti-inflammatory activity without causing cell death even at high concentrations. American Chemical Society 2021-01-19 /pmc/articles/PMC7860061/ /pubmed/33553902 http://dx.doi.org/10.1021/acsomega.0c05142 Text en © 2021 The Authors. Published by American Chemical Society This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes.
spellingShingle Tawornchat, Parichat
Pattarakankul, Thitiporn
Palaga, Tanapat
Intasanta, Varol
Wanichwecharungruang, Supason
Polymerized Luteolin Nanoparticles: Synthesis, Structure Elucidation, and Anti-Inflammatory Activity
title Polymerized Luteolin Nanoparticles: Synthesis, Structure Elucidation, and Anti-Inflammatory Activity
title_full Polymerized Luteolin Nanoparticles: Synthesis, Structure Elucidation, and Anti-Inflammatory Activity
title_fullStr Polymerized Luteolin Nanoparticles: Synthesis, Structure Elucidation, and Anti-Inflammatory Activity
title_full_unstemmed Polymerized Luteolin Nanoparticles: Synthesis, Structure Elucidation, and Anti-Inflammatory Activity
title_short Polymerized Luteolin Nanoparticles: Synthesis, Structure Elucidation, and Anti-Inflammatory Activity
title_sort polymerized luteolin nanoparticles: synthesis, structure elucidation, and anti-inflammatory activity
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7860061/
https://www.ncbi.nlm.nih.gov/pubmed/33553902
http://dx.doi.org/10.1021/acsomega.0c05142
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