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

Abstract

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 1H–1H correlated spectroscopy (COSY), 1H–13C heteronuclear single-quantum coherence (HSQC), and 1H–13C 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.

Formulation, Optimization and Evaluation of Luteolin-Loaded Topical Nanoparticulate Delivery System for the Skin Cancer

“…It helps to reduce the epidermal growth factor-induced markers as well as restoration of cell-cell junctions [1,7]. LT-loaded nanoformulations such as folacin-modified nanoparticle [8], nanoparticles [9,10], NLCs [11], folic acid-modified ROS-responsive nanoparticles [12], and nanospheres [13] have been prepared and enhanced bioavailability and efficacy have been reported. However, the application of LT vesicles in the skin cancer has not been reported.…”

Modern Nanocarriers as a Factor in Increasing the Bioavailability and Pharmacological Activity of Flavonoids

“…PLGA nanoparticles with rutin, a quercetin glycoside, had an antitumor effect provided by their ability to reduce the infiltration of inflammatory cells and the activity of proinflammatory cytokines [111]. Similar anticarcinogenic and anti-inflammatory activity was also found when using the PCL/PEG and PLA/PEG polymeric carriers loaded with the flavone luteolin [112,113]. Combinations of luteolin with PLA/PEG exhibited high anticarcinogenic effect in vitro on lung cancer cells (H292 line) and squamous cell carcinoma of head and neck (Tu212 line), as well as in vivo, on the SCCHN tumor xenograft in mice [114].…”

Mechanism of Erzhiwan in treating osteoporosis based on molecular docking technology and molecular dynamics simulation

“…Most of the chemical composition had fully studied the effect of the treatment of disease.For example, quercetin and luteolin were not only the common chemical components of Ligustri lucidi Fructus and Ecliptae Herba, but also contained the most therapeutic target genes. Luteolin is a natural avonoid chemical component with a variety of pharmacological activities, such as anti-in ammatory [13,14] , anti allergic [15] , reducing uric acid [16] , anti-tumor [17,18] , etc.…”