Intercalation of Apocarotenoids from Annatto (Bixa orellana L.) into Layered Double Hydroxides

Abstract

Synthetic conditions were evaluated to intercalate norbixin into layered double hydroxides (LDH). Norbixin was isolated from a hydrosoluble commercial annatto extract. LDH samples comprising M 2+ /Al 3+ (M = Mg, Zn) were synthesized by coprecipitation and characterized by X-ray diffraction, thermal analysis coupled to mass spectrometry, vibrational spectroscopies, and solid-state 13 C nuclear magnetic resonance. Radical scavenging activity of LDH hybrids was monitored by electron paramagnetic resonance towards the stable radical DPPH (1,1-diphenyl-2-picrylhydrazyl). LDH hosts presented more than 50 wt.% of norbixin and d-spacing (003) values of about 2.5 or 3.0 nm depending of the cation LDH composition. Vibrational spectra assignment (supported by density functional theory calculations) confirmed the chemical integrity of norbixin after intercalation into LDH. The inorganic layers were found to enhance the thermal stability of norbixin upon intercalation. The free radical scavenging capacity of norbixin was retained when immobilized into LDH. Considering that zinc and magnesium-LDH matrices are biocompatible and that norbixin presents biological activity, the hybrid materials appear as promising systems for biomedical assessment.

Biomaterials Based on Organic Polymers and Layered Double Hydroxides Nanocomposites: Drug Delivery and Tissue Engineering

“…[ 22 , 24 ], vitamins (vitamin C, folic etc.) [ 107 , 108 ], phytochemicals (curcumin, coumaric, abietic, norbixin) [ 109 , 110 , 111 , 112 ], and nucleotides (DNA and RNA) [ 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 ], as represented in Figure 8 . Hence, by combining different metal cations, stoichiometries and intercalated species, a huge number of LDH materials can be engendered to attend to pharmaceutical and medical needs.…”

Development of Dipeptide N–acetyl–L–cysteine Loaded Nanostructured Carriers Based on Inorganic Layered Hydroxides

“…The intercalated species studied cover a wide range of properties such as anti-inflammatory, antibiotic, antitumor, anticoagulant, antimicrobial, antidepressant, and antioxidant properties [ 44 , 45 ]. We have worked on the development of LDH host matrices for use as carriers of anionic species derived, for instance, from ibuprofen [ 46 ], sulindac [ 47 ], mefenamic acid [ 48 ], coumaric acid [ 49 , 50 ], pravastatin [ 51 ], naproxen [ 43 ], norbixin [ 52 ], and ciprofloxacin [ 53 ]. For some LDH materials, in vivo tests for phases intercalated with chloride ions (Mg 2 Al–Cl and Zn 2 Al–Cl [ 42 ], Mg 4 FeAl–Cl and Zn 4 FeAl–Cl [ 43 ]), or coumarate (Mg 2 Al–Cou and Zn 2 Al–Cou) [ 49 ] were performed to assess their biocompatibility by intramuscular implants, while in vitro assays of intercalated sulindac (Mg 2 Al–Sul and Zn 2 Al–Sul) [ 47 ] and mefenamate (Mg 2 Al–Mef) [ 48 ] materials were also studied.…”