Biophysical characterization of -glucan nanoparticles encapsulating feruloylated soy glycerides (FSG).

Water insoluble -glucans that were enzymatically synthesized using glucansucrase that was cloned from NRRL B-1118 were previously shown to form nanoparticles via high pressure homogenization. These -glucan nanoparticles were previously shown capable of encapsulating a small hydrophobic molecule. This work demonstrates that the same -glucan can be formed into nanoparticles that encapsulate feruloylated soy glycerides from modified soybean oil, a product of interest to the cosmetic and skin care industries because of the UV absorbance and antioxidant properties of the feruloyl moiety.

In Vitro Evaluation of the Adsorption Efficacy of Biochar Materials on Aflatoxin B, Ochratoxin A, and Zearalenone.

Mycotoxin sequestration materials are important tools to reduce mycotoxin illness and enable proper handling of mycotoxin-contaminated commodities. Three food-grade bentonite clays and four generally recognized as safe (GRAS) charcoal/biochar carbon materials that are marketed as feed additives and supplements were evaluated for their ability to sequester the mycotoxins aflatoxin B, ochratoxin A, and zearalenone. The surface area of the clays varied between 32.

Characterization and properties of starch-dicarboxylic acid inclusion complexes prepared by excess steam jet cooking.

A series of dicarboxylic-amylose inclusion complexes (AIC) were prepared by excess steam jet-cooking high amylose corn starch with linear C10, C12, C14, and C16 dicarboxylic acids to examine the influence of two polar head groups on complex formation. The C12, C14, and C16 dicarboxylic acid AIC were prepared in 48-63 % yields and contained 8.9-11.

Raman spectral analysis for rapid determination of zearalenone and alpha-zearalanol.

Mycotoxins, including zearalenone, are important natural products produced by fungi that occasionally contaminate agricultural commodities and pose serious health risks to consumers of food and feed. Zearalenone and its metabolite, α-zearalanol, are of significant concern due to their estrogenic and anabolic steroid activity. Several governments have regulatory standards and advisory guidelines for zearalenone and α-zearalanol.

Predictive Quantitative Structure-Activity Relationship Modeling of the Antifungal and Antibiotic Properties of Triazolothiadiazine Compounds.

Predictive models were developed using two-dimensional quantitative structure activity relationship (QSAR) methods coupled with B3LYP/6-311+G** density functional theory modeling that describe the antimicrobial properties of twenty-four triazolothiadiazine compounds against , and sp., as well as the bacteria , , , and . B3LYP/6-311+G** density functional theory calculations indicated the triazolothiadiazine derivatives possess only modest variation between the frontier orbital properties.

Development and Physical Characterization of α-Glucan Nanoparticles.

α-Glucans that were enzymatically synthesized from sucrose using glucansucrase cloned from NRRL B-1118 were found to have a glass transition temperature of approximately 80 °C. Using high-pressure homogenization (~70 MPa), the α-glucans were converted into nanoparticles of ~120 nm in diameter with a surface potential of ~-3 mV. Fluorescence measurements using 1,6-diphenyl-1,3,5-hexatriene (DPH) indicate that the α-glucan nanoparticles have a hydrophobic core that remains intact from 10 to 85 °C.

Enzymatic Synthesis and Flash Chromatography Separation of 1,3-Diferuloyl--Glycerol and 1-Feruloyl--Glycerol.

Ethyl ferulate was transesterified with Enova Oil (a soy-based vegetable oil containing 80-85% diacylglycerol) using Novozym 435 at 60 °C. The resultant feruloylated vegetable oil reaction product produced a precipitate (96.4 g, 4.

Rapid Raman spectroscopic determination of 1-feruloyl-sn-glycerol and 1,3-diferuloyl-sn-glycerol.

Ferulic acid and its derivatives are important natural products found throughout the plant kingdom and are of special interest due to their health benefits. 1-Feruloyl-sn-glycerol (FG) and 1,3-diferuloyl-sn-glycerol (FG) are two common bioproducts of ferulic acid that co-occur in nature and during the biocatalytic production of feruloylated lipids. In this paper, we report a comprehensive characterization of FG and FG using Raman and UV spectroscopies and theoretical density functional theory calculations at the B3LYP/6-311+G** level.

Determination of pH Effects on Phosphatidyl-Hydroxytyrosol and Phosphatidyl-Tyrosol Bilayer Behavior.

A robust method was developed to investigate the liposomal behavior of novel enzymatically-synthesized hydroxytyrosol and tyrosol phospholipids. Bilayer characteristic obtained by this method, including bilayer formation stability and adsorption properties, were explored using dynamic light scattering, zeta-potential measurements, and quartz crystal microbalance with dissipation monitoring (QCMD), respectively. Liposome diameters were found to typically increase from pH 5.

Charged phospholipid effects on AAPH oxidation assay as determined using liposomes.

The capacity of molecules to inhibit oxidation is widely tested using liposomes as host matrices of the antioxidant molecule of interest. Spectroscopic assays are readily used for this purpose, specifically assays using 2,2'-azobis(2-methylpropionamidine) dihydrochloride (AAPH). In this work the effect that charged lipids have on an AAPH antioxidation assay using 4,4-difluoro-5-(4-phenyl-1,3-butadienyl)-4-bora-3a,4a-diaza-s-indacene-3-undecanoic acid (C-BODIPY® 581/591) as the reporter molecule was investigated.

Phosphatidyl-hydroxytyrosol and phosphatidyl-tyrosol bilayer properties.

Hydroxytyrosol and tyrosol phospholipids were enzymatically synthesized and investigated for their bilayer properties. Dynamic light scattering demonstrated that hand extrusion at 100nm consistently resulted in liposomes of nearly 85nm diameter for both phosphatidyl-hydroxytyrosol (DOPHT) and phosphatidyl-tyrosol (DOPT). Transmission electron microscopy showed DOPT and DOPHT liposomes extruded at 100-nm to be spherical and non-distinctive from one another.

Experimental and theoretical study of the influence of water on hydrolyzed product formation during the feruloylation of vegetable oil.

Background: Feruloylated vegetable oil is a valuable green bioproduct that has several cosmeceutical applications associated with its inherent anti-oxidant and ultraviolet-absorption properties. Hydrolyzed vegetable oil by-products can influence product quality and consistency.

Results: The formation of by-products by residual water in the enzymatic synthesis of feruloylated vegetable oil was investigated using chemical theory and experimental studies by monitoring the reaction over a 22-day period.

Formation of inclusion complexes between high amylose starch and octadecyl ferulate via steam jet cooking.

Amylose-ligand inclusion complexes represent an interesting approach to deliver bioactive molecules. However, ferulic acid has been shown not to form single helical inclusion complexes with amylose from high amylose maize starch. To overcome this problem a lipophilic ferulic acid ester, octadecyl ferulate, was prepared and complexed with amylose via excess steam jet cooking.

Feruloyl glycerol and 1,3-diferuloyl glycerol antioxidant behavior in phospholipid vesicles.

Feruloyl-sn-glycerol (FG) and 1,3-diferuloyl-sn-glycerol (F2G), the by-product of biocatalytic transesterification soybean oil and ethyl ferulate, were examined for their behavior in phospholipid vesicles. Based on absorbance and fluorescence methods, FG and F2G both were found to partition into vesicles and incorporate well into 1,2-dioleoylphosphocholine (DOPC) vesicles. FG and F2G incorporation resulted in vesicles that were as or slightly more stable than the unloaded vesicles.

Octadecyl ferulate behavior in 1,2-Dioleoylphosphocholine liposomes.

Octadecyl ferulate was prepared using solid acid catalyst, monitored using Supercritical Fluid Chromatography and purified to a 42% yield. Differential scanning calorimetry measurements determined octadecyl ferulate to have melting/solidification phase transitions at 67 and 39°C, respectively. AFM imaging shows that 5-mol% present in a lipid bilayer induced domains to form.

Hydroxytyrosol and tyrosol esters partitioning into, location within, and effect on DOPC liposome bilayer behavior.

The phenols hydroxytyrosol and tyrosol made abundantly available through olive oil processing were enzymatically transesterified into effective lipophilic antioxidants with cuphea oil. The hydroxytyrosyl and tyrosyl esters made from cuphea oil were assessed for their ability to partition into, locate within and effect the bilayer behavior of 1,2-dioloeoylphosphatidylcholine liposomes and compared to their counterparts made from decanoic acid. Partitioning into liposomes was on the same scale for both hydroxytyrosyl derivatives and both tyrosyl derivatives.

Phenol esterase activity of porcine skin.

The alkyl esters of plant-derived phenols may serve as slow-release sources for cutaneous delivery of antioxidants. The ability of skin esterases to hydrolyze phenolic esters was examined. Esters of tyrosol and hydroxytyrosol were prepared from decanoic and lipoic acids.

Co-pyrolysis of swine manure with agricultural plastic waste: laboratory-scale study.

Manure-derived biochar is the solid product resulting from pyrolysis of animal manures. It has considerable potential both to improve soil quality with high levels of nutrients and to reduce contaminants in water and soil. However, the combustible gas produced from manure pyrolysis generally does not provide enough energy to sustain the pyrolysis process.

Stability of a liposomal formulation containing lipoyl or dihydrolipoyl acylglycerides.

Context: The acylglycerides of lipoic and dihydrolipoic acids may serve as slow-release sources for cutaneous delivery of these antioxidants when formulated in a liposomal vehicle.

Objective: Testing was conducted to determine the storage stability of lipoyl glycerides in phospholipid-based liposomes.

Materials And Methods: Lipoyl glycerides prepared by transesterification of lipoic acid with high oleic sunflower oil were incorporated into unilamellar liposomes comprised of soy phosphatidylcholine (soyPC) or dioleoylphosphatidylcholine (DOPC).

Synthesis and tribological investigation of lipoyl glycerides.

Lipoyl glycerides were synthesized by enzymatic transesterification of lipoic acid with high-oleic sunflower oil in 2-methyl-2-butanol solvent. The synthesis gave a crude product mixture comprising unreacted lipoic acid, free fatty acids, and several lipoyl glyceride structures of varying lipoic acid substitution. A more purified product mixture, devoid of unreacted lipoic acid and free fatty acids, was obtained in 61% yield.

Carboxyl-terminated PAMAM dendrimer interaction with 1-palmitoyl-2-oleoyl phosphocholine bilayers.

Polyanionic polymers and liposomes have a great potential use as individual drug delivery systems and greater potential as a combined drug delivery system. Thus, it is important to better understand the interactions of polymers with phospholipid bilayers. A mechanistic study of the interaction between carboxyl-terminated poly(amidoamine) (PAMAM) dendrimers with 1-palmitoyl-2-oleoyl-phosphatidylcholine (POPC) bilayer using fluorescence leakage and quartz crystal microbalance with dissipation monitoring (QCMD) was conducted.

Preservation of polyunsaturated fatty acyl glycerides via intramolecular antioxidant coupling.

Ferulic acid and its esters are known to be effective antioxidants. Feruloyl di-γ-linolenoylglycerol was assessed for its ability to serve as an antioxidant for preventing the oxidation of its γ-linolenoyl polyunsaturated fatty acyl groups in model membrane phospholipid vesicles. The molecule was incorporated into single-lamellar vesicles comprised of 1,2-dioleoyl-sn-glycero-3-phosphocholine.

Dihydrolipoyl dioleoylglycerol antioxidant capacity in phospholipid vesicles.

Antioxidants have critical roles in maintaining cellular homeostasis and disease-state prevention. The multi-functional agent α-lipoic acid offers numerous beneficial effects to oxidatively stressed tissues. α-Lipoic acid was enzymatically incorporated into a triglyceride in conjunction with oleic acid, creating lipoyl dioleoylglycerol, and chemically reduced to form dihydrolipoyl dioleoylglycerol.

Evaluation of soyscreen in an oil-based formulation for UV protection of Beauveria bassiana conidia.

Soyscreen oil was studied as a formulation ingredient to protect Beauveria bassiana (Balsamo) Vuillemin conidia from UV degradation. Feruloylated soy glycerides, referred to as Soyscreen oil, are biobased UV-absorbing molecules made by combining molecules of soybean oil with ferulic acid. Conidia stored in Soyscreen oil for 28 wk at 25, 30, and 35 degrees C retained viability as well as conidia stored in sunflower oil, demonstrating that Soyscreen did not adversely affect viability with prolonged storage.

1,3-Diferuloyl-sn-glycerol from the biocatalytic transesterification of ethyl 4-hydroxy-3-methoxy cinnamic acid (ethyl ferulate) and soybean oil.

1,3-Diferuloyl-sn-glycerol is found ubiquitously throughout the plant kingdom, possessing ultraviolet adsorbing and antioxidant properties. Diferuloyl glycerol was synthesized and isolated as a byproduct in up to 5% yield from a pilot plant scale packed-bed, biocatalytic transesterification of ethyl ferulate with soybean oil or mono- and diacylglycerols from soybean oil. The yield of the diferuloyl glycerol byproduct was directly proportional to the overall water concentration of the bioreactor.