Synthesis and Characterization of Fatty Acid Oat β-Glucan Ester and Its Structure–Curcumin Loading Capacity Relationship

Abstract

An amphiphilic fatty acid oat β-glucan ester (FAOGE) was first synthesized, and its structure-curcumin loading capacity (CLC) relationship was investigated. The DS of product increased with the addition of acyl imidazole, decreased with Mw of β-glucan, and did not relate to the acyl chain length. Characterizations by FT-IR and (1)H NMR evidenced the presence of ester groups in FAOGE and confirmed its successful synthesis. The aqueous self-aggregation behavior of FAOGE was revealed by transmission electron microcopy and dynamic light scattering. With the aid of response surface methodology, a quadratic polynomial equation was obtained to quantitatively describe the structure-CLC relationship of FAOGE by using Mw of β-glucan, acyl chain length, and DS as variables. The CLC increased with Mw of β-glucan and acyl chain length but maximized at a medium DS. The maximum CLC value was obtained as 4.05 μg/mg. Hence, FAOGE is a potential candidate in solubilizing and delivering hydrophobic food ingredients.

Hydrophobically Modified Glucan as an Amphiphilic Carbohydrate Polymer for Micellar Delivery of Myricetin

“…The residues were dried in a rotary evaporator (RE-2000A, Shanghai Yarong Biochemistry Instrument Factory, Shanghai, China) and the pellets were successively dialyzed against tap water, ultrapure water, and distilled water for 24 h in a dialysis bag (molecular weight cut-off: 8000–14,000 Da), respectively. A series of OGE with different degrees of substitution (DS) were obtained by drying with an ALPHA 1-2 freeze dryer (Martin Christ GmbH, Osterode im Harz, Germany) [30].…”

“…The values of DS was determined referring to previous reports [30,31] and slightly modified. A certain amount of OGE was completely dissolved in 0.50 mL DMSO, adding 1 mL 4 mg/mL prepared sodium methanol solution, and heating it airtight at 80 °C for 1 h. After the sample cooled, 1 mL n-heptane and 1 mL saturated sodium chloride solution was added, and the supernatant was filtered (0.22 μm).…”

Opportunities for the Use of Brazilian Biomass to Produce Renewable Chemicals and Materials

“…To solve this solubility problem, β‐glucan can be reacted with acetic acid via an esterification reaction, as the addition of acetyl groups enhances solubility [77] . β‐Glucan can also react with fatty acids in a transesterification reaction to produce a surfactant that can solubilise curcumin in water [78] . Despite these efforts, new research is needed to further modify this compound with a focus on improving its solubility.…”

“…[77] β-Glucan can also react with fatty acids in a transesterification reaction to produce a surfactant that can solubilise curcumin in water. [78] Despite these efforts, new research is needed to further modify this compound with a focus on improving its solubility.…”

Preparation of Grain β-glucan Gel and Characteristics of Its Slow-release

“…It was originally extracted from ancient Chinese medicine in China and had antioxidant, liver-protective, anti-inflammatory; it has anti-cancer, lowering blood lipids, inhibiting thrombus formation, and eliminating peroxides, and has no side effects on the body. It is considered to be one of the ideal natural anti-cancer compounds [60,61,62,63]. But its poor water solubility, less absorption in the body, too fast metabolism, and low bioavailability limit its applications.…”