Interaction of curcumin with phosphatidylcholine: A spectrofluorometric study

Curcumin [1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3, 5-dione], the main constituent of the rhizomes of the plant Curcume longa L. (turmeric), is a powerful antioxidant in both enzymatic and nonenzymatic systems. The interactions of curcumin with egg and soy phosphatidylcholine were followed by fluorescence spectroscopy. Curcumin had very weak fluorescence in aqueous system, which was enhanced in apolar environments. Curcumin emitted at 490 nm after being excited at 451 nm in phosphatidylcholine micelles. The equilibrium constants for the interaction of curcumin with egg and soy phosphatidylcholine were (3.26 +/- 0.2) x 10(5) and (2.64 +/- 0.2) x 10(5) M(-1), respectively. From the Scatchard plot of the fluorometric data, it was inferred that one molecule of curcumin could bind six molecules of phosphatidylcholine. The equilibrium constant for the phosphatidylcholine-curcumin interaction decreased with temperature, indicating the amphiphilic nature of curcumin. The DeltaG, DeltaH, and DeltaS values obtained for the interaction of egg phosphatidylcholine-curcumin were -7.8 +/- 0.3 kcal/mol, -9.6 +/- 0.4 kcal/mol, and -6.8 +/- 0.2 cal/mol/K, respectively. The fluorescence anisotropy measurements of curcumin with phosphatidylcholine suggested that the anisotropy of the curcumin molecule did not change in phosphatidylcholine. The interaction of divalent metal ions with phosphatidylcholine-curcumin in comparison with phosphatidylcholine-1-anilino-8-naphathalenesulfonic acid complex suggested the strong binding of curcumin to metal ions.     

Spectrophotometric evidence for the solubilization site of betalain pigments in membrane biomimetic systems

The solubilization site of two betalain pigments, namely, betanin and indicaxantin, into l-alpha-dipalmitoyl-phosphatidylcholine (DPPC) and dimyristoylphosphatidylcholine (DMPC) vesicles was investigated by a spectrophotometric study. Pigment absorbance was monitored by varying phospholipid concentration, at a constant temperature that was varied in a range including the main phase transition temperature (Tm) of the relevant phospholipid bilayer. Maximum betanin absorption increased with the increase of DPPC concentration within the entire temperature range, reaching a plateau. The binding constant (Kb) of the pigment, calculated according to a pseudo-two-phase model, varied with the temperature, indicating that betanin is located at the hydrophobic interior of the bilayer. Other measurements of binding of betanin to DMPC and of indicaxanthin to either DPPC or DMPC vesicles ruled out that these compounds were solubilized in the hydrophobic interior of these bilayers.     

Improving the oral bioavailability of curcumin using novel organogel-based nanoemulsions

Curcumin is a natural bioactive compound with many health-promoting benefits. Its low oral bioavailability limits its application in functional foods. In the present study, novel organogel-based nanoemulsions have been developed for oral delivery of curcumin and improvement of its bioavailability. Recently developed curcumin organogel was used as the oil phase in the curcumin nanoemulsion formulation. Tween 20 was selected as the emulsifier on the basis of maximum in vitro bioaccessibility of curcumin in the nanoemulsion. In vitro lipolysis profile revealed that the digestion of nanoemulsion was significantly faster and more complete than the organogel. Permeation experiments on Caco-2 cell monolayers suggested that digestion-diffusion was the major absorption mechanism for curcumin in the nanoemulsion. Furthermore, in vivo pharmacokinetics analysis on mice confirmed that the oral bioavailability of curcumin in the nanoemulsion was increased by 9-fold compared with unformulated curcumin. This novel formulation approach may also be used for oral delivery of other poorly soluble nutraceuticals with high loading capacity, which has significant impact in functional foods, dietary supplements and pharmaceutical industries.     

Effects of heating conditions on the glass transition parameters of amorphous sucrose produced by melt-quenching

This research investigates the effects of heating conditions used to produce amorphous sucrose on its glass transition (T(g)) parameters, because the loss of crystalline structure in sucrose is caused by the kinetic process of thermal decomposition. Amorphous sucrose samples were prepared by heating at three different scan rates (1, 10, and 25 °C/min) using a standard differential scanning calorimetry (SDSC) method and by holding at three different isothermal temperatures (120, 132, and 138 °C) using a quasi-isothermal modulated DSC (MDSC) method. In general, the quasi-isothermal MDSC method (lower temperatures for longer times) exhibited lower T(g) values, larger ΔC(p) values, and broader glass transition ranges (i.e., T(g end) minus T(g onset)) than the SDSC method (higher temperatures for shorter times), except at a heating rate of 1 °C/min, which exhibited the lowest T(g) values, the highest ΔC(p), and the broadest glass transition range. This research showed that, depending on the heating conditions employed, a different amount and variety of sucrose thermal decomposition components may be formed, giving rise to wide variation in the amorphous sucrose T(g) values. Thus, the variation observed in the literature T(g) values for amorphous sucrose produced by thermal methods is, in part, due to differences in the heating conditions employed.     

Chain length effects in isoflavonoid daidzein alkoxy derivatives as antioxidants: a quantum mechanical approach

Daidzein, an isoflavonoid with known prooxidative effects in heterogeneous lipid/water systems, changes to an antioxidant for 7-n-alkoxy derivatives of daidzein. For an alkyl length increasing from 4 to 8, 12, and 16 carbons, the oxidation potential decreases gradually from 1.09 V (vs NHE) for daidzein (D) to 0.94 V for D16 in tetrahydrofuran as determined by cyclic voltammetry at 25 °C. The prooxidative effects transform into antioxidative effects from D8 with a maximal effect for D12 for aqueous phase initiation of lipid oxidation in liposomes despite a gradual decrease in Trolox equivalent antioxidant capacity (TEAC) with increasing alkyl chain length. Quantum mechanical calculations using density functional theory (DFT) showed that the bond dissociation energy of the O-H bond of the 4'-phenol is constant along the homologue series in contrast to Δμ, the change in dipole moment upon hydrogen atom donation, which increases for increasing chain length. The frontier orbital energy gap goes through a maximum for D12. The change in the A-to-B dihedral angle upon hydrogen atom donation further shows a maximum for D12 of 6.45°. The importance of these microscopic properties for antioxidative activity was confirmed by a change in liposome fluorescence anisotropy using a fluorescent probe showing maximal penetration into the lipid bilayer for D12 along the homologue series.     

Effect of processing of black currant press-residue on polyphenol composition and cell proliferation

The press-residue of black currants provides a good source of phenolic antioxidants. The purpose of this study was to optimize the extraction of phenolic compounds from the press-residue by use of extraction conditions compatible with food use. The effects of temperature, extraction duration, and use of ultrasound-assisted extraction on the juice yield, total phenolics (TP), and anthocyanin content of aqueous extracts were studied. Within the variables and response factors tested, the optimal conditions were a 15 min extraction at 90 °C. No significant effect from ultrasound-assisted extraction was found. The composition of anthocyanins and polyphenols was highly dependent on the extraction temperature. The percentage contribution of delphinidin- and cyanidin-3-rutinoside to TP had a negative linear correlation with temperature, while delphinidin- and cyanidin-3-glucoside had a positive linear correlation with temperature, with a maximum amount obtained at 80 °C and 55 °C, respectively. Furthermore, extracts obtained at higher temperatures showed a stronger inhibition of proliferation of Caco-2, HT-29, and HCT 116 cells than extracts obtained at lower temperatures. This may be due to the decomposition of complex polyphenols at higher temperatures, making them more accessible to the cells.     

Preparation and enhancement of oral bioavailability of curcumin using microemulsions vehicle

A new microemulsions system of curcumin (CUR-MEs) was successfully developed to improve the solubility and bioavailability of curcumin. Several formulations of the microemulsions system were prepared and evaluated using different ratios of oils, surfactants, and co-surfactants (S&CoS). The optimal formulation, which consists of Capryol 90 (oil), Cremophor RH40 (surfactant), and Transcutol P aqueous solution (co-surfactant), could enhance the solubility of curcumin up to 32.5 mg/mL. The pharmacokinetic study of microemulsions was performed in rats compared to the corresponding suspension. The stability of microemulsions after dilution was excellence. Microemulsions have significantly increased the C(max) and area under the curve (AUC) in comparison to that in suspension (p < 0.05). The relative bioavailability of curcumin in microemulsions was 22.6-fold higher than that in suspension. The results indicated that the CUR-MEs could be used as an effective formulation for enhancing the oral bioavailability of curcumin.     

Modified fast procedure for the detection and screening of antiglycative phytochemicals

In an attempt to elevate temperature to facilitate glycation, a nonenzymatic reaction by incubation of bovine serum albumin (BSA) and fructose at 50 °C for 24 h has been developed. As conducted and compared to a routine procedure by incubation of BSA and fructose at 37 °C for 168 h, the reactant fluorescence intensities and SDS-PAGE-detected glycated BSA quantities produced by both test temperatures increased with time of incubation. As the Amadori products and α-dicarbonyl compounds during incubation were quantified, both quantities produced at each temperature also increased with an increase of time of incubation, and their trends of changes at both temperatures were similar. In practical application for the detection and screening of the antiglycative phytochemicals, each of 20 peanut root extracts was introduced to a series of BSA-fructose solutions and incubated at 37 and 50 °C for 168 and 24 h, correspondingly. All extracts exhibited notable activities and varied depending on peanut origins. Pair comparison of the resultant antiglycative activities determined at 37 and 50 °C showed that both determined activities for each peanut root extract deviated limitedly. As further analyzed, SDS-PAGE-detected glycated BSA quantities formed at 50 °C were closely proportional to the antiglycative activities determined on the basis of their fluorescence intensities. It is of merit to demonstrate that fluorescence-based determination of BSA-fructose reactant after incubation at 50 °C for 24 h is practical and time-saving in the detection and screening of antiglycative phytochemicals.     

Physical stability of liposomes prepared from milk fat globule membrane and soya phospholipids

Previous research has shown that liposomes prepared from a milk fat globule membrane (MFGM) phospholipid fraction had a significantly higher phase transition temperature, thicker membrane, and lower membrane permeability than liposomes prepared from soya phospholipid material. Subsequent investigations into the relative stability of the two liposome dispersions have found that the MFGM phospholipid liposomes are more stable than their soya counterparts in a range of pH conditions, at a variety of storage and processing temperatures, and in the presence of mono- and divalent cations. These results illustrate some potential advantages in the use of MFGM phospholipids for the manufacture of liposomes for use in food systems.     

Stability of white wine proteins: combined effect of pH, ionic strength, and temperature on their aggregation

Protein haze development in white wines is an unacceptable visual defect attributed to slow protein unfolding and aggregation. It is favored by wine exposure to excessive temperatures but can also develop in properly stored wines. In this study, the combined impact of pH (2.5-4.0), ionic strength (0.02-0.15 M), and temperature (25, 40, and 70 °C) on wine protein stability was investigated. The results showed three classes of proteins with low conformational stability involved in aggregation at room temperature: β-glucanases, chitinases, and some thaumatin-like protein isoforms (22-24 kDa). Unexpectedly, at 25 °C, maximum instability was observed at the lower pH, far from the protein isoelectric point. Increasing temperatures led to a shift of the maximum haze at higher pH. These different behaviors could be explained by the opposite impact of pH on intramolecular (conformational stability) and intermolecular (colloidal stability) electrostatic interactions. The present results highlight that wine pH and ionic strength play a determinant part in aggregation mechanisms, aggregate characteristics, and final haze.     

Textural properties and their correlation to cell structure in porous food materials

This paper focuses on understanding the role of structural parameters and starch crystallization on the toughness of cake samples. Accurate mechanical measurements were performed to obtain toughness values, and these were related to structural parameters obtained from image analyses. Three-dimensional skeletons of food samples were generated by using X-ray tomography technique. The structural parameters (cell diameter, cell wall thickness, thickness to radius ratio (t/R), fragmentation index) were obtained after processing of the images with CTan software. The basic hypothesis of the paper is to show that the structural parameter t/R is a determinant for predicting toughness, which is a critical indicator of freshness. Freshness in cakes and other baked products is a leading factor in consumer perception. For this purpose three different cake formulations were stored at 37 and 50 °C. Cycling from these temperatures to lower storage temperatures of 25 and 4 °C was done to accelerate the starch retrogradation rate. Experimental results indicated that there was a strong interrelationship between morphological structure and the mechanical properties with regression coefficients of 0.68 and 0.95. Starch retrogradation, which was followed by X-ray diffractometry, was found to be directly proportional to toughness values, where the percent relative crystallinity increased with storage temperature.     

Trapping of methylglyoxal by curcumin in cell-free systems and in human umbilical vein endothelial cells

Curcumin, the most active compound of curcuminoids, has been shown to inhibit formation of advanced glycation end products (AGEs) in streptozotocin-induced diabetic rats. However, little is known on whether curcumin may trap methylglyoxal (MGO), a major reactive dicarbonyl compound, to inhibit AGE formation. We found that one molecule of curcumin effectively trapped one molecule of MGO at a 1:3 ratio at 24 h of incubation under physiological conditions (pH 7.4, 37 °C). Curcumin decreased N(ε)-(carboxymethyl)lysine (CML) expression in human umbilical vein endothelial cells. We further used two curcumin analogues, dimethoxycurcumin (DIMC) and ferulic acid, to investigate the possible MGO-trapping mechanism of curcumin. Results reveal that DIMC, but not ferulic acid, exhibited MGO-trapping capacity, indicating curcumin traps MGO at the electron-dense carbon atom (C10) between the two keto carbon groups. Thus, curcumin may prevent MGO-induced endothelial dysfunction by directly trapping MGO.     

Can the thermodynamic melting temperature of sucrose, glucose, and fructose be measured using rapid-scanning differential scanning calorimetry (DSC)?

The loss of crystalline structure in sucrose, glucose, and fructose has been shown to be due to the kinetic process of thermal decomposition (termed apparent melting), rather than thermodynamic melting. The purpose of this research was to investigate whether or not it is possible to scan quickly enough to suppress the kinetic process of thermal decomposition and reach the thermodynamic melting temperature of these sugars using a new rapid-scanning DSC. Indium, a thermodynamic melting material, and sucrose, glucose, and fructose were analyzed at three heating rates from 1 to 25 °C/min using standard DSC and at seven heating rates from 50 to 2000 °C/min using rapid-scanning DSC. Thermodynamic melting was achieved when the onset temperature (T(m onset)) of the endothermic peak leveled off to a constant value independent of heating rate. The T(m onset) for indium was constant (156.74 ± 0.42 °C) at all heating rates. In the case of fructose, the T(m onset) increased considerably until a heating rate of approximately 698 °C/min, after which the average T(m onset) for the remaining three heating rates was constant at 135.83 ± 1.14 °C. Thus, 135.83 °C is proposed to be the thermodynamic melting temperature of fructose. It is important to note that the heating rate at which this thermodynamic melting temperature is achieved is most likely influenced by the type and amount of trace components (e.g., water and salts) contained in the fructose, which are known to vary widely in sugars. In the case of sucrose and glucose, thermodynamic melting temperatures were not able to be obtained, because the upper limit heating rate used was not fast enough to suppress thermal decomposition and achieve thermodynamic melting, perhaps due to the higher apparent T(m onset) for sucrose and glucose compared to that for fructose.     

2,4-D丁酯的水解与光解特性研究

通过室内模拟试验,研究2,4-D丁酯在不同pH值和温度下的水解动态和在有机溶剂中的光解特性。结果表明,2,4-D丁酯的水解与光解均符合一级动力学方程。在pH7以下的缓冲溶液中,2,4-D丁酯的水解反应十分缓慢,但在碱性溶液中其水解速率加快。25℃下2,4-D丁酯在pH5、7和9的缓冲溶液中的水解半衰期分别为23.5、5.8d和10.7min。2,4-D丁酯的水解速率随温度升高而增加,在温度为15、25℃和35℃的pH7缓冲溶液中的水解半衰期分别为21.5、5.8、3.9d,平均温度效应系数为2.57。2,4-D丁酯水解反应的活化能与温度之间无明显相关性,而活化熵与温度呈显著相关性。2,4-D丁酯的水解主要由活化熵所驱动。采用GC-MS技术对2,4-D丁酯水解产物进行鉴定,确定水解产物主要是2,4-二氯苯氧乙酸和2,4-二氯苯酚。2,4-D丁酯在正己烷中光解速率比在甲醇中快,在丙酮中几乎不发生光解,其光解速率随浓度的升高而减慢。     

Storage stability of ascorbic acid incorporated in edible whey protein films

The stability of ascorbic acid (AA) incorporated in whey protein isolate (WPI) film and the related color changes during storage were studied. No significant loss of AA content was found in any films prepared from pH 2.0 casting solution stored at 30% relative humidity (RH) and 22 °C over 84 days. Total visible color difference (ΔE*(ab)) of all films slowly increased over storage time. The ΔE*(ab) values of pH 3.5 films were significantly higher than those of pH 2.0 films. The stability of AA-WPI films was found to be mainly affected by the pH of the film-forming solution and storage temperature. Oxidative degradation of AA-WPI films followed Arrhenius behavior. Reduction of the casting solution pH to below the pK(a1) (4.04 at 25 °C) of AA effectively maintained AA-WPI storage stability by greatly reducing oxidative degradation, whereas anaerobic and nonenzymatic browning were insignificant. The half-life of pH 2.0 AA-WPI film at 30% RH and 22 °C was 520 days.     

Production system and storage temperature influence grapefruit vitamin C, limonoids, and carotenoids

Concentrations of grapefruit (cv. 'Rio Red'; Citrus paradisi Macf.) bioactives grown under organic and conventional production systems were evaluated after storage at various temperatures. The first experiment was conducted in November 2008 and the second experiment was conducted in February 2011 using commercial production, processing, and packing procedures. The harvested grapefruits were stored at 23 °C (room temperature) or 9 °C for 4 weeks and analyzed for vitamin C, limonoids, and carotenoids at the end of each week using HPLC. Vitamin C levels were higher in organically grown grapefruits (41.8 mg/100 g) compared to conventionally grown grapefruits (39.2 mg/100 g) at 0 days after harvest in the first experiment. However, production system did not significantly affect vitamin C levels in the second experiment. During storage at room temperature, vitamin C degradation losses ranged from 0.5 to 7% for organically produced grapefruits and from 3 to 18% for conventional grapefruits in both experiments. In the first experiment at harvest, organically produced grapefruits had 77% higher (p ≤ 0.05) nomilin than conventionally produced grapefruits, whereas grapefruits grown under the conventional production system had 2-fold higher lycopene levels compared to organic grapefruits. In the second experiment, both β-carotene and lycopene levels were significantly (p ≤ 0.05) higher in conventionally produced grapefruits than in organic grapefruits. Overall, conventional production significantly increased grapefruit carotenoid levels in both experiments. In general, storage temperature (room temperature and 9 °C) had minimal effects on vitamin C degradation but significant effects on the degradation of carotenoids in the first experiment.     

基于高光谱参数建立苗期高温条件下草莓叶片叶绿素含量估算模型

以“红颜”草莓（Fragaria×ananassa Duch“Benihope”）为试材,于2021年9−11月在人工气候室进行苗期（9～12片真叶,叶长≥5cm）动态高温环境控制实验,日最高温度以32℃为起点,设置日最高气温/日最低气温分别为32℃/22℃、35℃/25℃、38℃/28℃和41℃/31℃共4个水平,持续时间分别为2d、5d、8d和11d,以28℃/18℃为对照（CK）。试验期间空气相对湿度60%～70%,光周期12h/12h（6：00−18：00）,光照强度800μmolm⁻²s⁻¹。测定不同处理下叶片叶绿素含量及高光谱反射率,对原始光谱进行变换,从而细化光谱特征信息。在相关分析的基础上,建立原始和一阶敏感波段植被指数,进而筛选出表征叶绿素含量的光谱特征参数,以期构建叶绿素含量最佳估算模型。结果表明：（1）随着温度的升高和高温持续时间的延长,草莓叶片叶绿素a、叶绿素b和总叶绿素（a+b）含量呈下降趋势。（2）草莓叶片原始光谱在可见光区域均存在绿峰和红谷,除绿峰和红谷外各处理间差异不明显,高温条件下的近红外区域反射率与CK相比出现不同程度的上升。与原始光谱相比,一阶导数光谱曲线震荡更剧烈,且能够显著突出红边参数特征,各处理的红边位置λ_r稳定在716nm,红边幅值D_r与红边面积S_r差异显著;而在连续统去除光谱中各处理的绿峰（550nm附近）和红谷（675nm附近）被完全突显出来。（3）在光谱反射率与叶绿素含量相关性分析的基础上,选取原始光谱与一阶导数光谱在可见光和近红外波段相关性最强的R₇₄₇、R₈₀₀和R'₇₁₆、R'₉₀₆为敏感波段组合,构建植被指数。（4）PVI、MSAVI、TSAVI、TSAVI'、DVI'、MSAVI'、PVI'、SAVI'、D_r和S_r指数与叶绿素含量相关性达极显著水平,可作为表征设施草莓叶片叶绿素含量对苗期高温胁迫响应的高光谱特征参数。其中以TSAVI、DVI'和PVI'植被指数建立的逐步回归模型为叶绿素含量最佳估算模型,其决定系数（R²）为0.843,均方根误差（RMSE）为0.379,相对误差（RE）为12.65%。     

Fate of flavonoids in the outer skins of onion (Allium cepa L.) throughout curing

Reducing the current U.K. curing temperature from 28 to 20 °C would help to reduce energy costs; however, onion skin appearance and consumer acceptability may be detrimentally affected. The aim of this study was to elucidate the compounds responsible for the difference in color between brown and red onions cured at 20 and 28 °C by monitoring dynamic biochemical changes in the skin at set intervals during curing and after storage from two years' data. Sugar concentrations appeared to play no role in the difference in onion skin appearance when cured at different temperatures. Using regression, principal component, and partial least-squares discriminant analyses, the decrease in skin H° after the curing of brown onion cultivars at 28 °C was linked to a decrease in individual flavonol concentrations, possibly due to their oxidation at higher temperatures into brown pigmented compounds. Red onion cultivars cured at lower temperatures and for a shorter curing period had higher concentrations of individual anthocyanins as well as a darker skin color. Skin water content was reduced significantly in only the first 6 days of curing. Taken together, this suggests that current U.K. curing practice could be carried out at a lower temperature (20 °C) and/or for a shorter duration, resulting in reduced curing costs and possibly improved skin appearance.     

Effects of Preparation Temperature on Gelation Properties and Molecular Structure of High‐Amylose Maize Starch

In this study, 3% aqueous high‐amylose maize starch (Hylon VII) dispersions were heated to temperatures of 140–165°C. The onset and rate of gel formation was observed using a small‐strain oscillation rheometer as a function of temperature from 90 to 25°C. The gel formation clearly began earlier in high‐amylose starch paste preheated at lower temperatures, but the rate of gelation was slower and the resulting gel was weaker in comparison with starch pastes preheated at higher temperatures. In addition, the structure of the final gels was studied using large deformation compression measurements. The most rigid gel structure on the basis of small and large deformation tests was obtained for high‐amylose starch gel preheated to 150–152°C, depending on the type of measurement. The rate of gelation was also fastest in that temperature range. High‐amylose gels heated to higher temperatures lost their rigidity. The molecular weight distribution of starch molecules was measured by size‐exclusion chromatography. Heating caused extensive degradation of amylopectin, which had a great effect on amylose gel formation and the final gel properties of high‐amylose maize starch. Micrographs of Hylon VII gels showed that phase separation of starch components visible in light microscopy occurred on heating to higher temperatures.