Three extra virgin olive oils having different fatty acid compositions and total phenol contents were submitted to an accelerated storage test at 60°C for up to 21 weeks. Their oxidative status, evaluated by peroxide values and total phenolic content, was related to differential scanning calorimetry cooling profiles and thermal properties. Changes in crystallization profiles were consistent starting from 12 weeks for the two oil samples (B and C) that had a higher content of linoleic acid and medium/low amounts of phenols, respectively, whereas they became detectable at the end of the test for the remaining oil (sample A). Decrease of crystallization enthalpy and shift of transition towards lower temperature were also evident at 4 weeks of storage for samples B and C, whereas the same changes in the transition profile were noticeable at 12 weeks for sample A. Differential scanning calorimetry appears to be suitable for the discrimination of oxidative status of extra virgin olive oils with widely different fatty acid composition.
Detailed fatty acid compositions of five species of the brown algae Sargassum (S. fulvellum, S. horneri, S. boreale, S. thunbergii, and S. yezoense) were determined using silver ion solid phase extraction, gas chromatography (GC), and GC-mass spectrometry (GC-MS) techniques. In addition to a high number of typical saturated and unsaturated fatty acids, the GC-MS spectra of the 4,4-dimethyloxazoline derivatives of fatty acids revealed the occurrence of small amounts of unusual non-methylene-interrupted (NMI) fatty acids with Δ5 unsaturation, namely, 5,9-eicosadienoic (5,9-20:2), 5,11,14-eicosatrienoic (5,11,14-20:3), and 5,11,14,17-eicosatetraenoic (5,11,14,17-20:4) acids. Of these three NMI acids, the 5,9-20:2 acid was found to be the most abundant (0.4%–2.3% of the total fatty acids) and was detected for the first time in algae.
The present study was undertaken to examine the effect of cerebrosides derived from the sea cucumber Acaudina molpadioides and the starfish Asterias amurensis on the anti-tumor activity in vitro and in vivo. The results indicated that both Acaudina molpadioides cerebrosides (AMC) and Asterias amurensis cerebrosides (AAC) exhibited an inhibitory effect on cell proliferation through induction of apoptosis in S180 cells. Moreover, administration of AMC and AAC (50 mg/kg BW) on S180 tumor bearing mice reduced the tumor weight by 45.24 % and 35.71 %, respectively. In S180 ascites tumor model, AMC and AAC (50 mg/kg BW) treatment exhibited a significant ascites fluid growth inhibition of 31.23 % and 22.72 %. Furthermore, the ascites tumor cell viability ratio in AMC and AAC groups reduced to 50.89 % and 51.69 %, respectively. The life span of AMC and AAC administrated groups increased by 55.28 % and 35.77 % compared to control. Quantitative real-time PCR analysis demonstrated that the administration of AMC and AAC down-regulated the expression of Bcl-2, Bcl-xL, while on the other hand, up-regulated Bax, Cytochrome c, caspase-9 and caspase-3 mRNA level of the S180 ascites tumor cells. It was concluded that AMC and AAC should have potential anti-tumor activity both in vitro and in vivo by inducing apoptosis through the mitochondria-mediated apoptosis pathway. AAC seemed to be more effective than AMC in vitro but less potent in vivo. It may depend on the structural differences in their fatty acid groups and sphingoid bases.
We previously fed rats with an ester (90 ppm in a powdered AIN93G diet) synthesized from gallic acid and 1,2-dioleoyl glycerol and found that it promoted weight loss more effectively than either octyl gallate or gallic acid. Here, we esterified ferulic acid (FerA) with oleic acid, monooleoyl glycerol and dioleoyl glycerol to obtain oleoyl ferulic acid (FO), feruloyl monooleoyl glycerol (FMO) and feruloyl dioleoyl glycerol (FDO) esters, respectively. A mixture of AIN93G and 90 ppm of each ester and FerA was fed to 10-week-old male Wistar rats for 12 weeks. The FMO and FDO groups weighed less than the control group starting from approximately 16 weeks of age. At 21 and 22 weeks of age, weight significantly differed between the FMO and both groups, respectively, and controls. The FO, FerA and control groups did not significantly differ in terms of body, liver, kidney and retroperitoneal fat tissue weights and serum biochemical findings. We concluded that the hydroxyl group of FerA is essential for promoting weight loss and that the carboxyl group should be esterified with alcohol. In addition, monooleoyl glycerol and dioleoyl glycerol did not show any difference as the alcohol moiety of the ester in the weight loss effect.
2,3-O-Dipalmitoyl-D-glyceric acid (PA2-DGA) was synthesized from D-glyceric acid calcium salt and palmitoyl chloride with improved yield. Direct condensation between the D-glyceric acid calcium salt and palmitoyl chloride produced PA2-DGA with a yield of <10%, whereas stepwise synthesis yielded this compound at up to 24% of overall yield. PA2-DGA was then subjected to a cytotoxic test using normal human dermal fibroblasts and primary normal human dermal microvascular endothelial cells. This compound had no toxic effects on human cells in vitro at concentrations up to 34 μM.
Glyceric acid (GA) is one of the most promising functional hydroxyl acids, and it is abundantly obtained from glycerol by a bioprocess using acetic acid bacteria. In this study, several monoacyl GAs were synthesized by esterification of GA and saturated fatty acyl chlorides (C12, C14, C16, and C18), forming a new class of bio-based surfactants. By the present method, a mixture of two isomers, namely 2-O-acyl and 3-O-acyl GAs, was produced, in which the 2-O-acyl derivatives were obtained as a major product. These isomers were isolated, and their surface-active properties were investigated for the first time. The surface tensions of 2-O-acyl GAs with different chain lengths were determined by the Wilhelmy method. At concentrations below 10–4 M, the 2-O-acyl GAs exhibited higher surface-active properties compared to commercially available synthetic surfactants. For example, 2-O-lauroyl GA reduced the surface tension of water to around 25 mN/m above the critical micelle concentration (3.0×10–4 M). In addition, 2-O-acyl derivatives showed higher surface-tension-lowering activity than 3-O-acyl GAs. The monoacyl GAs synthesized herein can potentially be used as “green surfactants.”
Cinnamon bark (Cinnamomum zeylanicum) powder was treated with subcritical water at 150 and 200°C in a semi-continuous system at a constant flow rate (3 mL/min) and pressure (6 MPa). Major flavoring compounds, i.e., cinnamaldehyde, cinnamic acid, cinnamyl alcohol and coumarin, were extracted at lower recoveries than the extraction using methanol, suggesting that degradation of these components might occur during the subcritical water treatment. Caffeic, ferulic, p-coumaric, protocatechuic and vanillic acids were identified from the subcritical water treatment. Extraction using subcritical water was more effective to obtain these acids than methanol (50% v/v) in both number of components and recovery, especially at 200°C. Subcritical water treatment at 200°C also resulted in a higher total phenolic content and DPPH radical scavenging activity than the methanol extraction. The DPPH radical scavenging activity and total phenolic content linearly correlated but the results suggested that the extraction at 200°C might result in other products that possessed a free radical scavenging activity other than the phenolic compounds.