Effect of refining on the phenolic composition of crude olive oils

By definition, virgin olive oil is consumed unrefined, although a great proportion of the olive oil produced has to be refined to render it edible. Phenolic compounds are among the substances eliminated during the refining process; in the present work these were characterized by HPLC, and their evolution during the different refining steps was studied. The complete refining process removed most polyphenols from oils, but the behavior of individual compounds at each step also was observed. o-Diphenols (hydroxytyrosol, catechol, and hydroxytyrosol acetate) and flavonoids (luteolin and apigenin) were eliminated first during the alkaline treatment. Tyrosol and 4-ethylphenol remained in the oil until the deodorization step. A large amount of phenolic compounds was discovered in the refining by-products such as soapstocks and deodorization distillates. In the latter streams, the concentrations of tyrosol and 4-ethylphenol reached up to 149 and 3720 mg/kg by-product, respectively. This high level of 4-ethylphenol and its well-known strong off-odor can interfere during further processing of the deodorization distillates, and this must be taken into account when deciding what is to become of them. Similarly, the results of this work open the possibility of recovering phenolic compounds from the “second centrifugation olive oils” by adding a new washing step prior to the refining process. By including this new step, the most polar polyphenols, hydroxytyrosol and tyrosol, will diffuse from oil to water and a concentration of up to 1400 mg/L of hydroxytyrosol may be achieved.     

Recovery of Hydroxytyrosol Rich Extract from Two‐Phase Chemlali Olive Pomace by Chemical Treatment

Abstract: A very simple method is proposed to produce hydroxytyrosol, a commercially unavailable compound with well‐known biological properties which justify a potential commercial application. The 2‐phase Chemlali olive pomace is selected as substrate for chemical treatment. Different conditions of chemical treatment, including concentration of acid and alkaline solutions, time and temperature, were assayed. A high amount of hydroxytyrosol (1360 mg/kg of fresh 2‐phase olive pomace) was obtained using water bath after treatment at 80 °C for 90 min with 1 M of H₃PO₄. However, treatment of 2‐phase Chemlali olive pomace using autoclave apparatus could produce a large amount of hydroxytyrosol (1993.60 and 1515.88 mg/kg of fresh alperujo, 1 M acid and basic catalyst, respectively). By taking into consideration practical and economic aspects, acid‐catalyzed treatment was more effective using autoclave conditions, whereas the alkali catalyzed conditions were not very suitable. This study could provide useful information for industry to produce the potentially bioactive compound. Practical Application: The 2‐phase Chemlali olive pomace is selected as substrate for chemical treatment. Treatment of “alperujo” using water bath or autoclave apparatus was carried out. A high amount of hydroxytyrosol was obtained using autoclave apparatus.     

Evaluation of table olive by‐product as a source of natural antioxidants

The main by‐product from the table olive canning industry is the stone with some residual olive flesh. The purpose of this study was to evaluate the composition – phenolic compounds (hydroxytyrosol, tyrosol and oleuropein) and tocopherol – and the antioxidant activity in different fractions (flesh, stone and seed) from the table olive by‐product and the whole by‐product. The highest amounts of phenolic compounds (1710.0 ± 33.8 mg kg^?1) as well as the highest antioxidant activity (8226.9 ± 9.9 hydroxytyrosol equivalents mg kg^?1) were obtained in the seed. The highest amounts of hydroxytyrosol (854.8 ± 66.0 mg kg^?1) and tyrosol (423.6 ± 56.9 mg kg^?1) were found in the whole by‐product from the pepper stuffed olives, while the stone without seed had the maximum oleuropein content (750.2 ± 85.3 mg kg^?1). α‐Tocopherol values were between 79.8 ± 20.8 mg kg^?1 in the seed of the olive stone and 6.2 ± 1.2 mg kg^?1 in the whole by‐product from the anchovy‐stuffed olives. In light of the results obtained, it would seem possible to use table olive by‐product as a source of natural antioxidants in foods, cosmetics or pharmaceutical products, thus contributing to diminishing the environmental impact of table olive by‐product and to its revalorisation.     

The olive compound 4-hydroxytyrosol inactivates Staphylococcus aureus bacteria and Staphylococcal Enterotoxin A (SEA)

The foodborne pathogen Staphylococcus aureus produces the virulent staphylococcal enterotoxin A (SEA), a single chain protein which consists of 233 amino acid residues with a molecular weight of 27078 Da. SEA is a superantigen that is reported to contribute to animal (mastitis) and human (emesis, diarrhea, atopic dermatitis, arthritis, and toxic shock) syndromes. Changes in the native structural integrity may inactivate the toxin by preventing molecular interaction with cell membrane receptor sites of their host cells. In the present study, we evaluated the ability of the pure olive compound 4-hydroxytyrosol and a commercial olive powder called Hidrox-12, prepared by freeze-drying olive juice, to inhibit S. aureus bacteria and SEA's biological activity. Dilutions of both test substances inactivated the pathogens. Two independent cell assays (BrdU incorporation into newly synthesized DNA and glycyl-phenylalanyl-aminofluorocoumarin proteolysis) demonstrated that the olive compound 4-hydroxytyrosol also inactivated the biological activity of SEA at concentrations that were not toxic to the spleen cells. However, efforts to determine inhibition of the toxin by Hidrox-12 were not successful because the olive powder was cytotoxic to the spleen cells at concentrations found to be effective against the bacteria. The results suggest that food-compatible and safe antitoxin olive compounds can be used to inactivate both pathogens and toxins produced by the pathogens. Practical Application: The results of this study suggest that food-compatible and safe antitoxin olive compounds can be used to reduce both pathogens and toxins produced by the pathogens in foods.     

Influence of malaxation conditions on characteristic qualities of olive oil

While there has been considerable work examining the effect of extraction methods and malaxation conditions on different characteristics of olive oils, there have been few that deal with all the major aspects. Here we have evaluated three different extraction techniques and the influence of time and temperature during malaxation using a major Italian (cv. Coratina) and the main Cretan (cv. Koroneiki) cultivars. Standard characteristics were measured as well as detailed analyses of alcohols, steroids and phenolics were conducted. Quality was also assessed by Panel tests. The main variables were the total amount and composition of the phenolics. In turn, this influenced the oxidative stability and sensory quality. It was also clear that the cultivars behaved differently and this prevented general conclusions being made for all of the quality characteristics.     

羟基酪醇合成工艺研究

以邻苯二酚为起始原料,经过保护邻二酚羟基,溴化制得3,4-亚甲二氧基溴苯,制备其格氏试剂,再用格氏试剂与环氧乙烷反应,最后脱掉保护基团,以5步反应总收率24%得到高纯度羟基酪醇,并通过IR、MS等方法对终产物进行了表征。     

羟基酪醇酶促聚合产物的表征及其抗氧化和热稳定性

利用漆酶对羟基酪醇（hydroxytyrosol,HT）进行酶促氧化聚合,运用紫外-可见分光光度计、傅里叶红外光谱、凝胶色谱和液相色谱-质谱联用对聚合产物进行表征。结果表明,形成的聚合物呈现多分散性（D=2.1）,主要生成了三聚体、四聚体、六聚体化合物。同时,以VC和2,6-二叔丁基-4-甲基苯酚（dibutyl hydroxy toluene,BHT）为阳性对照,分别通过清除1,1-二苯基-2-三硝基苯肼自由基和热重-傅里叶变换红外光谱（thermogravimetry-Fourier transform infrared spectroscopy,TG-FTIR）联用的方法对其进行抗氧化性及热稳定性评价。结果表明,HT聚合物较HT和BHT具有更强的抗氧化性,分别约是其2.28?倍和5.7?倍,接近于VC（约是其72%）。基于热重微分曲线峰值温度（315.1?℃）和残余质量所占百分比（66.09%）结果可知,HT聚合物的热稳定性较VC（228.1?℃）、BHT（236.2?℃）和HT（314.9?℃）更强,且FTIR结果表明,HT聚合物及其他受试化合物均是以羟基断裂开始,脱氢形成醌式结构或脱水碳碳双键。这些数据可为HT的深加工利用提供理论和实践基础。     

The Importance and Potential Uses of Olive Leaves

Since phenolic compounds have been known as strong antioxidants, studies on olive leaves have attracted the investigators due to the richness of phenolic compounds in olive leaves. Recently, olive leaves are used in medicine, cosmetics, and in pharmaceutical products. It has a high potential for industrial exploitation in the food industry. In this study, the importance of olive leaves is briefly given, the composition of olive leaves, main phenolics in olive leaves and their health effects are described. Studies conducted on technological usage of olive leaves are reviewed. The future of olive leaves for the food industry is discussed. It is expected that this study will be beneficial to academic and industrial researchers interested in antioxidants, food additives, functional foods, and olive leaves.