This study provides an efficient pilot-scale liquid-liquid extraction process for the recovery of total phenolic fraction (TPF) from extra virgin olive oil (EVOO) and the further purification of the major TPF constituents (oleocanthal, oleacein, monoaldehydic form of oleuropein aglycone, monoaldehydic form of ligstroside aglycone and hydroxytyrosol) using successively centrifugal partition chromatography and reversed phase high performance liquid chromatography. Special attention was paid for the selection of the appropriate raw material, which should be rich in the targeted high-value compounds. For the extraction of the selected EVOOs, a green technique based on liquid-liquid partitioning using the biphasic system n-Hept/EVOO/EtOH/H2O 3:2:3:2 v/v was carried out, first on pioneering laboratory-scale annular centrifugal extractor (ACE) and then on pilot device. 240 L from three different EVOOs (3x80 L of each EVOO) were extracted yielding 285 g of TPF in approximately 2 h. The second step of this procedure was the purification of the target compounds. A preparative centrifugal partition chromatography (CPC) process was firstly applied for the initial TPF fractionation using a step gradient elution-extrusion method with a series of 4 biphasic systems composed of n-Hept/EtOAc/EtOH/H₂O in ratios 4:1:3:2, 3:2:3:2, 2:3:3:2 and 1:4:3:2 (v/v/v/v). Preparative reversed phase high performance liquid chromatography (prep-RP-HPLC) was then carried out to polish the target compounds from the enriched CPC fractions resulting in purity higher than 97%. In parallel, the above purification analysis led to the isolation of four minor TPF constituents of which three are new natural products (EDA lactone, (1R, 8E)-1-ethoxy-ligstroside aglycon and (1S, 8E)-1-ethoxy-ligstroside aglycon) and one ((9E, 11E)-13-oxotrideca-9,11-diencoic acid) is described for the first time as EVOO constituent.

这项研究为从特级初榨橄榄油（EVOO）中回收总酚类馏分（TPF）以及进一步纯化主要TPF成分（油酸，油酸甘油酯，橄榄醛糖苷配糖苷的单醛形式）提供了有效的中试液-液萃取工艺。 ，单糖醛糖苷甙元和羟基酪醇的单醛形式），采用连续离心分配色谱法和反相高效液相色谱法。特别注意选择合适的原材料，该原材料应富含目标高价值化合物。为了提取选定的EVOO，进行了基于液-液分配的绿色技术，使用双相系统n-Hept / EVOO / EtOH / H2O 3：2：3：2 v / v，首先是开创性的实验室规模的环形离心提取器（ACE），然后是先导装置。从三个不同的EVOO中提取240升（每个EVOO 3x80升），在大约2小时内产生285 g TPF。该步骤的第二步是目标化合物的纯化。首先，采用逐步梯度洗脱-挤压方法，将制备性离心分配色谱法（CPC）用于TPF的初始分馏，该方法由一系列由n-Hept / EtOAc / EtOH / H组成的4个双相系统组成₂ O的比例为4：1：3：2、3：2：3：2、2：3：3：2和1：4：3：2（v / v / v / v）。然后进行制备型反相高效液相色谱（制备型RP-HPLC），从浓缩的CPC馏分中纯化目标化合物，从而得到高于97％的纯度。同时，上述纯化分析导致分离出四种次要的TPF成分，其中三种是新的天然产物（EDA内酯，（1 R，8 E）-1-乙氧基-ligstroside糖苷配基和（1 S，8 E）- EVOO成分首次被描述为1-乙氧基-糖苷配基糖苷配基和一个（（9 E，11 E）-13-氧杂苯胺-9,11-二烯酸）。