Department of Food Phytochemistry, Instituto de la Grasa (Spanish National Research Council, CSIC), Ctra. de Utrera km. 1, Pablo de Olavide University Campus, Building 46, 41013 Seville, Spain.
Department of Food Phytochemistry, Instituto de la Grasa (Spanish National Research Council, CSIC), Ctra. de Utrera km. 1, Pablo de Olavide University Campus, Building 46, 41013 Seville, Spain.
Food Chem. 2024 Jan 30;432:137233. doi: 10.1016/j.foodchem.2023.137233. Epub 2023 Aug 23.
p-Coumaroyl-6́-secologanoside (comselogoside) is a secoiridoid identified in large amounts in olive fruits, although no studies in vitro or in vivo of comselogoside have been reported. This work focuses on the recovery and purification of this compound from olive mill waste (alperujo). The successive isolation on Amberlite XAD-16 and Sephadex LH-20 resins, allowed a comselogoside extract with 80-85% of purity. A photoisomerization of the vinyl-double bond in the p-coumaroyl moiety occurred when the extract was exposed to ultraviolet radiation and a mixture of the trans and cis-isomers was obtained. Both isomers were characterized using NMR, mass spectroscopy, and UV spectrometry. The J (coupling constant) of the protons on the C7 and C8 on the unsaturated chain were found to be the difference between cis (12.8 Hz) and trans- (15.9 Hz) comselogoside. Cis-isomer exhibited lower radical-scavenging activity than trans, although a synergistic effect occurred when the cis-isomer was supplement by the trans-isomer.
对映枯醇酰基-6′-槐糖苷（comselogoside）是一种在橄榄果实中大量存在的裂环环烯醚萜，尽管尚未报道其在体外或体内的研究。本工作重点是从橄榄加工废物（alperujo）中回收和纯化这种化合物。连续使用 Amberlite XAD-16 和 Sephadex LH-20 树脂进行分离，得到纯度为 80-85%的 comselogoside 提取物。当提取物暴露于紫外辐射时，对映枯酰基部分的乙烯基双键会发生光异构化，得到顺式和反式异构体的混合物。两种异构体均采用 NMR、质谱和紫外光谱进行了表征。不饱和链上 C7 和 C8 上的质子的 J（偶合常数）被发现是 cis（12.8 Hz）和 trans-comselogoside（15.9 Hz）之间的差异。顺式异构体的自由基清除活性低于反式异构体，但当顺式异构体被反式异构体补充时，会发生协同作用。
