Pérez Andy J, Pecio Łukasz, Kowalczyk Mariusz, Kontek Renata, Gajek Gabriela, Stopinsek Lidija, Mirt Ivan, Oleszek Wiesław, Stochmal Anna
Department of Biochemistry and Crop Quality, Institute of Soil Science and Plant Cultivation, State Research Institute , ul. Czartoryskich 8, 24-100 Puławy, Poland.
Área Productos Químicos, Unidad de Desarrollo Tecnológico (UDT) - Universidad de Concepción , Av. Cordillera No. 2634, Coronel 4191996, Concepción, Chile.
J Agric Food Chem. 2017 Jun 14;65(23):4611-4623. doi: 10.1021/acs.jafc.7b01396. Epub 2017 Jun 1.
For centuries oak wood (Quercus robur) has been used in aging of wines and spirits, which is based on pleasant flavors given to beverages by phenolics transferred to the liquid during the maturation process. Other metabolites, such as triterpenoids, can also be released. Searching for extractable triterpenoids in oak heartwood, 12 new, 1-12, and five known, 13-17, oleanane types were isolated and characterized. Their cytotoxicities were tested against cancer cells (PC3 and MCF-7) and lymphocytes. Breast cancer cells (MCF-7) were the most affected by triterpenoids, with roburgenic acid, 4, being the most active compound (IC = 19.7 μM). Selectivity was observed for compounds 1-3, 8, 9, and 16, exhibiting an IC > 200 μM against lymphocytes, while active against cancer cells. A galloyl unit attached to the triterpenoid moiety was established as the key feature for such effect. These results highlight the occurrence of triterpenoids in oak heartwood and their relevance for chemoprevention of breast cancer.
几个世纪以来，橡木（欧洲栎）一直用于葡萄酒和烈酒的陈酿，这是基于在成熟过程中酚类物质转移到液体中赋予饮料宜人的风味。其他代谢产物，如三萜类化合物，也可能被释放出来。在橡木心材中寻找可提取的三萜类化合物时，分离并鉴定了12种新的（1-12）和5种已知的（13-17）齐墩果烷型化合物。测试了它们对癌细胞（PC3和MCF-7）和淋巴细胞的细胞毒性。乳腺癌细胞（MCF-7）受三萜类化合物影响最大，其中罗布酸（4）是最具活性的化合物（IC = 19.7 μM）。观察到化合物1-3、8、9和16具有选择性，对淋巴细胞的IC>200 μM，而对癌细胞有活性。连接在三萜类部分的没食子酰基单元被确定为产生这种效果的关键特征。这些结果突出了橡木心材中三萜类化合物的存在及其对乳腺癌化学预防的相关性。
