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J Agric Food Chem. 2017 Jun 14;65(23):4611-4623. doi: 10.1021/acs.jafc.7b01396. Epub 2017 Jun 1.

Triterpenoid Components from Oak Heartwood (Quercus robur) and Their Potential Health Benefits.

Author information

1
Department of Biochemistry and Crop Quality, Institute of Soil Science and Plant Cultivation, State Research Institute , ul. Czartoryskich 8, 24-100 Puławy, Poland.
2
Área Productos Químicos, Unidad de Desarrollo Tecnológico (UDT) - Universidad de Concepción , Av. Cordillera No. 2634, Coronel 4191996, Concepción, Chile.
3
Laboratory of Cytogenetics, Faculty of Biology and Environmental Protection, University of Lodz , Banacha 12/16, 90 237 Lodz, Poland.
4
Tanin Sevnica d.d. , Hermanova 1, 8290 Sevnica, Slovenia.

Abstract

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 (IC50 = 19.7 μM). Selectivity was observed for compounds 1-3, 8, 9, and 16, exhibiting an IC50 > 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.

KEYWORDS:

Quercus robur; breast cancer; cytotoxicity; heartwood; structure−activity relationships; triterpenoids

PMID:
28535679
DOI:
10.1021/acs.jafc.7b01396
[Indexed for MEDLINE]

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