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Structure–Antioxidant–Antiproliferative Activity Relationships of Natural C7 and C7–C8 Hydroxylated Flavones and Flavanones

1
Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland
2
Department of Experimental Oncology, Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Weigla 12, 53-114 Wrocław, Poland
3
Department of Fruit, Vegetable and Plant Nutraceutical Technology, Wrocław University of Environmental and Life Sciences, Chełmońskiego 37, 51-630 Wrocław, Poland
*
Author to whom correspondence should be addressed.
Antioxidants 2019, 8(7), 210; https://doi.org/10.3390/antiox8070210
Received: 21 May 2019 / Revised: 4 July 2019 / Accepted: 5 July 2019 / Published: 7 July 2019
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Abstract

Common food flavonoids: chrysin, apigenin, luteolin, diosmetin, pinocembrin, naringenin, eriodictyol, hesperetin, and their analogues with an additional hydroxyl group at the C-8 position obtained via biotransformation were tested for antioxidant activity using the ABTS, DPPH, and ferric ion reducing antioxidant power (FRAP) methods. They were also tested for antiproliferative activity against selected human cancer cell lines—MV-4-11 (biphenotypic B myelomonocytic leukemia), MCF7 (breast carcinoma), LoVo (colon cancer), LoVo/DX (colon cancer doxorubicin resistant), and DU 145 (prostate cancer)—and two normal human cell lines—MCF 10A (breast cells) and HLMEC (lung microvascular endothelial cells). Flavonoids with a C7–C8 catechol moiety indicated much higher antioxidant activity compared with the C7 hydroxy analogues. However, because they were unstable under the assay conditions, they did not show antiproliferative activity or it was very low. View Full-Text
Keywords: flavones; flavanones; hydroxylation; catechol moiety; antioxidant activity; anticancer activity flavones; flavanones; hydroxylation; catechol moiety; antioxidant activity; anticancer activity
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Sordon, S.; Popłoński, J.; Milczarek, M.; Stachowicz, M.; Tronina, T.; Kucharska, A.Z.; Wietrzyk, J.; Huszcza, E. Structure–Antioxidant–Antiproliferative Activity Relationships of Natural C7 and C7–C8 Hydroxylated Flavones and Flavanones. Antioxidants 2019, 8, 210.

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