Abstract: As multiple mechanisms account for polyphenol-induced cytotoxicity, the development of structure-activity relationships (SARs) may facilitate research on cancer therapy. We studied SARs of representatives of 10 polyphenol structural types: (+)-catechin (1), (-)-epicatechin (2), (-)-epigallocatechin (3), (-)-epigallocatechin gallate (4), gallic acid (5), procyanidin B2 (6), procyanidin B3 (7), procyanidin B4 (8), procyanidin C1 (9), and procyanidin C2 (10). Amongst them, the polyphenols containing a pyrogallol moiety (3-5) showed the most potent cytotoxicic activity. These compounds evoked a typical DNA-laddering phenomenon in HEK293T, which indicated that the induction of apoptosis at least partly mediates their cytotoxic activity. Anti-oxidative capacity of compounds 3-5 were comparable to those of the trimers 9 and 10, which were not cytotoxic. Therefore, we suggest that pyrogallol moiety is important for fitting of polyphenols to their putative target molecule(s) in non-oxidative mechanism.
This is an open access article distributed under the
Creative Commons Attribution License which permits unrestricted use, distribution,
and reproduction in any medium, provided the original work is properly cited.
Export to BibTeX
MDPI and ACS Style
Mitsuhashi, S.; Saito, A.; Nakajima, N.; Shima, H.; Ubukata, M. Pyrogallol Structure in Polyphenols is Involved in Apoptosis-induction on HEK293T and K562 Cells. Molecules 2008, 13, 2998-3006.
Mitsuhashi S, Saito A, Nakajima N, Shima H, Ubukata M. Pyrogallol Structure in Polyphenols is Involved in Apoptosis-induction on HEK293T and K562 Cells. Molecules. 2008; 13(12):2998-3006.
Mitsuhashi, Shinya; Saito, Akiko; Nakajima, Noriyuki; Shima, Hiroshi; Ubukata, Makoto. 2008. "Pyrogallol Structure in Polyphenols is Involved in Apoptosis-induction on HEK293T and K562 Cells." Molecules 13, no. 12: 2998-3006.