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Pyrogallol Structure in Polyphenols is Involved in Apoptosis-induction on HEK293T and K562 Cells
Division of Applied Bioscience, Research Faculty of Agriculture, Hokkaido University, Kita-9, Nishi-9, Kita-ku, Sapporo 060-8589, Japan
Biotechnology Center, Toyama Prefecture, Kosugi, Toyama 939-0398, Japan
Present address: Antibiotics Laboratory, Discovery Research Institute, RIKEN 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan
Biotechnology Research Center, Toyama Prefectural University, Kosugi, Toyama 939-0398, Japan
Division of Cancer Chemotherapy, Research Institute, Miyagi Cancer Center, Natori, Japan
* Author to whom correspondence should be addressed.
Received: 28 October 2008; in revised form: 27 November 2008 / Accepted: 3 December 2008 / Published: 4 December 2008
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.
Keywords: Cytotoxicity; Apoptosis; Pyrogallol; polyphenol; Structure-activity relationship
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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.