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Molecules 2008, 13(12), 2998-3006; doi:10.3390/molecules13122998
Article

Pyrogallol Structure in Polyphenols is Involved in Apoptosis-induction on HEK293T and K562 Cells

1
,
2,3
,
4
,
5
 and
1,*
1 Division of Applied Bioscience, Research Faculty of Agriculture, Hokkaido University, Kita-9, Nishi-9, Kita-ku, Sapporo 060-8589, Japan 2 Biotechnology Center, Toyama Prefecture, Kosugi, Toyama 939-0398, Japan 3 Present address: Antibiotics Laboratory, Discovery Research Institute, RIKEN 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan 4 Biotechnology Research Center, Toyama Prefectural University, Kosugi, Toyama 939-0398, Japan 5 Division of Cancer Chemotherapy, Research Institute, Miyagi Cancer Center, Natori, Japan
* Author to whom correspondence should be addressed.
Received: 28 October 2008 / Revised: 27 November 2008 / Accepted: 3 December 2008 / Published: 4 December 2008
(This article belongs to the Special Issue Phenolics and Polyphenolics)
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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 Cytotoxicity; Apoptosis; Pyrogallol; polyphenol; Structure-activity relationship
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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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.

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