Pyrogallol structure in polyphenols is involved in apoptosis-induction on HEK293T and K562 cells

Molecules

Volumn 13, Issue 12, 2008, Pages 2998-3006

  Mitsuhashi, Shinya ^a   Saito, Akiko ^b,c   Nakajima, Noriyuki ^d   Shima, Hiroshi ^e   Ubukata, Makoto ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b Biotechnology Center   (Japan)

^c Discovery Research Institute   (Japan)

^d TOYAMA PREFECTURAL UNIVERSITY   (Japan)

^e MIYAGI CANCER CENTER RESEARCH INSTITUTE   (Japan)

Author keywords

Apoptosis; Cytotoxicity; Polyphenol; Pyrogallol; Structure activity relationship

Indexed keywords

ANTIOXIDANT; PYROGALLOL;

APOPTOSIS; ARTICLE; CELL LINE; CHEMISTRY; DRUG EFFECT; HUMAN; STRUCTURE ACTIVITY RELATION;

ANTIOXIDANTS; APOPTOSIS; CELL LINE; HUMANS; PYROGALLOL; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 58149234997     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules13122998     Document Type: Article

References (20)

1. Harborne, J. B. The Flavonoids: Advances in Research from 1986; Champion & Hall: London, UK, 1993.
2. Harborne, J. B.; Baxter, H. The Handbook of Natural Flavonoids. Wiley: New York, USA, 1999.
3. Knekt, P.; Jarvinen, R.; Seppanen, R.; Hellovaara, M.; Teppo, L.; Pukkala E.; Aromaa, A. Dietary flavonoids and the risk of lung cancer and other malignant neoplasms. Am. J. Epidemiol. 1997, 146, 223-230.
4. Keli, S.O.; Hertog, M.G.; Feskens E.J.; Kromhout, D. Dietary flavonoids, antioxidant vitamins, and incidence of stroke: the Zutphen study. Arch. Intern. Med. 1996, 156, 637-642.
5. Arts, I.C.; Hollman, P.C.; Feskens, E.J.; Bueno H.B. Mesquita, d.; Kromhout, D. Catechin intake might explain the inverse relation between tea consumption and ischemic heart disease: the Zutphen Elderly Study. Am. J. Clin. Nutr. 2001, 74, 227-232.
6. Seeram, N.P.; Adams, L.S.; Zhang, Y.; Lee, R.; Sand, D.; Scheuller, H.S.; Heber, D. Blackberry, black raspberry, blueberry, cranberry, red raspberry, and strawberry extracts inhibit growth and stimulate apoptosis of human cancer cells in vitro. J. Agric. Food Chem. 2006, 54, 9329-9339.
7. Soobrattee, M.A.; Bahorun, T.; Aruoma, O.I. Chemopreventive actions of polyphenolic compounds in cancer. Biofactors 2006, 27, 19-35.
8. Galati, G.; O'Brien, P.J. Potential toxicity of flavonoids and other dietary phenolics: significance for their chemopreventive and anticancer properties, Free Radic. Biol. Med. 2004, 37, 287-303.
9. Smith, D.M.; Dou, Q.P. Green tea polyphenol epigallocatechin inhibits DNA replication and consequently induces leukemia cell apoptosis. Int. J. Mol. Med. 2001, 7, 645-652.
10. Baatout, S.; Jacquet, P.; Derradji, H.; Ooms, D.; Michaux, A.; Mergeay, M. Study of the combined effect of X-irradiation and epigallocatechin-gallate (a tea component) on the growth inhibition and induction of apoptosis in human cancer cell lines. Oncol. Rep. 2004, 12, 159-167.
11. Vaux, D. L. Toward an understanding of the molecular mechanisms of physiological cell death. Proc. Natl. Acad. Sci. U. S. A. 1993, 90, 786-789.
12. Li, N.; Liu, J.H.; Zhang, J.; Yu BY. Comparative Evaluation of Cytotoxicity and Antioxidative Activity of 20 Flavonoids. J. Agric. Food Chem. 2008, 56, 3876-3883
13. Shimomura, O.; Wu, C.; Murai, A.; Nakamura, H. Evaluation of Five Imidazopyrazinone-Type Chemiluminescent Superoxide Probes and Their Application to the Measurement of Superoxide Anion Generated by Listeria monocytogenes. Anal. Biochem. 1998, 258, 230-235
14. Saito, A.; Tanaka, A.; Ubukata, M.; Nakajima, N. Stereoselection of 3,4-cis and 3,4-trans catechin and catechin condensation under intramolecular coupling method. Synlett 2004, 11, 2040-2042
15. Saito, A.; Doi, Y.; Tanaka, A.; Matsuura, N.; Ubukata, M.; Nakajima, N. Systematic synthesis of four epicatechin series procyanidin trimers and their inhibitory activity on the Maillard reaction and antioxidant activity. Bioorg. Med. Chem. 2004, 12, 4783-4790
16. Saito, A.; Nakajima, N.; Tanaka, A.; Ubukata, M. Synthetic studies of proanthocyanidins. Part 2: Stereoselective gram-scale synthesis of procyanidin-B3. Tetrahedron 2002, 58, 7829-7837
17. Saito, A.; Nakajima, N.; Matsuura, N.; Tanaka, A.; Ubukata, M. Synthetic studies of proanthocyanidins. Part 5. Highly stereoselective synthesis and inhibitory activity of maillard reaction of 3, 4-trans catechin and epicatechin dimers, procyanidin B1, B2, B3, B4 and their acetates. Heterocycles 2004, 62, 479-489
18. Saito, A.; Nakajima, N.; Tanaka, A.; Ubukata, M. Synthetic studies of proanthocyanidins. Part 3. Stereoselective 3, 4-cis catechin and catechin condensation by TMSOTf-catalyzed intramolecular coupling method. Tetrahedron Lett. 2003, 44, 5449-5452.
19. Saito, A.; Nakajima, N.; Tanaka, A.; Ubukata, M. Synthetic studies of proanthocyanidins. Part 4. The synthesis of procyanidin B1 and B4: TMSOTf-catalyzed cyclization of catechin and epicatechin condensation. Heterocycles 2003, 61, 287-298.
20. Saito, A.; Tanaka, A.; Ubukata, M.; Nakajima, N. Efficient stereoselective synthesis of proanthocyanidin trimers with TMSOTf-catalyzed intermolecular condensation. Synlett. 2004, 6, 1069-1073.