Synthesis of Tea Catechin Lactone Metabolite Analogues with a 2′-Hydroxyphenyl Group

Abstract

Tea catechins such as epicatechin, epigallocatechin, epicatechin gallate and epigallocatechin gallate afford many metabolites, including γ-valerolactone derivatives, through metabolic pathways in the human body. Two of these γ-valerolactone metabolite analogues with a 2′-hydroxyphenyl group were synthesized as optically active authentic standards.

Key words

tea catechins - stereocontrolled synthesis - reverse Brook rearrangement - γ-valerolactones

• References

• 1 Ariga T, Koshiyama I, Fukushima D. Agric. Biol. Chem. 1988; 52: 2717
• 2a Lu H, Meng X, Li C, Sang S, Patten C, Sheng S, Hong J, Bai N, Winnik B, Ho CT, Yang CS. Drug Metab. Dispos. 2003; 31: 452
• 2b Lu H, Meng X, Yang CS. Drug Metab. Dispos. 2003; 31: 572
• 3 Lambert JD, Lee MJ, Lu H, Meng X, Ju J, Hong J, Seril DN, Sturgill MG, Yang CS. J. Nutr. 2003; 133: 4172
• 4a Ohshima Y, Watanabe H, Isakari S. J. Biochem. 1958; 45: 861
• 4b Ohshima Y, Watanabe H. J. Biochem. 1958; 45: 973
• 4c Ohshima Y, Watanabe H, Kuwazuka S. Bull. Agric. Chem. Soc. Jpn. 1960; 24: 497
• 5a Meselhy MR, Nakamura N, Hattori M. Chem. Pharm. Bull. 1997; 45: 888
• 5b Wang L.-Q, Meselhy MR, Li Y, Nakamura N, Min B.-S, Qin G.-W, Hattori M. Chem. Pharm. Bull. 2001; 49: 1640
• 6a Li C, Lee M.-J, Sheng S, Meng X, Prabhu S, Winnik B, Huang B, Chung JY, Yan S, Ho C.-T, Yang CS. Chem. Res. Toxicol. 2000; 13: 177
• 6b Li C, Meng X, Winnik B, Lee M.-J, Lu H, Sheng S, Buckley B, Yang CS. Chem. Res. Toxicol. 2001; 14: 702
• 6c Meng X, Sang S, Zhu N, Lu H, Sheng S, Lee M.-J, Ho C.-T, Yang CS. Chem. Res. Toxicol. 2002; 15: 1042
• 7 Duweler KG, Rohdewald P. Pharmazie 2000; 55: 364
• 8a Kohri T, Matsumoto N, Yamakawa M, Suzuki M, Nanjo F, Hara Y, Oku N. J. Agric. Food Chem. 2001; 49: 4102
• 8b Kohri T, Suzuki M, Nanjyo F. J. Agric. Food Chem. 2003; 51: 5561
• 9 Lee M.-J, Maliakal P, Chen L, Meng X, Bondoc FY, Prabhu S, Lambert G, Mohr S, Yang CS. Cancer Epid. Biom. Prev. 2002; 11: 1025
• 10 Takizwa Y, Morota T, Tajeda S, Aburada M. Biol. Pharm. Bull. 2003; 26: 608
• 11 Fukai T, Ishigami T, Hara Y. Agric. Biol. Chem. 1991; 55: 1895
• 12 Watanabe H. Bull. Agr. Chem. Soc. Jpn. 1959; 23: 263
• 13 Lambert JD, Rice JE, Hong J, Hou Z, Yang CS. Bioorg. Med. Chem. Lett. 2005; 15: 873
• 14a Nakano S, Hamada M, Kishimoto T, Nakajima N. Heterocycles 2008; 76: 1001
• 14b Hamada M, Furuno A, Nakano S, Kishimoto T, Nakajima N. Synthesis 2010; 1512
• 15 Smith III AB, Xian M. J. Am. Chem. Soc. 2006; 128: 66
• 16 Smith III AB, Pitram SM, Armen M, Gaunt MJ, Sfouggatakiis C, Moser WH. J. Am. Chem. Soc. 2003; 125: 14435