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

Masahiro Hamada; Shunichi Naruse; Misaki Wada; Takao Kishimoto; Noriyuki Nakajima

doi:10.1055/s-0033-1341083

Synthesis, Table of Contents

Synthesis 2014; 46(13): 1779-1787
DOI: 10.1055/s-0033-1341083

paper

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

Authors

Masahiro Hamada*

^aDepartment of Biotechnology, Faculty of Engineering, Toyama Prefectural University, Imizu, Toyama 939-0398, Japan

^bBiotechnology Research Center, Toyama Prefectural University, Imizu, Toyama 939-0398, Japan Fax: +81(766)562498 Email: hamada@pu-toyama.ac.jp Email: nori@pu-toyama.ac.jp
Shunichi Naruse

^aDepartment of Biotechnology, Faculty of Engineering, Toyama Prefectural University, Imizu, Toyama 939-0398, Japan
Misaki Wada

^aDepartment of Biotechnology, Faculty of Engineering, Toyama Prefectural University, Imizu, Toyama 939-0398, Japan
Takao Kishimoto

^aDepartment of Biotechnology, Faculty of Engineering, Toyama Prefectural University, Imizu, Toyama 939-0398, Japan

^bBiotechnology Research Center, Toyama Prefectural University, Imizu, Toyama 939-0398, Japan Fax: +81(766)562498 Email: hamada@pu-toyama.ac.jp Email: nori@pu-toyama.ac.jp
Noriyuki Nakajima*

^aDepartment of Biotechnology, Faculty of Engineering, Toyama Prefectural University, Imizu, Toyama 939-0398, Japan

^bBiotechnology Research Center, Toyama Prefectural University, Imizu, Toyama 939-0398, Japan Fax: +81(766)562498 Email: hamada@pu-toyama.ac.jp Email: nori@pu-toyama.ac.jp

Abstract

All articles of this category

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

Full Text

References

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