Naturaly Occurring Nanomolecules, Tannins Their Structures and Functions Takashi Yoshida*, Tsutomu Hatano, and Hideyuki Ito Large-size secondary metab
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1 Naturaly Occurring Nanomolecules, Tannins Their Structures and Functions Takashi Yoshida*, Tsutomu Hatano, and Hideyuki Ito Large-size secondary metabolites with dimeric-oligomeric and/or dendrine-type structure from higher plants are regarded as natural nanomolecules which are constructed in a bottom-up pathway from small molecules under biological condition. Among them are polyphenols classified as tannins which have large molecular weights ranging from 500 to 4000, and strong affinity to proteins, alkaloids and heavy metals to form complex molecules (precipitates). They constitute two major groups: one is condensed tannins (proantocyanidins), which are composed of flavan-3-ol units linked through C-C bond, and the other is hydrolyzable tannins, which are principally multiple esters of D-glucose with gallic acid and its oxidative metabolites. This paper reviews the diverse structural characteristics of both tannins, especially ellagitannin oligomers up to pentamers, and examples of their biological activities. Formation of insoluble and soluble complex between tannins and proteins are also described. Key words: high molecular weight polyphenols, tannin, proanthocyanidin, hydrolyzable tannin oligomer, intermolecular C-O oxidative coupling, dendrimer, biological activity, cornplexation between tannin and protein
2 Fig. 1 Structures of ( H-epigallocatechin gallate and rosmarinic acid, and proposed biosynthesis of proanthocyanidins. Scheme 1 Biosynthesis of gallotannins. Vol.62 No
3 Fig. 2 Examples of ellagitannin monomers and oligomers.
4 Fig. 3 Structures of some ellagitannin oligomers from melastomataceous plants. Vol.62 No
5 Fig. 4 Examples of C-glucosidic ellagitannin dimers.
6 Fig. 5 Structures of corilagin, pedunculagin and epicatehin gallate. Vol.62 No
7 Fig. 6 Pictorial representation of protein coagulation through complexation with polyphenol. 530 (1990) Pharm. Bull., 37, 2083 (1989) 1) E. K. Seo, A. D. Kinghorn, "Studies in Natural Products Chemistry" Vol. 23, ed. by Atta-ur-Rahman, 2000, Elsevier, Amsterdam, p 531 2) N. Takeda, S. Seo, Y. Ogihara, U. Sankawa, I. Iitaka, I, Kitagawa, S. Shibata, Tetrahedron, 29, 3703 (1973) (a) E. Haslam, "Practical polyphenolies, from structure to molecular recognition and physiological action" Cambridge University Press, 1998; (b) T. Okuda, T. Yoshida, T. Hatano, Progress in the Chemistry of Organic Natural Products, 66, 1 (1995); (c) T. Yoshida, T. Hatano, H. Ito, "Studies in Natural Products Chemistry" Vol. 23, ed. by Atta-ur-Rahman, 2000, Elsevier, Amsterdam, 4) A. S. Hofmann, G. G. Gross, Arch. Biochem. Biophys., 283, 5) T. Okuda, T. Hatano, N. Ogawa, Chem. Pharm. Bull., 30, 4230 (1982) 6) T. Hatano, N. Ogawa, R. Kira, T. Yasuhara, T. Okuda, Chem. 7) T. Hatano, T. Yasuhara, M. Matsuda, K. Yazaki, T. Yoshida, T. Okuda, J. Chem. Soc. Perkin 1, 1990, ) T. Yoshida, T. Chou, A. Nitta, T. Okuda, Chem. Pharm. Bull., 40, 2023 (1992) 9) T. Yoshida, W. Ohwashi, K. Haba, H. Ohbayashi, K. Ishihara, Y. Okano, T. Shingu, T. Okuda, Chem. Pharm. Bull., 39, 2264
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