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Review
. 2010 Jan 6;11(1):79-106.
doi: 10.3390/ijms11010079.

Structural features and biological properties of ellagitannins in some plant families of the order Myrtales

Takashi Yoshida  1 , Yoshiaki Amakura  1 , Morio Yoshimura  1
Affiliations
Review

Structural features and biological properties of ellagitannins in some plant families of the order Myrtales

Takashi Yoshida et al. Int J Mol Sci. .

Abstract

Plant tannins, including hydrolysable and condensed varieties, are well known antioxidants in medicinal plants, foods, and edible fruits. Their diverse biological properties and potential for disease prevention have been demonstrated by various in vitro and in vivo assays. A number of ellagitannins, the largest group of hydrolysable tannins, have been isolated from dicotyledoneous angiosperms and characterized. This diverse class of tannins is sub-grouped into simple ellagitannins, C-glycosidic ellagitannins, complex tannins (condensates of C-glycosidic tannins with flavan-3-ol), and oligomers up to pentamers. This review outlines and describes the chemotaxonomic significance of structural features in various types of ellagitannins found in plants belonging to the Myrtaceae, Onagraceae, and Melastomataceae families, which are all included in the order Myrtales. Any biological activities that have been reported, including antitumor and antibacterial effects as well as enzyme inhibition, are also reviewed.

Keywords: C-glycosidic ellagitannins; Myrtales; biological activity; ellagitannins; oligomeric ellagitannins.

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Figures

Figure 1.
Figure 1.
Structures of monomeric ellagitannins 1–15.
Figure 2.
Figure 2.
Structures of C-glycosidic ellagitannins 16–29.
Figure 3.
Figure 3.
(a) Structures of complex tannins 30–40. (b) Structures of complex tannins 41–44.
Figure 3.
Figure 3.
(a) Structures of complex tannins 30–40. (b) Structures of complex tannins 41–44.
Figure 4.
Figure 4.
General oligomerization mode for the types 1 and 2. (1) examples of coupling mode for formation of valeoyl or its equivalent unit by C-O coupling. (2) macrocyclic dimer (double coupling for HHDP and galloyl).
Figure 5.
Figure 5.
Structures of C-glycosidic ellagitannin dimers 45–48.
Figure 6.
Figure 6.
(a) Structures of ellagitannin oligomers 49–59. (b) Structures of ellagitannin oligomers 60 and 61.
Figure 6.
Figure 6.
(a) Structures of ellagitannin oligomers 49–59. (b) Structures of ellagitannin oligomers 60 and 61.
Figure 7.
Figure 7.
(a) Structures of ellagitannin oligomers 62 and 66. (b) Structures of ellagitannin oligomers 63–65.
Figure 8.
Figure 8.
Coupling modes (a–d) to melasquanins A (62)–D (65).
Figure 9.
Figure 9.
Structures of ellagitannin oligomers 67 and 68.
Figure 10.
Figure 10.
Coupling mode of nobotanins.
Figure 11.
Figure 11.
(a) Structures of ellagitannin oligomers 72 and 73. (b) Structures of ellagitannin oligomers 74–77.
Figure 11.
Figure 11.
(a) Structures of ellagitannin oligomers 72 and 73. (b) Structures of ellagitannin oligomers 74–77.
Figure 12.
Figure 12.
Chemical degradation of nobotanin B (70).
Figure 13.
Figure 13.
HMBC data for melasquanin A (62).
Figure 14.
Figure 14.
Structures of metabolites from ellagitannins.
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References

    1. Okuda T, Yoshida T, Hatano T. Progress in the Chemistry of Organic Natural Products. Springer; New York, NY, USA: 1995. - PubMed
    1. Haslam E. Plant Polyphenols. Cambridge University Press; Cambridge, UK: 1989.
    1. Okuda T, Yoshida T, Hatano T. Classification of oligomeric hydrolysable tannins and specificity of their occurrence in plants. Phytochemistry. 1993;32:507–521.
    1. Bremer B, Bremer K, Chase MW, Reveal JL, Soltis DE, Soltis PS, Stevens PF, Anderberg AA, Fay MF, Goldblatt P, Judd WS, Källersjö M, Kårehed J, Kron KA, Lundberg J, Nickrent DL, Olmstead RG, Oxelman B, Pires JC, Rodman JE, Rudall PJ, Savolainen V, Sytsma KJ, Bank MVD, Wurdack K, Xiang JQY, Zmarzty S. An update of the angiosperm phylogeny group classification for the orders and families of flowering plants: APG II. Bot. J. Linn. Soc. 2003;141:399–436.
    1. Niemetz R, Gross GG. Enzymology of gallotannin and ellagitannin biosynthesis. Phytochemistry. 2005;66:2001–2011. - PubMed

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