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Chemical and Biological Significance of Oenothein B and Related Ellagitannin Oligomers with Macrocyclic Structure

1
College of Pharmaceutical Sciences, Matsuyama University, 4-2 Bunkyo-cho, Matsuyama, Ehime 790-8578, Japan
2
Okayama University, Okayama 701-1152, Japan
*
Author to whom correspondence should be addressed.
Molecules 2018, 23(3), 552; https://doi.org/10.3390/molecules23030552
Received: 5 February 2018 / Revised: 26 February 2018 / Accepted: 26 February 2018 / Published: 2 March 2018
In 1990, Okuda et al. reported the first isolation and characterization of oenothein B, a unique ellagitannin dimer with a macrocyclic structure, from the Oenothera erythrosepala leaves. Since then, a variety of macrocyclic analogs, including trimeric–heptameric oligomers have been isolated from various medicinal plants belonging to Onagraceae, Lythraceae, and Myrtaceae. Among notable in vitro and in vivo biological activities reported for oenothein B are antioxidant, anti-inflammatory, enzyme inhibitory, antitumor, antimicrobial, and immunomodulatory activities. Oenothein B and related oligomers, and/or plant extracts containing them have thus attracted increasing interest as promising targets for the development of chemopreventive agents of life-related diseases associated with oxygen stress in human health. In order to better understand the significance of this type of ellagitannin in medicinal plants, this review summarizes (1) the structural characteristics of oenothein B and related dimers; (2) the oxidative metabolites of oenothein B up to heptameric oligomers; (3) the distribution of oenotheins and other macrocyclic analogs in the plant kingdom; and (4) the pharmacological activities hitherto documented for oenothein B, including those recently found by our laboratory. View Full-Text
Keywords: oenothein B; ellagitannin; macrocyclic oligomer; Onagraceae; Myrtaceae; Lythraceae; antioxidants; antitumor effect; immunomodulatory effect; anti-inflammation oenothein B; ellagitannin; macrocyclic oligomer; Onagraceae; Myrtaceae; Lythraceae; antioxidants; antitumor effect; immunomodulatory effect; anti-inflammation
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Yoshida, T.; Yoshimura, M.; Amakura, Y. Chemical and Biological Significance of Oenothein B and Related Ellagitannin Oligomers with Macrocyclic Structure. Molecules 2018, 23, 552.

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