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Oenothein B, dimeric hydrolysable tannin inhibiting HCV invasion from Oenothera erythrosepala

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Abstract

The envelope proteins of the hepatitis C virus (HCV), E1 and E2, have been revealed to be essential for invasion of HCV. Thus, we were engaged in the search for the inhibitors against HCV invasion through the assay system using the model virus expressing recombinant HCV envelopes, E1 and E2. Now, we disclosed dimeric hydrolysable tannin oenothein B (1) from MeOH extract of Oenothera erythrosepala as an active principle for inhibition of HCV invasion and its potency was almost the same as that of monomeric hydrolysable tannin, tellimagrandin I (2). Furthermore, by use of stereoselectively prepared 1-β- and 1-α-O-methyl tellimagrandin Is (4 and 5), the introduction of methyl moiety into 1-hydroxy group of 2 was clarified to result in slightly reduction of activity and β-isomer was revealed to exhibit a little stronger activity than α-one.

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Acknowledgements

This work was supported by JSPS KAKENHI Grant number JP16790011, Grant-in-Aid for Young Scientists (B) and Research funds from San-Ei Gen F. F. I. Inc.

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Authors and Affiliations

  1. Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka, 565-0871, Japan

    Satoru Tamura, Gang-Ming Yang, Teruaki Koitabashi & Nobutoshi Murakami

  2. School of Pharmacy, Iwate Medical University, 2-1-1 Nishitokuda Yahaba-cho Siwa-gun, Iwate, 019-3694, Japan

    Satoru Tamura & Tomikazu Kawano

  3. Research Center for Emerging Infectious Diseases, Research Institute for Microbial Diseases, Osaka University, 3-1 Yamada-oka, Suita, Osaka, 565-0871, Japan

    Yoshiharu Matsuura & Yasumasa Komoda

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  1. Satoru Tamura
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  2. Gang-Ming Yang
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  4. Yoshiharu Matsuura
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Correspondence to Satoru Tamura.

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Tamura, S., Yang, GM., Koitabashi, T. et al. Oenothein B, dimeric hydrolysable tannin inhibiting HCV invasion from Oenothera erythrosepala. J Nat Med 73, 67–75 (2019). https://doi.org/10.1007/s11418-018-1239-1

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  • DOI: https://doi.org/10.1007/s11418-018-1239-1

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