Top

Published in:

01-01-2019 | Original Paper

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

Authors: Satoru Tamura, Gang-Ming Yang, Teruaki Koitabashi, Yoshiharu Matsuura, Yasumasa Komoda, Tomikazu Kawano, Nobutoshi Murakami

Published in: Journal of Natural Medicines | Issue 1/2019

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.

Available only for authorised users

Homepage of World Health Organization (WHO); www.who.int/en/news-room/fact-sheets/detail/hepatitis-c

Saito I, Miyamura T, Ohbayashi A, Harada H, Katayama T, Kikuchi S, Watanabe Y, Koi S, Onji M, Ohta Y, Choo Q-L, Houghton M, Kuo G (1990) Chronic active hepatitis in transgenic mice expressing interferon-gamma in the liver. Proc Natl Acad Sci USA 87:6547–6549. https://doi.org/10.1073/pnas.91.2.614 CrossRefPubMedPubMedCentral

Wakita T (2007) HCV research and anti-HCV drug discovery: toward the next generation. Adv Drug Deliv Rev 59:1196–1199. https://doi.org/10.1016/j.addr.2007.08.021 CrossRefPubMed

Lohmann V, Korner F, Koch J, Herian U, Theilmann L, Bartenschlager R (1999) Replication of subgenomic hepatitis C virus RNAs in a hepatoma cell line. Science 285:110–113. https://doi.org/10.1126/science.285.5424.110 CrossRefPubMed

Matsuura Y, Tani H, Suzuki K, Kimura-Someya T, Suzuki R, Aizaki H, Ishii K, Moriishi K, Robison CS, Whitt MA, Miyamura T (2001) Characterization of Pseudotype VSV possessing HCV envelope proteins. Virology 286:263–275. https://doi.org/10.1006/viro.2001.0971 CrossRefPubMed

Tamura S, Yang G-M, Yasueda N, Matsuura Y, Komoda Y, Murakami N (2010) Tellimagrandin I, HCV invasion inhibitor from Rosae Rugosae Flos. Bioorg Med Chem Lett 20:1598–1600. https://doi.org/10.1016/j.bmcl.2010.01.084 CrossRefPubMed

Oenothera erythrosepala was purchased from Maechu Co. Ltd

Hatano T, Yasuhara T, Matsuda M, Yazaki K, Yoshida T, Okuda T (1990) Oenothein B, a dimeric, hydrolysable tannin with macrocyclic structure, and accompanying tannins from Oenothera erythrosepala. J Chem Soc Perkin Trans I:2735–2743. https://doi.org/10.1039/P19900002735 CrossRef

Yoshida T, Chou T, Shingu T, Okuda T (1995) Oenotheins D, F and G, hydrolysable tannin dimers from Oenothera laciniata. Phytochemistry 40:555–561. https://doi.org/10.1016/0031-9422(95)00267-B CrossRef

10.

Nayeshiro K, Eugster CH (1989) Notiz über Ellagitannine und Flavonol-glycoside aus Rosenblüten. Helv Chim Acta 72:985–992. https://doi.org/10.1002/hlca.19890720515 CrossRef

11.

Feldman K, Ensel S, Minard R (1994) Ellagitannin chemistry. The first total chemical synthesis of an Ellagitannin natural product, Tellimagrandin I. J Am Chem Soc 116:1742–1745. https://doi.org/10.1021/ja00084a015 CrossRef

12.

Takeuchi H, Ueda Y, Furuta T, Kawabata T (2017) Total synthesis of Ellagitannins via sequential site-selective functionalization of unprotected D-glucose. Chem Pharm Bull 65:25–32. https://doi.org/10.1248/cpb.c16-00436 CrossRef

13.

Yamada H, Ohara K, Ogura T (2013) Total Synthesis of Cercidinin A. Eur J Org Chem. https://doi.org/10.1002/ejoc.201301219 CrossRef

14.

Yamaguchi S, Hirokane T, Yoshida T, Tanaka T, Hatano T, Ito H, Nonakai G, Yamada H (2013) Roxbin B is cuspinin: structural revision and total synthesis. J Org Chem 78:5410–5417. https://doi.org/10.1021/jo400562k CrossRefPubMed

15.

Michihata N, Kaneko Y, Kasai Y, Tanigawa K, Hirokane T, Higasa S, Yamada H (2013) High-yield total synthesis of (−)-strictinin through intramolecular coupling of gallates. J. Org. Chem. 78:4319–4328. https://doi.org/10.1021/jo4003135 CrossRefPubMed

16.

Yamagauchi S, Ashikaga Y, Nishii K, Yamada H (2012) Total synthesis of the proposed structure of roxbin B; the nonidentical outcome. Org Lett 14:5928–5931. https://doi.org/10.1021/ol302845n CrossRef

17.

Kasai Y, Michihata N, Nishimura H, Hirokane T, Yamada H (2012) Total synthesis of (+)-davidiin. Angew Chem Int Ed 51:8026–8029. https://doi.org/10.1002/anie.201203305 CrossRef

18.

Hirokane T, Hirata Y, Ishimoto T, Nishii K, Yamada H (2014) A unified strategy for the synthesis of highly oxygenated diaryl ethers featured in ellagitannins. Nat Commun 5:3478. https://doi.org/10.1038/ncomms4478 CrossRefPubMed

19.

Asakura N, Fujimoto S, Michihata N, Nishii K, Imagawa H, Yamada H (2011) Synthesis of chiral and modifiable hexahydroxydiphenoyl compounds. J Org Chem 76:9711–9719. https://doi.org/10.1021/jo201750d CrossRefPubMed

20.

Bringmann G, Hartung T (1993) Atropo-enantioselective biaryl synthesis by stereocontrolled cleavage of configuratively labile lactone-bridged precursors using chiral H-nucleophiles. Tetrahedron 49:7891–7902. https://doi.org/10.1016/S0040-4020(01)88014-5 CrossRef

21.

Corey EJ, Bakshi RK, Shibata S, Chen C-P, Singh VK (1987) A stable and easily prepared catalyst for the enantioselective reduction of ketones. Applications to multistep syntheses. J Am Chem Soc 109:7925–7926. https://doi.org/10.1021/ja00259a075 CrossRef

22.

Shiina I, Kubota M, Ibuka R (2002) A novel and efficient macrolactonization of ω-hydroxycarboxylic acids using 2-methyl-6-nitrobenzoic anhydride (MNBA). Tetrahedron Lett 43:7535–7539. https://doi.org/10.1016/S0040-4039(02)01819-1 CrossRef

23.

Gross GG, Hemingway RW, Yoshida T (1999) Plant polyphenols 2: chemistry, biology, pharmacology, ecology. Springer, New York, pp 614–618CrossRef

24.

Zheng S, Laraia L, O’Connor CJ, Sorrell D, Tan YS, Xu Z, Venkitaraman AR, Wu W, Spring DR (2012) Synthesis and biological profiling of tellimagrandin I and analogues reveals that the medium ring can significantly modulate biological activity. Org Biomol Chem 10:2590–2593. https://doi.org/10.1039/c2ob25065a CrossRefPubMed

25.

Reddy BU, Mullick R, Kumar A, Sudha G, Srinivasan N, Das S (2014) Small molecule inhibitors of HCV replication from pomegranate. Sci Rep 4:5411. https://doi.org/10.1038/srep05411 CrossRefPubMedPubMedCentral

26.

Arapitsas P, Menichetti S, Vincieri F, Romani A (2007) Hydrolyzable tannins with the hexahydroxydiphenoyl unit and the m-depsidic link: HPLC-DAD-MS identification and model synthesis. J Agric Food Chem 55:48–55. https://doi.org/10.1021/jf0622329 CrossRefPubMed

Title: Oenothein B, dimeric hydrolysable tannin inhibiting HCV invasion from Oenothera erythrosepala
Authors: Satoru Tamura
Gang-Ming Yang
Teruaki Koitabashi
Yoshiharu Matsuura
Yasumasa Komoda
Tomikazu Kawano
Nobutoshi Murakami
Publication date: 01-01-2019
Publisher: Springer Singapore
Published in: Journal of Natural Medicines / Issue 1/2019
Print ISSN: 1340-3443
Electronic ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-018-1239-1

At a glance: The ONWARDS insulin icodec trials

Springer Medicine

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

Abstract

At a glance: The ONWARDS insulin icodec trials

Springer Medicine

Abstract

Please log in to get access to this content

Other articles of this Issue 1/2019

Aloin promotes osteogenesis of bone-marrow-derived mesenchymal stem cells via the ERK1/2-dependent Runx2 signaling pathway

Seven new resin glycosides from the seeds of Quamoclit × multifida

Effects of fermented Sorghum bicolor L. Moench extract on inflammation and thickness in a vascular cell and atherosclerotic mice model

Juzentaihoto hot water extract alleviates muscle atrophy and improves motor function in streptozotocin-induced diabetic oxidative stress mice

Cholestane glycosides from Ornithogalum saundersiae bulbs and the induction of apoptosis in HL-60 cells by OSW-1 through a mitochondrial-independent signaling pathway

Neuroprotective effect of naturally occurring RXR agonists isolated from Sophora tonkinensis Gagnep. on amyloid-β-induced cytotoxicity in PC12 cells