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Naphthalene glycosides in the Thai medicinal plant Diospyros mollis

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Abstract

This study evaluated methanol extracts from the leaves and branches of the Thai medicinal plant Diospyros mollis (Ebenaceae). Seven triterpenes and 22 aromatic compounds, including five new compounds, were isolated, and their structures were determined. The new compounds had the following structures: diospyrol glycoside (makluoside A, 1), 8,8′-di-O-6-β-d-apiofuranosyl-β-d-glucopyranosyl-6,6′-dimethyl-2,3′-binaphthalene-1-ol-1′,4′- dione (makluoside B, 2), and 3-methyl-1,8- naphthalenediol glycosides (makluosides C-E, 3–5). Makluoside B is the first example of a naphthoquinone glycoside that has both a 3-methyl-1,8-naphthalenediol unit and a 5-hydroxy-7-methyl-1,4-naphthoquinone unit. The hyaluronidase inhibitory activity of the isolates was evaluated, revealing that one of the triterpene derivatives possessed moderate inhibitory activity.

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Acknowledgements

This work was partially supported by the Japan Society for the Promotion of Science (JSPS) KAKENHI Grant Number 25460126 to K.U. We thank Philip Hawke of the University of Shizuoka Scientific English Program for proofreading the English in the manuscript.

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Author notes

  1. Kaoru Umehara

    Present address: Faculty of Pharmaceutical Sciences, Yokohama University of Pharmacy, 601 Matano-cho, Totsuka-ward, Yokohama, Kanagawa, 245-0066, Japan

Authors and Affiliations

  1. School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Shizuoka, 422-8526, Japan

    Takaharu Suwama, Keisuke Watanabe, Hiroshi Noguchi, Kenji Watanabe & Kaoru Umehara

  2. Faculty of Pharmaceutical Sciences, Khon Kaen University, Khon Kaen, 40002, Thailand

    Orawan Monthakantirat & Prathan Luecha

Authors
  1. Takaharu Suwama
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  2. Keisuke Watanabe
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  3. Orawan Monthakantirat
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  4. Prathan Luecha
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  5. Hiroshi Noguchi
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Correspondence to Kaoru Umehara.

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Suwama, T., Watanabe, K., Monthakantirat, O. et al. Naphthalene glycosides in the Thai medicinal plant Diospyros mollis . J Nat Med 72, 220–229 (2018). https://doi.org/10.1007/s11418-017-1134-1

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  • DOI: https://doi.org/10.1007/s11418-017-1134-1

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