Journal of Natural Medicines

, Volume 72, Issue 1, pp 220–229 | Cite as

Naphthalene glycosides in the Thai medicinal plant Diospyros mollis

  • Takaharu Suwama
  • Keisuke Watanabe
  • Orawan Monthakantirat
  • Prathan Luecha
  • Hiroshi Noguchi
  • Kenji Watanabe
  • Kaoru UmeharaEmail author
Original Paper


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, 35). 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.


Diospyros mollis Ebenaceae Diospyrol glycoside Naphthoquinone glycoside Naphthalene glycoside Makluoside A–E Hyaluronidase inhibition 



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.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Supplementary material

11418_2017_1134_MOESM1_ESM.pdf (4.7 mb)
Supplementary material 1 (PDF 4859 kb)


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Copyright information

© The Japanese Society of Pharmacognosy and Springer Japan KK 2017

Authors and Affiliations

  1. 1.School of Pharmaceutical SciencesUniversity of ShizuokaShizuokaJapan
  2. 2.Faculty of Pharmaceutical SciencesKhon Kaen UniversityKhon KaenThailand
  3. 3.Faculty of Pharmaceutical SciencesYokohama University of PharmacyYokohamaJapan

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