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Journal of Natural Medicines

, Volume 72, Issue 3, pp 667–674 | Cite as

Three new 5,6,7,8-tetrahydroxy-5,6,7,8-tetrahydrochromone derivatives enantiomeric to agarotetrol from agarwood

  • Takuji Sugiyama
  • Yuji Narukawa
  • Shunsuke Shibata
  • Ryo Masui
  • Fumiyuki KiuchiEmail author
Original Paper

Abstract

Agarwood (jinkoh in Japanese) is a resinous wood from Aquilaria species of the family Thymelaeaceae and has been used as incense and in traditional medicines. Characteristic chromone derivatives such as agarotetrol have been isolated from agarwood. In previous study, we isolated two new 2-(2-phenylethyl)chromones together with six known compounds from MeOH extract of agarwood. Further chemical investigation of the MeOH extract led to isolation of eighteen 2-(2-phenylethyl)chromones, including three new 5,6,7,8-tetrahydroxy-5,6,7,8-tetrahydrochromones with stereochemistry enantiomeric to agarotetrol-type, viz. (5R,6S,7S,8R)-2-[2-(3′-hydroxy-4′-methoxyphenyl)ethyl]-5,6,7,8-tetrahydroxy-5,6,7,8-tetrahydrochromone (2), (5R,6S,7S,8R)-2-[2-(4′-methoxyphenyl)ethyl]-5,6,7,8-tetrahydroxy-5,6,7,8-tetrahydrochromone (6), and (5R,6S,7S,8R)-2-[2-(4′-hydroxy-3′- methoxyphenyl)ethyl]-5,6,7,8-tetrahydroxy-5,6,7,8-tetrahydrochromone (13). The absolute configurations of the new compounds were determined by exciton chirality method. All isolated compounds were tested for their phosphodiesterase (PDE) 3A inhibitory activity by fluorescence polarization method. Compounds 8, 1215, 2124 showed moderate PDE 3A inhibitory activity.

Keywords

Agarwood 2-(2-Phenylethyl)chromone 5,6,7,8-Tetrahydroxy-5,6,7,8-tetrahydrochromone Enantiomer Phosphodiesterase inhibitor 

Notes

Acknowledgements

This work was supported in part by Keio Gijyuku Academic Development Funds and MEXT-Supported Program for the Strategic Research Foundation at Private Universities.

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Copyright information

© The Japanese Society of Pharmacognosy and Springer Japan KK, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Faculty of PharmacyKeio UniversityTokyoJapan
  2. 2.Tokyo Research CenterKyushin Pharmaceutical Co. Ltd.TokyoJapan

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