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Chemistry of Natural Compounds

, Volume 54, Issue 5, pp 833–836 | Cite as

9-Hydroxy-, 9-Acetyloxy-, and 9-Hexanoyloxy Fatty Acids from the Glandular Trichome Exudate of Silene latifolia subsp. alba

  • A. Ohkawa
  • K. Ohyama
  • Y. Fujimoto
Article

Chemical investigation of the glandular trichome exudate from Silene latifolia subsp. alba (Caryophyllaceae) resulted in the identification of 9-hydroxyoctadecanoic acid (1) and five new fatty acids 9-hydroxyicosanoic acid (2), 9-acetyloxyoctadecanoic acid (3), 9-acetyloxyicosanoic acid (4), 9-hexanoyloxyhexadecanoic acid (5) and 9-hexanoyloxyoctadecanoic acid (6). The oxygenated positions in these fatty acid derivatives were determined to be at C-9 by GC-MS analysis of their trimethylsilyl (TMS) derivatives, while the configurations at C-9 of compounds 1 and 2 were established as S by application of the Akasaka-Ohrui method to their methyl esters.

Keywords

Silene latifolia subsp. alba Caryophyllaceae glandular trichome hydroxy-fatty acid 9-acetyloxyoctadecanoic acid 9-hexanoyloxyoctadecanoic acid 

Notes

Acknowledgment

The authors thank Ms. Itoh Satsuki, Tokyo Institute of Technology, for the FAB-MS measurement.

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department of Chemistry and Materials ScienceTokyo Institute of TechnologyTokyoJapan

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