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

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Chemistry of Natural Compounds Aims and scope

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.

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References

  1. S. O. Duke, C. Canel, A. M. Rimando, M. R. Tellez, M. V. Duke, and R. N. Paul, Adv. Bot. Res., 31, 121 (2000).

    Article  CAS  Google Scholar 

  2. O. Spring, Adv. Bot. Res., 31, 153 (2000).

    Article  CAS  Google Scholar 

  3. A. L. Schilmiller, R. L. Last, and E. Pichersky, Plant J., 54, 702 (2008).

    Article  CAS  Google Scholar 

  4. T. Asai and Y. Fujimoto, Phytochemistry, 71, 1410 (2010).

    Article  CAS  Google Scholar 

  5. T. Asai, N. Nakamura, Y. Hirayama, K. Ohyama, and Y. Fujimoto, Phytochemistry, 82, 149 (2012).

    Article  CAS  Google Scholar 

  6. T. Shimizu, Asahi Encyclopedia – the World of Plants, Vol. 7, The Asahi Shimbun Co., Tokyo, 1995, p. 239.

  7. T. Ohtaki, K. Akasaka, C. Kabuto, and H. Ohrui, Chirality, 17, S171 (2005).

    Article  CAS  Google Scholar 

  8. J. Tian, W. C. Gao, D. M. Zhou, and C. Zhang, Org. Lett., 14, 3020 (2012).

    Article  CAS  Google Scholar 

Download references

Acknowledgment

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

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Authors and Affiliations

  1. Department of Chemistry and Materials Science, Tokyo Institute of Technology, Meguro, Tokyo, 152-8551, Japan

    A. Ohkawa, K. Ohyama & Y. Fujimoto

Authors
  1. A. Ohkawa
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  2. K. Ohyama
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  3. Y. Fujimoto
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Corresponding author

Correspondence to Y. Fujimoto.

Additional information

Published in Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2018, pp. 709–712.

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Ohkawa, A., Ohyama, K. & Fujimoto, Y. 9-Hydroxy-, 9-Acetyloxy-, and 9-Hexanoyloxy Fatty Acids from the Glandular Trichome Exudate of Silene latifolia subsp. alba. Chem Nat Compd 54, 833–836 (2018). https://doi.org/10.1007/s10600-018-2493-x

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  • DOI: https://doi.org/10.1007/s10600-018-2493-x

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