9-Hydroxy-, 9-Acetyloxy-, and 9-Hexanoyloxy Fatty Acids from the Glandular Trichome Exudate of Silene latifolia subsp. alba
- 88 Downloads
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 acidNotes
Acknowledgment
The authors thank Ms. Itoh Satsuki, Tokyo Institute of Technology, for the FAB-MS measurement.
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).CrossRefGoogle Scholar
- 2.O. Spring, Adv. Bot. Res., 31, 153 (2000).CrossRefGoogle Scholar
- 3.A. L. Schilmiller, R. L. Last, and E. Pichersky, Plant J., 54, 702 (2008).CrossRefGoogle Scholar
- 4.T. Asai and Y. Fujimoto, Phytochemistry, 71, 1410 (2010).CrossRefGoogle Scholar
- 5.T. Asai, N. Nakamura, Y. Hirayama, K. Ohyama, and Y. Fujimoto, Phytochemistry, 82, 149 (2012).CrossRefGoogle Scholar
- 6.T. Shimizu, Asahi Encyclopedia – the World of Plants, Vol. 7, The Asahi Shimbun Co., Tokyo, 1995, p. 239.Google Scholar
- 7.T. Ohtaki, K. Akasaka, C. Kabuto, and H. Ohrui, Chirality, 17, S171 (2005).CrossRefGoogle Scholar
- 8.J. Tian, W. C. Gao, D. M. Zhou, and C. Zhang, Org. Lett., 14, 3020 (2012).CrossRefGoogle Scholar