Submitted on August 30, 2006
Revised on November 27, 2006
Accepted on December 12, 2006
Novel free ceramides as components of the soldier defense gland of the Formosan subterranean termite (Coptotermes formosanus)
Masaya Ohta, Fumito Matsuura, Gregg Henderson, and Roger A. Laine
Department of Biotechnology, Fukuyama University, Fukuyama-shi, Hiroshima 729-0292
Corresponding Author: ohta{at}bt.fubt.fukuyama-u.ac.jp
On HPTLC analysis, no glycolipids and phospholipids were detected but one spot corresponding to free fatty acids and three spots (termed TL-1, TL-2 and TL-3) migrating in the region of ceramides were detected in the lipids from the frontal gland secretions. Free fatty acids were confirmed to be lignoceric acid (C24:0) and hexacosanoic acid (C26:0) as previously described (Chen et al., 1999, J. Chem. Ecol. 25, 817-824). The TL-1, TL-2 and TL-3 were confirmed to be ceramides differing in their hydrophobicity based on the results of MALDI-TOF MS analysis, mild alkaline treatment, GC-MS analysis of fatty acid methylester, and GC-MS analysis of LCBs as TMS-derivatives. The structures of LCBs were further confirmed by GC-MS of aldehydes derived from LCBs by NaIO4 oxidation and of alcohols derived from aldehydes by reduction with NaBH4. Double bond positions in LCBs were determined by GC-MS of polyhydroxy alcohols derived from alcohols by OsO4 oxidation. Fatty acids in TL-1 and TL-2 were C18:0, C20:0 and C22:0 and TL-3 2-hydroxy C18:0, C20:0 and C22:0. The structures and composition of LCBs were quite unique. TL-1 contained only C18-sphinganine. The most predominant LCB in TL-2 was detected to be a novel trihydroxy C14-sphingosine, 1,3,9-trihydroxy-2-amino-6-tetradecene. TL-3 contained C18-sphinganine and two kinds of novel sphingadienines, 1,3-dihydroxy-2-amino-7,10-hexadecadiene and 1,3-dihydroxy-2-amino-11,14-eicosadiene.
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