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Journal of Biochemistry Advance Access published online on April 16, 2008
Journal of Biochemistry, doi:10.1093/jb/mvn050
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© 2008 The Japanese Biochemical Society

Chemical and apoptotic properties of hydroxy-ceramides containing long-chain bases with unusual alkyl chain lengths

Mamoru Kyogashima1,2, Keiko Tadano-Aritomi3, Toshifumi Aoyama4, Akiko Yusa1, Yoshiko Goto1, Keiko Tamiya-Koizumi1,5, Hiromi Ito5, Takashi Murate5, Reiji Kannagi1 and Atsushi Hara4

1Division of Molecular Pathology, Aichi Cancer Center Research Institute, 1-1 Kanokoden, Chikusa-ku, Nagoya, Aichi, 464-8681, Japan
2Department of Oncology, Graduate School of Pharmaceutical Sciences, Nagoya City University, 3-1 Tanabe-dori, Mizuho-ku, Nagoya, 467-8603, Japan
3Department of Biochemistry, Teikyo University School of Medicine, 2-11-1 Kaga, Itabashi-ku, Tokyo, 173-8605, Japan
4Department of Metabolic Regulation, Institute on Aging and Adaptation, Shinshu University Graduate School of Medicine, 3-1-1 Asahi, Matsumoto, Nagano, 390-8621, Japan
5Department of Medical Technology, Nagoya University Graduate School of Health Sciences, 1-1-20, Daiko-Minami, Higashi-ku, Nagoya, Aichi, 461-8673, Japan

Corresponding author: Dr. Mamoru Kyogashima, Kanokoden Chikusa-ku, Nagoya 464-8681, Japan, Ph: +81-52-762-6111, Fax: +81-52-763-5233, E-mail: mkyogashi{at}aichi-cc.jp

Received February 29, 2008; Accepted March 20, 2008


  Abstract

We analyzed 4 types of free ceramides (Cer 1, Cer 2, Cer 3 and Cer 4) from equine kidneys by electrospray ionization mass spectrometry. Cer 1 was composed of dihydroxy long-chain bases (dLCBs) of (4E)-sphingenine (d18:1), sphinganine and nonhydroxy fatty acids (NFAs); Cer 2 was composed of trihydroxy LCBs (tLCBs) of 4-hydroxysphinganine, t16:0, t18:0, t19:0 and t20:0, and NFAs; Cer 3 was composed of dLCBs, d16:1, d17:1, d18:1, d19:1 and d20:1, and hydroxy FAs (HFAs); and Cer 4 was composed of tLCBs, t16:0, t17:0, t18:0, t19:0 and t20:0, and HFAs. The results indicate all ceramide species containing LCBs with non-octadeca lengths (NOD-LCBs) can be classified into hydroxy-ceramides since these species always consist of tLCBs, and/or HFAs. Furthermore, such species tend to contain FAs with longer acyl chains but contain neither palmitate (C16:0) nor its hydroxylated form (C16:0h). The apoptosis-inducing activities of these hydroxyl-ceramides towards tumor cell lines were compared with that of non-hydroxy-ceramides, dLCB-NFA (Cer 1). Monohydroxy-ceramides, tLCB-NFA (Cer 2) and dLCB-HFA (Cer 3), exhibited stronger activities, whereas dihydroxy-ceramide, tLCB-HFA (Cer 4), exhibited similar or weaker activity than dLCB-NFA (Cer 1), depending on cell lines.

Key Words: Ceramides, Hydroxy-ceramides, Long-chain bases, Mass spectrometry, Apoptosis


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