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J. Biol. Chem., Vol. 279, Issue 31, 32028-32034, July 30, 2004

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Newly Discovered Neutral Glycosphingolipids in Aureobasidin A-resistant Zygomycetes

IDENTIFICATION OF A NOVEL FAMILY OF GALA-SERIES GLYCOLIPIDS WITH CORE Gal1-6Gal1-6Gal SEQUENCES^*

Kazuhiro Aoki, Ryosuke Uchiyama, Suguru Yamauchi, Takane Katayama, Saki Itonori¶, Mutsumi Sugita¶, Noriyasu Hada||, Junko Yamada-Hada||, Tadahiro Takeda||, Hidehiko Kumagai, and Kenji Yamamoto

From the Graduate School of Biostudies, Kyoto University, Oiwake-cho, Kitashirakawa, Sakyo-ku, Kyoto 606-8502, Japan, the ^¶Faculty of Liberal Arts and Education, Shiga University, 2-5-1, Hiratsu, Otsu, Shiga 520-0862, Japan, and the ^||Kyoritsu University of Pharmacy, 1-5-30, Shibakoen, Minato-ku, Tokyo 105-8512, Japan

We found for the first time that Zygomycetes species showed resistance to Aureobasidin A, an antifungal agent. A novel family of neutral glycosphingolipids (GSLs) was found in these fungi and isolated from Mucor hiemalis, which is a typical Zygomycetes species. Their structures were completely determined by compositional sugar, fatty acid, and sphingoid analyses, methylation analysis, matrix-assisted laser desorption ionization time-of-flight/mass spectrometry, and ¹H NMR spectroscopy. They were as follows: Gal1-6Gal1-1Cer (CDS), Gal1-6Gal1-6Gal1-1Cer (CTS), Gal1-6Gal1-6Gal1-6Gal1-1Cer (CTeS), and Gal1-6Gal1-6Gal1-6Gal1-6Gal1-1Cer (CPS). The ceramide moieties of these GSLs consist of 24:0, 25:0, and 26:0 2-hydroxy acids as major fatty acids and 4-hydroxyoctadecasphinganine (phytosphingosine) as the sole sphingoid. However, the glycosylinositolphosphoceramide families that are the major GSLs components in fungi were not detected in Zygomycetes at all. This seems to be the reason that Aureobasidin A is not effective for Zygomycetes as an antifungal agent. Our results indicate that the biosynthetic pathway for GSLs in Zygomycetes is significantly different from those in other fungi and suggest that any inhibitor of this pathway may be effective for mucormycosis, which is a serious pathogenic disease for humans.

Received for publication, November 26, 2003 , and in revised form, May 12, 2004.

^* The costs of publication of this article were defrayed in part by the payment of page charges. This article must therefore be hereby marked "advertisement" in accordance with 18 U.S.C. Section 1734 solely to indicate this fact.

Supported by the 21st Century COE Program of the Ministry of Education, Culture, Sports, Science and Technology to the Graduate School of Biostudies and Institute for Virus Research, Kyoto University. To whom correspondence should be addressed. Tel.: 81-75-753-6278; Fax: 81-75-753-6275; E-mail: kaoki{at}lif.kyoto-u.ac.jp.

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