Newly discovered neutral glycosphingolipids in Aureobasidin A-resistant Zygomycetes. Identification of a novel family of gala-series glycolipids with core Galα1-6Galβ1-6Galβ sequences

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

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

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 ionisation lime-of-flight/mass spectrometry, and 1H NMR spectroscopy. They were as follows: Galβ1-6Galβ1-1Cer (CDS), Galα1-6Galβ1- 6Galβ1-1Cer (CTS), Galα1-6Galα1-6Galβ1-6Galβ1-1Cer (CTeS), and Galα1-6Galα1-6Galα1-6Galβ1-6Galβ1-1Cer (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.

Original languageEnglish
Pages (from-to)32028-32034
Number of pages7
JournalJournal of Biological Chemistry
Volume279
Issue number31
DOIs
Publication statusPublished - 2004 Jul 30

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Neutral Glycosphingolipids
Glycosphingolipids
Glycolipids
Fungi
phytosphingosine
Antifungal Agents
Fatty Acids
Mucormycosis
Mucor
Sugar Acids
Hydroxy Acids
Methylation
Ceramides
Biosynthetic Pathways
Sugars
Nuclear magnetic resonance spectroscopy
Ionization
Mass spectrometry
Desorption
Mass Spectrometry

ASJC Scopus subject areas

  • Biochemistry

Cite this

Newly discovered neutral glycosphingolipids in Aureobasidin A-resistant Zygomycetes. Identification of a novel family of gala-series glycolipids with core Galα1-6Galβ1-6Galβ sequences. / Aoki, Kazuhiro; Uchiyama, Ryosuke; Yamauchi, Suguru; Katayama, Takane; Itonori, Saki; Sugita, Mutsumi; Hada, Noriyasu; Yamada-Hada, Junko; Takeda, Tadahiro; Kumagai, Hidehiko; Yamamoto, Kenji.

In: Journal of Biological Chemistry, Vol. 279, No. 31, 30.07.2004, p. 32028-32034.

Research output: Contribution to journalArticle

Aoki, K, Uchiyama, R, Yamauchi, S, Katayama, T, Itonori, S, Sugita, M, Hada, N, Yamada-Hada, J, Takeda, T, Kumagai, H & Yamamoto, K 2004, 'Newly discovered neutral glycosphingolipids in Aureobasidin A-resistant Zygomycetes. Identification of a novel family of gala-series glycolipids with core Galα1-6Galβ1-6Galβ sequences', Journal of Biological Chemistry, vol. 279, no. 31, pp. 32028-32034. https://doi.org/10.1074/jbc.M312918200
Aoki, Kazuhiro ; Uchiyama, Ryosuke ; Yamauchi, Suguru ; Katayama, Takane ; Itonori, Saki ; Sugita, Mutsumi ; Hada, Noriyasu ; Yamada-Hada, Junko ; Takeda, Tadahiro ; Kumagai, Hidehiko ; Yamamoto, Kenji. / Newly discovered neutral glycosphingolipids in Aureobasidin A-resistant Zygomycetes. Identification of a novel family of gala-series glycolipids with core Galα1-6Galβ1-6Galβ sequences. In: Journal of Biological Chemistry. 2004 ; Vol. 279, No. 31. pp. 32028-32034.
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