Furanodictine A and B: Amino sugar analogues produced by cellular slime mold Dictyostelium discoideum showing neuronal differentiation activity

Haruhisa Kikuchi, Y. Saito, J. Komiya, Y. Takaya, S. Honma, N. Nakahata, A. Ito, Yoshiteru Oshima

Research output: Contribution to journalArticlepeer-review

59 Citations (Scopus)

Abstract

We investigated the constituents of Dictyostelium discoideum to clarify the diversity of secondary metabolites of Dictyostelium cellular slime molds and to explore biologically active substances that could be useful in the development of novel drugs. From a methanol extract of the multicellular fruit body of D. discoideum, we isolated two novel amino sugar analogues, furanodictine A (1) and B (2). They are the first 3,6-anhydrosugars to be isolated from natural sources. Their relative structures were elucidated by spectral means, and the absolute configurations were confirmed by asymmetric syntheses of 1 and 2. These furanodictines potently induce neuronal differentiation of rat pheochromocytoma (PC-12) cells.

Original languageEnglish
Pages (from-to)6982-6987
Number of pages6
JournalJournal of Organic Chemistry
Volume66
Issue number21
DOIs
Publication statusPublished - 2001 Oct 19

ASJC Scopus subject areas

  • Organic Chemistry

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