Furanodictine A and B:  Amino Sugar Analogues Produced by Cellular Slime Mold Dictyostelium d iscoideum Showing Neuronal Differentiation Activity

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 frui...

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Bibliographic Details
Published in:Journal of organic chemistry 2001-10, Vol.66 (21), p.6982-6987
Main Authors: Kikuchi, Haruhisa, Saito, Yoshinori, Komiya, Jun, Takaya, Yoshiaki, Honma, Shigeyoshi, Nakahata, Norimichi, Ito, Akira, Oshima, Yoshiteru
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo015657x