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

• Published in: Journal of organic chemistry Vol. 66; no. 21; pp. 6982 - 6987
• Main Authors: KIKUCHI, Haruhisa, SAITO, Yoshinori, KOMIYA, Jun, TAKAYA, Yoshiaki, HONMA, Shigeyoshi, NAKAHATA, Norimichi, ITO, Akira, OSHIMA, Yoshiteru
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 19.10.2001; Amer Chemical Soc
• Subjects: Amino Sugars - chemistry; Amino Sugars - isolation & purification; Amino Sugars - pharmacology; Animals; Antineoplastic Agents - chemistry; Antineoplastic Agents - isolation & purification; Antineoplastic Agents - pharmacology; Cell Differentiation - drug effects; Chemistry; Chemistry, Organic; Dictyostelium - chemistry; Drug Synergism; Molecular Conformation; Molecular Structure; Nerve Growth Factor - pharmacology; Neurites - drug effects; Neurites - ultrastructure; Neurons - drug effects; Neurons - pathology; Neurons - ultrastructure; Nuclear Magnetic Resonance, Biomolecular; Physical Sciences; Rats; Science & Technology; Tumor Cells, Cultured; CELLS; MORPHOGEN
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo015657x

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.