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

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.

Debenzylative Cycloetherification: An Overlooked Key Strategy for Complex Tetrahydrofuran Synthesis

“…Moreover, tetrahydrofurans are found in a large number of bioactive natural products and synthetic compounds . For example, molecules such as jaspine B, (+)‐davanone, (+)‐artemone, (−)‐gymnodimine, (+)‐varitriol, trilobacin, furanodictine A and B, and ι‐ and κ‐carrageenan have shown biological properties including antiviral, antitumor, antihyperlipidemic, antioxidative, and antiinflammatory activities (Figure ). As an example, eribulin, which mimics part of the structure of the marine macrolide halichondrin B, is now in clinical trials as a promising breast anticancer agent…”

Natural Products from Social Amoebae

“…Several syntheses of the furanodictines exist. The first synthesis of furanodictine A ( 93 ) by Kikuchi et al . (Scheme a) started with treatment of N ‐acetyl‐ d ‐glucosamine ( 87 ) with sulfuric acid in methanol to afford a mixture of α‐ and β‐anomers and their deacetylated products.…”

“…Staudinger reduction of the azido group afforded amine 119 , which was subsequently acetylated with acetic anhydride in pyridine; debenzylation of amide 120 gave methyl 3,6‐anhydro‐ N ‐acetylamino‐β‐ d ‐mannofuranoside dia ‐90 . The previously reported synthesis for furanodictine B ( 112 ) from alcohol 90 (Scheme a) was then followed for dia ‐ 90 to yield the natural product …”

Lycoperdinoside A and B, New Glycosides from the Slime Mold Enteridium lycoperdon

“…These furanodictines show the potential to induce neuronal differentiation of rat pheochromocytoma (PC-12) cells. [8] A novel, chloro-containing, antibacterial substance, AB0022, was isolated from the cellular slime mold Dictyostelium purpureum K1001. It inhibited the growth of Grampositive bacteria, and its MICs ranged from 0.39 to 50 µg/ ml.…”