Representative LC/UV chromatogram under typical analytical conditions (C18 column; mobile phase: 5–100% ACN / H2O (0.05% H3PO4), linear gradient 20 min; flow rate: 0.2 mL/min; detection: 210 nm).
NMR Spectral Data
Representative 1H NMR (500 MHz) spectrum confirming the structure of Neoxaline. Representative 13C NMR (125 MHz) spectrum supporting structural assignment of Neoxaline.
Source Organism
Aspergillus japonicus.
Summary
Neoxaline is a fungal indoline spiroaminal alkaloid with weak central nervous system activity.
Details
Neoxaline is a prenylated indoline spiroaminal alkaloid isolated from Aspergillus japonicus. Structurally characterized by a tetracyclic indoline spiroaminal framework containing a reverse-prenyl group and a dehydrohistidine-derived unit, it represents a unique fungal alkaloid scaffold. Although it lacks antimicrobial activity, neoxaline exhibits weak central nervous system stimulant effects, indicating interaction with neuroactive pathways. It has primarily served as a structural and synthetic target, with multiple stereoselective total syntheses establishing its absolute configuration and highlighting its complex spirocyclic architecture.