Lampteromyces Bioluminescence---production of the light emitter from riboflavin

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The molecular mechanism of the bioluminescence in moon-night mushroom (TSUKIYOTAKE) is to be elucidated in this project. The chromophore of the light emitter in this luminescence was assigned to be isoalloxazine from the facts that the bioluminescence spectrum showed its maximum at 524 nm and that the extracts showed an identical fluorescence spectrum. Luminous myceria was cultivated to exhibit the same light as the gills from the mushroom. The light emitter was named as lampteroflavin. It was isolated from an acidic solution in which fresh gills were immerged and luminesced for overnight under oxygen atmosphere. The solution was passed through columns which combined the hydrophobic substances. Methanol eluate afforded a single green fluorescent compound, lampteroflavin, which showed m/z 509 in FAB-MS spectrum. Lampteroflavin was readily hydrolyzed by acid into riboflavin, m/x 377; the mass difference 133 suggested the presence of pentse. This sugar was identified by tandem MS/MS of hexaacetate of Lf at m/z 259 as parent ion. From comparison of four authentic MS/MS spectra the sugar was identified to be ribose. This was further supported from nmr spectra. NOE experiments disclosed the connection of the ribose in alpha linkage at the 5' position of riboflavin. CD spectrum of the hydrolysate concluded the D-ribose; and thus the absolute structure of lampteroflavin is 5'- -D-ribofuranosyl-riboflavin. Further studies will be followed by stereoselective synthesis of lampteroflavin to supply for the investigation of the molecular mechanism of the mushroom bioluminescence.