title: LC-MS and microscale NMR analysis of luciferin-related compounds from the bioluminescent earthworm Fridericia heliota.
abstract: This paper presents the main results of RP-HPLC-MS and microscale NMR analysis performed on Accompanying similar to Luciferin (AsLn(x)), compounds present in extracts of the bioluminescent earthworm Fridericia heliota that display similarities with Fridericia's luciferin, the substrate of the bioluminescent reaction. Three isomers of AsLn were discovered, AsLn(1), AsLn(2) and AsLn(3), all of which present a molecular weight of 529 Da. Their UV-Vis absorption spectra show maxima at 235 nm for AsLn(1), 238 and 295 nm for AsLn(2) and 241 and 295nm for AsLn(3). MS(n) fragmentation patterns suggest the existence of carboxylic acid and hydroxyl moieties, and possibly chemical groups found in other luciferins like pterin or benzothiazole. The major isomer, AsLn(2), presents an aromatic ring and alkene and alkyl moieties. These luciferin-like compounds can be used as models that could give further insights into the structure of this newly discovered luciferin.
authors.affiliation: Centro de Investigação em Química (CIQ), Department of Chemistry and Biochemistry, Faculty of Sciences, Universidade do Porto, Rua do Campo Alegre 687, 4169-007 Porto, Portugal.
authors.forename: Simone M
authors.initials: SM
authors.lastname: Marques
authors.forename: Valentin N
authors.initials: VN
authors.lastname: Petushkov
authors.forename: Natalja S
authors.initials: NS
authors.lastname: Rodionova
authors.forename: Joaquim C G Esteves
authors.initials: JC
authors.lastname: da Silva
mesh_terms: D000818:Animals; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D056148:Chromatography, Reverse-Phase; D049454:Firefly Luciferin / Q000737:chemistry*; D049408:Luminescent Agents / Q000737:chemistry* / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D013058:Mass Spectrometry; D009835:Oligochaeta / Q000737:chemistry*
chemical_list: D049408:Luminescent Agents; D049454:Firefly Luciferin