Precursors of 6,6′-dibromoindigotin (Tyrian purple) from the mollusc Dicathais orbita (Gmelin). Isolation of choline ester salts of tyrindoxyl sulphate from the marine molluscs Dicathais orbita and Mancinella keineri. Isolation from the hypobranchial glands of marine molluscs of 6-bromo-2,2-dimethylthioindolin-3-one and 6-bromo-2-methylthioindoleninone as alternative precursors to Tyrian purple. The Elder Pliny’s Chapters on Chemical Subjects, Part 1.

Characterization of natural indigo and Tyrian purple by mass spectrometric techniques. Heterocycles 32:1391–1452.Ī ndreotti, A., B onaduce, I., C olombini, M., and ibechini, E.

Marine, nitrogen-containing heterocyclic natural products- structures and syntheses of compounds containing indole units. These findings provide a model for investigating sex-specific chemical divergences in marine invertebrates and support the involvement of Tyrian purple genesis in muricid reproduction.Ī lvares, M., and S alas, M. Dye precursors were also present in male and female gonoduct extracts, establishing a mechanism for the incorporation of bioactive intermediates into muricid egg masses. Multivariate analysis revealed statistically significant differences in the dye composition of male and female hypobranchial glands (ANOSIM, P = 0.002), thus providing evidence for sex-specific genesis of Tyrian purple in the Muricidae. Intermediates tyrindoxyl, tyrindoleninone, and tyriverdin were detected in female hypobranchial glands, along with 6,6′-dibromoindigo, while males contained 6-bromoisatin and 6,6′-dibromoindirubin. The prochromogen, tyrindoxyl sulfate, was detected for the first time, by using this method in hypobranchial gland extracts of both sexes. A liquid chromatography-mass spectrometry (LQ-MS) method was developed to simultaneously quantify dye pigments and precursors in male and female Dicathais orbita. Nevertheless, there remains a paucity of information on the biosynthetic routes leading to observed sexual differences in pigmentation. Exploitation of Tyrian purple from muricid molluscs, since antiquity, has prompted much interest in its chemical composition.

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