The dyeing with Murex extracts, an unusual dyeing method of wool to the biblical sky blue. Recherches sur la pourpre et sur quelques autres pigments animaux. Dyes in History and Archaeology 16–17:91–96.ĭ ubois, R. Life in Progress Editions, Roscoff, France.Ĭ ooksey, C., and W ithnall, R. Marine indirubins, Indirubin, the Red Shade of Indigo. Dyes in History and Archaeology 16–17:97–104.Ĭ ooksey, C. The synthesis and properties of 6-bromoindigo: Indigo blue or Tyrian purple? The effect of physical state on the colours of indigo and bromoindigos. Tyrian Purple: 6,6′-dibromoindigo and related compounds. Letter to the philosophical society of oxford containing observations on the purple fish. Bromoindirubins: the synthesis and properties of minor components of Tyrian purple and the composition of the colourant from Nucella lapillus. A revised structure of tyriverdin: The precursor to Tyrian purple. Marine Natural Products, Chemical and Biological PerspectivesAcademic, New York, U.S.A.Ĭ hristophersen, C., W atjen, F., B uchardt, O., and A nthoni, U.
Observations of purple pigments in the egg capsules, hypobranchial and reproductive glands from seven species of the Muricidae (Gastropoda: Mollusca). Molecules 6:70–78.ī enkendorff, K., W estley, C., and G allardo, C. Indole derivatives from the egg masses of muricid molluscs.
Tyrian purple precursors in the egg masses of the Australian muricid, Dicathais orbita: A possible defensive role. The nature of pigments in marine invertebrates. 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.