Tyrian Purple: 6,6’-Dibromoindigo and Related Compounds

Molecules (Impact Factor: 2.42). 09/2001; 6(9):736-769. DOI: 10.3390/60900736
Source: DOAJ

ABSTRACT The genesis of the purple dye from shellfish, its composition, origin, intermediates, analysis and synthesis of the components, 6,6'-dibromoindigo, 6- bromoindigo and 6,6'-dibromoindirubin are reviewed

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    • "Supercritical CO 2 could therefore act as a natural dye extraction medium for precursor compounds prior to Tyrian purple dye development. The reaction of precursors leading to Tyrian purple formation is an interesting example of a novel reactive dye, where the precursor characteristics are more suitable to both the dyeing process and the impregnation in natural fibers, whilst the resulting dye is insoluble in the dyeing medium and is colorfast [23]. Supercritical dyeing has not been previously tested using Tyrian purple or Muricidae mollusc extracts. "
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    ABSTRACT: Supercritical CO2 provides considerable advantages over traditional solvents for the extraction of bioactive compounds from organic matter. Here we demonstrate the use of supercritical CO2 as an efficient and safe alternative to traditional solvent extraction for the recovery of bioactive Tyrian purple precursors tyrindoleninone, 6-bromoisatin and tyriverdin from the marine mollusc Dicathais orbita. The effect of pressure on the selective extraction of brominated indoles was tested at 15,30 and 50 MPa CO2, and was compared to traditional chloroform extract composition and yields. Extracts obtained from 15 MPa selectively concentrated 6-bromoisatin, at 78% of the extract composition, whereas increased pressures of 30 and 50 MPa increased the solvating power of supercritical CO2 to include the more lipophilic tyrindoleninone at 35 and 29% respectively, and tyriverdin at 23 and 40% respectively. This extraction method was also effective in separating the brominated indoles from toxic choline esters in the mollusc extracts. Extract yields from supercritical CO2 were comparable to solvent extraction relative to whole whelk weight. This provides a viable alternative for nutraceutical development that does not rely on the use of toxic solvents.
    Journal of Supercritical Fluids The 10/2014; 94. DOI:10.1016/j.supflu.2014.06.016 · 2.57 Impact Factor
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    • "The characteristic colorant of Tyrian purple, DBI, was identified by Friedländer [22]. Subsequently many syntheses of it have appeared, which have been reviewed by Cooksey [13], who, along with Clark also developed a synthesis of MBI [23]. A more recent treatment of existing DBI syntheses has been presented by Wolk and Frimer [24]. "
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    ABSTRACT: Fundamental dyeing properties of three dyes of historical importance - indigo, 6-bromoindigo, and 6,6’-dibromoindigo - on 13 fabrics are examined. The hues of the dyed fabrics vary from blue-green to blue for indigo, blue to violet for 6-bromoindigo, and violet-blue to purple for 6,6’-dibromoindigo, as determined by reflectance measurements. Many of the dyed fabrics change color markedly with application of gentle heat. For indigo and 6-bromoindigo, the color changes are predominantly towards absorption of longer wavelengths (giving a bluer fabric color), while for 6,6’-dibromoindigo, the color changes are towards absorption of shorter wavelengths (giving a redder fabric color). The greatest thermochromic effects are seen for dyed wool: with 6-bromoindigo, the color changes from violet to blue, while with 6,6’-dibromoindigo, the color changes from violet to red-purple upon brief boiling in water. Transmission electron microscopy analysis of 6-bromoindigo-dyed carbon nanotubes, used as surrogates for dyed fabric fibers, suggests that the basis of the thermochromic effect is a change in the size distribution of dye aggregates.
    Dyes and Pigments 02/2013; 96(2):581-589. DOI:10.1016/j.dyepig.2012.07.014 · 3.97 Impact Factor
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    • "Severe population disruption of some commercially fished muricids (whelks) has provided impetus for research into aquaculture of this family to ensure sustainable supply (Nugranad et al., 1994; Xavier Ramesh et al. 1994; Gutiérrez and Gallardo, 1999; Woodcock and Benkendorff, 2008). Muricids are also highly valued for the production of their purple dye secretion, best known as Tyrian purple (Cooksey, 2001; Naegel, 2004). The bioactive precursors of Tyrian purple are of continuing interest for antibiotic and anticancer activities (Benkendorff et al., 2000; Westley et al., 2006; Meijer et al., 2003; Naegel and Murillo Alvarez, 2005; Benkendorff et al., in press). "
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    ABSTRACT: Anaesthetics are used extensively on marine molluscs for non-destructive sampling and to manipulate specimens in ecological studies and aquaculture. Dicathais orbita is an edible southern Australian muricid (Neogastropoda) with potential for use as an indicator species for ecological monitoring and new species development in aquaculture. This species produces bioactive compounds that are currently under investigation for the development of a novel anticancer therapy. No previous studies have investigated the use of anaesthetics to collect bioactive compounds. Thus, a suite of anaesthetics was trialled for their efficacy in relaxing D. orbita out of the shell to identify sex and for stimulating bioactive compound production. The recovery time significantly varied between the different anaesthetic applications (P < 0.001). Magnesium chloride proved most effective in relaxing specimens enough to identify sex and recovery time did not differ from the seawater control (P > 0.05). This method was successfully applied to field populations of D. orbita in order to establish a 1:1 sex ratio at 6 sites in South Australia. No evidence of imposex was observed at any location. Benzocaine and the carrier solvent ethanol were less effective for identifying sex, but stimulated expulsion of the bioactive precursors. This indicates that ethanol may be inducing a stress response in these gastropods rather than a standard anaesthetisation. Consequently, the most suitable anaesthetic for use on gastropods will depend on the specific use and requires testing for species specific responses.
    Journal of Experimental Marine Biology and Ecology 11/2009; DOI:10.1016/j.jembe.2009.09.006 · 2.48 Impact Factor
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