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Molecules 2016, 21(12), 1672; doi:10.3390/molecules21121672

Extraction and Quantification of Bioactive Tyrian Purple Precursors: A Comparative and Validation Study from the Hypobranchial Gland of a Muricid Dicathais orbita

1
Marine Ecology Research Centre, School of Environment, Science and Engineering, Southern Cross University, Lismore, NSW 2480, Australia
2
Southern Cross Plant Science, Southern Cross University, Lismore, NSW 2480, Australia
*
Author to whom correspondence should be addressed.
Academic Editor: Michael Wink
Received: 6 October 2016 / Revised: 21 November 2016 / Accepted: 28 November 2016 / Published: 5 December 2016
(This article belongs to the Special Issue Diversity of Alkaloids)
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Abstract

Muricidae are marine molluscs known for the production of Tyrian purple and bioactive precursor compounds. A validation study for the extraction and analysis of secondary metabolites found in the hypobranchial gland of the muricid Dicathais orbita is reported, using high performance liquid chromatography–mass spectrometry (HPLC-MS) with diode array detector (DAD). Quantification of the dominant secondary metabolites from D. orbita is described, followed by a comparison of solvent extraction procedures and stability studies. The intra- and inter-day relative standard deviation (RSD) for tyrindoxyl sulphate was 0.46% and 0.17%, respectively. The quantification was linear for standards murexine, 6-bromoisatin, and tyrindoxyl sulphate. The limits of detection were 0.03, 0.004, and 0.07 mg/mL, respectively, and the limits of quantification were 0.09, 0.01, and 0.22 mg/mL, respectively. The results showed that alcoholic solvents were better for extracting choline ester and indoxyl sulphate ultimate precursors, while chloroform was more suitable for the extraction of the intermediate precursors. Multivariate analysis revealed significant differences in extract composition according to the solvent used. Stability testing showed an increase of the oxidative compounds 6-bromoisatin and putative tyrindoxyl S-oxide sulphate in the ethanol extracts while more degradation products were seen in the chloroform extracts after months of cold storage. The validated method was found to be simple, reproducible, precise, and suitable for quantification of the secondary metabolites of muricid molluscs for dye precursor and nutraceutical quality control, as well as applications in marine chemical ecology. View Full-Text
Keywords: brominated indole; marine natural products; nutraceutical; marine mollusc; liquid chromatography–mass spectrometry brominated indole; marine natural products; nutraceutical; marine mollusc; liquid chromatography–mass spectrometry
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MDPI and ACS Style

Valles-Regino, R.; Mouatt, P.; Rudd, D.; Yee, L.H.; Benkendorff, K. Extraction and Quantification of Bioactive Tyrian Purple Precursors: A Comparative and Validation Study from the Hypobranchial Gland of a Muricid Dicathais orbita. Molecules 2016, 21, 1672.

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