Abstract
The predatory marine gastropod Dicathais orbita has been the subject of a significant amount of biological and chemical research over the past five decades. Natural products research on D. orbita includes the isolation and identification of brominated indoles and choline esters as precursors of Tyrian purple, as well as the synthesis of structural analogues, bioactivity testing, biodistributional and biosynthetic studies. Here I also report on how well these compounds conform to Lipinski’s rule of five for druglikeness and their predicted receptor binding and enzyme inhibitor activity. The composition of mycosporine-like amino acids, fatty acids and sterols has also been described in the egg masses of D. orbita. The combination of bioactive compounds produced by D. orbita is of interest for further studies in chemical ecology, as well as for future nutraceutical development. Biological insights into the life history of this species, as well as ongoing research on the gene expression, microbial symbionts and biosynthetic capabilities, should facilitate sustainable production of the bioactive compounds. Knowledge of the phylogeny of D. orbita provides an excellent platform for novel research into the evolution of brominated secondary metabolites in marine molluscs. The range of polarities in the brominated indoles produced by D. orbita has also provided an effective model system used to develop a new method for biodistributional studies. The well characterized suite of chemical reactions that generate Tyrian purple, coupled with an in depth knowledge of the ecology, anatomy and genetics of D. orbita provide a good foundation for ongoing natural products research.
Highlights
Dicathais orbita, commonly known as the Australian Dogwhelk or Cartrut shell, is a predatory marine gastropod in the family Muricidae
Commonly known as the Australian Dogwhelk or Cartrut shell, is a predatory marine gastropod in the family Muricidae. This family of marine molluscs is well known for the production of the ancient dye Tyrian purple [1,2], which was the first marine natural product to be structurally elucidated by Friedlander in 1909 [3]
After a twenty year gap, my Ph.D. study into the antimicrobial properties of Australian molluskan egg masses identified the precursors of Tyrian purple from D. orbita as interesting lead compounds for bioactivity studies [17]
Summary
Commonly known as the Australian Dogwhelk or Cartrut shell, is a predatory marine gastropod in the family Muricidae. D. orbita has been subsequently included as a model species in several other student theses investigating environmental stressors and human impacts [34,35] These insights into the ecology and life history of D. orbita have greatly facilitated ongoing natural products research, through interesting biological insights and population assessments, which help ensure sustainable collection. The combination of natural products chemistry and biological research undertaken on D. orbita to date establishes this species as potentially useful model for future studies on the evolution and biosynthesis of marine secondary metabolites, as well as for new method development e.g., [52]
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