title: Enantiodivergence in the Biosynthesis of Bromotyrosine Alkaloids from Sponges?
abstract: The isolation of bromotyrosine alkaloids, some of which are enantiomers of previously isolated compounds, has highlighted a possible enantiodivergence in their biosynthesis. Two new (1, 2) and six known bromotyrosine alkaloids (4-9), and the enantiomer (10) of a known compound, have been isolated from a Western Australian marine sponge, Pseudoceratina cf. verrucosa. The compounds inhibited the growth of multidrug-resistant and methicillin-resistant Staphylococcus aureus with comparable activity to vancomycin. In addition, one possible artifact of extraction (3) containing an ethoxy group was isolated. From analysis of the known bromotyrosine alkaloids, a biogenesis is proposed that explains the formation of antipodal natural products within this family of sponges.
authors.affiliation: Department of Chemistry and Biomolecular Sciences, Macquarie University , Sydney, NSW 2109, Australia.
authors.forename: Kavita
authors.initials: K
authors.lastname: Ragini
authors.affiliation: Department of Aquatic Zoology, Western Australian Museum , Western Australia 6106, Australia.
authors.forename: Jane
authors.initials: J
authors.lastname: Fromont
authors.affiliation: Department of Chemistry and Biomolecular Sciences, Macquarie University , Sydney, NSW 2109, Australia.
authors.forename: Andrew M
authors.identifier: 0000-0002-5308-5314
authors.initials: AM
authors.lastname: Piggott
authors.affiliation: Department of Chemistry and Biomolecular Sciences, Macquarie University , Sydney, NSW 2109, Australia.
authors.forename: Peter
authors.identifier: 0000-0002-0217-6021
authors.initials: P
authors.lastname: Karuso
mesh_terms: D000470:Alkaloids / Q000096:biosynthesis* / Q000737:chemistry; D000818:Animals; D001315:Australia; D001688:Biological Products / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects; D015394:Molecular Structure; D011161:Porifera; D013237:Stereoisomerism; D014443:Tyrosine / Q000031:analogs & derivatives* / Q000096:biosynthesis / Q000737:chemistry
chemical_list: D000470:Alkaloids; D001688:Biological Products; C475724:bromotyrosine; D014443:Tyrosine