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.
Bibliographical noteThis is the Accepted Manuscript version of the following article: Enantiodivergence in the biosynthesis of bromotyrosine alkaloids from sponges? (2017) Kavita Ragini, Jane Fromont, Andrew M. Piggott, & Peter Karuso, Journal of Natural Products, Vol. 80, No. 1, pp. 215-219.
which has been published in final form at:
Publisher: American Chemical Society
Copyright: 2017 American Chemical Society