The NMR-directed investigation of the New Zealand marine sponge Hamigera tarangaensis has afforded ten new compounds of the hamigeran family, and a new 13-epi-verrucosane congener. Notably, hamigeran F (6) possesses an unusual carbon–carbon bond between C-12 and C-13, creating an unprecedented skeleton within this class. In particular, the structural features of 6, hamigeran H (10) and hamigeran J (12) imply a diterpenoid origin, which has allowed the putative biogenesis of three hamigeran carbon skeletons to be proposed based on geranyl geranyl pyrophosphate. All new hamigerans exhibited micromolar activity towards the HL-60 promyelocytic leukaemic cell line, and hamigeran G also selectively displayed antifungal activity in the budding yeast Saccharomyces cerevisiae. Homozygous deletion profiling (HOP) analysis suggests Golgi apparatus function as a potential target of this unusual class of sponge-derived terpenoids.
Copyright © 2013 The Royal Society of Chemistry. This article first appeared in Organic & Biomolecular Chemistiry 11 (2013), 8041-8051.
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Singh, A. Jonathan, Jonathan D. Dattelbaum, Jessica J. Field, Zlatka Smart, Ethan F. Woolly, Jacqueline M. Barber, Rosemary Heathcott, John H. Miller, and Peter T. Northcote. "Structurally Diverse Hamigerans from the New Zealand Marine Sponge Hamigera Tarangaensis: NMR-directed Isolation, Structure Elucidation and Antifungal Activity." Organic & Biomolecular Chemistry 11, no. 46 (2013): 8041-051. doi:10.1039/c3ob41305e.