Probing the bioactive constituents from chemotypes of the sponge Psammocinia aff. bulbosa.
Since the report of (+)-psymberin (2) in 2004, many synthetic groups have pursued the synthesis of this compound, and our group has further collected Psammocinia aff. bulbosa to successfully isolate more 2. With more (+)-psymberin (2) in hand, additional clonogenic studies, a therapeutic efficacy assessment, and the hollow fiber assay have been completed. The inconsistent production of (+)-psymberin (2) and the classification of six Psammocinia species are further discussed herein. The most recent of these six collections resulted in the isolation of a new brominated cyclic peptide, (-)-psymbamide A (4), which is the first report of a Psammocinia-derived compound in this peptide class. The planar structure was solved via dereplication with Marinlit, HRESIMS, and 1D and 2D NMR techniques, and the absolute configuration determined using Marfey's method.
Robinson
Sarah J
SJ
Department of Chemistry and Biochemistry and Institute for Marine Sciences, University of California, Santa Cruz, Santa Cruz, California 95064, USA.
Tenney
Karen
K
Yee
Desiree F
DF
Martinez
Lizabeth
L
Media
Joseph E
JE
Valeriote
Frederick A
FA
van Soest
Rob W M
RW
Crews
Phillip
P
D000818:Animals; D003374:Coumarins; D004195:Disease Models, Animal; D004305:Dose-Response Relationship, Drug; D045325:HCT116 Cells; D006801:Humans; D051379:Mice; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010219:Papua New Guinea; D011161:Porifera / Q000737:chemistry* / Q000235:genetics; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
D003374:Coumarins; D011714:Pyrans; D011753:Pyrones; C498383:psymberin