title: Probing the bioactive constituents from chemotypes of the sponge Psammocinia aff. bulbosa.
abstract: 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.
authors.affiliation: Department of Chemistry and Biochemistry and Institute for Marine Sciences, University of California, Santa Cruz, Santa Cruz, California 95064, USA.
authors.forename: Sarah J
authors.initials: SJ
authors.lastname: Robinson
authors.forename: Karen
authors.initials: K
authors.lastname: Tenney
authors.forename: Desiree F
authors.initials: DF
authors.lastname: Yee
authors.forename: Lizabeth
authors.initials: L
authors.lastname: Martinez
authors.forename: Joseph E
authors.initials: JE
authors.lastname: Media
authors.forename: Frederick A
authors.initials: FA
authors.lastname: Valeriote
authors.forename: Rob W M
authors.initials: RW
authors.lastname: van Soest
authors.forename: Phillip
authors.initials: P
authors.lastname: Crews
mesh_terms: 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
chemical_list: D003374:Coumarins; D011714:Pyrans; D011753:Pyrones; C498383:psymberin