title: Brocaenols A-C: novel polyketides from a marine derived Penicillium brocae.
abstract: Chemical investigation of a Penicillium brocae, obtained from a tissue sample of a Fijian Zyzyya sp. sponge, yielded two known diketopiperazines and three novel cytotoxic polyketides, brocaenols A-C. The brocaenols contain an unusual enolized oxepine lactone ring system that to the best of our knowledge is unprecedented in the literature. The structures were elucidated by using 2D-NMR methods including an INADEQUATE experiment. The absolute stereochemistry of brocaenol A was established by using a modified Mosher method. The taxonomy of the producing fungus was elucidated by using both morphological and rDNA sequence analysis.
authors.affiliation: Department of Medicinal Chemistry, University of Utah, Salt Lake City, Utah 84112, USA.
authors.forename: Tim S
authors.initials: TS
authors.lastname: Bugni
authors.forename: Valerie S
authors.initials: VS
authors.lastname: Bernan
authors.forename: Michael
authors.initials: M
authors.lastname: Greenstein
authors.forename: Jeffrey E
authors.initials: JE
authors.lastname: Janso
authors.forename: William M
authors.initials: WM
authors.lastname: Maiese
authors.forename: Charles L
authors.initials: CL
authors.lastname: Mayne
authors.forename: Chris M
authors.initials: CM
authors.lastname: Ireland
mesh_terms: D000818:Animals; D005285:Fermentation; D005367:Fiji; D006575:Heterocyclic Compounds, 3-Ring / Q000737:chemistry / Q000302:isolation & purification*; D020128:Inhibitory Concentration 50; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010407:Penicillium / Q000737:chemistry*; D011161:Porifera / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D006575:Heterocyclic Compounds, 3-Ring; C476098:brocaenol A; C476099:brocaenol B; C476100:brocaenol C