Brocaenols A-C: novel polyketides from a marine derived Penicillium brocae.
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.
Bugni
Tim S
TS
Department of Medicinal Chemistry, University of Utah, Salt Lake City, Utah 84112, USA.
Bernan
Valerie S
VS
Greenstein
Michael
M
Janso
Jeffrey E
JE
Maiese
William M
WM
Mayne
Charles L
CL
Ireland
Chris M
CM
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
D006575:Heterocyclic Compounds, 3-Ring; C476098:brocaenol A; C476099:brocaenol B; C476100:brocaenol C