Expanding the strategies in natural product studies of marine-derived fungi: a chemical investigation of penicillium obtained from deep water sediment.
Three previously unknown pentaketides, (+)-formylanserinone B (3), (-)-epoxyserinone A (4), and (+)-epoxyserinone B (5), along with two known fungal pigments, anserinones A (1) and B (2), were isolated and identified from a deep water (-4380 ft), marine-derived saltwater fungal culture. Two other minor constituents, hydroxymethylanserinone B (6) and deoxyanserinone B (7), were also isolated, but not completely purified. The structures of 3-7, each expanding the dense functionalization of the anserinones, were determined by dereplication and spectroscopic analysis. Bioactivity was explored in two separate cell-based assays. Leukemia selectivity was greatest with 2 and 3, while 1-3 exhibited modest activity against the MDA-MB-435 cell line.
Gautschi
Jeffrey T
JT
Department of Chemistry and Biochemistry & Institute of Marine Sciences, University of California, Santa Cruz, California 95064, USA.
Amagata
Taro
T
Amagata
Akiko
A
Valeriote
Frederick A
FA
Mooberry
Susan L
SL
Crews
Phillip
P
D016227:Benzoquinones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001685:Biological Factors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D005658:Fungi / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010407:Penicillium / Q000737:chemistry*; D013237:Stereoisomerism; D014407:Tumor Cells, Cultured; D014871:Water Microbiology
D016227:Benzoquinones; D001685:Biological Factors; C107779:anserinone A; C107780:anserinone B; C484210:epoxyserinone A; C484211:formylanserinone B