Evariquinone, isoemericellin, and stromemycin from a sponge derived strain of the fungus Emericella variecolor.
From a strain of the fungus Emericella variecolor derived from the marine sponge Haliclona valliculata, two new natural products, evariquinone and isoemericellin, were isolated after HPLC-UV, -MS, and -NMR studies of the extract and their structures were elucidated by mass spectrometry and NMR experiments. Evariquinone showed antiproliferative activity towards KB and NCI-H460 cells at a concentration of 3.16 microg/ml. Furthermore, the fungus was found to produce the known metabolites stromemycin, shamixanthone, and 7-hydroxyemodin. Chemical degradation, NMR decoupling experiments, and spin-system simulation provided evidence for the double bonds in stromemycin to be all E-configured. ROESY experiments established the monosaccharide moiety to be glucose.
Bringmann
Gerhard
G
Institut für Organische Chemie der Universität, Am Hubland, D-97074 Würzburg, Germany. bringmann@chemie.uni-wuerzburg.de
Lang
Gerhard
G
Steffens
Stefan
S
Günther
Eckhard
E
Schaumann
Karsten
K
D000818:Animals; D000903:Antibiotics, Antineoplastic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D016227:Benzoquinones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001592:Benzyl Alcohols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D032842:Emericella / Q000737:chemistry* / Q000378:metabolism; D006801:Humans; D007536:Isomerism; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000382:microbiology; D014407:Tumor Cells, Cultured
D000903:Antibiotics, Antineoplastic; D016227:Benzoquinones; D001592:Benzyl Alcohols