Nocapyrones A-D, gamma-pyrones from a Nocardiopsis strain isolated from the marine sponge Halichondria panicea.
Four new gamma-pyrones, nocapyrones A-D (1-4), were isolated from an organic extract of the Nocardiopsis strain HB383, which was isolated from the marine sponge Halichondria panicea. These are the first gamma-pyrones reported from a Nocardiopsis strain. The structures were elucidated on the basis of one- and two-dimensional NMR experiments and supported by HPLC-UV/MS and HRESIMS analyses. The biosynthesis of nocapyrone A was investigated by feeding experiments with (13)C-labeled compounds. In addition, one diketopiperazine, which was only known as a synthetic compound before, was isolated. The bioactivies of 1, 2, and the diketopiperazine were evaluated in a panel of assays.
Schneemann
Imke
I
Kieler Wirkstoff-Zentrum (KiWiZ) at the Leibniz-Institute of Marine Sciences (IFM-GEOMAR), Am Kiel-Kanal 44, 24106 Kiel, Germany.
Ohlendorf
Birgit
B
Zinecker
Heidi
H
Nagel
Kerstin
K
Wiese
Jutta
J
Imhoff
Johannes F
JF
D000818:Animals; D001412:Bacillus subtilis / Q000187:drug effects; D002175:Candida / Q000187:drug effects; D041221:Candida glabrata; D002851:Chromatography, High Pressure Liquid; D044084:Erwinia amylovora / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D019073:HT29 Cells; D006801:Humans; D008386:Marine Biology; D051379:Mice; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D041681:NIH 3T3 Cells; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry*; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D044224:Pseudomonas syringae / Q000187:drug effects; D011753:Pyrones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D043368:Ralstonia solanacearum / Q000187:drug effects; D013210:Staphylococcus / Q000187:drug effects; D013237:Stereoisomerism; D016959:Xanthomonas campestris / Q000187:drug effects
D011753:Pyrones