Decaspirones A-E, bioactive spirodioxynaphthalenes from the freshwater aquatic fungus Decaisnella thyridioides.
Decaspirones A-E (1-5), five new compounds related to the palmarumycins, were isolated from cultures of the freshwater aquatic fungal species Decaisnella thyridioides. The known compound palmarumycin CP1 (6) was also obtained. The structures of 1-5 were determined by analysis of NMR and MS data, and their relative configurations were assigned by analysis of 1H NMR J-values and NOESY data. The structure of the lead compound 1 was confirmed by X-ray crystallographic analysis. Compounds 1-5 possess a trans ring fusion not previously reported in members of this structural class. The absolute configuration of 1 was assigned using the modified Mosher method. Compounds 1-5 showed potent antifungal and antibacterial activity.
Jiao
Ping
P
Department of Chemistry, University of Iowa, Iowa City, IA 52242, USA.
Swenson
Dale C
DC
Gloer
James B
JB
Campbell
Jinx
J
Shearer
Carol A
CA
D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001203:Ascomycota / Q000737:chemistry*; D001231:Aspergillus flavus / Q000187:drug effects; D002176:Candida albicans / Q000187:drug effects; D018360:Crystallography, X-Ray; D004146:Dioxanes / Q000737:chemistry / Q000302:isolation & purification; D004926:Escherichia coli / Q000187:drug effects; D005618:Fresh Water; D005670:Fusarium / Q000187:drug effects; D008968:Molecular Conformation; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D019906:Nuclear Magnetic Resonance, Biomolecular; D013141:Spiro Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013211:Staphylococcus aureus / Q000187:drug effects; D014922:Wisconsin
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D004146:Dioxanes; D009281:Naphthalenes; D013141:Spiro Compounds; C422643:palmarumycin CP(1)