5-N-acetylardeemin, a novel heterocyclic compound which reverses multiple drug resistance in tumor cells. II. Isolation and elucidation of the structure of 5-N-acetylardeemin and two congeners.
A family of novel compounds has been detected and isolated following an assay for the attenuation of multiple drug resistance in tumor cells from the fermentation broth and mycelia of a strain of Aspergillus fischeri which we have designated var. brasiliensis. The structures of three components were determined employing 1-D and 2-D homonuclear and heteronuclear NMR spectroscopy and mass spectrometry. The structure of 5-N-acetylardeemin was confirmed by single crystal X-ray diffraction. These compounds are most closely structurally related to asperlicin E1).
Hochlowski
J E
JE
Abbott Laboratories, Abbott Park, Illinois 60064.
Mullally
M M
MM
Spanton
S G
SG
Whittern
D N
DN
Hill
P
P
McAlpine
J B
JB
D000903:Antibiotics, Antineoplastic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001230:Aspergillus / Q000737:chemistry*; D004352:Drug Resistance, Microbial; D006571:Heterocyclic Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D011744:Pyrimidinones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D014407:Tumor Cells, Cultured / Q000187:drug effects
D000903:Antibiotics, Antineoplastic; D006571:Heterocyclic Compounds; D011744:Pyrimidinones; C080891:5-N-acetylardeemin