Isolation of labradorins 1 and 2 from Pseudomonas syringae pv. coronafaciens.
Investigation of Pseudomonas syringae pv. coronafaciens cancer cell growth inhibitory constituents led to the isolation of 2-isobutyl-5-(3-indolyl)oxazole (1) and 2-n-pentyl-5-(3-indolyl)oxazole (2f), designated labradorins 1 (1) and 2 (2f), related to pimprinine (2a). The structures were deduced by spectroscopic techniques and X-ray crystal structure determinations. Labradorin 1 (1) afforded GI(50) microg/mL values of 9.8 and 6.2 against the human cancer cell lines NCI-H 460 (lung-NSC) and BXPC-3 (pancreas-a).
Pettit
George R
GR
Cancer Research Institute and Department of Chemistry and Biochemistry, Arizona State University, Tempe, AZ 85287-2404, USA.
Knight
John C
JC
Herald
Delbert L
DL
Davenport
Richard
R
Pettit
Robin K
RK
Tucker
Bruce E
BE
Schmidt
Jean M
JM
D018360:Crystallography, X-Ray; D003840:Deoxycholic Acid; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008175:Lung Neoplasms; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010080:Oxazoles / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D010190:Pancreatic Neoplasms; D011549:Pseudomonas / Q000737:chemistry*; D014407:Tumor Cells, Cultured / Q000187:drug effects
C473431:2-isobutyl-5-(3-indolyl)oxazole; C473430:2-n-pentyl-5-(3-indolyl)oxazole; D010080:Oxazoles; D003840:Deoxycholic Acid; C008912:pimprinine