title: p-Sulfooxyphenylpyruvic acid from the red macro alga Ceratodictyon spongiosum and its sponge symbiont Haliclona cymaeformis.
abstract: Investigation of a Philippine specimen of the red alga Ceratodictyon spongiosum and its sponge symbiont Haliclona cymaeformis led to the isolation of p-sulfooxyphenylpyruvic acid, whose structure was elucidated using spectroscopic methods, with the Z-enol geometry determined through analysis of (3)J(C,H) coupling constants. The metabolite was tested for tyrosine kinase inhibition using a (3)H-thymidine incorporation assay, but was found inactive.
authors.affiliation: Department of Medicinal Chemistry, University of Utah, Salt Lake City, UT 84112, USA.
authors.forename: Tim S
authors.initials: TS
authors.lastname: Bugni
authors.forename: Gisela P
authors.initials: GP
authors.lastname: Concepción
authors.forename: Gina C
authors.initials: GC
authors.lastname: Mangalindan
authors.forename: Mary Kay
authors.initials: MK
authors.lastname: Harper
authors.forename: Robyn D
authors.initials: RD
authors.lastname: James
authors.forename: Chris M
authors.initials: CM
authors.lastname: Ireland
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D002294:Carcinoma, Squamous Cell / Q000201:enzymology / Q000378:metabolism; D002513:Cephamycins / Q000494:pharmacology; D002845:Chromatography / Q000379:methods; D003622:Dapsone / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D009682:Magnetic Resonance Spectroscopy; D010667:Phenylpyruvic Acids / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology; D010679:Philippines; D011161:Porifera / Q000737:chemistry*; D011505:Protein-Tyrosine Kinases / Q000037:antagonists & inhibitors; D000461:Rhodophyta / Q000737:chemistry* / Q000378:metabolism; D021241:Spectrometry, Mass, Electrospray Ionization; D014407:Tumor Cells, Cultured / Q000187:drug effects
chemical_list: D000970:Antineoplastic Agents; D002513:Cephamycins; D004791:Enzyme Inhibitors; D010667:Phenylpyruvic Acids; C467748:sulfooxyphenylpyruvic acid; C036115:sulfoxone; D003622:Dapsone; D011505:Protein-Tyrosine Kinases; C031606:phenylpyruvic acid