title: Sulfoureido Lipopeptides from the Marine Sponge Discodermia kiiensis.
abstract: New N-sulfoureidylated lipopeptides, sulfolipodiscamides A-C (1-3), were isolated by gel filtration chromatography of the n-butanol fraction of the marine sponge Discodermia kiiensis. By extensive NMR analyses and high-resolution mass spectrometry, the structures of 1-3 were elucidated as having an unprecedented N-sulfoureidyl group on the d-citrulline residue, a distinct feature that was not found in the structurally related lipodiscamides A-C (4-6), derived from the ether fraction of the same sponge. Furthermore, the absolute configurations of 1-3 were confirmed by comparisons of the HPLC retention times of the hydrolytic products and the corresponding authentic lipodiscamides. Interestingly, sulfolipodiscamide A displayed a 2.3-fold increase in cytotoxicity against murine leukemia (P388) cells, compared to the unconjugated parent compound.
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo , 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Karen Co
authors.initials: KC
authors.lastname: Tan
authors.affiliation: Graduate School of Pharmaceutical Sciences, Hokkaido University , Kita 12 Nishi 6, Kita-ku, Sapporo 060-0812, Japan.
authors.forename: Toshiyuki
authors.initials: T
authors.lastname: Wakimoto
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo , 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Ikuro
authors.initials: I
authors.lastname: Abe
mesh_terms: D000818:Animals; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007941:Leukemia P388; D055666:Lipopeptides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008386:Marine Biology; D051379:Mice; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry*
chemical_list: D055666:Lipopeptides