title: Bioactive lipids from the sponge Spirastrella abata.
abstract: Three sphingosine 4-sulfates (1-3) and a lysophosphatidylglycerol (4) were isolated from the Korean sponge Spirastrella abata. The structures of these compounds were determined based on the combined results of spectroscopic analyses. Based on the results of combined synthesis and comparison of specific rotation and circular dichroism, the absolute configurations of 1-3 were found to be enantiomeric to the previously isolated metabolites. The configurations of 4 were also partially determined by similar chemical and spectroscopic methods. The compounds exhibited significant cytotoxicity and weak antimicrobial activity (1), as well as weak-to-moderate inhibitory activity against isocitrate lyase and Na(+)/K(+)-ATPase. A structure-activity relationship was found for the sphingosine 4-sulfates.
authors.affiliation: Natural Products Research Institute, College of Pharmacy, Seoul National University, San 56-1, Sillim, Gwanak, Seoul 151-742, Republic of Korea.
authors.forename: Kyoung Hwa
authors.initials: KH
authors.lastname: Jang
authors.forename: Yoonyeong
authors.initials: Y
authors.lastname: Lee
authors.forename: Chung J
authors.initials: CJ
authors.lastname: Sim
authors.forename: Ki-Bong
authors.initials: KB
authors.lastname: Oh
authors.forename: Jongheon
authors.initials: J
authors.lastname: Shin
mesh_terms: D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D001682:Biological Availability; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D005658:Fungi / Q000187:drug effects; D006801:Humans; D007522:Isocitrate Lyase / Q000037:antagonists & inhibitors / Q000378:metabolism; D020014:K562 Cells; D008246:Lysophospholipids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D011161:Porifera / Q000737:chemistry*; D000254:Sodium-Potassium-Exchanging ATPase / Q000037:antagonists & inhibitors / Q000378:metabolism; D013110:Sphingosine / Q000031:analogs & derivatives / Q000302:isolation & purification* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013431:Sulfates / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
chemical_list: D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D000970:Antineoplastic Agents; D004791:Enzyme Inhibitors; D008246:Lysophospholipids; D013431:Sulfates; C026223:lysophosphatidylglycerol; D007522:Isocitrate Lyase; D000254:Sodium-Potassium-Exchanging ATPase; D013110:Sphingosine