1-<i>O</i>-Alkylglycerol Ethers from the Marine Sponge <i>Guitarra abbotti</i> and Their Cytotoxic Activity
Sergey A. Dyshlovoy,
Sergey N. Fedorov,
Vasily I. Svetashev,
Tatiana N. Makarieva,
Anatoliy I. Kalinovsky,
Olga P. Moiseenko,
Vladimir B. Krasokhin,
Larisa K. Shubina,
Alla G. Guzii,
Gunhild von Amsberg,
Valentin A. Stonik
Affiliations
Sergey A. Dyshlovoy
Department of Oncology, Hematology and Bone Marrow Transplantation with Section Pneumology, Hubertus Wald Tumorzentrum—University Cancer Center Hamburg (UCCH), University Medical Center Hamburg-Eppendorf, 20251 Hamburg, Germany
Sergey N. Fedorov
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-East Branch of the Russian Academy of Sciences, 690022 Vladivostok, Russia
Vasily I. Svetashev
National Scientific Center of Marine Biology, Far-East Branch of the Russian Academy of Sciences, 690041 Vladivostok, Russia
Tatiana N. Makarieva
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-East Branch of the Russian Academy of Sciences, 690022 Vladivostok, Russia
Anatoliy I. Kalinovsky
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-East Branch of the Russian Academy of Sciences, 690022 Vladivostok, Russia
Olga P. Moiseenko
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-East Branch of the Russian Academy of Sciences, 690022 Vladivostok, Russia
Vladimir B. Krasokhin
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-East Branch of the Russian Academy of Sciences, 690022 Vladivostok, Russia
Larisa K. Shubina
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-East Branch of the Russian Academy of Sciences, 690022 Vladivostok, Russia
Alla G. Guzii
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-East Branch of the Russian Academy of Sciences, 690022 Vladivostok, Russia
Gunhild von Amsberg
Department of Oncology, Hematology and Bone Marrow Transplantation with Section Pneumology, Hubertus Wald Tumorzentrum—University Cancer Center Hamburg (UCCH), University Medical Center Hamburg-Eppendorf, 20251 Hamburg, Germany
Valentin A. Stonik
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-East Branch of the Russian Academy of Sciences, 690022 Vladivostok, Russia
The cytotoxicity-bioassay-guided fractionation of the ethanol extract from the marine sponge Guitarra abbotti, whose 1-O-alkyl-sn-glycerol ethers (AGEs) have not been investigated so far, led to the isolation of a complex lipid fraction containing, along with previously known compounds, six new lipids of the AGE type. The composition of the AGE fraction as well as the structures of 6 new and 22 previously known compounds were established using 1H and 13C NMR, GC/MS, and chemical conversion methods. The new AGEs were identified as: 1-O-(Z-docos-15-enyl)-sn-glycerol (1), 1-O-(Z-docos-17-enyl)-sn-glycerol (2), 1-O-(Z-tricos-15-enyl)-sn-glycerol (3), 1-O-(Z-tricos-16-enyl)-sn-glycerol (4), 1-O-(Z-tricos-17-enyl)-sn-glycerol (5), and 1-O-(Z-tetracos-15-enyl)-sn-glycerol (6). The isolated AGEs show weak cytotoxic activity in THP-1, HL-60, HeLa, DLD-1, SNU C4, SK-MEL-28, and MDA-MB-231 human cancer cells. A further cytotoxicity analysis in JB6 P+ Cl41 cells bearing mutated MAP kinase genes revealed that ERK2 and JNK1 play a cytoprotective role in the cellular response to the AGE-induced cytotoxic effects.
