1-<i>O</i>-Alkylglycerol Ethers from the Marine Sponge <i>Guitarra abbotti</i> and Their Cytotoxic Activity

The cytotoxicity-bioassay-guided fractionation of the ethanol extract from the marine sponge <i>Guitarra abbotti</i>, whose 1-<i>O</i>-alkyl-<i>sn</i>-glycerol ethers (AGEs) have not been investigated so far, led to the isolation of a complex lipid fraction contai...

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Bibliographic Details
Main Authors: 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
Format: Article
Language:English
Published: MDPI AG 2022-06-01
Series:Marine Drugs
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Online Access:https://www.mdpi.com/1660-3397/20/7/409
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Summary:The cytotoxicity-bioassay-guided fractionation of the ethanol extract from the marine sponge <i>Guitarra abbotti</i>, whose 1-<i>O</i>-alkyl-<i>sn</i>-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 <sup>1</sup>H and <sup>13</sup>C NMR, GC/MS, and chemical conversion methods. The new AGEs were identified as: 1-<i>O</i>-(Z-docos-15-enyl)-<i>sn</i>-glycerol (<b>1</b>), 1-<i>O</i>-(Z-docos-17-enyl)-<i>sn</i>-glycerol (<b>2</b>), 1-<i>O</i>-(Z-tricos-15-enyl)-<i>sn</i>-glycerol (<b>3</b>), 1-<i>O</i>-(Z-tricos-16-enyl)-<i>sn</i>-glycerol (<b>4</b>), 1-<i>O</i>-(Z-tricos-17-enyl)-<i>sn</i>-glycerol (<b>5</b>), and 1-<i>O</i>-(Z-tetracos-15-enyl)-<i>sn</i>-glycerol (<b>6</b>). 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<sup>+</sup> 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.
ISSN:1660-3397