Rhabdastrellosides A and B: Two New Isomalabaricane Glycosides from the Marine Sponge <i>Rhabdastrella globostellata</i>, and Their Cytotoxic and Cytoprotective Effects
Investigation of the Vietnamese marine sponge <i>Rhabdastrella globostellata</i> led to the isolation of two new polar isomalabaricanes: rhabdastrellosides A (<b>1</b>) and B (<b>2</b>). Their structures and stereochemistry were elucidated with the application of...
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MDPI AG
2023-10-01
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| Series: | Marine Drugs |
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| author | Anastasia B. Kozhushnaya Sophia A. Kolesnikova Ekaterina A. Yurchenko Ekaterina G. Lyakhova Alexander S. Menshov Anatoly I. Kalinovsky Roman S. Popov Pavel S. Dmitrenok Natalia V. Ivanchina |
| author_facet | Anastasia B. Kozhushnaya Sophia A. Kolesnikova Ekaterina A. Yurchenko Ekaterina G. Lyakhova Alexander S. Menshov Anatoly I. Kalinovsky Roman S. Popov Pavel S. Dmitrenok Natalia V. Ivanchina |
| author_sort | Anastasia B. Kozhushnaya |
| collection | DOAJ |
| description | Investigation of the Vietnamese marine sponge <i>Rhabdastrella globostellata</i> led to the isolation of two new polar isomalabaricanes: rhabdastrellosides A (<b>1</b>) and B (<b>2</b>). Their structures and stereochemistry were elucidated with the application of 1D and 2D NMR, HRESIMS, and HRESIMS/MS methods, as well as chemical modifications and GC–MS analysis. Metabolites <b>1</b> and <b>2</b> are the first isomalabaricanes with non-oxidized cyclopentane ring in the tricyclic core system. Moreover, having a 3-O-disaccharide moiety in their structures, they increase a very rare group of isomalabaricane glycosides. We report here a weak cytotoxicity of <b>1</b> and <b>2</b> toward human neuroblastoma SH-SY5Y cells and normal rat H9c2 cardiomyocytes, as well as the cytoprotective activity of rhabdastrelloside B (<b>2</b>) at 1 µM evaluated using CoCl<sub>2</sub>-treated SH-SY5Y and H9c2 cells. |
| first_indexed | 2024-03-09T16:40:10Z |
| format | Article |
| id | doaj.art-857ed00064a0473892e8c4d6e574a1be |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-09T16:40:10Z |
| publishDate | 2023-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-857ed00064a0473892e8c4d6e574a1be2023-11-24T14:53:06ZengMDPI AGMarine Drugs1660-33972023-10-01211155410.3390/md21110554Rhabdastrellosides A and B: Two New Isomalabaricane Glycosides from the Marine Sponge <i>Rhabdastrella globostellata</i>, and Their Cytotoxic and Cytoprotective EffectsAnastasia B. Kozhushnaya0Sophia A. Kolesnikova1Ekaterina A. Yurchenko2Ekaterina G. Lyakhova3Alexander S. Menshov4Anatoly I. Kalinovsky5Roman S. Popov6Pavel S. Dmitrenok7Natalia V. Ivanchina8G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, Pr. 100-Let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, Pr. 100-Let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, Pr. 100-Let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, Pr. 100-Let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, Pr. 100-Let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, Pr. 100-Let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, Pr. 100-Let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, Pr. 100-Let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, Pr. 100-Let Vladivostoku 159, 690022 Vladivostok, RussiaInvestigation of the Vietnamese marine sponge <i>Rhabdastrella globostellata</i> led to the isolation of two new polar isomalabaricanes: rhabdastrellosides A (<b>1</b>) and B (<b>2</b>). Their structures and stereochemistry were elucidated with the application of 1D and 2D NMR, HRESIMS, and HRESIMS/MS methods, as well as chemical modifications and GC–MS analysis. Metabolites <b>1</b> and <b>2</b> are the first isomalabaricanes with non-oxidized cyclopentane ring in the tricyclic core system. Moreover, having a 3-O-disaccharide moiety in their structures, they increase a very rare group of isomalabaricane glycosides. We report here a weak cytotoxicity of <b>1</b> and <b>2</b> toward human neuroblastoma SH-SY5Y cells and normal rat H9c2 cardiomyocytes, as well as the cytoprotective activity of rhabdastrelloside B (<b>2</b>) at 1 µM evaluated using CoCl<sub>2</sub>-treated SH-SY5Y and H9c2 cells.https://www.mdpi.com/1660-3397/21/11/554isomalabaricanesglycosidesglycoconjugates<i>Rhabdastrella globostellata</i>marine spongeterpenoids |
| spellingShingle | Anastasia B. Kozhushnaya Sophia A. Kolesnikova Ekaterina A. Yurchenko Ekaterina G. Lyakhova Alexander S. Menshov Anatoly I. Kalinovsky Roman S. Popov Pavel S. Dmitrenok Natalia V. Ivanchina Rhabdastrellosides A and B: Two New Isomalabaricane Glycosides from the Marine Sponge <i>Rhabdastrella globostellata</i>, and Their Cytotoxic and Cytoprotective Effects Marine Drugs isomalabaricanes glycosides glycoconjugates <i>Rhabdastrella globostellata</i> marine sponge terpenoids |
| title | Rhabdastrellosides A and B: Two New Isomalabaricane Glycosides from the Marine Sponge <i>Rhabdastrella globostellata</i>, and Their Cytotoxic and Cytoprotective Effects |
| title_full | Rhabdastrellosides A and B: Two New Isomalabaricane Glycosides from the Marine Sponge <i>Rhabdastrella globostellata</i>, and Their Cytotoxic and Cytoprotective Effects |
| title_fullStr | Rhabdastrellosides A and B: Two New Isomalabaricane Glycosides from the Marine Sponge <i>Rhabdastrella globostellata</i>, and Their Cytotoxic and Cytoprotective Effects |
| title_full_unstemmed | Rhabdastrellosides A and B: Two New Isomalabaricane Glycosides from the Marine Sponge <i>Rhabdastrella globostellata</i>, and Their Cytotoxic and Cytoprotective Effects |
| title_short | Rhabdastrellosides A and B: Two New Isomalabaricane Glycosides from the Marine Sponge <i>Rhabdastrella globostellata</i>, and Their Cytotoxic and Cytoprotective Effects |
| title_sort | rhabdastrellosides a and b two new isomalabaricane glycosides from the marine sponge i rhabdastrella globostellata i and their cytotoxic and cytoprotective effects |
| topic | isomalabaricanes glycosides glycoconjugates <i>Rhabdastrella globostellata</i> marine sponge terpenoids |
| url | https://www.mdpi.com/1660-3397/21/11/554 |
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