Structure Diversity and Properties of Some Bola-like Natural Products
In their shapes, molecules of some bipolar metabolites resemble the so-called bola, a hunting weapon of the South American inhabitants, consisting of two heavy balls connected to each other by a long flexible cord. Herein, we discuss the structures and properties of these natural products (bola-like...
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MDPI AG
2024-12-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/23/1/3 |
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| author | Valentin A. Stonik Tatyana N. Makarieva Larisa K. Shubina Alla G. Guzii Natalia V. Ivanchina |
| author_facet | Valentin A. Stonik Tatyana N. Makarieva Larisa K. Shubina Alla G. Guzii Natalia V. Ivanchina |
| author_sort | Valentin A. Stonik |
| collection | DOAJ |
| description | In their shapes, molecules of some bipolar metabolites resemble the so-called bola, a hunting weapon of the South American inhabitants, consisting of two heavy balls connected to each other by a long flexible cord. Herein, we discuss the structures and properties of these natural products (bola-like compounds or bolaamphiphiles), containing two polar terminal fragments and a non-polar chain (or chains) between them, from archaea, bacteria, and marine invertebrates. Additional modifications of core compounds of this class, for example, interchain and intrachain cyclization, hydroxylation, methylation, etc., expand the number of known metabolites of this type, providing their great structural variety. Isolation of such complex compounds individually is problematic, since they usually exist as mixtures of regioisomers and stereoisomers, that are very difficult to be separated. The main approaches to the study of their structures combine various methods of HPLC/MS or GC/MS, 2D-NMR experiments and organic synthesis. The recent identification of new enzymes, taking part in their biosynthesis and metabolism, made it possible to understand molecular aspects of their origination and some features of evolution during geological times. The promising properties of these metabolites, such as their ability to self-assemble and stabilize biological or artificial membranes, and biological activities, attract additional attention to them. |
| format | Article |
| id | doaj-art-e90f5bea142e4b679d6e83e94a9e666e |
| institution | Kabale University |
| issn | 1660-3397 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj-art-e90f5bea142e4b679d6e83e94a9e666e2025-01-24T13:39:25ZengMDPI AGMarine Drugs1660-33972024-12-01231310.3390/md23010003Structure Diversity and Properties of Some Bola-like Natural ProductsValentin A. Stonik0Tatyana N. Makarieva1Larisa K. Shubina2Alla G. Guzii3Natalia V. Ivanchina4G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch, Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch, Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch, Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch, Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch, Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, RussiaIn their shapes, molecules of some bipolar metabolites resemble the so-called bola, a hunting weapon of the South American inhabitants, consisting of two heavy balls connected to each other by a long flexible cord. Herein, we discuss the structures and properties of these natural products (bola-like compounds or bolaamphiphiles), containing two polar terminal fragments and a non-polar chain (or chains) between them, from archaea, bacteria, and marine invertebrates. Additional modifications of core compounds of this class, for example, interchain and intrachain cyclization, hydroxylation, methylation, etc., expand the number of known metabolites of this type, providing their great structural variety. Isolation of such complex compounds individually is problematic, since they usually exist as mixtures of regioisomers and stereoisomers, that are very difficult to be separated. The main approaches to the study of their structures combine various methods of HPLC/MS or GC/MS, 2D-NMR experiments and organic synthesis. The recent identification of new enzymes, taking part in their biosynthesis and metabolism, made it possible to understand molecular aspects of their origination and some features of evolution during geological times. The promising properties of these metabolites, such as their ability to self-assemble and stabilize biological or artificial membranes, and biological activities, attract additional attention to them.https://www.mdpi.com/1660-3397/23/1/3archaeal bolaamphiphilesbacterial bola-like productsbolaamphiphiles of marine invertebratesstructurestaxonomic distributionbiosynthesis |
| spellingShingle | Valentin A. Stonik Tatyana N. Makarieva Larisa K. Shubina Alla G. Guzii Natalia V. Ivanchina Structure Diversity and Properties of Some Bola-like Natural Products Marine Drugs archaeal bolaamphiphiles bacterial bola-like products bolaamphiphiles of marine invertebrates structures taxonomic distribution biosynthesis |
| title | Structure Diversity and Properties of Some Bola-like Natural Products |
| title_full | Structure Diversity and Properties of Some Bola-like Natural Products |
| title_fullStr | Structure Diversity and Properties of Some Bola-like Natural Products |
| title_full_unstemmed | Structure Diversity and Properties of Some Bola-like Natural Products |
| title_short | Structure Diversity and Properties of Some Bola-like Natural Products |
| title_sort | structure diversity and properties of some bola like natural products |
| topic | archaeal bolaamphiphiles bacterial bola-like products bolaamphiphiles of marine invertebrates structures taxonomic distribution biosynthesis |
| url | https://www.mdpi.com/1660-3397/23/1/3 |
| work_keys_str_mv | AT valentinastonik structurediversityandpropertiesofsomebolalikenaturalproducts AT tatyananmakarieva structurediversityandpropertiesofsomebolalikenaturalproducts AT larisakshubina structurediversityandpropertiesofsomebolalikenaturalproducts AT allagguzii structurediversityandpropertiesofsomebolalikenaturalproducts AT nataliavivanchina structurediversityandpropertiesofsomebolalikenaturalproducts |