Indole Alkaloids of the Stigonematales (Cyanophyta): Chemical Diversity, Biosynthesis and Biological Activity
The cyanobacteria are well recognized as producers of a wide array of bioactive metabolites including toxins, and potential drug candidates. However, a limited number of taxa are generally considered with respect to both of these aspects. That said, the order Stigonematales, although largely overloo...
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| Format: | Article |
| Language: | English |
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MDPI AG
2016-04-01
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| Series: | Marine Drugs |
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| Online Access: | http://www.mdpi.com/1660-3397/14/4/73 |
| _version_ | 1811184348137783296 |
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| author | Katherine Walton John P. Berry |
| author_facet | Katherine Walton John P. Berry |
| author_sort | Katherine Walton |
| collection | DOAJ |
| description | The cyanobacteria are well recognized as producers of a wide array of bioactive metabolites including toxins, and potential drug candidates. However, a limited number of taxa are generally considered with respect to both of these aspects. That said, the order Stigonematales, although largely overlooked in this regard, has become increasingly recognized as a source of bioactive metabolites relevant to both human and environmental health. In particular, the hapalindoles and related indole alkaloids (i.e., ambiguines, fischerindoles, welwitindolinones) from the order, represent a diverse, and phylogenetically characteristic, class of secondary metabolites with biological activity suggestive of potential as both environmental toxins, and promising drug discovery leads. The present review gives an overview of the chemical diversity of biologically active metabolites from the Stigonematales—and particularly the so-called hapalindole-type alkaloids—including their biosynthetic origins, and their pharmacologically and toxicologically relevant bioactivities. Taken together, the current evidence suggests that these alkaloids, and the associated cyanobacterial taxa from the order, warrant future consideration as both potentially harmful (i.e., “toxic”) algae, and as promising leads for drug discovery. |
| first_indexed | 2024-04-11T13:10:42Z |
| format | Article |
| id | doaj.art-b5dfcd259ead453bbe9210263484dd58 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-04-11T13:10:42Z |
| publishDate | 2016-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-b5dfcd259ead453bbe9210263484dd582022-12-22T04:22:36ZengMDPI AGMarine Drugs1660-33972016-04-011447310.3390/md14040073md14040073Indole Alkaloids of the Stigonematales (Cyanophyta): Chemical Diversity, Biosynthesis and Biological ActivityKatherine Walton0John P. Berry1Department of Chemistry and Biochemistry, Marine Science Program, Florida International University, 3000 NE 151st Street, North Miami, FL 33181, USADepartment of Chemistry and Biochemistry, Marine Science Program, Florida International University, 3000 NE 151st Street, North Miami, FL 33181, USAThe cyanobacteria are well recognized as producers of a wide array of bioactive metabolites including toxins, and potential drug candidates. However, a limited number of taxa are generally considered with respect to both of these aspects. That said, the order Stigonematales, although largely overlooked in this regard, has become increasingly recognized as a source of bioactive metabolites relevant to both human and environmental health. In particular, the hapalindoles and related indole alkaloids (i.e., ambiguines, fischerindoles, welwitindolinones) from the order, represent a diverse, and phylogenetically characteristic, class of secondary metabolites with biological activity suggestive of potential as both environmental toxins, and promising drug discovery leads. The present review gives an overview of the chemical diversity of biologically active metabolites from the Stigonematales—and particularly the so-called hapalindole-type alkaloids—including their biosynthetic origins, and their pharmacologically and toxicologically relevant bioactivities. Taken together, the current evidence suggests that these alkaloids, and the associated cyanobacterial taxa from the order, warrant future consideration as both potentially harmful (i.e., “toxic”) algae, and as promising leads for drug discovery.http://www.mdpi.com/1660-3397/14/4/73cyanobacteriablue-green algaeStigonematalesindole alkaloidshapalindoleambiguinefischerindolewelwitindolinonetoxinsharmful algal blooms |
| spellingShingle | Katherine Walton John P. Berry Indole Alkaloids of the Stigonematales (Cyanophyta): Chemical Diversity, Biosynthesis and Biological Activity Marine Drugs cyanobacteria blue-green algae Stigonematales indole alkaloids hapalindole ambiguine fischerindole welwitindolinone toxins harmful algal blooms |
| title | Indole Alkaloids of the Stigonematales (Cyanophyta): Chemical Diversity, Biosynthesis and Biological Activity |
| title_full | Indole Alkaloids of the Stigonematales (Cyanophyta): Chemical Diversity, Biosynthesis and Biological Activity |
| title_fullStr | Indole Alkaloids of the Stigonematales (Cyanophyta): Chemical Diversity, Biosynthesis and Biological Activity |
| title_full_unstemmed | Indole Alkaloids of the Stigonematales (Cyanophyta): Chemical Diversity, Biosynthesis and Biological Activity |
| title_short | Indole Alkaloids of the Stigonematales (Cyanophyta): Chemical Diversity, Biosynthesis and Biological Activity |
| title_sort | indole alkaloids of the stigonematales cyanophyta chemical diversity biosynthesis and biological activity |
| topic | cyanobacteria blue-green algae Stigonematales indole alkaloids hapalindole ambiguine fischerindole welwitindolinone toxins harmful algal blooms |
| url | http://www.mdpi.com/1660-3397/14/4/73 |
| work_keys_str_mv | AT katherinewalton indolealkaloidsofthestigonematalescyanophytachemicaldiversitybiosynthesisandbiologicalactivity AT johnpberry indolealkaloidsofthestigonematalescyanophytachemicaldiversitybiosynthesisandbiologicalactivity |