Chemical and Biological Study of Novel Aplysiatoxin Derivatives from the Marine Cyanobacterium <i>Lyngbya</i> sp.
Since 1970s, aplysiatoxins (ATXs), a class of biologically active dermatoxins, were identified from the marine mollusk <i>Stylocheilus longicauda</i>, whilst further research indicated that ATXs were originally metabolized by cyanobacteria. So far, there have been 45 aplysiatoxin derivat...
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MDPI AG
2020-11-01
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| Series: | Toxins |
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| Online Access: | https://www.mdpi.com/2072-6651/12/11/733 |
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| author | Hui-Hui Zhang Xin-Kai Zhang Ran-Ran Si Si-Cheng Shen Ting-Ting Liang Ting-Ting Fan Wei Chen Lian-Hua Xu Bing-Nan Han |
| author_facet | Hui-Hui Zhang Xin-Kai Zhang Ran-Ran Si Si-Cheng Shen Ting-Ting Liang Ting-Ting Fan Wei Chen Lian-Hua Xu Bing-Nan Han |
| author_sort | Hui-Hui Zhang |
| collection | DOAJ |
| description | Since 1970s, aplysiatoxins (ATXs), a class of biologically active dermatoxins, were identified from the marine mollusk <i>Stylocheilus longicauda</i>, whilst further research indicated that ATXs were originally metabolized by cyanobacteria. So far, there have been 45 aplysiatoxin derivatives discovered from marine cyanobacteria with various geographies. Recently, we isolated two neo-debromoaplysiatoxins, neo-debromoaplysiatoxin G (<b>1</b>) and neo-debromoaplysiatoxin H (<b>2</b>) from the cyanobacterium <i>Lyngbya</i> sp. collected from the South China Sea. The freeze-dried cyanobacterium was extracted with liquid–liquid extraction of organic solvents, and then was subjected to multiple chromatographies to yield neo-debromoaplysiatoxin G (<b>1</b>) (3.6 mg) and neo-debromoaplysiatoxin H (<b>2</b>) (4.3 mg). They were elucidated with spectroscopic methods. Moreover, the brine shrimp toxicity of the aplysiatoxin derivatives representing differential structural classifications indicated that the debromoaplysiatoxin was the most toxic compound (half inhibitory concentration (IC<sub>50</sub>) value = 0.34 ± 0.036 µM). While neo-aplysiatoxins (neo-ATXs) did not exhibit apparent brine shrimp toxicity, but showed potent blocking action against potassium channel Kv1.5, likewise, compounds <b>1</b> and <b>2</b> with IC<sub>50</sub> values of 1.79 ± 0.22 µM and 1.46 ± 0.14 µM, respectively. Therefore, much of the current knowledge suggests the ATXs with different structure modifications may modulate multiple cellular signaling processes in animal systems leading to the harmful effects on public health. |
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| institution | Directory Open Access Journal |
| issn | 2072-6651 |
| language | English |
| last_indexed | 2024-03-10T14:39:03Z |
| publishDate | 2020-11-01 |
| publisher | MDPI AG |
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| series | Toxins |
| spelling | doaj.art-8fa1f9bf6fc14d159fdb123a54b09e452023-11-20T21:56:50ZengMDPI AGToxins2072-66512020-11-01121173310.3390/toxins12110733Chemical and Biological Study of Novel Aplysiatoxin Derivatives from the Marine Cyanobacterium <i>Lyngbya</i> sp.Hui-Hui Zhang0Xin-Kai Zhang1Ran-Ran Si2Si-Cheng Shen3Ting-Ting Liang4Ting-Ting Fan5Wei Chen6Lian-Hua Xu7Bing-Nan Han8Department of Development Technology of Marine Resources, College of Life Sciences and Medicine, Zhejiang Sci-Tech University, Hangzhou 310018, ChinaDepartment of Development Technology of Marine Resources, College of Life Sciences and Medicine, Zhejiang Sci-Tech University, Hangzhou 310018, ChinaSchool of Materials Science and Engineering, Zhejiang Sci-Tech University, Hangzhou 310018, ChinaDepartment of Development Technology of Marine Resources, College of Life Sciences and Medicine, Zhejiang Sci-Tech University, Hangzhou 310018, ChinaSchool of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, ChinaDepartment of Development Technology of Marine Resources, College of Life Sciences and Medicine, Zhejiang Sci-Tech University, Hangzhou 310018, ChinaDepartment of Development Technology of Marine Resources, College of Life Sciences and Medicine, Zhejiang Sci-Tech University, Hangzhou 310018, ChinaDepartment of Development Technology of Marine Resources, College of Life Sciences and Medicine, Zhejiang Sci-Tech University, Hangzhou 310018, ChinaDepartment of Development Technology of Marine Resources, College of Life Sciences and Medicine, Zhejiang Sci-Tech University, Hangzhou 310018, ChinaSince 1970s, aplysiatoxins (ATXs), a class of biologically active dermatoxins, were identified from the marine mollusk <i>Stylocheilus longicauda</i>, whilst further research indicated that ATXs were originally metabolized by cyanobacteria. So far, there have been 45 aplysiatoxin derivatives discovered from marine cyanobacteria with various geographies. Recently, we isolated two neo-debromoaplysiatoxins, neo-debromoaplysiatoxin G (<b>1</b>) and neo-debromoaplysiatoxin H (<b>2</b>) from the cyanobacterium <i>Lyngbya</i> sp. collected from the South China Sea. The freeze-dried cyanobacterium was extracted with liquid–liquid extraction of organic solvents, and then was subjected to multiple chromatographies to yield neo-debromoaplysiatoxin G (<b>1</b>) (3.6 mg) and neo-debromoaplysiatoxin H (<b>2</b>) (4.3 mg). They were elucidated with spectroscopic methods. Moreover, the brine shrimp toxicity of the aplysiatoxin derivatives representing differential structural classifications indicated that the debromoaplysiatoxin was the most toxic compound (half inhibitory concentration (IC<sub>50</sub>) value = 0.34 ± 0.036 µM). While neo-aplysiatoxins (neo-ATXs) did not exhibit apparent brine shrimp toxicity, but showed potent blocking action against potassium channel Kv1.5, likewise, compounds <b>1</b> and <b>2</b> with IC<sub>50</sub> values of 1.79 ± 0.22 µM and 1.46 ± 0.14 µM, respectively. Therefore, much of the current knowledge suggests the ATXs with different structure modifications may modulate multiple cellular signaling processes in animal systems leading to the harmful effects on public health.https://www.mdpi.com/2072-6651/12/11/733marine cyanobacterium<i>Lyngbya</i> sp.aplysiatoxinKv1.5 inhibitory activitybrine shrimp toxicity |
| spellingShingle | Hui-Hui Zhang Xin-Kai Zhang Ran-Ran Si Si-Cheng Shen Ting-Ting Liang Ting-Ting Fan Wei Chen Lian-Hua Xu Bing-Nan Han Chemical and Biological Study of Novel Aplysiatoxin Derivatives from the Marine Cyanobacterium <i>Lyngbya</i> sp. Toxins marine cyanobacterium <i>Lyngbya</i> sp. aplysiatoxin Kv1.5 inhibitory activity brine shrimp toxicity |
| title | Chemical and Biological Study of Novel Aplysiatoxin Derivatives from the Marine Cyanobacterium <i>Lyngbya</i> sp. |
| title_full | Chemical and Biological Study of Novel Aplysiatoxin Derivatives from the Marine Cyanobacterium <i>Lyngbya</i> sp. |
| title_fullStr | Chemical and Biological Study of Novel Aplysiatoxin Derivatives from the Marine Cyanobacterium <i>Lyngbya</i> sp. |
| title_full_unstemmed | Chemical and Biological Study of Novel Aplysiatoxin Derivatives from the Marine Cyanobacterium <i>Lyngbya</i> sp. |
| title_short | Chemical and Biological Study of Novel Aplysiatoxin Derivatives from the Marine Cyanobacterium <i>Lyngbya</i> sp. |
| title_sort | chemical and biological study of novel aplysiatoxin derivatives from the marine cyanobacterium i lyngbya i sp |
| topic | marine cyanobacterium <i>Lyngbya</i> sp. aplysiatoxin Kv1.5 inhibitory activity brine shrimp toxicity |
| url | https://www.mdpi.com/2072-6651/12/11/733 |
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