Aplysiadione and aplysiaenal: Truncated biosynthetic intermediates of aplysiatoxins from a cyanobacterium
Aplysiatoxin and its derivatives have been isolated from marine cyanobacteria. The biosynthesis of their characteristic bicyclic skeletons from a linear polyketide intermediate has been proposed. Two polyketides, aplysiadione (1) and aplysiaenal (2), were isolated from the marine cyanobacterium Moor...
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| Format: | Article |
| Language: | English |
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Elsevier
2021-01-01
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| Series: | Results in Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2211715621001119 |
| _version_ | 1818871818797187072 |
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| author | Masayuki Satake Kanon Iguchi Ryuichi Watanabe Hajime Uchida Hiroshi Nagai |
| author_facet | Masayuki Satake Kanon Iguchi Ryuichi Watanabe Hajime Uchida Hiroshi Nagai |
| author_sort | Masayuki Satake |
| collection | DOAJ |
| description | Aplysiatoxin and its derivatives have been isolated from marine cyanobacteria. The biosynthesis of their characteristic bicyclic skeletons from a linear polyketide intermediate has been proposed. Two polyketides, aplysiadione (1) and aplysiaenal (2), were isolated from the marine cyanobacterium Moorea producens (formerly Lyngbya majuscula) collected in the Okinawan coastal area. The polyketide chemical structures were elucidated from HR ESI-MS and NMR spectra. Aplysiadione (1) corresponds to a decarboxylated analog of the proposed biosynthetic intermediate of aplysiatoxins. Aplysiaenal (2) is a truncated analog of the linear intermediate. The isolation of aplysiadione (1) strongly supports the proposed ring formation mechanisms for the aplysiatoxins, and this compound is a rare example of a biosynthetic intermediate of polyketide secondary metabolites from marine cyanobacteria. |
| first_indexed | 2024-12-19T12:28:58Z |
| format | Article |
| id | doaj.art-eb83cd9fb56d41d5a60d0518b7c9ac80 |
| institution | Directory Open Access Journal |
| issn | 2211-7156 |
| language | English |
| last_indexed | 2024-12-19T12:28:58Z |
| publishDate | 2021-01-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Results in Chemistry |
| spelling | doaj.art-eb83cd9fb56d41d5a60d0518b7c9ac802022-12-21T20:21:27ZengElsevierResults in Chemistry2211-71562021-01-013100206Aplysiadione and aplysiaenal: Truncated biosynthetic intermediates of aplysiatoxins from a cyanobacteriumMasayuki Satake0Kanon Iguchi1Ryuichi Watanabe2Hajime Uchida3Hiroshi Nagai4Department of Chemistry, The University of Tokyo, Tokyo 113-0033, JapanDepartment of Ocean Sciences, Tokyo University of Marine Science and Technology, Tokyo 108-8477, JapanFisheries Technology Institute, Japan Fisheries Research and Education Agency, Yokohama 236-8648, JapanFisheries Technology Institute, Japan Fisheries Research and Education Agency, Yokohama 236-8648, JapanDepartment of Ocean Sciences, Tokyo University of Marine Science and Technology, Tokyo 108-8477, Japan; Corresponding author.Aplysiatoxin and its derivatives have been isolated from marine cyanobacteria. The biosynthesis of their characteristic bicyclic skeletons from a linear polyketide intermediate has been proposed. Two polyketides, aplysiadione (1) and aplysiaenal (2), were isolated from the marine cyanobacterium Moorea producens (formerly Lyngbya majuscula) collected in the Okinawan coastal area. The polyketide chemical structures were elucidated from HR ESI-MS and NMR spectra. Aplysiadione (1) corresponds to a decarboxylated analog of the proposed biosynthetic intermediate of aplysiatoxins. Aplysiaenal (2) is a truncated analog of the linear intermediate. The isolation of aplysiadione (1) strongly supports the proposed ring formation mechanisms for the aplysiatoxins, and this compound is a rare example of a biosynthetic intermediate of polyketide secondary metabolites from marine cyanobacteria.http://www.sciencedirect.com/science/article/pii/S2211715621001119AplysiatoxinsBiosynthetic intermediatesPolyketidesCyanobacteria |
| spellingShingle | Masayuki Satake Kanon Iguchi Ryuichi Watanabe Hajime Uchida Hiroshi Nagai Aplysiadione and aplysiaenal: Truncated biosynthetic intermediates of aplysiatoxins from a cyanobacterium Results in Chemistry Aplysiatoxins Biosynthetic intermediates Polyketides Cyanobacteria |
| title | Aplysiadione and aplysiaenal: Truncated biosynthetic intermediates of aplysiatoxins from a cyanobacterium |
| title_full | Aplysiadione and aplysiaenal: Truncated biosynthetic intermediates of aplysiatoxins from a cyanobacterium |
| title_fullStr | Aplysiadione and aplysiaenal: Truncated biosynthetic intermediates of aplysiatoxins from a cyanobacterium |
| title_full_unstemmed | Aplysiadione and aplysiaenal: Truncated biosynthetic intermediates of aplysiatoxins from a cyanobacterium |
| title_short | Aplysiadione and aplysiaenal: Truncated biosynthetic intermediates of aplysiatoxins from a cyanobacterium |
| title_sort | aplysiadione and aplysiaenal truncated biosynthetic intermediates of aplysiatoxins from a cyanobacterium |
| topic | Aplysiatoxins Biosynthetic intermediates Polyketides Cyanobacteria |
| url | http://www.sciencedirect.com/science/article/pii/S2211715621001119 |
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