Jorumycidine, a hexacyclic bis-tetrahydroisoquinoline alkaloid from marine symbiosis reveals new biosynthetic logic for anticancer design.
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| Autori principali: | , , , , , , , , , , |
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| Natura: | Artículo científico |
| Lingua: | en |
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Communications chemistry
2026
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| _version_ | 1868266064337436672 |
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| author | Nuzzo, Genoveffa Quaini, Giulia Albiani, Federica Gallo, Carmela Landi, Simone Carbone, Dalila Pescitelli, Gennaro Castiglia, Daniela Manzo, Emiliano d'Ippolito, Giuliana Fontana, Angelo |
| author_facet | Nuzzo, Genoveffa Quaini, Giulia Albiani, Federica Gallo, Carmela Landi, Simone Carbone, Dalila Pescitelli, Gennaro Castiglia, Daniela Manzo, Emiliano d'Ippolito, Giuliana Fontana, Angelo Nuzzo, Genoveffa Quaini, Giulia Albiani, Federica Gallo, Carmela Landi, Simone Carbone, Dalila Pescitelli, Gennaro Castiglia, Daniela Manzo, Emiliano d'Ippolito, Giuliana Fontana, Angelo |
| collection | PubMed - marine biology |
| contents | Jorumycidine, a hexacyclic bis-tetrahydroisoquinoline alkaloid from marine symbiosis reveals new biosynthetic logic for anticancer design. Nuzzo, Genoveffa Quaini, Giulia Albiani, Federica Gallo, Carmela Landi, Simone Carbone, Dalila Pescitelli, Gennaro Castiglia, Daniela Manzo, Emiliano d'Ippolito, Giuliana Fontana, Angelo Marine opisthobranch mollusks are a valuable source of structurally diverse bioactive metabolites arising from de novo biosynthesis or dietary origins. Jorumycidine (4) is a novel bis-tetrahydroisoquinoline (bis-THIQ) alkaloid with an unprecedented hexacyclic skeleton, isolated together with jorumycin (2), renieramycin E (3), and new 21-deoxy analogues (5, 6) from the nudibranch Jorunna funebris and its dietary sponge Haliclona sp. The structure of jorumycidine, featuring a unique oxazolidine ring, was elucidated by spectroscopic, spectrometric, and chiroptical analyses. LC-MS/MS diagnostic fragmentation filtering (DFF), combined with re-annotation of the ren biosynthetic gene cluster recently identified in a Haliclona endosymbiont, supported a hybrid NRPS-PKS origin and revealed enzymatic conversion of sponge-derived renieramycins into jorumycins by the nudibranch. Jorumycidine exhibited potent nanomolar cytotoxicity (IC₅₀ = 13.8 nM) against multiple myeloma cells, outperforming its congeners. These findings expand bis-THIQ chemical diversity and demonstrate how interspecies metabolic interplay can generate bioactive scaffolds with therapeutic potential. |
| format | Artículo científico |
| id | pubmed_41946897 |
| institution | PubMed |
| language | en |
| publishDate | 2026 |
| publisher | Communications chemistry |
| record_format | pubmed |
| spellingShingle | Jorumycidine, a hexacyclic bis-tetrahydroisoquinoline alkaloid from marine symbiosis reveals new biosynthetic logic for anticancer design. Nuzzo, Genoveffa Quaini, Giulia Albiani, Federica Gallo, Carmela Landi, Simone Carbone, Dalila Pescitelli, Gennaro Castiglia, Daniela Manzo, Emiliano d'Ippolito, Giuliana Fontana, Angelo Jorumycidine, a hexacyclic bis-tetrahydroisoquinoline alkaloid from marine symbiosis reveals new biosynthetic logic for anticancer design. Nuzzo, Genoveffa Quaini, Giulia Albiani, Federica Gallo, Carmela Landi, Simone Carbone, Dalila Pescitelli, Gennaro Castiglia, Daniela Manzo, Emiliano d'Ippolito, Giuliana Fontana, Angelo Marine opisthobranch mollusks are a valuable source of structurally diverse bioactive metabolites arising from de novo biosynthesis or dietary origins. Jorumycidine (4) is a novel bis-tetrahydroisoquinoline (bis-THIQ) alkaloid with an unprecedented hexacyclic skeleton, isolated together with jorumycin (2), renieramycin E (3), and new 21-deoxy analogues (5, 6) from the nudibranch Jorunna funebris and its dietary sponge Haliclona sp. The structure of jorumycidine, featuring a unique oxazolidine ring, was elucidated by spectroscopic, spectrometric, and chiroptical analyses. LC-MS/MS diagnostic fragmentation filtering (DFF), combined with re-annotation of the ren biosynthetic gene cluster recently identified in a Haliclona endosymbiont, supported a hybrid NRPS-PKS origin and revealed enzymatic conversion of sponge-derived renieramycins into jorumycins by the nudibranch. Jorumycidine exhibited potent nanomolar cytotoxicity (IC₅₀ = 13.8 nM) against multiple myeloma cells, outperforming its congeners. These findings expand bis-THIQ chemical diversity and demonstrate how interspecies metabolic interplay can generate bioactive scaffolds with therapeutic potential. |
| title | Jorumycidine, a hexacyclic bis-tetrahydroisoquinoline alkaloid from marine symbiosis reveals new biosynthetic logic for anticancer design. |
| url | https://pubmed.ncbi.nlm.nih.gov/41946897/ |