Unlocking the Diversity of Pyrroloiminoquinones Produced by Latrunculid Sponge Species
Sponges of the Latrunculiidae family produce bioactive pyrroloiminoquinone alkaloids including makaluvamines, discorhabdins, and tsitsikammamines. The aim of this study was to use LC-ESI-MS/MS-driven molecular networking to characterize the pyrroloiminoquinone secondary metabolites produced by six l...
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-01-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/19/2/68 |
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| author | Jarmo-Charles J. Kalinski Rui W. M. Krause Shirley Parker-Nance Samantha C. Waterworth Rosemary A. Dorrington |
| author_facet | Jarmo-Charles J. Kalinski Rui W. M. Krause Shirley Parker-Nance Samantha C. Waterworth Rosemary A. Dorrington |
| author_sort | Jarmo-Charles J. Kalinski |
| collection | DOAJ |
| description | Sponges of the Latrunculiidae family produce bioactive pyrroloiminoquinone alkaloids including makaluvamines, discorhabdins, and tsitsikammamines. The aim of this study was to use LC-ESI-MS/MS-driven molecular networking to characterize the pyrroloiminoquinone secondary metabolites produced by six latrunculid species. These are <i>Tsitsikamma favus</i>, <i>Tsitsikamma pedunculata</i>, <i>Cyclacanthia bellae,</i> and <i>Latrunculia apicalis</i> as well as the recently discovered species, <i>Tsitsikamma nguni</i> and <i>Tsitsikamma michaeli</i>. Organic extracts of 43 sponges were analyzed, revealing distinct species-specific chemical profiles. More than 200 known and unknown putative pyrroloiminoquinones and related compounds were detected, including unprecedented makaluvamine-discorhabdin adducts and hydroxylated discorhabdin I derivatives. The chemical profiles of the new species <i>T. nguni</i> closely resembled those of the known <i>T. favus</i> (chemotype I), but with a higher abundance of tsitsikammamines vs. discorhabdins. <i>T. michaeli</i> sponges displayed two distinct chemical profiles, either producing mostly the same discorhabdins as <i>T. favus</i> (chemotype I) or non- or monobrominated, hydroxylated discorhabdins. <i>C. bellae</i> and <i>L. apicalis</i> produced similar pyrroloiminoquinone chemistry to one another, characterized by sulfur-containing discorhabdins and related adducts and oligomers. This study highlights the variability of pyrroloiminoquinone production by latrunculid species, identifies novel isolation targets, and offers fundamental insights into the collision-induced dissociation of pyrroloiminoquinones. |
| first_indexed | 2024-03-09T03:26:06Z |
| format | Article |
| id | doaj.art-179850a76fc044dc9ac3fb538b03aec3 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-09T03:26:06Z |
| publishDate | 2021-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-179850a76fc044dc9ac3fb538b03aec32023-12-03T15:01:26ZengMDPI AGMarine Drugs1660-33972021-01-011926810.3390/md19020068Unlocking the Diversity of Pyrroloiminoquinones Produced by Latrunculid Sponge SpeciesJarmo-Charles J. Kalinski0Rui W. M. Krause1Shirley Parker-Nance2Samantha C. Waterworth3Rosemary A. Dorrington4Department of Biochemistry and Microbiology, Rhodes University, Makhanda 6140, South AfricaDepartment of Chemistry, Rhodes University, Makhanda 6140, South AfricaDepartment of Biochemistry and Microbiology, Rhodes University, Makhanda 6140, South AfricaDepartment of Biochemistry and Microbiology, Rhodes University, Makhanda 6140, South AfricaDepartment of Biochemistry and Microbiology, Rhodes University, Makhanda 6140, South AfricaSponges of the Latrunculiidae family produce bioactive pyrroloiminoquinone alkaloids including makaluvamines, discorhabdins, and tsitsikammamines. The aim of this study was to use LC-ESI-MS/MS-driven molecular networking to characterize the pyrroloiminoquinone secondary metabolites produced by six latrunculid species. These are <i>Tsitsikamma favus</i>, <i>Tsitsikamma pedunculata</i>, <i>Cyclacanthia bellae,</i> and <i>Latrunculia apicalis</i> as well as the recently discovered species, <i>Tsitsikamma nguni</i> and <i>Tsitsikamma michaeli</i>. Organic extracts of 43 sponges were analyzed, revealing distinct species-specific chemical profiles. More than 200 known and unknown putative pyrroloiminoquinones and related compounds were detected, including unprecedented makaluvamine-discorhabdin adducts and hydroxylated discorhabdin I derivatives. The chemical profiles of the new species <i>T. nguni</i> closely resembled those of the known <i>T. favus</i> (chemotype I), but with a higher abundance of tsitsikammamines vs. discorhabdins. <i>T. michaeli</i> sponges displayed two distinct chemical profiles, either producing mostly the same discorhabdins as <i>T. favus</i> (chemotype I) or non- or monobrominated, hydroxylated discorhabdins. <i>C. bellae</i> and <i>L. apicalis</i> produced similar pyrroloiminoquinone chemistry to one another, characterized by sulfur-containing discorhabdins and related adducts and oligomers. This study highlights the variability of pyrroloiminoquinone production by latrunculid species, identifies novel isolation targets, and offers fundamental insights into the collision-induced dissociation of pyrroloiminoquinones.https://www.mdpi.com/1660-3397/19/2/68molecular networkingLC-MS-MSmakaluvaminediscorhabdintsitsikammaminechemotype |
| spellingShingle | Jarmo-Charles J. Kalinski Rui W. M. Krause Shirley Parker-Nance Samantha C. Waterworth Rosemary A. Dorrington Unlocking the Diversity of Pyrroloiminoquinones Produced by Latrunculid Sponge Species Marine Drugs molecular networking LC-MS-MS makaluvamine discorhabdin tsitsikammamine chemotype |
| title | Unlocking the Diversity of Pyrroloiminoquinones Produced by Latrunculid Sponge Species |
| title_full | Unlocking the Diversity of Pyrroloiminoquinones Produced by Latrunculid Sponge Species |
| title_fullStr | Unlocking the Diversity of Pyrroloiminoquinones Produced by Latrunculid Sponge Species |
| title_full_unstemmed | Unlocking the Diversity of Pyrroloiminoquinones Produced by Latrunculid Sponge Species |
| title_short | Unlocking the Diversity of Pyrroloiminoquinones Produced by Latrunculid Sponge Species |
| title_sort | unlocking the diversity of pyrroloiminoquinones produced by latrunculid sponge species |
| topic | molecular networking LC-MS-MS makaluvamine discorhabdin tsitsikammamine chemotype |
| url | https://www.mdpi.com/1660-3397/19/2/68 |
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