Unlocking the Diversity of Pyrroloiminoquinones Produced by Latrunculid Sponge Species
- Kalinski, Jarmo-Charles J, Krause, Rui W M, Parker-Nance, Shirley, Waterworth, Samantha C, Dorrington, Rosemary A
- Authors: Kalinski, Jarmo-Charles J , Krause, Rui W M , Parker-Nance, Shirley , Waterworth, Samantha C , Dorrington, Rosemary A
- Date: 2021
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/191802 , vital:45165 , xlink:href="https://doi.org/10.3390/md19020068"
- 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 Tsitsikamma favus, Tsitsikamma pedunculata, Cyclacanthia bellae, and Latrunculia apicalis as well as the recently discovered species, Tsitsikamma nguni and Tsitsikamma michaeli. 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 T. nguni closely resembled those of the known T. favus (chemotype I), but with a higher abundance of tsitsikammamines vs. discorhabdins. T. michaeli sponges displayed two distinct chemical profiles, either producing mostly the same discorhabdins as T. favus (chemotype I) or non- or monobrominated, hydroxylated discorhabdins. C. bellae and L. apicalis 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.
- Full Text:
- Authors: Kalinski, Jarmo-Charles J , Krause, Rui W M , Parker-Nance, Shirley , Waterworth, Samantha C , Dorrington, Rosemary A
- Date: 2021
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/191802 , vital:45165 , xlink:href="https://doi.org/10.3390/md19020068"
- 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 Tsitsikamma favus, Tsitsikamma pedunculata, Cyclacanthia bellae, and Latrunculia apicalis as well as the recently discovered species, Tsitsikamma nguni and Tsitsikamma michaeli. 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 T. nguni closely resembled those of the known T. favus (chemotype I), but with a higher abundance of tsitsikammamines vs. discorhabdins. T. michaeli sponges displayed two distinct chemical profiles, either producing mostly the same discorhabdins as T. favus (chemotype I) or non- or monobrominated, hydroxylated discorhabdins. C. bellae and L. apicalis 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.
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Molecular Networking Reveals Two Distinct Chemotypes in Pyrroloiminoquinone-Producing Tsitsikamma favus Sponges
- Kalinski, Jarmo-Charles J, Waterworth, Samantha C, Noundou, Xavier S, Jiwaji, Meesbah, Parker-Nance, Shirley, Krause, Rui W M, McPhail, Kerry L, Dorrington, Rosemary A
- Authors: Kalinski, Jarmo-Charles J , Waterworth, Samantha C , Noundou, Xavier S , Jiwaji, Meesbah , Parker-Nance, Shirley , Krause, Rui W M , McPhail, Kerry L , Dorrington, Rosemary A
- Date: 2019
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/131618 , vital:36673 , https://doi.org/10.3390/md17010060
- Description: The temperate marine sponge, Tsitsikamma favus, produces pyrroloiminoquinone alkaloids with potential as anticancer drug leads. We profiled the secondary metabolite reservoir of T. favus sponges using HR-ESI-LC-MS/MS-based molecular networking analysis followed by preparative purification efforts to map the diversity of new and known pyrroloiminoquinones and related compounds in extracts of seven specimens. Molecular taxonomic identification confirmed all sponges as T. favus and five specimens (chemotype I) were found to produce mainly discorhabdins and tsitsikammamines. Remarkably, however, two specimens (chemotype II) exhibited distinct morphological and chemical characteristics: the absence of discorhabdins, only trace levels of tsitsikammamines and, instead, an abundance of unbranched and halogenated makaluvamines. Targeted chromatographic isolation provided the new makaluvamine Q, the known makaluvamines A and I, tsitsikammamine B, 14-bromo-7,8-dehydro-3-dihydro-discorhabdin C, and the related pyrrolo-ortho-quinones makaluvamine O and makaluvone. Purified compounds displayed different activity profiles in assays for topoisomerase I inhibition, DNA intercalation and antimetabolic activity against human cell lines. This is the first report of makaluvamines from a Tsitsikamma sponge species, and the first description of distinct chemotypes within a species of the Latrunculiidae family. This study sheds new light on the putative pyrroloiminoquinone biosynthetic pathway of latrunculid sponges
- Full Text:
- Authors: Kalinski, Jarmo-Charles J , Waterworth, Samantha C , Noundou, Xavier S , Jiwaji, Meesbah , Parker-Nance, Shirley , Krause, Rui W M , McPhail, Kerry L , Dorrington, Rosemary A
- Date: 2019
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/131618 , vital:36673 , https://doi.org/10.3390/md17010060
- Description: The temperate marine sponge, Tsitsikamma favus, produces pyrroloiminoquinone alkaloids with potential as anticancer drug leads. We profiled the secondary metabolite reservoir of T. favus sponges using HR-ESI-LC-MS/MS-based molecular networking analysis followed by preparative purification efforts to map the diversity of new and known pyrroloiminoquinones and related compounds in extracts of seven specimens. Molecular taxonomic identification confirmed all sponges as T. favus and five specimens (chemotype I) were found to produce mainly discorhabdins and tsitsikammamines. Remarkably, however, two specimens (chemotype II) exhibited distinct morphological and chemical characteristics: the absence of discorhabdins, only trace levels of tsitsikammamines and, instead, an abundance of unbranched and halogenated makaluvamines. Targeted chromatographic isolation provided the new makaluvamine Q, the known makaluvamines A and I, tsitsikammamine B, 14-bromo-7,8-dehydro-3-dihydro-discorhabdin C, and the related pyrrolo-ortho-quinones makaluvamine O and makaluvone. Purified compounds displayed different activity profiles in assays for topoisomerase I inhibition, DNA intercalation and antimetabolic activity against human cell lines. This is the first report of makaluvamines from a Tsitsikamma sponge species, and the first description of distinct chemotypes within a species of the Latrunculiidae family. This study sheds new light on the putative pyrroloiminoquinone biosynthetic pathway of latrunculid sponges
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Latrunculid sponges, their microbial communities and secondary metabolites: connecting conserved bacterial symbionts to pyrroloiminoquinone production
- Dorrington, Rosemary A, Hilliar, Storm Hannah, Kalinski, Jarmo-Charles J, Krause, Rui W M, McPhail, Kerry L, Parker-Nance, Shirley, Wlalmsley, Tara A, Waterworth, Samantha C
- Authors: Dorrington, Rosemary A , Hilliar, Storm Hannah , Kalinski, Jarmo-Charles J , Krause, Rui W M , McPhail, Kerry L , Parker-Nance, Shirley , Wlalmsley, Tara A , Waterworth, Samantha C
- Date: 2016
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/65915 , vital:28858 , https://doi.org/10.1055/s-0036-1596655
- Description: publisher version , The Latrunculiidae are cold water sponges known for their production of bioactive pyrroloiminoquinone alkaloids (e.g. makaluvamines, discorhabdins and tsitsikammamines). Since pyrroloiminoquinones have also been isolated from sponges belonging to other families, ascidians and microorganisms, the biosynthetic origin of these alkaloids in latrunculid sponges is likely microbial. This study focuses on the secondary metabolites produced by closely-related Tsitsikamma species and Cyclacanthia bellae, all latrunculid sponges endemic to Algoa Bay on the South African southeast coast. The sponges produced suites of related pyrroloiminoquinones, including tsitsikammine A and B, and discohabdin C and V, the combination and relative abundance of which is species-specific. Characterisation of the diversity of sponge-associated bacterial communities revealed the unprecedented conservation of two dominant bacterial species. The first, a Betaproteobacterium, is also found in other latrunculids and related sponge families, representing a novel clade of sponge endosymbionts that have co-evolved with their hosts. The second conserved bacterial symbiont is a spirochaete found only in Cyclacanthia and Tsitsikamma species that is likely to have been recruited from free-living spirochaetes in the environment. This study sheds new light on the interactions between latrunculid sponges, their dominant bacterial symbionts, and the potential involvement of these bacteria in pyrroloiminoquinone biosynthesis.
- Full Text: false
- Authors: Dorrington, Rosemary A , Hilliar, Storm Hannah , Kalinski, Jarmo-Charles J , Krause, Rui W M , McPhail, Kerry L , Parker-Nance, Shirley , Wlalmsley, Tara A , Waterworth, Samantha C
- Date: 2016
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/65915 , vital:28858 , https://doi.org/10.1055/s-0036-1596655
- Description: publisher version , The Latrunculiidae are cold water sponges known for their production of bioactive pyrroloiminoquinone alkaloids (e.g. makaluvamines, discorhabdins and tsitsikammamines). Since pyrroloiminoquinones have also been isolated from sponges belonging to other families, ascidians and microorganisms, the biosynthetic origin of these alkaloids in latrunculid sponges is likely microbial. This study focuses on the secondary metabolites produced by closely-related Tsitsikamma species and Cyclacanthia bellae, all latrunculid sponges endemic to Algoa Bay on the South African southeast coast. The sponges produced suites of related pyrroloiminoquinones, including tsitsikammine A and B, and discohabdin C and V, the combination and relative abundance of which is species-specific. Characterisation of the diversity of sponge-associated bacterial communities revealed the unprecedented conservation of two dominant bacterial species. The first, a Betaproteobacterium, is also found in other latrunculids and related sponge families, representing a novel clade of sponge endosymbionts that have co-evolved with their hosts. The second conserved bacterial symbiont is a spirochaete found only in Cyclacanthia and Tsitsikamma species that is likely to have been recruited from free-living spirochaetes in the environment. This study sheds new light on the interactions between latrunculid sponges, their dominant bacterial symbionts, and the potential involvement of these bacteria in pyrroloiminoquinone biosynthesis.
- Full Text: false
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