Discovery of ianthelliformisamines D–G from the sponge Suberea ianthelliformis and the total synthesis of ianthelliformisamine D
The marine sponge Suberea ianthelliformis was investigated for new chemistry after the recent discovery that polyamines ianthelliformisamines A–C (1–3) – originally sourced from this Australian sponge – act as Pseudomonas aeruginosa biofilm inhibitors and antibiotic enhancers. Large-scale extraction...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2024-12-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.20.266 |
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| author | Sasha Hayes Yaoying Lu Bernd H. A. Rehm Rohan A. Davis |
| author_facet | Sasha Hayes Yaoying Lu Bernd H. A. Rehm Rohan A. Davis |
| author_sort | Sasha Hayes |
| collection | DOAJ |
| description | The marine sponge Suberea ianthelliformis was investigated for new chemistry after the recent discovery that polyamines ianthelliformisamines A–C (1–3) – originally sourced from this Australian sponge – act as Pseudomonas aeruginosa biofilm inhibitors and antibiotic enhancers. Large-scale extraction and isolation studies resulted in the discovery of four new and minor natural products, ianthelliformisamines D–G (4–7) and the known steroid, aplysterol (8). Compounds 4–7 were fully characterised following 1D/2D NMR, MS and UV data analyses. All compounds were assessed for their inhibition on planktonic growth of P. aeruginosa PAO1 in addition to their ability to inhibit the formation of biofilms. None of the tested natural products inhibited planktonic growth or biofilm formation of PAO1 when screened at 50 µM. Ianthelliformisamine D (4) contains a rare N-(3-aminopropyl)-2-pyrrolidone moiety only found in <30 natural products. Owing to the novelty of compound 4, we undertook the first total synthesis of this natural product, which was achieved in three steps. |
| format | Article |
| id | doaj-art-baa80f1f10644602ac0fbb65636521e6 |
| institution | Kabale University |
| issn | 1860-5397 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj-art-baa80f1f10644602ac0fbb65636521e62025-01-06T12:27:36ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972024-12-012013205321410.3762/bjoc.20.2661860-5397-20-266Discovery of ianthelliformisamines D–G from the sponge Suberea ianthelliformis and the total synthesis of ianthelliformisamine DSasha Hayes0Yaoying Lu1Bernd H. A. Rehm2Rohan A. Davis3Institute for Biomedicine and Glycomics, Griffith University, Don Young Road, Brisbane, 4111, Australia Institute for Biomedicine and Glycomics, Griffith University, Don Young Road, Brisbane, 4111, Australia Institute for Biomedicine and Glycomics, Griffith University, Don Young Road, Brisbane, 4111, Australia Institute for Biomedicine and Glycomics, Griffith University, Don Young Road, Brisbane, 4111, Australia The marine sponge Suberea ianthelliformis was investigated for new chemistry after the recent discovery that polyamines ianthelliformisamines A–C (1–3) – originally sourced from this Australian sponge – act as Pseudomonas aeruginosa biofilm inhibitors and antibiotic enhancers. Large-scale extraction and isolation studies resulted in the discovery of four new and minor natural products, ianthelliformisamines D–G (4–7) and the known steroid, aplysterol (8). Compounds 4–7 were fully characterised following 1D/2D NMR, MS and UV data analyses. All compounds were assessed for their inhibition on planktonic growth of P. aeruginosa PAO1 in addition to their ability to inhibit the formation of biofilms. None of the tested natural products inhibited planktonic growth or biofilm formation of PAO1 when screened at 50 µM. Ianthelliformisamine D (4) contains a rare N-(3-aminopropyl)-2-pyrrolidone moiety only found in <30 natural products. Owing to the novelty of compound 4, we undertook the first total synthesis of this natural product, which was achieved in three steps.https://doi.org/10.3762/bjoc.20.266ianthelliformisaminemarine spongenatural productspseudomonassubereatotal synthesis |
| spellingShingle | Sasha Hayes Yaoying Lu Bernd H. A. Rehm Rohan A. Davis Discovery of ianthelliformisamines D–G from the sponge Suberea ianthelliformis and the total synthesis of ianthelliformisamine D Beilstein Journal of Organic Chemistry ianthelliformisamine marine sponge natural products pseudomonas suberea total synthesis |
| title | Discovery of ianthelliformisamines D–G from the sponge Suberea ianthelliformis and the total synthesis of ianthelliformisamine D |
| title_full | Discovery of ianthelliformisamines D–G from the sponge Suberea ianthelliformis and the total synthesis of ianthelliformisamine D |
| title_fullStr | Discovery of ianthelliformisamines D–G from the sponge Suberea ianthelliformis and the total synthesis of ianthelliformisamine D |
| title_full_unstemmed | Discovery of ianthelliformisamines D–G from the sponge Suberea ianthelliformis and the total synthesis of ianthelliformisamine D |
| title_short | Discovery of ianthelliformisamines D–G from the sponge Suberea ianthelliformis and the total synthesis of ianthelliformisamine D |
| title_sort | discovery of ianthelliformisamines d g from the sponge suberea ianthelliformis and the total synthesis of ianthelliformisamine d |
| topic | ianthelliformisamine marine sponge natural products pseudomonas suberea total synthesis |
| url | https://doi.org/10.3762/bjoc.20.266 |
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