HSQC-TOCSY Fingerprinting-Directed Discovery of Antiplasmodial Polyketides from the Marine Ascidian-Derived Streptomyces sp. (USC-16018)
Chemical investigations on the fermentation extract obtained from an ascidian-derived Streptomyces sp. (USC-16018) yielded a new ansamycin polyketide, herbimycin G (1), as well as a known macrocyclic polyketide, elaiophylin (2), and four known diketopiperazines (3–6). The structures of the...
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| Format: | Article |
| Language: | English |
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MDPI AG
2018-05-01
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| Series: | Marine Drugs |
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| Online Access: | http://www.mdpi.com/1660-3397/16/6/189 |
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| author | Larissa Buedenbender Luke P. Robertson Leonardo Lucantoni Vicky M. Avery D. İpek Kurtböke Anthony R. Carroll |
| author_facet | Larissa Buedenbender Luke P. Robertson Leonardo Lucantoni Vicky M. Avery D. İpek Kurtböke Anthony R. Carroll |
| author_sort | Larissa Buedenbender |
| collection | DOAJ |
| description | Chemical investigations on the fermentation extract obtained from an ascidian-derived Streptomyces sp. (USC-16018) yielded a new ansamycin polyketide, herbimycin G (1), as well as a known macrocyclic polyketide, elaiophylin (2), and four known diketopiperazines (3–6). The structures of the compounds were elucidated based on 1D/2D NMR and MS data. The absolute configuration of 1 was established by comparison of experimental and predicted electronic circular dichroism (ECD) data. Antiplasmodial activities were tested for the natural products against chloroquine sensitive (3D7) and chloroquine resistant (Dd2) Plasmodium falciparum strains; the two polyketides (1–2) demonstrated an inhibition of >75% against both parasite strains and while 2 was highly cytotoxic, herbimycin G (1) showed no cytotoxicity and good predicted water solubility. |
| first_indexed | 2024-04-11T13:37:44Z |
| format | Article |
| id | doaj.art-7b046e3c1d994c1e93e06bf2e8eec8b1 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-04-11T13:37:44Z |
| publishDate | 2018-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-7b046e3c1d994c1e93e06bf2e8eec8b12022-12-22T04:21:26ZengMDPI AGMarine Drugs1660-33972018-05-0116618910.3390/md16060189md16060189HSQC-TOCSY Fingerprinting-Directed Discovery of Antiplasmodial Polyketides from the Marine Ascidian-Derived Streptomyces sp. (USC-16018)Larissa Buedenbender0Luke P. Robertson1Leonardo Lucantoni2Vicky M. Avery3D. İpek Kurtböke4Anthony R. Carroll5Environmental Futures Research Institute, School of Environment and Science, Griffith University, Gold Coast Campus, QLD 4222, AustraliaEnvironmental Futures Research Institute, School of Environment and Science, Griffith University, Gold Coast Campus, QLD 4222, AustraliaGriffith Institute for Drug Discovery, Griffith University, Brisbane, QLD 4111, AustraliaGriffith Institute for Drug Discovery, Griffith University, Brisbane, QLD 4111, AustraliaGeneCology Research Centre, Faculty of Science, Health, Education and Engineering, University of the Sunshine Coast, Maroochydore, QLD 4558, AustraliaEnvironmental Futures Research Institute, School of Environment and Science, Griffith University, Gold Coast Campus, QLD 4222, AustraliaChemical investigations on the fermentation extract obtained from an ascidian-derived Streptomyces sp. (USC-16018) yielded a new ansamycin polyketide, herbimycin G (1), as well as a known macrocyclic polyketide, elaiophylin (2), and four known diketopiperazines (3–6). The structures of the compounds were elucidated based on 1D/2D NMR and MS data. The absolute configuration of 1 was established by comparison of experimental and predicted electronic circular dichroism (ECD) data. Antiplasmodial activities were tested for the natural products against chloroquine sensitive (3D7) and chloroquine resistant (Dd2) Plasmodium falciparum strains; the two polyketides (1–2) demonstrated an inhibition of >75% against both parasite strains and while 2 was highly cytotoxic, herbimycin G (1) showed no cytotoxicity and good predicted water solubility.http://www.mdpi.com/1660-3397/16/6/189actinomycetesStreptomycesascidian-associated actinomycetesSymplegma rubrapolyketideansamycin derivativeherbimycinantiplasmodial activity |
| spellingShingle | Larissa Buedenbender Luke P. Robertson Leonardo Lucantoni Vicky M. Avery D. İpek Kurtböke Anthony R. Carroll HSQC-TOCSY Fingerprinting-Directed Discovery of Antiplasmodial Polyketides from the Marine Ascidian-Derived Streptomyces sp. (USC-16018) Marine Drugs actinomycetes Streptomyces ascidian-associated actinomycetes Symplegma rubra polyketide ansamycin derivative herbimycin antiplasmodial activity |
| title | HSQC-TOCSY Fingerprinting-Directed Discovery of Antiplasmodial Polyketides from the Marine Ascidian-Derived Streptomyces sp. (USC-16018) |
| title_full | HSQC-TOCSY Fingerprinting-Directed Discovery of Antiplasmodial Polyketides from the Marine Ascidian-Derived Streptomyces sp. (USC-16018) |
| title_fullStr | HSQC-TOCSY Fingerprinting-Directed Discovery of Antiplasmodial Polyketides from the Marine Ascidian-Derived Streptomyces sp. (USC-16018) |
| title_full_unstemmed | HSQC-TOCSY Fingerprinting-Directed Discovery of Antiplasmodial Polyketides from the Marine Ascidian-Derived Streptomyces sp. (USC-16018) |
| title_short | HSQC-TOCSY Fingerprinting-Directed Discovery of Antiplasmodial Polyketides from the Marine Ascidian-Derived Streptomyces sp. (USC-16018) |
| title_sort | hsqc tocsy fingerprinting directed discovery of antiplasmodial polyketides from the marine ascidian derived streptomyces sp usc 16018 |
| topic | actinomycetes Streptomyces ascidian-associated actinomycetes Symplegma rubra polyketide ansamycin derivative herbimycin antiplasmodial activity |
| url | http://www.mdpi.com/1660-3397/16/6/189 |
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