Signalling and Bioactive Metabolites from <i>Streptomyces</i> sp. RK44
<i>Streptomyces</i> remains one of the prolific sources of structural diversity, and a reservoir to mine for novel natural products. Continued screening for new Streptomyces strains in our laboratory led to the isolation of <i>Streptomyces</i> sp. RK44 from the underexplored...
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| Format: | Article |
| Language: | English |
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MDPI AG
2020-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/3/460 |
| _version_ | 1818683496669904896 |
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| author | Qing Fang Fleurdeliz Maglangit Linrui Wu Rainer Ebel Kwaku Kyeremeh Jeanette H. Andersen Frederick Annang Guiomar Pérez-Moreno Fernando Reyes Hai Deng |
| author_facet | Qing Fang Fleurdeliz Maglangit Linrui Wu Rainer Ebel Kwaku Kyeremeh Jeanette H. Andersen Frederick Annang Guiomar Pérez-Moreno Fernando Reyes Hai Deng |
| author_sort | Qing Fang |
| collection | DOAJ |
| description | <i>Streptomyces</i> remains one of the prolific sources of structural diversity, and a reservoir to mine for novel natural products. Continued screening for new Streptomyces strains in our laboratory led to the isolation of <i>Streptomyces</i> sp. RK44 from the underexplored areas of Kintampo waterfalls, Ghana, Africa. Preliminary screening of the metabolites from this strain resulted in the characterization of a new 2-alkyl-4-hydroxymethylfuran carboxamide (AHFA) <b>1</b> together with five known compounds, cyclo-(L-Pro-Gly) <b>2</b>, cyclo-(L-Pro-L-Phe) <b>3</b>, cyclo-(L-Pro-L-Val) <b>4</b>, cyclo-(L-Leu-Hyp) <b>5</b>, and deferoxamine E <b>6</b>. AHFA <b>1</b>, a methylenomycin (MMF) homolog, exhibited anti-proliferative activity (EC<sub>50</sub> = 89.6 µM) against melanoma A2058 cell lines. This activity, albeit weak is the first report amongst MMFs. Furthermore, the putative biosynthetic gene cluster (<i>ahfa</i>) was identified for the biosynthesis of AHFA <b>1</b>. DFO-E <b>6</b> displayed potent anti-plasmodial activity (IC<sub>50</sub> = 1.08 µM) against <i>P. falciparum</i> 3D7. High-resolution electrospray ionization mass spectrometry (HR ESIMS) and molecular network assisted the targeted-isolation process, and tentatively identified six AHFA analogues, <b>7</b>−<b>12</b> and six siderophores <b>13</b>−<b>18</b>. |
| first_indexed | 2024-12-17T10:35:40Z |
| format | Article |
| id | doaj.art-52b1703ac4ee4717adb6c7e540451d28 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-17T10:35:40Z |
| publishDate | 2020-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-52b1703ac4ee4717adb6c7e540451d282022-12-21T21:52:23ZengMDPI AGMolecules1420-30492020-01-0125346010.3390/molecules25030460molecules25030460Signalling and Bioactive Metabolites from <i>Streptomyces</i> sp. RK44Qing Fang0Fleurdeliz Maglangit1Linrui Wu2Rainer Ebel3Kwaku Kyeremeh4Jeanette H. Andersen5Frederick Annang6Guiomar Pérez-Moreno7Fernando Reyes8Hai Deng9Marine Biodiscovery Centre, Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, UKMarine Biodiscovery Centre, Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, UKMarine Biodiscovery Centre, Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, UKMarine Biodiscovery Centre, Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, UKMarine and Plant Research Laboratory of Ghana, Department of Chemistry, University of Ghana, P.O. Box LG56 Legon, Accra, GhanaMarbio, UiT—The Arctic University of Norway, N-9037 Tromsø, NorwayFundación MEDINA, Avda. del Conocimiento 34, 18016 Armilla, Granada, SpainInstituto de Parasitología y Biomedicina “López-Neyra”, Consejo Superior de Investigaciones Científicas (CSIC) Avda. del Conocimiento 17, 18016 Armilla, Granada, SpainFundación MEDINA, Avda. del Conocimiento 34, 18016 Armilla, Granada, SpainMarine Biodiscovery Centre, Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, UK<i>Streptomyces</i> remains one of the prolific sources of structural diversity, and a reservoir to mine for novel natural products. Continued screening for new Streptomyces strains in our laboratory led to the isolation of <i>Streptomyces</i> sp. RK44 from the underexplored areas of Kintampo waterfalls, Ghana, Africa. Preliminary screening of the metabolites from this strain resulted in the characterization of a new 2-alkyl-4-hydroxymethylfuran carboxamide (AHFA) <b>1</b> together with five known compounds, cyclo-(L-Pro-Gly) <b>2</b>, cyclo-(L-Pro-L-Phe) <b>3</b>, cyclo-(L-Pro-L-Val) <b>4</b>, cyclo-(L-Leu-Hyp) <b>5</b>, and deferoxamine E <b>6</b>. AHFA <b>1</b>, a methylenomycin (MMF) homolog, exhibited anti-proliferative activity (EC<sub>50</sub> = 89.6 µM) against melanoma A2058 cell lines. This activity, albeit weak is the first report amongst MMFs. Furthermore, the putative biosynthetic gene cluster (<i>ahfa</i>) was identified for the biosynthesis of AHFA <b>1</b>. DFO-E <b>6</b> displayed potent anti-plasmodial activity (IC<sub>50</sub> = 1.08 µM) against <i>P. falciparum</i> 3D7. High-resolution electrospray ionization mass spectrometry (HR ESIMS) and molecular network assisted the targeted-isolation process, and tentatively identified six AHFA analogues, <b>7</b>−<b>12</b> and six siderophores <b>13</b>−<b>18</b>.https://www.mdpi.com/1420-3049/25/3/460ahfamethylenomycinmmfssignalling molecules<i>streptomyces</i> sp. rk44anticancerantimalaria |
| spellingShingle | Qing Fang Fleurdeliz Maglangit Linrui Wu Rainer Ebel Kwaku Kyeremeh Jeanette H. Andersen Frederick Annang Guiomar Pérez-Moreno Fernando Reyes Hai Deng Signalling and Bioactive Metabolites from <i>Streptomyces</i> sp. RK44 Molecules ahfa methylenomycin mmfs signalling molecules <i>streptomyces</i> sp. rk44 anticancer antimalaria |
| title | Signalling and Bioactive Metabolites from <i>Streptomyces</i> sp. RK44 |
| title_full | Signalling and Bioactive Metabolites from <i>Streptomyces</i> sp. RK44 |
| title_fullStr | Signalling and Bioactive Metabolites from <i>Streptomyces</i> sp. RK44 |
| title_full_unstemmed | Signalling and Bioactive Metabolites from <i>Streptomyces</i> sp. RK44 |
| title_short | Signalling and Bioactive Metabolites from <i>Streptomyces</i> sp. RK44 |
| title_sort | signalling and bioactive metabolites from i streptomyces i sp rk44 |
| topic | ahfa methylenomycin mmfs signalling molecules <i>streptomyces</i> sp. rk44 anticancer antimalaria |
| url | https://www.mdpi.com/1420-3049/25/3/460 |
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