New Hygrocins K–U and Streptophenylpropanamide A and Bioactive Compounds from the Marine-Associated <i>Streptomyces</i> sp. ZZ1956
Marine-derived <i>Streptomyces</i> actinomycetes are one of the most important sources for the discovery of novel bioactive natural products. This study characterized the isolation, structural elucidation and biological activity evaluation of thirty compounds, including twelve previously...
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MDPI AG
2022-10-01
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| Series: | Antibiotics |
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| Online Access: | https://www.mdpi.com/2079-6382/11/11/1455 |
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| author | Wenwen Yi Asif Wares Newaz Kuo Yong Mingzhu Ma Xiao-Yuan Lian Zhizhen Zhang |
| author_facet | Wenwen Yi Asif Wares Newaz Kuo Yong Mingzhu Ma Xiao-Yuan Lian Zhizhen Zhang |
| author_sort | Wenwen Yi |
| collection | DOAJ |
| description | Marine-derived <i>Streptomyces</i> actinomycetes are one of the most important sources for the discovery of novel bioactive natural products. This study characterized the isolation, structural elucidation and biological activity evaluation of thirty compounds, including twelve previously undescribed compounds, namely hygrocins K–U (<b>5</b>–<b>13</b>, <b>17</b> and <b>18</b>) and streptophenylpropanamide A (<b>23</b>), from the marine-associated actinomycete <i>Streptomyces</i> sp. ZZ1956. Structures of the isolated compounds were determined by a combination of extensive NMR spectroscopic analyses, HRESIMS data, the Mosher’s method, ECD calculations, single crystal X-ray diffraction and comparison with reported data. Hygrocins C (<b>1</b>), D (<b>2</b>), F (<b>4</b>), N (<b>8</b>), Q (<b>11</b>) and R (<b>12</b>), 2-acetamide-6-hydroxy-7-methyl-1,4-naphthoquinone (<b>22</b>), echoside C (<b>27</b>), echoside A (<b>28</b>) and 11,11′-<i>O</i>-dimethylelaiophylin (<b>30</b>) had antiproliferative activity (IC<sub>50</sub>: 0.16–19.39 μM) against both human glioma U87MG and U251 cells with hygrocin C as the strongest active compound (IC<sub>50</sub>: 0.16 and 0.35 μM, respectively). The analysis of the structure–activity relationship indicated that a small change in the structures of the naphthalenic ansamycins had significant influence on their antiglioma activities. Hygrocins N (<b>8</b>), O (<b>9</b>), R (<b>12</b>), T (<b>17</b>) and U (<b>18</b>), 2-amino-6-hydroxy-7-methyl-1,4-naphthoquinone (<b>21</b>), 2-acetamide-6-hydroxy-7-methyl-1,4-naphthoquinone (<b>22</b>), 3′-methoxy(1,1′,4′,1″-terphenyl)-2′,6′-diol (<b>26</b>), echoside C (<b>27</b>) and echoside A (<b>28</b>) showed antibacterial activity against methicillin-resistant <i>Staphylococcus aureus</i> and <i>Escherichia coli</i> with MIC values of 3–48 μg/mL. |
| first_indexed | 2024-03-09T19:19:49Z |
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| institution | Directory Open Access Journal |
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| language | English |
| last_indexed | 2024-03-09T19:19:49Z |
| publishDate | 2022-10-01 |
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| spelling | doaj.art-2963d52221e64a4a8e45c432c4f488872023-11-24T03:26:39ZengMDPI AGAntibiotics2079-63822022-10-011111145510.3390/antibiotics11111455New Hygrocins K–U and Streptophenylpropanamide A and Bioactive Compounds from the Marine-Associated <i>Streptomyces</i> sp. ZZ1956Wenwen Yi0Asif Wares Newaz1Kuo Yong2Mingzhu Ma3Xiao-Yuan Lian4Zhizhen Zhang5Ocean College, Zhoushan Campus, Zhejiang University, Zhoushan 316021, ChinaOcean College, Zhoushan Campus, Zhejiang University, Zhoushan 316021, ChinaOcean College, Zhoushan Campus, Zhejiang University, Zhoushan 316021, ChinaOcean College, Zhoushan Campus, Zhejiang University, Zhoushan 316021, ChinaCollege of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, ChinaOcean College, Zhoushan Campus, Zhejiang University, Zhoushan 316021, ChinaMarine-derived <i>Streptomyces</i> actinomycetes are one of the most important sources for the discovery of novel bioactive natural products. This study characterized the isolation, structural elucidation and biological activity evaluation of thirty compounds, including twelve previously undescribed compounds, namely hygrocins K–U (<b>5</b>–<b>13</b>, <b>17</b> and <b>18</b>) and streptophenylpropanamide A (<b>23</b>), from the marine-associated actinomycete <i>Streptomyces</i> sp. ZZ1956. Structures of the isolated compounds were determined by a combination of extensive NMR spectroscopic analyses, HRESIMS data, the Mosher’s method, ECD calculations, single crystal X-ray diffraction and comparison with reported data. Hygrocins C (<b>1</b>), D (<b>2</b>), F (<b>4</b>), N (<b>8</b>), Q (<b>11</b>) and R (<b>12</b>), 2-acetamide-6-hydroxy-7-methyl-1,4-naphthoquinone (<b>22</b>), echoside C (<b>27</b>), echoside A (<b>28</b>) and 11,11′-<i>O</i>-dimethylelaiophylin (<b>30</b>) had antiproliferative activity (IC<sub>50</sub>: 0.16–19.39 μM) against both human glioma U87MG and U251 cells with hygrocin C as the strongest active compound (IC<sub>50</sub>: 0.16 and 0.35 μM, respectively). The analysis of the structure–activity relationship indicated that a small change in the structures of the naphthalenic ansamycins had significant influence on their antiglioma activities. Hygrocins N (<b>8</b>), O (<b>9</b>), R (<b>12</b>), T (<b>17</b>) and U (<b>18</b>), 2-amino-6-hydroxy-7-methyl-1,4-naphthoquinone (<b>21</b>), 2-acetamide-6-hydroxy-7-methyl-1,4-naphthoquinone (<b>22</b>), 3′-methoxy(1,1′,4′,1″-terphenyl)-2′,6′-diol (<b>26</b>), echoside C (<b>27</b>) and echoside A (<b>28</b>) showed antibacterial activity against methicillin-resistant <i>Staphylococcus aureus</i> and <i>Escherichia coli</i> with MIC values of 3–48 μg/mL.https://www.mdpi.com/2079-6382/11/11/1455marine <i>Streptomyces</i> sp. ZZ1956Streptomycetaceaehygrocins K–Ustreptophenylpropanamide Astructure elucidationantiglioma activity |
| spellingShingle | Wenwen Yi Asif Wares Newaz Kuo Yong Mingzhu Ma Xiao-Yuan Lian Zhizhen Zhang New Hygrocins K–U and Streptophenylpropanamide A and Bioactive Compounds from the Marine-Associated <i>Streptomyces</i> sp. ZZ1956 Antibiotics marine <i>Streptomyces</i> sp. ZZ1956 Streptomycetaceae hygrocins K–U streptophenylpropanamide A structure elucidation antiglioma activity |
| title | New Hygrocins K–U and Streptophenylpropanamide A and Bioactive Compounds from the Marine-Associated <i>Streptomyces</i> sp. ZZ1956 |
| title_full | New Hygrocins K–U and Streptophenylpropanamide A and Bioactive Compounds from the Marine-Associated <i>Streptomyces</i> sp. ZZ1956 |
| title_fullStr | New Hygrocins K–U and Streptophenylpropanamide A and Bioactive Compounds from the Marine-Associated <i>Streptomyces</i> sp. ZZ1956 |
| title_full_unstemmed | New Hygrocins K–U and Streptophenylpropanamide A and Bioactive Compounds from the Marine-Associated <i>Streptomyces</i> sp. ZZ1956 |
| title_short | New Hygrocins K–U and Streptophenylpropanamide A and Bioactive Compounds from the Marine-Associated <i>Streptomyces</i> sp. ZZ1956 |
| title_sort | new hygrocins k u and streptophenylpropanamide a and bioactive compounds from the marine associated i streptomyces i sp zz1956 |
| topic | marine <i>Streptomyces</i> sp. ZZ1956 Streptomycetaceae hygrocins K–U streptophenylpropanamide A structure elucidation antiglioma activity |
| url | https://www.mdpi.com/2079-6382/11/11/1455 |
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