Pyrrole-Containing Alkaloids from a Marine-Derived Actinobacterium <i>Streptomyces zhaozhouensis</i> and Their Antimicrobial and Cytotoxic Activities
Two new alkaloids, streptopyrroles B and C (<b>1</b> and <b>2</b>), were discovered through a chemical investigation of the ethyl acetate (EtOAc) extract from a marine-derived actinomycete, <i>Streptomyces zhaozhouensis</i>, along with four known analogs (<b>...
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| Format: | Article |
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MDPI AG
2023-03-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/21/3/167 |
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| author | Chang-Su Heo Jong Soon Kang Joo-Hee Kwon Cao Van Anh Hee Jae Shin |
| author_facet | Chang-Su Heo Jong Soon Kang Joo-Hee Kwon Cao Van Anh Hee Jae Shin |
| author_sort | Chang-Su Heo |
| collection | DOAJ |
| description | Two new alkaloids, streptopyrroles B and C (<b>1</b> and <b>2</b>), were discovered through a chemical investigation of the ethyl acetate (EtOAc) extract from a marine-derived actinomycete, <i>Streptomyces zhaozhouensis</i>, along with four known analogs (<b>3</b>–<b>6</b>). The structures of the new compounds were elucidated by spectroscopic analysis (HR-ESIMS, 1D, and 2D NMR) and a comparison of their experimental data with literature values. The new compounds were evaluated for their antimicrobial activity by standard broth dilution assay, and the tested compounds showed significant activity against Gram-positive bacteria with minimum inhibitory concentration (MIC) values ranging from 0.7 to 2.9 µM, and kanamycin was used as a positive control with MIC values ranging from <0.5 to 4.1 µM. Additionally, <b>1</b>, <b>3</b>, and <b>5</b> were evaluated for their cytotoxicity against six tumor cell lines by sulforhodamine B (SRB) assay, and these compounds displayed cytotoxic activities against all the tested cell lines, with concentration causing 50% cell growth inhibition (GI<sub>50</sub>) values ranging from 4.9 to 10.8 µM, while a positive control, adriamycin, showed GI<sub>50</sub> values of 0.13–0.17 µM. |
| first_indexed | 2024-03-11T06:15:56Z |
| format | Article |
| id | doaj.art-18e340e43b494222ba93947f7fa0029e |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-11T06:15:56Z |
| publishDate | 2023-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-18e340e43b494222ba93947f7fa0029e2023-11-17T12:17:28ZengMDPI AGMarine Drugs1660-33972023-03-0121316710.3390/md21030167Pyrrole-Containing Alkaloids from a Marine-Derived Actinobacterium <i>Streptomyces zhaozhouensis</i> and Their Antimicrobial and Cytotoxic ActivitiesChang-Su Heo0Jong Soon Kang1Joo-Hee Kwon2Cao Van Anh3Hee Jae Shin4Marine Natural Products Chemistry Laboratory, Korea Institute of Ocean Science and Technology, 385 Haeyang-ro, Yeongdo-gu, Busan 49111, Republic of KoreaLaboratory Animal Resource Center, Korea Research Institute of Bioscience and Biotechnology, 30 Yeongudanjiro, Cheongju 28116, Republic of KoreaLaboratory Animal Resource Center, Korea Research Institute of Bioscience and Biotechnology, 30 Yeongudanjiro, Cheongju 28116, Republic of KoreaMarine Natural Products Chemistry Laboratory, Korea Institute of Ocean Science and Technology, 385 Haeyang-ro, Yeongdo-gu, Busan 49111, Republic of KoreaMarine Natural Products Chemistry Laboratory, Korea Institute of Ocean Science and Technology, 385 Haeyang-ro, Yeongdo-gu, Busan 49111, Republic of KoreaTwo new alkaloids, streptopyrroles B and C (<b>1</b> and <b>2</b>), were discovered through a chemical investigation of the ethyl acetate (EtOAc) extract from a marine-derived actinomycete, <i>Streptomyces zhaozhouensis</i>, along with four known analogs (<b>3</b>–<b>6</b>). The structures of the new compounds were elucidated by spectroscopic analysis (HR-ESIMS, 1D, and 2D NMR) and a comparison of their experimental data with literature values. The new compounds were evaluated for their antimicrobial activity by standard broth dilution assay, and the tested compounds showed significant activity against Gram-positive bacteria with minimum inhibitory concentration (MIC) values ranging from 0.7 to 2.9 µM, and kanamycin was used as a positive control with MIC values ranging from <0.5 to 4.1 µM. Additionally, <b>1</b>, <b>3</b>, and <b>5</b> were evaluated for their cytotoxicity against six tumor cell lines by sulforhodamine B (SRB) assay, and these compounds displayed cytotoxic activities against all the tested cell lines, with concentration causing 50% cell growth inhibition (GI<sub>50</sub>) values ranging from 4.9 to 10.8 µM, while a positive control, adriamycin, showed GI<sub>50</sub> values of 0.13–0.17 µM.https://www.mdpi.com/1660-3397/21/3/167marine-derived actinomycetes<i>Streptomyces zhaozhouensis</i>streptopyrroleantimicrobialcytotoxicityalkaloid |
| spellingShingle | Chang-Su Heo Jong Soon Kang Joo-Hee Kwon Cao Van Anh Hee Jae Shin Pyrrole-Containing Alkaloids from a Marine-Derived Actinobacterium <i>Streptomyces zhaozhouensis</i> and Their Antimicrobial and Cytotoxic Activities Marine Drugs marine-derived actinomycetes <i>Streptomyces zhaozhouensis</i> streptopyrrole antimicrobial cytotoxicity alkaloid |
| title | Pyrrole-Containing Alkaloids from a Marine-Derived Actinobacterium <i>Streptomyces zhaozhouensis</i> and Their Antimicrobial and Cytotoxic Activities |
| title_full | Pyrrole-Containing Alkaloids from a Marine-Derived Actinobacterium <i>Streptomyces zhaozhouensis</i> and Their Antimicrobial and Cytotoxic Activities |
| title_fullStr | Pyrrole-Containing Alkaloids from a Marine-Derived Actinobacterium <i>Streptomyces zhaozhouensis</i> and Their Antimicrobial and Cytotoxic Activities |
| title_full_unstemmed | Pyrrole-Containing Alkaloids from a Marine-Derived Actinobacterium <i>Streptomyces zhaozhouensis</i> and Their Antimicrobial and Cytotoxic Activities |
| title_short | Pyrrole-Containing Alkaloids from a Marine-Derived Actinobacterium <i>Streptomyces zhaozhouensis</i> and Their Antimicrobial and Cytotoxic Activities |
| title_sort | pyrrole containing alkaloids from a marine derived actinobacterium i streptomyces zhaozhouensis i and their antimicrobial and cytotoxic activities |
| topic | marine-derived actinomycetes <i>Streptomyces zhaozhouensis</i> streptopyrrole antimicrobial cytotoxicity alkaloid |
| url | https://www.mdpi.com/1660-3397/21/3/167 |
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