Sulfoxanthicillin from the deep-sea derived Penicillium sp. SCSIO sof101: an antimicrobial compound against Gram-positive and -negative pathogens
Natural products along with their analogs have been intensively explored for their antimicrobial potential against ‘ESKAPE’ pathogens. Herein, we report a new natural product with strong antibacterial activity, sulfoxanthocillin ( 1 ), along with its decomposed product peniformamide ( 2 ), and the k...
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Published in | Journal of antibiotics Vol. 76; no. 3; pp. 113 - 120 |
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Main Authors | , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
Tokyo
Springer Japan
01.03.2023
Springer Nature Nature Publishing Group |
Subjects | |
Online Access | Get full text |
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Abstract | Natural products along with their analogs have been intensively explored for their antimicrobial potential against ‘ESKAPE’ pathogens. Herein, we report a new natural product with strong antibacterial activity, sulfoxanthocillin (
1
), along with its decomposed product peniformamide (
2
), and the known compound xanthocillin X (
3
) from the deep-sea derived
Penicillium
sp. SCSIO sof101. The structures of compounds
1
and
2
were determined by extensive spectroscopic analysis. Compound
1
showed significant activity against series pathogens with MIC values ranging 0.06–8.0 μg mL
−1
. As an artificial unnatural product during the isolation process, compound
2
had lower antimicrobial activity than that of compound
1
, which could be attributed to a change in structural modification from an isonitrile group in compound
1
to a formamide group in compound
2
. In terms of cytotoxicity,
1
showed relatively low cytotoxicity against human tumor cell lines compared with xanthocillin X (
3
), suggesting that the sulfate group present in
1
should be a determinant of cytotoxic activities. Overall, sulfoxanthocillin (
1
) merits further attention as a potential lead compound for anti-infective interventions against Gram-negative and Gram-positive bacterial pathogens. |
---|---|
AbstractList | Natural products along with their analogs have been intensively explored for their antimicrobial potential against 'ESKAPE' pathogens. Herein, we report a new natural product with strong antibacterial activity, sulfoxanthocillin (1), along with its decomposed product peniformamide (2), and the known compound xanthocillin X (3) from the deep-sea derived Penicillium sp. SCSIO sof101. The structures of compounds 1 and 2 were determined by extensive spectroscopic analysis. Compound 1 showed significant activity against series pathogens with MIC values ranging 0.06-8.0 μg mL-1. As an artificial unnatural product during the isolation process, compound 2 had lower antimicrobial activity than that of compound 1, which could be attributed to a change in structural modification from an isonitrile group in compound 1 to a formamide group in compound 2. In terms of cytotoxicity, 1 showed relatively low cytotoxicity against human tumor cell lines compared with xanthocillin X (3), suggesting that the sulfate group present in 1 should be a determinant of cytotoxic activities. Overall, sulfoxanthocillin (1) merits further attention as a potential lead compound for anti-infective interventions against Gram-negative and Gram-positive bacterial pathogens.Natural products along with their analogs have been intensively explored for their antimicrobial potential against 'ESKAPE' pathogens. Herein, we report a new natural product with strong antibacterial activity, sulfoxanthocillin (1), along with its decomposed product peniformamide (2), and the known compound xanthocillin X (3) from the deep-sea derived Penicillium sp. SCSIO sof101. The structures of compounds 1 and 2 were determined by extensive spectroscopic analysis. Compound 1 showed significant activity against series pathogens with MIC values ranging 0.06-8.0 μg mL-1. As an artificial unnatural product during the isolation process, compound 2 had lower antimicrobial activity than that of compound 1, which could be attributed to a change in structural modification from an isonitrile group in compound 1 to a formamide group in compound 2. In terms of cytotoxicity, 1 showed relatively low cytotoxicity against human tumor cell lines compared with xanthocillin X (3), suggesting that the sulfate group present in 1 should be a determinant of cytotoxic activities. Overall, sulfoxanthocillin (1) merits further attention as a potential lead compound for anti-infective interventions against Gram-negative and Gram-positive bacterial pathogens. Natural products along with their analogs have been intensively explored for their antimicrobial potential against 'ESKAPE' pathogens. Herein, we report a new natural product with strong antibacterial activity, sulfoxanthocillin (1), along with its decomposed product peniformamide (2), and the known compound xanthocillin X (3) from the deep-sea derived Penicillium sp. SCSIO sof101. The structures of compounds 1 and 2 were determined by extensive spectroscopic analysis. Compound 1 showed significant activity against series pathogens with MIC values ranging 0.06-8.0 mu g mL(-1). As an artificial unnatural product during the isolation process, compound 2 had lower antimicrobial activity than that of compound 1, which could be attributed to a change in structural modification from an isonitrile group in compound 1 to a formamide group in compound 2. In terms of cytotoxicity, 1 showed relatively low cytotoxicity against human tumor cell lines compared with xanthocillin X (3), suggesting that the sulfate group present in 1 should be a determinant of cytotoxic activities. Overall, sulfoxanthocillin (1) merits further attention as a potential lead compound for anti-infective interventions against Gram-negative and Gram-positive bacterial pathogens. Natural products along with their analogs have been intensively explored for their antimicrobial potential against 'ESKAPE' pathogens. Herein, we report a new natural product with strong antibacterial activity, sulfoxanthocillin (1), along with its decomposed product peniformamide (2), and the known compound xanthocillin X (3) from the deep-sea derived Penicillium sp. SCSIO sof101. The structures of compounds 1 and 2 were determined by extensive spectroscopic analysis. Compound 1 showed significant activity against series pathogens with MIC values ranging 0.06-8.0 μg mL . As an artificial unnatural product during the isolation process, compound 2 had lower antimicrobial activity than that of compound 1, which could be attributed to a change in structural modification from an isonitrile group in compound 1 to a formamide group in compound 2. In terms of cytotoxicity, 1 showed relatively low cytotoxicity against human tumor cell lines compared with xanthocillin X (3), suggesting that the sulfate group present in 1 should be a determinant of cytotoxic activities. Overall, sulfoxanthocillin (1) merits further attention as a potential lead compound for anti-infective interventions against Gram-negative and Gram-positive bacterial pathogens. Natural products along with their analogs have been intensively explored for their antimicrobial potential against ‘ESKAPE’ pathogens. Herein, we report a new natural product with strong antibacterial activity, sulfoxanthocillin (1), along with its decomposed product peniformamide (2), and the known compound xanthocillin X (3) from the deep-sea derived Penicillium sp. SCSIO sof101. The structures of compounds 1 and 2 were determined by extensive spectroscopic analysis. Compound 1 showed significant activity against series pathogens with MIC values ranging 0.06–8.0 μg mL−1. As an artificial unnatural product during the isolation process, compound 2 had lower antimicrobial activity than that of compound 1, which could be attributed to a change in structural modification from an isonitrile group in compound 1 to a formamide group in compound 2. In terms of cytotoxicity, 1 showed relatively low cytotoxicity against human tumor cell lines compared with xanthocillin X (3), suggesting that the sulfate group present in 1 should be a determinant of cytotoxic activities. Overall, sulfoxanthocillin (1) merits further attention as a potential lead compound for anti-infective interventions against Gram-negative and Gram-positive bacterial pathogens. Natural products along with their analogs have been intensively explored for their antimicrobial potential against ‘ESKAPE’ pathogens. Herein, we report a new natural product with strong antibacterial activity, sulfoxanthocillin ( 1 ), along with its decomposed product peniformamide ( 2 ), and the known compound xanthocillin X ( 3 ) from the deep-sea derived Penicillium sp. SCSIO sof101. The structures of compounds 1 and 2 were determined by extensive spectroscopic analysis. Compound 1 showed significant activity against series pathogens with MIC values ranging 0.06–8.0 μg mL −1 . As an artificial unnatural product during the isolation process, compound 2 had lower antimicrobial activity than that of compound 1 , which could be attributed to a change in structural modification from an isonitrile group in compound 1 to a formamide group in compound 2 . In terms of cytotoxicity, 1 showed relatively low cytotoxicity against human tumor cell lines compared with xanthocillin X ( 3 ), suggesting that the sulfate group present in 1 should be a determinant of cytotoxic activities. Overall, sulfoxanthocillin ( 1 ) merits further attention as a potential lead compound for anti-infective interventions against Gram-negative and Gram-positive bacterial pathogens. |
Author | Ju, Jianhua Zhou, Zhenbin Wong, Nai-Kei Wang, Songtao Yuan, Jie Yan, Yan Song, Yongxiang Huang, Yun Yang, Jiafan |
Author_xml | – sequence: 1 givenname: Jiafan surname: Yang fullname: Yang, Jiafan organization: CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, College of Oceanology, University of Chinese Academy of Sciences – sequence: 2 givenname: Yongxiang surname: Song fullname: Song, Yongxiang email: songx@scsio.ac.cn organization: CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, College of Oceanology, University of Chinese Academy of Sciences – sequence: 3 givenname: Zhenbin surname: Zhou fullname: Zhou, Zhenbin organization: CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, College of Oceanology, University of Chinese Academy of Sciences – sequence: 4 givenname: Yun surname: Huang fullname: Huang, Yun organization: School of Basic Medical Sciences, Southern Medical University – sequence: 5 givenname: Songtao surname: Wang fullname: Wang, Songtao organization: CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, College of Oceanology, University of Chinese Academy of Sciences – sequence: 6 givenname: Jie surname: Yuan fullname: Yuan, Jie organization: Key Laboratory of Tropical Disease Control, Zhongshan School of Medicine, Sun Yat-sen University – sequence: 7 givenname: Nai-Kei surname: Wong fullname: Wong, Nai-Kei organization: Department of Pharmacology, Shantou University Medical College – sequence: 8 givenname: Yan surname: Yan fullname: Yan, Yan organization: CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, College of Oceanology, University of Chinese Academy of Sciences – sequence: 9 givenname: Jianhua orcidid: 0000-0001-7712-8027 surname: Ju fullname: Ju, Jianhua email: jju@scsio.ac.cn organization: CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, College of Oceanology, University of Chinese Academy of Sciences |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/36642755$$D View this record in MEDLINE/PubMed |
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Cites_doi | 10.1021/acs.jnatprod.7b00269 10.1021/np060509t 10.1021/acscentsci.1c00130 10.1086/595011 10.1038/s41586-019-1791-1 10.7164/antibiotics.21.671 10.1021/np500399v 10.7164/antibiotics.46.687 10.3390/md11124961 10.1128/mBio.00785-18 10.1038/s41429-020-0307-4 10.1586/eri.13.12 10.1055/s-0028-1119307 10.1038/ja.2006.98 10.1021/acs.jnatprod.9b01285 10.1021/acscentsci.0c01621 10.7164/antibiotics.43.456 10.1021/acs.jnatprod.0c00151 10.1021/np200255f 10.1002/cbdv.202000057 10.1586/ERI.13.12 |
ContentType | Journal Article |
Copyright | The Author(s), under exclusive licence to the Japan Antibiotics Research Association 2023. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law. 2023. The Author(s), under exclusive licence to the Japan Antibiotics Research Association. |
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Keywords | XANTHOCILLIN ESKAPE |
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An Update from the Infectious Diseases Society of America publication-title: CLINICAL INFECTIOUS DISEASES doi: 10.1086/595011 – year: 2020 ident: 000914033500001.4 publication-title: Lack of new antibiotics threatens global efforts to contain drug-resistant infections – volume: 7 start-page: 403 year: 2021 ident: WOS:000634764100006 article-title: Ironing out New Antibiotic Mechanisms with Xanthocillin X publication-title: ACS CENTRAL SCIENCE doi: 10.1021/acscentsci.1c00130 – volume: 74 start-page: 1653 year: 2011 ident: WOS:000293036100016 article-title: Induced Production of N-Formyl Alkaloids from Aspergillus fumigatus by Co-culture with Streptomyces peucetius publication-title: JOURNAL OF NATURAL PRODUCTS doi: 10.1021/np200255f |
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Snippet | Natural products along with their analogs have been intensively explored for their antimicrobial potential against ‘ESKAPE’ pathogens. Herein, we report a new... Natural products along with their analogs have been intensively explored for their antimicrobial potential against 'ESKAPE' pathogens. Herein, we report a new... |
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SubjectTerms | 631/326/22/1290 631/92/349 Anti-Bacterial Agents - chemistry Anti-Infective Agents - chemistry Antibacterial activity Antimicrobial activity Antimicrobial agents Bacteriology Biomedical and Life Sciences Bioorganic Chemistry Biotechnology & Applied Microbiology Cell Line, Tumor Cytotoxicity Deep sea Deep sea environments Fungi Humans Immunology Lead compounds Life Sciences Life Sciences & Biomedicine Medicinal Chemistry Microbiology Molecular Structure Natural products Organic Chemistry Pathogens Penicillium Penicillium - chemistry Pharmacology & Pharmacy Science & Technology Toxicity Tumor cell lines |
Title | Sulfoxanthicillin from the deep-sea derived Penicillium sp. SCSIO sof101: an antimicrobial compound against Gram-positive and -negative pathogens |
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