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Antibacterial activity against drug-resistant microbial pathogens of cytochalasan alkaloids from the arthropod-associated fungus Chaetomium globosum TW1-1.
Bioorg Chem. 2019 03; 83:98-104.BC

Abstract

By feeding 1-methyl-l-tryptophan (1-MT) into cultures of the arthropod-associated fungus Chaetomium globosum TW1-1, three novel cytochalasan alkaloids, termed as armochaetoglosins A-C (1-3), together with five known analogues, namely prochaetoglobosin I (4), chaetoglobosin T (5), chaetoglobosin C (6), armochaetoglobin Y (7), and chaetoglobosin Vb (8), were isolated and characterized. Their structures including absolute configurations were elucidated by means of NMR spectroscopy, single-crystal X-ray crystallography, and comparison of the experimental electronic circular dichroism (ECD) spectra. Structurally, compounds 1-3 represented the first examples of 1'-N-methyl-chaetoglobosins, which were possibly biosynthesized from the additive 1-MT rather than tryptophan. Additionally, compound 3 showed the highest antibacterial activity against K. pneumoniae and ESBL-E. coli with MIC values of 4.0 μg/mL and 16.0 μg/mL, respectively, wherein the inhibitory effect of 3 against K. pneumoniae was stronger than that of the clinically used antibiotic meropenem, with an MIC value of 8 μg/mL. Our findings may provide new chemical templates for the development of new antibacterial agents against drug-resistant microbial pathogens.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Gao W
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
He Y
Tongji Hospital, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
Li F
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
Chai C
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
Zhang J
Tongji Hospital, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
Guo J
Tongji Hospital, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
Chen C
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
Wang J
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
Zhu H
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
Hu Z
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China. Electronic address: hzx616@126.com.
Zhang Y
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China. Electronic address: zhangyh@mails.tjmu.edu.cn.

MeSH

AlkaloidsAnti-Bacterial AgentsChaetomiumCrystallography, X-RayCytochalasinsDose-Response Relationship, DrugDrug Resistance, BacterialEscherichia coliKlebsiella pneumoniaeMicrobial Sensitivity TestsModels, MolecularMolecular ConformationStructure-Activity Relationship

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

30343206

Citation

Gao, Weixi, et al. "Antibacterial Activity Against Drug-resistant Microbial Pathogens of Cytochalasan Alkaloids From the Arthropod-associated Fungus Chaetomium Globosum TW1-1." Bioorganic Chemistry, vol. 83, 2019, pp. 98-104.
Gao W, He Y, Li F, et al. Antibacterial activity against drug-resistant microbial pathogens of cytochalasan alkaloids from the arthropod-associated fungus Chaetomium globosum TW1-1. Bioorg Chem. 2019;83:98-104.
Gao, W., He, Y., Li, F., Chai, C., Zhang, J., Guo, J., Chen, C., Wang, J., Zhu, H., Hu, Z., & Zhang, Y. (2019). Antibacterial activity against drug-resistant microbial pathogens of cytochalasan alkaloids from the arthropod-associated fungus Chaetomium globosum TW1-1. Bioorganic Chemistry, 83, 98-104. https://doi.org/10.1016/j.bioorg.2018.10.020
Gao W, et al. Antibacterial Activity Against Drug-resistant Microbial Pathogens of Cytochalasan Alkaloids From the Arthropod-associated Fungus Chaetomium Globosum TW1-1. Bioorg Chem. 2019;83:98-104. PubMed PMID: 30343206.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Antibacterial activity against drug-resistant microbial pathogens of cytochalasan alkaloids from the arthropod-associated fungus Chaetomium globosum TW1-1. AU - Gao,Weixi, AU - He,Yan, AU - Li,Fengli, AU - Chai,Chenwei, AU - Zhang,Jinwen, AU - Guo,Jieru, AU - Chen,Chunmei, AU - Wang,Jianping, AU - Zhu,Hucheng, AU - Hu,Zhengxi, AU - Zhang,Yonghui, Y1 - 2018/10/10/ PY - 2018/09/06/received PY - 2018/10/05/revised PY - 2018/10/09/accepted PY - 2018/10/22/pubmed PY - 2019/12/4/medline PY - 2018/10/22/entrez KW - Antibacterial activity KW - Chaetomium globosum TW1-1 KW - Cytochalasan alkaloids KW - Feeding experiment SP - 98 EP - 104 JF - Bioorganic chemistry JO - Bioorg Chem VL - 83 N2 - By feeding 1-methyl-l-tryptophan (1-MT) into cultures of the arthropod-associated fungus Chaetomium globosum TW1-1, three novel cytochalasan alkaloids, termed as armochaetoglosins A-C (1-3), together with five known analogues, namely prochaetoglobosin I (4), chaetoglobosin T (5), chaetoglobosin C (6), armochaetoglobin Y (7), and chaetoglobosin Vb (8), were isolated and characterized. Their structures including absolute configurations were elucidated by means of NMR spectroscopy, single-crystal X-ray crystallography, and comparison of the experimental electronic circular dichroism (ECD) spectra. Structurally, compounds 1-3 represented the first examples of 1'-N-methyl-chaetoglobosins, which were possibly biosynthesized from the additive 1-MT rather than tryptophan. Additionally, compound 3 showed the highest antibacterial activity against K. pneumoniae and ESBL-E. coli with MIC values of 4.0 μg/mL and 16.0 μg/mL, respectively, wherein the inhibitory effect of 3 against K. pneumoniae was stronger than that of the clinically used antibiotic meropenem, with an MIC value of 8 μg/mL. Our findings may provide new chemical templates for the development of new antibacterial agents against drug-resistant microbial pathogens. SN - 1090-2120 UR - https://www.unboundmedicine.com/medline/citation/30343206/Antibacterial_activity_against_drug_resistant_microbial_pathogens_of_cytochalasan_alkaloids_from_the_arthropod_associated_fungus_Chaetomium_globosum_TW1_1_ DB - PRIME DP - Unbound Medicine ER -