<italic style="font-style: italic">β</italic>-cyclopiazonic acid binds iron demonstrating siderophore-like activity and promotes growth in <italic style="font-style: italic">Pseudomonas aeruginosa</italic>

Yuqi GUO; Youmin YING; Qihao WU; Bin WEI; Jianwei CHEN; Hong WANG

Your Location：

Home >

Browse articles >

β-cyclopiazonic acid binds iron demonstrating siderophore-like activity and promotes growth in Pseudomonas aeruginosa

Biology | Updated：2024-10-12

- β-cyclopiazonic acid binds iron demonstrating siderophore-like activity and promotes growth in Pseudomonas aeruginosa
- Journal of Oceanology and Limnology Vol. 41, Issue 3, Pages: 1159-1167(2023)
- Affiliations：
  
  College of Pharmaceutical Science & Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Key Laboratory of Marine Fishery Resources Exploitment & Utilization of Zhejiang Province, Zhejiang University of Technology, Hangzhou 310014, China
- Author bio：
  
  cjw983617@zjut.edu.cn
  hongw@zjut.edu.cn
- Funds：
- DOI：
  CLC：
- Received：08 January 2022，
  
  Published：01 May 2023
- Accepted：
Scan QR Code
GUO Yuqi,YING Youmin,WU Qihao,et al.,β-cyclopiazonic acid binds iron demonstrating siderophore-like activity and promotes growth in ,Pseudomonas aeruginosa[J].Journal of Oceanology and Limnology,2023,41(03):1159-1167.
DOI：

GUO Yuqi,YING Youmin,WU Qihao,et al.,β-cyclopiazonic acid binds iron demonstrating siderophore-like activity and promotes growth in ,Pseudomonas aeruginosa[J].Journal of Oceanology and Limnology,2023,41(03):1159-1167. DOI：

摘要

Abstract

This chemical study reports a novel siderophore-like compound

-cyclopiazonic acid (

-CPA) extracted from marine fungus

Aspergillus flavus

. The chemical structure of

-CPA was elucidated by a combination of extensive spectroscopic analyses and TDDFT-ECD calculations. The iron-binding ability and CAS assays demonstrate that

-CPA is a novel siderophore that features a different chemical structure from those of traditional siderophores. The

-CPA has no obvious influence on the growth of bacterium

Pseudomonas aeruginosa

PAO1. However

its iron chelator could promote the growth of

aeruginosa

PAO1

suggesting that

aeruginosa

employed siderophores to sequester iron

which is vital for their survival. The study provides the physiochemical evaluation of

-CPA

an unusual skeleton-structure siderophore

which for the first time

was proven to have the ability to bind iron and affect

aeruginosa

growth. This new discovery of siderophore provides an opportunity for developing novel anti-

aeruginosa

drugs.

关键词

Keywords

references

Amin S A , Green D H , Küpper F C et al . 2009 . Vibrioferrin, an unusual marine siderophore: iron binding, photochemistry, and biological implications . Inorganic Chemistry , 48 ( 23 ): 11451 - 11458 , https://doi.org/10.1021/ic9016883 https://doi.org/10.1021/ic9016883 .

Barry S M , Challis G L . 2009 . Recent advances in siderophore biosynthesis . Current Opinion in Chemical Biology , 13 ( 2 ): 205 - 215 , https://doi.org/10.1016/j.cbpa.2009.03.008 https://doi.org/10.1016/j.cbpa.2009.03.008 .

Boyce J H , Dang B B , Ary B et al . 2020 . Platform to discover protease-activated antibiotics and application to siderophore-antibiotic conjugates . Journal of the American Chemical Society , 142 ( 51 ): 21310 - 21321 , https://doi.org/10.26434/chemrxiv.12809603 https://doi.org/10.26434/chemrxiv.12809603 .

Braun V , Pramanik A , Gwinner T et al . 2009 . Sideromycins: tools and antibiotics . BioMetals , 22 ( 1 ): 3 - 13 , https://doi.org/10.1007/s10534-008-9199-7 https://doi.org/10.1007/s10534-008-9199-7 .

Breidenstein E B M , de la Fuente-Núñez C , Hancock R E W . 2011 . Pseudomonas aeruginosa : all roads lead to resistance . Trends in Microbiology , 19 ( 8 ): 419 - 426 , https://doi.org/10.1016/j.tim.2011.04.005 https://doi.org/10.1016/j.tim.2011.04.005 .

Butler A . 2005 . Marine siderophores and microbial iron mobilization . BioMetals , 18 ( 4 ): 369 - 374 , https://doi.org/10.1007/s10534-005-3711-0 https://doi.org/10.1007/s10534-005-3711-0 .

Chang P K , Ehrlich K C , Fujii I . 2009 . Cyclopiazonic acid biosynthesis of Aspergillus flavus and Aspergillus oryzae . Toxins , 1 ( 2 ): 74 - 99 , https://doi.org/10.3390/toxins1020074 https://doi.org/10.3390/toxins1020074 .

Chen J W , Guo Y Q , Lu Y J et al . 2019 . Chemistry and biology of siderophores from marine microbes . Marine Drugs , 17 ( 10 ): 562 , https://doi.org/10.3390/md17100562 https://doi.org/10.3390/md17100562 .

Chen J W , Lu Y J , Ye F et al . 2022 . A small-molecule inhibitor of the anthranilyl-coA synthetase PqsA for the treatment of multidrug-resistant Pseudomonas aeruginosa . Microbiology Spectrum , 10 ( 4 ): 1 , https://doi.org/10.1128/spectrum.02764-21 https://doi.org/10.1128/spectrum.02764-21 .

Chen J W , Lu Y J , Ye X Y et al . 2020 . Current advances in Vibrio harveyi quorum sensing as drug discovery targets . European Journal of Medicinal Chemistry , 207 : 112741 , https://doi.org/10.1016/j.ejmech.2020.112741 https://doi.org/10.1016/j.ejmech.2020.112741 .

Cornelis P . 2010 . Iron uptake and metabolism in pseudomonads . Applied Microbiology and Biotechnology , 86 ( 6 ): 1637 - 1645 , https://doi.org/10.1007/s00253-010-2550-2 https://doi.org/10.1007/s00253-010-2550-2 .

Cox C D , Rinehart K L , Moore M L et al . 1981 . Pyochelin: novel structure of an iron-chelating growth promoter for Pseudomonas aeruginosa . Proceedings of the National Academy of Sciences of the United States of America , 78 ( 7 ): 4256 - 4260 , https://doi.org/10.1073/pnas.78.7.4256 https://doi.org/10.1073/pnas.78.7.4256 .

Gellatly S L , Hancock R E W . 2013 . Pseudomonas aeruginosa : new insights into pathogenesis and host defenses . Pathogens and Disease , 67 ( 3 ): 159 - 173 , https://doi.org/10.1111/2049-632X.12033 https://doi.org/10.1111/2049-632X.12033 .

Górska A , Sloderbach A , Marszałł M P . 2014 . Siderophore-drug complexes: potential medicinal applications of the 'Trojan horse' strategy . Trends in Pharmacological Sciences , 35 ( 9 ): 442 - 449 , https://doi.org/10.1016/j.tips.2014.06.007 https://doi.org/10.1016/j.tips.2014.06.007 .

Guan L L , Kamino K . 2001 . Bacterial response to siderophore and quorum-sensing chemical signals in the seawater microbial community . BMC Microbiology , 1 : 27 , https://doi.org/10.1186/1471-2180-1-27 https://doi.org/10.1186/1471-2180-1-27 .

Hermenau R , Ishida K , Gama S et al . 2018 . Gramibactin is a bacterial siderophore with a diazeniumdiolate ligand system . Nature Chemical Biology , 14 ( 9 ): 841 - 843 , https://doi.org/10.1038/s41589-018-0101-9 https://doi.org/10.1038/s41589-018-0101-9 .

Hider R C , Kong X L . 2010 . Chemistry and biology of siderophores . Natural product Reports , 27 ( 5 ): 637 - 657 . https://do 10.1039/b906679a http://dx.doi.org/10.1039/b906679a

Holinsworth B , Martin J D . 2009 . Siderophore production by marine-derived fungi . BioMetals , 22 ( 4 ): 625 - 632 , https://doi.org/10.1007/s10534-009-9239-y https://doi.org/10.1007/s10534-009-9239-y .

Holzapfel C W , Kruger F W H . 1992 . The synthesis of optic ally pure β -cyclopiazonic acid, an indolic fungal metabolite . Australian Journal of Chemistry , 45 ( 1 ): 99 - 107 , https://doi.org/10.1071/CH9920099 https://doi.org/10.1071/CH9920099 .

Kaplan A R , Musaev D G , Wuest W M . 2021 . Pyochelin biosynthetic metabolites bind iron and promote growth in Pseudomonads demonstrating siderophore-like activity . ACS Infectious Diseases , 7 ( 3 ): 544 - 551 , https://doi.org/10.1021/acsinfecdis.0c00897 https://doi.org/10.1021/acsinfecdis.0c00897 .

Kaufmann G F , Sartorio R , Lee S H et al . 2005 . Revisiting quorum sensing: discovery of additional chemical and biological functions for 3-oxo- N -acylhomoserine lactones . Proceedings of the National Academy of Sciences of the United States of America , 102 ( 2 ): 309 - 314 , https://doi.org/10.1073/pnas.0408639102 https://doi.org/10.1073/pnas.0408639102 .

Khan A , Singh P , Srivastava A . 2018 . Synthesis, nature and utility of universal iron chelator-siderophore: a review . Microbiological Research , 212 - 213 : 103 - 111 , https://doi.org/10.1016/j.micres.2017.10.012 https://doi.org/10.1016/j.micres.2017.10.012 .

Kohira N , West J , Ito A et al . 2016 . In vitro antimicrobial activity of a siderophore cephalosporin, S-649266, against Enterobacteriaceae clinical isolates, including carbapenem-resistant strains . Antimicrobial Agents and Chemotherapy , 60 ( 2 ): 729 - 734 , https://doi.org/10.1128/AAC.01695-15 https://doi.org/10.1128/AAC.01695-15 .

Lamont L L , Beare P A , Ochsner U et al . 2002 . Siderophore-mediated signaling regulates virulence factor production in Pseudomonas aeruginosa . Proceedings of the National Academy of Sciences of the United States of America , 99 ( 10 ): 7072 - 7077 , https://doi.org/10.1073/pnas.092016999 https://doi.org/10.1073/pnas.092016999 .

Li S M . 2010 . Prenylated indole derivatives from fungi: structure diversity, biological activities, biosynthesis and chemoenzymatic synthesis . Natural Product Reports , 27 ( 1 ): 57 - 78 . https://do 10.1039/b909987p http://dx.doi.org/10.1039/b909987p

Luo M H , Zang R C , Wang X et al . 2019 . Natural hydroxamate-containing siderophore acremonpeptides A-D and an aluminum complex of acremonpeptide D from the marine-derived Acremonium persicinum SCSIO 115 . Journal of Natural Products , 82 ( 9 ): 2594 - 2600 , https://doi.org/10.1021/acs.jnatprod.9b00545 https://doi.org/10.1021/acs.jnatprod.9b00545 .

Maurice N M , Bedi B , Sadikot R T . 2018 . Pseudomonas aeruginosa biofilms: host response and clinical implications in lung infections . American Journal of Respiratory Cell and Molecular Biology , 58 ( 4 ): 428 - 439 , https://doi.org/10.1165/rcmb.2017-0321TR https://doi.org/10.1165/rcmb.2017-0321TR .

McPherson C J , Aschenbrenner L M , Lacey B M et al . 2012 . Clinically relevant Gram-negative resistance mechanisms have no effect on the efficacy of MC-1, a novel siderophore-conjugated monocarbam . Antimicrobial Agents and Chemotherapy , 56 ( 12 ): 6334 - 6342 , https://doi.org/10.1128/aac.01345-12 https://doi.org/10.1128/aac.01345-12 .

Miethke M , Marahiel M A . 2007 . Siderophore-based iron acquisition and pathogen control . Microbiology and Molecular Biology Reviews , 71 ( 3 ): 413 - 451 , https://doi.org/10.1128/MMBR.00012-07 https://doi.org/10.1128/MMBR.00012-07 .

Milagres A M F , Machuca A , Napoleão D . 1999 . Detection of siderophore production from several fungi and bacteria by a modification of chrome azurol S (CAS) agar plate assay . Journal of Microbiological Methods , 37 ( 1 ): 1 - 6 , https://doi.org/10.1016/S0167-7012(99)00028-7 https://doi.org/10.1016/S0167-7012(99)00028-7 .

Naseer S , Weinstein E A , Rubin D B et al . 2021 . US Food and Drug Administration (FDA): benefit-risk considerations for Cefiderocol (Fetroja) . Clinical Infectious Diseases , 72 ( 12 ): e1103 - e1111 , https://doi.org/10.1093/cid/ciaa1799 https://doi.org/10.1093/cid/ciaa1799 .

Nordmann P , Naas T , Fortineau N et al . 2007 . Superbugs in the coming new decade; multidrug resistance and prospects for treatment of Staphylococcus aureus , Enterococcus spp. and Pseudomonas aeruginosa in 2010 . Current Opinion in Microbiology , 10 ( 5 ): 436 - 440 , https://doi.org/10.1016/j.mib.2007.07.004 https://doi.org/10.1016/j.mib.2007.07.004 .

Osamu Y , Akira O , Shun H . 2001 . Metal ion-assisted weak interactions involving biological molecules. from small complexes to metalloproteins . Bulletin of the Chemical Society of Japan , 74 ( 9 ): 1525 - 1545 , https://doi.org/10.1246/bcsj.74.1525 https://doi.org/10.1246/bcsj.74.1525 .

Page M G P . 2013 . Siderophore conjugates . Annals of the New York Academy of Sciences , 1277 ( 1 ): 115 - 126 , https://doi.org/10.1111/nyas.12024 https://doi.org/10.1111/nyas.12024 .

Reygaert W C . 2018 . An overview of the antimicrobial resistance mechanisms of bacteria . AIMS Microbiology , 4 ( 3 ): 482 - 501 , https://doi.org/10.3934/microbiol.2018.3.482 https://doi.org/10.3934/microbiol.2018.3.482 .

Sandy M , Han A , Blunt J et al . 2010 . Vanchrobactin and anguibactin siderophores produced by Vibrio sp . DS 40 M 4 . Journal of Natural Products, 73 ( 6 ): 1038 - 1043 , https://doi.org/10.1021/np900750g https://doi.org/10.1021/np900750g .

Shimazaki Y , Yajima T , Takani M et al . 2009 . Metal complexes involving indole rings: structures and effects of metal-indole interactions . Coordination Chemistry Reviews , 253 ( 3-4 ): 479 - 492 , https://doi.org/10.1016/j.ccr.2008.04.012 https://doi.org/10.1016/j.ccr.2008.04.012 .

Souto A , Montaos M A , Rivas A J et al . 2012 . Structure and biosynthetic assembly of piscibactin, a siderophore from Photobacterium damselae subsp. piscicida , predicted from genome analysis . European Journal of Organic Chemistry , 2012 ( 29 ): 5693 - 5700 , https://doi.org/10.1002/ejoc.201200818 https://doi.org/10.1002/ejoc.201200818 .

Vinale F , Nigro M , Sivasithamparam K et al . 2013 . Harzianic acid: a novel siderophore from Trichoderma harzianum . FEMS Microbiology Letters , 347 ( 2 ): 123 - 129 , https://doi.org/10.1111/1574-6968.12231 https://doi.org/10.1111/1574-6968.12231 .

Wang S F , Xiang D D , Tian F B et al . 2021 . Lipopolysaccharide from biofilm-forming Pseudomonas aeruginosa PAO1 induces macrophage hyperinflammatory responses . Journal of Medical Microbiology , 70 ( 4 ): 001352 , https://doi.org/10.1099/jmm.0.001352 https://doi.org/10.1099/jmm.0.001352 .

Wencewicz T A , Mollmann U , Long T E et al . 2009 . Is drug release necessary for antimicrobial activity of siderophore-drug conjugates? Syntheses and biological studies of the naturally occurring salmycin "Trojan Horse" antibiotics and synthetic desferridanoxamine-antibiotic conjugates . Biometals , 22 ( 4 ): 633 - 648 , https://doi.org/10.1007/s10534-009-9218-3 https://doi.org/10.1007/s10534-009-9218-3 .

Wiegand I , Hilpert K , Hancock R E W . 2008 . Agar and broth dilution methods to determine the minimal inhibitory concentration (MIC) of antimicrobial substances . Nature Protocols , 3 ( 2 ): 163 - 175 , https://doi.org/10.1038/nprot.2007.521 https://doi.org/10.1038/nprot.2007.521 .

Wu Q H , Deering R W , Zhang G Y et al . 2018 . Albisporachelin, a new hydroxamate type siderophore from the deep ocean sediment-derived actinomycete Amycolatopsis albispora WP 1 T. Marine Drugs , 16 ( 6 ): 199 , https://doi.org/10.3390/md16060199 https://doi.org/10.3390/md16060199 .

Zaghouani M , Nay B . 2016 . 3-Acylated tetramic and tetronic acids as natural metal binders: myth or reality . Natural Product Reports , 33 ( 4 ): 540 - 548 , https://doi.org/10.1039/c5np00144g https://doi.org/10.1039/c5np00144g .

Zhang F , Barns K , Hoffmann F M et al . 2017 . Thalassosamide, a siderophore discovered from the marine-derived bacterium Thalassospira profundimaris . Journal of Natural Products , 80 ( 9 ): 2551 - 2555 , https://doi.org/10.1021/acs.jnatprod.7b00328 https://doi.org/10.1021/acs.jnatprod.7b00328 .

Views

Downloads

CSCD

Alert me when the article has been cited

Submit

Tools

Publicity Resources

Influence of nitrate concentrations on EH40 steel corrosion affected by coexistence of Desulfovibrio desulfuricans and Pseudomonas aeruginosa bacteria

Screening of marine fungus from Nanji Island and activity of their metabolites against pathogenic Vibrio from Pseudosciaena crocea

Effects of Rake Measurements on Turbine Efficiency

Research on Aging Characterization of Solid Propellantsby Electro-Mechanical Impedance

Influence of Structural Parameters of Diversion Cone on Smooth Effect of Gas Ejection Bottom Pressure Impact

Related Author

Youmin YING

Qihao WU

Bin WEI

Jianwei CHEN

Hong WANG

Yuqi GUO

Zhihua SUN

Ee LI

Related Institution

Key Laboratory of Marine Environmental Corrosion and Biofouling, Institute of Oceanology, Chinese Academy of Sciences

Open Studio for Marine Corrosion and Protection, Pilot National Laboratory for Marine Science and Technology(Qingdao)

Center for Ocean Mega-Science, Chinese Academic of Sciences

University of Chinese Academy of Sciences

Key Laboratory of Marine Materials and Related Technologies, Ningbo Institute of Materials Technology & Engineering, Chinese Academy of Sciences

Address：Editorial Office of JOL, 88 Haijun Rd. Qingdao, 266000, China
Tel：+86-532-82898754 Email：jol@qdio.ac.cn
Technical support is provided by Beijing Founder electronics co., LTD 京ICP备09064830号-19 京公网安备11010802024621
It is recommended to read the content of this site in Chrome&IE9+. Please switch to extreme mode in browser 360.
Cookies We use cookies to help provide and enhance our service and tailor content. By continuing, you agree to the use of cookies.

⁰

β-cyclopiazonic acid binds iron demonstrating siderophore-like activity and promotes growth in Pseudomonas aeruginosa

DOI：

摘要

Abstract

关键词

Keywords

references