Genome Mining and Metabolomics Unveil Pseudonochelin: A Siderophore Containing 5-Aminosalicylate from a Marine-Derived Sp. Bacterium

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2022 Jun 1

PMID 35649263

Authors

Fan Zhang

Rene F Ramos Alvarenga

Kurt Throckmorton

Shaurya Chanana

Doug R Braun

Jen Fossen

Miao Zhao

Sue McCrone

Mary Kay Harper

Scott R Rajski

Warren E Rose

David R Andes

Michael G Thomas

Tim S Bugni

Affiliations

Soon will be listed here.

Abstract

Pseudonochelin (), a siderophore from a marine-derived sp. bacterium, was discovered using genome mining and metabolomics technologies. A 5-aminosalicylic acid (5-ASA) unit, not previously found in siderophore natural products, was identified in . Annotation of a putative biosynthetic gene cluster combined with bioinformatics and isotopic enrichment studies enabled us to propose the biosynthesis of . Moreover, was found to display and antibacterial activity in an iron-dependent fashion.

Citing Articles

Advances in Natural Products from the Marine-Sponge-Associated Microorganisms with Antimicrobial Activity in the Last Decade.

Liang J, She J, Fu J, Wang J, Ye Y, Yang B Mar Drugs. 2023; 21(4).

PMID: 37103375 PMC: 10143917. DOI: 10.3390/md21040236.

References

Seyedsayamdost M, Traxler M, Zheng S, Kolter R, Clardy J . Structure and biosynthesis of amychelin, an unusual mixed-ligand siderophore from Amycolatopsis sp. AA4. J Am Chem Soc. 2011; 133(30):11434-7. PMC: 3144690. DOI: 10.1021/ja203577e. View

Daly J, Jerina D, WITKOP B . Migration of deuterium during hydroxylation of aromatic substrates by liver microsomes. I. Influence of ring substitutents. Arch Biochem Biophys. 1968; 128(2):517-27. DOI: 10.1016/0003-9861(68)90059-3. View

Chanana S, Thomas C, Zhang F, Rajski S, Bugni T . : Automated Hierarchical Clustering and Principal Component Analysis of Large Metabolomic Datasets in R. Metabolites. 2020; 10(7). PMC: 7407629. DOI: 10.3390/metabo10070297. View

Sarotti A, Pellegrinet S . A multi-standard approach for GIAO (13)C NMR calculations. J Org Chem. 2009; 74(19):7254-60. DOI: 10.1021/jo901234h. View

McMahon M, Rush J, Thomas M . Analyses of MbtB, MbtE, and MbtF suggest revisions to the mycobactin biosynthesis pathway in Mycobacterium tuberculosis. J Bacteriol. 2012; 194(11):2809-18. PMC: 3370630. DOI: 10.1128/JB.00088-12. View

Basset G, Quinlivan E, Ravanel S, Rebeille F, Nichols B, Shinozaki K . Folate synthesis in plants: the p-aminobenzoate branch is initiated by a bifunctional PabA-PabB protein that is targeted to plastids. Proc Natl Acad Sci U S A. 2004; 101(6):1496-501. PMC: 341757. DOI: 10.1073/pnas.0308331100. View

Sontag B, Gerlitz M, Paululat T, Rasser H, Grun-Wollny I, Hansske F . Oxachelin, a novel iron chelator and antifungal agent from Streptomyces sp. GW9/1258. J Antibiot (Tokyo). 2006; 59(10):659-63. DOI: 10.1038/ja.2006.88. View

Park S, Tripathi A, Wu J, Schultz P, Yim I, McQuade T . Discovery of cahuitamycins as biofilm inhibitors derived from a convergent biosynthetic pathway. Nat Commun. 2016; 7:10710. PMC: 4757757. DOI: 10.1038/ncomms10710. View

Hou Y, Braun D, Michel C, Klassen J, Adnani N, Wyche T . Microbial strain prioritization using metabolomics tools for the discovery of natural products. Anal Chem. 2012; 84(10):4277-83. PMC: 3352271. DOI: 10.1021/ac202623g. View

10.

Duncan K, Crusemann M, Lechner A, Sarkar A, Li J, Ziemert N . Molecular networking and pattern-based genome mining improves discovery of biosynthetic gene clusters and their products from Salinispora species. Chem Biol. 2015; 22(4):460-471. PMC: 4409930. DOI: 10.1016/j.chembiol.2015.03.010. View

11.

Felnagle E, Barkei J, Park H, Podevels A, McMahon M, Drott D . MbtH-like proteins as integral components of bacterial nonribosomal peptide synthetases. Biochemistry. 2010; 49(41):8815-7. PMC: 2974439. DOI: 10.1021/bi1012854. View

12.

Yan J, Chevrette M, Braun D, Harper M, Currie C, Bugni T . Madurastatin D1 and D2, Oxazoline Containing Siderophores Isolated from an . Org Lett. 2019; 21(16):6275-6279. PMC: 6941472. DOI: 10.1021/acs.orglett.9b02159. View

13.

Tyler A, Mosaei H, Morton S, Waddell P, Wills C, McFarlane W . Structural Reassignment and Absolute Stereochemistry of Madurastatin C1 (MBJ-0034) and the Related Aziridine Siderophores: Madurastatins A1, B1, and MBJ-0035. J Nat Prod. 2017; 80(5):1558-1562. PMC: 6544507. DOI: 10.1021/acs.jnatprod.7b00082. View

14.

Sun C, Yang Z, Zhang C, Liu Z, He J, Liu Q . Genome Mining of Streptomyces atratus SCSIO ZH16: Discovery of Atratumycin and Identification of Its Biosynthetic Gene Cluster. Org Lett. 2019; 21(5):1453-1457. DOI: 10.1021/acs.orglett.9b00208. View

15.

Stachelhaus T, Mootz H, Marahiel M . The specificity-conferring code of adenylation domains in nonribosomal peptide synthetases. Chem Biol. 1999; 6(8):493-505. DOI: 10.1016/S1074-5521(99)80082-9. View

16.

Moran G . 4-Hydroxyphenylpyruvate dioxygenase. Arch Biochem Biophys. 2004; 433(1):117-28. DOI: 10.1016/j.abb.2004.08.015. View

17.

Cociancich S, Pesic A, Petras D, Uhlmann S, Kretz J, Schubert V . The gyrase inhibitor albicidin consists of p-aminobenzoic acids and cyanoalanine. Nat Chem Biol. 2015; 11(3):195-7. DOI: 10.1038/nchembio.1734. View

18.

Perrotta C, Pellegrino P, Moroni E, De Palma C, Cervia D, Danelli P . Five-aminosalicylic Acid: an update for the reappraisal of an old drug. Gastroenterol Res Pract. 2015; 2015:456895. PMC: 4320793. DOI: 10.1155/2015/456895. View

19.

Fukuda T, Helfrich E, Mevers E, Melo W, Van Arnam E, Andes D . Specialized Metabolites Reveal Evolutionary History and Geographic Dispersion of a Multilateral Symbiosis. ACS Cent Sci. 2021; 7(2):292-299. PMC: 7908033. DOI: 10.1021/acscentsci.0c00978. View

20.

Chanana S, Thomas C, Braun D, Hou Y, Wyche T, Bugni T . Natural Product Discovery Using Planes of Principal Component Analysis in R (PoPCAR). Metabolites. 2017; 7(3). PMC: 5618319. DOI: 10.3390/metabo7030034. View