Isolation and Bioactivity of Natural Products from Sp. MA37

Overview

Journal Molecules

Publisher MDPI

Date 2025 Jan 25

PMID 39860176

Authors

Fleurdeliz Maglangit

Qing Fang

Jioji N Tabudravu

Kwaku Kyeremeh

Marcel Jaspars

Hai Deng

Affiliations

Soon will be listed here.

Abstract

The isolation and characterization of bioactive metabolites from species continue to represent a vital area of research, given their potential in natural product drug discovery. In this study, we characterize a new siderophore called legonoxamine I, together with a known compound, streptimidone, from the talented soil bacterium sp. MA37, using chromatographic techniques and spectroscopic analysis. Legonoxamine I is a new holo-siderophore, which is likely to be a derailed product from the biosynthetic pathway of legonoxamine A. We also demonstrate that legonoxamine A possesses potent anticancer activity (IC = 2.2 µM), exhibiting a remarkable ~30-fold increase in potency against MCF-7 ATCC HTB-22 breast cancer cells compared to desferrioxamine B, a structural analogue of legonoxamine A (IC = 61.1 µM). Comparing the structural difference between legonoxamine A and desferrioxamine B, it is deduced that the phenylacetyl moiety in legonoxamine A may have contributed significantly to its enhanced potency. Our findings contribute to the growing library of -derived metabolites and underscore the genus' potential as a promising source of lead compounds.

References

Fujita M, Nakano K, Sakai R . Bisucaberin B, a linear hydroxamate class siderophore from the marine bacterium Tenacibaculum mesophilum. Molecules. 2013; 18(4):3917-26. PMC: 6270104. DOI: 10.3390/molecules18043917. View

Elyashberg M, Williams A . ACD/Structure Elucidator: 20 Years in the History of Development. Molecules. 2021; 26(21). PMC: 8588187. DOI: 10.3390/molecules26216623. View

Saha R, Saha N, Donofrio R, Bestervelt L . Microbial siderophores: a mini review. J Basic Microbiol. 2012; 53(4):303-17. DOI: 10.1002/jobm.201100552. View

Becker A, RICKARDS R . The absolute configuration of the glutarimide antibiotics streptimiodone and 9-methylstreptimidone. Helv Chim Acta. 1976; 59(7):2393-401. DOI: 10.1002/hlca.19760590713. View

Li K, Chen W, Bruner S . Microbial siderophore-based iron assimilation and therapeutic applications. Biometals. 2016; 29(3):377-88. DOI: 10.1007/s10534-016-9935-3. View

Kim B, Moon S, Hwang B . Isolation, antifungal activity, and structure elucidation of the glutarimide antibiotic, streptimidone, produced by Micromonospora coerulea. J Agric Food Chem. 1999; 47(8):3372-80. DOI: 10.1021/jf981259s. View

Maglangit F, Alrashdi S, Renault J, Trembleau L, Victoria C, Tong M . Characterization of the promiscuous N-acyl CoA transferase, LgoC, in legonoxamine biosynthesis. Org Biomol Chem. 2020; 18(12):2219-2222. DOI: 10.1039/d0ob00320d. View

He R, Gu S, Xu J, Li X, Chen H, Shao Z . SIDERITE: Unveiling hidden siderophore diversity in the chemical space through digital exploration. Imeta. 2024; 3(2):e192. PMC: 11170966. DOI: 10.1002/imt2.192. View

Sidebottom A, Karty J, Carlson E . Accurate mass MS/MS/MS analysis of siderophores ferrioxamine B and E1 by collision-induced dissociation electrospray mass spectrometry. J Am Soc Mass Spectrom. 2015; 26(11):1899-902. DOI: 10.1007/s13361-015-1242-7. View

10.

Elyashberg M, Williams A, Blinov K . Structural revisions of natural products by Computer-Assisted Structure Elucidation (CASE) systems. Nat Prod Rep. 2010; 27(9):1296-328. DOI: 10.1039/c002332a. View

11.

Kachadourian R, Dellagi A, Laurent J, Bricard L, Kunesch G, Expert D . Desferrioxamine-dependent iron transport in Erwinia amylovora CFBP1430: cloning of the gene encoding the ferrioxamine receptor FoxR. Biometals. 1996; 9(2):143-50. DOI: 10.1007/BF00144619. View

12.

Maglangit F, Kyeremeh K, Deng H . Deletion of the accramycin pathway-specific regulatory gene activates the production of unrelated polyketide metabolites. Nat Prod Res. 2022; 37(16):2753-2758. DOI: 10.1080/14786419.2022.2126466. View

13.

Lee B, Son S, Lee J, Jang M, Heo K, Ko S . Isolation of new streptimidone derivatives, glutarimide antibiotics from Streptomyces sp. W3002 using LC-MS-guided screening. J Antibiot (Tokyo). 2019; 73(3):184-188. DOI: 10.1038/s41429-019-0264-y. View

14.

Maglangit F, Wang S, Moser A, Kyeremeh K, Trembleau L, Zhou Y . Accraspiroketides A-B, Phenylnaphthacenoid-Derived Polyketides with Unprecedented [6 + 6+6 + 6] + [5 + 5] Spiro-Architecture. J Nat Prod. 2024; 87(4):831-836. DOI: 10.1021/acs.jnatprod.3c01012. View

15.

Fang Q, Maglangit F, Wu L, Ebel R, Kyeremeh K, Andersen J . Signalling and Bioactive Metabolites from sp. RK44. Molecules. 2020; 25(3). PMC: 7037778. DOI: 10.3390/molecules25030460. View