Deuterium-Labeled Precursor Feeding Reveals a New p ABA-Containing Meroterpenoid from the Mango Pathogen Xanthomonas citri pv. mangiferaeindicae
Abstract
A new para-aminobenzoic-acid-containing natural product from the mango pathogenic organism Xanthomonas citri pv. mangiferaeindicae is described. By means of stable isotope precursor feeding combined with nontargeted LC-MS/MS, the generated spectra were clustered and visualized in a molecular network. This led to the identification of a new member of the meroterpenoids, termed xanthomonic acid, which is composed of an isoprenylated para-aminobenzoic acid. In vitro cytotoxicity assays demonstrated activity of xanthomonic acid against several human cancer cell lines by induction of autophagy.
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Stable-isotope precursor feeding has been used to identify natural products with specific biosynthetic precursors such as colibactin and xanthomonic acid, and to investigate the biosynthesis of fungisporin and related analogues.
“several studies have made use of stable-isotope precursor feeding to identify natural products with specific biosynthetic precursors such as colibactin,68 xanthomonic acid69 and to investigate the biosynthesis of fungisporin and the discovery of related analogues.70”
From Connecting metabolome and phenotype: recent advances in functional metabolomics tools for the identification of bioactive natural products (2024) · cites this paper as [69]
Cites
Mosmann, T. (1983) · Journal of Immunological Methods · doi:10.1016/0022-1759(83)90303-4 · Cited by 56,104 · see citing works
Ong, S.-E., Blagoev, B., Kratchmarova, I., Kristensen, D. B., Steen, H., Pandey, A., & Mann, M. (2002) · Molecular & Cellular Proteomics · doi:10.1074/mcp.m200025-mcp200 · Cited by 5,574 · see citing works
Cytoscape 2.8: new features for data integration and network visualization
Smoot, M. E., Ono, K., Ruscheinski, J., Wang, P., & Ideker, T. (2010) · Bioinformatics · doi:10.1093/bioinformatics/btq675 · Cited by 4,770 · see citing works
Autophagy: cellular and molecular mechanisms
Glick, D. R., Barth, S., & Macleod, K. F. (2010) · The Journal of Pathology · doi:10.1002/path.2697 · Cited by 3,815 · see citing works
Molecular Networking as a Dereplication Strategy
Yang, J. Y., Sanchez, L. M., Rath, C. M. B., Liu, X., Boudreau, P. D., Bruns, N., Glukhov, E., Wodtke, A., de Felício, R., Fenner, A. M., et al. (2013) · Journal of Natural Products · doi:10.1021/np400413s · Cited by 613 · see citing works
Terpenoids: Opportunities for Biosynthesis of Natural Product Drugs Using Engineered Microorganisms
Ajikumar, P. K., Tyo, K. E. J., Carlsen, S., Mucha, O., Too, H., & Stephanopoulos, G. N. (2008) · Molecular Pharmaceutics · doi:10.1021/mp700151b · Cited by 445 · see citing works
Role and regulation of autophagy in cancer
Chen, N., & Karantza‐Wadsworth, V. (2009) · Biochimica et Biophysica Acta (BBA) - Molecular Cell Research · doi:10.1016/j.bbamcr.2008.12.013 · Cited by 355 · see citing works
Employing ProteoWizard to Convert Raw Mass Spectrometry Data
Holman, J. D., Tabb, D. L., & Mallick, P. (2014) · Current Protocols in Bioinformatics · doi:10.1002/0471250953.bi1324s46 · Cited by 318 · see citing works
The colibactin warhead crosslinks DNA
Vizcaino, M. I., & Crawford, J. M. (2015) · Nature Chemistry · doi:10.1038/nchem.2221 · Cited by 247 · see citing works
Krug, D., & Müller, R. (2014) · Natural Product Reports · doi:10.1039/c3np70127a · Cited by 151 · see citing works
The gyrase inhibitor albicidin consists of p-aminobenzoic acids and cyanoalanine
Cociancich, S., Pesic, A., Petras, D., Uhlmann, S., Kretz, J., Schubert, V., Vieweg, L., Duplan, S., Marguerettaz, M., Noëll, J., et al. (2015) · Nature Chemical Biology · doi:10.1038/nchembio.1734 · Cited by 140 · see citing works
Self-citationAutophagy, Bafilomycin and Cell Death: The “A-B-Cs” of Plecomacrolide-Induced Neuroprotection
Shacka, J. J., Klocke, B. J., & Roth, K. A. (2006) · Autophagy · doi:10.4161/auto.2703 · Cited by 120 · see citing works
Aminobenzoates as building blocks for natural productassembly lines
Walsh, C. T., Haynes, S. W., & Ames, B. D. (2011) · Natural Product Reports · doi:10.1039/c1np00072a · Cited by 76 · see citing works
Weise, T., Kai, M., Gummesson, A., Tröger, A. G., von Reuß, S. H., Piepenborn, S., Kosterka, F., Sklorz, M., Zimmermann, R., Francke, W., et al. (2012) · Beilstein Journal of Organic Chemistry · doi:10.3762/bjoc.8.65 · Cited by 76 · see citing works
MG132-mediated inhibition of the ubiquitin–proteasome pathway ameliorates cancer cachexia
Zhang, L., Tang, H., Kou, Y., Li, R., Zheng, Y., Wang, Q., Zhou, X., & Jin, L. (2013) · Journal of Cancer Research and Clinical Oncology · doi:10.1007/s00432-013-1412-6 · Cited by 72 · see citing works
Combining Stable Isotope Labeling and Molecular Networking for Biosynthetic Pathway Characterization
Klitgaard, A., Nielsen, J. B., Frandsen, R. J. N., Andersen, M. R., & Nielsen, K. F. (2015) · Analytical Chemistry · doi:10.1021/acs.analchem.5b01934 · Cited by 54 · see citing works
Gagnevin, L., Leach, J. E., & Pruvost, O. (1997) · Applied and Environmental Microbiology · doi:10.1128/aem.63.1.246-253.1997 · Cited by 43 · see citing works
Erythrolic acids A–E, Meroterpenoids from a Marine-DerivedErythrobactersp.
Hu, Y., Legako, A. G., Espindola, A. P. D. M., et al. (2012) · The Journal of Organic Chemistry · doi:10.1021/jo300197z · Cited by 27 · see citing works
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Vitale, G. A., Geibel, C., Minda, V., Wang, M., Aron, A. T., & Petras, D. (2024) · Natural Product Reports · doi:10.1039/d3np00050h · Cited by 66 · see citing works
Self-citation
- Authors
- Saleh, H., Petras, D., Mainz, A., Kerwat, D., Nalbantsoy, A., Erzurumlu, Y., & Süssmuth, R. D.
- Affiliations
- Technische Universität Berlin (DE)
- Department of Bioengineering, Faculty of Engineering, Ege University, 35100 Bornova Izmir, Turkey
- Department of Biochemistry, Faculty of Pharmacy, Ege University, 35100 Bornova Izmir, Turkey
- Corresponding author
- Süssmuth, Roderich D.
- Venue
- Journal of Natural Products
- Publisher
- American Chemical Society (ACS)
- Published
- 2016-05-27
- Volume
- 79
- Issue
- 6
- Pages
- 1532-1537
- ISSN
- 0163-3864 (ISSN-L)
- 1520-6025
- OpenAlex
- W2400061033
- Cited by
- 13
- References
- 18
- Citations by year
- 2024: 3 · 2022: 1 · 2021: 1 · 2020: 3 · 2019: 1 · 2018: 1 · 2017: 2 · 2016: 1
- FWCI
- 1.35
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of Natural Products (publishedVersion)
- PubMed (publishedVersion)
- Funders
- German Academic Exchange Service
- Ministry of Higher Education
- Topics
- Health Sciences › Medicine › Pharmacology › Microbial Natural Products and Biosynthesis
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Bioactive natural compounds
- Life Sciences › Agricultural and Biological Sciences › Plant Science › Plant Pathogenic Bacteria Studies
- Keywords
- meroterpenoids, p-aminobenzoic acid, Xanthomonas citri pv. mangiferaeindicae, natural product discovery, molecular networking, cytotoxicity, autophagy induction, cancer cell lines
- MeSH terms
- Antineoplastic Agents, Autophagy, Deuterium, Drug Screening Assays, Antitumor, 4-Aminobenzoic Acid, Plant Diseases, Terpenes, Xanthomonas, Molecular Structure, Mangifera
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