Overview

Expertise: Isolation and structure characterization of marine natural products; algal toxin monitoring; secondary metabolite biosynthesis

Access to molecular diversity from unusual biological sources is important to developing new natural products in the therapeutic realm. The Bertin Lab is addressing this access gap by discovering new metabolites from cyanobacterial blooms of Trichodesmium collected from the Gulf of Mexico. We have discovered dozens of new molecules from these blooms using traditional bioassay-guided isolation procedures and innovative mass spectrometry-based approaches such as MS/MS-based molecular networking. We are also interested in investigating the chemistry of bacteria, algae, and invertebrates in Narragansett Bay, RI.

Research

Projects

New chemistry from cyanobacterial blooms

Our research group and our collaborators have been isolating and characterizing new molecules from Trichodesmium blooms collected from the Gulf of Mexico. We have isolated diverse metabolites such as polyketides, peptides, and hybrid polyketide-peptide molecules. We have used MS/MS-based molecular networking to provide a ‘metabolite map’ to ease our isolation efforts. Currently, we are investigating the biological activity of these molecules focusing on cytotoxicity to cancer cell lines and their ability to reduce inflammation in microglia cells.

Domoic acid concentrations in Narragansett Bay

As part of our RI Sea Grant project with the Jenkins Lab at URI, we are monitoring the concentrations of the neurotoxin domoic acid at select sites throughout Narragansett Bay. This toxin is produced by certain diatoms of the genus Pseudo-nitzschia and can affect shellfish in the Bay and cause amnesiac shellfish poisoning in humans.

Developing the Principle Rhode Island Secondary Metabolite (PRISM) Library

As part of an effort to introduce independent research in upper division undergraduate student laboratory classes, we have been building an extract library from specimens in the College of Pharmacy’s Heber W. Youngken Jr. Medicinal Garden. Students extract specimens from the garden and identify potential bioactive compounds with anti-bacterial and anti-oxidant properties. This research has found promising lead compounds against methicillin resistant Staphylococcus aureus and we are now exploring phytochemicals that can reverse E. coli quiescence, and important area for potentially treating recurrent urinary tract infections.

Publications

1. Kirk, R. D.; He, H.; Wahome, P. G.; Wu, S.; Carter, G. T.; Bertin, M. J.* New micropeptins with anti-neuroinflammatory activity isolated from a cyanobacterial bloom. ACS Omega 2021, 6, 15472-15478. doi: 10.1021/acsomega.1c02025.
2. Kirk, R. D.; Picard, K.; Christian, J. A.; Johnson, S. L.; DeBoef, B.; Bertin, M. J.* Unnarmicin D, an anti-inflammatory cyanobacterial metabolite with delta and mu opioid binding activity discovered via a pipeline approach designed to target neurotherapeutics. ACS Chem. Neurosci. 2020, 11, 4478-4488. doi: 10.1021/acschemneuro.0c00686. PMCID: PMC7811748.
3. Kirk, R. D.; Carro, M. A.; Wu, C.; Aldine, M. J.; Wharton, A. M.; Goldstein, D. G.; Rosario, M. E.; Gallucci, G. M. Zhao, Y.; Leibovitz, E.; Bertin, M. J.* Integrating natural product chemistry workflows into medicinal chemistry laboratory training: building the PRISM library and cultivating independent research. Chem. Ed. 2020, 98, 410-415. doi: 10.1021/acs.jchemed.0c00396.
4. Liu, C.; Xu, Y.; Kirk, R. D.; Bertin, M. J.; Seeram, N. P.; Ma, H. Inhibitory effects of skin permeable glucitol-core containing gallotannins from red maple leaves on elastase and their protective effects on human keratinocytes. Funct. Foods 2020, 75, 104208. doi: 10.1016/j.jff.2020.104208.
5. McManus, K. M.; Kirk, R. D.; Via, C. W. Lotti, J. S.; Roduit, A. F.; Teta, R.; Scarpato, S.; Mangoni, A.; Bertin, M. J.* Isolation of isotrichophycin C and trichophycins G-I from a collection of Trichodesmium thiebautii. Nat. Prod. 2020, 83, 2664-2671. doi: 10.1021/acs.jnatprod.0c00550. PMCID: PMC7815318.
6. Ndukwe, I. E.; Wang, X.; Lam, N. Y. S.; Ermanis, K.; Alexander, K. L.; Bertin, M. J.; Martin, G. E.; Muir, G.; Paterson, I.; Britton, R.; Goodman, J. M.; Helfrich, E. J. N.; Piel, J.; Gerwick, W. H.; Williamson, R. T. Synergism of anisotropic and computational NMR methods reveals the likely configuration of phormidolide A. Commun. 2020, 56, 7565-7568. doi: 10.1039/D0CC03055D. PMCID: PMC7436192.
7. Johnson, S. L.; Kirk, R. D.; DaSilva, N. A.; Ma, H.; Seeram, N. P.; Bertin, M.J.* Polyphenol microbial metabolites exhibit gut and blood-brain barrier permeability and protect murine microglia against LPS-induced inflammation. Metabolites 2019, 9, 78. doi: 10.3390/metabo9040078. PMCID: PMC6523162.
8. Teta, R.; Della Salla, G.; Esposito, G.; Via, C. W.; Mazzoccoli, C.; Piccoli, C.; Bertin, M. J.; Costantino, V.; Mangoni, A. A joint molecular networking study of a Smenospongia sponge and a cyanobacterial bloom revealed new antiproliferative chlorinated polyketides. Chem. Front. 2019, 6, 1762-1774. doi: 10.1039/C9QO00074G. PMCID: PMC6927677.
9. He, H.; Bertin, M. J.; Wu, S.; Wahome, P.; Beauchesne, K. R.; Youngs, R.; Zimba, P. V.; Moeller, P. D. R.; Sauri, J.; Carter, G. T. Cyanobufalins: cardioactive toxins from cyanobacterial blooms. Nat. Prod. 2018, 81, 2576-2581. doi: 10.1021/acs.jnatprod.8b00736.
10. Bertin, M. J.;* Sauri, J.; Liu, Y.; Via, C. W.; Roduit, A. F.; Williamson, R. T. Trichophycins B-F, chlorovinylidene-containing polyketides isolated from a cyanobacterial bloom. Org. Chem. 2018, 83, 13256-13266. doi: 10.1021/acs.joc.8b02070. PMCID: PMC7085936.
11. Via, C. W.; Glukhov, E.; Costa, S.; Zimba, P. V.; Moeller, P. D. R.; Gerwick, W. H.; Bertin, J.* The metabolome of a cyanobacterial bloom visualized by MS/MS-based molecular networking reveals new neurotoxic smenamide analogs (C, D, and E). Front. Chem. 2018, 6, 316. doi: 10.3389/fchem.2018.00316. PMCID: PMC6071517.
12. He, H.; Wahome, P. G.; Bertin, J.; Pedone, A. C.; Beauchesne, K. R.; Moeller, P. D. R.; Carter, G. T. Microcystins containing doubly homologated tyrosine residues from a Microcystis aeruginosa bloom: structures and cytotoxicity. J. Nat. Prod. 2018, 81, 1368-1375. doi: 10.1021/acs.jnatprod.7b00986.
13. Belisle, R. S.; Via, C. W.; Schock, T. B.; Villareal, T. A.; Zimba, P. V.; Beauchesne, K. R.; Moeller, P. D. R.; Bertin, M. J.* Trichothiazole A, a dichlorinated polyketide containing an embedded thiazole isolated from Trichodesmium Tetrahedron Lett. 2017, 58, 4066-4068. doi: 10.1016/j.tetlet.2017.09.027. PMCID: PMC7079771.
14. Bertin, M. J.;* Roduit, A. F.; Sun, J.; Alves, G.; Via, C. W.; Gonzalez, M. A.; Zimba, P. V.; Moeller, P. D. R. Tricholides A and B and unnarmicin D: new hybrid PKS-NRPS macrocycles isolated from an environmental collection of Trichodesmium thiebautii. Drugs 2017, 15, doi: 10.3390/md15070206. PMCID: PMC5532648.
15. Pye, C. R.; Bertin, M. J.; Lokey, R. S.; Gerwick, W. H.; Linington, R. G. Retrospective analysis of natural products provides insights for future discovery trends. Natl. Acad. Sci. U. S. A. 2017, 114, 5601-5606. doi: 10.1073/pnas.1614680114. PMCID: PMC5465889.
16. Bertin, M. J.;* Wahome, P. G.; Zimba, P. V.; He, H.; Moeller, P. D. R. Trichophycin A, a cytotoxic linear polyketide isolated from a Trichodesmium thiebautii Mar. Drugs 2017, 15, doi:10.3390/md15010010. PMCID: PMC5295230.
17. Bertin, M. J.;* Zimba, P. V.; He, H.; Moeller, P. D. R. Structure revision of trichotoxin, a chlorinated polyketide isolated from a Trichodesmium thiebautii Tetrahedron Lett. 2016, 57, 5864-5867. doi: 10.1016/j.tetlet.2016.11.062. PMCID: PMC7062361.

*corresponding author at URI

Research Team

Dr. Matthew Bertin

Dr. Matthew Bertin – Dr. Bertin began his appointment at URI in July of 2016. He completed his Ph.D. at the Medical University of South Carolina under the guidance of Peter Moeller. He completed his postdoctoral training under the supervision of William H. Gerwick at the Scripps Institution of Oceanography. Dr. Bertin contributes teaching effort to BPS 136, BPS 451, BPS 445, BPS 552, BPS 525, BPS 551, BPS 633 and other courses including those in the Certificate in Cannabis Studies (BPS 312 and BPS 316). When he’s not looking at mass spec and NMR data, Dr. Bertin enjoys hiking and reading science fiction.     

Image shows: Dr. Matt Bertin at the top of Mt. Katahdin in Maine

Christopher Via (Ph.D. student)

Chris grew up in the hill towns of western/central Massachusetts and earned his Bachelor of Science in Pharmaceutical Science at the University of Rhode Island in 2017. He was an undergraduate researcher in the Bertin Lab and stayed on to begin graduate school in the Fall of 2017. Chris’s Ph.D. research centers on the isolation of new secondary metabolites from Trichodesmium blooms and metabolite comparisons of blooms over time. Chris enjoys cooking and exploring restaurants.

Image shows: Chris presenting his research at the 2018 national meeting of the American Society of Pharmacognosy in Lexington, KY.

Riley Kirk (Ph.D. student)

Riley grew up in Maine and received her undergraduate degree at the University of New Hampshire. She cultivates her interest in pharmacognosy by foraging, extracting, and utilizing traditional medicinal plants and fungi that thrive in the Northeast. Her main interest in natural products is unvieling the biological function of secondary metabolites created by marine bacteria and terrestrial fungi, with the goal of determining how these compounds can be used to further the scope of medicine. Her favorite indoor activity is reading books with her cat asleep on her feet.     

Image Shows: Riley examining a water sample from Narragansett Bay under the microscope in order to isolate Pseudo-nitzschia cells

Andrew Kim (Ph.D. student)

Andrew grew up in New Jersey and received his undergraduate degree at Purdue University. He has a strong interest in medicinal chemistry and has a background in synthetic organic chemistry from his undergraduate research which focused on methodology and multi-step synthesis. Andrew’s main interest is in utilizing natural products to discover its biological properties and optimize compounds for potential drug leads. Andrew enjoys playing a variety of sports such as weight lifting and fencing.

Image Shows: Andrew at the Chicago Botanic Garden.

Terra Marie Jouaneh (M.S. student)

Terra grew up in coastal Rhode Island and earned her Bachelor of Science in Pharmaceutical Sciences from the University of Rhode Island in 2019. While her undergraduate research was in physical organic chemistry, Terra transitioned to natural products chemistry for her graduate studies. Her master’s research centers on the identification of novel compounds capable of reversing E. coli bacteria quiescence. When she is not on campus, she enjoys going on long walks and scoping out new coffee shops.

Image Shows: Terra in the Heber W. Youngken Jr. Medicinal Garden outside of the College of Pharmacy.

Matthew J. Bertin, Ph.D.

• Assistant Professor
• Office: 495M Lab: 420
• Phone:401.874.5016
• Email:mbertin@uri.edu

Full Bio