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Publications

Published Articles

  1. Singh, T.; Georgiou, C. D.; Jeffrey, C. S.; Tucker, M. J.; Philbin, C. S.; Mahmud, T.; McKay, C. P.; Sun, H. J. UVC-Intense Exoplanets May Not Be Uninhabitable: Evidence from a Desert Lichen. Astrobiology 2025, 25 (6), 404–413. https://doi.org/10.1089/ast.2024.0137.

  2. Philbin, C. S.; Burroughs, M.; Richards, L. A.; Faske, T. M.; Dyer, L. A.; Parchman, T. L.; Jeffrey, C. S. Leveraging Phytochemical Variation in Piper Scintillans Trel. to Discover Novel Flavanone Meroterpenes. Phytochemistry Letters 2025, 69, 103134. https://doi.org/10.1016/j.phytol.2025.103134.

  3. Oliveira, C. R.; Burroughs, M. J.; Richards, L. A.; Dyer, L. A.; Urbano-Muñoz, F.; Lee, C.; Warner, M.; Dodson, C. D.; Wallace, I. S.; Jeffrey, C. S. 1H-NMR Guided Isolation of Bioactive Compounds from Species of the Genus Piper. Molecules 2025, 30 (9), 2020. https://doi.org/10.3390/molecules30092020.

  4. Larson, G. E.; Mahmud, T.; Dergachev, I. D.; Philbin, C. S.; Feng, Y.; de Oliveira, C. R.; Sun, H. J.; Tucker, M. J.; Varganov, S. A.; Jeffrey, C. S. Structure Revision of Scytonemin Imine and Its Relationship to Scytonemin Chromism and Cyanobacterial Adaptability. Sci Rep 2025, 15 (1), 25630. https://doi.org/10.1038/s41598-025-10419-x.

  5. Kay, E. R.; Philbin, C. S.; Richards, L. A.; Forister, M. L.; Jeffrey, C.; Dyer, L. A. Effects of Water and Wind Stress on Phytochemical Diversity, Cannabinoid Composition, and Arthropod Diversity in Hemp. Plants (Basel) 2025, 14 (3), 474. https://doi.org/10.3390/plants14030474.

  6. Mahmud, T.; Moore, D. C.; Dergachev, I. D.; Sun, H.; Varganov, S. A.; Tucker, M. J.; Jeffrey, C. S. Cortical Polysaccharides Play a Crucial Role in Lichen UV Protection. CR-PHYS-SC 2024, 5 (10). https://doi.org/10.1016/j.xcrp.2024.102242.

  7. de Oliveira, C. R.; Ledvina, Z. D.; Leonard, M. D.; Odoh, S. O.; Dodson, C. D.; Jeffrey, C. S. Isolation of New Neolignans and an Unusual Meroterpenoid from Piper Cabagranum. Front. Nat. Prod. 2024, 2. https://doi.org/10.3389/fntpr.2023.1332436.

  8. Abusallout, I.; Song, M.; Chan, A.; McKenna, E.; Van Buren, J.; Mccoy, S.; Ledvina, Z.; Jeffrey, C.; McCurry, D. L.; Hanigan, D. Bacterial Dealkylation of Benzalkonium Chlorides in Wastewater Produces Benzyldimethylamine, a Potent N-Nitrosodimethylamine Precursor. Water Research 2024, 260, 121945. https://doi.org/10.1016/j.watres.2024.121945.

  9. Glassmire, A. E.; Carson, W. P.; Smilanich, A. M.; Richards, L. A.; Jeffrey, C. S.; Dodson, C. D.; Philbin, C. S.; Humberto, G. L.; Dyer, L. A. Multiple and Contrasting Pressures Determine Intraspecific Phytochemical Variation in a Tropical Shrub. Oecologia 2023, 201 (4), 991–1003. https://doi.org/10.1007/s00442-023-05364-3.

  10. Philbin, C. S.; Dyer, L. A.; Jeffrey, C. S.; Glassmire, A. E.; Richards, L. A. Structural and Compositional Dimensions of Phytochemical Diversity in the Genus Piper Reflect Distinct Ecological Modes of Action. Journal of Ecology 2022, 110 (1), 57–67. https://doi.org/10.1111/1365-2745.13691.

  11. Muth, F.; Philbin, C. S.; Jeffrey, C. S.; Leonard, A. S. Discovery of Octopamine and Tyramine in Nectar and Their Effects on Bumblebee Behavior. iScience 2022, 25 (8). https://doi.org/10.1016/j.isci.2022.104765.

  12. Massad, T. J.; Richards, L. A.; Philbin, C.; Yamaguchi, L. F.; Kato, M. J.; Jeffrey, C. S.; Oliveira Jr, C.; Ochsenrider, K.; de Moraes, M. M.; Tepe, E. J.; Cebrian-Torrejon, G.; Sandivo, M.; Dyer, L. A. The Chemical Ecology of Tropical Forest Diversity: Environmental Variation, Chemical Similarity, Herbivory, and Richness. Ecology 2022, 103 (9), e3762. https://doi.org/10.1002/ecy.3762.

  13. Uckele, K. A.; Jahner, J. P.; Tepe, E. J.; Richards, L. A.; Dyer, L. A.; Ochsenrider, K. M.; Philbin, C. S.; Kato, M. J.; Yamaguchi, L. F.; Forister, M. L.; Smilanich, A. M.; Dodson, C. D.; Jeffrey, C. S.; Parchman, T. L. Phytochemistry Reflects Different Evolutionary History in Traditional Classes versus Specialized Structural Motifs. Sci Rep 2021, 11 (1), 17247. https://doi.org/10.1038/s41598-021-96431-3.

  14. Decker, L. E.; Jeffrey, C. S.; Ochsenrider, K. M.; Potts, A. S.; de Roode, J. C.; Smilanich, A. M.; Hunter, M. D. Elevated Atmospheric Concentrations of CO2 Increase Endogenous Immune Function in a Specialist Herbivore. Journal of Animal Ecology 2021, 90 (3), 628–640. https://doi.org/10.1111/1365-2656.13395.

  15. Maynard, L. D.; Slinn, H. L.; Glassmire, A. E.; Matarrita-Carranza, B.; Dodson, C. D.; Nguyen, T. T.; Burroughs, M. J.; Dyer, L. A.; Jeffrey, C. S.; Whitehead, S. R. Secondary Metabolites in a Neotropical Shrub: Spatiotemporal Allocation and Role in Fruit Defense and Dispersal. Ecology 2020, 101 (12), e03192. https://doi.org/10.1002/ecy.3192.

  16. Matocq, M. D.; Ochsenrider, K. M.; Jeffrey, C. S.; Nielsen, D. P.; Richards, L. A. Fine-Scale Differentiation in Diet and Metabolomics of Small Mammals Across a Sharp Ecological Transition. Front. Ecol. Evol. 2020, 8. https://doi.org/10.3389/fevo.2020.00282.

  17. Glassmire, A. E.; Philbin, C.; Richards, L. A.; Jeffrey, C. S.; Snook, J. S.; Dyer, L. A. Proximity to Canopy Mediates Changes in the Defensive Chemistry and Herbivore Loads of an Understory Tropical Shrub, Piper Kelleyi. Ecology Letters 2019, 22 (2), 332–341. https://doi.org/10.1111/ele.13194.

  18. Richards, L. A.; Oliveira, C.; Dyer, L. A.; Rumbaugh, A.; Urbano-Muñoz, F.; Wallace, I. S.; Dodson, C. D.; Jeffrey, C. S. Shedding Light on Chemically Mediated Tri-Trophic Interactions: A 1H-NMR Network Approach to Identify Compound Structural Features and Associated Biological Activity. Front. Plant Sci. 2018, 9. https://doi.org/10.3389/fpls.2018.01155.

  19. Dyer, L. A.; Philbin, C. S.; Ochsenrider, K. M.; Richards, L. A.; Massad, T. J.; Smilanich, A. M.; Forister, M. L.; Parchman, T. L.; Galland, L. M.; Hurtado, P. J.; Espeset, A. E.; Glassmire, A. E.; Harrison, J. G.; Mo, C.; Yoon, S.; Pardikes, N. A.; Muchoney, N. D.; Jahner, J. P.; Slinn, H. L.; Shelef, O.; Dodson, C. D.; Kato, M. J.; Yamaguchi, L. F.; Jeffrey, C. S. Modern Approaches to Study Plant–Insect Interactions in Chemical Ecology. Nat Rev Chem 2018, 2 (6), 50–64. https://doi.org/10.1038/s41570-018-0009-7.

  20. Massad, T. J.; Martins de Moraes, M.; Philbin, C.; Oliveira Jr., C.; Cebrian Torrejon, G.; Fumiko Yamaguchi, L.; Jeffrey, C. S.; Dyer, L. A.; Richards, L. A.; Kato, M. J. Similarity in Volatile Communities Leads to Increased Herbivory and Greater Tropical Forest Diversity. Ecology 2017, 98 (7), 1750–1756. https://doi.org/10.1002/ecy.1875.

  21. Richards, L. A.; Glassmire, A. E.; Ochsenrider, K. M.; Smilanich, A. M.; Dodson, C. D.; Jeffrey, C. S.; Dyer, L. A. Phytochemical Diversity and Synergistic Effects on Herbivores. Phytochem Rev 2016, 15 (6), 1153–1166. https://doi.org/10.1007/s11101-016-9479-8.

  22. Gutierrez, Y. V.; Yamaguchi, L. F.; de Moraes, M. M.; Jeffrey, C. S.; Kato, M. J. Natural Products from Peperomia: Occurrence, Biogenesis and Bioactivity. Phytochem Rev 2016, 15 (6), 1009–1033. https://doi.org/10.1007/s11101-016-9461-5.

  23. Glassmire, A. E.; Jeffrey, C. S.; Forister, M. L.; Parchman, T. L.; Nice, C. C.; Jahner, J. P.; Wilson, J. S.; Walla, T. R.; Richards, L. A.; Smilanich, A. M.; Leonard, M. D.; Morrison, C. R.; Simbaña, W.; Salagaje, L. A.; Dodson, C. D.; Miller, J. S.; Tepe, E. J.; Villamarin-Cortez, S.; Dyer, L. A. Intraspecific Phytochemical Variation Shapes Community and Population Structure for Specialist Caterpillars. New Phytologist 2016, 212 (1), 208–219. https://doi.org/10.1111/nph.14038.

  24. Anumandla, D.; Acharya, A.; Jeffrey, C. S. Oxidative (3 + 2) Cycloaddition Reactions of Diaza-Oxyallyl Cationic Intermediates and Indoles for the Synthesis of Imidazoloindolines. Org. Lett. 2016, 18 (3), 476–479. https://doi.org/10.1021/acs.orglett.5b03527.

  25. Acharya, A.; Montes, K.; Jeffrey, C. S. Access to 4-Oxazolidinones: A (3 + 2) Cycloaddition Approach. Org. Lett. 2016, 18 (23), 6082–6085. https://doi.org/10.1021/acs.orglett.6b03069.

  26. Acharya, A.; A. Eickhoff, J.; Chen, K.; J. Catalano, V.; S. Jeffrey, C. Access to Bicyclic Hydroxamate Macrocycles via Intramolecular Aza-(4 + 3) Cyloaddition Reactions of Aza-Oxyallylic Cation Intermediates. Organic Chemistry Frontiers 2016, 3 (3), 330–334. https://doi.org/10.1039/C5QO00315F.

  27. Richards, L. A.; Dyer, L. A.; Forister, M. L.; Smilanich, A. M.; Dodson, C. D.; Leonard, M. D.; Jeffrey, C. S. Phytochemical Diversity Drives Plant–Insect Community Diversity. Proceedings of the National Academy of Sciences 2015, 112 (35), 10973–10978. https://doi.org/10.1073/pnas.1504977112.

  28. L. Barnes, K.; Chen, K.; J. Catalano, V.; S. Jeffrey, C. New Building Blocks for Iminosugars: A Concise Synthesis of Polyhydroxylated N -Alkoxypiperidines through an Intramolecular Azepine Ring Contraction. Organic Chemistry Frontiers 2015, 2 (5), 497–501. https://doi.org/10.1039/C4QO00330F.

  29. Acharya, A.; Anumandla, D.; Jeffrey, C. S. Dearomative Indole Cycloaddition Reactions of Aza-Oxyallyl Cationic Intermediates: Modular Access to Pyrroloindolines. J. Am. Chem. Soc. 2015, 137 (47), 14858–14860. https://doi.org/10.1021/jacs.5b10184.

  30. Song, M.; Gorzalski, A.; Nguyen, T. T.; Liu, X.; Jeffrey, C.; Blomquist, G. J.; Tittiger, C. Exo-Brevicomin Biosynthesis in the Fat Body of the Mountain Pine Beetle, Dendroctonus Ponderosae. J Chem Ecol 2014, 40 (2), 181–189. https://doi.org/10.1007/s10886-014-0381-9.

  31. Song, M.; Delaplain, P.; Nguyen, T. T.; Liu, X.; Wickenberg, L.; Jeffrey, C.; Blomquist, G. J.; Tittiger, C. Exo-Brevicomin Biosynthetic Pathway Enzymes from the Mountain Pine Beetle, Dendroctonus Ponderosae. Insect Biochemistry and Molecular Biology 2014, 53, 73–80. https://doi.org/10.1016/j.ibmb.2014.08.002.

  32. Jeffrey, C. S.; Leonard, M. D.; Glassmire, A. E.; Dodson, C. D.; Richards, L. A.; Kato, M. J.; Dyer, L. A. Antiherbivore Prenylated Benzoic Acid Derivatives from Piper Kelleyi. J. Nat. Prod. 2014, 77 (1), 148–153. https://doi.org/10.1021/np400886s.

  33. Gaia, A. M.; Yamaguchi, L. F.; Jeffrey, C. S.; Kato, M. J. Age-Dependent Changes from Allylphenol to Prenylated Benzoic Acid Production in Piper Gaudichaudianum Kunth. Phytochemistry 2014, 106, 86–93. https://doi.org/10.1016/j.phytochem.2014.06.013.

  34. Freitas, G. C.; Batista, J. M.; Franchi, G. C.; Nowill, A. E.; Yamaguchi, L. F.; Vilcachagua, J. D.; Favaro, D. C.; Furlan, M.; Guimarães, E. F.; Jeffrey, C. S.; Kato, M. J. Cytotoxic Non-Aromatic B-Ring Flavanones from Piper Carniconnectivum C. DC. Phytochemistry 2014, 97, 81–87. https://doi.org/10.1016/j.phytochem.2013.10.012.

  35. Dyer, L. A.; Parchman, T. L.; Jeffrey, C. S.; Richards, L. A. New Dimensions of Tropical Diversity: An Inordinate Fondness for Insect Molecules, Taxa, and Trophic Interactions. Current Opinion in Insect Science 2014, 2, 14–19. https://doi.org/10.1016/j.cois.2014.06.001.

  36. Barnes, K. L.; Koster, A. K.; Jeffrey, C. S. Trapping the Elusive Aza-Oxyallylic Cation: New Opportunities in Heterocycloaddition Chemistry. Tetrahedron Letters 2014, 55 (34), 4690–4696. https://doi.org/10.1016/j.tetlet.2014.06.050.

  37. Anumandla, D.; Littlefield, R.; Jeffrey, C. S. Oxidative 1,4-Diamination of Dienes Using Simple Urea Derivatives. Org. Lett. 2014, 16 (19), 5112–5115. https://doi.org/10.1021/ol502460j.

  38. Whitehead, S. R.; Jeffrey, C. S.; Leonard, M. D.; Dodson, C. D.; Dyer, L. A.; Bowers, M. D. Patterns of Secondary Metabolite Allocation to Fruits and Seeds in Piper Reticulatum. J Chem Ecol 2013, 39 (11), 1373–1384. https://doi.org/10.1007/s10886-013-0362-4.

  39. Acharya, A.; Eickhoff, J. A.; Jeffrey, C. S. Intramolecular Aza-[4+3] Cycloaddition Reactions of α-Halohydroxamates. Synthesis 2013, 45, 1825–1836. https://doi.org/10.1055/s-0033-1338883.

  40. Jeffrey, C. S.; Anumandla, D.; Carson, C. R. 1,4-Diamination of Cyclic Dienes via a (4 + 3) Cycloaddition of Diaza-Allyl Cationic Intermediates. Org. Lett. 2012, 14 (22), 5764–5767. https://doi.org/10.1021/ol302771z.

  41. Jeffrey, C. S.; Barnes, K. L.; Eickhoff, J. A.; Carson, C. R. Generation and Reactivity of Aza-Oxyallyl Cationic Intermediates: Aza-[4 + 3] Cycloaddition Reactions for Heterocycle Synthesis. J. Am. Chem. Soc. 2011, 133 (20), 7688–7691. https://doi.org/10.1021/ja201901d.

 

Mentored Publications

  1. Hoye, T. R.; Jeffrey, C. S.; Nelson, D. P. Dynamic Kinetic Resolution During a Vinylogous Payne Rearrangement: A Concise Synthesis of the Polar Pharmacophoric Subunit of (+)-Scyphostatin. Org. Lett. 2010, 12 (1), 52–55. https://doi.org/10.1021/ol902459z.

  2. Frie, J. L.; Jeffrey, C. S.; Sorensen, E. J. A Hypervalent Iodine-Induced Double Annulation Enables a Concise Synthesis of the Pentacyclic Core Structure of the Cortistatins. Org. Lett. 2009, 11 (23), 5394–5397. https://doi.org/10.1021/ol902168g.

  3. Hoye, T. R.; Jeffrey, C. S.; Shao, F. Mosher Ester Analysis for the Determination of Absolute Configuration of Stereogenic (Chiral) Carbinol Carbons. Nat Protoc 2007, 2 (10), 2451–2458. https://doi.org/10.1038/nprot.2007.354.

  4. Hoye, T. R.; Dvornikovs, V.; Fine, J. M.; Anderson, K. R.; Jeffrey, C. S.; Muddiman, D. C.; Shao, F.; Sorensen, P. W.; Wang, J. Details of the Structure Determination of the Sulfated Steroids PSDS and PADS:  New Components of the Sea Lamprey (Petromyzon Marinus) Migratory Pheromone. J. Org. Chem. 2007, 72 (20), 7544–7550. https://doi.org/10.1021/jo070957l.

  5. Hoye, T. R.; Jeffrey, C. S. Student Empowerment through “Mini-Microscale” Reactions: The Epoxidation of 1 Mg of Geraniol. J. Chem. Educ. 2006, 83 (6), 919. https://doi.org/10.1021/ed083p919.

  6. Sorensen, P. W.; Fine, J. M.; Dvornikovs, V.; Jeffrey, C. S.; Shao, F.; Wang, J.; Vrieze, L. A.; Anderson, K. R.; Hoye, T. R. Mixture of New Sulfated Steroids Functions as a Migratory Pheromone in the Sea Lamprey. Nat Chem Biol 2005, 1 (6), 324–328. https://doi.org/10.1038/nchembio739.

  7. Hoye, T. R.; Jeffrey, C. S.; Tennakoon, M. A.; Wang, J.; Zhao, H. Relay Ring-Closing Metathesis (RRCM):  A Strategy for Directing Metal Movement Throughout Olefin Metathesis Sequences. J. Am. Chem. Soc. 2004, 126 (33), 10210–10211. https://doi.org/10.1021/ja046385t.

 

Book Chapters and Proceedings

  1. Jeffrey, C. S.; Tucker, M. J.; Varganov, S. A.; Sun, H.; Barile, C. J.; Mahmud, T.; Moore, D. C.; Dergachev, I. D.; Larson, G.; Feng, Y. Unraveling the Photophysical and Redox Characteristics of Microbial Pigments That Are Relevant to Survivability on Early Earth; 2024; Vol. 3068, p 2103.

  2. Griffin, E. A.; English, A. R.; Jeffrey, C.; Carson, W. P. Foliar Microbes as Drivers of Plant Performance and Trophic Dynamics. 2024. https://doi.org/10.5479/si.26882395.

  3. Dyer, L. A.; Jeffrey, C. S. Chemically Mediated Multi-Trophic Interactions. In Plant-Animal Interactions: Source of Biodiversity; Del-Claro, K., Torezan-Silingardi, H. M., Eds.; Springer International Publishing: Cham, 2021; pp 17–38. https://doi.org/10.1007/978-3-030-66877-8_2.

 

Articles In-Review​​

  1. Salcido, D.; Richards, L. A.; Smilanich, A. M.; Wagner, D. L.; Sudta, C.; Pardikes, N. A.; Glassmire, A. E.; Jeffrey, C. S.; Massad, T. J.; Rullman, S.; Kania, S.; Dyer, L. A. Immersive Citizen Science Programs as a Partnership Model for Biodiversity Researchers to Engage Corporate Employees in Research. Biol. Conserv., (in revision), Apr 2025.

  2. Kato, M.J.; Yamaguchi, L.; Franco, T.; Stanton, M.; Jeffrey, C.S. Ecologica Quimica, in Natural Products Chemistry, Brazilian Chemical Society, 2023, submitted.

 

Patents and Patent Applications

  1. Nitrogen-Containing Heterocyclic Compounds and Methods of Making the Same, US Patent Application No. 13/450,914 (Inventor: C. Jeffrey).

  2. Chemical Synthesis Method for Making Scytonemin and Analogs and/or Derivatives Thereof, Provisional Patent Application No. 63/681,552, filed August 9, 2024.

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