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Publications

Published Articles

  1. 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.

  2. 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.

  3. 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.

  4. 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.

  5. 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.

  6. 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.

  7. 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.

  8. 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.

  9. 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.

  10. 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.

  11. 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.

  12. 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.

  13. 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.

  14. 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.

  15. 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.

  16. 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.

  17. 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.

  18. 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.

  19. 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.

  20. 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.

  21. 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.

  22. 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.

  23. 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.

  24. 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.

  25. 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.

  26. 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.

  27. 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.

  28. 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.

  29. 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.

  30. 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.

  31. 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.

  32. 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.

  33. 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.

  34. 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.

  35. 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.

  36. 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.

  37. 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. Garrett E. Larson, Tanzil Mahmud, Ilya D. Dergachev, Casey S. Philbin, Yingshi Feng, Celso R. de Oliveira, Henry Sun, Matthew J. Tucker, Sergey A. Varganov, Christopher S. Jeffrey. Revision of the Structure of Scytonemin Imine and Its Relationship to Scytonemin: Chromism and Implications for Astrobiology and Cyanobacterial Adaptability. (in review), April 14, 2025.

  2. Tejinder Singh, Christos Georgiou, Christopher Jeffrey, Matthew Tucker, Casey Philbin, Tanzil Mahmud, Christopher McKay, Henry Sun. UVC-intense exoplanets may not be uninhabitable: evidence from desert lichens. Astrobiology (in review), Manuscript ID: AST-2024-0137.R1; Submitted: March 14, 2025.

  3. Celso Oliveira, Megan Burroughs, Lora A. Richards, Lee A. Dyer, Federico Urbano-Munoz, Camryn Lee, Megan Warner, Craig D. Dodson, Ian S. Wallace, and Christopher S. Jeffrey. 1H-NMR Guided Isolation of Bioactive Compounds from Species of the Genus Piper. Molecules (Apr. 2025), In–Revision.

  4. 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.

  5. 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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