Keywords

• Discovery, isolation, and structure determination of new biologically active natural products from fungi
• Anticancer agents
• Antifungal agents
• Natural insecticides
• Fungal chemical ecology

Focus areas

• Natural Products/Medicinal

Biosketch

• Postdoctoral Research Associate, Cornell University (1983-84)
• Alfred P. Sloan Foundation Fellow (1990-92); NIH Research Career Development Award, (1990-95)
• President, American Society of Pharmacognosy, 1999-2000
• Collegiate Fellow, UI College of Liberal Arts and Sciences, 2004-2007
• 2007 Regents Award for Faculty Excellence
• 2010 Graduate College Outstanding Faculty Mentor Award (Math, Physical Sciences, and Engineering)
• Fellow of the American Society of Pharmacognosy, 2010-present
• Norman R. Farnsworth Research Achievement Award, 2018

Research interests

Our research program is dedicated mainly to the discovery, isolation, and structure determination of novel biologically active natural products from fungi.  Many antibiotics, anticancer agents, and other important pharmaceuticals and agrochemicals in use today have been discovered through studies of the chemistry of bacteria and fungi.  Our studies utilize observations in fungal ecology in order to target certain classes of fungi as logical sources of valuable new metabolites.  Through these studies, we also seek to contribute to a better understanding of the roles of these compounds in the life cycles of the organisms that produce them.  Current efforts in this area include studies of fungal metabolites involved in interspecies competition within natural ecosystems, and investigations of fungi that attack, colonize, and damage others as potential sources of antifungal agents.  This research is interdisciplinary, and most of our projects involve collaboration with mycologists and colleagues from other neighboring disciplines.

The process of discovering and isolating biologically active natural products is guided by assays that have pharmaceutical or agricultural relevance, including antifungal, antibacterial, antiinsectan, and anticancer screens.  Some of these bioassays are carried out by our research group, while others are conducted by collaborating scientists.  We employ a variety of chromatographic techniques, especially HPLC, in the analysis, isolation, and purification of compounds of interest.  State-of-the-art methods for structure determination, such as high resolution mass spectrometry, high-field ¹H and ¹³C NMR spectroscopy, and 2D-NMR techniques are then applied to the solution of structural and stereochemical problems.  Some representative new bioactive natural products discovered by our research group are shown in the accompanying figure.  These metabolites exemplify the prolific biosynthetic capabilities of fungi, and include compounds with new ring systems and representatives of other rare structural classes.

Recent publications

2020

• Campafungins: Inhibitors of Candida albicans and Cryptococcus neoformans Hyphal Growth.  Perlatti, B.; Harris, G.; Nichols, C.; Ekanayake, D.; Alspaugh, J.A.; Gloer, J.B.; Bills, G.F.  J. Nat. Prod. 2020, 83, 2718–2726.
• Photolysis of trenbolone acetate metabolites in the presence of nucleophiles: Evidence for metastable photoaddition products and reversible associations with dissolved organic matter.  Pflug, N.C.; Kral, A.; Hankard, M.; Breuckman, K.; Kolodziej, E.P.; Gloer, J.B.; Wammer, K.H.; Cwiertny, D.M.  Environ. Sci. Technol. 2020, 54, 12181–12190.
• Arenicolins: C-Glycosylated Depsides from Penicillium Arenicola.  Perlatti, B.; Lan, N.; Earp, C.E.; AghaAmiri, S.; Vargas, S.H.; Azhdarinia, A.; Bills, G.F.; Gloer, J. B.  J. Nat. Prod. 2020, 83, 668–674.
• Gakolanone: a new benzophenone derivative from Garcinia kola Heckel stem-bark.  Akoro, S.; Aiyelaagbe, O.; Onocha, P.; Gloer, J.B.  Nat. Prod. Res. 2020, 34, 241-250.  

2019

• Intramolecular [2+2] Photocycloaddition of Altrenogest: Confirmation of Product Structure, Theoretical Mechanistic Insight, and Bioactivity Assessment.  Pflug, N.C.; Patterson, E.V.; Martinovic-Weigelt, D.; Kolodziej, E.P.; Gloer, J.B.; McNeill, K.; Cwiertny, D.M.; Wammer, K.H.  J. Org. Chem. 2019, 84, 11366−11371.
• Bioactive Rearrangement Products from Aqueous Photolysis of Pharmaceutical Steroids. Pflug, N.C.; Knutson, C.J.; Martinovic-Weigelt, D.; Swenson, D.C.; Wammer, K. H.; Cwiertny, D.M.; Gloer, J.B.  Org. Lett.  2019, 21, 3568-3571.
• Wortmannin and Wortmannine Analogues from an Undescribed Niesslia sp.  Dischler, N. M., Xu, L., Li, Y., Nichols, C. B., Alspaugh, J. A., Bills, G. F., Gloer, J. B.  J. Nat. Prod. 2019, 82, 532-538.

2018

• Identification of cyclosporin C from Amphichorda felina using a Cryptococcus neoformans differential temperature sensitivity assay.  Xu, L.; Li, Y.; Gloer, J. B.; Alspaugh, A.; Bills, G. F., Appl. Microbiol. Biotechnol. 2018, 102, 2337-2350. 
• Isolation, Synthesis, and Radical-Scavenging Activity of Rhodomelin A, a Ureidobromophenol from the Marine Red Alga Rhodomela confervoides.  Li, K.; Wang, Y.-F.; Li, X.-M.; Wang, W.-J.; Ai, X.-Z.; Li, X.; Yang, S.-Q.; Gloer, J. B.; Wang, B.-G.; Xu, T.  Org. Lett. 2018, 20, 417-420.
• Biologically Active Secondary Metabolites from the Fungi.  Bills, G. F.; Gloer J. B.  Chapter 54 in The Fungal Kingdom.  Heitman, J.; Howlett, B. J.; Crous, P. W.; Stukenbrock, E. H.; James, T. Y., Gow, N. A. R., Eds.  American Society for Microbiology, Washington, DC.  2018, pp 1087-1119.

2017

• Environmental Photochemistry of Dienogest: Phototransformation to Estrogenic Products and Increased Environmental Persistence via Reversible Photohydration.  Pflug, N.C.; Hankard, M.K.; Berg, S.M.; O’Connor, M.; Gloer, J.B.; Kolodziej, Cwiertny, D.M.; Wammer, K. H.  Environ. Sci. Processes & Impacts 2017, 19, 1414-1426
• New Anti-Cryptococcus Phenalenones and Cyclic Tetrapeptides from Auxarthron pseudauxarthron.  Li, Y.; Yue, Q.; Jayanetti, D.R.; Swenson, D. C.; Bartholomeusz, G A.; An, Z.; Gloer, J. B.; Bills, G.F.  J. Nat. Prod. 2017, 80, 2101-2109.
• Formation of Bioactive Transformation Products during Glucocorticoid Chlorination.  Pflug, N.C.;  Kupsco, A.; Kolodziej, E.P.; Schlenk, D.; Teesch, L.M.; Gloer, J.B.; Cwiertny, D.M.    Environ. Sci.-Water Res. Tech., 2017, 3, 450-461. 
• Benzophenone and Fimetarone Derivatives from the Coprophilous Fungus Delitschia confertaspora.  Jayanetti, D.R.; Li, Y.; Bartholomeusz, G.A.; Bills, G.F.; Gloer, J. B.  J. Nat. Prod. 2017, 80, 707−712.

2016

• Emestrins: anti-Cryptococcus epipolythiodioxopiperazines from Podospora australis.  Li, Y.; Yue, Q.;Krausert, N.M.; An, Z.; Gloer, J.B.; Bills, G. F.  J. Nat. Prod., 2016, 79, 2357-2363.
• Biologically Active Secondary Metabolites from the Fungi.  Bills, G. F.; Gloer J. B.In The Fungal Kingdom, Heitman, J.; Howlett, B.; Crous, P.; Stukenbrock, E.; James, T.; Gow, N., Eds. ASM Press, Microbiol. Spectr. 2016, 4, FUNK-0009-2016, 32 pp. 
• Haenamindole and fumiquinazoline analogues from a fungicolous isolate of Penicillium lanosum.  Hwang, I. H.; Che, Y.; Swenson, D.C.; Gloer, J. B.; Wicklow, D. T.; Peterson, S. W.; Dowd, P. F.  J. Antibiot., 2016, 69, 631-636.
• New Punctaporonins from Two Fungicolous Isolates of Pestalotiopsis Sp.  Hwang, I. H.; Wicklow, D. T.; Gloer, J. B.  Phytochem. Lett., 2016, 16, 257-262
• New Monomeric Stilbenoids from Fungus-Challenged Peanut (Arachis hypogaea) Seeds.  Sobolev, V. S.; Krausert, N. M.; Gloer, J. B .J. Agric. Food Chem., 2016, 64, 579-584.
• Disseminins and Spiciferone Analogues:Polyketide-derived Metabolites from a Fungicolous Isolate of Pestalotiopsis disseminata.  Hwang, I. H.; Swenson, D. C.; Gloer, J. B., Wicklow, D. T.  J. Nat. Prod., 2016, 79, 523-530.

2015

• Cycloexpansamines A and B: Spiroindolinone alkaloids from a marine isolate of Penicillium sp. (SF-5292).  Oh, H.; Lee, C.; Sohn, J. H.; Jang, J.-H.; Ahn, J. S.; Baltrusaitis, J.; Hwang, I. H.; Gloer, J. B.  J. Antibiot., 2015, 68, 715-718.
• Pestaloporonins:  Caryophyllene-derived Sesquiterpenoids from a Fungicolous Isolate of Pestalotiopsis Sp.  Hwang, I. H.; Swenson, D. C.; Gloer, J. B., Wicklow, D. T.  Org. Lett. 2015, 17, 4284–4287.
• Hypocoprins A-C:  New Sesquiterpenoids from the Coprophilous Fungus Hypocopra rostrata (Xylariales).  Jayanetti, D. R.; Yue, Q.; Bills, G. F.; Gloer, J. B.  J. Nat. Prod., 2015, 78, 396-401.

2014

• Bioactive Natural Products from Fungicolous Hawaiian Isolates:  Secondary Metabolites from a Phialemoniopsis sp.  Kaur, A.; Rogers, K. D.; Swenson, D. E.; Dowd, P.F.; Wicklow, D.T.; Gloer, J. B.  Mycology 2014, 5, 120-129.
• First Total Syntheses and Antimicrobial Evaluation of Penicimonoterpene, a Marine-derived Monoterpenoid and Its Various Derivatives.  Zhao, J.-C.; Li, X.-M.; Gloer, J. B.; Wang, B-G.  Marine Drugs 2014, 12, 3352-3370.
• Pyrano-isoflavans from Glycyrrhiza uralensis with Antibacterial Activity against Streptococcus mutans and Porphyromonas gingivalis.  Villinski, J.; Bergeron, C.; Cannistra, J.; Gloer, J. B.; Coleman, C.; Ferreira, D.; Azelmat, J.; Grenier, D.; Gafner, S.  J. Nat. Prod. 2014, 77, 521-526.
• Diplodiatoxin, Chaetoglobosins, and Diplonine Associated with a Field Outbreak of Stenocarpella Ear Rot in Illinois.   Rogers, K. D.; Cannistra, J. C.; Gloer, J. B.; Wicklow, D.T., Mycotoxin Research 2014, 30, 61-70.

2013

• Coprophilous fungi: Antibiotic discovery and functions in an underexplored arena of microbial defensive mutualism.  Bills, G. F.; Gloer, J. B.; An, Z.  Curr. Opin. Microbiol., 2013, 16, 549–565.
• Product-to-Parent Reversion of Trenbolone: Unrecognized Risks for Endocrine Disruption.  Qu, S.;  Kolodziej, E. P.; Long, S. A.; Gloer, J. B.; Patterson, E. V.; Baltrusaitis, J.; Jones, G. D.; Benchetler, P. V.; Cole, E. A.; Kimbrough, K. C.; Tarnoff, M.; Cwiertny, D. M., Science 2013, 342, 347-351.
• Identification and Environmental Implications of Photo-Transformation Products of Trenbolone Acetate Metabolites.  Kolodziej, E.P.; Qu S.; Forsgren, K.; Long, S.A.; Gloer, J.B.; Jones, G.; Schlenk, D.; Baltrusaitis, J.; Cwiertny, D.M., Environ. Sci. Technol. 2013, 47, 5031−5041.
• Halogenated Organic Molecules of Rhodomelaceae Origin: Chemistry and Biology.  Wang, B.-G.; Gloer, J.B.; Ji, N.-Y; Zhao, J-C.  Chem. Rev. 2013, 113, 3632−3685.

2012

• New Nitrogen-containing Bromophenols from the Marine Red Alga Rhodomela confervoides and their Radical-Scavenging Activity.  Li, K.; Li, X.-M.; Gloer, J.B.; Wang, B.-G.  Food Chem. 2012, 135, 868-872.
• Fungal bis-Naphthopyrones as Inhibitors of Botulinum Neurotoxin Serotype A.  Cardellina, J.H., II;  Roxas-Duncan, V.I.; Montgomery, V.; Eccard, V.; Campbell,Y.; Hu, X.; Khavrutskii, I.; Tawa, G.J.; Wallqvist, A.; Gloer, J.B.; Phatak, N.L.; Höller, U.; Soman, A.G.; Joshi, B.K.;Hein, S.M.; Wicklow, D.T.; Smith, L.A.  ACS Med. Chem. Lett. 2012, 3, 387−391.
• Aflaquinolones A–G:  Secondary Metabolites from Marine and Fungicolous Isolates of Aspergillus Spp.  Neff, S.A; Lee, S. U.; Asami, Y; Ahn, J. S.; Oh, H.; Baltrusaitis, J.; Gloer, J. B.; Wicklow, D. T.  J. Nat. Prod. 2012, 75, 464-472.

2011

• Isolation, Characterization, and Antioxidant Activity of Bromophenols of the Marine Red Alga Rhodomela confervoides.  Li, K.; Li, X.-M.; Gloer, J.B.; Wang, B.-G.  J. Agric. Food Chem. 2011, 59, 9916-9921.
• Biological Activity of Peanut (Arachis hypogaea) Phytoalexins and Selected Natural and Synthetic Stilbenoids.  Sobolev, V. S; Khan, S.I.; Tabanca; N., Wedge, D.E.; Manly, S.P.; Cutler, S.J.; Coy, M.R.; Becnel, J.J.; Neff, S.A; Gloer, J.B.  J. Agric. Food Chem. 2011, 59, 1673-1682.
• Phomalevones A-C:  Dimeric and Pseudodimeric Polyketides from a Fungicolous Hawaiian Isolate of Phoma sp. (Cucurbitariaceae).  Shim, S. H.; Baltrusaitis, J.; Gloer, J. B.; Wicklow, D.T.  J. Nat. Prod. 2011, 72, 395-401.
• Bioactive Metabolites from Stenocarpella maydis, a Stalk and Ear Rot Pathogen of Maize.  Wicklow, D.T.; Rogers, K.D.; Dowd, P.F.; Gloer, J.B.  Fungal Biology 2011, 115, 133-142.

2010

• New Pterocarpenes Elicited by Aspergillus caelatus in Peanut (Arachis hypogaea) Seeds.  Sobolev, V. S; Neff, S.A; Gloer, J.B.; Khan, S.I.; Tabanca, N., De Lucca, A.J.; Wedge, D.E.  Phytochemistry 2010, 71, 2099-2107.
• New Nonadride Analogues from a Freshwater Isolate of an Undescribed Fungus Belonging to the Order Pleosporales.  Hosoe, T., Gloer, J. B.; Wicklow, D.T.; Raja, H..; Shearer, C. A.  Heterocycles 2010, 81, 2123-2130.
• New Dimeric Stilbenoids from Fungal-Challenged Peanut (Arachis hypogaea) Seeds.  Sobolev, V. S; Neff, S.A; Gloer, J.B.  J. Agric. Food Chem. 2010, 58, 875-881.
• Hymenopsins A and B and a Macrophorin Analogue from a Fungicolous Hymenopsis Sp.  Schmidt, L.E.; Deyrup, S.T.; Baltrusaitis, J.; Swenson, D.C.; Wicklow, D.T.; Gloer, J.B.  J. Nat. Prod. 2010, 73, 404-408.
• Radicinol Analogs from the Freshwater Aquatic Fungus Xylomyces chlamydosporus.  Hosoe, T., Gloer, J. B.; Raja, H..; Shearer, C. A.  Mycotoxins 2010, 60, 1-6.
• The Peanut Plant and Light: Spermidines from Peanut Flowers and Studies of their Photoisomerization.  Sobolev, V.S.; Sy, A.; Gloer, J. B., Chapter 2 in Organic Farming and Peanut Crops, Grossman, D.C.; Barrios, T.L., Eds., Nova Science Publishers, Inc., Hauppauge, NY, 2010, pp 65-102.

2009

• Antifungal metabolites (Monorden, Monocillins I, II, III) from Colletotrichum graminicola (Ces.) G.W. Wils. NRRL 47511, a systemic vascular pathogen of maize.  Wicklow, D. T.; Jordan, A. M; Gloer, J. B.  Mycol. Res., 2009, 113, 1433-1442.
• New Stilbenoids from Peanut (Arachis hypogaea) Seeds Challenged by an Aspergillus caelatus Strain.  Sobolev, V. S; Neff, S.A; Gloer, J.B.  J. Agric. Food Chem. 2009, 57, 62-68.

2008

• Halogenated sesquiterpenes and non-halogenated linear C15-acetogenins from the marine red alga Laurencia composita and their chemotaxonomic significance.  N.-Y. Ji, X.-M. Li, K. Li, J. B. Gloer, and B.-G. Wang.  Biochem.  Systemat. Ecol., 2008, 36, 938-941.
• Antifungal metabolites (Monorden, Monocillins I, II, III) from Colletotrichum graminicola (Ces.) G.W. Wils. NRRL 47511, a systemic vascular pathogen of maize.  Wicklow, D. T.; Jordan, A. M; Gloer, J. B.  Mycol. Res., 2009, 113, 1433-1442.
• Japodic acid, a novel aliphatic acid from Jatropha podagrica Hook. Aiyelaagbe, O.O.; Gloer, J.B. Rec. Nat. Prod. 2008, 2, 100-106.
• Urceolatin, a Structurally Unique Bromophenol from Polysiphonia urceolata.  Li, K.; Li,X.-M.; Ji, N.-Y.; Gloer, J. B.; Wang, B.-G., Org. Lett. 2008, 10, 1429-1432.
• Acremonium zeae, a Protective Endophyte of Maize, Produces Dihydroresorcylide and 7-Hydroxydihydroresorcylides.  Poling, S. M.; Wicklow, D. T.; Rogers, K.D.; Gloer, J. B.  J. Agric. Food Chem. 2008, 56, 3006-3009.
• Isolation, Structure Elucidation, and Biomimetic Total Synthesis of Versicolamide B and the Isolation of Antipodal (-)-Stephacidin A and (+)-Notoamide B from Aspergillus versicolor.  Greshock, T. J.; Grubbs, A.W.; Jiao, P.; Wicklow, D.T.; Gloer, J.B., Williams, R. M., Angew. Chem Int. Ed. Engl. 2008, 47, 3573-3577.(Selected as VIP article and also highlighted in Nature Chemistry)
• Spermidine and Flavonoid Conjugates from Peanut (Arachis hypogaea) Flowers.  Sobolev, V.S.; Sy, A.A.; Gloer, J. B.  J. Agric. Food Chem. 2008, 56, 2960-2969.
• Isolation of isocoumarin and isobenzofuran derivatives from a fungicolous isolate of Acremonium crotocinigenum.   Shim, S.-H.; Sy, A. A.; Gloer, J. B.; Wicklow, D. T.  Bull. Kor. Chem. Soc. 2008, 29, 863-865. 
• Botryolides A–E:  New Decarestrictine Analogues from a Fungicolous Botryotrichum Sp. (NRRL 38180).  Sy, A. A.; Swenson, D.C.; Gloer, J.B.; Wicklow, D.T.  J. Nat. Prod. 2008, 71, 415-419.

cv