Jordan K. Zjawiony
Professor of Pharmacognosy
Research Professor in the Research Institute of Pharmaceutical Sciences
Dr. Zjawiony received his B.S. and M.Sc. in Chemistry from the Technical University of Lodz, Poland in 1965, and the Ph.D. in Organic Chemistry in 1974 from the same University. He joined the Institute of Organic Chemistry of the Technical University in Lodz in 1965 as a Research Assistant to become later in 1968 a Senior Research Assistant. In 1975 he was promoted to Assistant Professor at the same Institute. In 1978 he came to the United States as a Postdoctoral Fellow, under the Fogarty International Fellowship to work in the area of beta-adrenergic antagonists in the Gerontology Research Center, National Institute on Aging, National Institutes of Health in Baltimore, Maryland. In 1988 he was awarded the Fulbright Grant for a research project in the field of new cardiovascular drugs, which was performed in the United States. In 1989 he joined The University of Mississippi, where he became Associate Professor of Pharmacognosy and Research Associate Professor in the Research Institute of Pharmaceutical Sciences in 1992. In 1999 he was promoted to Professor of Pharmacognosy and Research Professor in the Research Institute of Pharmaceutical Sciences.
Click here to see Research in Progress and Publications
Research in Progress
Dr. Zjawiony’s main research interest is focused on natural products chemistry of biologically active constituents of psychoactive plants and fungi. The strong emphasis in current research is placed on discovery and development of new kappa-opioid ligands from hallucinogenic plants. Dr. Zjawiony’s research group is developing new derivatives and analogs of salvinorin A, the major active component of hallucinogenic plant Salvia divinorum. Salvinorin A is the first known non-alkaloidal kappa-opioid receptor agonist with potency equal to the synthetic hallucinogen, LSD. Chemical modifications of the structure of salvinorin A may provide new ligands to kappa-opioid receptor, especially new antagonists that may serve as models for the development of new drugs for CNS disorders.
Another project in progress is oriented toward the synthesis of aplysinopsin analogs as new agents interacting with serotonin receptors. This work originated from a natural product aplysinopsin isolated from marine sponges. Synthesis of new analogs of this natural product produces compounds with selective affinity to to 5HT2A and 5HT2C subtypes of serotonin receptors responsible for controlling depression and obesity, respectively.
Dr. Zjawiony is involved in several collaborative projects such as synthesis and identification of new affinity ligands to kappa-opioid receptors (with Dr Bryan Roth, University of North Carolina at Chapel Hill), pharmacology of natural products from psychoactive plants and fungi (with Dr. Raffaele Capasso, University of Naples, Italy), identification of bioactive secondary metabolites from mushrooms (with Dr. Krzysztof Grzywnowicz, M. Curie-Sklodowska University, Lublin, Poland), and steroidogenesis and neuroendocrinology of the skin and connective tissue (with Dr. Andrzej Slominski, University of Tennessee in Memphis).
Abeer Moawad, Mona Hetta, Jordan K Zjawiony, Melissa R. Jacob, Mohamed Hifnawy, Jannie P. J. Marais and Daneel Ferreira. “Phytochemical investigation of Cycas circinalis and Cycas revoluta leaflets”. Link Planta Medica 2010, 76, 796-802.
Tae-Kang Kim, Jianjun Chen, Wei Li, Jordan Zjawiony, Duane Miller, Zorica Janjetovic, Robert C. Tuckey, Andrzej Slominski. “A new steroidal 5,7-diene derivative, 3b-hydroxyandrosta-5,7-diene-17b-carboxylic acid, shows potent antiproliferative activity”. Steroids, 2010, 75, 230-239.
Andrzej T. Slominski, Zorica Janjetovic, Brian E. Fuller, Michal A. Zmijewski, Robert C. Tuckey, Minh N, Nguyen, Trevor Sweatman, Wei Li, Jordan Zjawiony, Duane Miller, Tai C. Chen, Gerard Lozanski, Michael Holik. “Products of vitamin D3 or 7-dehydrocholesterol metabolism by cytochrome P450scc show anti-leukemia effects, having low or absent calcemic activity.” Link PLoS ONE, 2010, 5, e9907, 1-13.
Y. S. Hu, Hesham Fahmy, Jordan K. Zjawiony, G. E. Davies. “Inhibitory effect and transcriptional impact of berberine and evodiamine on human white preadipocyte differentiation.” Link Fitoterapia, 2010, 81, 259-268.
Lukasz M. Kutrzeba, Xing-Cong Li, Yuanqing Ding, Daneel Ferreira, and Jordan K. Zjawiony. “Intramolecular transacetylation in salvinorins D and E”, Link J. Nat. Prod., 2010, 73 (4), 707-708).
M. A. Zmijewski, W. Li, J. K. Zjawiony, J. Chen, D. D. Miller, A. T. Slominski, “Photo-conversion of two epimers (20R and 20S) of pregna-5,7-diene-3 ,17a,20-triol and their bioactivity in melanoma cells”, Link Steroids 2009, 74, 218-228.
Andrzej T. Slominski, Michal A. Zmijewski, Igor Semak, Trevor Sweatman, Zorica Janjetovic, Wei Li, Jordan K. Zjawiony, Robert C. Tuckey, “Sequential metabolism of 7-dehydrocholesterol to steroidal 5,7-dienes in adrenal glands and its biological implication in the skin”, Link PLoS ONE, 2009, 4, e4309, 1-18.
Paulo Carvalho, Lukasz M. Kutrzeba, Jordan K. Zjawiony and Mitchell A. Avery. “(2S, 4aR, 6aR, 7R, 9S, 10aS, 10bR)-7-carboxy-2-(3-furyl)-6a,10b-dimethyl-4,10-dioxoperhydrobenzo[f]isochromen-9-yl acetate”, Link Acta Cryst. E., 2009 E65, o471-o472.
Jordan Zjawiony. “Antimicrobial and Antiviral Metabolites from Polypore Fungi” in “Novel Therapeutic Agents from Plants”, Eds. M.C. Carpinella and M. Rai, Science Publishers, Enfield, New Hampshire, USA, 2009, 36-59.
Dobroslawa Bialonska and Jordan K. Zjawiony. “Aplysinopsins –marine indole alkaloids: chemistry, bioactivity and ecological significance”. Link Marine Drugs, 2009, 7, 166-183.
Feng Yan, Ruslan V. Bikbulatov,V. Mocanu, Nedyalka Dicheva, Carol E. Parker, William C. Wetsel, Philip D. Mosier, Richard B. Westkaemper, John A. Allen, Jordan K. Zjawiony and Bryan L. Roth. “Structure-Based Design, Synthesis, and Biochemical and Pharmacological Characterization of Novel Salvinorin A Analogues as Active State Probes of the κ-Opioid Receptor”. Link Biochemistry, 2009, 48, 6898-6908.
Lukasz M. Kutrzeba, Daneel Ferreira, and Jordan K. Zjawiony. “Salvinorins J from Salvia divinorum: Mutarotation in the Neoclerodane System”, Link J. Nat. Prod., 2009, 72, 1361-1363.
J. Fichna, R. Schicho, A. Janecka, J. K. Zjawiony, M. Storr. “Selective natural KOR and CB1 agonists with potential role in gastrointestinal dysfunction”,Link Drug News & Perspectives, 2009 in press.
Lukasz M. Kutrzeba, Vardan T. Karamyan, Robert C. Speth, John S. Williamson and Jordan K. Zjawiony. “In vitro studies on metabolism of salvinorin A”, Link Pharm. Biol, 2009, in press.
Jakub Fichna, Rudolf Schicho, Christopher N. Andrews, Mohammad Bashashati, M. Klompus, Derek McKay, K.A. Sharkey, Jordan K. Zjawiony, Anna Janecka, Martin A. Storr. “Salvinorin A inhibits colonic transit and neurogenic ion transport in mice by activating κ-opioid and cannabinoid receptors”, Link Neurogastroenterology and Motility, 2009, accepted.
Lukasz M. Kutrzeba, Daneel Ferreira, and Jordan K. Zjawiony. “Intramolecular transacetylation in salvinorins D and E”,Link J. Nat. Prod., 2009, submitted.
Ruslan V. Bikbulatov, Jeremy Stewart, Wentao Jin, Feng Yan, Bryan L. Roth, Daneel Ferriera and Jordan K. Zjawiony. Short Synthesis of a Novel Class of Salvinorin A Analogs with Hemiacetalic Structure”, Link Tetrahedron Lett., 2008, 49, 937-940.
R. Capasso, F. Borrelli, J. Zjawiony, L. Kutrzeba, G. Aviello, G. Sarnelli, F. Capasso, A.A. Izzo. “The hallucinogenic herb Salvia divinorum and its active ingredient salvinorin A reduce inflammation-induced hypermotility in mice”. Link Neurogastroenterology and Motility, 2008, 20, 142-148.
Lukasz M. Kutrzeba, Franck E. Dayan, José-Luis Giner, Jordan K. Zjawiony, “13C and 2H Labeled Deoxyxylulose as a Tool in Study of Kinetics and Mechanism of Salvinorin A Biosynthesis”, abstract from 7th Annual Oxford International Conference on the Science of Botanicals & American Society of Pharmacognosy 4th Interim Meeting, University, MS, April 12-16, 2008, Planta Medica, 2008, 74, 331-332.
Lukasz M. Kutrzeba, Jordan K. Zjawiony, Franck E. Dayan, “Salvinorin B as a Putative Biosynthetic Precursor of Salvinorin A. Study on O-acetyltransferase in Glandular Trichomes Isolated from Salvia divinorium”, abstract from 7th Annual Oxford International Conference on the Science of Botanicals & American Society of Pharmacognosy 4th Interim Meeting, University, MS, April 12-16, 2008, Planta Medica, 2008, 74, 332.
Paulo Carvalho, Ruslan Bikbulatov, Jordan K. Zjawiony and Mitchell Avery. “Unusual Hemi-acetal Structure Derived from Salvinorin A”, Link Acta Cryst. E., 2008 E64, o1370-o1371.
Robert C. Tuckey, Wei Li, Jordan K. Zjawiony, Michal A. Zmijewski, Minh N. Nguyen, Trevor Sweatman, Duane Miller and Andrzej Slominski, “Pathways and Products for the Metabolism of Vitamin D3 by Cytochrome P450scc (CYP11A1)”, Link FEBS J., 2008 275, 2585-2596.
M. A. Zmijewski, W. Li, J. K. Zjawiony, T. W. Sweatman, J. Chen, D. D. Miller, A. T. Slominski, “Synthesis and Photoconversion of Androsta- and Pregan-5,7-dienes to Vitamin D3-like derivatives”, Link Photochem. Photobiol. Sci., 2008, 7, 1570-1576.
Robert. C. Tuckey, Zorica Janetovic, Wei Li, Minh N. Nguyen. Micjal A Zmijewski, Jordan Zjawiony and Andrzej Slominski, “Metabolism of 1a-hydroxyvitamin D3 by cytochrome P450scc to biologically active 1a,20-dihydroxyvitamin D3”, J. Steroid Biochem. Mol. Biol., 2008, 112, 213-219.
R. Capasso, F. Borrelli, M. Cascio, G. Aviello, K. Huben, J. Zjawiony, P. Marini, B. Romano, V. DiMarzo, F. Capasso, A. Izzo. “Inhibitory effect of salvinorin A from Salvia divinorum on ileitis-induced hypermotility: cross-talk between κ-opioid and cannabinoid CB1 receptors”. Link Brit. J. Pharmacol. 2008, 155, 681-689.
Jose-Luis Giner, David J. Kiemle, Lukasz Kutrzeba and Jordan Zjawiony. “Unambiguous NMR spectral assignments of salvinorin A”, Link Magn. Reson. Chem., 2007, 45, 351-354.
Jordan K. Zjawiony. “Antitubercular Activity of Mushrooms (Basidiomycetes) and Their Metabolites”, Nat. Prod. Comm., 2007, 2, 315-318.
Ruslan V. Bikbulatov, Feng Yan, Bryan L. Roth, and Jordan K. Zjawiony. “Convenient Synthesis and in Vitro Pharmacological Activity of 2-Thioanalogs of Salvinorin A and B”, Link Bioorg, Med. Chem. Lett., 2007, 17, 2229-2232.
Jordan K. Zjawiony, Wentao Jin, Leif Ryvarden, Scott G. Franzblau. "Antitubercular Activity of Metabolites of Higher Basidiomycetes", Int. J Med. Mushr., 2007, 9,220-221.
Ruslan V. Bikbulatov, Feng Yan, Bryan L. Roth, and Jordan K. Zjawiony. “Convenient Synthesis and in Vitro PharmacologicalActivity of 2-Thioanalogs of Salvinorin A and B”, Link Bioorg, Med. Chem. Lett., 2007, 17, 2229-2232.
R. Capasso, F. Borrelli, F. Capasso, D. J. Siebert, D. J. Stewart, J. K. Zjawiony, and A. A. Izzo. “The hallucinogen herb Salvia divinorum and its active ingredient salvinorin A inhibit enteric cholinergic transmission in the guinea pig ileum”, Link Neurogastroenterology and Motilit, 2006. 18, 69-75.
Wentao Jin and Jordan K. Zjawiony. “5-Alkylresorcinols from Merulius incarnatus”, Link J. Nat. Prod., 2006, 69, 704-706.
Michael A. Ansonoff, Jiwen Zhang, Traci Czyzyk, Richard B. Rothman, Jeremy Stewart, Heng Xu, Jordan Zjawiony, Daniel J. Siebert, Feng Yan, Bryan L. Roth, and John E. Pintar. “Antinociceptive and Hypothermic Effects of Salvinorin A Are Abolished in a Novel Strain of k-Opioid Receptor-1 Knockout Mice”, Link J. Pharmacol. Exp. Ther., 2006, 318, 641-648.
F. Yang, P. D. Mosier, R. B. Westkaemper, J. Stewart, J. K. Zjawiony, T. A. Vortherms, D. J. Sheffler, B. L. Roth. “Identification of the Molecular Mechanism by which the Diterpenoid Salvinorin A Binds to k-Opioid Receptor”, Link Biochemistry, 2005, 44(24), 8643-8651.
A. Slominski, I. Sermak, J. Zjawiony, J. Wortsman, Wei Li, A. Szczesniewski, R.C. Tuckey. “The Cytochrome P450scc system Opens an Alternate Pathway of Vitamin D3 Metabolism” Link , FEBS Journal, 2005, 272, 4080-4090.
M. A. Ansonoff, J. Zhang, T. Czyzyk, R. B Rothman, J. Stewart, J. Zjawiony, D. J. Siebert, B. L. Roth, J. E. Pintar.” In vivo Actions of Salvinorin A are Mediated by the KOR-1 Gene”, 2005.
A. Slominski, J. Zjawiony, W. Li, J. Wortsman, I. Semak, B. Zbytek, R. C. Tuckey. "Enzymatic metabolism of ergosterol by cytochrome P450scc (CYP11A1) to biologically active 17,24-dihydroxyergosterol.", Link Chemistry and Biology, 2005.
H. Fahmy, S.I. Khalifa, T. Konoshima, J. K. Zjawiony. “An Improved Synthesis of 7, 8-Epoxy-1,3,11-cembratriene-15R(), 16-diol, a Cembranoid of Marine Origin with a Potent Cancer Chemopreventive Activity” ,Link Marine Drugs, 2004, 1, 1-7.
J. Stewart, I. Katsuyama, H. Fahmy, F.R. Fronczek, and J.K. Zjawiony,” A Direct Synthesis of 3,5-Dibromo-O-Methyl-L-Tyrosine”, Link Synthetic Commun., 2004, 34(3), 547-555.
Charles Chavkin, Sumit Sud, Wenzhen Jin, Jeremy Stewart, Jordan K. Zjawiony, Daniel J. Siebert, Beth Ann Toth, Sandra J. Hufeisen, and Bryan L. Roth, “Salvinorin A, an Active Component of the Hallucinogenic Sage Salvia divinorum, is a Highly Efficacious Kappa Opioid Receptor Agonist: Structural and Functional Considerations”, Link J. Pharmacol. Exp. Ther., 2004, 308(3), 1197-1203.
J. K. Zjawiony, “Biologically Active Compounds from Aphyllophorales (Polypore) Fungi”, Link J. Nat. Prod., 2004, 67, 300-310.
A. Slominski, J. Zjawiony, J. Wortsman, I. Semak, J. Stewart, A Pisarchik, T. Sweatman, J. Marcos, C. Dunbar, R.C. Tuckey. “A Novel Pathway for Sequential Transformation of 7-Dehydrocholesterol and Expression of the P450scc System in Mammalian Skin”, Link Eur. J. Biochem., 2004, 271, 4178-4188.
Hesham Fahmy, Jordan K. Zjawiony, Sheiref Khalifa and Frank Fronczek, „A Semisynthetic Analog of the Cembranoid Sarcophine”,Link Acta Cryst., 2003, C59, o85-o87.
Gochfeld, D.J., K.A. El Sayed, M. Yousaf, J.F. Hu, P. Bartyzel, D.C. Dunbar, S.P. Wilkins, J.K. Zjawiony, R.F. Schinazi, S.Schlueter-Wirtz P.M. Tharnish and M.T. Hamann, “Marine Natural Products as Lead Anti-HIV Agents", Link Mini Rev. Med. Chem., 2003, 3, 401-425.
Hesham T.Y. Fahmy, Sherif A.F. Rostom, Manal N. Saudi, Jordan K. Zjawiony, David J. Robins. Synthesis and in-vitro evaluation of the anticancer activity of novel fluorinated thiazolo[4,5-d]pyrimidines Link. Arch. Pharm. Pharm. Med. Chem., 2003, 336, 216-225.
I. Katsuyama, A.A. Khalil, C. Dunbar, and J. K. Zjawiony, “Concentration-Dependent Variation in 1H-NMR Chemical Shifts of Aromatic Protons in Sampangine Derivatives”, Link Spectroscopy Letters., 2003, 36(5 & 6), 477-485.
Xing-Cong Li, Alpana S. Joshi, Bo Tan, Hala N. ElSohly, Larry A. Walker, Jordan K. Zjawiony, and Daneel Ferreira, “Absolute Configuration, Conformation and Chiral Properties of Flavanone-(3-8’’)-flavone Biflavanoids from Rheedia acuminata”, Tetrahedron, 2002, 58, 8709-8717.
Isamu Katsuyama, H. Fahmy, and J. K. Zjawiony, Sherief I. Khalifa, Raouf W. Kilada, Takao Konoshima, Midori Takasaki, and Harakuni Tokuda, “Semisynthesis of New Sarcophine Derivatives with Chemopreventive Activity”, Link J. Nat. Prod., 2002, 65, 1809-1814.
I. Katsuyama, A. A. Khalil, J. Ren, J. K. Zjawiony, “The Identification, Mechanism, and Improved Synthesis of a New and Unique Heterocyclic System with a Fused Imidazole Ring”, Link Heterocycles, 2001, 54,721-726.
K. A. ElSayed, D. C. Dunbar, P. Bartyzel, J. K. Zjawiony, W. Day, and M.T. Hamann, "Marine Natural Products as Leads to Develop New Drugs and Insecticides", Link in Biologically Active Natural Products: Agrochemicals and Pharmaceuticals, CRC Press, Boca Raton, FL, 2000, 233-252.
Khalid A. El-Sayed, Piotr Bartyzel, Xiaoyu Shen, Tony L. Perry, Jordan K. Zjawiony, and Mark T. Hamann, "Marine Natural Products as Antituberculosis Agents," Link Tetrahedron, 56, 2000, 949-953.
I. Katsuyama and J.K. Zjawiony, "Theoretical and Experimental Aspects of Bromination of Sampangine," link Chem. Letters, 2000, 568-569.
F. E. Dayan, A. C. Vincent, J. G. Romagni, S. N. Allen, S. O. Duke, M. V. Duke, J. J. Bowling, and J. K. Zjawiony, “Amino-and Urea-substituted Thiazoles Inhibit Photosynthetic Electron Transfer”, Link J. Agric. Food Chem., 2000, 48, 3689-3693.