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School of Pharmacy Division of Pharmacognosy

Daneel Ferreira

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Chair and Professor of Pharmacognosy
Research Professor in the Research Institute of Pharmaceutical Sciences

Daneel Ferreira graduated (B.Sc./H.E.D.) from the University of Pretoria, South Africa in 1964, and completed the B.Sc.(Hons.), M.Sc. and D.Sc (1973) programs of the Chemistry Department, University of the Orange Free State, Bloemfontein through part time studies. In 1969 he was appointed as Technical Assistant in the Chemistry Department at UOFS, and progressed through the ranks to Professor of Organic Chemistry in 1985, serving as chairperson of the Chemistry Department from 1994 - 1997. He spent 1977 as a Visiting Lecturer at Imperial College, London where he worked under the supervision of the Nobel laureate, the late Sir Derek Barton, and was awarded the Diploma of Imperial College for his work on the synthesis of aminoglycoside antibiotics. As an A-rated scientist he was invited to establish a Research Unit for Polyphenol and Synthetic Chemistry at UOFS by the Foundation for Research Development, Pretoria, South Africa, and was duly appointed as Director in 1990. He held this position until 1999, when he joined the Thad Cochran National Center for Natural Products Research at The University of Mississippi, U.S.A., as Visiting Scholar. In 2000, he was promoted to Principal Scientist and then appointed as Chair of The Department of Pharmacognosy in April, 2004.

email: dferreir@olemiss.edu

Click here to see Research in Progress and Publications

    Research in Progress

    My current research interests focus on:

    1. Identification of the class of compounds in the American Cranberry that is responsible for protecting against urinary tract infections in humans. It has been accepted for several years that such protection is caused by the A-type proanthocyanidins that occurred in cranberry. In collaboration with scientists at the University of Wisconsin/Madison and Rutgers University, our recent analysis of the urine of pigs fed with cranberry powder, indicate that the causative secondary metabolites may be oligosaccharide- rather than A-type proanthocyanidin-related. Our current efforts thus have an oligosaccharide than an oligoflavonoid focus.

    2. Of similar importance is the development of a synthesis protocol to access the A-type proanthocyanidin pool of the American Cranberry. In spite of several claims of the successful oxidative conversion of B- to A-type proanthocyanidins, it only works in low yields for analogues possessing pyrogallol-type B-rings, i.e. for prorobinetinidins and prodelphinidins, classes of compounds absent in the cranberry. Claims for the successful conversion of procyanidins with their catechol-type B-rings occurred in extremely low yields, or were substantiated by MS data indicating an [M-2] molecular ion. No NMR data were presented and the [M-2] ions most likely represented transient B-ring quinone methide intermediates. Our current efforts focus on the total synthesis of the A-type analogues rather than the perceived simple oxidative B- to A-type conversion.

    3. A large percentage of research time is focused on the definition of the absolute configuration of naturally occurring and synthetic organic molecules of a wide variety of classes via application of experimental and theoretically calculated Electronic Circular Dichroism (ECD) spectroscopy. The addition of the theoretical component has eliminated a large part of the "guess work" that is associated with the classical interpretation of ECD data via empirical rules. An extremely rewarding and international network has rapidly developed and we are now working with scientists from the US and across the globe to define configurational properties with this powerful chiroptical method that is independent of the state of the matter of the compounds.

    Representative Publications

    Absolute Configuration of (-)-Gambogic Acid, an Antitumor Agent.
    Y. Ren, C-H. Yuan, H-B. Chai, Y-Q. Ding, X-C. Li, D. Ferreira, and A. D. Kinghorn, J. Nat. Prod.,  2011, 74, 460-463.

    Labdane Diterpenoids from Leonurus sibiricus.                                                                 H. Wu, F.R. Fronczek, D. Ferreira, C. L. Burandt Jr, and J. K. Zjawiony, J. Nat. Prod., 2011, 74, 831-836.

    Towards the Synthesis of Proanthocyanidins: Half a Century of Innovation.
    D. Ferreira and C. Coleman, Planta Med,, Special Issue, 2011, 77, 1071 – 1085.

    Isoflavonoids and Coumarins from Glycyrrhiza uralensis: Antibacterial ActivityAgainst Oral Pathogens, and Conversion of  Isoflavans into Isoflavan-quinones During Purification.
    S. Gafner, C. Bergeron, M. Godejohann, P. Kessler, J. H. Cardellina II, D. Ferreira, K. El Feghali, and D. Grenier, J. Nat. Prod., 2011,74, 2514-2519.

     3-Bromohomofascaplysin A, a Fascaplysin Analogue from a Fijian Didemnum sp.   Ascidian.
    Z. Lu, Y. Ding, X-C. Li, D.R. Djigbenou, B. T. Grimberg, D. Ferreira,  C. M. Ireland, and R. M. Van Wagoner, Bioorg. & Med. Chem., 2011, 19, 6604 – 6607.

    Manuka Oil, a Natural Herbicide with Pre-emergence Activity.
    Franck E. Dayan, J’Lynn Howell, Jannie P. J. Marais, Daneel Ferreira, and Marja Koivunen, Weed Science, 2011, 59, 464-469.

    Photochemistry synthesis. Part 2: Enantiomerically pure polyhydroxy-1,1,3triarylpropan-2-ols.
    A. Wilhelm-Mouton, S. L.  Bonnet, Y. Ding, X-C. Li,  D. Ferreira, and J. H.             van  der Westhuizen, J. Photochem. & Photobiol., 2012, 227, 18-24.

    Conversion of Pravastatin Into an Advanced Intermediate for the Synthesis of the HMG-CoA Reductase Inhibitor BB-476. J.J.C. Grove, P.S. van Heerden, D. Ferreira, and B.C.B.Bezuidenhoudt. Link Tetrahedron Lett., 2010, 51, 57-59.

    Colon Cancer Chemopreventive Effects of Pomegranate Juice Ellagitannins and their Colonic Microfloral Metabolites. S. Kasimsetty, D. Bialonska, G. Ma, S.I.Khan, and D.Ferreira, J. Agric. & Food Chem., 2010, 58, 2180 - 2187.

    4-Arylflavan-3-ols as Proanthocyanidin Models: Absolute Configuration via Density Functional Calculations of Electronic Circular Dichroism.Y. Ding, X-C. Li, and D. Ferreira, Link
    J. Nat. Prod., 2010, 73, 435-440

    Anti-Infective Discorhabdins from a Deep-Water Alaskan Sponge of the Genus Latrunculia. M-K. Na, Y. Ding, B. Wang, B.L. Tekwani, R.F. Schinazi, S. Franzblau, M. Kelly, R. Stone, X-C. Li, D. Ferreira, and M.T. Hamann, Link J. Nat. Prod., 2010, 73, 383-387.

    Intramolecular Transacetylation inSalvinorins D and E. L. Kutrzeba, D. Ferreira, and J.K. Zjawiony, Link J. Nat. Prod., 2010, 73, 707–708.

    Phytochemical Investigation of Cycas circinalis and Cycas revoluta Leaflets: Moderately Active Antibacterial Biflavonoids. A. Moawad, M. Hetta, J. K. Zjawiony, M. R. Jacob, M. Hifnawy, and D. Ferreira, Link Planta Med., 2010, 76, 796-802.

                        Antiplasmodial Activity of (I-3, II-3)-Biflavonoids and Other Constituents from Ormocarpum kirkii. L. Dhooghe, S. Maregesi, I. Mincheva, D. Ferreira, J.P.J. Marais, F. Lemière, P. Cos, L. Maes, A. Vlietinck, S. Apers, and L. Pieters , http://www.malaria-world.org/article/antiplasmodial-activity-i-3ii-3-biflavonoids-and-other-constituents-ormocarpum-kirkii Phytochemistry, 2010, 71, 785-791.

    Phytochemical and Biological Investigations of Elaeodendron schlechteranum. S.M. Maregesi, N. Hermans, L. Dhooghe, K. Cimanga, D. Ferreira, C. Pannecouque, D.A. Vanden Berghe, P. Cos, L. Maes, A.J. Vlietinck, S. Apers, and L.Pieters, J. Ethnopharmacol., 2010, 129, 319-326.

    The Influence of Pomegranate By-product and Punicalagins on Selected Groups of Human Intestinal Microbiota.D. Bialonska, P. Ramnani, S.G. Kasimsetty, K.R. Muntha, G.R. Gibson, and D. Ferreira, Int. J. Food Microbiol., 2010, 140, 175-182.

    Proteasome-Inhibitory and Cytotoxic Constituents of Garcinia laterifolia: Absolute Configuration of Caged Xanthones. Y. Ren, E.J.C. de Blanco, L.B.S. Kardono, S. Riswan, H. Chai, C.E. Cottrell, N.R. Farnsworth, S.M. Swanson, Y.Ding, X-C. Li, J.P.J. Marais, D. Ferreira, and A.D. Kinghorn, Tetrahedron, 2010, 66, 5311-5320.        

    Determination of Absolute Configuration of Natural Products: Theoretical Calculation of Electronic Circular Dichroism as a Tool.X-C. Li, D. Ferreira, and Y. Ding, Link
    Current Organic Chemistry, 2010, in the press

    Bioactive 1,4-Dihydroxy-5-phenyl-2-pyridinone Alkaloids from Septoria pistaciarum. M. Kumarihamy, F.R. Fronczek, D. Ferreira, M. Jacob, S.I. Khan, and N.P.D. Nanayakkara, Link
     J.Nat. Prod., 2010, 73, 1250-1253.

    Photochemistry of Flavonoids. M. Sisa, S.L. Bonnet, D. Ferreira, and J. H. Van der Westhuizen, Link Molecules, 2010, 15, 5196-5245.

    Beyond Polymaxenolide: Cembrane-Africanane Terpenoids from the Hybrid Soft Coral Sinularia maxima X S polydactyla. H. Kamel, X-C. Li, D. Ferreira, Y. Ding, M. Slattery, and F. Fronczek, Link J. Nat. Prod., 2009, 72, 900-905.

    Theoretical Calculation of Electronic Circular Dichroism of a Hexahydroxydiphenoyl-Containing Flavanone Glycoside. Y. Ding, X-C. Li, and D.Ferreira, Link J. Nat. Prod., 2009, 72, 327-335.

    Pregnane Glycosides from Hoodia gordonii. Y.J. Shukla, R.S. Pawar, Y. Ding, X-C. Li, D. Ferreira, and I.A. Khan, Link Phytochemistry, 2009, 70, 674-682.

    Naturally Occuring and Synthetic Cannabinoids and their Potential Therapeutic Applications. A.M. Galal, D.Slade, W.Gul, A.T. El-Alfy, D. Ferreira, and M.A. ElSohly, Link Recent Patents Reviews on CNS Drug Discovery, 2009, 4, 112-136.

    Cycloabiesesquinone A, a New Class of Sesquiterpenoid from Abies delavayi. X-W. Yang, X-C. Li, Y-H. Shen, Y-Q. Ding, S-M. Li, D. Ferreira, N. Wang, and W-D. Zhang, Chem. Commun., 2009, 3771-3733

    Salvinorins J from Salvia divinorum: Mutarotation in the Neoclerodane System. L. Kutrzeba, D. Ferreira, and J.K. Zjawiony, Link J. Nat. Prod., 2009, 72, 1361-1363

    Scuteflorins A and B, Dihydropyranocoumarins from Scutellaria lateriflora. J. Li, Y. Ding, X-C. Li, D. Ferreira, S.I. Khan, T. Smillie, and I. A. Khan, Link J. Nat. Prod., 2009, 72, 983-987.

    Reversal of Fluconazole Resistance by Sulfated Sterols from a Marine Sponge Topsentia sp. 1. J.A. DiGirolamo, X-C. Li, M.R. Jacob, P. Carvalo, A.M. Clark, and D. Ferreira, Link J. Nat. Prod., 2009, ms np-2009-00177m.

    Anti-Infective Pyrroloiminoquinone Alkaloids from a Deep-Water Alaskan Sponge of the Genus Latrunculia. M-K. Na, Y. Ding, B. Wang, R.F. Schinazi, M. Kelly, R. Stone, X-C. Li, D. Ferreira, and M.T. Hamann, Link J. Nat. Prod., 2009, np-2009-00281r

    Antioxidant Activity of the Dihydrochalcones, Aspalathin and Nothofagin, and Their Corresponding Flavones in Relation to Other Rooibos (Aspalathus linearis) Flavonoids, EGCG, and Trolox. P.W. Snyman, E. Joubert, D. Ferreira, Y. Ding, X-C. Li, W.C.A. Gelderblom, and I.R. Green, Link J. Agric. Food Chem., 2009, ms jf-2009-01417k.

    Scalarane Sesterterpenoids: Semisynthesis and Biological Activity. H. Kamel, J. Rimoldi, F. Fronczek, D. Ferreira, M. Slattery, and Y. Kim, Link J. Nat. Prod., 2009, np-2009-00326a.

    The Effect of Pomegranate (Punica granatum L.) Ellagitannins on the Growth of Human Gut Bacteria. D. Bialonska, S. Kasimsetty, K. Schrader, and D. Ferreira, Link J. Agric. & Food Chem., 2009, jf-2009-01931b.

    Pomegranate Phenolics from the Peels, Arils, and Flowers are Antiatherogenic: Studies in Vivo in Atherosclerotic Apolipoprotein E-Deficient (E0) Mice and in Vitro in Cultured Macrophages and Lipoproteins. M. Aviram, N. Volkova, R. Coleman, M. Dreher, M. K. Reddy, D. Ferreira, and M. Rosenblat,Link J. Agric. & Food Chem., 2008, 56, 1148-1157.

    A Pathogenic Fungi Diphenyl Ether Phytotoxin Targets Plant Enoyl (Acyl Carrier Protein) Reductase. F.E. Dayan, D. Ferreira, Y-H. Wang, I.A. Khan, and Z. Pan,Link Plant Physiology, 2008, 147, 1062-1071.

    Microbial Metabolism. Part 9. Structure and Antioxidant Significance of the Metabolites of 5,7-Dihydroxyflavone (Chrysin) and 5- and 6-Hydroxyflavones. W. Herath, J.L. Michael, A.L. Hale, D. Ferreira, and I.A. Khan,Link Chem. & Pharm. Bull., 2008, 56, 418-422.

    Synthesis of a Novel Class of Salvinorin A Analogs with Hemiacetalic Functionality. R.V. Bikbulatov, J. Stewart, W. Jin, F.Yan, B.L. Roth, D. Ferreira, and J.K. Zjawiony, Tetrahedron Lett., 2008, 49, 937-940.

    The Co-Occurrence of the Rare Indazole-Type Alkaloids, Nigellidine and its 4-O-sulfite in the Seeds of Nigella sativa. Z.Ali, D. Ferreira, P.Carvalho, M.A. Avery, and I.A.Khan, Link J. Nat. Prod., 2008, 71, 1111-1112.

    Enantiomeric Discorhabdin Alkaloids and Establishment of Their Absolute Configurations using Theoretical Calculations of Electronic Circular Dichroism Spectra. T. Grkovic, Y.Ding, X-C. Li, V.L. Webb, D. Ferreira, and B.R. Copp,Link J. Org. Chem., 2008, 73, 9133-9136

    Sorocenols G and H, Anti-MRSA Oxygen Heterocyclic Diels-Alder-type Adducts from Sorocea muriculata Roots. S.A. Ross, R. Rodríguez-Guzmán, M.M. Radwan, M. Jacob, Y. Ding, X-C. Li, D. Ferreira, and S.P. Manly,Link J. Nat. Prod., 2008, 71, 1764-1767.

    Microbial Transformations. Part 7. Curcumin. W.H.M.W. Herath, D. Ferreira, and I.A. Khan, Nat. Prod. Res., Part A., 2007, 21, 444-450.

    Flavan-3-ol-Phenylpropanoid Conjugates from Anemopaegma arvense and their Antioxidant Activities. N. Tabanca, R. S. Pawar, D. Ferreira, J. P. J. Marais, S.I. Khan, D. E. Wedge, and I.A. Khan,Link Planta Med., 2007, 73, 1107-1111.

    9,19-Cyclolanostane Derivatives from the Roots of Actaea pachypoda. Z. Ali, S.I. Khan, R.S. Pawar, D. Ferreira, and I.A. Khan,Link J. Nat. Prod., 2007, 70, 107-110.

    Synthesis, Spectroscopic and Anti-Tumor Studies of Polyphenol-Linoleates Derived from Natural Polyphenols. J. Mustafa, S.I. Khan, D. Ferreira, and I.A. Khan,Link Eur. J. of Lipid Sci. and Technology, 2007, 109, 552-559.

    Antioxidant, Antimalaria, and Antimicrobial Activity of Ellagitannins and Phenolic Acids from Punica granatum. M.K. Reddy, S.K. Gupta, M.R. Jacob, S.I. Khan, and D. Ferreira,Link Planta Med. 2007, 73, 461-467.

    Theoretical Calculation of Electronic Circular Dichroism of the Rotationally Restricted 3,8_-Biflavonoid Morelloflavone. Y. Ding, X.-C. Li, and D. Ferreira, J. Org. Chem., 2007, 72, 9010-9017.

    Cytotoxic Diterpenoids from the Hybrid Soft Coral Sinularia maxima x Sinularia polydactyla. H. N. Kamel, D. Ferreira, L.F. Garcia-Fernandez, and M. Slattery,Link J. Nat. Prod., 2007, 70, 1223-1227.

    Synthesis, Antifungal Activity, and Structure Activity Relationships of Coruscanone A Analogs. K. S. Babu, X-C. Li, M. R. Jacob, Q. Zhang, S. I. Khan, D. Ferreira, and A. M. Clark .Link J. Med. Chem., 2006, 49, 7877-7886.

    Podocarpaside, a Triterpenoid Possessing a New Backbone from Acatea podocarpa. Z.Ali, S.I. Khan, D. Ferreira, and I.A. Khan,Org. Lett., 2006, 8, 5529-5532.

    Schisandrene, a Dibenzocyclooctadiene Lignan from Schisandra chinensis: Stucture-Antioxidant Relationships of Dibenzocyclooctadiene Lignans. Y.-W. Choi, S Takamatsu, S.I. Khan, P.V. Srinivas, D.Ferreira, J. Zhao and I.A. Khan,Link J. Nat. Prod., 2006, 69, 356-359.

    Antiparasitic Activity of Some Xanthones and Biflavonoids from the Root Bark of Garcinia livingstonei. Z. H. Mbwambo, M. C. Kapingu, M. J. Moshi, F. Machumi, S. Apers, P. Cos, D. Ferreira, J. P. J. Marais, D. Vanden Berghe, L. Maes, A. Vlietinck, and L. Pieters,Link J. Nat. Prod., 2006, 69, 369-372.

    Capisterones A and B, which Enhance Fluconazole Activity in Saccharomyces cerevisiae, from the Marine Green Alga Penicillus capitatus X-C. Li, M.R. Jacob, Y. Ding, A.K. Agrawal, T.J. Smillie, S.I. Khan, D.G. Nagle, D.Ferreira and A.M. Clark Link J. Nat Prod., 2006, 69, 542-546.

    Newbouldiosides A-C, Phenylethanoid Glycosides from the Stem Bark of Newbouldia laevis. R. Gorman, M. Kaloga, D. Ferreira, J.P.J. Marais and H. Kolodziej Link Phytochemistry, 2006, 67, 805-811.

    Microbial Metabolism. Part 6. Metabolites of 3- and 7-Hydroxyflavones. W.H.M.W. Herath, J.R. Mikkel, A.R. Hale, D. Ferreira, and I.A. Khan,Link Chem. Pharm. Bull., 2006, 54, 320-324.

    Structurally Unique Biflavonoids from Selaginella chrysocaulos and Selaginella bryopteris. R. Swamy, O. Kunert, W Schuhly, F. Bucar, D. Ferreira, V.S. Rani, B. R.Kumar, and A.V.N.A. Rao Link, Chemistry & Biodiversity, 2006, 3, 405-413.

    Molecules of Interest: Epigallocatechin-3-gallate (EGCG). D. Ferreira, Y- D. Zhou, and D.G. Nagle, Phytochemistry, 2006, 67, 1949-1855.

    3-Benzyl-4-chromanones (Homoisoflavanones) from Bulbs of the Ethnomedicinal Geophyte Ledebouria revoluta (Hyacinthaceae). N. Moodley, N.R. Crouch, D. A. Mulholland, D.Slade, and D. Ferreira, Link South African Journal of Botany, 2006, 72, 517-520.

    Peer-Reviewed Chapters in Scholarly Books

    Proanthocyanidins: Chemistry and Biology. D. Ferreira, J.P.J. Marais, C.Coleman, and D.Slade, Comprehensive Natural Products Chemistry II, 2009, Chapter 6.15

    The Stereochemistry of Flavonoids. J.P.J. Marais, B. Deavours, R. A. Dixon and D. Ferreira, in The Science of Flavonoids, E. Grotewold (Ed.), Springer Science, New York, 2006, pp. 1-46.

    Flavans and Proanthocyanidins. D. Ferreira, D. Slade and J.P.J. Marais in Flavonoids: in Chemistry, Biochemistry and Applications, O Andersen, K.R Markham (Eds), CRC Publishers, Boca Raton, FL, 2006, pp. 553-616.

    Bi-, Tri-, Tetra-, Penta- and Hexaflavonoids. D. Ferreira, D. Slade and J.P.J. Marais in Flavonoids: Chemistry, Biochemistry and Application, O Andersen, K.R Markham (Eds), CRC Publishers, Boca Raton, FL, 2006, pp. 1101-1128.

    Editorials

    Tannins and Related Polyphenols: Perspectives on Their Chemistry, Biology, Ecological Effects, and Human Health Protection. D. Ferreira, G.G. Gross, A.E. Hagermann, H. Kolodziejk, and T. Yoshida, Phytochemistry Editorial, 2008 (5th Tannin Conference), 69, 3006-3008.

    Helen A. Stafford - 2008 Recipient of the PSNA Phytochemistry Pioneer Award. D. Ferreira and F. Loewes, Phytochemistry Editorial, 2008, 69, 3009-3011

    The 2006 Annual Meeting of the Phytochemical Society of North America: Special Issue of Phytochemistry, Phytochemistry Pioneer Awards and the 2006 Meeting Scientific Highlights - Editorial. C.L. Cantrell, D.D. Cook, F.E. Dayan, and D. Ferreira, Phytochemistry Editorial, 2007, 68, 1826-1829.

    Tannins and Related Polyphenols: Fascinating Natural Products with Diverse Implications for Biological Systems, Ecology, Industrial Applications and Health Protection. D. Ferreira, G. Gross, H. Kolodziej and T. Yoshida, Phytochemistry Editorial (4th Tannin Conference), 2005, 66, 1969-1971.