David R. Gang

Associate Professor of Plant Sciences and Biochemistry & Molecular Biophysics
Ph.D., Washington State University

Plant specialized metabolism (secondary metabolism); evolution of plant metabolic pathways; genomics-based approaches to elucidate biosynthetic pathways (biochemical genomics); function of plant natural products.

Research Interests

Plants produce an amazing diversity of small molecular weight compounds. While the chemical structures of close to 50,000 of them have already been elucidated, the total number of such compounds is probably in the hundreds of thousands to millions. Only a small number of these are part of what have been termed "primary" metabolic pathways; the rest of these molecules are called "secondary" metabolites, also known as specialized metabolites or natural products. The vast majority of these compounds are not found in the standard crop plants of the Western world, nor in standard laboratory model plants such as Arabidopsis thaliana and Medicago trunculata. These compounds are, however, believed to play vital roles in the physiology of the plants that produce them, particularly as elements of the plants' defensive arsenals. Because of the great diversity of life strategies and accompanying defense strategies, these compounds truly represent the great diversity in the plant kingdom. Yet, very little is known about the mechanisms involved in the formation of almost all plant natural products.

Aromatic plants (e.g., sweet basil, turmeric and ginger) present excellent model systems research to identify these mechanisms because i) they synthesize high amounts of specialized compounds, ii) a substantial diversity of compounds can be found in closely related species, and iii) these compounds are often synthesized in specialized structures, such as rhizomes or secretory glands, which makes it possible to investigate the exact role of specific enzymes and genes in the production of specific metabolites in isolation from other major biochemical pathways. We can do this with the glands because these structures (known as the secretory peltate glandular trichomes) can be isolated, intact, from the rest of the plant (as is also the case for the terpenoid-producing glands from mint).

Our research seeks to elucidate the biosynthetic pathways that produce novel and important plant specialized metabolites in aromatic plants, to uncover the mechanisms responsible for the evolution of these pathways in the plant kingdom and to understand the function of a given natural product in the biology and physiology of a given plant species. The most productive approach in this area has been a multidisciplinary one-which utilizes the best tools from the fields of chemistry, biochemistry, molecular biology, plant physiology, whole organism biology and ecology-because understanding the role that a specific metabolite plays in the plant requires an understanding of the whole complexity surrounding its formation and utilization. Tools are only now becoming available which allow us to gain this understanding.

Select Publications

Any link on the below references will take you off of the BMCB site and to an abstract of that particular paper.

Ma, X., and D.R. Gang. 2008. In vitro production of huperzine A, a promising drug candidate for Alzheimer's disease. Phytochemistry 69: 2022-2028.

Xie, Z., J. Kapteyn, and D.R. Gang. 2008. A systems biology investigation of the MEP/terpenoid and shikimate/phenylpropanoid pathways points to multiple levels of metabolic control in sweet basil glandular trichomes. The Plant Journal 54: 349-361.

Kapteyn, J., A.V. Qualley, Z. Xie, E. Fridman, N. Dudareva, and D.R. Gang. 2007. Evolution of Cinnamate/p-coumarate carboxyl methyltransferases and their role in the biosynthesis of methylcinnamate. The Plant Cell 19: 3212-3229.

Ma, X., C. Tan, D. Zhu, D.R. Gang, and P. Xiao. 2007. Huperzine A from Huperzia species--an ethnopharmacolgical review. Journal of Ethnopharmacology 113: 15-34.

Jiang, H., B.N. Timmermann, and D.R. Gang. 2007. Characterization and identification of diarylheptanoids in ginger (Zingiber officinale Rosc.) using high-performance liquid chromatography/electrospray ionization mass spectrometry. Rapid Communications in Mass Spectrometry 21: 509-518.

Ma, X., and D.R. Gang. 2006. Metabolic profiling of turmeric (Curcuma longa L.) plants derived from in vitro micropropagation and conventional greenhouse cultivation. Journal of Agricultural and Food Chemistry 54: 9573-9583.

Dixon, R.A., D.R. Gang, A.J. Charlton, O. Fiehn, H.A. Kuiper, T.L. Reynolds, R.S. Tjeerdema, E.H. Jeffery, J.B. German, W.P. Ridley, and J.N. Seiber. 2006. Applications of metabolomics in agriculture. Journal of Agricultural and Food Chemistry 54: 8984-8994.

Ma, X.Q., and D.R. Gang. 2006. Metabolic profiling of in vitro micropropagated and conventionally greenhouse grown ginger (Zingiber officinale). Phytochemistry 67: 2239-2255.

Ramirez Ahumada, M.C., B.N. Timmermann, and D.R. Gang. 2006. Biosynthesis of curcuminoids and gingerols in turmeric (Curcuma longa) and ginger (Zingiber officinale): identification of curcuminoid synthase and hydroxycinnamoyl-CoA thioesterases. Phytochemistry 67: 2017-2029.

Vassao. D.G., D.R. Gang, T. Koeduka, B. Jackson, E. Pichersky, L.B. Davin, and N.G. Lewis. 2006. Chavicol formation in sweet basil (Ocimum basilicum): cleavage of an esterified C9 hydroxyl group with NAD(P)H-dependent reduction. Organic & Biomolecular Chemistry 4: 2733-2744.

Koeduka, T., E. Fridman, D.R. Gang, D.G. Vassao, B.L. Jackson, C.M. Kish, I. Orlova, S.M. Spassova, N.G. Lewis, N.P. Noel, T.J. Baiga. N. Dudareva, and E. Pichersky. 2006. Eugenol and isoeugenol, characteristic aromatic constituents of spices, are biosynthesized via reduction of a coniferyl alcohol ester. Proceedings of the National Academy of Sciences U.S.A. 103: 10128-10133.

Jiang, H., B.N. Timmermann, and D.R. Gang. 2006. Use of liquid chromatography-electrospray ionization tandem mass spectrometry to identify diarylheptanoids in turmeric (Curcuma longa L.) rhizome. Journal of Chromatography. A 1111: 21-31.

Jiang, H., A. Somogyi, N.E. Jacobsen, B.N. Timmermann, and D.R. Gang. 2006. Analysis of curcuminoids by positive and negative electrospray ionization and tandem mass spectrometry. Rapid Communications in Mass Spectrometry 20: 1001-1012.

Jiang, H., A. Somogyi, B.N. Timmermann, and D.R. Gang. 2006. Instrument dependence of electrospray ionization and tandem mass spectrometric fragmentation of the gingerols. Rapid Communications in Mass Spectrometry 20: 3089-3100.

Jiang, H., Z. Xie, H.J. Koo, S.P. McLaughlin, B.N. Timmermann, and D.R. Gang. 2006. Metabolic profiling and phylogenetic analysis of medicinal Zingiber species: Tools for authentication of ginger (Zingiber officinale Rosc.). Phytochemistry 67: 1673-1685.

Ma, X., C. Tan, D. Zhu, and D.R. Gang. 2006. A survey of potential huperzine A natural resources in China: The Huperziaceae. Journal of Ethnopharmacology 104: 54-67.

Fridman, E., J. Wang, Y. Iijima, J.E. Froehlich, D.R. Gang, J. Ohlrogge, E. Pichersky. 2005. Metabolic, genomic, and biochemical analyses of glandular trichomes from the wild tomato species Lycopersicon hirsutum identify a key enzyme in the biosynthesis of methylketones. The Plant Cell 17: 1252-1267.

Ma, X., C. Tan, D. Zhu, and D.R. Gang. 2005. Is there a better source of huperzine A than Huperzia serrata? Huperzine A content of Huperziaceae species in China. Journal of Agricultural and Food Chemistry 53: 1393-1398.

Gang, D.R. 2005. Evolution of flavors and scents. Annual Review of Plant Biology 56: 301-325.

Jiang, H., A.M. Solyom, B.N. Timmermann, and D.R. Gang. 2005. Characterization of gingerol-related compounds in ginger rhizome (Zingiber officinale Rosc.) by high-performance liquid chromatography/electrospray ionization mass spectrometry. Rapid Communications in Mass Spectrometry 19: 2957-2964.

Ma, X., and D.R. Gang. 2004. The Lycopodium alkaloids. Natural Product Reports 21: 752-772.

Iijima, Y., R. Davidovich-Rikanati, E. Fridman, D.R. Gang, E. Bar, E. Lewinsohn, and E. Pichersky. 2004. The biochemical and molecular basis for the divergent patterns in the biosynthesis of terpenes and phenylpropenes in the peltate glands of three cultivars of basil. Plant Physiology 136: 3724-3736.

Iijima, Y., D.R. Gang, E. Fridman, E. Lewinsohn, and E. Pichersky. 2004. Characterization of geraniol synthase from the peltate glands of sweet basil. Plant Physiology 134: 370-379.

Min, T., H. Kasahara, D.L. Bedgar, B. Youn, P.K. Lawrence, D.R. Gang, S.C. Halls, H. Park, J.L. Hilsenbeck, L.B. Davin, N.G. Lewis, and C. Kang. 2003. Crystal structures of pinoresinol-lariciresinol and phenylcoumaran benzylic ether reductases and their relationship to isoflavone reductases. Journal of Biological Chemistry 278: 50714-50723.

Gang, D.R., T. Beuerle, P. Ullmann, D. Werck-Reichhart, and E. Pichersky. 2002. Differential production of meta hydroxylated phenylpropanoids in sweet basil peltate glandular trichomes and leaves is controlled by the activities of specific acyltransferases and hydroxylases. Plant Physiology 130: 1536-1544.

Gang, D.R., N. Lavid, C. Zubieta, F. Chen, T. Beuerle, E. Lewinsohn, J.P. Noel, and E. Pichersky. 2002. Characterization of phenylpropene O-methyltransferases from sweet basil: facile change of substrate specificity and convergent evolution within a plant O-methyltransferase family. The Plant Cell 14: 505-519.

Gang, D.R., J. Wang, N. Dudareva, K.H. Nam, J.E. Simon, E. Lewinsohn, and E. Pichersky. 2001. An investigation of the storage and biosynthesis of phenylpropenes in sweet basil. Plant Physiology 125: 539-555.

Pichersky, E., and D.R. Gang. 2000. Genetics and biochemistry of secondary metabolites in plants: an evolutionary perspective. Trends in Plant Science 5: 439-445.

Gang, D.R., M.A. Costa, M. Fujita, A.T. Dinkova-Kostova, H.B. Wang, V. Burlat, W. Martin, S. Sarkanen, L.B. Davin, and N.G. Lewis. 1999. Regiochemical control of monolignol radical coupling: a new paradigm for lignin and lignan biosynthesis. Chemistry & Biology 6: 143-151.

Gang, D.R., H. Kasahara, Z.Q. Xia, K. Vander Mijnsbrugge, G. Bauw, W. Boerjan, M. Van Montagu, L.B. Davin, and N.G. Lewis. 1999. Evolution of plant defense mechanisms. Relationships of phenylcoumaran benzylic ether reductases to pinoresinol-lariciresinol and isoflavone reductases. Journal of Biological Chemistry 274: 7516-7527.

Fujita, M., D.R. Gang, L.B. Davin, and N.G. Lewis. 1999. Recombinant pinoresinol-lariciresinol reductases from western red cedar (Thuja plicata) catalyze opposite enantiospecific conversions. Journal of Biological Chemistry 274: 618-627.

Dinkova-Kostova, A.T., D.R. Gang, L.B. Davin, D.L. Bedgar, A. Chu, and N.G. Lewis. 1996. (+)-Pinoresinol/(+)-lariciresinol reductase from Forsythia intermedia. Protein purification, cDNA cloning, heterologous expression and comparison to isoflavone reductase. Journal of Biological Chemistry 271: 29473-29482.

Gang, D.R., and D.J. Weber. 1995. Preparation of genomic DNA for RAPD analysis from thick-walled dormant teliospores of Tilletia species. BioTechniques 19: 92,94, 96-97.

Contact Information

Mailing: David R. Gang , Associate Professor Department of Plant Sciences University of Arizona Marley Building 441A P. O. Box 245217 Tucson, AZ 85724-0241

Telephone: 520-621-7154 (Office) 520-621-1718 (Lab) Fax: 520-621-7186 Email: gang@ag.arizona.edu

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