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Seiichi P.T. Matsuda

E. Dell Butcher Professor of Chemistry and Professor of Biochemistry & Cell Biology

Terpenoids are compounds derived from isopentenyl pyrophosphate. They are the most numerous and structurally diverse group of natural products, with 22,000 members displaying more than 300 ring systems. Terpenoids that play crucial roles in vertebrates include the retinoids, the geranylgeranyl and farnesyl protein anchors, the coenzymes Q, vitamins A, D, and E, cholesterol, and the steroid hormones. Terpenoid hormones and pheromones are equally important in invertebrates. Plants control growth and development using regulatory terpenes including matsuda_workthe gibberellins, the brassinosteroids, and abscissic acid. Many plants synthesize defense terpenoids that interfere with biological processes in potential herbivores. Some of these compounds are medicinally useful, such as taxol (anticancer), ginkgolide (which delays onset and progression of Alzheimer's disease), and artemisinin (antimalarial). We are cloning and characterizing genes encoding terpene cyclases and terpene oxidases, which catalyze terpene biosynthesis. We engineer microbial metabolic pathways by heterologously expressing these genes. The resultant strains produce natural products, many of which are difficult to obtain by existing methodology. Terpene synthases catalyze spectacular reactions, such as the conversion of epoxysqualene to cycloartenol. We are modifying terpene biosynthetic genes to produce catalysts that make novel natural products. In collaboration with Bonnie Bartel in this department, we are studying the function of terpenoids in the plant Arabidopsis thaliana.

Publications

Morlacchi, P., Wilson, W.K., Xiong, Q., Bhaduri, A., Sttivend, D., Kolesnikova, M.D., and Matsuda, S.P.T. Product Profile of PEN3: the Last Unexamined Oxidosqualene Cyclase in Arabidopsis thaliana.  Org. Lett., 11 2009: 2627-2630

Lodeiro, S., Xiong, Q.,Wilson, W.K., Ivanova, Y., Smith, M.L., May, G. S. and Matsuda, S. P. T. Protostadienol Biosynthesis and Metabolism in the Pathogenic Fungus Aspergillus fumigatus.  Org. Lett., 11 2009: 1241-1244

Shan, H., Wilson, W. K., Phillips, D. R., Bartel, B. and Matsuda, S. P. T. Trinorlupeol: a major nonsterol triterpenoid in Arabidopsis.  Org. Lett., 10 2008: 1897-1900

M. D. Kolesnikova, W. K. Wilson, William; D. A. Lynch, A. C. Obermeyer, S. P. T. Matsuda Arabidopsis camelliol C synthase evolved from enzymes that make pentacycles.  Org. Lett., 9 2007: 5223 -5226

S. Lodeiro, Q. Xiong, W. K. Wilson, M. D. Kolesnikova, C. S. Onak, and S. P. T. Matsuda An oxidosqualene cyclase makes numerous products by diverse mechanisms: a challenge to prevailing concepts of triterpene biosynthesis.  J. Am. Chem. Soc., 129 2007: 11213-11222

M. D. Kolesnikova, A. C. Obermeyer, W. K. Wilson, D. A. Lynch, Q. Xiong, and S. P. T. Matsuda The stereochemistry of water addition in triterpene synthesis: the structure of arabidiol.  Org. Lett., 9 2007: 2183-2186

Q. Xiong, W. K. Wilson, and S. P. T. Matsuda An Arabidopsis oxidosqualene cyclase catalyzes iridal skeleton formation via Grob fragmentation.  Angew. Chem., 45 2006: 1285-1288

D. R. Phillips, J. M. Rasbery, B. Bartel, and S. P. T. Matsuda Biosynthetic diversity in plant triterpene cyclization.  Curr. Opin. Plant Biol., 9 2006: 305-314

S. P. T. Matsuda, W. K. Wilson, and Q. Xiong Mechanistic insights into triterpene synthesis from quantum mechanical calculations. Detection of systematic errors in B3LYP cyclization energies.  Org. Biomol. Chem. 2006: 530-543

  • B.A. Chemistry (1984) Bethel College
  • Ph.D. Chemistry (1994) Harvard University
  • Department of BioSciences
  • Institute of Biosciences and Bioengineering
  • Recombinant biosynthetic approaches to natural product biosynthesis. Directed evolution and DNA shuffling to generate new oxidosqualene cyclases. Metabolic engineering to produce terpenes.
Email: matsuda@rice.edu
Phone: (713) 348-4002
Office: George R. Brown Hall, W300E