Xanthine Alkaloids: Occurrence, Biosynthesis, and Function in Plants

  • Hiroshi AshiharaEmail author
  • Kouichi Mizuno
  • Takao Yokota
  • Alan Crozier
Part of the Progress in the Chemistry of Organic Natural Products book series (POGRCHEM, volume 105)


Caffeine is a xanthine alkaloid found in non-alcoholic beverages such as tea, coffee, and cocoa. It was discovered in tea and coffee in the 1820s, but it was not until 2000 that details of molecular events associated with caffeine biosynthesis began to be unraveled. Reviewed are the occurrence of xanthine alkaloids in the plant kingdom and the elucidation of the caffeine biosynthesis pathway, providing details of the N-methyltransferases, belonging to the motif B′ methyltransferase family, which catalyze three steps in the four-step pathway leading from xanthosine to caffeine. Pathways for the metabolism and degradation of xanthine alkaloids are discussed, although as yet the genes and enzymes involved have not been isolated. This chapter also considers the in planta role of caffeine in chemical defense that has been demonstrated using transgenic caffeine-forming tobacco and chrysanthemum plants, which are resistant to attack by pathogens and herbivores. Finally, future research is considered that might lead to the production of naturally decaffeinated beverages and agricultural crops that contain elevated levels of “natural” pesticides.


Camellia sinensis Coffea spp Theobroma cacao Methylxanthines Caffeine Occurrence Biosynthesis Catabolism Transgenics Function 



We would like to thank Professor Andrew A. McCarthy, European Molecular Biology Laboratory, Grenoble, France for providing a personal communication on the current status of 7-methylxanthosine synthase. The authors also thank Professor Tatsuhito Fujimura, University of Tsukuba, Japan for drawing Fig. 2.


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Copyright information

© Springer International Publishing AG 2017

Authors and Affiliations

  • Hiroshi Ashihara
    • 1
    Email author
  • Kouichi Mizuno
    • 2
  • Takao Yokota
    • 3
  • Alan Crozier
    • 4
  1. 1.Department of BiologyOchanomizu UniversityTokyoJapan
  2. 2.Faculty of Bioresource of ScienceAkita Prefectural UniversityAkitaJapan
  3. 3.Department of BiosciencesTeikyo UniversityUtsunomiyaJapan
  4. 4.Department of NutritionUniversity of CaliforniaDavisUSA

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