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Xanthine Alkaloids: Occurrence, Biosynthesis, and Function in Plants; 1 Introduction; 2 Occurrence of Xanthine Alkaloids in the Plant Kingdom; 2.1 Ericales (Tea and Related Species); 2.2 Gentianales (Coffee and Related Species); 2.3 Aquifoliales (Maté and Related Species); 2.4 Malvales (Cacao, Cola, and Related Species); 2.5 Sapindales (Guaran, Citrus, and Related Plants); 2.6 Other Species; 3 Biosynthesis of Xanthine Alkaloids; 3.1 A Brief History of the Elucidation of the Biosynthesis Pathways; 3.2 Caffeine Biosynthesis Pathways from Xanthosine; 3.2.1 Formation of 7-Methylxanthine
Feeding ExperimentsEnzyme Studies; Genes and Proteins; 3.2.2 Conversion of 7-Methylxanthine to Caffeine via Theobromine; Feeding Experiments; Enzyme Studies; Genes and Proteins; 3.2.3 Evolutionary Relationship of the Caffeine Synthase Family Proteins; 3.3 Pathways that Supply Xanthosine for Caffeine Biosynthesis; 3.3.1 De Novo Route; 3.3.2 AMP Route; 3.3.3 SAM Cycle Route; 3.3.4 NAD Route; 3.3.5 GMP Route; 3.4 Localization of Xanthine Alkaloid Biosynthesis; 3.4.1 Organs and Tissues; Camellia; Coffea; Theobroma; Maté and Guaran; 3.4.2 Subcellular Accumulation of Xanthine Alkaloids
3.4.3 Subcellular Localization of Caffeine Biosynthesis EnzymesCaffeine Synthase; Enzymes Involved in the de Novo Route; Enzymes Involved in the AMP Route; Enzymes Involved in the SAM Route; 3.4.4 Subcellular Localization and Transport of Intermediates; 3.5 Regulation of Caffeine Biosynthesis; 4 Metabolism of Xanthine Alkaloids; 4.1 Methyluric Acid Biosynthesis; 4.2 Biodegradation and Inter-conversion of Xanthine Alkaloids; 4.2.1 The Major Pathway of Caffeine Degradation; 4.2.2 Conventional Purine Catabolic Pathways in Plants; 4.2.3 Diversity of Xanthine Alkaloid Metabolism in Plants; Coffea
Tea4.2.4 Xanthine Alkaloid Metabolism in Bacteria and Animals; Bacteria; Animals; 5 Ecological Roles of Xanthine Alkaloids; 5.1 Allelopathic Function Theory; 5.1.1 Effect of Xanthine Alkaloids on Germination and Growth of Plants; 5.1.2 Effect of Xanthine Alkaloids on Proliferation of Plant Cells; 5.1.3 Effect of Xanthine Alkaloids on Plant Metabolism; 5.1.4 Effect of Caffeine on Protein Expression Profiles; 5.1.5 Allelopathy in Natural Ecosystems; 5.2 Chemical Defense Theory; 5.2.1 Chemical Defense Against Microorganisms and Animals
5.2.2 Proof of the Chemical Defense Theory Demonstrated with Transgenic Plants6 Biotechnology of Xanthine Alkaloids; 6.1 Decaffeinated Coffee and Tea Plants; 6.2 Caffeine-Producing Transgenic Plants; 6.2.1 Antiherbivore Activity; 6.2.2 Antipathogen Activity; 7 Summary and Perspectives; References; The Iboga Alkaloids; 1 Introduction; 2 Biosynthesis; 3 Structural Elucidation and Reactivity; 4 New Molecules; 4.1 Monomers; 4.1.1 Ibogamine and Coronaridine Derivatives; 4.1.2 3-Alkyl- or 3-Oxo-ibogamine/-coronaridine Derivatives; 4.1.3 5- and/or 6-Oxo-ibogamine/-coronaridine Derivatives
Feeding ExperimentsEnzyme Studies; Genes and Proteins; 3.2.2 Conversion of 7-Methylxanthine to Caffeine via Theobromine; Feeding Experiments; Enzyme Studies; Genes and Proteins; 3.2.3 Evolutionary Relationship of the Caffeine Synthase Family Proteins; 3.3 Pathways that Supply Xanthosine for Caffeine Biosynthesis; 3.3.1 De Novo Route; 3.3.2 AMP Route; 3.3.3 SAM Cycle Route; 3.3.4 NAD Route; 3.3.5 GMP Route; 3.4 Localization of Xanthine Alkaloid Biosynthesis; 3.4.1 Organs and Tissues; Camellia; Coffea; Theobroma; Maté and Guaran; 3.4.2 Subcellular Accumulation of Xanthine Alkaloids
3.4.3 Subcellular Localization of Caffeine Biosynthesis EnzymesCaffeine Synthase; Enzymes Involved in the de Novo Route; Enzymes Involved in the AMP Route; Enzymes Involved in the SAM Route; 3.4.4 Subcellular Localization and Transport of Intermediates; 3.5 Regulation of Caffeine Biosynthesis; 4 Metabolism of Xanthine Alkaloids; 4.1 Methyluric Acid Biosynthesis; 4.2 Biodegradation and Inter-conversion of Xanthine Alkaloids; 4.2.1 The Major Pathway of Caffeine Degradation; 4.2.2 Conventional Purine Catabolic Pathways in Plants; 4.2.3 Diversity of Xanthine Alkaloid Metabolism in Plants; Coffea
Tea4.2.4 Xanthine Alkaloid Metabolism in Bacteria and Animals; Bacteria; Animals; 5 Ecological Roles of Xanthine Alkaloids; 5.1 Allelopathic Function Theory; 5.1.1 Effect of Xanthine Alkaloids on Germination and Growth of Plants; 5.1.2 Effect of Xanthine Alkaloids on Proliferation of Plant Cells; 5.1.3 Effect of Xanthine Alkaloids on Plant Metabolism; 5.1.4 Effect of Caffeine on Protein Expression Profiles; 5.1.5 Allelopathy in Natural Ecosystems; 5.2 Chemical Defense Theory; 5.2.1 Chemical Defense Against Microorganisms and Animals
5.2.2 Proof of the Chemical Defense Theory Demonstrated with Transgenic Plants6 Biotechnology of Xanthine Alkaloids; 6.1 Decaffeinated Coffee and Tea Plants; 6.2 Caffeine-Producing Transgenic Plants; 6.2.1 Antiherbivore Activity; 6.2.2 Antipathogen Activity; 7 Summary and Perspectives; References; The Iboga Alkaloids; 1 Introduction; 2 Biosynthesis; 3 Structural Elucidation and Reactivity; 4 New Molecules; 4.1 Monomers; 4.1.1 Ibogamine and Coronaridine Derivatives; 4.1.2 3-Alkyl- or 3-Oxo-ibogamine/-coronaridine Derivatives; 4.1.3 5- and/or 6-Oxo-ibogamine/-coronaridine Derivatives