The prevailing hypothesis of caffeine biosynthesis starting from xanthosine was combined with Kremers’ speculation on NAD as a biochemical precursor of caffeine and trigonelline in coffee. This bold sketch together with a few free-spirited ideas may channel future caffeine biosynthesis studies into novel directions.
AndersonL, GibbsM. (1962) The biosynthesis of caffeine in the coffee plant. Journal of Biological Chemistry, 237, 1941-1944.
2.
SuzukiT, TakahashiE. (1975) Biosynthesis of caffeine by tea-leaf extracts. Enzymic formation of theobromine from 7-methylxanthine and of caffeine from theobromine. Biochemical Journal, 146, 87-96.
3.
LooserE, BaumannTWWannerH. (1974) The biosynthesis of caffeine in the coffee plant. Phytochemistry, 13, 2515-2518.
4.
OgutugaDba, NorthcoteDH (1970) Biosynthesis of caffeine in tea callus tissue. Biochemical Journal, 117, 715-720.
5.
NegishiO, OzawaT, ImagawaH. (1985) Conversion of xanthosine into caffeine in tea plants. Agricultural and Biological Chemistry, 49, 251-253.
6.
NegishiO, OzawaT, ImagawaH. (1985) Methylation of xanthosine by tea-leaf extracts and caffeine biosynthesis. Agricultural and Biological Chemistry, 49, 887-890.
7.
NegishiO, OzawaT, ImagawaH. (1985) The role of xanthosine in the biosynthesis of caffeine in coffee plants. Agricultural and Biological Chemistry, 49, 2221-2222.
8.
SchulthessBHBaumannTW. (1995) Stimulation of caffeine biosynthesis in suspension-cultured coffee cells and the in situ existence of 7-methylxanthosine. Phytochemistry, 38, 1381-1386.
9.
SchulthessBHBaumannTW. (1995) Are xanthosine and 7-methylxanthosine caffeine precursors?Phytochemistry, 39, 1363-1370.
10.
AshiharaH, KubotaH. (1986) Patterns of adenine metabolism and caffeine biosynthesis in different parts of tea seedlings. Physiologia Plantarum, 69, 275-281.
11.
AshiharaH, KubotaH. (1987) Biosynthesis of purine alkaloids in Camellia plants. Plant & Cell Physiology, 28, 535-539.
12.
FujimoriN, AshiharaH. (1990) Adenine metabolism and the synthesis of purine alkaloids in the flowers of Camellia. Phytochemistry, 29, 3513– 3516.
13.
FujimoriN, SuzukiT, AshiharaH. (1991) Seasonal variations in biosynthetic capacity for the synthesis of caffeine in tea leaves. Phytochemistry, 30, 2245-2248.
14.
KyoungM, RussellSJKohnhorstCLEsemotoNNAnS. (2014) Dynamic architecture of the purinosome involved in human de novo purine biosynthesis. Biochemistry, 54, 870-880.
15.
CastellanaM, WilsonMZXuY, JoshiP, CristeaIMRabinowitzJDGitaiZ, WingreenNS. (2014) Enzyme clustering accelerates processing of intermediates through metabolic channeling. Nature Biotechnology, 32, 1011-1018.
16.
ZhaoA, TsechanskyM, EllingtonADMarcotteEM. (2013) Revisiting and revising the purinosome. Molecular BioSystems, 10, 369-374.
17.
SchulthessBHMorathP, BaumannTW. (1996) Caffeine biosynthesis starts with the metabolically-channelled formation of 7-methyl-XMP – a new hypothesis. Phytochemistry, 41, 169-175.
18.
MizunoK, KatoM, IrinoF, YoneyamaN, FujimuraT, AshiharaH. (2003) The first committed step reaction of caffeine biosynthesis: 7– methylxanthosine synthase is closely homologous to caffeine synthases in coffee (Coffea arabica L.)FEBS Letters, 547, 56-60.
19.
KatoM, MizunoK. (2004) Caffeine synthase and related methyltransferases in plants. Frontiers in Bioscience, 9, 1833-1842.
20.
SchimplFCKiyotaE, MayerJls, GonçalvesJfc, da SilvaJFMazzaferaP. (2004) Molecular and biochemical characterization of caffeine synthase and purine alkaloid concentration in guarana fruit. Phytochemistry, 105, 25-36.
21.
McCarthyAAMcCarthyJG. (2007) The structure of two N-methyltransferases from the caffeine biosynthetic pathway. Plant Physiology, 144, 879-889.
22.
WannerH, PesakovaM, BaumannTWCharubalaR, GuggisbergA, HesseM, SchmidH. (1975) O(2),1,9–Trimethyluric acid and 1,3,7,9– tetramethyluric acid in leaves of different Coffea species. Phytochemistry, 14, 747-750.
23.
PetermannJBBaumannTW. (1983) Metabolic relations between methylxanthines and methyluric acids in Coffea L. Plant Physiology, 73, 961-964.
24.
BernetS. (2000) 1-Methyluracil in Theobroma bicolor and related species; its relationship to caffeine biosynthesis. Master Thesis University of Zurich, Institute of Plant Biology (in German)
25.
JaffreyS. (2014) An expanding universe of mRNA modifications. Nature Structural & Molecular Biology, 21, 945-946.
26.
CarlileTMRojas-DuranMFZinshteynB, ShinH, BartoliKMGilbertWV. (2014) Pseudouridine profiling reveals regulated mRNA pseudouridylation in yeast and human cells. Nature, 515, 143–146.
27.
LovejoyAFRiordanDPBrownPO. (2014) Transcriptome-wide mapping of pseudouridines: Pseudouridine synthases modify specific mRNAs in S. cerevisiae. PLoS ONE9, e110799.
28.
WurmJPMeyerB, BahrU, HeldM, FrolowO, KötterP, EngelsJWHeckelA, KarasM, EntianK-D, WöhnertJ. (2010) The ribosome assembly factor Nep1 responsible for Bowen–Conradi syndrome is a pseudouridine-N1-specific methyltransferase. Nucleic Acids Research, 38, 2387-2398.
29.
CamargoTdeA. (1924) The presence of vernine (guanosine) in the green leaves and berries of the coffee tree (Coffea arabica L. and its relation to the origin of caffeine in this plant. Journal of Biological Chemistry, 58, 831-834.
30.
DahnckeK, WitteC-P. (2013) Plant purine nucleoside catabolism employs a guanosine deaminase required for the generation of xanthosine in Arabidopsis. Plant Cell, 25, 4101-4109.
31.
SuzukiT, AshiharaH, WallerGR. (1992) Purine and purine alkaloid metabolism in Camellia and Coffea plants. Phytochemistry, 91, 2575-2584.
32.
KremersRE. (1954) Speculation on DPN as a biochemical precursor of caffeine and trigonelline in coffee. Journal of American Pharmaceutical Association, 43, 423-424.
33.
KendeH. (1960) Untersuchungen über die biosynthese und bedeutung von trigonellin in Coffea arabica. Bericht der Schweizerischen Botanischen Gesellschaft, 70, 232-267.
34.
NottbohmFEMeyerF. (1931) Trigonellin gehalt des Kaffees. European Food Research and Technology, 61, 429–435.
35.
HadornH, SuterH. (1956) Über die analyse und zusammensetzung von rohkaffee verschiedener provenienzen. Mitteilungen Lebensmitteluntersuchung und Hygiene, 47, 33-51.
36.
MorathP. (1983) Untersuchungen zur Coffein-Biosynthese in Coffea arabica L. unter besonderer Berücksichtigung der Rolle des Adenins. Inaugural-Dissertation der Philosophischen Fakultät II der Universität Zürich.
37.
KoshiishiC, KatoA, YamaS, CrozierA, AshiharaH. (2001) A new caffeine biosynthetic pathway in tea leaves: utilisation of adenosine released from S-adenosyl-L-methionine cycle. FEBS letters, 499, 50-54.
38.
ZhouW, KarcherD, BockR. (2013) Importance of adenosine-to-inosine editing adjacent to the anticodon in an Arabidopsis alanine tRNA under environmental stress. Nucleic Acids Research, 41, 3362-3372.
39.
ZhouW, KarcherD, BockR. (2014) Identification of enzymes for adenosine-to-inosine editing and discovery of cytidine-to-uridine editing in nucleus-encoded transfer RNAs of Arabidopsis. Plant Physiology, 166, 1985-1997.
40.
WannerH, HagemannP. (1969) Über den Einfluss von Kinetin auf den Coffeingehalt der Blätter von Coffea arabica L. Planta, 86, 42-49.
41.
ChengQ, GuJ, CompaanKRSchaeferHF III. (2012) Isoguanine formation from adenine. Chemistry - A European Journal, 18, 4877-4886.
42.
KaplanNOColowickSPCiottiMM. (1952) Enzymatic deamination of adenosine derivatives. Journal of Biological Chemistry, 194, 579-591.
43.
KulikowskaE, KierdaszukB, ShugarD. (2004) Xanthine, xanthosine and its nucleotides: solution structures of neutral and ionic forms, and relevance to substrate properties in various enzyme systems and metabolic pathways. Acta Biochimica Polonica, 51, 493-531.
44.
MizunoK, MatsuzakiM, KanazawaS, TokiwanoT, YoshizawaY, KatoM. (2014) Conversion of nicotinic acid to trigonelline is catalyzed by N-methyltransferase belonged to motif B’ methyltransferase family in Coffea arabica. Biochemical and Biophysical. Research Communications, 452, 1060-1066.
45.
AshiharaH. (2015) Plant biochemistry: Trigonelline biosynthesis in Coffea arabica and Coffea canephora. In Coffee – In Health and Disease Prevention, ReedyVR. (Ed). Academic Press, 19-28.
46.
DongW-R, SunC-C, ZhuG, HuS-H, XiangL-X, ShaoJ-Z. (2014) New function for Escherichia coli xanthosine phosphorylase (xapA): genetic and biochemical evidences on its participation in NAD+ salvage from nicotinamide. BMC Microbiology, 14, 29.
