A few Camellia plants accumulate caffeine, theobromine and theacrine. The present article reviews the distribution of purine alkaloids and biosynthetic pathways, including properties and genes of the caffeine synthase family of enzymes, and catabolism. Plant physiological studies and ecology-related studies are also summarized briefly.
AshiharaH. (2006) Metabolism of alkaloids in coffee plants. Brazilian Journal of Plant Physiology, 18, 1–8.
2.
SealyJR. (1958) A revision of the genus Camellia. Royal Horticulture Society, London, 123–125.
3.
NagataT, SakaiS. (1984) Differences in caffeine, flavonols and amino acids contents in leaves of cultivated species of Camellia. Japanese Journal of Breeding, 34, 459–467.
4.
NagataT, SakaiS. (1985) Purine base pattern of Camellia irrawadiensis. Phytochemistry, 24, 2271–2272.
5.
YeC.-X, LinY, ZhouH, ChengF, LiX. (1997) Isolation and analysis of purine alkaloids from Camellia ptilophylla. Chang Acta Scientiarum Naturalium Universitatis Sunyatseni, 36, 30–33.
6.
ZhengXQ, YeCX, KatoM, CrozierA, AshiharaH. (2002) Theacrine (1,3,7,9-tetramethyluric acid) synthesis in leaves of a Chinese tea, kucha (Camellia assamica var. kucha). Phytochemistry, 60, 129–134.
7.
AshiharaH, KubotaH. (1987) Biosynthesis of purine alkaloids in Camellia plants. Plant & Cell Physiology, 28, 535–539.
8.
FujimoriF, AshiharaH. (1990) Adenine metabolism and the synthesis of purine alkaloids in flowers of Camellia plants. Phytochemistry, 29, 3513–3516.
9.
AshiharaH, KubotaH. (1986) Patterns of adenine metabolism and caffeine biosynthesis in different parts of tea seedlings. Physiologia Plantarum, 68, 275–281.
10.
SuzukiT, WallerGR. (1986) Total nitrogen and purine alkaloids in the tea plant throughout the year. Journal of the Science of Food & Agriculture, 37, 862–866.
11.
SuzukiT, WallerGR. (1985) Purine alkaloids of fruits of Camellia sinensis L. and Coffea arabica L. during fruit development. Annals of Botany, 56, 537–542.
12.
SuzukiT, WallerGR. (1985) Effects of light on the production and degradation of caffeine in Camellia sinensis L. seedlings. Plant & Cell Physiology, 26, 765–768.
13.
StasollaC, KatahiraR, ThorpeTA, AshiharaH. (2003) Purine and pyrimidine nucleotide metabolism in higher plants. Journal of Plant Physiology, 160, 1271–1295.
14.
AshiharaH, CrozierA. (1999) Biosynthesis and metabolism of caffeine and related purine alkaloids in plants. Advances in Botanical Research, 30, 118–205.
15.
ZrennerR, StittM, SonnewaldU, BoldtR. (2006) Pyrimidine and purine biosynthesis and degradation in plants. Annual Review of Plant Biology, 57, 805–836.
16.
ItoE, AshiharaH. (1999) Contribution of purine nucleotide biosynthesis de novo to the formation of caffeine in young tea (Camellia sinensis) leaves. Journal of Plant Physiology, 254, 145–151.
17.
KeyaCA, CrozierA, AshiharaH. (2003) Inhibition of caffeine biosynthesis in tea (Camellia sinensis) and coffee (Coffea arabica) plants by ribavirin. FEBS Letters, 554, 473–477.
18.
KoshiishiC, KatoA, YamaS, CrozierA, AshiharaH. (2001) A new caffeine biosynthetic pathway in tea leaves: utilisation of adenosine released from the S-adenosyl-L-methionine cycle. FEBS Letters, 499, 50–54.
19.
NegishiO, OzawaT, ImagawaH. (1994) Guanosine deaminase and guanine deaminase from tea leaves. Bioscience, Biotechnology & Biochemistry, 58, 1277–1281.
20.
AshiharaH, SuzukiT. (2004) Distribution and biosynthesis of caffeine in plants. Frontiers in Bioscience, 9, 1864–1876.
21.
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.
22.
UefujiH, OgitaS, YamaguchiY, KoizumiN, SanoH. (2003) Molecular cloning and functional characterization of three distinct N-methyltransferases involved in the caffeine biosynthetic pathway in coffee plants. Plant Physiology, 132, 372–380.
McCarthyAA, McCarthyJG. (2007) The structure of two N-methyltransferases from the caffeine biosynthetic Pathway. Plant Physiology, 144, 879–889.
25.
KatoM, MizunoK, FujimuraT, IwamaM, IrieM, CrozierA, AshiharaH. (1999) Purification and characterization of caffeine synthase from tea leaves. Plant Physiology, 120, 597–586.
26.
KatoM, MizunoK, CrozierA, FujimuraT, AshiharaH. (2000) A gene encoding caffeine synthase from tea leaves. Nature, 406, 956–957.
27.
AshiharaH, KatoM, YeC-X. (1998) Biosynthesis and metabolism of purine alkaloids in leaves of cocoa tea (Camellia ptilophylla). Journal of Plant Research, 111, 599–604.
28.
YoneyamaN, MorimotoH, YeC-X, AshiharaH, MizunoK, KatoM. (2006) Substrate specificity of N-methyltransferase involved in purine alkaloids synthesis is dependent upon one amino acid residue of the enzyme. Molecular Genetics & Genomics, 275, 125–135.
29.
SuzukiT. (1972) The participation of S-adenosylmethionine in the biosynthesis of caffeine in the tea plant. FEBS Letters, 24, 18–20.
30.
FujimoriN, SuzukiT, AshiharaH. (1991) Seasonal variations in biosynthetic capacity for the synthesis of caffeine in tea leaves. Phytochemistry, 30, 2245–2248.
MizunoK, OkudaA, KatoM, YoneyamaN, TanakaH, AshiharaH, FujimuraT. (2003) Isolation of a new dual-functional caffeine synthase gene encoding an enzyme for the conversion of 7-methylxanthine to caffeine from coffee (Coffea arabica L.). FEBS Letters, 534, 75–81.
33.
KatoM, MizunoK. (2004) Caffeine synthase and related methyltransferases in plants. Frontiers in Bioscience, 9, 1833–1842.
34.
RossJR, NamKH, D'AuriaJC, PicherskyE. (1999) S-Adenosyl-methionine: salicylic acid carboxyl methyltransferase, an enzyme involved in floral scent production and plant defense, represents a new class of plant methyltransferases. Archives of Biochemistry & Biophysics, 367, 9–16.
35.
FukamiH, AsakuraT, HiranoH, AbeK, ShimomuraK, YamakawaT. (2002) Salicylic acid carboxyl methyltransferase induced in hairy root cultures of Atropa belladonna after treatment with exogeneously added salicylic acid. Plant & Cell Physiology, 43, 1054–1058.
36.
NegreF, KolosovaN, KnollJ, KishCM, DudarevaN. (2002) Novel S-adenosyl-L-methionine: salicylic acid carboxyl methyltransferase, an enzyme responsible for biosynthesis of methyl salicylate and methyl benzoate, is not involved in floral scent production in snapdragon flowers. Archives of Biochemistry & Biophysics, 406, 261–270.
37.
DudarevaN, MurfittLM, MannCJ, GorensteinN, KolosovaN, KishCM, BonhamC, WoodK. (2000) Developmental regulation of methyl benzoate biosynthesis and emission in snapdragon flowers. The Plant Cell, 12, 949–961.
38.
SeoHS, SongJT, CheongJJ, LeeYH, LeeYW, HwangI, LeeJS, ChoiYD. (2001) Jasmonic acid carboxyl methyltransferase: A key enzyme for jasmonate-regulated plant responses. Proceedings of the National Academy of Sciences of the United States of America, 98, 4788–4793.
39.
YangY, YuanJS, RossJ, NoelJP, PicherskyE, ChenF. (2006) An Arabidopsis thaliana methyltransferase capable of methylating farnesoic acid. Archives of Biochemistry & Biophysics, 448, 123–132.
40.
HibiN, HigashiguchiS, HashimotoT, YamadaY. (1994) Gene expression in tobacco low-nicotine mutants. The Plant Cell, 6, 723–735.
41.
ChoiKB, MorishigeT, ShitanN, YazakiK, SatoF. (2002) Molecular cloning and characterization of coclaurine N-methyltransferase from cultured cells of Coptis japonica. Journal of Biological Chemistry, 277, 830–835.
42.
ZubietaC, RossJR, KoscheskiP, YangY, PicherskyE, NoelJP. (2003) Structural basis for substrate recognition in the salicylic acid carboxyl methyltransferase family. The Plant Cell, 15, 1704–1716.
43.
AshiharaH, GilliesFM, CrozierA. (1997) Metabolism of caffeine and related purine alkaloids in leaves of tea (Camellia sinensis L.). Plant & Cell Physiology, 38, 413–419.
44.
ItoE, CrozierA, AshiharaH. (1997) Theophylline metabolism in higher plants. Biochimica et Biophysica Acta, 1336, 323–330.
45.
FujimoriN, AshiharaH. (1993) Biosynthesis of caffeine in flower buds of Camellia sinensis. Annals of Botany, 71, 279–284.
46.
TerrasakiY, SuzukiT, AshiharaH. (1994) Purine metabolism and the biosynthesis of purine alkaloids in tea fruits during development. Plant Physiology (Life Science Advances), 13, 135–142.
47.
LiY, OgitaS, KeyaCA, AshiharaH. (2008) Expression of caffeine biosynthesis genes in tea (Camellia sinensis). Zeitschrift für Naturforschung, in press.
48.
CrozierA, BaumannTW, AshiharaH, SuzukiT, WallerGR. (1997) Pathways involved in the biosynthesis and catabolism of caffeine in Coffea and Camellia. Proceedings of the 17th ASIC Colloquium (Nairobi), 106–113.
49.
AnanT, NakagawaM. (1974) Effect of light on chemical constituents in tea leaves. Nippon Nogeikagaku Kaishi, 48, 91–98.
50.
KoshiishiC, ItoE, KatoA, YoshidaY, CrozierA, AshiharaH. (2000) Purine alkaloid biosynthesis in young leaves of Camellia sinensis in light and darkness. Journal of Plant Research, 113, 217–221.
51.
FriedmanJ, WallerGR. (1983) Caffeine hazards and their prevention in germinating seeds of coffee (Coffea arabica L.). Journal of Chemical Ecology, 9, 1099–1106.
52.
WallerGR. (1989) Biochemical frontiers of allelopathy. Biologia Plantarum, 31, 418–447.
53.
AnayaAL, Cruz-OrtegaR, WallerGR. (2006) Metabolism and ecology of purine alkaloids. Frontiers in Bioscience, 11, 2354–2370.
54.
FrischknechtPM, Ulmer-DufekJ, BaumannTW. (1986) Purine alkaloid formation in buds and developing leaflets of Coffea arabica: Expression of an optimal defense strategy?Phytochemistry, 25, 613–616.
55.
SuzukiT, WallerGR. (1987) Allelopathy due to purine alkaloids in tea seeds during germination. Plant & Soil, 98, 131–136.
