Caffeine and related purine alkaloids: Biosynthesis, catabolism, function and genetic engineering

Phytochemistry - Tập 69 - Trang 841-856 - 2008
Hiroshi Ashihara1, Hiroshi Sano2, Alan Crozier3
1Department of Biological Sciences, Graduate School of Humanities and Sciences, Ochanomizu University, Otsuka, Bunkyo-ku, Tokyo 112-8610, Japan
2Botanical Institute, Stockholm University, Stockholm 106 91, Sweden
3Graham Kerr Building, Division of Environmental and Evolutionary Biology, Institute of Biomedical and Life Sciences, University of Glasgow, Glasgow G12 8QQ, UK

Tài liệu tham khảo

Anan, 1974, Effect of light on chemical constituents in the tea leaves, Nippon Nogeikagaku Kaishi, 48, 91, 10.1271/nogeikagaku1924.48.91 Anaya, 2006, Metabolism and ecology of purine alkaloids, Front. Biosci., 11, 2354, 10.2741/1975 Aneja, 2001, Induction and accumulation of caffeine in young, actively growing leaves of cocoa (Theobroma cacao L.) by wounding or infection with Crinipellis perniciosa, Physiol. Mol. Plant Pathol., 59, 13, 10.1006/pmpp.2001.0337 Ashihara, 1993, Purine metabolism and the biosynthesis of caffeine in maté leaves, Phytochemistry, 33, 1427, 10.1016/0031-9422(93)85103-X Ashihara, 1999, Biosynthesis and metabolism of caffeine and related purine alkaloids in plants, Adv. Bot. Res., 30, 118 Ashihara, 1999, Biosynthesis and catabolism of caffeine in low-caffeine-containing species of Coffea, J. Agric. Food Chem., 47, 3425, 10.1021/jf981209n Ashihara, 1997, Metabolism of caffeine and related purine alkaloids in leaves of tea (C amellia sinensis L.), Plant Cell Physiol., 38, 413, 10.1093/oxfordjournals.pcp.a029184 Ashihara, 1998, Biosynthesis and metabolism of purine alkaloids in leaves of cocoa tea (Camellia ptilophylla), J. Plant Res., 111, 599, 10.1007/BF02507798 Ashihara, 1986, Patterns of adenine metabolism and caffeine biosynthesis in different parts of tea seedlings, Physiol. Plant., 68, 275, 10.1111/j.1399-3054.1986.tb01926.x Ashihara, 1987, Biosynthesis of purine alkaloids in Camellia plants, Plant Cell Physiol., 28, 535 Ashihara, 1996, Catabolism of caffeine and related purine alkaloids in leaves of Coffea arabica L, Planta, 198, 334, 10.1007/BF00620048 Ashihara, 2004, Distribution and biosynthesis of caffeine in plants, Front. Biosci., 9, 1864, 10.2741/1367 Ashihara, 1997, Metabolic fate of guanosine in higher plants, Physiol. Plant, 100, 909, 10.1111/j.1399-3054.1997.tb00017.x Ashihara, 2006, Caffeine biosynthesis and adenine metabolism in transgenic Coffea canephora plants with reduced expression of N-methyltransferase genes, Phytochemistry, 67, 882, 10.1016/j.phytochem.2006.02.016 Athaydea, 2000, Caffeine and theobromine in epicuticular wax of Ilex paraguariensis A. St.-Hil, Phytochemistry, 55, 853, 10.1016/S0031-9422(00)00324-1 Bailey, 2005, Developmental expression of stress response genes in Theobroma cacao leaves and their response to Nep1 treatment and a compatible infection by Phytophthora megakarya, Plant Physiol. Biochem., 43, 611, 10.1016/j.plaphy.2005.04.006 Baker, 1997, Signaling in plant–microbe interactions, Science, 267, 726, 10.1126/science.276.5313.726 Baumann, 1976, Caffeine and methylated uric acids: chemical patterns during vegetative development of Coffea liberica, Biochem. Physiol. Pflanzen., 170, 217, 10.1016/S0015-3796(17)30205-6 Baumann, 1980, The 1,3,7,9-tetramethyluric acid content of cupu (Theobroma grandiflorum), Acta Amaz., 10, 425, 10.1590/1809-43921980102425 Baumann, 1995, Guarana (Paullinia cupana) rewards seed dispersers without intoxicating them by caffeine, Phytochemistry, 39, 1063, 10.1016/0031-9422(94)00141-F Chang, 1988, A discovery of new tea resource Cocoa tea tree containing theobromine from China, Acta Sci. Natur. Univ. Sunyatseni, 27, 131 Coelho, 2007, Effect of light intensity on methylxanthine contents of Ilex paraguariensis A. St. Hil, Biochem. System. Ecol., 35, 75, 10.1016/j.bse.2006.09.001 Clifford, 1991, Caffeine from green beans of Mascarocoffea, Phytochemistry, 30, 4039, 10.1016/0031-9422(91)83461-S Frischknecht, 1986, Purine alkaloid formation in buds and developing leaflets of Coffea arabica: expression of an optimal defence strategy?, Phytochemistry, 25, 613, 10.1016/0031-9422(86)88009-8 Fujimori, 1990, Adenine metabolism and the synthesis of purine alkaloids in flowers of Camellia plants, Phytochemistry, 29, 3513, 10.1016/0031-9422(90)85266-I Fujimori, 1994, Biosynthesis of theobromine and caffeine in developing leaves of Coffea arabica, Phytochemistry, 36, 1359, 10.1016/S0031-9422(00)89724-1 Fujimori, 1991, Seasonal variations in biosynthetic capacity for the synthesis of caffeine in tea leaves, Phytochemistry, 30, 2245, 10.1016/0031-9422(91)83622-R Gluck, 1988, Heteroxanthinedemethylase, a new enzyme in the degradation of caffeine by Pseudomonas putida, Appl. Microbiol. Biotechnol., 28, 59, 10.1007/BF00250499 Green, 1972, Wound-induced protease inhibitor in plant leaves: a possible defense mechanism against insects, Science, 175, 776, 10.1126/science.175.4023.776 Guerreiro Filho, 2003, Caffeine and resistance of coffee to the berry borer Hypothenemus hampei (Coleoptera: Scolytidae), J. Agric. Food Chem., 51, 6987, 10.1021/jf0347968 Hammerstone, 1994, Purine alkaloid distribution within Herrania and Theobroma, Phytochemistry, 35, 1237, 10.1016/S0031-9422(00)94827-1 Hohnloser, 1980, Enzymological aspects of caffeine demethylation and formaldehyde oxidation by Pseudomonas putida C1, Hoppe Seyler’s Z. Physiol. Chem., 361, 1763, 10.1515/bchm2.1980.361.2.1763 Hollingsworth, 2002, Caffeine as a repellent for slugs and snails, Nature, 417, 915, 10.1038/417915a Huber, M., Baumann, T.W., 1998. The first step of caffeine degradation in coffee – still a mistery. In: Symposium Future Trends in Phytochemistry. The Phytochemical Society of Europe, Rolduc, The Netherlands. Ito, 1999, Contribution of purine nucleotide biosynthesis de novo to the formation of caffeine in young tea (Camellia sinensis) leaves, J. Plant Physiol., 254, 145, 10.1016/S0176-1617(99)80202-8 Ito, 1997, Theophylline metabolism in higher plants. Biochim, Biophys. Acta, 1336, 323, 10.1016/S0304-4165(97)00045-7 Iwasaki, M., 2006. Alkaloid metabolism in cacao (Theobroma cacao) plants. B.Sc Thesis, Faculty of Science, Ochanomizu University. Jouanin, 1998, Transgenic plants for insect resistance, Plant Sci., 131, 1, 10.1016/S0168-9452(97)00239-2 Kalberer, 1965, Breakdown of caffeine in the leaves of Coffea arabica L, Nature, 205, 597, 10.1038/205597a0 Kodama, Y., Shinya, T., Sano, H., 2007. Dimerization of N-methyltransferases involved in caffeine biosynthesis. Biochimie, in press. doi:10.1016/j.biochi.2007.10.001. Kato, 2004, Caffeine synthase and related methyltransferases in plants, Front. Biosci., 9, 1833, 10.2741/1364 Kato, 2000, A gene encoding caffeine synthase from tea leaves, Nature, 406, 956, 10.1038/35023072 Kato, 1999, Purification and characterization of caffeine synthase from tea leaves, Plant Physiol., 120, 586, 10.1104/pp.120.2.579 Keya, 2003, Inhibition of caffeine biosynthesis in tea (Camellia sinensis) and coffee (Coffea arabica) plants by ribavirin, FEBS Lett., 554, 473, 10.1016/S0014-5793(03)01213-4 Kim, 2006, Transgenic tobacco plants producing caffeine: a potential new strategy for insect pest control, Transgenic Res., 15, 667, 10.1007/s11248-006-9006-6 Kim, Y.-S., Sano, H., 2007. Pathogen resistance in transgenic tobacco plants producing caffeine. Phytochemistry, in press. doi:10.1016/j.phytochem.2007.10.021. Koshiishi, 2000, Purine alkaloid biosynthesis in young leaves of Camellia sinensis in light and darkness, J. Plant Res., 113, 217, 10.1007/PL00013902 Koshiishi, 2001, A new caffeine biosynthetic pathway in tea leaves: utilisation of adenosine released from the S-adenosyl-L-methionine cycle, FEBS Lett., 499, 50, 10.1016/S0014-5793(01)02512-1 Koshiro, 2006, Changes in content and biosynthetic activity of caffeine and trigonelline during growth and ripening of Coffea arabica and Coffea canephora fruits, Plant Sci., 171, 242, 10.1016/j.plantsci.2006.03.017 Koyama, 2003, Metabolism of purine bases, nucleosides and alkaloids in theobromine-forming Theobroma cacao leaves, Plant Physiol. Biochem., 41, 977, 10.1016/j.plaphy.2003.07.002 Kretschmar, 1999, Caffeine in Citrus flowers, Phytochemistry, 52, 19, 10.1016/S0031-9422(99)00119-3 Kumar, 1995, Attack on tea by Xyleborus fornicatus: inhibition of the symbiote, Monacrosporium ambrosium, by caffeine, Phytochemistry, 40, 1113, 10.1016/0031-9422(95)00396-O Li,Y., Ogita, S., Keya, C.A., Ashihara, H., accepted for publication. Expression of caffeine biosynthesis genes in tea (Camellia sinensis). Z. Naturforsch. 62c. Marx, 2003, Caffeine and theobromine composition of maté (Ilex paraguariensis) leaves in five plantations of Misiones, Argentina, Plant Foods Human Nutr., 58, 1, 10.1023/B:QUAL.0000041144.28025.fc Mazzafera, 1993, 7-Methylxanthine is not involved in caffeine catabolism in Coffea dewevrei, J. Agric. Food Chem., 41, 1541, 10.1021/jf00034a002 Mazzafera, 1994, Caffeine, theobromine and theophylline distribution in Ilex paraguariensis, Rev. Brasil Fisiol. Veg., 6, 149 Mazzafera, 1998, Growth and biochemical alterations in coffee due to selenite toxicity, Plant Soil, 201, 189, 10.1023/A:1004328717851 Mazzafera, 2004, Catabolism of caffeine in plants and microorganisms, Front. Biosci., 9, 1348, 10.2741/1339 Mazzafera, 1992, Breeding for low seed caffeine content of coffee (Coffea L.) by interspecific hybridization, Euphytica, 59, 55, 10.1007/BF00025361 McCarthy, 2007, The structure of two N-methyltransferases from the caffeine biosynthetic pathway, Plant Physiol., 144, 879, 10.1104/pp.106.094854 Mizuno, 2003, The first committed step reaction of caffeine biosynthesis: 7-methylxanthosine synthase is closely homologous to caffeine synthases in coffee (Coffea arabica L.), FEBS Lett., 547, 56, 10.1016/S0014-5793(03)00670-7 Mizuno, 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 Lett., 534, 75, 10.1016/S0014-5793(02)03781-X Mizuno, 2001 Nagata, 1984, Differences in caffeine, flavanols and amino acids contents in leaves of cultivated species of Camellia, Jpn. J. Breed., 34, 459, 10.1270/jsbbs1951.34.459 Nathanson, 1984, Caffeine and related methylxanthines: possible naturally occurring pesticides, Science, 226, 184, 10.1126/science.6207592 Negishi, 1988, N-methylnucleosidase from tea leaves, Agric. Biol. Chem., 52, 169, 10.1271/bbb1961.52.169 Negishi, 1994, Guanosine deaminase and guanine deaminase from tea leaves, Biosci. Biotech. Biochem., 58, 1277, 10.1271/bbb.58.1277 Ogawa, 2001, 7-Methylxanthine methyltransferase of coffee plants: gene isolation and enzymatic properties, J. Biol. Chem., 276, 8213, 10.1074/jbc.M009480200 Ogita, 2003, Production of decaffeinated coffee plants by genetic engineering, Nature, 423, 823, 10.1038/423823a Ogita, 2004, Application of RNAi to confirm theobromine as the major intermediate for caffeine biosynthesis in coffee plants with potential for construction of decaffeinated varieties, Plant Mol. Biol., 54, 931, 10.1007/s11103-004-0393-x Ogita, 2005, Metabolic engineering of caffeine production, Plant Biotechnol., 22, 461, 10.5511/plantbiotechnology.22.461 Ohta, 1990, Construction and expression in tobacco of a β-glucuronidase (GUS) reporter gene containing an intron within the coding sequence, Plant Cell Physiol., 31, 805 Petermann, 1983, Metabolic relations between methylxanthines and methyluric acids in Coffea, Plant Physiol., 73, 961, 10.1104/pp.73.4.961 Saijo, 1980, Effect of shade treatment on biosynthesis of catechins in tea plants, Plant Cell Physiol., 21, 989 Schulthess, 1996, Caffeine biosynthesis starts with the metabolically channelled formation of 7-methyl-XMP – a new hypothesis, Phytochemistry, 41, 169, 10.1016/0031-9422(95)00586-2 Senanayake, 1971, Theobromine and caffeine content of the cocoa bean during its growth, J. Sci. Food Agric., 22, 262, 10.1002/jsfa.2740220512 Silvarolla, 2004, A naturally decaffeinated arabica coffee, Nature, 429, 826, 10.1038/429826a Stasolla, 2003, Purine and pyrimidine nucleotide metabolism in higher plants, J. Plant Physiol., 160, 1271, 10.1078/0176-1617-01169 Suzuki, 1984, Biodegradation of caffeine: formation of theophylline and caffeine in mature Coffea arabica fruits, J. Sci. Food Agric., 35, 66, 10.1002/jsfa.2740350111 Suzuki, 1985, Purine alkaloids of fruits of Camellia sinensis L. and Coffea arabica L. during fruit development, Ann. Bot., 56, 537, 10.1093/oxfordjournals.aob.a087038 Suzuki, 1992, Purine and purine alkaloid metabolism in Camellia and Coffea plants, Phytochemistry, 31, 2575, 10.1016/0031-9422(92)83590-U Terrasaki, 1994, Purine metabolism and the biosynthesis of purine alkaloids in tea fruits during development, Plant Physiol. (Life Sci. Adv.), 13, 135 Uefuji, 2003, Molecular cloning and functional characterization of three distinct N-methyltransferases involved in the caffeine biosynthetic pathway in coffee plants, Plant Physiol., 132, 372, 10.1104/pp.102.019679 Uefuji, 2005, Caffeine production in tobacco plants by simultaneous expression of three coffee N-methyltransferases and its potential as a pest repellant, Plant Mol. Biol., 59, 221, 10.1007/s11103-005-8520-x Vitória, 1998, Caffeine degradation in leaves and fruits of Coffea arabica and Coffea dewevrei, Pesquisa Agropecuaria Brasil, 33, 1957 Weckerle, 2003, Purine alkaloids in Paullinia, Phytochemistry, 64, 735, 10.1016/S0031-9422(03)00372-8 Ye, 1997, Isolation and analysis of purine alkaloids from Camellia ptilophylla Chang, Acta Sci. Natur. Univ. Sunyatseni, 36, 30 Yoneyama, 2006, Substrate specificity of N-methyltransferase involved in purine alkaloids synthesis is dependent upon one amino acid residue of the enzyme, Mol. Gen. Genom., 275, 125, 10.1007/s00438-005-0070-z Zheng, 2004, Biosynthesis, accumulation and degradation of theobromine in developing Theobroma cacao fruits, J. Plant Physiol., 161, 363, 10.1078/0176-1617-01253 Zheng, 2004, Distribution, biosynthesis and function of purine and pyridine alkaloids in Coffea arabica seedlings, Plant Sci., 166, 807, 10.1016/j.plantsci.2003.11.024 Zheng, 2002, Theacrine (1,3,7,9-tetramethyluric acid) synthesis in leaves of a Chinese tea, kucha (Camellia assamica var. kucha), Phytochemistry, 60, 129, 10.1016/S0031-9422(02)00086-9 Zrenner, 2006, Pyrimidine and purine biosynthesis and degradation in plants, Annu. Rev. Plant Biol., 57, 805, 10.1146/annurev.arplant.57.032905.105421 Zubieta, 2003, Structural basis for substrate recognition in the salicylic acid carboxyl methyltransferase family, Plant Cell, 15, 1704, 10.1105/tpc.014548 Zulak, 2006, Alkaloids, 102