A Role for Trigonelline During Imbibition and Germination of Coffee Seeds

Abstract

Trigonelline was investigated as an NAD reserve during germination of coffee (Coffea arabica L.) seeds. Seeds were germinated on filter paper moistened with water or in agar and the endogenous content of trigonelline, nicotinic acid and NAD investigated in the endosperm, embryo and germination medium. Seeds were also fed with [carboxyl-¹⁴C]trigonelline and the distribution of the radioactivity in these compounds was investigated. In addition, trigonelline demethylase was detected in coffee for the first time, showing a K_m of 1.13 mM. The activity increased with germination. These data clearly show that in seeds there is a significant conversion of trigonelline to NAD, although a concomitant biosynthesis of the alkaloid is also observed. It is concluded that trigonelline is indeed a reserve molecule for NAD biosynthesis but this function may be limited to the very early stages of germination or restricted to specific tissues, such as the embryo.

Trigonelline - nicotinic acid - NAD - coffee seeds - germination - physiological role

References

• 01 Baumann,  T. W., and Gabriel,  H.. (1984);  Metabolism and excretion of caffeine during germination of Coffea arabica L.  Plant Cell Physiol.. 25 1431-1436
• 02 Berglund,  T.. (1994);  Nicotinamide, a missing link in the early stress response in eukaryotic cells: a hypothesis with special reference to oxidative stress in plants.  FEBS Letters. 351 145-149
• 03 Berglund,  T.,, Kalbin,  G.,, Strid,  A.,, Rydström,  J.,, and Ohlsson,  A. B.. (1996);  UV-B and oxidative stress-induced increase in nicotinamide and trigonelline and inhibition of defensive metabolism induction by poly(ADP-ribose)polymerase inhibitor in plant tissue.  FEBS Letters. 380 188-193
• 04 Bewley,  J. D., and Black,  M.. (1994) Seeds: physiology of development and germination. New York; Plenum Press pp. 445
• 05 Bino,  R. J.,, Lanteri,  S.,, Verhoeven,  H. A.,, and Kraak,  H. L.. (1993);  Flow cytometric determination of nuclear replication stages in seed tissues.  Ann. Bot.. 72 181-187
• 06 Blake,  C. O.. (1954);  Niacin metabolism in the corn seedling: the biosynthesis of trigonelline.  Am. J. Bot.. 41 231-238
• 07 Bradford,  M. N.. (1976);  A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding.  Anal. Biochem.. 72 248-254
• 08 Carvalho,  A.. (1962);  Variability of the niacin content in coffee.  Nature. 194 1096
• 09 Childs,  K. F.,, Ning,  X.-H.,, and Bolling,  S. F.. (1996);  Simultaneous detection of nucleotides, nucleosides and oxidative metabolites in myocardial biopsies.  J. Chromat. B. 678 181-186
• 10 Clifford,  M. N.. (1985) Chemical and physical aspects of green coffee and coffee products. Coffee: Botany, Biochemistry and Production of Beans and Beverage. Clifford, M. N. and Wilson, K. C., eds. Westport, Connecticut; AVI Publishing Conmpany, Inc. pp. 305-374
• 11 Coultate,  T. P.. (1996) Food: the chemistry of its components. Cambridge; The Royal Society of Chemistry pp. 360
• 12 Daglia,  M.,, Cuzzoni,  M. T.,, and Dacarro,  C.. (1994);  Antibacterial activity of coffee? Relationship between biological activity and chemical markers.  J. Agric. Food Chem.. 42 2273-2277
• 13 Dupriez,  H.. (1962);  L'imbibition des graines chez diverses espèces du genre Coffea L.  Agricultura. 10 151-168
• 14 Ellis,  R. H.,, Hong,  T. D.,, and Roberts,  E. H.. (1990);  An intermediate category of seed storage behaviour? I. coffee.  J. Exp. Bot.. 41 1167-1174
• 15 Joshi,  J. G., and Handler,  P.. (1962);  Metabolism of trigonelline.  J. Biol. Chem.. 237 3185-3188
• 16 Kalbin,  G.,, Ohlsson,  A. B.,, Berglund,  T.,, Rydström,  J.,, and Strid,  A.. (1997);  Ultraviolet-B-radiation-induced changes in nicotinamide and glutathione metabolism and gene expression in plants.  Eur. J. Biochem.. 249 465-472
• 17 Kraska,  T., and Schönbeck,  F.. (1993);  About changes in the chromatin structure after resistance induction in Hordeum vulgare L.  J. Phytopathol.. 137 10-14
• 18 Maestri,  M.,, Da Matta,  F. M.,, Regazzi,  A. J.,, and Barros,  R. S.. (1995);  Accumulation of proline and quaternary ammonium compounds in mature leaves of water stressed coffee plants (Coffea arabica and C. canephora).  J. Hort. Sci.. 70 229-233
• 19 Magni,  G.,, Amici,  A.,, Emanuelli,  M.,, Raffaelli,  N.,, and Ruggieri,  S.. (1999) Enzymology of NAD⁺ synthesis. Advances in Enzymology and Related Areas of Molecular Biology, Vol. 73: Mechanism of Enzyme Action, Part A. Purich, D. L., ed. New York; John Wiley & Sons, Inc. pp. 135-182
• 20 Mazzafera,  P.. (1991);  Trigonelline in coffee.  Phytochemistry. 30 2309-2310
• 21 Mazzuca,, Bitonti,  M. B.,, Pranno,  S.,, and Innocenti,  A. M.. (1997);  Nuclear metabolic changes in root meristem of Lactuca sativa induced by trigonelline treatment.  Cytobios. 89 39-50
• 22 Phillips,  D. A.,, Dakora,  F. D.,, Sande,  E.,, Joseph,  C. M.,, and Zon,  J.. (1995);  Synthesis, release, and transmission of alfafa signals to rhizobial symbionts.  Plant Soil. 161 69-80
• 23 Phillips,  D. A.,, Joseph,  C. M.,, and Maxwell,  C. A.. (1992);  Trigonelline and stachydrine released from alfafa seeds activate NodD2 protein in Rhizobium meliloti. .  Plant Physiol.. 99 1526-1531
• 24 Rena,  A. B., and Meastri,  M.. (1986) Fisiologia do cafeeiro. Cultura do Cafeeiro - Fatores que Afetam a Produtividade. Rena, A. B., Malavolta, E., Rocha, M., and Yamada, T., eds. Piracicaba, Brazil; Associação Brasileira para Pesquisa da Potassa e do Fosfato pp. 13-85
• 25 Salisbury,  F. B., and Ross,  C. W.. (1992) Plant physiology. Belmont; Wadsworth Publishing Company pp. 682
• 26 Taguchi,  H., and Shimabayashi,  Y.. (1983);  Findings of trigonelline demethylating enzyme activity in various organisms and some properties of the enzyme from hog liver.  Biochem. Biophys. Res. Commun.. 113 569-574
• 27 Taguchi,  H.,, Nishitani,  H.,, Okumura,  K.,, Shimabayashi,  Y.,, and Iwai,  K.. (1989);  Biosynthesis and metabolism of trigonelline in Lemna paucicostata 151.  Agric. Biol. Chem.. 53 2867-2871
• 28 Tramontano,  W. A., and Jouve,  D.. (1997);  Trigonelline accumulation in salt-stressed legumes and the role of other osmoregulators as cell cycle control agents.  Phytochemistry. 44 1037-1040
• 29 Tramontano,  W. A.,, Lynn,  D. G.,, and Evans,  L. S.. (1983);  Trigonelline, nicotinic acid and nicotinamide in seedlings of Pisum sativum. .  Phytochemistry. 22 673-678
• 30 Ueda,  M.,, Niwa,  M.,, and Yamamura,  S.. (1995);  Trigonelline, a leaf-closing factor of the nyctinastic plant, Aeschynomene indica. .  Phytochemistry. 39 817-819
• 31 Upmeier,  B.,, Gross,  W.,, Köster,  S.,, and Barz,  W.. (1988);  Purification and properties of S-adenosyl-L-methionine:nicotinic acid-N-methyltransferase from cell suspension cultures of Glycine max L.  Arch. Biochem. Biophys.. 262 445-454
• 32 Válio,  I. F. M.. (1976);  Germination of coffee seeds (Coffea arabica L. cv. Mundo Novo).  J. Exp. Bot.. 27 983-991
• 33 Wanner,  H., and Blaim,  K.. (1961);  Ein Beitrag zur Biosynthese und Physiologie von Kaffein und Trigonellin bei Coffea arabica. .  Planta. 56 499-510
• 34 Willeke,  U.,, Heeger,  V.,, Meise,  M.,, Neuhann,  H.,, Schindelmeiser,  I.,, Vordemfelde,  K.,, and Barz,  W.. (1979);  Mutually exclusive occurrence and metabolism of trigonelline and nicotinic acid arabinoside in plant cell cultures.  Phytochemistry. 18 105-110

Section Editor: A. Laeuchli