Aroma production by tissue cultures

Journal of Agricultural and Food Chemistry

Volumn 54, Issue 4, 2006, Pages 1116-1123

  Hrazdina, G ^a  

^a New York State Agricultural Experiment Station   (United States)

Author keywords

(+) S (1 Propenyl) L cysteine sulfoxide; (+) S allyl L cysteine sulfoxide; (+) S methyl L cysteine sulfoxide; (+) S propyl L cysteine sulfoxide; Alliin; Aroma; Benzalacetone synthase; Callus; Cell culture; Chalcone synthase; Chitosan; Garlic; Onion

Indexed keywords

ALKANONE; BENZALDEHYDE DERIVATIVE; RASPBERRY KETONE; VANILLIN;

GARLIC; METABOLISM; ODOR; ONION; PLANT; REVIEW; ROSACEAE; STRAWBERRY; TISSUE CULTURE TECHNIQUE; VANILLA;

BENZALDEHYDES; BUTANONES; FRAGARIA; GARLIC; ODORS; ONIONS; PLANTS; ROSACEAE; TISSUE CULTURE TECHNIQUES; VANILLA;

ALLIUM CEPA; ALLIUM SATIVUM; FRAGARIA X ANANASSA; RUBUS GLAUCUS;

EID: 33644851863     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf053146w     Document Type: Review

References (66)

1. Haberland, O. Experiments on the culture of isolated plant cells. Sitzungsber. Acad. Wiss. Wien, Math.-Naturwiss. Kl., Abt. 3 1902, 111, 69-92.
2. Laimer, M., Rücker, W., Eds. Plant Tissue Culture - 100 Years since Gottlieb Haberlandt; Springer Life Sciences: Berlin, Germany, 2003; ISBN 3-211-83839-2.
3. Murashige, T.; Skoog, F. A revised medium for rapid growth and bio assays with tobacco tissue cultures. Physiol. Plant. 1962, 15, 472-475.
4. Misawa, M. Plant Tissue Culture: an Alternative for Production of Useful Metabolites; FAO Agricultural Services Bulletin 108; FAO: Rome, Italy, 1994; ISBN 92-5-103391-9.
5. Yang, R.; Potter, T. P.; Curtis, O. F.; Shetty, K. Tissue culture based selection of high rosmarinic acid producing clones of rosemary (Rosmarinus officinalis L.) using Pseudomonas strain F. Food Biotechnol. 1997, 11, 73-88.
6. Zabetakis, I.; Holden, M. A. Strawberry flavor: analysis and biosynthesis. J. Sci. Food Agric. 1997, 74, 421-434.
7. Havkin-Frenkel, D.; Dorn, R. Vanilla. In Spices: Flavor Chemistry and Antioxidant Properties; ACS Symposium Series 660; American Chemical Society: Washington, DC, 1997.
8. Ramachandra Rao, S.; Ravishankar, G. Vanilla flavor: production by conventional and biotechnical routes. J. Sci. Food Agric. 2000, 80, 289-304.
9. Funk, C.; Brodelius, P. Influence of growth regulators and an elicitor on phenylpropanoid metabolism in suspension cultures of Vanilla plantifolia. Phytochemistry 1990, 29, 845-848.
10. Brodelius, P.; Funk, C.; Häner, A.; Villegas, M. A procedure for the determination of optimal chitosan concentrations for elicitation of cultured plant cells. Phytochemistry 1989, 28, 2651-2654.
11. Funk, C.; Gügler, K.; Brodelius, P. Increased secondary product formation in plant cell suspension cultures after treatment with a yeast carbohydrate preparation (elicitor). Phytochemistry 1987, 26, 401-405.
12. Kurz, W. G. W.; Chatson, K. B.; Constabel, F.; Kutney, J. P.; Choi, L. S. L.; Kolodziejczyk, P.; Sleigh, S. K.; Stuart, K. L. The production of catharanthine and other indole alkaloids by cell-suspension cultures of Catharanthus-roseus. Planta Med. 1980, 39 (3), 284-284.
13. Zenk, M. H.; El-Shagi, H.; Schulte, U. Anthraquinone production by cell-suspension cultures of Morinda-citrifolia. Planta Med. Suppl. 1975, 79.
14. Zenk, M. H. Biosynthese von Vanillin in Vanilla plantifolia Andr. Z. Pflanzenphysiol. 1965, 55, 404-414.
15. Funk, C.; Brodelius, P. Phenylpropanoid metabolism in suspension cultures of Vanilla planifolia Andr. Plant Physiol. 1990, 94, 95-101.
16. Amrhein, N.; Gödeke, K. H. α-Aminooxy-β-phenylpropionic acid, a potent inhibitor of L-phenylalanine ammonia-lyase in vitro and in vivo. Plant Sci. Lett. 1977, 8, 313-317.
17. Grand, C.; Sarni, F.; Boudet, A. M. Inhibition of cinnamylalcohol dehydrogenase activity and lignin synthesis in poplar (Populus euroamericana Dode) tissues by two organic compounds. Planta 1985, 163, 232-237.
18. Funk, C.; Brodelius, P. Phenylpropanoid metabolism in suspension cultures of Vanilla planifolia Andr. IV. Induction of vanillic acid formation. Plant Physiol. 1992, 99, 256-262.
19. Gasson, M. J.; Kitamura, Y.; McLauchlan, W. R.; Narbad, A.; Parr, A. J.; Parsons, E. L. H.; Payne, J.; Rhodes, M. J. C.; Walton, N. J. Metabolism of ferulic acid to vanillin. J. Biol. Chem. 1998, 237, 4163-4170.
20. Podstolski, A,; Havkin-Frenkel, D.; Malinowski, J.; Blount, J. W.; Kourteva, G.; Dixon, R. A. Unusual 4-hydroxybenzaldehyde synthase activity from tissue cultures of the vanilla orchid Vanilla planifloria. Phytochemistry 2002, 61, 611-620.
21. Yazaki, K.; Heide, L.; Tabata, M. Formation of p-hydroxybenzoic acid from p-coumaric acid by cell free extract of Lithospermum erythrorhizon cell cultures. Phytochemistry 1991, 30, 2233-2236.
22. Schnitzler, J. P.; Madlung, J.; Rose, A.; Seitz, H. U. Biosynthesis of p-hydroxybenzoic acid in elicitor treated carrot cell cultures. Planta 1992, 188, 594-600.
23. Hertz, L. E. Dynamics and regulatory control of the vanillin biosynthetic pathway in V. planifolia embryo cultures. Ph.D. Thesis, Rutgers University, 2000.
24. Liu, B.; Beyerle, T.; Klundt, T.; Beerhues, L. Biphenyl synthase from yeast extract-treated cell cultures of Sorbus aucuparia. Planta 2004, 218, 492-496.
25. Bramble, J. L.; Graves, D. J.; Brodelius, P. Plant cell culture using a novel bioreactor: the magnetically stabilized fluidized bed. Biotechnol. Prog. 1990, 6, 452-457.
26. Walton, N. J.; Mayer, M. J.; Narbad, A. Molecules of interest: vanillin. Phytochemistry 2003, 63, 505-515.
27. van der Heuvel, R. H. H.; Fraaije, M. W.; Laane, C.; van Berkel, W. J. H. Enzymatic synthesis of vanillin. J. Agric. Food Chem. 2001, 49, 2954-2958.
28. Priefert, H.; Rabenhorst, J.; Steinbüchel, A. Biotechnological production of vanillin. Appl. Microbiol. Biotechnol. 2002, 56, 296-314.
29. Maarse, H. Volatile Compounds in Foods, 6th ed.; TNO-CIVO: Zeist, The Netherlands, 1989.
30. Schinz, H.; Seidel, C. F. Untersuchungen über Aromastoffe. Helv. Chim. Acta 1957, 40, 1839-1859.
31. Braun, G.; Hieke, E. Zur Analyse von Aromastoffen in Lebensmitteln. Dtsch. Lebensm. Rundsch. 1977, 73, 273-278.
32. Winter, M. Aroma and constitution XIX. Homologues and analogues of p-hydroxyphenyl-1-butanone-2 ("raspberry ketone"). Helv. Chim. Acta 1961, 44, 2110-2121.
33. Borejsza-Wysocki, W.; Goers, S. K.; McArdle, R. N. Hrazdina, G. p-Hydrozyphenylbutanone levels in raspberries determined by chromatographic and organoleptic methods. J. Agric. Food Chem. 1992, 40, 1176-1177.
34. Glynka, R.; Cieslinski, M.; Soszynski, M. New way of 1-(4-hydroxyphenyl)- butanone-3 (raspberry ketone) synthesis. Przem. Chem. 1986, 65, 549-550.
35. Tateiwa, J.; Horiuchi, H.; Hashimoto, K.; et al. Cation exchanged montmorillonate-catalyzed facile Friedel-Crafts alkylation of hydroxy and methoxy aromatics with 4-hydroxybutane-2-one to produce raspberry ketone and some pharmaceutically active compounds. J. Org. Chem. 1994, 59, 5901-5904.
36. Tateiwa, J.; Nishimura, T.; Horiuchi, H.; et al. Rearrangement of alkyl phenyl ethers to alkylphenols in the presence of cation exchanged montmorillonate (M(N+)-Mont. J. Chem. Soc., Perkin Trans. 1 1994, 3367-3371.
37. Borejsza-Wysocki, W.; Hrazdina, G. Biosynthesis of p-hydroxypenylbutan-2- one in raspberry fruits and tissue cultures. Phytochemistry 1994, 35, 623-628.
38. Pedapudi, S.; Chin, C. K.; Pedersen, H. Production and elicitation of benzalacetone and the raspberry ketone in cell suspension cultures of Rubus idaeus. Biotechnol. Prog. 2000, 16, 346-349.
39. Borejsza-Wysocki, W.; Hrazdina, G. Establishment of callus and cell suspension cultures of raspberry (Rubus idaeus cv. Royalty). Plant Cell Tissue Org. Cult. 1994, 36, 1-4.
40. Borejsza-Wysocki, W.; Hrazdina, G. Aromatic polyketide synthases: purification, characterization and antibody development to benzalacetone synthase from raspberry fruits. Plant Physiol. 1996, 110, 791-799.
41. Schröder, J. A family of plant specific polyketide synthases: facts and predictions. Trends Plant Sci. 1997, 2, 373-378.
42. Zheng, D.; Schröder, G.; Schröder. J.; Hrazdina, G. Molecular and biochemical characterization of three aromatic polyketide synthase genes from Rubus idaeus. Plant Mol. Biol. 2001, 46, 1-15.
43. Kumar, A.; Ellis, B. E. A family of polyketide synthase genes expressed in ripening Rubus fruits. Phytochemistry 2003, 62, 513-526.
44. Abe, I.; Takahashi, Y.; Morita, H.; Noguchi, H. Benzalacetone synthase: a novel polyketide synthase that plays a crucial role in the biosynthesis of phenylbutanones in Rheum palmatum. Eur. J. Biochem. 2001, 268, 1-7.
45. Kollmansberger, H.; Berger, R. G. Industrial recovery of strawberry flavor - fractional distillation vs plate condensation. Z. Lebensm. Unters. Forsch. 1994, 198, 491-494.
46. Hong, Y. C.; Harlander, S. K. Plant tissue culture systems for flavor production. In Flavor Chemistry of Lipid Foods; Min, D. B., Smouse, T. H., Eds.; American Oil Chemists' Society: Champaign, IL, 1989; pp 348-366.
47. Hong, Y. C.; Huang, L. C.; Reineccius, G. A.; Harlander, S. K.; Labuza, T. P. Production of aroma compounds from strawberry cell suspension cultures by addition of precursors. Plant Cell, Tissue Organ Cult. 1990, 21, 245-251.
48. Zabetakis, I.; Holden, M. A. The effect of 6-deoxy-D-fructose on flavor bioformation from strawberry (Fragaria ananassa cv. Elsanta) callus cultures. Plant Cell, Tissue Organ Cult. 1996, 45, 25-29.
49. Zabetakis, M.; Holden, M. A. Strawberry flavor: analysis and biosynthesis. J. Sci. Food Agric. 1997, 74, 421-434.
50. Jain, S. M.; Pehue, E. The prospect of tissue-culture and genetic engineering for strawberry improvement. Acta Agric. Scand., B, Soil Plant Sci. 1992, 42, 133-139.
51. Nehra, N. S.; Kartha, K. K.; Stushnoff, C.; Giles, K. L. The influence of plant growth regulator concentrations and callus age on somaclonal variation in callus-culture regenerants of strawberry. Plant Cell, Tissue Organ Cult. 1992, 29, 257-268.
52. Mohamed, F. H.; Swartz, H. J. Hormonal control of phenotypic behavior of tissue culture propagated strawberry. HortScience 1988, 23, 557.
53. Zhang, W.; Seki, M.; Furusaki, S.; Middelberg, A. P. J. Anthocyanin synthesis, growth and nutrient uptake in suspension cultures of strawberry cells. J. Ferm. Bioeng. 1998, 86, 72-78.
54. Wertheim, T. Investigation on garlic oil. Annals 1844, 51, 289-315.
55. Wertheim, T. On the relationship between mustard and garlic oils. Annals 1845, 55, 297-364.
56. Semmler, F. W. The essential oil of onion (Allium cepa L.). Arch. Pharm. 1892, 230, 434-443.
57. Whitaker, J. R. Development of flavor, odor and pungency in onion and garlic. Adv. Food Res. 1976, 22, 73-133.
58. Cavalito, C. J.; Bailey, J. H. Alliin, the antibacterial principle of Allium. J. Am. Chem. Soc. 1944, 66, 1950-1953.
59. Nock, L. P.; Mazelis, M. The C-S lyases of higher plants. Direct comparison of the physical properties of homogeneous alliin lyase of garlic (Allium sativum) and onion (Allium cepa). Plant Physiol. 1987, 85, 1079-1083.
60. Freeman, G. G.; Whenham, R. J.; Mackenzie, I. A.; Davey, M. R. Flavour components in tissue cultures of onion (Allium cepa L.). Plant Sci. Lett. 1974, 3, 121-125.
61. Davey, M. R.; Mackenzie, I. A.; Freeman, G. G.; Short, K. C. Studies of some aspects of the growth, fine structure and flavour production of onion tissue grown in vitro. Plant Sci. Lett. 1974, 3, 113-120.
62. Turnbull, A.; Galpin, J.; Smith, J. L.; Collin, H. A. Comparison of the onion (Allium cepa) and onion tissue culture. IV. Effect of shoot and root morphogenesis on flavour precursor synthesis in onion tissue cultures. New Phytol. 1981, 87, 257-268.
63. Malpathak, N.; David, S. B. Flavor formation in tissue cultures of garlic (Allium sativum L.). Plant Cell Rep. 1986, 5, 446-447.
64. Ohsumi, C.; Hayashi, T.; Sano, K. Formation of alliin in the culture tissues of Allium sativum. Oxidation of S-allyl-cysteine. Phytochemistry 1993, 33, 107-111.
65. Melouki, F.; Vannereau, A.; Auger, J.; Marcotte, J. L.; Cosson, L. Flavor production in tissue cultures of chive (A. schoenoprasum L.): callus structure and flavor production. Plant Sci. 1994, 95, 165-173.
66. Fu, T. J. Safety considerations for food ingredients produced by plant cell and tissue culture. CHEMTECH 1998, 40-48.