Flavonoid distribution during the development of leaves, Flowers, stems, and roots of Rosmarinus officinalis. Postulation of a biosynthetic pathway

Journal of Agricultural and Food Chemistry

Volumn 52, Issue 16, 2004, Pages 4987-4992

  Del Baño, María José ^a   Lorente, Juan ^a   Castillo, Julian ^a   Benavente García, Obdulio ^a   Marín, María Piedad ^a   Del Río, José Antonio ^b   Ortuño, Ana ^b   Ibarra, Isidro ^c  

^a 80320 Alcantarilla   (Spain)

^b UNIVERSITY OF MURCIA   (Spain)

^c TECHNICAL UNIVERSITY OF CARTAGENA   (Spain)

Author keywords

Diosmin; Eriocitrin; Flavonoids; Genkwanin; Hesperidin; Hispidulin 7 O glucoside; Isoscutellareln 7 O glucoside; Luteolin 3 O D glucuronide; Rosmarinus officinalis

Indexed keywords

DIOSMIN; DITERPENE; ERIOCITRIN; FLAVANOID; FLAVONE; GENKWANIN; HESPERIDIN; HISPIDULIN 7 O GLUCOSIDE; ISOSCUTELLAREIN 7 O GLUCOSIDE; LUTEOLIN; LUTEOLIN 3' O BETA DEXTRO GLUCURONIDE; ROSMARINIC ACID; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; CHEMICAL STRUCTURE; ENZYME ACTIVATION; FLOWER; PHYTOCHEMISTRY; PLANT DEVELOPMENT; PLANT LEAF; PLANT ROOT; PLANT STEM; ROSEMARY; SEASON;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FLAVONOIDS; FLOWERS; PLANT LEAVES; PLANT ROOTS; ROSMARINUS; SEASONS;

LAMIACEAE; ROSMARINUS OFFICINALIS;

EID: 3843087535     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf040078p     Document Type: Article

References (35)

1. Aeschbach, R.; Aeschbacher, H. V.; Phillippossian, G. Process for obtaining carnosic acid and its utilization for its anticarcinogenic and antiviral property. Eur. Patent 90119218.7, 1990.
2. Schwarz, K.; Ternes, W. Antioxidative constituents of Rosmarinus officinalis and Salvia officinalis. Z. Lebensm. Unters. Forsch. 1992, 195, 95-107.
3. Richheimer, S. L.; Bernart, M. W.; King, G. A.; Kent, M. C.; Bailey, D. T. Antioxidant activity of lipid-soluble phenolic diterpenes from rosemary. J. Am. Oil Chem. Soc. 1996, 73, 507-514.
4. Frankel, E. N.; Huang, S.; Aeschbach R.; Prior E. Antioxidant activity of a rosemary extract and its constituents, carnosic acid, carnosol, and rosmarinic acid, in bulk oil and oil-in-water emulsion. J. Agric. Food Chem. 1996, 44, 131-135.
5. Munné-Bosch, S.; Alegre, L.; Schwarz, K. The formation of phenolic diterpenes in Rosmarinus officinalis L. under Mediterranean climate. Eur. Food Res. Technol. 2000, 210, 263-267.
6. Masuda, T.; Inaba, Y.; Takeda, Y. Antioxidant mechanism of carnosic acid: Structural identification of two oxidation products. J. Agric. Food Chem. 2001, 49, 5560-5565.
7. Benavente-García, O.; Castillo, J.; Marin, F. R.; Ortuño, A.; del Río J. A. Uses and properties of Citrus flavonoids. J. Agric. Food Chem. 1997, 45, 4505-4515.
8. Tomás-Barberán, F. A.; Grayer-Barkmeijer, R. J.; Gil, M. I.; Harbome, J. B. Distribution of 6-hydroxy-, 6-methoxy- and 8-hydroxyflavone glycosides in the Labiatae, the Scrophulariaceae and related families. Phytochemistry 1988, 27, 2631-2645.
9. Cuvelier, M. E.; Berset, C.; Richard, H. Antioxidant constituents in sage (Salvia officinalis). J. Agric. Food Chem. 1994, 42, 665-669.
10. Okamura, N.; Haraguchi, H.; Hashimoto, K.; Yagi, A. Flavonoids in Rosmarinus officinalis leaves. Phytochemistry 1994, 37, 1463-1466.
11. Cuvelier, M. E.; Richard, H.; Berset, C. Antioxidative activity and phenolic composition of pilot plant extracts of sage and rosemary. J. Am. Oil Chem. Soc. 1996, 73, 645-652.
12. Señoráns, F. J.; Ibañez, E.; Cavero, S.; Tabera, J.; Reglero, G.; Liquid chromatographic-mass spectrometric analysis of super-critical-fluid extracts of rosemary plants. J. Chromatogr. 2000, 870, 491-499.
13. Justesen, U.; Knuthsen, P. Composition of flavonoids in fresh herbs and calculation of flavonoid intake by use of herbs in traditional Danish dishes. Food Chem. 2001, 73, 245-250.
14. El-Sayed, N. H.; Khalifa, T. I.; Ibrahim, M. T.; Mabry, T. J. Constituents from Salvia triloba. Fitoterapia 2001, 72, 850-853.
15. Del Baño, M. J.; Lorente, J.; Castillo, J.; Benavente-Gacía, O.; del Río, J. A.; Ortuño, A. Quirin, K. W.; Gerard, D. Phenolic diterpenes, flavones, and rosmarinic acid distribution during the development of leaves, flowers, stems, and roots of Rosmarinus officinalis. Antioxidant activity. J. Agric. Food Chem. 2003, 51, 4247-4253.
16. Munné-Bosch, S.; Schwarz, K.; Alegre, L. Enhanced formation of α-tocopherol and highly oxidized abietane diterpenes in water-stressed rosemary plants. Plant Physiol. 1999, 121, 1047-1052.
17. Castillo, J.; Benavente-García, O.; Del Río, J. A. Study and optimitation of citrus flavanone and flavone elucidation by reverse phase HPLC with several mobile phases: influence of the structural characteristics. J. Liq. Chromatogr. 1994, 17, 1497-1523.
18. Gracza, L.; Ruff, P. The occurrence and analysis of phenylpropane derivatives. 5. Rosmarinic acid in pharmacopoeial drugs and its determination by HPLC. Arch. Pharm. (Weinheim) 1984, 317, 339-345.
19. Lamaison, J. L.; Petitjean-Freytet, C.; Carnat, A. Medicinal Lamiaceae with antioxidant properties, a potential source of rosmarinic acid. Pharm. Acta Helv. 1991, 66, 185-188.
20. Mabry, T. J.; Markham, K. R.; Thomas, M. B. In The NMR Spectra of Flavonoids. The Systematic Identification of Flavonoids; Springer-Verlag: New York, 1970; pp 330-333.
21. Santos-Gomes, P. C.; Seabra, R. M.; Andrade, P. B.; Fernández- Ferreira, M. Phenolic antioxidant compounds produced by in vitro shoots of sage (Salvia officinalis L.). Plant Sci. 2002, 162, 981-987.
22. Castillo, J.; Benavente-García, O.; Del Rio, J. A. Naringin and neohesperidin levels during development of leaves, flower buds and fruits of Citrus aurantium. Plant Physiol. 1992, 99, 67-73.
23. Castillo, J.; Benavente-García, O.; Del Río, J. A. Hesperetin 7-O-glucoside and prurin in Citrus species (C. aurantium and C. paradisi). A study of their quantitative distribution in immature fruits and as immediate precursors of neohesperidin and naringin in Citrus aurantium. J. Agric. Food Chem. 1993, 41, 1920-1919.
24. Benavente-García, O.; Castillo, J.; Del Río, J. A. Changes in neodiosmin levels during the development of Citrus aurantium leaves and fruits. Postulation of a neodiosmin biosynthetic pathway. J. Agric. Food Chem. 1993, 41, 1916-1919.
25. Macleod, N. J.; Pridham, J. B. Translocation of phenolic compounds. Phytochemistry 1966, 5, 777-781.
26. 14C. Phytochemistry 1968, 7, 769-771
27. Hasegawa, S.; Hoagland, J. E. Biosynthesis of limonoids in citrus, Phytochemistry 1977, 16, 469-471.
28. Jourdan P. S.; McIntosh C. A.; Mansell, R. L. Naringin levels in citrus tissues. II. Quantitative distribution of naringin in Citrus paradisi Macfad. Plant Physiol. 1985, 77, 903-908.
29. Berhow; M. A.; Vandercook, C. E. Biosynthesis of naringin and prunin in detached grapefruit. Phytochemistry 1989, 28, 1627-1630.
30. Furuya, M.; Galston, A. W.; Stowe, B. B. Isolation from peas of cofactors and inhibitors of indolyl-3-acetic acid oxidase. Nature 1962, 193, 456-457.
31. Galston, A. W. Perspectives in Phytochemistry; Harborne, J. B., Swaon, T., Eds.; Academic Press: London, U.K., 1969; pp 193-204.
32. Ritzer, R. W.; Hemphill, D. D.; Sell, H. M.; Bukovac, M. J. Indole-3-acetic acid oxidase activity from developing peach seeds and its inhibition by extractable catechol. J. Am. Soc. Hortic. Sci. 1972, 97, 48-51.
33. Fuster, M. J. D.; Benavente-García, O.; Castillo, J.; Ortuño, A.; Sabater, F.; Porras, I.; García Lidón, A.; del Rio, J. A. Hesperidina un posible modulador del catabolismo auxínico en Tangenlo nova. Proceedings of the IV Symposium on Metabolism and Mode of Action of Phytohormones; 1994; Vol. 1, pp 24-29.
34. Harbome, J. B.; Willians, C. A. Flavone and flavonol glycosides In The Flavonoids: Advances in Research since 1980; Harbome, J. B. Ed.; Chapman and Hall: New York, 1988; pp 303-328.
35. Ebel, J.; Hahlbrock, K. Biosynthesis. In The Flavonoids: Advances in Research; Harborne, J. B., Mabry, T. J., Eds.; Chapman and Hall: New York, 1982; pp 641-679.