Fractionation of orange peel phenols in ultrafiltered molasses and mass balance studies of their antioxidant levels

Journal of Agricultural and Food Chemistry

Volumn 52, Issue 25, 2004, Pages 7586-7592

  Manthey, John A ^a  

^a AGRICULTURAL RESEARCH SERVICE   (United States)

Author keywords

Antioxidants; Citrus byproducts; Flavone glycosides; Flavonoids; Hydroxycinnamates; Peel

Indexed keywords

COUMARIC ACID; FLAVANONE; FLAVANONE DERIVATIVE; FLAVANONE DISACCHARIDE; FLAVANONE TRISCCHARIDE; FLAVONE DERIVATIVE; FLAVONE DISACCHARIDE; FLAVONE GLYCOSIDE; FLAVONOID; MOLASSES; PHENOL DERIVATIVE; POLYMETHOXYLATED FLAVONE; UNCLASSIFIED DRUG;

ADSORPTION CHROMATOGRAPHY; ANTIOXIDANT ACTIVITY; ARTICLE; CHEMICAL COMPOSITION; CONTROLLED STUDY; FRACTIONATION; GEL PERMEATION CHROMATOGRAPHY; ION EXCHANGE CHROMATOGRAPHY; MASS SPECTROMETRY; NITROBLUE TETRAZOLIUM TEST; NONHUMAN; ORANGE (FRUIT);

ANTIOXIDANTS; BEVERAGES; CHEMICAL FRACTIONATION; CHROMATOGRAPHY; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CITRUS SINENSIS; FILTRATION; FRUIT; PHENOLS;

CITRUS;

EID: 10644267586     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf049083j     Document Type: Article

References (29)

1. Manthey, J. A.; Guthrie, N.; Grohmann, K. Biological properties of citrus flavonoids pertaining to cancer and inflammation. Curr. Med. Chem. 2001, 8, 135-153.
2. Rusznyák, S.; Szent-Györgyi, A. Vitamin P. Flavonols as vitamins. Nature 1936, 138, 27.
3. Manthey, J. A.; Grohmann, K.; Montanari, A.; Ash, K.; Manthey, C. L. Polymethoxylated flavones derived from citrus suppress tumor necrosis factor-α expression by human monocytes. J. Nat. Prod. 1999, 62, 441-444.
4. Delbarre, B.; Delabarre, G.; Calinon, F. Effect of Daflon 500 mg, a flavonoid drug, on neurological signs, levels of free radicals and electroretinogram in the gerbil after ischemia-reperfusion injury. Int. J. Microcirc.: Clin. Exp. 1995, 15 (Suppl. 1), 27-33.
5. Korthuis, R. J.; Gute, D. C. Antiinflammatory actions of a micronized purified flavonoid fraction in ischemia/reperfusion. In Flavonoids in Cell Function; Buslig, B. S., Manthey, J. A., Eds.; Kluwer Academic/Plenum Publishers: New York, 2002; pp 181-190.
6. Lonchampt, M.; Guardiola, B.; Sicot, N.; Bertrand, M.; Pedrix, L.; Duhault, J. Protective effect of a purified flavonoid fraction against reactive oxygen radicals. Drug Res. 1989, 39, 882-885.
7. Jean, T.; Bodinier, M. C. Mediators involved in inflammation: effects of Daflon 500 mg on their release. Angiology 1994, 45, 554-559.
8. Landolfi, R.; Mower, R. L.; Steiner, M. Modification of platelet function and arachidonic acid metabolism by bioflavonoids. Biochem. Pharmacol. 1984, 33, 1525-1530.
9. Sadik, C. D.; Sies, H.; Schewe, T. Inhibition of 15-lipoxygenase by flavonoids: structure-activity relations and mode of action. Biochem. Pharmacol. 2003, 65, 773-781.
10. Manthey, J. A.; Grohmann, K. Concentrations of hesperidin and other orange peel flavonoids in citrus processing byproducts. J. Agric. Food Chem. 1996, 44, 811-814.
11. Manthey, J. A.; Grohmann, K. Phenols in citrus peel byproducts. Concentrations of hydroxycinnamates and polymethoxylated flavones in citrus peel molasses. J. Agric. Food Chem. 2001, 49, 3268-3273.
12. Grohmann, K.; Manthey, J. A.; Cameron, R. G.; Buslig, B. Purification of citrus peel juice and molasses. J. Agric. Food Chem. 1999, 47, 4859-4867.
13. Sellappan, S.; Akoh, C. C.; Krewer, G. Phenolic compounds and antioxidant capacity of Georgia-grown blueberries and blackberries. J. Agric. Food Chem. 2002, 50, 2432-2438.
14. Yamaguchi, F.; Ariga, T.; Yoshimura, Y.; Nakazawa, H. Antioxidative and anti-glycation activity of garcinol from Garcinia indica fruit rind. J. Agric. Food Chem. 2000, 48, 180-185.
15. Robak, J.; Gryglewski, R. J. Flavonoids are scavengers of superoxide anions. Biochem. Pharmacol. 1988, 37, 837-841.
16. Choi, H. S.; Song, H. S.; Ukeda, H.; Sawamura, M. Radical-scavenging activities of citrus essential oils and their componenets: detection using 1,1-diphenyl-2-picrylhydrazyl. J. Agric. Food Chem. 2000, 48, 4156-4161.
17. Bocco, A.; Cuvelier, M. E.; Richard, H.; Berset, C. Antioxidant activity and phenolic composition of citrus peel and seed extracts. J. Agric. Food Chem. 1998, 46, 2123-2129.
18. Rapisarda, P.; Tomaino, A.; Lo Cascio, R.; Bonina, F.; De Pasquale, A.; Saija, A. Antioxidant effectiveness as influenced by phenolic content of fresh orange juices. J. Agric. Food Chem. 1999, 47, 4718-4723.
19. Horowitz, R. M.; Gentili, B. In Citrus Science and Technology; Nagy, S., Shaw, P. E., Veldhuis, M. K., Eds.; Avi Publishing: Westport, CT, 1977; Vol. 1, pp 397-426.
20. Matsubara, Y.; Yonemoto, H.; Kumamoto, H.; Iizuka, Y.; Okamoto, K.; Yokoi, K. Flavonoid glycosides in citrus fruits peelings. Structure and hypotenisve effects of flavonoid glycosides on zabon (Citrus grandis Osbeck.), grapefruit (Citrus paradisi Macf.) and hassaku (Citrus hassaku Hort.) peelings. Yukagaku 1986, 35, 435-437.
21. Kumamoto, H.; Matsubara, Y.; Iizuka, Y.; Okamoto, K.; Yokoi, K. Structures and hypotensive effect of flavonoid glycosides in unshiu peel. II. Studies on physiologically active substances in citrus peel. Part VII. Yukagaku 1986, 35, 379-381.
22. Sawabe, A.; Kumamoto, H.; Matsubara, Y. Structure-function relationship of bioactive compounds in citrus fruit peels. Recent Res. Dev. Agric. Biol. Chem. 1998, 2, 143-166.
23. Friesenecker, B.; Tsai, A. G.; Allegra, C.; Intaglietta, M. Oral administration of purified micronized flavonoid fraction suppresses leukocyte adhesion in ischemia-reperfusion injury: in vivo observations in the hamster skin fold. Int. J. Microcirc: Clin Exp. 1994, 14, 50-55.
24. Damon, M.; Flandre, O.; Michel, F.; Perdix, L.; Labrid, C.; Crastes de Paulet, A. Effect of chronic treatment with a purified flavonoid fraction on inflammatory granuloma in the rat. Study of prostaglandin E2 and F2a and thromboxane B2 release and histological changes. Arzneim.-Forsch. 1987, 37, 1149-1153.
25. Schüssler, M.; Hölzl, J.; Rump, A. F. E.; Fricke, U. Functional and antiischaemic effects of monoacetyl-vitexinrhamnoside in different in vitro models. Gen. Pharmacol. 1995, 26, 1565-1570.
26. Schüssler, M.; Hölzl, J.; Fricke, U. Myocardial effects of flavonoids from Crataegus species. Drug Res. 1995, 45, 842-845.
27. Peleg, H.; Naim, M.; Rouseff, R. L.; Zehavi, U. Distribution of bound and free phenolic acids in oranges and grapefruit. J. Sci. Food Agric. 1991, 417-426.
28. Risch, B.; Herrmann, K.; Wray, V. (E)-O-p-coumaroyl-, (E)-O-feruloyl-derivatives of glucaric acid in citrus. Phytochemistry 1988, 10, 3327-3329.
29. Risch, B.; Herrmann, K.; Wray, V.; Grotjahn, L. 2′-(E)-O-p- courmaroylgalactaric acid and 2′-(E)-O-feruloylgalactaric acid in citrus. Phytochemistry 1987, 26, 509-510.