2,2′-Diphenyl-1-picrylhydrazyl radical-scavenging active components from adlay (Coix lachryma-jobi L. var. ma-yuen Stapf) hulls

Journal of Agricultural and Food Chemistry

Volumn 50, Issue 21, 2002, Pages 5850-5855

  Kuo, Ching Chuan ^a,b   Chiang, Wenchang ^a   Liu, Guey Ping ^a   Chien, Ya Lin ^a   Chang, Jang Yang ^b   Lee, Ching Kuo ^a   Lo, Jir Mehng ^a   Huang, Shou Ling ^a   Shih, Ming Chih ^c   Kuo, Yueh Hsiung ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^b NATIONAL HEALTH RESEARCH INSTITUTES   (Taiwan)

^c Deh Yu College of Nursing and Management   (Taiwan)

Author keywords

Active components; Adlay hulls; Antioxidant activity; Free radical

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; 4 KETOPINORESINOL; ACETIC ACID ETHYL ESTER; BUTANOL; COIX LACHRYMA JOBI EXTRACT; CONIFERYL ALCOHOL; FERULIC ACID; HEXANE; LIGNAN; MAYUENOLIDE; METHANOL; NATURAL PRODUCT; PLANT EXTRACT; RADICAL; SYRINGARESINOL; SYRINGIC ACID; UNCLASSIFIED DRUG; WATER; 2,2-DIPHENYL-1-PICRYLHYDRAZYL; ANTIOXIDANT; PICRIC ACID; SCAVENGER;

ANTIOXIDANT ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHROMATOGRAPHY; COIX LACRYMA JOBI; DRUG STRUCTURE; FRACTIONATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; PURIFICATION; SCAVENGING SYSTEM; SEED HUSK; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLANT; PLANT SEED; POACEAE;

COIX; COIX LACRYMA-JOBI;

ANTIOXIDANTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FREE RADICAL SCAVENGERS; MAGNETIC RESONANCE SPECTROSCOPY; METHANOL; PICRATES; PLANT COMPONENTS; PLANT EXTRACTS; POACEAE; SEEDS;

EID: 0037048523     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf020391w     Document Type: Article

References (38)

1. Otsuka, H.; Hirai, Y.; Nagao, T.; Yamaski, K. Antiinflammatory activity of benzoxaninoids from roots of Coix lachryma-jobi L. var. ma-yuen. J. Nat. Prod. 1988, 51, 74-79.
2. Tanimura, A. Studies on the antitumor components in the seeds of Coix lachryma-jobi L var. ma-yuen (Roman.) Stapf. II. The structure of coixenolide. Chem. Pharm. Bull. 1961, 9, 47-53.
3. Takahashi, M.; Konno, C.; Hikino, H. Isolation and hypoglycemic activity of coixan A, B, C, glycans of Coix lachrymajobi var. ma-yuen seeds. Planta Med. 1986, 52, 64-65.
4. Ishiguro, Y.; Okamoto, K.; Sakamoto, H.; Sonoda, Y. Antimicrobial substances coixindens A and B in etiolated seedlings of adlay. Nippon Nogei Kagaku Kaishi 1993, 67, 1405-1410.
5. Kondo, Y.; Nakajima, K.; Nozoe, S.; Suzuki, S. Isolation of ovulatory-active substances from crops of Job's tears (Coix lachryma-jobi var. ma-yuen stapf.). Chem. Pharm. Bull. 1998, 36, 3147-3152.
6. Halliwell, B. Reactive oxygen species in living systems: Source, biochemistry, and role in human disease. Am. J. Med. 1991, 91, 14S-22S.
7. Kehrer, J. P. Free radicals as mediators of tissue injury and disease. Crit. Rev. Toxicol. 1993, 23, 21-48.
8. Toda, S.; Tanizawa, H.; Arichi, S.; Takino, Y. Inhibitory effects of methanolic extract of crude drugs on the air oxidation of linoleic acid. Yakugaku Zasshi 1984, 104, 394-397.
9. Su, J. D. Investigation of antioxidative activity and tocopherol contents on Chinese crude drugs of fruits or seeds. Food Sci. 1992, 19, 12-24.
10. Liou, B. K.; Chen, H. Y.; Yen, G. C. Antioxidative activity of the methanolic extracts from various traditionally edible plants. J. Chin. Agric. Chem. Soc. 1999, 37, 105-116.
11. Kuo, C.-C.; Shih, M.-C.; Kuo, Y.-H.; Chiang, W. Antagonism of free-radical-induced damage of adlay seed and its antiproliferative effect in human histolytic lymphoma U937 monocytic cells. J. Agric. Food Chem. 2001, 49, 1564-1570.
12. Song, Y.-N.; Shibuya, M. S.; Ebizuka, Y.; Sankawa, U. Identification of plant factors inducing virulence gene expression in Agrobacterium tumefaciens. Chem. Pharm. Bull. 1991, 39, 2347-2350.
13. Chiji, H.; Tanaka, S.; Izawa, M. Phenolic germination inhibitors in the seed balls of red beet (Beta vulgaris L. var. rubra). Agric. Biol. Chem. 1980, 44, 205-207.
14. Kim, S. R.; Kim, Y. C. Neuroprotective phenylpropanoid esters of rhamnose isolated from roots of Scrophularia buergeriana. Phytochemistry 2000, 54, 503-509.
15. Russel, G. B.; Fenemore, P. G. New lignans from leaves of Macropiper excelsum. Phytochemistry 1973, 12, 1799-1803.
16. Otsuka, H.; Takeuchi, M.; Inoshiri, S.; Sato, T.; Yamasaki, K. Phenolic compounds from Coix lachryma-jobi var. ma-yuen. Phytochemistry 1989, 28, 883-886.
17. Palph, J.; Grabber, J. H.; Hatfield, R. D. Lignin-ferulate polysaccharide esters into ryegrass lignin. Carbohydr. Res. 1995, 275, 167-178.
18. Shimada, K.; Fujikawa, K.; Yahara, K.; Nakamura, T. Antioxidative properties of xanthan on the autoxidation of soybean oil in cyclodextrin emulsion. J. Agric. Food Chem. 1992, 40, 945-948.
19. Dinis, T. C. P.; Madeira, V. M. C.; Almeida, L. M. Action of phenolic derivatives (acetaminophen, salicylate, and 5-aminosalicylate) as inhibitors of membrane lipid peroxidation and as peroxyl radical scavengers. Arch. Biochem. Biophys. 1994, 315, 161-169.
20. Wang, M. F.; Li, J. G.; Rangarajan, M.; Shao, Y.; LaVoie, E. J.; Huang, T.-C.; Ho, C.-T. Antioxidative phenolic compounds from sage (Salvia officinalis). J. Agric. Food Chem. 1998, 46, 4869-4873.
21. Chen, Y.; Wang, M.; Rosen, R. T.; Ho, C.-T. 2,2′-Diphenyl-1-picrylhydrazyl (DPPH) radical- scavenging active compounents from Polygonum multiflorum Thunb. J. Agric. Food Chem. 1999, 47, 2226-2228.
22. Constantin, M.; Bromont, C.; Fickat, R.; Massingham, R. Studies on the activity of bepridil as a scavenger of free radicals. Biochem. Pharmacol. 1990, 40, 1615-1622.
23. Yokozawa, T.; Chen, C.-P.; Dong, E.; Tanaka, T.; Nonaka, G.I.; Nishioka, I. Study on the inhibitory effect of tannins and flavonoids against the 2,2′-diphenyl-1-picrylhydrazyl radical. Biochem. Pharmacol. 1998, 56, 213-222.
24. Malterud, K. E.; Farbrot, T. L.; Huse, A. E.; Sund, R. B. Antioxidant and radical scavenging effects of anthraquinones and anthrones. Pharmacology 1993, 47 (suppl. 1), 77-85.
25. Joyeux, M.; Mortier, F.; Fleurentin, J. Screening of antiradical, antilipoperoxidant and hepatoprotective effects of nine plant extracts used in Caribbean folk medicine. Phytother. Res. 1995, 9, 228-230.
26. Heilmann, J.; Calis, I.; Kirmizibekmez, H.; Schuhly, W.; Harput, S.; Sticher, O. Radical scavenger activity of phenylethanoid glycosides in FMLP stimulated human polymorphonuclear leukocytes: Structure-activity relationships. Planta Med. 2000, 66, 746-748.
27. 2 system) by syringic acid. C. R. Hebd. Seances Acad. Sci. D: Sci. Nat. 1975, 281, 1897-1900.
28. Hirota, A.; Taki, S.; Kawaii, S.; Yano, M.; Abe, N. 2,2′-Diphenyl1-picrylhydrazyl radical-scavenging compounds from soybean miso and antiproliferative activity of isoflavones from soybean miso toward the cancer cell lines. Biosci. Biotechnol. Biochem. 2000, 64, 1038-1040.
29. Nakasone, Y.; Takara, K.; Wada, K.; Tanaka, J.; Yogi, S.; Nakatani, N. Antioxidative compounds isolated from kokuto, noncentrifugal cane sugar. Biosci. Biotechnol. Biochem. 1996, 60, 1714-1716.
30. Chen, C. C.; Chen, H. Y.; Shiao, M. S.; Lin, Y. L.; Kuo, Y. H.; Ou, J. C. Inhibition of low-density lipoprotein oxidation by tetrahydrofurofuran lignans from Forsythia suspensa and Magnolia coco. Planta Med. 1999, 65, 709-711.
31. Graf, E. Antioxidant potential of ferulic acid. Free Radical Biol. Med. 1992, 13, 435-448.
32. Terao, J.; Karasawa, H.; Arai, HI.; Nagao, A.; Suzuki, T.; Takawa, K. Peroxyl radical scavenging activity of caffeic acid and its related phenolic compounds in solution. Biosci. Biotechnol. Biochem. 1993, 57, 1204-1205.
33. Uchida, M.; Nakajin, S.; Toyoshima, S.; Shinoda, M. Antioxidative effect of sesamol and related compounds on lipid peroxidation. Biol. Pharm. Bull. 1996, 19, 623-626.
34. Kaul, A.; Khanduja, K. L. Plant polyphenols inhibit benzoyl peroxide-induced superoxide anion radical production and diacylglyceride formation in murine peritioneal macrophages. Nutr. Cancer 1999, 35, 207-211.
35. Kaul, A.; Khanduja, K. L. Polyphenols inhibit promotional phase of tumororigenesis: relevance of superoxide radicals. Nutr. Cancer 1998, 32, 81-85.
36. Sakai, S.; Ochiai, H.; Nakajima, K.; Tersawa, K. Inhibitory effect of ferulic acid on macrophage inflammatory protein-2 production in a murine macrophage cell line, RAW264.7. Cytokines 1997, 9, 242-248.
37. Hirabayashi, T.; Ochiai, H.; Sakai, S.; Nakajima, K.; Terasawa, K. Inhibitory effect of ferulic acid and isoferulic acid on murine interleukin-8 production in response to influenza virus infections in vitro and in vivo. Planta Med. 1995, 61, 221-226.
38. Brand-Williams, W.; Cuvelier, M. E.; Berset, C. Use of a free radical method to evaluate antioxidant activity. Lebensm. Wiss. u. Technol. 1995, 28, 25-30.