Effect of benzylic oxygen on the cytotoxic activity for colon 26 cell line of phenolic lignans

Bioscience, Biotechnology and Biochemistry

Volumn 70, Issue 12, 2006, Pages 2942-2947

  Yamauchi, Satoshi ^a   Sugahara, Takuya ^a   Nakashima, Yuki ^a   Abe, Koki ^a   Hayashi, Yoshimasa ^a   Akiyama, Koichi ^a   Kishida, Taro ^a   Maruyama, Masafumi ^a  

^a EHIME UNIVERSITY   (Japan)

Author keywords

Cytotoxic activity; Matairesinol; Oxidized matairesinol

Indexed keywords

CELL CULTURE; CYTOLOGY; METHANOL;

CYTOTOXIC ACTIVITY; MATAIRESINOL; OXIDIZED MATAIRESINOL;

OXYGEN;

LIGNAN; OXYGEN; PHENOL DERIVATIVE;

ANIMAL; ARTICLE; BAGG ALBINO MOUSE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG SCREENING; ELECTROSPRAY MASS SPECTROMETRY; METABOLISM; MOUSE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TUMOR CELL LINE;

ANIMALS; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; LIGNANS; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MICE, INBRED BALB C; MOLECULAR STRUCTURE; OXYGEN; PHENOLS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 33845902302     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.60353     Document Type: Article

References (20)

1. Yamauchi, S., Hayashi, Y., Nakashima, Y., Kirikihira, T., Yamada, K., and Masuda, T., Effect of benzylic oxygen on the antioxidant activity of phenolic lignans. J. Nat. Prod., 68, 1459-1470 (2005).
2. Yamauchi, S., Sugahara, T., Nakashima, Y., Okada, A., Akiyama, K., Kishida, T., Maruyama, M., and Masuda, T., Radical and superoxide scavenging activity of matairesinol and oxidized matairesinol. Biosci. Biotechnol. Biochem., 70, 1934-1940 (2006).
3. Eklund, P. C., and Sjöholm, R. E., Oxidative transformation of the natural lignan hydroxymatairesinol with 2,3-dichloro-5,6-dicyano-1,4- benziquinone. Tetrahedron, 59, 4515-4523 (2003).
4. Ayres, D. C., and Loike, J. D., "Lignans," Cambridge University Press (1990).
5. Osawa, T., Phenolic antioxidants in dietary plants as antimutagens. In "Phenolic Compounds in Food and Their Effects on Health II," eds. Huang, M.-T., Ho, C.-T., and Lee, C. Y., American Chemical Society, Washington, DC, pp. 135-149 (1992).
6. Barton, G. M., and Gardner, J. A. F., The occurrence of matairesinol in mountain hemlock (Tsuga mertensiana), western hemlock (Tsuga heterophylla), and balsam (Abies amabilis). J. Org. Chem., 27, 322-323 (1962).
7. Umezawa, T., Okunishi, T., and Shimada, M., Stereochemical diversity in lignan biosynthesis. Wood Res., 84, 62-75 (1997).
8. Umezawa, T., Biosynthesis of lignans, lignins, and norlignans. ASEAA (in Japanese), 43, 461-467 (2005).
9. Umezawa, T., Diversity in lignan biosynthesis. Phytochem. Rev., 2, 371-390 (2003).
10. Hirano, T., Gotoh, M., and Oka, K., Natural flavonoids and lignans are potent cytostatic agents against human leukemic HL-60. Life Sci., 55, 1061-1069 (1994).
11. Kulling, S. E., Jacobs, E., Pfeiffer, E., and Metzler, M., Studies on the genotoxicity of the mammalian lignans enterolactone and enterodiol and their metabolic precursors at various endpoints in vitro. Mutat. Res., 416, 115-124 (1998).
12. Chen, J. J., Fang, H. Y., Duh, C. Y., and Chen, I. S., New indolopyridoquinazoline, benzo[c]phenanthridines and cytotoxic constituents from zanthoxylum integrifoliolum. Planta Med., 71, 470-475 (2005).
13. MacRae, W. D., and Towers, G. H. N., Biological activity of lignans. Phytochemistry, 23, 1207-1220 (1984).
14. Ralph, J., Peng, J., Lu, F., Hatfield, R. D., and Helm, R. F., Are lignans optically active? J. Agric. Food Chem., 47, 2991-2996 (1999).
15. Shain, L., and Hillis, W. E., Phenolic extractives in Norway spruce and their effects on Fomes annosus. Phytopathology, 61, 841-845 (1971).
16. Schottner, M., Spiteller, G., and Gansser, D., Lignans interfering with 5 α-dihydrotestosterone binding to human sex hormone-binding globulin. J. Nat. Prod., 61, 119-121 (1998).
17. Lina, B., Korte, H., Nyman, L., and Unkila, M., A thirteen week dietary toxicity study with 7-hydroxymatairesinol potassium acetate (HMRlignan) in rats. Regul. Toxicol. Pharmacol., 41, 28-38 (2005).
18. Gordaliza, M., Castro, M. A., Corral, J. M. M., and Feliciano, A. S., Antitumor properties of podophyllotoxin and related compounds. Curr. Pharm. Des., 6, 1811-1839 (2000).
19. Koura, S., Yoshida, N., Ishikawa, T., Higashihara, H., and Sakamoto, N., Interleukin-10 plasmid DNA inhibits subcutaneous tumor growth of colon26 adenocarcinoma in mice. Cancer Lett., 218, 171-179 (2005).
20. Corbett, T. H., Grisworld Jr., D. P., Roberts, B. J., Peckham, J. C., and Schabel Jr., F. M., Tumor induction relationships in development of transplantable cancers of the colon in mice for chemotherapy assay, with a note on carcinogen structure. Cancer Res., 35, 2434-2439 (1975).