Antitumor activity of (10E, 12Z)-9-hydroxy-10,12-octadecadienoic acid from rice bran

Journal of Fermentation and Bioengineering

Volumn 86, Issue 2, 1998, Pages 149-153

  Hayashi, Yoshiki ^a,d   Nishikawa, Yasushi ^a,d   Mori, Hirotaka ^a,d   Tamura, Hirotoshi ^b   Matsushita, Yoh Ichi ^c   Matsui, Takanao ^c  

^a Research Laboratories II   (Japan)

^b KAGAWA UNIVERSITY   (Japan)

^c UNIVERSITY OF MIYAZAKI   (Japan)

^d Tamanoi Vinegar Co Ltd   (Japan)

Author keywords

(10E, 12z) 9 hydroxy 10,12 octadecadienoic acid; (9Z, 11E) 13 hydroxy 9,11 octadecadienoic acid; Antitumor activity; Lipoxygenase; Rice bran

Indexed keywords

CELLS; CYTOLOGY; ENZYMES; FATTY ACIDS; ONCOLOGY; TOXICITY; VIRUSES;

ANTITUMOR ACTIVITY; CELL INHIBITION; HYDROXY OCTADECADIENOIC ACID;

BIOTECHNOLOGY;

DIMORPHECOLIC ACID; POLYUNSATURATED FATTY ACID;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; BRAN; CELL STRAIN 3T3; CELL TRANSFORMATION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYTOTOXICITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INTRAPERITONEAL DRUG ADMINISTRATION; LEUKEMIA CELL; RAT; RICE;

ANIMALIA; SIMIAE; SIMIAN VIRUS; SIMIAN VIRUS 40;

EID: 0031783858     PISSN: 0922338X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0922-338X(98)80053-6     Document Type: Article

References (22)

1. Begin, M. E., Das, U. N., Ells, G., and Horrobin, D. F.: Selective killing of human cancer cells by polyunsaturated fatty acids. Prostagl. Leukotr. Med., 19, 177-186 (1985).
2. Girao, L. A., Ruck, A. C., Cantrill, R. C., and Davidson, B. C.: The effect of C18 fatty acids on cancer cells in culture. Anticancer Res., 6, 241-244 (1986).
3. Begin, M. E., Ells, G., Das, U. N., and Horrobin, D. F.: Differential killing of human carcinoma cells supplemented with n-3 and n-6 polyunsaturated fatty acids. J. Natl. Cancer Inst., 77, 1053-1062 (1986).
4. Begin, M. E. and Ells, G.: Effects of C18 fatty acids on breast carcinoma cells in culture. Anticancer Res., 7, 215-217 (1986).
5. Baxter, E. D.: Lipoxidases in malting and mashing. J. Inst. Brew., 88, 390-396 (1982).
6. Drost, B. W., van den Berg, R., Freijiee, F. J. M., van der Velde, E. G., and Hollemans, M.: Flavor stability. J. Am. Soc. Brew. Chem., 48, 124-131 (1990).
7. Kobayashi, N., Kaneda, H., Kano, Y., and Koshino, S.: The production of linoleic acid and linolenic acid hydroperoxides during mashing. J. Ferment. Bioeng., 5, 371-375 (1993).
8. Ishihara, N., Nakagawa, K., Saito, F., Uenakai, K., Kuga, H., Ejima, A., Mitui, I., and Sato, K.: Antitumor activities of ketol forms of unsaturated fatty acids from a water extract of corn grain. Nippon Nougeikagaku Kaishi, 67, 1411-1416 (1993). (in Japanese)
9. Gardner, H. W.: Sequential enzymes of linoleic acid oxidation in corn germ: lipoxygenase and linoleate hydroperoxide isomerase. J. Lipid Res., 11, 311-321 (1970).
10. Iacazio, G., Langrand, G., Baratti, J., Buono, G., and Triantaphylidès, C.: Preparation, enzymatic synthesis of linoleic acid (13S)-hydroperoxide using soybean lipoxygenase-1. J. Org. Chem., 55, 1690-1691 (1990).
11. Phillips, B. E., Smith, C. R., Jr., and Tjarks, L. W.: (S)-13-Hydroxy-cis,9,rans-11-octadecadienoic acid lactone, a 14-membered-ring compound from Monnina emarginata seed oil. J. Org. Chem., 35, 1916-1919 (1970).
12. Miyakado, M., Meinwald, J., and Gilbert, L. E.: (R)-(Z, E)-9,11-Octadecadien-13-olide: an intriguing lactone from Heliconius pachinus (Lepidoptera). Experientia, 45, 1006-1008 (1989).
13. Hayashi, Y., Ishihara, N., Takahashi, M., Fujii, E., Uenakai, K., Masada, S., and Ichimoto, I.: A new cytotoxic compound from a water extract of corn. Biosci. Biotech. Biochem., 60, 1115-1117(1996).
14. Kato, T., Yamaguchi, Y., Hirano, T., Yokoyama, T., Uyehara, T., Namai, T., Yamanaka, S., and Harada, N.: Unsaturated hydroxy fatty acids, the self defensive substances in rice plant against rice diease. Chem. Lett., 409-412 (1984).
15. Bhalerao, U. T., Dasaradhi, L., Neelakantan, P., and Fadnavis, N. W.: Lipase catalyzed regio-and enantio-selective hydrolysis: molecular recognition phenomenon and synthesis of (R)-dimorphecolic acid. J. Chem. Soc., Chem. Commun., 1197-1198 (1991).
16. Hatanaka, A., Kajiwara, T., Sekiya, J., and Asano, M.: Product specificity during incubation of methyl linoleate with soybean lipoxygenase-I. Z. Naturforsch, 39c, 171-173 (1984).
17. Inanaga, J., Hirata, K., Saeki, H., Katsuki, T., and Yamaguchi, M.: A rapid esterification by means of mixed anhydride and its application to large-ring lactonization. Bull. Chem. Soc. Jpn., 52, 1989-1993 (1979).
18. Shultz, T. D., Chew, B. P., and Seaman, W. R.: Differential stimulatory and inhibitory responses of human MCF-7 breast cancer cells to linoleic acid and conjugated linoleic acid in culture. Anticancer Res., 12, 2143-2145 (1992).
19. Pandalai, P. K., Pilat, M., Yamazaki, K., Naik, H., and Pienta, K.: The effects of omega-3 and omega-6 fatty acids on in vitro prostate cancer growth. Anticancer Res., 16, 815-820 (1996).
20. Hayashi, Y., Fukushima, S., Kishimoto, S., Kawaguchi, T., Numata, M., Isoda, Y., Hirano, J., and Nakano, M.: Anticancer effects of free polyunsaturated fatty acids in an oily lymphographic agent following intrahepatic arterial administration to a rabbit bearing VX-2 tumor. Cancer Res., 52, 400-405 (1992).
21. Fukui, H., Akiyoshi, K., Sato, T., Sunamoto, J., Yamaguchi, S., and Numata, M.: Anticancer activity of polyunsaturated fatty acid emulsion stabilized by hydrophobized polysaccharide. J. Bioactive and Compatible Polym., 8, 305-316 (1993).
22. Begin, M. E.: Effects of Polyunsaturated fatty acids and of their oxidation products on cell survival. Chem. Phys. Lipids, 45, 269-313 (1987).