Isolation and characterization of new lactam compounds that inhibit lung and colon cancer cells from adlay (Coix lachryma-jobi L. var. ma-yuen Stapf) bran

Food and Chemical Toxicology

Volumn 46, Issue 6, 2008, Pages 1933-1939

  Lee, Ming Yi ^a   Lin, Huan You ^b   Cheng, Faiwen ^a   Chiang, Wenchang ^a   Kuo, Yueh Hsiung ^a,b,c,d  

^a Center for Food and Biomolecules   (Taiwan)

^b NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^c CHINA MEDICAL UNIVERSITY   (Taiwan)

^d AGRICULTURAL BIOTECHNOLOGY RESEARCH CENTER   (Taiwan)

Author keywords

Adlay bran; Anti proliferative; Colorectal carcinoma; Lactam; Lung cancer

Indexed keywords

3 (4,5 DIMETHYL 2 THIAZOLYL) 2,5 DIPHENYLTETRAZOLIUM BROMIDE; ACETIC ACID ETHYL ESTER; COIX LACHRYMA JOBI EXTRACT; COIXLACTAM; COIXSPIROLACTAM A; COIXSPIROLACTAM B; COIXSPIROLACTAM C; LACTAM DERIVATIVE; METHANOL; METHYL DIOXINDOLE 3 ACETATE; PLANT EXTRACT;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BRAN; CANCER CELL; CELL PROLIFERATION; COIX; COIX LACRYMA JOBI; COLORECTAL CARCINOMA; CONTROLLED STUDY; DRUG ACTIVITY; DRUG ISOLATION; DRUG STRUCTURE; HUMAN; HUMAN CELL; LUNG CANCER; MEDICINAL PLANT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; CELL PROLIFERATION; COIX; COLONIC NEOPLASMS; HT29 CELLS; HUMANS; LACTAMS; LUNG NEOPLASMS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; METHANOL; SOLVENTS; SPECTROPHOTOMETRY, INFRARED; SPECTROPHOTOMETRY, ULTRAVIOLET; TETRAZOLIUM SALTS; THIAZOLES;

COIX LACRYMA-JOBI;

EID: 42749090638     PISSN: 02786915     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.fct.2008.01.033     Document Type: Article

References (28)

1. Banik K.B., Becker F.F., and Banik I. Synthesis of anticancer β-lactams: mechanism of action. Bioorgan. Med. Chem. 12 (2004) 2523-2528
2. Barnes S. Effect of genistein on in vitro and in vivo models of cancer. J. Nutr. 125 (1995) 777-783
3. Barve V., Ahmed F., Adsule S., Banerjee S., Kulkarni S., Katiyar P., Anson C.E., Powell A.K., Padhye S., and Sarkar F.H. Synthesis, molecular characterization, and biological activity of novel synthetic derivatives of chromen-4-one in human cancer cells. J. Med. Chem. 49 (2006) 3800-3808
4. Chang H.C., Huang Y.C., and Hung W.C. Antiproliferative and chemopreventive effects of adlay seed on lung cancer in vitro and in vivo. J. Agric. Food Chem. 51 (2003) 3656-3660
5. Chiang W., Cheng C.Y., Chiang M.T., and Chung K.T. Effects of dehulled adlay on the culture count of some microbiota and their metabolism in the gastrointestinal tract of rats. J. Agric. Food Chem. 48 (2000) 829-832
6. Chiang W., Shyu M.L., Su J.P., and Pang V.F. Evaluation of the accessory anti-tumor effect of adlay processing food. J. Health Sci. 2 (2000) 113-122
7. Crotti C., Cenini S., Rindone B., Tollari S., and Demartin F. Deoxygenation reactions of ortho-nitrostyrenes with carbon monoxide catalysed by metal carbonyls: a new route to indoles. J. Chem. Soc. Chem. Commun. (1986) 784-786
8. Felicia V.S., Najla G., Ann F.C., Madeleine M., and Kenneth K.C. Inhibition of human breast cancer cell proliferation and delay of mammary tumorigenesis by flavonoids and citrus juices. Nutr. Cancer 26 (1996) 167-181
9. Hansen M.B., Nielsen S.E., and Berg K. Reexamination and further development of a precise and rapid dye method for measuring cell growth/cell kill. J. Immunol. Methods 119 (1989) 203-210
10. Hidaka Y., Kaneda T., Amino N., and Miyai K. Chinese medicine, Coix seed increase peripheral cytotoxic T and NK cells. Biotherapy 5 (1992) 201-203
11. Hsu H.Y., Lin B.F., Lin J.Y., Kuo C.C., and Chiang W. Suppression of allergic reactions by dehulled adlay in association with the balance of TH1/TH2 cell responses. J. Agric. Food Chem. 51 (2003) 3763-3769
12. Huang S.L., and Chiang W. Composition of the different fractions of adlay seed and the demutagenic effect of their acetone extract. Food Sci. 26 (1999) 121-130
13. Kazi A., Hill R., Long T.E., Kuhn D.J., Turos E., and Dou Q.P. Novel N-thiolated beta-lactam antibiotics selectively induce apoptosis in human tumor and transformed, but not normal or nontransformed, cells. Biochem. Pharmacol. 67 (2004) 365-374
14. Kuo C.C., Shih M.C., Kuo Y.H., and 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. 49 (2001) 1564-1570
15. Kuo C.C., Chiang W., Liu G.P., Chien Y.L., Lee C.K., Lo J.M., Huang S.L., Shih M.C., and Kuo Y.H. 2,2′-Diphenyl-1-picrylhydrazyl radical-scavenging active components from adlay (Coix lachryma-jobi L. var. ma-yuen Stapf) hulls. J. Agric. Food Chem. 50 (2002) 5850-5855
16. Li, S.C., 1596. Pen-t'sao kang mu (Systematic Pharmacopoeia). China.
17. Messina M., and Erdman J.W. Modern applications for an ancient bean: soybeans and the prevention and treatment of chronic disease. J. Nutr. 125 (1995) 567-569
18. Nagao T., Otsuka H., Kohda H., Sato T., and Yamasaki K. Benzoxazinone from Coix lachryma-jobi L var. ma-yuen. Phytochemistry 24 (1985) 2959-2962
19. Numata M., Yamamoto A., Moribayashi A., and Yamada H. Antitumor components isolated from the Chinese herbal medicine Coix lachryma-jobi. Planta Med. 60 (1994) 356-359
20. Shih C.K., Chiang W., and Kuo M.L. Effects of adlay on azoxymethane-induced colon carcinogenesis in rats. Food Chem. Toxicol. 42 (2004) 1339-1347
21. Smith D.M., Kazi A., Smith L., Long T.E., Heldreth B., Turos E., and Dou Q.P. A novel beta-lactam antibiotic activates tumor cell apoptotic program by inducing DNA damage. Mol. Pharmacol. 61 (2002) 1348-1358
22. Sun H.D., Lin Z.W., Niu F.D., Lin L.Z., Chai H.B., and Pezzuto J.M. Cordell G. A. Cytotoxic ent-kaurene diterpenoids from three Isodon species. Phytochemistry 38 (1995) 437-442
23. Taichi O., Kyoko Y., Keiji I., Ohmoto T., Yamaguchi K., and Ikeda K. Constituents of Hibiscus moscheutos L. Chem. Pharm. Bull. 36 (1988) 578-581
24. Takahashi M., Konno C., and Hikino H. Isolation and hypoglycemic activity of coixan A, B, C, glycans of Coix lachryma-jobi var. ma-yuen seeds. Planta Med. 52 (1986) 64-65
25. Tanimura A. Studies on the anti-tumor component in the seeds of Coix lachryma-jobi L. var. ma-yuen (Roman.) Stapf. II. The structure of coixenolide. Chem. Pharm. Bull. 9 (1961) 47-53
26. Tokuda H., Matsumoto T., Konoshima T., Kozuka M., Nishino H., and Iwashima A. Inhibitory effects on Epstein-Barr virus activation and anti-tumor promoting activities of coix seed. Planta Med. 56 (1990) 653-654
27. Tsai C.E., Yang L.J., and Hsu H.C. Ingestion of adlay may reduce liver fat accumulation in hamsters fed high fat diets. Food Sci. 26 (1999) 265-276
28. Ukita T., and Tanimura A. Studies on the anti-tumor component in the seeds of Coix lachryma-jobi L. var. ma-yuen (Roman.) Stapf. I. Isolation and anti-tumor activity of coixenolide. Chem. Pharm. Bull. 9 (1961) 43-46