Photochemistry and photocytotoxicity of alkaloids from goldenseal (Hydrastis canadensis L.). 2. Palmatine, hydrastine, canadine, and hydrastinine

Chemical Research in Toxicology

Volumn 19, Issue 6, 2006, Pages 739-744

  Inbaraj, J J ^a   Kukielczak, B M ^a   Bilski, P ^a   He, Y Y ^a   Sik, R H ^a   Chignell, C F ^a  

^a NATIONAL INSTITUTE OF ENVIRONMENTAL HEALTH SCIENCES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5,5 DIMETHYL 1 PYRROLINE 1 OXIDE; ACETONITRILE; ALKALOID; BERBERINE; BUFFER; CANADINE; HYDRASTINE; METHYL CHLORIDE; NITROGEN; OXYGEN; OXYGEN RADICAL; PALMATINE;

AQUEOUS SOLUTION; ARTICLE; CELL DEATH; CELL VIABILITY; COMET ASSAY; CONTROLLED STUDY; DIET SUPPLEMENTATION; DNA DAMAGE; HERB; HUMAN; HUMAN CELL; HYDRASTIS; KERATINOCYTE; LIGHT EXPOSURE; NONHUMAN; PHOTOCHEMISTRY; PHOTOTOXICITY; PLANT ROOT; REDUCTION; SPIN TRAPPING; ULTRAVIOLET A RADIATION;

ALKALOIDS; BENZYLISOQUINOLINES; BERBERINE; BERBERINE ALKALOIDS; CELL LINE; CELL SURVIVAL; HUMANS; HYDRASTIS; MOLECULAR STRUCTURE; OXYGEN; PHOTOCHEMISTRY; PHOTOSENSITIZING AGENTS; SPECTRUM ANALYSIS; TETRAHYDROISOQUINOLINES;

HYDRASTIS CANADENSIS;

EID: 33745302586     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx050356u     Document Type: Article

References (24)

1. Drew, A. (2000) Goldenseal. Curr. Ther. 41, 47-48.
2. Harmon, N. W. (1990) Goldenseal. Can. Pharm. J. 123, 508-510.
3. Palanisamy, A., Haller, C., and Olson, K. R. (2003) Photosensitivity reaction in a woman using an herbal supplement containing ginseng, goldenseal, and bee pollen. J. Toxicol. Clin. Toxicol. 41, 865-867.
4. Inbaraj, J. J., Kukielczak, B. M., Bilski, P., Sandvik, S. L., and Chignell, C. F. (2001) Photochemistry and photocytotoxicity of alkaloids from Goldenseal (Hydrastis canadensix L.). I. Berberine. Chem. Res. Toxicol. 14, 1529-1534.
5. Weber, H. A., Zart, M. K., Hodges, A. E., Molloy, H. M., O'Brien, B. M., Moody, L. A., Clark, A. P., Harris, R. K., Overstreet, J. D., and Smith, C. S. (2003) Chemical comparison of goldenseal (Hydrastis canadensis L.) root powder from three commercial suppliers. J. Agric. Food Chem. 51, 7352-7358.
6. Weber, H. A., Zart, M. K., Ferguson, S. L., Greaves, J. G., Clark, A. P., Harris, R. K., Overstreet, D., and Smith, C. (2001) Separation and quantitation of isoquinoline alkaloids occurring in Goldenseal. J. Liq. Chromatogr. Relat. Technol. 24, 87-95.
7. Weber, H. A., Zart, M. K., Hodges, A. E., White, K. D., Barnes, S. M., Moody, L. A., Clark, A. P., Harris, R. K., Overstreet, J. D., and Smith, C. S. (2003) Method validation for determination of alkaloid content in goldenseal root powder. J. AOAC Int. 86, 476-483.
8. 1Δg) decay in solution. J. Biochem. Biophys. Methods 33, 73-80.
9. Hall, R. D., Buettner, G. R., Motten, A. G., and Chignell, C. F. (1987) Near-infrared detection of singlet molecular oxygen produced by photosensitization with promazine and chlorpromazine. Photochem. Photobiol. 46, 295-300.
10. Duling, D. R. (1994) Simulation of multiple isotropic spin-trap EPR spectra. J. Magn. Reson. B 104, 105-110.
11. Boukamp, P., Petrussevska, R. T., Breitkreutz, D., Hornung, J., Markham, A., and Fusenig, N. E. (1988) Normal keratinization in a spontaneously immortalized aneuploid human keratinocyte cell line. J. Cell Biol. 106, 761-771.
12. Singh, N. P., McCoy, M. T., Tice, R. R., and Schneider, E. L. (1988) A simple technique for quantitation of low levels of DNA damage in individual cells. Exp. Cell Res. 175, 184-191.
13. Mikes, V., and Dadak, V. (1983) Berberine derivatives as cationic fluorescent probes for the investigation of the energized state of mitochondria. Biochim. Biophys. Acta 723, 231-239.
14. Hirakawa, K., Kawanishi, S., and Hirano, T. (2005) The mechanism of guanine specific photooxidation in the presence of berberine and palmatine: Activation of photosensitized singlet oxygen generation through DNA-binding interaction. Chem. Res. Toxicol. 18, 1545-1552.
15. Buxton, G. V., Greenstock, C. L., Helman, W. P., and Ross, A. B. (1988) Critical review of rate constants for reactions of hydrated electrons, hydrogen atoms and hydroxyl radicals (OH/O-) in aqueous solution. J. Phys. Chem. Ref. Data 17, 513-886.
16. Suau, R., Najera, F., and Rico, R. (1996) Photochemical hydroxymethylation of protoberberine alkaloids. Total synthesis of (±)-solidaline. Tetrahedron Lett. 37, 3575-3578.
17. Reszka, K., Bilski, P., Sik, R. H., and Chignell, C. F. (1993) Photosensitized generation of superoxide radical in aprotic solvents: An EPR and spin trapping study. Free Radical Res. Commun. 19 (Suppl. 1), S33-S44.
18. Chignell, C. F., Motten, A. G., Sik, R. H., Parker, C. E., and Reszka, K. (1994) A spin trapping study of the photochemistry of 5,5-dimethyl-1-pyrroline N-oxide (DMPO). Photochem. Photobiol. 59, 5-11.
19. Ren, J., and Chaires, J. B. (1999) Sequence and structural selectivity of nucleic acid binding ligands. Biochemistry 38, 16067-16075.
20. Gong, G. Q., Zong, Z. X., and Song, Y. M. (1999) Spectrofluorometric determination of DNA and RNA with berberine. Spectrochim. Acta, Part A 55A, 1903-1907.
21. Finkelstein, E., Rosen, G. M., Rauckman, E. J., and Paxton, J. (1979) Spin trapping of Superoxide. Mol. Pharmacol. 16, 676-685.
22. Bilski, P., Reszka, K., Bilska, M., and Chignell, C. F. (1996) Oxidation of the spin trap 5,5-dimethyl-1-pyrroline N-oxide by singlet oxygen in aqueous solution. J. Am. Chem. Soc. 118, 1330-1338.
23. Girotti, A. W., and Kriska, T. (2004) Role of lipid hydroperoxides in photo-oxidative stress signaling. Antioxid. Redox Signaling 6, 301-310.
24. Davies, M. J. (2003) Singlet oxygen-mediated damage to proteins and its consequences. Biochem. Biophys. Res. Commun. 305, 761-770.