Evaluation of the light-sensitive cytotoxicity of Hypericum perforatum extracts, fractions, and pure compounds

Journal of Agricultural and Food Chemistry

Volumn 54, Issue 8, 2006, Pages 2881-2890

  Schmitt, Laura A ^a   Liu, Yi ^a   Murphy, Patricia A ^a   Birt, Diane F ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

8 isoprostane; Chlorogenic acid; Cytotoxicity; Hypericin; Hypericum perforatum; Hyperoside; Isoquercitrin; Phototoxicity; Pseudohypericin; Quercetin; Quercitrin; Rutin; St. John's wort

Indexed keywords

PLANT EXTRACT;

ARTICLE; CELL LINE; CELL SURVIVAL; CHEMISTRY; DRUG EFFECT; HUMAN; HYPERICUM; KERATINOCYTE; LIGHT; RADIATION EXPOSURE;

CELL LINE; CELL SURVIVAL; HUMANS; HYPERICUM; KERATINOCYTES; LIGHT; PLANT EXTRACTS;

HYPERICUM PERFORATUM;

EID: 33646509647     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf052344k     Document Type: Article

References (32)

1. Bilia, A. R.; Gallori, S.; Vincieri, F. F. St. John's wort and depression: Efficacy, safety and tolerability-an update. Life Sci. 2002, 70 (26), 3077-3096.
2. Greeson, J. M.; Sanford, B.; Monti, D. A. St. John's wort (Hypericum perforatum): A review of the current pharmacological, toxicological, and clinical literature. Psychopharmacology (Berlin) 2001, 153 (4), 402-414.
3. Kasper, S. Hypericum perforatum - A review of clinical studies. Pharmacopsychiatry 2001, 34 (Suppl. 1), S51-S55.
4. Barnes, J.; Anderson, L. A.; Phillipson, J. D. St. John's wort (Hypericum perforatum L.): A review of its chemistry, pharmacology and clinical properties. J. Pharm. Pharmacol. 2001, 53 (5), 583-600.
5. Rodriguez-Landa, J. F.; Contreras, C. M. A review of clinical and experimental observations about antidepressant actions and side effects produced by Hypericum perforatum extracts. Phytomedicine 2003, 10 (8), 688-699.
6. Linde, K.; Berner, M.; Egger, M.; Mulrow, C. St. John's wort for depression: Meta-analysis of randomised controlled trials. Br. J. Psychiatry 2005, 186, 99-107.
7. Henderson, L.; Yue, Q. Y.; Bergquist, C.; Gerden, B.; Arlett, P. St. John's wort (Hypericum perforatum): Drug interactions and clinical outcomes. Br. J. Clin. Pharmacol. 2002, 54 (4), 349-356.
8. Bernd, A.; Simon, S.; Ramirez, B. A.; Kippenberger, S.; Diaz, A. J.; Miquel, J.; Villalba Garcia, J. F.; Pamies, M. D.; Kaufmann, R. Phototoxic effects of Hypericum extract in cultures of human keratinocytes compared with those of psoralen. Photochem. Photobiol. 1999, 69 (2), 218-221.
9. Hostanska, K.; Reichling, J.; Bommer, S.; Weber, M.; Saller, R. Aqueous ethanolic extract of St. John's wort (Hypericum perforatum L.) induces growth inhibition and apoptosis in human malignant cells in vitro. Pharmazie 2002, 57 (5), 323-331.
10. Meruelo, D.; Lavie, G.; Lavie, D. Therapeutic agents with dramatic antiretroviral activity and little toxicity at effective doses: Aromatic polycyclic diones hypericin and pseudohypericin. Proc. Natl. Acad. Sci. U.S.A. 1988, 55 (14), 5230-5234.
11. Kraus, G. A.; Melekhov, A.; Carpenter, S.; Wannemuhler, Y.; Petrich, J. Phenanthrenequinone antiretroviral agents. Bioorg. Med. Chem. Lett. 2000, 10 (1), 9-11.
12. Carpenter, S.; Kraus, G. A. Photosensitization is required for inactivation of equine infectious anemia virus by hypericin 5. Photochem. Photobiol. 1991, 53 (2), 169-174.
13. Lenard, J.; Rabson, A.; Vanderoef, R. Photodynamic inactivation of infectivity of human immunodeficiency virus and other enveloped viruses using hypericin and rose bengal: Inhibition of fusion and syncytia formation. Proc. Natl. Acad. Sci. U.S.A. 1993, 90 (1), 158-162.
14. Laakmann, G.; Schule, C.; Baghai, T.; Kieser, M. St. John's wort in mild to moderate depression: The relevance of hyperforin for the clinical efficacy 21. Pharmacopsychiatry 1998, 31 (Suppl. 1), 54-59.
15. Carpenter, S.; Fehr, M. J.; Kraus, G. A.; Petrich, J. W. Chemiluminescent activation of the antiviral activity of hypericin: A molecular flashlight. Proc. Natl. Acad. Sci. U.S.A. 1994, 91 (25), 12273-12277.
16. Yu, H.; Wolford, S. T.; Kegode, R.; Zhao, W.; Osweller, G. D. Hypericin-induced phototoxicity in cultured fibroblasts and swine erythrocytes 1. Photochem. Photobiol. 1996, 64 (1), 168-173.
17. Bruggisser, R.; von, D. K.; Jundt, G.; Schaffner, W.; Tullberg-Reinert, H. Interference of plant extracts, phytoestrogens and antioxidants with the MTT tetrazolium assay. Planta Med. 2002, 68 (5), 445-448.
18. Littell, R. C.; Milliken, G. A.; Stroup, W. W.; Wolfinger, R. D. SAS System for Mixed Models; SAS Institute Inc.: Cary, NC, 1996; 633 pp.
19. Bilia, A. R.; Bergonzi, M. C.; Morgenni, F.; Mazzi, G.; Vincieri, F. F. Evaluation of chemical stability of St. John's wort commercial extract and some preparations. Int. J. Pharm. 2001, 213 (1-2), 199-208.
20. Roscetti, G.; Franzese, O.; Comandini, A.; Bonmassar, E. Cytotoxic activity of Hypericum perforatum L. on K562 erythroleukemic cells: Differential effects between methanolic extract and hypericin. Phytother. Res. 2004, 18 (1), 66-72.
21. Wilhelm, K. P.; Biel, S.; Siegers, C. P. Role of flavonoids in controlling the phototoxicity of Hypericum perforatum extracts. Phytomedicine 2001, 8 (4), 306-309.
22. Varriale, L.; Coppola, E.; Quarto, M.; Veneziani, B. M.; Palumbo, G. Molecular aspects of photodynamic therapy: Low energy pre-sensitization of hypericin-loaded human endometrial carcinoma cells enhances phototolerance, alters gene expression and affects the cell cycle. FEBS Lett. 2002, 512 (1-3), 287-290.
23. Vantieghem, A.; Assefa, Z.; Vandenabeele, P.; Declercq, W.; Courtois, S.; Vandenheede, J. R.; Merlevede, W.; de, W. P.; Agostinis, P. Hypericin-induced photosensitization of HeLa cells leads to apoptosis or necrosis. Involvement of cytochrome c and procaspase-3 activation in the mechanism of apoptosis. FEBS Lett. 1998, 440 (1-2), 19-24.
24. Kawaii, S.; Tomono, Y.; Katase, E.; Ogawa, K.; Yano, M. Antiproliferative activity of flavonoids on several cancer cell lines. Biosci., Biotechnol., Biochem. 1999, 63 (5), 896-899.
25. Wills, N. J.; Park, J.; Wen, J.; Kesavan, S.; Kraus, G. A.; Petrich, J. W.; Carpenter, S. Tumor cell toxicity of hypericin and related analogues. Photochem. Photobiol. 2001, 74 (2), 216-220.
26. Dougherty, T. J. Photodynamic therapy. Adv. Exp. Med. Biol. 1985, 193, 313-328.
27. Piette, J.; Volanti, C.; Vantieghem, A.; Matroule, J. Y.; Habraken, Y.; Agostinis, P. Cell death and growth arrest in response to photodynamic therapy with membrane-bound photosensitizers. Biochem. Pharmacol. 2003, 66 (8), 1651-1659.
28. Park, J.; English, D. S.; Wannemuehler, Y.; Carpenter, S.; Petrich, J. W. The role of oxygen in the antiviral activity of hypericin and hypocrellin 5. Photochem. Photobiol. 1998, 68 (4), 593-597.
29. Kubin, A.; Wierrani, F.; Burner, U.; Alth, G.; Grunberger, W. Hypericin - The facts about a controversial agent 1. Curr. Pharm. Des. 2005, 11 (2), 233-253.
30. Schempp, C. M.; Simon-Haarhaus, B.; Heine, A.; Schopf, E.; Simon, J. C. In vitro and in vivo activation of hypericin with the incoherent light source PDT 1200 SOA (520-750 nm) and with solar simulated radiation (290-2500 nm) 21. Photodermatol. Photoimmunol. Photomed. 1999, 15 (1), 13-17.
31. Leccia, M. T.; Richard, M. J.; Joanny-Crisci, F.; Beani, J. C. UV-A1 cytotoxicity and antioxidant defence in keratinocytes and fibroblasts. Eur. J. Dermatol. 1998, 8 (7), 478-482.
32. Wang, W.; VanAlstyne, P. C.; Irons, K. A.; Chen, S.; Stewart, J. W.; Birt, D. F. Individual and interactive effects of apigenin analogues on G2/M cell-cycle arrest in human colon carcinoma cell lines 1. Nutr. Cancer 2004, 48 (1), 106-114.