Photooxygenation of β-sitosterol and stigmasterol and DNA-damaging properties of their hydroperoxide products

Chinese Pharmaceutical Journal

Volumn 54, Issue 6, 2002, Pages 471-476

  Dawidar, A M ^a   Abou Elzahab, M M ^a   Berghot, M A ^a   Al Maah, K H ^a  

^a Mansoura University   (Egypt)

Author keywords

Sitosterol; Endoperoxides; Hydroperoxides; Photooxygenation; Singlet oxygen; Stigmasterol

Indexed keywords

INFRARED SPECTROSCOPY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOOXIDATION; SOLVENTS;

SPECTRAL DATAS;

HYDROGEN PEROXIDE;

5 HYDROPEROXY BETA SITOSTEROL; 5 HYDROPEROXY BETA SITOSTEROL 3 ACETATE; 5,23 DIHYDROPEROXYSTIGMASTEROL; HYDROPEROXIDE DERIVATIVE; SITOSTEROL; STIGMASTEROL; UNCLASSIFIED DRUG;

ARTICLE; DNA DAMAGE; DNA DEGRADATION; INFRARED SPECTROMETRY; MASS SPECTROMETRY; PHOTOOXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0037988802     PISSN: 10161015     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (23)

1. Chung, S. K.; Ryoo, C. H.; Yung, H. W.; Shim, J. Y.; Kang, M. G.; Lee, K. W.; Kong, H. I. Synthesis and bioactivities of steroid derivatives. Tetrahedron 1998, 54, 15899-15914.
2. Elkihel, L.; Bourass, J.; Dherbomez, M.; Letourneux, Y. Synthesis of aminocholesterol derivatives with antibiotic properties. Syn. Commun. 1997, 27, 1951-1962.
3. Potterat, O.; Hostettmann, K.; Hottzel, A.; Jung, G.; Diehl, P. A.; Petrini, O. Boophiline an antimicrobial sterol amide from the cattletick Boophilus microplus. Helv. Chim. Acta 1997, 80, 2066-2072.
4. Asanuma, H.; Wada, H.; Yamada, Y. Preparation of cis sterols as anticancer agents, (Taisho Pharmaceutical Co., Ltd., Japan) Jpn. Kokai Tokkyo Koho JP10251, 294[98.251, 294], 22 Sep. 1998, Appl. 97/57, 220, 12 Mar., 10 pp (1997); Chem. Abstr., 1998, 129, 290281p.
5. Awad, A. B.; Von Holtz, R. L.; Cone, J. P.; Fink, C. S.; Chen, Y. C. β-Sitosterol inhibits the growth of HT-29 human colon cancer cells by activating the sphingomyelin cycle. Anticancer Res. 1998, 18, 471-473; Chem. Abstr. 1998, 129, 62530p.
6. Awad, A. B.; Von Holtz, R. L.; Cone, J. P.; Fink, C. S.; Chen, Y. C. β-Sitosterol inhibits the growth of HT-29 human colon cancer cells by activating the sphingomyelin cycle. Anticancer Res. 1998, 18, 471-473; Chem. Abstr. 1998, 129, 62530p.
7. Kochevar, I. E.; and Dunn, D. A. Photosensitized reactions of DNA: Cleavage and addition. In Morrison M. (ed.), Bioorganic Photochemistry, Vol. I, John Wiley and Sons: New York, 1990; pp 273-316.
8. Saito, I.; Takayama, M.; and Matsuura, T. Phthalimide hydroperoxides as efficient photochemical hydroxy radical generators. A novel DNA-cleaving agent. J. Am. Chem. Soc. 1990, 112, 883-884.
9. Shapiro, E. L.; Legatt, T.; Oliveto, E. P. 0-Hydroepoxy-19-norsteroids. Tetrahedron Lett. 1964, 663-667.
10. Denny, R. W.; Nichon, A. Organic Reactions: Sensitized photooxygenation of Olefins (ed. Blatt et al.) New York, John Wiley & Sons, Inc.: London, 1973, Vol. 20, Chap. 2, pp 133-335.
11. Nickon, A.; Digiorgio, J. B.; Daniels, P. J. Chemical evidence of transition state geometry in reaction of olefines with singlet oxygen J. Org. Chem. 1973, 38, 533-539.
12. Adam, W.; Staub, E. L. Regio and stereo controlled oxygen functionalization of cholesterol by photooxygenation. Liebigs Ann. Chem. 1988, 757.
13. Jiamg, Z.; Zeng, D.; Liu, Y. Singlet oxygen photooxidation of cholesterol sensitized by lumiflavine. Huaxue Xuebao. 1989, 47, 194.
14. Dang, H. S.; Davies, A. G.; Schiesser, C. H. Allylic hydroperoxides formed by singlet oxygenation of cholest-5-en-3-one. J. Chem. Soc., Perkin Trans. 1990, 1, 789-794.
15. Jiang, Z.; Zeng, D. Studies on photooxidation: Synthesis of cholestene derivatives by sensitized photooxidation. Ganguang Kexueyn Kuang Huaxue. 1989, 53; Chem. Abstr. 1991, 114, 69346.
16. Jiang, Z.; Zeng, D. Studies on photooxidation: Synthesis of cholestene derivatives by sensitized photooxidation. Ganguang Kexueyn Kuang Huaxue. 1989, 53; Chem. Abstr. 1991, 114, 69346.
17. Joshi, S.; Dhar, D. N. A novel photooxygenation reaction of diosgene. Indian J. Chem. 1986, 25B, 432.
18. Kropf, H.; Reichwaldt, R. J. Photooxygenation of phenyl substituted propene, reactivity, selectivity and stereoselectivity. Chem. Res. 1987, 412.
19. Schenck, G. O.; Neumiiller, O. A. Photosensitized autoxidation of steroids synthesis. Ann. Chem. 1958, 618, 194.
20. Epe, B.; Haring, M.; Ramaiah, D.; Stopper, H.; Abou-Elzahab, M. M.; Adam, W.; Saha-Moller, C. R. DNA damage induced by furocoumarin hydroperoxide plus u.v. Carcinog. 1993, 14, 2271-2276.
21. Saito, I.; Takayama, M.; Matsuura, T.; Matsugo, S.; Kawanishi, S. Phthalimide hydroperoxides as efficient photochemical hydroxyl radical generators - A novel DNA-cleaving agent. J. Am. Chem. Soc. 1990, 112, 883-884.
22. Matsugo, S.; Saito, I. Photochemical cleavage of N-(hydroperoxyalkyl)phthalimides by intramolecular energy-transfer. Tetrahedron Lett. 1991, 32, 2949-2950.
23. Kochevar, I. E.; Dunm, D. A. "Photosensitized reactions of DNA cleavage" Morrison, M., (ed.), Biorganic photochemistry, Vol. 1, John Wiley and Sons: New York, 1990, p 273.