Sterol peroxidation by Pseudomonas fluorescens cholesterol oxidase

Steroids

Volumn 61, Issue 11, 1996, Pages 627-633

  Teng, Jon Ie ^a   Smith, Leland L ^a,b  

^a University of Texas Medical Branch School of Medicine   (United States)

^b NONE   (United States)

Author keywords

6 hydroperoxycholest 4 en 3 one; cholest 4 en 3 one; cholesterol; cholesterol oxidase; flavoprotein dioxygenase; sterol

Indexed keywords

CHOLESTEROL OXIDASE; STEROL;

ARTICLE; CONTROLLED STUDY; ENZYME ACTIVITY; NONHUMAN; PEROXIDATION; PSEUDOMONAS FLUORESCENS; STEROL METABOLISM;

PSEUDOMONAS; PSEUDOMONAS FLUORESCENS;

EID: 0030298528     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0039-128X(96)00135-3     Document Type: Article

References (49)

1. 1. Smith AG, Brooks CJW (1974). Application of cholesterol oxidase in the analysis of steroids. J Chromatogr 101:373-378.
2. 2. Ogishima T, Okuda K (1986). An improved method of assay of cholesterol 7α-hydroxylase activity. Anal Biochem 158:228-232.
3. 3. Goh EH, Colles SM, Otte KD (1989). HPLC analysis of desmosterol, 7-dehydrocholesterol, and cholesterol. Lipids 24:652-655.
4. 14C]cholesterol as substrates. Anal Biochem 182:212-216.
5. 5. Chiang JYL, Miller WF, Lin G-M (1990). Regulation of cholesterol 7α-hydroxylase in the liver. Purification of cholesterol 7α-hydroxylase and the immunochemical evidence for the induction of cholesterol 7α-hydroxylase by cholestyramine and circadian rhythm. J Biol Chem 265:3889-3897.
6. 6. Mike JH, Vernell RJ, Hutterer F (1990). HPLC determination of hepatic cholesterol 7α-hydroxylase activity using immobilized cholesterol oxidase and chemiluminescence detection. J Liquid Chromatogr 13:1215-1236.
7. 7. Song W, Pierce WM, Prough RA, Redinger RN (1991). Characteristics of cholesterol 7α-hydroxylase and 7α-hydroxycholesterol hydroxylase activities of rodent liver. Biochem Pharmacol 41:1439-1447.
8. 8. Petrack B, Latario BJ (1993). Synthesis of 27-hydroxycholesterol in rat liver mitochondria: HPLC assay and marked activation by exogenous cholesterol. J Lipid Res 34:643-649.
9. 4-3-ketone derivatives. J Chromatogr A 691:247-254.
10. 10. Lee KM, Biellman J-F (1986). Cholesterol oxidase in microemulsion: Enzymatic activity on a substrate of low water solubility and inactivation by hydrogen peroxide. Bioorg Chem 14:262-273.
11. 11. Alexander DL, Fisher JF (1995). A convenient synthesis of 7α-hydroxycholest-4-en-3-one by the hydroxypropyl-β-cyclodextrin-facilitated cholesterol oxidase oxidation of 3β,7α-cholest-5-ene-3,7-diol. Steroids 60:290-294.
12. 12. Liu K, Maddaford TG, Ramjiawan B, Kutryk MJB, and Pierce GN (1991). Effects of cholesterol oxidase on cultured vascular smooth muscle cells. Mol Cell Biochem 108:39-49.
13. 13. Liu K, Ramjiawan B, Kutryk MJB, Pierce GN (1991). Effects of oxidative modification of cholesterol in isolated low density lipoproteins on cultured smooth muscle cells. Mol Cell Biochem 108: 49-56.
14. 14. Molnár I, Hayashi N, Choi K-P, Yamamoto H, Yamashita M, Murooka Y (1993). Bacterial cholesterol oxidases are able to act as flavoprotein-linked ketosteroid monooxygenases that catalyse the hydroxylation of cholesterol to 4-cholesten-6-ol-3-one. Mol Microbiol 7:419-428.
15. 4-Δ5-isomerase components of cholesterol oxidase from Nocardia rhodochrous. J Appl Biochem 1:51-59.
16. 16. Kagan VE, Monovich O, Ribarov SR (1985). Induction of lipid peroxidation in erythrocytes during cholesterol oxidation catalyzed by cholesterol oxidase. Bull Exp Biol Med 100:1052-1054.
17. 17. Smith LL, Hill FL (1972). Detection of sterol hydroperoxides on thin-layer chromatoplates by means of the Wurster dyes. J Chromatogr 66:101-109.
18. 13C N.M.R. spectra of steroids - a survey and commentary. Org Magn Res 9:439-464.
19. 4-3-ketosteroids via their iminium salts, by 1,4-dihydropyridine derivatives. Rec Trav Chim 99:334-340.
20. 5 and saturated 4,4-disubstituted 3-ketosteroids. J Org Chem 46:1127-1132.
21. 21. Römer J, Scheller D, Grossmann G (1987). Carbon-13 nuclear magnetic resonance study of the bromo derivatives of 5α-cholestan-3-one and cholest-4-en-3-one. Mag Res Chem 25:135-140.
22. 27-steroid hydroperoxides. J Chromatogr 115:648-651.
23. 23. Teng JI, Kulig MJ, Smith LL, Kan G, van Lier JE (1973). Sterol metabolism. XX. Cholesterol 7β-hydroperoxide. J Org Chem 38: 119-123.
24. 24. de la Mare PBD, Wilson RD (1977). Autoxidation of cholest-5-en-3-one, and its accompanying isomerization, in acetic acid. J Chem Soc (Perkin II) 157-162.
25. 25. Dang H-S, Davies AG, Schiesser CH (1990). Allylic hydroperoxides formed by singlet oxygenation of cholest-5-en-3-one. J Chem Soc Parkin Trans 1) 789-794.
26. 26. Kulig MJ, Smith LL (1974). Sterol metabolism. XXXII. Radiationinduced oxidation of isomeric cholest-3β-ols. J Org Chem 39:3398-3402.
27. 27. Teng JI, Smith LL (1976). Sterol metabolism. XXXVIII. Oxidation of 4-cholesten-3β-ol by soybean lipoxygenase. J Steroid Biochem 7:577-581.
28. 28. Ansari GAS, Smith LL (1978). Sterol metabolism. XLI. Cholesterol A-ring autoxidations. Chem Phys Lipids 22:55-62.
29. 29. Teng JI, Smith LL (1973). Sterol metabolism, XXIV. On the unlikely participation of singlet molecular oxygen in several enzyme oxygenations. J Am Chem Soc 95:4060-4061.
30. 30. Teng JI, Smith LL (1976). Sterol Metabolism. XXXVII. On the oxidation of cholesterol by dioxygenases. Bioorg Chem 5:99-119.
31. 31. Smith LL (1981). Cholesterol Autoxidation. Plenum Press, New York.
32. 27 steroids by soybean lipoxygenase and rat liver microsomes. Lipids 15:563-571.
33. 33. Schneck GO, Gollnick K, Neumüller O-A (1957). Darstellung von Steroid-Hydroperoxyden mittels phototoxischer Photosensibilisatoren. Liebigs Ann Chem 603:46-59.
34. 34. Nickson A, Mendelson WL (1965). Reactivity and geometry in allylic systems. V. Oxygenation of cholest-5-en-3-one. J Org Chem 30:2087-2089.
35. 35. Fieser LF, Greene TW, Bischoff F, Lopez G, Rupp JJ (1955). A carcinogenic oxidation product of cholesterol. J Am Chem Soc 77: 3928-3929.
36. 4-cholestenone. J Org Chem 30:2052-2053.
37. 4-3-ketones. J Org Chem 32:2647-2649.
38. 38. Cheillan E, Lafont H, Termine E, Fernandez F, Suave P, Lesgards G (1989). Molecular characteristics of the cholesterol oxidase and factors influencing its activity. Biochim Biophys Acta 999:233-238.
39. 39. Loubat-Hugel C, Tritsch D, Biellmann J-F (1994). Modification de la cholestérol oxydase de Brevibacterium sterolicum et spécificité de substrat. C R Acad Sci 317:299-303.
40. 40. Li J, Vrielink A, Brick P, Blow DM (1993). Crystal structure cholesterol oxidase complexed with a steroid substrate: Implications for flavin adenine dinucleotide dependent alcohol oxidases. Biochemistry 32:11507-11515.
41. 41. Müller F (1987). Flavin radicals: Chemistry and biochemistry. Free Radic Biol Med 3:215-230.
42. 42. Massey V (1994). Activation of molecular oxygen by flavins and flavoproteins. J Biol Chem 269:22459-22462.
43. 43. Smith AG, Brooks CJW (1977). The mechanism of the isomerization of cholest-5-en-3-one to cholest-4-en-3-one by cholesterol oxidase. Biochem Soc Trans 5:1088-1090.
44. 5-isomerase component of cholesterol oxidase. Biochem J 167: 121-129.
45. 45. Kass IJ, Sampson NS (1995). The isomerization catalyzed by Brevibacterium sterolicum cholesterol oxidase proceeds stereospecifically with one base. Biochem Biophys Res Commun 206:688-693.
46. 46. Schwab JM, Henderson BS (1990). Enzyme-catalyzed allylic rearrangements. Chem Rev 90:1203-1245.
47. 47. Smith LL, Goodman JJ, Mendelsohn H, Bernstein S (1961). 6β-Hydroxylation of 9α-fluorohydrocortisone. J Org Chem 26:974-975.
48. 48. Tsuji A, Smulowitz M, Liang JSC, Fukushima D (1974). Synthesis of corticosteroid haptens. Steroids 24:739-751.
49. 49. Chaudhuri R, Cooley G, Coulson WF (1978). An improved synthesis of 6β-hydroxy-5β-pregnane-3,20-dione. Steroids 31:495-500.