메뉴 건너뛰기




Volumn 94, Issue 5, 2005, Pages 405-420

New assumptions about oxidative processes involved in steroid hormone biosynthesis: Is the role of cytochrome P-450-activated dioxygen limited to hydroxylation reactions or are dioxygen insertion reactions also possible?

Author keywords

Aldosterone; Cortisol; Cyclic peroxides; Cytochrome P 450 activated dioxygen; Estradiol; Hydroxylation; Peroxides; Steroidogenesis

Indexed keywords

11BETA,19 DIHYDROXYDEOXYCORTICOSTERONE; 18 HYDROXYESTRONE; 18 HYDROXYHYDROCORTISONE; 19 HYDROXYDEOXYCORTICOSTERONE; ALDOSTERONE; CARBON; CORTICOSTERONE; CORTICOSTERONE DERIVATIVE; CYTOCHROME P450; DIOXANE; ESTROGEN; ESTRONE DERIVATIVE; HYDROCORTISONE; HYDROPEROXIDE; OXYGEN; PREGNANE DERIVATIVE; STEROID; UNCLASSIFIED DRUG;

EID: 18144407254     PISSN: 09600760     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jsbmb.2004.12.040     Document Type: Article
Times cited : (8)

References (58)
  • 2
    • 18144396296 scopus 로고
    • A new C-18-oxygenated corticosteroid from bullfrog adrenals
    • S. Ulick, and K. Kusch A new C-18-oxygenated corticosteroid from bullfrog adrenals J. Am. Chem. Soc. 82 1960 6421 6422
    • (1960) J. Am. Chem. Soc. , vol.82 , pp. 6421-6422
    • Ulick, S.1    Kusch, K.2
  • 3
    • 18144413307 scopus 로고
    • Conversion of 19-hydroxy-delta-4-androstene-3,17-dione to estrone by endocrine tissue
    • A.S. Meyer Conversion of 19-hydroxy-delta-4-androstene-3,17-dione to estrone by endocrine tissue Biochchim. Biophys. Acta 24 1955 1435 1442
    • (1955) Biochchim. Biophys. Acta , vol.24 , pp. 1435-1442
    • Meyer, A.S.1
  • 5
    • 0035165548 scopus 로고    scopus 로고
    • 17-Hydroxylase: An evaluation of the present view of its catalytic role in steroidogenesis
    • S. Lieberman, and P.A. Warne 17-Hydroxylase: an evaluation of the present view of its catalytic role in steroidogenesis J. Steroid Biochem. Mol. Biol. 78 2001 299 312
    • (2001) J. Steroid Biochem. Mol. Biol. , vol.78 , pp. 299-312
    • Lieberman, S.1    Warne, P.A.2
  • 10
    • 0006566970 scopus 로고
    • Androgen formation by cytochrome P450-CYP-17
    • D.C. Swinney, and A.Y. May Androgen formation by cytochrome P450-CYP-17 Biochemistry 33 1994 2183 2190
    • (1994) Biochemistry , vol.33 , pp. 2183-2190
    • Swinney, D.C.1    May, A.Y.2
  • 11
    • 0031831881 scopus 로고    scopus 로고
    • The dioxygenase-catalyzed formation of vicinal cis-diols
    • D.R. Boyd, and G.N. Sheldrake The dioxygenase-catalyzed formation of vicinal cis-diols Nat. Prod. Res. 15 1998 309
    • (1998) Nat. Prod. Res. , vol.15 , pp. 309
    • Boyd, D.R.1    Sheldrake, G.N.2
  • 12
    • 0347264753 scopus 로고    scopus 로고
    • Crystal structure of naphthalene dioxygenase: Side-on binding of dioxygen to iron
    • A. Karlsson, J.V. Parales, R.E. Parales, D.T. Gibson, H. Eklund, and S. Ramaswamy Crystal structure of naphthalene dioxygenase: side-on binding of dioxygen to iron Science 299 2003 1039 1042
    • (2003) Science , vol.299 , pp. 1039-1042
    • Karlsson, A.1    Parales, J.V.2    Parales, R.E.3    Gibson, D.T.4    Eklund, H.5    Ramaswamy, S.6
  • 13
    • 0011146572 scopus 로고
    • The chemistry of 1,2-dioxetanes
    • A. Waldemar The chemistry of 1,2-dioxetanes Adv. Hetericycl. Chem. 21 1977 437 481
    • (1977) Adv. Hetericycl. Chem. , vol.21 , pp. 437-481
    • Waldemar, A.1
  • 14
    • 0000579094 scopus 로고
    • Ground states of molecules
    • M.J.S. Dewar, and W. Thiel Ground states of molecules J. Am. Chem. Soc. 97 1975 3978 3986
    • (1975) J. Am. Chem. Soc. , vol.97 , pp. 3978-3986
    • Dewar, M.J.S.1    Thiel, W.2
  • 16
    • 0035059352 scopus 로고    scopus 로고
    • Allosteric behavior in cytochrome P450 dependent in vitro drug-drug interactions
    • W.M. Atkins, R.W. Wang, and A.Y.H. Lu Allosteric behavior in cytochrome P450 dependent in vitro drug-drug interactions Chem. Res. Toxicol. 14 2001 338 347
    • (2001) Chem. Res. Toxicol. , vol.14 , pp. 338-347
    • Atkins, W.M.1    Wang, R.W.2    Lu, A.Y.H.3
  • 17
  • 19
    • 0016156788 scopus 로고
    • The stoichiometry of the conversion of cholesterol and hydroxycholesterols to pregnenolone (3β-hydroxypregn-5-en-20-one) catalyzed by adrenal cytochrome P-450
    • M. Shikita, and P.F. Hall The stoichiometry of the conversion of cholesterol and hydroxycholesterols to pregnenolone (3β-hydroxypregn-5-en- 20-one) catalyzed by adrenal cytochrome P-450 Proc. Natl. Acad. Sci. U.S.A. 71 1974 1441 1445
    • (1974) Proc. Natl. Acad. Sci. U.S.A. , vol.71 , pp. 1441-1445
    • Shikita, M.1    Hall, P.F.2
  • 20
    • 0016293443 scopus 로고
    • Utilization of oxygen and reduced nicotinamide adenine dinucleotide phosphate by human placental microsomes during aromatization of androstenedione
    • E.A. Thompson, and P.K. Siiteri Utilization of oxygen and reduced nicotinamide adenine dinucleotide phosphate by human placental microsomes during aromatization of androstenedione J. Biol. Chem. 249 1974 5364 5372
    • (1974) J. Biol. Chem. , vol.249 , pp. 5364-5372
    • Thompson, E.A.1    Siiteri, P.K.2
  • 21
    • 0017800232 scopus 로고
    • Cytochrome P-450 for 11β and 18-hydroxylase activities of bovine adrenocortical mitochondria
    • M. Watanuki, B.E. Tilley, and P.F. Hall Cytochrome P-450 for 11β and 18-hydroxylase activities of bovine adrenocortical mitochondria J. Am. Chem. Soc. 17 1978 127 131
    • (1978) J. Am. Chem. Soc. , vol.17 , pp. 127-131
    • Watanuki, M.1    Tilley, B.E.2    Hall, P.F.3
  • 23
    • 0023919155 scopus 로고
    • Conversion of 11-deoxycorticosterone and corticosterone to aldosterone by cytochrome P-450 11β-18-hydroxylase from porcine adrenal
    • K. Yanagibashi, C.H. Shackleton, and P.F. Hall Conversion of 11-deoxycorticosterone and corticosterone to aldosterone by cytochrome P-450 11β-18-hydroxylase from porcine adrenal J. Steroid Biochem. 29 1988 665 675
    • (1988) J. Steroid Biochem. , vol.29 , pp. 665-675
    • Yanagibashi, K.1    Shackleton, C.H.2    Hall, P.F.3
  • 25
    • 0018619822 scopus 로고
    • Side-chain cleavage of 4-cholesten-3-one, 5-cholesten-3α-ol, β-sitosterol, and related steroids in endocrine tissues from rat and man
    • L. Aringer, P. Encroth, and L. Nordstrom Side-chain cleavage of 4-cholesten-3-one, 5-cholesten-3α-ol, β-sitosterol, and related steroids in endocrine tissues from rat and man J. Steroid Biochem. 11 1979 127 185
    • (1979) J. Steroid Biochem. , vol.11 , pp. 127-185
    • Aringer, L.1    Encroth, P.2    Nordstrom, L.3
  • 26
    • 0017157278 scopus 로고
    • Oxidation of cholesterol and cholesterol analogues by mitochondrial preparations of steroid-hormone-producing tissue
    • J.R. Arthur, H.A.F. Blair, G.S. Boyd, J.I. Mason, and K.C. Suckling Oxidation of cholesterol and cholesterol analogues by mitochondrial preparations of steroid-hormone-producing tissue Biochem. J. 158 1976 47 51
    • (1976) Biochem. J. , vol.158 , pp. 47-51
    • Arthur, J.R.1    Blair, H.A.F.2    Boyd, G.S.3    Mason, J.I.4    Suckling, K.C.5
  • 27
    • 18144372112 scopus 로고
    • Metabolism of cholesterol in the chick embryo. II. Isolation and chemical nature of two companion sterols
    • W.M. Stokes, W.A. Fish, and F.C. Hickey Metabolism of cholesterol in the chick embryo. II. Isolation and chemical nature of two companion sterols J. Biol. Chem. 220 1956 415 430
    • (1956) J. Biol. Chem. , vol.220 , pp. 415-430
    • Stokes, W.M.1    Fish, W.A.2    Hickey, F.C.3
  • 28
    • 0018070754 scopus 로고
    • Biosynthesis of pregnenolone from cholesterol by mitochondrial enzymes of bovine adrenal cortex
    • B.A. Teicher, N. Koizumi, M. Korfeda, M. Korfeda, M. Shikita, and P. Talalay Biosynthesis of pregnenolone from cholesterol by mitochondrial enzymes of bovine adrenal cortex Eur. J. Biochem. 91 1978 11 18
    • (1978) Eur. J. Biochem. , vol.91 , pp. 11-18
    • Teicher, B.A.1    Koizumi, N.2    Korfeda, M.3    Korfeda, M.4    Shikita, M.5    Talalay, P.6
  • 29
    • 0014938174 scopus 로고
    • Conversion of cholesterol 20α-hydroperoxide to 20α, 21- and 20α, 22-R-dihydroxycholesterol by adrenal cortex mitochondria
    • J.E. Van Lier, and L.L. Smith Conversion of cholesterol 20α-hydroperoxide to 20α, 21- and 20α, 22-R- dihydroxycholesterol by adrenal cortex mitochondria Biochim. Biophys. Acta 210 1970 153 203
    • (1970) Biochim. Biophys. Acta , vol.210 , pp. 153-203
    • Van Lier, J.E.1    Smith, L.L.2
  • 30
    • 18144379641 scopus 로고
    • Rearrangement of alkyl hydroperoxides mediated by cytochrome P-450
    • J.D. Miners *et al.
    • K.M. Fish, G.E. Avaria, and J.T. Groves Rearrangement of alkyl hydroperoxides mediated by cytochrome P-450 J.D. Miners Microsomes and Drug Interactions 1988 176 183
    • (1988) Microsomes and Drug Interactions , pp. 176-183
    • Fish, K.M.1    Avaria, G.E.2    Groves, J.T.3
  • 31
    • 0000340145 scopus 로고
    • The chemistry of hydroperoxides
    • M.S. Kharasch, and J.G. Burt The chemistry of hydroperoxides J. Org. Chem. 1951 150 160
    • (1951) J. Org. Chem. , pp. 150-160
    • Kharasch, M.S.1    Burt, J.G.2
  • 32
    • 0027315887 scopus 로고
    • Mechanistic studies on aromatase and relied CC bond cleaving P-450 enzymes
    • M. Akhtar, V.C.O. Njar, and J. Neville Wright Mechanistic studies on aromatase and relied CC bond cleaving P-450 enzymes J. Steroid Biochem. Mol. Biol. 44 1993 375 387
    • (1993) J. Steroid Biochem. Mol. Biol. , vol.44 , pp. 375-387
    • Akhtar, M.1    Njar, V.C.O.2    Neville Wright, J.3
  • 34
    • 18144414398 scopus 로고
    • Adrenocortical factors in hypertension. Significance of 18-hydroxy 11 deoxycorticosterone
    • S. Ulick Adrenocortical factors in hypertension. Significance of 18-hydroxy 11 deoxycorticosterone Am. J. Cardiol. 38 1976 38 814
    • (1976) Am. J. Cardiol. , vol.38 , pp. 38-814
    • Ulick, S.1
  • 36
    • 0016425112 scopus 로고
    • 18-Hydroxylation of deoxycorticosterone by reconstituted systems from rat and bovine adrenals
    • I. Bjorkhem, and K.-E. Karlmar 18-Hydroxylation of deoxycorticosterone by reconstituted systems from rat and bovine adrenals Eur. J. Biochem. 51 1975 51 145
    • (1975) Eur. J. Biochem. , vol.51 , pp. 51-145
    • Bjorkhem, I.1    Karlmar, K.-E.2
  • 37
    • 0017800232 scopus 로고
    • Cytochrome P-450 for 11β- and 18-hydroxylase activities of bovine adrenal mitochondria. One enzyme or two?
    • M. Watanuki, B.E. Tillely, and P.F. Hall Cytochrome P-450 for 11β- and 18-hydroxylase activities of bovine adrenal mitochondria. One enzyme or two? Biochemistry 1978 17 127
    • (1978) Biochemistry , pp. 17-127
    • Watanuki, M.1    Tillely, B.E.2    Hall, P.F.3
  • 38
    • 0017249629 scopus 로고
    • Mutant forms of cytochrome P-450 controlling both 18 and 11β-steroid hydroxylation in the rat
    • J.T. Rapp, and L.K. Dahl Mutant forms of cytochrome P-450 controlling both 18 and 11β-steroid hydroxylation in the rat Biochemistry 15 1976 1235 1240
    • (1976) Biochemistry , vol.15 , pp. 1235-1240
    • Rapp, J.T.1    Dahl, L.K.2
  • 39
    • 0001008029 scopus 로고
    • An efficient method for finding the minimum of a function of several variables without calculating derivatives
    • M. Powell An efficient method for finding the minimum of a function of several variables without calculating derivatives Comput. J. 7 1964 155 162
    • (1964) Comput. J. , vol.7 , pp. 155-162
    • Powell, M.1
  • 40
    • 33750639677 scopus 로고
    • The key-lock theory and the induced fit theory
    • D.E. Koshland Jr. The key-lock theory and the induced fit theory Angew. Chem. Inl. Ed. Engl. 33 1994 2375 2378
    • (1994) Angew. Chem. Inl. Ed. Engl. , vol.33 , pp. 2375-2378
    • Koshland Jr., D.E.1
  • 41
    • 0035432947 scopus 로고    scopus 로고
    • Molecular recognition by induced fit: How fit is the concept?
    • H.R. Bosshard Molecular recognition by induced fit: how fit is the concept? News Physiol. Sci. 16 2001 171 173
    • (2001) News Physiol. Sci. , vol.16 , pp. 171-173
    • Bosshard, H.R.1
  • 43
    • 0026518151 scopus 로고
    • Steroidogenic potential of lyophilized mitochondria from bovine adrenocortical tissue
    • V.V.K. Prasad, C. Mathur, M. Welch, and S. Lieberman Steroidogenic potential of lyophilized mitochondria from bovine adrenocortical tissue Proc. Natl. Acad. Sci. U.S.A. 89 1992 4173 4177
    • (1992) Proc. Natl. Acad. Sci. U.S.A. , vol.89 , pp. 4173-4177
    • Prasad, V.V.K.1    Mathur, C.2    Welch, M.3    Lieberman, S.4
  • 44
    • 0027346746 scopus 로고
    • 11-Beta-hydroxysteroi dehydrogenase
    • C. Monder, and P.C. White 11-Beta-hydroxysteroi dehydrogenase Vitam. Horm. 47 1993 187 271
    • (1993) Vitam. Horm. , vol.47 , pp. 187-271
    • Monder, C.1    White, P.C.2
  • 45
    • 0021752001 scopus 로고
    • A heuristic proposal for understanding steroidogenic processes
    • S. Lieberman, N.J. Greenfield, and A. Wolfson A heuristic proposal for understanding steroidogenic processes Endocr. Rev. 5 1984 128 200
    • (1984) Endocr. Rev. , vol.5 , pp. 128-200
    • Lieberman, S.1    Greenfield, N.J.2    Wolfson, A.3
  • 48
    • 0032444160 scopus 로고    scopus 로고
    • Characterization of the enzyme involved in the production of 19-nordeoxycorticosterone in hamster
    • J. Courtemanche, and J.G. LeHoux Characterization of the enzyme involved in the production of 19-nordeoxycorticosterone in hamster Endocr. Res. 24 1998 653 657
    • (1998) Endocr. Res. , vol.24 , pp. 653-657
    • Courtemanche, J.1    Lehoux, J.G.2
  • 50
    • 18144394455 scopus 로고
    • Isolierung und Konstitutionsermittlung weiterer pregnanverbindungen aus nebennieren
    • R. Neher, and A. Wettstein Isolierung Und Konstitutionsermittlung weiterer pregnanverbindungen aus nebennieren Helvet. Chim. Acta 39 1956 2062
    • (1956) Helvet. Chim. Acta , vol.39 , pp. 2062
    • Neher, R.1    Wettstein, A.2
  • 51
    • 18144428008 scopus 로고
    • Isolatin of estrone from beef adrenal glands
    • D. Beall Isolatin of estrone from beef adrenal glands Nature 144 1939 76
    • (1939) Nature , vol.144 , pp. 76
    • Beall, D.1
  • 52
    • 18144376459 scopus 로고
    • The isolation of a sixth Kober chromogen from the urine of pregnant women and its provisional identification as 18-hydroxyoestrone
    • K.H. Loke, E.J.D. Watson, and G.F. Marrian The isolation of a sixth Kober chromogen from the urine of pregnant women and its provisional identification as 18-hydroxyoestrone Biochim. Biophys. Acta 26 1957 230 231
    • (1957) Biochim. Biophys. Acta , vol.26 , pp. 230-231
    • Loke, K.H.1    Watson, E.J.D.2    Marrian, G.F.3
  • 54
    • 0020321013 scopus 로고
    • Isolation and identification of 18-hydroxycortisol from the urine of patients with primary aldosteronism
    • M.D. Chu, and S. Ulick Isolation and identification of 18-hydroxycortisol from the urine of patients with primary aldosteronism J. Biol. Chem. 257 1982 2218 2224
    • (1982) J. Biol. Chem. , vol.257 , pp. 2218-2224
    • Chu, M.D.1    Ulick, S.2
  • 55
    • 0020541134 scopus 로고
    • Biosynthesis of 18-oxocortisol by aldosterone-producing adrenal tissue
    • S. Ulick, M.D. Chu, and M. Land Biosynthesis of 18-oxocortisol by aldosterone-producing adrenal tissue J. Biol. Chem. 258 1983 5498 5502
    • (1983) J. Biol. Chem. , vol.258 , pp. 5498-5502
    • Ulick, S.1    Chu, M.D.2    Land, M.3
  • 56
    • 0030068024 scopus 로고
    • Molecular genetics of human blood pressure variation
    • R.P. Lifton Molecular genetics of human blood pressure variation Science 272 1995 676 680
    • (1995) Science , vol.272 , pp. 676-680
    • Lifton, R.P.1
  • 57
    • 13044298753 scopus 로고
    • Isolation of pregnane-3,17,20-triol from urine of women showing adreno-genital syndrome
    • G.C. Butler, and G.F. Marrian Isolation of pregnane-3,17,20-triol from urine of women showing adreno-genital syndrome J. Biol. Chem. 119 1937 565 572
    • (1937) J. Biol. Chem. , vol.119 , pp. 565-572
    • Butler, G.C.1    Marrian, G.F.2
  • 58
    • 0006539444 scopus 로고
    • Metabolism of 17α,20α-dihydroxy-20-isocholesterol by guinea pig adrenal preparations
    • S. Burstein, H.L. Kimball, N.K. Chaudhuri, and M. Gut Metabolism of 17α,20α-dihydroxy-20-isocholesterol by guinea pig adrenal preparations J. Biol. Chem. 10 1969 4417 4425
    • (1969) J. Biol. Chem. , vol.10 , pp. 4417-4425
    • Burstein, S.1    Kimball, H.L.2    Chaudhuri, N.K.3    Gut, M.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.