Steroids biochemical hydroxylation

Pellissier, H. and Santelli, M. (2001) Chemical and biochemical hydroxylations of steroids. A review. Organic Preparations and Procedures International, 33 (1), 1-58. 

Joannou GE (1981) Identification of 15/5-hydroxylated C21 Steroids in the neo-natal period the role of 3a,15/),17a-trihydroxy-5/ -pregnan-20-one in the perinatal diagnosis of congenital adrenal hyperplasia (CAH) due to a 21-hydroxylase deficiency. J Steroid Biochem 14 901-912... 

Menard, R.H., EC. Bartter, and J.R. Gillette (1976). Spironolactone and cytochrome P-450 Impairment of steroid 21-hydroxylation in the adrenal cortex. Arch. Biochem. Biophys. 173, 395-A02. 

Kremers P. Progesterone and pregnenolone 17a-hydroxylase substrate specificity and selective inhibition by 17a-hydroxylated products. J Steroid Biochem 1976 7 571-575. 

Jordan VC, Gosden B (1983) Differential antiestrogen action in the immature rat uterus a comparison of hydroxylated antiestrogens with high affinity for the estrogen receptor. J Steroid Biochem 19 1249-1258... 

Once formed cholesterol undergoes a number of biochemical transformations A very common one is acylation of its C 3 hydroxyl group by reaction with coenzyme A derivatives of fatty acids Other processes convert cholesterol to the biologically impor tant steroids described m the following sections... 

The interconversion of alcohols to ketones is a common biochemical reaction. The introduction of hydroxyl groups into toe steroid nucleus and side chain creates a variety of secondary alcohols. Some of these, especially at positions 3, 7, 11 and 17 are frequently oxidised to ketones. 

The synthesis of triterpenoid saponins from the skeletons shown in Fig. 2 involves a series of further modifications that may include a variety of different oxidation and substitution events [9]. Very little is known about the enzymes and genes involved in the elaboration of the triterpenoid skeleton, although genetic and biochemical analysis of saponin-deficient mutants of plants is likely to accelerate the dissection of these processes [16]. Progress has been made in the characterisation of saponin glucosyltransferases (primarily for steroidal and steroidal alkaloid saponins), and the first of these enzymes (StSGT from potato) has been cloned. Since glycosylation at the C-3 hydroxyl position confers am-... 

Ohno, H., K. Suzuki, and T. Kimura A non-heme iron protein from pig testis and its substitution for adrenal non-heme iron protein (adrenodoxin) in steroid 11 p-hydroxylation. Biochem. Biophys. Res. Commun. 26, 651 (1967). 

Methylene groups are hydroxylated to give alcoholic groups. Such hydroxylations are rarely achieved chemically but occur frequently in biochemical processes. The vast majority of such hydroxylations takes place in steroidal ketones and will be discussed in the section on ketones. 

Secondary steroidal alcohols react in preference to primary allylic alcohols in biochemical oxidations usingJihizopus arrhizus and Helicostylum piriforme or Cunninghamella blakesleeana. However, the reaction is complicated by hydroxylations in positions 6 (with Rhizopus arrhizus) and 9 (with Helicostylum piriforme or Cunninghamella blakesleeana) [1059]. 

Oxidations of steroidal keto alcohols to diketones are frequently accomplished biochemically. In addition, isomerization of double bonds, dehydrogenations, and hydroxylations often take place. 

As is the case for other steroids, the Hver is the primary site for the inactivation of estrogens. The main biochemical reactions are hydroxylation, oxidation, reduction, and methylation. Conjugation with glucuronic or sulfuric acid, which imparts more water solubility to these steroids and thus allows them to be eliminated rapidly through the... 

The 5-hydroxylated analog of indolacetic acid is the principal urinary metabolite of serotonin. On the basis of two biochemical observations, the possible role of serotonin in inflammatory processes and the increase of urinary metabolites of tryptophan in rheumatic patients, Shen, from the Merck Laboratories, designed anti-inflammatory compounds derived from indolacetic acid. Among them he found indomethacin in 1963, one of the most powerful non-steroidal anti-inflammatory drugs currently known. ... 

E.F. Johnson (1988). Selective inactivation by 21-chlorinated steroids of rabbit liver and adrenal microsomal cytochromes P-450 involved in progesterone hydroxylation. Arch. Biochem. Biophys. 264,462 71. 

Macrides, T.A., Shihata, A., Kalafatis, N., and Wright, P.F.A., A comparison of the hydroxyl radical scavenging properties of the shark bile steroid 5-b-scynmol and plant pycnogenols, Biochem. Mol. Biol. Int., 42, 1249-1260, 1997. 

Estabrook RW (2005) Steroid hydroxylations a paradigm for cytochrome P450 catalyzed mammalian monooxygenation reactions. Biochem Biophys Res Commun 338 290-298... 

Narasimhulu S (1971) Uncoupling of oxygen activation from hydroxylation in the steroid C-21 hydroxylase of bovine adrenocortical microsomes. Arch Biochem Biophys 147 384-390... 

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