Androstenediones

Testosterone, the principal male sex steroid hormone, is synthesized in five steps from cholesterol, as shown below. In the last step, five isozymes catalyze the 17/3-hydroxysteroid dehydrogenase reactions that interconvert 4-androstenedione and testosterone. Defects in the synthesis or action of testosterone can impair the development of the male phenotype during embryogenesis and cause the disorders of human sexuality termed male pseudohermaphroditism. Specifically, mutations in isozyme 3 of the 17/3-hydroxysteroid dehydrogenase in the fetal testis impair the for-... 

Sex Hormones Testosterone and androsterone are the two most important male sex hormones, or androgens. Androgens are responsible for the development of male secondary sex characteristics during puberty and for promoting tissue and muscle growth. Both are synthesized in the testes from cholesterol. Androstenedione is another minor hormone that has received particular attention because of its use by prominent athletes. 

Estrogens are formed by the aromatization of androgens in a complex process that involves three hydroxyla-tion steps, each of which requires O2 and NADPH. The aromatase enzyme complex is thought to include a P450 monooxygenase. Estradiol is formed if the substrate of this enzyme complex is testosterone, whereas estrone results from the aromatization of androstenedione. 

The ceUular source of the various ovarian steroids has been difficult to unravel, but a transfer of substrates between two cell types is involved. Theca cells are the source of androstenedione and testosterone. These are converted by the aromatase enzyme in granulosa cells to estrone and estradiol, respectively. Progesterone, a precursor for all steroid hormones, is produced and secreted by the corpus luteum as an end-product hormone because these cells do not contain the enzymes necessary to convert progesterone ro other steroid hormones (Figure 42-8). 

The 17P-hydroxysteroid oxidoreductase enzymes (HSOR) occur as two distinct isoforms (I and II). They are involved in the conversion of estrone to estradiol. The type I enzyme converts estrone to estradiol (also androstenedione to testosterone) and the type II catalyses the reverse reaction. Phytoestrogens have been shown to inhibit both HSOR enzymes in vitro. 

Mooradian (1993) has studied the antioxidant properties of 14 steroids in a non-membranous system in which the fluorescence of the protein phycoerythrin was measured in the presence of a lipid peroxyl radical generator (ABAP). Oxidation of the protein produces a fluorescent species. Quenching of fluorescence by a test compound indicates antioxidant activity. Oestrone, testosterone, progesterone, androstenedione, dehydroepian-drosterone, cortisol, tetrahydrocortisone, deoxycorti-... 

The zona reticularis produces the androgens androstene-dione, dehydroepiandrosterone (DHEA), and the sulfated form of dehydroepiandrosterone (DHEA-S). Only small amounts of testosterone and estrogen are produced in the adrenal glands. Androstenedione and DHEA are converted in the periphery, largely to testosterone and estrogen. 

Testosterone, the major androgenic hormone, accounts for 95% of the androgen concentration. The primary source of testosterone is the testes however, 3% to 5% of the testosterone concentration is derived from direct adrenal cortical secretion of testosterone or C-19 steroids such as androstenedione.17,18... 

Recently, Voogt et al. [91] have reported on the d5-pathway in steroid metabolism of Asterias rubens. These workers established the existence of the d5-pathway (Scheme 20), analogous to the pathway found in mammals this conclusion was based on the observation that radiolabeled cholesterol (1) was converted to pregnenolone (112), 17a-hydroxypregnenolone (141), and androstenediol (142). Labeled pregnenolone was converted additionally to progesterone (129). Androstenediol (142) was the main metabolite of de-hydroepiandrosterone (143), a reaction catalyzed by 17/i-hydroxysteroid dehydrogenase (17/1-HSD). The metabolic conversion of androstenedione (131) to testosterone (132) is also mediated by 17/J-HSD and is related to... 

Occurrence in molluscs of steroidogenesis along a pathway very similar to that found in vertebrates has been claimed. Testosterone (64) - androstenedione (65) interconversion has been demonstrated in gonads of the male and female bivalve - Mytilus edulis [117] and of the gastropod Crepidula fornicata [118], by using labelled testosterone and androstenedione. Moreover, several steroids have been identified in the gonads and hepatopancreas of the opisthobranch... 

The aromatization of testosterone to form estradiol, and of androstenedione to form estrone (Fig. 52-4), has been described in brain tissue in vitro and in vivo [1, 9]. Aromatization is higher in hypothalamus and limbic... 

Androstenedione Androstenedione ELISA kit Oxford Biomedical Research http //www.oxfordbiomed.com/... 

An interesting pair of compounds is caffeine and theophylline [97] these compounds are relatively polar compounds with different functional groups (tertiary and secondary amine). In a few cases, more appropriate comparisons have been made such as between androstenedione/testoster-one and methyl benzoate/anisole these compounds are expected to be different in Snyder interaction groups. 

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