Abstract
A formula of a steroid compound is easily recognized by its four-membered hydrocarbon core (Fig. 1.1a). My little grand daughter called it “a little cottage”, more advanced beginners may recall the term “cyclopentenoperhydrophenanthrene”. All the thousands of natural and synthetic steroids are derivatives of that core. Ring A is the cyclohexane ring on the left; it is attached to another six-membered ring B. The C ring follows, the D ring is a cyclopentane system.
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References
Applezweig N (1964) Steroid Drug, Vol. II, Index of Biologically Active Steroids. Holden-Day, San Francisco, CA.
Cahn RS, Ingold CK, Prelog V (1966) Specification of molecular chirality. Angew. Chem. Int. Ed. 5; 385–415.
Covey DF, Evers AS, Mennerick S, Zorumski CF, Purdy RH (2001) Recent developments in structure-activity relationships for steroid modulators of GABA(A) receptors. Brain Res. Rev. 37; 91–97.
Degtyar VG, Kushlinskii NE (2006) Metabolism of androgens in rat pituitary gland and hypothalamus: catabolism of dihydrotestosterone or transformation of androgen signal? Bull. Exp. Biol. Med. 129; 407–412.
Duax WL, Norton DA (eds) (1975) Atlas of Steroid Structure, Vol 1. Plenum, New York.
Fieser LF, Fieser M (1959) Steroids. Reinhold, New York.
Fischer DS, Woo LWL, Mahon MF, Purohit A, Reed MJ, Potter BVL (2003) D-ring modified estrone derivatives as novel potent inhibitors of steroid sulfatase. Bioorg. Med. Chem. 11; 1685–1700.
Griffin JF, Duax WL, Weeks CM (eds) (1984) Atlas of Steroid Structure, Vol 2. Plenum, New York.
Hill RA, Kirk DN, Makin HLJ, Murphy GM (eds) (1991) Dictionary of Steroids. Chapman & Hall, London.
Hu Y, Covey DF (1993) Synthesis of l, 10-seco-5 a -estr-l-ynes - potential mechanism-based inhibitors of 3 a -hydroxysterafcd alid 3|3-hydroxysteroid dehydrogenases. J. Chem. Soc. Perkin. Trans. 1; 417–422.
IUPAC-IUB (1982) Joint Commission on Biochemical Nomenclature (JCBN). Nomenclature of vitamin D. Recommendations. Mol. Cell. Biochem. 49; 177–181; Eur. J. Biochem. 124; 223–227.
Katona BW, Cummins CL, Ferguson AD, Li TT, Schmidt DR, Mangelsdorf DJ, Covey DF (2007) Synthesis, characterization, and receptor interaction profiles of enantiomeric bile acids. J. Med. Chem. 50; 6048–6058.
Klinger W, Lupp A, Karge E, Baumbach H, Eichhorn F, Feix A, Fuldner F, Gernhardt S, Knels L, Kost B, Mertens G, Werner F, Oettel M, Romer W, Schwarz S, Elger W, Schneider B (2002) Estradiol, testosterone, dehydroepiandrosterone and androstenedione: novel derivatives and enantiomers. Interactions with rat liver microsomal cytochrome P450 and antioxidant/radical scavenger activities in vitro. Toxicol. Lett. 128; 129–144.
Li W, Covey DF, Alakoskela JM, Kinnunen PK, Steinbach JH (2006) Enantiomers of neuroactive steroids support a specific interaction with the GABA-C receptor as the mechanism of steroid action. Mol. Pharmacol. 69; 1779–1782.
Moss GP (1989) Nomenclature of steroids (International Union of Pure and Applied Chemistry and International Union of Biochemistry). Pure Appl. Chem. 61; 1783–1822; Eur. J. Biochem. 186; 429–458.
Prelog V, Helmchen G (1982) Angew. Chem. 94; 614–631.
Reichstein T, Shoppee CW (1943) Hormones of the adrenal cortex. Vitam. Horm. 1; 345–113.
Simpkins JW, Yang SH, Liu R, Perez E, Cai ZY, Covey DF, Green PS (2004) Estrogen-like compounds for ischemic neuroprotection. Stroke. 35; 2648–2651.
Stárka L, Hampl R, Kasal A, Kohout L (1982) Androgen receptor binding and antiandrogenic activity of some 4, 5-secoandrostanes and ring B cyclopropanoandrostanes. J. Steroid Biochem. 17; 331–334.
Van Landingham JW, Cutler SM, Virmani S, Hoffman SW, Covey DF, Krishnan K, Hammes SR, Jamnongjit M, Stein DG (2006) The enantiomer of progesterone acts as a molecular neuropro-tectant after traumatic brain injury. Neuropharmacology 51; 1078–1085.
Wang X, Dykens JA, Perez E, Liu R, Yang S, Covey DF, Simpkins JW (2006) Neuroprotective effects of 17 beta-estradiol and nonfeminizing estrogens against H2O2 toxicity in human neuro-blastoma SK-N-SH cells. Mol. Pharmacol. 70; 395–404.
Additional General Bibliography
Field LD, Sternhell S, Kalman JR (2008) Organic Structures from Spectra. Wiley, Chichester.
Florkin M, Stotz EH (eds.) (1963) Comprehensive Biochemistry, Vol. 10, Sterols, Bile Acids, and Steroids. Elsevier, New York.
Gower DB (1980) Steroid Hormones. Mosby-Year Book, St. Louis, MO.
Hanson JR (1968) Introduction to Steroid Chemistry. Pergamon, Oxford.
Klyne W (1965) The Chemistry of the Steroids. Methuen, London.
Shoppee CW (1964) Chemistry of the Steroids, 2nd edn. Butterworths, London.
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Kasal, A. (2010). Structure and Nomenclature of Steroids. In: Makin, H., Gower, D. (eds) Steroid Analysis. Springer, Dordrecht. https://doi.org/10.1023/b135931_1
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