Steroid

From Wikipedia, the free encyclopedia

Steroid skeleton of lanosterol. The total number of carbons (30) reflects its triterpenoid origin.

A steroid is a terpenoid lipid characterized by a carbon skeleton with four fused rings, generally arranged in a 6-6-6-5 fashion.

Steroids vary by the functional groups attached to these rings and the oxidation state of the rings. Hundreds of distinct steroids are found in plants, animals, and fungi. All steroids are made in cells either from the sterol lanosterol (animals and fungi) or the sterol cycloartenol (plants). Both sterols are derived from the cyclization of the triterpene squalene.^[1]

Origin

Simplified version of the steroid synthesis pathway with the intermediates isopentenyl pyrophosphate (IPP), dimethylallyl pyrophosphate (DMAPP), geranyl pyrophosphate (GPP) and squalene shown. Some intermediates are omitted.

Steroids include estrogen (US spelling) or oestrogen (UK/AUS spelling), progesterone and testosterone. Estrogen and progesterone are made primarily in the ovary and in the placenta during pregnancy and testosterone in the testes. Testosterone is also converted into estrogen to regulate the supply of each, in the bodies of both females and males. Certain neurons and glia in the central nervous system (CNS) express the enzymes that are required for the local synthesis of pregnane neurosteroids, either de novo or from peripherally derived sources. The rate limiting step of steroid synthesis is the conversion of cholesterol to pregnenolone which occurs inside the mitochondrion.^[2]

Classification

Taxonomical/Functional

Some of the common categories of steroids:

• Animal steroids
  • Insect steroids
    • Ecdysteroids such as ecdysterone
  • Vertebrate steroids
    • Steroid hormones
      • Sex steroids are a subset of sex hormones that produce sex differences or support reproduction. They include androgens, estrogens, and progestagens.
      • Corticosteroids include glucocorticoids and mineralocorticoids. Glucocorticoids regulate many aspects of metabolism and immune function, whereas mineralocorticoids help maintain blood volume and control renal excretion of electrolytes.
      • Anabolic steroids are a class of steroids that interact with androgen receptors to increase muscle and bone synthesis. There are natural and synthetic anabolic steroids. In popular language the word "steroids" usually refers to anabolic steroids.
    • Cholesterol which modulates the fluidity of cell membranes and is the principle constituent of the plaques implicated in atherosclerosis.
• Plant steroids
  • Phytosterols
  • Brassinosteroids
• Fungus steroids
  • Ergosterols

Structural

It is also possible to classify steroids based upon their chemical composition. One example of how MeSH performs this classification is available at the Wikipedia MeSH catalog. Examples from this classification include:

See also

• Batrachotoxin
• List of steroid abbreviations
• Steroid biosynthesis

References

Further reading

• G. P. Moss (1989). "Nomenclature of Steroids (Recommendations 1989)". Pure & Appl. Chem. 61 (10): 1783-1822. 

External links

• Michael W. King's Medical Biochemistry. Steroids and retinoids are both terpenes which are hydrophobic, pass through cell membranes and bind to intracellular receptors. However, retinoic acid is not a steroid because it does not have the defining ring structure. See: Steroids and Related Hydrophobic Molecules.
• "Biochemistry" by Jeremy M. Berg, John L. Tymoczko and Lubert Stryer (2002) W. H. Freeman and Co. steroid topics in this
• Steroids, Rage and Criminal Activity -- Video: Insidermedicine.com's Maria Radina on Anabolic Androgenic Steroids, as presented in a study in Archives of General Psychiatry.
• Nomenclature of Steroids Home Page at Queen Mary University of London.
• Steroid abbreviations at ISAS (page now defunct, web archive version)