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Secosteroid

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Cholecalciferol (vitamin D3), an example of a 9,10-secosteroid. The hydroxyl group (HO-) is in position C3 of the parent steroid A-ring. The triene substructure attached to the ring bearing the hydroxyl group is a result of the ring scission (cleavage) giving rise to this secosteroid.
The parent steroid skeleton. The B-ring of the parent steroid is broken between C9 and C10 to yield the vitamins D.

Secosteroids (sec·o·ster·oid, sek'ō-stēr'oyd) are a subclass of the tetracyclic steroid class that are structural relatives bearing a cleavage of one of the four rings of that parent class.[1][2][3][4] The subclass nomenclature derives from the verb Template:Lang-lat meaning "to cut", and Template:Lang-lat of steroid, meaning "solid, three-dimensional".[5] Subclasses are defined by the carbon atoms of the parent steroid skeleton where the ring cleavage has taken place, e.g., 9,10-secosteroids for derivatives deriving from cleavage between carbon atoms C9 and C10 of the steroid B-ring (similarly 5,6-secosteroids, 13,14-steroids, etc.).

The prototypical secosteroid is cholecalciferol, vitamin D3.[6]

References

  1. ^ G.P. Moss and the Working Party of the IUPAC-IUB Joint Commission on Biochemical Nomenclature, "The Nomenclature of Steroids", hosted at Queen Mary University of London, Section 3S-1 (esp. 3S-1.4, incl. note 4) See [1] and [2], accessed 10 May 2014. Also available from same authors at Pure Appl. Chem. 1989, 61, 1783-1822 (esp. p. 1786f), or R.A. Hill, D.N. Kirk, H.L.J. Makin, H.L.J. & G.M. Murphy, 1991, "Dictionary of Steroids" London:Chapman and Hall, pp. xxx-lix. The Working Party of the IUPAC-IUB JCBN were P. Karlson (chairman), J.R. Bull, K. Engel, J. Fried, H.W. Kircher, K.L. Loening, G.P. Moss, G. Popják and M.R. Uskokovic.
  2. ^ R.A. Hill, D.N. Kirk, H.L.J. Makin, H.L.J. & G.M. Murphy, 1991, "Dictionary of Steroids" London:Chapman and Hall, passim.
  3. ^ Hanson JR (2010). "Steroids: partial synthesis in medicinal chemistry". Nat Prod Rep. 27 (6): 887–99. doi:10.1039/c001262a. PMID 20424788. {{cite journal}}: Unknown parameter |month= ignored (help)
  4. ^ See also the drugs.com [3], free (medical) dictionary [4], biology-online [5], and medilexicon [6] entries for this term, which in their more brief renditions of the definition sometimes indicate secosteroids as derivatives of steroids.
  5. ^ Donald Ayers, 1972, Bioscientific Terminology, Tucson: University of Arizona Press, pp. 241, 129. ISBN 978-0-8165-0305-6. See http://www.uapress.arizona.edu/Books/bid18.htm, accessed 10 May 2014.
  6. ^ See, for instance, J.R. Hanson, 2010, "Steroids: partial synthesis in medicinal chemistry, Nat Prod Rep. 27(6):887-99. doi: 10.1039/c001262a, PMID: 20424788. See http://pubs.rsc.org/en/content/articlelanding/2010/np/c001262a#!divAbstract, accessed 10 May 2014.