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{{Short description|Class of chemicals derived from steroids}}
[[Image:Cholecalciferol.svg|thumb|[[Cholecalciferol]] (vitamin D{{ssub|3}}), 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.]]
{{nodisplay-span|1={{r|n1=IUPAC-IUB|r1={{cite web | url = http://www.chem.qmul.ac.uk/sbcs/iupac/steroid/ | title = The Nomenclature of Steroids | author = Moss GP and the Working Party of the IUPAC-IUB Joint Commission on Biochemical Nomenclature | publisher = Queen Mary University of London}} also available as {{cite journal | journal = [[Pure and Applied Chemistry|Pure Appl. Chem.]] | volume = 61 | issue = 10 | pages = 1786f | year = 1989 | title = Nomenclature of Steroids (Recommendations 1989) | author = Moss GP | doi = 10.1351/pac198961101783| quote = | doi-access = free }}}}}}
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[[Image:Trimethyl steroid-nomenclature.svg|thumb|right|250px|The parent steroid skeleton. The B-ring of the parent steroid is broken between C9 and C10 to yield the vitamins D.]]
[[File:Cholecalciferol-numbered.svg|thumb|[[Cholecalciferol]], an example of a 9,10-secosteroid. [[IUPAC]]-approved carbon numbering and ring labeling is shown in the picture. Since secosteroids are derived from steroids, they retain the same labeling system as steroids.
{{r|n1=IUPAC-IUB|loc1=&sect;3S-8|a1=#<sup>'''''[[#L1a|a]] [[#L1b|b]] [[#L1c|c]]'''''</sup> Chapters [https://iupac.qmul.ac.uk/steroid/3S089.html 3S-8 "Ring fission" and 3S-9 "Vitamin D group"]|link-id=L1a}}]]
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[[Image:Trimethyl steroid-nomenclature.svg|thumb|right|250px|The parent steroid skeleton. The B-ring of the parent steroid is broken between C9 and C10 to yield D vitamins.]]


A '''secosteroid''' ({{IPAc-en|'|s|ɛ|k|oʊ|,|s|t|ɛ|r|ɔɪ|d}}) is a type of [[steroid]] with a "broken" ring. The word ''secosteroid ''derives from the Latin verb ''secare'' meaning "to cut",<ref name = "Ayers">{{cite book | author = Ayers D | title = Bioscientific Terminology | year = 1972 | publisher = University of Arizona Press | location = Tucson | url = https://books.google.com/books?id=CTwh-QaifQkC | isbn = 978-0-8165-0305-6 }}</ref>{{rp|241}} and 'steroid'. Secosteroids are described as a subclass of steroids under the [[IUPAC]] nomenclature.{{r|n1=IUPAC-IUB|loc1=&sect;3S-1|a1=#[[#L2|^]] (esp. 3S-1.4, incl. note 4) "Steroids are compounds possessing the skeleton of cyclopenta[a]phenanthrene or a skeleton derived therefrom by one or more bond scissions or ring expansions or contractions."|link-id=L2}}<ref name=HillDict>{{cite book |author1=Hill RA |author2=Makin HL |author3=Kirk DN |author4=Murphy GM | title = Dictionary of Steroids | date = 1991 | publisher = Chapman & Hall | location = London | isbn = 978-0-412-27060-4 | edition = 1st }}</ref> Some sources instead describe them as compounds derived from steroids.<ref name = "TheFreeDictionary">{{cite web | url = http://medical-dictionary.thefreedictionary.com/secosteroid | title = Definition of secosteroid | publisher = TheFreeDictionary.com | work = Farlex Partner Medical Dictionary | quote = A compound derived from a steroid in which there has been a ring cleavage. }}</ref>
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.<ref name=MossIUPAC_3S1>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 [http://www.chem.qmul.ac.uk/iupac/steroid/] and [http://www.chem.qmul.ac.uk/iupac/steroid/3S01.html], 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, [[Josef Fried|J. Fried]]<sup>†</sup>, H.W. Kircher, K.L. Loening, G.P. Moss, G. Popják and M.R. Uskokovic.</ref><ref>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.</ref><ref name="pmid20424788">{{cite journal | author = Hanson JR | title = Steroids: partial synthesis in medicinal chemistry | journal = Nat Prod Rep | volume = 27 | issue = 6 | pages = 887–99 | year = 2010 | month = June | pmid = 20424788 | doi = 10.1039/c001262a | url = http://pubs.rsc.org/en/content/articlelanding/2010/np/c001262a#!divAbstract }}</ref><ref>See also the drugs.com [http://www.drugs.com/dict/secosteroid.html], free (medical) dictionary [http://medical-dictionary.thefreedictionary.com/secosteroid], biology-online [http://www.biology-online.org/dictionary/Secosteroid], and medilexicon [http://www.medilexicon.com/medicaldictionary.php?t=80500] entries for this term, which their more brief renditions of the definition, in some cases indicate secosteroids as derivatives of steroids.</ref> The subclass nomenclature derives from the verb {{lang-lat|secare}} meaning "to cut", and {{lang-lat|stere}} of steroid, meaning "solid, three-dimensional".<ref>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.</ref> 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.).


Types or subclasses of secosteroids are defined by the carbon atoms of the parent steroid skeleton where the ring cleavage has taken place. For example, 9,10-secosteroids are derived from [[bond cleavage|cleavage of the bond]] between carbon atoms C9 and C10 of the steroid B-ring (similarly 5,6-secosteroids, 13,14-secosteroids, etc.).{{r|n1=IUPAC-IUB|loc1=&sect;3S-8|link-id=L1c}}
The prototypical secosteroid is [[cholecalciferol]], [[vitamin D|vitamin D3]].<ref>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.</ref>


The prototypical secosteroid is [[cholecalciferol]] (vitamin D<sub>3</sub>).<ref name="pmid20424788">{{cite journal | author = Hanson JR | title = Steroids: partial synthesis in medicinal chemistry | journal = Nat Prod Rep | volume = 27 | issue = 6 | pages = 887–99 | year = 2010 | pmid = 20424788 | doi = 10.1039/c001262a }}</ref> Its IUPAC systematic is "(5''Z'',7''E'')-(3''S'')-'''9,10-seco'''cholestra-5,7,10(19)-trien-3-ol".{{r|n1=IUPAC-IUB|loc1=&sect;3S-8|link-id=L1b}}
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== References ==

{{reflist}}
Some [[nonsteroidal estrogen]]s, like [[doisynolic acid]] (cleaved on the D ring)<ref>{{cite journal |last1=Meyers |first1=CY |last2=Kolb |first2=VM |last3=Gass |first3=GH |last4=Rao |first4=BR |last5=Roos |first5=CF |last6=Dandliker |first6=WB |title=Doisynolic-type acids--uterotropically potent estrogens which compete poorly with estradiol for cytosolic estradiol receptors. |journal=Journal of Steroid Biochemistry |date=October 1988 |volume=31 |issue=4A |pages=393–404 |doi=10.1016/0022-4731(88)90307-x |pmid=3172773}}</ref> and [[allenolic acid]],{{citation needed|date=June 2022}} are also secosteroids or secosteroid-like compounds.

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==References==
{{Reflist|refs=

}}


==External links==
==External links==
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[[Category:Secosteroids| ]]
[[Category:Secosteroids| ]]

{{steroid-stub}}

Latest revision as of 11:20, 28 February 2024

[1]

Cholecalciferol, an example of a 9,10-secosteroid. IUPAC-approved carbon numbering and ring labeling is shown in the picture. Since secosteroids are derived from steroids, they retain the same labeling system as steroids. [1]: §3S-8 
The parent steroid skeleton. The B-ring of the parent steroid is broken between C9 and C10 to yield D vitamins.

A secosteroid (/ˈsɛkoʊˌstɛrɔɪd/) is a type of steroid with a "broken" ring. The word secosteroid derives from the Latin verb secare meaning "to cut",[2]: 241  and 'steroid'. Secosteroids are described as a subclass of steroids under the IUPAC nomenclature.[1]: §3S-1 [3] Some sources instead describe them as compounds derived from steroids.[4]

Types or subclasses of secosteroids are defined by the carbon atoms of the parent steroid skeleton where the ring cleavage has taken place. For example, 9,10-secosteroids are derived from cleavage of the bond between carbon atoms C9 and C10 of the steroid B-ring (similarly 5,6-secosteroids, 13,14-secosteroids, etc.).[1]: §3S-8 

The prototypical secosteroid is cholecalciferol (vitamin D3).[5] Its IUPAC systematic is "(5Z,7E)-(3S)-9,10-secocholestra-5,7,10(19)-trien-3-ol".[1]: §3S-8 

Some nonsteroidal estrogens, like doisynolic acid (cleaved on the D ring)[6] and allenolic acid,[citation needed] are also secosteroids or secosteroid-like compounds.

References

[edit]
  1. ^ a b c d e Moss GP and the Working Party of the IUPAC-IUB Joint Commission on Biochemical Nomenclature. "The Nomenclature of Steroids". Queen Mary University of London. also available as Moss GP (1989). "Nomenclature of Steroids (Recommendations 1989)". Pure Appl. Chem. 61 (10): 1786f. doi:10.1351/pac198961101783.
    1. a b c Chapters 3S-8 "Ring fission" and 3S-9 "Vitamin D group"
    2. ^ (esp. 3S-1.4, incl. note 4) "Steroids are compounds possessing the skeleton of cyclopenta[a]phenanthrene or a skeleton derived therefrom by one or more bond scissions or ring expansions or contractions."
  2. ^ Ayers D (1972). Bioscientific Terminology. Tucson: University of Arizona Press. ISBN 978-0-8165-0305-6.
  3. ^ Hill RA; Makin HL; Kirk DN; Murphy GM (1991). Dictionary of Steroids (1st ed.). London: Chapman & Hall. ISBN 978-0-412-27060-4.
  4. ^ "Definition of secosteroid". Farlex Partner Medical Dictionary. TheFreeDictionary.com. A compound derived from a steroid in which there has been a ring cleavage.
  5. ^ Hanson JR (2010). "Steroids: partial synthesis in medicinal chemistry". Nat Prod Rep. 27 (6): 887–99. doi:10.1039/c001262a. PMID 20424788.
  6. ^ Meyers, CY; Kolb, VM; Gass, GH; Rao, BR; Roos, CF; Dandliker, WB (October 1988). "Doisynolic-type acids--uterotropically potent estrogens which compete poorly with estradiol for cytosolic estradiol receptors". Journal of Steroid Biochemistry. 31 (4A): 393–404. doi:10.1016/0022-4731(88)90307-x. PMID 3172773.
[edit]
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