Secosteroid: Difference between revisions
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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 alternatively described as a subclass of steroids<ref name = "IUPAC-IUB">{{cite web | url = http://www.chem.qmul.ac.uk/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 | page = Section 3S-1 (esp. 3S-1.4, incl. note 4) }}; {{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 | url = http://www.chem.qmul.ac.uk/iupac/steroid/ | quote = 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. | doi-access = free }}; {{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> or 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> |
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 alternatively described as a subclass of steroids<ref name = "IUPAC-IUB">{{cite web | url = http://www.chem.qmul.ac.uk/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 | page = Section 3S-1 (esp. 3S-1.4, incl. note 4) }}; {{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 | url = http://www.chem.qmul.ac.uk/iupac/steroid/ | quote = 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. | doi-access = free }}; {{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> or 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> |
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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 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-steroids, etc.).{{cn}} |
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 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-steroids, etc.).{{cn|date=June 2022}} |
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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> |
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> |
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Some [[nonsteroidal estrogen]]s, like [[doisynolic acid]] and [[allenolic acid]], are also secosteroids or secosteroid-like compounds.{{cn}} |
Some [[nonsteroidal estrogen]]s, like [[doisynolic acid]] and [[allenolic acid]], are also secosteroids or secosteroid-like compounds.{{cn|date=June 2022}} |
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==References== |
==References== |
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Revision as of 13:01, 15 June 2022
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 alternatively described as a subclass of steroids[3] or 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 derived from cleavage of the bond between carbon atoms C9 and C10 of the steroid B-ring (similarly 5,6-secosteroids, 13,14-steroids, etc.).[citation needed]
The prototypical secosteroid is cholecalciferol (vitamin D3).[5]
Some nonsteroidal estrogens, like doisynolic acid and allenolic acid, are also secosteroids or secosteroid-like compounds.[citation needed]
References
- ^ "3S-8 and 3S9". qmul.ac.uk.
- ^ Ayers D (1972). Bioscientific Terminology. Tucson: University of Arizona Press. ISBN 978-0-8165-0305-6.
- ^ Moss GP and the Working Party of the IUPAC-IUB Joint Commission on Biochemical Nomenclature. "The Nomenclature of Steroids". Queen Mary University of London. p. Section 3S-1 (esp. 3S-1.4, incl. note 4).; Moss GP (1989). "Nomenclature of Steroids (Recommendations 1989)". Pure Appl. Chem. 61 (10): 1786f. doi:10.1351/pac198961101783.
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.
; Hill RA; Makin HL; Kirk DN; Murphy GM (1991). Dictionary of Steroids (1st ed.). London: Chapman & Hall. ISBN 978-0-412-27060-4. - ^ "Definition of secosteroid". Farlex Partner Medical Dictionary. TheFreeDictionary.com.
A compound derived from a steroid in which there has been a ring cleavage.
- ^ Hanson JR (2010). "Steroids: partial synthesis in medicinal chemistry". Nat Prod Rep. 27 (6): 887–99. doi:10.1039/c001262a. PMID 20424788.
External links
- Secosteroids at the U.S. National Library of Medicine Medical Subject Headings (MeSH)