Secosteroid
Asecosteroid(/ˈsɛkoʊˌstɛrɔɪd/) is a type ofsteroidwith a "broken" ring. The wordsecosteroidderives from the Latin verbsecaremeaning "to cut",[2]: 241 and 'steroid'. Secosteroids are described as a subclass of steroids under theIUPACnomenclature.[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 fromcleavage of the bondbetween carbon atoms C9 and C10 of the steroid B-ring (similarly 5,6-secosteroids, 13,14-secosteroids, etc.).[1]: §3S-8
The prototypical secosteroid ischolecalciferol(vitamin D3).[5]Its IUPAC systematic is "(5Z,7E)-(3S)-9,10-secocholestra-5,7,10(19)-trien-3-ol ".[1]: §3S-8
Somenonsteroidal estrogens,likedoisynolic acid(cleaved on the D ring)[6]andallenolic acid,[citation needed]are also secosteroids or secosteroid-like compounds.
References[edit]
- ^abcdeMoss 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 asMoss GP (1989)."Nomenclature of Steroids (Recommendations 1989)".Pure Appl. Chem.61(10): 1786f.doi:10.1351/pac198961101783.
- abcChapters3S-8 "Ring fission" and 3S-9 "Vitamin D group"
- ^(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."
- ^Ayers D (1972).Bioscientific Terminology.Tucson: University of Arizona Press.ISBN978-0-8165-0305-6.
- ^Hill RA; Makin HL; Kirk DN; Murphy GM (1991).Dictionary of Steroids(1st ed.). London: Chapman & Hall.ISBN978-0-412-27060-4.
- ^"Definition of secosteroid".Farlex Partner Medical Dictionary.TheFreeDictionary.
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.PMID20424788.
- ^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.PMID3172773.
External links[edit]
- Secosteroidsat the U.S. National Library of MedicineMedical Subject Headings(MeSH)