A secosteroid (/หsษkoสหstษrษษชd/) is a type of steroid with a "broken" ring. The word secosteroid derives from the Latin verb secare meaning "to cut",[2]:โ241โ and 'steroid'. Secosteroids are described as a subclass of steroids under the IUPAC nomenclature.[1]:โยง3S-1โ[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]:โยง3S-8โ
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]:โยง3S-8โ
Some nonsteroidal estrogens, like doisynolic acid (cleaved on the D ring)[6] and allenolic acid,[citation needed] are also secosteroids or secosteroid-like compounds.
See also
editReferences
edit- ^ 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 asMoss GP (1989). "Nomenclature of Steroids (Recommendations 1989)". Pure Appl. Chem. 61 (10): 1786f. doi:10.1351/pac198961101783.
- a b c Chapters 3S-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. ISBNย 978-0-8165-0305-6.
- ^ Hill RA; Makin HL; Kirk DN; Murphy GM (1991). Dictionary of Steroids (1stย ed.). London: Chapman & Hall. ISBNย 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): 887โ99. doi:10.1039/c001262a. PMIDย 20424788.
- ^ 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): 393โ404. doi:10.1016/0022-4731(88)90307-x. PMIDย 3172773.
External links
edit- Secosteroids at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
