Secosteroid

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File:Cholecalciferol-numbered.svg
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]Template:R/superscript
File:Trimethyl steroid-nomenclature.svg
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]Template:Rp and 'steroid'. Secosteroids are described as a subclass of steroids under the IUPAC nomenclature.[1]Template:R/superscript[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]Template:R/superscript

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]Template:R/superscript

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

References

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  1. ^ a b c d
    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. ^ Page Module:Citation/CS1/styles.css has no content.Ayers D (1972). Bioscientific Terminology. Tucson: University of Arizona Press. ISBN 978-0-8165-0305-6.
  3. ^ Page Module:Citation/CS1/styles.css has no content.Hill RA; Makin HL; Kirk DN; Murphy GM (1991). Dictionary of Steroids (1st ed.). London: Chapman & Hall. ISBN 978-0-412-27060-4.
  4. ^ Page Module:Citation/CS1/styles.css has no content."Definition of secosteroid". Farlex Partner Medical Dictionary. TheFreeDictionary.com. A compound derived from a steroid in which there has been a ring cleavage.
  5. ^ Page Module:Citation/CS1/styles.css has no content.Hanson JR (2010). "Steroids: partial synthesis in medicinal chemistry". Nat Prod Rep. 27 (6): 887–99. doi:10.1039/c001262a. PMID 20424788.
  6. ^ Page Module:Citation/CS1/styles.css has no content.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.

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