Secosteroid Explained

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

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.).

The prototypical secosteroid is cholecalciferol (vitamin D3).[4] Its IUPAC systematic is "(5Z,7E)-(3S)-9,10-secocholestra-5,7,10(19)-trien-3-ol".

Some nonsteroidal estrogens, like doisynolic acid (cleaved on the D ring)[5] and allenolic acid, are also secosteroids or secosteroid-like compounds.

Notes and References

  1. Book: Ayers D . Bioscientific Terminology . 1972 . University of Arizona Press . Tucson . 978-0-8165-0305-6 .
  2. Book: Hill RA . Makin HL . Kirk DN . Murphy GM . Dictionary of Steroids . 1991 . Chapman & Hall . London . 978-0-412-27060-4 . 1st .
  3. Web site: Definition of secosteroid . TheFreeDictionary.com . Farlex Partner Medical Dictionary . A compound derived from a steroid in which there has been a ring cleavage. .
  4. Hanson JR . Steroids: partial synthesis in medicinal chemistry . Nat Prod Rep . 27 . 6 . 887–99 . 2010 . 20424788 . 10.1039/c001262a .
  5. Meyers . CY . Kolb . VM . Gass . GH . Rao . BR . Roos . CF . Dandliker . WB . Doisynolic-type acids--uterotropically potent estrogens which compete poorly with estradiol for cytosolic estradiol receptors. . Journal of Steroid Biochemistry . October 1988 . 31 . 4A . 393–404 . 10.1016/0022-4731(88)90307-x . 3172773.