Difference between revisions of "Spirostan"

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! C-5
 
! C-5
 
! C-25
 
! C-25
 +
! Other
 
|-
 
|-
 
| [[sarsasapogenin]]
 
| [[sarsasapogenin]]
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| align=center | ''R''
 
| align=center | ''R''
 
|-
 
|-
| [[disogenin]]
+
| [[diosgenin]]
 
| align=center | Δ<sup>5</sup>
 
| align=center | Δ<sup>5</sup>
 
| align=center | ''R''
 
| align=center | ''R''
 +
|-
 +
| [[anzurogenin-D]]
 +
| α
 +
| ''R''
 +
| 3β-OH, 5α-OH, 6β-OH
 +
|-
 +
| [[sisalgenin]]
 +
| α
 +
| ''S''
 +
| C=O at C-12
 +
|-
 +
| [[roscogenin]]
 +
| Δ<sup>5</sup>
 +
| ''S''
 +
|
 
|-
 
|-
 
|}
 
|}

Revision as of 16:24, 8 March 2010

Spirostan.png

Spirostan is a defined parent hydride in the nomenclature of steroids.[1] It is characterised by a bicyclic side chain containing a ketone spiro acetal group. In the spirostan structure, the configurations of carbons 5 and 25 is not defined, and so must be specified for each derivative. Spirostan steroids include:

  C-5 C-25 Other
sarsasapogenin β S
smilagenin β R
tigogenin α R
diosgenin Δ5 R
anzurogenin-D α R 3β-OH, 5α-OH, 6β-OH
sisalgenin α S C=O at C-12
roscogenin Δ5 S

References

  1. Revised Section F: Natural Products and Related Compounds (IUPAC Recommendations 1999). Pure Appl. Chem., 71 (4), 587–643. DOI: 10.1351/pac199971040587.