Difference between revisions of "Spirostan"
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| − | [[File:Spirostan.png|thumb|right]] | + | [[File:Spirostan.png|thumb|right|The spirostan fundamental parent structure.]] |
| − | '''Spirostan''' is a defined [[parent | + | [[File:Spirostan side-chain alt.png|thumb|right|An alternative depiction of the spirostan side chain, emphasizing the fact that rings E and F are perpendicular to one another. Carbon-25 is shown with an (''R'')-configuration in this diagram.]] |
| + | '''Spirostan''' is a defined [[fundamental parent structure]] in the [[nomenclature of steroids]].<ref>{{IUPAC natural products 1999}}.</ref><ref>{{IUPAC-IUB steroids 1989}}.</ref> 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 are not defined, and so must be specified for each derivative. | ||
| + | |||
| + | ==Occurrence== | ||
| + | Spirostan steroids are common as the [[Glycoside|aglycosidic]] portions of plant [[saponin]]s, and include: | ||
| + | |||
{| class="wikitable" | {| class="wikitable" | ||
|- | |- | ||
| Line 11: | Line 16: | ||
| align=center | β | | align=center | β | ||
| align=center | ''S'' | | align=center | ''S'' | ||
| + | | align=center | 3β-OH | ||
|- | |- | ||
| [[smilagenin]] | | [[smilagenin]] | ||
| align=center | β | | align=center | β | ||
| align=center | ''R'' | | align=center | ''R'' | ||
| + | | align=center | 3β-OH | ||
|- | |- | ||
| [[tigogenin]] | | [[tigogenin]] | ||
| align=center | α | | align=center | α | ||
| align=center | ''R'' | | align=center | ''R'' | ||
| + | | align=center | 3β-OH | ||
|- | |- | ||
| [[diosgenin]] | | [[diosgenin]] | ||
| align=center | Δ<sup>5</sup> | | align=center | Δ<sup>5</sup> | ||
| align=center | ''R'' | | align=center | ''R'' | ||
| + | | align=center | 3β-OH | ||
|- | |- | ||
| [[anzurogenin-D]] | | [[anzurogenin-D]] | ||
| − | | α | + | | align=center | α |
| − | | ''R'' | + | | align=center | ''R'' |
| − | | 3β-OH, 5α-OH, 6β-OH | + | | align=center | 3β-OH, 5α-OH, 6β-OH |
|- | |- | ||
| [[sisalgenin]] | | [[sisalgenin]] | ||
| − | | α | + | | align=center | α |
| − | | ''S'' | + | | align=center | ''S'' |
| − | | C=O at C-12 | + | | align=center | 3β-OH, C=O at C-12 |
|- | |- | ||
| [[roscogenin]] | | [[roscogenin]] | ||
| − | | Δ<sup>5</sup> | + | | align=center | Δ<sup>5</sup> |
| − | | ''S'' | + | | align=center | ''S'' |
| − | | | + | | align=center | 1β-OH, 3β-OH |
|- | |- | ||
|} | |} | ||
| Line 46: | Line 55: | ||
[[Category:Spirostan steroids|*]] | [[Category:Spirostan steroids|*]] | ||
[[Category:Nomenclature of steroids]] | [[Category:Nomenclature of steroids]] | ||
| + | |||
| + | {{CC-BY-3.0}} | ||
Latest revision as of 06:15, 11 March 2010
Spirostan is a defined fundamental parent structure in the nomenclature of steroids.[1][2] 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 are not defined, and so must be specified for each derivative.
Occurrence
Spirostan steroids are common as the aglycosidic portions of plant saponins, and include:
| C-5 | C-25 | Other | |
|---|---|---|---|
| sarsasapogenin | β | S | 3β-OH |
| smilagenin | β | R | 3β-OH |
| tigogenin | α | R | 3β-OH |
| diosgenin | Δ5 | R | 3β-OH |
| anzurogenin-D | α | R | 3β-OH, 5α-OH, 6β-OH |
| sisalgenin | α | S | 3β-OH, C=O at C-12 |
| roscogenin | Δ5 | S | 1β-OH, 3β-OH |
References
- ↑ Revised Section F: Natural Products and Related Compounds (IUPAC Recommendations 1999). Pure Appl. Chem., 71 (4), 587–643. DOI: 10.1351/pac199971040587.
- ↑ Nomenclature of Steroids (IUPAC–IUB Recommendations 1989). Pure Appl. Chem., 61 (10), 1783–1822. DOI: 10.1351/pac198961101783.
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