Structure via PubChem · Public domain (PubChem)
sarsagenin
Sign in to saveAlso known as Parigenin, (3beta,5beta,25S)-spirostan-3-ol
Sarsasapogenin is a steroidal spirostanol sapogenin, that is the aglycosidic portion of a plant saponin. It is named after sarsaparilla (Smilax sp.), a family of climbing plants found in subtropical regions. It was one of the first sapogenins to be identified, and the first spirostan steroid to be identified as such. The identification of the spirostan structure, with its ketone spiro acetal functionality, was fundamental in the development of the Marker degradation, which allowed the industrial production of progesterone and other sex hormones from plant steroids.
Chemical data
- Formula
- C27H44O3
- Molecular weight
- 416.6 g/mol
- IUPAC name
- (1R,2S,4S,5'S,6R,7S,8R,9S,12S,13S,16S,18R)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-ol
- SMILES
- C[C@H]1CC[C@@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC[C@H]6[C@@]5(CC[C@@H](C6)O)C)C)C)OC1
- InChIKey
- GMBQZIIUCVWOCD-WWASVFFGSA-N
- XLogP
- 6.5
- Polar surface area
- 38.7 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 416.329045
Show 4 more facts
- chemical formula
- C₂₇H₄₄O₃
- isomeric SMILES
- C[C@H]1CC[C@@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC[C@H]6[C@@]5(CC[C@@H](C6)O)C)C)C)OC1
- canonical SMILES
- CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CCC6C5(CCC(C6)O)C)C)C)OC1
- found in taxon
- Yucca gloriosa
via Wikidata · CC0
~4 min read
Encyclopedic overview
4 sectionsContents
- Occurrence and isolation
- History
- Pharmacological interest
- References
Sarsasapogenin is a steroidal spirostanol sapogenin, that is the aglycosidic portion of a plant saponin. It is named after sarsaparilla (Smilax sp.), a family of climbing plants found in subtropical regions. It was one of the first sapogenins to be identified, and the first spirostan steroid to be identified as such. The identification of the spirostan structure, with its ketone spiro acetal functionality, was fundamental in the development of the Marker degradation, which allowed the industrial production of progesterone and other sex hormones from plant steroids.
Sarsasapogenin is unusual in that it has a cis-linkage between rings A and B of the steroid nucleus, as opposed to the more usual trans-linkage found in other saturated steroids. This 5β configuration is biologically significant, as a specific enzyme – sarsasapogenin 3β-glucosyltransferase – is found in several plants for the glycosylation of sarsasapogenin. The (S)-configuration at C-25 is also in contrast to other spirostan sapogenins: the epimer with a (25R)-configuration is known as smilagenin.
Excerpted from Wikipedia’s “sarsagenin” article, available under the CC BY-SA 4.0 licence.