Structure Database (LMSD)

Common Name
Sarsasapogenenin
Systematic Name
(25S)-5β-spirostan-3β-ol
Synonyms
  • Parigenin
  • Sarsasapogenin
LM ID
LMST01080007
Formula
Exact Mass
Calculate m/z
416.329045
Sum Composition
Status
Curated



Classification

Biological Context

Sarsasapogenin is a steroid sapogenin originally isolated from Smilax that has antiproliferative, pro-apoptotic, anti-inflammatory, neuroprotective, and antidepressant-like properties.1,2,3,4,5,6 Sarsasapogenin inhibits proliferation of HeLa cervical, MCF-7 breast, HepG2 liver, A549 lung, A375.S2 melanoma, and HT-1080 fibrosarcoma cells (IC50s = 31.36-48.79 μM) and dose-dependently induces apoptosis of HeLa cells.2,3 It also protects human SH-SY5Y neuroblastoma cells from hydrogen peroxide-induced death with a neuroprotective ratio of 27.3% when used at a concentration of 100 μM.5 In vivo, sarsasapogenin (10 mg/kg) reduces 2,3,4-trinitrobenzene sulfonic acid-induced colon shortening, myeloperoxidase activity, NF-κB activation, and IL-1β, TNF-α, and IL-6 levels in mice.4 It also increases the percentage of correct responses in the Y-maze test in aged rats when administered at a dose of 3.6 mg/kg per day.7 Sarsasapogenin (12.5 mg/kg per day) reduces the amount of time mice spend immobile in the forced swim test, indicating antidepressant-like behavior.6

This information has been provided by Cayman Chemical

References

2. Power, F.B., and Salway, A.H. XXV-Chemical examination of sarsaparilla root. J. Chem. Soc. 105, 201-219 (1914).
6. Ren, L.-X., Luo, Y.-F., Li, X., et al. Antidepressant-like effects of sarsasapogenin from Anemarrhena asphodeloides BUNGE (Liliaceae). Biol. Pharm. Bull. 29(11), 2304-2306 (2006).
7. Hu, Y., Xia, Z., Sun, Q., et al. A new approach to the pharmacological regulation of memory: Sarsasapogenin improves memory by elevating the low muscarinic acetylcholine receptor density in brains of memory-deficit rat models. Brain Res. 1060(1-2), 26-39 (2005).

String Representations

InChiKey (Click to copy)
GMBQZIIUCVWOCD-WWASVFFGSA-N
InChi (Click to copy)
InChI=1S/C27H44O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-24,28H,5-15H2,1-4H3/t16-,17-,18+,19-,20+,21-,22-,23-,24-,25-,26-,27+/m0/s1
SMILES (Click to copy)
C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@H]5[C@@H]([C@]6(O[C@H]5C[C@@]4([H])[C@]3([H])CC[C@]2([H])C[C@@H](O)C1)CC[C@H](C)CO6)C

Other Databases

KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 30
Rings 6
Aromatic Rings 0
Rotatable Bonds 0
Van der Waals Molecular Volume 427.87
Topological Polar Surface Area 42.83
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 3
logP 6.94
Molar Refractivity 119.75

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Updated at
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