Alisol B Chemical Properties

Melting point:

166-168 °C

Boiling point:

575.1±50.0 °C(Predicted)

Density 

1.12±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Soluble in chloroform, DMSO and methanol;

form 

powder

pka

14.35±0.20(Predicted)

color 

White

Water Solubility 

insoluble in water

InChIKey

GBJKHDVRXAVITG-GMGBHDGLNA-N

SMILES

C[C@]12CC[C@@]3([H])C(C(=O)CC[C@]3(C)[C@]1([H])[C@H](CC1=C([C@H](C)C[C@@H]([C@@]3([H])OC3(C)C)O)CC[C@]21C)O)(C)C |&1:1,4,11,13,15,19,22,23,32,r|

Safety Information

HS Code 

29329990

Alisol B Usage And Synthesis

Chemical Properties

White crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from the rhizome of Alisma orientalis.

Uses

Alisol B is a potentially novel therapeutic compound for bone disorders by targeting the differentiation of osteoclasts as well as their functions. IC50 Value: Target: In vitro: The in vitro cultured human renal tubular epithelial HK-2 cells were intervened with 5 ng/mL transforming growth factor-beta (TGF-beta), 0.1 micromol C3a, and 0.1 micromol C3a + 10 micromol alisol B, respectively. Exogenous C3a could induce renal tubular EMT. Alisol B was capable of suppressing C3a induced EMT [1]. Alisol-B strongly inhibited RANKL-induced osteoclast formation when added during the early stage of cultures, suggesting that alisol-B acts on osteoclast precursors to inhibit RANKL/RANK signaling. Among the RANK signaling pathways, alisol-B inhibited the phosphorylation of JNK, which are upregulated in response to RANKL in bone marrow macrophages, alisol-B also inhibited RANKL-induced expression of NFATc1 and c-Fos, which are key transcription factors for osteoclastogenesis. In addition, alisol-B suppressed the pit-forming activity and disrupted the actin ring formation of mature osteoclasts [2]. Alisol B induced calcium mobilization from internal stores, leading to autophagy through the activation of the CaMKK-AMPK-mammalian target of rapamycin pathway. Moreover, the disruption of calcium homeostasis induces endoplasmic reticulum stress and unfolded protein responses in alisol B-treated cells, leading to apoptotic cell death. Finally, by computational virtual docking analysis and biochemical assays, it was showed that the molecular target of alisol B is the sarcoplasmic/endoplasmic reticulum Ca(2+) ATPase [3]. In vivo:

Definition

ChEBI: Alisol B is a triterpenoid.

target

TGF-β/Smad | JNK | AMPK | Calcium Channel | ATPase

References

[1] Zhang RF, et al.[Alisol B inhibited complement 3a-induced human renal tubular epithelial to mesenchymal transition]. Zhongguo Zhong Xi Yi Jie He Za Zhi. 2012 Oct;32(10):1407-12. PMID:23163157
[2] Lee JW, et al. Alisol-B, a novel phyto-steroid, suppresses the RANKL-induced osteoclast formation and prevents bone loss in mice. Biochem Pharmacol. 2010 Aug 1;80(3):352-61. DOI:10.1016/j.bcp.2010.04.014
[3] Law BY, et al. Alisol B, a novel inhibitor of the sarcoplasmic/endoplasmic reticulum Ca(2+) ATPase pump, induces autophagy, endoplasmic reticulum stress, and apoptosis. Mol Cancer Ther. 2010 Mar;9(3):718-30. DOI:10.1158/1535-7163.MCT-09-0700

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