Atractylenolide-1 Chemical Properties

Melting point:

121-123 °C(Solv: ligroine (8032-32-4))

Boiling point:

405.0±44.0 °C(Predicted)

Density 

1.12

Flash point:

170℃

storage temp. 

2-8°C

solubility 

methanol: soluble1mg/mL, clear, colorless

form 

powder

color 

White

InChI

InChI=1S/C15H18O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h8,12H,1,4-7H2,2-3H3/t12-,15+/m0/s1

InChIKey

ZTVSGQPHMUYCRS-SWLSCSKDSA-N

SMILES

O1C(=O)C(C)=C2C[C@]3([H])[C@@](C)(C=C12)CCCC3=C

Safety Information

WGK Germany 

3

Atractylenolide-1 Usage And Synthesis

Description

Atractylenolide I is a sesquiterpene that has been found in the rhizomes of A. macrocephala and has diverse biological activities, including anti-inflammatory, anti-angiogenic, anti-tumor, and antidepressant properties. It inhibits LPS-induced increases in TNF-α and nitric oxide (NO) production, as well as inducible nitric oxide synthase (iNOS) activity, in murine peritoneal macrophages (IC₅₀s = 23.1, 41, and 67.3 μM, respectively). Atractylenolide I reduces pouch fluid weight, inflammatory cell count, granuloma weight, and vascular index (ID₅₀s = 24.18, 19.46, 14.44, and 15.15 mg/kg, respectively) in a mouse air pouch granuloma model induced by Freund''s complete adjuvant (FCA). It also reduces the number of microvessels in the air pouch wall by 58.27% when administered at a dose of 20 mg/kg and reduces the blood levels of TNF-α, IL-1β, IL-6, VEGF, placenta growth factor (PlGF), and bFGF in a dose-dependent manner in a mouse model of FCA-induced granuloma. Atractylenolide I inhibits the growth of T-24, 5637, RT4, and 253J bladder cancer cells in vitro (IC₅₀s = 12.8-63.7 μM) and reduces tumor growth in T-24 and 253J mouse xenograft models in a dose-dependent manner. In a mouse model of depression induced by chronic unpredictable mild stress, atractylenolide I reverses stress-induced decreases in hippocampal levels of serotonin (5-HT; ) and norepinephrine and reduces immobility time in the forced swim and tail suspension tests in a dose-dependent manner, indicating antidepressant-like activity.

Chemical Properties

Off-white crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from Atractylodes macrocephala Koidz.

Uses

Atractylenolide I (Standard) is the analytical standard of Atractylenolide I. This product is intended for research and analytical applications. Atractylenolide I is a sesquiterpene derived from the rhizome of Atractylodes macrocephala, possesses diverse bioactivities, such as neuroprotective, anti-allergic, anti-inflammatory and anticancer properties. Atractylenolide I reduces protein levels of phosphorylated JAK2 and STAT3 in A375 cells, and acts as a TLR4-antagonizing agent.

References

[1] CUI-QIN LI  Ju Q J  Lang Chong He. Atractylenolide I and atractylenolide III inhibit Lipopolysaccharide-induced TNF-alpha and NO production in macrophages.[J]. Phytotherapy Research, 2007, 21 4: 347-353. DOI: 10.1002/ptr.2040
[2] CHANGHE WANG  Langchong H  Haijie Duan. Inhibitory effect of atractylenolide I on angiogenesis in chronic inflammation in vivo and in vitro[J]. European journal of pharmacology, 2009, 612 1: Pages 143-152. DOI: 10.1016/j.ejphar.2009.04.001
[3] RUI YU. Anti-tumor effects of Atractylenolide I on bladder cancer cells[J]. Journal of Experimental & Clinical Cancer Research, 2016, 110 1. DOI: 10.1186/s13046-016-0312-4
[4] HAIYAN GAO. Anti-depressant-like effect of atractylenolide I in a mouse model of depression induced by chronic unpredictable mild stress.[J]. Experimental and therapeutic medicine, 2018: 1574-1579. DOI: 10.3892/etm.2017.5517

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