A sesquiterpene with diverse biological activities
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Isomer(s)
25402Micheliolide
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Atractylenolide III

Item No. 24911

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(4aS,8aR,9aS)-4a,5,6,7,8,8a,9,9a-octahydro-9a-hydroxy-3,8a-dimethyl-5-methylene-naphtho[2,3-b]furan-2(4H)-one
CAS Number
73030-71-4
Synonyms
  • Atractylenolide β
  • Codonolactone
Molecular Formula
C15H20O3
Formula Weight
248.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 2 mg/mlDMSO: 2 mg/mlDMSO:PBS (pH 7.2) (1:10): 0.09 mg/mlEthanol: 1 mg/ml
λmax
219 nm
SMILES
O=C(O1)C(C)=C2[C@]1(O)C[C@](CCCC3=C)(C)[C@@]3([H])C2
InChi Code
InChI=1S/C15H20O3/c1-9-5-4-6-14(3)8-15(17)12(7-11(9)14)10(2)13(16)18-15/h11,17H,1,4-8H2,2-3H3/t11-,14+,15-/m0/s1
InChi Key
FBMORZZOJSDNRQ-GLQYFDAESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

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    50 mg

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    Product Description

    Atractylenolide III is a sesquiterpene that has been isolated from Atractylodes and has diverse biological activities, including anti-inflammatory, anti-angiogenic, pro- and anti-apoptotic, and neuroprotective properties.1,2,3,4,5 It inhibits the release of nitric oxide (NO), prostaglandin E2 (PGE2; Item No. 14010), TNF-α, and IL-6 induced by LPS from RAW264.7 macrophages when used at a concentration of 50 µM.1 Atractylenolide III (100 µM) induces apoptosis and cell cycle arrest, as well as increases caspase-3, caspase-9, and poly(ADP-ribose) polymerase (PARP) cleavage in A549 human lung carcinoma cells.3 However, in primary embryonic mouse cerebral cortical neurons, it inhibits glutamate-induced apoptosis and DNA fragmentation when used at a concentration of 40 µM.4 It inhibits angiogenesis in an MDA-MB-231 human breast cancer mouse xenograft model when administered at a dose of 25 mg/kg per day.2 Atractylenolide III (0.6 mg/kg per day) also decreases the latency to find the platform in the Morris water maze in a rat model of learning deficits induced by high-dose homocysteine.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ji, G.-Q., Chen, R.-Q., and Wang, L. Anti-inflammatory activity of atractylenolide III through inhibition of nuclear factor-κB and mitogen-activated protein kinase pathways in mouse macrophages. Immunopharmacol. Immunotoxicol. 38(2), 98-102 (2016).

    2. Wang, S., Cai, R., Ma, J., et al. The natural compound codonolactone impairs tumor induced angiogenesis by downregulating BMP signaling in endothelial cells. Phytomedicine 22(11), 1017-1026 (2015).

    3. Kang, T.-H., Bang, J.-Y., Kim, M.-H., et al. Atractylenolide III, a sesquiterpenoid, induces apoptosis in human lung carcinoma A549 cells via mitochondria-mediated death pathway. Food Chem. Toxicol. 49(2), 514-519 (2011).

    4. Liu, C., Zhao, H., Ji, Z.-H., et al. Neuroprotection of atractylenolide III from Atractylodis macrocephalae against glutamate-induced neuronal apoptosis via inhibiting caspase signaling pathway. Neurochem. Res. 39(9), 1753-1758 (2014).

    5. Zhao, H., Ji, Z.-H., Liu, C., et al. Neuroprotection and mechanisms of atractylenolide III in preventing learning and memory impairment induced by chronic high-dose homocysteine administration in rats. Neuroscience 290, 485-491 (2015).