Atractylenolide III

Names

[ Name ]:
Atractylenolide III

[Synonym ]:
Atractylenolide III
Naphtho(2,3-b)furan-2(4H)-one, 4a,5,6,7,8,8a,9,9a-octahydro-9a-hydroxy-3,8a-dimethyl-5-methylene-, (4aS,8aR,9aS)-
codonolactone
ATRACTYLENOLIDE
8-HYDROXYASTEROLIDE
(4aS,8aR,9aS)-9a-Hydroxy-3,8a-dimethyl-5-methylene-4a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(4H)-one
Naphtho[2,3-b]furan-2(4H)-one, 4a,5,6,7,8,8a,9,9a-octahydro-9a-hydroxy-3,8a-dimethyl-5-methylene-, (4aS,8aR,9aS)-

Biological Activity

[Description]:

Atractylenolide III is a major component of Atractylodes rhizome can induce apoptosis of the lung carcinoma cells.IC50 value:Target: Anticancer natural compoundin vitro: ATL-III inhibited cell growth, increased lactate dehydrogenase release and modulated cell cycle on human lung carcinoma A549 cells. ALT-III induced the activation of caspase-3 and caspase-9 and cleavage of poly-(ADP)-ribose polymerase. ATL-III induced the release of cytochrome c, upregulation of bax expression, and translocation of apoptosis-inducing factor [1]. Atractylenolide II did not show cytoprotective effects, but oral administration of atractylenolide III dose-dependently prevented ethanol-induced PRGM cell death and cell membrane damage. The EC50 values were 0.27 and 0.34 mm, respectively [2]. Against adult D. pteronyssinus, atractylenolide III (LD50, 73.8 mg/m2) and atractylon (72.1 mg/m2) were eight times more active than Deet and 2.5-fold more toxic than dibutyl phthalate [3].in vivo: In the in-vivo assay, atractylenolide III 10 mg/kg significantly reduced 70% ethanol-induced Wistar rat gastric ulcer. Atractylenolide III could inhibit matrix metalloproteinase (MMP)-2 and MMP-9 expression through upregulation of tissue inhibitors of metalloproteinase from the gastric ulcerated tissues [2].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Cancer

Natural Products >> Terpenoids and Glycosides

[References]

[1]. Kang TH, et al. Atractylenolide III, a sesquiterpenoid, induces apoptosis in human lung carcinoma A549 cells via mitochondria-mediated death pathway. Food Chem Toxicol. 2011 Feb;49(2):514-9.

[2]. Wang KT, et al. Gastroprotective activity of atractylenolide III from Atractylodes ovata on ethanol-induced gastric ulcer in vitro and in vivo. J Pharm Pharmacol. 2010 Mar;62(3):381-8.

[3]. Kim HK, et al. Toxicity of atractylon and atractylenolide III Identified in Atractylodes ovata rhizome to Dermatophagoides farinae and Dermatophagoides pteronyssinus. J Agric Food Chem. 2007 Jul 25;55(15):6027-31.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
424.6±45.0 °C at 760 mmHg

[ Melting Point ]:
200-201ºC

[ Molecular Formula ]:
C₁₅H₂₀O₃

[ Molecular Weight ]:
248.318

[ Flash Point ]:
181.1±21.5 °C

[ Exact Mass ]:
248.141251

[ PSA ]:
46.53000

[ LogP ]:
2.36

[ Appearance of Characters ]:
white to off-white

[ Vapour Pressure ]:
0.0±2.3 mmHg at 25°C

[ Index of Refraction ]:
1.558

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
methanol: soluble1mg/mL, clear, colorless

MSDS

Click to get detail MSDS

Safety Information

[ RIDADR ]:
NONH for all modes of transport

Articles

Sesquiterpenoids from Atractylodes macrocephala act as farnesoid X receptor and progesterone receptor modulators.

Bioorg. Med. Chem. Lett. 22 , 2326-2329, (2012)

Two sesquiterpenoids, atractylenolide II and III, were isolated and identified from Atractylodes macrocephala (Asteraceae) to be subsequently evaluated for their activity against farnesoid X receptor ...

Targeting of the Sonic Hedgehog pathway by atractylenolides promotes chondrogenic differentiation of mesenchymal stem cells.

Biol. Pharm. Bull. 35 , 1328-1335, (2012)

Molecules that enhance chondrogenic differentiation in mesenchymal stem cells (MSCs) were identified and isolated using an in vitro Gli reporter gene assay in MSCs incorporating a Sonic Hedgehog (Shh)...

Pharmacokinetic Profiles of Active Ingredients and Its Metabolites Derived from Rikkunshito, a Ghrelin Enhancer, in Healthy Japanese Volunteers: A Cross-Over, Randomized Study.

PLoS ONE 10 , e0133159, (2015)

Rikkunshito, a traditional Japanese (Kampo) medicine, has been used to treat upper gastrointestinal disorders such as functional dyspepsia and gastroesophageal reflux. This study investigated the expo...