CAS 73030-71-4|Atractylenolide III

Introduction：Basic information about CAS 73030-71-4|Atractylenolide III, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Atractylenolide III BiologicalActivity
3. Chemical & Physical Properties
4. Safety Information
5. Articles4
6. Synonyms

Common Name	Atractylenolide III
CAS Number	73030-71-4	Molecular Weight	248.318
Density	1.2±0.1 g/cm3	Boiling Point	424.6±45.0 °C at 760 mmHg
Molecular Formula	C₁₅H₂₀O₃	Melting Point	200-201ºC
MSDS	USA	Flash Point	181.1±21.5 °C

Names

Name	Atractylenolide III
Synonym	More Synonyms

Atractylenolide III BiologicalActivity

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 >>OthersResearch Areas >>CancerNatural 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.

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 >>OthersResearch Areas >>CancerNatural 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.

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
InChIKey	FBMORZZOJSDNRQ-GLQYFDAESA-N
SMILES	C=C1CCCC2(C)CC3(O)OC(=O)C(C)=C3CC12
Storage condition	2-8°C
Water Solubility	methanol: soluble1mg/mL, clear, colorless

Safety Information

RIDADR	NONH for all modes of transport

Articles4

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...

Synonyms

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)-

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