BiatractylolideCAS# 182426-37-5 |
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| Cas No. | 182426-37-5 | SDF | Download SDF |
| PubChem ID | 10813930 | Appearance | Powder |
| Formula | C30H38O4 | M.Wt | 462.6 |
| Type of Compound | Sesquiterpenoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (4aR,8aS,9aR)-9a-[(4aS,8aR,9aS)-3,8a-dimethyl-5-methylidene-2-oxo-4,4a,6,7,8,9-hexahydrobenzo[f][1]benzofuran-9a-yl]-3,8a-dimethyl-5-methylidene-4,4a,6,7,8,9-hexahydrobenzo[f][1]benzofuran-2-one | ||
| SMILES | CC1=C2CC3C(=C)CCCC3(CC2(OC1=O)C45CC6(CCCC(=C)C6CC4=C(C(=O)O5)C)C)C | ||
| Standard InChIKey | RBJDJJGMGHKQMI-IBROYFQSSA-N | ||
| Standard InChI | InChI=1S/C30H38O4/c1-17-9-7-11-27(5)15-29(23(13-21(17)27)19(3)25(31)33-29)30-16-28(6)12-8-10-18(2)22(28)14-24(30)20(4)26(32)34-30/h21-22H,1-2,7-16H2,3-6H3/t21-,22+,27+,28-,29-,30+ | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Biatractylolide has a neuroprotective effect on glutamate-induced injury in PC12 and SH-SY5Y cells through a mechanism of the PI3K-Akt-GSK3β-dependent pathways. The molecular mechanisms of inhibitory activities of biatractylolide on AChE are not only through binding to AChE, but also via reducing AChE expression by inhibiting the activity of GSK3β. |
| Targets | PI3K | Akt | GSK3β | AChR |
| In vitro | Biatractylolide Modulates PI3K-Akt-GSK3β-Dependent Pathways to Protect against Glutamate-Induced Cell Damage in PC12 and SH-SY5Y Cells.[Pubmed: 29075302]Evid Based Complement Alternat Med. 2017;2017:1291458.Biatractylolide, isolated from the ethyl acetate extract of Atractylodes macrocephala, has shown various pharmacological activities such as antitumor and antioxidant activities. |
| Kinase Assay | Primary Investigation for the Mechanism of Biatractylolide from Atractylodis Macrocephalae Rhizoma as an Acetylcholinesterase Inhibitor.[Pubmed: 27642355]Evid Based Complement Alternat Med. 2016;2016:7481323.
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| Structure Identification | Chem Pharm Bull (Tokyo). 2002 Jul;50(7):964-5.The crystal structure of biatractylolide, an 8,8' (C-C) linked dimeric 12,8-eudesmanolide from the resin of Trattinickia rhoifolia WILLD.[Pubmed: 12130855 ]
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Biatractylolide Dilution Calculator
Biatractylolide Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.1617 mL | 10.8085 mL | 21.6169 mL | 43.2339 mL | 54.0424 mL |
| 5 mM | 0.4323 mL | 2.1617 mL | 4.3234 mL | 8.6468 mL | 10.8085 mL |
| 10 mM | 0.2162 mL | 1.0808 mL | 2.1617 mL | 4.3234 mL | 5.4042 mL |
| 50 mM | 0.0432 mL | 0.2162 mL | 0.4323 mL | 0.8647 mL | 1.0808 mL |
| 100 mM | 0.0216 mL | 0.1081 mL | 0.2162 mL | 0.4323 mL | 0.5404 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Biatractylolide Modulates PI3K-Akt-GSK3beta-Dependent Pathways to Protect against Glutamate-Induced Cell Damage in PC12 and SH-SY5Y Cells.[Pubmed:29075302]
Evid Based Complement Alternat Med. 2017;2017:1291458.
Biatractylolide, isolated from the ethyl acetate extract of Atractylodes macrocephala, has shown various pharmacological activities such as antitumor and antioxidant activities. In this work, we aim to study the protective effect of Biatractylolide on glutamate-induced rat adrenal pheochromocytoma cell (PC12) and human bone marrow neuroblastoma cell line (SH-SY5Y) injury and preliminarily explore its mechanism. The results showed that glutamate was cytotoxic with an inhibitory concentration 50% (IC50) of 8.5 mM in PC12 and 10 mM in SH-SY5Y cells. In this work, the preincubation with Biatractylolide (10, 15, and 20 muM) observably improved cell viability, inhibited the apoptosis of cells induced by glutamate, and reduced the activity of LDH. AO staining revealed that apoptosis of cells was decreased. Additionally, the results of western blotting manifested that pretreatment with Biatractylolide could downregulate GSK3beta protein expression and upregulate p-Akt protein expression, thereby protecting PC12 and SH-SY5Y cells from injury. All these findings indicate that Biatractylolide has a neuroprotective effect on glutamate-induced injury in PC12 and SH-SY5Y cells through a mechanism of the PI3K-Akt-GSK3beta-dependent pathways.
Primary Investigation for the Mechanism of Biatractylolide from Atractylodis Macrocephalae Rhizoma as an Acetylcholinesterase Inhibitor.[Pubmed:27642355]
Evid Based Complement Alternat Med. 2016;2016:7481323.
Biatractylolide was isolated from ethyl acetate extract of dried Atractylodis Macrocephalae Rhizoma root by multistep chromatographic processing. Structure of Biatractylolide was confirmed by (1)H-NMR and (13)C-NMR. The IC50 on acetylcholinesterase (AChE) activity was 6.5458 mug/mL when the control IC50 value of huperzine A was 0.0192 mug/mL. Molecular Docking Software (MOE) was used to discover molecular sites of action between Biatractylolide and AChE protein by regular molecular docking approaches. Moreover, Biatractylolide downregulated the expression of AChE of MEF and 293T cells in a dose-dependent manner. These results demonstrated that the molecular mechanisms of inhibitory activities of Biatractylolide on AChE are not only through binding to AChE, but also via reducing AChE expression by inhibiting the activity of GSK3beta.
Gastroprotective activity of atractylenolide III from Atractylodes ovata on ethanol-induced gastric ulcer in vitro and in vivo.[Pubmed:20487223]
J Pharm Pharmacol. 2010 Mar;62(3):381-8.
OBJECTIVES: The rhizome of Atractylodes ovata De Candolle is popularly used in traditional Chinese medicine to treat gastrointestinal diseases. However, the major gastroprotective compounds of A. ovata have not been identified. This study reports on the principal gastro- protective component of A. ovata. METHODS: Five sesquiterpenoids (atractylon, atractylenolides I, II, III and Biatractylolide) were isolated from the extracts of A. ovata rhizome via silica gel column chromatography. The gastroprotective effects of these five sesquiterpenoids were measured in in-vitro ethanol-induced primary culture rat gastric mucosal (PRGM) cell damage and in-vivo ethanol-induced acute rat gastric ulcer models. KEY FINDINGS: Atractylon, atractylenolide I and Biatractylolide were strongly toxic in PRGM cells, whilst atractylenolides II and III were not. 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. 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. CONCLUSIONS: Atractylenolide III was the major gastroprotective component of A. ovata in ethanol-induced acute gastric ulcer. It is suggested that the gastroprotective mechanism of atractylenolide III was via inhibition of the MMP-2 and MMP-9 pathway.
Dimerization of butenolide structures. A biomimetic approach to the dimeric sesquiterpene lactones (+/-)-biatractylolide and (+/-)-biepiasterolide.[Pubmed:15609943]
J Org Chem. 2004 Dec 24;69(26):9100-8.
The biomimetic synthesis of the bisesquiterpene lactones (+/-)-Biatractylolide 1 and (+/-)-biepiasterolide 2 via dimerization of the captodative stabilized radical 8 is reported. Atractylon 7 has also been shown to be a possible intermediate during the biosynthesis of Biatractylolide 1, biepiasterolide 2, atractylolide 3, and hydroxyatractylolide 4.
Biomimetic synthesis of biatractylolide and biepiasterolide.[Pubmed:12916978]
Org Lett. 2003 Aug 21;5(17):3049-52.
[reaction: see text] The biomimetic synthesis of the bisesquiterpenoids Biatractylolide 1 and biepiasterolide 2 is reported.
The crystal structure of biatractylolide, an 8,8' (C-C) linked dimeric 12,8-eudesmanolide from the resin of Trattinickia rhoifolia WILLD.[Pubmed:12130855]
Chem Pharm Bull (Tokyo). 2002 Jul;50(7):964-5.
A symmetrical dimeric sesquiterpenoid, Biatractylolide (1), was isolated from the resin of Trattinickia rhoifolia WILLD. The structure of compound 1 was elucidated by one- and two-dimensional NMR techniques and electron impact-mass spectra (EI-MS) data, and confirmed by X-ray crystallographic analysis.
