Shizukaol BCAS# 142279-40-1 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 142279-40-1 | SDF | Download SDF |
| PubChem ID | 131847922 | Appearance | Powder |
| Formula | C40H44O13 | M.Wt | 732.77 |
| Type of Compound | Sesquiterpenoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| SMILES | CC1=CCOC(=O)CCC(=O)OCC2=C3CC4C(C5CC5C4(COC1=O)O)(C6C3(C7C8=C(C6)C9CC9C8(C(C(=O)C7=C(C)C(=O)OC)O)C)OC2=O)C | ||
| Standard InChIKey | NCEFZVURTXZBJM-QSDRZCANSA-N | ||
| Standard InChI | InChI=1S/C40H44O13/c1-16-8-9-50-27(41)6-7-28(42)51-14-20-22-13-25-37(3,23-12-24(23)39(25,48)15-52-34(16)45)26-11-19-18-10-21(18)38(4)30(19)31(40(22,26)53-36(20)47)29(32(43)33(38)44)17(2)35(46)49-5/h8,18,21,23-26,31,33,44,48H,6-7,9-15H2,1-5H3/b16-8-,29-17-/t18-,21-,23-,24+,25-,26+,31+,33+,37+,38+,39+,40+/m1/s1 | ||
| 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 | 1. Shizukaol B exerts anti-inflammatory effects in LPS-activated microglia partly by modulating JNK-AP-1 signaling pathway. 2. Shizukaol B shows significant anti-neuroinflammatory effects by inhibiting nitric-oxide (NO) production in lipopolysaccharide (LPS)-stimulated murine BV-2 microglial cells with relatively low cytotoxicity. 3. Shizukaol B exhibits anti-HIV-1 replication activities in both wild-type HIV-1 and two NNRTIs-resistant strains, it also has significant cytotoxicities against C8166 cells. 4. Shizukaol B prevents monocyte adhesion to HUVEC through the inhibition of cell adhesion molecules expression stimulated by TNF-alpha. |
| Targets | NO | PGE | TNF-α | COX | NOS | NF-kB | IL Receptor | JNK | ERK | AP-1 | HIV | p38MAPK |
Shizukaol B Dilution Calculator
Shizukaol B Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 1.3647 mL | 6.8234 mL | 13.6468 mL | 27.2937 mL | 34.1171 mL |
| 5 mM | 0.2729 mL | 1.3647 mL | 2.7294 mL | 5.4587 mL | 6.8234 mL |
| 10 mM | 0.1365 mL | 0.6823 mL | 1.3647 mL | 2.7294 mL | 3.4117 mL |
| 50 mM | 0.0273 mL | 0.1365 mL | 0.2729 mL | 0.5459 mL | 0.6823 mL |
| 100 mM | 0.0136 mL | 0.0682 mL | 0.1365 mL | 0.2729 mL | 0.3412 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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Sesquiterpenoids from Chloranthus henryi and their anti-neuroinflammatory activities.[Pubmed:24934677]
Chem Biodivers. 2014 Jun;11(6):919-28.
Five new and seven known mono-sesquiterpenoids (1-5 and 6-12, resp.) together with five known lindenane-type disesquiterpenoids, 13-17, were isolated from the whole plant of Chloranthus henryi. Based on spectroscopic methods, the new structures were established to be (5S,6R,8S,10R)-6-hydroxyeudesma-4(15),7(11)-diene-12,8-olide (1), 6alpha-hydroxyeudesma-4(15),7(11),8(9)-triene-12,8-olide (2), 8,12-epoxy-1beta-hydroxyeudesma-4(15),7,11-trien-6-one (3), 12-oxochloraniolide A (4), and (4alpha)-8-hydroxy-12-norcardina-6,8,10-trien-11-one (5), respectively. Among the isolates, compound 2, zederone epoxide (8), spicachlorantin G (13), chloramultilide A (14), Shizukaol B (15), and spicachlorantin B (17) showed significant anti-neuroinflammatory effects by inhibiting nitric-oxide (NO) production in lipopolysaccharide (LPS)-stimulated murine BV-2 microglial cells with relatively low cytotoxicity.
Lindenane disesquiterpenoids with anti-HIV-1 activity from Chloranthus japonicus.[Pubmed:21650224]
J Nat Prod. 2011 Jun 24;74(6):1408-13.
Five new lindenane disesquiterpenoids, chlorajaponilides A-E (1-5), together with 11 known analogues were isolated from whole plants of Chloranthus japonicus. The structure and absolute configuration of 1 was confirmed by X-ray crystallography. Compounds 1 and 2 represent the first examples of lindenane disesquiterpenoids with a C-5 hydroxy group and a C-4-C-15 double bond. Compounds 8, 9, 11, and 12 showed anti-HIV-1 replication activities in both wild-type HIV-1 and two NNRTIs-resistant strains. Shizukaol B (8) exhibited the best activity against HIV(wt), HIV(RT-K103N), and HIV(RT-K103N) with EC(5)(0) values of 0.22, 0.47, and 0.50 muM, respectively. Compounds 8, 9, 11, and 12 had significant cytotoxicities against C8166 cells with CC(5)(0) values of 0.020, 0.089, 0.047, and 0.022, respectively, and exhibited inhibitory activities against HIV-1 with EC(5)(0) values of 0.0014, 0.016, 0.0043, and 0.0033 muM, respectively.
Dimeric sesquiterpenoids isolated from Chloranthus japonicus inhibited the expression of cell adhesion molecules.[Pubmed:16229979]
J Ethnopharmacol. 2006 Mar 8;104(1-2):270-7.
In the search for cell adhesion inhibitors from natural sources, three active compounds were isolated from Chloranthus japonicus Sieb. (Chloranthaceae) roots. The compounds were identified as dimeric sesquiterpenoids of Shizukaol B (1), cycloshizukaol A (2) and shizukaol F (3). These compounds inhibited PMA-induced homotypic aggregation of HL-60 cells without cytotoxicity with MIC values of 34.1 nM (1), 0.9 microM (2) and 27.3 nM (3), respectively. Although 1-3 did not affect the direct binding of LFA-1 to ICAM-1, these compounds markedly inhibited ICAM-1 expression in HL-60 cells in a dose-dependent fashion. On the other hand, when HUVEC were pretreated with 1-3 and stimulated with TNF-alpha, adhesion of THP-1 cells to HUVEC decreased in dose-dependent manner with IC(50) values of 54.6 nM, 1.2 microM and 34.1 nM, respectively. In fact, 1 inhibited TNF-alpha-induced surface expression of the ICAM-1, VCAM-1 and E-selectin in HUVEC with IC(50) values of 5.4 nM, 13.6 microM and 95.6 nM, respectively. The present findings suggest that 1-3 prevent monocyte adhesion to HUVEC through the inhibition of cell adhesion molecules expression stimulated by TNF-alpha.
Shizukaol B, an active sesquiterpene from Chloranthus henryi, attenuates LPS-induced inflammatory responses in BV2 microglial cells.[Pubmed:28178617]
Biomed Pharmacother. 2017 Apr;88:878-884.
The objective of the current study was to evaluate the anti-inflammatory effects of Shizukaol B, a lindenane-type dimeric sesquiterpene isolated from the whole plant of Chloranthus henryi, on lipopolysaccharide (LPS)-induced activation of BV2 microglial cells in vitro. Our data showed that Shizukaol B concentration-dependently suppressed expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2), production of nitric oxide (NO), tumor necrosis factor-alpha (TNF-alpha), and interleukin-1beta (IL-1beta) in LPS-stimulated BV2 microglia. Meanwhile, Shizukaol B concentration- and time-dependently inhibited LPS-mediated c-Jun N-terminal kinase 1/2 (JNK) activation, but had little effect on extracellular signal-regulated kinase 1/2 or p38 phosphorylation. Furthermore, Shizukaol B significantly blocked LPS-induced activator protein-1 (AP-1) activation, evidenced by reduced phosphorylation and nuclear translocation of c-Jun and DNA binding activity of AP-1. Taken together, our findings suggest that Shizukaol B exerts anti-inflammatory effects in LPS-activated microglia partly by modulating JNK-AP-1 signaling pathway.
