Glaucocalyxin B

CAS# 80508-81-2

Glaucocalyxin B

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Chemical structure

Glaucocalyxin B

3D structure

Chemical Properties of Glaucocalyxin B

Cas No. 80508-81-2 SDF Download SDF
PubChem ID 14193399 Appearance White crystalline powder
Formula C22H30O5 M.Wt 374.5
Type of Compound Diterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name [(1R,2R,4S,9R,10S,13S,16R)-2-hydroxy-5,5,9-trimethyl-14-methylidene-6,15-dioxo-16-tetracyclo[11.2.1.01,10.04,9]hexadecanyl] acetate
SMILES CC(=O)OC1C2CCC3C1(C(CC4C3(CCC(=O)C4(C)C)C)O)C(=O)C2=C
Standard InChIKey LSUXOKVMORWDLT-KEXKRWMXSA-N
Standard InChI InChI=1S/C22H30O5/c1-11-13-6-7-14-21(5)9-8-16(24)20(3,4)15(21)10-17(25)22(14,18(11)26)19(13)27-12(2)23/h13-15,17,19,25H,1,6-10H2,2-5H3/t13-,14-,15+,17+,19+,21-,22-/m0/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.
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.
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.

Source of Glaucocalyxin B

The herbs of Rabdosia rubescens.

Biological Activity of Glaucocalyxin B

Description1. Glaucocalyxin B alleviates lipopolysaccharide-induced Parkinson's disease by inhibiting TLR/NF-κB and activating Nrf2/HO-1 Pathway. 2. Glaucocalyxin B is a potent NF-κB inhibitor for Alzheimer's disease treatment. 3. Glaucocalyxin B shows sensitization of gastric cancer cells to alkylating agents via cell cycle arrest and enhances cell death. 4. Glaucocalyxin B induces apoptosis and autophagy in human cervical cancer cells. 5. Glaucocalyxin B has anti-inflammatory effects, it exhibits neuroprotective effect by preventing over-activated microglia induced neurotoxicity in a microglia/neuron co-culture model.
TargetsTLR | NF-kB | HO-1 | Nrf2 | IkB | PARP | Akt | Autophagy | COX | NO | TNF-α | IL Receptor | NOS | ROS | p38MAPK | IKK

Glaucocalyxin B Dilution Calculator

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Glaucocalyxin B Molarity Calculator

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Preparing Stock Solutions of Glaucocalyxin B

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.6702 mL 13.3511 mL 26.7023 mL 53.4045 mL 66.7557 mL
5 mM 0.534 mL 2.6702 mL 5.3405 mL 10.6809 mL 13.3511 mL
10 mM 0.267 mL 1.3351 mL 2.6702 mL 5.3405 mL 6.6756 mL
50 mM 0.0534 mL 0.267 mL 0.534 mL 1.0681 mL 1.3351 mL
100 mM 0.0267 mL 0.1335 mL 0.267 mL 0.534 mL 0.6676 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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Background on Glaucocalyxin B

Glaucocalyxin B is an ent kaurane diterpenoid isolated from the Chinese traditional medicine Rabdosia japonica with anticancer and antitumor activity; decreases the growth of HL-60 cells with an IC50 of approximately 5.86 μM at 24 h.

In Vitro:Glaucocalyxin A (GlnA) and (GlnB) dose-dependently decrease the growth of HL-60 cells with an IC50 of approximately 6.15 and 5.86 µM at 24 h, respectively. Both Gln A and B could induce apoptosis, G2/M-phase cycle arrest, DNA damage and the accumulation of reactive oxygen species (ROS) in HL-60 cells[1]. GlnB inhibits the proliferation of human cervical cancer cells in vitro through the induction of apoptosis andautophagy, which may be mediated by the phosphatidylinositol 4,5 bisphosphate 3 kinase/Akt signaling pathway. Treatment with GlnB inhibits the proliferation of HeLa and SiHa cervical cancer cell lines in a dose dependent manner. GlnB increases the apoptotic cell population of and enhanced poly (ADP ribose) polymerase 1 cleavage. GlnB also induces increased light chain 3 II/I protein cleavage, indicating the induction of autophagy. GlnB treatment increases the expression of phosphatase and tensin homolog and decreases the expression of phosphorylated protein kinase B[2]. Glaucocalyxin B (GLB), one of five ent-kauranoid diterpenoids, significantly decreased the generation of nitric oxide (NO), tumor necrosis factor (TNF)-α, interleukin (IL)-1β, cyclooxygenase (COX)-2 and inducible nitric oxide synthase (iNOS) in the lipopolysaccharide (LPS)-activated microglia cells[3].

References:
[1]. Yang WH, et al. Glaucocalyxin A and B-induced cell death is related to GSH perturbation in human leukemia HL-60 cells. Anticancer Agents Med Chem. 2013 Oct;13(8):1280-90. [2]. Pan Y, et al. Glaucocalyxin B induces apoptosis and autophagy in human cervical cancer cells. Mol Med Rep. 2016 Aug;14(2):1751-5. [3]. Gan P, et al. Anti-inflammatory effects of glaucocalyxin B in microglia cells. J Pharmacol Sci. 2015 May;128(1):35-46.

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References on Glaucocalyxin B

Simultaneous determination of glaucocalyxin A and glaucocalyxin B in rat plasma by LC-MS/MS and its application to a pharmacokinetic study after oral administration of Rabdosia japonica extract.[Pubmed:28873500]

Biomed Chromatogr. 2018 Feb;32(2).

A specific and sensitive liquid chromatography tandem mass spectrometry (LC-MS/MS) method was developed and validated for the analysis of glaucocalyxin A and Glaucocalyxin B in rat plasma using praeruptorin A as an internal standard. Separation was performed on a Hypurity C18 column (2.1 x 50 mm, 5 mum) with isocratic elution using 0.2% formic acid in water-acetonitrile (20:80, v/v). Mass spectrometric detection was conducted using selected reaction monitoring via an electrospray ionization source. Both analytes exhibited good linearity within their concentration ranges (r(2) > 0.9932). The lower limit of quantitation of glaucocalyxin A and Glaucocalyxin B was 1.10 ng/mL. Intra- and inter-day precision exhibited an RSD within 14.5%, and the accuracy (RE) ranged from -12.1 to 15.0% at the lower limit of quantitation and three quality control levels. The developed assay was successfully applied to a pharmacokinetic study of glaucocalyxin A and Glaucocalyxin B in rats after oral administration of Rabdosia japonica extract.

Phytochemicals as inhibitors of NF-kappaB for treatment of Alzheimer's disease.[Pubmed:29179999]

Pharmacol Res. 2018 Mar;129:262-273.

Alzheimer's disease (AD) is the most prevalent form of dementia. The exact pathophysiology of this disease remains incompletely understood and safe and effective therapies are required. AD is highly correlated with neuroinflammation and oxidative stress in brain causing neuronal loss. Nuclear factor of activated B-cells (NF-kappaB) is involved in physiological inflammatory processes and thus representing a promising target for inflammation-based AD therapy. Phytochemicals are able to interfere with the NF-kappaB pathway. They inhibit the phosphorylation or the ubiquitination of signaling molecules, and thus, inhibit the degradation of IkappaB. The translocation of NF-kappaB to the nucleus and subsequent transcription of pro-inflammatory cytokines are inhibited by the actions of phytochemicals. Additionally, natural compounds preventing the interaction of NF-kappaB can block NF-kappaB's transcriptional activity by inhibiting its binding to target DNA. Many polyphenols including curcumin, resveratrol, pterostilbene, punicalagin, macranthoin G, salidroside, 4-O-methylhonokiol, lycopene, genistein, obovatol and gallic acid were reported as potent NF-kappaB inhibitors for AD treatment. Several alkaloids such as galantamine, Glaucocalyxin B, tetrandrine, berberine, oridonin, anatabine have been shown anti-inflammatory effects in AD models in vitro as well as in vivo. Besides, vitamins, tanshinone IIA, artemisinin, dihydroasparagusic acid, geniposide, xanthoceraside, l-theranine, 1,8-cineole and paeoniflorin were described as promising NF-kappaB inhibitors. In conclusion, natural products from plants represent interesting candidates for AD treatment. They may qualify as promising compounds for the development of derivatives providing enhanced pharmacological features.

Anti-inflammatory effects of glaucocalyxin B in microglia cells.[Pubmed:26003084]

J Pharmacol Sci. 2015 May;128(1):35-46.

Over-activated microglia is involved in various kinds of neurodegenerative process including Parkinson, Alzheimer and HIV dementia. Suppression of microglial over activation has emerged as a novel strategy for treatment of neuroinflammation-based neurodegeneration. In the current study, anti-inflammatory and neuroprotective effects of the ent-kauranoid diterpenoids, which were isolated from the aerial parts of Rabdosia japonica (Burm. f.) var. glaucocalyx (Maxim.) Hara, were investigated in cultured microglia cells. Glaucocalyxin B (GLB), one of five ent-kauranoid diterpenoids, significantly decreased the generation of nitric oxide (NO), tumor necrosis factor (TNF)-alpha, interleukin (IL)-1beta, cyclooxygenase (COX)-2 and inducible nitric oxide synthase (iNOS) in the lipopolysaccharide (LPS)-activated microglia cells. In addition, GLB inhibited activation of nuclear factor-kappaB (NF-kappaB), p38 mitogen-activated protein kinase (MAPK) and generation of reactive oxygen species (ROS) in LPS-activated microglia cells. Furthermore, GLB strongly induced the expression of heme oxygenase (HO)-1 in BV-2 microglia cells. Finally, GLB exhibited neuroprotective effect by preventing over-activated microglia induced neurotoxicity in a microglia/neuron co-culture model. Taken together, the present study demonstrated that the GLB possesses anti-nueroinflammatory activity, and might serve as a potential therapeutic agent for treating neuroinflammatory diseases.

Sensitization of gastric cancer cells to alkylating agents by glaucocalyxin B via cell cycle arrest and enhanced cell death.[Pubmed:28860714]

Drug Des Devel Ther. 2017 Aug 22;11:2431-2441.

Severe side effects are major problems with chemotherapy of gastric cancer (GC). These side effects can be reduced by using sensitizing agents in combination with therapeutic drugs. In this study, the low/nontoxic dosage of Glaucocalyxin B (GLB) was used with other DNA linker agents mitomycin C (MMC), cisplatin (DDP), or cyclophosphamide (CTX) to treat GC cells. Combined effectiveness of GLB with drugs was determined by proliferation assay. The molecular mechanisms associated with cell proliferation, migration, invasion, cell cycle, DNA repair/replication, apoptosis, and autophagy were investigated by immunoblotting for key proteins involved. Cell cycle and apoptosis analysis were performed by flow cytometry. Reactive oxygen species level was also examined for identification of its role in apoptosis. Proliferation assay revealed that the addition of 5 microM GLB significantly sensitizes gastric cancer SGC-7901 cells to MMC, DDP, and CTX by decreasing half-maximal inhibitory concentration (IC50) by up to 75.40%+/-5%, 45.10%+/-5%, and 52.10%+/-5%, respectively. GLB + drugs decreased the expression level of proteins involved in proliferation and migration, suggesting the anticancer potential of GLB + drugs. GLB + MMC, GLB + CTX, and GLB + DDP arrest the cells in G0/G1 and G1/S phase, respectively, which may be the consequence of significant decrease in the level of enzymes responsible for DNA replication and telomerase shortening. Combined use of GLB with these drugs also induces DNA damage and apoptosis by activating caspase/PARP pathways and increased production of reactive oxygen species and increased autophagy in GC cells. GLB dosage sensitizes GC cells to the alkylating agents via arresting the cell cycle and enhancing cell death. This is of significant therapeutic importance in the reduction of side effects associated with these drugs.

An ent-kaurane diterpenoid from Isodon japonica var. glaucocalyx.[Pubmed:21583588]

Acta Crystallogr Sect E Struct Rep Online. 2009 Jul 18;65(Pt 8):o1898.

The title compound, 14beta-acet-oxy-7alpha-hydr-oxy-ent-kaur-16-ene-3,15-dione or Glaucocalyxin B, C(22)H(30)O(5), a natural ent-kaurane diterpenoid, is composed of four rings with the expected cis and trans ring junctions. In the crystal structure, there are two mol-ecules in the asymmetric unit related by a noncrystallographic twofold screw axis, and ring A is disordered [ratio occupancies 0.829 (19):0.171 (19)], such that both chair and boat conformations are present, but with the boat conformation as the major component. In the crystal, mol-ecules are linked by inter-molecular O-Hcdots, three dots, centeredO hydrogen bonds.

Glaucocalyxin B Alleviates Lipopolysaccharide-Induced Parkinson's Disease by Inhibiting TLR/NF-kappaB and Activating Nrf2/HO-1 Pathway.[Pubmed:29241205]

Cell Physiol Biochem. 2017;44(6):2091-2104.

BACKGROUND/AIMS: Parkinson's disease (PD) is a common neurodegenerative disease in the old population, characterized by dopaminergic neuron loss, inflammation and oxidative stress injury in the substantia nigra. Glaucocalyxin B (GLB), an ent-kauranoid diterpenoid isolated from Rabdosia japonica, has anti-inflammation and anti-tumor effects. However, its effects on PD remain unclear. METHODS: PD was introduced in rats via injection of lipopolysaccharide (LPS) into cerebral corpus striatum, and GLB was given intracerebroventricularly to these rats. Their walking, climbing and sensory states were detected by Stepping, Whisker and Cylinder Tests. The expression of tyrosine hydroxylase (TH), glial fibrillary acidic protein (GFAP), CD11b and ionized calcium binding adaptor molecule (IBA)-1 were detected by immunohischemical staining. The levels of a series of inflammatory factors, oxidative stress-related factors and apoptosis-related factors were measured by real-time PCR, immunoblotting and ELISA. In addition, Toll-like receptor (TLR)/nuclear factor kappa B (NF-kappaB) and nuclear factor erythroid 2-related factor 2 (Nrf2)/heme oxygenase (HO)-1 pathways were investigated to illustrate the underlying mechanism. In vitro, microglial cells exposed to LPS were treated with GLB. RESULTS: The injection of LPS caused walking, climbing and sensory disturbances in rats, induced inflammation, oxidative stress response and apoptosis, and activated TLR/NF-kappaB and Nrf2/ HO-1 pathways in the cerebral tissue. GLB administration attenuated LPS-induced alterations. The TLR/NF-kappaB pathway was deactivated and Nrf2/HO-1 was activated after application of GLB. In vitro, cytotoxic effects induced by the conditioned medium derived from microglial cells exposed to LPS in PC12 cells were attenuated by GLB. CONCLUSION: GLB suppresses LPS-induced PD symptoms by modification of TLR/NF-kappaB and Nrf2/HO-1 pathways in vivo and in vitro.

Description

Glaucocalyxin B is an ent kaurane diterpenoid isolated from the Chinese traditional medicine Rabdosia japonica with anticancer and antitumor activity; decreases the growth of HL-60 cells with an IC50 of approximately 5.86 μM at 24 h.

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