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15-Methoxypinusolidic acid

CAS# 769928-72-5

15-Methoxypinusolidic acid

Catalog No. BCN4321----Order now to get a substantial discount!

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15-Methoxypinusolidic acid: 5mg $903 In Stock
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Quality Control of 15-Methoxypinusolidic acid

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Chemical structure

15-Methoxypinusolidic acid

3D structure

Chemical Properties of 15-Methoxypinusolidic acid

Cas No. 769928-72-5 SDF Download SDF
PubChem ID 11152671 Appearance Powder
Formula C21H30O5 M.Wt 362.5
Type of Compound Diterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (1S,4aR,5S,8aR)-5-[2-(2-methoxy-5-oxo-2H-furan-4-yl)ethyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
SMILES CC12CCCC(C1CCC(=C)C2CCC3=CC(OC3=O)OC)(C)C(=O)O
Standard InChIKey OREKSZUASHFFQA-OBNOUSFBSA-N
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 15-Methoxypinusolidic acid

The leaves of Biota orientalis

Biological Activity of 15-Methoxypinusolidic acid

Description1. 15-Methoxypinusolidic acid induced apoptosis in murine microglial cells, presumably via inhibition of the cell cycle progression. 2. 15-Methoxypinusolidic acid inhibits LPS-induced iNOS expression and NO production, independent on MAPK and NF-kappaB, suggesting a potential anti-inflammatory effect of the compound on microglial cells. 3. 15-Methoxypinusolidic acid suppresses adipocyte differentiation through the inhibition of PPARgamma-dependent adipogenic gene expression. 4. 15-Methoxypinusolidic acid attenuates glutamate-induced excitotoxicity via stabilization of [Ca2+]i homeostasis and suppression of oxidative stress possibly through the actions on the NMDA receptors.
TargetsNOS | NO | PPAR | Calcium Channel | NF-kB | NMDAR | p38MAPK | ERK | JNK | IL Receptor | COX

15-Methoxypinusolidic acid Dilution Calculator

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15-Methoxypinusolidic acid Molarity Calculator

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Preparing Stock Solutions of 15-Methoxypinusolidic acid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.7586 mL 13.7931 mL 27.5862 mL 55.1724 mL 68.9655 mL
5 mM 0.5517 mL 2.7586 mL 5.5172 mL 11.0345 mL 13.7931 mL
10 mM 0.2759 mL 1.3793 mL 2.7586 mL 5.5172 mL 6.8966 mL
50 mM 0.0552 mL 0.2759 mL 0.5517 mL 1.1034 mL 1.3793 mL
100 mM 0.0276 mL 0.1379 mL 0.2759 mL 0.5517 mL 0.6897 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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References on 15-Methoxypinusolidic acid

Suppression of adipocyte differentiation by 15-methoxypinusolidic acid through inhibition of PPARgamma activity.[Pubmed:20661713]

Arch Pharm Res. 2010 Jul;33(7):1035-41.

Pinusolide and its derivative, 15-Methoxypinusolidic acid (15-MPA) are diterpenoid compounds isolated from Biota orientalis, which has been used as a Korean folk medicine for treating inflammatory disorders. Pinusolide and 15-MPA suppress nitric oxide generation by suppressing inducible nitric oxide synthase and exerted anti-inflammatory functions, whereas other functions and regulatory mechanisms are largely unknown. In this study, we investigated whether pinusolide and 15-MPA modulate adipocyte differentiation from pre-adipocytes 3T3-L1 cells. We found that 15-MPA, not pinusolide, suppressed adipocyte differentiation in a dose-dependent manner, as revealed by lipid droplet formation and expression of adipogenic genes such as adiponectin and aP2. 15-MPA did not affect mRNA and protein levels of PPARgamma, a key adipogenic transcription factor, whereas transcriptional activity of PPARgamma was significantly attenuated by 15-MPA. While aP2 promoter activity was increased by ectopic overexpression of PPARgamma or by rosiglitazone-induced endogenous PPARgamma activation, PPARgamma-induced aP2 promoter activity was inhibited in the presence of 15-MPA. These results suggest that 15-MPA suppresses adipocyte differentiation through the inhibition of PPARgamma-dependent adipogenic gene expression.

15-Methoxypinusolidic acid from Biota orientalis attenuates glutamate-induced neurotoxicity in primary cultured rat cortical cells.[Pubmed:16564156]

Toxicol In Vitro. 2006 Sep;20(6):936-41.

15-Methoxypinusolidic acid (15-MPA), a pinusolide derivative isolated from Biota orientalis (Cupressaceae) leaves prevented glutamate-induced excitotoxicity in primary cultured rat cortical cells in vitro. 15-MPA had more selectivity in protecting neurons against N-methyl-D-aspartate (NMDA)-induced neurotoxicity than that induced by kainic acid (KA). The glutamate-induced increase of intracellular calcium ([Ca2+]i) in cortical cells was effectively reduced by 15-MPA. Moreover, 15-MPA could successfully reduce the subsequent overproduction of nitric oxide (NO) and the level of cellular peroxide, and inhibit glutathione (GSH) depletion and lipid peroxidation induced by glutamate in our cultures. Collectively, these results suggested that 15-MPA attenuated glutamate-induced excitotoxicity via stabilization of [Ca2+]i homeostasis and suppression of oxidative stress possibly through the actions on the NMDA receptors.

A pinusolide derivative, 15-methoxypinusolidic acid from Biota orientalis inhibits inducible nitric oxide synthase in microglial cells: implication for a potential anti-inflammatory effect.[Pubmed:18328446]

Int Immunopharmacol. 2008 Apr;8(4):548-55.

The inhibitory effect of 15-Methoxypinusolidic acid (15-MPA) isolated from Biota orientalis (Cupressaceae) on lipopolysaccharide (LPS)-induced inflammation in microglial BV2 cells was investigated. 15-MPA significantly reduced the expression of inducible nitric oxide synthase (iNOS), the activity of iNOS, and the production of nitric oxide (NO) in LPS-stimulated BV2 cells. In addition, 15-MPA significantly suppressed the expressions of tumor necrosis factor (TNF)-alpha, interleukin (IL)-6, and cyclooxygenase (COX)-2. However, 15-MPA did not affect LPS-induced degradation of inhibitor kappaB-alpha (IkappaB-alpha) and translocation of nuclear factor-kappaB (NF-kappaB) into the nucleus. LPS-activated p38 MAPK, extracellular signal-regulated kinase (ERK)-1/2, and stress-activated protein kinase/c-Jun N-terminal kinase (SAPK/JNK) were not affected by 15-MPA. Taken together, this study demonstrates that 15-MPA inhibits LPS-induced iNOS expression and NO production, independent on MAPK and NF-kappaB, suggesting a potential anti-inflammatory effect of the compound on microglial cells.

Oligonucleotide microarray analysis of apoptosis induced by 15-methoxypinusolidic acid in microglial BV2 cells.[Pubmed:19466985]

Br J Pharmacol. 2009 Jul;157(6):1053-64.

BACKGROUND AND PURPOSE: We conducted a genome wide gene expression analysis to explore the biological aspects of 15-Methoxypinusolidic acid (15-MPA) isolated from Biota orientalis and tried to confirm the suitability of 15-MPA as a therapeutic candidate for CNS injuries focusing on microglia. EXPERIMENTAL APPROACH: Murine microglial BV2 cells were treated with 15-MPA, and their transcriptome was analysed by using oligonucleotide microarrays. Genes differentially expressed upon 15-MPA treatment were selected for RT-PCR (reverse transcription-polymerase chain reaction) analysis to confirm the gene expression. Inhibition of cell proliferation and induction of apoptosis by 15-MPA were examined by bromodeoxyuridine assay, Western blot analysis of poly-ADP-ribose polymerase and flow cytometry. KEY RESULTS: A total of 514 genes were differentially expressed by 15-MPA treatment. Biological pathway analysis revealed that 15-MPA induced significant changes in expression of genes in the cell cycle pathway. Genes involved in growth arrest and DNA damage [gadd45alpha, gadd45gamma and ddit3 (DNA damage-inducible transcript 3)] and cyclin-dependent kinase inhibitor (cdkn2b) were up-regulated, whereas genes involved in cell cycle progression (ccnd1, ccnd3 and ccne1), DNA replication (mcm4, orc1l and cdc6) and cell proliferation (fos and jun) were down-regulated. RT-PCR analysis for representative genes confirmed the expression levels. 15-MPA significantly reduced bromodeoxyuridine incorporation, increased poly-ADP-ribose polymerase cleavage and the number of apoptotic cells, indicating that 15-MPA induces apoptosis in BV2 cells. CONCLUSION AND IMPLICATIONS: 15-MPA induced apoptosis in murine microglial cells, presumably via inhibition of the cell cycle progression. As microglial activation is detrimental in CNS injuries, these data suggest a strong therapeutic potential of 15-MPA.

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