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Isopimaric Acid Sale

(Synonyms: 异海松酸) 目录号 : GC49306

A diterpenoid resin acid

Isopimaric Acid Chemical Structure

Cas No.:5835-26-7

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产品描述

Isopimaric acid is a diterpenoid resin acid that has been found in P. nigra and has diverse biological activities.1,2,3,4 It is active against clinical isolates of epidemic methicillin-resistant S. aureus (EMRSA; MICs = 32-64 µg/ml).1 Isopimaric acid is an agonist of retinoid X receptor alpha (RXRα), RXRβ, and RXRγ in a reporter assay using HEK293T cells expressing human receptors (EC50s = 26, 32, and 33 µM, respectively).2 It opens large conductance calcium-activated potassium channels (BKCa1.1/KCa1.1) in HEK293 cells expressing recombinant channels and the activating β1 regulatory subunit when used at a concentration of 10 µM.3 Isopimaric acid potentiates reductions in field excitatory postsynaptic potential (fEPSP) slopes in hippocampal slices and decreases escape latency in the Morris water maze in a 3xTg mouse model of Alzheimer’s disease.4 It has been found as an environmental contaminant in pulp and paper mill effluent.5

1.Smith, E., Williamson, E., Zloh, M., et al.Isopimaric acid from Pinus nigra shows activity against multidrug-resistant and EMRSA strains of Staphylococcus aureusPhytother. Res.19(6)538-542(2005) 2.Merk, D., Grisoni, F., Friedrich, L., et al.Computer-assisted discovery of retinoid X receptor modulating natural products and isofunctional mimeticsJ. Med. Chem.61(12)5442-5447(2018) 3.Imaizumi, Y., Sakamoto, K., Yamada, A., et al.Molecular basis of pimarane compounds as novel activators of large-conductance Ca2+-activated K+ channel α-subunitMol. Pharmacol.62(4)836-846(2002) 4.Wang, L., Kang, H., Li, Y., et al.Cognitive recovery by chronic activation of the large-conductance calcium-activated potassium channel in a mouse model of Alzheimer’s diseaseNeuropharmacology928-15(2015) 5.van den Heuvel, M.R., Ellis, R.J., Tremblay, L.A., et al.Exposure of reproductively maturing rainbow trout to a New Zealand pulp and paper mill effluentEcotoxicol. Environ. Saf.51(1)65-75(2002)

Chemical Properties

Cas No. 5835-26-7 SDF
别名 异海松酸
Canonical SMILES C[C@@]12[C@](CC=C3[C@]2([H])CC[C@@](C)(C3)C=C)([H])[C@@](C)(CCC1)C(O)=O
分子式 C20H30O2 分子量 302.5
溶解度 Chloroform: slightly soluble,Methanol: slightly soluble 储存条件 -20°C
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1 mM 3.3058 mL 16.5289 mL 33.0579 mL
5 mM 0.6612 mL 3.3058 mL 6.6116 mL
10 mM 0.3306 mL 1.6529 mL 3.3058 mL
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Research Update

Synthesis and biological activity of pyridine acylhydrazone derivatives of Isopimaric Acid

J Asian Nat Prod Res 2021 Jun;23(6):545-555.PMID:32856467DOI:10.1080/10286020.2020.1810668.

Pyridine acylhydrazone derivatives of Isopimaric Acid were synthesized and characterized. The minimum inhibitory concentrations of the compounds against five bacteria were determined and most of the compounds displayed some degree of antibacterial activity. The results showed that antimicrobial activity against Streptococcus pneumoniae improved when halogen atoms were introduced into the Isopimaric Acid, especially when one bromine atom was introduced in the para-position of Isopimaric Acid. Compound Isopimaric Acid (5-bromo pyridine-2-formaldehyde) acylhydrazone exhibited a significant antitumorial activity against hepatocarcioma cells (HepG-2) and breast cancer cells (MDA-MB-231), with inhibition degrees of 74.21% and 70.39%, respectively, at 100 μM.[Formula: see text].

Isopimaric Acid from Pinus nigra shows activity against multidrug-resistant and EMRSA strains of Staphylococcus aureus

Phytother Res 2005 Jun;19(6):538-42.PMID:16114093DOI:10.1002/ptr.1711.

The diterpene Isopimaric Acid was extracted from the immature cones of Pinus nigra (Arnold) using bioassay-guided fractionation of a crude hexane extract. Isopimaric Acid was assayed against multidrug-resistant (MDR) and methicillin-resistant Staphylococcus aureus (MRSA). The minimum inhibitory concentrations (MIC) were 32-64 microg/mL and compared with a commercially obtained resin acid, abietic acid, with MICs of 64 microg/mL. Resin acids are known to have antibacterial activity and are valued in traditional medicine for their antiseptic properties. These results show that Isopimaric Acid is active against MDR and MRSA strains of S. aureus which are becoming increasingly resistant to antibiotics. Both compounds were evaluated for modulation activity in combination with antibiotics, but did not potentiate the activity of the antibiotics tested. However, the compounds were also assayed in combination with the efflux pump inhibitor reserpine, to see if inhibition of the TetK or NorA efflux pump increased their activity. Interestingly, rather than a potentiation of activity by a reduction in MIC, a two to four-fold increase in MIC was seen. It may be that Isopimaric Acid and abietic acid are not substrates for these efflux pumps, but it is also possible that an antagonistic interaction with reserpine may render the antibiotics inactive. 1H-NMR of abietic acid and reserpine taken individually and in combination, revealed a shift in resonance of some peaks for both compounds when mixed together compared with the spectra of the compounds on their own. It is proposed that this may be due to complex formation between abietic acid and reserpine and that this complex formation is responsible for a reduction in activity and elevation of MIC.

Isopimaric Acid - a multi-targeting ion channel modulator reducing excitability and arrhythmicity in a spontaneously beating mouse atrial cell line

Acta Physiol (Oxf) 2018 Jan;222(1).PMID:28514017DOI:10.1111/apha.12895.

Aim: Atrial fibrillation is the most common persistent cardiac arrhythmia, and it is not well controlled by present drugs. Because some resin acids open voltage-gated potassium channels and reduce neuronal excitability, we explored the effects of the resin acid Isopimaric Acid (IPA) on action potentials and ion currents in cardiomyocytes. Methods: Spontaneously beating mouse atrial HL-1 cells were investigated with the whole-cell patch-clamp technique. Results: 1-25 μmol L-1 IPA reduced the action potential frequency by up to 50%. The effect of IPA on six different voltage-gated ion channels was investigated; most voltage-dependent parameters of ion channel gating were shifted in the negative direction along the voltage axis, consistent with a hypothesis that a lipophilic and negatively charged compound binds to the lipid membrane close to the positively charged voltage sensor of the ion channels. The major finding was that IPA inactivated sodium channels and L- and T-type calcium channels and activated the rapidly activating potassium channel and the transient outward potassium channel. Computer simulations of IPA effects on all of the ion currents were consistent with a reduced excitability, and they also showed that effects on the Na channel played the largest role to reduce the action potential frequency. Finally, induced arrhythmia in the HL-1 cells was reversed by IPA. Conclusion: Low concentrations of IPA reduced the action potential frequency and restored regular firing by altering the voltage dependencies of several voltage-gated ion channels. These findings can form the basis for a new pharmacological strategy to treat atrial fibrillation.

Heterologous expression of the Isopimaric Acid pathway in Nicotiana benthamiana and the effect of N-terminal modifications of the involved cytochrome P450 enzyme

J Biol Eng 2015 Dec 22;9:24.PMID:26702299DOI:10.1186/s13036-015-0022-z.

Background: Plant terpenoids are known for their diversity, stereochemical complexity, and their commercial interest as pharmaceuticals, food additives, and cosmetics. Developing biotechnology approaches for the production of these compounds in heterologous hosts can increase their market availability, reduce their cost, and provide sustainable production platforms. In this context, we aimed at producing the antimicrobial diterpenoid Isopimaric Acid from Sitka spruce. Isopimaric Acid is synthesized using geranylgeranyl diphosphate as a precursor molecule that is cyclized by a diterpene synthase in the chloroplast and subsequently oxidized by a cytochrome P450, CYP720B4. Results: We transiently expressed the Isopimaric Acid pathway in Nicotiana benthamiana leaves and enhanced its productivity by the expression of two rate-limiting steps in the pathway (providing the general precursor of diterpenes). This co-expression resulted in 3-fold increase in the accumulation of both isopimaradiene and Isopimaric Acid detected using GC-MS and LC-MS methodology. We also showed that modifying or deleting the transmembrane helix of CYP720B4 does not alter the enzyme activity and led to successful accumulation of Isopimaric Acid in the infiltrated leaves. Furthermore, we demonstrated that a modified membrane anchor is a prerequisite for a functional CYP720B4 enzyme when the chloroplast targeting peptide is added. We report the accumulation of 45-55 μg/g plant dry weight of Isopimaric Acid four days after the infiltration with the modified enzymes. Conclusions: It is possible to localize a diterpenoid pathway from spruce fully within the chloroplast of N. benthamiana and a few modifications of the N-terminal sequences of the CYP720B4 can facilitate the expression of plant P450s in the plastids. The coupling of terpene biosynthesis closer to photosynthesis paves the way for light-driven biosynthesis of valuable terpenoids.

Isopimaric Acid, an ion channel regulator, regulates calcium and oxidative phosphorylation pathways to inhibit breast cancer proliferation and metastasis

Toxicol Appl Pharmacol 2023 Mar 1;462:116415.PMID:36754215DOI:10.1016/j.taap.2023.116415.

Breast cancer is the globally most common malignant tumor and the biggest threat to women. Even though the diagnosis and treatment of breast cancer are progressing continually, a large number of breast cancer patients eventually develop a metastatic tumor, especially triple-negative breast cancer (TNBC). Recently, metal ion homeostasis and ion signaling pathway have become important targets for cancer therapy. In this study, We analyzed the effects and mechanisms of Isopimaric Acid (IPA), an ion channel regulator, on the proliferation and metastasis of breast cancer cells (4 T1, MDA-MB-231and MCF-7) by cell functional assay, flow cytometry, western blot, proteomics and other techniques in vitro and in vivo. Results found that IPA significantly inhibited the proliferation and metastasis of breast cancer cells (especially 4 T1). Further studies on the anti-tumor mechanism of IPA suggested that IPA might affect EMT and Wnt signaling pathways by targeting mitochondria oxidative phosphorylation and Ca2+ signaling pathways, and then inducing breast cancer cell cycle arrest and apoptosis. Our research reveals the therapeutic value of IPA in breast cancer and provides a theoretical basis for the new treatment of breast cancer.