Palmatine

CAS# 3486-67-7

Palmatine

Catalog No. BCN5285----Order now to get a substantial discount!

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Quality Control of Palmatine

Number of papers citing our products

Chemical structure

Palmatine

3D structure

Chemical Properties of Palmatine

Cas No. 3486-67-7 SDF Download SDF
PubChem ID 19009 Appearance Yellow Powder
Formula C21H22NO4 M.Wt 352.4
Type of Compound Alkaloids Storage Desiccate at -20°C
Synonyms Berbericinine
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 2,3,9,10-tetramethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium
SMILES COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)OC)OC)OC
Standard InChIKey QUCQEUCGKKTEBI-UHFFFAOYSA-N
Standard InChI InChI=1S/C21H22NO4/c1-23-18-6-5-13-9-17-15-11-20(25-3)19(24-2)10-14(15)7-8-22(17)12-16(13)21(18)26-4/h5-6,9-12H,7-8H2,1-4H3/q+1
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 Palmatine

The rhizomes of Coptis chinensis Franch.

Biological Activity of Palmatine

DescriptionPalmatine shows significant antidepressant-like, anti-hyperlipidemia, hepatoprotective, and antioxidant effects, it inhibited MAO-A, I(K) and I(CRAC) activity, and activated the AhR-CYP1A pathway. Palmatine shows the strong toxic action on T. thermophila BF5 growth, it is toxic to insects and vertebrates and inhibited the multiplication of bacteria, fungi and viruses, it is active at the alpha 2-receptor ( IC50 of 956 nM).
TargetsP450 (e.g. CYP17) | MAO | NF-kB | LDL | DNA/RNA Synthesis | 5-HT Receptor | Adrenergic Receptor | AChR | Antifection | alpha 2-receptor
In vitro

Palmatine inhibits growth and invasion in prostate cancer cell: Potential role for rpS6/NFκB/FLIP.[Pubmed: 25043857]

Mol Carcinog. 2015 Oct;54(10):1227-34.

Novel agents are desperately needed for improving the quality of life and 5-year survival to more than 30% for metastatic castrate-resistant prostate cancer. Previously we showed that Nexrutine, Phellodendron amurense bark extract, inhibits prostate tumor growth in vitro and in vivo. Subsequently using biochemical fractionation we identified butanol fraction contributes to the observed biological activities.
METHODS AND RESULTS:
We report here that Palmatine, which is present in the butanol fraction, selectively inhibits growth of prostate cancer cells without significant effect on non-tumorigenic prostate epithelial cells. By screening receptor tyrosine kinases in a protein kinase array, we identified ribosomal protein S6, a downstream target of p70S6K and the Akt/mTOR signaling cascade as a potential target. We further show that Palmatine treatment is associated with decreased activation of NFκB and its downstream target gene FLIP. These events led to inhibition of invasion. Similar results were obtained using parent extract Nexrutine (Nx) suggesting that Palmatine either in the purified form or as one of the components in Nx is a potent cytotoxic agent with tumor invasion inhibitory properties. Synergistic inhibition of rpS6/NFκB/FLIP axis with Palmatine may have therapeutic potential for the treatment of prostate cancer and possibly other malignancies with their constitutive activation.
METHODS AND RESULTS:
These data support a biological link between rpS6/NFκB/FLIP in mediating Palmatine-induced inhibitory effects and warrants additional preclinical studies to test its therapeutic efficacy.

Effects of palmatine on potassium and calcium currents in isolated rat hepatocytes.[Pubmed: 12532460]

World J Gastroenterol. 2003 Feb;9(2):329-33.

To study the effects of Palmatine, a known inhibitor on delayed rectifier potassium current and L-type calcium current (I(Ca,L)) in guinea pig ventricular myocytes, on the potassium and calcium currents in isolated rat hepatocytes.
METHODS AND RESULTS:
Tight-seal whole-cell patch-clamp techniques were performed to investigate the effects of Palmatine on the delayed outward potassium currents (I(K)), inward rectifier potassium current (I(K1)) and Ca(2+) release-activated Ca(2+) current (I(CRAC)) in enzymatically isolated rat hepatocytes. Palmatine 0.3-100 microM reduced I(K) in a concentration-dependent manner with EC(50) of 41.62+/-10.11 microM and n(H), 0.48+/-0.07 (n=8). The effect of the drug was poorly reversible after washout. When the bath solution was changed to tetraethylammonium (TEA) 8 mM, IK was inhibited. Palmatine 10 microM and 100 microM shifted the I-V curves of I(K) downward, and the block of I(K) was voltage-independent. Palmatine 0.3-100 microM also inhibited I(CRAC) in a concentration-dependent manner. The fitting parameters were as follows: EC(50)=51.19+/-15.18 microM, and n(H)=0.46+/-0.07 (n=8). The peak value of I(CRAC) in the I-V relationship was decreased by Palmatine 10 microM and 100 microM. But the reverse potential of I(CRAC) occurred at Voltage=0 mV in all cells. Palmatine 0.3-100 microM failed to have any significant effect on either inward or outward components of I(K1) at any membrane potential examined.
CONCLUSIONS:
The inhibitory effects on I(K) and I(CRAC) could be one of the mechanisms that Palmatine exerts protective effect on hepatocytes.

In vivo

Action of palmatine on Tetrahymena thermophila BF5 growth investigated by microcalorimetry.[Pubmed: 19286310 ]

J Hazard Mater. 2009 Sep 15;168(2-3):609-13.


METHODS AND RESULTS:
Using a thermal activity monitor (TAM) air isothermal microcalorimeter with ampoule mode, the thermo-genic curves of the metabolism of Tetrahymena thermophila BF(5) growth at 28 degrees C were obtained and the action of Palmatine on it was investigated. Meanwhile, the biomass change during the process of T. thermophila BF(5) growth coexisted with Palmatine was studied by a haemacytometer. The results showed that a low concentration (50 microg/mL) of Palmatine began to inhibit the growth of T. thermophila BF(5), and when the concentration of Palmatine reached 600 microg/mL, T. thermophila BF(5) could not grow at all. The relationship between the growth rate constant (k) and the concentration c was almost linear with the correlation coefficient of 0.9957, showing the strong toxic action of Palmatine on T. thermophila BF(5) growth.
CONCLUSIONS:
The biomass during T. thermophila BF(5) growth decreased obviously by the addition of Palmatine at different concentrations. The investigation of biomass agreed well with the results obtained by means of microcalorimetry.

Protocol of Palmatine

Kinase Assay

Biochemical activities of berberine, palmatine and sanguinarine mediating chemical defence against microorganisms and herbivores.[Pubmed: 9004542]

Phytochemistry. 1997 Jan;44(2):257-66.

The alkaloids berberine, Palmatine and sanguinarine are toxic to insects and vertebrates and inhibit the multiplication of bacteria, fungi and viruses. Biochemical properties which may contribute to these allelochemical activities were analysed.
METHODS AND RESULTS:
Acetylcholine esterase, butyrylcholinesterase, choline acetyl transferase, alpha 1- and alpha 2-adrenergic, nicotinergic, muscarinergic and serotonin2 receptors were substantially affected. Sanguinarine appears to be the most effective inhibitor of choline acetyl-transferase (IC50 284 nM), while the protoberberines were inactive at this target. Berberine and Palmatine were most active at the alpha 2-receptor (binding with IC50 476 and 956 nM, respectively). Furthermore, berberine and sanguinarine intercalate DNA, inhibit DNA synthesis and reverse transcriptase. In addition, sanguinarine (but not berberine) affects membrane permeability and berberine protein biosynthesis.
CONCLUSIONS:
In consequence, these biochemical activities may mediate chemical defence against microorganisms, viruses and herbivores in the plants producing these alkaloids.

Cell Research

Palmatine activates AhR and upregulates CYP1A activity in HepG2 cells but not in human hepatocytes.[Pubmed: 24583342]

Toxicol In Vitro. 2014 Jun;28(4):693-9.

The protoberberine alkaloid Palmatine is present in preparations from medicinal plants such as Coptis chinensis and Corydalis yanhusuo.
METHODS AND RESULTS:
This study examined whether Palmatine affects the expression of cytochromes P450 (CYPs) 1A1 and 1A2 in primary cultures of human hepatocytes and human hepatoma HepG2 cells grown as monolayer or spheroids. Gene reporter assays showed that Palmatine significantly activated the aryl hydrocarbon receptor (AhR) and increased the activity of CYP1A1 gene promoter in transiently transfected HepG2 cells. In HepG2 monolayer culture, Palmatine also significantly increased mRNA and activity levels of CYP1A1, albeit with considerably less potency than 2,3,7,8-tetrachlorodibenzo-p-dioxin, a prototypical CYP1A inducer. On the other hand, CYP1A activity was not significantly elevated by Palmatine in HepG2 spheroids. Moreover, Palmatine induced mild or negligible changes in CYP1A1 and CYP1A2 mRNA expression without affecting CYP1A activity levels in primary human hepatocytes.
CONCLUSIONS:
It is concluded that Palmatine activates the AhR-CYP1A pathway in HepG2 monolayer, while the potential for CYP1A induction is irrelevant in cell systems which are closer to the in vivo situation, i.e. in HepG2 spheroids and primary cultures of human hepatocytes. Possible induction of CYP1A enzymes by Palmatine in vivo remains to be investigated.

Animal Research

Hypolipidemic Effect and Mechanism of Palmatine from Coptis chinensis in Hamsters Fed High-Fat diet.[Pubmed: 25586479]

Behavioral and biochemical evidences for antidepressant-like activity of palmatine in mice subjected to chronic unpredictable mild stress.[Pubmed: 24905299 ]

Pharmacol Rep. 2014 Feb;66(1):1-9.

In the present study, antidepressant-like activity of Palmatine was evaluated in unstressed and stressed young male Swiss albino mice.
METHODS AND RESULTS:
The animals were subjected to unpredictable mild stress daily for 21 successive days to induce depression-like behavior. Palmatine (0.25, 0.5, 1 mg/kg, ip) was administered for 21 successive days to unstressed and stressed mice. The antidepressant-like activity was evaluated using the tail suspension test, forced swim test and sucrose preference test. Palmatine (0.5 and 1 mg/kg, ip) significantly decreased immobility periods of unstressed and stressed mice in the forced swim test and tail suspension test, thus indicating its significant antidepressant-like activity. Only the highest dose (1 mg/kg) of Palmatine significantly reversed the stress-induced decrease in sucrose preference. There was no significant effect on locomotor activity of the mice by Palmatine and fluoxetine. The antidepressant-like activity of Palmatine was found to be comparable to fluoxetine (10 mg/kg) administered for successive 21 days. Palmatine (0.5 and 1 mg/kg, ip) significantly reversed the stress-induced increase in brain catalase levels, MAO-A activity, lipid peroxidation, plasma nitrite and corticosterone levels.
CONCLUSIONS:
Palmatine showed significant antidepressant-like activity in unstressed and stressed mice probably through inhibition of MAO-A activity, decrease in plasma nitrite levels and due to its antioxidant activity. In addition, Palmatine also showed antidepressant-like activity in stressed mice probably through decrease in plasma corticosterone levels.

Phytother Res. 2015 May;29(5):668-73.

Palmatine (PAL) is one of the main alkaloids in Coptis chinensis. The present aim was to investigate the hypolipidemic effect and mechanism of Palmatine in hamsters fed with high-fat diet (HFD).
METHODS AND RESULTS:
PAL treatment decreased serum total cholesterol (TC), triglyceride (TG), and low-density lipoprotein cholesterol (LDL-C) levels, as well as increased fecal excretion of TC and total bile acids (TBA) in hyperlipidemic hamsters. Furthermore, PAL treatment up-regulated low-density lipoprotein receptor (LDLR) and cholesterol 7α-hydroxylase (CYP7A1) mRNA and protein expression and down-regulated apical sodium-dependent bile salt transporter (ASBT) mRNA and protein expression. These results demonstrated that PAL as a potential natural cholesterol lowering agent works by up-regulating LDLR and CYP7A1 mRNA and protein expression, down-regulating ASBT mRNA and protein expression, as well as enhancing fecal excretion of TC and TBA.
CONCLUSIONS:
The findings in our study suggest that Palmatine could be a potential natural agent for treating hyperlipidemia.

Palmatine Dilution Calculator

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Preparing Stock Solutions of Palmatine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.8377 mL 14.1884 mL 28.3768 mL 56.7537 mL 70.9421 mL
5 mM 0.5675 mL 2.8377 mL 5.6754 mL 11.3507 mL 14.1884 mL
10 mM 0.2838 mL 1.4188 mL 2.8377 mL 5.6754 mL 7.0942 mL
50 mM 0.0568 mL 0.2838 mL 0.5675 mL 1.1351 mL 1.4188 mL
100 mM 0.0284 mL 0.1419 mL 0.2838 mL 0.5675 mL 0.7094 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 Palmatine

Biochemical activities of berberine, palmatine and sanguinarine mediating chemical defence against microorganisms and herbivores.[Pubmed:9004542]

Phytochemistry. 1997 Jan;44(2):257-66.

The alkaloids berberine, Palmatine and sanguinarine are toxic to insects and vertebrates and inhibit the multiplication of bacteria, fungi and viruses. Biochemical properties which may contribute to these allelochemical activities were analysed. Acetylcholine esterase, butyrylcholinesterase, choline acetyl transferase, alpha 1- and alpha 2-adrenergic, nicotinergic, muscarinergic and serotonin2 receptors were substantially affected. Sanguinarine appears to be the most effective inhibitor of choline acetyl-transferase (IC50 284 nM), while the protoberberines were inactive at this target. Berberine and Palmatine were most active at the alpha 2-receptor (binding with IC50 476 and 956 nM, respectively). Furthermore, berberine and sanguinarine intercalate DNA, inhibit DNA synthesis and reverse transcriptase. In addition, sanguinarine (but not berberine) affects membrane permeability and berberine protein biosynthesis. In consequence, these biochemical activities may mediate chemical defence against microorganisms, viruses and herbivores in the plants producing these alkaloids.

Palmatine inhibits growth and invasion in prostate cancer cell: Potential role for rpS6/NFkappaB/FLIP.[Pubmed:25043857]

Mol Carcinog. 2015 Oct;54(10):1227-34.

Novel agents are desperately needed for improving the quality of life and 5-year survival to more than 30% for metastatic castrate-resistant prostate cancer. Previously we showed that Nexrutine, Phellodendron amurense bark extract, inhibits prostate tumor growth in vitro and in vivo. Subsequently using biochemical fractionation we identified butanol fraction contributes to the observed biological activities. We report here that Palmatine, which is present in the butanol fraction, selectively inhibits growth of prostate cancer cells without significant effect on non-tumorigenic prostate epithelial cells. By screening receptor tyrosine kinases in a protein kinase array, we identified ribosomal protein S6, a downstream target of p70S6K and the Akt/mTOR signaling cascade as a potential target. We further show that Palmatine treatment is associated with decreased activation of NFkappaB and its downstream target gene FLIP. These events led to inhibition of invasion. Similar results were obtained using parent extract Nexrutine (Nx) suggesting that Palmatine either in the purified form or as one of the components in Nx is a potent cytotoxic agent with tumor invasion inhibitory properties. Synergistic inhibition of rpS6/NFkappaB/FLIP axis with Palmatine may have therapeutic potential for the treatment of prostate cancer and possibly other malignancies with their constitutive activation. These data support a biological link between rpS6/NFkappaB/FLIP in mediating Palmatine-induced inhibitory effects and warrants additional preclinical studies to test its therapeutic efficacy.

Palmatine activates AhR and upregulates CYP1A activity in HepG2 cells but not in human hepatocytes.[Pubmed:24583342]

Toxicol In Vitro. 2014 Jun;28(4):693-9.

The protoberberine alkaloid Palmatine is present in preparations from medicinal plants such as Coptis chinensis and Corydalis yanhusuo. This study examined whether Palmatine affects the expression of cytochromes P450 (CYPs) 1A1 and 1A2 in primary cultures of human hepatocytes and human hepatoma HepG2 cells grown as monolayer or spheroids. Gene reporter assays showed that Palmatine significantly activated the aryl hydrocarbon receptor (AhR) and increased the activity of CYP1A1 gene promoter in transiently transfected HepG2 cells. In HepG2 monolayer culture, Palmatine also significantly increased mRNA and activity levels of CYP1A1, albeit with considerably less potency than 2,3,7,8-tetrachlorodibenzo-p-dioxin, a prototypical CYP1A inducer. On the other hand, CYP1A activity was not significantly elevated by Palmatine in HepG2 spheroids. Moreover, Palmatine induced mild or negligible changes in CYP1A1 and CYP1A2 mRNA expression without affecting CYP1A activity levels in primary human hepatocytes. It is concluded that Palmatine activates the AhR-CYP1A pathway in HepG2 monolayer, while the potential for CYP1A induction is irrelevant in cell systems which are closer to the in vivo situation, i.e. in HepG2 spheroids and primary cultures of human hepatocytes. Possible induction of CYP1A enzymes by Palmatine in vivo remains to be investigated.

Behavioral and biochemical evidences for antidepressant-like activity of palmatine in mice subjected to chronic unpredictable mild stress.[Pubmed:24905299]

Pharmacol Rep. 2014 Feb;66(1):1-9.

BACKGROUND: In the present study, antidepressant-like activity of Palmatine was evaluated in unstressed and stressed young male Swiss albino mice. METHODS: The animals were subjected to unpredictable mild stress daily for 21 successive days to induce depression-like behavior. Palmatine (0.25, 0.5, 1 mg/kg, ip) was administered for 21 successive days to unstressed and stressed mice. The antidepressant-like activity was evaluated using the tail suspension test, forced swim test and sucrose preference test. RESULTS: Palmatine (0.5 and 1 mg/kg, ip) significantly decreased immobility periods of unstressed and stressed mice in the forced swim test and tail suspension test, thus indicating its significant antidepressant-like activity. Only the highest dose (1 mg/kg) of Palmatine significantly reversed the stress-induced decrease in sucrose preference. There was no significant effect on locomotor activity of the mice by Palmatine and fluoxetine. The antidepressant-like activity of Palmatine was found to be comparable to fluoxetine (10 mg/kg) administered for successive 21 days. Palmatine (0.5 and 1 mg/kg, ip) significantly reversed the stress-induced increase in brain catalase levels, MAO-A activity, lipid peroxidation, plasma nitrite and corticosterone levels. CONCLUSIONS: Palmatine showed significant antidepressant-like activity in unstressed and stressed mice probably through inhibition of MAO-A activity, decrease in plasma nitrite levels and due to its antioxidant activity. In addition, Palmatine also showed antidepressant-like activity in stressed mice probably through decrease in plasma corticosterone levels.

Action of palmatine on Tetrahymena thermophila BF5 growth investigated by microcalorimetry.[Pubmed:19286310]

J Hazard Mater. 2009 Sep 15;168(2-3):609-13.

Using a thermal activity monitor (TAM) air isothermal microcalorimeter with ampoule mode, the thermo-genic curves of the metabolism of Tetrahymena thermophila BF(5) growth at 28 degrees C were obtained and the action of Palmatine on it was investigated. Meanwhile, the biomass change during the process of T. thermophila BF(5) growth coexisted with Palmatine was studied by a haemacytometer. The results showed that a low concentration (50 microg/mL) of Palmatine began to inhibit the growth of T. thermophila BF(5), and when the concentration of Palmatine reached 600 microg/mL, T. thermophila BF(5) could not grow at all. The relationship between the growth rate constant (k) and the concentration c was almost linear with the correlation coefficient of 0.9957, showing the strong toxic action of Palmatine on T. thermophila BF(5) growth. The biomass during T. thermophila BF(5) growth decreased obviously by the addition of Palmatine at different concentrations. The investigation of biomass agreed well with the results obtained by means of microcalorimetry.

Effects of palmatine on potassium and calcium currents in isolated rat hepatocytes.[Pubmed:12532460]

World J Gastroenterol. 2003 Feb;9(2):329-33.

AIM: To study the effects of Palmatine, a known inhibitor on delayed rectifier potassium current and L-type calcium current (I(Ca,L)) in guinea pig ventricular myocytes, on the potassium and calcium currents in isolated rat hepatocytes. METHODS: Tight-seal whole-cell patch-clamp techniques were performed to investigate the effects of Palmatine on the delayed outward potassium currents (I(K)), inward rectifier potassium current (I(K1)) and Ca(2+) release-activated Ca(2+) current (I(CRAC)) in enzymatically isolated rat hepatocytes. RESULTS: Palmatine 0.3-100 microM reduced I(K) in a concentration-dependent manner with EC(50) of 41.62+/-10.11 microM and n(H), 0.48+/-0.07 (n=8). The effect of the drug was poorly reversible after washout. When the bath solution was changed to tetraethylammonium (TEA) 8 mM, IK was inhibited. Palmatine 10 microM and 100 microM shifted the I-V curves of I(K) downward, and the block of I(K) was voltage-independent. Palmatine 0.3-100 microM also inhibited I(CRAC) in a concentration-dependent manner. The fitting parameters were as follows: EC(50)=51.19+/-15.18 microM, and n(H)=0.46+/-0.07 (n=8). The peak value of I(CRAC) in the I-V relationship was decreased by Palmatine 10 microM and 100 microM. But the reverse potential of I(CRAC) occurred at Voltage=0 mV in all cells. Palmatine 0.3-100 microM failed to have any significant effect on either inward or outward components of I(K1) at any membrane potential examined. CONCLUSION: The inhibitory effects on I(K) and I(CRAC) could be one of the mechanisms that Palmatine exerts protective effect on hepatocytes.

Hypolipidemic Effect and Mechanism of Palmatine from Coptis chinensis in Hamsters Fed High-Fat diet.[Pubmed:25586479]

Phytother Res. 2015 May;29(5):668-73.

Palmatine (PAL) is one of the main alkaloids in Coptis chinensis. The present aim was to investigate the hypolipidemic effect and mechanism of Palmatine in hamsters fed with high-fat diet (HFD). PAL treatment decreased serum total cholesterol (TC), triglyceride (TG), and low-density lipoprotein cholesterol (LDL-C) levels, as well as increased fecal excretion of TC and total bile acids (TBA) in hyperlipidemic hamsters. Furthermore, PAL treatment up-regulated low-density lipoprotein receptor (LDLR) and cholesterol 7alpha-hydroxylase (CYP7A1) mRNA and protein expression and down-regulated apical sodium-dependent bile salt transporter (ASBT) mRNA and protein expression. These results demonstrated that PAL as a potential natural cholesterol lowering agent works by up-regulating LDLR and CYP7A1 mRNA and protein expression, down-regulating ASBT mRNA and protein expression, as well as enhancing fecal excretion of TC and TBA. The findings in our study suggest that Palmatine could be a potential natural agent for treating hyperlipidemia.

Description

Palmatine is an orally active and irreversible indoleamine 2,3-dioxygenase 1 (IDO-1) inhibitor. Palmatine can ameliorate DSS-induced colitis by mitigating colonic injury, preventing gut microbiota dysbiosis, and regulating tryptophan catabolism. Palmatine has the potential for colitis treatment.

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