Jatrorrhizine

CAS# 3621-38-3

Jatrorrhizine

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Quality Control of Jatrorrhizine

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Chemical structure

Jatrorrhizine

3D structure

Chemical Properties of Jatrorrhizine

Cas No. 3621-38-3 SDF Download SDF
PubChem ID 72323 Appearance Yellow powder
Formula C20H20NO4 M.Wt 338.4
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 2,9,10-trimethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium-3-ol
SMILES COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)O)OC)OC
Standard InChIKey MXTLAHSTUOXGQF-UHFFFAOYSA-O
Standard InChI InChI=1S/C20H19NO4/c1-23-18-5-4-12-8-16-14-10-19(24-2)17(22)9-13(14)6-7-21(16)11-15(12)20(18)25-3/h4-5,8-11H,6-7H2,1-3H3/p+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 Jatrorrhizine

The barks of Phellodendron chinense Schneid.

Biological Activity of Jatrorrhizine

DescriptionJatrorrhizine has neuroprotective, antioxidative, anti-inflammatory, antihypercholesterolemic, and anti-hyperglycemia effects.Jatrorrhizine is expected to be developed as a new gastric prokinetic drug, it is metabolized by human CYP1A2 and multiple UGT1A isoforms. It has inhibitory activities against the expression of inducible NO syntase (iNOS) and cyclooxygenase-2 (COX-2), and can improve the utilization and excretion of cholesterol by up-regulating the mRNA and protein expression of LDLR and CYP7A1.
TargetsLDL | P450 (e.g. CYP17) | NOS | COX | 5-HT Receptor | HMG-CoA Reductase
In vitro

Anti-inflammatory Effect of Jatrorrhizine from Phellodendron amurense in Lipopolysaccharide-stimulated Raw264.7 Cells.[Reference: WebLink]

J.Appl.Biol. Chem.,2011,54(2):.114-9.

n-Butanol extracts from Phellodendron amurense have about 50% inhibitory activity against hyaluronidase.
METHODS AND RESULTS:
The anti-inflammatory compound was isolated from P. amurense by Sephadex LH-20 and MCI-gel CHP-20 column chromatography with gradient elution. As a the result, its structure was identified as Jatrorrhizine by the interpretation of spectroscopic analyses including - and -NMR. In anti-inflammatory activity, the expression of nitric oxide (NO) was inhibited as above 60% at 100 concentration of extracts and then purified Jatrorrhizine from P. amurense. The inhibitory activities against the expression of inducible NO syntase (iNOS) and cyclooxygenase-2 (COX-2) were 45% and 29%.
CONCLUSIONS:
It seems that the extracts and purified Jatrorrhizine from P. amurense were expected anti-inflammatory effect in lipopolysaccharide (LPS)-stimulated Raw264.7 cells.

In vivo

The antihypercholesterolemic effect of jatrorrhizine isolated from Rhizoma Coptidis.[Pubmed: 24894270]

Phytomedicine. 2014 Sep 25;21(11):1373-81.


METHODS AND RESULTS:
Current work was conducted to evaluate the safety and antihypercholesterolemic activity of Jatrorrhizine extracted from Rhizoma Coptidis (RC) and its potential mechanism on regulating cholesterol metabolism. It was found that the LD50 of Jatrorrhizine in mice was more than 5,500 mg/kg and there were no influences on clinical signs, organ weight changes, urinalysis and hematological parameters, gross necropsy and histological alterations in Jatrorrhizine-treated rats during the 3-month period, compared to the control group. Jatrorrhizine showed a strong lipid-lowering effect in a dose-dependent manner. Oral administration of 70.05 mg/kg of Jatrorrhizine on Mesocricetus auratus (Syrian golden hamsters) exhibited significant decrease in TC, TG, and LDL-c levels by 20%, 43%, and 19%, respectively, and increase in HDL-c and total bile acids (TBA) content in feces (p<0.01), compared to high-fat and high-cholesterol (HFHC) group. Besides, Jatrorrhizine dose-dependently slowed the rate of weight gain. The results of qRT-PCR, western blotting and ELISA revealed that Jatrorrhizine significantly up-regulated the mRNA and protein expression of LDLR and CYP7A1, but exhibited no significant effect on mRNA and protein expression of HMGR and ASBT in hamsters.
CONCLUSIONS:
In conclusion, Jatrorrhizine was a safe and potential antihypercholesterolemic agent from RC which could improve the utilization and excretion of cholesterol by up-regulating the mRNA and protein expression of LDLR and CYP7A1.

Effect of jatrorrhizine on delayed gastrointestinal transit in rat postoperative ileus.[Pubmed: 22309273 ]

J. Pharm. Pharmacol., 2012, 64(3):413-9.

Postoperative ileus is major cause of postoperative complication and prolonged hospitalization. Jatrorrhizine, which is a protoberberine alkaloid isolated from the medicinal plants Berberis aristata and Coptis chinensis, has been found to increase contractility of gastric antral and ileum smooth muscles of rat gastrointestinal tract. We have investigated whether Jatrorrhizine could offset gastrointestinal transit in rat with postoperative ileus.
METHODS AND RESULTS:
Postoperative ileus was induced by laparotomy with intestinal manipulation under anaesthesia. Gastrointestinal transit was evaluated by measurement of gastric emptying, geometric centre and the migration of Evans blue. Postoperative ileus significantly delayed gastric emptying and intestinal transit. Jatrorrhizine dose-dependently (0.1, 0.3 and 1 mg/kg) offset delayed gastric emptying and intestinal transit (geometric centre and the migration of Evans blue) in postoperative ileus. Pretreatment of animals with atropine inhibited the action of Jatrorrhizine on gastric emptying and intestinal transit, but pretreatment of animals with SB204070 did not influence the effect of Jatrorrhizine on gastric emptying and intestinal transit in postoperative ileus.
CONCLUSIONS:
Jatrorrhizine offset postoperative ileus-induced delayed gastric emptying and intestinal transit in rats, an action mediated via the cholinergic pathway, but not involving activation of 5-HT(4) receptors.

Protocol of Jatrorrhizine

Kinase Assay

CYP450 1A2 and multiple UGT1A isoforms are responsible for jatrorrhizine metabolism in human liver microsomes.[Pubmed: 23299247 ]

Biopharm Drug Dispos. 2013 Apr;34(3):176-85.

Jatrorrhizine, one of the protoberberine alkaloids derived from the plant Coptis chinensis, is expected to be developed as a new gastric prokinetic drug, but its metabolic characteristics in humans remain unknown.
METHODS AND RESULTS:
This study characterized the phase I and phase II metabolites, metabolic kinetics, and cytochrome P450 (CYP) and UDP-glucuronosyltransferase (UGT) enzymes responsible for the metabolism of Jatrorrhizine in human liver microsomes (HLMs). Chemical inhibition in HLMs and metabolism by recombinant human CYP or UGT enzymes were employed to determine the key metabolic enzyme subtypes. In HLMs, demethyleneberberine (demethylated product) and Jatrorrhizine glucuronide were identified as the phase I and phase II metabolites, respectively. The enzyme kinetics for both demethylation and glucuronidation were fitted to the Michaelis-Menten equation. Demethylation was inhibited significantly by furafylline and predominantly catalysed by recombinant CYP1A2, whereas glucuronidation was inhibited by silibinin, quercetin, as well as 1-naphthol and catalysed by recombinant UGT1A1, UGT1A3, UGT1A7, UGT1A8, UGT1A9 and UGT1A10.
CONCLUSIONS:
These results showed that Jatrorrhizine is metabolized by human CYP1A2 and multiple UGT1A isoforms.

Animal Research

Effect of jatrorrhizine, berberine, Huanglian Decoction and compound-mimic prescription on blood glucose in mice.[Reference: WebLink]

Chinese Traditional & Herbal Drugs, 2005, 36(4):548-51.

To study the hypoglycemic activity of Jatrorrhizine (Jat) and compare the effects of Jat, berberine (Ber), Huanglian Decoction (HLD), and compounds-mimic prescription (Ber+Jat) on blood glucose level in mice.
METHODS AND RESULTS:
TLC-scanning method was adopted for the determination of Ber and Jat in HLD. Ber+Jat was made artificially according to the result of the TLC-scanning. Diabetic model mice were made by ip alloxan, diabetic and normal mice were given Jat, Ber, HLD, and Ber+Jat in different dose by ig and applied in the study. Blood glucose level was analyzed by spectrophotometry with glucose-oxidase. Jat, Ber, HLD, and Ber+Jat decreased blood glucose level of diabetic and normal mice at different degrees. HLD showed the most significant hypoglycemic activity. Jat also possessed the function of decreasing blood glucose, which was less than that of Ber at the same dose. There was no significant difference between Ber+Jat and Ber.
CONCLUSIONS:
It implies that there are some other hypoglycemic ingredients in HLD besides Ber and Jat. Jat has no evident synergistic or antagonistic action when coexisted with Ber in natural ratio.

Jatrorrhizine Dilution Calculator

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Preparing Stock Solutions of Jatrorrhizine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.9551 mL 14.7754 mL 29.5508 mL 59.1017 mL 73.8771 mL
5 mM 0.591 mL 2.9551 mL 5.9102 mL 11.8203 mL 14.7754 mL
10 mM 0.2955 mL 1.4775 mL 2.9551 mL 5.9102 mL 7.3877 mL
50 mM 0.0591 mL 0.2955 mL 0.591 mL 1.182 mL 1.4775 mL
100 mM 0.0296 mL 0.1478 mL 0.2955 mL 0.591 mL 0.7388 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 Jatrorrhizine

The antihypercholesterolemic effect of jatrorrhizine isolated from Rhizoma Coptidis.[Pubmed:24894270]

Phytomedicine. 2014 Sep 25;21(11):1373-81.

Current work was conducted to evaluate the safety and antihypercholesterolemic activity of Jatrorrhizine extracted from Rhizoma Coptidis (RC) and its potential mechanism on regulating cholesterol metabolism. It was found that the LD50 of Jatrorrhizine in mice was more than 5,500 mg/kg and there were no influences on clinical signs, organ weight changes, urinalysis and hematological parameters, gross necropsy and histological alterations in Jatrorrhizine-treated rats during the 3-month period, compared to the control group. Jatrorrhizine showed a strong lipid-lowering effect in a dose-dependent manner. Oral administration of 70.05 mg/kg of Jatrorrhizine on Mesocricetus auratus (Syrian golden hamsters) exhibited significant decrease in TC, TG, and LDL-c levels by 20%, 43%, and 19%, respectively, and increase in HDL-c and total bile acids (TBA) content in feces (p<0.01), compared to high-fat and high-cholesterol (HFHC) group. Besides, Jatrorrhizine dose-dependently slowed the rate of weight gain. The results of qRT-PCR, western blotting and ELISA revealed that Jatrorrhizine significantly up-regulated the mRNA and protein expression of LDLR and CYP7A1, but exhibited no significant effect on mRNA and protein expression of HMGR and ASBT in hamsters. In conclusion, Jatrorrhizine was a safe and potential antihypercholesterolemic agent from RC which could improve the utilization and excretion of cholesterol by up-regulating the mRNA and protein expression of LDLR and CYP7A1.

Effect of jatrorrhizine on delayed gastrointestinal transit in rat postoperative ileus.[Pubmed:22309273]

J Pharm Pharmacol. 2012 Mar;64(3):413-9.

OBJECTIVES: Postoperative ileus is major cause of postoperative complication and prolonged hospitalization. Jatrorrhizine, which is a protoberberine alkaloid isolated from the medicinal plants Berberis aristata and Coptis chinensis, has been found to increase contractility of gastric antral and ileum smooth muscles of rat gastrointestinal tract. We have investigated whether Jatrorrhizine could offset gastrointestinal transit in rat with postoperative ileus. METHODS: Postoperative ileus was induced by laparotomy with intestinal manipulation under anaesthesia. Gastrointestinal transit was evaluated by measurement of gastric emptying, geometric centre and the migration of Evans blue. KEY FINDINGS: Postoperative ileus significantly delayed gastric emptying and intestinal transit. Jatrorrhizine dose-dependently (0.1, 0.3 and 1 mg/kg) offset delayed gastric emptying and intestinal transit (geometric centre and the migration of Evans blue) in postoperative ileus. Pretreatment of animals with atropine inhibited the action of Jatrorrhizine on gastric emptying and intestinal transit, but pretreatment of animals with SB204070 did not influence the effect of Jatrorrhizine on gastric emptying and intestinal transit in postoperative ileus. CONCLUSIONS: Jatrorrhizine offset postoperative ileus-induced delayed gastric emptying and intestinal transit in rats, an action mediated via the cholinergic pathway, but not involving activation of 5-HT(4) receptors.

CYP450 1A2 and multiple UGT1A isoforms are responsible for jatrorrhizine metabolism in human liver microsomes.[Pubmed:23299247]

Biopharm Drug Dispos. 2013 Apr;34(3):176-85.

Jatrorrhizine, one of the protoberberine alkaloids derived from the plant Coptis chinensis, is expected to be developed as a new gastric prokinetic drug, but its metabolic characteristics in humans remain unknown. This study characterized the phase I and phase II metabolites, metabolic kinetics, and cytochrome P450 (CYP) and UDP-glucuronosyltransferase (UGT) enzymes responsible for the metabolism of Jatrorrhizine in human liver microsomes (HLMs). Chemical inhibition in HLMs and metabolism by recombinant human CYP or UGT enzymes were employed to determine the key metabolic enzyme subtypes. In HLMs, demethyleneberberine (demethylated product) and Jatrorrhizine glucuronide were identified as the phase I and phase II metabolites, respectively. The enzyme kinetics for both demethylation and glucuronidation were fitted to the Michaelis-Menten equation. Demethylation was inhibited significantly by furafylline and predominantly catalysed by recombinant CYP1A2, whereas glucuronidation was inhibited by silibinin, quercetin, as well as 1-naphthol and catalysed by recombinant UGT1A1, UGT1A3, UGT1A7, UGT1A8, UGT1A9 and UGT1A10. These results showed that Jatrorrhizine is metabolized by human CYP1A2 and multiple UGT1A isoforms.

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