5,6-Dihydro-9-hydroxy-10-methoxybenzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium chloride
berberrubine
CAS: 15401-69-1
Molecular Formula: C19H16ClNO4
5,6-Dihydro-9-hydroxy-10-methoxybenzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium chloride - Names and Identifiers
5,6-Dihydro-9-hydroxy-10-methoxybenzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium chloride - Physico-chemical Properties
| Molecular Formula | C19H16ClNO4 |
| Molar Mass | 357.78764 |
| Density | 1.45g/cm3 |
| Melting Point | 245℃ (DEC.) |
| Boling Point | 596.9°C at 760 mmHg |
| Flash Point | 314.8°C |
| Solubility | Soluble in acidic solution, insoluble in petroleum ether, chloroform and other solvents. |
| Vapor Presure | 4.28E-15mmHg at 25°C |
| Appearance | Red needle crystal |
| Color | Off-White to Dark Yellow |
| Storage Condition | Hygroscopic, -20°C Freezer, Under inert atmosphere |
| Stability | Hygroscopic |
| Refractive Index | 1.724 |
| MDL | MFCD01658905 |
| Physical and Chemical Properties | Soluble in acidic solution, insoluble in petroleum ether, chloroform and other solvents. It is derived from the root of thaliictum polygamun Muhl. |
5,6-Dihydro-9-hydroxy-10-methoxybenzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium chloride - Reference
| Reference Show more | 1. Wang, Kun, et al. "Metabolites identification of berberine in rats using ultra-high performance liquid chromatography/quadrupole time-of-flight mass spectrometry." Journal of pharmaceutical and biomedical analysis 139 (2017): 73-86.https://doi.org/10.1016/ 2. Zhu, Jianzhong, et al. "In-vitro inhibitory effects of flavonoids in Rosa roxburghii and R. sterilis fruits on α-glucosidase: Effect of stomach digestion on flavonoids alone and in combination with acarbose." Journal of Functional Foods 54 (2019): 13-21.ht 3. [IF=4.411] Jinjun Shan et al."Liquid Chromatography Coupled with Linear Ion Trap Hybrid OrbitrapMass Spectrometry for Determination of Alkaloids in Sinomeniumacutum."Molecules. 2018 Jul;23(7):1634 4. [IF=3.935] Kun Wang et al."Metabolites identification of berberine in rats using ultra-high performance liquid chromatography/quadrupole time-of-flight mass spectrometry."J Pharmaceut Biomed. 2017 May;139:73 5. [IF=2.882] Kun Wang et al."Identification of berberrubine metabolites in rats by using ultra-high performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry."Fitoterapia. 2018 Jan;124:23 6. [IF=5.81] Xinchi Feng et al."Pharmacokinetics and Excretion of Berberine and Its Nine Metabolites in Rats."Front Pharmacol. 2020; 11: 594852 7. [IF=1.902] Xinchi Feng et al."Systematic screening and characterization of absorbed constituents and in vivo metabolites in rats after oral administration of Rhizoma coptidis using UPLC-Q-TOF/MS."Biomed Chromatogr. 2020 Oct;34(10):e4919 8. [IF=1.345] Ya-Li Zhang et al."Coptisine suppresses proliferation and inhibits metastasis in human pancreatic cancer PANC-1 cells."J Asian Nat Prod Res. 2020;22(5):452-463 |
5,6-Dihydro-9-hydroxy-10-methoxybenzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium chloride - Reference Information
| alkaloid | berberine is first an alkaloid isolated from Berberise Vulgaris l. and can also be isolated from Coptis chinensis. due to the low content of berberine in Chinese herbal medicines such as Coptis chinensis, it has not been taken seriously. |
| plant extraction berberine | due to the low natural content of berberine in coptis chinensis, phellodendron and other original medicinal materials, it is difficult to extract, separate and purify from the original medicinal materials. now, berberine demethylation is generally used to produce berberine. Phellodendron amurense is the dry bark of the rutaceae plant yellow bark. It was first published in the "Shen Nong's Materia Medica" and was listed as the top grade. It has the effects of clearing heat and dampness, purging fire and steaming, detoxifying and healing sores. Ancient books of traditional Chinese medicine record several kinds of processed products such as honey-roasted phellodendron, wine-roasted phellodendron, salt-roasted phellodendron, phellodendron charcoal, etc. The "Chinese Pharmacopoeia" (2005 edition) contains salt-roasted phellodendron and phellodendron charcoal. Figure 2 is a physical picture of the plant Phellodendron amurense. |
| synthesis method | 1. vacuum pyrolysis: BBR is heated at a vacuum of 190 ℃ for 15 min, crude product is recrystallized with ethanol/methanol, and the yield is 69%; Or react for 1~2 h, and the crude product is subjected to chloroform/methanol 9: 1 silica gel column chromatography with a yield of 90%. 2. microwave radiation method: add a certain amount of BBR and DMF with a solid-liquid ratio of 1 ∶ 25(g: mL) into a round bottom flask, several zeolites are refluxed and condensed, and react for 15 min under 400 W microwave radiation. Take out the reaction bottle, add 1.5 times the water to dilute and cool while it is hot, refrigerate overnight, make the crystallization complete, filter and dry to obtain red needle crystals with a yield of about 72%; the filtrate is separated by a PiPo-02 macroporous resin column, and then used 40%, 45%, 50%, 55%, 60%, 65% and 70% methanol elution, collect the 70% methanol elution site, concentrate to obtain red needle crystals with a yield of about 21%; the total yield of the product is about 93%, and the purity is ≥ 98%. 3. pyridine hydrochloride melting method: berberine hydrochloride and pyridine hydrochloride are heated at 160~170 ℃ to remove berberine from methyl to obtain berberine. However, this method has no selectivity in demethylation, and berberine structure has-OCH3 at 9-and 10-positions, so this method produces more by-products and is less used in practical work. 4. urea method: berberine hydrochloride and urea are heated and reacted at 200 ℃ to produce berberine. there are many reaction by-products in this method, and subsequent purification is quite difficult. it is recommended not to use it. 5. aluminum trichloride method: demethylation of aluminum trichloride is a common classical method. the specific operation is to dissolve berberine in toluene, then add anhydrous A1C13, and heat reflux at 110 ℃ for 1 h to smoothly produce berberine. 6. First esterification followed by hydrolysis method: First, berberine hydrochloride is refluxed with newly distilled acetic anhydride and pyridine hydrochloride to produce berberine esterified 9-O-acetyl berberberine, and then the product is hydrolyzed in NaOH alkaline aqueous solution to obtain berberine. Since the intermediate product 9-O-acetyl berberis red alkali obtained by this method is easy to separate, the problem of many by-products of the simple pyridine hydrochloride melting method is eliminated to a certain extent. |
| analysis method | 1.YMC-Pack ODS-AQ column (250mm × 4.6mm,5 μm); Mobile phase: acetonitrile-0.2% formic acid aqueous solution (25: 75); Column temperature: 30 ℃; Flow rate: 1 mL/min; Detection wavelength: 265 nm. 2. agilent TC-C18(150mm × 4.6mm,5 μm); Elution phase: acetonitrile-0.1% phosphoric acid solution (50:50)( SDS 0.1g/100 mL); The detection wavelength is 265nm. |
| conversion | at 40min baking time, with the increase of temperature, some berberine hydrochloride in the baked products is converted into berberine, and the content of berberine increases, reaching the highest at 180 ℃. With the increase of baking time, the content of berberine hydrochloride decreased, and the content of berberine increased first, reached the peak at 60min, and then decreased. |
| pharmacological activity | 1, antibacterial activity: berberine alkaloids isolated from Coptis chinensis or Cortex Phellodendri have antibacterial activity of different sizes. the inhibitory activity of these compounds against gram-positive bacteria is much stronger than that against gram-negative bacteria. Berberine also has certain in vitro antibacterial activity. The structure-activity relationship of its antibacterial activity is: the presence of 9-position substituent of berberine molecule has a great influence on its antibacterial activity, such as 9-position lipophilic substituent The presence of the group will greatly enhance its in vitro activity, so the in vitro antibacterial activity of berberine and palmatine (9-position OH without substitution) is weaker than berberine. 2, anti-tumor activity: Hoshi et al. found that berberine and its 9-hydroxyl esterified derivatives have strong anti-tumor activity in vitro. Studies believe that berberine 9-hydroxyl is beneficial to anti-tumor activity. The results of anti-tumor studies on 4 kinds of tumors (S-180,NF sarcoma, Ehrlich carcinoma and L-1210) experimental mice show that berberine has good anti-tumor activity in vivo, and berberine 9-OH is the necessary structure for these compounds to show anti-tumor activity. 3, cardiovascular pharmacological activity: Berberine is mainly used as a calcium blocker to produce antihypertensive and antiarrhythmic effects, and also has an effect on Na channel or K channel. In recent years, the lipid-lowering activity of berberine has attracted more attention. Because its mechanism of action is completely different from statins and has good safety, it is considered to be a new target drug that is expected to replace statins. |
| toxicology | 1. acute toxicity LD50: the LD50 of berberine is 154.02 mg/kg. compared with the LD50 value of berberine hydrochloride (763.5 mg/kg), the LD50 value of berberine is much smaller. the results show that the toxicity of berberine is much greater than berine. The kidney was found to be abnormal when the internal organs of the mice died in the later period. It was initially suspected that berberine was toxic to kidney damage. 2. Daily behavior: compared with the control group, the daily behavior of the rats in the berberine group did not change significantly at the initial stage of administration, but on the 5th day of administration, it was found that most of the rats in the berberine group were depressed and their appetite began to decline. On the 10th day, hematuria in rats in the berberine group was visible to the naked eye. On the 16th day, 3 rats in the berberine group died. At the end of the experiment, 6 rats in the berberine group died pathologically. 3. visceral observation: Berberine had no obvious effect on the ratio of thymus, liver and spleen of experimental rats, but had obvious effect on kidney, which was significantly different from that of control group. The visceral ratio of the kidney of the rats in the berberine group was about 3 times that of the control group. All experimental rats in the Berberine group were found to have obvious swelling of both kidneys, and both kidneys were diffuse yellow granules, which were directly judged to be severely damaged kidneys. |
| Metabolism | The two-way transport Papp values of coptis hydrochloride (COP) and berberine (BRB) are both on the order of 10-5. It is inferred that they are all well transported compounds. The PappA-B/PappB-A value of BRB is between 0.5 and 2.0, and the degree of bidirectional transport is not different, which indicates that its transport pathway in Caco-2 cell model may be mainly transcellular passive transport, but from the ratio point of view, the transport from BL end to AP end is slightly dominant. Since the absorption of COP from the intestinal lumen side into the systemic circulation is absolutely dominant, and the transport of berberine from the systemic circulation side back to the intestinal lumen side is slightly dominant, the net absorption of COP will be higher than that of BRB. References: Ma Lian, Yang Xiuwei. Absorption of copberine hydrochloride and berberine in human Caco-2 cell monolayer model [J]. Chinese Journal of Traditional Chinese Medicine, 2007,23:2523-2527. |
| storage method | 2-8 ℃, stored in dark and at low temperature. |
| use | used for content determination/identification/pharmacological experiments, etc. Pharmacological effect: antibacterial effect. |
Last Update：2024-04-09 21:00:56
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View History
5,6-Dihydro-9-hydroxy-10-methoxybenzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium chloride
433703-10-7
901397-84-0
2-bromo-6,7-dihydrothieno[3,2-c]pyridin-4(5H)-one
1080467-52-2
(35Cl)Sodium chloride
2-chloro-3,5-dimethylpyridine
2(3H)-Furanone, dihydro-5-phenyl-4-(phenylthio)-
6-Iodo-8-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid
Linotroban
433703-10-7
901397-84-0
2-bromo-6,7-dihydrothieno[3,2-c]pyridin-4(5H)-one
1080467-52-2
(35Cl)Sodium chloride
2-chloro-3,5-dimethylpyridine
2(3H)-Furanone, dihydro-5-phenyl-4-(phenylthio)-
6-Iodo-8-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid
Linotroban