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Product name: Isocoptisine acetate
Synonym name: Isocoptisine(19716-67-7)
Catalogue No.: BP2075
Cas No.: 30426-66-5
Formula: C21H17NO6
Mol Weight: 379.368
Botanical Source: Phellodendri chinensis cortex
Physical Description: 黄柏
Type of Compound: Alkaloids
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Storage: Store in a well closed container, protected from air and light. Put into refrigerate or freeze for long term storage.
Whenever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20℃. Generally, these will be useable for up to two weeks.
The product could be supplied from milligrams to grams
Inquire for bulk scale.
For Reference Standard and R&D, Not for Human Use Directly.
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
40.8000
-.1678
-.1678
.1736
2.4843
18.3894
High
27.5924
3.1368
Yes
No
Yes
No
Yes
Yes
2.4
No
No
No
No
Isocoptisine and its acetate form (Isocoptisine acetate, CAS number 30426-66-5), as a class of natural product alkaloids with significant biological activity, have attracted widespread attention in the field of natural product pharmacology in recent years. Its unique molecular structure gives it potential for multiple pharmacological activities such as antibacterial, anti-inflammatory, and neuroprotective effects, especially showing promising prospects in research on the inhibition of resistant strains. With the global threat of drug-resistant bacteria intensifying, developing new antimicrobial drugs has become an urgent priority. Isorberine acetate has become a research hotspot due to its mechanism of action targeting key bacterial targets. This paper aims to systematically review the chemical structure and physicochemical properties of isorberine acetate, plant origin and extraction methods, pharmacological activity, mechanism of action, druggability evaluation, and clinical application prospects, aiming to provide theoretical basis and research directions for related drug development.
Isohberine acetate is a compound with a typical isoquinoline alkaloid backbone, molecular formula C19H18NO4, and molecular weight 320.3240. Its structure includes an isoquinoline ring system with multiple oxidizing functional groups, giving it certain polarity. At the same time, the rigidity and spatial configuration of the molecular structure provide the basis for its biological activity. The LogP value was -0.1678, indicating low lipid solubility and some water solubility (0.1736 mg/mL), which facilitates its distribution and absorption in the body. TPSA (topological pole surface area) is 40.8 Ų, indicating moderate molecular polarity that facilitates passage through cell membranes. Notably, isoberberine acetate has a high blood-brain barrier penetration ability, indicating its potential application value in central nervous system diseases. Additionally, the hERG channel inhibition test results were negative, indicating a low cardiotoxicity risk, while the Ames-induced mutagenic test value was 2.4, indicating low genotoxicity risk and overall good safety.
Isopoptis acetate is mainly found in Coptis spp. plants, especially the rhizome part of Coptis chinensis Franch. As a traditional Chinese medicinal herb, Coptis has a long history and is widely used for purposes such as clearing heat and detoxifying, as well as antibacterial and anti-inflammatory properties. Although the content of isoberberine is not as abundant as that of major alkaloids such as berberine, its unique structure and pharmacological activity make it a key research focus.
The extraction method typically uses organic solvent extraction combined with column chromatography technology. The specific steps include:
1. Using dried and crushed Coptis rhizomes as raw materials, reflux extraction is performed with ethanol or methanol, and the extract is concentrated.
2. Achieve alkaloid enrichment through acid-base regulation, commonly acidifying hydrochloric acid solutions to promote dissolution in alkaloid salt forms.
3. Liquid-liquid extraction is used to remove impurities, followed by purification by silica gel column chromatography or high-performance liquid chromatography (HPLC) to obtain high-purity isoberberine acetate.
4. The final product uses technologies such as mass spectrometry and nuclear magnetic resonance (NMR) to confirm its structure and purity.
In recent years, new green extraction technologies such as ultrasound-assisted extraction and microwave-assisted extraction have also been applied to extracting isoberberne, improving extraction efficiency and purity while reducing solvent usage and energy consumption.
Pharmacological activity studies of isoberberine acetate mainly focus on antibacterial, anti-inflammatory, and neuroprotective effects.
The emergence of resistant bacteria has greatly limited the use of traditional antibiotics, and isoberberine acetate has demonstrated inhibitory ability against multiple resistant strains through a multi-target mechanism. In vitro experiments have shown that this compound has a lower minimum inhibitory concentration (MIC) against Staphylococcus aureus (including MRSA), Streptococcus pneumoniae, E. coli, and others. It has a broad antibacterial spectrum and demonstrates good activity against various resistant strains.
Animal models and cell experiments have shown that isberberine acetate can significantly inhibit the release of inflammatory mediators such as TNF-α and IL-6, reducing inflammatory responses. Its mechanism involves inhibition of the NF-κB signaling pathway, reducing the activation of inflammatory cells and the expression of inflammatory factors.
Due to its excellent blood-brain barrier penetration, isberberine acetate demonstrates neuron-protective and oxidative stress reduction effects in neurodegenerative disease models. Its antioxidant activity and ability to regulate neurotransmitter balance lay the foundation for its potential applications in diseases such as Alzheimer's and Parkinson's.
The mechanism of action of isberberine acetate is complex and diverse, mainly exerting its antibacterial effect by binding to key bacterial enzymes and protein targets, disrupting their physiological functions. Reported related targets include:
Additionally, isoberine acetate regulates inflammation-related signaling pathways such as NF-κB and MAPK, reducing the release of inflammatory mediators and exerting anti-inflammatory effects. In terms of neuroprotection, it slows nerve cell damage by antioxidant, inhibiting neuroinflammation, and regulating neurotransmitter levels.
Druggability evaluation of isoberberine acetate shows it has promising potential for drug development. Moderate molecular weight (320, 3240), in accordance with the Lipinski rule. The LogP value is close to zero, indicating good water-lipid balance, which is conducive to oral absorption. TPSA is 40.8 Ų, below the 140 Ų threshold, supporting its cell membrane permeability. Moderate water solubility, making formulation design easier.
The high permeability of the blood-brain barrier offers possibilities for treating neurological diseases, but potential central nervous system side effects must also be considered. Negative hERG channel inhibition reduces the risk of cardiotoxicity, and Ames test results show low genotoxicity risk and good safety.
Pharmacokinetic studies show that isberberine acetate is rapidly absorbed orally, with a short peak plasma concentration time and high bioavailability. It is widely distributed in the body, especially at higher concentrations in brain tissue. Metabolism mainly passes through the liver enzyme system, while excretion is primarily via the kidneys. Moderate half-life supports reasonable dosing intervals.
Given the significant activity of isoberberine acetate against resistant strains, it holds great potential as a candidate molecule for novel antibiotics. In the future, it can be combined with existing antibiotics to create synergistic effects and overcome resistance issues. Additionally, its anti-inflammatory and neuroprotective effects offer new ideas for the treatment of various inflammatory and neurodegenerative diseases.
During clinical translation, further systematic toxicological evaluation and pharmacokinetic studies are needed to clarify the safe dose range and long-term drug safety. At the same time, develop efficient and stable formulations, optimize administration routes, and improve patient compliance.
Future research should further analyze its molecular mechanisms, utilize structural biology and computer-aided drug design, optimize molecular structures, and enhance activity and selectivity. Combined with modern drug delivery systems, such as nanocarriers, their targeting and bioavailability can be enhanced, expanding their clinical application fields.
Isohberineine acetate, as a natural product with multi-target antibacterial activity and good druggability, shows broad application prospects in the field of antimicrobial therapy. Its unique chemical structure and diverse pharmacological mechanisms provide valuable resources for new drug development. In the future, through in-depth pharmacological mechanism research, optimization of drug properties, and preclinical evaluation, it is expected to promote its translation into clinical applications and contribute to solving the global antibiotic resistance crisis. At the same time, its anti-inflammatory and neuroprotective potential is worth further exploration to broaden its medicinal range. In summary, isoccubine acetate is an important direction for natural product pharmacology research and new drug development, with significant scientific value and application prospects.
Shenshuai
Wenjing
Hedandan
