Product name: 6-Methoxyldihydrochelerythrine
Synonym name: (±)-6-Methoxyldihydrochelerythrine;(±)-13-Methoxydihydrochelerythrine;(±)-Angoline；CAS:49702-49-0
Catalogue No.: BP2133
Cas No.: 21080-31-9
Formula: C22H21NO5
Mol Weight: 379.412
Botanical Source: Macleaya cordata (Willd.) R. Br.
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.
HPLC of 6-Methoxyldihydrochelerythrine
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
49.3900
4.0782
4.0779
.0007
6.9523
27.8547
High
89.1051
3.2308
Yes
No
Yes
No
Yes
Yes
1.8
Yes
No
Yes
Yes
6-methoxydihydrochelerythrine (CAS number: 21080-31-9) is an important benzophenanthrene alkaloid that has attracted much attention due to its unique chemical structure and diverse biological activities. Benzophenanthridine alkaloids are widely present in the plant kingdom, especially in poppy plants, and have significant pharmacological activities such as anti-tumor, anti-inflammatory, antibacterial, and neuroprotective effects. 6-methoxydihydroquercetin, as a derivative of this class of compounds, has gradually demonstrated its potential clinical application value in the field of natural product pharmacology in recent years, especially in the treatment research of malignant tumors such as gastric cancer, showing good prospects.
Gastric cancer is one of the digestive system malignancies with high incidence rate and mortality worldwide. Traditional treatment methods include surgery, radiotherapy and chemotherapy, but the efficacy is limited and side effects are significant. Molecular targeted therapy for gastric cancer has become a current research hotspot. 6-methoxydihydroquercetin exhibits the potential to inhibit tumor cell proliferation, induce apoptosis, and reverse drug resistance by regulating various molecular targets closely related to the occurrence and development of gastric cancer, such as BCL2, STAT3, ABCB1, etc., suggesting its application value in the treatment of gastric cancer.
This article will provide a systematic review of the chemical structure and physicochemical properties, plant sources and extraction methods, pharmacological activity and mechanism of action of 6-methoxydihydroquercetin, combined with drug evaluation and pharmacokinetic characteristics, to explore its prospects and challenges in clinical applications. The aim is to provide theoretical basis and research direction for the in-depth study and drug development of this natural product.
6-methoxydihydroquercetin belongs to the benzophenanthridine alkaloid class, with a molecular formula of C22H23NO4 and a molecular weight of 379.4120. The core of its structure is the benzophenanthrene skeleton, which contains methoxy substituents and hydrogenation modifications, endowing it with unique spatial configuration and electronic distribution characteristics. The LogP value of this compound is 4.0782, indicating its high lipophilicity, which is beneficial for penetrating cell membranes and the blood-brain barrier (BBB penetration is high). This has positive implications for the therapeutic potential of central nervous system diseases.
Its polar surface area (TPSA) is 49.3900, which belongs to the moderate polarity range and has a certain degree of water solubility and lipid solubility. The actual water solubility is extremely low (0.0007 mg/mL), indicating the need to consider solubility enhancement strategies in drug formulation design. The negative result of hERG channel inhibition experiment indicates a low risk of cardiac toxicity and good safety. The Ames test result is 1.8, indicating a low risk of genotoxicity and meeting the basic requirements for drug safety.
Overall, 6-methoxydihydroquercetin has good drug compatibility and safety foundation, making it suitable for further pharmacological and pharmacokinetic studies.
6-methoxydihydroquercetin mainly exists in the genus Chelidonium spp. of the family Papaveraceae, especially in the rhizomes and aboveground parts of Chelidonium majus L. As a traditional Chinese medicinal herb, Bai Qu Cai has always been used to treat liver and gallbladder diseases, digestive system inflammation, and tumors. Benzophenanthridine alkaloids are its main active ingredients.
The common methods for extracting 6-methoxydihydroquercetin include:
Solvent extraction method Using organic solvents such as methanol, ethanol, or ethyl acetate to extract dried plant materials, combined with ultrasound assisted or reflux extraction, to improve extraction efficiency.
Liquid-liquid distribution method Using solvents of different polarities for layered extraction, removing impurities, and enriching target alkaloids.
Chromatographic separation and purification Further purify 6-methoxydihydroquercetin by techniques such as silica gel column chromatography and reverse phase high-performance liquid chromatography (RP-HPLC) to ensure its high purity and structural integrity.
In recent years, the application of supercritical CO2 extraction and molecular imprinting technology has also provided new ideas for the efficient extraction and purification of this compound, which is expected to achieve industrial scale production.
The pharmacological activity research of 6-methoxydihydroquercetin mainly focuses on the anti-tumor field, especially its inhibitory effect on gastric cancer cells. Multiple in vitro cell experiments and in vivo animal model studies have shown that this compound can significantly inhibit the proliferation, migration, and invasion of gastric cancer cells, induce cell cycle arrest and apoptosis.
In addition, 6-methoxydihydroquercetin also exhibits the following pharmacological activities:
Anti multidrug resistance (MDR) effect By regulating the expression of ABC transporters (such as ABCB1), the resistance of tumor cells to chemotherapy drugs can be reversed, and chemotherapy sensitivity can be improved.
anti-inflammatory effect Inhibiting the release of inflammatory mediators and reducing the inflammatory response in the tumor microenvironment can help suppress tumor progression.
Antioxidant effect Activate the NFE2L2 signaling pathway, enhance cellular antioxidant defense capabilities, and protect cells from oxidative stress damage.
These multi-target and multi mechanism pharmacological properties make 6-methoxydihydroquercetin a potential candidate molecule for multifunctional anticancer drugs.
6-methoxydihydroquercetin regulates the biological behavior of gastric cancer cells through multiple signaling pathways, mainly involving the following key molecular targets:
BCL2 and BCL2L1 As anti apoptotic proteins, BCL2 family members play a central role in tumor cell survival. 6-methoxydihydroquercetin can downregulate the expression of BCL2 and BCL2L1, and promote mitochondrial mediated apoptosis.
STAT3 Signal transducer and activator of transcription factor 3 (STAT3) plays an important role in tumor cell proliferation, immune escape, and inflammatory response. This compound inhibits the phosphorylation activation of STAT3, blocks its transcriptional function, and suppresses tumor progression.
ABCB1 As a multidrug resistance associated protein, ABCB1 reduces intracellular drug concentration through drug efflux. 6-methoxydihydroquercetin inhibits the expression and function of ABCB1, reversing the drug-resistant phenotype.
NFE2L2（NRF2）Key transcription factors that regulate cellular antioxidant stress response. This compound activates the NFE2L2 signaling pathway, enhancing the cell's resistance to oxidative damage.
TOP1 Topoisomerase I is an important enzyme for DNA replication and transcription. 6-methoxydihydroquercetin inhibits TOP1 activity, blocks tumor cell DNA metabolism, and suppresses cell proliferation.
MAPK1 and PIK3CA Belonging to key members of the MAPK and PI3K signaling pathways respectively, they regulate cell growth, differentiation, and survival. This compound affects the biological behavior of tumor cells by regulating these two pathways.
MMP9 Matrix metalloproteinase 9 is involved in matrix degradation and metastasis of tumor cells. 6-methoxydihydroquercetin inhibits MMP9 expression and reduces the invasive ability of tumor cells.
In summary, 6-methoxydihydroquercetin regulates the proliferation, apoptosis, migration, and drug resistance of tumor cells through multi-target synergistic effects, demonstrating its potential as an anti gastric cancer drug.
Medicinal properties are an important consideration in the development of natural product drugs. The pharmacological parameters of 6-methoxydihydroquercetin are as follows:
Molecular weight (379.4120)The ideal range that complies with Lipinski's rules is beneficial for oral absorption.
LogP（4.0782）This indicates that it has good lipid solubility, which is conducive to cell membrane penetration, but excessive solubility may affect water solubility and bioavailability.
TPSA（49.3900）Moderate, helps balance polarity and lipophilicity, and promotes drug absorption.
Very low water solubility (0.0007 mg/mL)This poses challenges for the development of its formulations, requiring the use of nanocarriers, solid dispersions, and other technologies to improve solubility.
High blood-brain barrier penetration It is suggested that it may be used for central nervous system related diseases, but potential neurotoxicity should also be considered.
HERG inhibition negative Reduce the risk of cardiac toxicity.
Ames test value 1.8 It shows a low risk of genotoxicity.
In terms of pharmacokinetics, existing research is relatively limited, but based on its chemical properties, it is speculated that 6-methoxydihydroquercetin may experience first pass effects in the liver after oral administration, and its high lipid solubility is beneficial for tissue distribution. In the future, systematic research on in vivo absorption, distribution, metabolism, and excretion (ADME) is needed to clarify its pharmacokinetic characteristics and safety indicators.
6-methoxydihydroquercetin, as a natural product with multi-target anti-tumor activity, has shown increasing potential in the treatment of gastric cancer. Its mechanism of action covers tumor cell proliferation inhibition, apoptosis induction, drug resistance reversal, and tumor microenvironment regulation, which is in line with modern precision medicine and multi-target therapy concepts.
The future clinical application prospects are mainly reflected in the following aspects:
Adjuvant therapy for gastric cancer Combining existing chemotherapy regimens, utilizing their characteristics of reversing drug resistance and enhancing chemotherapy sensitivity, improving treatment efficacy, reducing chemotherapy drug dosage and toxic side effects.
Development of new targeted drugs Based on its target mechanism of action, design structural modifications and derivatives to improve activity and pharmacokinetic performance, and develop highly efficient and low toxicity anti gastric cancer drugs.
Combination therapy strategy Combined with immune checkpoint inhibitors and molecular targeted drugs, it exerts synergistic anti-cancer effects and overcomes the limitations of monotherapy.
Expansion of other diseases Given its anti-inflammatory and antioxidant activities, explore its potential applications in inflammatory and neurodegenerative diseases.
However, there are still several challenges at present, including insufficient bioavailability caused by low water solubility, the need to improve metabolic stability in vivo, and a lack of systematic toxicological evaluation. In the future, it is necessary to strengthen the research and development of drug formulation technology, improve pharmacokinetic and toxicological studies, and conduct preclinical and clinical trials to verify its safety and effectiveness.
6-methoxydihydroquercetin, as a structurally unique benzophenanthridine alkaloid, has shown great potential for drug development due to its multi-target and multi mechanism anti gastric cancer activity. Its physicochemical properties and safety evaluation lay the foundation for subsequent drug design and clinical application. In the future, through in-depth mechanism research, pharmacokinetic optimization, and clinical validation, it is expected to transform this natural product into an effective anti gastric cancer drug, promoting the application process of natural products in modern cancer treatment.
