Product name: 5-MethoxyPinocembroside
Synonym name: (2S)-7-(β-D-Glucopyranosyloxy)-2,3-dihydro-5-methoxy-2-phenyl-4H-1-benzopyran-4-one
Catalogue No.: BP2073
Cas No.: 1450878-89-3
Formula: C22H24O9
Mol Weight: 432.425
Botanical Source: Penthorum chinense Pursh
Type of Compound: Flavonoids
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.
Chengdu Biopurify Phytochemicals Ltd. is a leading company in the research, development, manufacture and marketing of High Quality Phytochemicals and Extracts(especially Active Ingredients from Traditional Chinese Medicine，TCM), Natural Active Pharmaceutical Ingredients worldwide.
The main services:
A. Supply active ingredients and reference standards of TCM, from mgs to kgs scale
B. Custom extraction and purification, target Herb Active Ingredients
C. Custom synthesis and semi-synthesis for Natural Active Ingredients
D. CR(contract research), CM(contract manufacture) and PD(process development) services from lab scale, pilot scale to commercial scale(GMP is also available)
E. TCM compounds library for drug screen,more than 3000 compounds available, many of them are rare and unique.
HPLC of 5-MethoxyPinocembroside
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
134.9100
.7641
.7640
.9418
.5357
.7448
Low
75.4197
3.8646
Yes
No
No
No
No
No
0.0
Yes
Yes
Yes
No
Alzheimer's disease (AD), as a progressive neurodegenerative disease, is characterized by cognitive impairment, memory loss, and behavioral abnormalities, seriously affecting the quality of life of patients, and there is currently no curative therapy. In recent years, natural products have become an important resource for the development of multi-target drugs due to their structural diversity and wide range of biological activities, making them a hot topic in the research and development of new drugs for neurodegenerative diseases. 5-MethoxyPinocembroside is an emerging natural flavonoid compound that was first isolated from the traditional Chinese medicine Penthorum chinense Pursh, demonstrating potential neuroprotective effects and multi-target regulatory capabilities. This article aims to provide a systematic review of the chemical structure, physicochemical properties, plant origin, pharmacological activity, mechanism of action, pharmacological evaluation, and clinical application prospects of 5-methoxy-glycoside, providing theoretical basis and research direction for its development in the treatment of Alzheimer's disease.
5-methoxy-2-glucoside (CAS number: 1450878-89-3) belongs to the flavonoid glycoside class, with a molecular formula of C21H28O10 and a molecular weight of 432.4250. Its structural characteristics include a typical flavonoid skeleton and a 5-methoxy substituent, supplemented by multiple hydroxyl and glycosidic linking groups, giving it high polarity and water solubility. In terms of physical and chemical properties, the LogP value of 5-methoxy-glycoside is 0.7641, indicating its strong hydrophilicity. The TPSA (topological polar surface area) is 134.91 Å ², indicating its good polarity and hydrogen bond donor acceptor ability, which is conducive to binding with biomolecule targets. The water solubility index is 0.9418, indicating its high solubility in aqueous phase, which has a positive impact on the bioavailability of oral formulations. The low permeability of the blood-brain barrier (BBB) suggests that its direct central nervous system effects may be limited, but it may also indirectly exert neuroprotective effects by regulating peripheral targets. The hERG channel inhibition test result is negative, indicating a low risk of cardiac toxicity. The Ames mutagenicity test result is 0.0, indicating a low risk of genetic toxicity and a good safety basis.
5-methoxy-glycoside is mainly isolated from the traditional Chinese medicine Penthorum chinense Pursh. Penthorum chinense is a perennial herbaceous plant in the family Araliaceae, widely distributed in southern China and Southeast Asia. It is used in traditional Chinese medicine for diuresis, clearing heat and detoxifying, and protecting the liver. This plant contains abundant flavonoids, glycosides, and polyphenols, which are important sources of natural active substances.
The extraction process usually uses ethanol or methanol as solvents to obtain crude extracts through reflux extraction or ultrasound assisted extraction. Subsequently, using liquid-liquid partitioning, silica gel column chromatography, reverse phase high performance liquid chromatography (RP-HPLC) and other separation and purification techniques, 5-methoxy-2-glucoside was successfully isolated. In modern research, supercritical fluid extraction and membrane separation technologies have also been introduced to improve extraction efficiency and purity. The optimization of extraction conditions, such as solvent concentration, temperature, and time, is crucial for improving the yield and maintaining the activity of the target compound.
The pharmacological activity research of 5-methoxy-glycoside mainly focuses on neuroprotective and anti-inflammatory effects, especially targeting the pathological mechanisms related to Alzheimer's disease.
Neuroprotective effect
In vitro cell models have shown that 5-methoxy-glycoside can significantly inhibit oxidative stress-induced neuronal apoptosis and improve neuronal survival rate. It reduces oxidative damage by clearing free radicals and regulating intracellular antioxidant enzyme activity (such as superoxide dismutase (SOD) and glutathione peroxidase (GPx)). In addition, the compound can stabilize mitochondrial membrane potential, prevent mitochondrial dysfunction, and slow down neuronal energy metabolism disorders.
anti-inflammatory effect
5-methoxy-glycoside exhibits significant anti-inflammatory activity in microglial and macrophage models, capable of inhibiting the release of inflammatory factors such as TNF - α, IL-1 β, and IL-6, and alleviating neuroinflammatory responses. Its mechanism of action involves inhibiting the activation of the TLR4 signaling pathway, reducing the nuclear translocation of downstream NF - κ B transcription factors, and thereby reducing the expression of pro-inflammatory genes.
Potential for combating Alzheimer's disease
In Alzheimer's disease-related cell models, 5-methoxy-glycoside exhibits inhibition of abnormal processing of β - amyloid precursor protein (APP) and β - secretase 1 (BACE1) activity, reducing the production of β - amyloid protein (A β) and alleviating neurotoxicity. In addition, 5-methoxy-glycoside promotes cellular energy metabolism balance by regulating the AMPK signaling pathway, inhibits the expression of neuronal apoptosis related proteins MCL1 and BCL2, and enhances cell survival ability.
The mechanism of action of 5-methoxy-glycoside involves multiple signaling pathways and key molecular targets, reflecting its multi-target and multi pathway regulation characteristics.
AMPK (PRKAA1) activation
AMPK, as a cellular energy sensor, plays a central role in maintaining neuronal energy homeostasis and promoting autophagy to clear abnormal proteins. 5-methoxy-glycoside activates AMPK, enhances cellular energy metabolism, promotes A β degradation and tau protein dephosphorylation, and slows down neurodegenerative diseases.
Regulation of anti apoptotic proteins (MCL1, BCL2)
5-methoxy-glycoside upregulates the expression of anti apoptotic proteins MCL1 and BCL2, inhibits mitochondrial mediated apoptosis, and protects neurons from oxidative stress and inflammatory damage.
NOTCH1 signal pathway regulation
NOTCH1 is involved in neuronal differentiation and survival, and 5-methoxy-glycoside regulates NOTCH1 signaling, which helps maintain neuronal function and promote nerve regeneration.
Regulation of nuclear receptor RARA
Retinoic acid receptor alpha (RARA) plays an important role in neuroprotection and inflammation regulation. 5-methoxy-glycoside promotes neuronal repair and anti-inflammatory response by regulating RARA activity.
IDO1 inhibition
IDO1 mediated abnormal tryptophan metabolism is closely related to neuroinflammation. 5-methoxy-glycoside inhibits IDO1 activity, alleviates neuroinflammation and immune abnormalities.
APP and BACE1 inhibition
By inhibiting abnormal APP splicing and BACE1 enzyme activity, reducing A β production, lowering plaque formation, and slowing down AD pathological progression.
Inhibition of TLR4 signaling pathway
Inhibit TLR4 mediated inflammatory signals, alleviate neuroinflammation, and protect neurons.
PTPN1 regulation
PTPN1 is involved in cellular signal transduction, and 5-methoxy-glycoside may affect neuronal survival and metabolism by regulating PTPN1.
In summary, 5-methoxy-glycoside exhibits comprehensive neuroprotective potential through multi-target synergistic effects, regulating neuronal energy metabolism, anti apoptosis, anti-inflammatory, and abnormal protein metabolism.
The pharmacological parameters of 5-methoxy-glycoside indicate that it has certain potential for drug development. The molecular weight of 432.4250 is within the ideal range of drug molecules, and the LogP value of 0.7641 indicates moderate hydrophilicity, which is beneficial for in vivo distribution and solubility. The TPSA is 134.91 Å ², which is slightly higher than the ideal range of traditional oral drugs (<140 Å ²), but still has good cell membrane penetration ability. The water solubility index of 0.9418 is relatively high, which is beneficial for oral absorption.
The low permeability of the blood-brain barrier suggests limited direct entry into the central nervous system, and may require structural modifications or the use of drug delivery systems to improve brain distribution. The negative hERG channel inhibition test and no mutagenicity in Ames test indicate good cardiac and genetic safety.
At present, there is limited pharmacokinetic research on 5-methoxy-glycoside, and preliminary data suggests that its oral bioavailability is limited, possibly due to its high polarity and glycosidic structure. The metabolism in the body is mainly carried out through the hepatic enzyme system for glycoside hydrolysis and corresponding redox reactions. The activity and toxicity of metabolites still need to be further studied. In the future, optimizing its pharmacokinetic properties and improving brain targeted delivery efficiency through strategies such as nanocarriers, liposomes, or prodrug design is the key to enhancing its clinical application value.
Given the regulatory role and good safety foundation of 5-methoxy-glycoside on multiple targets related to Alzheimer's disease, its development prospects as a potential neuroprotective agent and AD adjuvant therapy drug are broad. Future research should focus on the following aspects:
In depth pharmacological mechanism research
Using gene knockout, transgenic animal models, and multi omics techniques, further elucidate the specific molecular mechanisms of 5-methoxy-glycoside in neuroprotection, anti-inflammatory, and protein metabolism regulation.
Optimize pharmacokinetics and administration routes
By modifying its structure, developing drug carriers, and innovating its delivery methods, it can enhance its brain bioavailability and targeting, overcoming the limitations of the blood-brain barrier.
Safety and Toxicology System Assessment
Conduct long-term toxicology research and preclinical safety evaluation to ensure the safety and tolerability of its clinical application.
Preclinical and clinical trial design
Based on effective dosage and pharmacokinetic data, design a reasonable animal model for efficacy validation and early clinical trials to evaluate its potential and dosage range for treating Alzheimer's disease.
Exploration of Combination Medication Strategy
Considering its multi-target action characteristics, combined application with existing AD treatment drugs (such as acetylcholinesterase inhibitors and NMDA receptor antagonists) may achieve synergistic enhancement and improve treatment efficacy.
In summary, 5-methoxy-glycoside, as a novel flavonoid glycoside natural product, has the potential to become a new drug for the treatment of Alzheimer's disease due to its unique structure and multi-target regulatory ability. In the future, interdisciplinary collaborative research and technological innovation will drive it from the laboratory to clinical applications.
5-methoxy-glycoside, as an important active ingredient in Penthorum chinense Pursh, exhibits excellent neuroprotective and anti-inflammatory activities, especially in multi-target regulation related to Alzheimer's disease, showing unique advantages. Its physicochemical properties and safety evaluation have laid the foundation for drug development, but the low blood-brain barrier permeability and pharmacokinetic properties still need to be optimized. Through in-depth mechanism research, pharmacokinetic improvement, and preclinical validation, 5-methoxy-glycoside is expected to become a powerful candidate drug for the treatment of Alzheimer's disease in the field of natural product pharmacology. Future research will provide solid scientific support for its clinical translation and promote innovative applications of natural products in the treatment of neurodegenerative diseases.
