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Product name: Quercetagitrin
Synonym name: Quercetagetin 7-glucoside;Quercetagetin 7-O-β-D-glucosi
Catalogue No.: BP4113
Cas No.: 548-75-4
Formula: C21H20O13
Mol Weight: 480.378
Botanical Source: Tagetes erecta L
Physical Description:
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.
The product could be supplied from milligrams to grams
Inquire for bulk scale.
For Reference Standard and R&D, Not for Human Use Directly.
Description:
Quercetagetin-7-O-glucoside, a potent inhibitor of beta-glucuronidase and lysozyme release, shows anti-inflammatory activity, can significantly inhibit arachidonic acid release from membranes.
References:
Z Naturforsch C. 1994 Mar-Apr;49(3-4):235-40.
Influence of anti-inflammatory flavonoids on degranulation and arachidonic acid release in rat neutrophils.
We assessed the effects of 24 flavonoid derivatives, reported as anti-inflammatory, on lysosomal enzyme secretion and arachidonic acid release in rat neutrophils.
METHODS AND RESULTS:
Amentoflavone, Quercetagetin-7-O-glucoside, apigenin, fisetin, kaempferol, luteolin and quercetin were the most potent inhibitors of beta-glucuronidase and lysozyme release. The first compound was also able to inhibit basal release. These flavonoids besides chrysin and to a reduced extent, naringenin, significantly inhibited arachidonic acid release from membranes.
CONCLUSIONS:
A correlation between degranulation and arachidonic acid release was found for this series of compounds. Structure-activity relationships and implications for the anti-inflammatory effects of these flavonoids were discussed.
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
230.7400
-.2782
-.9594
1.0713
.6706
.1017
Low
77.8089
4.1433
Yes
No
No
No
Yes
No
1.2
Yes
No
Yes
No
Quercetagitrin (CAS number: 548-75-4) is a type derived from African marigold (Tagetes erecta). ) Natural flavonoid glycoside compounds isolated from the site. As one of the quercetin derivatives, marigold quercetin has attracted widespread attention in recent years due to its remarkable biological activity, especially its potential in anti-inflammation, antioxidant, and neuroprotective properties. This compound not only regulates pathological processes related to neurodegenerative diseases such as Alzheimer's disease (AD), but also positively impacts type 2 diabetes (T2DM) by modulating glucose metabolism pathways. Its multi-target mechanism of action and good safety profile have made it a research hotspot in natural product pharmacology and new drug development.
This paper will systematically review the chemical structure and physicochemical properties of Marigold querquer glycoside, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation, and pharmacokinetic characteristics, and finally explore its potential for clinical application and future development directions, aiming to provide theoretical basis and reference for in-depth research and drug development of this natural product.
The chemical name of quercetagetin-7-O-glucoside is Quercetagetin-7-O-glucoside, with the molecular formula C21H20O13 and a molecular weight of 480.3780. Its structure is based on the core of quercetagetin, forming an O-glycosidic bond with glucose via a hydroxyl group at 7 positions, forming a flavonoid-7-O-glucoside. This structure imparts strong hydrophilicity, with a LogP value of -0.2782, indicating strong hydrophilicity. Water solubility is 1.0713, with good water solubility, which is beneficial for absorption and distribution in the body.
Its topological polar surface area (TPSA) reaches as high as 230.74 Ų, reflecting the molecule's presence of multiple polar groups, especially multiple hydroxyl and glycoside groups, enhancing its binding ability with biological macromolecules. Marigold quercein has low blood-brain barrier permeability, suggesting limited direct penetration in the central nervous system, but it is likely to exert indirect neuroprotective effects by modulating peripheral or intracranial targets. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity; The Ames-induced mutagenic test value was 1.2, indicating a low genotoxicity risk and good safety.
Quercus marigold glycoside mainly comes from African marigold (Tagetes erecta), a herbaceous plant widely distributed in tropical and subtropical regions, commonly used in horticulture and traditional medicine. African marigold inflorescences are rich in various flavonoid compounds, with marigold in querces being particularly abundant.
Common methods for extracting querceran marigold glycoside include:
In recent years, new technologies such as supercritical CO₂ extraction and microwave-assisted extraction have also been attempted to improve extraction efficiency and purity, promoting the large-scale preparation of querces marigold glycoside.
The pharmacological activities of quercester marigold include anti-inflammatory, antioxidant, neuroprotection, and metabolic regulation.
Research shows that marigold in querces can significantly inhibit the release of inflammatory mediators and the activation of inflammatory signaling pathways. By inhibiting activation of the nuclear factor κB (NF-κB) signaling pathway, it reduces the expression of pro-inflammatory cytokines such as TNF-α, IL-1β, and IL-6, demonstrating good anti-inflammatory effects. In the P301S-Tau transgenic mouse model, quercester marigold glycoside can reverse neuroinflammatory responses and alleviate cognitive impairment, suggesting its potential application value in neuroinflammation-related diseases.
Marigoldin querces can inhibit abnormal accumulation of tau protein and slow down neuronal damage. Abnormal phosphorylation and aggregation of tau protein are among the pathological features of Alzheimer's disease and other neurodegenerative diseases. Marigold quercus glycoside regulates related signaling pathways, alleviates pathological changes in tau, protects neuronal function, and improves cognitive ability.
As a flavonoid compound, quercester marigold glycoside has significant antioxidant capacity. It activates the nuclear factor 2-related factor 2 (NRF2) signaling pathway, promotes the expression of downstream antioxidant enzymes such as superoxide dismutase (SOD1, SOD2), catalase (CAT), glutathione peroxidase (GPX1), and heme oxygenase 1 (HMOX1), clears excess reactive oxygen species (ROS), and reduces cellular damage caused by oxidative stress.
Querces marigold glycoside can enhance glucose uptake by mature C2C12 myoblasts, suggesting its potential in regulating glucose metabolism and insulin sensitivity. This characteristic has made it highly regarded in adjuvant therapy research for type 2 diabetes.
The multi-target mechanism of quercetic marigold glycoside is the foundation for its diverse pharmacological activity.
Quercetin marigold glycoside is a dual-target inhibitor of the protein tyrosine phosphatase PTPN6 and PTPN9, with IC50s of 1 μM and 1.7 μM, respectively. PTPN6 and PTPN9 are involved in various cellular signal transduction processes, regulating immune responses and cellular metabolism. By inhibiting these two targets, quercepha marigoldin can regulate inflammatory responses and metabolic homeostasis, exerting anti-inflammatory and metabolic regulatory effects.
NF-κB is a key transcription factor regulating inflammation and immune responses. Quercester marigold glycoside inhibits NF-κB nuclear translocation by blocking the phosphorylation and degradation of IκBα, reducing the expression of pro-inflammatory genes and thereby alleviating inflammatory responses.
Marigold querces can activate the NFE2L2/NRF2 signaling pathway, induce the expression of antioxidant enzyme genes, and enhance cellular antioxidant defense capabilities. Additionally, it may maintain extracellular matrix stability and slow tissue inflammation and damage by regulating matrix metalloproteinases MMP1 and MMP3.
Marigoldin querces can inhibit abnormal aggregation of tau proteins, which may reduce neuronal toxicity and improve cognitive function by regulating the phosphorylation state of tau and promoting its degradation.
The druggability parameters of marigold in querces indicate that it has certain potential for drug development:
Currently, pharmacokinetic data on marigold in querces are relatively limited. Given its high polarity and glycoside structure, it is speculated that its oral absorption may be limited, and in vivo metabolism may involve glycosidic hydrolase-mediated glycosidic bond break, releasing active querci marigold. Future studies on in vivo absorption, distribution, metabolism, and excretion (ADME) are needed to clarify its pharmacokinetic characteristics and the biological activity of its metabolites.
With its multi-target and multi-mechanism pharmacological activity, marigold querces shows broad application prospects in the fields of neurodegenerative and metabolic diseases.
The pathogenesis of Alzheimer's disease is complex, involving multiple pathological processes such as abnormal accumulation of tau protein, neuroinflammation, and oxidative stress. Marigold quercus glycoside demonstrates potential neuroprotective effects by inhibiting Tau accumulation, reducing neuroinflammation, and enhancing antioxidant capacity. Its efficacy in the P301S-Tau transgenic mouse model provides strong support for its clinical translation. In the future, drug delivery technology can be combined to increase effective concentrations in the brain and enhance treatment outcomes.
Marigold querces enhance the glucose uptake ability of myoblasts, suggesting it may improve insulin resistance and regulate blood sugar levels. Combined with its anti-inflammatory and antioxidant effects, it is expected to become an adjunctive therapy for type 2 diabetes and its complications. Further preclinical and clinical studies will help clarify its efficacy and safety.
The anti-inflammatory and antioxidant properties of querceran marigold also give it potential application value in inflammatory diseases, cardiovascular diseases, and oncology. In particular, its role in regulating immune responses and cellular signaling pathways has made it possible for its multi-domain development.
As a natural flavonoid glycoside derived from African marigold, querces marigold glycoside exhibits rich pharmacological activity and good safety. Its multi-target inhibitory inhibition of PTPN6 and PTPN9 regulates the NF-κB and NRF2 signaling pathways, suppresses tau protein accumulation, enhances glucose uptake, and establishes a multi-functional mechanism of anti-inflammatory, antioxidant, neuroprotective, and metabolic regulation. Although its blood-brain barrier permeability is relatively low, marigold querces still has potential as a candidate drug for treating diseases such as Alzheimer's disease and type 2 diabetes through optimized administration strategies and structural modifications.
Future research should focus on its pharmacokinetic characteristics, in vivo metabolic pathways, and long-term safety evaluation, while exploring combination therapy and structural optimization strategies to promote the clinical application of quercetic marigold glycosides. In summary, querces marigold glycoside not only enriches the research content of natural product pharmacology but also provides new ideas and candidate molecules for the treatment of related diseases.
Shenshuai
Wenjing
Hedandan
