Product name: Quercetagetin
Synonym name: 3,3',4',5,6,7-Hexahydroxyflavone; 3,5,6,7,3',4'-Hexahydroxyflavone; 6-Hydroxyquercetin
Catalogue No.: BP4114
Cas No.: 90-18-6
Formula: C₁₅H₁₀O₈
Mol Weight: 318.237
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.
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.

Description:

Quercetagetin may be a potent inhibitor of the STAT1 signal, which could be a new molecular target for anti-inflammatory treatment, and may thus have therapeutic applications as an immune modulator in inflammatory diseases such as AD. It has stronger inhibitory effects on the protein and mRNA expression of TARC and MDC than other flavonoids.

References:

Biomolecules and Therapeutics, 2013, 21(2):138-145.    

Anti-Inflammatory Effect of Quercetagetin, an Active Component of Immature Citrus unshiu, in HaCaT Human Keratinocytes.

Citrus fruit contain various flavonoids that have multiple biological activities. However, the content of these flavonoids are changed during maturation and immature Citrus is known to contain larger amounts than mature. Chemokines are significant mediators for cell migration, while thymus and activation-regulated chemokine (TARC/CCL17) and macrophage-derived chemokine (MDC/CCL22) are well known as the typical inflammatory chemokines in atopic dermatitis (AD), a pruritic and chronic inflammatory skin disease. We reported recently that the EtOH extract of immature Citrus unshiu inhibits TARC and MDC production.

METHODS AND RESULTS:

Therefore, we investigated the activity of flavonoids contained in immature Citrus on TARC and MDC levels. As a result, among the various flavonoids, Quercetagetin has stronger inhibitory effects on the protein and mRNA expression of TARC and MDC than other flavonoids. Quercetagetin particularly has better activity on TARC and MDC level than quercetin. In HPLC analysis, the standard peak of Quercetagetin matches the peaks of extract of immature C. unshiu. 

CONCLUSIONS:

This suggests that Quercetagetin is an anti-inflammatory component in immature C. unshiu.    

HPLC of Quercetagetin

Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃

Introduction/Overview

Quercetagetin (CAS No.: 90-18-6) is a natural flavonoid compound and belongs to the category of 6-hydroxyquercetin derivatives. As a secondary metabolite of plants, marigold quercus has attracted widespread attention in the field of natural product pharmacology in recent years due to its unique chemical structure and diverse biological activities. It exhibits significant pharmacological activity in antioxidant, anti-inflammatory, and antitumor aspects, especially as a moderately potent and selective PIM-1 kinase inhibitor, demonstrating potential anti-cancer therapeutic value. This paper will systematically review the chemical structure, plant origin, pharmacological effects, mechanism of action, druggability evaluation, and clinical application prospects of Marigold querce, aiming to provide theoretical basis and reference for subsequent research and development.

Chemical structure and physicochemical properties

The chemical name of marigold-quercetin is 6-hydroxyquercetin, with the molecular formula C15H10O8 and a molecular weight of 318.2370. Its structural core is a typical flavonoid framework (2-phenyl-4H-1-benzopyran-4-one), which introduces a hydroxyl group at the C-6 position on top of quercetin, giving it unique chemical properties and bioactivity. The topological polar surface area (TPSA) of marigoldin querces is 151.59 Ų, indicating high polarity and hydrogen bond donor/acceptor capacity, which is significant for binding to biological macromolecule targets. The LogP value was 1.8223, indicating moderate lipid solubility that facilitates cell membrane penetration, but low water solubility (0.0382 mg/mL), suggesting limited solubility in the aqueous phase and potentially affecting bioavailability.

Additionally, the permeability of marigoldin in querces is relatively low, indicating limited distribution in the central nervous system. 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 a solid safety foundation.

Plant Origins and Extraction Methods

Quercephalin is mainly found in plants of the Asteraceae family, especially abundant in plants of the genus Tagetes (Tagetes spp.). Marigold, as a traditional medicinal and ornamental plant, has flowers, leaves, stems, and other parts that can all serve as sources of querceran marigold. Besides marigolds, some other plants with higher flavonoid content have also been reported.

Common methods for extracting querceran marigoldin include organic solvent extraction, ultrasound-assisted extraction, and high-performance liquid chromatography (HPLC) separation and purification. Ethanol or methanol is generally used as extraction solvents, combined with ultrasonic-assisted technology, which can improve extraction efficiency. The extract undergoes steps such as concentration, liquid-liquid separation, and silica gel column chromatography, and is finally purified by reversed-phase HPLC to obtain high-purity querces marigold. In recent years, the application of supercritical CO2 extraction technology and molecular blotting technology has also provided new ideas for efficient extraction and separation of marigold querce.

Pharmacological activity research

Antioxidant activity

As an important member of flavonoids, marigold-querquer bark demonstrates remarkable antioxidant capacity. It protects by scavenging free radicals, inhibiting lipid peroxidation, and regulating endogenous antioxidant enzyme systems. In vitro experiments show that marigoldin querces can effectively activate the nuclear factor red 2-related factor 2 (Nrf2) signaling pathway, inducing the expression of downstream antioxidant enzymes such as superoxide dismutase (SOD1, SOD2), catalase (CAT), glutathione peroxidase (GPX1), and heme oxygenase 1 (HMOX1), thereby enhancing cellular antioxidant defense. In addition, marigold-querquel regulates matrix metalloproteinases (MMP1, MMP3) and tyrosinase (TYR) and other related molecules, indirectly participating in tissue repair and anti-inflammatory processes.

Anti-inflammatory effects

Marigoldin querces exerts anti-inflammatory effects by inhibiting the production and release of inflammatory mediators. It can downregulate the expression of pro-inflammatory cytokines such as tumor necrosis factor-α (TNF-α), interleukin-6 (IL-6), and cyclooxygenase-2 (COX-2), thereby reducing inflammatory responses. The related mechanism involves inhibition of the NF-κB signaling pathway and regulation of the MAPK pathway, thereby reducing the transcriptional activity of inflammation-related genes. Animal model studies have also confirmed the protective effects of querceran marigold in inflammatory diseases.

Antitumor activity

Marigoldin, as a moderate-intensity and selective pim-1 kinase inhibitor (IC50 0.34 μM), has shown promise in antitumor research. PIM-1 kinase is an important molecule for regulating cell proliferation, survival, and apoptosis, and its overexpression is closely related to the occurrence and development of various tumors. Marigold querceil blocks cancer cell proliferation signals by inhibiting PIM-1 kinase activity, inducing cell cycle arrest and apoptosis. Additionally, it can influence the migration and invasion capabilities of cancer cells, inhibiting tumor metastasis. Various in vitro tumor cell line experiments and in vivo tumor models support the antitumor effects of querceran marigold.

Mechanism of action and molecular targets

The pharmacological effects of marigold querce are exerted synergistically across multiple targets and pathways, mainly involving the following aspects:

1. PIM-1 kinase inhibition
   As the main target of querceran marigold, pim-1 kinase directly affects the expression of cell cycle regulatory proteins (such as Cyclin D1) and anti-apoptotic proteins (such as the Bcl-2 family), promoting cancer cell apoptosis. Marigoldin querces inhibits enzyme activity by competitively binding to the pim-1 kinase ATP binding site.

2. Regulation of antioxidant signaling pathways
   Marigoldin in querces activates the Nrf2 transcription factor, promotes its nuclear translocation, enhances the expression of antioxidant enzyme genes, and alleviates oxidative stress damage. Its regulation of SOD1, SOD2, CAT, GPX1, and HMOX1 helps maintain intracellular redox balance.

3. Suppression of inflammatory signaling pathways
   By inhibiting the NF-κB and MAPK signaling pathways, querces marigoldin reduces the production of pro-inflammatory factors and alleviates inflammatory responses. This mechanism of action is of great significance for chronic inflammation-related diseases.

4. Matrix metalloproteinase regulation
   Marigoldin's inhibition of MMP1 and MMP3 helps prevent degradation of the extracellular matrix and blocks tumor cell invasion and metastasis.

Overall, marigold querces exerts its antioxidant, anti-inflammatory, and anti-tumor pharmacological effects through multi-target synergistic regulation.

Druggability evaluation and pharmacokinetics

The druggability parameters of querceran marigoldin indicate that it has promising potential for drug development. The molecular weight of 318.2370 conforms to the Lipinski rule, with a LogP of 1.8223, indicating moderate lipid solubility and facilitation for absorption and distribution in the body. A higher TPSA value (151.59 Ų) indicates strong polarity, which may limit oral absorption and membrane penetration, but its cellular permeability has still been confirmed to be at a certain level.

Low water solubility may pose challenges in formulation development, requiring improvements in solubility and bioavailability through drug carriers or chemical modifications. The blood-brain barrier has low permeability, reducing the risk of central nervous system side effects, but limiting its application in neurological diseases.

In terms of safety, hERG channel inhibition is negative and Ames tests have low mutagenicity, indicating lower risks of cardiotoxicity and genotoxicity, meeting drug safety requirements.

Currently, pharmacokinetic data on marigoldin querces are limited. Preliminary studies show that its metabolism in the body mainly occurs through hepatic enzyme systems, and the activity and toxicity of these metabolites require further investigation. In the future, systematic studies on absorption, distribution, metabolism, excretion (ADME), and toxicology are needed to provide a basis for clinical development.

Prospects and outlooks for clinical applications

Given the multiple activities of marigold querce in antioxidant, anti-inflammatory, and antitumor aspects, it has broad application prospects in the treatment of various diseases. Especially in the field of tumor treatment, as a PIM-1 kinase inhibitor, marigold-querquer is expected to become a novel candidate for targeted therapy. Its anti-inflammatory and antioxidant properties also offer potential for adjunctive treatment of chronic inflammatory diseases, cardiovascular diseases, and metabolic syndromes.

However, the clinical translation of marigold querces still faces many challenges, including poor water solubility, low bioavailability, and a lack of systematic pharmacokinetic data. Future research should focus on:

1. Optimize extraction and purification processes to improve yield and purity;
2. Structural modification and drug carrier development to improve pharmacokinetic properties;
3. In-depth revealing its molecular mechanisms of action, clarifying key targets and signaling pathways;
4. Systematic in vivo pharmacodynamics and toxicology evaluations to ensure safety;
5. Design reasonable clinical trials to verify efficacy and safety.

In addition, the synergistic effects of marigold quercein and other drugs and its potential in multi-target drug development are also important directions for future research.

Conclusion

Marigold querce, as a natural flavonoid with multiple biological activities, demonstrates promising drug development potential due to its significant pharmacological effects such as antioxidant, anti-inflammatory, and anti-tumor effects. Its discovery as a PIM-1 kinase inhibitor offers new ideas for targeted tumor therapy. Although there are still certain limitations in pharmacokinetics and clinical applications, with continuous advances in extraction technology, drug design, and clinical research, marigoldin querces is expected to become an important candidate for future natural product drug development. Future systematic research will lay a solid foundation for its clinical translation and promote its widespread application in disease prevention and treatment.