| Catalog No | Package | Original Price | Price | Inventory | Quantity | Operating |
|---|---|---|---|---|---|---|
| SBP02651-5mg | 5mg | $350.00 | Sign in |
|
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
110.3800
1.3000
.5000
Low
.7500
null
No
No
No
No
No
No
null
2-Hydroxynaringenin (CAS No.: 58124-18-8), as an important natural flavonoid compound, has attracted widespread attention in the field of natural product pharmacology in recent years. Its unique structural features and multi-target pharmacological activity give it potential application value in biomedical fields such as antioxidant, anti-inflammatory, anti-diabetic, anti-tumor, and neuroprotective fields. 2-hydroxynaringin is mainly isolated from Taiwanese Paeonia lactiflora Pall. It belongs to the members of 2-hydroxyflavanone and tetrahydroxyflavanone, and has a tetrahydroxyflavanone backbone structure with hydroxyl groups at 2, 4', 5, and 7 positions. This paper will systematically review the chemical structure and physicochemical properties of 2-hydroxynaringin, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation, pharmacokinetic characteristics, and clinical application prospects, aiming to provide scientific basis and theoretical support for subsequent research and drug development.
The chemical name of 2-hydroxynaringin is 2,5,7-trihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one, with a molecular formula of C15H12O6 and a molecular weight of 290.25. Its core structure is a flavonone backbone, with four hydroxyl sites (positions 2, 4', 5, 7), which impart excellent hydrophilicity and bioactivity. The compound has a LogP value of about 1.3, showing moderate lipid solubility, which benefits its distribution in organisms and its ability to penetrate cell membranes. The topological pole surface area (TPSA) is 110.38 Ų, indicating strong polarity and hydrogen bond formation, with 6 hydrogen bond receptors, further indicating its binding potential with biomacromolecules such as enzymes and receptors.
From the perspective of physicochemical properties, 2-hydroxynaringin has good water solubility and stability, and does not show significant hepatotoxicity, cardiotoxicity, or hERG channel inhibition. The Ames test result was negative, indicating a low genotoxicity risk. Its blood-brain barrier penetration capacity is relatively low, suggesting that its direct role in the central nervous system may be limited, but it still has potential for neuroprotective effects through peripheral or indirect mechanisms.
2-Hydroxynaringin is mainly found in Taiwan Paeonia lactiflora Pall. and is one of the plant's important flavonoid metabolites. Taiwan white peony root, as a traditional Chinese medicinal herb, is rich in flavonoids and phenylpropanoid compounds. Although the content of 2-hydroxynaringin is not as high as mainstream flavonoids, its unique structure and biological activity make it a research hotspot.
Common methods for extracting 2-hydroxynaringin include solvent extraction, chromatographic separation, and crystallization purification. Generally, ethanol or methanol is used as extraction solvents, and extraction efficiency is improved through ultrasound-assisted extraction or reflux extraction. After concentration, the extract was separated and purified using silica gel column chromatography and reversed-phase high-performance liquid chromatography (RP-HPLC). In recent years, the application of supercritical CO2 extraction and membrane separation technology has provided new ideas for improving the extraction purity and yield of 2-hydroxynaringin. In addition, enzyme-assisted extraction technologies have also been explored to improve extraction efficiency and the stability of active ingredients.
2-hydroxynaringin exhibits a wide range of pharmacological activities, covering antioxidant, anti-inflammatory, antidiabetic, antitumor, and neuroprotective fields.
2-hydroxynaringin activates the nuclear factor E2-related factor 2 (NRF2) signaling pathway, inducing the expression of downstream antioxidant enzymes such as catalase (CAT), glutathione peroxidase 1 (GPX1), heme oxygenase 1 (HMOX1), and superoxide dismutase 2 (SOD2), significantly enhancing cellular antioxidant defense capacity and reducing oxidative stress damage. Both in vitro and in vivo experiments have shown that it can effectively eliminate free radicals, delay cellular aging, and has strong anti-aging potential.
2-Hydroxynaringin can inhibit the production and release of inflammatory mediators, mainly by downregulating key inflammatory signaling molecules such as cyclooxygenase-2 (PTGS2), nuclear factor κB (NFKB1), tumor necrosis factor α (TNF), interleukin-6 (IL6), and mitogen-activated protein kinase (MAPK1), thereby reducing inflammatory responses. It demonstrates significant anti-inflammatory effects in inflammatory disease models, suggesting its potential for application in chronic inflammatory diseases such as arthritis and inflammatory bowel disease.
2-Hydroxynaringin promotes insulin signaling and glucose uptake by regulating insulin receptor (INSR), glucose transporter 4 (SLC2A4), AMP-activated protein kinase (PRKAA1), protein kinase B (AKT1), and peroxisome proliferator-activated receptor γ (PPARG), thereby improving insulin resistance and lowering blood glucose levels. Additionally, its antioxidant and anti-inflammatory effects help alleviate diabetes-related microvascular and neuropathy, demonstrating the advantages of multi-target integrated therapy.
2-Hydroxynaringin exhibits effects in various tumor cell lines that inhibit proliferation, induce apoptosis, and suppress metastasis. Its mechanism of action involves regulation of signaling pathways such as epidermal growth factor receptor (EGFR), B-cell lymphoma-2 protein (BCL2), tumor suppressor protein p53 (TP53), phosphatidylinositol 3-kinase (PIK3CA), and mitogen-activated protein kinase (MAPK1). By regulating cell cycle and apoptosis-related proteins, 2-hydroxynaringin can effectively induce tumor cell apoptosis and inhibit tumor growth and invasion.
Research on 2-hydroxynaringin in the field of neuroprotection is gradually increasing. By regulating targets such as β-amyloid precursor proteasome (BACE1), α-synuclein (SNCA), superoxide dismutase (SOD1), nerve growth factor receptor (NGFR), and nuclear factor E2-related factor 2 (NFE2L2), it alleviates oxidative stress and inflammatory responses in nerve cells, inhibits abnormal accumulation of neurotoxic proteins, and delays the progression of neurodegenerative diseases such as Alzheimer's and Parkinson's.
The multi-target mechanism of 2-hydroxynaringin forms the basis of its broad pharmacological activity. It mainly regulates intracellular signaling pathways and transcription factor activity, affecting gene expression and protein function, thereby achieving multiple biological effects such as antioxidant, anti-inflammatory effects, metabolic regulation, and apoptosis.
NRF2 pathway activation: 2-hydroxynaringin promotes the translocation of NRF2 from the cytoplasm to the nucleus, enhancing the transcription of antioxidant enzyme genes and improving cellular resistance to oxidative stress.
NF-κB signaling inhibition: By suppressing NF-κB activation, it reduces the expression of pro-inflammatory factors and alleviates inflammatory responses.
Regulation of insulin signaling pathways: promotes phosphorylation of INSR and AKT1, enhances insulin signaling, and promotes glucose uptake and metabolism.
PI3K/Akt and MAPK pathway regulation: In tumor cells, PIK3CA and MAPK1 signaling are regulated, inhibiting cell proliferation and promoting apoptosis.
Neuroprotective mechanism: regulates the expression of BACE1 and SNCA, reduces the accumulation of neurotoxic proteins, and promotes neuronal survival.
2-Hydroxynaringin has relatively ideal druggable parameters. Its molecular weight is moderate (290.25), and the LogP value (1.3) indicates suitable lipid solubility, which is beneficial for cell membrane penetration. A higher TPSA (110.38) and hydrogen bond receptor count (6) suggest strong polarity, which may limit its oral bioavailability but favors binding to target proteins.
Toxicological evaluation showed that 2-hydroxynaringetin showed no significant hepatotoxicity, cardiotoxicity, or hERG channel inhibition, and the Ames-induced mutagenic test was negative, indicating a relatively high safety. The blood-brain barrier has a relatively low penetration capacity, suggesting limited direct efficacy in the central nervous system, but it can exert neuroprotective effects by improving the peripheral nervous environment.
Pharmacokinetics, existing research is relatively limited. Preliminary data indicate that its oral absorption rate is moderate, metabolism in the body mainly occurs through hepatic enzyme systems, and metabolites require further identification. In the future, systematic research into its distribution, metabolic pathways, and excretion mechanisms in vivo is needed to optimize administration regimens and dosage form design.
Based on the significant pharmacological activity of 2-hydroxynaringin in various disease models, its clinical application prospects are broad. First, its antioxidant and anti-inflammatory properties make it a potential therapeutic agent for chronic inflammatory diseases and age-related illnesses. Second, the multi-target regulatory effect on diabetes and its complications makes it possible to develop novel adjunctive therapies for diabetes. Third, antitumor activity suggests it can serve as a candidate molecule for adjuvant therapy, especially in combination chemotherapy or targeted therapy, where synergistic effects may be achieved. Finally, the neuroprotective effects of neurodegenerative diseases provide a theoretical basis for their clinical translation in fields such as Alzheimer's and Parkinson's disease.
Future research should focus on preclinical pharmacokinetic optimization, formulation development, and safety evaluation of 2-hydroxynaringetin, while integrating modern molecular biology and medicinal chemistry methods to deeply analyze its mechanism of action and promote its clinical application. In addition, enhancing bioavailability and targeting through structural modification and nanocarrier technology will also be important research directions.
As a natural flavoloid compound with multiple pharmacological activities, 2-hydroxynaringin demonstrates promising drug development potential and broad application prospects. Its unique chemical structure endows it with excellent antioxidant, anti-inflammatory, antidiabetic, anti-tumor, and neuroprotective activities. Although research on its pharmacokinetics and clinical applications is still in its early stages, as research progresses, 2-hydroxynaringetin is expected to become an important candidate molecule in the development of natural product drugs. In the future, it is necessary to strengthen mechanistic research, pharmacokinetic optimization, and preclinical evaluation to lay a solid foundation for clinical translation and promote its application in the prevention and treatment of various diseases.
