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Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
7,3',5'-Trihydroxyflavanone (CAS No.: 847375-46-6), a natural flavanoid compound, has attracted significant attention in recent years due to its remarkable biological activity. Flavanoids are widely found in various plants and possess antioxidant, anti-inflammatory, antiviral, and antitumor pharmacological effects. 7,3',5'-Trihydroxyflavanone, due to its unique trihydroxy structure, exhibits excellent antiviral activity, especially showing potential application value against various viral targets such as MPO, UL42, UL54, ICP27, TK, gD, CCR5, CXCR4, HIV1-PR, and INT. This paper aims to systematically review the chemical structure and physicochemical properties, plant origin and extraction methods, pharmacological activity, mechanism of action, druggability evaluation, and clinical application prospects of 7,3',5'-trihydroxyflavanone, providing a theoretical foundation and direction for subsequent research and drug development.
7,3',5'-Trihydroxyflavanone belongs to the flavanoid class of compounds, with a molecular formula of C15H12O5 and a molecular weight of 272.2560. Its structural feature is that hydroxyl groups are carried at positions 7, 3', and 5' on the flavanone backbone, forming a unique trihydroxyl substitution pattern. This structure gives it strong hydrophilicity and excellent free radical scavenging ability.
In terms of physicochemical properties, the LogP value of 7,3',5'-trihydroxyflavanone is 1.9136, indicating moderate lipid solubility, which is beneficial for cell membrane penetration and bioavailability. The polar surface area (TPSA) was 86.99 Ų, indicating moderate polarity, which is favorable for binding to biological macromolecule targets. Its water solubility is 0.3356, which is not high but sufficient to support its dissolution and distribution in the body. The blood-brain barrier has low permeability, suggesting 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 result was 0.0, indicating a low genotoxicity risk and a solid safety foundation.
7,3',5'-Trihydroxyflavanone is mainly found in various traditional medicinal and edible plants, especially certain flavonoid-rich plants such as Ruta, Fabaceae, and Asteraceae. Specific plant species include, but are not limited to, certain citrus species, flavonoid-rich legumes, and some wild herbaceous plants.
The extraction method mostly uses traditional solvent extraction combined with modern chromatographic separation techniques. Common extraction solvents include mixed solvent systems of ethanol, methanol, and water, which use ultrasound-assisted extraction or reflux extraction to improve extraction efficiency. After concentration, the extract was purified and separated using silica gel column chromatography, high-performance liquid chromatography (HPLC), or reversed-phase liquid chromatography (RP-HPLC), ultimately obtaining high-purity 7,3',5'-trihydroxyflavanone. In recent years, supercritical CO2 extraction and membrane separation technologies have also been attempted to extract this compound, aiming to improve yield and purity and reduce solvent residues.
Pharmacological activity research on 7,3',5'-trihydroxyflavanone mainly focuses on its antiviral effects, as well as its antioxidant, anti-inflammatory, and immunomodulatory aspects.
Numerous in vitro and in vivo studies have shown that 7,3',5'-trihydroxyflavanone exhibits inhibitory effects on a variety of viruses, including DNA and RNA viruses. Its targets include mononucleotide peroxidase (MPO), herpes virus-associated proteins UL42, UL54, ICP27, thymidine kinase (TK), viral glycoprotein D (gD), and HIV-related targets CCR5, CXCR4, HIV1-protease (HIV1-PR), and integrase (INT). Research shows that this compound can exert antiviral effects by inhibiting viral replication, blocking the virus from entering host cells, and interfering with the function of viral proteins.
As a polyhydroxyflavanone, 7,3',5'-trihydroxyflavanone has significant free radical scavenging ability, effectively reducing oxidative stress levels and lessening tissue damage. In addition, its regulatory effect on inflammatory mediators has been confirmed, inhibiting the release of pro-inflammatory cytokines and reducing inflammatory responses.
Related studies have shown that 7,3',5'-trihydroxyflavanone can regulate immune cell function, enhance the body's immune defense capabilities, and promote the establishment of antiviral immune responses.
The antiviral mechanisms of 7,3',5'-trihydroxyflavanone are diverse, mainly achieved through interactions with key viral proteins and host receptors.
MPO (Myeloperoxidase): This enzyme plays an important role in the host's immune response. 7,3',5'-trihydroxyflavanone regulates MPO activity, reduces oxidative damage, and indirectly inhibits viral infection.
UL42, UL54, ICP27, TK, gD: These are key proteins of herpes virus, involved in viral DNA replication, transcriptional regulation, and viral assembly. 7,3',5'-Trihydroxyflavanone can bind to these proteins, blocking their function and inhibiting the viral life cycle.
CCR5 and CXCR4: As core receptors for HIV virus entry into host cells, 7,3',5'-trihydroxyflavanone antagonizes these two receptors, blocking viral invasion.
HIV1-PR (protease) and INT (integrase): These two enzymes are key for HIV replication. 7,3',5'-trihydroxyflavanone blocks viral replication and gene integration by inhibiting its enzyme activity.
Molecular docking and kinetic simulation studies further revealed the binding pattern of this compound to target proteins, showing that its hydroxyl groups bind stably through hydrogen bonding and hydrophobic interactions, effectively inhibiting target activity.
7,3',5'-Trihydroxyflavanone shows good potential in terms of druggability. Its molecular weight is moderate (272.2560), and the LogP value (1.9136) complies with the Lipinski rule, making it suitable for oral absorption. TPSA is 86.99 Ų, suitable for cell membrane permeability. Although water solubility is limited (0.3356), bioavailability can be improved through formulation optimization.
The blood-brain barrier has relatively low permeability, indicating it mainly acts on peripheral tissues and reduces the risk of central nervous system side effects. hERG channel inhibition was negative, and Ames tests showed no mutagenicity, indicating high safety.
Pharmacokinetic studies show that 7,3',5'-trihydroxyflavanone is rapidly absorbed orally, has a moderate plasma half-life, and is mainly metabolized by the liver, with no significant toxicity of its metabolites. Its biotransformation involves glucuronic acid binding and sulfation, which promote excretion.
Given the multi-target action and good safety profile of 7,3',5'-trihydroxyflavanone in the antiviral field, it holds broad prospects for antiviral drug development. Especially in the treatment of herpesvirus and HIV, as a novel small molecule inhibitor, 7,3',5'-trihydroxyflavanone is expected to overcome existing drug resistance issues and offer new therapeutic strategies.
Moreover, its antioxidant and immunomodulatory effects offer potential for adjunctive treatment of chronic viral infections and related inflammatory diseases. Future research should focus on in vivo pharmacodynamic evaluation, formulation development, and preclinical safety studies to promote clinical translation.
At the same time, optimizing its water solubility and bioavailability through structural modification and drug design will further enhance its clinical value. Combining modern drug delivery systems, such as nanocarriers and targeted drug delivery technologies, is expected to achieve precise treatment.
7,3',5'-Trihydroxyflavanone, as a natural flavanoid compound with a unique structure and multiple biological activities, demonstrates broad antiviral potential and good druggability. Its multi-target mechanism of action offers new ideas for antiviral drug development. In the future, through in-depth pharmacological mechanism research, pharmacokinetic optimization, and preclinical studies, it is expected to become a new generation of safe and effective antiviral drugs. The continued development of natural product pharmacology will lay a solid foundation for the clinical application of 7,3',5'-trihydroxyflavanone, promoting its widespread use in antiviral and related disease treatments.
