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Product name: Dihydrokaempferol
Synonym name: Aromadendrin; Aromadendrine; Aromadendrol; (+)-Dihydrokaempferol; (2R,3R)-3,4',5,7-Tetrahydroxyflavanone
Catalogue No.: SBP00122
Cas No.: 480-20-6
Formula: C15H12O6
Mol Weight: 288.255
Botanical Source:
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.
HPLC of Dihydrokaempferol
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
107.2200
1.4369
1.2528
.6352
1.3791
1.6715
Low
80.4480
3.2059
Yes
No
Yes
No
Yes
No
1.2
Yes
No
Yes
No
Dihydrokaempferol (CAS No.: 480-20-6) is a natural flavonoid compound widely found in various plants, especially successfully isolated from the medicinal herb Bauhinia championii. As an important branch of flavonoids, dihydrokamarol has attracted widespread attention in the field of natural product pharmacology in recent years due to its unique chemical structure and diverse biological activities. Numerous studies have shown that dihydrokasanol not only has significant antioxidant capacity, but also demonstrates potential anti-inflammatory and anti-arthritis activities by regulating the expression of apoptosis-related proteins. Its inhibitory effects on Bcl-2 and Bcl-xL proteins provide a molecular basis for inducing apoptosis, demonstrating great potential as a candidate molecule for novel anti-arthritis drugs.
This paper will systematically review the chemical structure and physicochemical properties of dihydrohyphenol, plant origin and extraction methods, pharmacological activity, and mechanism of action, conduct a comprehensive evaluation based on druggability parameters, and explore its clinical application prospects and future research directions, aiming to provide theoretical basis and research reference for drug development of this natural product.
Dihydrokamarol belongs to the flavanonol subclass of flavonoid compounds, with the chemical formula C15H12O6 and a molecular weight of 288.2550. Its structural features include a typical flavanone backbone containing three hydroxyl substituents located at positions 3, 5, and 7, which give it strong hydrophilicity and antioxidant activity. The topological surface area (TPSA) of dihydrokamarol is 107.22 Ų, indicating a good polarity distribution that facilitates binding to biological macromolecules such as enzymes and receptors.
In terms of physicochemical properties, the LogP value of dihydrokasanol is 1.4369, indicating moderate lipid solubility and a certain degree of water solubility (0.6352), which is beneficial for absorption and distribution in the body. Additionally, this compound has a low blood-brain barrier penetration capacity, suggesting its limited role in the central nervous system. The hERG channel inhibition test was negative, indicating that dihydrokamarol has good safety in terms of cardiotoxicity. The Ames mutagenic test value was 1.2, basically ruling out its potential genotoxicity risk.
Dihydrokamarol was first isolated from the traditional Chinese medicinal herb Bauhinia championii, an important medicinal plant of the legume family, specifically Bauhinia genus, traditionally used to treat rheumatoid arthritis and muscle pain. Besides Bauhinia championii, dihydrokamarol is also found in various other plants, such as certain vegetables, fruits, and medicinal plants, demonstrating its wide natural distribution.
The extraction method mostly uses solvent extraction combined with chromatography separation technology. Common extraction solvents include ethanol, methanol, and their aqueous solutions, which can be improved by ultrasound-assisted extraction or reflux extraction. The extract is purified by liquid-liquid separation, column chromatography (such as silica gel columns, C18 reversed-phase columns), and high-performance liquid chromatography (HPLC), ultimately obtaining high-purity dihydrokasanol. In recent years, the application of supercritical CO2 extraction and membrane separation technologies has further optimized extraction processes, improved yield and purity, and reduced the use of organic solvents, aligning with the concept of green chemistry.
As a natural flavonoid product, dihydrophylamine exhibits strong antioxidant capacity. It significantly reduces oxidative stress damage by scavenging free radicals, inhibiting lipid peroxidation, and activating endogenous antioxidant enzyme systems. In vitro studies have shown that dihydrokasanol can enhance the activity of antioxidant enzymes such as superoxide dismutase (SOD1, SOD2), catalase (CAT), and glutathione peroxidase (GPX1), promoting the activation of intracellular antioxidant defense mechanisms. Additionally, dihydrokasanol induces activation of the NFE2L2/NRF2 signaling pathway, enhancing the expression of downstream antioxidant enzyme genes such as HMOX1 (heme oxygenase 1), further enhancing the cell's ability to resist oxidative damage.
Inflammatory responses are the core pathological process of arthritis onset. Dihydrohypanol demonstrates significant anti-inflammatory effects by inhibiting the production and release of inflammatory mediators. It can downregulate the expression of matrix metalloproteinases (MMP1, MMP3), reduce the degradation of articular cartilage, and protect the structural integrity of joints. In vivo arthritis model studies show that dihydrokasanol significantly reduces joint swelling and inflammatory cell infiltration, improves joint function, suggesting its potential as a new anti-arthritis drug.
Dihydrokamarol demonstrates the ability to induce apoptosis in various tumor cell lines. Its mechanism mainly involves inhibiting the expression of anti-apoptotic proteins Bcl-2 and Bcl-xL, disrupting mitochondrial membrane potentials, activating intracellular apoptosis signaling pathways, and promoting programmed cell death. This effect not only aids in anti-tumor treatment but also provides theoretical support for regulating abnormal cell proliferation.
The multi-target mechanism of dihydrokamarol forms the basis of its multiple pharmacological effects. Its main targets include:
Antioxidant-related targets: By activating the NFE2L2/NRF2 signaling pathway, it regulates the expression of downstream antioxidant enzyme genes (SOD1, SOD2, CAT, GPX1, HMOX1), enhancing cellular antioxidant defense capacity and reducing oxidative stress damage.
Matrix metalloproteinases (MMP1, MMP3): Inhibit the expression of MMPs, prevent extracellular matrix degradation, protect cartilage tissue, and slow down arthritis progression.
Apoptotic regulatory proteins (Bcl-2, Bcl-xL): Downregulate the expression of anti-apoptotic proteins, promote mitochondria-mediated apoptosis, and regulate the balance between cell proliferation and death.
Tyrosinase (TYR): Although mainly related to melanin synthesis, its regulation may indirectly affect cellular redox states.
The synergistic regulation of these targets enables dihydrokasanol to exhibit pleiotropy in antioxidant, anti-inflammatory, and cytoptotic regulation, highlighting its unique advantages as a natural drug candidate.
The druggability parameters of dihydrokasanol indicate that it has promising potential for drug development. Moderate molecular weight (288.2550) and LogP (1.4369) comply with the Lipinski rule, which is beneficial for oral absorption. The TPSA value was 107.22, indicating certain polarity that may affect membrane permeability, but overall it remains suitable for distribution in vivo. Moderate water solubility (0.6352), which aids formulation development and dissolution in the body.
In terms of safety, the hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames test result was 1.2, which basically ruled out the risk of genotoxicity. The blood-brain barrier has a relatively low penetration capacity, suggesting a lower risk of side effects in the central nervous system, but also limits its application in neurological diseases.
Currently, pharmacokinetic research on dihydrokamarol is relatively limited. Preliminary data indicate that its oral bioavailability is moderate, and its metabolism in the body mainly occurs through hepatic enzyme systems. The metabolites still require further identification. In the future, systematic research into its in vivo absorption, distribution, metabolism, and excretion (ADME) characteristics needs to be strengthened to optimize dosage formulation design and administration regimens.
Based on the multiple pharmacological activities of dihydrokamarol, especially its significant effects in antioxidant and anti-arthritis fields, it has broad prospects as a candidate molecule for new drugs. As a common chronic inflammatory disease, arthritis currently has limited clinical treatment options and side effects. Dihydrokasanol offers a natural, safe, and well-defined new therapeutic strategy.
Future research should focus on the following directions:
Systematic pharmacokinetic and toxicological evaluation: Improving in vivo behavioral and safety data of dihydrokamarol to provide scientific basis for clinical trials.
Dosage form optimization and drug delivery route exploration: developing oral, topical, or injectable dosage forms to improve bioavailability and targeting.
Preclinical multi-model validation: Using various arthritis animal models and other inflammatory disease models, systematically evaluate efficacy and mechanisms of action.
Combination drug studies: exploring synergistic effects with existing anti-inflammatory drugs or immunomodulators to enhance treatment efficacy and reduce adverse reactions.
Structural modification and derivative development: Designing novel derivatives based on the dihydrokamarol framework to optimize pharmacodynamics and pharmacokinetic properties.
In addition, the potential applications of dihydrokamarol in fields such as antitumor and neuroprotection are also worth further exploration to expand its clinical indications.
Dihydrophysamphenol, a natural flavonoid compound derived from Bauhinia championii, demonstrates great potential as a candidate for new anti-arthritis drugs due to its significant antioxidant, anti-inflammatory, and apoptosis-inducing activities. Its multi-target mechanism of action and favorable druggability parameters have laid a solid foundation for its drug development. Although research on its pharmacokinetics and clinical applications is still in its early stages, with the development of modern medicinal chemistry and biotechnology, dihydrokasanol is expected to become a major breakthrough in the field of natural product pharmacology, providing new solutions for the treatment of related diseases. Future systematic research and clinical validation will be key to driving its translational application.
Shenshuai
Wenjing
Hedandan
