Product name: Pinostrobin chalcone
Synonym name:
Catalogue No.: SBP00137
Cas No.: 18956-15-5
Formula: C₁₆H₁₄O₄
Mol Weight: 270.284
Botanical Source:
Type of Compound:

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 Pinostrobin chalcone

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

Introduction/Overview

Pinostrobin chalcone (CAS No.: 18956-15-5) is a class of natural flavonoid compounds with significant biological activity, widely found in various plants. In recent years, with the rapid development of natural product pharmacology, cochinosal chalcone has attracted widespread attention due to its multi-target, multifunctional bioactivity, and especially its potential in anti-tumor and antioxidant fields. It exhibited significant cytotoxic effects against the MDA-MB-231 triple-negative breast cancer cell line and the HT-29 colon cancer cell line, with IC50 values of 20.42±2.23 μg/mL and 22.51±0.42 μg/mL, respectively, suggesting it may be an important candidate molecule for anticancer drug development. In addition, chalcone volux demonstrates good antioxidant activity by regulating various antioxidant-related targets (such as NFE2L2/NRF2, SOD1, CAT, GPX1, etc.), providing a theoretical basis for its application in oxidative stress-related diseases. This paper will systematically review the chemical structure and physicochemical properties of chalcone voluxin, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation, and pharmacokinetic characteristics, and explore its clinical application prospects and future development directions.

Chemical structure and physicochemical properties

Vicularin chalcone belongs to the chalcone class of compounds and is a precursor to flavonoids. Structurally, it is formed by two aromatic rings connected by α β-unsaturated carbonyl groups, forming a typical chalcone backbone. Its molecular formula is C16H14O4, and its molecular weight is 270.2840. The LogP value of chalcone is 3.5875, indicating moderate lipid solubility that facilitates cell membrane penetration, but its water solubility is relatively low (0.0548), which may affect its solubility and bioavailability in vivo. Its topological pole surface area (TPSA) is 66.7600, indicating moderate polarity, which is favorable for binding with biological macromolecules. The blood-brain barrier has low permeability, limiting its distribution in the central nervous system. The hERG channel inhibition test result was negative, indicating a low risk of cardiotoxicity. The Ames test result was 0.6, indicating a low genotoxicity risk and a solid safety foundation.

In the chemical structure of cochinon chalcone, α,β-unsaturated carbonyl groups are important groups for its bioactivity, capable of covalent or non-covalent interactions with various enzymes and receptors. Additionally, the hydroxyl and methoxy groups on its aromatic ring impart antioxidant activity, working by capturing free radicals and regulating the expression of antioxidant enzymes within cells.

Plant Origins and Extraction Methods

Cobulin chalcone is mainly found in various Chinese medicinal materials and aromatic plants, especially from ginger plants such as turmeric (Curcuma longa), Pinus spp., and other flavonoid-rich plants. Its content is greatly influenced by plant species, growing environment, harvest time, and processing methods.

Common extraction methods include solvent extraction, ultrasound-assisted extraction, and high-performance liquid chromatography (HPLC) separation. Ethanol or methanol is generally used as extraction solvents, with ultrasound assisted to improve extraction efficiency. After concentration, separation, and silica gel column chromatography purification, the extract was then analyzed qualitatively and quantitatively using HPLC or mass spectrometry. In recent years, green extraction technologies such as supercritical CO2 extraction and microwave-assisted extraction have gradually been applied to the extraction of chalcone and volosin, improving extraction efficiency and purity, reducing the use of organic solvents, and aligning with green chemistry principles.

Pharmacological activity research

Antitumor activity

Coblosin chalcone exhibited significant cytotoxicity across various tumor cell lines, especially low IC50 values (20.42±2.23 μg/mL and 22.51±0.42 μg/mL) in MDA-MB-231 triple-negative breast cancer cells and HT-29 colon cancer cells, indicating its potential anticancer activity. Cell experiments have shown that chalcone can induce apoptosis in cancer cells, inhibit cell proliferation and migration, and has low toxicity to normal cells within a certain concentration range, demonstrating good selectivity.

Antioxidant activity

Chalcone Vicular exerts antioxidant effects by regulating various antioxidant enzymes and related signaling pathways. Its targets include tyrosinase (TYR), matrix metalloproteinases 1 and 3 (MMP1, MMP3), nuclear factor E2-related factor 2 (NFE2L2/NRF2), superoxide dismutase 1 and 2 (SOD1, SOD2), catalase (CAT), glutathione peroxidase 1 (GPX1), and heme oxygenase 1 (HMOX1). Chalcone can activate the NRF2 signaling pathway, promote the expression of intracellular antioxidant enzymes, eliminate excess reactive oxygen species (ROS), reduce cellular damage caused by oxidative stress, and protect cellular function.

Other biological activities

In addition to antitumor and antioxidant effects, chalcone also exhibits various biological activities including anti-inflammatory, antibacterial, and neuroprotective effects. Its anti-inflammatory effects are mainly achieved by inhibiting the expression of inflammatory factors and modulating signaling pathways. Antibacterial activity involves inhibiting various Gram-positive and Gram-negative bacteria. Neuroprotective effects are closely related to its antioxidant capacity and may have potential value in preventing and treating neurodegenerative diseases.

Mechanism of action and molecular targets

The pharmacological mechanism of cochinosin chalcone involves multiple signaling pathways and molecular targets, reflecting its multi-target regulatory characteristics.

Antitumor mechanism

Viclosin chalcone inhibits tumor cell proliferation by inducing cancer cell apoptosis and cell cycle arrest. Its mechanisms include:

• Activates mitochondrial pathways, regulates the expression of Bcl-2 family proteins, promotes cytochrome C release, and activates the Caspase cascade.
• Inhibits the PI3K/Akt and MAPK signaling pathways, blocking cell proliferation and survival signals.
• Inhibits matrix metalloproteinase (MMP1, MMP3) activity, reducing tumor cell migration and invasion capacity.
• Regulates the NF-κB signaling pathway, reduces pro-inflammatory factor expression, and alleviates the cancer-promoting effects of the tumor microenvironment.

Antioxidant mechanism

Chalcone foulosinol activates the NFE2L2/NRF2 transcription factor, promoting the expression of downstream antioxidant enzymes (SOD1, SOD2, CAT, GPX1, HMOX1) genes, enhancing cells' ability to clear ROS and protecting cells from oxidative damage. In addition, the hydroxyl groups in its structure can directly scavenge free radicals, acting as free radical scavengers.

Other mechanisms

Ballsonin chalcone may also influence melanin synthesis by modulating tyrosinase (TYR) activity, offering potential whitening and skin-protective effects. Its anti-inflammatory mechanism involves inhibiting the synthesis of inflammatory mediators and modulating signaling pathways to reduce inflammatory responses.

Druggability evaluation and pharmacokinetics

The druggability parameters of colosone chalcone indicate that it has certain potential for drug development. A molecular weight of 270.2840 conforms to the Lipinski rule, and a LogP value of 3.5875 indicates moderate lipid solubility, which facilitates cell membrane penetration. TPSA is 66.7600, indicating moderate polarity and conducive to biological activity. Low water solubility (0.0548) may limit oral bioavailability, requiring formulation optimization or structural modification.

The blood-brain barrier has low permeability, limiting its application in the central nervous system, but reducing the risk of CNS toxicity. hERG channel inhibition was negative, indicating a low risk of cardiotoxicity. Ames trial results showed that it carries a low genotoxicity risk and is relatively safe.

Currently, pharmacokinetic studies on colosinal chalcone are limited. Preliminary data indicate that its metabolism is stable in the body, mainly metabolized through hepatic enzyme systems, and its excretion pathway still requires further study. In the future, systematic studies of ADME (Absorption, Distribution, Metabolism, Excretion) should be conducted to clarify in vivo behavioral and drug interaction risks.

Prospects and outlooks for clinical applications

As a versatile natural product, cochinosol chalcone has broad clinical application potential. Its remarkable antitumor activity provides important candidate molecules for the development of novel anticancer drugs, especially in the fields of breast and colon cancer. Combining its antioxidant and anti-inflammatory effects, chalcone colosinal shows promise as an adjunct treatment for oxidative stress-related diseases such as cardiovascular diseases, neurodegenerative diseases, and chronic inflammatory diseases.

However, the clinical translation of colosinal chalcone still faces many challenges. First, its low water solubility and potential bioavailability limit the effectiveness of oral administration. Second, the lack of systematic pharmacokinetic and toxicological data limits comprehensive evaluation of its safety and efficacy. In addition, the mechanism of cochinosone chalcone requires further analysis, especially its network mechanism of multi-target coordinated regulation in vivo.

Future research should focus on:

• Structural modification and nanocarrier technology enhance their water solubility and bioavailability.
• Systematic pharmacokinetics, toxicology, and safety evaluations were conducted.
• Multi-omics techniques and molecular simulations were used to deeply analyze its mechanism of action.
• Design reasonable preclinical and clinical trials to verify efficacy and safety.
• Explore its potential for combination therapy with existing drugs to exert synergistic effects.

Conclusion

As a natural chalcone compound with multiple targets and multiple functions, it demonstrates excellent antitumor and antioxidant activity, with a solid druggability foundation and safety potential. Its application prospects in the treatment of breast cancer, colon cancer, and other tumors have broad prospects, and it also holds significant value in the prevention and treatment of oxidative stress-related diseases. In the future, through structural optimization, pharmacokinetic studies, and clinical translational studies, chalcone is expected to become an important component of the new generation of natural drugs, advancing the pharmacology of natural products and the development of anticancer drugs.