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Product name: Isookanin
Synonym name: Flavanokanin; Flavanookanin；Flavanone, 3',4',7,8-tetrahydroxy
Catalogue No.: BP2140
Cas No.: 1036-49-3
Formula: C15H12O6
Mol Weight: 288.255
Botanical Source: Coreopsis tinctoria Nutt.
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 Isookanin
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
107.2200
1.8429
1.6936
.1867
4.9527
2.9461
Low
83.5736
3.0531
No
No
Yes
No
Yes
No
0.6
Yes
No
Yes
No
Isookanin (CAS No.: 1036-49-3) is a natural flavonoid compound that has attracted significant attention in pharmacology and natural product research in recent years due to its broad biological activity and potential medicinal value. As a versatile natural product, isoocanine demonstrates significant activity in anti-tumor, anti-inflammatory, antiviral, antioxidant, and metabolic disease regulation, especially in the antiviral field, showing good inhibitory effects against herpes simplex virus (HSV) and varicella-zoster virus (VZV). Additionally, isoocanine has potential inhibitory effects on the pathogen causing skin diseases such as acne—Cutibacterium acnes. Related targets include DNA gyrase subunits (GYRA, GYRB), dihydrofolate reductase (DHFR), folate reductase (FOLA), and epidermal growth factor receptor 2 (ERBB2), providing a molecular basis for its application in skin disease treatment.
This paper will systematically review the chemical structure and physicochemical properties of isoocanine as well as its plant origin and extraction methods, focusing on analyzing its pharmacological activity and mechanism of action. Combined with druggability evaluation and pharmacokinetic characteristics, it explores its potential and future development directions in clinical applications, aiming to provide theoretical support and reference for in-depth research and drug development of isoocanine research.
Isoocanine belongs to the flavonoid class of compounds with a molecular formula of C15H12O6 and a molecular weight of 288.2550. Its structural feature is a typical flavonoid backbone, containing multiple hydroxyl substituents, which impart excellent antioxidant activity. Its LogP value is 1.8429, indicating moderate lipid solubility, which facilitates membrane penetration and improved bioavailability. The polar surface area (TPSA) is 107.22 Ų, indicating a certain polarity that facilitates binding to multiple biological targets.
Isocanene has relatively low water solubility (0.1867 mg/mL), which somewhat limits its application in aqueous systems, but also suggests that formulation improvements or structural modifications can optimize its pharmacokinetic properties. The low permeability of the blood-brain barrier suggests its limited distribution in the central nervous system, which may reduce CNS-related side effects. The hERG channel inhibition test results were negative, indicating that isoocanine carries a lower risk of cardiotoxicity. The Ames trial scored 0.6, indicating a low genotoxicity risk and relatively good safety.
Isoocanine is mainly found in various traditional medicinal plants, especially certain flavonoid-rich plants such as those in the Asteraceae and legume families. Common plant sources include Chrysanthemum spp. and Scutellaria baicalensis, which are widely used in traditional Chinese medicine for clearing heat and detoxifying, anti-inflammatory, and antiviral properties.
The extraction method for isoocadin mostly combines traditional organic solvent extraction with modern technology. Common extraction solvents include ethanol, methanol, and their aqueous solutions, combined with ultrasound-assisted extraction (UAE) and microwave-assisted extraction (MAE) technologies to improve extraction efficiency and purity. The crude extract after extraction is usually separated and purified by liquid-liquid separation, column chromatography (such as silica gel columns, reversed-phase C18 columns), and high-performance liquid chromatography (HPLC), ultimately yielding high-purity isoocanine.
In recent years, green extraction technologies such as supercritical fluid extraction (SFE) and enzyme-assisted extraction (EAE) have gradually been applied to isoocanene extraction, aiming to improve extraction efficiency, reduce environmental pollution, and protect the stability of active ingredients.
The pharmacological activities of isocanine cover multiple disease areas, mainly including anti-tumor, anti-inflammatory, antiviral, antioxidant, and metabolic disease regulation.
Multiple in vitro cell experiments have shown that isoocanine can exert anti-tumor effects by inducing tumor cell apoptosis, inhibiting cell proliferation, and migration. Its mechanism involves regulating cell cycle-related proteins, activating mitochondria-dependent apoptotic pathways, and inhibiting tumor-related signaling pathways (such as the ERBB2 signaling pathway). In addition, isoocanine has shown some reversal in drug resistance to certain tumor cells, suggesting its potential in adjuvant chemotherapy.
Isoocanine has a significant inhibitory effect on skin inflammatory responses, reducing the release of inflammatory mediators and the infiltration of inflammatory cells, thereby alleviating rashes and allergic reactions. Especially in treating acne causes, isoocanine reduces skin inflammation and lesions by inhibiting the growth of Propionibacterium acnes and its related target activity, making it a promising new drug for safe and effective acne treatment.
Isoocanine exhibits inhibitory activity against various viruses, especially showing significant antiviral effects against herpes simplex virus (HSV) and varicella-zoster virus (VZV). Its antiviral mechanism may include inhibiting viral DNA replication, interfering with viral protein synthesis, and blocking key steps in blocking viral invasion of cells, providing important clues for antiviral drug development.
Iocanine contains multiple phenolic hydroxyl groups, which have excellent free radical scavenging abilities and can effectively reduce oxidative stress damage. Its antioxidant activity not only protects cells from oxidative damage but also acts by regulating antioxidant enzyme systems (such as superoxide dismutase and glutathione peroxidase), helping to prevent the development of various chronic diseases.
Preliminary studies show that isoocanine also shows certain therapeutic potential in metabolic-related diseases such as diabetes and diarrhea. It assists disease management by regulating inflammatory responses, improving insulin sensitivity, and protecting intestinal barrier function.
The multi-target mechanism of isoocanine forms the basis of its various pharmacological activities. Against Propionibacterium acnes, isoocanine can bind to and inhibit key enzyme targets:
In terms of antiviral effects, isocanine blocks viral replication cycles by inhibiting viral DNA polymerase activity. Its antioxidant mechanism relies on directly scavenging reactive oxygen species (ROS) and regulating intracellular antioxidant enzyme expression, thereby reducing cellular damage caused by oxidative stress.
Additionally, isoocanine may exert anti-inflammatory and immunomodulatory effects by regulating signaling pathways such as NF-κB and MAPK, enhancing the body's resistance to disease.
The druggability parameters of isocanine indicate that it has good potential for drug development. A molecular weight of 288.2550 conforms to the Lipinski rule, and a LogP value of 1.8429 indicates moderate lipid solubility, which is beneficial for cell membrane penetration. A higher TPSA (107.22 Ų) indicates certain polarity, which may affect oral absorption but also facilitates binding to polar targets.
Low water solubility (0.1867 mg/mL) is a challenge in drug formulation development, requiring improved bioavailability through strategies such as nanocarriers, liposomes, or salt formation. The low permeability of the blood-brain barrier reduces the risk of central nervous system side effects, but limits its application in neurological diseases.
Negative hERG channel inhibition and low mutagenicity in Ames tests suggest a high safety profile of isoocanine and low risks of cardiotoxicity and genotoxicity.
Pharmacokinetic research is still in its early stages, and metabolic pathways in vivo may involve the hepatic enzyme system. The activity and toxicity of these metabolites require further evaluation. In the future, systematic in vivo pharmacokinetics and toxicology studies are needed to provide data support for clinical development.
As a versatile natural product, isoocanene shows broad clinical application prospects due to its broad pharmacological activity and good safety profile. Its potential in the antiviral field is particularly outstanding, particularly targeting HSV and VZV infections, and it may become an important candidate for new antiviral drugs. Moreover, the application of isoocanine in skin disease treatment, especially its inhibitory effect on Propionibacterium acnes, offers new ideas for treating inflammatory skin diseases such as acne.
Future research should focus on the following aspects:
In addition, the design and synthesis of derivatives based on the isoocanin structure will also be an important direction for future drug development, with the potential to obtain more efficient and safer candidate drugs.
Isoocanine, as a natural flavonoid compound with multiple biological activities, demonstrates significant potential for drug development due to its antiviral, anti-inflammatory, antioxidant, and antitumor pharmacological effects. Its excellent safety and druggability parameters provide strong support for further drug development. In the future, through in-depth mechanistic research, drug formulation optimization, and systematic clinical evaluation, isocanine is expected to become a novel natural drug for treating various diseases, especially viral infections and skin conditions. With continuous advances in natural product pharmacology and modern medicinal chemistry technologies, research on isocanine and its derivatives will inject new vitality into the development of natural product drugs and promote the widespread application of natural products in modern medicine.
Shenshuai
Wenjing
Hedandan
