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Product name: Okanin
Synonym name: 2',3,3',4,4'-Pentahydroxychalcone
Catalogue No.: BP2137
Cas No.: 484-76-4
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.
The product could be supplied from milligrams to grams
Inquire for bulk scale.
For Reference Standard and R&D, Not for Human Use Directly.
Description:
1. Okanin shows significant activities on both linoleic acid peroxidation inhibition and DPPH radical scavenging effect.
2. Okanin shows significant protective effects against tacrine-induced cytotoxicity in human liver-derived Hep G2 cells with the EC50 value of 29.8±1.1 uM.
3. Okanin can inhibit nitric oxide production and inducible nitric oxide synthase expression via nuclear factor-erythroid 2-related factor 2-dependent heme oxygenase-1 expression in lipopolysaccharide-activated macrophages.
4. Okanin attenuates LPS-induced microglial activation through inhibition of the TLR4/NF-κB signaling pathways, suggests that okanin may have potential as a nutritional preventive strategy for neurodegenerative disorders.
References:
Korean Journal of Pharmacognosy, 2009 , 40 (4) :345-50.
Antioxidative and hepatoprotective effect of compounds from the flowers of bidens Bipinnata L.
METHODS AND RESULTS:
Activity-guided fractionation of the EtOH extract of flowers of Bidens bipinnata L. have been furnished five flavonoids, sulfuretin(1), butein(2), 7,8,3′,4′-tetrahydroxyflavanone(3), maritimetin(4) and Okanin(5). All of the compounds showed significant activities on both linoleic acid peroxidation inhibition and DPPH radical scavenging effect. The evaluation for protective effect of isolated compounds against tacrine-induced cytotoxicity in human liver-derived Hep G2 cells was conducted. Compounds 1, 3, 4 and 5 showed significant protective effects with the EC50 values of 36.1±0.9, 23.3±0.7, 41.0±1.0 and 29.8±1.1 μM, respectively.
CONCLUSIONS:
Silybin, one of the well-known hepatoprotective agents, used as a positive control, and also showed protective effect with an EC50 value of 84.3±0.7 μM.
J Clin Biochem Nutr. 2012 Jan; 50(1): 53–58.
Okanin, a chalcone found in the genus Bidens, and 3-penten-2-one inhibit inducible nitric oxide synthase expression via heme oxygenase-1 induction in RAW264.7 macrophages activated with lipopolysaccharide
Okanin is one of the most abundant chalcones found in the genus Bidens (Asteraceae) that is used as various folk medications in Korea and China for treating inflammation.
METHODS AND RESULTS:
Here, we found that Okanin (possessing the α-β unsaturated carbonyl group) induced heme oxygenase-1 expression via nuclear factor-erythroid 2-related factor 2 activation in RAW264.7 macrophages. 3-Penten-2-one, of which structure, as in Okanin, possesses the α-β unsaturated carbonyl group, also induced nuclear factor-erythroid 2-related factor 2-dependent heme oxygenase-1 expression, while both 2-pentanone (lacking a double bond) and 2-pentene (lacking a carbonyl group) were virtually inactive. In lipopolysaccharide-activated RAW264.7 macrophages, both Okanin and 3-penten-2-one inhibited nitric oxide production and inducible nitric oxide synthase expression via heme oxygenase-1 expression.
CONCLUSIONS:
Collectively, our findings suggest that by virtue of its α-β unsaturated carbonyl functional group, Okanin can inhibit nitric oxide production and inducible nitric oxide synthase expression via nuclear factor-erythroid 2-related factor 2-dependent heme oxygenase-1 expression in lipopolysaccharide-activated macrophages.
HPLC of Okanin
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
118.2200
2.4941
1.5195
.0803
5.5265
4.8384
Low
88.3454
2.3925
Yes
Yes
No
No
Yes
No
0.6
Yes
No
Yes
Yes
Okanin (CAS number: 484-76-4) is a natural flavonoid compound mainly found in Coreopsis tinctoria. As one of the plant's main active ingredients, Okanine has attracted widespread attention in recent years due to its diverse biological activities. Research shows that okanine exhibits significant anti-inflammatory, antioxidant, and antimicrobial activities, especially in regulating immune responses and inhibiting inflammatory signaling pathways. By inhibiting the Toll-like receptor 4 (TLR4)-mediated nuclear factor κB (NF-κB) signaling pathway, it effectively weakens lipopolysaccharide-induced microglial activation, suggesting its potential application value in neuroinflammation and related neurodegenerative diseases.
In addition, ocanine has shown certain activity in the field of antifungal infections, involving multiple key targets such as MAPK1, ERG11, and CDR1, all of which are important molecules in fungal growth and resistance mechanisms. This paper aims to systematically review the chemical structure, physicochemical properties, plant origin, and extraction methods of occanine, delve into its pharmacological activity and mechanism of action, evaluate its druggability and pharmacokinetic characteristics, and finally look ahead to its clinical application prospects, providing theoretical basis and research directions for natural product pharmacology and new drug development.
Okanin has the molecular formula C15H12O6 and a molecular weight of 288.2550. Its chemical structure belongs to the flavonoid class, specifically dihydroxyflavonoid derivatives, containing multiple hydroxyl and ketone groups, which impart strong polarity and antioxidant capacity. Its LogP value is 2.4941, showing moderate lipid solubility that facilitates membrane penetration, but its water solubility is relatively low (0.0803), indicating limited solubility in the aqueous phase. The polar surface area (TPSA) is 118.2200, indicating that its molecules have strong polar characteristics, which have an important impact on their binding to biological macromolecules and their distribution in vivo.
The structural characteristics of ocanine give it excellent multi-target action in terms of biological activity. It does not inhibit the hERG channel, and the Ames test result is 0.6, indicating a low genotoxicity risk and good safety. The blood-brain barrier has relatively low permeability, suggesting that its direct role in the central nervous system may be limited, but by regulating peripheral immune cell activation, it can still indirectly influence the neuroinflammatory process.
Okani mainly comes from Coreopsis tinctoria, a herbaceous plant widely distributed in North America and parts of China. As a traditional herbal and natural dye plant, dyed chrysanthemum is rich in flavonoids and polyphenolic compounds. As one of its main active ingredients, ocanine is usually obtained through plant extraction and separation purification.
Common extraction methods include solvent extraction, ultrasound-assisted extraction, and liquid-liquid partitioning. Using ethanol or methanol as extraction solvents combined with ultrasound-assisted technology can effectively improve the extraction rate of ocanine extraction. After concentration, separation, and column chromatography purification, the extract was identified and content determined using high-performance liquid chromatography (HPLC) and mass spectrometry (MS) techniques. In recent years, green extraction technologies such as supercritical CO2 extraction and microwave-assisted extraction have also been applied to the extraction of okanene to improve extraction efficiency and reduce the use of organic solvents, meeting the environmental requirements of modern natural product development.
Ocanin exerts anti-inflammatory effects by inhibiting the TLR4/NF-κB signaling pathway, significantly weakening LPS-induced microglial activation and reducing the expression of pro-inflammatory factors such as TNF-α, IL-1β, and IL-6. Multiple in vitro cell experiments and animal model studies have confirmed that okanin can regulate the inflammatory response of immune cells and reduce neuroinflammatory damage, suggesting its potential therapeutic value in neurodegenerative diseases such as Alzheimer's and Parkinson's.
Okanin has shown inhibitory activity against various fungal infection-related targets, including mitogen-activated protein kinase (MAPK1), fungal cell membrane synthase ERG11 (CYP51 homologolase), efflux pump CDR1, β-1,3-glucan synthase FKS1, chitin synthase CHS3, cell attachment protein ALS3, and protease SAP2. Through multi-target synergistic action, okanine interferes with the synthesis and function of fungal cell walls and membranes, inhibiting fungal growth and pathogenicity, and has good antifungal potential, especially showing certain inhibitory effects against drug-resistant strains.
In addition to its anti-inflammatory and antifungal activities, Okanine also exhibits certain antioxidant, anti-tumor, and neuroprotective effects. Its antioxidant activity mainly comes from the phenolic hydroxyl group structure in its molecules, which can eliminate free radicals and reduce oxidative stress damage. Some studies have shown that okanine can induce tumor cell apoptosis and inhibit tumor cell proliferation, but the related mechanisms still require further in-depth exploration.
The main mechanism of action of okanine focuses on its regulation of inflammatory signaling pathways and key fungal enzymes.
TLR4 is a key receptor for the immune system to recognize bacterial lipopolysaccharides (LPS). After activation, it activates NF-κB signaling via the MyD88-dependent pathway, inducing inflammatory factor expression. Ocanine can block TLR4 activation, inhibit downstream IκBα phosphorylation and NF-κB nuclear translocation, reduce the production of pro-inflammatory cytokines, and alleviate inflammatory responses. This is especially prominent in microglia, showing neuroprotective effects.
Ocanine exerts its antifungal effect by interfering with the synthesis and function of fungal cell membranes and cell walls. Its targets include:
These multi-target mechanisms give okanine potential advantages in antifungal therapy, especially providing new ideas for treating resistant strains.
The druggability parameters of occanine indicate that it has certain development potential. The molecular weight of 288.2550 complies with the Lipinski rule, and the LogP value of 2.4941 is moderate, indicating good membrane permeability. TPSA is 118.2200, slightly above the ideal range, which may limit oral absorption efficiency. Low water solubility (0.0803) suggests that strategies to improve solubility, such as nanocarriers or solid dispersion technologies, should be considered in formulation development.
The low permeability of the blood-brain barrier limits its ability to directly enter the central nervous system, but this is still beneficial for regulating peripheral inflammation. hERG channel inhibition negative, reducing the risk of cardiotoxicity. Ames test results showed low genotoxicity and good safety.
Currently, pharmacokinetic research on occanine is relatively limited. Preliminary data indicate that its oral bioavailability is limited, and its metabolism mainly occurs through hepatic enzyme systems. The activity and toxicity of these metabolites require further evaluation. In the future, systematic ADME (absorption, distribution, metabolism, excretion) research and pharmacokinetic analysis are needed to provide a basis for clinical translation.
As a versatile natural product, ocanine possesses broad pharmacological activity and good safety, demonstrating high clinical application potential. Its role in regulating neuroinflammation, especially targeting the inhibition of microglial activation, offers new ideas for adjunctive treatment of neurodegenerative diseases such as Alzheimer's and Parkinson's disease. Combined with its multi-target antifungal mechanism, okanin is expected to become a candidate molecule for novel antifungal drugs, especially of great significance in the treatment of drug-resistant fungal infections.
Future research should focus on optimizing the pharmacokinetics, formulation development, and preclinical safety evaluation of occanine. In addition, by combining modern molecular biology and medicinal chemistry methods, in-depth analysis of its mechanisms of action, screening for structure-optimized derivatives, and improving bioavailability and targeting will promote its clinical translational process. The launch of multicenter clinical trials will be a key step in verifying its efficacy and safety.
In summary, as an important active ingredient in Coreopsis tinctoria, Ocanin, with its unique chemical structure and multi-target mechanism, shows broad application prospects in anti-inflammatory, antifungal, and neuroprotective fields. By inhibiting the TLR4/NF-κB signaling pathway, it effectively regulates immune inflammatory responses, while also acting synergistically against key fungal enzymes and proteins, providing a valuable natural molecular template for new drug development. Although challenges remain in pharmacokinetics and clinical applications, with deeper research and technological advancements, occanine is expected to become a star molecule in the field of natural product pharmacology, driving therapeutic innovation for related diseases. Future research should focus on mechanism analysis, structural optimization, and clinical validation to achieve translational applications from the laboratory to clinical practice.
Shenshuai
Wenjing
Hedandan
