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Product name: Tectorigenin
Synonym name:
Catalogue No.: BP1369
Cas No.: 548-77-6
Formula: C16H12O6
Mol Weight: 300.266
Botanical Source: Baptisia spp., Centrosema spp., Dalbergia spp. and Ononis spinosa (all Leguminosae, Papilionoideae) and also Iris germanica
Physical Description: Yellow cryst.
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, up to kilograms
Inquire for bulk scale.
Descriptions:
Tectorigenin (Tg) and tectoridin (Td) are the major compounds isolated from the rhizomes of iridaceous plant Belamcanda chinensis which is well known as a chinese traditional medicine for the treatment of inflammatory diseases; Tectorigenin inhibits IFN-γ/LPS-induced inflammatory responses in murine macrophage RAW 264.7 cells, it appears to have the potential to prevent inflammation.[1]
Tectorigenin and several other phytochemicals downregulate PDEF, PSA and IGF-1 receptor mRNA expression in vitro, the downregulation of PDEF, PSA, hTERT and IGF-1 receptor gene expression by tectorigenin demonstrates the antiproliferative potential of these agents, they might be new and established targets for therapies in prostate cancer.[2]
Tectorigenin and kaikasaponin III have hypoglycemic and hypolipidemic effects in the streptozotocin-induced diabetic rat and their antioxidant activity.[3]
Tectorigenin-paclitaxel-induces nuclear translocation of NFκB and the phosphorylation of IκB and IKK, suggests that tectorigenin could sensitize paclitaxel-resistant human ovarian cancer cells through inactivation of the Akt/IKK/IκB/NFκB signaling pathway, and promise a new intervention to chemosensitize paclitaxel-induced cytotoxicity in ovarian cancer.[4]
Tectorigenin has inhibitory effect of the activities of plasma ALT, the effects is much more potent than that of a commercially available dimethyl diphenyl bicarboxylate; Orally administered tectoridin shows hepatoprotective activity; tectorigenin also protects against the cytotoxicity of HepG2 cells induced by t-BHP, this protection may have originated from the inhibition of apoptosis; tectorigenin may be hepatoprotective and tectoridin should be a prodrug that is transformed to tectorigenin.[5]
Tectorigenin inhibits the in vitro proliferation and enhances miR-338* expression of pulmonary fibroblasts in rats with idiopathic pulmonary fibrosis.[6]
References:
[1] Pan C H, Kim E S, Sang H J, et al. Arch Pharm Res, 2008, 31(11):1447-56.
[2] Thelen P, Scharf J G, Burfeind P, et al. Carcinogenesis, 2005, 26(8):1360-7.
[3] Lee K T, Sohn I C, Dong H K, et al. Arch Pharm Res, 2000, 23(5):461-6.
[4] Genead R, Fischer H, Hussain A, et al. Carcinogenesis, 2012, 33(12):2488-98.
[5] Lee H U, Bae E A, Kim D H. J Pharmacol Sci, 2005, 97(97):541-4.
[6] Zhang H, Liu X, Shi C, et al. J Ethnopharmacol, 2010, 131(1):165-73.
[7] Zhao N, Liu D, Wang Y P, et al. J Pharm Practice, 2012, 3.
HPLC of Tectorigenin
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
100.1300
1.9839
1.6875
.0387
3.9117
34.4620
Low
91.6376
2.4411
Yes
No
Yes
No
Yes
Yes
1.8
No
No
No
No
Tectorigenin (CAS No.: 548-77-6) is a naturally occurring methoxyisoflavone compound, first isolated from dried flowers in the traditional Chinese medicine Kudzu Decoction. As an important member of the isoflavone family, irisoxin has attracted widespread attention in the field of natural product pharmacology in recent years due to its unique chemical structure and diverse bioactivity. Research shows that iris flavin not only possesses significant anti-inflammatory, antioxidant, and antitumor activities, but also shows potential pharmacological value in regulating cell signaling pathways, inhibiting tumor cell proliferation, and inducing apoptosis. This paper aims to systematically review the chemical structure and physicochemical properties of iris flavin, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation and pharmacokinetic characteristics, and to explore its clinical application prospects and future research directions, aiming to provide theoretical basis and research reference for drug development of this compound.
The chemical name of iris is 5,7,4'-trihydroxy-6-methoxyisoflavone, with a molecular formula C17H12O6 and a molecular weight of 300.2660. Its chemical structure features a typical isoflavone backbone, with 6 replaced by a methoxy group, and hydroxyl groups at positions 5, 7, and 4' respectively. This structure gives iris flavonin strong polarity and a certain lipophilicity, giving it excellent penetration of cell membranes within living organisms.
In terms of physicochemical properties, the LogP value of iris xanthin is 1.9839, indicating moderate lipid solubility, which is beneficial for distribution in the body and uptake by cells. The topological pole surface area (TPSA) is 100.13 Ų, indicating certain polarity and hydrogen bond donor/acceptor capacity, which facilitates binding to biological macromolecule targets. Low water solubility (0.0387 mg/mL) limits its oral bioavailability to some extent. The ability of irisin to penetrate the blood-brain barrier is relatively low, suggesting its role in the central nervous system is limited. Toxicological evaluation showed that it does not have hERG channel inhibitory activity; the Ames test value was 1.8, indicating a low genotoxicity risk and a solid safety foundation.
Iridin is mainly found in various traditional Chinese medicinal materials, especially isoflavone-rich plants represented by plants in the Iridaceae and legume families. Initially, the compound was isolated from dried flowers in kudzu root decoction. In addition, irisexanthin is also present in traditional medicinal plants such as Iris species, Scutellaria baicalensis, and Coptis. Its content is influenced by multiple factors such as plant species, growth environment, harvest time, and processing method.
The extraction method mainly uses organic solvent extraction combined with chromatography separation technology. Common extraction solvents include methanol, ethanol, and their aqueous solutions, as they have good solubility for isoflavones compounds. The extraction process typically includes:
1. Crush and dry plant materials;
2. Extraction using reflux or ultrasound-assisted extraction;
3. Removes impurities through liquid-liquid distribution;
4. Purification using silica gel column chromatography, reversed-phase high-performance liquid chromatography (RP-HPLC), and other methods;
5. Finally, the structure and purity are confirmed using techniques such as mass spectrometry and nuclear magnetic resonance (NMR).
In recent years, supercritical CO2 extraction and microwave-assisted extraction technologies have also been used to improve the extraction efficiency and purity of irisin, reduce the use of organic solvents, and align with the concept of green chemistry.
Iris xanthin has diverse pharmacological activities, covering anti-tumor, anti-inflammatory, antioxidant, antibacterial, and metabolic regulation aspects.
Iridin showed significant inhibitory effects across various tumor models. In vitro experiments have shown that it can inhibit the proliferation of various tumor cell lines, including breast cancer, lung cancer, liver cancer, and colorectal cancer cells. Its anti-tumor mechanism involves inducing cell cycle arrest, promoting apoptosis, and inhibiting tumor cell migration and invasion. In vivo animal models, iris flavonin significantly reduced tumor size and weight, and extended survival in experimental animals.
Irisin reduces inflammatory responses by inhibiting the production and release of inflammatory mediators. It can downregulate the expression of pro-inflammatory cytokines such as TNF-α, IL-6, and IL-1β, inhibit activation of the NF-κB signaling pathway, and reduce damage to inflammatory tissues. Relevant studies have shown that iris flavin demonstrates good therapeutic effects across various models of inflammatory diseases.
Iris xanthin has the ability to eliminate free radicals and inhibit oxidative stress, protecting cells from oxidative damage. Its antioxidant effect is achieved by enhancing the activity of endogenous antioxidant enzymes (such as superoxide dismutase SOD and glutathione peroxidase GSH-Px), reducing reactive oxygen species (ROS) levels and maintaining cellular homeostasis.
Iris flavin also exhibits potential effects such as antibacterial, regulating glycolipid metabolism, and neuroprotection, but related research is still in its early stages and requires further validation.
The pharmacological effects of iris flavonoids are mainly realized through multi-target and multi-pathway synergistic actions. Its antitumor activity involves multiple key proteins and signaling pathways:
In addition, iris flavonin exerts its anti-inflammatory and antioxidant effects by modulating signaling pathways such as NF-κB, PI3K/Akt, and Nrf2. Its multi-target properties make it a natural compound with broad-spectrum pharmacological activity.
The druggability parameters of irisin indicate that it has certain potential for drug development. A moderate molecular weight and LogP value facilitate its absorption and distribution in the body. TPSA values suggest it may enter cells through passive diffusion, but its low water solubility limits its oral absorption efficiency. The blood-brain barrier penetration capacity is relatively low, indicating limited application in the central nervous system.
Toxicological evaluation showed that iris flavin does not inhibit hERG channels, reducing the risk of cardiotoxicity. Ames test results indicate low genotoxicity and good safety. In vivo pharmacokinetic studies show that iris xanthin has limited bioavailability after oral administration, mainly metabolized by the liver, with metabolic pathways including hydroxylation and methylation. Its half-life is moderate, making it suitable for multiple doses to maintain blood concentration.
To overcome the issues of poor water solubility and low bioavailability, researchers have tried to use nanocarriers, liposomal encapsulation, and drug eutectic technologies to improve irisin solubility and in vivo stability, thereby enhancing its efficacy and safety.
As a multifunctional natural isoflavone, iris has broad pharmacological activity and good safety, demonstrating promising clinical application potential. Its research in the field of anti-tumor is particularly outstanding, and it is expected to develop into a natural anti-cancer drug that can adjuvant or replace traditional chemotherapy in the future. In addition, irisin's anti-inflammatory and antioxidant effects provide a theoretical basis for its application in chronic inflammatory diseases, metabolic syndromes, and neurodegenerative diseases.
However, clinical research on iris flavonin is still in its early stages and lacks systematic clinical trial data. Future research should focus on optimizing its pharmacokinetics, formulation development, and safety evaluation, integrating modern drug design techniques to deeply analyze its mechanisms of action and expand its indication range. At the same time, by combining multi-omics technology and network pharmacology, it systematically reveals its multi-target action network, providing support for precision treatment.
As a natural methoxyisoflavone with a unique structure and diverse biological activity, iris shows broad prospects for pharmacological research and drug development. Its remarkable activity in anti-tumor, anti-inflammation, and antioxidant properties, combined with favorable safety and druggability parameters, provides a valuable research example for the field of natural product pharmacology. In the future, with optimization of extraction processes, improvements in pharmacokinetics, and advancement of clinical research, iris is expected to become an important member of the new generation of natural medicines, contributing new strength to the treatment of human diseases.
Shenshuai
Wenjing
Hedandan
