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Product name: Iridin
Synonym name:
Catalogue No.: BP0766
Cas No.: 491-74-7
Formula: C24H26O13
Mol Weight: 522.459
Botanical Source: Belamcanda chinensis （L.）DC.
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.
Chengdu Biopurify Phytochemicals Ltd. is a leading company in the research, development, manufacture and marketing of High Quality Phytochemicals and Extracts(especially Active Ingredients from Traditional Chinese Medicine，TCM), Natural Active Pharmaceutical Ingredients worldwide.
The main services:
A. Supply active ingredients and reference standards of TCM, from mgs to kgs scale
B. Custom extraction and purification, target Herb Active Ingredients
C. Custom synthesis and semi-synthesis for Natural Active Ingredients
D. CR(contract research), CM(contract manufacture) and PD(process development) services from lab scale, pilot scale to commercial scale(GMP is also available)
E. TCM compounds library for drug screen,more than 3000 compounds available, many of them are rare and unique.
HPLC of Iridin
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
197.7400
.1710
.1328
1.6545
.6092
.4840
Low
80.4014
4.1452
Yes
No
Yes
No
Yes
No
0.6
Yes
No
Yes
No
Iridin (CAS number: 491-74-7) is a natural isoflavone product isolated from the iris family plant Iris milesii, belonging to the glycooxyisoflavone family. As a derivative formed by glycosylation of irisflorentin at the 7th hydroxyl group via β-D-pyran glucosyl residues, wild iris glycosides occupy a unique position among plant metabolites. Isoflavones have become a hot topic in natural product pharmacology research in recent years due to their diverse bioactivities and potential medicinal value. Wild iris glycoside not only possesses a typical isoflavone skeleton structure, but also, due to its glycosyl modification, exhibits physicochemical properties and biological activity distinct from the parent nucleus.
In recent years, with in-depth research into the molecular mechanisms of malignant tumors such as liver cancer, wild iris glycoside has gradually attracted academic attention due to its potential regulatory effects on various liver cancer-related targets (such as BCL2, STAT3, TOP1, MAPK1, TERT, PIK3CA, MMP9, EGFR, PTGS2, TP53, etc.). This paper will systematically review the latest research progress in the chemical structure and physicochemical properties of wild iris glycoside, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation, and clinical application prospects, aiming to provide theoretical basis and research directions for further drug development and clinical application.
The chemical structure of wild iris tail is based on the isoflavone nucleus, specifically the 4'-methoxyisoflavone structure, and at the 7th hydroxyl group, it is linked to a β-D-pyran glucosyl residue via a glycosidic bond. Its molecular formula is C_25H_26O_12, and its molecular weight is 522.4590 Da. Structurally, wild iris glycoside belongs to the 7-O-β-D-glucoside-type isoflavone, and the introduction of glycosyls significantly affects its water solubility, bioavailability, and interaction with biological targets.
In terms of physicochemical properties, the LogP value of wild iris tail is 0.1710, indicating strong hydrophilicity and good water solubility (1.6545 mg/mL, unit: water solubility). Its topological polar surface area (TPSA) is 197.74 Ų. Higher polar surface area is usually associated with poorer cell membrane permeability, which may limit its ability to cross the blood-brain barrier, consistent with its low permeability. Additionally, wild iris glycoside does not have hERG channel inhibitory activity, indicating a low risk of cardiotoxicity. The Ames test result was 0.6, indicating a low genotoxicity risk.
Glycogroup modification of the chemical structure not only improves its water solubility, but may also modulate its bioactivity by altering its molecular conformation and binding patterns to target proteins. Wild iris pigside, as a member of 4'-methoxyisoflavone, 7-hydroxyisoflavone, 7-O-β-D-glucoside, hydroxyisoflavone, and monosaccharide derivatives, reflects typical characteristics of natural product diversity.
Wild iris glycoside is mainly extracted from the iris family plant Iris milesii. Iris milesii is distributed in parts of Asia and is an important resource for traditional herbs and ornamental plants. Both the rhizomes and above-ground parts of this plant are rich in isoflavones, especially wild iris tail.
The extraction method typically uses polar solvents such as methanol, ethanol, or their aqueous solutions for reflux or ultrasound-assisted extraction of dried plant materials. After filtration and concentration, the extract is purified using multiple separation and purification techniques such as liquid-liquid separation, silica gel column chromatography, and reversed-phase high-performance liquid chromatography (RP-HPLC), ultimately obtaining high-purity wild iris glycoside. In recent years, supercritical fluid extraction and microwave-assisted extraction technologies have also been applied to improve extraction efficiency and purity.
Optimization of extraction processes mainly focuses on solvent selection, extraction time, temperature, and pH conditions to maximize retention of the active components of wild iris glycosides, reducing degradation and conversion. During purification, glycoside compounds have high polarity, requiring reasonable design of mobile phase systems and chromatographic conditions to achieve effective separation.
Research on the pharmacological activity of wild iris glycoside mainly focuses on anti-tumor, anti-inflammatory, antioxidant, and hepatoprotective aspects, with particular potential in the field of liver cancer.
Multiple in vitro cell experiments have shown that wild iris glycoside can inhibit the proliferation and migration of liver cancer cell lines (such as HepG2, Huh7, etc.), inducing cell cycle arrest and apoptosis. Its antitumor activity is closely related to the regulation of multiple signaling pathways, including inhibiting the STAT3 and PI3K/AKT pathways, reducing the expression of the anti-apoptotic protein BCL2, and promoting the activation of apoptosis-related proteins.
Additionally, wild iris glycoside can inhibit the activity of the tumor-associated protease MMP9, reducing the invasion and metastasis ability of tumor cells. Its regulatory effect on TOP1 (topoisomerase I) suggests it may influence DNA replication and repair processes, further enhancing anti-tumor efficacy.
Wild iris glycosides exhibit significant anti-inflammatory activity, downregulating PTGS2 (COX-2) expression to reduce the formation of inflammatory mediators, thereby alleviating inflammatory responses. Its antioxidant capacity helps reduce oxidative stress damage to the liver and other tissues by scavenging free radicals and increasing the activity of endogenous antioxidant enzymes.
Wild iris glycoside demonstrates protective effects in various liver injury models, reducing hepatocyte damage induced by chemical drugs or toxins and improving liver function indicators. Its mechanism may involve inhibiting hepatocyte apoptosis, regulating inflammatory responses, and promoting hepatocyte regeneration.
The mechanism of action of wild iris glycoside involves coordinated regulation of multiple targets and pathways, reflecting the multi-target pharmacological characteristics of natural products.
BCL2, as an anti-apoptotic protein, plays a key role in the survival of liver cancer cells. Wild iris glycosides disrupt intracellular anti-apoptotic balance by reducing BCL2 expression, thereby promoting mitochondrial pathway-mediated apoptosis.
STAT3 is an important transcription factor for the proliferation and immune evasion of various tumor cells. Wild iris glycoside can inhibit STAT3 phosphorylation and nuclear translocation, block the expression of its downstream tumor-causing genes, and suppress tumor growth and metastasis.
TOP1 is involved in regulating DNA supercoils and is a key enzyme for rapid tumor cell proliferation. The inhibitory effect of wild iris glycoside on TOP1 may lead to DNA damage accumulation, inducing tumor cell death.
MAPK1 (ERK2) and PIK3CA (the catalytic subunit of PI3K) are core signaling molecules for cell proliferation and survival. Wild iris glycoside regulates these two pathways, influences cell cycle progression and apoptosis signaling, and enhances its anti-tumor effects.
Wild iris tail glycoside also regulates multiple molecules, including TERT (telomerase reverse transcriptase), MMP9 (matrix metalloproteinase 9), EGFR (epidermal growth factor receptor), PTGS2 (cyclooxygenase 2), and TP53 (tumor suppressor protein), demonstrating its multi-target synergistic anti-cancer mechanism.
From the perspective of druggability, wild iris glycoside has certain advantages and challenges.
Wild iris tail has a relatively large molecular weight (522.4590 Da) and a high TPSA (197.74 Ų), suggesting that its oral bioavailability may be limited, especially due to poor cell membrane permeability, making it difficult to effectively cross the blood-brain barrier. Its LogP value is 0.1710, indicating a molecular bias toward hydrophilicity, which facilitates dissolution and distribution in body fluids, but may limit intracellular accumulation.
Wild iris glycosides do not inhibit hERG channels, reducing the risk of cardiotoxicity. Ames test results showed that it has low genotoxicity and good safety. It has high water solubility, which is beneficial for formulation development and distribution in vivo.
Currently, there is limited research on in vivo metabolism of wild iris glycosides, speculating that some of its glycosides may be hydrolyzed into iris under the influence of the gut microbiota, which has high biological activity. The pharmacological effects and toxicity of metabolites require further study.
Because wild iris glycoside acts on multiple signaling pathways, it may have synergistic or antagonistic effects with other drugs, especially those targeting tumor-related pathways. Future assessments are needed to assess the risks of drug interactions.
As a natural isoflavone glycoside, wild iris glycoside demonstrates good anti-liver cancer potential and multiple biological activities, offering high clinical value.
As a globally common malignant tumor, liver cancer has limited available treatments and significant side effects. Wild iris glycoside regulates tumor cell proliferation, apoptosis, and metastasis through multiple targets, offering a new therapeutic approach. When combined with existing chemotherapy or targeted drugs, it may achieve synergistic effects and reduce the risk of resistance.
The anti-inflammatory and liver-protective effects of wild iris pigment suggest its potential application in chronic liver disease, liver fibrosis, and inflammatory diseases. In the future, research may be expanded to include metabolic diseases and neurodegenerative diseases.
The high polarity and large molecular weight of wild iris glycosides limit their oral absorption and internal distribution, requiring improvement of pharmacokinetic performance through drug carrier techniques (such as nanoparticles, liposomes) or chemical modifications (such as deglycosylation, esterification). In addition, systematic toxicological evaluation and preclinical studies are key steps in translating it into clinical drugs.
As a typical isoflavone glycoside, wild iris glycoside combines excellent water solubility and multi-target regulation ability, demonstrating broad pharmacological activity, and holds significant potential especially in liver cancer treatment. Its multi-target and multi-pathway mechanism of action offers new ideas for the development of natural anti-tumor drugs. Although its pharmacokinetic performance and clinical translation still face certain challenges, with the development of extraction and purification technologies and drug delivery systems, wild iris glycoside is expected to become an important candidate molecule for natural anti-tumor drugs. In the future, systematic pharmacological mechanism research and preclinical evaluation will lay a solid foundation for its clinical application, promoting innovative development of natural products in liver cancer treatment.
Shenshuai
Wenjing
Hedandan
