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Product name: Silybin A
Synonym name: Silymarine I；Silybine; Silybum substance E6; Silymarin I; Silymarin MZ 80
Catalogue No.: BP5185
Cas No.: 22888-70-6
Formula: C25H22O10
Mol Weight: 482.441
Botanical Source:
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.
For Reference Standard and R&D, Not for Human Use Directly.
HPLC of Silybin A
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
155.1400
1.8482
1.7104
.2082
1.8367
.7008
Low
89.1451
3.9920
No
No
No
No
Yes
No
0.0
Yes
No
Yes
No
Silybin A (CAS No.: 22888-70-6), as one of the main active ingredients in Silybum marianum, has attracted widespread attention in the field of natural product pharmacology in recent years due to its remarkable biological activity. Silymarin A is a type of flavonoid lignan compound with multiple pharmacological effects, including antioxidant, anti-tumor, liver-protecting, and chemotherapy support. Its unique chemical structure endows it with excellent bioactivity and good safety, making it a research hotspot in the fields of natural drug development and liver disease treatment.
This paper aims to systematically review the chemical structure and physicochemical properties of silymarin A, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation, pharmacokinetic characteristics, and its clinical application prospects, comprehensively presenting the research progress and future directions of this compound in natural product pharmacology.
Silymarin A is a flavonoid lignan with the molecular formula C25H22O10 and a molecular weight of 482.4410. Its structural features include α-hydroxy ketones, polyphenolic hydroxyl groups, aromatic ethers, and benzodioxin rings, forming its complex three-dimensional configuration. The chemical framework of silymarin A gives it powerful free radical scavenging capabilities and the potential to bind to multiple biological targets.
In terms of physicochemical properties, the LogP value of silymarin A is 1.8482, indicating moderate lipid solubility that facilitates cell membrane penetration. The polar surface area (TPSA) is 155.14 Ų, indicating high molecular polarity, which affects its water solubility and bioavailability. Water solubility is 0.2082 (unspecified, usually mg/mL or g/L), indicating low water solubility and limiting oral absorption efficiency. The low permeability of the blood-brain barrier suggests a low risk of central nervous system side effects. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. Ames mutagenic test results were zero, indicating an extremely low risk of genotoxicity.
Silybin A is mainly isolated from the fruit of Silybum marianum. Milk thistle is a traditional herb widely distributed in Europe, the Mediterranean region, and parts of Asia. Its fruit contains a rich mixture of flavonoids and lignans, with silymarin A being one of the most abundant isomers.
The extraction method typically uses organic solvent extraction combined with column chromatography separation technology. Common solvents include methanol, ethanol, ethyl acetate, etc. The extracts are purified by silica gel columns or reversed-phase high-performance liquid chromatography (RP-HPLC) to obtain high-purity silybin A. In recent years, green extraction technologies such as ultrasound-assisted extraction, microwave-assisted extraction, and supercritical CO2 extraction have also been applied to silymarin A, improving extraction efficiency and purity and reducing environmental pollution.
Silymarin A has significant antioxidant activity, scavenging free radicals and reducing oxidative stress damage. Its polyphenolic hydroxyl structure enables it to effectively capture reactive oxygen species (ROS) and active nitrogen (RNS), protecting cells from oxidative damage. In vitro studies show that silybin A can enhance the activity of intracellular antioxidant enzymes such as superoxide dismutase (SOD), catalase (CAT), and glutathione peroxidase (GPX1), reducing lipid peroxidation and DNA oxidative damage.
Silymarin A has shown effects in inhibiting cell proliferation, inducing apoptosis, and inhibiting migration across various tumor models. Its anticancer activity involves multiple signaling pathways, including NF-κB, PI3K/Akt, MAPK, and Wnt/β-catenin. Silymarin A induces tumor cell apoptosis by regulating the expression of cyclins, pro-apoptotic proteins, and anti-apoptotic proteins, thereby inhibiting the invasion and metastasis abilities of tumor cells.
As a classic hepatoprotective agent, silymarin A has a liver-protective mechanism involving antioxidant, anti-inflammatory, antifibrotic, and hepatocyte regeneration. By activating the nuclear factor red 2-related factor 2 (NRF2) signaling pathway, silybin A upregulates the expression of antioxidant enzymes such as NQO1 and HMOX1, thereby alleviating oxidative liver damage. At the same time, silymarin A inhibits matrix metalloproteinase 9 (MMP9) and transforming growth factor β1 (TGFB1), slowing the progression of liver fibrosis. In addition, silymarin A can reduce liver inflammation and protect the structure and function of liver cells.
Silymarin A also exhibits multiple pharmacological activities, including anti-inflammation, antiviral, immunomodulatory, and neuroprotective effects, providing a theoretical basis for its clinical application.
The mechanism of action of silymarin A is complex, involving coordinated regulation of multiple targets and multiple pathways. Its main molecular targets include:
In addition, silymarin A achieves multi-level regulation of tumor cells and liver pathological states by regulating cell cycle-related proteins, apoptosis-related proteins, and inflammatory factors.
The druggability parameters of silymarin A indicate that it has good potential for drug development. Moderate molecular weight and LogP values facilitate cell membrane penetration and distribution in vivo. High TPSA and lower water solubility suggest limited oral bioavailability, requiring drug formulation optimization or improved absorption through nanocarrier technology.
The blood-brain barrier has low permeability, reducing the risk of central nervous system side effects. No hERG channel inhibition and no mutagenicity, resulting in relatively high safety.
Pharmacokinetic studies show that silymarin A is slowly absorbed orally and has low bioavailability, mainly metabolized and excreted through the liver. Its metabolic pathways include glucuronylation and sulfation, with most metabolites being water-soluble conjugates. It has a moderate half-life in vivo, making it suitable for multiple doses to maintain effective concentrations.
To overcome its poor water solubility and low bioavailability, researchers have recently tried to use new drug carrier systems such as liposomes, nanoparticles, and solid dispersions to improve their in vivo stability and targeting.
As a versatile natural product, silymarin A has broad clinical application prospects. Its hepatoprotective effects have been validated in various liver disease models, especially with great potential in hepatitis, liver fibrosis, and drug-induced liver injury. Its antitumor activity makes it a strong candidate for adjunct cancer treatment, especially showing good synergistic effects in solid tumors such as liver, breast, and lung cancers.
In the future, clinical translation of silymarin A will focus on addressing its bioavailability and targeted delivery issues. By combining modern drug formulation technology with precision medicine concepts, developing efficient and safe delivery systems will greatly enhance their clinical application value.
In addition, the multi-target mechanism of silymarin A provides a theoretical basis for combination drug strategies, and is expected to be used synergistically with existing antitumor and anti-inflammatory drugs to enhance efficacy and reduce toxic side effects.
As the main active ingredient in milk thistle, silymarin A demonstrates significant value in the field of natural product pharmacology due to its unique chemical structure and diverse pharmacological activities. Its antioxidant, antitumor, and hepatoprotective mechanisms are clear, molecular targets are well-defined, safety is good, and it has high drug potential.
Future research should focus on optimizing its pharmacokinetic properties, deepening the analysis of its mechanism of action, expanding clinical indications, and integrating modern formulation technologies to promote its clinical translation. Silymarin A is expected to become a model in the development of natural product drugs, offering new therapeutic strategies and drug options for liver disease and tumor treatment.
Shenshuai
Wenjing
Hedandan
