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Product name: Silybin(Mixture A&B)
Synonym name: Silibinin; Silymarin; 802918-57-6
Catalogue No.: BP1305
Cas No.: 802918-57-6
Formula: C25H22O10
Mol Weight: 482.441
Botanical Source:
Physical Description: White powder
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:
Silymarin (SIL), a standardized plant extract containing about 60% polyphenole silibinin, is used as a hepatoprotective agent, it retards collagen accumulation in early and advanced biliary fibrosis secondary to complete bile duct obliteration in rats, it also may play a role in the therapy of (alcoholic) liver cirrhosis.[1,2]
Silymarin modulates imbalance between cell survival and apoptosis through interference with the expressions of cell cycle regulators and proteins involved in apoptosis; it also shows anti-inflammatory as well as anti-metastatic activity; it has the protective effects in various tissues, suggest a clinical application in cancer patients as an adjunct to established therapies, to prevent or reduce chemotherapy as well as radiotherapy-induced toxicity.[3]
Silymarin possesses antioxidant, anti-inflammatory and immunomodulatory properties which may lead to the prevention of skin cancer in in vivo animal models, suggests that it is a promising chemopreventive and pharmacologically safe agent which can be exploited or tested against skin cancer in human system, moreover, it may favorably supplement sunscreen protection and provide additional anti-photocarcinogenic protection.[4]
Silymarin induces apoptosis primarily through a p53-dependent pathway involving Bcl-2/Bax, cytochrome c release, and caspase activation.[5]
Silymarin and silibinin cause G1 and G2–M cell cycle arrest via distinct circuitries in human prostate cancer PC3 cells.[6]
References:
[1] Boigk G, Stroedter L, Herbst H, et al. Hepatology, 1997, 26(3):643-9.
[2] Saller R, Meier R, Brignoli R. Drugs, 2001, 61(14):2035-63.
[3] Ramasamy K, Agarwal R. Cancer Lett, 2008, 269(269):352-62.
[4] Katiyar S K. Int J Oncol, 2005, 26(1):169-76.
[5] Katiyar S K, Roy A M, Baliga M S. Mol Cancer Ther, 2005, 4(2):207-16.
[6] Deep G, Singh R P, Agarwal C, et al. Oncogene, 2006, 25(7):1053-69.
[7] Korany M A, Haggag R S, Ragab M A A, et al. Arab J Chem, 2013, 06.021.
HPLC of Silybin
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 (CAS No.: 802918-57-6) is a flavonoid compound isolated from the seeds of Silybum marianum and belongs to the flavonoid oligosaccharide family. As the main active ingredient in silymarin mixtures, silymarin has become a hot topic in natural product pharmacology research in recent years due to its remarkable biological activity, especially in liver protection, antioxidant, anti-inflammatory, and antitumor properties. Silymarin not only induces apoptosis but also exhibits multi-target regulatory capabilities, involving multiple signaling pathways and enzyme systems, demonstrating good pharmacological activity and safety. This paper aims to systematically review the chemical structure and physicochemical properties of silymarin, its plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation, and pharmacokinetic characteristics, as well as to explore its clinical application prospects and future development directions.
Silymarin is chemically composed of a flavonoid compound, with a molecular formula of C25H22O10 and a molecular weight of 482.4410. Its structural features include a typical flavonoid backbone, combined with multiple hydroxyl and glycosyl groups, giving it strong polarity and biological activity. The topological pole surface area (TPSA) of silymarin is 155.1400, indicating high polarity, which facilitates hydrogen bonding and van der Waals forces interactions with multiple biological targets.
In terms of physicochemical properties, silymarin has a LogP value of 1.8482, indicating moderate lipid solubility and some water solubility (solubility about 0.2082 mg/mL), which positively affects both oral absorption and internal distribution. Its low blood-brain barrier permeability suggests that silymarin has limited distribution in the central nervous system, which may reduce CNS-related adverse reactions. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames test result was 0.0, supporting the absence of significant mutagenicity and good safety.
Silybin mainly comes from the mature seeds of the Asteraceae plant Silybum marianum. Grass thistle is native to the Mediterranean region and is now widely cultivated in many parts of the world. Its seeds are rich in flavonoids, especially silymarin complexes, with silymarin being the main proportion.
There are various methods for extracting silybrabin, commonly including solvent extraction, ultrasound-assisted extraction, microwave-assisted extraction, and supercritical fluid extraction. Traditional solvent extraction usually uses ethanol or methanol as solvents, combined with thermal reflux or impregnation technologies, resulting in higher extraction efficiency. Modern technologies such as ultrasound and microwave-assisted extraction can significantly shorten extraction time, improve extraction rates, and reduce solvent usage and environmental pollution. After extraction, purification and separation are usually performed using chromatography techniques (such as HPLC) to obtain high-purity silymarbin.
Silymarin is renowned for its remarkable liver-protective effects, effectively resisting liver cell damage and dysfunction caused by various liver injury factors. Its mechanism of action mainly involves antioxidant, anti-inflammatory, anti-fibrotic, and hepatocyte regeneration. Multiple in vivo and in vitro experiments have shown that silymarin can upregulate antioxidant enzymes (such as SOD1, SOD2, CAT, GPX1) and detoxifying enzymes (NQO1, HMOX1), reduce the generation of reactive oxygen species (ROS), alleviate oxidative stress, and protect the structural integrity of hepatocyte membranes. In addition, silymarin can regulate the expression of transforming growth factor β1 (TGFB1) and actin α2 (ACTA2), inhibit hepatic stellate cell activation, and reduce the progression of liver fibrosis.
Silymarin activates the nuclear factor 2-related factor 2 (NRF2) signaling pathway, inducing downstream antioxidant gene expression and enhancing cellular antioxidant defense capacity. Activation of NRF2 promotes the expression of antioxidant enzymes such as NQO1 and HMOX1, significantly reducing oxidative damage and alleviating inflammatory responses. This mechanism plays an important role in liver protection, neuroprotection, and cardiovascular disease prevention and treatment.
Silymarin has significant anti-inflammatory activity and can inhibit the release of various inflammatory mediators, such as tumor necrosis factor α (TNF-α), interleukin-6 (IL-6), and cyclooxygenase-2 (COX-2). Its anti-inflammatory effect mainly works by regulating the nuclear factor κB (NF-κB) signaling pathway, inhibiting inflammatory gene transcription, reducing inflammatory responses, and protecting tissues from inflammatory damage.
In recent years, research on silymarin in the field of cancer prevention has gradually increased. It exerts anti-tumor effects through multiple mechanisms including inducing cancer cell apoptosis, inhibiting cell proliferation, blocking the cell cycle, and suppressing tumor invasion and metastasis. Silymarin can regulate multiple signaling pathways, including PI3K/Akt, MAPK, and Wnt/β-catenin, promoting cancer cell apoptosis and inhibiting tumor growth. In addition, silymarin can enhance the sensitivity of chemotherapy drugs, reduce chemotherapy-related toxic side effects, and demonstrate promising potential as an adjunct therapy.
The multi-target mechanism of silymarin is the foundation for its multiple pharmacological activities. Its main targets and mechanisms of action include:
In summary, silymarin achieves broad pharmacological activity through coordinated regulation through multiple targets and multiple pathways.
The druggability parameters of silymarin indicate its promising potential for drug development. A moderate molecular weight (482.4410) and LogP value (1.8482) are beneficial for drug membrane permeability and distribution in vivo. A higher TPSA (155.1400) suggests strong polarity, which may affect oral bioavailability, but also helps bind to the target with high affinity.
Silymarin has low water solubility (0.2082 mg/mL), limiting its oral absorption and prompting researchers to develop various formulation technologies (such as nanoparticles, liposomes, solid dispersions) to improve its bioavailability. Its low blood-brain barrier permeability reduces the risk of central nervous system toxicity. The negative and mutagenic ingenicity of the hERG channel (Ames test 0.0) further supports its safety.
Pharmacokinetic studies show that silymarin is mainly metabolized in the liver in the body, with metabolites primarily excreted via bile, and a moderate half-life. Its oral bioavailability is limited by intestinal absorption and first-pass effects, but through formulation optimization and combination therapy, bioavailability can be significantly improved.
As a natural product with multiple pharmacological activities, silymarin has broad clinical application prospects. Its most mature application area is adjunctive treatment of liver diseases, especially viral hepatitis, alcoholic liver disease, non-alcoholic fatty liver, and drug-induced liver injury. Multiple clinical trials have shown that silymarin can improve liver function indicators, reduce liver inflammation and fibrosis, and enhance patients' quality of life.
Moreover, silymarbin's potential in antioxidant and anti-inflammatory fields makes it a potential therapeutic candidate for cardiovascular diseases, metabolic syndromes, and neurodegenerative disorders. Its anti-cancer activity has also attracted widespread attention, and in the future, it is expected to serve as an adjunct therapy for tumors, enhancing chemotherapy efficacy and reducing side effects.
However, the clinical promotion of silymarin still faces challenges such as low bioavailability, suboptimal pharmacokinetics, and insufficient formulation development. Future research should focus on formulation technology innovation, in-depth analysis of mechanisms of action, and large-scale clinical validation to promote silymarbin's clinical translation.
Silymarin, a flavonoid derived from the seeds of thistle, demonstrates highly valuable pharmacological potential due to its remarkable liver protection, antioxidant, anti-inflammatory, and anticancer activities. Its multi-target mechanism of action provides a theoretical basis for the development of novel multifunctional drugs. Despite limitations in bioavailability and pharmacokinetics, with advances in formulation technology and deepening clinical research, silymarin is expected to become an important player in the development of natural product drugs. In the future, research into its pharmacological mechanisms, optimization of drug formulations, and systematic clinical evaluation should be conducted to promote the widespread application of silymarin in the treatment of liver diseases and other related conditions.
Shenshuai
Wenjing
Hedandan
