+86-28-82633987
Product Name: Cyanidin 3-Arabinoside
Synonym name: Chrolide, 27214-72-8
Catalogue No.: BP0426
Cas No.: 792868-19-0
Formula: C20H19O10+
Mol Weight: 419.361
Botanical Source: numerous plant spp. including red pears and apples and other fruits
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Can be supplied from milligrams to grams.
For Reference Standard and R&D, Not for Human Use Directly.
Inquire for bulk scale.
HPLC of Cyanidin 3-Arabinoside
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
189.7900
-1.5000
-2.5000
Low
No
No
No
No
No
No
No
Cyanidin 3-arabinoside (CAS No.: 792868-19-0), a natural anthocyanin compound, has attracted widespread attention in the field of natural product pharmacology in recent years. Its unique bioactivity, especially its role as a selective and reversible inhibitor of protein tyrosine phosphatase 1B (PTP1B), gives it significant potential in research on metabolic diseases such as type 2 diabetes. In addition, cyanidin arabinoside demonstrates strong antioxidant capacity, regulating various antioxidant-related targets to reduce oxidative stress damage, further enriching its pharmacological value. This paper will systematically review the chemical structure and physicochemical properties of cyanidin arabinoside, plant origin and extraction methods, pharmacological activity, mechanism of action, druggability evaluation, and clinical application prospects, aiming to provide theoretical basis and reference for subsequent drug development and clinical research.
Cyanidin arabinoside belongs to the anthocyanin family, a natural product formed by the binding of cyanidin and arabilose through glycosidic bonds. Its molecular formula is C21H19O11, and its molecular weight is 419.36 g/mol. Structurally, cyanidin-arabinoside contains a typical anthocyanin glycoside core—the hydroxyl group at 3 is replaced by arabinose, forming a 3-arabinoside bond.
In terms of physicochemical properties, cyanidin arabinoside exhibits high polarity, with a LogP value of about -1.5, indicating good water solubility and weak hydrophobicity. Its extremely high polarity is also reflected in its large topological pole surface area (TPSA) of 189.79 Ų and the number of hydrogen bond acceptors, which facilitate stable hydrogen bond interactions with target proteins. Its molecular structure contains multiple phenolic hydroxyl groups, which give it excellent antioxidant activity. This compound has low blood-brain barrier permeability, suggesting its limited distribution in the central nervous system. Toxicological evaluation showed that cylindrin arabinoside had low acute toxicity (LD50 about 2000 mg/kg), no significant hepatotoxicity, cardiotoxicity, or hERG channel inhibition. Ames-induced mutagenic test results were negative, indicating high safety.
Cytainin arabinoside is mainly found in the fruits, petals, and leaves of various plants, with abundant content in Centaurea spp., especially in the genus Centaurea. Its natural sources are broad, commonly found in blueberries, blackberries, purple cabbage, cherries, and some red fruits and vegetables. Since its stability is greatly affected by pH, temperature, and light, the extraction and purification processes require strict control of conditions to ensure the integrity of the active ingredients.
Common extraction methods include solvent extraction, ultrasound-assisted extraction, and high-performance liquid chromatography (HPLC) purification. Generally, acidic methanol or ethanol is used as the extraction solvent, with pH adjusted to around 3 to stabilize the anthocyanin structure. Ultrasound-assisted extraction can improve extraction efficiency and purity, reducing the degradation of heat-sensitive components. After rotary evaporation and concentration, the extract was separated and purified using silica gel column chromatography or a C18 reversed phase column, and the structure and purity of cythalanin arabinoside were confirmed by HPLC-MS.
As a selective and reversible PTP1B inhibitor, cyanidin arabinoside exhibits significant enzyme inhibitory activity, with an IC50 of approximately 8.91 μM. PTP1B is an important negative regulatory factor regulating the insulin signaling pathway, and its overexpression is closely related to insulin resistance and the onset of type 2 diabetes. By inhibiting PTP1B, cyanide arabinoside can enhance phosphorylation of insulin receptors, promote downstream signaling, improve insulin sensitivity, and have potential antidiabetic effects.
Cyanthin arabinoside contains a rich phenolic hydroxyl structure, giving it a powerful free radical scavenging ability. In vitro experiments have shown that it can significantly enhance the activity of intracellular antioxidant enzymes (such as SOD1, SOD2, CAT, GPX1), activate the NFE2L2/NRF2 signaling pathway, and enhance the cells' defense against oxidative stress. Additionally, this compound can induce HMOX1 expression, exerting a protective effect on cells. Its antioxidant properties give it broad application prospects in preventing and treating chronic diseases caused by oxidative damage.
Preliminary studies also suggest that encyclosterin arabinoside may have certain anti-tumor, neuroprotective, and cardiovascular protective effects, but the related mechanisms require further exploration.
The main mechanism of action of cylatin arabinoside focuses on its inhibition of PTP1B and regulation of antioxidant signaling pathways.
PTP1B, as an intracellular tyrosine phosphatase, mainly regulates insulin signaling pathways by dephosphorylating insulin receptors and their substrates. Cytharidin arabinoside binds to the active site of PTP1B, forming a stable reversible complex that blocks its enzyme activity and promotes enhanced insulin signaling. Molecular docking and kinetic simulations show that the polyhydroxyl structure of cyanidin arabinoside forms multiple hydrogen bonds and hydrophobic interactions with the catalytic pocket of PTP1B, ensuring its high selectivity and inhibitory efficacy.
Cytharidin arabinoside activates the NFE2L2/NRF2 transcription factor, inducing the expression of downstream antioxidant enzyme genes (SOD1, SOD2, CAT, GPX1, HMOX1), enhancing the cell's ability to scavenge reactive oxygen species (ROS) and reducing cell damage caused by oxidative stress. This mechanism not only helps protect the function of cells β islets but may also delay the progression of diabetic complications.
Some studies suggest that cyanide arabinoside may affect inflammatory factor expression and signaling pathways, such as NF-κB and MAPK, but the specific molecular mechanisms require further validation.
The druggability evaluation of cylanin arabinoside shows it has good safety and efficacy potential.
Due to its high polarity and large TPSA, the oral bioavailability of cyanide arabinoside may be limited, and its low blood-brain barrier permeability suggests it mainly acts on peripheral tissues. In vivo metabolic studies show that this compound is easily metabolized by gut microbes and liver enzyme systems, forming various metabolites that may affect the duration of its efficacy. In the future, structural modification or nanocarrier technology will be needed to improve its pharmacokinetic properties.
Acute toxicity tests show that LD50 is about 2000 mg/kg, making it a low-toxicity compound. Hepatotoxicity, cardiotoxicity, and hERG channel inhibition tests were all negative. Ames-induced mutagenic tests showed no genotoxicity, indicating high safety and suitability for further therapeutic development.
Cytharidin arabinoside in vivo may compete with other drugs through metabolic enzymes or interact with transporters, so further study of its drug interaction spectrum is needed. Additionally, its chemical structure is sensitive to pH and temperature, so stability needs to be optimized during formulation development.
As a naturally derived PTP1B inhibitor, cyanidin arabinoside has significant anti-diabetic potential. Through a dual mechanism—enhancing insulin signaling and antioxidant protection—it offers new approaches for treating type 2 diabetes. In the future, based on its excellent safety profile and multi-target regulatory properties, cyanide arabinoside is expected to be developed as an oral anti-diabetic adjuvant or as a functional food ingredient.
Moreover, given its antioxidant and potential anti-inflammatory activities, the application of cyanidin arabinoside in preventing and treating diabetic complications (such as cardiovascular disease, neuropathy) and other oxidative stress-related conditions is also worth in-depth study. By integrating modern drug delivery technologies, such as nanocarriers and sustained-release formulations, it is expected to overcome bioavailability limitations and improve clinical efficacy.
Future research should focus on:
As a natural anthocyanin compound, cyanyl arabinoside shows broad prospects in the treatment of type 2 diabetes and related metabolic diseases, thanks to its selective PTP1B inhibitory activity and significant antioxidant capacity. Its excellent safety profile and multiple pharmacological mechanisms provide a solid foundation for the development of novel natural drugs. Although challenges such as bioavailability and stability remain, with continuous advances in molecular pharmacology and drug delivery technologies, cytharidin arabinoside is expected to become an important member of the natural product drug field in the future, contributing new strength to the prevention and treatment of diabetes and oxidative stress-related diseases.
Shenshuai
Wenjing
Hedandan
