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Product name: Cyanidin-3-glucoside chloride
Synonym name: Kuromanin; Chrysanthemin
Catalogue No.: BP0430
Cas No.: 7084-24-4
Formula: C21H21ClO11
Mol Weight: 484.838
Botanical Source: Found in many plants and fruits, e.g. cherries, olives, grapes, Allium spp., Cotoneaster spp. and Ilex spp. First Chrysanthemum indicum.
Physical Description: Yellow powder
Type of Compound: Anthocyanins
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:
Cyanidin-3- O -glucoside, is one of the main component of mulberry anthocyanins,has protective effects from blackberry extract against peroxynitrite-induced endothelial dysfunction and vascular failure.[1]
Cyanidin-3- O -glucoside exhibits strong antioxidant activities including DPPH radical scavenging activities, ABTS radical scavenging activities and ORAC values.[2]
Cyanidin-3-O-glucoside chloride decreases mutant p21 expression, and increases the ratio of Bax/Bcl-2 and the activation of caspase-3 to induce apoptosis.[3]
References:
[1] Serraino I, Dugo L, Dugo P, et al. Life Sci, 2003, 73(9):1097-114.
[2] Chen M, Meng H, Zhao Y, et al. Bmc Complem Altern M, 2015, 15(1):1-8.
[3] Chen M, Zhao Z, Yu S. Int J Mol Sci, 2016, 17(7).
[4] Liu Z Y, Liu X Q, Bai S F, et al. Food Sci, 2011, 32(18):256-9.
HPLC of Cyanidin-3-glucoside chloride
HNMR of Cyanidin-3-glucoside chloride
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
203.2400
-2.5000
-2.0000
100.0000
Low
No
No
No
No
No
No
Cyanidin-3-glucoside chloride (C3G-Cl) is a natural anthocyanin compound widely found in various plants and is an important member of the flavonoid group. As a water-soluble natural pigment, C3G-Cl not only gives plants its vivid red-purple hues but also attracts attention for its remarkable biological activity. In recent years, with in-depth research into the pharmacological effects of natural products, C3G-Cl has shown broad application potential in areas such as antioxidant damage, anti-inflammation, anti-tumor, and neuroprotection. By regulating various antioxidant enzymes and transcription factors within cells, it plays a role in scavenging free radicals and reducing oxidative stress, making it a hot topic in natural antioxidant research.
This paper aims to systematically review the chemical structure and physicochemical properties, plant origin and extraction methods, pharmacological activity and mechanism of action of cylindrine chloride-3-glucoside, druggability evaluation and pharmacokinetic characteristics, and, combined with the latest research progress, explore its clinical application prospects and development directions, providing reference and guidance for researchers in related fields.
The chemical structure of cyanidin-3-glucoside chloride is based on the core backbone of cyanidin, with the molecular formula C21H21ClO11 and a molecular weight of 484.84. Its structural features include the benzene ring A and B formed by a triple-carbon bridge forming a flavonoid backbone, with three hydroxyl groups modified by glucose groups to form a 3-glucoside structure. Chloride ions bind to cationic portions in the form of ionic bonds, giving them excellent water solubility.
In terms of physicochemical properties, C3G-Cl exhibits low lipid solubility (LogP about -2.5), indicating strong hydrophilicity and readily solubility in water (solubility about 100 mg/mL), which facilitates absorption and distribution in the body. Its extremely high polar surface area (TPSA approximately 203.24 Ų) and the number of hydrogen bond receptors (11) suggest certain limitations in cell membrane penetration, especially its low ability to penetrate the blood-brain barrier. In addition, the stability of C3G-Cl is greatly affected by pH, remaining more stable in acidic environments but prone to structural changes under alkaline conditions, affecting its biological activity.
Cythalanin chloride-3-glucoside is widely found in various red or purple fruits and vegetables, such as blueberries, blackberries, purple cabbage, red grapes, and cornflower plants. Its content is significantly influenced by plant variety, growing environment, maturity, and harvest time.
The extraction methods mainly include solvent extraction, ultrasound-assisted extraction, microwave-assisted extraction, and enzymatic hydrolysis extraction. Traditional solvent extraction mostly uses a mixture of methanol, ethanol, or ethyl acetate with water, supplemented by acidic conditions (such as adding a small amount of hydrochloric acid) to stabilize the anthocyanin structure. Ultrasound-assisted extraction can improve extraction efficiency, shorten the time, and reduce solvent usage. In recent years, green extraction technologies such as supercritical CO2 extraction and natural deep eutectic solvents have been increasingly used, aiming to improve extraction purity and the stability of bioactive ingredients.
After extraction, high-performance liquid chromatography (HPLC) combined with mass spectrometry (MS) technology is commonly used for qualitative and quantitative analysis to ensure that the purity and content of cyanide chloride-3-glucoside meet the needs of pharmacological research and application.
As a natural anthocyanin, C3G-Cl has significant antioxidant capacity. Numerous in vitro and in vivo studies have shown that it can effectively scavenge free radicals (such as hydroxyl radicals and superoxide anions) and reduce cell damage caused by oxidative stress. Its antioxidant effects rely not only on direct free radical scavenging but also on regulating intracellular antioxidant enzyme systems.
Oxidative stress is closely related to inflammatory responses. C3G-Cl reduces inflammation by inhibiting the expression of pro-inflammatory factors (such as TNF-α, IL-6, IL-1β). It can inhibit activation of the nuclear factor κB (NF-κB) signaling pathway, reduce the release of inflammatory mediators, and exert multi-target anti-inflammatory effects.
Due to its antioxidant and anti-inflammatory properties, C3G-Cl exhibits neuroprotective effects in models of neurodegenerative diseases. Research shows that C3G-Cl can alleviate neuronal apoptosis induced by oxidative stress, improve cognitive function, and have potential therapeutic value for neurological diseases such as Alzheimer's and Parkinson's.
C3G-Cl exhibits cardiovascular protective effects by antioxidant and improved vascular endothelial function, lowering blood lipids and preventing atherosclerosis. It can regulate the synthesis of vasodilatory factor nitric oxide (NO), inhibit platelet aggregation, and reduce the risk of cardiovascular events.
Some studies have shown that C3G-Cl exerts anti-tumor activity by inducing tumor cell apoptosis, inhibiting tumor cell proliferation and migration. Its mechanism involves regulating cell cycle-related proteins, activating apoptotic signaling pathways, and suppressing inflammatory responses in the tumor microenvironment.
The main mechanism of action of C3G-Cl focuses on regulating antioxidant signaling pathways, especially by activating the nuclear factor red 2-associated factor 2 (NFE2L2, NRF2) signaling pathway, thereby enhancing cellular antioxidant defense capabilities. NRF2, as a key intracellular transcription factor, regulates the expression of various antioxidant enzyme genes, including superoxide dismutase 1 (SOD1), superoxide dismutase 2 (SOD2), catalase peroxidase (CAT), glutathione peroxidase 1 (GPX1), and heme oxygenase 1 (HMOX1).
C3G-Cl promotes the translocation of NRF2 from the cytoplasm to the nucleus, enhances its binding to antioxidant response elements (AREs), initiates transcription of downstream antioxidant enzyme genes, significantly improves cells' ability to scavenge reactive oxygen species (ROS), and reduces cell damage caused by oxidative stress. Additionally, C3G-Cl can inhibit pro-inflammatory signaling pathways such as NF-κB, reducing the production of inflammatory factors and synergistically exerting cellular protective effects.
At the molecular level, the multihydroxyl structure of C3G-Cl gives it strong free radical capture capability, and its interaction with antioxidant enzyme active centers enhances enzyme activity, forming a multi-layered, multi-target protective network.
C3G-Cl has a molecular weight of 484.84, classifying it as a medium molecular weight compound. Its LogP value is -2.5, indicating high hydrophilicity and excellent water solubility (about 100 mg/mL), which is beneficial for oral preparation and absorption. However, the higher polarity and number of hydrogen bond receptors (11) limit its cell membrane permeability, especially the low permeability of the blood-brain barrier, suggesting that its direct role in the central nervous system may be limited.
Toxicological evaluation showed that C3G-Cl's LD50 was about 2000 mg/kg, with low toxicity, no significant hepatotoxicity, cardiotoxicity, or hERG channel inhibition. Ames mutagenic test was negative, safety was good, and it has promising drug potential.
Currently, pharmacokinetic research on C3G-Cl is relatively limited. Previous studies have shown that after oral administration, C3G-Cl has poor stability in the gastrointestinal tract, with some being metabolized by gastric acid and gut microbes, resulting in low bioavailability. Its main metabolic pathways include deglycosylation mediated by the gut microbiota and phase I and II metabolism in the liver, generating various metabolic products.
The half-life of C3G-Cl and its metabolites in plasma is relatively short, suggesting that formulation modifications or administration route optimization are needed to increase in vivo exposure. Its excretion is mainly carried out through urine and bile.
Based on its excellent antioxidant, anti-inflammatory, and neuroprotective multiple pharmacological activities, cyanide chloride-3-glucoside has broad application prospects in preventing and treating various diseases related to oxidative stress. Its potential value is especially evident in neurodegenerative diseases, cardiovascular diseases, metabolic syndromes, and certain inflammatory diseases.
Future clinical development should focus on the following aspects:
Dosage form optimization: Given its strong water solubility but limited bioavailability, new drug delivery systems such as nanocarriers, liposomes, and inclusion compounds need to be developed to improve in vivo stability and targeting.
Combination Therapy Strategy: Combine with other antioxidants or anti-inflammatory drugs to create synergistic effects and enhance treatment outcomes.
Clinical trial design: Conduct systematic pharmacokinetics, pharmacodynamics, and safety evaluations, clarify effective dosage and therapeutic windows, and promote clinical translation.
Disease-targeted research: Deeply analyze its mechanisms in specific disease models, especially neurological and cardiovascular diseases, to uncover potential therapeutic targets.
Metabolite research: Given that metabolites may have unique biological activities, it is necessary to strengthen research into their metabolic pathways and biological functions.
As a natural anthocyanin with significant antioxidant and multiple pharmacological activities, cyanocylin-3-glucoside has demonstrated good safety and pharmaceutical potential. By regulating NRF2 and related antioxidant enzyme systems, it effectively alleviates oxidative stress and inflammatory damage, offering broad value for disease prevention and treatment. Although its bioavailability and pharmacokinetic properties still need optimization, with ongoing advances in extraction technology, formulation development, and molecular mechanism research, C3G-Cl is expected to become an important candidate molecule in natural product drug development. Future research should strengthen its clinical translation and application studies to promote its widespread use in diseases related to antioxidant damage.
Shenshuai
Wenjing
Hedandan
