Product Name: Delphinidin chloride
Synonym name: Delphinidol; Delphinidin
Catalogue No.: BP0466
Cas No.: 528-53-0
Formula: C₁₅H₁₁ClO₇
Mol Weight: 338.70
Botanical Source: Pigment various plants. Widespread for example in the Plumbaginaceae, Hamamelidaceae and Anacardiaceae

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 Delphinidin

NMR of Delphinidin

Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃

Introduction/Overview

Delphinidin chloride (CAS No.: 528-53-0) is a typical anthocyanin natural product, widely found in berries, red wine, and various plants. As a water-soluble natural pigment, delphinin chloride not only gives plants a vivid blue-purple hue but also attracts widespread attention in pharmacology and natural product chemistry due to its diverse biological activity. In recent years, with in-depth research into the antioxidant, anti-inflammatory, and antitumor effects of natural products, diphthionin chloride has become a potential candidate for multi-target drug development due to its significant endothelial-dependent vasodilatory effect, anticancer activity, and signaling pathway regulation capabilities.

This review aims to systematically summarize the chemical structure and physicochemical properties of delphinin chloride, plant origin and extraction methods, pharmacological activity and mechanism of action. Combining druggability parameters and pharmacokinetic characteristics, it explores its clinical application prospects and development directions, providing theoretical basis and reference for subsequent basic research and clinical translation.

Chemical structure and physicochemical properties

Diphthian chloride belongs to the anthocyanidin family and is a flavonoid compound with 3,5,7,3',4',5'-hydroxy-substituted flavonoids. Its molecular formula is C15H11ClO7, with a molecular weight of 303.2460. Structurally, the core of flavonid delphinin is a flavonoid tricyclic structure (C6-C3-C6), containing multiple hydroxyl groups and a chloride ion coordination, giving it unique chemical properties and biological activity.

In terms of physicochemical properties, the LogP value of diphnitide chloride is -0.8871, indicating strong hydrophilicity, and water solubility is 0.0882 (unit unclear, but indicating moderate solubility). Its topological pole surface area (TPSA) is 132.68 Ų, indicating high molecular polarity, which may affect membrane permeability and bioavailability. The penetration rate of the blood-brain barrier is relatively low, indicating its limited distribution in the central nervous system. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames test value was 1.2, indicating a relatively low genotoxicity risk.

In summary, the chemical structure of delphinin chloride gives it good water solubility and low lipid solubility, making it suitable for distribution in the body in blood and extracellular fluids, but its penetration ability to the central nervous system is limited.

Plant Origins and Extraction Methods

Delphinin chloride is mainly found in various berry fruits (such as blueberries, blackberries, blackcurrants) and red wine, and is an important component of these plant pigments. Its content is greatly influenced by plant variety, growing environment, maturity, and processing methods.

Traditional extraction methods mostly use acidic methanol or ethanol solutions to extract plant raw materials, leveraging the stability advantages of anthocyanins under acidic conditions to prevent their degradation. Common steps include:

1. Sample pretreatment: Fresh or frozen berries are washed, crushed, and dried.
2. Solvent extraction: Use methanol or ethanol containing 0.1% hydrochloric acid, extracted at room temperature or low temperature for several hours.
3. Filtration and concentration: Solid impurities are removed by filter paper or centrifugation, then rotary evaporation concentrates the extract.
4. Purification and separation: Use column chromatography (such as C18 reversed-phase column) and high-performance liquid chromatography (HPLC) for separation and purification to obtain high-purity delphinin chloride.

In recent years, modern technologies such as ultrasound-assisted extraction, microwave-assisted extraction, and enzymatic hydrolysis-assisted extraction have been applied to improve extraction efficiency and yield, while also reducing solvent usage and extraction time. In addition, the introduction of nanotechnology and membrane separation technology has provided new ideas for the industrial production of delphinium chloride.

Pharmacological activity research

The pharmacological activities of delphinial chloride cover cardiovascular protection, antioxidant, anti-inflammatory, and antitumor properties, demonstrating a wide range of biological functions.

1. Endothelium-dependent vasodilatory effect

Delphinin chloride can induce relaxation of vascular smooth muscle by promoting nitric oxide (NO) release from endothelial cells and regulating calcium channels, showing significant vasodilatory effects. In vitro experiments have shown that it has a protective effect against models of vascular endothelial dysfunction and may help prevent and treat cardiovascular diseases such as hypertension and arteriosclerosis.

2. Antioxidant and anti-inflammatory effects

As a natural antioxidant containing anthocyanins, delphinin chloride can effectively eliminate free radicals and reduce cellular damage caused by oxidative stress. It can also inhibit the expression of pro-inflammatory factors such as TNF-α and IL-6, reducing inflammatory responses and offering potential anti-inflammatory effects.

3. Anticancer activity

Delphinium chloride exhibits anti-proliferative and apoptosis-inducing effects in various cancer cell lines. Especially in colon cancer HCT116 cells, delphinitide chloride promotes cell apoptosis and inhibits tumor growth by regulating the JAK/STAT3 and MAPK signaling pathways. Additionally, as an effective inhibitor of epidermal growth factor receptor (EGFR) (IC50 1.3 μM), it can shut down the downstream signaling cascade of EGFR, blocking tumor cell proliferation and metastasis signals.

4. Other potential activities

Some studies suggest that delphinin chloride may have neuroprotective and metabolic regulatory functions, but related research is still in its early stages and requires further validation.

Mechanism of action and molecular targets

The pharmacological effects of delphinin chloride are mainly realized through multiple signaling pathways, involving multiple molecular targets:

1. JAK/STAT3 signaling pathway

The JAK/STAT3 pathway plays a key role in cell proliferation, differentiation, and apoptosis. Delphinin chloride can inhibit activation of this pathway, reduce STAT3 phosphorylation, block its nuclear transcriptional activity, induce apoptosis of HCT116 cells, and suppress tumor growth.

2. MAPK signaling pathway

The MAPK pathway includes subtypes such as ERK, JNK, and p38, which regulate cellular stress responses and apoptosis. Delphinin chloride promotes programmed death of cancer cells by regulating the activation state of the MAPK pathway.

3. EGFR inhibitory effect

EGFR is an important driver of tumor cell proliferation. As an effective inhibitor of EGFR, delphinin chloride can bind to its kinase domain, block receptor activation and downstream signaling, and suppress tumor cell proliferation and migration.

4. Nitric oxide (NO) related mechanisms

Delphinin chloride promotes the activity of NO synthase within endothelial cells, increases NO production, leads to vasodilation, improves hemodynamics, and exerts cardiovascular protective effects.

5. Antioxidant mechanism

By directly scavenging reactive oxygen species (ROS) and activating the Nrf2/ARE antioxidant signaling pathway, delphinin chloride enhances cells' antioxidant defenses and reduces oxidative damage.

Druggability evaluation and pharmacokinetics

The druggability evaluation of delphinin chloride shows that it has certain advantages and limitations:

• Molecular weight and polarity: A molecular weight of 303.2460 and higher polarity (TPSA 132.68) give it good water solubility, but may limit its cell membrane permeability and oral absorption.
• Lipid solubility: A negative LogP value (-0.8871) indicates strong hydrophilicity, which facilitates plasma distribution, but may affect its ability to penetrate lipid membranes.
• Blood-brain barrier penetration: Low permeability limits its application potential in the central nervous system.
• Safety: hERG channels have no inhibitory effects, reducing the risk of cardiotoxicity; Ames test results showed low genotoxicity and good safety.
• Pharmacokinetics: Currently, there is limited research on the absorption, distribution, metabolism, and excretion (ADME) of delphinium chloride. Some literature reports low oral bioavailability and rapid metabolism in vivo, mainly through hepatic enzyme transformation. The activity of these metabolites still requires further study.

To address its insufficient druggability, researchers have attempted to improve its bioavailability and targeting by methods such as nanocarriers, liposome encapsulation, and structural modification.

Prospects and outlooks for clinical applications

As a multifunctional natural product, delphinin chloride possesses excellent pharmacological activity and safety, with broad clinical application potential:

1. Prevention and treatment of cardiovascular diseases: Its endothelium-dependent vasodilatory effect and antioxidant capacity make it a candidate for adjunctive treatment of hypertension, arteriosclerosis, and coronary heart disease.
2. Tumor Therapy: By regulating tumor-related signaling pathways through multiple targets, delphinium chloride is expected to serve as a lead compound in anti-tumor drugs, especially showing potential in digestive system tumors such as colon cancer.
3. Anti-inflammatory and metabolic diseases: Its anti-inflammatory effects and possible metabolic regulatory functions suggest its application prospects in chronic inflammation and metabolic syndrome.
4. Functional foods and health products: As a natural pigment and antioxidant, delphinin chloride can be widely used in the fields of functional foods and nutritional supplements.

Future research should focus on:

• In-depth analysis of metabolic pathways in vivo and the activity of metabolic products.
• Optimize dosage form design to improve oral bioavailability.
• Conduct systematic preclinical toxicology and pharmacodynamic evaluations.
• Explore its combination therapy potential and synergistic effects with existing treatment regimens.

Conclusion

As a typical anthocyanin natural product, delphinin chloride demonstrates broad application potential in cardiovascular protection, anti-tumor, and anti-inflammatory fields due to its unique chemical structure and diverse biological activities. By regulating key molecular targets such as JAK/STAT3, MAPK, and EGFR, it exerts multi-target synergistic effects, offering excellent safety and druggability advantages. Although its pharmacokinetic characteristics and clinical applications still face certain challenges, with continuous advances in extraction and purification technologies and drug delivery systems, delphinin chloride is expected to become an important direction for future natural product drug development. Future research should further integrate chemistry, pharmacology, and clinical science to promote phasperithin-chloride from the laboratory to clinical practice, contributing new natural medicinal resources to human health.