Product name: Malvidin chloride
Synonym name: Malvidol; Malvinidin; Malvinidol chloride; Oenidin; Primulidin; Syringidin; Syringidin chloride 

Catalogue No.: BP0919
Cas No.: 643-84-5
Formula: C₁₇H₁₅ClO₇
Mol Weight: 366.75
Botanical Source:

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.

HNMR of Malvidin chloride

HPLC of Malvidin chloride

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

Introduction/Overview

Malvidin chloride (CAS No.: 643-84-5) is a natural anthocyanin compound widely found in grapes and their products. Due to its remarkable biological activity and potential medicinal value, it has attracted significant attention in the field of natural product pharmacology in recent years. As a typical anthocyanin, chloride mallow pigments not only give grapes and red wine their unique colors but also exhibit various biological functions, especially showing good application potential in antioxidant, anti-inflammatory, and antitumor areas. By regulating the cell cycle, inducing tumor cell apoptosis, and modulating various antioxidant-related signaling pathways, it has become an important molecule in cancer and related disease research.

This paper aims to systematically review the chemical structure and physicochemical properties of chlorinated mallow pigment, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation, and pharmacokinetic characteristics. Combined with current research progress, it explores its clinical application prospects and development trends, providing theoretical support and reference for subsequent basic and clinical research.

Chemical structure and physicochemical properties

Chloride mallowium pigment belongs to the anthocyanin class of compounds, chemically named 3,5,7-trihydroxy-2-(3,4-dihydroxyphenyl)-1-phenylbenzopyranate, molecular formula C17H15ClO7, molecular weight 331.30. Its structural core is the benzopyran ring system, which contains multiple hydroxyl groups and a positively charged oxygen heterocycle, with chloride ions present as paired anions, forming a stable salt structure.

In terms of physicochemical properties, chloride mallow pigment exhibits high polarity, with a LogP value of about -0.19, indicating good water solubility (about 0.18 mg/mL), which is beneficial for dissolution and absorption in organisms. Its topological pole surface area (TPSA) is 110.68 Ų, indicating strong polarity and hydrogen bond donor/acceptor capability. Low blood-brain barrier permeability means limited distribution in the central nervous system. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames-induced mutagenic test scored 0.6, indicating a lower risk of genotoxicity.

Plant Origins and Extraction Methods

Chloride mallowum pigment is mainly found in the peel and seeds of grapes (Vitis vinifera), with abundant content in red grape varieties. Its natural form is usually anthocyanin salts, giving grapes and wines a deep purplish-red color. Besides grapes, some berry plants such as blueberries and blackberries also contain small amounts of these anthocyanins.

Traditional extraction methods mostly use organic solvents, commonly using ethanol-water mixed solutions (such as 70% ethanol) as extractants, and improving extraction efficiency through ultrasound-assisted extraction, microwave-assisted extraction, or hot reflux extraction. After concentration and freeze-drying, the extract is purified and identified using high-performance liquid chromatography (HPLC) combined with mass spectrometry (MS) or nuclear magnetic resonance (NMR) technology. In recent years, supercritical CO2 extraction and membrane separation technologies have also been applied to improve the purity and yield of chlorinated mallow pigments.

During extraction, attention must be paid to the effects of pH, temperature, and light on anthocyanin stability. Acidic conditions help maintain their stable cationic form, preventing degradation and discoloration. Moreover, optimizing the extraction process is of great significance for ensuring biological activity and subsequent pharmacological research.

Pharmacological activity research

Pharmacological studies on the pharmacological activity of chloride mallow pigments mainly focus on their antioxidant, anti-inflammatory, anti-tumor, and cell-protective effects. Numerous in vitro and in vivo studies have shown that this compound can effectively eliminate free radicals and reduce cell damage caused by oxidative stress.

Antioxidant effects

Mallowium chloride pigments activate the nuclear factor 2-related factor 2 (NFE2L2/NRF2) signaling pathway, enhancing the expression and activity of intracellular antioxidant enzymes such as superoxide dismutase (SOD1, SOD2), catalase (CAT), glutathione peroxidase (GPX1), and heme oxygenase 1 (HMOX1), significantly improving cell resistance to oxidative damage. Its antioxidant capacity not only helps slow cellular aging but also prevents the development of various chronic diseases.

Antitumor activity

Malva chloride pigments exhibit significant cytotoxicity across various tumor cell lines. Its main mechanism includes blocking cell cycle progression during the G2/M phase and inducing tumor cell apoptosis. Related studies show that this compound can regulate multiple signaling pathways, such as inhibiting the PI3K/Akt and MAPK/ERK pathways, activating mitochondria-dependent apoptosis pathways, promoting cytochrome C release and caspase activation, thereby achieving anti-tumor effects.

Additionally, chloride mallowium pigment has shown potential to inhibit tumor cell migration and invasion, possibly slowing tumor metastasis by regulating matrix metalloproteinases (MMPs) and cell adhesion molecule expression.

Cell protection and anti-inflammatory effects

In the oxidative stress and inflammation model, chloride mallow-pigment can reduce the expression of inflammatory factors such as TNF-α, IL-6, and IL-1β, thereby alleviating inflammatory responses. Its anti-inflammatory effect is closely related to regulating the NF-κB signaling pathway, promoting the expression of intracellular antioxidant enzymes and reducing cellular damage.

Mechanism of action and molecular targets

The bioactivity of chloride mallow pigment mainly depends on its interactions with various intracellular molecular targets, especially its key role in antioxidant and antitumor mechanisms.

Antioxidant-related targets

• NFE2L2/NRF2: As the main regulator of antioxidant stress, NRF2 is activated under the action of chloride mallowium pigment, translocating to the nucleus and inducing the expression of downstream antioxidant enzyme genes.
• SOD1/SOD2: Superoxide dismutase catalyzes the conversion of superoxide anion radicals into hydrogen peroxide, reducing oxidative damage.
• CAT: Catalase breaks down hydrogen peroxide into water and oxygen, further reducing oxidative stress.
• GPX1: Glutathione peroxidase protects cell membrane lipids from oxidative damage by reducing peroxides.
• HMOX1: Hemoglobin oxygenase 1 has antioxidant and anti-inflammatory functions and participates in cell protection.

Anti-tumor-related mechanisms

• Cell cycle regulation: Malva chloride pigment blocks cell cycle stagnation during the G2/M phase by modulating cyclins and their dependent kinases, thereby halting tumor cell proliferation.
• Apoptotic signaling pathway: Activates mitochondrial pathways, promotes activation of caspase-3 and -9, and induces apoptosis.
• Signaling pathway regulation: Inhibits PI3K/Akt and MAPK/ERK pathways, reduces cell viability signals, and enhances apoptosis sensitivity.
• Migration and invasion: Regulates MMPs and cell adhesion molecules, inhibiting the metastatic ability of tumor cells.

Druggability evaluation and pharmacokinetics

Chloride mallow pigment has good druggability characteristics. Its molecular weight is 331.3, meeting the molecular weight requirements for drugs under the Lipinski rules. The LogP value was -0.19, indicating strong hydrophilicity, which is beneficial for oral absorption and internal distribution. A TPSA value of 110.68 Ų indicates good polarity and hydrogen bonding ability, which helps bind to biomacromolecules.

Moderate water solubility (0.1799 mg/mL), which is beneficial for formulation development. The blood-brain barrier has lower permeability, reducing the risk of central nervous system side effects. hERG channel inhibition was negative, indicating a lower risk of cardiotoxicity. Ames test results showed that it carries a low genotoxicity risk and is relatively safe.

Pharmacokinetics, existing studies show that chloride mallow pigment metabolizes rapidly in the body, mainly through hepatic enzyme systems to produce various metabolic products. Its oral bioavailability is limited, possibly related to gastrointestinal pH and enzymatic hydrolysis. In the future, drug carrier technology or structural modification will be needed to improve in vivo stability and bioavailability.

Prospects and outlooks for clinical applications

As a natural active anthocyanin, chlorinated mallow pigment demonstrates broad clinical application potential due to its multi-target and multi-mechanism biological activity. It holds particular value in cancer prevention and treatment, chronic inflammation, and oxidative stress-related diseases (such as cardiovascular diseases and neurodegenerative diseases).

Currently, chloride mallowum pigment is mainly in basic research and early pharmacological validation stages, lacking systematic clinical trial data. Future research should focus on the following directions:

1. Dosage form development and drug route optimization: Technologies such as nanocarriers and liposome encapsulation are used to improve bioavailability and targetability.
2. Safety and toxicological evaluation: Conduct long-term toxicological studies to clarify safe dose ranges.
3. Clinical trial design: Conduct clinical trials targeting specific diseases to verify efficacy and safety.
4. Combination drug research: Exploring synergistic effects with existing anticancer or anti-inflammatory drugs to enhance treatment outcomes.
5. In-depth analysis of molecular mechanisms: Using multi-omics techniques to further reveal its network of action and potential targets.

Through these efforts, mallow chloride pigments are expected to become important candidate molecules for natural product drug development, promoting the application of natural anthocyanin compounds in modern medicine.

Conclusion

As a natural anthocyanin derived from grapes, mallow chloride pigments possess significant antioxidant and antitumor activities, exerting biological effects by regulating the cell cycle, inducing apoptosis, and activating various antioxidant enzymes. Its excellent physicochemical properties and safety provide a foundation for druggability, but challenges such as bioavailability and metabolic stability still need to be overcome. In the future, combining modern drug formulation technologies with molecular biology methods, and conducting in-depth preclinical and clinical research, it will help promote the transformation of chlorinated mallowum pigment into clinical applications and realize its potential value in cancer and related disease prevention and treatment.