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Synonym name: Myrtillin; Myrtillin A
Catalogue No.: BP0469
Cas No.: 50986-17-9
Formula: C21H21O12+
Mol Weight: 465.386
Botanical Source: grapes and many other plant spp.
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.
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
211.8300
-1.8944
-2.4890
.9217
.5381
.1163
Low
58.7686
4.3669
Yes
No
Yes
No
Yes
No
1.2
Yes
No
Yes
No
Delphinidin 3-Glucoside (D3G) is a widely found natural anthocyanin compound in the plant kingdom and belongs to the anthocyanin cation family. As a 3-O-β-D-glucoside derivative of delphinidin, D3G plays an important role in plant pigment synthesis and antioxidant defense. In recent years, with the deepening of research into pharmacology of natural products and functional foods, D3G has attracted widespread attention due to its excellent bioactivity, especially its potential therapeutic value in metabolic diseases such as type 2 diabetes mellitus (T2DM). This paper systematically reviews the chemical structure, plant origin, extraction methods, pharmacological activity, mechanism of action, druggability evaluation, and clinical application prospects of delphinitinoside glucosides, aiming to provide a theoretical foundation and research direction for drug development and functional utilization of this natural product.
The chemical structure of delphinin glucoside consists of the core of delphinin (3,4′,5,5′,7-pentahydroxyanthocyanidin cation) and the β-D-glucoside residue connected by glycosidic bonds at the 3-OH site. Its molecular formula is C21H21O12, and its molecular weight is 465.3870 Da. Its structure contains multiple hydroxyl groups, giving it high hydrophilicity and strong antioxidant capacity.
In terms of physicochemical properties, D3G has a LogP value of -1.8944, indicating strong hydrophilicity, and water solubility of 0.9217, indicating good solubility in aqueous media. Its topological pole surface area (TPSA) is 211.8300 Ų, reflecting a relatively large molecular polar surface area, which has an important impact on molecular binding to biological targets and membrane permeability. D3G has a relatively low blood-brain barrier penetration ability, suggesting it mainly acts on peripheral tissues rather than the central nervous system. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames test result was 1.2, indicating a low genotoxicity risk and high safety.
Delphinithol glucoside is widely found in various fruits, vegetables, and flowers, especially abundant in blueberries, blackberries, purple cabbage, pomegranates, and purple grape skins. In plants, it mainly acts as a pigment component, participating in the formation of petal color and attracting pollinating insects.
Common methods for extracting D3G include solvent extraction, ultrasound-assisted extraction, microwave-assisted extraction, and solid-phase extraction. Typically, ethanol or methanol containing water is used as extraction solvents to ensure the stability and efficiency of anthocyanins. During extraction, pH regulation is critical; acidic conditions (pH 1-3) help maintain the stable structure of anthocyanin cations and reduce degradation. After concentration and purification, the extract is often analyzed qualitatively and quantitatively using high-performance liquid chromatography (HPLC) combined with mass spectrometry (MS).
In recent years, green extraction technologies such as supercritical CO₂ extraction and enzyme-assisted extraction have gradually been applied to D3G extraction, aiming to improve extraction efficiency, reduce solvent residues and environmental pollution, and promote its industrial-scale production.
As a natural anthocyanin, delphinial glucoside exhibits a variety of biological activities, mainly including antioxidant, anti-inflammatory, antidiabetic, cardiovascular protection, and neuroprotection.
D3G has a significant free radical scavenging ability, effectively neutralizing reactive oxygen species (ROS) and nitrogen radicals, reducing cellular damage caused by oxidative stress. Its hydroxyl structure enables it to capture free radicals through electron transfer and hydrogen donor mechanisms, protecting cell membrane lipids and DNA from oxidative damage.
Numerous in vitro and in vivo studies have shown that D3G has potential therapeutic effects for type 2 diabetes. Its main manifestations include improving insulin sensitivity, promoting glucose metabolism, and regulating lipid metabolism. Animal model studies show that D3G can lower blood sugar levels, improve the function of pancreatic islet β cells, and alleviate diabetes-related inflammatory responses and oxidative stress.
D3G exerts anti-inflammatory effects by inhibiting the nuclear factor κB (NF-κB) signaling pathway, reducing the expression of pro-inflammatory factors such as tumor necrosis factor α (TNF-α) and interleukin-6 (IL-6). This role is of great significance for the prevention and treatment of diabetes and its complications.
D3G can improve vascular endothelial function, inhibit low-density lipoprotein oxidation, and reduce the risk of atherosclerosis. Additionally, its antioxidant and anti-inflammatory properties help reduce heart muscle damage and improve heart function.
Although D3G has low blood-brain barrier permeability, its antioxidant and anti-inflammatory effects may still indirectly protect the nervous system through peripheral mechanisms, slowing the progression of neurodegenerative diseases.
The mechanism of action of delphinin glucoside in metabolic diseases such as type 2 diabetes involves multiple signaling pathways and key molecular targets.
AMP-activated protein kinase (AMPK) is a core regulator of cellular energy metabolism. D3G can activate AMPK (the PRKAA1 subunit), promote glucose uptake and fatty acid oxidation, and improve insulin resistance. Activating AMPK also inhibits fat synthesis and regulates energy homeostasis.
GCK promotes glucose phosphorylation in liver and pancreatic islet β cells and is a key enzyme for glucose metabolism. D3G regulates GCK activity, enhances glucose utilization efficiency, and lowers blood sugar levels.
PTPN1 is a negative regulator of the insulin signaling pathway, and excessive activity leads to insulin resistance. Research shows that D3G can inhibit PTPN1 activity, enhance insulin signaling, and improve glucose metabolism.
Overall, D3G demonstrates multidimensional therapeutic potential through multi-target and multi-pathway synergistic effects to regulate glycolipid metabolism, provide antioxidant and anti-inflammatory effects, and protect cellular function.
The druggability evaluation of delphinin glucoside shows it has certain development potential, but there are also challenges.
D3G has a moderate molecular weight (465.3870 Da), but its higher polarity (TPSA 211.83) and negative LogP value (-1.8944) limit its cell membrane permeability and oral bioavailability. It has good water solubility (0.9217), which is beneficial for formulation development and in vivo distribution. The low permeability of the blood-brain barrier suggests it mainly acts on peripheral tissues, reducing the risk of central nervous system side effects.
The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames test result was 1.2, indicating a low risk of genotoxicity. Overall, it has a good safety profile and is suitable for further drug development.
Currently, data on the absorption, distribution, metabolism, and excretion (ADME) of D3G in vivo are limited. Previous studies have shown that anthocyanin compounds are easily hydrolyzed in the gastrointestinal tract after oral administration, with glycosidic bonds breaking to release free anthocyanins, which are then metabolized by gut microbes to produce various metabolic products. The metabolic stability and bioavailability of D3G urgently require systematic research to guide formulation design and administration regimen optimization.
Due to D3G's strong polarity and low oral bioavailability, novel formulation technologies such as nanocarriers, liposomes, and inclusion compounds are needed to enhance its in vivo stability and targeting. In addition, the synergistic effects of combining other natural products or drugs are also worth exploring.
As a natural active ingredient, delphinin glucoside shows broad application prospects in the prevention and treatment of type 2 diabetes and related metabolic diseases. Its multi-target regulation and low toxicity advantages make it an important candidate for functional foods, health products, and novel drug development.
The key to future clinical applications lies in:
In addition, by utilizing modern biotechnological approaches such as metabolomics, proteomics, and molecular docking techniques, the in-depth exploration of D3G's network of action and potential targets will provide scientific evidence for its clinical translation.
As an important natural anthocyanin glucoside, delphiniferin glucoside shows significant potential in the prevention and treatment of metabolic diseases, especially type 2 diabetes, due to its unique chemical structure and diverse biological activity. By modulating the AMPK signaling pathway, improving glucose metabolism, suppressing inflammatory responses, and protecting cellular function, it exerts multi-target synergistic effects. Although there are currently certain limitations in drug-taking and pharmacokinetics, with advances in extraction and purification technologies and formulation processes, D3G is expected to become an important direction for natural product drug development. In the future, combining systematic clinical research and multidisciplinary innovations will promote the widespread application of delphinin glucoside in disease prevention and health promotion.
Shenshuai
Wenjing
Hedandan
