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Product name: 2-O-β-D-Glucopyranosyl-L-ascorbic acid
Synonym name:
Catalogue No.: BP2077
Cas No.: 562043-82-7
Formula: C12H18O11
Mol Weight: 338.265
Botanical Source: Lycii Fructus
Physical Description: 枸杞子
Type of Compound:
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
Inquire for bulk scale.
2-O-β-D-Glucopyranosyl-L-ascorbic acid (AA-2βG), isolated from Lycium Fruit, is a stable vitamin C analog with anti-tumor activity.
HPLC of 2-O-β-D-Glucopyranosyl-L-ascorbic acid
HNMR of 2-O-β-D-Glucopyranosyl-L-ascorbic acid
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
186.3700
-2.3020
-2.6029
165.6154
.4637
.2195
Low
32.3375
4.4179
Yes
No
No
No
No
No
0.0
Yes
No
Yes
Yes
Citanic acid (2-O-β-D-Glucopyranosyl-L-ascorbic acid), as an emerging natural product, has attracted widespread attention in the fields of natural medicinal chemistry and pharmacology in recent years. This compound was originally isolated from plants such as goji berries (Lycium barbarum) and possesses unique structural characteristics and significant biological activity. As the incidence of autoimmune diseases rises year by year, finding safe and effective treatments has become a research hotspot. Due to its excellent antioxidant properties and potential to regulate immune function, lyric acid is gradually being regarded as a promising candidate compound for treating autoimmune diseases.
This paper will systematically review the chemical structure and physicochemical properties of goji acid, its plant origin, and extraction methods, focusing on analyzing its pharmacological activity and mechanism of action, exploring its interactions with autoimmune disease-related targets, evaluating its druggability and pharmacokinetic characteristics, and looking ahead to its clinical application prospects. Through comprehensive literature integration and analysis, the aim is to provide scientific basis and theoretical support for subsequent research and clinical development of lycoric acid.
The chemical name of lycine acid is 2-O-β-D-Glucopyranosyl-L-ascorbic acid, with the molecular formula C12H18O10 and a molecular weight of 338.2650. Its structure is formed by the connection of L-ascorbic acid (vitamin C) and β-D-glucose via a glycosidic bond formed at the 2-hydroxyl position. This glycosylation modification not only improves its water solubility but also enhances the compound's stability, especially its antioxidant activity under physiological conditions.
From the perspective of physicochemical properties, the LogP value of lycoric acid is -2.3020, indicating strong hydrophilicity and good water solubility (165.6154 mg/mL), which is beneficial for absorption and distribution in the body. Its polar surface area (TPSA) reaches as high as 186.37 Ų, suggesting that its molecular polarity may be high, which may limit its ability to penetrate lipid membranes. The low permeability of the blood-brain barrier suggests its role in the central nervous system may be limited. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames test result was 0.0, indicating that lycoric acid does not have obvious mutagenicity and is relatively safe.
In summary, the structural characteristics and physicochemical properties of goji acid provide a solid foundation for its role as a pharmaceutical molecule, making it especially suitable for targeted immunomodulatory and antioxidant therapies.
Lycium barbarum is mainly found in goji berries (Lycium barbarum) and its related plants. As a traditional Chinese medicine and functional food, goji berries are rich in various bioactive components, including polysaccharides, flavonoids, vitamins, and various secondary metabolic products. As one of the important vitamin C derivatives, cidic acid has been successfully isolated and identified in recent years.
Common methods for extracting goji acid include water extraction and alcohol extraction, combined with column chromatography separation technology. The general steps are as follows:
In recent years, ultrasound-assisted extraction and microwave-assisted extraction technologies have also been applied to the extraction of goji acid, improving extraction efficiency and purity, and reducing energy consumption and time costs.
Research on the pharmacological activity of triberic acid mainly focuses on antioxidant, immunomodulatory, and anti-inflammatory effects, especially its potential in autoimmune disease models.
As a glycoside derivative of vitamin C, citanic acid demonstrates significant free radical scavenging ability. In vitro experiments show that lycium acid can effectively eliminate hydroxyl radicals, superoxide anions, and hydrogen peroxide, reducing oxidative stress damage. Its stable structure gives it a longer half-life in the body, extending the duration of antioxidant effects.
Lycoric acid exerts immune modulatory effects by regulating immune cell function. Research shows that citrus acid can promote the proliferation of regulatory T cells (Treg) and enhance FOXP3 expression, thereby suppressing autoimmune responses. At the same time, citanic acid inhibits the secretion of pro-inflammatory cytokines such as IL-17A, reducing inflammatory responses. In addition, goji acid can regulate the expression of anti-inflammatory factors such as IL-10 and TGFβ1, maintaining immune homeostasis.
In various inflammatory models, citanic acid has shown good anti-inflammatory activity. By downregulating the activity of the STAT3 signaling pathway, it reduces the expression of pro-inflammatory cytokines and alleviates tissue inflammatory damage. Animal experiments have shown that triberic acid can significantly alleviate symptoms of autoimmune-related diseases such as arthritis and inflammatory bowel disease.
The mechanism of action of citanic acid in autoimmune diseases mainly involves regulation of multiple signaling pathways and key molecular targets.
STAT3 is an important transcription factor regulating immune cell differentiation and inflammatory responses. Citeric acid reduces inflammatory responses and autoimmune pathological damage by inhibiting STAT3 phosphorylation, blocking its nuclear translocation, and reducing the expression of pro-inflammatory cytokines such as IL-17A.
Transforming growth factor β1 (TGFB1/TGFβ1) plays a bidirectional role in immune regulation. Lycoric acid can promote TGFB1 expression, enhance Treg cell function, inhibit the activation of effector T cells, maintain immune tolerance, and prevent excessive activation of autoimmune responses.
IL-10, as a major anti-inflammatory cytokine, promotes its secretion, enhances negative feedback regulation of the immune system, inhibits the release of inflammatory factors, and reduces tissue damage.
FOXP3 is a key transcription factor for regulatory T cells. Lycoric acid promotes the generation and function of Treg cells by upregulating FOXP3 expression, enhances immunosuppressive capacity, and prevents the occurrence and progression of autoimmune diseases.
IL-17A is a pro-inflammatory factor secreted by Th17 cells, involved in the pathological processes of various autoimmune diseases. Lycoric acid inhibits IL-17A expression, reduces inflammatory responses, and improves disease symptoms.
In summary, cistern berry acid regulates immune balance and suppresses inflammatory responses through multi-target and multi-pathway synergistic effects, demonstrating potential for treating autoimmune diseases.
Druggability evaluations of lycitinic acid indicate good safety and efficacy potential.
Lycoric acid has a moderate molecular weight and high water solubility, making it easy to absorb orally. However, its low lipophilubility and high polar surface area limit its ability to transmembrane, especially the low permeability of the blood-brain barrier, suggesting it mainly acts on the peripheral immune system. In the body, metabolism mainly involves glycosidic bond hydrolysis through hepatic enzyme systems, releasing the active ascorbic acid portion, which exerts antioxidant and immunomodulatory effects.
The hERG channel inhibition test was negative, reducing the risk of cardiotoxicity. Ames test results showed no mutagenicity, further confirming its safety. Additionally, animal toxicology studies have not shown significant toxic side effects, supporting its feasibility as a drug candidate.
Currently, research on the interaction between gourgic acid and commonly used drugs is limited. Future evaluation is needed to evaluate its safety and synergistic effects when combined with immunosuppressants, anti-inflammatory drugs, and others.
As a natural immunomodulator, citronic acid has broad clinical application prospects. Its potential efficacy in autoimmune diseases such as rheumatoid arthritis, multiple sclerosis, and systemic lupus erythematosus has been preliminarily validated in vitro and animal models. Future research should focus on the following directions:
In addition, citabic acid also shows potential in antioxidant, anti-inflammatory, and anti-aging fields, with potential to expand its indications.
As a natural product with a unique structure and significant biological activity, cidic acid shows broad application prospects in the treatment of autoimmune diseases thanks to its excellent antioxidant and immunomodulatory abilities. Its multi-target and multi-pathway mechanisms provide a theoretical foundation for the development of novel immunomodulatory drugs. Although research is still in its early stages, with the deep integration of pharmacology, molecular biology, and clinical medicine, trichinic acid is expected to become a safe and effective new drug for treating autoimmune diseases. In the future, it is necessary to strengthen its pharmacokinetics, toxicology, and clinical research to promote its transition from laboratory to clinical application, benefiting a broad range of patients.
Shenshuai
Wenjing
Hedandan
