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Product Name: Ginkgolic Acid C13:0
Synonym name: 6-Tridecylsalicylic acid; Ginkgolic Acid C13-0
Catalogue No.: BP0643
Cas No.: 20261-38-5
Formula: C20H32O3
Mol Weight: 320.473
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.
NMR of Ginkgolic Acid C13:0
HPLC of Ginkgolic Acid C13:0
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
57.5300
7.5019
5.0051
.0246
4.0685
1.8641
Low
95.4496
2.0269
Yes
No
No
No
No
No
0.0
No
No
No
No
Ginkgolic acid (Ginkgolic acid C13:0, CAS No.: 20261-38-5), a class of natural fatty acid derivatives found in the leaves and seeds of ginkgo biloba L., has attracted widespread attention in recent years due to its diverse biological activity. As an ancient gymnosperm plant, ginkgo has a long history of medicinal value in traditional medicine. Modern research reveals that its active ingredients have significant pharmacological effects on various compounds such as ginkgo acid sulfate. Ginkgo Neoic Acid (C13:0), with its unique structural characteristics and biological functions, shows potential application value in antibacterial, antiparasitic, caries prevention, and immune regulation fields, especially as a PI3Kδ inhibitor and mast cell degranulation inhibitor, offering new ideas for the treatment of related immune and inflammatory diseases.
This review aims to systematically summarize the chemical structure and physicochemical properties, plant origins and extraction methods, pharmacological activity, and mechanisms of action of Ginkgonic acid (Gink Cinic acid, C13:0), with a focus on evaluating its molecular targets and druggability parameters, and exploring its clinical application prospects and development trends, aiming to provide a theoretical foundation and research direction for the pharmacology of natural products and related drug development.
Ginkgolic acid (Ginkgolic acid C13:0) has a chemical formula of C21H34O3 and a molecular weight of 320.4730 Da. Its structural feature is a long-chain fatty acid side chain with 13 carbon atoms, connected to a carboxyl group and benzene ring, making it a natural product of carboxylic acids. The compound has a LogP value as high as 7.5019, showing strong hydrophobicity but low water solubility (0.0246 mg/mL), which is closely related to its long-chain fatty acid structure. The topological pole surface area (TPSA) is 57.53 Ų, indicating moderate polarity, which may affect its cell membrane penetration capability.
In the structure of ginkgo neoacid, the hydroxyl and carboxyl groups on the benzene ring impart certain acidic and polar characteristics, while the long-chain fatty acid side chains enhance its affinity for the lipid environment. This structure enables it to exhibit unique activity in biofilm binding and protein interactions. Additionally, Ginkgo Neoic Acid showed no hERG channel inhibitory activity, and the Ames mutagenic test was negative, suggesting good safety and certain drug potential.
Ginkgo neoacid mainly comes from the leaves and seeds of the ginkgo tree, especially in the high levels of fat-soluble components in the ginkgo seed shell. As a widely distributed medicinal plant, ginkgo's leaves and seeds are used to prepare various medicines and health products. The extraction of new acid from ginkgo nuts is usually done using organic solvent extraction methods, such as ethanol, methanol, ethyl acetate, combined with ultrasound-assisted extraction or Soxhlet extraction technology to improve extraction efficiency and purity.
The extraction process generally includes the following steps: first, dry and crush the ginkgo leaves or seeds, then extract with an appropriate organic solvent. After filtering and concentration, the extract is separated and purified by column chromatography (such as silica gel columns or reversed-phase C18 columns). High-performance liquid chromatography (HPLC) and mass spectrometry (MS) technologies are widely used for identifying and determining the content of new ginkgo acid. In addition, in recent years, supercritical fluid extraction and membrane separation technologies have also been attempted to improve extraction efficiency and environmental friendliness.
As a multifunctional natural product, Ginkgo New Acid exhibits a variety of pharmacological activities, mainly including antibacterial, antiparasitic, anti-caries, immunomodulatory, and anti-inflammatory properties.
Ginkgoneoic acid exhibited significant inhibitory effects on various Gram-positive and Gram-negative bacteria. Research shows that it has a strong antibacterial effect against oral caries bacteria such as Streptococcus mutans, making it a potential anti-caries agent. Its antibacterial mechanisms may involve cell membrane destruction, disruption of energy metabolism, and inhibition of cell wall synthesis. In addition, Ginkgo Neoic Acid also shows certain inhibitory effects against certain drug-resistant strains, providing new candidate molecules for antimicrobial drug development.
Ginkgo neoacid has inhibitory effects on various parasites, especially showing good activity against protozoan parasites. Relevant in vitro and in vivo experiments have shown that ginkgo neoic acid can interfere with parasite metabolic pathways and cell structures, reducing their survival rate and reproductive capacity. This activity provides a potential natural medicinal resource for the treatment of parasitic infections.
Ginkgoneoic acid can significantly inhibit mast cell degranulation, with an IC50 of 2.40 μM, indicating its important role in regulating allergic reactions and inflammation. Mast cell degranulation is a key step in allergic reactions; inhibiting this process helps alleviate allergic diseases and chronic inflammation. Ginkgo neoic acid exerts anti-inflammatory effects by regulating mast cell signaling and reducing the release of histamine and other inflammatory mediators.
Additionally, Ginkgo neoic acid acts as a PI3Kδ inhibitor (IC50: 2.49 μM) and participates in regulating various immune cell functions. PI3Kδ plays a key role in the activation and proliferation of B cells, T cells, and other immune cells. Its inhibitors have therapeutic potential in autoimmune diseases, inflammatory diseases, and certain tumors. This activity of ginkgo neoacids lays the foundation for its application in immunomodulation.
The multi-target mechanism of ginkgo neoacid forms the basis of its diverse biological activity. Its main molecular targets include PI3Kδ and mast cell-related signaling pathways.
PI3Kδ is an important member of the phosphatidyl-inositol 3-kinase (PI3K) family, mainly expressed in immune cells and involved in regulating cell proliferation, differentiation, migration, and survival. Ginkgo neoic acid competitively inhibits the kinase activity of PI3Kδ, blocking the downstream Akt/mTOR signaling pathway, and suppresses immune cell overactivation and inflammatory responses. This mechanism gives it potential value in the treatment of autoimmune diseases and certain inflammatory tumors.
Ginkgo neoic acid alleviates allergic reactions by inhibiting the degranulation process of mast cells, reducing the release of histamine and other inflammatory mediators. Its mechanism of action may involve inhibiting the increase in intracellular calcium ion concentration and blocking the activation of degranulation-related signaling pathways such as Syk kinase and PLCγ. Additionally, Ginkgo Neoic Acid may influence vesicle fusion and release during degranulation by regulating the lipid environment of cell membranes.
The antibacterial and antiparasitic mechanisms of Ginkgo Neoic Acid have not been fully elucidated, but existing research suggests it may cause microbial death by disrupting the integrity of microbial cell membranes, interfering with energy metabolism and protein synthesis. Its hydrophobic structure facilitates the insertion of lipid bilayers into the cell membrane, increasing membrane permeability and inducing leakage of cell contents. Additionally, ginkgo neoacids may influence microbial signal transduction and gene expression, enhancing their antibacterial effects.
The druggability evaluation of Ginkgo New Acid shows it has certain potential for drug development, but also faces challenges.
Ginkgo neoacids have a moderate molecular weight (320.47 Da), meeting the Lipinski rule molecular weight requirements, but their high LogP value (7.50) shows strong hydrophobicity, which may lead to reduced bioavailability and limited distribution in vivo. Its low water solubility (0.0246 mg/mL) limits the development of oral formulations, requiring nanocarriers, liposomes, or other solvent systems to improve solubility and absorption.
The low blood-brain barrier permeability of Ginkgoneoic acid suggests its limited application in treating central nervous system diseases, but this also reduces the risk of potential toxicity to the central nervous system.
Ginkgo neoic acid did not exhibit hERG channel inhibitory activity, reducing the risk of cardiotoxicity. The Ames mutagenic test result was negative, indicating low genotoxicity. Overall, the safety is good, providing a solid foundation for further drug development.
Currently, in vivo pharmacokinetic research on Ginkgo Neoacid is limited. It is speculated that its high hydrophobicity may lead to stronger tissue binding and slow clearance, affecting the drug's half-life and distribution. In the future, systematic studies on in vivo absorption, distribution, metabolism, and excretion (ADME) are needed to clarify its pharmacokinetic characteristics and optimize dosing regimens.
As a versatile natural product, Ginkgo New Acid has demonstrated good pharmacological activity and safety in preclinical studies, showing broad application potential.
Given its inhibitory effect on oral cariogenic bacteria, Ginkgo New Acid is expected to be developed as a new anti-caries agent or oral care product, filling the gap of existing anti-caries drugs. Combined with modern oral preparation technologies, such as sustained-release capsules and mouthwashes, their clinical value can be enhanced.
As a PI3Kδ inhibitor and mast cell degranulation inhibitor, Ginkgo Acid holds promise in the treatment of allergic diseases (such as asthma and urticaria) and autoimmune diseases (such as rheumatoid arthritis and multiple sclerosis). In the future, through structural modification and optimization of drug delivery systems, innovative drugs targeting immune inflammation are expected to be developed.
The antibacterial and antiparasitic activities of Ginkgo New Acid provide a foundation for its application in the field of infectious diseases. Especially against the backdrop of increasingly severe infections by resistant bacteria and parasites, developing drugs based on Ginkgo New Acid is of great significance.
Future research should focus on structural optimization, pharmacokinetic improvement, and in-depth analysis of the mechanism of action of new acid in ginkgo nuts. By combining modern medicinal chemistry and biotechnology, we develop efficient and safe ginkgo nut new acid derivatives and compound formulations to promote their clinical translation. At the same time, systematic toxicological evaluations and preclinical efficacy validation are conducted to ensure safety and efficacy.
Ginkgolic acid (Ginkgolic acid C13:0), as an important bioactive component in ginkgo, shows broad application prospects in fields such as antibacterial, antiparasitic, caries prevention, and immune regulation due to its unique chemical structure and diverse pharmacological activities. As a PI3Kδ inhibitor and mast cell degranulation inhibitor, its mechanism of action provides new targets and strategies for the treatment of related diseases. Although its high hydrophobicity and low water solubility pose certain challenges for drug development, its good safety and multi-target activity make it an important candidate for natural product pharmacology research and new drug development.
In the future, it is necessary to strengthen systematic pharmacokinetic research and preclinical evaluation of new ginkgo acid and combine modern drug delivery technologies to optimize druggability and promote its clinical application. In-depth research on new ginkgo acid not only enriches the pharmacological understanding of ginkgo chemical components but also provides new paradigms and ideas for the application of natural products in modern medicine.
Shenshuai
Wenjing
Hedandan
