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Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
Shikimic acid (CAS number 138-59-0), as a key metabolic intermediate in the biosynthesis pathway of aromatic amino acids, is widely present in plants, microorganisms, and some fungi. Its unique chemical structure and biological activity have attracted much attention in the field of natural product pharmacology. Shikimic acid is not only a precursor of various aromatic compounds, but also an important starting material for the synthesis of antiviral drugs, especially playing a key role in the production of the anti influenza virus drug Tamiflu. In recent years, with the in-depth study of its pharmacological activity and molecular mechanism, shikimic acid has shown great potential for applications in antiviral, anti-inflammatory, and immune regulation. This article will provide a systematic review of the chemical structure and physicochemical properties of shikimic acid, plant sources and extraction methods, pharmacological activity research, mechanism of action and molecular targets, pharmacological evaluation and pharmacokinetics, and finally explore its clinical application prospects and future development directions.
The chemical name of shikimic acid is 3,4,5-trihydroxycyclohex-1-en-1-carboxylic acid, with a molecular formula of C7H10O5 and a molecular weight of 174.1520. Its structural feature is a cyclohexene ring, with hydroxyl groups replacing positions 3, 4, and 5 respectively, and possessing specific stereochemical configurations (3R, 4S, 5R), endowing it with high stereoselectivity. As a cyclohexene carboxylic acid, shikimic acid combines the chemical properties of hydroxymonocarboxylic acid and α, β - unsaturated monocarboxylic acid, exhibiting good water solubility (109.5634 mg/mL) and a LogP value of -1.4628, indicating its strong hydrophilicity and difficulty in freely diffusing through lipid membranes, as well as low blood-brain barrier permeability.
The polar surface area (TPSA) of shikimic acid is 97.99 Å ², indicating its strong polarity and hydrogen bond donor/acceptor ability, which is of great significance for its binding to biomolecule targets. It has good chemical stability and does not exhibit hERG channel inhibition. The Ames mutagenicity test result is negative, indicating its high safety and good potential for drug development.
Shikimic acid is widely present in various plants and microorganisms, especially in the fruit of star anise (Illicium verum), which is rich in content and is the main source of industrial extraction. In addition, certain strains of bacteria such as brewing yeast and Escherichia coli can also synthesize shikimic acid, making them important targets for biosynthesis research.
The traditional extraction method of shikimic acid mainly relies on the extraction of plant materials with water or alcohol solvents, combined with acid-base adjustment and crystallization purification processes. In recent years, the application of ultrasound assisted extraction, microwave-assisted extraction, and membrane separation technologies has significantly improved extraction efficiency and purity. The biological fermentation method utilizes genetic engineering to modify microbial strains, achieving efficient production of shikimic acid and becoming an important alternative to traditional plant extraction.
The pharmacological activity of shikimic acid is mainly concentrated in the field of antiviral, covering the inhibitory effects on various viral targets. Research has shown that shikimic acid and its derivatives have significant inhibitory effects on viruses such as influenza virus, herpes virus, and HIV. Its antiviral activity involves multiple interventions in virus replication, transcription, and viral protein function.
In addition, shikimic acid exhibits certain anti-inflammatory activity, which can regulate immune cell function and inhibit the release of inflammatory factors. Some studies suggest that shikimic acid also has potential in antioxidant and neuroprotective aspects. Although its blood-brain barrier permeability is low, it is expected to exert its pharmacological effects in the central nervous system through structural modifications or carrier systems.
The antiviral mechanism of shikimic acid involves multiple virus related targets, including myeloperoxidase (MPO), herpes virus gene products UL42, UL54, ICP27, TK (thymidine kinase), viral envelope glycoprotein gD, as well as HIV related CCR5, CXCR4 receptors, HIV1 protease (HIV1-PR), and integrase (INT).
Shikimic acid interferes with the replication cycle and infection process of viruses by binding to these targets. For example, shikimic acid can inhibit the function of UL42 and UL54 proteins, blocking the replication of herpes virus DNA; Regulation of CCR5 and CXCR4 receptors in HIV reduces the virus's ability to enter host cells; Simultaneously inhibiting HIV1-PR and integrase activity, blocking the maturation of viral proteins and genome integration.
In addition, shikimic acid exerts indirect antiviral effects by regulating host immune responses, enhancing antiviral immunity. These multi-target and multi mechanism characteristics make shikimic acid an ideal candidate molecule for antiviral drug development.
Shikimic acid has a moderate molecular weight, high polarity, and good water solubility, which meets the physical and chemical properties requirements of most oral drugs. Its negative LogP value indicates strong hydrophilicity and poor lipid solubility, which limits its passive diffusion ability through the cell membrane. The low permeability of the blood-brain barrier suggests that its application in central nervous system diseases requires the use of drug delivery systems or structural optimization.
In terms of safety, shikimic acid does not inhibit hERG channels, reducing the risk of cardiac toxicity; The Ames test is negative, indicating that it does not have mutagenicity and has a good safety basis.
Pharmacokinetic studies have shown that shikimic acid is absorbed rapidly in vivo, but its bioavailability is limited by its polarity and metabolic stability. By means of nanocarriers, liposome encapsulation, and chemical modification, its in vivo distribution and stability can be improved, enhancing drug efficacy.
As a molecule with significant antiviral activity in natural products, shikimic acid has broad clinical application prospects. As a key precursor for anti influenza drugs such as oseltamivir, it has played an important role in the pharmaceutical industry. In the future, shikimic acid and its derivatives are expected to be developed as broad-spectrum antiviral drugs against various viral infections, especially in the prevention and treatment of emerging viruses and drug-resistant strains.
In addition, the immunomodulatory and anti-inflammatory activities of shikimic acid provide new ideas for its application in autoimmune and inflammatory diseases. Combining modern drug delivery technology and structural optimization strategies, shikimic acid is expected to break through the limitations of the blood-brain barrier and expand into the treatment of neurological diseases.
Future research should focus on the mechanism of action analysis, pharmacokinetic optimization, and preclinical safety evaluation of shikimic acid, in order to promote its clinical translation. At the same time, advances in biosynthetic technology will promote the sustainable production of shikimic acid, reduce costs, and enhance industrialization levels.
As a key intermediate in the biosynthesis pathway of aromatic amino acids, shikimic acid has become an important subject of natural product pharmacology research due to its unique chemical structure and multi-target antiviral activity. Its excellent physicochemical properties and safety lay the foundation for medicinal properties, and its abundant sources of plants and microorganisms ensure its supply. With a deeper understanding of its pharmacological mechanism and optimization of pharmacokinetics, the application prospects of shikimic acid in the fields of antiviral and immune regulation are becoming increasingly broad. In the future, combined with modern drug development technology, shikimic acid is expected to become an important representative of the new generation of natural product drugs, providing strong support for human antiviral therapy.
