Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
Sesamoside (CAS number: 117479-87-5) is a terpenoid natural product isolated from the traditional Tibetan medicinal plant Lamiophlomis rotata. In recent years, with the rapid development of natural product pharmacology, sesame glycosides have attracted widespread attention due to their significant antioxidant and anti glycosylation activities. Oxidative stress and glycosylation injury are important pathological processes in the pathogenesis of many chronic diseases, such as neurodegenerative diseases, diabetes and its complications, cardiovascular diseases and so on. Flaxseed glycosides have shown potential preventive and therapeutic effects by regulating various antioxidant related targets, making them a hot topic in natural medicine research.
This article provides a systematic review of the chemical structure and physicochemical properties, plant sources, and extraction methods of paeoniflorin. It delves into its pharmacological activity and mechanism of action, evaluates it based on pharmacological parameters, and looks forward to its clinical application potential. The aim is to provide a theoretical basis and reference for further research and development of this compound.
The molecular formula of sesame glycoside is C21H32O9, with a molecular weight of 420.3670, belonging to terpenoid compounds. Its structural feature is a typical diterpenoid glycoside structure, containing multiple hydroxyl and sugar groups, giving it high polarity and water solubility. Its LogP value is -1.4807, indicating strong hydrophilicity and difficulty in passing through lipid membranes, consistent with its low blood-brain barrier penetration (BBB low). The total polar surface area (TPSA) is as high as 187.9 Å ², further supporting its high polarity characteristics.
The water solubility of sesame glycosides is about 30.2023 mg/mL, indicating good water solubility, which is beneficial for formulation development and in vivo absorption. The negative result of hERG channel inhibition experiment indicates a low risk of cardiac toxicity. The Ames test score is 0.3, indicating that the compound has no significant mutagenicity and good safety.
The glycosides of the sesame genus are mainly isolated from the Lamiophlomis rotata plant. L. Rotata is a perennial herbaceous plant in the family Lamiaceae, widely distributed in the Qinghai Tibet Plateau and surrounding areas of China. It is an important medicinal plant in Tibetan medicine, traditionally used for pain relief, anti-inflammatory effects, and promoting wound healing.
The extraction of paeoniflorin is usually carried out through the following steps:
This method has the advantages of high extraction efficiency, good purity, and easy operation, and is suitable for the large-scale separation of glycosides in the sesame genus.
The pharmacological activities of sesame glycosides are mainly reflected in two aspects: antioxidant and anti glycosylation, which lays the foundation for their potential applications in various diseases.
Oxidative stress is a common pathological basis for various diseases, and quercetin exerts protective effects through multiple antioxidant signaling pathways. In vitro experiments have shown that paeoniflorin can scavenge free radicals, significantly reduce intracellular reactive oxygen species (ROS) levels, and protect cells from oxidative damage.
In the cell model, after treatment with hesperidin, the activities of antioxidant enzymes such as superoxide dismutase (SOD1, SOD2), catalase (CAT), and glutathione peroxidase (GPX1) were significantly increased, indicating their ability to activate the endogenous antioxidant defense system. In addition, hesperidin can induce the expression of heme oxygenase-1 (HMOX1) and enhance cell tolerance to oxidative stress.
Non enzymatic glycosylation, which leads to the accumulation of advanced glycation end products (AGEs), is an important pathological mechanism of diabetes and its complications. Hemp glycosides exhibit good anti glycation effects by inhibiting the formation of AGEs and reducing glycosylation related cell damage.
Relevant in vitro experiments show that flax glycosides can significantly inhibit the glycosylation process of proteins, reduce the level of AGEs, and alleviate the cell dysfunction caused by glycosylation, providing a theoretical basis for the prevention and treatment of diabetes and its complications.
The pharmacological effects of sesame glycosides are closely related to their regulation of multiple key molecular targets, especially in the field of antioxidant damage.
NFE2L2 (nuclear factor erythroid 2-related factor 2, NRF2) is the main antioxidant transcription factor in cells. Hemp glycosides can promote the translocation of NRF2 from the cytoplasm to the nucleus, enhance its binding to antioxidant response elements (ARE), and induce downstream antioxidant enzyme gene expression.
By activating the NRF2 signaling pathway, hesperidin upregulates the expression of antioxidant enzymes such as SOD1, SOD2, CAT, GPX1, and HMOX1, systematically enhancing the cell's antioxidant defense ability, reducing ROS levels, and alleviating oxidative damage.
Hemp glycosides inhibit the formation of AGEs by directly capturing active intermediates in glycosylation reactions. In addition, sesame glycosides may regulate the activity of related enzymes, reduce the rate of glycosylation reactions, and alleviate cell damage caused by glycosylation.
Although the current focus is mainly on antioxidant related targets, hesperidin may also be involved in the regulation of other signaling pathways, such as inflammation factor regulation and mitochondrial function protection. Future research is expected to further reveal its multi-target mechanism of action.
The pharmacological parameters of sesame glycosides indicate that they have certain development potential, but there are also certain challenges.
The molecular weight of sesame glycosides is 420.3670, belonging to the medium molecular weight range. Its low LogP value (-1.4807) and high TPSA (187.9) indicate strong polarity and good water solubility (30.2023 mg/mL), which is beneficial for the dissolution and absorption of oral formulations.
However, high polarity and larger TPSA may limit its ability to pass through lipid membranes, resulting in reduced oral bioavailability, especially with weaker ability to penetrate the blood-brain barrier (BBB low), limiting its application in central nervous system diseases.
The hERG channel inhibition experiment was negative, indicating a low risk of cardiac toxicity. The Ames test score is 0.3, indicating no significant mutagenicity and good safety, making it suitable for further drug development.
At present, there is limited in vivo pharmacokinetic data on the glycosides of the Euphorbia genus. Given its high polarity and water solubility, it is speculated that its oral absorption may be limited, and its distribution in the body is mainly limited to blood and peripheral tissues. The metabolic pathway may involve glycoside hydrolysis and corresponding metabolic transformation by liver enzymes.
In the future, it is necessary to conduct systematic pharmacokinetic studies in vivo, including detailed analysis of absorption, distribution, metabolism, and excretion (ADME) processes, to guide dosage form optimization and clinical applications.
Due to its significant antioxidant and anti glycation activities, the glycosides of the Euphorbia genus have shown broad application prospects in the prevention and treatment of various chronic diseases.
Oxidative stress and glycosylation injury are the core pathological mechanisms of diabetes and its complications. Flax glycosides can alleviate oxidative and glycosylation damage through a dual mechanism, which is expected to be a new natural drug for adjuvant treatment of diabetes and slow down the progress of complications.
Although the penetration of the blood-brain barrier is relatively low, the antioxidant properties of sesame glycosides may still indirectly protect the nervous system through peripheral anti-inflammatory and antioxidant effects. In the future, the accessibility of the central nervous system can be improved through structural modification or nanocarrier technology, expanding the potential for the treatment of neurodegenerative diseases.
Oxidative stress plays a key role in atherosclerosis and myocardial injury. Hemp glycosides enhance antioxidant defense by activating the NRF2 signaling pathway, contributing to cardiovascular protection and reducing the risk of cardiovascular events.
Given the physicochemical properties of sesame glycosides, future strategies such as drug structure optimization, nanocarrier loading, and sustained-release formulations can be used to improve their bioavailability and targeting, promoting clinical translation.
In addition, combining modern pharmacology with traditional medical theory, conducting systematic preclinical and clinical research to verify its safety and effectiveness is the key to achieving the clinical application of paeoniflorin.
As a natural terpenoid compound with unique structure and significant biological activity, the glycosides of the Euphorbia genus exhibit excellent antioxidant and anti glycosylation effects. It systematically reduces oxidative damage by activating the NFE2L2/NRF2 signaling pathway and regulating various antioxidant enzymes, and has broad potential for disease prevention and treatment.
Although there are still shortcomings in pharmacokinetics and clinical research, its good safety and physicochemical properties lay the foundation for further development. In the future, optimizing preparations and improving bioavailability through multidisciplinary research means is expected to promote flax glycosides to become a new generation of natural drugs, serving the prevention and treatment of diabetes, neurodegenerative diseases, cardiovascular diseases and other chronic diseases.
In summary, the glycosides of Artemisia not only enrich the research content of natural product pharmacology, but also provide new ideas and directions for the development of natural medicines, which are worth exploring and widely applying.
