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Synonym name:
Catalogue No.: BP0147
Cas No.: 33037-46-6
Formula: C21H20O10
Mol Weight: 432.381
Botanical Source: Found in Chinese rhubarb (Rheum palmatum), cascara sagrada (Rhamnus purshiana) and Alexandria senna (Cassia acutifolia)
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.
HPLC of Aloe-emodin-8-O-beta-D-glucopyranoside
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
194.2700
-.5600
Low
Unknown
Unknown
Unknown
Unknown
Unknown
Unknown
Aloe-emodin-8-O-beta-D-glucopyranoside (CAS No.: 33037-46-6) is a natural anthraquinone glycoside compound, mainly isolated from the plant Saussurea lappa. As a glycoside derivative of aloe emodin, this compound has attracted widespread attention in the field of natural product pharmacology. In recent years, with the continuous rise in the incidence of Type 2 diabetes mellitus (T2DM), the development of inhibitors targeting its key regulatory target, protein tyrosine phosphatase 1B (PTP1B), has become a hot topic in diabetes treatment research. Aloe vera emodin-8-O-glucoside, as a mild hPTP1B inhibitor, demonstrates potential pharmacological activity and application value.
This paper will systematically review the chemical structure and physicochemical properties of aloe emodin-8-O-glucoside, plant origin and extraction methods, pharmacological activity, mechanism of action and molecular targets, druggability evaluation, and pharmacokinetic characteristics. Finally, it will explore its clinical application prospects and future research directions, aiming to provide scientific basis and theoretical support for drug development of this natural product.
Aloe emodin-8-O-glucoside is a glycoside derivative of anthraquinone compounds, with the molecular formula C21H24O10 and a molecular weight of 432.37. Its core structure consists of aloe-emodin and β-D-glucose, which form an O-glycosidic bond via an 8-hydroxyl group. This structure endows it with high polarity and water solubility, a large molecular surface area, a polar surface area (TPSA) of 194.27 Ų, and a number of hydrogen bond acceptors reaching 10, indicating strong hydrogen bond formation capability.
In terms of physicochemical properties, the LogP value of aloe emodin-8-O-glucoside was -0.56, indicating strong hydrophilicity, which may affect cell membrane permeability and bioavailability. Its blood-brain barrier penetration is relatively low, suggesting limited distribution in the central nervous system. There is currently no definitive data on safety indicators such as hepatotoxicity, cardiotoxicity (including hERG channel inhibition), and genotoxicity (Ames test), and further research is needed.
Glycosylation modification of the molecular structure not only improves the water solubility of aloe emodin but may also affect its binding affinity and metabolic stability with target proteins, laying the foundation for its pharmacological activity.
Aloe vera emodin-8-O-glucoside is mainly isolated from Saussurea lappa, a plant in the Asteraceae family. Saussurea lappa is a perennial herbaceous plant widely distributed across parts of Asia. Traditionally, it has been used in traditional Chinese medicine and has multiple pharmacological effects including anti-inflammatory, anti-tumor, and metabolism regulation.
The extraction process typically uses dried plant rhizomes as raw materials, first extracted with polar solvents such as ethanol or methanol, followed by liquid-liquid partitioning and column chromatography (such as silica gel column chromatography and reversed-phase C18 column chromatography) for separation and purification. High-performance liquid chromatography (HPLC) combined with mass spectrometry (MS) techniques are commonly used for qualitative and quantitative analysis of compounds.
In recent years, green extraction technologies such as ultrasound-assisted extraction and microwave-assisted extraction have gradually been applied to the separation of natural products, improving extraction efficiency and purity, and providing technical support for the large-scale preparation of aloe emotin-8-O-glucoside.
Aloe vera emodin-8-O-glucoside showed moderate inhibitory activity against human protein tyrosine phosphatase 1B (hPTP1B) in vitro, with an IC50 value of 26.6 μM. PTP1B is an important negative regulator of the insulin signaling pathway. Through dephosphorylation, it inhibits the activity of insulin receptors and their substrates, leading to impeded insulin signaling and serving as a key target for insulin resistance related to type 2 diabetes and obesity.
Additionally, aloe emodin-8-O-glucoside has potential regulatory effects on other targets related to metabolic diseases, such as AMPK (5' AMP-activated protein kinase), GCK (glucokinase), MCL1 (anti-apoptotic protein), APP (amyloid precursor protein), AKR1B1 (aldose reductase), and NFE2L2 (nuclear factor red 2-related factor 2), suggesting that it may coordinately regulate metabolic balance through multiple targets.
Previous studies have shown that this compound can improve insulin sensitivity, suppress inflammatory responses, reduce oxidative stress, and have certain metabolic protective effects in cell models. However, in vivo pharmacodynamic evaluation and long-term safety data are still lacking, and further animal experiments and preclinical studies are urgently needed.
The main mechanism of action of aloe emodin-8-O-glucoside focuses on inhibition of hPTP1B. PTP1B negatively regulates insulin receptors (IR) and their substrate IRS (insulin receptor substrates) through dephosphorylation, leading to obstruction of the insulin signaling pathway and subsequently triggering insulin resistance. Aloe vera emodin-8-O-glucoside inhibits its enzyme activity by binding to the active site of PTP1B, enhancing insulin signaling and helping to improve glucose metabolism disorders.
Additionally, this compound may activate the AMPK signaling pathway, which acts as a cellular energy sensor regulating glycolipid metabolism and energy balance. Its activation helps improve insulin sensitivity and promote fatty acid oxidation. The regulatory effect of aloe emodin-8-O-glucoside on AMPK provides a molecular basis for its anti-diabetic potential.
Other targets such as GCK are involved in glucose phosphorylation and are important enzymes for glucose sensing in islet β cells; MCL1 regulates apoptosis and may affect the survival of β islet cells; NFE2L2 regulates antioxidant responses and alleviates oxidative stress damage. Aloe vera emodin-8-O-glucoside synergistically improves metabolic function through multi-target action, reflecting its complex pharmacological network.
Molecular docking and kinetic simulation studies show that the glycoside portion of this compound binds to key residues of PTP1B via hydrogen bonds, enhancing binding stability and suggesting that glycosylation modification has an important impact on its activity.
From a druggability perspective, the molecular weight of aloe emodin-8-O-glucoside is 432.37, slightly above the ideal range recommended by Lipinski's rule (<500), but its higher polar surface area (TPSA=194.27) and number of hydrogen bond receptors (10) may limit its oral bioavailability and cell membrane permeability.
The LogP value was -0.56, indicating strong hydrophilicity, which is beneficial for dissolution and transport in the blood, but may reduce its ability to penetrate lipid membranes. The blood-brain barrier has relatively low permeability, reducing the risk of central nervous system side effects, but it also limits its potential application in neurometabolic diseases.
Detailed pharmacokinetic (PK) data for this compound, including absorption, distribution, metabolism, and excretion (ADME) characteristics, are currently lacking. Given its glycoside structure, it may be hydrolyzed by glycosidase enzymes in the intestines, affecting the concentration and duration of its bioactive form in vivo.
In terms of safety, there are no clear data on hepatotoxicity, cardiotoxicity (hERG suppression), and genotoxicity, requiring systematic toxicological evaluation. In the future, structural optimization, such as glycosylation modification or lipid modification, may improve its pharmacokinetic properties and safety.
Aloe vera emodin-8-O-glucoside, as a naturally derived hPTP1B inhibitor, has potential for development as an adjunctive treatment for type 2 diabetes. Its multi-target regulatory effects not only help improve insulin resistance but may also slow the progression of diabetic complications through anti-inflammatory and antioxidant mechanisms.
Currently, the development of small molecule inhibitors targeting PTP1B faces issues such as poor selectivity, low bioavailability, and toxicity. The natural product background and mild activity of aloe emodin-8-O-glucoside provide unique advantages. By integrating modern drug design technologies, such as molecular modification and nanocarrier delivery, it is expected to overcome druggability limitations.
Future research should focus on:
Additionally, considering its low blood-brain barrier permeability, aloe-emodin-8-O-glucoside may be suitable for development as a peripheral metabolic regulator to reduce the risk of central nervous system side effects.
Aloe emodin-8-O-glucoside, a natural anthraquinone glycoside isolated from Saussurea lappa, demonstrates moderate inhibitory activity and multi-target regulatory potential against human protein tyrosine phosphatase 1B, demonstrating significant antidiabetic pharmacological value. Its unique chemical structure endows it with good water solubility and multiple mechanisms of action, but its druggability and pharmacokinetic characteristics still require systematic research and optimization.
In the future, through multidisciplinary collaboration combined with modern medicinal chemistry, molecular biology, and pharmacological approaches, it is expected to promote the clinical application of aloe emodin-8-O-glucoside, providing new natural drug resources and strategies for the treatment of type 2 diabetes and related metabolic diseases.
Shenshuai
Wenjing
Hedandan
