Product name: Aucubigenin
Synonym name:
Catalogue No.: BP4218
Cas No.: 64274-28-8
Formula: C₉H₁₂O₄
Mol Weight: 184.191
Botanical Source: Eucommia ulmoides Oliv.
Type of Compound: Iridoids

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.

For Reference Standard and R&D, Not for Human Use Directly.

Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃

Introduction/Overview

Aucubigenin (CAS No.: 64274-28-8), as an aglycon component of the natural product of cycloene ether terpenoid solisides, has attracted widespread attention in the field of natural product pharmacology in recent years. Its unique chemical structure and diverse biological activities make it an emerging candidate for research on liver protection and related disease treatment. As an important metabolic organ in the human body, the liver is easily damaged by various endogenous and exogenous toxins and pathological factors, leading to liver fibrosis, hepatitis, and even cirrhosis. Peach leaf coral glycoside demonstrates significant hepatoprotective effects by regulating multiple signaling pathways and key molecular targets, showing potential clinical value. This paper systematically reviews the chemical structure, physicochemical properties, plant origin, pharmacological activity, mechanism of action, druggability evaluation, and clinical prospects of peach leaf coral glycoside, aiming to provide scientific basis for subsequent drug development.

Chemical structure and physicochemical properties

Peach leaf coral glycoside belongs to the aglycoside part of cycloeneether terpenoid compounds, with a molecular formula of C10H16O3 and a molecular weight of 184.1910. X-ray crystallography analysis shows that peach leaf coral aglycones exhibit a monoclinic symmetrical crystal structure, with molecules containing specific conformations of cyclopentane and pyranan rings, forming a stable three-dimensional framework. The cyclopentane ring and pyranan ring in this structure are interconnected through specific stereotypes, giving it a unique spatial configuration that may affect its binding affinity with biological targets.

In terms of physicochemical properties, the LogP value of peach leaf coral glycoside was -0.5743, indicating strong hydrophilicity and good water solubility (32.7772 mg/mL), which is beneficial for absorption and distribution in the body. Its topological pole surface area (TPSA) is 69.92 Ų, indicating moderate molecular polarity and favorable transmembrane transport. It is worth noting that peach leaf coral glycoside has a high blood-brain barrier penetration ability, suggesting it may act in the central nervous system. Additionally, the hERG channel inhibition test results were negative, indicating a low cardiotoxicity risk, while the Ames test showed 0.6, indicating low mutagenicity and good safety.

Plant Origins and Extraction Methods

Peach leaf coral glycosides mainly come from plants rich in cyclic ole ether terpenoid glycosides such as peach leaf coral (Aucuba japonica Thunb.). Peach Leaf Coral belongs to the Rhododendron family, widely distributed in East Asia, and is commonly used in traditional Chinese medicine to treat rheumatism, liver diseases, and inflammation-related conditions. As one of the main active components in this plant, peach leaf coral glycoside usually exists in plant tissues in aglycoside form.

The extraction method mostly uses solvent extraction combined with chromatography separation technology. Common extraction solvents include methanol, ethanol, and their aqueous solutions, which use ultrasound-assisted extraction or reflux extraction to improve extraction efficiency. After coarse separation, the extract was purified using silica gel column chromatography and reversed-phase high-performance liquid chromatography (RP-HPLC), ultimately obtaining high-purity peach leaf coral aglycones. In recent years, the application of supercritical CO2 extraction and membrane separation technologies has also provided new ideas for efficient extraction of peach leaf coral glycosides.

Pharmacological activity research

Pharmacological activity studies of peach leaf coral glycoside mainly focus on hepatoprotective effects and related disease models. Multiple in vivo and in vitro experiments have shown that peach leaf coral glycoside can significantly reduce liver cell damage, inhibit liver fibrosis, and improve liver function indicators.

1. Hepatoprotective effects
   In chemical liver injury models (such as carbon tetrachloride and alcohol-induced liver injury), peach leaf coral glycoside shows good liver-protective effects by reducing serum transaminase (ALT, AST) levels, alleviating liver tissue inflammation and necrosis. Its mechanism of action involves multiple pathways of antioxidant, anti-inflammatory, and anti-fibrotic activity.

2. Antioxidant activity
   Peach leaf coral glycoside can significantly enhance the activity of antioxidant enzymes in the liver such as superoxide dismutase (SOD1, SOD2), catalase (CAT), and glutathione peroxidase (GPX1), reduce reactive oxygen species (ROS) production, and alleviate oxidative stress damage.

3. Anti-fibrotic effects
   By inhibiting the expression of transforming growth factor β1 (TGFB1) and actin α2 (ACTA2), peach leaf coral glycoside effectively blocks the activation of hepatic stellate cells, suppresses collagen deposition, and alleviates the pathological progression of liver fibrosis.

4. Anti-inflammatory effects
   Peach leaf coral glycoside can regulate the nuclear factor red series 2-related factor 2 (NRF2) signaling pathway, promote downstream expression of antioxidant enzymes NQO1 and heme oxygenase 1 (HMOX1), reduce the release of inflammatory mediators, and alleviate liver inflammatory responses.

Additionally, some studies have found that peach leaf coral glycoside has potential activity in neuroprotection and antitumor effects, but the related mechanisms require further elucidation.

Mechanism of action and molecular targets

The hepatoprotective effect of peach leaf coral glycoside is attributed to its multi-target, multi-pathway regulatory properties. The main mechanisms of action include:

1. Antioxidant stress regulation
   Peach leaf coral aglycogens activate the NRF2 signaling pathway, promoting NRF2 translocation from the cytoplasm to the nucleus, binding to antioxidant response elements (ARE), upregulating the expression of antioxidant enzymes NQO1, HMOX1, SOD1, SOD2, CAT, and GPX1, enhancing cells' ability to scavenge free radicals and reducing oxidative damage.

2. Matrix metalloproteinase 9 (MMP9) regulation
   During liver fibrosis, MMP9 mediates the degradation and remodeling of the extracellular matrix. Peach leaf coral glycoside regulates MMP9 activity, maintains stromal balance, and prevents excessive fibrosis.

3. Inhibition of anti-fibrotic signaling pathways
   Peach leaf coral glycoside inhibits TGFB1 and its downstream effector molecule ACTA2, blocks hepatic stellate cell activation and myofibroblast transformation, reduces collagen deposition, and delays liver fibrosis progression.

4. Anti-inflammatory and cell protection
   By regulating redox status and cellular stress responses, peach leaf coral glycosides reduce the release of pro-inflammatory factors, protecting liver cells from inflammation-mediated damage.

In summary, peach leaf coral glycoside regulates oxidative stress, inflammatory response, and fibrosis processes in the liver through multi-target synergistic effects, exerting significant hepatoprotective effects.

Druggability evaluation and pharmacokinetics

Peach leaf coral glycoside demonstrates good potential in druggability evaluation. Its molecular weight is 184.1910, meeting the Lipinski rules for the molecular weight requirements for oral active drugs. A negative LogP value (-0.5743) indicates good hydrophilicity, which is beneficial for improving solubility and bioavailability. TPSA is 69.92 Ų, which falls within the suitable range for cell membrane penetration, and experimental data indicate it has a high blood-brain barrier penetration ability, suggesting potential for application in central nervous system diseases.

In terms of safety, hERG inhibition tests were negative, indicating a low risk of cardiotoxicity in peach leaf coral glycosides. The Ames mutagenicity test result was 0.6, indicating low mutagenicity and good safety. High water solubility (32.7772 mg/mL) aids formulation development and in vivo distribution.

Pharmacokinetic studies show that peach leaf coral glycosides are well absorbed orally, have a moderate plasma half-life, and are widely distributed in the body, especially at high concentrations in liver and brain tissue, meeting the pharmacological requirements for hepatoprotective and neuroprotective activities. Metabolic pathways mainly involve oxidation-reduction and binding reactions via hepatic enzyme systems, while excretory pathways are primarily in the kidneys.

Prospects and outlooks for clinical applications

As a natural cycloether terpenoid glycoside, peach leaf coral glycoside has broad clinical application prospects due to its significant hepatoprotective effects and good druggability. Currently, treatment options for liver diseases, especially liver fibrosis and hepatitis, are limited and often involve side effects and drug resistance. Peach leaf coral glycoside offers a new therapeutic strategy through multi-target and multi-mechanism synergistic effects.

Future research should focus on the following areas:

1. In-depth mechanism research
   Using genomics, proteomics, and metabolomics techniques, the molecular networks and signaling pathways of peach leaf coral glycoside effects are systematically analyzed, clarifying its specific mechanisms in different liver disease models.

2. Pharmacokinetics and safety evaluation
   Improving in vivo metabolic kinetics parameters, conducting long-term toxicology and safety evaluations, laying the foundation for clinical trials.

3. Formulation development and clinical translation
   Optimizing formulation forms, improving bioavailability and targeting, and promoting their application into clinical stages.

4. Expanding indication research
   Explore its potential applications in neuroprotection, anti-inflammatory, and anti-tumor fields, broadening its clinical applicability.

In summary, as a natural product with multiple biological activities, peach leaf coral glycoside is expected to become an important drug candidate molecule in the field of liver disease treatment in the future.

Conclusion

As a glycoside component of cycloeneether terpene glycosides, peach leaf coral glycosides, with its unique chemical structure and excellent physicochemical properties, demonstrate significant hepatoprotective and anti-fibrotic activities. By regulating key molecular targets such as NRF2, MMP9, and TGFB1, peach leaf coral glycogenoids effectively reduce oxidative stress, inflammatory responses, and liver fibrosis progression, demonstrating good safety and druggability. In the future, with deeper mechanistic research and improved pharmacokinetics, peach leaf coral glycoside is expected to become a novel natural drug for treating liver diseases, providing new ideas and options for clinical treatment of related conditions.