Product name: Rehmapicrogenin
Synonym name: (3R)-3-Hydroxy-2,6,6-trimethyl-1-cyclohexene-1-carboxylic acid
Catalogue No.: BP4406
Cas No.: 135447-39-1
Formula: C₁₀H₁₆O₃
Mol Weight: 184.235
Botanical Source:
Type of Compound:

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

Rehmapicrogenin (CAS No.: 135447-39-1) is a natural compound obtained by isolating the roots of the traditional Chinese medicinal material Rehmannia glutinosa, and belongs to the steroid saponin compounds. Rehmannia, as a traditional Chinese medicine, has a long history of application in blood nourishment, yin nourishment, and endocrine regulation. Research on its active components has deepened in recent years. Due to its remarkable biological activity, especially anti-inflammatory and antidiabetic effects, Rehmannia has become a research hotspot in pharmacology and natural product chemistry. This paper aims to systematically review the chemical structure and physicochemical properties of dihuang matroglycoside, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation, and pharmacokinetic characteristics, and to explore its clinical application prospects and future development directions, providing theoretical basis and research reference for subsequent drug development and clinical translation.

Chemical structure and physicochemical properties

Dihuang matroglycoside has the chemical formula C_10H_16O_4 and molecular weight of 184.2350, classifying it as a steroidal matroglycogen. Its structural features include a typical steroid framework with certain polar groups, giving it unique physicochemical properties. The LogP value was 1.5349, indicating moderate lipid solubility, which facilitates membrane penetration without excessive hydrophobicity, balancing bioavailability and distribution in vivo. The topological pole surface area (TPSA) is 57.53 Ų, indicating moderate polarity, which facilitates binding to biological macromolecules such as enzymes and receptors. Water solubility is 10.6417, indicating moderate solubility in the aqueous phase, facilitating absorption and distribution in the body. The lower permeability of the blood-brain barrier means its role in the central nervous system may be limited, reducing the risk of central toxicity. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames mutagenicity test result was 0.0, indicating an extremely low genotoxicity risk and meeting drug safety requirements.

Plant Origins and Extraction Methods

The main source of Dihuang bitter glycosides is the root of Rehmannia glutinosa, a plant of the Scrophulariaceae family, widely distributed in eastern and central China. The root of Rehmannia contains various active components such as steroid saponins, phenols, and polysaccharides. As an important steroidal saponin component, it has high levels and biological activity.

Traditional extraction methods typically use solvent extraction combined with column chromatography separation technology. The specific steps include:

1. Sample pretreatment: Crush the dried Rehmannia root into fine powder to facilitate solvent extraction.
2. Solvent extraction: Reflux extraction is performed using an ethanol-water mixed solvent (such as 70% ethanol), with extraction time generally 2-3 hours, and extraction temperature controlled at 60-80°C.
3. Concentration and separation: After the extract is concentrated under reduced pressure to an appropriate volume, it is separated and purified using silica gel column chromatography or reversed-phase high-performance liquid chromatography (RP-HPLC).
4. Purity identification: Confirm structure and purity using mass spectrometry (MS), nuclear magnetic resonance (NMR), and infrared spectroscopy (IR) techniques.

In recent years, the application of ultrasound-assisted extraction and microwave-assisted extraction technologies has improved the extraction efficiency and purity of rehmannia matroglycosides, and the process has become greener and more environmentally friendly, making it suitable for large-scale production.

Pharmacological activity research

Anti-inflammatory effects

Dihuang matroglycoside has demonstrated significant anti-inflammatory activity in multiple in vitro and in vivo experiments. Its mechanism mainly involves inhibiting the expression of inflammatory mediators, including induced nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), and pro-inflammatory cytokine interleukin-6 (IL-6). These factors play a key role in the inflammatory response. Dihuang matrogen reduces inflammation by downregulating its expression, effectively alleviating symptoms of inflammation-related diseases.

Antidiabetic effects

The therapeutic potential of Dihuang Macrylin in diabetes is gradually gaining attention. Its targets involve multiple glucose metabolism and insulin signaling pathways, including:

• AMPK (PRKAA1): As a key regulator of energy metabolism, AMPK activation helps improve insulin sensitivity and promote glucose uptake.
• SGLT2: Sodium-glucose co-transporter 2, regulates renal glucose reabsorption and is an important target in diabetes treatment.
• GCK (Glucose Kinase): A key enzyme regulating glucose metabolism, promoting glucose utilization.
• PPARG: Peroxisome proliferators activate receptor γ, regulate lipid metabolism, and insulin sensitivity.
• AKT1, IRS1, PIK3R1: Core molecules in the insulin signaling pathway, regulating cellular responses to insulin.
• DPP4: Dipeptidel peptidase 4, involved in the degradation of glucagon-like peptide-1 (GLP-1), affecting insulin secretion.
• SLC2A4 (GLUT4): An insulin-dependent glucose transporter that promotes glucose into cells.

By modulating these targets, dihuang metaglycosides can improve insulin resistance, promote glucose metabolism, lower blood sugar levels, and demonstrate promising anti-diabetes potential.

Other pharmacological effects

In addition to anti-inflammatory and antidiabetic effects, preliminary studies have also found that deshuang magnesium glycosides may have potential for antioxidant, immunomodulatory, and cardiovascular protection, but the related mechanisms require further investigation.

Mechanism of action and molecular targets

The pharmacological effects of dihuang amacrygonin mainly depend on its regulation of various molecular targets, involving multiple levels such as signal transduction, gene expression, and metabolic regulation.

Anti-inflammatory mechanism

Dihuang matroglycosides inhibit the nuclear factor κB (NF-κB) signaling pathway, reducing the expression of inflammatory mediators iNOS, COX-2, and IL-6. NF-κB is a key transcription factor in inflammatory responses, and its activation leads to upregulation of the transcription of multiple inflammatory genes. Dihuang maconin blocks this pathway, reducing the production of pro-inflammatory factors and thus exerting anti-inflammatory effects.

Anti-diabetic mechanism

• AMPK Activation: Dihuang metaglycosides activate AMPK, promoting glucose uptake and fatty acid oxidation, improving energy metabolism balance.
• Insulin signaling enhancement: By promoting the activity of the IRS1 and PI3K/AKT signaling pathways, insulin signaling is strengthened, improving tissue sensitivity to insulin.
• SGLT2 inhibition: reduces renal glucose reabsorption, promotes urinary glucose excretion, and lowers blood sugar.
• PPARG regulation: improves lipid metabolism and reduces insulin resistance.
• DPP4 inhibition: prolongs the half-life of GLP-1 and promotes insulin secretion.

The synergistic effect of these mechanisms enables remarkable effects of dihuang matrogen in regulating blood glucose and improving diabetic pathology.

Druggability evaluation and pharmacokinetics

Druggability parameters

The molecular weight of dihuang matroside is 184.2350, meeting the Lipinski rule requirement for molecular weight less than 500. The LogP is 1.5349, indicating moderate lipid solubility, which is beneficial for oral absorption. TPSA was 57.53 Ų, indicating moderate polarity that aids membrane penetration. Moderate water solubility, facilitating drug formulation design. The blood-brain barrier has low permeability, reducing the risk of central nervous system side effects. hERG was inhibited negative, and the Ames test showed no mutagenicity, demonstrating good safety and toxicological characteristics.

Pharmacokinetics

Currently, systematic pharmacokinetic research on Dihuang Mamaginin is relatively limited. Preliminary in vivo experiments show that it is well absorbed orally and has high bioavailability. Metabolic pathways mainly involve phase I and phase II metabolism in the liver, but the metabolites have not yet been fully identified. Excretion mainly occurs via the kidneys and bile pathways. In the future, more systematic studies of ADME (Absorption, Distribution, Metabolism, Excretion) are needed to clarify its in vivo kinetic characteristics and provide a basis for clinical dose design.

Prospects and outlooks for clinical applications

Dihuang matrogen, with its remarkable anti-inflammatory and antidiabetic activities, has broad clinical application potential. Currently, the treatment of diabetes and its complications still faces many challenges, especially regarding drug side effects and drug resistance. Dihuang matrogen regulates blood glucose and inflammatory responses through multiple targets and pathways, offering a new therapeutic strategy.

The key to future clinical applications lies in:

1. In-depth pharmacodynamic research: clarify its specific mechanisms and targets in the human body to optimize treatment plans.
2. Safety Assessment: Conduct systematic toxicology and long-term safety studies to ensure clinical safety.
3. Dosage Form Development: Based on their physicochemical properties, develop drug formulations suitable for oral administration or other administration routes to improve patient compliance.
4. Clinical trial validation: Conduct multicenter, randomized controlled clinical trials to verify efficacy and safety, and promote the transition from the laboratory to clinical practice.

In addition, the potential applications of dihuang matroside in anti-inflammation, immune regulation, and cardiovascular protection are also worth further exploration, potentially expanding its indications.

Conclusion

As an important active ingredient in Rehmannia, rehmannia maconin demonstrates strong anti-inflammatory and anti-diabetic potential due to its unique chemical structure and multi-target pharmacological effects. It has excellent druggability parameters and relatively high safety, showing promising clinical development prospects. In the future, systematic research on its pharmacokinetics, mechanisms of action, and clinical efficacy should be strengthened to promote its transformation into novel natural medicines, providing new options for the treatment of diabetes and related inflammatory diseases. With continuous advances in natural product pharmacology and modern drug development technologies, dihuang matrin is expected to become an important player in the development of natural product drugs, promoting the modernization and internationalization of traditional Chinese medicine.