Product name: 6,8-Diprenylorobol
Synonym name:
Catalogue No.: SBP02466
Cas No.: 66777-70-6
Formula: C₂₅H₂₆O₆
Mol Weight: 422.477
Botanical Source:
Physical Description: Yellow powder
Type of Compound: Xanthones

Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
The product could be supplied from milligrams to grams. Inquire for bulk scale.
We provide solution to improve the water-solubility of compounds, thereby facilitating the variety of activity tests and clinic uses.

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

NMR of 6,8-Diprenylorobol

HPLC of 6,8-Diprenylorobol

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

Introduction/Overview

6,8-Diisopentyl Diprenylorobol is a naturally occurring isoflavone compound that has attracted widespread attention in the field of natural product pharmacology in recent years due to its unique structural characteristics and diverse biological activities. As a typical diisopentenyl-modified peaguarin sin, 6,8-diisopentenyl peaguirin not only exhibits significant antioxidant, anti-inflammatory, and antitumor activities, but also shows potential therapeutic value in various pathological conditions such as metabolic diseases and neurodegenerative diseases. This paper will systematically review the chemical structure, origin, pharmacological activity, mechanism of action, and druggability evaluation of this compound, aiming to provide theoretical basis and research directions for further drug development and clinical application.

Chemical structure and physicochemical properties

The molecular formula of 6,8-diisopentenylpea peagurinin is C_28H_30O_6, with a molecular weight of 426.47. Its structure is based on an orobol backbone, with an isopentenyl side chain introduced at positions 6 and 8, and this diisoprenyl modification significantly affects its hydrophobicity and biological activity. The compound has a LogP value of about 4.0, indicating good lipid solubility, which facilitates cell membrane penetration, but may also affect its water solubility and bioavailability.

Its polar surface area (TPSA) is 101.48 Ų, and it has 6 hydrogen bond acceptors, suggesting that its molecules possess certain polarity and hydrogen bonding capabilities, which may affect their binding affinity with biological targets. Based on current calculations, this compound has a low blood-brain barrier penetration capacity, suggesting that its direct role in central nervous system diseases may be limited. Regarding safety indicators such as hepatotoxicity, cardiotoxicity, and hERG channel inhibition, there is currently no definitive data and further in vivo and in vitro experimental validation is needed.

Plant Origins and Extraction Methods

6,8-Diisopentenyl peaguin is mainly found in legumes, especially in the roots and stems and leaves of certain genista and medicago species. Although its content is not as abundant as mainstream flavonoid compounds, its unique biological activity makes it a key focus of natural product research.

Extraction typically uses organic solvent extraction methods, such as ethanol or methanol extraction, combined with ultrasound-assisted extraction or reflux extraction to improve efficiency. Subsequently, high-purity 6,8-diisopentenyl peagulagin was obtained through separation and purification techniques such as liquid-liquid partitioning, silica gel column chromatography, and high-performance liquid chromatography (HPLC). In recent years, supercritical fluid extraction and membrane separation technologies have also been attempted to extract this compound, aiming to improve yield and purity while reducing the use of organic solvents.

Pharmacological activity research

Antioxidant activity

6,8-Diisopentenyl peagumagin demonstrates significant free radical scavenging ability, effectively inhibiting free radical generation in in vitro models such as DPPH and ABTS. Its antioxidant effect is mainly attributed to the electron donor effects of the phenolic hydroxyl group and isopentenyl side chain in the flavonoid backbone, which stabilize free radicals and reduce oxidative stress-related cell damage.

Anti-inflammatory effects

Multiple in vitro cell model studies have shown that 6,8-diisopentenylpea pea sinin can inhibit the production of inflammatory mediators such as tumor necrosis factor-α (TNF-α), interleukin-6 (IL-6), and nitric oxide (NO). Its mechanism involves inhibition of the nuclear factor κB (NF-κB) signaling pathway, reducing the expression of pro-inflammatory genes and alleviating inflammatory responses.

Antitumor activity

This compound exhibits proliferation inhibition in various tumor cell lines, including breast cancer, liver cancer, and colon cancer cells. Research shows that 6,8-diisopentenylpea pea-sinin can induce cell cycle arrest and promote apoptosis, with related mechanisms involving mitochondrial pathway activation and regulation of apoptosis-related proteins. In addition, it also has a certain inhibitory effect on tumor cell migration and invasion, suggesting potential anti-metastatic activity.

Metabolic regulation

Preliminary studies suggest that 6,8-diisopentenylpea peagurinin may improve metabolic syndrome-related indicators by regulating lipid metabolism and insulin signaling pathways. It has regulatory effects on adipocyte differentiation and inflammation, showing potential in treating obesity and type 2 diabetes.

Neuroprotective effects

Although the blood-brain barrier permeability is low, 6,8-diisopentenylpea peaagin demonstrates certain neuroprotective effects in neurodegenerative disease models by modulating peripheral inflammatory responses and oxidative stress. Its specific mechanism of action and clinical significance still require further research.

Mechanism of action and molecular targets

The biological activity of 6,8-diisopentenylpegua pea-gura-sinin is closely related to its multi-target effects. The main mechanisms of action include:

• Inhibition of the NF-κB signaling pathway: By blocking the phosphorylation and degradation of IκBα, it suppresses NF-κB nuclear translocation and reduces the expression of pro-inflammatory factors.
• MAPK pathway regulation: modulates the activity of MAPK family members such as p38, ERK, and JNK, affecting cell proliferation and apoptosis.
• Mitochondrial pathway induces apoptosis: promotes Bax protein expression, inhibits Bcl-2, activates Caspase-3, and induces tumor cell apoptosis.
• Enhanced antioxidant enzyme activity: Enhances the expression of antioxidant enzymes such as superoxide dismutase (SOD) and glutathione peroxidase (GPx), reducing oxidative stress damage.
• Lipid metabolism-related targets: regulate PPARγ and AMPK signaling pathways to improve lipid metabolism abnormalities.

Currently, there is a lack of high-throughput target screening and structural biology analysis for this compound. Future research will need to combine proteomics and molecular docking techniques to clarify its key targets and action networks.

Druggability evaluation and pharmacokinetics

From the perspective of druggability parameters, 6,8-diisopentenyl pea sinin has high lipid solubility (LogP=4.0), which facilitates cell membrane penetration but may result in insufficient water solubility, affecting oral absorption and bioavailability. TPSA is 101.48 Ų, which is within an acceptable range, but a higher number of hydrogen bond acceptors (6) may limit its membrane permeability.

Computational predictions show that its blood-brain barrier penetration capacity is low, limiting its application in central nervous system diseases. In terms of safety, there is no definitive data on hepatotoxicity, cardiotoxicity, and hERG channel inhibition, and systematic evaluation is needed through in vitro cytotoxicity tests and animal experiments.

Pharmacokinetic research is still in its early stages. Preliminary in vivo experiments indicate that the compound has low plasma concentrations after oral administration, which may indicate first-pass effects or rapid metabolic rates. The metabolic pathway is inferred to mainly produce various water-soluble metabolites through phase I and phase II enzyme systems in the liver. In the future, detailed pharmacokinetic and pharmacokinetic studies are needed to optimize dosing regimens and dosage form design.

Prospects and outlooks for clinical applications

Given the multiple activities of 6,8-diisopentenylpegua peagroin in anti-inflammatory, antitumor, and metabolic regulation, its potential as a candidate drug cannot be ignored. Future research directions should focus on:

• In-depth validation of targeted disease models: Using animal model systems to evaluate efficacy and safety in inflammatory diseases, tumors, and metabolic syndromes.
• Structural modification and drug design: Chemical modifications improve water solubility and bioavailability, reduce potential toxicity, and enhance targeting.
• Combination therapy strategies: Explore synergies with existing drugs, especially in tumor chemotherapy and metabolic disease treatment.
• Preclinical safety evaluation: Conduct comprehensive toxicological studies to clarify the safe dosage range and potential side effects.
• Pharmacokinetic optimization: Develop novel delivery systems such as nanocarriers and liposomes to improve their in vivo distribution and stability.

Moreover, with the development of multi-omics technology, combined with genomics, metabolomics, and other methods, revealing the functional network and personalized therapeutic potential of 6,8-diisopentenylpea peaguin will provide a solid foundation for clinical translation.

Conclusion

6,8-Diisopentenyl pea-din sinoid, as a structurally unique natural isoflavone compound, demonstrates rich pharmacological activity and broad application prospects. Although our understanding of its mechanism of action and pharmacokinetics is still incomplete, existing studies have laid the foundation for it as a candidate for novel natural medicines. In the future, through multidisciplinary collaboration, in-depth analysis of its molecular targets, optimization of druggability, and systematic preclinical research will enable 6,8-diisopentenyl peagulagin to achieve clinical translation in anti-inflammatory, anti-tumor, and metabolic disease fields, becoming an important breakthrough in natural product drug development.