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Product name: 6-Feruloylcatalpol
Synonym name:
Catalogue No.: SBP01656
Cas No.: 770721-33-0
Formula: C25H30O13
Mol Weight: 538.502
Botanical Source:
Physical Description: Powder
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
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.
HPLC of 6-Feruloylcatalpol
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
197.1300
-.1022
-.1047
3.8664
.5332
.3155
Low
65.4164
5.0297
No
No
No
No
Yes
No
0.0
Yes
Yes
Yes
Yes
6-Feruloylcatalpol (CAS No.: 770721-33-0) is a naturally occurring hydroxycinnamic acid derivative and belongs to the ester class of natural products. Due to its unique chemical structure and diverse biological activities, it has attracted widespread attention in the field of natural product pharmacology in recent years. As a metabolite, 6-feruloylzisol is found in various plants, especially showing significant pharmacological potential in traditional Chinese medicinal materials. Its role in immunomodulation is particularly prominent, involving multiple key signaling pathways and molecular targets such as TLR4, STAT3, NFKB1, and others, demonstrating potential for modulating immune responses, anti-inflammation, and immune tolerance.
This paper aims to systematically review the chemical structure and physicochemical properties, plant origin and extraction methods, pharmacological activity and mechanism of action of 6-feruloylzidol, druggability evaluation, and clinical application prospects, aiming to provide researchers in related fields with comprehensive and in-depth reference materials to promote further development and application of this natural product.
6-Feruloylzisol is a complex formed by ferulic acid and aziol connected by ester bonds, with the molecular formula C_27H_34O_12 and a molecular weight of 538.5020. Its structural features include a hydroxycinnamic acid group (ferulic acid) connected to a polyhydroxy cyclic glycoside (zitonol), which imparts abundant hydroxyl and phenolic hydroxyl functional groups, resulting in strong polarity.
In terms of physicochemical properties, the LogP value of 6-feruloylzisol is -0.1022, indicating strong hydrophilicity and good water solubility (3.8664), which facilitates its dissolution and distribution in the body. Its topological pole surface area (TPSA) is 197.13 Ų. A higher pole surface area is usually related to molecular polarity and hydrogen bonding capacity, suggesting possible limitations in cell membrane permeability. The blood-brain barrier penetration ability is low, indicating its limited distribution in the central nervous system. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. Ames mutagenic assay results were 0.0, indicating a low genotoxicity risk.
In summary, 6-feruloylzidinol has good water solubility and safety profiles, but its high polarity and low lipophilic solubility may limit its oral bioavailability and cell membrane penetration ability, providing direction for subsequent pharmacokinetic optimization.
6-Feruloylzisol is mainly found in various traditional Chinese medicinal plants, especially those rich in catarulol derivatives and cinnamic acid compounds. For example, it has been reported in plants of the Scrophulariaceae family, cataloid plants, and certain medicinal plants with immunomodulatory functions. Although its content is not high, it can be effectively extracted and purified through modern separation technology.
Common extraction methods include:
Solvent extraction method
Using methanol, ethanol, or their aqueous solutions as extraction solvents, and extracting with reflux or ultrasound-assisted extraction, can efficiently dissolve 6-feruloylzisol. Extraction conditions such as temperature, time, and solvent polarity have a significant impact on yield.
Liquid-liquid distribution and column chromatography separation
After liquid-liquid distribution to remove lipophilic impurities, the extract was separated and purified using a silica gel column, C18 reversed phase column, or high-performance liquid chromatography (HPLC) to obtain high-purity 6-feruloylzisol.
Modern extraction technology
New technologies such as supercritical CO_2 extraction and microwave-assisted extraction have shown advantages in improving extraction efficiency, reducing solvent usage, and protecting active ingredients, gradually becoming research hotspots for extracting 6-feruloylzisol.
In addition, the harvest time, location, and growth environment of the plants all significantly affect the content of 6-feruloylzisol, making optimizing planting and harvesting conditions key to ensuring raw material quality.
Pharmacological activity studies of 6-feruletazisol mainly focus on immunomodulatory and anti-inflammatory effects. It regulates immune responses through multiple targets and pathways, demonstrating potential for treating autoimmune diseases, inflammatory diseases, and immune dysfunction.
6-Feruletylzisol can regulate various immune cell functions, including T cells, B cells, and macrophages. In vitro experiments have shown that it can regulate cytokine expression, promote the expression of immune tolerance-related factors such as FOXP3, inhibit the activity of pro-inflammatory factors like NFKB1, and balance Th1/Th2 cell responses.
By inhibiting the TLR4 signaling pathway, 6-ferulylzisol reduces the release of pro-inflammatory cytokines such as IL2 and IFNG, thereby alleviating inflammatory responses. In animal models, this compound demonstrated effects in reducing inflammatory tissue damage and lowering inflammatory markers.
Some studies suggest that 6-feruloylzidinol may have antioxidant, antitumor, and neuroprotective effects, but the related mechanisms require further elucidation.
The mechanism of action of 6-feruloylzisol involves multiple immune signaling pathways and key molecular targets, reflecting its multi-target regulation characteristics.
TLR4, as an important receptor for innate immunity, mediates the initiation of inflammatory responses. 6-Feruletylzisol inhibits TLR4 activation, blocks downstream MyD88-dependent signaling, reduces NFKB1 nuclear translocation, lowers the expression of pro-inflammatory cytokines such as IL2 and IFNG, thereby alleviating inflammatory responses.
6-Ferululetylzisol regulates the activities of STAT3 and STAT4, influences cytokine signaling, and regulates immune cell differentiation and function. Inhibition of STAT3 helps suppress inflammatory responses and immune suppression of the tumor microenvironment, while regulation of STAT4 affects the function of Th1 cells.
This compound promotes the expression of immunosuppressive factors such as CTLA4, IL10, and FOXP3, enhances regulatory T cell (Treg) function, maintains immune homeostasis, and prevents excessive immune responses.
6-Feruloylzisol can regulate TGFB1 expression, participate in immune tolerance and tissue repair processes, and promote post-inflammatory tissue recovery.
In summary, 6-feruloylzidinol regulates immune system balance through multi-target synergistic action and demonstrates good immunomodulatory potential.
Based on Lipinski's rule and other drug similarity indicators, 6-feruloylozisol has a large molecular weight (538.5 Da) and high polarity (TPSA 197.13 Ų), with a LogP close to zero, indicating good water solubility but poor lipid solubility, which may affect oral absorption and cell membrane penetration. It does not inhibit hERG channels, is genotoxic negative, and has relatively high safety.
Currently, in vivo pharmacokinetic studies of 6-feruloylzidinol are limited. Based on its physicochemical properties, it is speculated that its oral bioavailability may be limited, and its blood-brain barrier penetration ability is low, suggesting that it mainly acts on the peripheral immune system.
Metabolic pathways may involve phase I and II metabolic reactions such as hydroxylation of liver enzyme systems and glucuronic acid binding. The excretion route may be mainly through the kidneys.
In the future, systematic in vivo pharmacokinetic studies, including absorption, distribution, metabolism, and excretion (ADME) characteristics, are needed to guide dosage formulation design and administration regimen optimization.
6-Feruloylozisol, as a natural product with significant immunomodulatory activity, shows broad clinical application potential. Its application in autoimmune diseases, chronic inflammatory diseases, and immune dysfunction is particularly noteworthy.
By regulating Treg cells and inhibiting pro-inflammatory factors, 6-feruloylzisol may effectively alleviate pathological processes in autoimmune diseases such as rheumatoid arthritis and multiple sclerosis.
Its anti-inflammatory effect by inhibiting the TLR4/NFKB1 pathway suggests therapeutic potential in inflammatory bowel disease, chronic obstructive pulmonary disease, and other conditions.
Promoting the expression of immune tolerance-related factors may help control immune rejection in organ transplantation.
Although 6-ferululylazisol has good bioactivity and safety, its high polarity and molecular weight limit oral bioavailability. In the future, pharmacokinetic performance can be improved through medicinal chemical modifications and nanocarrier delivery systems.
In addition, systematic preclinical safety evaluation and clinical trial design will be key to driving its clinical application.
6-Feruloylzidol, as a natural product with a unique structure and multi-target immunomodulatory activity, shows broad prospects for pharmacological research and clinical applications. By regulating key molecules such as TLR4, STAT3, and NFKB1, it modulates immune responses and demonstrates anti-inflammatory and immunomodulatory potential. Despite challenges in druggability, its good safety provides a valuable natural molecular template for the development of novel immunomodulatory drugs.
In the future, combined with modern drug design technologies and systematic pharmacokinetic research, it is expected to promote clinical translation of 6-feruloylzisol and benefit patients with immune-related diseases. Researchers should strengthen in-depth analysis of its mechanism of action, optimize extraction and purification processes, conduct systematic preclinical and clinical studies, and fully explore its medicinal value.
Shenshuai
Wenjing
Hedandan
