Product name: Caulilexin C
Synonym name:
Catalogue No.: SBP02781
Cas No.: 30536-48-2
Formula: C₁₁H₁₀N₂O
Mol Weight: 186.214
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

1-Methoxy-3-Indole-Caulilexin C (CAS No.: 30536-48-2) is a natural product derived from cruciferous plants and belongs to the indole class of compounds. As a plant antitoxin, Caulilexin C demonstrates significant antifungal activity and has attracted widespread attention in the field of natural product pharmacology in recent years. Its unique structural features and multi-target mechanism of action make it potentially valuable for treating various disease models including antifungal, anti-tumor, anti-inflammatory, and metabolic diseases. This article will systematically review the chemical structure, origin, pharmacological activity, mechanism of action, druggability, and clinical application prospects of Caulilexin C, aiming to provide a theoretical foundation and reference for in-depth research and drug development of this compound.

Chemical structure and physicochemical properties

1-Methoxy-3-indole-acetonitrile has the chemical formula C11H10N2O and a molecular weight of 186.21, making it a small-molecule natural product. Its core structure is an indole ring system, with three positions linked to acetonitrile groups and one position substituted by methoxy. This structure imparts good lipid solubility (LogP=2.0), moderate polarity (TPSA=50.96 Ų), and three hydrogen bond acceptor sites, facilitating stable binding with biological macromolecules. Its physicochemical properties support good cell membrane permeability and blood-brain barrier penetration (BBB has high permeability), and its in vitro safety is good, with no hepatotoxicity, cardiotoxicity, or hERG channel inhibition. Ames mutagenicity test is negative, demonstrating good safety and drug potential.

Plant Origins and Extraction Methods

Caulilexin C is mainly isolated from cruciferous plants, which have been widely studied due to their abundance of secondary metabolites. This compound was first identified in certain wild and cultivated cruciferous plants, and plant tissues including roots, stems, and leaves can contain this compound. The commonly used extraction method is organic solvent extraction combined with column chromatography separation. The specific steps include:

1. Collect fresh plant materials, dry and crush them.
2. Methanol or ethanol is used for cold leaching or reflux extraction.
3. After concentration, the extract is purified by silica gel column chromatography or high-performance liquid chromatography (HPLC).
4. Structure confirmation is achieved using methods such as mass spectrometry (MS) and nuclear magnetic resonance imaging (NMR).

In recent years, green extraction technologies such as ultrasound-assisted extraction and supercritical fluid extraction have also been applied to extract these compounds, improving extraction efficiency and purity.

Pharmacological activity research

Antifungal activity

As a plant antitoxin, Caulilexin C exhibits significant antifungal activity. In vitro experiments have shown that it inhibits various pathogenic fungi such as Candida albicans, Aspergillus spp., and dermatophytes. Its minimum inhibitory concentration (MIC) is at the micromolar level, demonstrating strong antifungal efficacy. This activity gives it potential application value in the prevention and treatment of fungal infections, especially in the context of increasingly severe drug resistance, where natural products offer new directions for drug development.

Antitumor activity

Caulilexin C exhibits certain cytotoxicity and proliferation-inhibiting effects in prostate and breast cancer cell lines. By regulating various tumor-related signaling pathways, it can induce cancer cell apoptosis and inhibit tumor growth. Especially in prostate cancer models, Caulilexin C regulates key targets such as BCL2, STAT3, and AR, affecting the cell cycle and apoptosis mechanisms. In breast cancer, it acts by regulating signaling molecules such as ESR1, ERBB2, and PIK3CA, demonstrating the potential of multi-target synergistic anti-cancer treatment.

Anti-inflammatory and immunomodulatory

Caulilexin C demonstrated anti-inflammatory activity against inflammatory bowel disease (IBD) models. By inhibiting the nuclear factor κB (NFKB1) signaling pathway, it reduces the expression of tumor necrosis factor α (TNF), interleukin-6 (IL6), and cyclooxygenase-2 (PTGS2), alleviates inflammatory responses, and protects intestinal mucosal integrity. Moreover, its regulatory effect on immune cell function also provides theoretical support for its application in inflammatory diseases.

Metabolic diseases

In diabetes and related metabolic disease models, Caulilexin C improves insulin sensitivity and glucose metabolism by modulating key molecules such as insulin receptor (INSR), glucose transporter 4 (SLC2A4), protein kinase B (AKT1), and AMP-activated protein kinase (PRKAA1), demonstrating potential antidiabetic effects.

Mechanism of action and molecular targets

The multi-target mechanism of Caulilexin C forms the basis of its pharmacological diversity. Molecular docking and cell experiment validation have shown that this compound can bind highly to multiple protein targets, modulating its function:

• Antifungal targets: Mainly acts on synthases that make up fungal cell membranes, such as ergosterol synthase (ERG11), β-glucan synthase (FKS1), mitomycin target protein (CHS1), and protein kinase C (PKC1), destroying fungal cell walls and membrane structures, leading to cell death.
• Tumor-related targets: regulates the BCL2 family protein-mediated apoptotic pathway, inhibits the STAT3 signaling pathway, modulates estrogen receptors (ESR1/ESR2), androgen receptors (AR), and PI3K/AKT pathways, and suppresses tumor cell proliferation and metastasis.
• Inflammatory targets: Inhibiting NFKB1 transcription activity, reducing the expression of inflammatory mediators TNF, IL6, and PTGS2, and alleviating chronic inflammatory states.
• Metabolic target: activates insulin signaling pathways, promotes glucose uptake and metabolism, and improves insulin resistance.

The coordinated regulation of these targets enables Caulilexin C to exhibit broad biological activity across various disease models.

Druggability evaluation and pharmacokinetics

From a druggability perspective, Caulilexin C possesses several excellent properties. Its molecular weight is moderate, the LogP value is suitable for cell membrane penetration, and the TPSA value indicates good oral absorption potential. High blood-brain barrier permeability suggests its potential for treating central nervous system-related diseases. In vitro safety assessments showed no significant hepatotoxicity, cardiotoxicity, or mutagenic risks, reducing clinical development risks.

Pharmacokinetic research is still in its early stages. Current in vivo studies show that this compound is well absorbed orally, has a moderate plasma half-life, is mainly metabolized by the liver, and no significant toxic side effects have been observed. In the future, further systematic pharmacokinetics and toxicology studies are needed to clarify its distribution, metabolic pathways, and excretion mechanisms in vivo, laying a foundation for clinical application.

Prospects and outlooks for clinical applications

Based on its multi-target and multi-mechanism pharmacological activity, Caulilexin C shows broad application prospects in antifungal, anti-tumor, anti-inflammatory, and metabolic disease fields. Especially in the treatment of fungal infections, its unique mechanism of action is expected to overcome the resistance issues of traditional antifungal drugs. In tumor treatment, Caulilexin C can enhance efficacy and reduce side effects as an adjunct or combination drug. The treatment of inflammatory diseases and diabetes also provides new directions.

Future research should focus on the following aspects:

1. In-depth mechanism research: Using multi-omics techniques to analyze its action network and reveal more potential targets.
2. Pharmacokinetics and safety assessment: Systematic in vivo metabolic and long-term toxicology studies.
3. Structural optimization and drug design: Chemical modification based on molecular structure to enhance activity and stability.
4. Preclinical and clinical research: Conducting animal model validation and early clinical trials to evaluate efficacy and safety.

Through multidisciplinary collaboration, Caulilexin C is expected to become an important candidate for novel natural product drugs.

Conclusion

1-Methoxy-3-indole-Caulilexin C, as a natural product with multiple biological activities, demonstrates broad application potential in antifungal, antitumor, anti-inflammatory, and metabolic disease treatments due to its unique chemical structure and multi-target mechanism. Its excellent druggability and safety provide a solid foundation for drug development. In the future, through in-depth mechanistic research and systematic pharmacokinetic evaluation, combined with structural optimization and clinical validation, Caulilexin C is expected to become a star compound in the field of natural product pharmacology, bringing new hope and options for the treatment of related diseases.