Product name: Lobetyolin
Synonym name: 129277-38-9
Catalogue No.: BP0882
Cas No.: 136085-37-5
Formula: C₂₀H₂₈O₈
Mol Weight: 396.436
Botanical Source: the hairy roots of Lobelia inflata; also from Pratia nummularia
Physical Description: Powder
Type of Compound: Miscellaneous

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, up to kilograms
Inquire for bulk scale.

Descriptions:
Lobetyolin has a protective role in gastric mucosa injury,and the mechanism may be relate to the increase in level of 6-K-PGF1αand the inhibition the excretion of gastric acid and EGF.[1]
Lobetyolin, lobetyol, and methyl linoleate inhibit the gene expression of MUC5AC mucin induced by PMA, however lobetyolin did not affect PMA-induced MUC5AC mucin production. [2]

References:
[1] Song D, Wang Z T, Long-Yun L I. Journal of Emergency in Traditional Chinese Medicine, 2008, 17(7):963-4.
[2] Yoon Y P, Ryu J, Park S H, et al. Tuberculosis & Respiratory Diseases, 2014, 77(5):203-8.
[3] Song D, Cheng X M, Long-Yun L I, et al.China Journal of Chinese Materia Medica, 2008, 33(17):2133-5.

HPLC of Lobetyolin

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

Introduction/Overview

Lobetyolin, CAS number 136085-37-5, is an active natural product isolated from the traditional Chinese medicinal herb Codonopsis pilosula. Codonopsis, as an important tonic herb in traditional Chinese medicine, has long been used to enhance immune function, improve physical constitution, and regulate various diseases. In recent years, with the development of modern pharmacology and natural product chemistry, codonopsis has gradually become a research hotspot due to its unique chemical structure and diverse biological activities. Numerous studies have shown that codonindyne glycosides exhibit significant anti-inflammatory, antioxidant, and xanthine oxidase inhibitory activities, and show potential in inducing apoptosis in tumor cell metabolic regulation, especially by inhibiting the ASCT2-mediated glutamine metabolic pathway. In addition, its regulatory effects on key targets such as TLR4, STAT3, and NFKB1 provide a theoretical basis for its application in immune-related diseases and tumor treatment. This paper systematically reviews the chemical structure, pharmacological activity, mechanism of action, druggability evaluation, and clinical application prospects of codonaxinyne, aiming to provide scientific reference for subsequent drug development and clinical translation.

Chemical structure and physicochemical properties

Codonaxlyne glycoside is a natural glycoside compound with a characteristic alkyl structure, molecular formula C_21H_32O_7, and molecular weight 396.4360. Its chemical structure contains alkyne groups (-C≡C-) and glycoside components, giving it unique physicochemical properties. The LogP of codonindyne is -0.0983, indicating strong hydrophilicity. Combined with its high polar surface area (TPSA 139.84 Ų), it indicates high molecular polarity and good water solubility (15.0053 mg/mL), which is beneficial for absorption and distribution in the body. However, codonosintylyne has relatively low blood-brain barrier permeability, suggesting that its direct role in central nervous system diseases may be limited. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. Ames mutagenic test score was 0.6, indicating low genotoxicity risk and meeting safety requirements.

The structural characteristics of codonsinoside determine its ability to bind to various biomacromolecules, especially its interactions with protein receptors and enzymes, laying the foundation for its multi-target pharmacological activity. Its alkyne group may participate in covalent or non-covalent binding to target proteins, while the glycoside portion enhances its water solubility and bioavailability.

Plant Origins and Extraction Methods

Codonopsis pyloside mainly comes from the root of Codonopsis pilosula, a perennial herbaceous plant of the Bellflower family, widely distributed in northern and southwestern China. Codonopsis root contains various active components, including polysaccharides, saponins, and various glycoside compounds, with codonopsis dynelycoside being the main component.

Traditional methods for extracting codonsinoside mainly use water or alcohol solvents (such as ethanol or methanol) for extraction. Modern extraction processes often combine ultrasound-assisted extraction and microwave-assisted extraction techniques to improve extraction efficiency and purity. The general steps include:

1. Raw material pretreatment: Codonopsis roots are washed, dried, and crushed.
2. Solvent extraction: Use 70%-80% ethanol or pure water, ultrasound-assisted extraction for 1-2 hours.
3. Filtration and concentration: After filtering the extract, reduce pressure and concentrate to an appropriate volume.
4. Separation and purification: further purification of codoninyl glycosides through silica gel column chromatography, reversed-phase high-performance liquid chromatography (RP-HPLC), and other methods.
5. Structural identification: Confirm the compound structure using methods such as mass spectrometry (MS) and nuclear magnetic resonance (NMR).

In recent years, supercritical fluid extraction and membrane separation technologies have also been explored for efficient extraction of codonaxinylenes, balancing environmental friendliness with industrial production needs.

Pharmacological activity research

Research on the pharmacological activity of codonosintylene covers multiple fields including anti-inflammatory, antioxidant, immunomodulatory, and antitumor effects.

Anti-inflammatory effects

Codonaxinylen demonstrates significant anti-inflammatory effects across various inflammatory models. In vitro cell experiments show that codonintylyne can inhibit the expression of pro-inflammatory factors such as TNF-α, IL-6, and IL-1β in macrophages, thereby reducing inflammatory responses. Its mechanism partially works by inhibiting the TLR4/NF-κB signaling pathway, blocking the transmission of inflammatory signals and thereby reducing the release of inflammatory mediators. In vivo experiments, codonoside showed significant inhibitory effects on acute inflammation models such as mouse ear swelling and cotton ball granulomas.

Antioxidant activity

Codonaxintylene has excellent free radical scavenging ability, effectively lowering intracellular ROS levels and protecting cells from oxidative stress damage. Its antioxidant mechanisms include direct scavenging of free radicals and activation of endogenous antioxidant enzyme systems such as superoxide dismutase (SOD) and glutathione peroxidase (GPx). Its antioxidant properties give codonosinyl glycosides potential application value in preventing and treating oxidative stress-related diseases (such as cardiovascular diseases and neurodegenerative diseases).

Xanthine oxidase inhibitory activity

Xanthine oxidase (XO) is a key enzyme in purine metabolism, and its overactivation is associated with hyperuricemia and gout. Codonaxinylyne showed significant inhibitory effects on XO, with inhibitor activity comparable to the standard drug allopurinol, suggesting its potential in treating gout and related metabolic diseases.

Immunomodulatory effects

Codonindyne exerts immunomodulatory effects by modulating various immune-related targets. Research has found that it can regulate the expression of key factors such as TLR4, STAT3, NFKB1, IL-2, IL-10, and FOXP3, promoting immune balance. Specifically, it enhances the body's immune response, suppresses excessive inflammatory responses, and regulates the proportion of immune cell subsets, showing promising prospects especially in autoimmune disease and tumor immunotherapy.

Antitumor activity

Codonintylyne induces tumor cell apoptosis by inhibiting glutamine metabolism mediated by ASCT2 (glutamine transporter). Glutamine metabolism is an important source of energy and biosynthesis for tumor cells. Codonosinyls weaken tumor cells' survival ability by blocking this pathway. Additionally, codonosintylene can inhibit tumor cell proliferation and metastasis by regulating the STAT3 and NF-κB signaling pathways, demonstrating multi-target anti-tumor potential.

Mechanism of action and molecular targets

The mechanisms of action of codonoside are complex and diverse, involving multiple signaling pathways and molecular targets, mainly including:

1. TLR4/NF-κB signaling pathway

As a key receptor for innate immunity, TLR4 activates the NF-κB signaling pathway, inducing pro-inflammatory factor expression. Codoninyl glycosides block downstream NF-κB nuclear translocation by inhibiting TLR4 activation, reducing the production of inflammatory mediators, and exerting anti-inflammatory and immunomodulatory effects.

2. STAT3 signaling pathway

STAT3 is a key transcription factor for various cell proliferation, apoptosis, and immune regulation. Codonaxintylene can inhibit the phosphorylation and activation of STAT3, block the expression of its regulated genes, suppress tumor cell proliferation and promote apoptosis, and simultaneously regulate immune cell function.

3. ASCT2-mediated glutamine metabolism

ASCT2 is the main glutamine transporter, and tumor cells rely on glutamine as an energy and synthesis precursor. Codonintylene inhibits ASCT2 function and reduces glutamine uptake, leading to metabolic disorders in tumor cells and inducing apoptosis.

4. Immunomodulatory-related targets

Codonosinyls regulate various immune-related factors, including IL-2, IL-10, IFN-γ, FOXP3, CTLA4, etc., modulating T cell subset balance, promoting immune tolerance or activation, and adapting to immune needs of different pathological states.

5. Xanthine oxidase inhibition

By directly binding to the XO enzyme active site, codonaxinytylene inhibits its catalytic activity, reduces uric acid production, and alleviates symptoms related to hyperuricemia.

Druggability evaluation and pharmacokinetics

The druggability evaluation of codonodyne shows it has good potential for drug development. The molecular weight is 396.4360, moderate, with a LogP value close to zero, indicating a good balance between water solubility and lipid solubility, which is beneficial for absorption in the body. A higher TPSA value suggests greater polarity, which may limit its oral bioavailability, but its good water solubility is beneficial for formulation development.

Low blood-brain barrier permeability suggests that codonodyne glycosides are limited in central nervous system drug development, but this also reduces the risk of CNS side effects. The hERG channel was inhibited negatively, indicating a low risk of cardiotoxicity. Ames trial results showed that it carries a low genotoxicity risk and is relatively safe.

In terms of pharmacokinetics, current research is relatively limited. Metabolism in the body mainly occurs through hepatic enzyme systems, possibly involving glucoside hydrolysis and redox reactions. The half-life, central distribution, and excretion pathway of codonsinoside still require further study. In the future, its pharmacokinetic and toxicological evaluation should be strengthened to provide a basis for clinical application.

Prospects and outlooks for clinical applications

Codonopsoryxin, with its multi-target and multifunctional pharmacological properties, shows broad prospects for clinical application.

1. Immune regulation and autoimmune diseases: Codonopsis adjunct glycosides regulate immune cell function and balance pro-inflammatory and anti-inflammatory factors, making them suitable for adjunctive therapy of autoimmune diseases such as rheumatoid arthritis and systemic lupus erythematosus.

2. Antitumor therapy: Its ability to inhibit tumor metabolism and regulate the tumor microenvironment makes it a potential candidate for adjuvant therapy, especially in the field of targeted therapy for tumor metabolism.

3. Anti-inflammatory and antioxidant: Codonopshylene glycosides can be used to treat chronic inflammatory diseases such as chronic obstructive pulmonary disease (COPD) and inflammatory bowel disease (IBD), reducing inflammatory damage.

4. Metabolic diseases: By inhibiting xanthine oxidase, codonoside shows potential in treating gout and hyperuricemia.

Future research should focus on optimizing the dosage form, clinical safety evaluation, and multicenter clinical trials of codoninaltylene to verify its efficacy and safety. At the same time, combining modern molecular biology techniques, the mechanism of action is deeply analyzed to promote the conversion of codonostyne glycosides into novel natural medicines.

Conclusion

Codonaxlycylin, as an important active ingredient in Codonopsis, demonstrates broad pharmacological potential thanks to its unique alkyneside structure and diverse biological activities. Its mechanisms of action in anti-inflammation, antioxidant, immunomodulatory, and antitumor effects are becoming increasingly clear, with related targets such as TLR4, STAT3, and ASCT2 laying the foundation for its multi-target pharmacology. Druggability evaluations show that codonodyne has good safety and drug development potential, but its pharmacokinetic characteristics still require further study. In the future, codonopsis glycoside is expected to become an important candidate for natural product drug development, promoting the modernization of traditional Chinese medicine and providing new therapeutic strategies for immune-related diseases and tumor treatment. Systematic pharmacological mechanism research and clinical translational studies will be key to realizing its clinical application.