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| Targets |
Lobetyolin targets multiple molecular pathways to exert its biological effects. One of its primary actions is the inhibition of xanthine oxidase, an enzyme that catalyzes the oxidation of hypoxanthine to xanthine and xanthine to uric acid, thereby playing a key role in purine metabolism. By inhibiting xanthine oxidase, Lobetyolin may reduce the production of uric acid and the generation of reactive oxygen species (ROS) associated with this reaction. Another important target is the alanine-serine-cysteine transporter 2 (ASCT2), a glutamine transporter that is upregulated in various cancers to support glutamine metabolism. Lobetyolin induces apoptosis by inhibiting ASCT2-mediated glutamine metabolism, thereby depriving cancer cells of a key nutrient for their growth and survival. Additionally, Lobetyolin exhibits anti-inflammatory activity, likely through the modulation of inflammatory signaling pathways and the reduction of pro-inflammatory cytokine production. Its anti-oxidative effects are attributed to its ability to scavenge reactive oxygen species and protect cells from oxidative damage.
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| ln Vitro |
Lobetyolin is produced from Codonopsis pilosula and possesses antioxidant effects. Pretreatment with Lobetyolin, lobetyol, or methyl linoleate reduced phorbol 12-myristate 13-acetate (PMA)-induced MUC5AC gene expression from NCI-H292 cells. Lobetyolin does not influence PMA-induced MUC5AC synthesis in NCI-H292 cells. The amount of mucin in cells from cultures treated with lobetolin was 100±25%, 487±33%, 524±38%, 411±24% and 402±45% (control, 10 ng/mL PMA alone, PMA) plus Lobetyolin 1 μM, PMA plus Lobetyolin 10 μM and PMA plus Lobetyolin 100 μM accordingly [1].
Lobetyolin demonstrates significant in vitro activity across multiple biological assays. It exhibits anti-oxidative effects, as demonstrated by its ability to reduce oxidative stress in various cell models. In NCI-H292 lung epithelial cells, Lobetyolin has been shown to inhibit phorbol 12-myristate 13-acetate (PMA)-induced MUC5AC gene expression, although it does not affect PMA-induced MUC5AC production. The amounts of mucin in Lobetyolin-treated cultures were 100±25%, 487±33%, 524±38%, 411±24%, and 402±45% for control, 10 ng/mL of PMA alone, PMA plus Lobetyolin 1 μM, PMA plus Lobetyolin 10 μM, and PMA plus Lobetyolin 100 μM, respectively. This suggests that Lobetyolin may modulate mucin gene expression through a mechanism distinct from its effect on mucin production. The compound also shows xanthine oxidase inhibitory activity, which may contribute to its anti-inflammatory and anti-oxidative effects. Furthermore, its ability to induce apoptosis by inhibiting ASCT2-mediated glutamine metabolism highlights its potential as an anti-cancer agent. |
| ln Vivo |
In vivo, Lobetyolin has been shown to exert anti-inflammatory and anti-oxidative effects, although detailed in vivo studies are not extensively documented in the available sources. Its inhibition of xanthine oxidase suggests potential benefits in conditions associated with hyperuricemia, such as gout. Its anti-inflammatory properties may be useful in the treatment of inflammatory diseases. The compound's ability to induce apoptosis by targeting glutamine metabolism suggests potential applications in cancer therapy. However, further in vivo studies are needed to fully characterize its pharmacokinetics, efficacy, and safety profile.
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| Enzyme Assay |
In vitro biochemical assays for Lobetyolin are focused on measuring its inhibitory activity against xanthine oxidase and its antioxidant capacity. Xanthine oxidase activity can be measured using a spectrophotometric assay, where the enzyme is incubated with xanthine as a substrate and the production of uric acid is monitored at 295 nm. The compound's IC50 value for xanthine oxidase inhibition can be determined from dose-response curves. Antioxidant activity is commonly assessed using assays such as DPPH radical scavenging, ABTS radical scavenging, or the ferric reducing antioxidant power (FRAP) assay. These assays provide a measure of the compound's ability to neutralize free radicals. Additionally, the compound's ability to inhibit ASCT2-mediated glutamine uptake can be measured using radiolabeled glutamine uptake assays in cells expressing ASCT2.
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| Cell Assay |
In vitro cell-based assays for Lobetyolin are used to evaluate its effects on cell viability, apoptosis, and inflammation. Cancer cell lines are treated with the compound, and cell viability is measured using assays such as MTT or CellTiter-Glo. Apoptosis is assessed by measuring caspase-3/7 activity, Annexin V staining, or by detecting the cleavage of PARP by western blotting. The compound's effects on glutamine metabolism can be studied by measuring glutamine uptake and the levels of downstream metabolites. For anti-inflammatory activity, immune cells (e.g., macrophages) are stimulated with LPS in the presence or absence of the compound, and the production of pro-inflammatory cytokines (e.g., TNF-α, IL-6) is measured by ELISA. These assays provide a comprehensive view of the compound's cellular activities.
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| Animal Protocol |
In vivo animal studies for Lobetyolin are not extensively documented in the available sources. However, based on its in vitro activities, potential studies could include models of inflammation (e.g., carrageenan-induced paw edema), hyperuricemia (e.g., potassium oxonate-induced hyperuricemia), or cancer (e.g., xenograft models). In these studies, Lobetyolin would be administered orally or intraperitoneally, and endpoints such as inflammatory markers, serum uric acid levels, or tumor growth would be measured. Pharmacokinetic parameters, including plasma exposure and tissue distribution, would also be evaluated.
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| ADME/Pharmacokinetics |
The pharmacokinetic (PK) properties of Lobetyolin have been characterized to support its use in preclinical studies. The compound has a molecular weight of 396.43 and is soluble in DMSO and water at 50 mg/mL. For in vivo administration, it can be formulated in various vehicles, including PBS (33.33 mg/mL), 10% DMSO, 40% PEG300, 5% Tween-80, and 45% saline (≥2.5 mg/mL), or 10% DMSO and 90% corn oil (≥2.5 mg/mL). The compound is stable as a powder at -20°C for up to three years or in solution at -80°C for up to six months, protected from light. Detailed PK parameters, such as half-life, clearance, and oral bioavailability, are not specified in the available sources but would be determined in standard preclinical PK studies.
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| Toxicity/Toxicokinetics |
The toxicological profile of Lobetyolin is not extensively documented in publicly available sources. As a natural product derived from a plant used in traditional medicine, it is generally considered to have a favorable safety profile. However, systematic toxicity studies, including acute, subchronic, and genotoxicity testing, would be required for its development as a therapeutic agent. For laboratory handling, standard safety precautions for research chemicals should be observed, including the use of personal protective equipment (gloves, lab coat, safety goggles) and working in a well-ventilated area. The compound is intended for research use only and is not for human therapeutic or diagnostic use.
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| References |
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| Additional Infomation |
See also: Lobetiline (note moved to).
Lobetyolin is a bioactive compound derived from Codonopsis pilosula. It has a molecular formula of C₂₀H₂₈O₈ and a molecular weight of 396.43. The compound is supplied as a white to yellow solid powder with a purity of ≥98%. Its IUPAC name is (2R,3R,4S,5S,6R)-2-(((4E,12E)-1,7-dihydroxytetradeca-4,12-dien-8,10-diyn-6-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol. Lobetyolin contains an alkyne group, making it a click chemistry reagent for CuAAC reactions. It exhibits anti-inflammatory, anti-oxidative, and xanthine oxidase inhibitory activities, and induces apoptosis by inhibiting ASCT2-mediated glutamine metabolism. Lobetyolin is a valuable tool for studying inflammation, oxidative stress, purine metabolism, and cancer biology. |
| Molecular Formula |
C20H28O8
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| Molecular Weight |
396.43152
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| Exact Mass |
396.178
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| CAS # |
129277-38-9
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| PubChem CID |
6369123
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| Appearance |
White to yellow solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
698.5±55.0 °C at 760 mmHg
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| Flash Point |
376.2±31.5 °C
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| Vapour Pressure |
0.0±5.0 mmHg at 25°C
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| Index of Refraction |
1.607
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| LogP |
2.02
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| Hydrogen Bond Donor Count |
6
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
9
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| Heavy Atom Count |
28
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| Complexity |
646
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C/C=C/C#CC#CC(C(/C=C/CCCO)OC1C(C(C(C(O1)CO)O)O)O)O
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| InChi Key |
MMMUDYVKKPDZHS-FWTOVJONSA-N
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| InChi Code |
InChI=1S/C20H28O8/c1-2-3-4-5-7-10-14(23)15(11-8-6-9-12-21)27-20-19(26)18(25)17(24)16(13-22)28-20/h2-3,8,11,14-26H,6,9,12-13H2,1H3/b3-2+,11-8+
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| Chemical Name |
2-[(4E,12E)-1,7-dihydroxytetradeca-4,12-dien-8,10-diyn-6-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
H2O : ~50 mg/mL (~126.13 mM)
DMSO : ~50 mg/mL (~126.13 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.31 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (6.31 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (6.31 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 33.33 mg/mL (84.08 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.5225 mL | 12.6126 mL | 25.2251 mL | |
| 5 mM | 0.5045 mL | 2.5225 mL | 5.0450 mL | |
| 10 mM | 0.2523 mL | 1.2613 mL | 2.5225 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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