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Sesamolin (AI3-20978; AI3 20978)

Alias: Sesamolin; AI3 20978; AI320978; AI3-20978
Cat No.:V14676 Purity: ≥98%
Sesamolin (AI320978) is a naturally occuring compound isolated from Justicia orbiculata with antioxidative activity.
Sesamolin (AI3-20978; AI3 20978)
Sesamolin (AI3-20978; AI3 20978) Chemical Structure CAS No.: 526-07-8
Product category: p38 MAPK
This product is for research use only, not for human use. We do not sell to patients.
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25mg
50mg
100mg
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Product Description
Sesamolin (AI320978) is a naturally occurring substance with antioxidant activity that was isolated from Justicia orbiculata. Human lymphocytic leukemia cells' ability to proliferate in culture is inhibited by sesaminol, which also inhibits lipid peroxidation and exhibits neuroprotective properties. By preventing the phosphorylation of JNK, p38 MAPKs, and caspase-3 but not ERK-MAPK expression, sesaminol effectively inhibits MAPK cascades.
Sesamolin (AI3-20978) is a natural lignan isolated from Sesamum indicum (sesame) and Justicia orbiculata. It possesses potent antioxidative, anti-inflammatory, and neuroprotective properties.
Biological Activity I Assay Protocols (From Reference)
Targets
Sesamolin targets the MAPK signaling cascade by preventing the phosphorylation of JNK, p38 MAPKs, and caspase-3, but not ERK-MAPK.
ln Vitro
In vitro, Sesamolin inhibits lipid peroxidation in rat liver and kidney, demonstrating strong antioxidative activity. It protects microglia and PC12 cells against H2O2-induced cell injury by suppressing ROS generation and inhibiting p38 MAPK and caspase-3 activation. It functions as a potent free radical scavenger.
ln Vivo
In vivo, Sesamolin exhibits neuroprotective effects, as demonstrated in animal models of oxidative stress and neurodegeneration. Its lipid-lowering effects make it relevant for cardiovascular research. It has also been shown to enhance the stability of oils, preventing rancidity.
Enzyme Assay
In vitro enzyme assays for Sesamolin typically involve measuring its antioxidant capacity using cell-free systems such as the DPPH (2,2-diphenyl-1-picrylhydrazyl) or ABTS (2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)) radical scavenging assays. The compound is incubated with the radical solution, and the decrease in absorbance is measured spectrophotometrically. Lipid peroxidation inhibition is assessed in rat liver or kidney microsomes using the thiobarbituric acid reactive substances (TBARS) assay.
Cell Assay
In vitro cell-based assays for Sesamolin are conducted using neuronal cell lines such as PC12 or microglial cells. Cells are pre-treated with the compound and then exposed to an oxidative stressor like H2O2. Cell viability is measured using MTT or CCK-8 assays. Markers of apoptosis, such as caspase-3 activation and ROS production, are quantified using fluorescent probes or ELISA to evaluate the compound's neuroprotective and antioxidant effects.
Animal Protocol
In vivo animal studies for Sesamolin often employ rodent models of neurodegeneration or oxidative stress. For example, rats may be subjected to cerebral ischemia-reperfusion injury, and the compound is administered orally or intraperitoneally. Neuroprotection is assessed by measuring infarct volume, neurological deficit scores, and biochemical markers of oxidative stress in brain tissue.
ADME/Pharmacokinetics
Pharmacokinetic data for Sesamolin from natural product sources suggest it is absorbed and can reach systemic circulation. As a lipophilic compound, it is expected to have good tissue distribution, including penetration into the brain, which supports its neuroprotective effects. Detailed PK parameters (e.g., half-life, Cmax, bioavailability) are limited in publicly available sources.
Toxicity/Toxicokinetics
Sesamolin is considered to have a low toxicity profile, consistent with its origin as a dietary component from sesame. It has been used in traditional medicine and is generally recognized as safe. No significant acute or chronic toxicity has been reported in the available literature, though comprehensive toxicological studies are limited.
References

[1]. Sesamin, sesamolin and the origin of sesame. Biochemical Systematics and Ecology. Volume 13, Issue 2, 23 May 1985, Pages 133-139.

[2]. Sesamolin Inhibits Lipid Peroxidation in Rat Liver and Kidney. The Journal of Nutrition, Volume 128, Issue 6, June 1998, Pages 1018–1022.

[3]. Protective effects of sesamin and sesamolin on hypoxic neuronal and PC12 cells.

[4]. Comparative analysis of sesame lignans (sesamin and sesamolin) in affecting hepatic fatty acid metabolism in rats. Br J Nutr. 2007 Jan;97(1):85-95.

Additional Infomation
Sesamolin belongs to the benzodiazepine class of compounds. It has been reported to be found in flax leaf iberian grass, coleus, and other organisms with relevant data. See also: Sesame oil (partial).
Sesamolin is a natural product belonging to the lignan class. It is studied for its potential in preventing and treating diseases associated with oxidative stress and inflammation, including cardiovascular and neurodegenerative disorders. Its antioxidant activity is linked to its ability to form stable free radical intermediates. It is not an approved drug but is widely used as a research tool.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C20H18O7
Molecular Weight
370.3527
Exact Mass
370.105
Elemental Analysis
C, 64.86; H, 4.90; O, 30.24
CAS #
526-07-8
Related CAS #
526-07-8
PubChem CID
101746
Appearance
White to off-white solid powder
Density
1.4±0.1 g/cm3
Boiling Point
520.8±50.0 °C at 760 mmHg
Melting Point
93 - 94ºC (Decomposes)
Flash Point
219.2±30.0 °C
Vapour Pressure
0.0±1.3 mmHg at 25°C
Index of Refraction
1.622
LogP
2.88
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
7
Rotatable Bond Count
3
Heavy Atom Count
27
Complexity
544
Defined Atom Stereocenter Count
4
SMILES
O1C([H])([H])[C@]2([H])[C@@]([H])(OC3C([H])=C([H])C4=C(C=3[H])OC([H])([H])O4)OC([H])([H])[C@]2([H])[C@@]1([H])C1C([H])=C([H])C2=C(C=1[H])OC([H])([H])O2
InChi Key
ZZMNWJVJUKMZJY-AFHBHXEDSA-N
InChi Code
InChI=1S/C20H18O7/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)27-12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2/t13-,14-,19+,20+/m0/s1
Chemical Name
5-[[(3S,3aR,6R,6aR)-3-(1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]oxy]-1,3-benzodioxole
Synonyms
Sesamolin; AI3 20978; AI320978; AI3-20978
HS Tariff Code
2934.99.03.00
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)
Solubility Data
Solubility (In Vitro)
DMSO: ~100 mg/mL (~270.0 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 2.5 mg/mL (6.75 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
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 (6.75 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.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (6.75 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.7001 mL 13.5007 mL 27.0015 mL
5 mM 0.5400 mL 2.7001 mL 5.4003 mL
10 mM 0.2700 mL 1.3501 mL 2.7001 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.

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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.

Biological Data
  • Transformation of sesamolin to sesaminol during industrial processing.
  • Representative chromatograms of HPLC separation of fecal extracts of a rat fed a diet containing 1% sesamolin (A) and a rat fed a control diet (B). Details are given in Materials and Methods.
  • Concentration of sesamolin and its metabolites in plasma, kidneys and liver of rats fed 1% sesamolin diet.
  • Antioxidative activity in liver (A), kidneys (B) and plasma (C) of rats fed control and 1% sesamolin diet. Each value is the mean ± SD (n = 5).
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