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| Targets |
Lariciresinol does not have a single defined molecular target but acts through multiple mechanisms. Its antioxidant activity is attributed to its ability to scavenge free radicals and chelate metal ions, thereby reducing oxidative stress. It inhibits α-glucosidase, an enzyme involved in carbohydrate metabolism, suggesting potential for managing blood glucose levels. Its anticancer effects involve the modulation of the NF-κB pathway and reduction of Bcl-2 expression. As a phytoestrogen, it may also interact with estrogen receptors, though this activity is less characterized.
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| ln Vitro |
In vitro, (+)-Lariciresinol demonstrates potent antioxidant activity, effectively scavenging free radicals and inhibiting the generation of reactive oxygen species (ROS) in murine macrophage cells (RAW 264.7) in a dose-dependent manner. It shows significant cytotoxicity against human cancer cells. It inhibits α-glucosidase activity with an IC₅₀ of 6.97 μM. These in vitro activities confirm its potential as an antioxidant, anticancer, and antidiabetic agent.
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| ln Vivo |
Detailed in vivo activity data for (+)-Lariciresinol are not extensively provided in the referenced sources. However, as an orally active compound, it is expected to have in vivo bioavailability. Its antioxidant and anti-inflammatory properties suggest potential for in vivo protective effects in models of oxidative stress and inflammation. Its anticancer effects have been observed in vivo in studies using phenolic compounds isolated from the bark of Picea jezoensis var. jezoensis. Further studies are needed to fully characterize its in vivo efficacy.
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| Enzyme Assay |
Non-cell-based assays for (+)-Lariciresinol typically involve measuring its antioxidant capacity. Common assays include the DPPH radical scavenging assay, the ABTS radical cation decolorization assay, and the ferric reducing antioxidant power (FRAP) assay. Its ability to chelate metal ions can be assessed using a ferrozine-based assay. α-Glucosidase inhibition assays are performed using the enzyme and a chromogenic substrate (e.g., p-nitrophenyl-α-D-glucopyranoside), with the IC₅₀ determined.
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| Cell Assay |
Cellular assays for (+)-Lariciresinol are performed using various cell lines. For antioxidant studies, cells such as RAW 264.7 macrophages are treated with the compound and then stimulated with an oxidative stressor, and ROS levels are measured using fluorescent probes. For anticancer studies, cancer cell lines are treated with the compound, and cell viability, apoptosis, and mitochondrial membrane potential are assessed.
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| Animal Protocol |
In vivo animal models for (+)-Lariciresinol are not extensively detailed in the referenced sources. However, as an anticancer agent, it could be studied in xenograft models in immunodeficient mice. For its anti-inflammatory effects, models such as carrageenan-induced paw edema or LPS-induced sepsis could be used. For its antidiabetic effects, models such as diet-induced obese (DIO) mice or streptozotocin-induced diabetic rats could be used. The compound would be administered orally.
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| ADME/Pharmacokinetics |
(+)-Lariciresinol has a molecular weight of 360.40 g/mol and a molecular formula of C₂₀H₂₄O₆. Its CAS number is 27003-73-2. The compound is a solid. Purity is typically ≥98%. It is soluble in DMSO. Storage conditions: -20°C. The compound is supplied for research use only. Detailed pharmacokinetic parameters such as half-life and bioavailability are not extensively reported.
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| Toxicity/Toxicokinetics |
Detailed toxicological data for (+)-Lariciresinol are not extensively provided in the referenced sources. As a naturally occurring compound found in food sources, it is generally considered safe at dietary levels. The compound is intended for research use only and is not for human consumption. Standard laboratory safety precautions should be followed when handling the compound.
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| References |
Xiao Y, Ji Q, Gao S, Tan H, Chen R, Li Q, Chen J, Yang Y, Zhang L, Wang Z, Chen W, Hu Z. Combined transcriptome and metabolite profiling reveals that IiPLR1 plays an important role in lariciresinol accumulation in Isatis indigotica. J Exp Bot. 2015 Oct;66(20):6259-71. doi: 10.1093/jxb/erv333. Epub 2015 Jul 10. PubMed PMID: 26163698.
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| Additional Infomation |
(+)-Larchirenol is a lignan with the structure tetrahydrofuran, substituted at positions 2, 3, and 4 with 4-hydroxy-3-methoxyphenyl, hydroxymethyl, and 4-hydroxy-3-methoxybenzyl groups, respectively (2S,3R,4R-diastereomers). It possesses antifungal activity and is a plant metabolite. It belongs to the oxacyclopentanes, phenols, lignans, primary alcohols, and aromatic ethers. It is the enantiomer of (-)-lararchirenol. Lararchirenol has been reported to exist in tea (Camellia sinensis), radish (Raphanus sativus var. sativus), and other organisms with relevant data. See also: Acai berry pulp (partial).
(+)-Lariciresinol is a naturally occurring lignan with potent antioxidant properties. It is found in flaxseeds, sesame seeds, and various medicinal plants. The compound inhibits α-glucosidase activity (IC₅₀ = 6.97 μM) and exhibits anti-inflammatory, anticancer, and antimicrobial effects. It is an orally active compound. Its CAS number is 27003-73-2. |
| Molecular Formula |
C20H24O6
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|---|---|
| Molecular Weight |
360.40096
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| Exact Mass |
360.157
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| CAS # |
27003-73-2
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| PubChem CID |
332427
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
568.4±50.0 °C at 760 mmHg
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| Flash Point |
297.6±30.1 °C
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| Vapour Pressure |
0.0±1.6 mmHg at 25°C
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| Index of Refraction |
1.595
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| LogP |
1.64
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
26
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| Complexity |
433
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| Defined Atom Stereocenter Count |
3
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| SMILES |
COC1=C(C=CC(=C1)C[C@H]2CO[C@@H]([C@H]2CO)C3=CC(=C(C=C3)O)OC)O
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| InChi Key |
MHXCIKYXNYCMHY-AUSJPIAWSA-N
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| InChi Code |
InChI=1S/C20H24O6/c1-24-18-8-12(3-5-16(18)22)7-14-11-26-20(15(14)10-21)13-4-6-17(23)19(9-13)25-2/h3-6,8-9,14-15,20-23H,7,10-11H2,1-2H3/t14-,15-,20+/m0/s1
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| Chemical Name |
4-((2S,3R,4R)-4-(4-hydroxy-3-methoxybenzyl)-3-(hydroxymethyl)tetrahydrofuran-2-yl)-2-methoxyphenol
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| Synonyms |
NSC-329247 NSC 329247 NSC329247
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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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.7747 mL | 13.8735 mL | 27.7469 mL | |
| 5 mM | 0.5549 mL | 2.7747 mL | 5.5494 mL | |
| 10 mM | 0.2775 mL | 1.3873 mL | 2.7747 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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