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MedKoo Cat#: 464672 | Name: Myrislignan
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Myrislignan is a lignan that has been found in M. fragrans and has diverse biological activities. It inhibits hypocotyl or root growth of cress (IC50s = 429 and 517 µM, respectively). Myrislignan (50 µg/ml) inhibits production of nitric oxide (NO), increases in inducible nitric oxide synthase (iNOS) and COX-2 levels, and release of TNF-α and IL-6 in LPS-stimulated RAW 264.7 cells. It inhibits the proliferation of, and induces apoptosis in, A549 lung cancer cells. Myrislignan (3, 5, and 8 mg/kg) reduces tumor growth in an A549 lung cancer mouse xenograft model. It decreases parasite burden in the liver, brain, and spleen in a mouse model of T. gondii infection when administered at a dose of 100 mg/kg.

Chemical Structure

Myrislignan
Myrislignan
CAS#171485-39-5

Theoretical Analysis

MedKoo Cat#: 464672

Name: Myrislignan

CAS#: 171485-39-5

Chemical Formula: C21H26O6

Exact Mass: 374.1729

Molecular Weight: 374.43

Elemental Analysis: C, 67.36; H, 7.00; O, 25.64

Price and Availability

Size Price Availability Quantity
5mg USD 750.00 2 Weeks
10mg USD 1,250.00 2 Weeks
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Related CAS #
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Synonym
Myrislignan;
IUPAC/Chemical Name
4-((1R,2S)-2-(4-allyl-2,6-dimethoxyphenoxy)-1-hydroxypropyl)-2-methoxyphenol
InChi Key
ULZFTGWWPHYLGI-RBZFPXEDSA-N
InChi Code
InChI=1S/C21H26O6/c1-6-7-14-10-18(25-4)21(19(11-14)26-5)27-13(2)20(23)15-8-9-16(22)17(12-15)24-3/h6,8-13,20,22-23H,1,7H2,2-5H3/t13-,20-/m0/s1
SMILES Code
COC1=C(O[C@H]([C@H](O)C(C=C2)=CC(OC)=C2O)C)C(OC)=CC(CC=C)=C1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Myrislignan, a lignan isolated from Myristica fragrans Houtt, possesses anti-inflammatory activities.
In vitro activity:
In the present study, the antiinflammatory effects and the underlying mechanisms of myrislignan in lipopolysaccharide (LPS)-induced inflammation in murine RAW 264.7 macrophage cells were investigated. Myrislignan significantly inhibited LPS-induced production of nitric oxide (NO) in a dose-dependent manner. It inhibited mRNA expression and release of interleukin-6 (IL-6) and tumour necrosis factor-α (TNF-α). Reference: Phytother Res. 2012 Sep;26(9):1320-6. https://pubmed.ncbi.nlm.nih.gov/22294521/
In vivo activity:
The current study tested the anti-T. gondii activity of myrislignan both in vitro and in vivo and explored its potential mechanism of action. In the in vivo murine model, myrislignan treatment significantly reduced the parasite burden in tissues compared to no treatment. Reference: Front Microbiol. 2019 Sep 18;10:2152. https://pubmed.ncbi.nlm.nih.gov/31620108/
Solvent mg/mL mM
Solubility
DMF 15.0 40.06
DMF:PBS (pH 7.2) (1:2) 0.3 0.88
DMSO 5.0 13.35
Ethanol 1.0 2.67
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 374.43 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Zhou Y, Qian W, Li X, Wei W. NF-κB Inhibitor Myrislignan Induces Ferroptosis of Glioblastoma Cells via Regulating Epithelial-Mesenchymal Transformation in a Slug-Dependent Manner. Oxid Med Cell Longev. 2023 Jan 16;2023:7098313. doi: 10.1155/2023/7098313. PMID: 36699318; PMCID: PMC9870699. 2. Jin H, Zhu ZG, Yu PJ, Wang GF, Zhang JY, Li JR, Ai RT, Li ZH, Tian YX, Zhang WX, Wu SG. Myrislignan attenuates lipopolysaccharide-induced inflammation reaction in murine macrophage cells through inhibition of NF-κB signalling pathway activation. Phytother Res. 2012 Sep;26(9):1320-6. doi: 10.1002/ptr.3707. Epub 2012 Feb 1. PMID: 22294521. 3. Zhang J, Si H, Li B, Zhou X, Zhang J. Myrislignan Exhibits Activities Against Toxoplasma gondii RH Strain by Triggering Mitochondrial Dysfunction. Front Microbiol. 2019 Sep 18;10:2152. doi: 10.3389/fmicb.2019.02152. PMID: 31620108; PMCID: PMC6759950. 4. Lu X, Yang L, Chen J, Zhou J, Tang X, Zhu Y, Qiu H, Shen J. The action and mechanism of myrislignan on A549 cells in vitro and in vivo. J Nat Med. 2017 Jan;71(1):76-85. doi: 10.1007/s11418-016-1029-6. Epub 2016 Aug 4. PMID: 27491743.
In vitro protocol:
1. Zhou Y, Qian W, Li X, Wei W. NF-κB Inhibitor Myrislignan Induces Ferroptosis of Glioblastoma Cells via Regulating Epithelial-Mesenchymal Transformation in a Slug-Dependent Manner. Oxid Med Cell Longev. 2023 Jan 16;2023:7098313. doi: 10.1155/2023/7098313. PMID: 36699318; PMCID: PMC9870699. 2. Jin H, Zhu ZG, Yu PJ, Wang GF, Zhang JY, Li JR, Ai RT, Li ZH, Tian YX, Zhang WX, Wu SG. Myrislignan attenuates lipopolysaccharide-induced inflammation reaction in murine macrophage cells through inhibition of NF-κB signalling pathway activation. Phytother Res. 2012 Sep;26(9):1320-6. doi: 10.1002/ptr.3707. Epub 2012 Feb 1. PMID: 22294521.
In vivo protocol:
1. Zhang J, Si H, Li B, Zhou X, Zhang J. Myrislignan Exhibits Activities Against Toxoplasma gondii RH Strain by Triggering Mitochondrial Dysfunction. Front Microbiol. 2019 Sep 18;10:2152. doi: 10.3389/fmicb.2019.02152. PMID: 31620108; PMCID: PMC6759950. 2. Lu X, Yang L, Chen J, Zhou J, Tang X, Zhu Y, Qiu H, Shen J. The action and mechanism of myrislignan on A549 cells in vitro and in vivo. J Nat Med. 2017 Jan;71(1):76-85. doi: 10.1007/s11418-016-1029-6. Epub 2016 Aug 4. PMID: 27491743.
1: Zhang J, Si H, Li B, Zhou X, Zhang J. Myrislignan Exhibits Activities Against Toxoplasma gondii RH Strain by Triggering Mitochondrial Dysfunction. Front Microbiol. 2019 Sep 18;10:2152. doi: 10.3389/fmicb.2019.02152. PMID: 31620108; PMCID: PMC6759950. 2: Yang X, Zan T, Yan H, Liu B. UPLC-MS/MS determination of flavokawain B, a novel anti-tumor chemotherapeutic agent in rat plasma and its application to a pharmacokinetic study in rats. Biomed Chromatogr. 2019 Feb;33(2):e4391. doi: 10.1002/bmc.4391. Epub 2018 Oct 15. PMID: 30238480. 3: Zhao Q, Zhang JL, Li F. Application of Metabolomics in the Study of Natural Products. Nat Prod Bioprospect. 2018 Aug;8(4):321-334. doi: 10.1007/s13659-018-0175-9. Epub 2018 Jun 29. PMID: 29959744; PMCID: PMC6102178. 4: Yang XN, Liu XM, Fang JH, Zhu X, Yang XW, Xiao XR, Huang JF, Gonzalez FJ, Li F. PPARα Mediates the Hepatoprotective Effects of Nutmeg. J Proteome Res. 2018 May 4;17(5):1887-1897. doi: 10.1021/acs.jproteome.7b00901. Epub 2018 Apr 25. PMID: 29664296; PMCID: PMC6628927. 5: Lu X, Yang L, Chen J, Zhou J, Tang X, Zhu Y, Qiu H, Shen J. The action and mechanism of myrislignan on A549 cells in vitro and in vivo. J Nat Med. 2017 Jan;71(1):76-85. doi: 10.1007/s11418-016-1029-6. Epub 2016 Aug 4. PMID: 27491743. 6: Wu N, Xu W, Cao GY, Yang YF, Yang XB, Yang XW. The Blood-Brain Barrier Permeability of Lignans and Malabaricones from the Seeds of Myristica fragrans in the MDCK-pHaMDR Cell Monolayer Model. Molecules. 2016 Jan 22;21(2):134. doi: 10.3390/molecules21020134. PMID: 26805808; PMCID: PMC6274353. 7: Zhu Z, Yang S, Zhao W, Li R, Zhao C. A Comparative Pharmacokinetic Study of Myrislignan by UHPLC-MS After Oral Administration of a Monomer and Myristica fragrans Extract to Rats. J Chromatogr Sci. 2016 May-Jun;54(5):689-96. doi: 10.1093/chromsci/bmv227. Epub 2016 Jan 15. PMID: 26774114; PMCID: PMC4890437. 8: Cao GY, Xu W, Yang XW, Gonzalez FJ, Li F. New neolignans from the seeds of Myristica fragrans that inhibit nitric oxide production. Food Chem. 2015 Apr 15;173:231-7. doi: 10.1016/j.foodchem.2014.09.170. Epub 2014 Oct 13. PMID: 25466017; PMCID: PMC6338084. 9: Jin H, Zhu ZG, Yu PJ, Wang GF, Zhang JY, Li JR, Ai RT, Li ZH, Tian YX, Zhang WX, Wu SG. Myrislignan attenuates lipopolysaccharide-induced inflammation reaction in murine macrophage cells through inhibition of NF-κB signalling pathway activation. Phytother Res. 2012 Sep;26(9):1320-6. doi: 10.1002/ptr.3707. Epub 2012 Feb 1. PMID: 22294521. 10: Li F, Yang X. Quantification of myrislignan in rat plasma by solid-phase extraction and reversed-phase high-performance liquid chromatography. Biomed Chromatogr. 2008 Jun;22(6):601-5. doi: 10.1002/bmc.975. PMID: 18254153. 11: Li F, Yang XW. Biotransformation of myrislignan by rat liver microsomes in vitro. Phytochemistry. 2008 Feb;69(3):765-71. doi: 10.1016/j.phytochem.2007.09.008. Epub 2007 Oct 26. PMID: 17964618.