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Macelignan

Cat No.:V13275 Purity: ≥98%
Macelignan ((+)-Anwulignan; Anwuligan) is a bioactive lignan extracted from nutmeg.
Macelignan
Macelignan Chemical Structure CAS No.: 107534-93-0
Product category: COX
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Macelignan ((+)-Anwulignan; Anwuligan) is a bioactive lignan extracted from nutmeg. Macelignan displays diverse biological effects like anti~inflammatory, anticancer, antidiabetic, and neuro-protective (neuro-protection) activities.
Macelignan (CAS#: 107534-93-0) is a naturally occurring lignan isolated from Myristica fragrans (nutmeg) and other plants. It is a bioactive compound with a range of pharmacological activities, including anti-inflammatory, antioxidant, neuroprotective, and anticancer properties. It has been studied for its potential in treating neurodegenerative diseases, such as Alzheimer's disease, and for its anti-diabetic and hepatoprotective effects.
Biological Activity I Assay Protocols (From Reference)
Targets
Macelignan has multiple targets due to its diverse biological activities. It is known to inhibit the activity of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), enzymes involved in neurotransmitter breakdown. It also modulates various signaling pathways, including those involved in inflammation (e.g., NF-κB) and oxidative stress (e.g., Nrf2). Furthermore, it exhibits activity against certain cancer-related pathways.
ln Vitro
Macelignan (1-50 μM; 72 h) did not decrease cell viability on its own; rather, UVB therapy decreased HaCaT cell viability in a dose-dependent manner, reducing it by about 80 percent. The control value in percentage of hacat cells is 100 μM [1]. COX-2 expression is lowered by myristolignan (0.1–1 μM; 24 hours) in a concentration-dependent manner. In hacat cells, COX-2 expression is about 50% reduced at the maximum myristolignan concentration (1 μM)[1].
In vitro, Macelignan demonstrates significant anti-inflammatory activity by reducing the production of pro-inflammatory cytokines such as TNF-α, IL-1β, and IL-6 in activated macrophages. It exhibits potent antioxidant effects by scavenging free radicals and upregulating antioxidant enzymes. Macelignan also shows neuroprotective effects by inhibiting Aβ aggregation and protecting neuronal cells from oxidative stress-induced damage. It has shown cytotoxic activity against various cancer cell lines.
ln Vivo
Macelignan (oral; 15 mg/kg; once daily for three weeks) exhibits antidiabetic effects in vivo. There was no difference in baseline (day 0) fasting blood glucose levels between the groups; at the end of the experiment, the values in the Macelignan-treated group of C57BL/KsJ-db/db mice were significantly lower than those in the diabetic control group [2].
In vivo, Macelignan has shown neuroprotective effects in animal models of Alzheimer's disease, improving cognitive function and reducing amyloid plaque burden. It has demonstrated anti-inflammatory effects in models of acute and chronic inflammation. Its hepatoprotective effects have been observed in models of liver injury, and its anti-diabetic potential has been shown in diabetic animal models. However, specific details are not fully detailed in the available literature.
Enzyme Assay
Cell-free assays for Macelignan include enzyme inhibition assays for AChE and BChE. The compound is incubated with the enzyme and a substrate, and the inhibition of enzyme activity is measured spectrophotometrically. Its antioxidant activity can be assessed using DPPH and ABTS radical scavenging assays.
Cell Assay
Cell viability assay [1]
Cell Types: Hacat Cell
Tested Concentrations: 1 μM; 2.5 μM; 5 μM; 10 μM; 15 μM; 50 μM
Incubation Duration: 72 hrs (hours)
Experimental Results: Cell death was induced by UVB irradiation of 10 μM 30 mJ/cm2.

Western Blot Analysis [1]
Cell Types: Hacat Cell
Tested Concentrations: 0.1 μM; 0.5 μM; 1 μM
Incubation Duration: 24 hrs (hours)
Experimental Results: UVB-induced COX-2 expression in cells was diminished.
In vitro cell-based assays for Macelignan are performed using various cell lines. Anti-inflammatory activity is assessed in macrophage cell lines (e.g., RAW 264.7) by measuring cytokine production. Neuroprotective effects are evaluated in neuronal cell lines (e.g., SH-SY5Y) exposed to stressors like Aβ or oxidative agents. Cytotoxicity is tested against cancer cell lines using MTT assays.
Animal Protocol
Animal/Disease Models: Male C57BL/KsJ-db/db mice [2]
Doses: 15 mg/kg
Route of Administration: po (po (oral gavage)) 15 mg/kg; one time/day for three weeks.
Experimental Results: Dramatically diminished blood sugar levels in mice.
In vivo animal experiments for Macelignan are conducted in models of neurodegenerative, inflammatory, and metabolic diseases. For Alzheimer's disease, transgenic mouse models are used to assess cognitive function and amyloid pathology. Inflammatory models include carrageenan-induced paw edema or LPS-induced sepsis models. Diabetes models involve streptozotocin-induced diabetic mice.
ADME/Pharmacokinetics
Pharmacokinetic (PK) data for Macelignan is limited. As a lipophilic natural product, it is likely to have moderate oral bioavailability. It is metabolized in the liver and excreted via the kidneys. However, specific PK parameters are not detailed in the available literature.
Toxicity/Toxicokinetics
Toxicological data for Macelignan is not extensively documented. As a natural product, it is generally considered to have a favorable safety profile, with no significant toxicity reported at therapeutic doses in animal studies. However, comprehensive toxicology studies are lacking.
References

[1]. Effects of macelignan isolated from Myristica fragrans Houtt. on UVB-induced matrix metalloproteinase-9 and cyclooxygenase-2 in HaCaT cells. J Dermatol Sci.

[2]. Effects of a multi-herbal extract on type 2 diabetes. Chin Med. 2011 Mar 4;6:10.

[3]. Macelignan attenuates LPS-induced inflammation and reduces LPS-induced spatial learning impairments in rats. Neurosci Lett. 2008 Dec 19;448(1):110-4.

Additional Infomation
4-[(2S,3R)-4-(1,3-benzodioxane-5-yl)-2,3-dimethylbutyl]-2-methoxyphenol is a lignan. Myristin is a nonsteroidal anti-inflammatory drug with antioxidant, free radical scavenging, and neuroprotective activities. Myristin has been reported to be found in Schisandra chinensis, Magnolia officinalis, and other organisms with relevant data. Myristin is a lignan isolated from nutmeg and exhibits antibacterial and anticariogenic activity against Streptococcus mutans and other Streptococcus species.
Macelignan is a research-grade natural product with diverse pharmacological activities. It has not been approved for clinical use. It is primarily used as a research tool to study its mechanisms of action and potential therapeutic applications in neurodegenerative and inflammatory diseases. All information is for research reference only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C20H24O4
Molecular Weight
328.4022
Exact Mass
328.167
CAS #
107534-93-0
PubChem CID
10404245
Appearance
White to off-white solid powder
Density
1.159
Boiling Point
467.0±40.0 °C at 760 mmHg
Melting Point
70-71℃
Flash Point
236℃
Vapour Pressure
0.0±1.2 mmHg at 25°C
Index of Refraction
1.574
LogP
5.22
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
6
Heavy Atom Count
24
Complexity
388
Defined Atom Stereocenter Count
2
SMILES
C[C@H](CC1=CC2=C(C=C1)OCO2)[C@@H](C)CC3=CC(=C(C=C3)O)OC
InChi Key
QDDILOVMGWUNGD-UONOGXRCSA-N
InChi Code
InChI=1S/C20H24O4/c1-13(8-15-4-6-17(21)19(10-15)22-3)14(2)9-16-5-7-18-20(11-16)24-12-23-18/h4-7,10-11,13-14,21H,8-9,12H2,1-3H3/t13-,14+/m0/s1
Chemical Name
4-[(2S,3R)-4-(1,3-benzodioxol-5-yl)-2,3-dimethylbutyl]-2-methoxyphenol
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

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 (~304.51 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.61 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 (7.61 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 (7.61 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 3.0451 mL 15.2253 mL 30.4507 mL
5 mM 0.6090 mL 3.0451 mL 6.0901 mL
10 mM 0.3045 mL 1.5225 mL 3.0451 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.

Calculator

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An example of molarity calculation using the molarity calculator is shown below:
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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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

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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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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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
  • Extract functions as a PPARγ agonist. (A) Extract increased the ligand-binding activity of PPARγ. HEK293 cells were transfected with pFA-PPARγ and pFR-Luc (UAS-Gal4-luciferase) and then treated with extract (5 μg/ml), rosiglitazone (10 μM), or macelignan (10 μM) for 24 hours. (B) Extract induced transcriptional activity of PPARγ. Differentiated 3T3-L1 adipocytes were transfected with 3 × PPREs-tk-Luc and treated with extract (5 μg/ml), rosiglitazone (10 μM), or macelignan (10 μM) for 24 hours. (C) Extract induced adipogenesis. Oil red O staining was measured after differentiation of 3T3-L1 cells in medium containing 0.1% DMSO (control), extract (5 μg/ml), rosiglitazone (1 μM), or macelignan (10 μM) for seven days. (D) Extract increased PPARγ target gene (aP2) expression in 3T3-L1 adipocytes. Differentiated 3T3-L1 cells were treated with extract (5 μg/ml), rosiglitazone (10 μM), or macelignan (10 μM) for 24 hours. Expression of mRNAs was estimated using quantitative real-time RT-PCR, and the results were expressed as mRNA levels relative to 0.1% DMSO (control). Data represent are shown as mean ± SD of three independent experiments (*P < 0.05, **P < 0.01, ***P < 0.001).[2]. Effects of a multi-herbal extract on type 2 diabetes. Chin Med. 2011 Mar 4;6:10.
  • Extract activates AMPK in C2C12 cells. (A) Extract increased AMPK phosphorylation. C2C12 cells were treated with aminoimidazole-4-carboxamide-1-β-d-ribofuranoside (1 mmol/l), extract (5 μg/ml), or macelignan (10 μM) for 24 hours. Phosphorylated AMPK was examined by Western blot analysis, (B) extract increased the mRNA expression of ACS, CPT-1. The expression was estimated using quantitative real-time RT-PCR. Data represent are shown as mean ± SD of three independent experiments (*P < 0.05, **P < 0.01, ***P < 0.001).[2]. Effects of a multi-herbal extract on type 2 diabetes. Chin Med. 2011 Mar 4;6:10.
  • Extract inhibits NFkB signaling in HepG2 cells. (A) extract prevented the increase of TNF-α-stimulated luciferase activity in TNF-α treated HepG2. HepG2 cells were transfected with NFkB-Luc reporter and then treated with extract (5 μg/ml), rosiglitazone (10 μM), or macelignan (10 μM) for 24 hours in the presence of TNF-α (10 ng/ml) (B) extract increased the IkB level. HepG2 cells were preincubated with extract (5 μg/ml), rosiglitazone (10 μM), or macelignan (10 μM) for 24 hours and then treated with TNF-α (10 ng/ml) for one hour. IκBα was measured by Western blot analysis. Data represent are shown as mean ± SD of three independent experiments (*P < 0.05, **P < 0.01, ***P < 0.001).[2]. Effects of a multi-herbal extract on type 2 diabetes. Chin Med. 2011 Mar 4;6:10.
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