Grossamide

CAS# 80510-06-1

Grossamide

Catalog No. BCN4571----Order now to get a substantial discount!

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Chemical structure

Grossamide

3D structure

Chemical Properties of Grossamide

Cas No. 80510-06-1 SDF Download SDF
PubChem ID 5322012 Appearance Powder
Formula C36H36N2O8 M.Wt 624.69
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 2-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-5-[(E)-3-[2-(4-hydroxyphenyl)ethylamino]-3-oxoprop-1-enyl]-7-methoxy-2,3-dihydro-1-benzofuran-3-carboxamide
SMILES COC1=CC(=CC2=C1OC(C2C(=O)NCCC3=CC=C(C=C3)O)C4=CC(=C(C=C4)O)OC)C=CC(=O)NCCC5=CC=C(C=C5)O
Standard InChIKey DROXVBRNXCRUHP-VGOFMYFVSA-N
Standard InChI InChI=1S/C36H36N2O8/c1-44-30-21-25(8-13-29(30)41)34-33(36(43)38-18-16-23-5-11-27(40)12-6-23)28-19-24(20-31(45-2)35(28)46-34)7-14-32(42)37-17-15-22-3-9-26(39)10-4-22/h3-14,19-21,33-34,39-41H,15-18H2,1-2H3,(H,37,42)(H,38,43)/b14-7+
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Grossamide

The herbs of Cannabis sativa L.

Biological Activity of Grossamide

DescriptionGrossamide possesses potential anti-inflammatory effects, it also has potential anti-neuroinflammatory effects against lipopolysaccharide (LPS)-induced inflammatory response in BV2 microglia cells. Cis-Grossamide K exerts a particularly strong anti-melanogenic activity on the cells without high cell toxicity.
TargetsTLR | NF-kB | TNF-α | p65 | IL Receptor
In vitro

Lignans from the tuber-barks of Colocasia antiquorum var. esculenta and their antimelanogenic Activity.[Pubmed: 20359228]

J Agric Food Chem. 2010 Apr 28;58(8):4779-85.

Colocasia antiquorum var. esculenta , a variant of C. antiquorum , commonly known as "Imperial Taro", is an edible vegetable in many tropical and subtropical regions of the world.
METHODS AND RESULTS:
This study with the aim of evaluating the potential of C. antiquorum var. esculenta as a functional food with a depigmenting effect resulted in the identification of a new sesquilignan, named colocasinol A (1), and a new acyclic phenylpropane lignanamide, named cis-Grossamide K (2), together with 10 known compounds (3-12). The identification and structural elucidation of these compounds were based on 1D and 2D nuclear magnetic resonance (NMR) spectroscopic data analysis as well as high-resolution fast atom bombardment mass spectrometry (FABMS) and electron impact mass spectrometry (EIMS). Quantitation of the melanin contents and cell viability in murine melanocyte melan-a cells was used to assess the antimelanogenic activities of the isolated compounds. Among them, cis-Grossamide K (2), isoamericanol A (3), americanol A (4), 2-hydroxy-3,2'-dimethoxy-4'-(2,3-epoxy-1-hydroxypropyl)-5-(3-hydroxy-1-propenyl)biphenyl (5), and (-)-pinoresinol (6) showed inhibitory effects on melanin production. Compounds 2, 5, and 6 exerted a particularly strong antimelanogenic activity on the cells without high cell toxicity (IC(50) = 54.24, 53.49, and 56.26 microM, and LD(50) = 163.60, 110.23, and >500 microM, respectively).

Protocol of Grossamide

Kinase Assay

Anti-neuroinflammatory effects of grossamide from hemp seed via suppression of TLR-4-mediated NF-κB signaling pathways in lipopolysaccharide-stimulated BV2 microglia cells.[Pubmed: 28224333 ]

Mol Cell Biochem. 2017 Apr;428(1-2):129-137.

Grossamide, a representative lignanamide in hemp seed, has been reported to possess potential anti-inflammatory effects. However, the potential anti-neuroinflammatory effects and underlying mechanisms of action of Grossamide are still unclear. Therefore, the present study investigated the possible effects and underlying mechanisms of Grossamide against lipopolysaccharide (LPS)-induced inflammatory response in BV2 microglia cells.
METHODS AND RESULTS:
BV2 microglia cells were pre-treated with various concentrations of Grossamide before being stimulated with LPS to induce inflammation. The levels of pro-inflammatory cytokines were determined using the enzyme-linked immunoassay (ELISA) and mRNA expression levels were measured by real-time PCR. The translocation of nuclear factor-kappa B (NF-κB) and contribution of TLR4-mediated NF-κB activation on inflammatory effects were evaluated by immunostaining and Western blot analysis. This study demonstrated that Grossamide significantly inhibited the secretion of pro-inflammatory mediators such as interleukin 6 (IL-6) and tumor necrosis factor α (TNF-α), and decreased the level of LPS-mediated IL-6 and TNF-α mRNA. In addition, it significantly reduced the phosphorylation levels of NF-κB subunit p65 in a concentration-dependent manner and suppressed translocation of NF-κB p65 into the nucleus. Furthermore, Grossamide markedly attenuated the LPS-induced expression of Toll-like receptor 4 (TLR4) and myeloid differentiation factor 88 (MyD88).
CONCLUSIONS:
Taken together, these data suggest that Grossamide could be a potential therapeutic candidate for inhibiting neuroinflammation in neurodegenerative diseases.

Grossamide Dilution Calculator

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Grossamide Molarity Calculator

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Preparing Stock Solutions of Grossamide

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.6008 mL 8.004 mL 16.0079 mL 32.0159 mL 40.0198 mL
5 mM 0.3202 mL 1.6008 mL 3.2016 mL 6.4032 mL 8.004 mL
10 mM 0.1601 mL 0.8004 mL 1.6008 mL 3.2016 mL 4.002 mL
50 mM 0.032 mL 0.1601 mL 0.3202 mL 0.6403 mL 0.8004 mL
100 mM 0.016 mL 0.08 mL 0.1601 mL 0.3202 mL 0.4002 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Grossamide

Lignans from the tuber-barks of Colocasia antiquorum var. esculenta and their antimelanogenic Activity.[Pubmed:20359228]

J Agric Food Chem. 2010 Apr 28;58(8):4779-85.

Colocasia antiquorum var. esculenta , a variant of C. antiquorum , commonly known as "Imperial Taro", is an edible vegetable in many tropical and subtropical regions of the world. This study with the aim of evaluating the potential of C. antiquorum var. esculenta as a functional food with a depigmenting effect resulted in the identification of a new sesquilignan, named colocasinol A (1), and a new acyclic phenylpropane lignanamide, named cis-Grossamide K (2), together with 10 known compounds (3-12). The identification and structural elucidation of these compounds were based on 1D and 2D nuclear magnetic resonance (NMR) spectroscopic data analysis as well as high-resolution fast atom bombardment mass spectrometry (FABMS) and electron impact mass spectrometry (EIMS). Quantitation of the melanin contents and cell viability in murine melanocyte melan-a cells was used to assess the antimelanogenic activities of the isolated compounds. Among them, cis-Grossamide K (2), isoamericanol A (3), americanol A (4), 2-hydroxy-3,2'-dimethoxy-4'-(2,3-epoxy-1-hydroxypropyl)-5-(3-hydroxy-1-propenyl)b iphenyl (5), and (-)-pinoresinol (6) showed inhibitory effects on melanin production. Compounds 2, 5, and 6 exerted a particularly strong antimelanogenic activity on the cells without high cell toxicity (IC(50) = 54.24, 53.49, and 56.26 microM, and LD(50) = 163.60, 110.23, and >500 microM, respectively).

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