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Amarogentin

Cat No.:V10958 Purity: ≥98%
Amarogentin is a secoiridoid glycoside mainly found in Swertia and Gentiana roots.
Amarogentin
Amarogentin Chemical Structure CAS No.: 21018-84-8
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Amarogentin is a secoiridoid glycoside mainly found in Swertia and Gentiana roots. Amarogentin displays numerous biological effects like antioxidant, antitumor, and antidiabetic activities. Amarogentin has hepatoprotective and Immune-modulatory effects. Amarogentin promotes apoptosis, blocks the G2/M cell cycle and downregulates the PI3K/Akt/mTOR signaling pathway. Amarogentin exerts beneficial vascular metabolic effects by activating AMPK.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
Through transcription factors, amarogentin (0–20 μM, 24 hours) suppresses H2O2-induced oxidative damage in PC12 cells, reducing intracellular oxidative damage [3]. MDA content and ROS levels)[3].
ln Vivo
Amarogentin (100 mg/kg, face) can ameliorate carbon tetrachloride-induced liver fibrosis and lower the expression of α-SMA and TGF-β1 in mice [1].
Animal Protocol
Animal/Disease Models: Carbon tetrachloride-induced liver fibrosis mouse model [1] ]
Doses: 100 mg/kg
Route of Administration: Oral
Experimental Results:diminished expression of hepatic α-SMA and TGF-β1. Inhibits the phosphorylation of JNK, ERK and p38.
References

[1]. Protective Effects of Amarogentin against Carbon Tetrachloride-Induced Liver Fibrosis in Mice. Molecules. 2017 May 6;22(5). pii: E754.

[2]. Amarogentin Displays Immunomodulatory Effects in Human Mast Cells and Keratinocytes. Mediators Inflamm. 2015;2015:630128.

[3]. Amarogentin from Gentiana rigescens Franch Exhibits Antiaging and Neuroprotective Effects through Antioxidative Stress. Oxid Med Cell Longev. 2020 Aug 1;2020:3184019.

Additional Infomation
Amarogentin is a secoiridoid glycoside that consists of (4aS,5R,6R)-5-ethenyl-6-hydroxy-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-1-one having a 2-O-[(3,3',5-trihydroxybiphenyl-2-yl)carbonyl]-beta-D-glucopyranosyl group attached at position 6 via a glycosidic linkage. It has a role as an EC 5.99.1.2 (DNA topoisomerase) inhibitor and a metabolite. It is a secoiridoid glycoside and a monosaccharide derivative.
Amarogentin has been reported in Swertia japonica, Gentianella nitida, and other organisms with data available.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C29H30O13
Molecular Weight
586.5407
Exact Mass
586.168
CAS #
21018-84-8
PubChem CID
115149
Appearance
White to off-white solid powder
Density
1.6±0.1 g/cm3
Boiling Point
928.5±65.0 °C at 760 mmHg
Melting Point
229-230ºC
Flash Point
306.9±27.8 °C
Vapour Pressure
0.0±0.3 mmHg at 25°C
Index of Refraction
1.693
LogP
2.79
Hydrogen Bond Donor Count
6
Hydrogen Bond Acceptor Count
13
Rotatable Bond Count
8
Heavy Atom Count
42
Complexity
1020
Defined Atom Stereocenter Count
8
SMILES
C=C[C@@H]1[C@@H]2CCOC(=O)C2=CO[C@H]1O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)OC(=O)C4=C(C=C(C=C4O)O)C5=CC(=CC=C5)O
InChi Key
DBOVHQOUSDWAPQ-WTONXPSSSA-N
InChi Code
InChI=1S/C29H30O13/c1-2-16-17-6-7-38-26(36)19(17)12-39-28(16)42-29-25(24(35)23(34)21(11-30)40-29)41-27(37)22-18(9-15(32)10-20(22)33)13-4-3-5-14(31)8-13/h2-5,8-10,12,16-17,21,23-25,28-35H,1,6-7,11H2/t16-,17+,21-,23-,24+,25-,28+,29+/m1/s1
Chemical Name
[(2S,3R,4S,5S,6R)-2-[[(3S,4R,4aS)-4-ethenyl-8-oxo-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 2,4-dihydroxy-6-(3-hydroxyphenyl)benzoate
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 (~170.49 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.17 mg/mL (3.70 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 21.7 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: ≥ 2.17 mg/mL (3.70 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 21.7 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: ≥ 2.17 mg/mL (3.70 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 21.7 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 1.7049 mL 8.5246 mL 17.0491 mL
5 mM 0.3410 mL 1.7049 mL 3.4098 mL
10 mM 0.1705 mL 0.8525 mL 1.7049 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.

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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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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
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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
  • Amarogentin inhibits substance P- (SP-) triggered mediator release from the human mast cell line LAD-2. LAD-2 cells were stimulated with increasing concentrations of SP. LAD-2 cells stimulated with 2 μM SP were preincubated with amarogentin (100 μM) or the positive control azelastine (24 μM). A part of the amarogentin stimulated group was preincubated for 30 min with the PLC inhibitor U73122 (10 μM). Histamine (a) and TNF-α (b) release was measured 20 min after SP stimulation. The data are shown with standard deviation (SEM) and were analyzed with the unpaired, two-tailed t-test (∗ p < 0.05; ns: not statistically significant; n = 3).[2]. Amarogentin Displays Immunomodulatory Effects in Human Mast Cells and Keratinocytes. Mediators Inflamm. 2015;2015:630128.
  • Impact of amarogentin on IL-6 secretion in stimulated HaCaT keratinocytes. HaCaT cells were costimulated with 100 μM histamine and 25 ng/mL TNF-α and preincubated with amarogentin (100 μM) or the control azelastine (24 μM) for 30 minutes. After 24 h IL-6 expression was assessed in the cell supernatant. The data are shown with standard deviation (SEM) and were analyzed with the unpaired, two-tailed t-test (∗ p < 0.05; ns: not statistically significant; n = 3).[2]. Amarogentin Displays Immunomodulatory Effects in Human Mast Cells and Keratinocytes. Mediators Inflamm. 2015;2015:630128.
  • Amarogentin does not inhibit IL-8 and MMP-1 secretion in stimulated HaCaT keratinocytes. HaCaT cells were costimulated with 10 μM histamine and 25 ng/mL TNF-α and preincubated with amarogentin (100 μM) or azelastine (24 μM) for 30 minutes. A part of the amarogentin stimulated group was preincubated for 30 min with the PLC inhibitor U73122 (10 μM). After 24 h IL-8 (a) and MMP-1 (b) expression was assessed in the cell supernatant. The data are shown with standard deviation (SEM) and were analyzed with the unpaired, two-tailed t-test (∗ p < 0.05; bs: borderline significant 0.05 < p < 0.06, ns: not statistically significant; n = 3).[2]. Amarogentin Displays Immunomodulatory Effects in Human Mast Cells and Keratinocytes. Mediators Inflamm. 2015;2015:630128.
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