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Asperulosidic Acid

Cat No.:V11745 Purity: ≥98%
Asperulosidic Acid (ASPA) Asperulosidic acid is a bioactive iridoid glycoside found in the herb Hedyotis diffusa Willd.
Asperulosidic Acid
Asperulosidic Acid Chemical Structure CAS No.: 25368-11-0
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
Asperulosidic Acid (ASPA) Asperulosidic acid is a bioactive iridoid glycoside found in the herb Hedyotis diffusa Willd. Asperulosidic Acid (ASPA) has anti-tumor, antioxidant and anti~inflammatory effects. Asperulosidic Acid (ASPA) exerts anti~inflammatory effects by inhibiting the NF-κB and mitogen-activated protein kinase (MAPK) signaling pathways and inhibiting the release of inflammatory cytokines (TNF-α, IL-6).
Biological Activity I Assay Protocols (From Reference)
ln Vitro
When compared to the group treated with LPS alone, Asperulosidic Acid (ASPA) (40-160 μg/mL; first hour) dramatically down-regulated the mRNA levels of TNF-α and IL-6 in LPS-induced RAW 264.7 cells [1]. Asperulosidic Acid (ASPA) (40-160 μg/mL; first hour) had no effect on p-p38 but decreases Erk1/2 phosphorylation at all concentration levels and IκB-α phosphorylation in a concentration-dependent manner [1].
Cell Assay
RT-PCR[2]
Cell Types: RAW 264.7 Cell
Tested Concentrations: 40 μg/mL, 80 μg/mL and 160 μg/mL
Incubation Duration: 1 hour pretreatment
Experimental Results: TNF-α and IL-6 mRNA expression diminished.

Western Blot Analysis[2]
Cell Types: RAW 264.7 Cell
Tested Concentrations: 40 μg/mL, 80 μg/mL and 160 μg/mL
Incubation Duration: 1 hour pretreatment
Experimental Results: IκB-α phosphorylation and Erk1/2 phosphorylation were diminished.
References

[1]. Anti-renal fibrosis effect of asperulosidic acid via TGF-β1/smad2/smad3 and NF-κB signaling pathways in a rat model of unilateral ureteral obstruction. Phytomedicine. 2019 Feb;53:274-285.

[2]. Asperuloside and Asperulosidic Acid Exert an Anti-Inflammatory Effect via Suppression of the NF-κB and MAPK Signaling Pathways in LPS-Induced RAW 264.7 Macrophages. Int J Mol Sci. 2018 Jul 12;19(7). pii: E2027.

Additional Infomation
Asperulosidic acid is a glycoside and an iridoid monoterpenoid.
Asperulosidic acid has been reported in Oldenlandia herbacea var. herbacea, Galium rivale, and other organisms with data available.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C18H24O12
Molecular Weight
432.3760
Exact Mass
432.127
CAS #
25368-11-0
PubChem CID
11968867
Appearance
White to off-white solid powder
Density
1.64±0.1 g/cm3
LogP
-3.2
Hydrogen Bond Donor Count
6
Hydrogen Bond Acceptor Count
12
Rotatable Bond Count
7
Heavy Atom Count
30
Complexity
733
Defined Atom Stereocenter Count
9
SMILES
CC(=O)OCC1=C[C@@H]([C@H]2[C@@H]1[C@@H](OC=C2C(=O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
InChi Key
DGDWCRWJRNMRKX-DILZHRMZSA-N
InChi Code
InChI=1S/C18H24O12/c1-6(20)27-4-7-2-9(21)12-8(16(25)26)5-28-17(11(7)12)30-18-15(24)14(23)13(22)10(3-19)29-18/h2,5,9-15,17-19,21-24H,3-4H2,1H3,(H,25,26)/t9-,10+,11+,12-,13+,14-,15+,17-,18-/m0/s1
Chemical Name
(1S,4aS,5S,7aS)-7-(acetyloxymethyl)-5-hydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid
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 (~231.28 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.78 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 (5.78 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 (5.78 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 2.3128 mL 11.5639 mL 23.1278 mL
5 mM 0.4626 mL 2.3128 mL 4.6256 mL
10 mM 0.2313 mL 1.1564 mL 2.3128 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.

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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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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
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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
  • Chemical structures of the five iridoids. (A) Asperuloside (ASP); (B) Asperulosidic acid (ASPA); (C) Desacetyl asperulosidic acid (DAA); (D) Scandoside methyl ester (SME); and (E) E-6-O-p-Coumaroyl scandoside methyl ester (CSME).[2]. Asperuloside and Asperulosidic Acid Exert an Anti-Inflammatory Effect via Suppression of the NF-κB and MAPK Signaling Pathways in LPS-Induced RAW 264.7 Macrophages. Int J Mol Sci. 2018 Jul 12;19(7). pii: E2027.
  • Effects of five iridoids on the viability of RAW 264.7 cells. RAW 264.7 cells were treated with asperuloside (ASP), asperulosidic acid (ASPA), desacetyl asperulosidic acid (DAA), scandoside methyl ester (SME) and E-6-O-p-coumaroyl scandoside methyl ester (CSME) at the concentration of 0, 50, 100, and 200 μg/mL, respectively, for 1 h, and then induced with 50 ng/mL lipopolysaccharide (LPS) for 24 h. Cell viability was measured by the Cell Counting Kit-8 (CCK-8) assay (n = 3).[2]. Asperuloside and Asperulosidic Acid Exert an Anti-Inflammatory Effect via Suppression of the NF-κB and MAPK Signaling Pathways in LPS-Induced RAW 264.7 Macrophages. Int J Mol Sci. 2018 Jul 12;19(7). pii: E2027.
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