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Deacetylasperulosidic Acid

Alias: Deacetylasperulosidic Acid; DAA
Cat No.:V19339 Purity: ≥98%
Deacetylasperulosidic acid (DAA) is the main phytochemical component of Morinda citrifolia fruits.
Deacetylasperulosidic Acid
Deacetylasperulosidic Acid Chemical Structure CAS No.: 14259-55-3
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
Deacetylasperulosidic acid (DAA) is the main phytochemical component of Morinda citrifolia fruits. Deacetylasperulosidic acid has anti-oxidant effect by increasing superoxide dismutase activity. Deacetylasperulosidic acid has antigenic activity and inhibits the induction of chromosomal aberrations in hamster ovary cells and mice. Deacetylasperulosidic acid prevents 4-nitroquinoline 1-oxide (4NQO)-induced DNA damage in vitro, inhibits IL-2 production and natural killer cell activation.
Deacetylasperulosidic acid is a monoterpene glycoside originally isolated from D. macropodum and other plants. It has the molecular formula C16H22O11 and molecular weight of 390.34. Deacetylasperulosidic acid has antioxidant, anti-inflammatory, hepatoprotective, and anticancer properties. It decreases serum malondialdehyde levels and increases superoxide dismutase activity. The compound also has antigenic activity and inhibits the induction of chromosomal aberrations in hamster ovary cells and mice.
Biological Activity I Assay Protocols (From Reference)
Targets
Deacetylasperulosidic acid does not have a single defined pharmacological target but exhibits multiple biological activities. It has antioxidant activity by increasing superoxide dismutase activity. The compound may act as a vitamin D receptor agonist. Its diverse biological effects suggest interactions with multiple cellular pathways involved in oxidative stress, inflammation, and cell proliferation.
ln Vitro
Deacetylasperulosidic acid scavenges free radicals, suppresses pro-inflammatory mediators, and protects tissues from oxidative damage. It has antioxidant activity by increasing superoxide dismutase activity. The compound has antigenic activity and inhibits the induction of chromosomal aberrations in hamster ovary cells. In vitro studies demonstrate its potential for antioxidant and anti-inflammatory applications.
ln Vivo
Deacetylasperulosidic acid decreases serum malondialdehyde levels and increases superoxide dismutase activity in rats at 50 mg/kg per day for seven days. It has hepatoprotective effects and inhibits chromosomal aberrations in mice. In vivo studies support its potential as an antioxidant and hepatoprotective agent. The compound can be used to prepare vitamin D receptor agonists and compositions for preventing atherosclerosis.
Enzyme Assay
In vitro enzyme assays for Deacetylasperulosidic acid may involve measuring superoxide dismutase (SOD) activity or assessing lipid peroxidation by measuring malondialdehyde (MDA) levels. The compound's antioxidant activity can be evaluated using DPPH, ABTS, or other free radical scavenging assays. Binding assays for vitamin D receptor could also be performed.
Cell Assay
Cellular assays for Deacetylasperulosidic acid are performed using various cell lines to assess its biological activities. Antioxidant activity is evaluated by measuring intracellular ROS levels using fluorescent probes. Anti-inflammatory activity is assessed by measuring pro-inflammatory cytokine production (e.g., TNF-α, IL-6) in stimulated cells. Anticancer activity is evaluated by assessing cell proliferation, apoptosis, and cell cycle progression in cancer cell lines. Chromosomal aberration assays are performed in hamster ovary cells.
Animal Protocol
In vivo animal studies for Deacetylasperulosidic acid are performed in rats. Animals are administered Deacetylasperulosidic acid at 50 mg/kg per day for seven days. Serum malondialdehyde levels and superoxide dismutase activity are measured to assess antioxidant effects. Hepatoprotective effects are evaluated in models of liver injury. Chromosomal aberration studies are performed in mice. The compound can be used to study prevention of atherosclerosis.
ADME/Pharmacokinetics
Deacetylasperulosidic acid has a molecular weight of 390.34 and molecular formula C16H22O11. It is soluble in DMF (5 mg/ml), DMSO (10 mg/ml), and PBS pH 7.2 (5 mg/ml). The compound has a UV absorbance maximum at 235 nm. It should be stored at -20°C and shipped at room temperature. Purity is typically ≥98%.
Toxicity/Toxicokinetics
Deacetylasperulosidic acid is generally considered to have low toxicity based on its use in animal studies at 50 mg/kg per day. The compound has antioxidant and hepatoprotective properties that may provide protection against oxidative damage. Standard laboratory safety precautions should be followed when handling the compound. No specific acute toxicity data have been reported in the literature.
References

[1]. In vivo antioxidant activity of deacetylasperulosidic Acid in noni. J Anal Methods Chem. 2013;2013:804504.

[2]. Activation of cell-mediated immunity by Morinda citrifolia fruit extract and its constituents. Nat Prod Commun. 2014 Apr;9(4):445-50.

Additional Infomation
According to reports, gardenias, madder, and other organisms with available data contain deacetylated lasperosides.
Deacetylasperulosidic acid is a monoterpene glycoside originally isolated from D. macropodum. It has antioxidant, anti-inflammatory, hepatoprotective, and anticancer properties. The compound is known to scavenge free radicals, suppress pro-inflammatory mediators, and protect tissues from oxidative damage. Deacetylasperulosidic acid is an active ingredient of Hedyotis diffusa and can be used to prepare vitamin D receptor agonists and compositions for preventing atherosclerosis. The compound is for research use only and has not been approved for clinical use. It is also known as 10-Deacetylasperulosidic Acid.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C16H22O11
Molecular Weight
390.34
Exact Mass
390.116
CAS #
14259-55-3
PubChem CID
12315350
Appearance
White to off-white solid powder
Density
1.7±0.1 g/cm3
Boiling Point
744.1±60.0 °C at 760 mmHg
Flash Point
271.7±26.4 °C
Vapour Pressure
0.0±5.6 mmHg at 25°C
Index of Refraction
1.683
LogP
-2.48
Hydrogen Bond Donor Count
7
Hydrogen Bond Acceptor Count
11
Rotatable Bond Count
5
Heavy Atom Count
27
Complexity
632
Defined Atom Stereocenter Count
9
SMILES
C1=C([C@@H]2[C@H]([C@H]1O)C(=CO[C@H]2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C(=O)O)CO
InChi Key
ZVXWFPTVHBWJOU-YYFGDFGFSA-N
InChi Code
InChI=1S/C16H22O11/c17-2-5-1-7(19)10-6(14(23)24)4-25-15(9(5)10)27-16-13(22)12(21)11(20)8(3-18)26-16/h1,4,7-13,15-22H,2-3H2,(H,23,24)/t7-,8+,9+,10-,11+,12-,13+,15-,16-/m0/s1
Chemical Name
(1S,4aS,5S,7aS)-5-hydroxy-7-(hydroxymethyl)-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
Synonyms
Deacetylasperulosidic Acid; DAA
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

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
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 (~256.19 mM)
H2O : ~50 mg/mL (~128.09 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.40 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 (6.40 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 (6.40 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 2.5619 mL 12.8093 mL 25.6187 mL
5 mM 0.5124 mL 2.5619 mL 5.1237 mL
10 mM 0.2562 mL 1.2809 mL 2.5619 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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Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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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.

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