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Aucubin

Cat No.:V11888 Purity: ≥98%
Aucubin is an iridoid glycoside found in many traditional herbal medicines.
Aucubin
Aucubin Chemical Structure CAS No.: 479-98-1
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
Aucubin is an iridoid glycoside found in many traditional herbal medicines. Aucubin has many bioactivities like antioxidant, anti-aging, anti~inflammatory, antibacterial, anti-fibrotic, anti-cancer, hepatoprotective, neuro-protective (neuro-protection) and osteoprotective effects.
Aucubin (CAS# 479-98-1) is an iridoid glycoside with a wide range of biological activities, including anti-inflammatory, anti-microbial, anti-algesic, anti-tumor, hepatoprotective, neuroprotective, antiaging, antiosteoporosis, and cardioprotective effects. It is a chromogene iridoid glucoside isolated from the genus Veronica L. Aucubin exhibits antioxidant and protective effects in mice.
Biological Activity I Assay Protocols (From Reference)
Targets
Aucubin has multiple targets and mechanisms of action. It targets NF-κB, IL Receptor, and has antibacterial activity. Aucubin alleviates oxidative stress and inflammation via Nrf2-mediated signaling activity. It inhibits the classical complement pathway activation at 4 µM with significantly higher inhibition (89.3%) in the presence of beta glucosidase. Its broad bioactivity profile includes wound healing and immune modulation.
ln Vitro
IgE-induced TNF-α and IL-6 production and expression in RBL-2H3 cells are dose-dependently inhibited by aucubin (0.001-1 μg/mL; actual 30 minutes) with IC50 values of 0.101 and 0.19 μg/mL[2]. Aucubin (0.01 μg/mL; rest for 30 minutes) inhibits IgE-induced nuclear translocation of NF-κB p65 subunit and degrades IκBα in RBL-2H3 cells [2]. Aucubin rises (0.001–1 mM; 12 h). PC12 cell survival and strongly reduced H2O2-induced fluorescence in cells [4].
In vitro, Aucubin demonstrates a wide range of biological activities. It inhibits the classical complement pathway activation at 4 µM with significantly higher inhibition (89.3%) in the presence of beta glucosidase. It has anti-inflammatory, anti-microbial, anti-algesic, and anti-tumor activities. It exhibits antioxidant effects and protects cells from oxidative stress. Aucubin is soluble in DMSO at 68 mg/mL (196.34 mM).
ln Vivo
In streptozotocin-induced diabetes, aucubin (5 mg/kg/d; intraperitoneal injection; 15 d) has protective effects on the pancreas and antioxidant properties [1]. In BLM-stimulated mice, aucubin (40–200 mg/kg; intraperitoneal injection, single dose) and aucubin (5 mg/kg/d; intraperitoneal injection; 21 days) decrease respiratory frequency, increase lung dynamic compliance, comprehend alterations in pulmonary parenchymal fibrosis, and lessen collagen deposition and inflammatory damage in the lungs [6].
In vivo, Aucubin alleviates oxidative stress and inflammation via Nrf2-mediated signaling activity in experimental traumatic brain injury. Administration of Aucubin improved nerve regeneration in the rat model of sciatic nerve injury. It exhibits hepatoprotective, antitoxic, neuroprotective, antiaging, antiosteoporosis, and cardioprotective effects in various animal models. It supports cell regeneration and reduces oxidative stress.
Enzyme Assay
The activity of Aucubin can be assessed using cell-free assays to measure its antioxidant and anti-inflammatory properties. The DPPH radical scavenging assay and ABTS radical cation decolorization assay can be used to evaluate its antioxidant capacity. Its anti-inflammatory activity can be assessed by measuring the inhibition of inflammatory mediators such as NO, TNF-α, and IL-6 in cell-free systems.
Cell Assay
To evaluate the cellular effects of Aucubin, various cell lines are treated with the compound. The inhibition of NF-κB activation and inflammatory cytokine production is measured. Its cytoprotective effects are evaluated by treating cells with Aucubin prior to exposure to oxidative stress and measuring cell viability. Its effects on cell proliferation and migration are assessed in wound healing assays.
Animal Protocol
Animal/Disease Models: Diabetes induced by injection of streptozotocin in male Wistar rats (200-230 g) [1]
Doses: 5 mg/kg
Route of Administration: intraperitoneal (ip) injection, twice (two times) daily for the first 5 days, then at the end Results of daily injections for 10 days: Weight gain in streptozotocin-treated diabetic rats. Lowers blood sugar levels. Reduces lipid peroxidation levels and increases antioxidant enzyme activity. Insulin immunoreactivity and the number of immunoreactive beta cells were increased compared with untreated diabetic rats.
In vivo studies with Aucubin typically involve administration to animal models via oral or intraperitoneal routes. In models of traumatic brain injury, its neuroprotective effects are assessed by measuring oxidative stress markers, inflammatory cytokines, and neurological deficits. In models of sciatic nerve injury, its effects on nerve regeneration are evaluated. Its hepatoprotective and cardioprotective effects are assessed in appropriate disease models.
ADME/Pharmacokinetics
Aucubin has a molecular formula of C₁₅H₂₂O₉ and a molecular weight of 346.33 g/mol. Its CAS number is 479-98-1. It is an analytical standard with a purity of ≥98.0% (HPLC). It should be stored at 2-8°C. It is soluble in DMSO.
Toxicity/Toxicokinetics
Aucubin is classified as Acute Tox. 4 Oral (signal word: Warning). It should be handled with appropriate safety precautions, including the use of personal protective equipment such as eyeshields and gloves. Specific LD₅₀ values and detailed toxicological profiles are not provided in the available literature.
References

[1]. Antioxidant and pancreas-protective effect of aucubin on rats with streptozotocin-induced diabetes. Eur J Pharmacol. 2008 Mar 17;582(1-3):162-7.

[2]. Inhibition of TNF-alpha and IL-6 production by Aucubin through blockade of NF-kappaB activation RBL-2H3 mast cells. Cytokine. 2002 Jun 7;18(5):252-9.

[3]. A review of the pharmacology and toxicology of aucubin. Fitoterapia. 2020 Jan;140:104443.

[4]. Protective effects of aucubin on H₂O₂-induced apoptosis in PC12 cells. Phytother Res. 2012 Mar;26(3):369-74.

[5]. Aucubin: potential antidote for alpha-amanitin poisoning. J Toxicol Clin Toxicol. 1984 Jul;22(1):77-85.

[6]. Aucubin Alleviates Bleomycin-Induced Pulmonary Fibrosis in a Mouse Model. Inflammation. 2017 Dec;40(6):2062-2073.

Additional Infomation
Aucupin is an organic molecular entity that functions as a metabolite. It has been reported to be found in Veronica kellereri, Plantago uniflora, and other organisms with relevant data. See also: Chaste tree fruit (partial); Rehmannia glutinosa root (partial); Plantago ovata seed (partial).
Aucubin is an iridoid glycoside with a wide range of biological activities, including anti-inflammatory, anti-microbial, anti-algesic, anti-tumor, hepatoprotective, neuroprotective, antiaging, antiosteoporosis, and cardioprotective effects. It alleviates oxidative stress and inflammation via Nrf2-mediated signaling activity. Aucubin is used as a research tool to study inflammation, oxidative stress, neuroprotection, and liver protection. It is not a clinically approved drug.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C15H22O9
Molecular Weight
346.3298
Exact Mass
346.126
CAS #
479-98-1
PubChem CID
91458
Appearance
White to light yellow solid powder
Density
1.6±0.1 g/cm3
Boiling Point
669.0±55.0 °C at 760 mmHg
Melting Point
180 - 184ºC
Flash Point
358.4±31.5 °C
Vapour Pressure
0.0±4.6 mmHg at 25°C
Index of Refraction
1.660
LogP
-3.17
Hydrogen Bond Donor Count
6
Hydrogen Bond Acceptor Count
9
Rotatable Bond Count
4
Heavy Atom Count
24
Complexity
507
Defined Atom Stereocenter Count
9
SMILES
C1=CO[C@H]([C@H]2[C@@H]1[C@@H](C=C2CO)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
InChi Key
RJWJHRPNHPHBRN-FKVJWERZSA-N
InChi Code
InChI=1S/C15H22O9/c16-4-6-3-8(18)7-1-2-22-14(10(6)7)24-15-13(21)12(20)11(19)9(5-17)23-15/h1-3,7-21H,4-5H2/t7-,8+,9+,10+,11+,12-,13+,14-,15-/m0/s1
Chemical Name
(2S,3R,4S,5S,6R)-2-[[(1S,4aR,5S,7aS)-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
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 (~288.74 mM)
H2O : ≥ 100 mg/mL (~288.74 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.22 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 (7.22 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 saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

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Solubility in Formulation 3: 2.5 mg/mL (7.22 mM) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication.
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 2.8874 mL 14.4371 mL 28.8742 mL
5 mM 0.5775 mL 2.8874 mL 5.7748 mL
10 mM 0.2887 mL 1.4437 mL 2.8874 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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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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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
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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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.

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