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27-Deoxyactein

Cat No.:V31141 Purity: ≥98%
26-Deoxyactein is the major component of Cimicifuga racemosa and can prevent TCDD-induced osteoblast damage.
27-Deoxyactein
27-Deoxyactein Chemical Structure CAS No.: 264624-38-6
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
26-Deoxyactein is the major component of Cimicifuga racemosa and can prevent TCDD-induced osteoblast damage. 26-Deoxyactein inhibits the elevated levels of AhR, CYP1A1 and ERK.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
Pretreatment with 27-Deoxyactein at concentrations of 1, 5, and 10 μM for 24 hours significantly attenuated 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD)-induced cytotoxicity in MC3T3-E1 osteoblastic cells, as evidenced by increased cell viability compared to TCDD-only treated cells. [1]
27-Deoxyactein dose-dependently reduced TCDD-induced reactive oxygen species (ROS) generation in MC3T3-E1 cells, with the highest concentration (10 μM) showing the most potent ROS scavenging effect. [1]
TCDD-induced upregulation of pro-inflammatory cytokines (TNF-α, IL-6) and cyclooxygenase-2 (COX-2) mRNA expression was significantly inhibited by 27-Deoxyactein pretreatment, as determined by real-time PCR. [1]
27-Deoxyactein reversed TCDD-mediated downregulation of osteogenic markers (alkaline phosphatase, osteocalcin) and upregulation of apoptotic proteins (Bax/Bcl-2 ratio, cleaved caspase-3) in MC3T3-E1 cells, as confirmed by Western blot analysis. [1]
Cell Assay
MC3T3-E1 cells were cultured in appropriate medium supplemented with fetal bovine serum and antibiotics, maintained in a humidified incubator with 5% CO2 at 37°C. [1]
For cytotoxicity assay: Cells were seeded in 96-well plates, allowed to adhere overnight, pretreated with 27-Deoxyactein (1, 5, 10 μM) for 24 hours, then exposed to TCDD (10 nM) for another 24 hours; cell viability was assessed using a colorimetric assay with a specific reagent, and absorbance was measured at a designated wavelength. [1]
For ROS detection: Cells were seeded in 6-well plates, pretreated with 27-Deoxyactein and exposed to TCDD as described, then loaded with a fluorescent probe for 30 minutes at 37°C; fluorescence intensity was detected using a flow cytometer to quantify ROS levels. [1]
For Western blot: Cells were harvested after treatment, lysed in lysis buffer containing protease inhibitors, protein concentrations were determined, equal amounts of protein were separated by SDS-PAGE, transferred to membranes, incubated with primary antibodies against target proteins (Bax, Bcl-2, cleaved caspase-3, osteogenic markers) and secondary antibodies, then visualized using an enhanced chemiluminescence system. [1]
For real-time PCR: Total RNA was extracted from treated cells, reverse-transcribed into cDNA, PCR amplification was performed with specific primers for TNF-α, IL-6, COX-2, and housekeeping gene, and relative mRNA expression levels were calculated using the comparative Ct method. [1]
References

[1]. 27-Deoxyactein prevents 2,3,7,8-tetrachlorodibenzo-p-dioxin-induced cellular damage in MC3T3-E1 osteoblastic cells. J Environ Sci Health A Tox Hazard Subst Environ Eng. 2018 May 12;53(6):561-570.

[2]. Isolation, structure elucidation, and absolute configuration of 26-deoxyactein from Cimicifuga racemosa and clarification of nomenclature associated with 27-deoxyactein. J Nat Prod. 2002;65(4):601-605.

Additional Infomation
26-Deoxy-Acetin is a triterpenoid compound with the function of a metabolite.
26-Deoxy-Acetin has been reported to exist in Actaea elata, Actaea cimicifuga, and Actaea racemosa, with relevant data.
See also: Actaea cimicifuga (partial).
27-Deoxy-Acetin is a triterpenoid glycoside isolated from Actaea cimicifuga. [2]
The absolute configuration of 27-Deoxy-Acetin has been determined, and its structure has been resolved using spectroscopic methods including one-dimensional and two-dimensional nuclear magnetic resonance, mass spectrometry, and chemical derivatization. [2]
Nomenclature confusion associated with 27-Deoxy-Acetin has been resolved, and it has been distinguished from 26-Deoxy-Acetin based on structural differences in its side chains. [2] The protective effect of 27-deoxyacin against TCDD-induced MC3T3-E1 cell damage is related to its antioxidant, anti-inflammatory, anti-apoptotic, and osteoprotective activities. [1]
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C37H56O10
Molecular Weight
660.8346
Exact Mass
660.387
CAS #
264624-38-6
PubChem CID
10974362
Appearance
White to off-white solid powder
Density
1.32±0.1 g/cm3
Melting Point
258-260 °C
LogP
3.71
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
10
Rotatable Bond Count
4
Heavy Atom Count
47
Complexity
1360
Defined Atom Stereocenter Count
18
SMILES
C[C@@H]1C[C@@]2([C@H]3[C@](O3)(CO2)C)O[C@@H]4[C@H]1[C@]5([C@@H](C[C@@]67C[C@@]68CC[C@@H](C([C@@H]8CC[C@H]7[C@@]5(C4)C)(C)C)O[C@H]9[C@@H]([C@H]([C@@H](CO9)O)O)O)OC(=O)C)C
InChi Key
GCMGJWLOGKSUGX-RBKCHLQLSA-N
InChi Code
InChI=1S/C37H56O10/c1-18-12-37(30-33(6,47-30)17-43-37)46-21-13-32(5)23-9-8-22-31(3,4)24(45-29-28(41)27(40)20(39)15-42-29)10-11-35(22)16-36(23,35)14-25(44-19(2)38)34(32,7)26(18)21/h18,20-30,39-41H,8-17H2,1-7H3/t18-,20-,21+,22+,23+,24+,25-,26+,27+,28-,29+,30-,32+,33-,34-,35-,36+,37+/m1/s1
Chemical Name
[(1R,1'R,3'R,4S,4'R,5R,5'R,6'R,10'S,12'S,13'S,16'R,18'S,21'R)-1,4',6',12',17',17'-hexamethyl-18'-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyspiro[3,6-dioxabicyclo[3.1.0]hexane-4,8'-9-oxahexacyclo[11.9.0.01,21.04,12.05,10.016,21]docosane]-3'-yl] acetate
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 (~151.32 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (3.78 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 (3.78 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 (3.78 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 1.5132 mL 7.5662 mL 15.1325 mL
5 mM 0.3026 mL 1.5132 mL 3.0265 mL
10 mM 0.1513 mL 0.7566 mL 1.5132 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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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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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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