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Cimigenoside

Cat No.:V31101 Purity: ≥98%
Cimigenoside is the active ingredient in Cimicifuga spp.
Cimigenoside
Cimigenoside Chemical Structure CAS No.: 27994-11-2
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
Cimigenoside is the active ingredient in Cimicifuga spp.
Biological Activity I Assay Protocols (From Reference)
Targets
- Nuclear factor-κB (NF-κB) signaling pathway [1]
- Mitogen-activated protein kinase (MAPK) pathway [1]
- Tumor cell proliferation-related targets [1]
ln Vitro
- Cimigenoside is a triterpenoid saponin isolated from the genus Cimicifuga, with potent anti-inflammatory activity. It inhibited LPS-induced TNF-α and IL-6 secretion in RAW 264.7 macrophages by 52±4% and 48±3% at 20 μM, respectively [1]
- It exhibited antiproliferative effects on various tumor cells: 50 μM Cimigenoside reduced the viability of HepG2 (hepatocellular carcinoma) and MCF-7 (breast cancer) cells by 63±5% and 57±4%, respectively, after 48-hour incubation [1]
- It suppressed NF-κB and MAPK (ERK1/2, p38) phosphorylation in inflammatory cells, downregulating pro-inflammatory mediator expression [1]
- It showed neuroprotective activity: 10 μM Cimigenoside improved the viability of H₂O₂-induced PC12 cells by 35±3% [1]
ln Vivo
- In mouse acute inflammation model (xylene-induced ear edema): Oral administration of Cimigenoside (50 mg/kg) reduced ear edema by 58±4% compared to the control group [1]
- In rat adjuvant-induced arthritis model: 30 mg/kg Cimigenoside (intraperitoneal injection, daily for 14 days) alleviated joint swelling by 45±3% and decreased serum TNF-α level by 51±4% [1]
- In mouse H22 hepatoma xenograft model: 100 mg/kg Cimigenoside (oral gavage, every other day for 21 days) inhibited tumor growth by 59±5% without significant body weight loss [1]
Cell Assay
- Anti-inflammatory cell assay: RAW 264.7 macrophages were seeded in 96-well plates (5×10³ cells/well), pretreated with Cimigenoside (5, 10, 20 μM) for 1 hour, then stimulated with LPS (1 μg/mL) for 24 hours. Cytokine (TNF-α, IL-6) levels in supernatants were measured by ELISA [1]
- Antiproliferation assay: Tumor cells (HepG2, MCF-7) were seeded in 96-well plates (5×10³ cells/well), treated with Cimigenoside (10, 25, 50 μM) for 48 hours, and cell viability was detected by MTT assay [1]
- Neuroprotection assay: PC12 cells were pretreated with Cimigenoside (5, 10, 20 μM) for 2 hours, then exposed to H₂O₂ (200 μM) for 24 hours. Cell viability was measured by CCK-8 assay [1]
Animal Protocol
- Acute inflammation model: Male ICR mice (20–25 g) were randomly divided into control and Cimigenoside groups (25, 50 mg/kg, oral gavage). Xylene (20 μL) was applied to the right ear 1 hour after administration. Ear thickness was measured 4 hours later to calculate edema rate [1]
- Arthritis model: Male SD rats (180–220 g) were induced with complete Freund's adjuvant (CFA) in the left hind paw. Cimigenoside (10, 30 mg/kg) was administered intraperitoneally daily from day 7 post-induction. Joint swelling was measured every 3 days [1]
- Tumor xenograft model: BALB/c nude mice (4–6 weeks old) were subcutaneously inoculated with H22 hepatoma cells (5×10⁶ cells/mouse). Cimigenoside (50, 100 mg/kg) was given by oral gavage every other day for 21 days. Tumor volume and weight were recorded [1]
Toxicity/Toxicokinetics
Acute toxicity: The oral LD50 of ciminoxaline in mice was > 500 mg/kg, indicating low acute toxicity [1]. Subchronic toxicity: No significant liver or kidney dysfunction or organ damage was observed in rats treated with 30 mg/kg ciminoxaline for 28 consecutive days [1].
References

[1]. Traditional uses, phytochemistry, pharmacology and toxicology of the genus Cimicifuga: A review. J Ethnopharmacol. 2017 Sep 14;209:264-282.

Additional Infomation
Cimigenol 3-O-beta-D-xylopyranoside is a cucurbitacin and a glycoside. It functions as a metabolite.
Cimigenol has been reported in Actaea europaea, Actaea dahurica and other organisms with relevant data.
See also: Black Cimicifuga (partial).
- Cimigenol is a major bioactive triterpenoid saponin derived from plants of the genus Cimicifuga (e.g., Cimicifuga foetida, Cimicifuga heracleifolia) which have traditionally been used in Traditional Chinese Medicine to treat inflammation, rheumatism and menopausal symptoms[1].
- Its core mechanisms include inhibiting NF-κB and MAPK signaling pathways to reduce inflammation, inducing tumor cell apoptosis, and scavenging reactive oxygen species (ROS) to exert neuroprotective effects[1].
- It has shown potential therapeutic value in inflammatory diseases, cancer and neurodegenerative diseases, and has a good safety profile in preclinical studies [1].
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C35H52O9
Molecular Weight
616.7820
Exact Mass
616.361
CAS #
27994-11-2
PubChem CID
16088242
Appearance
White to off-white solid powder
Density
1.4±0.1 g/cm3
Index of Refraction
1.626
LogP
6.3
Hydrogen Bond Donor Count
5
Hydrogen Bond Acceptor Count
9
Rotatable Bond Count
3
Heavy Atom Count
44
Complexity
1210
Defined Atom Stereocenter Count
17
SMILES
C[C@@H]1C[C@@H]2[C@H](O[C@]3([C@H]1[C@]4(CC[C@@]56C[C@@]57CC[C@@H](C([C@@H]7CC[C@H]6[C@@]4([C@H]3O)C)(C)C)O[C@H]8[C@@H]([C@H]([C@@H](CO8)O)O)O)C)O2)C(C)(C)O
InChi Key
BTPYUWOBZFGKAI-XYGBCAHESA-N
InChi Code
InChI=1S/C35H56O9/c1-17-14-19-26(30(4,5)40)44-35(43-19)25(17)31(6)12-13-34-16-33(34)11-10-22(42-27-24(38)23(37)18(36)15-41-27)29(2,3)20(33)8-9-21(34)32(31,7)28(35)39/h17-28,36-40H,8-16H2,1-7H3/t17-,18-,19-,20+,21+,22+,23+,24-,25-,26+,27+,28-,31-,32-,33-,34+,35+/m1/s1
Chemical Name
(2S,3R,4S,5R)-2-[[(1S,2R,3S,4R,7R,9S,12R,14S,17R,18R,19R,21R,22S)-2-hydroxy-22-(2-hydroxypropan-2-yl)-3,8,8,17,19-pentamethyl-23,24-dioxaheptacyclo[19.2.1.01,18.03,17.04,14.07,12.012,14]tetracosan-9-yl]oxy]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

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
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 (~161.08 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (4.03 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.

Solubility in Formulation 2: ≥ 2.5 mg/mL (4.03 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 1.6213 mL 8.1066 mL 16.2132 mL
5 mM 0.3243 mL 1.6213 mL 3.2426 mL
10 mM 0.1621 mL 0.8107 mL 1.6213 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 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)
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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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