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Ziyuglycoside I

Cat No.:V30785 Purity: ≥98%
Ziyuglycoside I, extracted from S. officinalis roots, has anti-wrinkle activity and increases the expression of type I collagen.
Ziyuglycoside I
Ziyuglycoside I Chemical Structure CAS No.: 35286-58-9
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
Ziyuglycoside I, extracted from S. officinalis roots, has anti-wrinkle activity and increases the expression of type I collagen. Ziyuglycoside I can be used as an active ingredient in cosmetics. Ziyuglycoside I triggers p53-mediated cell cycle arrest and apoptosis and may be utilized in research related to triple-negative breast cancer.
Ziyuglycoside I (CAS#: 35286-58-9), also known as Gouguside 7, is a naturally occurring pentacyclic triterpenoid saponin isolated from the roots of Sanguisorba officinalis L. (Chinese burnet or Di Yu), a medicinal plant widely used in traditional Chinese medicine for its hemostatic, anti-inflammatory, and wound-healing properties. This compound has a molecular formula of C₄₁H₆₆O₁₃ and a molecular weight of 766.95. Ziyuglycoside I is one of the major bioactive constituents of Sanguisorba officinalis and has garnered significant research interest due to its diverse pharmacological activities. It has been shown to possess anti-inflammatory, antioxidant, anti-wrinkle, and anticancer properties. The compound triggers p53-mediated cell cycle arrest and apoptosis, making it a potential drug candidate for treating triple-negative breast cancer (TNBC). Additionally, it increases the expression of type I collagen, which underlies its anti-wrinkle activity and potential use as an active ingredient in cosmetics. Ziyuglycoside I is frequently utilized in studies exploring antioxidant mechanisms and signal transduction pathways.
Biological Activity I Assay Protocols (From Reference)
Targets
Ziyuglycoside I targets multiple cellular pathways involved in inflammation, oxidative stress, and cancer. Its primary mechanism involves the activation of the tumor suppressor protein p53, which mediates cell cycle arrest and apoptosis. The compound induces G2/M phase arrest and apoptosis in cancer cells through both intrinsic and extrinsic apoptotic pathways. It triggers the cleavage of caspase-8, caspase-9, and caspase-3, upregulates the pro-apoptotic protein Bax, and downregulates the anti-apoptotic protein Bcl-2. Ziyuglycoside I also modulates oxidative stress by interacting with cellular membranes and influencing signal transduction pathways. The compound's anti-inflammatory effects are mediated through the inhibition of NF-κB activation and the reduction of pro-inflammatory cytokine production. Its ability to increase type I collagen expression suggests involvement in extracellular matrix remodeling and skin regeneration pathways.
ln Vitro
In MDA-MB-231 cells, ziyugluside I (5-160 µM; 24 hours) exhibits strong anti-proliferative action, with an IC50 value of 13.96 µM [2]. Ziyugluside I (5–20 µM; 24 hours) increases the proportion of apoptotic cells from 2.43% to 44.76% (20 µM) in MDA-MB-231 cells, hence inducing apoptosis [2]. Induction of caspase-8, caspase-9, and caspase-3 cleavage, upregulation of the pro-apoptotic protein Bax, downregulation of the anti-apoptotic protein Bal-2, and dose-dependent reduction of mitochondrial cell c expression level are all caused by ziyugluside I (5–20 µM; 24-hour exposure)[2].
In vitro studies have demonstrated that Ziyuglycoside I exhibits potent anti-proliferative activity against various cancer cell lines. In MDA-MB-231 triple-negative breast cancer cells, the compound shows strong anti-proliferative action with an IC₅₀ value of 13.96 µM. Treatment with Ziyuglycoside I at concentrations of 5-20 µM for 24 hours increases the proportion of apoptotic cells from 2.43% to 44.76% at 20 µM. The compound induces G2/M phase arrest and apoptosis through the activation of both intrinsic and extrinsic pathways, as evidenced by the cleavage of caspase-8, caspase-9, and caspase-3, upregulation of Bax, and downregulation of Bcl-2. Ziyuglycoside I also exhibits anti-inflammatory activity by modulating oxidative stress and reducing the production of pro-inflammatory mediators. Its antioxidant properties have been demonstrated through its capacity to scavenge free radicals and reduce oxidative stress in various cell systems. Additionally, the compound increases type I collagen expression, which contributes to its anti-wrinkle activity.
ln Vivo
In vivo studies on Ziyuglycoside I have focused on its therapeutic potential in various disease models. As a bioactive constituent of Sanguisorba officinalis, a plant traditionally used for its hemostatic and anti-inflammatory properties, Ziyuglycoside I has been investigated for its effects in models of inflammation, oxidative stress-related disorders, and cancer. The compound's ability to trigger p53-mediated apoptosis suggests potential anti-tumor efficacy in vivo, particularly in triple-negative breast cancer. Its anti-inflammatory and antioxidant activities indicate potential benefits in managing inflammatory conditions and oxidative stress-related diseases. However, detailed pharmacokinetic and pharmacodynamic studies in animal models are still needed to fully characterize the compound's in vivo efficacy and safety profile.
Enzyme Assay
For non-cellular enzyme/receptor binding assays, Ziyuglycoside I can be evaluated for its interactions with various molecular targets using biochemical techniques. The compound's ability to modulate caspase activity can be assessed using fluorometric or colorimetric substrate cleavage assays with purified caspase enzymes. Its effects on p53 activation can be studied using DNA binding assays or fluorescence polarization techniques. The compound's antioxidant activity can be evaluated using cell-free assays such as DPPH, ABTS, or FRAP radical scavenging assays. Its interaction with cellular membranes can be studied using liposome-based assays or surface plasmon resonance (SPR) techniques. The compound's ability to modulate NF-κB activity can be assessed using electrophoretic mobility shift assays (EMSA) or luciferase reporter assays with purified components.
Cell Assay
Cell Viability Assay[1]
Cell Types: MDA-MB-231 Cell
Tested Concentrations: 5 µM, 10 µM, 20 µM, 40 µM, 80 µM and 160 µM
Incubation Duration: 24 hrs (hours)
Experimental Results: MDA-MB-231 shows cytotoxic cells .
Cell cycle analysis[1]
Cell Types: MDA-MB-231 Cell
Tested Concentrations: 5 µM, 10 µM and 20 µM
Incubation Duration: 24 hrs (hours)
Experimental Results: Induction of G2/M phase arrest and apoptosis in MDA-MB-231 cells Western Blot analysis [1]
Cell Types: MDA-MB-231 Cell
Tested Concentrations: 5 µM, 10 µM and 20 µM
Incubation Duration: 24 hrs (hours)
Experimental Results: Induction of apoptosis in MDA-MB-231 cells via intrinsic and extrinsic pathways.
For in vitro cell-based assays, a variety of cell culture models have been established to evaluate the biological activities of Ziyuglycoside I. For anticancer studies, MDA-MB-231 triple-negative breast cancer cells are cultured and treated with Ziyuglycoside I at concentrations ranging from 5 to 160 µM for 24 hours. Cell proliferation is assessed using MTT or CCK-8 assays to determine IC₅₀ values. Apoptosis is evaluated by flow cytometry using Annexin V/PI staining. Cell cycle analysis is performed using propidium iodide staining and flow cytometry. Protein expression of caspases, Bax, Bcl-2, and p53 is analyzed by Western blotting. For anti-inflammatory studies, macrophages or other inflammatory cell models are treated with the compound, and the production of pro-inflammatory cytokines is measured by ELISA. For antioxidant studies, cells are exposed to oxidative stress and the compound's protective effects are assessed.
Animal Protocol
For in vivo animal studies, Ziyuglycoside I can be administered to various disease models. In cancer models, the compound can be evaluated in xenograft models of triple-negative breast cancer, where tumor growth, apoptosis markers, and survival are assessed. In inflammation models, the compound can be tested in models of acute or chronic inflammation, such as carrageenan-induced paw edema or DSS-induced colitis. In oxidative stress-related disorder models, the compound's protective effects can be evaluated. For pharmacokinetic studies, the compound can be administered orally or intraperitoneally to rodents, and plasma and tissue concentrations are measured using HPLC or LC-MS/MS.
ADME/Pharmacokinetics
The pharmacokinetic properties of Ziyuglycoside I include a molecular weight of 766.95 and a molecular formula of C₄₁H₆₆O₁₃. The compound is a white to off-white solid powder with a melting point of 198-202°C. It has a LogP of 6.59, indicating high lipophilicity. The compound is soluble in appropriate organic solvents such as DMSO. For in vivo administration, the compound can be formulated using various solvent systems depending on the route of administration. The powder should be stored at -20°C for long-term stability (up to 3 years) and at 4°C for up to 2 years. The compound's pharmacokinetic profile, including absorption, distribution, metabolism, and excretion, has not been fully characterized and requires further investigation.
Toxicity/Toxicokinetics
The toxicological profile of Ziyuglycoside I has not been fully characterized. As a natural product from Sanguisorba officinalis, a plant used in traditional medicine, the compound is generally considered to have a favorable safety profile at therapeutic doses. No significant toxicity has been reported in preclinical studies. However, comprehensive toxicological evaluations, including acute, subacute, and chronic toxicity studies, are needed to establish the compound's safety for potential therapeutic use. The compound is intended for research use only and is not for human use.
References

[1]. Anti-wrinkle activity of ziyuglycoside I isolated from a Sanguisorba officinalis root extract and its application as a cosmeceutical ingredient. Biosci Biotechnol Biochem. 2008 Feb;72(2):303-11. Epub 2008 Feb 7.

[2]. Ziyuglycoside I Inhibits the Proliferation of MDA-MB-231 Breast Carcinoma Cells through Inducing p53-Mediated G2/M Cell Cycle Arrest and Intrinsic/Extrinsic Apoptosis. Int J Mol Sci. 2016 Nov 22;17(11). pii: E1903.

Additional Infomation
Ziyuglycoside I has been reported to have been found in larch, Paraguayan holly, and other organisms with available data.
Ziyuglycoside I is also known by the synonym Gouguside 7. It is a natural triterpenoid saponin found in the roots of Sanguisorba officinalis and Zygophyllum eichwaldii. The compound's diverse pharmacological activities include anti-inflammatory, antioxidant, anti-wrinkle, and anticancer effects. Its mechanism of action involves the activation of p53-mediated cell cycle arrest and apoptosis through both intrinsic and extrinsic pathways. Ziyuglycoside I increases the expression of type I collagen, which contributes to its anti-wrinkle activity and potential use in cosmetics. The compound shows promise as a potential drug candidate for treating triple-negative breast cancer. It is frequently utilized in studies exploring antioxidant mechanisms and signal transduction pathways. The compound is not currently approved for clinical use and is available only for research purposes.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C41H66O13
Molecular Weight
766.95494
Exact Mass
766.45
CAS #
35286-58-9
PubChem CID
71609288
Appearance
White to off-white solid powder
Density
1.35
Boiling Point
841.9±65.0 °C at 760 mmHg
Melting Point
198-202ºC
Flash Point
247.2±27.8 °C
Vapour Pressure
0.0±0.6 mmHg at 25°C
Index of Refraction
1.610
LogP
6.59
Hydrogen Bond Donor Count
8
Hydrogen Bond Acceptor Count
13
Rotatable Bond Count
6
Heavy Atom Count
54
Complexity
1470
Defined Atom Stereocenter Count
19
SMILES
C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O[C@H]6[C@@H]([C@H]([C@H](CO6)O)O)O)C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
InChi Key
WCHBFWOEFOZHMK-MLHVESHNSA-N
InChi Code
InChI=1S/C41H66O13/c1-20-10-15-41(35(49)54-34-31(48)29(46)28(45)23(18-42)52-34)17-16-38(5)21(32(41)40(20,7)50)8-9-25-37(4)13-12-26(36(2,3)24(37)11-14-39(25,38)6)53-33-30(47)27(44)22(43)19-51-33/h8,20,22-34,42-48,50H,9-19H2,1-7H3/t20-,22+,23-,24+,25-,26+,27+,28-,29+,30-,31-,32-,33+,34+,37+,38-,39-,40-,41+/m1/s1
Chemical Name
[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-1-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-10-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
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)
MEthanol : ~125 mg/mL (~162.98 mM)
DMSO : ~100 mg/mL (~130.38 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (2.71 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 20.8 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: ≥ 2.08 mg/mL (2.71 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 20.8 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: ≥ 2.08 mg/mL (2.71 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 20.8 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 1.3038 mL 6.5192 mL 13.0385 mL
5 mM 0.2608 mL 1.3038 mL 2.6077 mL
10 mM 0.1304 mL 0.6519 mL 1.3038 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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