Cimiside E (25-Anhydrocimigenol xyloside) is a triterpene xyloside that has an apoptotic effect on gastric cancer cells with IC50 of 14.58 μM. Cimiside E induces cell cycle arrest and mediates apoptosis through induction of the extrinsic and intrinsic pathways of the caspase cascade.

Physicochemical Properties

Molecular Formula	C35H54O8
Molecular Weight	602.798
Exact Mass	602.381
CAS #	154822-57-8
PubChem CID	102147078
Appearance	Typically exists as solid at room temperature
Density	1.3±0.1 g/cm3
Boiling Point	723.8±60.0 °C at 760 mmHg
Flash Point	391.6±32.9 °C
Vapour Pressure	0.0±5.3 mmHg at 25°C
Index of Refraction	1.602
LogP	6.81
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	3
Heavy Atom Count	43
Complexity	1210
Defined Atom Stereocenter Count	17
SMILES	C=C(C)[C@H]1[C@H]2C[C@@H](C)[C@@H]3[C@@]4(C)CC[C@]56C[C@]76CC[C@@H](C(C)(C)[C@@H]7CC[C@H]5[C@]4(C)[C@H]([C@@]3(O2)O1)O)O[C@H]8[C@@H]([C@H]([C@@H](CO8)O)O)O
InChi Key	CVBALRXHSITZGC-VLHBPTQJSA-N
InChi Code	InChI=1S/C35H54O8/c1-17(2)26-20-14-18(3)27-31(6)12-13-34-16-33(34)11-10-23(41-28-25(38)24(37)19(36)15-40-28)30(4,5)21(33)8-9-22(34)32(31,7)29(39)35(27,42-20)43-26/h18-29,36-39H,1,8-16H2,2-7H3/t18-,19-,20-,21+,22+,23+,24+,25-,26+,27-,28+,29-,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-3,8,8,17,19-pentamethyl-22-prop-1-en-2-yl-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
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	Caspase 3
ln Vitro	In ASG cells, Cimiside E (30-90 μM; 24 h) inhibits the cell cycle and causes apoptosis[1]. Cimiside E (30-90 μM; 12-48 h) possesses anti-proliferative action and significant cytotoxicity against AGS cells [1]. Cimiside E (30-90 μM; 3-24 h) mediates the caspase cascade, raises the Bax/Bcl-2 ratio, decreases mutant p53 and procaspase 3 protein levels, and promotes DNA fragmentation in ASG cells (15-60 μM; 1-6 h) and activates FasL expression at 3 h and Fas at 1 h[1].
Cell Assay	Western Blot Analysis[1] Cell Types: Cimiside E. AGS cells Tested Concentrations: 30 μM, 60 μM, and 90 μM Incubation Duration: 3 h, 6 h, 12 h, and 24 h Experimental Results: Increased the ratio of Bax/Bcl-2 expression from 60 μM. diminished mutant type (mt) p53 levle from 12 h at 30 μM. Suppressed the protein level of procaspase 3 in a dose-dependent manner from 30 μM. Cell Proliferation Assay[1] Cell Types: Cimiside E. AGS cells Tested Concentrations: 30 μM, 60 μM, and 90 μM Incubation Duration: 12 h, 24 h, and 48 h Experimental Results: Inhibited ASG cells proliferation with IC50s of 28.7, 14.6 and 8.1 µM, respectively, for 30 μM, 60 μM, and 90 μM treatment. Cell Cycle Analysis[1] Cell Types: Cimiside E. AGS cells Tested Concentrations: 30 μM, 60 μM, and 90 μM Incubation Duration: 3 h, 6 h, and 24 h Experimental Results: Induced cell cycle arrest at S phase in a low concentration (30 μM), but arrested cell cycle at G2/M phase in higher concentration (60 μM and 90 μM ).
References	[1]. Cimiside E arrests cell cycle and induces cell apoptosis in gastric cancer cells. Arch Pharm Res. 2009 Oct;32(10):1385-92. [2]. One new and six known triterpene xylosides from Cimicifuga racemosa: FT-IR, Raman and NMR studies and DFT calculations. Spectrochim Acta A Mol Biomol Spectrosc. 2012 Jul;93:10-8.
Additional Infomation	Cimiside E has been reported in Actaea asiatica, Actaea cimicifuga, and Actaea heracleifolia with data available.

Solubility Data

Solubility (In Vitro)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *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. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	1.6589 mL	8.2946 mL	16.5893 mL
	5 mM	0.3318 mL	1.6589 mL	3.3179 mL
	10 mM	0.1659 mL	0.8295 mL	1.6589 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.