Vanicoside B is a phenylpropyl sucrose analogue that can be extracted from Polygonum multiflorum (Persicaria dissitiflora). Vanadyl glycoside B targets cyclin-dependent kinase 8 (CDK8) and displays anti-tumor activity. The potential mechanism is that vanadium glycoside B blocks the CDK8-mediated signaling pathway and inhibits the expression of epithelial-mesenchymal transition proteins, thereby leading to cell cycle arrest and apoptosis (apoptosis).

Physicochemical Properties

Molecular Formula	C49H48O20
Molecular Weight	956.89
Exact Mass	956.273
CAS #	155179-21-8
PubChem CID	10033855
Appearance	White to off-white solid powder
Density	1.5±0.1 g/cm3
Boiling Point	1165.0±65.0 °C at 760 mmHg
Melting Point	157-159 °C
Flash Point	339.6±27.8 °C
Vapour Pressure	0.0±0.3 mmHg at 25°C
Index of Refraction	1.695
LogP	7.3
Hydrogen Bond Donor Count	8
Hydrogen Bond Acceptor Count	20
Rotatable Bond Count	22
Heavy Atom Count	69
Complexity	1780
Defined Atom Stereocenter Count	9
SMILES	COC1=C(C=CC(=C1)/C=C/C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](O2)O[C@]3([C@H]([C@@H]([C@H](O3)COC(=O)/C=C/C4=CC=C(C=C4)O)O)OC(=O)/C=C/C5=CC=C(C=C5)O)COC(=O)/C=C/C6=CC=C(C=C6)O)O)O)O)O
InChi Key	ALSDWGAQQGXOHC-PWYSLETCSA-N
InChi Code	InChI=1S/C49H48O20/c1-62-36-24-31(8-19-35(36)53)12-22-40(55)63-25-37-43(58)45(60)46(61)48(66-37)69-49(27-65-41(56)21-10-29-4-15-33(51)16-5-29)47(67-42(57)23-11-30-6-17-34(52)18-7-30)44(59)38(68-49)26-64-39(54)20-9-28-2-13-32(50)14-3-28/h2-24,37-38,43-48,50-53,58-61H,25-27H2,1H3/b20-9+,21-10+,22-12+,23-11+/t37-,38-,43-,44-,45+,46-,47+,48-,49+/m1/s1
Chemical Name	[(2R,3R,4S,5S)-3-hydroxy-4-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-5-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxyoxolan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
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	CDK3 STAT3
ln Vitro	On triple-negative breast cancer (TNBC) MDA-MB-231 and HCC38 cancer cells, vanadyl glycoside B (2.5–20 μM; 72 h) has anti-proliferative action [1]. Vanadyl glycoside B (2.5–20 μM; 14 d, 72 h, and 14 d) disrupts the cell cycle and lowers TNBC cell viability and colony formation [1]. Inducing TNBC cell apoptosis by controlling the expression of Skp2-p27 family proteins, vanadyl glycoside B (2.5-10 μM; 48 h) decreases the protein levels of p-STAT1, p-STAT3, and p-S6 [1].
ln Vivo	In a mouse model implanted with MDAMB-231 cells, vanadyl glycoside B (5 mg/kg or 20 mg/kg; intraperitoneal injection; three times per week for four weeks) reduces tumor formation [1].
Cell Assay	Western Blot Analysis[1] Cell Types: MDA-MB-231 cells and HCC38 cells Tested Concentrations: 0, 2.5, 5, 10 μM Incubation Duration: 48 hrs (hours) Experimental Results: Increased cleaved PARP, and p27 protein expressions, but diminished Skp2 protein level. Suppressed CDK8 target genes and the expression of EMT-associated proteins. Suppressed the expression of the cell proliferation marker Ki-67 in tumor tissues, also Dramatically suppressed the expressions of p-STAT1 (S727) and AXL. Cell Cycle Analysis[1] Cell Types: MDA-MB-231 cells and HCC38 cells Tested Concentrations: 0, 2.5, 5, 10 μM Incubation Duration: 72 hrs (hours) Experimental Results: Inhibited cell cycle at sub-G1 phase.
Animal Protocol	Animal/Disease Models: MDA-MB-231 cell-implanted xenograft mouse model[1] Doses: 5 mg/kg, 20 mg/kg Route of Administration: intraperitoneal (ip)injection; 3 times per week over 4 weeks Experimental Results: Dramatically diminished tumor volumes at 5 mg/kg and 20 mg/kg by 53.85% and 65.72%, respectively.
References	[1]. Antitumor Activity of Vanicoside B Isolated from Persicaria dissitiflora by Targeting CDK8 in Triple-Negative Breast Cancer Cells. J Nat Prod. 2019 Nov 22;82(11):3140-3149. [2]. Cancer chemopreventive activity of phenylpropanoid esters of sucrose, vanicoside B and lapathoside A, from Polygonum lapathifolium. Cancer Lett. 2001 Nov 28;173(2):133-8.
Additional Infomation	Vanicoside B has been reported in Persicaria bungeana, Persicaria pensylvanica, and Persicaria perfoliata 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	1.0451 mL	5.2253 mL	10.4505 mL
	5 mM	0.2090 mL	1.0451 mL	2.0901 mL
	10 mM	0.1045 mL	0.5225 mL	1.0451 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.