vanicoside B

Names

[ Name ]:
vanicoside B

[Synonym ]:
[(2R,3R,4S,5R)-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-trihy
1,3,6-Tris-O-[(2E)-3-(4-hydroxyphenyl)-2-propenoyl]-β-D-fructofuranosyl 6-O-[(2E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoyl]-α-D-glucopyranoside
α-D-glucopyranoside, 1,3,6-tris-O-[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propen-1-yl]-β-D-fructofuranosyl 6-O-[(2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl]-
1,3,6-Tris-O-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-β-D-fructofuranosyl 6-O-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-α-D-glucopyranoside

Biological Activity

[Description]:

Vanicoside B is a phenylpropanoyl sucrose derivative, can be isolated from the herb Persicaria dissitiflora. Vanicoside B targets cyclin-dependent kinase 8 (CDK8) and exhibits anti-tumor activity. The potential mechanism is Vanicoside B blocks CDK8-mediated signaling pathways and decreases the expression of epithelial-mesenchymal transition proteins, so that it leads to cell cycle arrest and apoptosis[1][2].

[Related Catalog]:

Signaling Pathways >> Stem Cell/Wnt >> STAT

Research Areas >> Cancer

Signaling Pathways >> JAK/STAT Signaling >> STAT

Signaling Pathways >> Cell Cycle/DNA Damage >> CDK

[Target]

CDK3

STAT3

[In Vitro]

钒苷 B (2.5-20 μM; 72 h) 对三阴性乳腺癌 (TNBC) MDA-MB-231 和 HCC38 癌细胞具有抗增殖活性[1]。钒苷 B (2.5-20 μM; 72 h, 14 d 和 72 h) 抑制 TNBC 细胞的细胞活力、集落形成，干扰细胞周期[1]。钒苷 B (2.5-10 μM; 48 h) 降低了 p-STAT1，p-STAT3 和 p-S6 的蛋白水平，并通过调节 Skp2-p27 系列蛋白表达而诱导 TNBC 细胞凋亡[1]。 Western Blot Analysis[1] Cell Line: MDA-MB-231 cells and HCC38 cells Concentration: 0, 2.5, 5, 10 μM Incubation Time: 48 hours Result: Increased cleaved PARP, and p27 protein expressions, but decreased 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 significantly suppressed the expressions of p-STAT1 (S727) and AXL. Cell Cycle Analysis[1] Cell Line: MDA-MB-231 cells and HCC38 cells Concentration: 0, 2.5, 5, 10 μM Incubation Time: 72 hours Result: Inhibited cell cycle at sub-G1 phase.

[In Vivo]

钒苷 B (5 mg/kg 或 20 mg/kg; 腹腔注射; 每周 3 次, 共 4 周) 抑制 MDAMB-231 细胞移植的小鼠模型中的肿瘤生长[1]。 Animal Model: MDA-MB-231 cell-implanted xenograft mouse model[1] Dosage: 5 mg/kg, 20 mg/kg Administration: Intraperitoneal injection; 3 times per week over 4 weeks Result: Significantly reduced tumor volumes at 5 mg/kg and 20 mg/kg by 53.85% and 65.72%, respectively.

[References]

[1]. Kim D, et al. 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]. Takasaki M, et al. 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.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
1165.0±65.0 °C at 760 mmHg

[ Melting Point ]:
157-159 °C

[ Molecular Formula ]:
C₄₉H₄₈O₂₀

[ Molecular Weight ]:
956.893

[ Flash Point ]:
339.6±27.8 °C

[ Exact Mass ]:
956.273865

[ PSA ]:
303.96000

[ LogP ]:
7.30

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.695

Related Compounds

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.