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Esculentoside H

$202

  • Brand : BIOFRON

  • Catalogue Number : BD-P0844

  • Specification : 98.0%(HPLC&TLC)

  • CAS number : 66656-92-6

  • Formula : C48H76O21

  • Molecular Weight : 989.1

  • PUBCHEM ID : 101920412

  • Volume : 20mg

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Catalogue Number

BD-P0844

Analysis Method

HPLC,NMR,MS

Specification

98.0%(HPLC&TLC)

Storage

2-8°C

Molecular Weight

989.1

Appearance

Powder

Botanical Source

Structure Type

Triterpenoids

Category

SMILES

CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CC(C(C5(C)CO)OC6C(C(C(CO6)OC7C(C(C(C(O7)CO)O)O)O)O)O)O)C)C)C2C1)C)C(=O)OC8C(C(C(C(O8)CO)O)O)O)C(=O)OC

Synonyms

2-O-methyl 4a-O-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2R,4aR,6aR,6aS,6bR,9R,10R,11S,12aR,14bR)-10-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-11-hydroxy-9-(hydroxymethyl)-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-2,4a-dicarboxylate

IUPAC Name

2-O-methyl 4a-O-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2S,4aR,6aR,6aS,6bR,8aR,9R,10R,11S,12aR,14bS)-10-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-11-hydroxy-9-(hydroxymethyl)-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-2,4a-dicarboxylate

Applications

Effect of esculentoside H on release of tumor necrosis factor from mouse peritoneal macrophages. PUMID/DOI:8010057 Zhongguo Yao Li Xue Bao. 1993 Nov;14(6):550-2. Effect of Esculentoside H (EH) on release of tumor necrosis factor (TNF) from murine peritoneal macrophage (Mphi) in vitro was studied. The results showed that Esculentoside H (12.5-200 micrograms.ml-1) induced the thioglycolate-broth elicited peritoneal Mphi to release TNF into supernatants in a dose-dependent manner, and higher levels of TNF activity were detected in the supernatants from Esculentoside H-stimulated calcimycin-primed Mø culture. Esculentoside H-induced TNF release had a different type of kinetics compared with that of lipopolysaccharides (LPS). LPS-induced release of TNF increased rapidly until 6 h after LPS stimulation, then declined gradually, while Esculentoside H-induced TNF release increased gradually after Esculentoside H stimulation and reached its peak at approximately 24 h later. These results suggested that the anti-tumor mechanisms of Phytolaccaceae may be related to the capacity of Esculentoside H for TNF release.

Density

1.5±0.1 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

295.3±27.8 °C

Boiling Point

1042.8±65.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C48H76O21/c1-43(41(61)63-6)11-13-48(42(62)69-40-36(60)33(57)30(54)25(18-50)66-40)14-12-46(4)21(22(48)15-43)7-8-28-44(2)16-23(52)37(45(3,20-51)27(44)9-10-47(28,46)5)68-38-34(58)31(55)26(19-64-38)67-39-35(59)32(56)29(53)24(17-49)65-39/h7,22-40,49-60H,8-20H2,1-6H3/t22-,23+,24-,25-,26-,27?,28-,29-,30-,31+,32+,33+,34-,35-,36-,37+,38+,39+,40+,43-,44+,45+,46-,47-,48+/m1/s1

InChl Key

UQCUBQIHIKJPHI-IEGHAIBGSA-N

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:66656-92-6) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

30525244

Abstract

A water-soluble saponin, Esculentoside H (EsH), 3-O-(O-β-d-glucopyranosyl-(1→4)-β-d-xylopyranosyl)-28-β-d-glucopyranosylphytolaccagenin has been isolated and purified from the root extract of perennial plant Phytolacca esculenta. EsH is known to be an anticancer compound, having a capacity for TNF-α release. However, the effects of EsH on migration and growth in tumor cells have not yet been reported. In the current study, the suppressive effects of EsH on phorbol 12-myristate 13-acetate (PMA)-induced cell migration were examined in murine colon cancer CT26 cells and human colon cancer HCT116 cells. Interestingly, the transwell assay and wound healing show that EsH suppresses the PMA-induced migration and growth potential of HCT116 and CT26 colon cancer cells, respectively. EsH dose-dependently suppressed matrix metalloproteinases-9 (MMP-9) expression that was upregulated upon PMA treatment in messenger RNA levels and protein secretion. Since the expression of MMP-9 is correlated with nuclear factor-κB (NF-κB) signaling, it has been examined whether EsH inhibits PMA-induced IκB phosphorylation that leads to the suppression of NK-κB nuclear translocation. EsH repressed the phosphorylation level of JNK, but not extracellular signal-regulated kinase and p38 signaling when the cells were treated with PMA. Overall, these results demonstrated that EsH could suppress cancer migration through blockage of the JNK1/2 and NF-κB signaling-mediated MMP-9 expression.

KEYWORDS

cancer; cancer growth; colon cancer; migration; mitogen-activated protein kinase-9.

Title

Esculentoside H inhibits colon cancer cell migration and growth through suppression of MMP-9 gene expression via NF-kB signaling pathway

Author

Sun-Hyung Ha 1, Kyung-Min Kwon 1, Jun-Young Park 1, Fukushi Abekura 1, Young-Choon Lee 2, Tae-Wook Chung 3, Ki-Tae Ha 3, Hyeun Wook Chang 4, Seung-Hak Cho 5, Jong-Suk Kim 6, Cheorl-Ho Kim 1

Publish date

2019 Jun

PMID

8010057

Abstract

Effect of esculentoside H (EH) on release of tumor necrosis factor (TNF) from murine peritoneal macrophage (Mphi) in vitro was studied. The results showed that EH (12.5-200 micrograms.ml-1) induced the thioglycolate-broth elicited peritoneal Mphi to release TNF into supernatants in a dose-dependent manner, and higher levels of TNF activity were detected in the supernatants from EH-stimulated calcimycin-primed Mø culture. EH-induced TNF release had a different type of kinetics compared with that of lipopolysaccharides (LPS). LPS-induced release of TNF increased rapidly until 6 h after LPS stimulation, then declined gradually, while EH-induced TNF release increased gradually after EH stimulation and reached its peak at approximately 24 h later. These results suggested that the anti-tumor mechanisms of Phytolaccaceae may be related to the capacity of EH for TNF release.

Title

Effect of esculentoside H on release of tumor necrosis factor from mouse peritoneal macrophages

Author

Z L Hu 1, J P Zhang, Y H Yi, D H Qian

Publish date

1993 Nov

PMID

2482514

Abstract

A new water-soluble saponin (esculentoside H) has been isolated from the roots of Phytolacca esculenta and identified as 3-O-[beta-D-glucopyranosyl-(1—-4)-beta-D-xylopyranosyl]-28-O-beta-D- glucopyranosyl phytolaccagenin.

Title

A new active saponin from Phytolacca esculenta

Author

Y H Yi, C L Wang

Publish date

1989 Dec