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Hederacolchiside A1

$198

  • Brand : BIOFRON

  • Catalogue Number : BF-H4004

  • Specification : 98%(HPLC)

  • CAS number : 106577-39-3

  • Formula : C47H76O16

  • Molecular Weight : 897.1

  • PUBCHEM ID : 11622076

  • Volume : 20mg

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Catalogue Number

BF-H4004

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

2-8°C

Molecular Weight

897.1

Appearance

White crystalline powder

Botanical Source

Pulsatilla chinensis,Anemone raddeana

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1C(C(C(C(O1)OC2C(C(COC2OC3CCC4(C(C3(C)C)CCC5(C4CC=C6C5(CCC7(C6CC(CC7)(C)C)C(=O)O)C)C)C)OC8C(C(C(C(O8)CO)O)O)O)O)O)O)O

Synonyms

(3β,5ξ,18α)-3-{[6-Deoxy-α-L-mannopyranosyl-(1->2)-[β-D-glucopyranosyl-(1->4)]-α-L-arabinopyranosyl]oxy}olean-12-en-28-oic acid/Olean-12-en-28-oic acid, 3-[[O-6-deoxy-α-L-mannopyranosyl-(1->2)-O-[β-D-glucopyranosyl-(1->4)]-α-L-arabinopyranosyl]oxy]-, (3β,5ξ,18α)-

IUPAC Name

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

Applications

Hederacolchiside A1, isolated from Pulsatilla chinensis, suppresses proliferation of tumor cells by inducing apoptosis through modulating PI3K/Akt/mTOR signaling pathway[1]. Hederacolchiside A1 has antischistosomal activity, affecting parasite viability both in vivo and in vitro[2].

Density

1.36±0.1 g/cm3 (20 ºC 760 Torr)

Solubility

Methanol

Flash Point

276.2±27.8 °C

Boiling Point

967.2±65.0 °C at 760 mmHg

Melting Point

253-255℃ (methanol , water )

InChl

InChI=1S/C47H76O16/c1-22-30(49)33(52)35(54)38(59-22)63-37-32(51)26(61-39-36(55)34(53)31(50)25(20-48)60-39)21-58-40(37)62-29-12-13-44(6)27(43(29,4)5)11-14-46(8)28(44)10-9-23-24-19-42(2,3)15-17-47(24,41(56)57)18-16-45(23,46)7/h9,22,24-40,48-55H,10-21H2,1-8H3,(H,56,57)/t22-,24-,25+,26-,27-,28+,29-,30-,31+,32-,33+,34-,35+,36+,37+,38-,39-,40-,44-,45+,46+,47-/m0/s1

InChl Key

FYSAXYBPXKLMJO-IFECXJOTSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:106577-39-3) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

15490165

Abstract

Purpose: Neoangiogenesis is critical to cancer proliferation and metastasis and constitutes an attractive target for cancer therapy. It has previously been demonstrated that hederacolchiside-A1 (HCol-A1), a triterpenoid saponin from Hedera colchica Koch, has antimelanoma potential. The goal of this study was to evaluate, in vitro, if in addition to its tumoricidal effect on melanoma cells, HCol-A1 might affect endothelial cell network formation.
Methods: We investigated whether HCol-A1 affects matrigel-induced tubulogenesis and inhibits the viability (WST-1 assay) of human umbilical vein endothelial cells (HUVECs). To provide structure-activity relationships (SAR), studies were conducted on HCol-A1, oleanolic acid and hederacolchiside A (HCol-A), a triterpenoid saponin which possess the same sugar sequence as Hcol-A1. Plasma membrane cholesterol sequestration was studied by labelling with [3H]cholesterol and assayed with HCol-A1-cholesterol complexes. HCol-A1 signalling was investigated using immunoassays.
Results: In contrast to HCol-A and oleanolic acid, HCol-A1 inhibited matrigel-induced angiogenesis at micromolar concentration. Plasma membrane cholesterol sequestration was found to be critical for this activity. Activation of the Ras/MEK/ERK cascade appears to be one of the mechanisms by which Hcol-A1 affects HUVEC network formation. The predominant activation of the Ha-Ras isoform, which decreases HUVEC-tolerance to apoptosis, might contribute to the high susceptibility of this cell line to HCol-A1.
Conclusion: Since cholesterol sequestration affects cell confluence-dependent remodelling of endothelial membranes and vascular endothelial growth factor receptor-2 activity, these results raise the possibility that Hcol-A1 might slow-down cancer proliferation and metastasis in vivo by inhibiting critical aspects of neoangiogenesis. Further in vivo studies are needed to verify this hypothesis.

Title

Inhibition of HUVEC Tubulogenesis by hederacolchiside-A1 Is Associated With Plasma Membrane Cholesterol Sequestration and Activation of the Ha-Ras/MEK/ERK Cascade

Author

Chantal Barthomeuf 1 , Dominique Boivin, Richard Beliveau

Publish date

2004 Nov;

PMID

29899232

Abstract

Background: Schistosomiasis is a major neglected disease for which the current control strategy involves mass treatment with praziquantel, the only available drug. Hence, there is an urgent need to develop new antischistosomal compounds. Methods: The antischistosomal activity of hederacolchiside A1 (HSA) were determined by total or female worm burden reductions in mice harboring Schistosoma japonicum or S. mansoni. Pathology parameters were detected on HSA against 1-day-old S. japonicum-harboring mice. Moreover, we confirmed the antischistosomal effect of HSA on newly transformed schistosomula (NTS) of S. japonicum in vitro. Results: HSA, a natural product isolated from Pulsatilla chinensis (Bunge) Regel, was initially corroborated to possess promising antischistosomal properties. We demonstrated that HSA had high activity against S. japonicum and S. mansoni less in 11 days old parasites harbored in mice. The antischistosomal effect was even more than the currently used drugs, praziquantel, and artesunate. Furthermore, HSA could ameliorate the pathology parameters in mice harboring 1-day-old juvenile S. japonicum. We also confirmed that HSA-mediated antischistosomal activity is partly due to the morphological changes in the tegument system when NTS are exposed to HSA. Conclusions: HSA may have great potential to be an antischistosomal agent for further research.

KEYWORDS

Schistosoma japonicum; Schistosoma mansoni; antischistosomal; hederacolchiside A1.

Title

Antischistosomal Properties of Hederacolchiside A1 Isolated From Pulsatilla chinensis

Author

Naixin Kang 1 , Wenhua Shen 2 , Hongwei Gao 3 , Yulin Feng 4 , Weifeng Zhu 5 , Shilin Yang 6 7 , Yanli Liu 8 , Qiongming Xu 9 , Di Yu 10

Publish date

2018 Jun 13

PMID

18338859

Abstract

Hederacolchiside A1 was used to progressively permeabilize the membrane of human melanoma MEL-5 cells. Holes formation was followed by Scanning Electron Microscopy and interaction of the saponin with cholesterol and phospholipids by TOF-SIMS. 2D-LC-MS/MS and 2D-SDS-PAGE show that the release of soluble proteins into serum-free culture media increases with time. This can lead to a new rapid and efficient strategy to analyze the cytosolic subproteome and it opens the door to get information from the cytosolic compartment for clinical proteomic studies.

Title

Pores Formation on Cell Membranes by Hederacolchiside A1 Leads to a Rapid Release of Proteins for Cytosolic Subproteome Analysis

Author

Gabriel D Mazzucchelli 1 , Nicolas A Cellier, Vakhtang Mshviladzade, Riad Elias, Yong-Ho Shim, David Touboul, Loïc Quinton, Alain Brunelle, Olivier Laprevote, Edwin A De Pauw, Marie-Claire A De Pauw-Gillet

Publish date

2008 Apr