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
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
MSDS
15490165
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.
Inhibition of HUVEC Tubulogenesis by hederacolchiside-A1 Is Associated With Plasma Membrane Cholesterol Sequestration and Activation of the Ha-Ras/MEK/ERK Cascade
Chantal Barthomeuf 1 , Dominique Boivin, Richard Beliveau
2004 Nov;
29899232
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.
Schistosoma japonicum; Schistosoma mansoni; antischistosomal; hederacolchiside A1.
Antischistosomal Properties of Hederacolchiside A1 Isolated From Pulsatilla chinensis
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
2018 Jun 13
18338859
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.
Pores Formation on Cell Membranes by Hederacolchiside A1 Leads to a Rapid Release of Proteins for Cytosolic Subproteome Analysis
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
2008 Apr
