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Picfeltarraenin IA

CAS# 97230-47-2

Picfeltarraenin IA

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Quality Control of Picfeltarraenin IA

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Chemical structure

Picfeltarraenin IA

3D structure

Chemical Properties of Picfeltarraenin IA

Cas No. 97230-47-2 SDF Download SDF
PubChem ID 91884878 Appearance White powder
Formula C41H62O13 M.Wt 762.92
Type of Compound Triterpenoids Storage Desiccate at -20°C
Solubility Soluble in methanol and pyridine
Chemical Name (2R)-2-[(3R,8S,9R,10R,13R,14S,16R,17R)-3-[(2S,3R,4S,5R)-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-16-hydroxy-4,4,9,13,14-pentamethyl-11-oxo-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-2-methyl-5-propan-2-ylfuran-3-one
SMILES CC1C(C(C(C(O1)OC2C(C(COC2OC3CCC4C(=CCC5C4(C(=O)CC6(C5(CC(C6C7(C(=O)C=C(O7)C(C)C)C)O)C)C)C)C3(C)C)O)O)O)O)O
Standard InChIKey WPXIIGGPWPYUSJ-CUXXYAFUSA-N
Standard InChI InChI=1S/C41H62O13/c1-18(2)24-14-26(44)41(9,54-24)34-22(42)15-38(6)25-12-10-20-21(40(25,8)27(45)16-39(34,38)7)11-13-28(37(20,4)5)52-36-33(30(47)23(43)17-50-36)53-35-32(49)31(48)29(46)19(3)51-35/h10,14,18-19,21-23,25,28-36,42-43,46-49H,11-13,15-17H2,1-9H3/t19-,21+,22+,23+,25-,28+,29-,30-,31+,32+,33+,34-,35-,36-,38-,39+,40-,41-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Picfeltarraenin IA

The herbs of Picria felterrae Lour.

Biological Activity of Picfeltarraenin IA

DescriptionPicfeltarraenin IA has anti-inflammatory activity, it is a strong AChE inhibitior, and an potential PI3K and epidermal growth factor receptor (EGFR ) inhibitor. It acts as an inhibitor on both the classical and alternative pathways of the complement system.
TargetsIL Receptor | PGE | NF-kB | COX | p65 | EGFR | PI3K | Akt
In vitro

Picfeltarraenin IA inhibits lipopolysaccharide-induced inflammatory cytokine production by the nuclear factor-κB pathway in human pulmonary epithelial A549 cells.[Pubmed: 26893718 ]

Oncol Lett. 2016 Feb;11(2):1195-1200.

The present study aimed to investigate the effect of Picfeltarraenin IA (IA) on respiratory inflammation by analyzing its effect on interleukin (IL)-8 and prostaglandin E2 (PGE2) production. The expression of cyclooxygenase 2 (COX2) in human pulmonary adenocarcinoma epithelial A549 cells in culture was also examined.
METHODS AND RESULTS:
Human pulmonary epithelial A549 cells and the human monocytic leukemia THP-1 cell line were used in the current study. Cell viability was measured using a methylthiazol tetrazolium assay. The production of IL-8 and PGE2 was investigated using an enzyme-linked immunosorbent assay. The expression of COX2 and nuclear factor-κB (NF-κB)-p65 was examined using western blot analysis. Treatment with lipopolysaccharide (LPS; 10 μg/ml) resulted in the increased production of IL-8 and PGE2, and the increased expression of COX2 in the A549 cells. Furthermore, IA (0.1-10 μmol/l) significantly inhibited PGE2 production and COX2 expression in cells with LPS-induced IL-8, in a concentration-dependent manner. The results suggested that IA downregulates LPS-induced COX2 expression, and inhibits IL-8 and PGE2 production in pulmonary epithelial cells. Additionally, IA was observed to suppress the expression of COX2 in THP-1 cells, and also to regulate the expression of COX2 via the NF-κB pathway in the A549 cells, but not in the THP-1 cells.
CONCLUSIONS:
These results indicate that IA regulates LPS-induced cytokine release in A549 cells via the NF-κB pathway.

Protocol of Picfeltarraenin IA

Kinase Assay

In Silico Analysis of Picfeltarraenin IA and IB as Potential PI3K and EGFR Inhibitor.[Reference: WebLink]

Der PharmaChemica, 2016, 8(19):666-670.

Picfeltarraenin IA and IB are the steroid glycoside from Picria fel-terrae Lour., Have been traditionally used in medication. Epidermal growth factor receptor (EGFR) plays a critical role in the initiation and progression of a variety of human cancers, including breast cancer. An important signaling pathway downstream of EGFR is the PI3K/AKt pathway, which regulates cellular processes as diverse as cell growth, survival, proliferation and migration. In silico docking using PLANTS program and visualized by Yasara program.
METHODS AND RESULTS:
The model of three dimension enzyme structures used in this research were EGFR and Phosphatidylinositol-3-kinase (PI3K), binding pocket with the Protein Data Bank (PDB) code 1M17 and 3DBS . Two and three dimension of Picfeltarraenin IA, IB and ZSTK474 as the standard were generated using Marvin Sketch program.
CONCLUSIONS:
Both compounds and ZSTK474 inhibited EGFR and PI3K with docking score -101.7930; -104.6410, -91.7920 and -90.6176 -87.7705; -94.7491 respectively.

Structure Identification
Pharmacogn Mag. 2013 Oct;9(Suppl 1):S25-31.

Bioassay- and liquid chromatography/mass spectrometry-guided acetylcholinesterase inhibitors from Picriafel-terrae.[Pubmed: 24143041]

Picria fel-terrae is a traditional Chinese medicine.
METHODS AND RESULTS:
: A new approach to the search for acetylcholinesterase (AChE) inhibitors from Picria fel-terrae is presented. RESULTS: Bioassay- and LC-MS-guided fractionation of the ethyl acetate extract was from traditional Chinese medicine P.fel-terrae. Following primary extraction, the ethyl acetate extracts fraction of P.fel-terrae showed strong AChE inhibitory activities. So the sample was separated using highperformance liquid chromatography (HPLC). The effluent was split towards two identical 96-well fraction collectors, and the presence of the biologically interesting portion and chromatographic fractions could be readily detected by analyzing selected ion chromatograms through an electrophoresis-electrospray ionization mass spectrometry (ESIMS) system for accurate mass measurement. One 96-well plate was used for a bioassay (AChE-inhibitory assay) and detected the bioactivity and position of the relevant peak in the chromatogram. The positive well in the second 96-well plate was used for identification by LC-(+) ESIMS.
CONCLUSIONS:
As abovementioned, the AChE inhibitory constituents from P.fel-terrae by LC-bioassay-ESIMS were rapid identified. Liquid chromatography/ mass spectrometry (LC-MS) screening detected the presence of six active compounds, identified as Picfeltarraenin IA (1), picfeltarraenin IB (2), picfeltarraenin IV (3), picfeltarraenin X (4), picfeltarraenin XI (5), and one unknown compound. The structures were further determined by 13C NMR. The six compounds expressed stronger AChE inhibition than the known AChE inhibitorTacrine. Above all, the value of this LC-bioassay-ESIMS methodology is highlighted by the finding and structure elucidation of the active constituents from many other structural families of natural products.

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Preparing Stock Solutions of Picfeltarraenin IA

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.3108 mL 6.5538 mL 13.1075 mL 26.2151 mL 32.7688 mL
5 mM 0.2622 mL 1.3108 mL 2.6215 mL 5.243 mL 6.5538 mL
10 mM 0.1311 mL 0.6554 mL 1.3108 mL 2.6215 mL 3.2769 mL
50 mM 0.0262 mL 0.1311 mL 0.2622 mL 0.5243 mL 0.6554 mL
100 mM 0.0131 mL 0.0655 mL 0.1311 mL 0.2622 mL 0.3277 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Picfeltarraenin IA

Bioassay- and liquid chromatography/mass spectrometry-guided acetylcholinesterase inhibitors from Picriafel-terrae.[Pubmed:24143041]

Pharmacogn Mag. 2013 Oct;9(Suppl 1):S25-31.

BACKGROUND: Picria fel-terrae is a traditional Chinese medicine. MATERIALS AND METHODS: A new approach to the search for acetylcholinesterase (AChE) inhibitors from Picria fel-terrae is presented. RESULTS: Bioassay- and LC-MS-guided fractionation of the ethyl acetate extract was from traditional Chinese medicine P.fel-terrae. Following primary extraction, the ethyl acetate extracts fraction of P.fel-terrae showed strong AChE inhibitory activities. So the sample was separated using highperformance liquid chromatography (HPLC). The effluent was split towards two identical 96-well fraction collectors, and the presence of the biologically interesting portion and chromatographic fractions could be readily detected by analyzing selected ion chromatograms through an electrophoresis-electrospray ionization mass spectrometry (ESIMS) system for accurate mass measurement. One 96-well plate was used for a bioassay (AChE-inhibitory assay) and detected the bioactivity and position of the relevant peak in the chromatogram. The positive well in the second 96-well plate was used for identification by LC-(+) ESIMS. CONCLUSION: As abovementioned, the AChE inhibitory constituents from P.fel-terrae by LC-bioassay-ESIMS were rapid identified. Liquid chromatography/ mass spectrometry (LC-MS) screening detected the presence of six active compounds, identified as Picfeltarraenin IA (1), picfeltarraenin IB (2), picfeltarraenin IV (3), picfeltarraenin X (4), picfeltarraenin XI (5), and one unknown compound. The structures were further determined by 13C NMR. The six compounds expressed stronger AChE inhibition than the known AChE inhibitorTacrine. Above all, the value of this LC-bioassay-ESIMS methodology is highlighted by the finding and structure elucidation of the active constituents from many other structural families of natural products.

Complement-inhibiting cucurbitacin glycosides from Picria fel-terrae.[Pubmed:9644059]

J Nat Prod. 1998 Jun 26;61(6):757-61.

Four cucurbitacin glycosides were isolated from Picriafel-terrae and identified by MS and NMR spectroscopy as Picfeltarraenin IA (1), picfeltarraenin IB (2), picfeltarraenin IV (4), and a new compound picfeltarraenin VI (3) (picfeltarraegenin I 3-O-beta-D-xylopyranoside). All four compounds acted as inhibitors on both the classical and alternative pathways of the complement system, with compound 3 exhibiting the highest inhibitory activity (IC50 29 +/- 2 microM and 21 +/- 1 microM, respectively). Compounds 1-4 showed no antiviral, antibacterial, or antifungal activities. Picfeltarraenin IA and IB were tested in an in vitro human tumor cell line panel, but displayed no cytotoxic activity.

Picfeltarraenin IA inhibits lipopolysaccharide-induced inflammatory cytokine production by the nuclear factor-kappaB pathway in human pulmonary epithelial A549 cells.[Pubmed:26893718]

Oncol Lett. 2016 Feb;11(2):1195-1200.

The present study aimed to investigate the effect of Picfeltarraenin IA (IA) on respiratory inflammation by analyzing its effect on interleukin (IL)-8 and prostaglandin E2 (PGE2) production. The expression of cyclooxygenase 2 (COX2) in human pulmonary adenocarcinoma epithelial A549 cells in culture was also examined. Human pulmonary epithelial A549 cells and the human monocytic leukemia THP-1 cell line were used in the current study. Cell viability was measured using a methylthiazol tetrazolium assay. The production of IL-8 and PGE2 was investigated using an enzyme-linked immunosorbent assay. The expression of COX2 and nuclear factor-kappaB (NF-kappaB)-p65 was examined using western blot analysis. Treatment with lipopolysaccharide (LPS; 10 microg/ml) resulted in the increased production of IL-8 and PGE2, and the increased expression of COX2 in the A549 cells. Furthermore, IA (0.1-10 micromol/l) significantly inhibited PGE2 production and COX2 expression in cells with LPS-induced IL-8, in a concentration-dependent manner. The results suggested that IA downregulates LPS-induced COX2 expression, and inhibits IL-8 and PGE2 production in pulmonary epithelial cells. Additionally, IA was observed to suppress the expression of COX2 in THP-1 cells, and also to regulate the expression of COX2 via the NF-kappaB pathway in the A549 cells, but not in the THP-1 cells. These results indicate that IA regulates LPS-induced cytokine release in A549 cells via the NF-kappaB pathway.

Description

Picfeltarraenin IA, a triterpenoid obtained from Picriafel-terrae Lour (P.fel-terrae), is an acetylcholinesterase (AChE) inhibitor. Picfeltarraenin IA can be used for the treatment of herpes infections, cancer and inflammation.

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