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Episesartemin A

CAS# 77449-31-1

Episesartemin A

2D Structure

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Episesartemin A

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Chemical Properties of Episesartemin A

Cas No. 77449-31-1 SDF Download SDF
PubChem ID 342739 Appearance Powder
Formula C23H26O8 M.Wt 430.45
Type of Compound Lignans Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 6-[(3aR,6S,6aR)-6-(3,4,5-trimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-4-methoxy-1,3-benzodioxole
SMILES COC1=CC(=CC2=C1OCO2)C3C4COC(C4CO3)C5=CC(=C(C(=C5)OC)OC)OC
Standard InChIKey DHWUVPPRBIJJKS-MDOOXIRGSA-N
Standard InChI InChI=1S/C23H26O8/c1-24-16-5-12(6-17(25-2)22(16)27-4)20-14-9-29-21(15(14)10-28-20)13-7-18(26-3)23-19(8-13)30-11-31-23/h5-8,14-15,20-21H,9-11H2,1-4H3/t14-,15-,20+,21?/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 Episesartemin A

The roots of Artemisia absinthium.

Biological Activity of Episesartemin A

DescriptionEpisesartemin A is a natural product from Artemisia absinthium.
In vitro

Sensory active piperine analogues from Macropiper excelsum and their effects on intestinal nutrient uptake in Caco-2 cells.[Pubmed: 28065397]

Phytochemistry. 2017 Mar;135:181-190.

The phytochemical profile of Macropiper excelsum (G.Forst.) Miq. subsp. excelsum (Piperaceae), a shrub which is widespread in New Zealand, was investigated by LC-MS-guided isolation and characterization via HR-ESI-TOF-MS and NMR spectroscopy.
METHODS AND RESULTS:
The isolated compounds were sensorily evaluated to identify their contribution to the overall taste of the crude extract with sweet, bitter, herbal and trigeminal impressions. Besides the known non-volatile Macropiper compounds, the lignans (+)-diayangambin and (+)-excelsin, four further excelsin isomers, (+)-diasesartemin, (+)-sesartemin, (+)-Episesartemin A and episesartemin B were newly characterized. Moreover, piperine and a number of piperine analogues as well as trans-pellitorine and two homologues, kalecide and (2E,4E)-tetradecadienoic acid N-isobutyl amide were identified in M. excelsum, some of them for the first time.

Protocol of Episesartemin A

Structure Identification
Tetrahedron, 1980, 36(24):3551-3558.

New unsymmetrically substituted tetrahydrofurofuran lignans from artemisia absinthium: Assignment of the relative stereochemistry by lanthanide induced chemical shifts.[Reference: WebLink]

The isolation of thirteen tetrahydrofurofuran lignans from the roots of A. absinthium and six closely related species is reported.
METHODS AND RESULTS:
A new group of four lignans, all stereoisomers of 1- [(3,4-methylenedioxy-5-methoxy) phenyl]-4-(3,4,5-trimethoxyphenyl)-tetrahydro-1H,3H-furo[3,4-c]furan, was found. The compounds, named sesartemin, Episesartemin A, episesartemin B, and diasesartemin, were characterized by 1H NMR (including lanthanide induced shifts), UV, IR and MS.
CONCLUSIONS:
A fifth new lignan of the sesamin type (the eq/eq isomer of fargesin) could be identified as a minor constituent. The relative configurations of two further products (fargesin and epiashantin) could be confirmed by the lanthanide induced shift technique.

Episesartemin A Dilution Calculator

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Episesartemin A Molarity Calculator

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Preparing Stock Solutions of Episesartemin A

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.3232 mL 11.6158 mL 23.2315 mL 46.463 mL 58.0788 mL
5 mM 0.4646 mL 2.3232 mL 4.6463 mL 9.2926 mL 11.6158 mL
10 mM 0.2323 mL 1.1616 mL 2.3232 mL 4.6463 mL 5.8079 mL
50 mM 0.0465 mL 0.2323 mL 0.4646 mL 0.9293 mL 1.1616 mL
100 mM 0.0232 mL 0.1162 mL 0.2323 mL 0.4646 mL 0.5808 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 Episesartemin A

Sensory active piperine analogues from Macropiper excelsum and their effects on intestinal nutrient uptake in Caco-2 cells.[Pubmed:28065397]

Phytochemistry. 2017 Mar;135:181-190.

The phytochemical profile of Macropiper excelsum (G.Forst.) Miq. subsp. excelsum (Piperaceae), a shrub which is widespread in New Zealand, was investigated by LC-MS-guided isolation and characterization via HR-ESI-TOF-MS and NMR spectroscopy. The isolated compounds were sensorily evaluated to identify their contribution to the overall taste of the crude extract with sweet, bitter, herbal and trigeminal impressions. Besides the known non-volatile Macropiper compounds, the lignans (+)-diayangambin and (+)-excelsin, four further excelsin isomers, (+)-diasesartemin, (+)-sesartemin, (+)-Episesartemin A and B were newly characterized. Moreover, piperine and a number of piperine analogues as well as trans-pellitorine and two homologues, kalecide and (2E,4E)-tetradecadienoic acid N-isobutyl amide were identified in M. excelsum, some of them for the first time. Methyl(2E,4E)-7-(1,3-benzodioxol-5-yl)hepta-2,4-dienoate was identified and characterized for the first time in nature. Sensory analysis of the pure amides indicated that they contributed to the known chemesthetic effects of Macropiper leaves and fruits. Since the pungent piperine has been shown to affect glucose and fatty acid metabolism in vivo in previous studies, piperine itself and four of the isolated compounds, piperdardine, chingchengenamide A, dihydropiperlonguminine, and methyl(2E,4E)-7-(1,3-benzodioxol-5-yl)hepta-2,4-dienoate, were investigated regarding their effects on glucose and fatty acid uptake by enterocyte-like Caco-2 cells, in concentrations ranging from 0.1 to 100 muM. Piperdardine showed the most pronounced effect, with glucose uptake increased by 83 +/- 18% at 100 muM compared to non-treated control cells. An amide group seems to be advantageous for glucose uptake stimulation, but not necessarily for fatty acid uptake-stimulating effects of piperine-related compounds.

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