Sesartemin

CAS# 77394-27-5

Sesartemin

Catalog No. BCN4779----Order now to get a substantial discount!

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Chemical structure

Sesartemin

3D structure

Chemical Properties of Sesartemin

Cas No. 77394-27-5 SDF Download SDF
PubChem ID 342737 Appearance Powder
Formula C23H26O8 M.Wt 430.5
Type of Compound Lignans Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 6-[(3S,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-VUEDXXQZSA-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 Sesartemin

The herbs of Rhaphidophora decursiva

Biological Activity of Sesartemin

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 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.
CONCLUSIONS:
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 μM. Piperdardine showed the most pronounced effect, with glucose uptake increased by 83 ± 18% at 100 μM 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.

In vivo

An ethnopharmacological examination of Virola elongata bark: a South American arrow poison.[Pubmed: 6097773]

J Ethnopharmacol. 1984 Oct;12(1):75-92.

The use of the resin of Virola elongata as an arrow poison was investigated.
METHODS AND RESULTS:
Aqueous and methanolic extracts of the dried bark were not observed to have toxic effects when administered intraperitoneally to mice. In an attempt to determine if the hallucinogenic indole alkaloid constituents of the bark, which form the basis for the alternate use of this material as a ceremonial snuff, could also be responsible for its use as an arrow poison, alkaloidal and non-alkaloidal extracts were compared with respect to their behavioral effects on mice. The non-alkaloidal extract was more effective in producing an observable alteration in behavior. This consisted of a marked reduction in spontaneous locomotor activity. The extract was fractionated and 13 of the major constituents assayed for their ability to reduce spontaneous locomotor activity.
CONCLUSIONS:
Most of this biological activity of the extract was attributable to the presence of the bis-tetrahydrofuran lignans, epi-Sesartemin, Sesartemin, epi-yangambin and yangambin. Each of these compounds was also observed to reduce isolation induced aggression when administered to mice.

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Preparing Stock Solutions of Sesartemin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.3229 mL 11.6144 mL 23.2288 mL 46.4576 mL 58.072 mL
5 mM 0.4646 mL 2.3229 mL 4.6458 mL 9.2915 mL 11.6144 mL
10 mM 0.2323 mL 1.1614 mL 2.3229 mL 4.6458 mL 5.8072 mL
50 mM 0.0465 mL 0.2323 mL 0.4646 mL 0.9292 mL 1.1614 mL
100 mM 0.0232 mL 0.1161 mL 0.2323 mL 0.4646 mL 0.5807 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 Sesartemin

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.

An ethnopharmacological examination of Virola elongata bark: a South American arrow poison.[Pubmed:6097773]

J Ethnopharmacol. 1984 Oct;12(1):75-92.

The use of the resin of Virola elongata as an arrow poison was investigated. Aqueous and methanolic extracts of the dried bark were not observed to have toxic effects when administered intraperitoneally to mice. In an attempt to determine if the hallucinogenic indole alkaloid constituents of the bark, which form the basis for the alternate use of this material as a ceremonial snuff, could also be responsible for its use as an arrow poison, alkaloidal and non-alkaloidal extracts were compared with respect to their behavioral effects on mice. The non-alkaloidal extract was more effective in producing an observable alteration in behavior. This consisted of a marked reduction in spontaneous locomotor activity. The extract was fractionated and 13 of the major constituents assayed for their ability to reduce spontaneous locomotor activity. Most of this biological activity of the extract was attributable to the presence of the bis-tetrahydrofuran lignans, epi-Sesartemin, Sesartemin, epi-yangambin and yangambin. Each of these compounds was also observed to reduce isolation induced aggression when administered to mice.

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