d-Laserpitin

CAS# 134002-17-8

d-Laserpitin

2D Structure

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3D structure

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d-Laserpitin

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Chemical Properties of d-Laserpitin

Cas No. 134002-17-8 SDF Download SDF
PubChem ID 51396729 Appearance Powder
Formula C19H20O6 M.Wt 344.4
Type of Compound Coumarins Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name [(9S,10S)-9-hydroxy-8,8-dimethyl-2-oxo-9,10-dihydropyrano[2,3-f]chromen-10-yl] (Z)-2-methylbut-2-enoate
SMILES CC=C(C)C(=O)OC1C(C(OC2=C1C3=C(C=C2)C=CC(=O)O3)(C)C)O
Standard InChIKey QPLSCFLMIOADPA-LNUYWUECSA-N
Standard InChI InChI=1S/C19H20O6/c1-5-10(2)18(22)24-16-14-12(25-19(3,4)17(16)21)8-6-11-7-9-13(20)23-15(11)14/h5-9,16-17,21H,1-4H3/b10-5-/t16-,17-/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 d-Laserpitin

The herbs of Seseli gummiferum

Biological Activity of d-Laserpitin

In vitro

Application of stepwise gradients in counter-current chromatography: a rapid and economical strategy for the one-step separation of eight coumarins from Seseli resinosum.[Pubmed: 23992840]

J Chromatogr A. 2013 Oct 4;1310:66-73.

The targeted purification of compounds with a broad polarity range from traditional medicinal plants is a big challenge for counter-current chromatography (CCC). Gradient elution was introduced in CCC to address this problem. However, once a suitable solvent system is selected, the separation process requires optimization of operational parameters.
METHODS AND RESULTS:
The present study was conducted to optimize various operational parameters to integrate the flow rate and solvent gradients for the rapid isolation of eight coumarins from Seseli resinosum in a single run. An increase in the system temperature from 15°C to 35°C increased the stationary phase retention and solubility of the sample, whereas the operation time and viscosity of the system were decreased. The high purity of each compound was ensured by collecting the fractions from the main peaks while all the shoulder peaks were mixed and separated under the same conditions with semi-preparative CCC. GC-FID was used to analyze the components of each phase, which was prepared without presaturation to save the time and solvent consumption. Finally, eight coumarins were purified, including (1) d-Laserpitin, (2) (3'S,4'S)-3'-angeloyloxy-4'-hydroxy-3',4'-dihydroseselin, (3) (+)-samidin, (4) (3'S,4'S)-3'-acetoxy-4'-angeloyloxy-3',4'-dihydroseselin, (5) deltoin (6), calipteryxin, (7) (3'S,4'S)-3',4'-disenecioyloxy-3',4'-dihydroseselin, and (8) (-)-anomalin.
CONCLUSIONS:
The present technique has successfully accomplished the goal of one-step separation of these compounds with high purity and recovery in an economic and time efficient manner.

In vivo

Anti-inflammatory and antinociceptive activity of coumarins from Seseli gummiferum subsp. corymbosum (Apiaceae).[Pubmed: 19323267]

Z Naturforsch C. 2009 Jan-Feb;64(1-2):56-62.

n-Hexane and ethyl acetate extracts as well as coumarin derivatives obtained from the n-hexane extract of the aerial parts of Seseli gummiferum Pall. ex Sm. subsp. corymbosum (Boiss. & Heldr.) P.H. Davis (Apiaceae) were evaluated in vivo for their anti-inflammatory and antinociceptive activities.
METHODS AND RESULTS:
The n-hexane and ethyl acetate extracts of the species were shown to possess significant inhibitory activity against the carrageenan-induced hind paw edema and p-benzoquinone-induced writhing models in mice. Among the isolated coumarin derivatives; (-)-(3'S,4'S)-3'-acetoxy-4'-isovaleryloxy-3',4'-dihydroseselin (1), (-)-(3'S,4'S)-3'-acetoxy-4'-angeloyloxy-3',4'-dihydroseselin (2), (+)-(3'S,4'S)-3'-hydroxy-4'-angeloyloxy-3',4'-dihydroseselin (d-Laserpitin) (3), (-)-(3'S,4'S)-3'-angeloyloxy-4'-hydroxy-3',4'-dihydroseselin (4), and osthole (5), only the 3'-acetoxy derivatives 1 and 2 were found to possess potent antinociceptive and anti-inflammatory activities, per os, without inducing any apparent acute toxicity as well as gastric damage, while all other compounds and extracts were found to be ineffective in the TPA-induced mouse ear edema model assay.

d-Laserpitin Dilution Calculator

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Preparing Stock Solutions of d-Laserpitin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.9036 mL 14.518 mL 29.036 mL 58.072 mL 72.59 mL
5 mM 0.5807 mL 2.9036 mL 5.8072 mL 11.6144 mL 14.518 mL
10 mM 0.2904 mL 1.4518 mL 2.9036 mL 5.8072 mL 7.259 mL
50 mM 0.0581 mL 0.2904 mL 0.5807 mL 1.1614 mL 1.4518 mL
100 mM 0.029 mL 0.1452 mL 0.2904 mL 0.5807 mL 0.7259 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 d-Laserpitin

Anti-inflammatory and antinociceptive activity of coumarins from Seseli gummiferum subsp. corymbosum (Apiaceae).[Pubmed:19323267]

Z Naturforsch C. 2009 Jan-Feb;64(1-2):56-62.

n-Hexane and ethyl acetate extracts as well as coumarin derivatives obtained from the n-hexane extract of the aerial parts of Seseli gummiferum Pall. ex Sm. subsp. corymbosum (Boiss. & Heldr.) P.H. Davis (Apiaceae) were evaluated in vivo for their anti-inflammatory and antinociceptive activities. The n-hexane and ethyl acetate extracts of the species were shown to possess significant inhibitory activity against the carrageenan-induced hind paw edema and p-benzoquinone-induced writhing models in mice. Among the isolated coumarin derivatives; (-)-(3'S,4'S)-3'-acetoxy-4'-isovaleryloxy-3',4'-dihydroseselin (1), (-)-(3'S,4'S)-3'-acetoxy-4'-angeloyloxy-3',4'-dihydroseselin (2), (+)-(3'S,4'S)-3'-hydroxy-4'-angeloyloxy-3',4'-dihydroseselin (d-Laserpitin) (3), (-)-(3'S,4'S)-3'-angeloyloxy-4'-hydroxy-3',4'-dihydroseselin (4), and osthole (5), only the 3'-acetoxy derivatives 1 and 2 were found to possess potent antinociceptive and anti-inflammatory activities, per os, without inducing any apparent acute toxicity as well as gastric damage, while all other compounds and extracts were found to be ineffective in the TPA-induced mouse ear edema model assay.

Application of stepwise gradients in counter-current chromatography: a rapid and economical strategy for the one-step separation of eight coumarins from Seseli resinosum.[Pubmed:23992840]

J Chromatogr A. 2013 Oct 4;1310:66-73.

The targeted purification of compounds with a broad polarity range from traditional medicinal plants is a big challenge for counter-current chromatography (CCC). Gradient elution was introduced in CCC to address this problem. However, once a suitable solvent system is selected, the separation process requires optimization of operational parameters. The present study was conducted to optimize various operational parameters to integrate the flow rate and solvent gradients for the rapid isolation of eight coumarins from Seseli resinosum in a single run. An increase in the system temperature from 15 degrees C to 35 degrees C increased the stationary phase retention and solubility of the sample, whereas the operation time and viscosity of the system were decreased. The high purity of each compound was ensured by collecting the fractions from the main peaks while all the shoulder peaks were mixed and separated under the same conditions with semi-preparative CCC. GC-FID was used to analyze the components of each phase, which was prepared without presaturation to save the time and solvent consumption. Finally, eight coumarins were purified, including (1) d-Laserpitin, (2) (3'S,4'S)-3'-angeloyloxy-4'-hydroxy-3',4'-dihydroseselin, (3) (+)-samidin, (4) (3'S,4'S)-3'-acetoxy-4'-angeloyloxy-3',4'-dihydroseselin, (5) deltoin (6), calipteryxin, (7) (3'S,4'S)-3',4'-disenecioyloxy-3',4'-dihydroseselin, and (8) (-)-anomalin. The present technique has successfully accomplished the goal of one-step separation of these compounds with high purity and recovery in an economic and time efficient manner.

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