Thapsigargicin
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| Category | Others |
| Catalog number | BBF-05809 |
| CAS | 67526-94-7 |
| Molecular Weight | 622.70 |
| Molecular Formula | C32H46O12 |
| Purity | ≥90% |
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Description
It is a hexaoxygenated tetra-acylated sesquiterpene lactone tetraester isolated from roots of Thapsia garganica. It induces mast cell degranulation and histamine release.
Specification
| Synonyms | Hexanoic acid, (3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-(acetyloxy)-2,3,3a,4,5,6,6a,7,8,9b-decahydro-3,3a-dihydroxy-3,6,9-trimethyl-8-[[(2Z)-2-methyl-1-oxo-2-buten-1-yl]oxy]-2-oxo-4-(1-oxobutoxy)azuleno[4,5-b]furan-7-yl ester |
| Storage | Store at -20°C |
| IUPAC Name | [(3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-acetyloxy-4-butanoyloxy-3,3a-dihydroxy-3,6,9-trimethyl-8-[(Z)-2-methylbut-2-enoyl]oxy-2-oxo-4,5,6a,7,8,9b-hexahydroazuleno[4,5-b]furan-7-yl] hexanoate |
| Canonical SMILES | CCCCCC(=O)OC1C2C(=C(C1OC(=O)C(=CC)C)C)C3C(C(CC2(C)OC(=O)C)OC(=O)CCC)(C(C(=O)O3)(C)O)O |
| InChI | InChI=1S/C32H46O12/c1-9-12-13-15-22(35)41-26-24-23(18(5)25(26)42-28(36)17(4)11-3)27-32(39,31(8,38)29(37)43-27)20(40-21(34)14-10-2)16-30(24,7)44-19(6)33/h11,20,24-27,38-39H,9-10,12-16H2,1-8H3/b17-11-/t20-,24+,25-,26-,27-,30-,31+,32+/m0/s1 |
| InChI Key | LXWLOFYIORKNSA-FFOGNQQCSA-N |
Properties
| Appearance | White Powder |
| Boiling Point | 673.3±55.0°C at 760 mmHg |
| Density | 1.3±0.1 g/cm3 |
| Solubility | Soluble in Acetonitrile |
Reference Reading
1. Effects of the sesquiterpene lactone tetraesters thapsigargicin and thapsigargin, from roots of Thapsia garganica L., on isolated spinach chloroplasts
K A Santarius, H Haddad, G Falsone Toxicon . 1987;25(4):389-99. doi: 10.1016/0041-0101(87)90072-9.
The effect of thapsigargicin and thapsigargin, extracted from the roots of Thapsia garganica L., on isolated photosynthetic membranes (thylakoids) and intact chloroplasts from spinach leaves (Spinacia oleracea L.) was investigated. Both sesquiterpene lactone tetraesters impair membranes and organelles in an identical, chlorophyll-dependent manner. In thylakoids these compounds primarily act as inhibitors of photophosphorylation. At lower sesquiterpene lactone tetraester/chlorophyll ratios, cyclic and non-cyclic photophosphorylation, ADP-stimulated electron transport and the photosynthetic control ratio progressively decreased with increasing concentrations of thapsigargicin and thapsigargin, whereas the state 4 electron flow, the coupling efficiency of photophosphorylation, the light-induced proton gradient, and the H+ flux across the membranes remained nearly unaffected. Half-maximal inhibition of photophosphorylation was obtained with 4-5 X 10(-7) moles sesquiterpene lactone tetraesters per mg chlorophyll. At higher sesquiterpene lactone tetraester/chlorophyll ratios, uncoupling of photophosphorylation from electron transport occurred. This was evident from stimulation of the state 4 electron flow, decline in the ADP/2e- ratio, increase in proton permeability and decrease in delta pH, whereas the uncoupled electron transport was only little impaired. In intact chloroplasts inhibition of HCO-3, 3-phosphoglycerate and oxaloacetate reduction by thapsigargicin and thapsigargin was not caused by inactivation of the photochemical reactions of the thylakoid membranes but were rather due to alterations in the permeability properties of the chloroplast envelope. This was concluded from similarities in the kinetics of these reactions. It is suggested that the highly lipid soluble sesquiterpene lactone tetraesters effectively disrupt the lipid-protein associations of biomembranes.
2. [Effects of thapsigargicin on Ca2+ movements in L1210 cells permeabilized with digitonin]
E Oztetik Biomed Khim . 2009 Sep-Oct;55(5):651-62.
The effect of Thapsigargicin (TGC), a non-phorbol ester type tumor promoter, on Ca2+ movements has been investigated using L1210 mouse lymphoma cells. Ca2+ release from intact and digitonin permeabilized cells was evaluated using Fura-2 and Fura-3. TGC like Thapsigargin (TG) has the ability to discharge the intracellular Ca2+ stores and to increase intracellular free Ca2+ concentrations. TGC in a concentration dependent manner (0.16-16 nM) also inhibited cell growth and this effect was at least partially reversed by arachidonate.
3. Actions of ethanolamine on cultured sensory neurones from neonatal rats
Gloria Adjei, Keith Allen-Redpath, Hesham Khairy, Roderick H Scott Neurosci Lett . 2010 Jan 14;468(3):326-9. doi: 10.1016/j.neulet.2009.11.025.
Some of the analgesic and antinociceptive properties of the endocannabinoid anandamide can be explained by modulation of voltage-activated ion channels. However, the products of anandamide metabolism by fatty acid amide hydroxylase may also contribute to the altered excitability of sensory neurones. Ethanolamine is a product of metabolism of acylethanolamines including anandamide. In this study whole cell patch clamp recording and fura-2 Ca(2+) imaging techniques were used to characterize its actions on neonatal rat cultured dorsal root ganglion neurones. Ethanolamine (1muM) increased the mean Ca(2+) transient produced by 1mM caffeine and modulated Ca(2+) transients evoked by 60mM KCl. Thapsigargicin (500nM) inhibited the ethanolamine-evoked enhancement of Ca(2+) transients evoked by depolarisation. Voltage-activated K(+) currents were evoked from a holding potential of -70mV by voltage step commands to 0mV. Acute application of 1muM ethanolamine produced irreversible current modulation. However, application of 100nM ethanolamine reversibly increased or decreased K(+) currents. These effects of ethanolamine on voltage-activated K(+) currents were not sensitive to continual application of thapsigargicin. When applied alone thapsigargicin (500nM) had no action on the mean K(+) current. In conclusion, ethanolamine may play distinct roles in the modulation of sensory neurone excitability by acting via different mechanisms to modulate K(+) channels and a component of intracellular Ca(2+) signalling. These data suggest that in a therapeutic context it may be difficult to predict the consequences of manipulating anandamide levels.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
