Swainsonine
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| Category | Others |
| Catalog number | BBF-05810 |
| CAS | 72741-87-8 |
| Molecular Weight | 173.21 |
| Molecular Formula | C8H15NO3 |
| Purity | ≥98% |
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Description
Swainsonine is a plant alkaloid derived from Swainsona canescens (a leguminous plant). It is a reversible, active-site directed inhibitor of α-mannosidase at concentrations of 5-10 mM.
Specification
| Synonyms | Tridolgosir; 8α,β-Octahydroindolizidine-1α,2α,8β-triol; (-)-Swainsonine; (1S,2R,8R,8aR)-Octahydroindolizidinetriol; 1,2,8-Indolizinetriol, octahydro-, (1S-(1alpha,2alpha,8beta,8abeta))- |
| Storage | Store at -20°C |
| IUPAC Name | (1S,2R,8R,8aR)-1,2,3,5,6,7,8,8a-octahydroindolizine-1,2,8-triol |
| Canonical SMILES | C1CC(C2C(C(CN2C1)O)O)O |
| InChI | InChI=1S/C8H15NO3/c10-5-2-1-3-9-4-6(11)8(12)7(5)9/h5-8,10-12H,1-4H2/t5-,6-,7-,8-/m1/s1 |
| InChI Key | FXUAIOOAOAVCGD-WCTZXXKLSA-N |
| Source | Swainsonine is a plant toxin found in locoweed (families Fabaceae, Oxytropis, Astragalus and Swainsona) and some fungi (Metarhizium anisopliae, Rizoctonia leguminicola). |
Properties
| Appearance | White to Off-white Solid |
| Boiling Point | 353.3±21.0°C (Predicted) |
| Melting Point | >125°C (dec.) |
| Density | 1.38±0.1 g/cm3 at 20°C 760 Torr |
| Solubility | Soluble in DMSO (Slightly), Methanol (Slightly) |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Swainsonine inhibits the activity of glycoside hydrolases, especially N-linked glycosylation. Inhibition of Golgi mannosidase II and other alpha-mannosidases causes the accumulation of atypical hybrid glycoproteins and oligosaccarides because the proper processing cannot occur. This also results in intracellular vacuolization. |
Reference Reading
1.A swainsonine survey of North American Astragalus and Oxytropis taxa implicated as locoweeds.
Cook D1, Gardner DR2, Lee ST2, Pfister JA2, Stonecipher CA2, Welsh SL3. Toxicon. 2016 Apr 13;118:104-111. doi: 10.1016/j.toxicon.2016.04.033. [Epub ahead of print]
Swainsonine, an indolizidine alkaloid with significant physiological activity, is an α-mannosidase and mannosidase II inhibitor that causes lysosomal storage disease and alters glycoprotein processing. Swainsonine is found in a number of plant species worldwide, and causes severe toxicosis in livestock grazing these plants, leading to a chronic wasting disease characterized by weight loss, depression, altered behavior, decreased libido, infertility, and death. Swainsonine has been detected in 19 Astragalus and 2 Oxytropis species in North America by thin layer chromatography, gas chromatography-mass spectrometry, liquid chromatography-mass spectrometry and a jack bean α-mannosidase inhibition assay. In addition, 5 species in North America are presumed to contain swainsonine based upon reports from field cases. Many of these plant species have not been analyzed for swainsonine using modern instrumentation such as gas or liquid chromatography coupled with mass spectrometry.
2.Epimerization of C5 of an N-hydroxypyrrolidine in the synthesis of swainsonine related iminosugars.
Qian BC1, Kamori A2, Kinami K2, Kato A2, Li YX3, Fleet GW4, Yu CY5. Org Biomol Chem. 2016 Apr 19. [Epub ahead of print]
Epimerization of C5 of an N-hydroxypyrrolidine ring by regioselective oxidation to a nitrone followed by diastereoselective reduction provides a new approach to the synthesis of swainsonine and related compounds. The only protection in the synthesis of the potent mannosidase inhibitor DIM (1,4-dideoxy-1,4-imino-d-mannitol) was the acetonation of d-mannose.
Spectrum
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C8H15NO3
Molecular Weight (Monoisotopic Mass): 173.1052 Da
Molecular Weight (Avergae Mass): 173.2096 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C8H15NO3
Molecular Weight (Monoisotopic Mass): 173.1052 Da
Molecular Weight (Avergae Mass): 173.2096 Da
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C8H15NO3
Molecular Weight (Monoisotopic Mass): 173.1052 Da
Molecular Weight (Avergae Mass): 173.2096 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C8H15NO3
Molecular Weight (Monoisotopic Mass): 173.1052 Da
Molecular Weight (Avergae Mass): 173.2096 Da
13C NMR Spectrum
Experimental Conditions
Solvent: D2O
Nucleus: 13C
Frequency: 100
Nucleus: 13C
Frequency: 100
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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 ╳
