Synonym
(-)-Lasiocarpine, 7-Angelyleuropine, AI3-51770, Europine 7-angelate, Lasiocarpine
IUPAC/Chemical Name
2,3,5,7alphabeta-Tetrahydro-1-hydroxy-1H-pyrrolizine-7-methanol-1-angelate-7-(2,3-dihydroxy-2(1-methoxyethyl))-3-methyl-butyrate
InChi Key
QHOZSLCIKHUPSU-LPLKQDONSA-N
InChi Code
InChI=1S/C21H33NO7/c1-7-13(2)18(23)29-16-9-11-22-10-8-15(17(16)22)12-28-19(24)21(26,14(3)27-6)20(4,5)25/h7-8,14,16-17,25-26H,9-12H2,1-6H3/b13-7-/t14-,16-,17+,21-/m0/s1
SMILES Code
O=C(/C(C)=C\C)O[C@H]1CCN2[C@@H]1C(COC([C@@](C(C)(O)C)(O)[C@H](C)OC)=O)=CC2
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
411.50
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Luckert C, Braeuning A, Lampen A, Hessel-Pras S. PXR: Structure-specific activation by hepatotoxic pyrrolizidine alkaloids. Chem Biol Interact. 2018 May 25;288:38-48. doi: 10.1016/j.cbi.2018.04.017. Epub 2018 Apr 14. PubMed PMID: 29665350.
2: Forsch K, Schöning V, Disch L, Siewert B, Unger M, Drewe J. Development of an in vitro screening method of acute cytotoxicity of the pyrrolizidine alkaloid lasiocarpine in human and rodent hepatic cell lines by increasing susceptibility. J Ethnopharmacol. 2018 May 10;217:134-139. doi: 10.1016/j.jep.2018.02.018. Epub 2018 Feb 14. PubMed PMID: 29454024.
3: Fashe MM, Juvonen RO, Petsalo A, Räsänen J, Pasanen M. Species-Specific Differences in the in Vitro Metabolism of Lasiocarpine. Chem Res Toxicol. 2015 Oct 19;28(10):2034-44. doi: 10.1021/acs.chemrestox.5b00253. Epub 2015 Oct 2. PubMed PMID: 26395423.
4: Xia Q, Zhao Y, Von Tungeln LS, Doerge DR, Lin G, Cai L, Fu PP. Pyrrolizidine alkaloid-derived DNA adducts as a common biological biomarker of pyrrolizidine alkaloid-induced tumorigenicity. Chem Res Toxicol. 2013 Sep 16;26(9):1384-96. doi: 10.1021/tx400241c. Epub 2013 Aug 26. PubMed PMID: 23937665.
5: Xia Q, Chou MW, Edgar JA, Doerge DR, Fu PP. Formation of DHP-derived DNA adducts from metabolic activation of the prototype heliotridine-type pyrrolizidine alkaloid, lasiocarpine. Cancer Lett. 2006 Jan 8;231(1):138-45. PubMed PMID: 16356839.
