Amabiline

Amabiline
Names
Preferred IUPAC name
[(7aS)-5,6,7,7a-Tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C15H25NO4/c1-10(2)15(19,11(3)17)14(18)20-9-12-6-8-16-7-4-5-13(12)16/h6,10-11,13,17,19H,4-5,7-9H2,1-3H3/t11-,13-,15-/m0/s1
    Key: DRVWTOSBCBKXOR-WHOFXGATSA-N
  • C[C@@H]([C@@](C(C)C)(C(=O)OCC1=CCN2[C@H]1CCC2)O)O
Properties
C15H25NO4
Molar mass 283.368 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Amabiline is a pyrrolizidine alkaloid first isolated in 1967 from Cynoglossum amabile.[1] It is also found in the seeds and flowers of borage (Borago officinalis)[2] and in borage seed oil.[3][4]

Chemically, it is the ester derived from viridifloric acid and supinidine.[5]

Amabiline is hepatotoxic and may contribute to the potential liver damage caused by consumption of borage and its seed oil.[6]

References

[edit]
  1. ^ Culvenor, CCJ; Smith, LW (1967). "The alkaloids of Cynoglossum australe R.Br. And C. Amabile Stapf & Drummond". Australian Journal of Chemistry. 20 (11): 2499. doi:10.1071/CH9672499.
  2. ^ Dodson, Craig D.; Stermitz, Frank R. (1986). "Pyrrolizidine Alkaloids from Borage (Borago officinalis) Seeds and Flowers". Journal of Natural Products. 49 (4): 727–728. doi:10.1021/np50046a045.
  3. ^ Parvais, O.; Vander Stricht, B.; Vanhaelen-Fastre, R.; Vanhaelen, M. (1994). "TLC detection of pyrrolizidine alkaloids in oil extracted from the seeds of Borago officinalis". Journal of Planar Chromatography--Modern TLC. 7 (1): 80–82.
  4. ^ Wretensjoe, Inger; Karlberg, Bo. (2003). "Pyrrolizidine alkaloid content in crude and processed borage oil from different processing stages". Journal of the American Oil Chemists' Society. 80 (10): 963–970. doi:10.1007/s11746-003-0804-z. S2CID 94575246.
  5. ^ The Alkaloids: Chemistry and Physiology. Academic Press. 1970. pp. 302–303.
  6. ^ "Borage". Memorial Sloan Kettering Cancer Center. 31 March 2022.
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