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Amabiline

Amabiline is a pyrrolizidine alkaloid first isolated in 1967 from Cynoglossum amabile. It is also found in the seeds and flowers of borage and in borage seed oil.

Last revised
Jul 20, 2026
Read time
≈ 1 min
Length
263 w
Citations
6
Source
Wikipedia ↗
Amabiline
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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.34

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

References

  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. Bibcode:1986JNAtP..49..727D. 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.