Gynocardin

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Gynocardin
Gynocardin.svg
Names
IUPAC name
(1R,4S,5R)-4,5-Dihydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclopent-2-ene-1-carbonitrile
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
  • InChI=1S/C12H17NO8/c13-4-12(2-1-5(15)10(12)19)21-11-9(18)8(17)7(16)6(3-14)20-11/h1-2,5-11,14-19H,3H2/t5-,6+,7+,8-,9+,10+,11-,12+/m0/s1
    Key: HASDUOHKNMHNJA-GDLVSTOPSA-N
  • C1=C[C@]([C@@H]([C@H]1O)O)(C#N)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
Properties
C12H17NO8
Molar mass 303.267 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Gynocardin is a chemical compound with the molecular formula C12H17NO8. It is classified as a cyanogenic glycoside.

It was first isolated from Gynocardia odorata , from which it gets it name, and characterized in 1905. [1] [2] It has since been found in a variety of other plants, including those in the genus Passiflora (passionflowers). [3]

Gynocardin may contribute to the toxicity of plants that contain it because, like other cyanogenic glycosides, cyanide is formed upon its hydrolysis. [3]

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Roslyn M. Gleadow is an Australian plant scientist, who leads the Plant Ecophysiological and Cyanogenesis Groups at Monash University, and was elected a Fellow of the Australian Academy of Science in 2024. Gleadow is Emerita Professor in the School of Biological Sciences at Monash University. She is also Honorary Professor The Queensland Alliance for Agriculture and Food Innovation University of Queensland and a Visiting Fellow, Institute for Climate, Energy & Disaster Solutions Australian National University.

References

  1. Power, Frederick Belding; Lees, Frederic Herbert (1905). "XLII.—Gynocardin, a new cyanogenetic glucoside". J. Chem. Soc., Trans. 87: 349–357. doi:10.1039/CT9058700349.
  2. Coburn, Robert A.; Long, Louis (1966). "Gynocardin". The Journal of Organic Chemistry. 31 (12): 4312–4315. doi:10.1021/jo01350a550.
  3. 1 2 Spencer, Kevin; Seigler, David (1984). "Gynocardin from Passiflora". Planta Medica. 50 (4): 356–357. doi:10.1055/s-2007-969732. PMID   17340327.