Coronatine

Last updated
Coronatine
Coronatine structure.svg
Names
Preferred IUPAC name
(1S,2S)-2-Ethyl-1-[(3aS,6R,7aS)-6-ethyl-1-oxo-2,3,3a,6,7,7a-hexahydro-1H-indene-4-carboxamido]cyclopropane-1-carboxylic acid
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C18H25NO4/c1-3-10-7-13-12(5-6-15(13)20)14(8-10)16(21)19-18(17(22)23)9-11(18)4-2/h8,10-13H,3-7,9H2,1-2H3,(H,19,21)(H,22,23)/t10-,11+,12+,13+,18+/m1/s1
    Key: FMGBNISRFNDECK-CZSBRECXSA-N
  • InChI=1/C18H25NO4/c1-3-10-7-13-12(5-6-15(13)20)14(8-10)16(21)19-18(17(22)23)9-11(18)4-2/h8,10-13H,3-7,9H2,1-2H3,(H,19,21)(H,22,23)/t10-,11+,12+,13+,18+/m1/s1
    Key: FMGBNISRFNDECK-CZSBRECXBX
  • O=C(O)[C@@]3(NC(=O)/C1=C/[C@@H](C[C@@H]2C(=O)CC[C@H]12)CC)[C@@H](CC)C3
Properties
C18H25NO4
Molar mass 319.401 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Coronatine (COR) is a toxin produced by the bacterium Pseudomonas syringae . It is involved in causing stomata to re-open after they close in response to pathogen-associated molecular patterns, as well as interfering with the responses mediated by salicylic acid after the infection has begun. It consists of coronafacic acid (CFA), which is an analog of methyl jasmonic acid (MeJA), and coronamic acid (CMA), joined by an amide bond between the acid group of CFA and the amino group of CMA. [1]

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References

  1. Melotto, Maeli; Underwood, William; He, Sheng Yang (2008). "Role of Stomata in Plant Innate Immunity and Foliar Bacterial Diseases". Annual Review of Phytopathology. 46: 101–22. doi:10.1146/annurev.phyto.121107.104959. PMC   2613263 . PMID   18422426.