Capsidiol

Capsidiol
Names
IUPAC name
4α-Eremophila-9,11-diene-1β,3α-diol
Systematic IUPAC name
(1R,3R,4S,4aR,6R)-4,4a-Dimethyl-6-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene-1,3-diol
Identifiers
3D model (JSmol)
2331764
ChEBI
ChemSpider
ECHA InfoCard 100.247.709 Edit this at Wikidata
KEGG
UNII
  • InChI=1/C15H24O2/c1-9(2)11-5-6-12-14(17)7-13(16)10(3)15(12,4)8-11/h6,10-11,13-14,16-17H,1,5,7-8H2,2-4H3/t10-,11-,13-,14-,15-/m1/s1
    Key: BXXSHQYDJWZXPB-OKNSCYNVBL
  • O[C@H]2/C1=C/C[C@@H](\C(=C)C)C[C@@]1([C@H](C)[C@H](O)C2)C
Properties
C15H24O2
Molar mass 236.35 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Capsidiol is a terpenoid compound that accumulates in tobacco Nicotiana tabacum and chili pepper Capsicum annuum in response to fungal infection.[1] Capsidiol is categorized under the broad term of phytoalexin, a class of low molecular weight plant secondary metabolites that are produced during infection.[2]  Phytoalexins are also characterized as a part of a two pronged response to infection which involves a short term response consisting of production of free radicals near the site of infection and a long term response involving the production of hormones and an increase in enzymes to biosynthesize phytoalexins such as capsidiol.

  1. ^ Maldonado-Bonilla LD, Betancourt-Jiménez M, Lozoya-Gloria E (2008) "Local and systemic gene expression of sesquiterpene phytoalexin biosynthetic enzymes in plant leaves". European J. Plant Path. 121(4), 439-449.
  2. ^ Hammerschmidt R. (1999). "Phytoalexins: What have we learned after 60 years?" Anni. Rev. Phytopathol. 37, 285-306.