Updated BioCyc iOS App now
available in iTunes store
Updated BioCyc iOS App now
available in iTunes store
Updated BioCyc iOS App now
available in iTunes store
Updated BioCyc iOS App now
available in iTunes store
Updated BioCyc iOS App now
available in iTunes store

MetaCyc Pathway: lacinilene C biosynthesis
Inferred from experiment

Pathway diagram: lacinilene C biosynthesis

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Superclasses: BiosynthesisSecondary Metabolites BiosynthesisTerpenoids Biosynthesis

Some taxa known to possess this pathway include : Gossypium arboreum

Expected Taxonomic Range: Gossypium

Lacinilene C is a cotton terpenoid derived from cadinene, which is also a precursor for gossypol biosynthesis. 8-hydroxylation of cadinene leads to gossypol, whereas 7-hydroxylation leads to lacinilene. 7-hydroxylated cadinanes, such as 2,7-dihydroxycadalene and lacinilene C, are phytoalexins induced to accumulate in the foliar tissues after bacteria attack. Inhalation of lacinilene C 7-methyl ether from cotton processing dust was thought to be the cause of chronic respiration distress seen in some fiber mill workers.

The occurrence of the lacinilenes in an optically active form indicates that they are formed enzymatically in vivo. They can also be formed non-enzymatically by in vitro auto-oxidation of 2,7-dihydroxycadalene [Stipanovic81].

Citations: [Chen96b, Townsend05]

Created 03-Mar-2008 by Zhang P, TAIR


Chen96b: Chen XY, Wang M, Chen Y, Davisson VJ, Heinstein P (1996). "Cloning and heterologous expression of a second (+)-delta-cadinene synthase from Gossypium arboreum." J Nat Prod 59(10);944-51. PMID: 8904844

Stipanovic81: Stipanovic R, Greenblatt G, Beier R, Bell A (1981). "2-Hydroxy-7-methoxycadalene. The precursor of lacinilene C 7-methyl ether in Gossypium." Phytochemistry, 20(4): 729-730.

Townsend05: Townsend BJ, Poole A, Blake CJ, Llewellyn DJ (2005). "Antisense suppression of a (+)-delta-cadinene synthase gene in cotton prevents the induction of this defense response gene during bacterial blight infection but not its constitutive expression." Plant Physiol 138(1);516-28. PMID: 15849309

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Chen95: Chen XY, Chen Y, Heinstein P, Davisson VJ (1995). "Cloning, expression, and characterization of (+)-delta-cadinene synthase: a catalyst for cotton phytoalexin biosynthesis." Arch Biochem Biophys 324(2);255-66. PMID: 8554317

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Steele98: Steele CL, Crock J, Bohlmann J, Croteau R (1998). "Sesquiterpene synthases from grand fir (Abies grandis). Comparison of constitutive and wound-induced activities, and cDNA isolation, characterization, and bacterial expression of delta-selinene synthase and gamma-humulene synthase." J Biol Chem 273(4);2078-89. PMID: 9442047

Tan00: Tan XP, Liang WQ, Liu CJ, Luo P, Heinstein P, Chen XY (2000). "Expression pattern of (+)-delta-cadinene synthase genes and biosynthesis of sesquiterpene aldehydes in plants of Gossypium arboreum L." Planta 210(4);644-51. PMID: 10787059

Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by Pathway Tools version 19.5 (software by SRI International) on Tue May 3, 2016, biocyc14.