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MetaCyc Pathway: germacrene biosynthesis

Enzyme View:

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.

Synonyms: germacrene pathway

Superclasses: Biosynthesis Secondary Metabolites Biosynthesis Terpenoids Biosynthesis Sesquiterpenoids Biosynthesis

Some taxa known to possess this pathway include ? : Artemisia annua , Cichorium intybus , Cistus creticus , Lactuca sativa romaine , Pogostemon cablin , Solanum habrochaites , Solanum lycopersicum , Solidago canadensis , Zingiber officinale

Expected Taxonomic Range: Magnoliophyta

Summary:
Germacrenes are the bitter sesquiterpene olefins produced by a number of plants representing compounds that possess antifeedant, antimicrobial and insecticidal properties and also function as insect pheromones [Rostelien00]. There are 4 known types of germacrenes, germacrene A, (E,E)-germacrene B, germacrene C, (-)-germacrene D, which are unstable due to their susceptibility to proton-induced cyclization towards α-selinene and β-selinene [deKraker98].

Most of these compounds can exist as enantiomers. Germacrene A is postulated to be an intermediate bound to sesquiterpene cyclase(s) involved in the biosynthesis of patchoulol, aristolochene, capsidiol and vetispiradiene. Insect response studies show that (-)-germacrene D targets insect neurons in a highly selective way and significantly stands out amongst a host of similar compounds [Rostelien00].

Germacrene synthases, the specific sesquiterpene synthases that cyclize (2E,6E)-farnesyl diphosphate into germacrenes have been isolated from a number of plants including, Solidago canadensis [Prosser02], Solanum lycopersicum [Colby98], Lactuca sativa romaine [Bennett02] and others. The enantiomer-specific synthases produce different enantiomeric products [Picaud06]. The biosynthesis of these compounds involves stereoselective oxidative enzymes that might be useful as catalysts in organic syntheses [deKraker98]. Active site modification and mutagenesis studies show that subtle changes in the active site residues are necessary for carrying out the synthesis of enantiomeric germacrenes. On the other side it has been demonstrated that the Mg2+-binding motif of the sesquiterpene synthases might not be as stringent as previously thought as the aspartate at position 303 can either be replaced by asparagine or might even be lacking as found for the germacrene D synthase (Sc11) of Solidago canadensis [Prosser02].

Credits:
Created 29-Nov-2007 by Pujar A , Cornell University
Revised 02-Jul-2012 by Foerster H , Boyce Thompson Institute


References

Bennett02: Bennett MH, Mansfield JW, Lewis MJ, Beale MH (2002). "Cloning and expression of sesquiterpene synthase genes from lettuce (Lactuca sativa L.)." Phytochemistry 60(3);255-61. PMID: 12031443

Colby98: Colby SM, Crock J, Dowdle-Rizzo B, Lemaux PG, Croteau R (1998). "Germacrene C synthase from Lycopersicon esculentum cv. VFNT cherry tomato: cDNA isolation, characterization, and bacterial expression of the multiple product sesquiterpene cyclase." Proc Natl Acad Sci U S A 95(5);2216-21. PMID: 9482865

deKraker98: de Kraker JW , Franssen MC, de Groot A , Konig WA, Bouwmeester HJ (1998). "(+)-Germacrene A biosynthesis . The committed step in the biosynthesis of bitter sesquiterpene lactones in chicory." Plant Physiol 117(4);1381-92. PMID: 9701594

Picaud06: Picaud S, Olsson ME, Brodelius M, Brodelius PE (2006). "Cloning, expression, purification and characterization of recombinant (+)-germacrene D synthase from Zingiber officinale." Arch Biochem Biophys 452(1);17-28. PMID: 16839518

Prosser02: Prosser I, Phillips AL, Gittings S, Lewis MJ, Hooper AM, Pickett JA, Beale MH (2002). "(+)-(10R)-Germacrene A synthase from goldenrod, Solidago canadensis; cDNA isolation, bacterial expression and functional analysis." Phytochemistry 60(7);691-702. PMID: 12127586

Rostelien00: Rostelien, T, Borg-Karlson, A.-K, Faldt, J, Jacobsson, U, Mustaparta, H (2000). "The plant sesquiterpene germacrene D specifcally activates a major type of antennal receptor neuron of the tobacco budworm moth heliothis virescens." Chem. Senses, 25, 141-148.

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

Bertea06: Bertea CM, Voster A, Verstappen FW, Maffei M, Beekwilder J, Bouwmeester HJ (2006). "Isoprenoid biosynthesis in Artemisia annua: cloning and heterologous expression of a germacrene A synthase from a glandular trichome cDNA library." Arch Biochem Biophys 448(1-2);3-12. PMID: 16579958

Bouwmeester02: Bouwmeester HJ, Kodde J, Verstappen FW, Altug IG, de Kraker JW, Wallaart TE (2002). "Isolation and characterization of two germacrene A synthase cDNA clones from chicory." Plant Physiol 129(1);134-44. PMID: 12011345

Deguerry06: Deguerry F, Pastore L, Wu S, Clark A, Chappell J, Schalk M (2006). "The diverse sesquiterpene profile of patchouli, Pogostemon cablin, is correlated with a limited number of sesquiterpene synthases." Arch Biochem Biophys 454(2);123-36. PMID: 16970904

Falara08: Falara V, Fotopoulos V, Margaritis T, Anastasaki T, Pateraki I, Bosabalidis AM, Kafetzopoulos D, Demetzos C, Pichersky E, Kanellis AK (2008). "Transcriptome analysis approaches for the isolation of trichome-specific genes from the medicinal plant Cistus creticus subsp. creticus." Plant Mol Biol 68(6);633-51. PMID: 18819010

Kumeta10: Kumeta Y, Ito M (2010). "Characterization of {delta}-Guaiene Synthases from Cultured Cells of Aquilaria, Responsible for the Formation of the Sesquiterpenes in Agarwood." Plant Physiol 154(4);1998-2007. PMID: 20959422

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

Majdi11: Majdi M, Liu Q, Karimzadeh G, Malboobi MA, Beekwilder J, Cankar K, Vos Rd, Todorovic S, Simonovic A, Bouwmeester H (2011). "Biosynthesis and localization of parthenolide in glandular trichomes of feverfew (Tanacetum parthenium L. Schulz Bip.)." Phytochemistry 72(14-15);1739-50. PMID: 21620424

Nabeta97: Nabeta, K., Fujita, M., Komuro, K., Katayama, K., Takasawa, T. (1997). "In vitro biosynthesis of cadinanes by cell-free extracts of cultured cells of Heteroscyphus planus." J. Chem. Soc., Perkin Trans. 1 :2065-2070.

Prosser04: Prosser I, Altug IG, Phillips AL, Konig WA, Bouwmeester HJ, Beale MH (2004). "Enantiospecific (+)- and (-)-germacrene D synthases, cloned from goldenrod, reveal a functionally active variant of the universal isoprenoid-biosynthesis aspartate-rich motif." Arch Biochem Biophys 432(2);136-44. PMID: 15542052

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

vanDer00: van Der Hoeven RS, Monforte AJ, Breeden D, Tanksley SD, Steffens JC (2000). "Genetic control and evolution of sesquiterpene biosynthesis in Lycopersicon esculentum and L. hirsutum." Plant Cell 12(11);2283-94. PMID: 11090225


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 SRI International Pathway Tools version 18.5 on Fri Nov 21, 2014, BIOCYC14A.