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discounted EARLY registration ends Dec 31, 2014
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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
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MetaCyc Pathway: β-caryophyllene 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.

Superclasses: Biosynthesis Secondary Metabolites Biosynthesis Terpenoids Biosynthesis Sesquiterpenoids Biosynthesis

Some taxa known to possess this pathway include ? : Arabidopsis thaliana col , Artemisia annua , Cannabis sativa , Cucumis sativus , Oryza sativa , Solanum lycopersicum , Syzygium aromaticum , Zea luxurians , Zea mays , Zea mays huehuetenangensis , Zea mays mexicana , Zea mays parviglumis

Expected Taxonomic Range: Viridiplantae

Summary:
beta-caryophyllene is bicyclic sesquiterpenoid found in the essential oils of Cannabis sativa, Clove and rosemary. The beta-caryophyllene is the first dietary cannabinoid approved by FDA. It selectively binds to the cannabinoid receptor type 1 (CB1) and (CB2). It is used in the treatment regimens of inflamation, pain, osteoporosis and atheroscelerosis [Gertsch08]. (E)-BCP is identified as a functional nonpsychoactive CB2 receptor ligand in foodstuff and as a macrocyclic antiinflammatory cannabinoid in Cannabis [Gertsch08]. As a component of clove oil extracted from syzigium, used in herbal medicine to treat pain, it is shown to posses aneasthetic activity [Ghelardini].

Since it is extensively used as a fragrance chemical in food and cosmetics, its allergen potential was evaluated and shown that it rapidly oxidizes upon exposure to air and the caryophyllene oxide can be a mild skin allergen [Skold06].

The enzyme that catalyzes the cyclization of FPP to form beta-caryophyllene has been characterized from a number of plant species included maize where it has been shown that this trait was lost and regained during cycles of domestication [Kollner08].

Credits:
Created 15-Jun-2009 by Pujar A , Boyce Thompson Institute


References

Gertsch08: Gertsch J, Leonti M, Raduner S, Racz I, Chen JZ, Xie XQ, Altmann KH, Karsak M, Zimmer A (2008). "Beta-caryophyllene is a dietary cannabinoid." Proc Natl Acad Sci U S A 105(26);9099-104. PMID: 18574142

Ghelardini: Ghelardini C, Galeotti N, Di Cesare Mannelli L, Mazzanti G, Bartolini A "Local anaesthetic activity of beta-caryophyllene." Farmaco 56(5-7);387-9. PMID: 11482764

Kollner08: Kollner TG, Held M, Lenk C, Hiltpold I, Turlings TC, Gershenzon J, Degenhardt J (2008). "A maize (E)-beta-caryophyllene synthase implicated in indirect defense responses against herbivores is not expressed in most American maize varieties." Plant Cell 20(2);482-94. PMID: 18296628

Skold06: Skold M, Karlberg AT, Matura M, Borje A (2006). "The fragrance chemical beta-caryophyllene-air oxidation and skin sensitization." Food Chem Toxicol 44(4);538-45. PMID: 16226832

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

Abbott89: Abbott RJ, Gomes MF (1989). "Population genetic structure and outcrossing rate of Arabidopsis thaliana (L) Heynh." Heredity 62:411-418.

Aubourg02: Aubourg S, Lecharny A, Bohlmann J (2002). "Genomic analysis of the terpenoid synthase ( AtTPS) gene family of Arabidopsis thaliana." Mol Genet Genomics 267(6);730-45. PMID: 12207221

Cai02: Cai Y, Jia JW, Crock J, Lin ZX, Chen XY, Croteau R (2002). "A cDNA clone for beta-caryophyllene synthase from Artemisia annua." Phytochemistry 61(5);523-9. PMID: 12409018

Chen03a: Chen F, Tholl D, D'Auria JC, Farooq A, Pichersky E, Gershenzon J (2003). "Biosynthesis and emission of terpenoid volatiles from Arabidopsis flowers." Plant Cell 15(2);481-94. PMID: 12566586

Cheng07a: Cheng AX, Xiang CY, Li JX, Yang CQ, Hu WL, Wang LJ, Lou YG, Chen XY (2007). "The rice (E)-beta-caryophyllene synthase (OsTPS3) accounts for the major inducible volatile sesquiterpenes." Phytochemistry 68(12);1632-41. PMID: 17524436

Cowan99: Cowan MM (1999). "Plant products as antimicrobial agents." Clin Microbiol Rev 12(4);564-82. PMID: 10515903

Koch00: Koch MA, Haubold B, Mitchell-Olds T (2000). "Comparative evolutionary analysis of chalcone synthase and alcohol dehydrogenase loci in Arabidopsis, Arabis, and related genera (Brassicaceae)." Mol Biol Evol 17(10);1483-98. PMID: 11018155

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

Loreto01: Loreto F, Velikova V (2001). "Isoprene produced by leaves protects the photosynthetic apparatus against ozone damage, quenches ozone products, and reduces lipid peroxidation of cellular membranes." Plant Physiol 127(4);1781-7. PMID: 11743121

Mercke04: Mercke P, Kappers IF, Verstappen FW, Vorst O, Dicke M, Bouwmeester HJ (2004). "Combined transcript and metabolite analysis reveals genes involved in spider mite induced volatile formation in cucumber plants." Plant Physiol 135(4);2012-24. PMID: 15310834

Pichersky02: Pichersky E, Gershenzon J (2002). "The formation and function of plant volatiles: perfumes for pollinator attraction and defense." Curr Opin Plant Biol 5(3);237-43. PMID: 11960742

Ro06a: Ro DK, Ehlting J, Keeling CI, Lin R, Mattheus N, Bohlmann J (2006). "Microarray expression profiling and functional characterization of AtTPS genes: duplicated Arabidopsis thaliana sesquiterpene synthase genes At4g13280 and At4g13300 encode root-specific and wound-inducible (Z)-gamma-bisabolene synthases." Arch Biochem Biophys 448(1-2);104-16. PMID: 16297850

Schilmiller10: Schilmiller AL, Miner DP, Larson M, McDowell E, Gang DR, Wilkerson C, Last RL (2010). "Studies of a biochemical factory: tomato trichome deep expressed sequence tag sequencing and proteomics." Plant Physiol 153(3);1212-23. PMID: 20431087

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

Tholl05: Tholl D, Chen F, Petri J, Gershenzon J, Pichersky E (2005). "Two sesquiterpene synthases are responsible for the complex mixture of sesquiterpenes emitted from Arabidopsis flowers." Plant J 42(5);757-71. PMID: 15918888

Yu08a: Yu F, Okamto S, Nakasone K, Adachi K, Matsuda S, Harada H, Misawa N, Utsumi R (2008). "Molecular cloning and functional characterization of alpha-humulene synthase, a possible key enzyme of zerumbone biosynthesis in shampoo ginger (Zingiber zerumbet Smith)." Planta 227(6);1291-9. PMID: 18273640


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 Sun Dec 21, 2014, biocyc14.