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
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].
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
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
Cheng07: 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
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
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
Ro06: 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
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