monoterpene biosynthesis

Perestrelo R, Barros AS, Rocha SM, Câmara JS. Optimisation of solid-phase microextraction combined with gas chromatography-mass spectrometry based methodology to establish the global volatile signature in pulp and skin of Vitis vinifera L. grape varieties. Talanta. 2011 Sep 15;85(3):1483–93. doi: 10.1016/j.talanta.2011.06.025. PMID: 21807213.; Sun Q, Gates MJ, Lavin EH, Acree TE, Sacks GL. Comparison of odor-active compounds in grapes and wines from vitis vinifera and non-foxy American grape species. J Agric Food Chem. 2011 Oct 12;59(19):10657–64. doi: 10.1021/jf2026204. PMID: 21879766.; Martin DM, Aubourg S, Schouwey MB, Daviet L, Schalk M, Toub O, Lund ST, Bohlmann J. Functional Annotation, Genome Organization and Phylogeny of the Grapevine (Vitis vinifera) Terpene Synthase Gene Family Based on Genome Assembly, FLcDNA Cloning, and Enzyme Assays. BMC Plant Biology. 2010 Oct 21;10(1):226. doi: 10.1186/1471-2229-10-226.; BRILLI F, CICCIOLI P, FRATTONI M, PRESTININZI M, SPANEDDA AF, LORETO F. Constitutive and herbivore-induced monoterpenes emitted by Populus × euroamericana leaves are key volatiles that orient Chrysomela populi beetles. Plant Cell & Environment. 2009 Apr 07;32(5):542–52. doi: 10.1111/j.1365-3040.2009.01948.x.; El-Ghorab A, El-Massry KF, Shibamoto T. Chemical composition of the volatile extract and antioxidant activities of the volatile and nonvolatile extracts of Egyptian corn silk (Zea mays L.). J Agric Food Chem. 2007 Oct 31;55(22):9124–7. doi: 10.1021/jf071646e. PMID: 17914872.; Rocha SM, Coelho E, Zrostlíková J, Delgadillo I, Coimbra MA. Comprehensive two-dimensional gas chromatography with time-of-flight mass spectrometry of monoterpenoids as a powerful tool for grape origin traceability. J Chromatogr A. 2007 Aug 17;1161(1-2):292–9. doi: 10.1016/j.chroma.2007.05.093. PMID: 17585921.; Grimplet J, Deluc LG, Tillett RL, Wheatley MD, Schlauch KA, Cramer GR, Cushman JC. Tissue-specific mRNA expression profiling in grape berry tissues. BMC Genomics. 2007 Jun 21;8():187. PMID: 17584945; PMCID: PMC1925093.; Birkett MA, Chamberlain K, Khan ZR, Pickett JA, Toshova T, Wadhams LJ, Woodcock CM. Electrophysiological Responses of the Lepidopterous Stemborers Chilo partellus and Busseola fusca to Volatiles from Wild and Cultivated Host Plants. Journal of Chemical Ecology. 2006 Nov 01;32(11):2475–87. doi: 10.1007/s10886-006-9165-1.; Gouinguené S, Pickett JA, Wadhams LJ, Birkett MA, Turlings TCJ. Antennal Electrophysiological Responses of Three Parasitic Wasps to Caterpillar-Induced Volatiles from Maize (Zea mays mays), Cotton (Gossypium herbaceum), and Cowpea (Vigna unguiculata). Journal of Chemical Ecology. 2005 May 27;31(5):1023–38. doi: 10.1007/s10886-005-4245-1.; Chen F, Ro DK, Petri J, Gershenzon J, Bohlmann J, Pichersky E, Tholl D. Characterization of a root-specific Arabidopsis terpene synthase responsible for the formation of the volatile monoterpene 1,8-cineole. Plant Physiol. 2004 Aug;135(4):1956–66. PMID: 15299125; PMCID: PMC520767.; Martin DM, Bohlmann J. Identification of Vitis vinifera (-)-alpha-terpineol synthase by in silico screening of full-length cDNA ESTs and functional characterization of recombinant terpene synthase. Phytochemistry. 2004 May;65(9):1223–9. doi: 10.1016/j.phytochem.2004.03.018. PMID: 15184006.; Fäldt J, Arimura G, Gershenzon J, Takabayashi J, Bohlmann J. Functional identification of AtTPS03 as (E)-beta-ocimene synthase: a monoterpene synthase catalyzing jasmonate- and wound-induced volatile formation in Arabidopsis thaliana. Planta. 2003 Mar;216(5):745–51. doi: 10.1007/s00425-002-0924-0. PMID: 12624761.; Bohlmann J, Martin D, Oldham NJ, Gershenzon J. Terpenoid secondary metabolism in Arabidopsis thaliana: cDNA cloning, characterization, and functional expression of a myrcene/(E)-beta-ocimene synthase. Arch Biochem Biophys. 2000 Mar 15;375(2):261–9. doi: 10.1006/abbi.1999.1669. PMID: 10700382.; Bohlmann J, Phillips M, Ramachandiran V, Katoh S, Croteau R. cDNA Cloning, Characterization, and Functional Expression of Four New Monoterpene Synthase Members of the Tpsd Gene Family from Grand Fir (Abies grandis). Archives of Biochemistry and Biophysics. 1999 Aug;368(2):232–43. doi: 10.1006/abbi.1999.1332.; Steele CL, Crock J, Bohlmann J, Croteau R. 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. 1998 Jan 23;273(4):2078–89. doi: 10.1074/jbc.273.4.2078. PMID: 9442047.

Metabolites

(-)-alpha-Pinene

Formula: C10H16 (136.1251936)

CAS ID: 7785-26-4

(-)-beta-Pinene

Formula: C10H16 (136.1251936)

CAS ID: 18172-67-3

(+)-Camphene

Formula: C10H16 (136.1251936)

CAS ID: 5794-03-6

(E)-beta-Ocimene

Formula: C10H16 (136.1251936)

CAS ID: 3779-61-1

(R)-Limonene

Formula: C10H16 (136.1251936)

CAS ID: 5989-27-5

1,8-Cineole

Formula: C10H18O (154.1357578)

CAS ID: 470-82-6

H2O

Formula: H2O (18.0105642)

CAS ID: 7732-18-5

Myrcene

Formula: C10H16 (136.1251936)

CAS ID: 123-35-3

Sabinene

Formula: C10H16 (136.1251936)

CAS ID: 3387-41-5

Terpinolene

Formula: C10H16 (136.1251936)

CAS ID: 586-62-9

cis-Ocimene

Formula: C10H16 (136.1251936)

CAS ID: 3338-55-4



Enzyme

EC Number name full name note


Proteins

Protein ID name full name