9, 4915–4927. Other bicyclic monoterpenes include carene, sabinene, camphene, and thujene. Atmos. Sci. doi: 10.1007/s00018-009-0066-7, Ziemann, P. J., and Atkinson, R. (2012). The public is invited to comment on this report during the 60-day public comment period ending on May 13, 2020. doi: 10.1093/aob/mcm240, Sharkey, T. D., and Yeh, S. S. (2001). Monocyclic monoterpenes. Steviol is the aglycone of stevia's sweet glycosides, one of them being made up by substituting one hydrogen atom (that is, bottom) having glucose through an ester link, and the other hydrogen atom (top) with a disaccharide (like, glucose and rhamnose). doi: 10.1071/CH9861739, Chang, H. C., Gage, D. A., and Oriel, P. J. The most common ring size in monoterpenes is a six-membered ring. Sesquiterpene structures present some acyclic, mono-, bi-, tri- and tetracyclic systems. Chem. Microbiological transformations of terpenes. Appl. Exploration of A-pinene degradation pathway of Pseudomonas rhodesiae cip 107491. A α-terpineol dehydratase from P. gladioli was isolated and partially purified. Seubert, W., and Remberger, U. Exposure of Canadians to alpha-pinene or the main components of sweet orange oil, turpentine oil/turpentine, fir oil and pine oil is also expected from the environment (for example, indoor and outdoor air). Microbiol. J. Geophys. Released throughout predator attack, it causes aphids to stop feeding, disperse and provide birth to winged (instead of wingless) forms that leave their host plants. (2009). Pseudomonas rhodesiae (CIP 107491) and P. fluorescens (NCIMB 11671) grew on α-pinene as sole carbon source. Deeper soil layers do contain significant less monoterpenes than the surface soil layer. J. Gen. Microbiol. Rev. Most of the substances in this grouping are of unknown or variable composition, complex reaction products, or biological materials (UVCBs). Rep. 37, 1787–1791. Among the BVOCs, isoprene and monoterpenes dominate with estimated emission rates of about 500 Tg C yr−1 and 127 Tg C yr−1, respectively (Guenther et al., 1995). Initially, (R)-limonene is hydroxylated by a NADPH-dependent limonene 6-monooxygenase (EC 18.104.22.168) to trans-carveol . Without detailed knowledge of genes or the availability of strains, the observations of biotransformation experiments are of limited value for future studies. Pseudomonas rhodesiae PF1: a new and efficient biocatalyst for production of isonovalal from α-pinene oxide. The oxidation of 1,8-cineole by Pseudomonas flava. Seubert, W., Fass, E., and Remberger, U. Park, Y. J., Kim, I. C., and Chang, H. C. (2003). (2008). Monoterpenes (C10H16) consist of two linked isoprene (C5H8) units and include in the strict sense only hydrocarbons. (2010). Microbiol. Atmos. Bacterial metabolism of alpha- and beta-pinene and related monoterpenes by Pseudomonas sp. p-Cumate catabolic pathway in Pseudomonas putida F1: cloning and characterization of DNA carrying the cmt operon. doi: 10.1007/978-3-642-22144-6_122, Trudgill, P. W. (1990). Only three pathways are completely known on the genetic and enzymatic level: the ones for camphor (CAM), p-cymene (CYM/CMT), and citronellol/geraniol (ATU/LIU). Figure 6. isopropenyl-7-methyl-2-oxo-oxepanone ; γ -terpineol ; p-menth-1-ene-6,8-diol . Appl. After hydrolysis of the lactone, the linear product is oxidized to isobutanoyl-CoA and three acetyl-CoA. Wood plants mainly accumulate pinene and other pure hydrocarbon monoterpenes as constituents of their resins, whereas citrus plants are the major source of limonene. They are of fungal or plant origin and are mainly found in resins, gummy exudates and in the resinous high-boiling fractions remaining after the distillation of essential oils. J. Appl. Li, H. J., and Lan, W. J. Microbial oxidation of α-pinene by Serratia marcescens. Recently, Grosmannia clavigera, a bark beetle-associated fungal pathogen of pine trees, was shown to grow on a mono- and diterpene mixture, containing α/β-pinene and 3-carene (Diguistini et al., 2011). (2000). Lett. Environ. Rev. Such compounds to be expected mediate the interaction among herbivores and their natural enemies, fascinated by Terpenes. Indeed, most monoterpene transforming bacteria have been enriched or isolated from soil and freshwater samples in habitats with monoterpene emitting vegetation. doi: 10.1128/AEM.70.9.5102-5110.2004, Diguistini, S., Wang, Y., Liao, N. Y., Taylor, G., Tanguay, P., Feau, N., et al. A classic example is the cyclization of geranyl pyrophosphate to form limonene. Biosynthetically, isopentenyl pyrophosphate and dimethylallyl pyrophosphate are combined to form geranyl pyrophosphate. doi: 10.1007/BF00993688. Appl. Plant Mol. Fungi excrete laccases which are copper-containing oxidases. Microbiol. R. opacus PWD4 uses (R)-limonene on the same pathway. Wilt, F. M., Miller, G. C., Everett, R. L., and Hackett, M. (1993). Microbiol. 79, 3468–3475. They have as well antioxidant properties, -Terpenes and hydroxytyrosol being among the most efficient. Isoprene emission from plants. J. Bacteriol. There were limited health effects (hazard) data for mandarin and tangerine oils, turpentine oil/turpentine, and fir oil. (1998). Thus, several fungi were described to transform monoterpenes during growth in rich medium (reviewed by Farooq et al., 2004). Name Number of Carbons Examples; Hemiterpenes: 5: Isoprene: Monoterpenes: 10: Menthol, Geraniol: Flavors, Food Additives: Sesquiterpenes: 15: ... Monocyclic Monoterpenes. Current uncertainties in the size of emission based on shipborne measurements in comparison to satellite data (Luo and Yu, 2010) may be resolved by incorporating an export from the continental atmosphere to the oceanic atmosphere (Hu et al., 2013). Rep. 3:1869. doi: 10.1038/srep01869, Cheong, T. K., and Oriel, P. J. The linalool dehydratase-isomerase (EC 22.214.171.124 and 126.96.36.199) of C. defragrans 65Phen catalyzes a regio- and stereo-specific hydration of β-myrcene yielding the tertiary alcohol (S)-(+)-linalool  and the isomerization to the primary alcohol geraniol (Brodkorb et al., 2010; Lueddeke and Harder, 2011). Kinetics, products, and mechanisms of secondary organic aerosol formation. The atmosphere is loaded with an estimated VOC emission rate of about 1150 Tg C yr−1 (Stotzky and Schenck, 1976; Guenther et al., 1995; Atkinson and Arey, 2003). 42, 461–469. Linalool dehydratase-isomerase, a bifunctional enzyme in the anaerobic degradation of monoterpenes. The two oxidation products were considered to be dead-end products as they accumulated in cultures (Wright et al., 1986). 78, 2128–2136. Emission rates into the atmosphere alone are estimated to be over 500 Tg per year. The acyclic monoterpene β-myrcene  (C10H16) is transformed by Pseudomonas aeruginosa (PTCC 1074) into dihydrolinalool, 2,6-dimethyloctane and α-terpineol. doi: 10.1111/j.1574-6976.1998.tb00382.x, Insam, H., and Seewald, M. S. A. Chem. Often the term monoterpene is applied including monoterpenoids which are characterized by oxygen-containing functional groups. Monoterpenes are derived biosynthetically from units of isopentenyl pyrophosphate, which is formed from acetyl-CoA via the intermediacy of mevalonic acid in the HMG-CoA reductase pathway. doi: 10.1016/j.fgb.2012.10.002, Leisch, H., Shi, R., Grosse, S., Morley, K., Bergeron, H., Cygler, M., et al. doi: 10.1007/BF00058829. No sequence information was found in public databases. For non-ruminant animals (such as, rodents, chickens and humans), (-)- gossypol is considerably more toxic than the (+) enantiomers. A specialized ABC efflux transporter GcABC-G1 confers monoterpene resistance to Grosmannia clavigera, a bark beetle-associated fungal pathogen of pine trees. Biosynthesis, function and metabolic engineering of plant volatile organic compounds. A general precaution has to be mentioned here for many biotransformation studies: monoterpenes contain often impurities and oxidation products which may be utilized as substrates resulting in traces of monoterpene and monoterpenoid transformation products that are not further metabolized. 179, 3171–3180. doi: 10.1007/s00253-010-2644-x, Foss, S., and Harder, J. Start Excelling in your courses, Ask an Expert and get answers for your homework and assignments!! U.S.A. 108, 2504–2509. Biol. doi: 10.1021/es803669a, Gantt, B., Meskhidze, N., and Kamykowski, D. (2009). doi: 10.1016/S0723-2020(98)80028-3, Fu, P. Q., Kawamura, K., Chen, J., and Barrie, L. A. doi: 10.5194/acp-10-2007-2010, Mahmoud, S. S., and Croteau, R. B. linalool) (Kesselmeier and Staudt, 1999 and references therein, Sharkey and Yeh, 2001; Bicas et al., 2009). 61, 269–277. 52, 380–385. Examples of monoterpenes and monoterpenoids include geraniol, terpineol (present in lilacs), limonene (present in citrus fruits), myrcene (present in hops), linalool (present in lavender) or pinene (present in pine trees). Chem. Since 2009, Tutorsglobe has proactively helped millions of students to get better grades in school, college or university and score well in competitive tests with live, one-on-one online tutoring. (2013). 3. Phys. 2010:408696. doi: 10.1155/2010/408696, Speelmans, G., Bijlsma, A., and Eggink, G. (1998). These include reviews by the. In the absence of molecular oxygen, Castellaniella defragrans 65Phen has an unique enzyme for the linalool transformation, the linalool dehydratase-isomerase (Brodkorb et al., 2010). Esmaeili, A., and Hashemi, E. (2011). doi: 10.1016/S0032-9592(01)00262-X, Yu, F. N. A., and Utsumi, R. (2009). J. Chem. Several monoterpenes derivatives have antibacterial activity, such as linalool. Pseudomonas putida F1 (ATCC 700007) degrades p-cymene to p-cumate  via the CYM-pathway (cymBCAaAbDE). Int. A cytochrome P450 monooxygenase from Bacillus cereus UI-1477 catalyzes the hydroxylation of 1,8-cineole, yielding either 2R-endo- or 2R-exo-hydroxy-1,8-cineole  (Liu and Rosazza, 1990, 1993).
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