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Organic Chemistry

Generation of (2-Nitroethyl)benzene and related benzenoids from L-Phenylalanine; flower scents of the Japanese Loquat Eriobotrya japonica [Rosales: Rosaceae]

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Pages 1855-1866 | Received 24 Dec 2017, Accepted 18 Jun 2018, Published online: 25 Jul 2018

References

  • Kuwahara Y, Ichiki Y, Morita M, et al (2-Nitroethyl)benzene: a major flower scent from the Japanese loquat Eriobotrya japonica [Rosales: rosaceae]. Biosci Biotech Biochem. 2014;78:1320–1323.
  • Adeoti SB, Ayedoun MA, Leciercq PA. Essential oil of Denettia tripetala leaves from Benin. J Essent Oil Res. 2000;12:412–414.
  • Ajaiyeoba EO, Ekundaya O, Okogun JI, et al Antifungal agents: syntheses and antifungal activities of 2-phenylnitroethane; a component of Dennettia tripetala fruits and nitro vinyl derivatives. J Pharm Res Develop. 1999;4:47–52.
  • Naranjo P, Kijjoa A, Giesbrecht AM, et al Ocotea quixos, American cinnamon. J Ethnopharmacol. 1981;4:233–236.
  • Pott MB, Pichersky E, Piechulla B. Characterization of an acyltransferase capable of synthesizing benzyl benzoate and other volatile esters in flowers and damaged leaves of Clarkia breweri. J Plant Physiol. 2002;159:925–934.
  • Kaiser R, Lamparsky D. Constituants azotes en trace de quelques absolues de fleurs et leurs headspaces correspondants. In: Grasse F, editor. Proceedings of 8th International Congrress of Essential Oils; (Cannes, 1980); Fedarom, Grasse, France 1982. p. 287–294.
  • Kaiser R. The scents of orchids, olfactory and chemical investigations. Amsterdam: Elsevier;1993. p. 259. ISBN10:0444898417/ISBN 13: 9780444898418.
  • Stashenko EE, Prada NQ, Martínez JR. HRGC/FID/NPD and HRGC/MSD study of Colombian Ylang-Ylang (Cananga odorata) oils obtained by different extraction techniques. J High Resol Chromatogr. 1996;19:353–358.
  • Rg B, Teranishi R, Lc L, et al Quantitative and sensory studies on tomato paste volatiles. J Agric Food Chem. 1990;36:336–340.
  • Kuwahara Y, Tanabe T, Asano Y. Changes in defense allomone compositions of Eutrichodesmus legans and Eutrichodesmus armatus (Polydesmida: haplodesmidae)during different stages of their life cycles. Appl Entomol Zool. 2017;52:305–312.
  • Matsuo M, Kirkland DF, Underhill EW. 1-Nitro-2-phenylethane, a possible intermediate in the biosynthesis of benzylglucosinolate. Phytochem. 1972;11:697–701.
  • Koeduka T, Kajiyama M, Suzuki H, et al Benzenoid biosynthesis in the flowers of Eriobotrya japonica: molecular cloning and functional characterization of p-methoxybenzoic acid carboxyl methyltransferase. Planta. 2016;244:725–736.
  • Kuwahara Y, Shimizu N, Tanabe T. Release of hydrogen cyanide via a post-secretion Schotten-Baumann reaction in defensive fluids of polydesmoid millipedes. J Chem Ecol. 2011;37:232–238.
  • Kuwahara Y, Mori N, Sakuma M, et al (1Z)- and (1E)-2-Nitroethenylbenzenes, and 2-nitroethylbenzene as natural products in defense secretions of a millipede Thelodesmus armatus Miyosi (Polydesmida: pyrgodesmidae). Jpn J Environ Entomol Zool. 2003;14:149–155.
  • McKenna R, Nielsen DR. Styrene biosynthesis from glucose by engineered E. coli. Metab Eng. 2011;13:544–554.
  • Yamaguchi T, Kuwahara Y, Asano Y. A novel cytochrome P450, CYP3201B1, is involved in (R)-mandelonitrile biosynthesis in a cyanogenic millipede. FEBS Open Bio. 2017. DOI:10.1002/2211-5463.12170
  • Ueatrongchit T, Kayo A, Komeda H, et al Purification and characterization of a novel R-hydroxynitrile lyase from Eriobotrya japonica (Loquat). Biosci Biotech Biochem. 2008;72:1513–1522.
  • Vilegas JH, Lanças FM, Vilegas W. Composition of the volatile compounds from Aniba canelilla (HBK) Mez. extracted by CO2 in the supercritical state. Rev bras farmacogn. 1998;7:13–19.
  • Gbolade AA, Arcoraci T, D’Arrigo M, et al Essential oils of Dennettia tripetala Bak. f. stem bark and leaf. Constituents and biological activities. Planta Med. 2009;75(09):PI32.
  • Kuwahara Y, Ômura H, Tanabe T. 2-Nitroethenylbenzene as natural products in millipede defense secretions. Naturwissenschaften. 2002;89:308–310.
  • El-Sayed AM. (2017). The pherobase: database of pheromones and semiochemicals. Available from: http://www.pherobase.com
  • Buttery RG. Quantitative and sensory aspects of flavor of tomato and other vegetables and fruits. In: Acree T, Teranishi R, editor. Flavor Science: sensible principles and techniques,”. Washington, DC, USA: ACS; 1993. p. 259–286.
  • Noge K, Tamogami S. Isovaleronitrile co-induced with its precursor, L-leusine, by herbivory in the common evening primrose stimulates foraging behavior of the predatory blue shield bug. Biosci Biotech Biochem. 2018;82:395–406.
  • Knudsen JT, Tollsten L, Bergstrom LG. Floral scents—a checklist of volatile compounds isolated by head-space techniques. Phytochemistry. 1993;33:253–280.
  • Imai T, Maekawa M, Tsuchiya S. Attractiveness of p-anisaldehyde to the varied carpet beetle, Anthrenus verbasci (L.)(Coleoptera: dermestidae). Appl Entomol Zool. 2002;37:505–508.

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